# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_1_100K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921985'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_1_100K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      37.18 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT355_complex_1_100K_shelxl 
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O3       - H1       .       1.09 Ang.  
RESPONSE: The long O-H distance is characteristic of H1 being in a 
short O-H...O hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea phthalic acid 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C3 H8 N2 O1), (C8 H6 O4)'
_chemical_formula_sum            'C14 H22 N4 O6'
_chemical_formula_weight         342.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0076 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0133 0.0073 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.8576(5)
_cell_length_b                   6.4443(4)
_cell_length_c                   32.5997(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.616(3)
_cell_angle_gamma                90
_cell_volume                     1645.39(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    5923
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      43.26

_exptl_crystal_description       'rectangular needle'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9017
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22440
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.734
_diffrn_reflns_theta_max         30.650
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3940
_reflns_number_gt                2933
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

SHEL 1000 0.76 command used to make multi_T datasets comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (300 K) data set.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+0.5010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3940
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H5 H 0.079(2) 0.100(3) 0.2354(6) 0.018(5) Uiso 1 1 d . . . . .
H6 H 0.217(2) 0.420(3) 0.2369(6) 0.020(5) Uiso 1 1 d . . . . .
H4 H -0.069(2) -0.023(3) 0.1752(6) 0.019(5) Uiso 1 1 d . . . . .
H3 H -0.078(3) 0.188(4) 0.1163(7) 0.036(6) Uiso 1 1 d . . . . .
H2 H 0.340(3) 0.913(4) 0.1469(7) 0.054(8) Uiso 1 1 d . . . . .
H1 H -0.102(4) 0.812(5) 0.0822(9) 0.078(9) Uiso 1 1 d . . . . .
O2 O 0.27150(15) 0.77988(19) 0.14506(3) 0.0169(3) Uani 1 1 d . . . . .
O1 O 0.30947(14) 0.76925(18) 0.21367(3) 0.0171(3) Uani 1 1 d . . . . .
O3 O -0.07439(15) 0.72730(18) 0.11090(3) 0.0183(3) Uani 1 1 d . . . . .
O4 O 0.06600(16) 0.51638(19) 0.07059(3) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.14827(19) 0.5011(2) 0.17829(4) 0.0133(3) Uani 1 1 d . . . . .
C6 C 0.0559(2) 0.4338(2) 0.14188(4) 0.0140(3) Uani 1 1 d . . . . .
C8 C 0.24931(19) 0.6978(2) 0.18061(4) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.1548(2) 0.3748(3) 0.21300(5) 0.0154(3) Uani 1 1 d . . . . .
C5 C -0.0205(2) 0.2397(3) 0.14079(5) 0.0164(3) Uani 1 1 d . . . . .
C4 C -0.0128(2) 0.1154(3) 0.17574(5) 0.0171(3) Uani 1 1 d . . . . .
C7 C 0.0214(2) 0.5664(3) 0.10424(5) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.0730(2) 0.1845(3) 0.21191(5) 0.0169(3) Uani 1 1 d . . . . .
H16 H -0.293(3) 1.282(4) 0.0294(8) 0.049(7) Uiso 1 1 d . . . . .
H20 H -0.128(3) 0.719(3) -0.0244(7) 0.031(6) Uiso 1 1 d . . . . .
H21 H -0.069(3) 0.665(4) 0.0226(7) 0.040(6) Uiso 1 1 d . . . . .
H19 H -0.326(4) 0.845(5) -0.0576(8) 0.065(8) Uiso 1 1 d . . . . .
H17 H -0.457(3) 1.250(4) 0.0003(7) 0.048(7) Uiso 1 1 d . . . . .
H15 H -0.302(3) 1.365(4) -0.0173(7) 0.048(7) Uiso 1 1 d . . . . .
H18 H -0.215(5) 1.037(6) -0.0689(10) 0.100(12) Uiso 1 1 d . . . . .
H22 H -0.403(4) 1.084(5) -0.0643(9) 0.076(9) Uiso 1 1 d . . . . .
O6 O -0.16946(17) 0.96958(19) 0.05401(3) 0.0237(3) Uani 1 1 d . . . . .
N3 N -0.27490(19) 1.0510(2) -0.01069(4) 0.0222(3) Uani 1 1 d . . . . .
C12 C -0.1890(2) 0.9242(3) 0.01621(5) 0.0195(4) Uani 1 1 d . . . . .
N4 N -0.1280(2) 0.7444(2) 0.00249(5) 0.0237(3) Uani 1 1 d . . . . .
C14 C -0.3045(3) 1.0014(3) -0.05427(5) 0.0288(4) Uani 1 1 d . . . . .
C13 C -0.3346(3) 1.2517(3) 0.00244(6) 0.0268(4) Uani 1 1 d . . . . .
H9 H 0.430(3) 1.464(3) 0.1054(6) 0.024(5) Uiso 1 1 d . . . . .
H13 H 0.595(3) 1.199(3) 0.2260(7) 0.031(6) Uiso 1 1 d . . . . .
H11 H 0.773(3) 1.449(3) 0.1998(6) 0.032(6) Uiso 1 1 d . . . . .
H12 H 0.604(3) 1.551(3) 0.2123(7) 0.036(6) Uiso 1 1 d . . . . .
H14 H 0.472(3) 1.014(3) 0.2116(6) 0.028(5) Uiso 1 1 d . . . . .
H8 H 0.586(3) 1.613(4) 0.1149(7) 0.042(7) Uiso 1 1 d . . . . .
H7 H 0.613(3) 1.383(4) 0.0990(7) 0.038(6) Uiso 1 1 d . . . . .
H10 H 0.710(3) 1.650(4) 0.1767(7) 0.043(6) Uiso 1 1 d . . . . .
O5 O 0.42559(15) 1.10853(19) 0.13992(3) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.53837(19) 1.1324(2) 0.20605(4) 0.0182(3) Uani 1 1 d . . . . .
N1 N 0.57222(17) 1.3967(2) 0.15870(4) 0.0173(3) Uani 1 1 d . . . . .
C9 C 0.5099(2) 1.2105(3) 0.16778(5) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.6717(2) 1.5213(3) 0.18940(5) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.5516(2) 1.4663(3) 0.11576(5) 0.0203(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.2984(18) . ?
O1 C8 1.2311(18) . ?
O3 C7 1.309(2) . ?
O4 C7 1.2216(19) . ?
C1 C2 1.391(2) . ?
C1 C6 1.409(2) . ?
C1 C8 1.494(2) . ?
C6 C5 1.387(2) . ?
C6 C7 1.502(2) . ?
C2 C3 1.384(2) . ?
C5 C4 1.390(2) . ?
C4 C3 1.384(2) . ?
O6 C12 1.2636(19) . ?
N3 C12 1.340(2) . ?
N3 C13 1.452(2) . ?
N3 C14 1.456(2) . ?
C12 N4 1.345(2) . ?
O5 C9 1.2642(19) . ?
N2 C9 1.347(2) . ?
N1 C9 1.338(2) . ?
N1 C10 1.460(2) . ?
N1 C11 1.467(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.20(15) . . ?
C2 C1 C8 118.06(13) . . ?
C6 C1 C8 122.64(14) . . ?
C5 C6 C1 119.46(14) . . ?
C5 C6 C7 116.30(13) . . ?
C1 C6 C7 124.06(14) . . ?
O1 C8 O2 124.02(15) . . ?
O1 C8 C1 121.77(14) . . ?
O2 C8 C1 114.17(13) . . ?
C3 C2 C1 120.73(15) . . ?
C6 C5 C4 120.57(15) . . ?
C3 C4 C5 119.95(16) . . ?
O4 C7 O3 124.63(15) . . ?
O4 C7 C6 122.51(15) . . ?
O3 C7 C6 112.54(13) . . ?
C4 C3 C2 120.01(15) . . ?
C12 N3 C13 120.49(14) . . ?
C12 N3 C14 122.48(16) . . ?
C13 N3 C14 116.94(15) . . ?
O6 C12 N3 120.83(16) . . ?
O6 C12 N4 120.35(16) . . ?
N3 C12 N4 118.79(15) . . ?
C9 N1 C10 121.81(13) . . ?
C9 N1 C11 118.12(14) . . ?
C10 N1 C11 119.85(14) . . ?
O5 C9 N1 119.15(14) . . ?
O5 C9 N2 120.65(16) . . ?
N1 C9 N2 120.20(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O5 1.01(3) 1.46(3) 2.4520(16) 167(2) . yes
O5 H2 O1 1.46(3) 2.40(2) 3.4275(16) 123.8(14) . yes
O3 H1 O6 1.09(3) 1.44(3) 2.4925(16) 160(3) . yes
O3 H1 N4 1.09(3) 2.63(3) 3.5272(18) 139(2) . yes
O6 H1 O4 1.44(3) 2.37(3) 3.4762(18) 130.3(17) . yes
N4 H20 O4 0.89(2) 2.22(2) 2.9872(18) 144.2(19) 3_565 yes
N4 H21 O4 0.93(2) 2.06(2) 2.9778(19) 174(2) . yes
N2 H13 O1 0.87(2) 2.10(2) 2.9243(18) 159(2) 2_655 yes
N2 H14 O1 0.95(2) 2.03(2) 2.9743(19) 170.1(18) . yes

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.056


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_150K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921990'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_150K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.69 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H9 N2 O1, C7 H3 N2 O6'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   22.97700(7)
_cell_length_b                   19.20650(6)
_cell_length_c                   5.83570(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2575.340(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    29069
_cell_measurement_theta_min      1.71120705438
_cell_measurement_theta_max      36.0673892193

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.993692626842
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37203
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         27.740
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3315
_reflns_number_gt                2902
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       GDA
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.9.3-gb491019a-release'
_computing_data_reduction        
;
 aimless (Evans, P. R. and Murshudov, G. N., 2013)
 ccp4 (Winn, M. D. et al., 2011) 
 DIALS 1.9.3-gb491019a-release (Winter, G. et al., 2018) 
 pointless (Evans, P., 2006) 
 XIA2 0.5.546-gdf2e0b53-dials-1.9 (Winter, G., 2010) 
;
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.74 command used to make multi_T datasets comparable: 0.74 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+0.6590P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3315
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H10 H 0.1088(6) 0.6894(7) 1.526(2) 0.029(3) Uiso 1 1 d . . . . .
H11 H 0.1935(6) 0.7118(8) 1.745(3) 0.037(4) Uiso 1 1 d . . . . .
H12 H 0.2900(6) 0.5977(7) 1.297(3) 0.031(3) Uiso 1 1 d . . . . .
H3 H -0.0395(7) 0.5254(9) 0.778(3) 0.043(4) Uiso 1 1 d . . . . .
H2 H 0.0007(7) 0.5670(8) 0.933(3) 0.035(4) Uiso 1 1 d . . . . .
H6 H -0.1064(8) 0.5671(9) 0.266(3) 0.054(5) Uiso 1 1 d . . . . .
H4 H -0.0701(8) 0.5182(9) 0.433(3) 0.047(4) Uiso 1 1 d . . . . .
H7 H -0.0576(9) 0.6709(11) 0.184(4) 0.073(6) Uiso 1 1 d . . . . .
H5 H -0.1263(8) 0.5556(9) 0.525(3) 0.052(5) Uiso 1 1 d . . . . .
H8 H -0.1024(9) 0.7014(10) 0.357(4) 0.069(6) Uiso 1 1 d . . . . .
H9 H -0.0341(9) 0.7130(10) 0.386(3) 0.061(5) Uiso 1 1 d . . . . .
H1 H 0.0418(9) 0.6672(10) 0.847(4) 0.073(6) Uiso 1 1 d . . . . .
O1 O 0.00785(3) 0.67328(4) 0.71624(15) 0.02880(18) Uani 1 1 d . . . . .
N2 N -0.05679(4) 0.61922(5) 0.48716(16) 0.0256(2) Uani 1 1 d . . . . .
N1 N -0.01971(4) 0.56307(5) 0.80574(19) 0.0314(2) Uani 1 1 d . . . . .
C1 C -0.02282(4) 0.61858(5) 0.67000(19) 0.0237(2) Uani 1 1 d . . . . .
C2 C -0.09249(5) 0.55945(6) 0.4264(2) 0.0327(3) Uani 1 1 d . . . . .
C3 C -0.06192(6) 0.68150(7) 0.3452(2) 0.0352(3) Uani 1 1 d . . . . .
O2 O 0.09023(3) 0.66716(4) 0.98062(14) 0.02897(19) Uani 1 1 d . . . . .
O3 O 0.05729(3) 0.57937(4) 1.19730(15) 0.03084(19) Uani 1 1 d . . . . .
C5 C 0.14950(4) 0.63008(5) 1.28087(17) 0.0208(2) Uani 1 1 d . . . . .
C10 C 0.20364(4) 0.60281(5) 1.21970(17) 0.0209(2) Uani 1 1 d . . . . .
O5 O 0.25795(4) 0.54705(4) 0.93981(14) 0.03113(19) Uani 1 1 d . . . . .
C8 C 0.24866(4) 0.65566(5) 1.53877(17) 0.0221(2) Uani 1 1 d . . . . .
C4 C 0.09436(4) 0.62263(5) 1.14083(18) 0.0225(2) Uani 1 1 d . . . . .
N3 N 0.20918(4) 0.55801(5) 1.01670(16) 0.0255(2) Uani 1 1 d . . . . .
N4 N 0.30136(4) 0.66956(5) 1.67447(16) 0.0272(2) Uani 1 1 d . . . . .
C9 C 0.25382(4) 0.61499(5) 1.34430(18) 0.0221(2) Uani 1 1 d . . . . .
C6 C 0.14667(5) 0.67047(5) 1.47924(18) 0.0243(2) Uani 1 1 d . . . . .
O6 O 0.34749(4) 0.64572(5) 1.60633(16) 0.0388(2) Uani 1 1 d . . . . .
O7 O 0.29609(4) 0.70406(5) 1.84979(16) 0.0398(2) Uani 1 1 d . . . . .
C7 C 0.19595(5) 0.68318(5) 1.60963(18) 0.0246(2) Uani 1 1 d . . . . .
O4 O 0.16475(4) 0.53389(5) 0.93343(19) 0.0466(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2934(13) . ?
N2 C1 1.3222(14) . ?
N2 C2 1.4548(14) . ?
N2 C3 1.4597(15) . ?
N1 C1 1.3301(14) . ?
O2 C4 1.2707(13) . ?
O3 C4 1.2346(12) . ?
C5 C6 1.3950(14) . ?
C5 C10 1.3961(13) . ?
C5 C4 1.5144(14) . ?
C10 C9 1.3832(14) . ?
C10 N3 1.4696(13) . ?
O5 N3 1.2252(12) . ?
C8 C9 1.3829(14) . ?
C8 C7 1.3847(15) . ?
C8 N4 1.4713(13) . ?
N3 O4 1.2220(12) . ?
N4 O6 1.2211(13) . ?
N4 O7 1.2250(13) . ?
C6 C7 1.3858(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 121.49(10) . . ?
C1 N2 C3 120.87(10) . . ?
C2 N2 C3 117.57(10) . . ?
O1 C1 N2 118.85(10) . . ?
O1 C1 N1 119.84(10) . . ?
N2 C1 N1 121.31(10) . . ?
C6 C5 C10 117.54(9) . . ?
C6 C5 C4 117.48(9) . . ?
C10 C5 C4 124.88(9) . . ?
C9 C10 C5 123.02(9) . . ?
C9 C10 N3 116.77(9) . . ?
C5 C10 N3 120.20(9) . . ?
C9 C8 C7 122.39(9) . . ?
C9 C8 N4 118.27(9) . . ?
C7 C8 N4 119.34(9) . . ?
O3 C4 O2 126.71(10) . . ?
O3 C4 C5 119.79(9) . . ?
O2 C4 C5 113.32(8) . . ?
O4 N3 O5 123.59(10) . . ?
O4 N3 C10 118.04(9) . . ?
O5 N3 C10 118.37(9) . . ?
O6 N4 O7 124.11(10) . . ?
O6 N4 C8 118.10(9) . . ?
O7 N4 C8 117.79(9) . . ?
C8 C9 C10 117.09(9) . . ?
C7 C6 C5 121.03(9) . . ?
C8 C7 C6 118.91(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H3 O3 0.870(17) 2.058(17) 2.8690(13) 154.6(14) 5_567 yes
N1 H2 O3 0.883(17) 2.030(17) 2.9068(13) 171.9(14) . yes
C2 H6 O4 0.997(19) 2.631(18) 3.2218(15) 118.0(13) 5_566 yes
C2 H5 O5 0.970(19) 2.673(19) 3.5321(15) 147.8(14) 8_557 yes
C3 H9 O1 0.91(2) 2.585(19) 3.3038(15) 136.2(16) 7_575 yes
O1 H1 O2 1.10(2) 1.36(2) 2.4448(11) 169(2) . yes
O2 H1 N1 1.36(2) 2.46(2) 3.3791(13) 121.7(12) . yes

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_100K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921988'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_100K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.69 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H9 N2 O1, C7 H3 N2 O6'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   22.95610(12)
_cell_length_b                   19.16910(11)
_cell_length_c                   5.80590(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2554.87(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    22150
_cell_measurement_theta_max      35.801330704
_cell_measurement_theta_min      1.7132182364

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.986942279488
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

_diffrn_ambient_temperature      100
_diffrn_detector                 
;
Photon counting pixel array, data_PILATUS_2M_S_N_24_0107_Diamond
;
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36127
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         27.739
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3283
_reflns_number_gt                2782
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       GDA
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.9.3-gb491019a-release'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.9.3-gb491019a-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.546-gdf2e0b53-dials-1.9 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.74 command used to make multi_T datasets comparable: 0.74 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.6285P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3283
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H10 H 0.1105(6) 0.6896(7) 1.524(2) 0.020(3) Uiso 1 1 d . . . . .
H11 H 0.1947(6) 0.7120(7) 1.750(3) 0.026(3) Uiso 1 1 d . . . . .
H12 H 0.2908(6) 0.5973(7) 1.297(2) 0.022(3) Uiso 1 1 d . . . . .
H3 H -0.0403(7) 0.5255(8) 0.781(3) 0.033(4) Uiso 1 1 d . . . . .
H2 H 0.0016(7) 0.5667(7) 0.931(3) 0.028(4) Uiso 1 1 d . . . . .
H6 H -0.1057(7) 0.5658(8) 0.262(3) 0.034(4) Uiso 1 1 d . . . . .
H4 H -0.0705(7) 0.5168(8) 0.433(3) 0.036(4) Uiso 1 1 d . . . . .
H7 H -0.0562(8) 0.6696(9) 0.176(3) 0.048(5) Uiso 1 1 d . . . . .
H5 H -0.1260(7) 0.5563(8) 0.521(3) 0.041(4) Uiso 1 1 d . . . . .
H8 H -0.1021(8) 0.7014(9) 0.349(3) 0.054(5) Uiso 1 1 d . . . . .
H9 H -0.0320(8) 0.7141(9) 0.377(3) 0.052(5) Uiso 1 1 d . . . . .
H1 H 0.0426(9) 0.6671(10) 0.845(3) 0.062(6) Uiso 1 1 d . . . . .
O1 O 0.00864(3) 0.67347(4) 0.71371(13) 0.02047(16) Uani 1 1 d . . . . .
N2 N -0.05602(4) 0.61935(4) 0.48266(15) 0.01836(18) Uani 1 1 d . . . . .
N1 N -0.01958(4) 0.56309(5) 0.80447(17) 0.0223(2) Uani 1 1 d . . . . .
C1 C -0.02216(4) 0.61870(5) 0.66739(18) 0.0174(2) Uani 1 1 d . . . . .
C2 C -0.09199(5) 0.55940(6) 0.4226(2) 0.0227(2) Uani 1 1 d . . . . .
C3 C -0.06125(5) 0.68176(6) 0.3396(2) 0.0246(2) Uani 1 1 d . . . . .
O2 O 0.09096(3) 0.66740(4) 0.97976(13) 0.02067(17) Uani 1 1 d . . . . .
O3 O 0.05800(3) 0.57914(4) 1.19730(13) 0.02200(17) Uani 1 1 d . . . . .
C5 C 0.15037(4) 0.63000(5) 1.28112(17) 0.01575(19) Uani 1 1 d . . . . .
C10 C 0.20454(4) 0.60276(5) 1.21912(17) 0.01550(19) Uani 1 1 d . . . . .
O5 O 0.25901(3) 0.54695(4) 0.93729(13) 0.02187(17) Uani 1 1 d . . . . .
C8 C 0.24978(4) 0.65560(5) 1.54002(17) 0.0165(2) Uani 1 1 d . . . . .
C4 C 0.09506(4) 0.62266(5) 1.14080(17) 0.01628(19) Uani 1 1 d . . . . .
N3 N 0.21005(4) 0.55804(4) 1.01423(15) 0.01824(18) Uani 1 1 d . . . . .
N4 N 0.30258(4) 0.66944(5) 1.67623(15) 0.01900(18) Uani 1 1 d . . . . .
C9 C 0.25496(4) 0.61509(5) 1.34427(17) 0.01627(19) Uani 1 1 d . . . . .
C6 C 0.14760(4) 0.67043(5) 1.48066(18) 0.0177(2) Uani 1 1 d . . . . .
O6 O 0.34881(3) 0.64523(5) 1.60794(14) 0.02686(19) Uani 1 1 d . . . . .
O7 O 0.29743(4) 0.70423(4) 1.85300(14) 0.02750(19) Uani 1 1 d . . . . .
C7 C 0.19700(4) 0.68319(5) 1.61173(18) 0.0181(2) Uani 1 1 d . . . . .
O4 O 0.16539(4) 0.53412(5) 0.93052(16) 0.0318(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2940(12) . ?
N2 C1 1.3247(13) . ?
N2 C2 1.4575(13) . ?
N2 C3 1.4614(14) . ?
N1 C1 1.3315(14) . ?
O2 C4 1.2723(12) . ?
O3 C4 1.2359(12) . ?
C5 C6 1.3953(14) . ?
C5 C10 1.3959(13) . ?
C5 C4 1.5151(13) . ?
C10 C9 1.3869(14) . ?
C10 N3 1.4718(13) . ?
O5 N3 1.2281(11) . ?
C8 C9 1.3817(14) . ?
C8 C7 1.3861(14) . ?
C8 N4 1.4712(13) . ?
N3 O4 1.2237(12) . ?
N4 O6 1.2245(12) . ?
N4 O7 1.2296(12) . ?
C6 C7 1.3873(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 121.25(9) . . ?
C1 N2 C3 121.08(9) . . ?
C2 N2 C3 117.58(9) . . ?
O1 C1 N2 118.76(9) . . ?
O1 C1 N1 120.07(9) . . ?
N2 C1 N1 121.17(9) . . ?
C6 C5 C10 117.54(9) . . ?
C6 C5 C4 117.38(8) . . ?
C10 C5 C4 124.97(9) . . ?
C9 C10 C5 123.01(9) . . ?
C9 C10 N3 116.81(8) . . ?
C5 C10 N3 120.18(9) . . ?
C9 C8 C7 122.46(9) . . ?
C9 C8 N4 118.21(9) . . ?
C7 C8 N4 119.33(9) . . ?
O3 C4 O2 126.82(9) . . ?
O3 C4 C5 119.79(9) . . ?
O2 C4 C5 113.24(8) . . ?
O4 N3 O5 123.88(9) . . ?
O4 N3 C10 117.86(8) . . ?
O5 N3 C10 118.26(8) . . ?
O6 N4 O7 124.00(9) . . ?
O6 N4 C8 118.14(9) . . ?
O7 N4 C8 117.86(8) . . ?
C8 C9 C10 117.06(9) . . ?
C7 C6 C5 121.08(9) . . ?
C8 C7 C6 118.85(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H3 O3 0.873(16) 2.051(16) 2.8656(12) 154.8(14) 5_567 yes
N1 H2 O3 0.884(16) 2.030(16) 2.9100(12) 173.1(14) . yes
C2 H6 O4 0.993(16) 2.606(15) 3.2024(13) 118.6(11) 5_566 yes
C2 H5 O5 0.968(17) 2.657(17) 3.5238(14) 149.2(13) 8_557 yes
C3 H9 O1 0.940(19) 2.533(18) 3.2878(14) 137.4(14) 7_575 yes
O1 H1 O2 1.10(2) 1.36(2) 2.4435(10) 168.6(18) . yes
O2 H1 N1 1.36(2) 2.463(19) 3.3873(12) 122.2(11) . yes

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_3_300K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921996'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_3_300K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      24.24 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 3,5-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O6, C3 H8 N2 O1'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5476(4)
_cell_length_b                   11.4257(6)
_cell_length_c                   7.9214(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.763(4)
_cell_angle_gamma                90
_cell_volume                     671.10(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    4139
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      29.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10837
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.262
_diffrn_reflns_theta_max         36.177
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3282
_reflns_number_gt                1880
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.990

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.75 command used to make multi_T datasets for complex 2 comparable: 0.75 Angstroms
is the maximum diffraction resolution of high T (300 K) data set.

Deviating H-C-H angle for methyl group C9, C10. H-atoms were placed geometrically
using HFIX 137 for these methyl groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 689 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3282
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 0.663(4) 0.727(4) 0.403(4) 0.060(9) Uiso 1 1 d . . . . .
H4 H 0.719(6) 0.371(4) 0.382(5) 0.088(12) Uiso 1 1 d . . . . .
H2 H 1.075(4) 0.580(3) 0.228(4) 0.052(8) Uiso 1 1 d . . . . .
H12 H 1.080(5) 0.105(4) 0.194(5) 0.074(11) Uiso 1 1 d . . . . .
H11 H 1.152(5) -0.018(5) 0.176(5) 0.089(14) Uiso 1 1 d . . . . .
H1 H 1.239(8) 0.276(6) 0.156(7) 0.148(19) Uiso 1 1 d . . . . .
N3 N 0.4977(5) 0.5349(5) 0.4613(4) 0.0880(10) Uani 1 1 d . . . . .
O3 O 0.9656(4) 0.2546(2) 0.2892(4) 0.0855(8) Uani 1 1 d . . . . .
O2 O 1.1481(4) 0.3737(2) 0.1810(4) 0.0873(9) Uani 1 1 d . . . . .
O5 O 0.8759(5) 0.8667(3) 0.3169(4) 0.0971(9) Uani 1 1 d . . . . .
C2 C 0.9166(4) 0.4584(3) 0.2989(4) 0.0564(8) Uani 1 1 d . . . . .
C4 C 0.8876(4) 0.6662(3) 0.3118(4) 0.0599(8) Uani 1 1 d . . . . .
C6 C 0.6677(4) 0.5467(4) 0.3968(4) 0.0616(9) Uani 1 1 d . . . . .
C7 C 0.7563(5) 0.4470(3) 0.3619(4) 0.0645(9) Uani 1 1 d . . . . .
O6 O 0.4124(4) 0.6217(4) 0.4790(6) 0.1262(14) Uani 1 1 d . . . . .
C5 C 0.7300(5) 0.6575(4) 0.3738(5) 0.0650(9) Uani 1 1 d . . . . .
O4 O 1.0965(5) 0.7885(2) 0.2274(5) 0.1172(12) Uani 1 1 d . . . . .
N2 N 0.9576(5) 0.7821(3) 0.2833(4) 0.0731(9) Uani 1 1 d . . . . .
C1 C 1.0122(5) 0.3519(3) 0.2563(5) 0.0632(8) Uani 1 1 d . . . . .
O7 O 0.4534(5) 0.4362(4) 0.4933(5) 0.1257(13) Uani 1 1 d . . . . .
C3 C 0.9811(4) 0.5690(3) 0.2727(4) 0.0585(8) Uani 1 1 d . . . . .
O1 O 1.3367(3) 0.2114(2) 0.1089(3) 0.0828(8) Uani 1 1 d . . . . .
N1 N 1.4454(4) 0.0322(3) 0.0777(4) 0.0685(8) Uani 1 1 d . . . . .
N4 N 1.1708(5) 0.0577(3) 0.1667(4) 0.0715(8) Uani 1 1 d . . . . .
C8 C 1.3194(5) 0.1031(3) 0.1180(4) 0.0609(8) Uani 1 1 d . . . . .
C10 C 1.4314(5) -0.0949(3) 0.0850(6) 0.0804(11) Uani 1 1 d . . . . .
H10A H 1.453002 -0.119789 0.202850 0.121 Uiso 1 1 calc R U . . .
H10B H 1.519277 -0.129796 0.027269 0.121 Uiso 1 1 calc R U . . .
H10C H 1.312759 -0.118761 0.029805 0.121 Uiso 1 1 calc R U . . .
C9 C 1.6132(5) 0.0815(4) 0.0468(6) 0.0931(12) Uani 1 1 d . . . . .
H9A H 1.605729 0.165333 0.047256 0.140 Uiso 1 1 calc R U . . .
H9B H 1.634714 0.055358 -0.062771 0.140 Uiso 1 1 calc R U . . .
H9C H 1.710431 0.056332 0.135473 0.140 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 O6 1.204(5) . ?
N3 O7 1.216(6) . ?
N3 C6 1.473(4) . ?
O3 C1 1.209(4) . ?
O2 C1 1.303(5) . ?
O5 N2 1.203(4) . ?
C2 C3 1.383(5) . ?
C2 C7 1.398(5) . ?
C2 C1 1.486(5) . ?
C4 C5 1.373(5) . ?
C4 C3 1.382(5) . ?
C4 N2 1.459(5) . ?
C6 C5 1.374(6) . ?
C6 C7 1.375(6) . ?
O4 N2 1.215(4) . ?
O1 C8 1.249(4) . ?
N1 C8 1.332(4) . ?
N1 C9 1.448(4) . ?
N1 C10 1.458(5) . ?
N4 C8 1.356(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 N3 O7 124.4(4) . . ?
O6 N3 C6 118.9(4) . . ?
O7 N3 C6 116.6(4) . . ?
C3 C2 C7 119.4(3) . . ?
C3 C2 C1 121.0(3) . . ?
C7 C2 C1 119.6(3) . . ?
C5 C4 C3 122.3(4) . . ?
C5 C4 N2 118.9(3) . . ?
C3 C4 N2 118.7(3) . . ?
C5 C6 C7 123.0(3) . . ?
C5 C6 N3 118.2(4) . . ?
C7 C6 N3 118.8(4) . . ?
C6 C7 C2 118.7(3) . . ?
C4 C5 C6 117.1(3) . . ?
O5 N2 O4 123.1(3) . . ?
O5 N2 C4 118.7(3) . . ?
O4 N2 C4 118.2(3) . . ?
O3 C1 O2 124.1(3) . . ?
O3 C1 C2 122.1(3) . . ?
O2 C1 C2 113.9(3) . . ?
C4 C3 C2 119.5(3) . . ?
C8 N1 C9 119.4(3) . . ?
C8 N1 C10 122.4(3) . . ?
C9 N1 C10 117.8(3) . . ?
O1 C8 N1 120.1(3) . . ?
O1 C8 N4 119.8(4) . . ?
N1 C8 N4 120.1(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H12 O3 0.93(5) 2.12(5) 2.994(5) 157(3) . yes
N4 H11 O4 0.88(6) 2.30(6) 3.179(5) 174(4) 1_545 yes
O1 H1 O3 1.15(7) 2.50(6) 3.409(4) 135(5) . yes
O1 H1 O2 1.15(7) 1.34(7) 2.468(4) 162(6) . yes
C10 H10A O7 0.96 2.46 3.310(6) 147.0 2_746 yes
C10 H10B O1 0.96 2.46 3.365(4) 156.2 2_845 yes
C10 H10C O4 0.96 2.68 3.240(5) 117.6 1_545 yes
C9 H9B O2 0.96 2.91 3.654(5) 135.6 2_845 yes

_refine_diff_density_max         0.137
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 30 degreesC'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_1_200K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921987'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_1_200K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      37.23 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea phthalic acid 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C3 H8 N2 O1), (C8 H6 O4)'
_chemical_formula_sum            'C14 H22 N4 O6'
_chemical_formula_weight         342.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0076 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0133 0.0073 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9905(5)
_cell_length_b                   6.4455(4)
_cell_length_c                   32.7612(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.375(3)
_cell_angle_gamma                90
_cell_volume                     1679.87(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    200
_cell_measurement_reflns_used    5059
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      41.70

_exptl_crystal_description       'rectangular needle'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9341
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22109
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.723
_diffrn_reflns_theta_max         30.646
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4026
_reflns_number_gt                2843
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.76 command used to make multi_T datasets comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (300 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0630P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4026
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H5 H 0.077(2) 0.095(3) 0.2340(6) 0.034(5) Uiso 1 1 d . . . . .
H6 H 0.212(2) 0.417(3) 0.2364(6) 0.036(5) Uiso 1 1 d . . . . .
H4 H -0.075(2) -0.022(3) 0.1751(6) 0.038(5) Uiso 1 1 d . . . . .
H3 H -0.081(3) 0.183(3) 0.1157(7) 0.049(6) Uiso 1 1 d . . . . .
H2 H 0.337(3) 0.913(4) 0.1469(8) 0.082(9) Uiso 1 1 d . . . . .
H1 H -0.103(3) 0.813(4) 0.0824(8) 0.076(8) Uiso 1 1 d . . . . .
O2 O 0.26520(15) 0.77468(18) 0.14523(3) 0.0304(3) Uani 1 1 d . . . . .
O1 O 0.30729(14) 0.76150(18) 0.21341(3) 0.0313(3) Uani 1 1 d . . . . .
O3 O -0.07736(14) 0.71995(18) 0.11061(3) 0.0306(3) Uani 1 1 d . . . . .
O4 O 0.06138(18) 0.5113(2) 0.07096(3) 0.0405(3) Uani 1 1 d . . . . .
C1 C 0.14491(18) 0.4951(2) 0.17813(4) 0.0231(3) Uani 1 1 d . . . . .
C6 C 0.05270(19) 0.4282(2) 0.14181(4) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.24583(18) 0.6912(2) 0.18063(4) 0.0237(3) Uani 1 1 d . . . . .
C2 C 0.1517(2) 0.3691(3) 0.21277(5) 0.0272(3) Uani 1 1 d . . . . .
C5 C -0.0240(2) 0.2345(3) 0.14084(5) 0.0294(3) Uani 1 1 d . . . . .
C4 C -0.0161(2) 0.1118(3) 0.17564(5) 0.0322(4) Uani 1 1 d . . . . .
C7 C 0.0177(2) 0.5604(2) 0.10430(4) 0.0270(3) Uani 1 1 d . . . . .
C3 C 0.0702(2) 0.1802(3) 0.21171(5) 0.0311(3) Uani 1 1 d . . . . .
H16 H -0.298(5) 1.274(6) 0.0306(12) 0.129(14) Uiso 1 1 d . . . . .
H20 H -0.128(3) 0.726(4) -0.0251(8) 0.058(7) Uiso 1 1 d . . . . .
H21 H -0.063(3) 0.664(4) 0.0231(8) 0.078(8) Uiso 1 1 d . . . . .
H19 H -0.307(4) 0.851(6) -0.0604(10) 0.117(12) Uiso 1 1 d . . . . .
H17 H -0.460(4) 1.251(4) 0.0000(8) 0.071(8) Uiso 1 1 d . . . . .
H15 H -0.302(4) 1.372(5) -0.0128(10) 0.104(11) Uiso 1 1 d . . . . .
H18 H -0.219(6) 1.071(7) -0.0668(13) 0.159(18) Uiso 1 1 d . . . . .
H22 H -0.398(6) 1.088(7) -0.0633(14) 0.160(17) Uiso 1 1 d . . . . .
O6 O -0.17446(18) 0.9626(2) 0.05380(3) 0.0408(3) Uani 1 1 d . . . . .
N3 N -0.2727(2) 1.0512(2) -0.01063(4) 0.0375(4) Uani 1 1 d . . . . .
C12 C -0.1898(2) 0.9213(3) 0.01606(5) 0.0321(4) Uani 1 1 d . . . . .
N4 N -0.1272(2) 0.7450(3) 0.00216(5) 0.0419(4) Uani 1 1 d . . . . .
C14 C -0.2964(4) 1.0095(4) -0.05455(6) 0.0525(6) Uani 1 1 d . . . . .
C13 C -0.3371(3) 1.2465(3) 0.00348(7) 0.0476(5) Uani 1 1 d . . . . .
H9 H 0.431(3) 1.451(4) 0.1058(7) 0.061(7) Uiso 1 1 d . . . . .
H13 H 0.592(3) 1.194(3) 0.2271(7) 0.045(6) Uiso 1 1 d . . . . .
H11 H 0.767(4) 1.443(5) 0.2017(9) 0.087(9) Uiso 1 1 d . . . . .
H12 H 0.607(3) 1.554(4) 0.2111(7) 0.057(7) Uiso 1 1 d . . . . .
H14 H 0.472(3) 1.009(3) 0.2118(7) 0.044(6) Uiso 1 1 d . . . . .
H8 H 0.587(3) 1.599(4) 0.1153(8) 0.073(8) Uiso 1 1 d . . . . .
H7 H 0.610(3) 1.374(4) 0.1014(7) 0.060(7) Uiso 1 1 d . . . . .
H10 H 0.705(4) 1.640(5) 0.1758(9) 0.095(10) Uiso 1 1 d . . . . .
O5 O 0.42144(16) 1.1016(2) 0.14074(3) 0.0372(3) Uani 1 1 d . . . . .
N2 N 0.53383(19) 1.1266(3) 0.20658(4) 0.0335(3) Uani 1 1 d . . . . .
N1 N 0.56990(17) 1.3868(2) 0.15902(4) 0.0306(3) Uani 1 1 d . . . . .
C9 C 0.50646(19) 1.2027(3) 0.16835(5) 0.0280(3) Uani 1 1 d . . . . .
C10 C 0.6684(2) 1.5135(3) 0.18937(6) 0.0338(4) Uani 1 1 d . . . . .
C11 C 0.5478(3) 1.4577(3) 0.11659(6) 0.0375(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.3008(17) . ?
O1 C8 1.2254(18) . ?
O3 C7 1.3063(19) . ?
O4 C7 1.2192(18) . ?
C1 C2 1.392(2) . ?
C1 C6 1.407(2) . ?
C1 C8 1.497(2) . ?
C6 C5 1.390(2) . ?
C6 C7 1.500(2) . ?
C2 C3 1.380(2) . ?
C5 C4 1.384(2) . ?
C4 C3 1.383(2) . ?
O6 C12 1.2592(19) . ?
N3 C12 1.340(2) . ?
N3 C13 1.452(3) . ?
N3 C14 1.458(2) . ?
C12 N4 1.339(2) . ?
O5 C9 1.2606(19) . ?
N2 C9 1.344(2) . ?
N1 C9 1.337(2) . ?
N1 C11 1.458(2) . ?
N1 C10 1.459(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.20(14) . . ?
C2 C1 C8 117.91(13) . . ?
C6 C1 C8 122.79(13) . . ?
C5 C6 C1 119.30(14) . . ?
C5 C6 C7 116.33(13) . . ?
C1 C6 C7 124.15(14) . . ?
O1 C8 O2 123.85(15) . . ?
O1 C8 C1 121.98(14) . . ?
O2 C8 C1 114.14(12) . . ?
C3 C2 C1 120.79(15) . . ?
C4 C5 C6 120.57(15) . . ?
C3 C4 C5 120.15(16) . . ?
O4 C7 O3 124.44(15) . . ?
O4 C7 C6 122.65(15) . . ?
O3 C7 C6 112.59(13) . . ?
C2 C3 C4 119.93(15) . . ?
C12 N3 C13 120.14(15) . . ?
C12 N3 C14 122.61(18) . . ?
C13 N3 C14 117.20(17) . . ?
O6 C12 N4 120.55(16) . . ?
O6 C12 N3 120.34(16) . . ?
N4 C12 N3 119.08(15) . . ?
C9 N1 C11 118.77(14) . . ?
C9 N1 C10 122.21(14) . . ?
C11 N1 C10 118.92(15) . . ?
O5 C9 N1 119.04(14) . . ?
O5 C9 N2 120.63(16) . . ?
N1 C9 N2 120.33(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O5 1.06(3) 1.41(3) 2.4606(16) 168(3) . yes
O5 H2 O1 1.41(3) 2.42(3) 3.4223(16) 124.3(16) . yes
O3 H1 O6 1.11(3) 1.42(3) 2.4984(16) 162(2) . yes
O3 H1 N4 1.11(3) 2.65(3) 3.5414(19) 136.8(19) . yes
O6 H1 O4 1.42(3) 2.40(3) 3.4827(19) 129.6(15) . yes
N4 H20 O4 0.90(3) 2.24(2) 2.9967(19) 141(2) 3_565 yes
N4 H21 O4 0.97(3) 2.03(3) 2.997(2) 175(2) . yes
N2 H13 O1 0.89(2) 2.09(2) 2.9350(18) 159.0(19) 2_655 yes
N2 H14 O1 0.93(2) 2.07(2) 2.990(2) 169(2) . yes

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_250K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921989'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_250K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.69 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N4 O7'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   23.08380(10)
_cell_length_b                   19.28500(10)
_cell_length_c                   5.90715(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2629.69(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    250
_cell_measurement_reflns_used    20082
_cell_measurement_theta_min      0.848883432955
_cell_measurement_theta_max      35.6819203977

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.993008074575
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37981
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         27.740
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3383
_reflns_number_gt                2627
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       GDA
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.9.3-gb491019a-release'
_computing_data_reduction        
;
 aimless (Evans, P. R. and Murshudov, G. N., 2013)
 ccp4 (Winn, M. D. et al., 2011) 
 DIALS 1.9.3-gb491019a-release (Winter, G. et al., 2018) 
 pointless (Evans, P., 2006) 
 XIA2 0.5.546-gdf2e0b53-dials-1.9 (Winter, G., 2010) 
;
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.74 command used to make multi_T datasets comparable: 0.74 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.

Deviating H-C-H angle for methyl group C3. H-atoms were placed geometrically
using HFIX 137.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.2324P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3383
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H10 H 0.1083(7) 0.6892(8) 1.511(3) 0.052(4) Uiso 1 1 d . . . . .
H11 H 0.1920(7) 0.7104(8) 1.734(3) 0.063(4) Uiso 1 1 d . . . . .
H12 H 0.2864(6) 0.5979(8) 1.301(3) 0.049(4) Uiso 1 1 d . . . . .
H3 H -0.0403(7) 0.5269(10) 0.781(3) 0.067(5) Uiso 1 1 d . . . . .
H2 H 0.0029(8) 0.5658(8) 0.927(3) 0.062(5) Uiso 1 1 d . . . . .
H6 H -0.1076(10) 0.5683(11) 0.277(4) 0.098(7) Uiso 1 1 d . . . . .
H4 H -0.0703(8) 0.5170(10) 0.436(3) 0.081(6) Uiso 1 1 d . . . . .
H5 H -0.1248(11) 0.5543(12) 0.543(4) 0.109(8) Uiso 1 1 d . . . . .
H1 H 0.0428(10) 0.6676(11) 0.868(4) 0.112(7) Uiso 1 1 d . . . . .
O1 O 0.00703(4) 0.67237(5) 0.71888(17) 0.0525(2) Uani 1 1 d . . . . .
N2 N -0.05772(4) 0.61913(6) 0.49517(19) 0.0467(3) Uani 1 1 d . . . . .
N1 N -0.01984(6) 0.56308(7) 0.8059(2) 0.0578(3) Uani 1 1 d . . . . .
C1 C -0.02340(5) 0.61812(6) 0.6740(2) 0.0428(3) Uani 1 1 d . . . . .
C2 C -0.09338(7) 0.55988(9) 0.4342(3) 0.0608(4) Uani 1 1 d . . . . .
C3 C -0.06267(7) 0.68117(8) 0.3562(3) 0.0651(4) Uani 1 1 d . . . . .
H3A H -0.032623 0.713280 0.396533 0.098 Uiso 1 1 calc R U . . .
H3B H -0.099793 0.702298 0.380859 0.098 Uiso 1 1 calc R U . . .
H3C H -0.058871 0.668835 0.199414 0.098 Uiso 1 1 calc R U . . .
O2 O 0.08942(4) 0.66651(5) 0.97955(16) 0.0527(3) Uani 1 1 d . . . . .
O3 O 0.05668(4) 0.57979(5) 1.19433(18) 0.0566(3) Uani 1 1 d . . . . .
C5 C 0.14829(5) 0.63018(6) 1.2771(2) 0.0373(2) Uani 1 1 d . . . . .
C10 C 0.20206(5) 0.60288(6) 1.2180(2) 0.0374(2) Uani 1 1 d . . . . .
O5 O 0.25614(5) 0.54715(5) 0.94261(17) 0.0579(3) Uani 1 1 d . . . . .
C8 C 0.24662(5) 0.65567(6) 1.5328(2) 0.0393(3) Uani 1 1 d . . . . .
C4 C 0.09358(5) 0.62260(6) 1.1378(2) 0.0407(3) Uani 1 1 d . . . . .
N3 N 0.20784(5) 0.55804(5) 1.01830(19) 0.0459(3) Uani 1 1 d . . . . .
N4 N 0.29897(5) 0.66975(6) 1.6665(2) 0.0497(3) Uani 1 1 d . . . . .
C9 C 0.25174(5) 0.61514(6) 1.3416(2) 0.0389(3) Uani 1 1 d . . . . .
C6 C 0.14539(5) 0.67041(6) 1.4719(2) 0.0431(3) Uani 1 1 d . . . . .
O6 O 0.34476(5) 0.64654(7) 1.5998(2) 0.0707(3) Uani 1 1 d . . . . .
O7 O 0.29367(5) 0.70386(6) 1.83908(19) 0.0727(3) Uani 1 1 d . . . . .
C7 C 0.19419(6) 0.68304(7) 1.6013(2) 0.0444(3) Uani 1 1 d . . . . .
O4 O 0.16414(5) 0.53396(7) 0.9356(2) 0.0844(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2878(15) . ?
N2 C1 1.3205(17) . ?
N2 C2 1.4535(19) . ?
N2 C3 1.4556(19) . ?
N1 C1 1.3191(18) . ?
O2 C4 1.2648(15) . ?
O3 C4 1.2323(14) . ?
C5 C6 1.3893(17) . ?
C5 C10 1.3929(16) . ?
C5 C4 1.5146(16) . ?
C10 C9 1.3801(16) . ?
C10 N3 1.4686(16) . ?
O5 N3 1.2195(15) . ?
C8 C9 1.3783(17) . ?
C8 C7 1.3809(18) . ?
C8 N4 1.4693(16) . ?
N3 O4 1.2131(15) . ?
N4 O6 1.2136(16) . ?
N4 O7 1.2192(15) . ?
C6 C7 1.3830(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 121.75(12) . . ?
C1 N2 C3 120.70(11) . . ?
C2 N2 C3 117.52(12) . . ?
O1 C1 N1 119.87(12) . . ?
O1 C1 N2 118.69(11) . . ?
N1 C1 N2 121.44(12) . . ?
C6 C5 C10 117.51(10) . . ?
C6 C5 C4 117.63(10) . . ?
C10 C5 C4 124.76(11) . . ?
C9 C10 C5 122.88(11) . . ?
C9 C10 N3 116.78(10) . . ?
C5 C10 N3 120.33(10) . . ?
C9 C8 C7 122.15(11) . . ?
C9 C8 N4 118.35(11) . . ?
C7 C8 N4 119.51(11) . . ?
O3 C4 O2 126.61(11) . . ?
O3 C4 C5 119.58(11) . . ?
O2 C4 C5 113.60(10) . . ?
O4 N3 O5 123.13(11) . . ?
O4 N3 C10 118.25(11) . . ?
O5 N3 C10 118.61(10) . . ?
O6 N4 O7 123.91(12) . . ?
O6 N4 C8 118.27(11) . . ?
O7 N4 C8 117.82(11) . . ?
C8 C9 C10 117.36(11) . . ?
C7 C6 C5 121.11(11) . . ?
C8 C7 C6 118.98(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H3 O3 0.856(19) 2.097(19) 2.8836(16) 152.6(15) 5_567 yes
N1 H2 O3 0.89(2) 2.03(2) 2.9137(17) 175.3(16) . yes
C2 H6 O4 1.00(2) 2.68(2) 3.2736(19) 118.5(16) 5_566 yes
C2 H5 O5 0.98(3) 2.75(3) 3.558(2) 140.1(19) 8_557 yes
C3 H3A O1 0.96 2.61 3.3504(19) 134.4 7_575 yes
O1 H1 O2 1.21(3) 1.26(2) 2.4496(13) 164(2) . yes
O2 H1 N1 1.26(3) 2.51(2) 3.3751(16) 123.7(14) . yes

_refine_diff_density_max         0.222
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_3_250K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921995'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_3_250K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      24.29 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 3,5-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O6, C3 H8 N2 O1'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5150(4)
_cell_length_b                   11.4026(6)
_cell_length_c                   7.8998(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.509(4)
_cell_angle_gamma                90
_cell_volume                     663.33(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    250
_cell_measurement_reflns_used    4714
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      30.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10617
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.279
_diffrn_reflns_theta_max         36.164
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3231
_reflns_number_gt                2179
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.75 command used to make multi_T datasets for complex 2 comparable: 0.75 Angstroms
is the maximum diffraction resolution of high T (300 K) data set.

Deviating H-C-H angle for methyl group C9, C10. H-atoms were placed geometrically
using HFIX 137 for these methyl groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3231
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 0.663(4) 0.727(4) 0.406(4) 0.050(9) Uiso 1 1 d . . . . .
H4 H 0.714(6) 0.373(4) 0.383(5) 0.073(12) Uiso 1 1 d . . . . .
H2 H 1.079(4) 0.583(3) 0.230(4) 0.045(8) Uiso 1 1 d . . . . .
H12 H 1.086(6) 0.105(4) 0.191(5) 0.068(12) Uiso 1 1 d . . . . .
H11 H 1.158(5) -0.020(5) 0.184(5) 0.083(14) Uiso 1 1 d . . . . .
H1 H 1.235(8) 0.284(6) 0.150(7) 0.14(2) Uiso 1 1 d . . . . .
N3 N 0.4974(4) 0.5340(4) 0.4622(4) 0.0707(9) Uani 1 1 d . . . . .
O3 O 0.9666(3) 0.2543(2) 0.2898(4) 0.0683(7) Uani 1 1 d . . . . .
O2 O 1.1471(4) 0.3741(2) 0.1795(4) 0.0700(8) Uani 1 1 d . . . . .
O5 O 0.8739(4) 0.8677(2) 0.3165(4) 0.0768(8) Uani 1 1 d . . . . .
C2 C 0.9161(4) 0.4584(3) 0.2991(4) 0.0463(7) Uani 1 1 d . . . . .
C4 C 0.8875(4) 0.6666(3) 0.3121(4) 0.0489(7) Uani 1 1 d . . . . .
C6 C 0.6670(4) 0.5460(4) 0.3979(3) 0.0502(8) Uani 1 1 d . . . . .
C7 C 0.7568(5) 0.4470(3) 0.3618(4) 0.0519(8) Uani 1 1 d . . . . .
O6 O 0.4125(4) 0.6217(3) 0.4811(5) 0.1005(11) Uani 1 1 d . . . . .
C5 C 0.7296(4) 0.6577(4) 0.3751(4) 0.0524(8) Uani 1 1 d . . . . .
O4 O 1.0962(4) 0.7893(2) 0.2277(5) 0.0920(10) Uani 1 1 d . . . . .
N2 N 0.9567(4) 0.7831(2) 0.2840(4) 0.0576(8) Uani 1 1 d . . . . .
C1 C 1.0128(5) 0.3518(3) 0.2556(4) 0.0506(8) Uani 1 1 d . . . . .
O7 O 0.4527(4) 0.4349(4) 0.4937(4) 0.1023(11) Uani 1 1 d . . . . .
C3 C 0.9815(4) 0.5695(3) 0.2728(4) 0.0457(7) Uani 1 1 d . . . . .
O1 O 1.3367(3) 0.2116(2) 0.1077(3) 0.0653(7) Uani 1 1 d . . . . .
N1 N 1.4448(4) 0.0314(3) 0.0763(4) 0.0555(7) Uani 1 1 d . . . . .
N4 N 1.1703(4) 0.0572(3) 0.1663(4) 0.0570(7) Uani 1 1 d . . . . .
C8 C 1.3184(4) 0.1031(3) 0.1171(4) 0.0482(7) Uani 1 1 d . . . . .
C10 C 1.4300(5) -0.0956(3) 0.0837(5) 0.0646(10) Uani 1 1 d . . . . .
H10A H 1.453631 -0.120556 0.202102 0.097 Uiso 1 1 calc R U . . .
H10B H 1.516885 -0.130897 0.025214 0.097 Uiso 1 1 calc R U . . .
H10C H 1.309762 -0.119187 0.028539 0.097 Uiso 1 1 calc R U . . .
C9 C 1.6132(5) 0.0803(3) 0.0461(6) 0.0736(10) Uani 1 1 d . . . . .
H9A H 1.604751 0.164264 0.042905 0.110 Uiso 1 1 calc R U . . .
H9B H 1.635707 0.052055 -0.062197 0.110 Uiso 1 1 calc R U . . .
H9C H 1.711091 0.056917 0.137564 0.110 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 O6 1.212(5) . ?
N3 O7 1.218(5) . ?
N3 C6 1.470(4) . ?
O3 C1 1.211(4) . ?
O2 C1 1.298(4) . ?
O5 N2 1.204(4) . ?
C2 C3 1.388(4) . ?
C2 C7 1.390(5) . ?
C2 C1 1.492(5) . ?
C4 C5 1.379(5) . ?
C4 C3 1.382(5) . ?
C4 N2 1.460(5) . ?
C6 C7 1.374(5) . ?
C6 C5 1.382(6) . ?
O4 N2 1.219(4) . ?
O1 C8 1.249(4) . ?
N1 C8 1.340(4) . ?
N1 C9 1.446(4) . ?
N1 C10 1.454(5) . ?
N4 C8 1.356(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 N3 O7 124.5(3) . . ?
O6 N3 C6 118.7(4) . . ?
O7 N3 C6 116.8(4) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 120.4(3) . . ?
C7 C2 C1 119.9(3) . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 N2 118.7(3) . . ?
C3 C4 N2 118.8(3) . . ?
C7 C6 C5 122.4(3) . . ?
C7 C6 N3 119.4(4) . . ?
C5 C6 N3 118.2(3) . . ?
C6 C7 C2 119.3(3) . . ?
C4 C5 C6 117.0(3) . . ?
O5 N2 O4 123.4(3) . . ?
O5 N2 C4 118.8(3) . . ?
O4 N2 C4 117.8(3) . . ?
O3 C1 O2 124.6(3) . . ?
O3 C1 C2 121.5(3) . . ?
O2 C1 C2 113.9(3) . . ?
C4 C3 C2 119.0(3) . . ?
C8 N1 C9 119.4(3) . . ?
C8 N1 C10 122.3(3) . . ?
C9 N1 C10 117.8(3) . . ?
O1 C8 N1 119.9(3) . . ?
O1 C8 N4 120.4(3) . . ?
N1 C8 N4 119.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H12 O3 0.89(5) 2.14(5) 2.990(4) 160(4) . yes
N4 H11 O4 0.90(6) 2.26(6) 3.159(4) 174(4) 1_545 yes
O1 H1 O3 1.21(7) 2.51(6) 3.411(3) 129(5) . yes
O1 H1 O2 1.21(7) 1.27(7) 2.472(3) 168(6) . yes
C10 H10A O7 0.96 2.45 3.297(5) 147.2 2_746 yes
C10 H10B O1 0.96 2.45 3.354(4) 157.0 2_845 yes
C10 H10C O4 0.96 2.67 3.233(5) 117.6 1_545 yes
C9 H9B O2 0.96 2.87 3.637(5) 137.5 2_845 yes

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 30 degreesC'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_350K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921992'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex_2_350K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      47.69 %
RESPONSE: Data collection at non-standard wavelength. Fprime used for anomalous dispersion and absorption coefficients.
;
_vrf_PLAT355_complex_2_350K_shelxl 
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O2       - H1       .       1.15 Ang.
RESPONSE: Long distance is characteristic of H1 being in short strong O2-H1...O1 hydrogen bond.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H8 N2 O1, C7 H4 N2 O6'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   23.2312(3)
_cell_length_b                   19.3458(3)
_cell_length_c                   6.00460(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2698.62(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    350
_cell_measurement_reflns_used    11423
_cell_measurement_theta_min      1.69380406263
_cell_measurement_theta_max      35.4051469394

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.991418910165
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      350
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38400
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         27.739
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3474
_reflns_number_gt                1728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       GDA
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.9.3-gb491019a-release'
_computing_data_reduction        
;
 aimless (Evans, P. R. and Murshudov, G. N., 2013)
 ccp4 (Winn, M. D. et al., 2011) 
 DIALS 1.9.3-gb491019a-release (Winter, G. et al., 2018) 
 pointless (Evans, P., 2006) 
 XIA2 0.5.546-gdf2e0b53-dials-1.9 (Winter, G., 2010) 
;
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.74 command used to make multi_T datasets comparable: 0.74 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.

Deviating H-C-H angle for methyl group C3. H-atoms were placed geometrically
using HFIX 137.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0888P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3474
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.979
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H10 H 0.1080(9) 0.6882(10) 1.491(3) 0.093(6) Uiso 1 1 d . . . . .
H11 H 0.1900(9) 0.7066(11) 1.695(4) 0.092(6) Uiso 1 1 d . . . . .
H12 H 0.2833(7) 0.5991(8) 1.296(3) 0.067(5) Uiso 1 1 d . . . . .
H3 H -0.0423(10) 0.5288(13) 0.778(4) 0.112(8) Uiso 1 1 d . . . . .
H2 H 0.0060(11) 0.5680(11) 0.940(4) 0.103(6) Uiso 1 1 d . . . . .
H1 H 0.0463(13) 0.6688(13) 0.883(5) 0.146(9) Uiso 1 1 d . . . . .
O1 O 0.00732(5) 0.67107(6) 0.7192(2) 0.0900(4) Uani 1 1 d . . . . .
N2 N -0.05830(6) 0.61925(8) 0.5026(3) 0.0815(4) Uani 1 1 d . . . . .
N1 N -0.01966(8) 0.56279(9) 0.8048(3) 0.0981(6) Uani 1 1 d . . . . .
C1 C -0.02330(7) 0.61787(9) 0.6762(3) 0.0736(5) Uani 1 1 d . . . . .
C2 C -0.09395(9) 0.56085(12) 0.4424(4) 0.1060(7) Uani 1 1 d . . . . .
H2A H -0.070625 0.519968 0.434053 0.159 Uiso 1 1 calc R U . . .
H2B H -0.111534 0.569264 0.300312 0.159 Uiso 1 1 calc R U . . .
H2C H -0.123343 0.554562 0.552960 0.159 Uiso 1 1 calc R U . . .
C3 C -0.06304(11) 0.68098(12) 0.3671(4) 0.1130(7) Uani 1 1 d . . . . .
H3A H -0.032866 0.712644 0.406113 0.170 Uiso 1 1 calc R U . . .
H3B H -0.099719 0.702413 0.392793 0.170 Uiso 1 1 calc R U . . .
H3C H -0.059693 0.668764 0.212714 0.170 Uiso 1 1 calc R U . . .
O2 O 0.08941(6) 0.66576(7) 0.9759(2) 0.0884(4) Uani 1 1 d . . . . .
O3 O 0.05675(6) 0.58031(7) 1.1865(2) 0.0975(4) Uani 1 1 d . . . . .
C5 C 0.14743(6) 0.63022(7) 1.2680(3) 0.0640(4) Uani 1 1 d . . . . .
C10 C 0.20100(6) 0.60296(7) 1.2121(3) 0.0618(4) Uani 1 1 d . . . . .
O5 O 0.25460(7) 0.54724(8) 0.9429(2) 0.0991(4) Uani 1 1 d . . . . .
C8 C 0.24481(7) 0.65560(8) 1.5211(3) 0.0657(4) Uani 1 1 d . . . . .
C4 C 0.09351(7) 0.62241(8) 1.1317(3) 0.0707(4) Uani 1 1 d . . . . .
N3 N 0.20716(7) 0.55845(7) 1.0165(3) 0.0769(4) Uani 1 1 d . . . . .
N4 N 0.29650(7) 0.66992(8) 1.6548(3) 0.0840(4) Uani 1 1 d . . . . .
C9 C 0.24964(7) 0.61528(8) 1.3354(3) 0.0657(4) Uani 1 1 d . . . . .
C6 C 0.14473(8) 0.67012(9) 1.4592(3) 0.0730(5) Uani 1 1 d . . . . .
O6 O 0.34197(7) 0.64714(10) 1.5899(3) 0.1179(5) Uani 1 1 d . . . . .
O7 O 0.29109(7) 0.70349(9) 1.8235(3) 0.1205(6) Uani 1 1 d . . . . .
C7 C 0.19275(8) 0.68260(9) 1.5863(3) 0.0754(5) Uani 1 1 d . . . . .
O4 O 0.16425(8) 0.53476(10) 0.9333(3) 0.1364(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.277(2) . ?
N2 C1 1.322(2) . ?
N2 C2 1.447(3) . ?
N2 C3 1.449(3) . ?
N1 C1 1.319(2) . ?
O2 C4 1.260(2) . ?
O3 C4 1.2250(19) . ?
C5 C6 1.385(2) . ?
C5 C10 1.393(2) . ?
C5 C4 1.504(2) . ?
C10 C9 1.372(2) . ?
C10 N3 1.463(2) . ?
O5 N3 1.2068(19) . ?
C8 C9 1.365(2) . ?
C8 C7 1.375(2) . ?
C8 N4 1.471(2) . ?
N3 O4 1.205(2) . ?
N4 O6 1.209(2) . ?
N4 O7 1.210(2) . ?
C6 C7 1.373(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 122.23(16) . . ?
C1 N2 C3 120.40(16) . . ?
C2 N2 C3 117.36(17) . . ?
O1 C1 N1 119.80(17) . . ?
O1 C1 N2 119.05(15) . . ?
N1 C1 N2 121.15(17) . . ?
C6 C5 C10 116.84(15) . . ?
C6 C5 C4 117.98(14) . . ?
C10 C5 C4 125.11(14) . . ?
C9 C10 C5 122.69(15) . . ?
C9 C10 N3 117.07(14) . . ?
C5 C10 N3 120.24(14) . . ?
C9 C8 C7 121.48(16) . . ?
C9 C8 N4 119.10(15) . . ?
C7 C8 N4 119.42(16) . . ?
O3 C4 O2 126.10(16) . . ?
O3 C4 C5 120.08(15) . . ?
O2 C4 C5 113.58(13) . . ?
O4 N3 O5 122.37(16) . . ?
O4 N3 C10 118.37(16) . . ?
O5 N3 C10 119.26(15) . . ?
O6 N4 O7 123.80(17) . . ?
O6 N4 C8 117.95(16) . . ?
O7 N4 C8 118.25(17) . . ?
C8 C9 C10 118.19(15) . . ?
C7 C6 C5 121.47(17) . . ?
C6 C7 C8 119.31(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H3 O3 0.86(3) 2.15(3) 2.900(2) 146(2) 5_567 yes
N1 H2 O3 1.01(3) 1.91(3) 2.919(2) 177.4(19) . yes
C2 H2B O4 0.96 2.74 3.344(3) 121.4 5_566 yes
C2 H2C O5 0.96 2.84 3.595(3) 136.3 8_557 yes
C3 H3A O1 0.96 2.68 3.414(3) 133.4 7_575 yes
O2 H1 O1 1.15(3) 1.34(3) 2.4543(17) 162(3) . yes
O2 H1 N1 1.15(3) 2.60(3) 3.383(2) 124.2(17) . yes
N1 H3 O3 0.86(3) 2.15(3) 2.900(2) 146(2) 5_567 yes
N1 H2 O3 1.01(3) 1.91(3) 2.919(2) 177.4(19) . yes
O1 H1 O3 1.34(3) 2.51(3) 3.5037(18) 128.4(17) . yes
O2 H1 O1 1.15(3) 1.34(3) 2.4543(17) 162(3) . yes
O2 H1 N1 1.15(3) 2.60(3) 3.383(2) 124.2(17) . yes

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_3_150K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921998'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_3_150K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      23.99 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O6, C3 H8 N2 O1'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4488(4)
_cell_length_b                   11.3580(5)
_cell_length_c                   7.8908(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.062(3)
_cell_angle_gamma                90
_cell_volume                     650.31(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    5782
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      41.12

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.182
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10340
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.302
_diffrn_reflns_theta_max         36.176
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3166
_reflns_number_gt                2673
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_max     0.971
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.75 command used to make multi_T datasets for complex 2 comparable: 0.75 Angstroms
is the maximum diffraction resolution of high T (300 K) data set.

Deviating H-C-H angle for methyl group C9, C10. H-atoms were placed geometrically
using HFIX 137 for these methyl groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1081 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3166
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 0.660(4) 0.722(3) 0.405(3) 0.028(7) Uiso 1 1 d . . . . .
H4 H 0.713(5) 0.370(3) 0.381(4) 0.045(9) Uiso 1 1 d . . . . .
H2 H 1.082(4) 0.588(3) 0.228(3) 0.024(6) Uiso 1 1 d . . . . .
H12 H 1.085(5) 0.106(4) 0.184(5) 0.055(11) Uiso 1 1 d . . . . .
H11 H 1.152(4) -0.013(4) 0.180(4) 0.041(9) Uiso 1 1 d . . . . .
H1 H 1.237(8) 0.291(6) 0.143(7) 0.124(19) Uiso 1 1 d . . . . .
N3 N 0.4972(3) 0.5322(3) 0.4633(3) 0.0412(6) Uani 1 1 d . . . . .
O3 O 0.9708(3) 0.25325(16) 0.2928(3) 0.0381(5) Uani 1 1 d . . . . .
O2 O 1.1456(3) 0.37434(17) 0.1759(3) 0.0411(5) Uani 1 1 d . . . . .
O5 O 0.8699(3) 0.87018(18) 0.3156(3) 0.0445(5) Uani 1 1 d . . . . .
C2 C 0.9166(4) 0.4584(2) 0.2989(3) 0.0269(5) Uani 1 1 d . . . . .
C4 C 0.8856(3) 0.6674(3) 0.3124(3) 0.0279(5) Uani 1 1 d . . . . .
C6 C 0.6670(3) 0.5461(3) 0.3984(3) 0.0298(6) Uani 1 1 d . . . . .
C7 C 0.7579(4) 0.4457(2) 0.3627(3) 0.0282(5) Uani 1 1 d . . . . .
O6 O 0.4128(3) 0.6202(2) 0.4836(4) 0.0593(7) Uani 1 1 d . . . . .
C5 C 0.7282(4) 0.6581(3) 0.3751(3) 0.0290(6) Uani 1 1 d . . . . .
O4 O 1.0960(3) 0.79123(19) 0.2304(3) 0.0522(6) Uani 1 1 d . . . . .
N2 N 0.9551(3) 0.78486(19) 0.2847(3) 0.0333(5) Uani 1 1 d . . . . .
C1 C 1.0142(4) 0.3515(2) 0.2559(3) 0.0275(5) Uani 1 1 d . . . . .
O7 O 0.4512(3) 0.4327(3) 0.4926(3) 0.0594(7) Uani 1 1 d . . . . .
C3 C 0.9805(3) 0.5700(2) 0.2731(3) 0.0261(5) Uani 1 1 d . . . . .
O1 O 1.3381(3) 0.21249(18) 0.1071(2) 0.0365(5) Uani 1 1 d . . . . .
N1 N 1.4428(3) 0.0299(2) 0.0734(3) 0.0321(5) Uani 1 1 d . . . . .
N4 N 1.1703(3) 0.0570(2) 0.1671(3) 0.0323(5) Uani 1 1 d . . . . .
C8 C 1.3175(3) 0.1029(2) 0.1171(3) 0.0279(5) Uani 1 1 d . . . . .
C10 C 1.4266(4) -0.0977(2) 0.0829(4) 0.0350(6) Uani 1 1 d . . . . .
H10A H 1.459226 -0.122241 0.202373 0.052 Uiso 1 1 calc R U . . .
H10B H 1.507930 -0.134241 0.019979 0.052 Uiso 1 1 calc R U . . .
H10C H 1.301917 -0.120759 0.032647 0.052 Uiso 1 1 calc R U . . .
C9 C 1.6138(4) 0.0795(3) 0.0447(4) 0.0422(7) Uani 1 1 d . . . . .
H9A H 1.587473 0.150968 -0.021340 0.063 Uiso 1 1 calc R U . . .
H9B H 1.671123 0.024127 -0.018316 0.063 Uiso 1 1 calc R U . . .
H9C H 1.695429 0.096297 0.154737 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 O6 1.211(4) . ?
N3 O7 1.218(4) . ?
N3 C6 1.476(3) . ?
O3 C1 1.215(3) . ?
O2 C1 1.305(4) . ?
O5 N2 1.213(3) . ?
C2 C3 1.385(4) . ?
C2 C7 1.392(4) . ?
C2 C1 1.494(4) . ?
C4 C5 1.376(4) . ?
C4 C3 1.385(4) . ?
C4 N2 1.466(3) . ?
C6 C5 1.378(4) . ?
C6 C7 1.388(4) . ?
O4 N2 1.222(3) . ?
O1 C8 1.259(3) . ?
N1 C8 1.351(3) . ?
N1 C9 1.457(3) . ?
N1 C10 1.458(4) . ?
N4 C8 1.351(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 N3 O7 124.3(2) . . ?
O6 N3 C6 118.0(3) . . ?
O7 N3 C6 117.7(3) . . ?
C3 C2 C7 119.8(2) . . ?
C3 C2 C1 120.6(2) . . ?
C7 C2 C1 119.6(2) . . ?
C5 C4 C3 122.6(3) . . ?
C5 C4 N2 118.8(2) . . ?
C3 C4 N2 118.6(2) . . ?
C5 C6 C7 122.7(2) . . ?
C5 C6 N3 118.7(2) . . ?
C7 C6 N3 118.6(3) . . ?
C6 C7 C2 118.7(2) . . ?
C4 C5 C6 116.9(2) . . ?
O5 N2 O4 123.6(2) . . ?
O5 N2 C4 118.6(2) . . ?
O4 N2 C4 117.8(2) . . ?
O3 C1 O2 124.6(2) . . ?
O3 C1 C2 121.5(2) . . ?
O2 C1 C2 113.9(2) . . ?
C4 C3 C2 119.2(2) . . ?
C8 N1 C9 118.7(2) . . ?
C8 N1 C10 121.8(2) . . ?
C9 N1 C10 118.6(2) . . ?
O1 C8 N1 119.4(2) . . ?
O1 C8 N4 121.2(3) . . ?
N1 C8 N4 119.4(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H12 O3 0.88(4) 2.14(5) 2.971(3) 158(3) . yes
N4 H11 O4 0.82(4) 2.31(4) 3.129(3) 177(3) 1_545 yes
O1 H1 O3 1.24(6) 2.57(6) 3.415(3) 124(4) . yes
O2 H1 O1 1.23(6) 1.24(6) 2.466(3) 176(6) . yes
C10 H10A O7 0.96 2.43 3.285(4) 148.3 2_746 yes
C10 H10B O1 0.96 2.42 3.340(3) 159.6 2_845 yes
C10 H10C O4 0.96 2.62 3.210(4) 120.0 1_545 yes
C9 H9B O2 0.96 2.66 3.617(4) 175.6 2_845 yes

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 30 degreesC'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_200K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921993'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_200K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      47.66 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H9 N2 O1, C7 H3 N2 O6'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   23.02270(8)
_cell_length_b                   19.24130(7)
_cell_length_c                   5.87020(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2600.421(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    200
_cell_measurement_reflns_used    25459
_cell_measurement_theta_min      1.70419623743
_cell_measurement_theta_max      36.0064993709

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.994890606381
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37690
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         27.740
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3350
_reflns_number_gt                2851
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       GDA
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.9.3-gb491019a-release'
_computing_data_reduction        
;
 aimless (Evans, P. R. and Murshudov, G. N., 2013)
 ccp4 (Winn, M. D. et al., 2011) 
 DIALS 1.9.3-gb491019a-release (Winter, G. et al., 2018) 
 pointless (Evans, P., 2006) 
 XIA2 0.5.546-gdf2e0b53-dials-1.9 (Winter, G., 2010) 
;
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.74 command used to make multi_T datasets comparable: 0.74 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.4724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1035
_refine_ls_wR_factor_gt          0.0990
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H10 H 0.1087(6) 0.6888(7) 1.518(2) 0.039(3) Uiso 1 1 d . . . . .
H11 H 0.1927(6) 0.7106(8) 1.742(3) 0.049(4) Uiso 1 1 d . . . . .
H12 H 0.2869(6) 0.5976(7) 1.299(2) 0.039(3) Uiso 1 1 d . . . . .
H3 H -0.0404(7) 0.5260(9) 0.782(3) 0.056(5) Uiso 1 1 d . . . . .
H2 H 0.0006(8) 0.5670(8) 0.928(3) 0.052(4) Uiso 1 1 d . . . . .
H6 H -0.1083(9) 0.5680(10) 0.272(4) 0.081(6) Uiso 1 1 d . . . . .
H4 H -0.0704(8) 0.5175(10) 0.434(3) 0.063(5) Uiso 1 1 d . . . . .
H7 H -0.0592(9) 0.6686(12) 0.190(4) 0.091(7) Uiso 1 1 d . . . . .
H5 H -0.1259(9) 0.5548(10) 0.531(4) 0.076(6) Uiso 1 1 d . . . . .
H8 H -0.1014(10) 0.7010(11) 0.361(4) 0.089(7) Uiso 1 1 d . . . . .
H9 H -0.0334(10) 0.7105(11) 0.385(4) 0.082(6) Uiso 1 1 d . . . . .
H1 H 0.0435(9) 0.6669(11) 0.857(4) 0.087(6) Uiso 1 1 d . . . . .
O1 O 0.00731(4) 0.67292(4) 0.71805(16) 0.0397(2) Uani 1 1 d . . . . .
N2 N -0.05734(4) 0.61920(5) 0.49133(17) 0.0352(2) Uani 1 1 d . . . . .
N1 N -0.01982(5) 0.56305(6) 0.8061(2) 0.0437(3) Uani 1 1 d . . . . .
C1 C -0.02317(4) 0.61839(6) 0.6723(2) 0.0323(2) Uani 1 1 d . . . . .
C2 C -0.09298(6) 0.55959(7) 0.4303(3) 0.0459(3) Uani 1 1 d . . . . .
C3 C -0.06239(7) 0.68131(8) 0.3505(3) 0.0488(3) Uani 1 1 d . . . . .
O2 O 0.08976(4) 0.66682(4) 0.98051(15) 0.0397(2) Uani 1 1 d . . . . .
O3 O 0.05685(4) 0.57959(4) 1.19633(16) 0.0424(2) Uani 1 1 d . . . . .
C5 C 0.14881(4) 0.63015(5) 1.27947(18) 0.0281(2) Uani 1 1 d . . . . .
C10 C 0.20276(4) 0.60281(5) 1.21921(18) 0.0282(2) Uani 1 1 d . . . . .
O5 O 0.25695(4) 0.54710(5) 0.94164(15) 0.0431(2) Uani 1 1 d . . . . .
C8 C 0.24760(5) 0.65563(5) 1.53625(18) 0.0302(2) Uani 1 1 d . . . . .
C4 C 0.09391(4) 0.62265(5) 1.13976(19) 0.0306(2) Uani 1 1 d . . . . .
N3 N 0.20840(4) 0.55802(5) 1.01777(17) 0.0349(2) Uani 1 1 d . . . . .
N4 N 0.30013(4) 0.66966(5) 1.67103(17) 0.0375(2) Uani 1 1 d . . . . .
C9 C 0.25275(5) 0.61501(5) 1.34337(18) 0.0296(2) Uani 1 1 d . . . . .
C6 C 0.14592(5) 0.67049(6) 1.47619(19) 0.0331(2) Uani 1 1 d . . . . .
O6 O 0.34612(4) 0.64614(6) 1.60333(17) 0.0534(3) Uani 1 1 d . . . . .
O7 O 0.29486(4) 0.70394(5) 1.84506(17) 0.0550(3) Uani 1 1 d . . . . .
C7 C 0.19503(5) 0.68320(6) 1.60589(19) 0.0335(2) Uani 1 1 d . . . . .
O4 O 0.16435(4) 0.53385(6) 0.9352(2) 0.0642(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2904(13) . ?
N2 C1 1.3218(15) . ?
N2 C2 1.4550(16) . ?
N2 C3 1.4577(17) . ?
N1 C1 1.3253(16) . ?
O2 C4 1.2670(13) . ?
O3 C4 1.2346(13) . ?
C5 C6 1.3930(15) . ?
C5 C10 1.3945(14) . ?
C5 C4 1.5136(14) . ?
C10 C9 1.3824(15) . ?
C10 N3 1.4689(14) . ?
O5 N3 1.2221(13) . ?
C8 C9 1.3809(15) . ?
C8 C7 1.3833(16) . ?
C8 N4 1.4702(14) . ?
N3 O4 1.2165(13) . ?
N4 O6 1.2180(14) . ?
N4 O7 1.2220(14) . ?
C6 C7 1.3848(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 121.61(10) . . ?
C1 N2 C3 120.85(10) . . ?
C2 N2 C3 117.50(11) . . ?
O1 C1 N2 118.77(10) . . ?
O1 C1 N1 119.88(11) . . ?
N2 C1 N1 121.35(11) . . ?
C6 C5 C10 117.58(9) . . ?
C6 C5 C4 117.55(9) . . ?
C10 C5 C4 124.77(9) . . ?
C9 C10 C5 122.94(10) . . ?
C9 C10 N3 116.77(9) . . ?
C5 C10 N3 120.28(9) . . ?
C9 C8 C7 122.30(10) . . ?
C9 C8 N4 118.33(10) . . ?
C7 C8 N4 119.36(10) . . ?
O3 C4 O2 126.62(10) . . ?
O3 C4 C5 119.69(10) . . ?
O2 C4 C5 113.50(9) . . ?
O4 N3 O5 123.44(10) . . ?
O4 N3 C10 118.12(10) . . ?
O5 N3 C10 118.43(9) . . ?
O6 N4 O7 124.03(10) . . ?
O6 N4 C8 118.11(10) . . ?
O7 N4 C8 117.85(10) . . ?
C8 C9 C10 117.20(10) . . ?
C7 C6 C5 121.02(10) . . ?
C8 C7 C6 118.96(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H3 O3 0.868(18) 2.070(18) 2.8741(14) 153.7(15) 5_567 yes
N1 H2 O3 0.860(19) 2.053(19) 2.9096(15) 173.6(16) . yes
C2 H6 O4 1.01(2) 2.64(2) 3.2460(16) 118.4(14) 5_566 yes
C2 H5 O5 0.96(2) 2.71(2) 3.5439(17) 145.7(16) 8_557 yes
C3 H9 O1 0.89(2) 2.62(2) 3.3236(18) 136.0(17) 7_575 yes
O1 H1 O2 1.17(2) 1.29(2) 2.4477(11) 169(2) . yes
O2 H1 N1 1.29(2) 2.49(2) 3.3764(14) 123.3(13) . yes

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_3_100K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921994'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_3_100K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      24.33 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 3,5-dinitrobenzoate acid 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O6, C3 H8 N2 O1'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4233(4)
_cell_length_b                   11.3405(5)
_cell_length_c                   7.8840(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.648(3)
_cell_angle_gamma                90
_cell_volume                     644.96(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    6140
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      42.78

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.183
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7101
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10290
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.313
_diffrn_reflns_theta_max         36.180
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3155
_reflns_number_gt                2780
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.989

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.75 command used to make multi_T datasets for complex 2 comparable: 0.75 Angstroms
is the maximum diffraction resolution of high T (300 K) data set.

Deviating H-C-H angle for methyl group C9, C10. H-atoms were placed geometrically
using HFIX 137 for these methyl groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0584P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3155
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 0.662(4) 0.725(3) 0.405(3) 0.018(7) Uiso 1 1 d . . . . .
H4 H 0.715(4) 0.368(3) 0.378(4) 0.023(7) Uiso 1 1 d . . . . .
H2 H 1.079(4) 0.590(3) 0.229(3) 0.017(7) Uiso 1 1 d . . . . .
H12 H 1.090(5) 0.109(4) 0.187(5) 0.047(11) Uiso 1 1 d . . . . .
H11 H 1.156(4) -0.013(4) 0.182(4) 0.029(9) Uiso 1 1 d . . . . .
H1 H 1.235(8) 0.287(6) 0.143(8) 0.12(2) Uiso 1 1 d . . . . .
N3 N 0.4972(3) 0.5318(2) 0.4634(3) 0.0297(5) Uani 1 1 d . . . . .
O3 O 0.9731(2) 0.25286(16) 0.2951(2) 0.0270(4) Uani 1 1 d . . . . .
O2 O 1.1440(3) 0.37453(16) 0.1740(3) 0.0301(5) Uani 1 1 d . . . . .
O5 O 0.8674(3) 0.87105(17) 0.3140(3) 0.0329(5) Uani 1 1 d . . . . .
C2 C 0.9164(3) 0.4583(2) 0.2991(3) 0.0202(5) Uani 1 1 d . . . . .
C4 C 0.8853(3) 0.6677(2) 0.3122(3) 0.0212(5) Uani 1 1 d . . . . .
C6 C 0.6666(3) 0.5451(3) 0.3983(3) 0.0234(6) Uani 1 1 d . . . . .
C7 C 0.7575(4) 0.4452(2) 0.3627(3) 0.0217(5) Uani 1 1 d . . . . .
O6 O 0.4126(3) 0.6201(2) 0.4849(3) 0.0425(6) Uani 1 1 d . . . . .
C5 C 0.7271(3) 0.6581(2) 0.3755(3) 0.0214(5) Uani 1 1 d . . . . .
O4 O 1.0968(3) 0.79237(17) 0.2319(3) 0.0372(5) Uani 1 1 d . . . . .
N2 N 0.9540(3) 0.78539(19) 0.2843(3) 0.0246(5) Uani 1 1 d . . . . .
C1 C 1.0150(4) 0.3513(2) 0.2562(3) 0.0207(5) Uani 1 1 d . . . . .
O7 O 0.4505(3) 0.4313(2) 0.4911(3) 0.0438(6) Uani 1 1 d . . . . .
C3 C 0.9805(3) 0.5701(2) 0.2731(3) 0.0195(5) Uani 1 1 d . . . . .
O1 O 1.3391(2) 0.21279(17) 0.1075(2) 0.0267(4) Uani 1 1 d . . . . .
N1 N 1.4416(3) 0.0294(2) 0.0722(3) 0.0239(5) Uani 1 1 d . . . . .
N4 N 1.1702(3) 0.0569(2) 0.1675(3) 0.0238(5) Uani 1 1 d . . . . .
C8 C 1.3178(3) 0.1030(2) 0.1169(3) 0.0209(5) Uani 1 1 d . . . . .
C10 C 1.4252(4) -0.0984(2) 0.0829(4) 0.0257(6) Uani 1 1 d . . . . .
H10A H 1.461846 -0.122577 0.202819 0.039 Uiso 1 1 calc R U . . .
H10B H 1.504084 -0.135332 0.018018 0.039 Uiso 1 1 calc R U . . .
H10C H 1.298981 -0.121291 0.034997 0.039 Uiso 1 1 calc R U . . .
C9 C 1.6141(3) 0.0792(3) 0.0446(4) 0.0307(6) Uani 1 1 d . . . . .
H9A H 1.586955 0.148836 -0.026152 0.046 Uiso 1 1 calc R U . . .
H9B H 1.674293 0.022339 -0.013444 0.046 Uiso 1 1 calc R U . . .
H9C H 1.694291 0.099259 0.155200 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 O6 1.215(3) . ?
N3 O7 1.226(3) . ?
N3 C6 1.474(3) . ?
O3 C1 1.217(3) . ?
O2 C1 1.303(3) . ?
O5 N2 1.218(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.394(4) . ?
C2 C1 1.497(3) . ?
C4 C5 1.384(4) . ?
C4 C3 1.386(3) . ?
C4 N2 1.464(3) . ?
C6 C7 1.381(4) . ?
C6 C5 1.383(4) . ?
O4 N2 1.228(3) . ?
O1 C8 1.259(3) . ?
N1 C8 1.349(3) . ?
N1 C10 1.458(3) . ?
N1 C9 1.462(3) . ?
N4 C8 1.356(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 N3 O7 124.4(2) . . ?
O6 N3 C6 118.4(2) . . ?
O7 N3 C6 117.3(2) . . ?
C3 C2 C7 120.0(2) . . ?
C3 C2 C1 120.3(2) . . ?
C7 C2 C1 119.7(2) . . ?
C5 C4 C3 122.5(2) . . ?
C5 C4 N2 118.8(2) . . ?
C3 C4 N2 118.7(2) . . ?
C7 C6 C5 123.0(2) . . ?
C7 C6 N3 119.0(2) . . ?
C5 C6 N3 118.0(2) . . ?
C6 C7 C2 118.7(2) . . ?
C6 C5 C4 116.7(2) . . ?
O5 N2 O4 123.4(2) . . ?
O5 N2 C4 118.7(2) . . ?
O4 N2 C4 117.94(19) . . ?
O3 C1 O2 124.9(2) . . ?
O3 C1 C2 121.3(2) . . ?
O2 C1 C2 113.8(2) . . ?
C4 C3 C2 119.1(2) . . ?
C8 N1 C10 121.9(2) . . ?
C8 N1 C9 118.3(2) . . ?
C10 N1 C9 118.7(2) . . ?
O1 C8 N1 119.6(2) . . ?
O1 C8 N4 121.3(2) . . ?
N1 C8 N4 119.1(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H12 O3 0.88(4) 2.11(5) 2.964(3) 162(3) . yes
N4 H11 O4 0.81(4) 2.30(4) 3.113(3) 176(3) 1_545 yes
O1 H1 O3 1.22(7) 2.54(6) 3.416(2) 127(4) . yes
O1 H1 O2 1.22(7) 1.26(7) 2.469(3) 172(6) . yes
C10 H10A O7 0.96 2.42 3.283(3) 148.8 2_746 yes
C10 H10B O1 0.96 2.42 3.338(3) 160.5 2_845 yes
C10 H10C O4 0.96 2.59 3.195(3) 121.1 1_545 yes
C9 H9B O2 0.96 2.65 3.612(3) 176.6 2_845 yes

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 30 degreesC'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_300K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921991'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_300K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.69 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H12 N4 O7'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   23.1543(2)
_cell_length_b                   19.32370(17)
_cell_length_c                   5.95150(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2662.86(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    300
_cell_measurement_reflns_used    16293
_cell_measurement_theta_min      1.69764954856
_cell_measurement_theta_max      34.2644147636

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.994646578694
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Diamond Light Source Beamline I19-1'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'shutterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38298
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.988
_diffrn_reflns_theta_max         27.740
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3428
_reflns_number_gt                2300
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       GDA
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.9.3-gb491019a-release'
_computing_data_reduction        
;
 aimless (Evans, P. R. and Murshudov, G. N., 2013)
 ccp4 (Winn, M. D. et al., 2011) 
 DIALS 1.9.3-gb491019a-release (Winter, G. et al., 2018) 
 pointless (Evans, P., 2006) 
 XIA2 0.5.546-gdf2e0b53-dials-1.9 (Winter, G., 2010) 
;
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.74 command used to make multi_T datasets comparable: 0.74 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.

Deviating H-C-H angle for methyl group C3. H-atoms were placed geometrically
using HFIX 137.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0820P)²+0.0095P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3428
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H10 H 0.1075(8) 0.6890(9) 1.507(3) 0.074(5) Uiso 1 1 d . . . . .
H11 H 0.1910(7) 0.7073(9) 1.711(3) 0.073(5) Uiso 1 1 d . . . . .
H12 H 0.2860(7) 0.5985(8) 1.295(3) 0.059(4) Uiso 1 1 d . . . . .
H3 H -0.0414(8) 0.5265(11) 0.777(3) 0.085(6) Uiso 1 1 d . . . . .
H2 H 0.0026(9) 0.5671(9) 0.931(4) 0.072(5) Uiso 1 1 d . . . . .
H6 H -0.1064(12) 0.5726(14) 0.275(5) 0.127(9) Uiso 1 1 d . . . . .
H4 H -0.0694(10) 0.5189(12) 0.424(4) 0.100(7) Uiso 1 1 d . . . . .
H5 H -0.1247(12) 0.5550(13) 0.546(5) 0.123(9) Uiso 1 1 d . . . . .
H1 H 0.0434(12) 0.6685(13) 0.865(5) 0.127(8) Uiso 1 1 d . . . . .
O1 O 0.00703(5) 0.67173(5) 0.7195(2) 0.0685(3) Uani 1 1 d . . . . .
N2 N -0.05806(5) 0.61910(7) 0.4991(2) 0.0614(3) Uani 1 1 d . . . . .
N1 N -0.01980(6) 0.56295(8) 0.8053(3) 0.0749(4) Uani 1 1 d . . . . .
C1 C -0.02347(5) 0.61799(7) 0.6751(3) 0.0564(3) Uani 1 1 d . . . . .
C2 C -0.09362(9) 0.56014(11) 0.4386(4) 0.0804(5) Uani 1 1 d . . . . .
C3 C -0.06297(9) 0.68105(10) 0.3622(3) 0.0858(5) Uani 1 1 d . . . . .
H3A H -0.032003 0.712183 0.398074 0.129 Uiso 1 1 calc R U . . .
H3B H -0.099276 0.703236 0.391900 0.129 Uiso 1 1 calc R U . . .
H3C H -0.060880 0.668687 0.206197 0.129 Uiso 1 1 calc R U . . .
O2 O 0.08925(5) 0.66618(6) 0.97800(19) 0.0683(3) Uani 1 1 d . . . . .
O3 O 0.05671(5) 0.58000(6) 1.1907(2) 0.0743(3) Uani 1 1 d . . . . .
C5 C 0.14793(5) 0.63028(6) 1.2732(2) 0.0485(3) Uani 1 1 d . . . . .
C10 C 0.20156(5) 0.60289(6) 1.2152(2) 0.0483(3) Uani 1 1 d . . . . .
O5 O 0.25546(5) 0.54717(6) 0.94269(18) 0.0757(3) Uani 1 1 d . . . . .
C8 C 0.24568(6) 0.65562(6) 1.5277(2) 0.0513(3) Uani 1 1 d . . . . .
C4 C 0.09354(6) 0.62249(7) 1.1345(2) 0.0532(3) Uani 1 1 d . . . . .
N3 N 0.20746(6) 0.55817(6) 1.0173(2) 0.0595(3) Uani 1 1 d . . . . .
N4 N 0.29777(6) 0.66980(7) 1.6611(2) 0.0644(3) Uani 1 1 d . . . . .
C9 C 0.25078(6) 0.61523(7) 1.3387(2) 0.0503(3) Uani 1 1 d . . . . .
C6 C 0.14502(6) 0.67044(7) 1.4663(2) 0.0561(3) Uani 1 1 d . . . . .
O6 O 0.34332(5) 0.64677(8) 1.5957(2) 0.0921(4) Uani 1 1 d . . . . .
O7 O 0.29245(6) 0.70360(7) 1.8316(2) 0.0947(4) Uani 1 1 d . . . . .
C7 C 0.19346(7) 0.68288(8) 1.5942(3) 0.0575(4) Uani 1 1 d . . . . .
O4 O 0.16403(6) 0.53427(9) 0.9348(3) 0.1082(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2832(17) . ?
N2 C1 1.3189(19) . ?
N2 C2 1.451(2) . ?
N2 C3 1.453(2) . ?
N1 C1 1.319(2) . ?
O2 C4 1.2611(17) . ?
O3 C4 1.2300(16) . ?
C5 C6 1.388(2) . ?
C5 C10 1.3933(18) . ?
C5 C4 1.5133(18) . ?
C10 C9 1.3769(18) . ?
C10 N3 1.4675(18) . ?
O5 N3 1.2154(17) . ?
C8 C9 1.3738(19) . ?
C8 C7 1.377(2) . ?
C8 N4 1.4698(18) . ?
N3 O4 1.2107(18) . ?
N4 O6 1.2092(18) . ?
N4 O7 1.2131(18) . ?
C6 C7 1.377(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 121.94(14) . . ?
C1 N2 C3 120.42(13) . . ?
C2 N2 C3 117.62(14) . . ?
O1 C1 N1 119.76(14) . . ?
O1 C1 N2 118.98(13) . . ?
N1 C1 N2 121.26(14) . . ?
C6 C5 C10 117.43(12) . . ?
C6 C5 C4 117.83(11) . . ?
C10 C5 C4 124.66(12) . . ?
C9 C10 C5 122.65(12) . . ?
C9 C10 N3 116.98(11) . . ?
C5 C10 N3 120.37(11) . . ?
C9 C8 C7 121.87(13) . . ?
C9 C8 N4 118.53(12) . . ?
C7 C8 N4 119.60(12) . . ?
O3 C4 O2 126.37(13) . . ?
O3 C4 C5 119.67(12) . . ?
O2 C4 C5 113.70(11) . . ?
O4 N3 O5 123.01(13) . . ?
O4 N3 C10 118.23(12) . . ?
O5 N3 C10 118.77(12) . . ?
O6 N4 O7 123.80(14) . . ?
O6 N4 C8 118.23(13) . . ?
O7 N4 C8 117.97(13) . . ?
C8 C9 C10 117.67(12) . . ?
C7 C6 C5 121.05(13) . . ?
C6 C7 C8 119.32(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H3 O3 0.88(2) 2.10(2) 2.8916(18) 149.6(16) 5_567 yes
N1 H2 O3 0.91(2) 2.01(2) 2.9166(19) 175.3(17) . yes
C2 H6 O4 1.04(3) 2.76(3) 3.305(2) 112.7(18) 5_566 yes
C2 H5 O5 0.97(3) 2.78(3) 3.574(3) 140(2) 8_557 yes
C3 H3A O1 0.96 2.64 3.382(2) 134.3 7_575 yes
O1 H1 O2 1.21(3) 1.26(3) 2.4502(14) 166(2) . yes
O2 H1 N1 1.26(3) 2.53(3) 3.3780(18) 122.3(15) . yes

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol, acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_3_200K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921997'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_3_200K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      24.22 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 3,5-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O6, C3 H8 N2 O1'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.4809(4)
_cell_length_b                   11.3782(6)
_cell_length_c                   7.8924(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.334(3)
_cell_angle_gamma                90
_cell_volume                     656.29(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    5158
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      36.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10496
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.292
_diffrn_reflns_theta_max         36.185
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3191
_reflns_number_gt                2407
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.986

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.75 command used to make multi_T datasets for complex 2 comparable: 0.75 Angstroms
is the maximum diffraction resolution of high T (300 K) data set.

Deviating H-C-H angle for methyl group C9, C10. H-atoms were placed geometrically
using HFIX 137 for these methyl groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0587P)²+0.0093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 909 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3191
_refine_ls_number_parameters     216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 0.659(4) 0.725(3) 0.405(4) 0.036(8) Uiso 1 1 d . . . . .
H4 H 0.711(5) 0.372(3) 0.379(4) 0.044(9) Uiso 1 1 d . . . . .
H2 H 1.079(4) 0.586(3) 0.224(4) 0.037(8) Uiso 1 1 d . . . . .
H12 H 1.084(5) 0.107(4) 0.186(5) 0.056(11) Uiso 1 1 d . . . . .
H11 H 1.155(5) -0.017(4) 0.176(4) 0.054(11) Uiso 1 1 d . . . . .
H1 H 1.251(8) 0.277(6) 0.137(8) 0.14(2) Uiso 1 1 d . . . . .
N3 N 0.4977(4) 0.5333(3) 0.4628(3) 0.0560(8) Uani 1 1 d . . . . .
O3 O 0.9689(3) 0.25388(19) 0.2912(3) 0.0526(6) Uani 1 1 d . . . . .
O2 O 1.1464(4) 0.37410(19) 0.1776(3) 0.0551(6) Uani 1 1 d . . . . .
O5 O 0.8720(4) 0.8691(2) 0.3162(4) 0.0607(7) Uani 1 1 d . . . . .
C2 C 0.9163(4) 0.4585(3) 0.2986(3) 0.0367(6) Uani 1 1 d . . . . .
C4 C 0.8863(4) 0.6668(3) 0.3124(4) 0.0376(6) Uani 1 1 d . . . . .
C6 C 0.6673(4) 0.5462(3) 0.3981(3) 0.0405(7) Uani 1 1 d . . . . .
C7 C 0.7577(5) 0.4461(3) 0.3625(4) 0.0401(7) Uani 1 1 d . . . . .
O6 O 0.4124(4) 0.6211(3) 0.4820(4) 0.0795(10) Uani 1 1 d . . . . .
C5 C 0.7289(4) 0.6581(3) 0.3750(4) 0.0403(7) Uani 1 1 d . . . . .
O4 O 1.0962(4) 0.7904(2) 0.2289(4) 0.0724(8) Uani 1 1 d . . . . .
N2 N 0.9558(4) 0.7840(2) 0.2841(4) 0.0452(7) Uani 1 1 d . . . . .
C1 C 1.0135(4) 0.3516(3) 0.2558(4) 0.0385(7) Uani 1 1 d . . . . .
O7 O 0.4523(4) 0.4339(3) 0.4931(4) 0.0794(9) Uani 1 1 d . . . . .
C3 C 0.9811(4) 0.5697(2) 0.2732(4) 0.0360(6) Uani 1 1 d . . . . .
O1 O 1.3373(3) 0.2118(2) 0.1069(3) 0.0501(6) Uani 1 1 d . . . . .
N1 N 1.4434(3) 0.0305(2) 0.0745(3) 0.0439(6) Uani 1 1 d . . . . .
N4 N 1.1705(4) 0.0570(3) 0.1669(3) 0.0434(6) Uani 1 1 d . . . . .
C8 C 1.3175(4) 0.1026(3) 0.1169(4) 0.0375(6) Uani 1 1 d . . . . .
C10 C 1.4281(5) -0.0969(3) 0.0838(4) 0.0478(8) Uani 1 1 d . . . . .
H10A H 1.457343 -0.121322 0.202905 0.072 Uiso 1 1 calc R U . . .
H10B H 1.511666 -0.132909 0.022476 0.072 Uiso 1 1 calc R U . . .
H10C H 1.305353 -0.120341 0.031973 0.072 Uiso 1 1 calc R U . . .
C9 C 1.6131(4) 0.0799(3) 0.0448(5) 0.0582(9) Uani 1 1 d . . . . .
H9A H 1.590245 0.156953 -0.004744 0.087 Uiso 1 1 calc R U . . .
H9B H 1.660838 0.030301 -0.033376 0.087 Uiso 1 1 calc R U . . .
H9C H 1.700501 0.085273 0.153049 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 O6 1.212(4) . ?
N3 O7 1.220(5) . ?
N3 C6 1.473(4) . ?
O3 C1 1.210(3) . ?
O2 C1 1.302(4) . ?
O5 N2 1.209(4) . ?
C2 C3 1.385(4) . ?
C2 C7 1.392(5) . ?
C2 C1 1.492(4) . ?
C4 C5 1.374(4) . ?
C4 C3 1.383(4) . ?
C4 N2 1.466(4) . ?
C6 C5 1.379(5) . ?
C6 C7 1.383(5) . ?
O4 N2 1.222(4) . ?
O1 C8 1.256(4) . ?
N1 C8 1.344(4) . ?
N1 C9 1.453(4) . ?
N1 C10 1.456(4) . ?
N4 C8 1.349(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 N3 O7 124.3(3) . . ?
O6 N3 C6 118.5(3) . . ?
O7 N3 C6 117.2(3) . . ?
C3 C2 C7 119.8(3) . . ?
C3 C2 C1 120.6(2) . . ?
C7 C2 C1 119.6(3) . . ?
C5 C4 C3 122.8(3) . . ?
C5 C4 N2 118.7(3) . . ?
C3 C4 N2 118.5(2) . . ?
C5 C6 C7 122.8(3) . . ?
C5 C6 N3 118.3(3) . . ?
C7 C6 N3 118.9(3) . . ?
C6 C7 C2 118.8(3) . . ?
C4 C5 C6 116.8(3) . . ?
O5 N2 O4 123.4(3) . . ?
O5 N2 C4 118.7(3) . . ?
O4 N2 C4 117.9(2) . . ?
O3 C1 O2 124.5(3) . . ?
O3 C1 C2 121.6(3) . . ?
O2 C1 C2 113.9(2) . . ?
C4 C3 C2 119.0(3) . . ?
C8 N1 C9 119.1(3) . . ?
C8 N1 C10 121.9(3) . . ?
C9 N1 C10 118.3(3) . . ?
O1 C8 N1 119.4(3) . . ?
O1 C8 N4 120.9(3) . . ?
N1 C8 N4 119.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N4 H12 O3 0.90(5) 2.13(5) 2.981(4) 158(3) . yes
N4 H11 O4 0.86(5) 2.29(5) 3.141(4) 173(3) 1_545 yes
O1 H1 O3 1.05(7) 2.67(6) 3.414(3) 128(5) . yes
O1 H1 O2 1.05(7) 1.43(7) 2.470(3) 175(6) . yes
C10 H10A O7 0.96 2.43 3.286(4) 148.1 2_746 yes
C10 H10B O1 0.96 2.44 3.348(4) 158.6 2_845 yes
C10 H10C O4 0.96 2.63 3.215(4) 119.4 1_545 yes
C9 H9B O2 0.96 2.69 3.627(4) 165.3 2_845 yes

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 30 degreesC'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_1_300K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921986'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_1_300K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      37.21 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT414_complex_1_300K_shelxl 
;
PROBLEM: Short Intra D-H..H-X       H19      ..H20              1.77 Ang.  
RESPONSE: H19 and H20 are in different groups of a N,N-dimethylurea molecule 
and are close in proximity. The distance is made closer due to the large thermal 
ellipsoid of H19; where it is large, increased thermal motion of the methyl group 
is likely. This methyl group has been modelled using HFIX 137.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea phthalic acid 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C3 H8 N2 O1), (C8 H6 O4)'
_chemical_formula_sum            'C14 H22 N4 O6'
_chemical_formula_weight         342.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0076 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0133 0.0073 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1487(4)
_cell_length_b                   6.4317(3)
_cell_length_c                   32.9567(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.369(3)
_cell_angle_gamma                90
_cell_volume                     1716.60(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    300
_cell_measurement_reflns_used    4298
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      26.28

_exptl_crystal_description       'rectangular needle'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9133
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
 SADABS-2014/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23830
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.712
_diffrn_reflns_theta_max         30.646
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4102
_reflns_number_gt                2468
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.76 command used to make multi_T datasets comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (300 K) data set.

Deviating H-C-H angle for methyl group C10, C13, C14. H-atoms were placed geometrically
using HFIX 137 for these methyl groups.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+0.0954P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4102
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H5 H 0.075(3) 0.087(4) 0.2332(7) 0.064(7) Uiso 1 1 d . . . . .
H6 H 0.204(2) 0.411(3) 0.2339(6) 0.043(5) Uiso 1 1 d . . . . .
H4 H -0.078(3) -0.035(4) 0.1756(7) 0.070(7) Uiso 1 1 d . . . . .
H3 H -0.085(3) 0.181(4) 0.1175(8) 0.073(7) Uiso 1 1 d . . . . .
H2 H 0.331(3) 0.902(4) 0.1490(7) 0.078(8) Uiso 1 1 d . . . . .
H1 H -0.112(3) 0.798(5) 0.0810(9) 0.101(9) Uiso 1 1 d . . . . .
O2 O 0.25765(17) 0.7687(2) 0.14540(4) 0.0484(4) Uani 1 1 d . . . . .
O1 O 0.30527(18) 0.7526(2) 0.21294(4) 0.0514(4) Uani 1 1 d . . . . .
O3 O -0.08164(17) 0.7121(2) 0.11019(4) 0.0487(4) Uani 1 1 d . . . . .
O4 O 0.0558(2) 0.5051(3) 0.07143(4) 0.0642(5) Uani 1 1 d . . . . .
C1 C 0.1413(2) 0.4885(3) 0.17800(5) 0.0367(4) Uani 1 1 d . . . . .
C6 C 0.0478(2) 0.4223(3) 0.14187(5) 0.0383(4) Uani 1 1 d . . . . .
C8 C 0.2410(2) 0.6829(3) 0.18048(5) 0.0380(4) Uani 1 1 d . . . . .
C2 C 0.1479(2) 0.3624(3) 0.21219(6) 0.0432(5) Uani 1 1 d . . . . .
C5 C -0.0278(3) 0.2293(3) 0.14118(7) 0.0472(5) Uani 1 1 d . . . . .
C4 C -0.0194(3) 0.1074(3) 0.17581(7) 0.0524(5) Uani 1 1 d . . . . .
C7 C 0.0128(2) 0.5528(3) 0.10435(5) 0.0432(5) Uani 1 1 d . . . . .
C3 C 0.0673(3) 0.1762(4) 0.21137(7) 0.0514(5) Uani 1 1 d . . . . .
H20 H -0.135(3) 0.734(4) -0.0249(9) 0.085(9) Uiso 1 1 d . . . . .
H21 H -0.064(4) 0.663(5) 0.0238(10) 0.116(11) Uiso 1 1 d . . . . .
O6 O -0.1798(2) 0.9536(3) 0.05337(4) 0.0659(5) Uani 1 1 d . . . . .
N3 N -0.2707(2) 1.0520(3) -0.01058(5) 0.0584(5) Uani 1 1 d . . . . .
C12 C -0.1910(3) 0.9184(4) 0.01568(6) 0.0499(5) Uani 1 1 d . . . . .
N4 N -0.1265(3) 0.7460(3) 0.00179(6) 0.0668(6) Uani 1 1 d . . . . .
C14 C -0.2885(4) 1.0198(5) -0.05455(7) 0.0848(9) Uani 1 1 d . . . . .
H19 H -0.270753 0.875696 -0.060303 0.127 Uiso 1 1 calc R U . . .
H22 H -0.208815 1.103013 -0.066543 0.127 Uiso 1 1 calc R U . . .
H18 H -0.397744 1.059360 -0.065827 0.127 Uiso 1 1 calc R U . . .
C13 C -0.3398(4) 1.2422(4) 0.00410(8) 0.0791(8) Uani 1 1 d . . . . .
H16 H -0.456740 1.244694 -0.003826 0.119 Uiso 1 1 calc R U . . .
H17 H -0.289474 1.359849 -0.007500 0.119 Uiso 1 1 calc R U . . .
H15 H -0.318774 1.247769 0.033319 0.119 Uiso 1 1 calc R U . . .
H9 H 0.426(4) 1.443(5) 0.1052(9) 0.108(10) Uiso 1 1 d . . . . .
H13 H 0.588(3) 1.188(4) 0.2253(7) 0.060(7) Uiso 1 1 d . . . . .
H14 H 0.454(3) 0.999(4) 0.2110(8) 0.078(8) Uiso 1 1 d . . . . .
H8 H 0.575(4) 1.584(6) 0.1158(10) 0.117(12) Uiso 1 1 d . . . . .
H7 H 0.615(4) 1.382(5) 0.1006(10) 0.111(12) Uiso 1 1 d . . . . .
O5 O 0.41721(19) 1.0936(3) 0.14157(4) 0.0600(4) Uani 1 1 d . . . . .
N2 N 0.5293(3) 1.1203(3) 0.20702(5) 0.0548(5) Uani 1 1 d . . . . .
N1 N 0.5671(2) 1.3775(3) 0.15938(5) 0.0491(4) Uani 1 1 d . . . . .
C9 C 0.5027(2) 1.1946(3) 0.16875(6) 0.0443(5) Uani 1 1 d . . . . .
C10 C 0.6645(3) 1.5051(4) 0.18938(7) 0.0558(6) Uani 1 1 d . . . . .
H12 H 0.599169 1.541239 0.210862 0.084 Uiso 1 1 calc R U . . .
H10 H 0.698349 1.629527 0.176544 0.084 Uiso 1 1 calc R U . . .
H11 H 0.760258 1.428978 0.200590 0.084 Uiso 1 1 calc R U . . .
C11 C 0.5434(4) 1.4474(5) 0.11721(8) 0.0626(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.302(2) . ?
O1 C8 1.223(2) . ?
O3 C7 1.308(2) . ?
O4 C7 1.216(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.406(2) . ?
C1 C8 1.488(3) . ?
C6 C5 1.385(3) . ?
C6 C7 1.496(3) . ?
C2 C3 1.365(3) . ?
C5 C4 1.380(3) . ?
C4 C3 1.373(3) . ?
O6 C12 1.256(2) . ?
N3 C12 1.336(3) . ?
N3 C13 1.452(3) . ?
N3 C14 1.455(3) . ?
C12 N4 1.330(3) . ?
O5 C9 1.254(2) . ?
N2 C9 1.344(2) . ?
N1 C9 1.338(3) . ?
N1 C10 1.452(3) . ?
N1 C11 1.453(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.70(18) . . ?
C2 C1 C8 118.39(16) . . ?
C6 C1 C8 122.83(16) . . ?
C5 C6 C1 118.92(17) . . ?
C5 C6 C7 116.47(17) . . ?
C1 C6 C7 124.45(17) . . ?
O1 C8 O2 123.01(18) . . ?
O1 C8 C1 122.30(16) . . ?
O2 C8 C1 114.67(15) . . ?
C3 C2 C1 121.5(2) . . ?
C4 C5 C6 121.0(2) . . ?
C3 C4 C5 119.7(2) . . ?
O4 C7 O3 124.16(18) . . ?
O4 C7 C6 123.25(19) . . ?
O3 C7 C6 112.30(16) . . ?
C2 C3 C4 120.1(2) . . ?
C12 N3 C13 120.31(19) . . ?
C12 N3 C14 122.8(2) . . ?
C13 N3 C14 116.9(2) . . ?
O6 C12 N4 120.2(2) . . ?
O6 C12 N3 120.1(2) . . ?
N4 C12 N3 119.71(19) . . ?
C9 N1 C10 122.59(17) . . ?
C9 N1 C11 118.63(18) . . ?
C10 N1 C11 118.7(2) . . ?
O5 C9 N1 119.45(18) . . ?
O5 C9 N2 120.4(2) . . ?
N1 C9 N2 120.18(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O5 1.05(3) 1.45(3) 2.472(2) 164(2) . yes
O5 H2 O1 1.45(3) 2.35(2) 3.4138(19) 126.3(14) . yes
O3 H1 O6 1.11(3) 1.42(3) 2.4954(19) 159(2) . yes
O3 H1 N4 1.11(3) 2.62(3) 3.557(3) 141(2) . yes
O6 H1 O4 1.42(3) 2.37(3) 3.480(2) 131.7(16) . yes
N4 H20 O4 0.88(3) 2.31(3) 3.012(2) 137(2) 3_565 yes
N4 H21 O4 0.99(3) 2.03(3) 3.020(3) 176(3) . yes
N2 H13 O1 0.85(2) 2.16(2) 2.951(2) 155(2) 2_655 yes
N2 H14 O1 1.01(3) 2.00(3) 3.008(3) 174(2) . yes

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_150K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922004'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_5_150K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.59 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_150K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.12 Ang.  
RESPONSE: The long N-H distance is characteristic of H3 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_weight         410.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0100 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0883(3)
_cell_length_b                   14.3309(6)
_cell_length_c                   18.3184(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.8585(18)
_cell_angle_gamma                90
_cell_volume                     1858.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      43.82

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7014
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34116
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         41.365
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6415
_reflns_number_gt                5337
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.67 command used to make multi_T datasets comparable: 0.67 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+0.3069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6415
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 1.133(2) 0.6671(11) 0.3975(8) 0.038(4) Uiso 1 1 d . . . . .
H8 H 1.064(2) 0.5618(10) 0.1879(7) 0.029(3) Uiso 1 1 d . . . . .
H7 H 1.105(2) 0.6925(11) 0.2694(8) 0.037(4) Uiso 1 1 d . . . . .
H5 H 1.127(2) 0.5142(10) 0.4446(8) 0.030(3) Uiso 1 1 d . . . . .
H1 H 1.103(3) 0.2772(15) 0.4635(12) 0.077(6) Uiso 1 1 d . . . . .
O3 O 0.88914(10) 0.34022(4) 0.21522(4) 0.02063(14) Uani 1 1 d . . . . .
O1 O 1.07415(11) 0.34450(5) 0.44459(4) 0.02413(15) Uani 1 1 d . . . . .
O2 O 1.14564(12) 0.28298(5) 0.33652(4) 0.02593(16) Uani 1 1 d . . . . .
O4 O 1.17248(12) 0.36521(5) 0.16985(4) 0.02758(16) Uani 1 1 d . . . . .
C4 C 1.09660(12) 0.44692(6) 0.34407(5) 0.01690(15) Uani 1 1 d . . . . .
C2 C 1.05008(13) 0.38186(6) 0.21397(4) 0.01861(16) Uani 1 1 d . . . . .
C1 C 1.10767(13) 0.34992(6) 0.37399(5) 0.01810(16) Uani 1 1 d . . . . .
C7 C 1.09972(15) 0.62846(6) 0.28789(6) 0.02514(19) Uani 1 1 d . . . . .
C3 C 1.07883(12) 0.46101(6) 0.26809(5) 0.01670(15) Uani 1 1 d . . . . .
C5 C 1.11317(13) 0.52390(6) 0.39100(5) 0.02141(17) Uani 1 1 d . . . . .
C6 C 1.11595(14) 0.61418(7) 0.36292(6) 0.02490(19) Uani 1 1 d . . . . .
C8 C 1.08015(14) 0.55209(6) 0.24079(5) 0.02174(17) Uani 1 1 d . . . . .
H20 H 1.201(2) 0.0238(10) 0.6290(8) 0.030(3) Uiso 1 1 d . . . . .
H19 H 1.113(2) 0.1806(10) 0.5968(8) 0.028(3) Uiso 1 1 d . . . . .
H18 H 1.199(2) 0.1372(11) 0.3902(8) 0.035(4) Uiso 1 1 d . . . . .
H2A H 1.341(2) -0.1599(11) 0.4458(9) 0.039(4) Uiso 1 1 d . . . . .
H17 H 1.283(2) -0.0199(11) 0.4097(8) 0.036(4) Uiso 1 1 d . . . . .
H2B H 1.372(2) -0.2343(11) 0.5063(8) 0.036(4) Uiso 1 1 d . . . . .
O5 O 1.29506(12) -0.13639(5) 0.60958(4) 0.02668(16) Uani 1 1 d . . . . .
N1 N 1.15122(11) 0.16949(5) 0.49168(4) 0.01976(15) Uani 1 1 d . . . . .
N2 N 1.34055(12) -0.17525(6) 0.49205(4) 0.02164(16) Uani 1 1 d . . . . .
C15 C 1.29745(13) -0.11479(6) 0.54417(5) 0.01824(16) Uani 1 1 d . . . . .
C20 C 1.20173(14) 0.04533(6) 0.57799(5) 0.02039(17) Uani 1 1 d . . . . .
C16 C 1.24955(12) -0.01568(6) 0.52279(5) 0.01663(15) Uani 1 1 d . . . . .
C19 C 1.15190(14) 0.13651(6) 0.56004(5) 0.02093(17) Uani 1 1 d . . . . .
C17 C 1.24891(14) 0.01812(6) 0.45159(5) 0.02025(17) Uani 1 1 d . . . . .
C18 C 1.20051(14) 0.11097(6) 0.43871(5) 0.02133(17) Uani 1 1 d . . . . .
H11 H 0.869(2) 0.0353(10) 0.0319(8) 0.032(4) Uiso 1 1 d . . . . .
H13 H 0.937(2) 0.1306(11) 0.2763(8) 0.034(4) Uiso 1 1 d . . . . .
H12 H 0.870(2) 0.1965(10) 0.0686(8) 0.030(3) Uiso 1 1 d . . . . .
H14 H 0.944(2) -0.0334(11) 0.2517(8) 0.038(4) Uiso 1 1 d . . . . .
H4A H 0.832(2) -0.2410(12) 0.1464(9) 0.043(4) Uiso 1 1 d . . . . .
H4B H 0.784(2) -0.1587(11) 0.2045(8) 0.035(4) Uiso 1 1 d . . . . .
H3 H 0.898(2) 0.2453(13) 0.1909(9) 0.051(5) Uiso 1 1 d . . . . .
O6 O 0.95098(12) -0.13747(5) 0.05307(4) 0.02819(17) Uani 1 1 d . . . . .
N4 N 0.84278(13) -0.17897(6) 0.16304(4) 0.02245(16) Uani 1 1 d . . . . .
N3 N 0.90152(11) 0.17024(5) 0.17477(4) 0.02042(15) Uani 1 1 d . . . . .
C9 C 0.89972(13) -0.11702(6) 0.11476(5) 0.01909(16) Uani 1 1 d . . . . .
C11 C 0.88268(13) 0.05220(6) 0.08408(5) 0.01897(16) Uani 1 1 d . . . . .
C10 C 0.90075(12) -0.01590(6) 0.13820(5) 0.01731(15) Uani 1 1 d . . . . .
C14 C 0.92239(15) 0.01162(6) 0.21108(5) 0.02257(18) Uani 1 1 d . . . . .
C12 C 0.88350(13) 0.14506(6) 0.10420(5) 0.02002(16) Uani 1 1 d . . . . .
C13 C 0.92155(15) 0.10596(7) 0.22785(5) 0.02410(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.2886(11) . ?
O1 C1 1.3289(10) . ?
O2 C1 1.2175(11) . ?
O4 C2 1.2381(11) . ?
C4 C5 1.4000(12) . ?
C4 C3 1.4058(11) . ?
C4 C1 1.4949(12) . ?
C2 C3 1.5136(12) . ?
C7 C6 1.3887(15) . ?
C7 C8 1.3962(13) . ?
C3 C8 1.3979(12) . ?
C5 C6 1.3928(13) . ?
O5 C15 1.2386(11) . ?
N1 C19 1.3383(11) . ?
N1 C18 1.3421(12) . ?
N2 C15 1.3359(11) . ?
C15 C16 1.5076(12) . ?
C20 C19 1.3887(12) . ?
C20 C16 1.3913(12) . ?
C16 C17 1.3910(12) . ?
C17 C18 1.3914(12) . ?
O6 C9 1.2393(11) . ?
N4 C9 1.3300(11) . ?
N3 C13 1.3418(13) . ?
N3 C12 1.3420(12) . ?
C9 C10 1.5113(12) . ?
C11 C12 1.3809(12) . ?
C11 C10 1.3924(12) . ?
C10 C14 1.3933(12) . ?
C14 C13 1.3865(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 C3 119.70(8) . . ?
C5 C4 C1 120.42(8) . . ?
C3 C4 C1 119.81(7) . . ?
O4 C2 O3 124.90(8) . . ?
O4 C2 C3 119.75(8) . . ?
O3 C2 C3 115.20(8) . . ?
O2 C1 O1 123.90(8) . . ?
O2 C1 C4 122.35(8) . . ?
O1 C1 C4 113.74(7) . . ?
C6 C7 C8 119.79(9) . . ?
C8 C3 C4 119.10(8) . . ?
C8 C3 C2 117.94(8) . . ?
C4 C3 C2 122.91(7) . . ?
C6 C5 C4 120.49(9) . . ?
C7 C6 C5 120.03(9) . . ?
C7 C8 C3 120.87(9) . . ?
C19 N1 C18 117.84(8) . . ?
O5 C15 N2 122.95(8) . . ?
O5 C15 C16 118.23(8) . . ?
N2 C15 C16 118.82(8) . . ?
C19 C20 C16 119.18(8) . . ?
C17 C16 C20 118.23(8) . . ?
C17 C16 C15 124.18(8) . . ?
C20 C16 C15 117.59(7) . . ?
N1 C19 C20 122.88(8) . . ?
C16 C17 C18 118.77(8) . . ?
N1 C18 C17 123.08(8) . . ?
C13 N3 C12 121.00(8) . . ?
O6 C9 N4 124.12(8) . . ?
O6 C9 C10 119.23(8) . . ?
N4 C9 C10 116.65(8) . . ?
C12 C11 C10 119.10(8) . . ?
C11 C10 C14 119.06(8) . . ?
C11 C10 C9 118.08(8) . . ?
C14 C10 C9 122.85(8) . . ?
C13 C14 C10 119.13(9) . . ?
N3 C12 C11 121.01(8) . . ?
N3 C13 C14 120.68(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.04(2) 1.66(2) 2.6992(10) 179(2) . yes
C18 H18 O2 0.963(15) 2.332(15) 3.1078(11) 137.1(12) . yes
N2 H2A O4 0.876(16) 2.146(16) 3.0188(11) 174.3(15) 2_745 yes
C17 H17 O4 0.981(15) 2.231(15) 3.1914(12) 165.6(13) 2_745 yes
N2 H2B O6 0.910(16) 2.092(16) 2.9963(11) 172.3(14) 4_656 yes
C11 H11 O6 0.986(15) 2.527(15) 3.0808(11) 115.4(10) 3_755 yes
N4 H4A O5 0.941(17) 1.896(17) 2.8358(10) 175.9(15) 4 yes
N4 H4B O3 0.929(16) 1.964(16) 2.8491(11) 158.5(14) 2_645 yes
N3 H3 O3 1.115(18) 1.435(18) 2.5490(10) 176.9(16) . yes
N3 H3 O4 1.115(18) 2.639(18) 3.3944(11) 124.2(11) . yes

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.053

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_4_100K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1921999'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_4_100K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      47.16 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT430_complex_4_100K_shelxl 
;
PROBLEM: Short Inter D...A Contact  O9       ..N5       .       2.86 Ang.  
RESPONSE: O9 and N5 atoms are in different layers of the crystal structure.
;
_vrf_PLAT772_complex_4_100K_shelxl 
;
PROBLEM: Suspect O-H Bond in CIF: O14      --H13       ..       1.45 Ang.  
RESPONSE: Short H...O distance is charactersitic of H13 being part of a strong 
O-H...O hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 3,5-dinitrobenzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H4 N2 O6, C3 H8 N2 O1)'
_chemical_formula_sum            'C20 H24 N8 O14'
_chemical_formula_weight         600.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.3637(2)
_cell_length_b                   6.10113(4)
_cell_length_c                   29.8215(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.5650(10)
_cell_angle_gamma                90
_cell_volume                     5155.46(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21541
_cell_measurement_theta_max      35.4191109474
_cell_measurement_theta_min      1.31609190799

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             2496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.989567627575
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.067: AIMLESS, version 0.7.3 : 15/08/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

_diffrn_radiation_wavelength     0.6889
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Photon counting pixel'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36276
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.325
_diffrn_reflns_theta_max         27.338
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6377
_reflns_number_gt                5652
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
 Methyl H-atoms are placed geometrically for C20 using HFIX 137.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+2.8185P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6377
_refine_ls_number_parameters     464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H19 H 0.4830(7) -0.145(3) 0.1677(7) 0.063(6) Uiso 1 1 d . . . . .
H20 H 0.5126(8) -0.131(4) 0.2100(8) 0.078(7) Uiso 1 1 d . . . . .
H21 H 0.5319(9) -0.083(4) 0.1657(8) 0.082(7) Uiso 1 1 d . . . . .
H3 H 0.3027(6) 0.562(3) 0.4793(5) 0.040(4) Uiso 1 1 d . . . . .
O8 O 0.39274(3) 0.64880(13) 0.24781(3) 0.02691(17) Uani 1 1 d . . . . .
O9 O 0.34076(3) 0.37449(14) 0.23835(3) 0.03110(19) Uani 1 1 d . . . . .
O12 O 0.28658(3) 1.28747(14) 0.37271(3) 0.03020(18) Uani 1 1 d . . . . .
O13 O 0.35549(3) 1.26078(14) 0.34462(3) 0.03154(19) Uani 1 1 d . . . . .
O10 O 0.19109(3) 0.41948(15) 0.31074(3) 0.03247(19) Uani 1 1 d . . . . .
O11 O 0.17691(3) 0.68561(16) 0.35608(3) 0.0352(2) Uani 1 1 d . . . . .
N6 N 0.31554(3) 1.19256(15) 0.35037(3) 0.02402(19) Uani 1 1 d . . . . .
N5 N 0.20141(3) 0.59385(16) 0.32911(3) 0.02520(19) Uani 1 1 d . . . . .
C17 C 0.33250(4) 0.88187(18) 0.30099(3) 0.0219(2) Uani 1 1 d . . . . .
C13 C 0.27557(4) 0.59069(18) 0.28972(3) 0.0215(2) Uani 1 1 d . . . . .
C12 C 0.31933(4) 0.68222(17) 0.28144(3) 0.0213(2) Uani 1 1 d . . . . .
C16 C 0.30135(4) 0.98443(17) 0.32858(3) 0.0216(2) Uani 1 1 d . . . . .
C14 C 0.24624(4) 0.69872(18) 0.31815(3) 0.0218(2) Uani 1 1 d . . . . .
C11 C 0.35217(4) 0.55423(18) 0.25328(4) 0.0236(2) Uani 1 1 d . . . . .
C15 C 0.25781(4) 0.89711(18) 0.33826(3) 0.0222(2) Uani 1 1 d . . . . .
O14 O 0.45099(3) 0.45278(14) 0.20386(3) 0.03112(19) Uani 1 1 d . . . . .
N8 N 0.49655(4) 0.16517(18) 0.18666(4) 0.0342(2) Uani 1 1 d . . . . .
N7 N 0.42244(4) 0.11100(19) 0.21527(4) 0.0342(2) Uani 1 1 d . . . . .
C18 C 0.45645(4) 0.2469(2) 0.20192(4) 0.0278(2) Uani 1 1 d . . . . .
C20 C 0.53325(5) 0.3171(3) 0.17399(5) 0.0419(3) Uani 1 1 d . . . . .
H20A H 0.521178 0.410394 0.150225 0.063 Uiso 1 1 calc R U . . .
H20B H 0.559809 0.236176 0.163940 0.063 Uiso 1 1 calc R U . . .
H20C H 0.542952 0.405031 0.199465 0.063 Uiso 1 1 calc R U . . .
C19 C 0.50530(6) -0.0698(3) 0.18311(6) 0.0416(3) Uani 1 1 d . . . . .
C8 C 0.55192(4) -0.32377(18) 0.42662(3) 0.0233(2) Uani 1 1 d . . . . .
C10 C 0.62114(4) -0.3202(2) 0.38143(4) 0.0293(2) Uani 1 1 d . . . . .
C9 C 0.59616(6) -0.6630(2) 0.41845(5) 0.0425(3) Uani 1 1 d . . . . .
N4 N 0.58946(4) -0.42922(15) 0.41155(3) 0.0263(2) Uani 1 1 d . . . . .
N3 N 0.51957(4) -0.43291(18) 0.44929(4) 0.0313(2) Uani 1 1 d . . . . .
O7 O 0.54802(3) -0.11865(13) 0.42056(3) 0.02890(18) Uani 1 1 d . . . . .
O1 O 0.47875(3) 0.10459(13) 0.43498(3) 0.02766(18) Uani 1 1 d . . . . .
O2 O 0.44701(3) -0.14611(13) 0.47977(3) 0.02806(18) Uani 1 1 d . . . . .
O6 O 0.38878(3) 0.74774(15) 0.39073(3) 0.0348(2) Uani 1 1 d . . . . .
O5 O 0.32494(3) 0.83377(15) 0.42411(3) 0.0368(2) Uani 1 1 d . . . . .
N2 N 0.35857(4) 0.71233(16) 0.41787(3) 0.0289(2) Uani 1 1 d . . . . .
O3 O 0.29690(4) 0.0320(2) 0.54651(4) 0.0513(3) Uani 1 1 d . . . . .
O4 O 0.27081(4) 0.3666(2) 0.54297(4) 0.0535(3) Uani 1 1 d . . . . .
N1 N 0.29773(4) 0.2205(2) 0.53218(4) 0.0390(3) Uani 1 1 d . . . . .
C2 C 0.40561(4) 0.18644(18) 0.46560(4) 0.0234(2) Uani 1 1 d . . . . .
C7 C 0.40148(4) 0.37735(18) 0.44004(4) 0.0239(2) Uani 1 1 d . . . . .
C1 C 0.44637(4) 0.03230(18) 0.46070(3) 0.0236(2) Uani 1 1 d . . . . .
C6 C 0.36298(4) 0.51216(18) 0.44556(4) 0.0251(2) Uani 1 1 d . . . . .
C3 C 0.37121(4) 0.13405(19) 0.49565(4) 0.0262(2) Uani 1 1 d . . . . .
C4 C 0.33371(4) 0.2760(2) 0.49999(4) 0.0294(2) Uani 1 1 d . . . . .
C5 C 0.32844(4) 0.4682(2) 0.47550(4) 0.0293(2) Uani 1 1 d . . . . .
H16 H 0.3621(5) 0.947(2) 0.2954(5) 0.033(4) Uiso 1 1 d . . . . .
H2 H 0.3737(5) 0.007(3) 0.5134(5) 0.030(4) Uiso 1 1 d . . . . .
H15 H 0.2388(5) 0.968(2) 0.3575(5) 0.031(4) Uiso 1 1 d . . . . .
H14 H 0.2665(5) 0.457(3) 0.2773(5) 0.029(3) Uiso 1 1 d . . . . .
H5 H 0.4961(7) -0.353(3) 0.4594(6) 0.048(5) Uiso 1 1 d . . . . .
H4 H 0.4241(5) 0.413(2) 0.4190(5) 0.030(3) Uiso 1 1 d . . . . .
H6 H 0.5197(7) -0.567(3) 0.4500(6) 0.055(5) Uiso 1 1 d . . . . .
H7 H 0.5836(6) -0.711(3) 0.4468(6) 0.046(4) Uiso 1 1 d . . . . .
H17 H 0.3943(6) 0.172(3) 0.2209(6) 0.045(4) Uiso 1 1 d . . . . .
H9 H 0.6315(7) -0.689(3) 0.4192(7) 0.061(5) Uiso 1 1 d . . . . .
H18 H 0.4260(7) -0.037(3) 0.2129(6) 0.054(5) Uiso 1 1 d . . . . .
H10 H 0.6157(6) -0.171(3) 0.3826(6) 0.050(5) Uiso 1 1 d . . . . .
H12 H 0.6155(8) -0.373(4) 0.3513(8) 0.073(6) Uiso 1 1 d . . . . .
H11 H 0.6554(7) -0.357(3) 0.3903(6) 0.059(5) Uiso 1 1 d . . . . .
H8 H 0.5817(7) -0.743(4) 0.3944(8) 0.073(7) Uiso 1 1 d . . . . .
H13 H 0.4142(8) 0.549(4) 0.2300(8) 0.082(7) Uiso 1 1 d . . . . .
H1 H 0.5070(8) -0.006(4) 0.4302(8) 0.082(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C11 1.3041(13) . ?
O8 H13 1.03(2) . ?
O9 C11 1.2218(14) . ?
O12 N6 1.2259(13) . ?
O13 N6 1.2263(12) . ?
O10 N5 1.2261(13) . ?
O11 N5 1.2220(13) . ?
N6 C16 1.4742(13) . ?
N5 C14 1.4732(13) . ?
C17 C16 1.3836(15) . ?
C17 C12 1.3942(15) . ?
C17 H16 0.950(15) . ?
C13 C14 1.3814(15) . ?
C13 C12 1.3931(14) . ?
C13 H14 0.926(15) . ?
C12 C11 1.5009(15) . ?
C16 C15 1.3871(15) . ?
C14 C15 1.3837(15) . ?
C15 H15 0.913(15) . ?
O14 C18 1.2671(15) . ?
O14 H13 1.45(2) . ?
N8 C18 1.3401(15) . ?
N8 C20 1.4563(17) . ?
N8 C19 1.4596(18) . ?
N7 C18 1.3458(16) . ?
N7 H17 0.905(18) . ?
N7 H18 0.91(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19 0.89(2) . ?
C19 H20 0.90(3) . ?
C19 H21 0.94(3) . ?
C8 O7 1.2685(13) . ?
C8 N4 1.3388(15) . ?
C8 N3 1.3409(15) . ?
C10 N4 1.4594(14) . ?
C10 H10 0.926(19) . ?
C10 H12 0.96(2) . ?
C10 H11 1.02(2) . ?
C9 N4 1.4525(16) . ?
C9 H7 0.977(18) . ?
C9 H9 1.02(2) . ?
C9 H8 0.94(2) . ?
N3 H5 0.890(19) . ?
N3 H6 0.82(2) . ?
O7 H1 1.39(2) . ?
O1 C1 1.2998(13) . ?
O1 H1 1.06(2) . ?
O2 C1 1.2279(13) . ?
O6 N2 1.2239(14) . ?
O5 N2 1.2286(14) . ?
N2 C6 1.4764(14) . ?
O3 N1 1.2273(17) . ?
O4 N1 1.2261(16) . ?
N1 C4 1.4716(16) . ?
C2 C3 1.3911(16) . ?
C2 C7 1.3942(15) . ?
C2 C1 1.5025(15) . ?
C7 C6 1.3827(16) . ?
C7 H4 0.943(15) . ?
C6 C5 1.3813(17) . ?
C3 C4 1.3822(17) . ?
C3 H2 0.939(15) . ?
C4 C5 1.3859(17) . ?
C5 H3 0.937(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O8 H13 110.4(13) . . ?
O12 N6 O13 124.15(10) . . ?
O12 N6 C16 118.03(9) . . ?
O13 N6 C16 117.81(9) . . ?
O11 N5 O10 124.07(10) . . ?
O11 N5 C14 117.97(9) . . ?
O10 N5 C14 117.97(9) . . ?
C16 C17 C12 118.52(10) . . ?
C16 C17 H16 120.7(9) . . ?
C12 C17 H16 120.8(9) . . ?
C14 C13 C12 118.90(10) . . ?
C14 C13 H14 120.1(9) . . ?
C12 C13 H14 121.0(9) . . ?
C13 C12 C17 120.03(10) . . ?
C13 C12 C11 118.09(9) . . ?
C17 C12 C11 121.81(9) . . ?
C17 C16 C15 123.24(10) . . ?
C17 C16 N6 118.85(9) . . ?
C15 C16 N6 117.86(9) . . ?
C13 C14 C15 123.07(10) . . ?
C13 C14 N5 118.57(10) . . ?
C15 C14 N5 118.31(9) . . ?
O9 C11 O8 124.91(10) . . ?
O9 C11 C12 120.67(10) . . ?
O8 C11 C12 114.39(9) . . ?
C14 C15 C16 116.23(10) . . ?
C14 C15 H15 123.5(10) . . ?
C16 C15 H15 120.3(9) . . ?
C18 O14 H13 121.1(9) . . ?
C18 N8 C20 118.58(11) . . ?
C18 N8 C19 122.67(12) . . ?
C20 N8 C19 118.73(11) . . ?
C18 N7 H17 116.8(11) . . ?
C18 N7 H18 120.4(12) . . ?
H17 N7 H18 121.7(16) . . ?
O14 C18 N8 119.46(11) . . ?
O14 C18 N7 120.43(11) . . ?
N8 C18 N7 120.11(11) . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C19 H19 115.0(13) . . ?
N8 C19 H20 112.1(15) . . ?
H19 C19 H20 112(2) . . ?
N8 C19 H21 105.5(15) . . ?
H19 C19 H21 103.9(19) . . ?
H20 C19 H21 107(2) . . ?
O7 C8 N4 119.47(10) . . ?
O7 C8 N3 120.29(11) . . ?
N4 C8 N3 120.20(10) . . ?
N4 C10 H10 108.5(12) . . ?
N4 C10 H12 109.9(13) . . ?
H10 C10 H12 110.2(17) . . ?
N4 C10 H11 110.2(11) . . ?
H10 C10 H11 111.4(16) . . ?
H12 C10 H11 106.6(17) . . ?
N4 C9 H7 111.5(10) . . ?
N4 C9 H9 106.3(11) . . ?
H7 C9 H9 109.4(15) . . ?
N4 C9 H8 110.4(14) . . ?
H7 C9 H8 109.8(17) . . ?
H9 C9 H8 109.3(17) . . ?
C8 N4 C9 121.70(10) . . ?
C8 N4 C10 120.56(10) . . ?
C9 N4 C10 117.05(10) . . ?
C8 N3 H5 116.0(12) . . ?
C8 N3 H6 120.4(13) . . ?
H5 N3 H6 122.8(17) . . ?
C8 O7 H1 121.8(10) . . ?
C1 O1 H1 115.0(13) . . ?
O6 N2 O5 124.40(10) . . ?
O6 N2 C6 118.14(10) . . ?
O5 N2 C6 117.45(10) . . ?
O4 N1 O3 124.62(12) . . ?
O4 N1 C4 117.51(12) . . ?
O3 N1 C4 117.87(11) . . ?
C3 C2 C7 119.99(10) . . ?
C3 C2 C1 118.94(10) . . ?
C7 C2 C1 121.06(10) . . ?
C6 C7 C2 118.65(10) . . ?
C6 C7 H4 120.3(9) . . ?
C2 C7 H4 121.0(9) . . ?
O2 C1 O1 125.31(10) . . ?
O2 C1 C2 120.34(10) . . ?
O1 C1 C2 114.34(9) . . ?
C5 C6 C7 123.24(11) . . ?
C5 C6 N2 118.53(10) . . ?
C7 C6 N2 118.23(10) . . ?
C4 C3 C2 118.77(11) . . ?
C4 C3 H2 120.1(9) . . ?
C2 C3 H2 121.1(9) . . ?
C3 C4 C5 123.10(11) . . ?
C3 C4 N1 118.42(11) . . ?
C5 C4 N1 118.48(11) . . ?
C6 C5 C4 116.24(11) . . ?
C6 C5 H3 122.6(10) . . ?
C4 C5 H3 121.2(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20B O13 0.96 2.43 3.2468(15) 142.5 2_645 yes
N3 H5 O2 0.890(19) 1.99(2) 2.8795(14) 173.9(17) . yes
N3 H6 O1 0.82(2) 2.35(2) 3.0726(13) 147.8(18) 1_545 yes
C9 H7 O2 0.977(18) 2.545(18) 3.5213(16) 177.1(14) 5_646 yes
N7 H17 O9 0.905(18) 2.041(18) 2.9272(14) 166.0(16) . yes
C9 H9 O11 1.02(2) 2.45(2) 3.1526(16) 125.8(15) 3_535 yes
N7 H18 O8 0.91(2) 2.393(19) 3.1108(14) 135.5(15) 1_545 yes
C9 H8 O7 0.94(2) 2.62(2) 3.0988(17) 112.1(16) 1_545 yes
O8 H13 O14 1.03(2) 1.45(2) 2.4640(11) 167(2) . yes
O14 H13 O9 1.45(2) 2.36(2) 3.3688(12) 122.2(13) . yes
O7 H1 O2 1.39(2) 2.46(2) 3.4363(12) 124.0(14) . yes
O1 H1 N3 1.06(2) 2.69(2) 3.4974(14) 132.9(16) . yes
O1 H1 O7 1.06(2) 1.39(2) 2.4445(12) 170(2) . yes

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 4 degreesC'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_4_300K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922001'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_4_300K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.17 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT230_complex_4_300K_shelxl 
;
PROBLEM: Hirshfeld Test Diff for    O6       --N2       .        8.0 s.u.  
RESPONSE: Atoms O6 and N2 are different atom types.
;
_vrf_PLAT414_complex_4_300K_shelxl 
;
PROBLEM: Short Intra D-H..H-X       H3B      ..H9A              1.85 Ang.  
RESPONSE: H3B and H9A are in the same N,N-dimethylurea molecule and are
geometrically close being 'cis' to one another.
;
_vrf_PLAT776_complex_4_300K_shelxl 
;
PROBLEM: Suspect D-H Dist in CIF: O14      --H13       ..       1.55 Ang.  
RESPONSE: .Short H...O distance is charactersitic of H being part of a strong 
O-H...O hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 3,5-dinitrobenzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H4 N2 O6, C3 H8 N2 O1)'
_chemical_formula_sum            'C20 H24 N8 O14'
_chemical_formula_weight         600.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.61360(19)
_cell_length_b                   6.10500(4)
_cell_length_c                   30.8489(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.1270(6)
_cell_angle_gamma                90
_cell_volume                     5385.16(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    16828
_cell_measurement_theta_max      31.4837922064
_cell_measurement_theta_min      1.27358331844

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             2496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.995951233724
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.067: AIMLESS, version 0.7.3 : 15/08/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

_diffrn_radiation_wavelength     0.6889
_diffrn_ambient_temperature      300(2)
_diffrn_detector                 'Photon counting pixel'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39335
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.280
_diffrn_reflns_theta_max         27.339
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6662
_reflns_number_gt                4826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
 Methyl H-atoms are placed geometrically for C19, C20 using HFIX 137.
 Amine H-atoms are place geometrically for N3 and N7 using HFIX 93.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0882P)²+0.6644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6662
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1677
_refine_ls_wR_factor_gt          0.1564
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 0.3062(9) 0.536(4) 0.4801(8) 0.112(8) Uiso 1 1 d . . . . .
O8 O 0.39110(4) 0.6587(2) 0.24764(4) 0.0791(3) Uani 1 1 d . . . . .
O9 O 0.34069(4) 0.3831(2) 0.23867(5) 0.0922(4) Uani 1 1 d . . . . .
O12 O 0.28827(5) 1.2782(2) 0.37252(4) 0.0927(4) Uani 1 1 d . . . . .
O13 O 0.35550(5) 1.2525(2) 0.34504(5) 0.0968(4) Uani 1 1 d . . . . .
O10 O 0.19218(5) 0.4223(3) 0.31003(5) 0.0975(4) Uani 1 1 d . . . . .
O11 O 0.17859(5) 0.6808(3) 0.35439(5) 0.1048(5) Uani 1 1 d . . . . .
N6 N 0.31649(5) 1.1848(2) 0.35043(4) 0.0708(3) Uani 1 1 d . . . . .
N5 N 0.20269(4) 0.5918(2) 0.32818(4) 0.0727(3) Uani 1 1 d . . . . .
C17 C 0.33224(5) 0.8806(2) 0.30121(5) 0.0601(3) Uani 1 1 d . . . . .
C13 C 0.27598(5) 0.5926(2) 0.28987(4) 0.0587(3) Uani 1 1 d . . . . .
C12 C 0.31924(4) 0.6844(2) 0.28161(4) 0.0581(3) Uani 1 1 d . . . . .
C16 C 0.30195(5) 0.9801(2) 0.32870(4) 0.0591(3) Uani 1 1 d . . . . .
C14 C 0.24728(4) 0.6969(2) 0.31791(4) 0.0593(3) Uani 1 1 d . . . . .
C11 C 0.35133(5) 0.5603(3) 0.25336(5) 0.0657(4) Uani 1 1 d . . . . .
C15 C 0.25902(5) 0.8915(2) 0.33794(5) 0.0612(3) Uani 1 1 d . . . . .
O14 O 0.45027(4) 0.4679(2) 0.20445(5) 0.0935(4) Uani 1 1 d . . . . .
N8 N 0.49713(5) 0.1910(3) 0.18709(6) 0.0908(5) Uani 1 1 d . . . . .
N7 N 0.42370(6) 0.1244(3) 0.21317(7) 0.1050(5) Uani 1 1 d . . . . .
H7A H 0.397734 0.172966 0.222546 0.126 Uiso 1 1 calc R U . . .
H7B H 0.428310 -0.014395 0.211211 0.126 Uiso 1 1 calc R U . . .
C18 C 0.45692(6) 0.2647(3) 0.20162(6) 0.0791(4) Uani 1 1 d . . . . .
C20 C 0.53225(8) 0.3503(5) 0.17489(9) 0.1231(9) Uani 1 1 d . . . . .
H20A H 0.528494 0.381923 0.144472 0.185 Uiso 1 1 calc R U . . .
H20B H 0.562903 0.291374 0.180929 0.185 Uiso 1 1 calc R U . . .
H20C H 0.528465 0.482573 0.191222 0.185 Uiso 1 1 calc R U . . .
C19 C 0.50765(9) -0.0410(4) 0.18330(9) 0.1203(8) Uani 1 1 d . . . . .
H19A H 0.510206 -0.105196 0.211693 0.180 Uiso 1 1 calc R U . . .
H19B H 0.536664 -0.058970 0.169046 0.180 Uiso 1 1 calc R U . . .
H19C H 0.483026 -0.112048 0.166645 0.180 Uiso 1 1 calc R U . . .
C8 C 0.55212(5) -0.3271(2) 0.42658(5) 0.0643(3) Uani 1 1 d . . . . .
C10 C 0.61952(7) -0.3136(3) 0.38151(6) 0.0862(5) Uani 1 1 d . . . . .
H10A H 0.611876 -0.356904 0.352178 0.129 Uiso 1 1 calc R U . . .
H10B H 0.651510 -0.350401 0.388631 0.129 Uiso 1 1 calc R U . . .
H10C H 0.615260 -0.158358 0.384368 0.129 Uiso 1 1 calc R U . . .
C9 C 0.59843(10) -0.6581(3) 0.41840(9) 0.1191(9) Uani 1 1 d . . . . .
H9A H 0.583493 -0.704353 0.444207 0.179 Uiso 1 1 calc R U . . .
H9B H 0.631559 -0.680720 0.421870 0.179 Uiso 1 1 calc R U . . .
H9C H 0.586439 -0.741915 0.394112 0.179 Uiso 1 1 calc R U . . .
N4 N 0.58906(5) -0.4275(2) 0.41084(4) 0.0736(3) Uani 1 1 d . . . . .
N3 N 0.52275(6) -0.4370(2) 0.45117(5) 0.0875(4) Uani 1 1 d . . . . .
H3A H 0.499471 -0.370596 0.462142 0.105 Uiso 1 1 calc R U . . .
H3B H 0.527100 -0.574352 0.456044 0.105 Uiso 1 1 calc R U . . .
O7 O 0.54582(4) -0.12743(18) 0.41948(4) 0.0821(3) Uani 1 1 d . . . . .
O1 O 0.47686(5) 0.09544(19) 0.43516(4) 0.0816(3) Uani 1 1 d . . . . .
O2 O 0.44728(4) -0.15078(18) 0.48020(4) 0.0790(3) Uani 1 1 d . . . . .
O6 O 0.38751(6) 0.7306(2) 0.39189(5) 0.1053(5) Uani 1 1 d . . . . .
O5 O 0.32410(7) 0.8129(3) 0.42355(6) 0.1163(5) Uani 1 1 d . . . . .
N2 N 0.35787(7) 0.6954(2) 0.41798(5) 0.0870(4) Uani 1 1 d . . . . .
O3 O 0.29852(7) 0.0293(4) 0.54565(8) 0.1538(8) Uani 1 1 d . . . . .
O4 O 0.27332(8) 0.3604(5) 0.54230(7) 0.1610(9) Uani 1 1 d . . . . .
N1 N 0.29939(7) 0.2160(4) 0.53131(7) 0.1154(6) Uani 1 1 d . . . . .
C2 C 0.40523(5) 0.1768(2) 0.46584(5) 0.0647(3) Uani 1 1 d . . . . .
C7 C 0.40043(6) 0.3651(2) 0.44050(5) 0.0677(4) Uani 1 1 d . . . . .
C1 C 0.44551(5) 0.0249(2) 0.46117(5) 0.0665(4) Uani 1 1 d . . . . .
C6 C 0.36267(6) 0.4985(2) 0.44583(5) 0.0712(4) Uani 1 1 d . . . . .
C3 C 0.37170(6) 0.1285(3) 0.49546(5) 0.0734(4) Uani 1 1 d . . . . .
C4 C 0.33467(6) 0.2678(3) 0.49973(6) 0.0836(5) Uani 1 1 d . . . . .
C5 C 0.32922(7) 0.4566(3) 0.47532(6) 0.0833(5) Uani 1 1 d . . . . .
H16 H 0.3596(6) 0.945(3) 0.2954(5) 0.073(5) Uiso 1 1 d . . . . .
H2 H 0.3725(6) -0.002(3) 0.5132(6) 0.084(5) Uiso 1 1 d . . . . .
H15 H 0.2407(6) 0.966(3) 0.3556(6) 0.080(5) Uiso 1 1 d . . . . .
H14 H 0.2665(5) 0.458(3) 0.2770(5) 0.062(4) Uiso 1 1 d . . . . .
H4 H 0.4225(7) 0.385(3) 0.4203(6) 0.089(6) Uiso 1 1 d . . . . .
H13 H 0.4124(10) 0.578(4) 0.2315(9) 0.134(9) Uiso 1 1 d . . . . .
H1 H 0.5008(9) -0.011(4) 0.4289(8) 0.118(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C11 1.3045(18) . ?
O8 H13 0.94(3) . ?
O9 C11 1.2076(19) . ?
O12 N6 1.2172(19) . ?
O13 N6 1.2075(18) . ?
O10 N5 1.2095(19) . ?
O11 N5 1.2106(19) . ?
N6 C16 1.4712(19) . ?
N5 C14 1.4729(18) . ?
C17 C16 1.376(2) . ?
C17 C12 1.386(2) . ?
C17 H16 0.901(18) . ?
C13 C14 1.371(2) . ?
C13 C12 1.3913(19) . ?
C13 H14 0.947(17) . ?
C12 C11 1.495(2) . ?
C16 C15 1.381(2) . ?
C14 C15 1.375(2) . ?
C15 H15 0.896(19) . ?
O14 C18 1.258(2) . ?
N8 C18 1.329(2) . ?
N8 C19 1.454(3) . ?
N8 C20 1.458(3) . ?
N7 C18 1.338(2) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C8 O7 1.2502(18) . ?
C8 N4 1.330(2) . ?
C8 N3 1.3338(19) . ?
C10 N4 1.456(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 N4 1.450(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
O1 C1 1.2988(19) . ?
O1 H1 0.97(3) . ?
O2 C1 1.2228(18) . ?
O6 N2 1.210(2) . ?
O5 N2 1.221(2) . ?
N2 C6 1.481(2) . ?
O3 N1 1.223(3) . ?
O4 N1 1.212(3) . ?
N1 C4 1.463(3) . ?
C2 C3 1.381(2) . ?
C2 C7 1.394(2) . ?
C2 C1 1.491(2) . ?
C7 C6 1.368(2) . ?
C7 H4 0.91(2) . ?
C6 C5 1.369(3) . ?
C3 C4 1.369(3) . ?
C3 H2 0.97(2) . ?
C4 C5 1.382(3) . ?
C5 H3 0.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O8 H13 114.7(17) . . ?
O13 N6 O12 123.56(14) . . ?
O13 N6 C16 118.36(14) . . ?
O12 N6 C16 118.07(13) . . ?
O10 N5 O11 123.70(14) . . ?
O10 N5 C14 118.41(13) . . ?
O11 N5 C14 117.89(14) . . ?
C16 C17 C12 119.02(13) . . ?
C16 C17 H16 120.1(11) . . ?
C12 C17 H16 120.8(11) . . ?
C14 C13 C12 119.08(13) . . ?
C14 C13 H14 120.0(9) . . ?
C12 C13 H14 121.0(9) . . ?
C17 C12 C13 119.64(13) . . ?
C17 C12 C11 122.11(12) . . ?
C13 C12 C11 118.18(13) . . ?
C17 C16 C15 122.64(13) . . ?
C17 C16 N6 118.80(13) . . ?
C15 C16 N6 118.52(13) . . ?
C13 C14 C15 122.87(13) . . ?
C13 C14 N5 118.49(13) . . ?
C15 C14 N5 118.60(13) . . ?
O9 C11 O8 124.81(14) . . ?
O9 C11 C12 121.41(13) . . ?
O8 C11 C12 113.76(13) . . ?
C14 C15 C16 116.74(13) . . ?
C14 C15 H15 125.0(12) . . ?
C16 C15 H15 118.2(12) . . ?
C18 N8 C19 122.79(19) . . ?
C18 N8 C20 118.36(18) . . ?
C19 N8 C20 118.85(18) . . ?
C18 N7 H7A 120.0 . . ?
C18 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
O14 C18 N8 119.48(17) . . ?
O14 C18 N7 120.14(17) . . ?
N8 C18 N7 120.38(19) . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O7 C8 N4 119.81(13) . . ?
O7 C8 N3 120.04(15) . . ?
N4 C8 N3 120.11(14) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 N4 C9 122.27(14) . . ?
C8 N4 C10 120.59(14) . . ?
C9 N4 C10 116.88(15) . . ?
C8 N3 H3A 120.0 . . ?
C8 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C1 O1 H1 114.3(14) . . ?
O6 N2 O5 124.55(17) . . ?
O6 N2 C6 118.56(17) . . ?
O5 N2 C6 116.9(2) . . ?
O4 N1 O3 123.8(2) . . ?
O4 N1 C4 118.4(2) . . ?
O3 N1 C4 117.8(2) . . ?
C3 C2 C7 119.40(15) . . ?
C3 C2 C1 119.31(14) . . ?
C7 C2 C1 121.28(14) . . ?
C6 C7 C2 119.03(16) . . ?
C6 C7 H4 124.9(13) . . ?
C2 C7 H4 116.0(13) . . ?
O2 C1 O1 124.77(15) . . ?
O2 C1 C2 121.17(14) . . ?
O1 C1 C2 114.05(13) . . ?
C7 C6 C5 122.93(16) . . ?
C7 C6 N2 118.04(17) . . ?
C5 C6 N2 119.03(17) . . ?
C4 C3 C2 119.33(16) . . ?
C4 C3 H2 117.4(11) . . ?
C2 C3 H2 123.3(11) . . ?
C3 C4 C5 122.54(18) . . ?
C3 C4 N1 119.02(18) . . ?
C5 C4 N1 118.44(19) . . ?
C6 C5 C4 116.76(18) . . ?
C6 C5 H3 125.8(17) . . ?
C4 C5 H3 117.4(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20B O13 0.96 2.51 3.346(3) 145.9 2_645 yes
C10 H10A O14 0.96 2.67 3.522(3) 148.2 2_645 yes
C9 H9A O2 0.96 2.67 3.628(2) 172.7 5_646 yes
C9 H9B O11 0.96 2.66 3.235(3) 119.0 3_535 yes
N3 H3A O2 0.86 2.10 2.9434(19) 167.3 . yes
N3 H3B O1 0.86 2.55 3.1729(19) 130.6 1_545 yes
N7 H7A O9 0.86 2.15 2.982(2) 163.1 . yes
N7 H7B O8 0.86 2.54 3.187(2) 132.4 1_545 yes
O8 H13 O14 0.94(3) 1.55(3) 2.4832(16) 174(3) . yes
O14 H13 O9 1.55(3) 2.39(3) 3.3853(17) 117.0(14) . yes
O7 H1 O2 1.51(3) 2.40(2) 3.4455(17) 121.9(14) . yes
O1 H1 N3 0.97(3) 2.76(3) 3.5337(19) 137.6(18) . yes
O1 H1 O7 0.97(3) 1.51(3) 2.4596(18) 166(2) . yes

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.032


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 4 degreesC'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_350K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922005'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_5_350K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.91 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_350K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.19 Ang.  
RESPONSE: The long N-H distance is characteristic of H3 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_weight         410.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0100 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2897(3)
_cell_length_b                   14.3165(6)
_cell_length_c                   18.4105(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.410(2)
_cell_angle_gamma                90
_cell_volume                     1919.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    350
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      43.79

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.141
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      350
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35430
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         41.361
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6608
_reflns_number_gt                4120
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.67 command used to make multi_T datasets comparable: 0.67 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+0.2074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6608
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1299
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 1.126(3) 0.6680(14) 0.3960(10) 0.077(6) Uiso 1 1 d . . . . .
H8 H 1.057(3) 0.5631(14) 0.1899(10) 0.078(6) Uiso 1 1 d . . . . .
H7 H 1.097(3) 0.6925(15) 0.2699(11) 0.081(6) Uiso 1 1 d . . . . .
H5 H 1.126(2) 0.5138(12) 0.4433(9) 0.064(5) Uiso 1 1 d . . . . .
H1 H 1.112(3) 0.2787(17) 0.4606(12) 0.106(7) Uiso 1 1 d . . . . .
O3 O 0.90030(16) 0.33990(7) 0.21707(5) 0.0557(3) Uani 1 1 d . . . . .
O1 O 1.08239(18) 0.34590(8) 0.44380(5) 0.0638(3) Uani 1 1 d . . . . .
O2 O 1.15074(19) 0.28470(8) 0.33710(5) 0.0701(3) Uani 1 1 d . . . . .
O4 O 1.17261(19) 0.36675(9) 0.17087(6) 0.0750(4) Uani 1 1 d . . . . .
C4 C 1.09882(18) 0.44794(8) 0.34377(7) 0.0434(3) Uani 1 1 d . . . . .
C2 C 1.0549(2) 0.38268(9) 0.21502(7) 0.0490(3) Uani 1 1 d . . . . .
C1 C 1.1135(2) 0.35131(9) 0.37373(7) 0.0468(3) Uani 1 1 d . . . . .
C7 C 1.0951(3) 0.62888(10) 0.28821(11) 0.0662(4) Uani 1 1 d . . . . .
C3 C 1.07973(19) 0.46185(8) 0.26864(7) 0.0438(3) Uani 1 1 d . . . . .
C5 C 1.1134(2) 0.52518(10) 0.39000(8) 0.0553(3) Uani 1 1 d . . . . .
C6 C 1.1125(2) 0.61480(11) 0.36192(11) 0.0648(4) Uani 1 1 d . . . . .
C8 C 1.0776(2) 0.55270(10) 0.24166(9) 0.0569(4) Uani 1 1 d . . . . .
H20 H 1.196(2) 0.0230(13) 0.6273(10) 0.069(5) Uiso 1 1 d . . . . .
H19 H 1.119(2) 0.1799(13) 0.5964(9) 0.068(5) Uiso 1 1 d . . . . .
H18 H 1.208(3) 0.1380(13) 0.3920(10) 0.076(5) Uiso 1 1 d . . . . .
H2A H 1.337(3) -0.1569(14) 0.4482(11) 0.075(6) Uiso 1 1 d . . . . .
H17 H 1.286(3) -0.0180(13) 0.4113(10) 0.076(5) Uiso 1 1 d . . . . .
H2B H 1.365(3) -0.2316(15) 0.5073(11) 0.081(6) Uiso 1 1 d . . . . .
O5 O 1.2899(2) -0.13587(7) 0.60889(6) 0.0720(4) Uani 1 1 d . . . . .
N1 N 1.15597(18) 0.17016(8) 0.49248(6) 0.0523(3) Uani 1 1 d . . . . .
N2 N 1.3342(2) -0.17404(9) 0.49264(8) 0.0580(3) Uani 1 1 d . . . . .
C15 C 1.2927(2) -0.11416(9) 0.54440(7) 0.0482(3) Uani 1 1 d . . . . .
C20 C 1.1988(2) 0.04589(9) 0.57736(7) 0.0537(3) Uani 1 1 d . . . . .
C16 C 1.24728(18) -0.01479(8) 0.52331(7) 0.0428(3) Uani 1 1 d . . . . .
C19 C 1.1527(2) 0.13686(10) 0.55964(8) 0.0563(4) Uani 1 1 d . . . . .
C17 C 1.2509(2) 0.01923(10) 0.45330(8) 0.0541(3) Uani 1 1 d . . . . .
C18 C 1.2053(2) 0.11174(10) 0.44050(8) 0.0576(4) Uani 1 1 d . . . . .
H11 H 0.869(2) 0.0347(12) 0.0333(10) 0.068(5) Uiso 1 1 d . . . . .
H13 H 0.944(3) 0.1286(15) 0.2742(11) 0.083(6) Uiso 1 1 d . . . . .
H12 H 0.876(2) 0.1963(13) 0.0711(9) 0.066(5) Uiso 1 1 d . . . . .
H14 H 0.937(3) -0.0329(14) 0.2495(11) 0.080(6) Uiso 1 1 d . . . . .
H4A H 0.828(3) -0.2410(15) 0.1456(10) 0.076(5) Uiso 1 1 d . . . . .
H4B H 0.785(3) -0.1584(13) 0.2049(10) 0.074(6) Uiso 1 1 d . . . . .
H3 H 0.910(3) 0.2499(17) 0.1928(12) 0.101(7) Uiso 1 1 d . . . . .
O6 O 0.9396(2) -0.13704(8) 0.05284(6) 0.0757(4) Uani 1 1 d . . . . .
N4 N 0.8377(2) -0.17823(8) 0.16187(7) 0.0603(3) Uani 1 1 d . . . . .
N3 N 0.90707(18) 0.17007(8) 0.17488(7) 0.0536(3) Uani 1 1 d . . . . .
C9 C 0.8930(2) -0.11654(9) 0.11413(7) 0.0493(3) Uani 1 1 d . . . . .
C11 C 0.8837(2) 0.05274(9) 0.08492(7) 0.0488(3) Uani 1 1 d . . . . .
C10 C 0.89798(18) -0.01557(8) 0.13792(7) 0.0440(3) Uani 1 1 d . . . . .
C14 C 0.9203(3) 0.01130(10) 0.20982(8) 0.0604(4) Uani 1 1 d . . . . .
C12 C 0.8891(2) 0.14502(9) 0.10539(8) 0.0520(3) Uani 1 1 d . . . . .
C13 C 0.9235(3) 0.10538(11) 0.22655(9) 0.0644(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.2843(18) . ?
O1 C1 1.3215(16) . ?
O2 C1 1.2056(16) . ?
O4 C2 1.2281(17) . ?
C4 C5 1.3968(18) . ?
C4 C3 1.3986(17) . ?
C4 C1 1.4914(17) . ?
C2 C3 1.5090(17) . ?
C7 C6 1.372(3) . ?
C7 C8 1.390(2) . ?
C3 C8 1.3923(17) . ?
C5 C6 1.383(2) . ?
O5 C15 1.2284(16) . ?
N1 C19 1.3264(18) . ?
N1 C18 1.3317(19) . ?
N2 C15 1.3261(18) . ?
C15 C16 1.5077(17) . ?
C20 C16 1.3782(18) . ?
C20 C19 1.3807(19) . ?
C16 C17 1.3792(18) . ?
C17 C18 1.3834(19) . ?
O6 C9 1.2275(16) . ?
N4 C9 1.3211(18) . ?
N3 C13 1.329(2) . ?
N3 C12 1.3299(18) . ?
C9 C10 1.5103(17) . ?
C11 C12 1.3739(18) . ?
C11 C10 1.3823(18) . ?
C10 C14 1.3815(19) . ?
C14 C13 1.382(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 C3 119.46(12) . . ?
C5 C4 C1 120.43(12) . . ?
C3 C4 C1 120.03(11) . . ?
O4 C2 O3 124.71(13) . . ?
O4 C2 C3 120.29(14) . . ?
O3 C2 C3 114.86(12) . . ?
O2 C1 O1 123.48(12) . . ?
O2 C1 C4 122.77(12) . . ?
O1 C1 C4 113.76(11) . . ?
C6 C7 C8 119.79(14) . . ?
C8 C3 C4 119.02(12) . . ?
C8 C3 C2 117.97(12) . . ?
C4 C3 C2 122.98(11) . . ?
C6 C5 C4 120.50(14) . . ?
C7 C6 C5 120.31(14) . . ?
C7 C8 C3 120.91(15) . . ?
C19 N1 C18 117.40(12) . . ?
O5 C15 N2 122.99(13) . . ?
O5 C15 C16 118.38(12) . . ?
N2 C15 C16 118.63(12) . . ?
C16 C20 C19 119.43(13) . . ?
C20 C16 C17 117.89(12) . . ?
C20 C16 C15 117.97(11) . . ?
C17 C16 C15 124.14(12) . . ?
N1 C19 C20 123.06(13) . . ?
C16 C17 C18 118.90(13) . . ?
N1 C18 C17 123.31(13) . . ?
C13 N3 C12 120.18(12) . . ?
O6 C9 N4 123.76(13) . . ?
O6 C9 C10 119.42(12) . . ?
N4 C9 C10 116.82(12) . . ?
C12 C11 C10 119.10(13) . . ?
C14 C10 C11 118.79(12) . . ?
C14 C10 C9 123.01(12) . . ?
C11 C10 C9 118.18(11) . . ?
C10 C14 C13 119.03(14) . . ?
N3 C12 C11 121.58(13) . . ?
N3 C13 C14 121.30(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.03(2) 1.69(2) 2.7166(15) 177(2) . yes
C18 H18 O2 0.970(19) 2.359(19) 3.1384(17) 136.9(15) . yes
N2 H2A O4 0.85(2) 2.22(2) 3.0646(18) 171.4(18) 2_745 yes
C17 H17 O4 0.981(19) 2.268(19) 3.2263(19) 165.4(16) 2_745 yes
N2 H2B O6 0.89(2) 2.12(2) 3.0105(17) 174.2(18) 4_656 yes
C11 H11 O6 0.987(17) 2.609(18) 3.1343(17) 113.4(12) 3_755 yes
N4 H4A O5 0.95(2) 1.90(2) 2.8509(16) 175.4(17) 4 yes
N4 H4B O3 0.94(2) 2.02(2) 2.8929(17) 155.2(17) 2_645 yes
N3 H3 O3 1.19(2) 1.37(2) 2.5536(14) 175(2) . yes
N3 H3 O4 1.19(2) 2.58(2) 3.4195(17) 125.8(14) . yes

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.038

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_100K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922002'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_5_100K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.44 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_100K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.10 Ang.  
RESPONSE: The long N-H distance is characteristic of H3 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_weight         410.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0100 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.0539(3)
_cell_length_b                   14.3314(6)
_cell_length_c                   18.3058(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.9626(19)
_cell_angle_gamma                90
_cell_volume                     1848.10(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      43.78

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6859
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33784
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         41.364
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6362
_reflns_number_gt                5347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.67 command used to make multi_T datasets comparable: 0.67 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0656P)²+0.3727P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6362
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 1.135(2) 0.6675(10) 0.3981(8) 0.027(4) Uiso 1 1 d . . . . .
H8 H 1.065(2) 0.5623(10) 0.1879(8) 0.025(4) Uiso 1 1 d . . . . .
H7 H 1.106(2) 0.6928(11) 0.2696(8) 0.028(4) Uiso 1 1 d . . . . .
H5 H 1.125(2) 0.5133(10) 0.4443(8) 0.024(3) Uiso 1 1 d . . . . .
H1 H 1.102(3) 0.2771(15) 0.4631(12) 0.068(6) Uiso 1 1 d . . . . .
O3 O 0.88759(10) 0.34037(4) 0.21498(3) 0.01468(13) Uani 1 1 d . . . . .
O1 O 1.07257(11) 0.34434(5) 0.44471(3) 0.01708(14) Uani 1 1 d . . . . .
O2 O 1.14487(11) 0.28280(5) 0.33647(4) 0.01826(14) Uani 1 1 d . . . . .
O4 O 1.17285(11) 0.36486(5) 0.16972(4) 0.01945(14) Uani 1 1 d . . . . .
C4 C 1.09629(12) 0.44687(6) 0.34408(5) 0.01233(15) Uani 1 1 d . . . . .
C2 C 1.04997(13) 0.38179(6) 0.21385(4) 0.01351(15) Uani 1 1 d . . . . .
C1 C 1.10686(12) 0.34984(6) 0.37399(4) 0.01283(15) Uani 1 1 d . . . . .
C7 C 1.10122(14) 0.62854(6) 0.28778(5) 0.01784(17) Uani 1 1 d . . . . .
C3 C 1.07907(12) 0.46105(6) 0.26802(4) 0.01224(15) Uani 1 1 d . . . . .
C5 C 1.11315(13) 0.52389(6) 0.39105(5) 0.01553(16) Uani 1 1 d . . . . .
C6 C 1.11677(14) 0.61424(6) 0.36300(5) 0.01769(17) Uani 1 1 d . . . . .
C8 C 1.08117(13) 0.55205(6) 0.24062(5) 0.01545(16) Uani 1 1 d . . . . .
H20 H 1.203(2) 0.0238(10) 0.6288(8) 0.023(3) Uiso 1 1 d . . . . .
H19 H 1.1120(19) 0.1799(9) 0.5972(7) 0.019(3) Uiso 1 1 d . . . . .
H18 H 1.197(2) 0.1375(10) 0.3894(8) 0.024(4) Uiso 1 1 d . . . . .
H2A H 1.344(2) -0.1597(11) 0.4454(9) 0.031(4) Uiso 1 1 d . . . . .
H17 H 1.281(2) -0.0210(10) 0.4092(8) 0.025(3) Uiso 1 1 d . . . . .
H2B H 1.376(2) -0.2334(11) 0.5066(8) 0.031(4) Uiso 1 1 d . . . . .
O5 O 1.29637(11) -0.13639(5) 0.60975(4) 0.01874(14) Uani 1 1 d . . . . .
N1 N 1.15017(11) 0.16946(5) 0.49148(4) 0.01417(14) Uani 1 1 d . . . . .
N2 N 1.34191(12) -0.17538(5) 0.49205(4) 0.01548(15) Uani 1 1 d . . . . .
C15 C 1.29847(12) -0.11489(6) 0.54421(5) 0.01312(15) Uani 1 1 d . . . . .
C20 C 1.20247(13) 0.04533(6) 0.57808(5) 0.01460(16) Uani 1 1 d . . . . .
C16 C 1.24999(12) -0.01569(6) 0.52271(4) 0.01203(15) Uani 1 1 d . . . . .
C19 C 1.15171(13) 0.13656(6) 0.56008(5) 0.01470(16) Uani 1 1 d . . . . .
C17 C 1.24833(13) 0.01798(6) 0.45127(5) 0.01424(16) Uani 1 1 d . . . . .
C18 C 1.19944(13) 0.11084(6) 0.43843(5) 0.01517(16) Uani 1 1 d . . . . .
H11 H 0.871(2) 0.0347(10) 0.0318(8) 0.027(4) Uiso 1 1 d . . . . .
H13 H 0.935(2) 0.1308(10) 0.2762(8) 0.022(3) Uiso 1 1 d . . . . .
H12 H 0.8694(19) 0.1948(10) 0.0682(7) 0.018(3) Uiso 1 1 d . . . . .
H14 H 0.945(2) -0.0331(11) 0.2515(8) 0.028(4) Uiso 1 1 d . . . . .
H4A H 0.835(2) -0.2417(12) 0.1474(8) 0.034(4) Uiso 1 1 d . . . . .
H4B H 0.784(2) -0.1594(10) 0.2043(8) 0.027(4) Uiso 1 1 d . . . . .
H3 H 0.895(2) 0.2445(13) 0.1901(9) 0.045(5) Uiso 1 1 d . . . . .
O6 O 0.95293(11) -0.13765(5) 0.05315(4) 0.01968(15) Uani 1 1 d . . . . .
N4 N 0.84401(12) -0.17911(5) 0.16331(4) 0.01594(15) Uani 1 1 d . . . . .
N3 N 0.90013(11) 0.17034(5) 0.17447(4) 0.01465(14) Uani 1 1 d . . . . .
C9 C 0.90101(13) -0.11713(6) 0.11487(5) 0.01354(15) Uani 1 1 d . . . . .
C11 C 0.88247(13) 0.05202(6) 0.08381(5) 0.01352(15) Uani 1 1 d . . . . .
C10 C 0.90102(12) -0.01597(6) 0.13815(4) 0.01237(15) Uani 1 1 d . . . . .
C14 C 0.92200(14) 0.01176(6) 0.21123(5) 0.01599(16) Uani 1 1 d . . . . .
C12 C 0.88250(13) 0.14497(6) 0.10383(5) 0.01413(15) Uani 1 1 d . . . . .
C13 C 0.92039(14) 0.10618(6) 0.22785(5) 0.01686(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.2913(11) . ?
O1 C1 1.3315(10) . ?
O2 C1 1.2190(10) . ?
O4 C2 1.2391(11) . ?
C4 C5 1.4004(11) . ?
C4 C3 1.4060(11) . ?
C4 C1 1.4950(11) . ?
C2 C3 1.5148(11) . ?
C7 C6 1.3908(14) . ?
C7 C8 1.3980(12) . ?
C3 C8 1.3977(11) . ?
C5 C6 1.3937(13) . ?
O5 C15 1.2397(11) . ?
N1 C19 1.3408(11) . ?
N1 C18 1.3433(11) . ?
N2 C15 1.3369(11) . ?
C15 C16 1.5096(11) . ?
C20 C19 1.3907(12) . ?
C20 C16 1.3928(11) . ?
C16 C17 1.3935(11) . ?
C17 C18 1.3918(12) . ?
O6 C9 1.2410(10) . ?
N4 C9 1.3317(11) . ?
N3 C12 1.3429(11) . ?
N3 C13 1.3438(12) . ?
C9 C10 1.5111(12) . ?
C11 C12 1.3816(12) . ?
C11 C10 1.3939(11) . ?
C10 C14 1.3959(11) . ?
C14 C13 1.3872(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 C3 119.63(8) . . ?
C5 C4 C1 120.47(8) . . ?
C3 C4 C1 119.82(7) . . ?
O4 C2 O3 124.85(8) . . ?
O4 C2 C3 119.87(8) . . ?
O3 C2 C3 115.12(7) . . ?
O2 C1 O1 123.89(8) . . ?
O2 C1 C4 122.34(8) . . ?
O1 C1 C4 113.77(7) . . ?
C6 C7 C8 119.75(8) . . ?
C8 C3 C4 119.23(8) . . ?
C8 C3 C2 117.92(7) . . ?
C4 C3 C2 122.80(7) . . ?
C6 C5 C4 120.57(8) . . ?
C7 C6 C5 119.98(8) . . ?
C3 C8 C7 120.84(8) . . ?
C19 N1 C18 117.85(7) . . ?
O5 C15 N2 123.00(8) . . ?
O5 C15 C16 118.20(8) . . ?
N2 C15 C16 118.80(7) . . ?
C19 C20 C16 119.11(8) . . ?
C20 C16 C17 118.36(8) . . ?
C20 C16 C15 117.48(7) . . ?
C17 C16 C15 124.16(8) . . ?
N1 C19 C20 122.83(8) . . ?
C18 C17 C16 118.65(8) . . ?
N1 C18 C17 123.17(8) . . ?
C12 N3 C13 121.06(8) . . ?
O6 C9 N4 124.17(8) . . ?
O6 C9 C10 119.24(8) . . ?
N4 C9 C10 116.60(7) . . ?
C12 C11 C10 119.08(8) . . ?
C11 C10 C14 119.10(8) . . ?
C11 C10 C9 118.08(7) . . ?
C14 C10 C9 122.81(8) . . ?
C13 C14 C10 119.09(8) . . ?
N3 C12 C11 121.01(8) . . ?
N3 C13 C14 120.65(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.04(2) 1.66(2) 2.6955(10) 179(2) . yes
C18 H18 O2 0.975(14) 2.318(15) 3.1034(11) 137.0(12) . yes
N2 H2A O4 0.884(16) 2.133(16) 3.0134(11) 173.3(15) 2_745 yes
C17 H17 O4 0.988(14) 2.218(14) 3.1870(11) 166.5(12) 2_745 yes
N2 H2B O6 0.902(16) 2.095(16) 2.9922(10) 173.1(14) 4_656 yes
C11 H11 O6 0.983(15) 2.517(15) 3.0725(11) 115.6(10) 3_755 yes
N4 H4A O5 0.945(17) 1.892(17) 2.8340(10) 174.6(14) 4 yes
N4 H4B O3 0.925(15) 1.957(15) 2.8438(10) 160.0(13) 2_645 yes
N3 H3 O3 1.102(18) 1.449(18) 2.5499(10) 176.7(16) . yes
N3 H3 O4 1.102(18) 2.652(18) 3.3907(11) 123.8(11) . yes

_refine_diff_density_max         0.538
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_6_100K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922007'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_6_100K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      50.03 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N2 O1, C7 H3 N2 O6'
_chemical_formula_sum            'C13 H10 N4 O7'
_chemical_formula_weight         334.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.03460(7)
_cell_length_b                   11.48110(8)
_cell_length_c                   11.85960(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.6910(6)
_cell_angle_gamma                90
_cell_volume                     1431.431(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14563
_cell_measurement_theta_max      35.6371773965
_cell_measurement_theta_min      1.87623169344

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.993434764474
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.067: AIMLESS, version 0.7.3 : 15/08/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30463
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.451
_diffrn_reflns_theta_max         36.017
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6889
_reflns_number_gt                5629
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'

_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'

_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
 Peak Q1 is likely to be water solvent. It is not possible to fully resolve
 the water structure. An isotropic refinement is the most stable. It's refined
 occupancy is 9% and so it has been left out of the structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0748P)²+0.0624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6889
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1257
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.4805(12) 0.3022(10) 0.4174(11) 0.020(3) Uiso 1 1 d . . . . .
H10 H 0.9803(14) 0.4271(12) 0.6857(13) 0.032(3) Uiso 1 1 d . . . . .
H7 H 0.5692(13) 0.6134(11) 0.3256(12) 0.023(3) Uiso 1 1 d . . . . .
H3 H 0.2823(12) 0.3069(11) 0.2603(11) 0.022(3) Uiso 1 1 d . . . . .
H8 H 0.9221(12) 0.0998(11) 0.8966(11) 0.021(3) Uiso 1 1 d . . . . .
H9 H 1.1446(14) 0.3652(11) 0.8548(12) 0.028(3) Uiso 1 1 d . . . . .
H4 H 0.0683(15) 0.5648(13) -0.0257(15) 0.040(4) Uiso 1 1 d . . . . .
H5 H 0.2115(13) 0.6084(12) 0.0247(12) 0.025(3) Uiso 1 1 d . . . . .
H6 H 0.3737(12) 0.6307(11) 0.1668(11) 0.022(3) Uiso 1 1 d . . . . .
H1 H 0.6228(16) 0.4582(14) 0.4428(16) 0.048(4) Uiso 1 1 d . . . . .
O1 O 0.73682(6) 0.43991(5) 0.55895(5) 0.02001(12) Uani 1 1 d . . . . .
O2 O 0.70756(6) 0.25378(6) 0.50141(6) 0.02413(13) Uani 1 1 d . . . . .
O3 O 0.62358(6) 0.18381(6) 0.69560(7) 0.02544(13) Uani 1 1 d . . . . .
O5 O 1.25878(6) 0.22778(6) 1.00588(6) 0.02447(13) Uani 1 1 d . . . . .
O6 O 1.12776(7) 0.11223(6) 1.05517(6) 0.02595(14) Uani 1 1 d . . . . .
O4 O 0.73371(6) 0.02367(5) 0.71544(7) 0.02573(13) Uani 1 1 d . . . . .
N3 N 0.72426(6) 0.13041(6) 0.71773(6) 0.01761(12) Uani 1 1 d . . . . .
C1 C 0.75792(7) 0.33207(6) 0.57341(6) 0.01551(12) Uani 1 1 d . . . . .
N4 N 1.15281(6) 0.18510(6) 0.99018(6) 0.01863(12) Uani 1 1 d . . . . .
C5 C 1.04917(7) 0.22412(6) 0.88628(6) 0.01585(12) Uani 1 1 d . . . . .
C2 C 0.85602(7) 0.29661(6) 0.68843(6) 0.01416(12) Uani 1 1 d . . . . .
C7 C 0.96923(7) 0.35925(6) 0.72855(6) 0.01593(12) Uani 1 1 d . . . . .
C3 C 0.84326(7) 0.19800(6) 0.75268(6) 0.01498(12) Uani 1 1 d . . . . .
C4 C 0.93729(7) 0.16012(6) 0.85267(6) 0.01599(12) Uani 1 1 d . . . . .
C6 C 1.06756(7) 0.32311(6) 0.82654(6) 0.01622(12) Uani 1 1 d . . . . .
O7 O 0.09845(5) 0.39918(5) 0.11573(5) 0.02024(12) Uani 1 1 d . . . . .
N2 N 0.15473(6) 0.55749(6) 0.02847(6) 0.01802(12) Uani 1 1 d . . . . .
N1 N 0.53462(6) 0.45983(6) 0.37702(6) 0.01729(12) Uani 1 1 d . . . . .
C10 C 0.30878(7) 0.46898(6) 0.19863(6) 0.01474(12) Uani 1 1 d . . . . .
C11 C 0.17817(7) 0.47306(6) 0.10907(6) 0.01517(12) Uani 1 1 d . . . . .
C8 C 0.50794(7) 0.55382(7) 0.30725(7) 0.01780(13) Uani 1 1 d . . . . .
C9 C 0.39517(7) 0.56090(6) 0.21575(7) 0.01670(13) Uani 1 1 d . . . . .
C13 C 0.45394(7) 0.36884(7) 0.36069(7) 0.01835(13) Uani 1 1 d . . . . .
C12 C 0.33949(7) 0.37147(6) 0.27161(7) 0.01716(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2619(9) . ?
O2 C1 1.2480(9) . ?
O3 N3 1.2255(9) . ?
O5 N4 1.2288(9) . ?
O6 N4 1.2247(9) . ?
O4 N3 1.2309(9) . ?
N3 C3 1.4723(10) . ?
C1 C2 1.5168(10) . ?
N4 C5 1.4733(9) . ?
C5 C6 1.3863(10) . ?
C5 C4 1.3871(11) . ?
C2 C7 1.3939(10) . ?
C2 C3 1.3955(10) . ?
C7 C6 1.3906(10) . ?
C7 H10 0.958(14) . ?
C3 C4 1.3871(10) . ?
C4 H8 0.913(13) . ?
C6 H9 0.946(14) . ?
O7 C11 1.2417(9) . ?
N2 C11 1.3305(10) . ?
N2 H4 0.978(16) . ?
N2 H5 0.868(14) . ?
N1 C8 1.3371(10) . ?
N1 C13 1.3479(10) . ?
N1 H1 1.046(18) . ?
C10 C12 1.3925(10) . ?
C10 C9 1.3951(10) . ?
C10 C11 1.5090(10) . ?
C8 C9 1.3827(10) . ?
C8 H7 0.940(13) . ?
C9 H6 0.976(12) . ?
C13 C12 1.3788(10) . ?
C13 H2 1.001(12) . ?
C12 H3 0.957(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N3 O4 124.80(7) . . ?
O3 N3 C3 118.01(6) . . ?
O4 N3 C3 117.17(6) . . ?
O2 C1 O1 126.03(7) . . ?
O2 C1 C2 118.02(6) . . ?
O1 C1 C2 115.94(6) . . ?
O6 N4 O5 124.29(7) . . ?
O6 N4 C5 117.90(7) . . ?
O5 N4 C5 117.81(7) . . ?
C6 C5 C4 122.90(6) . . ?
C6 C5 N4 118.67(7) . . ?
C4 C5 N4 118.43(7) . . ?
C7 C2 C3 117.44(6) . . ?
C7 C2 C1 119.29(6) . . ?
C3 C2 C1 123.09(6) . . ?
C6 C7 C2 121.47(7) . . ?
C6 C7 H10 119.6(9) . . ?
C2 C7 H10 118.9(9) . . ?
C4 C3 C2 123.22(7) . . ?
C4 C3 N3 116.54(6) . . ?
C2 C3 N3 120.22(6) . . ?
C5 C4 C3 116.66(7) . . ?
C5 C4 H8 122.7(8) . . ?
C3 C4 H8 120.5(8) . . ?
C5 C6 C7 118.26(7) . . ?
C5 C6 H9 119.5(8) . . ?
C7 C6 H9 122.2(8) . . ?
C11 N2 H4 118.2(9) . . ?
C11 N2 H5 122.8(9) . . ?
H4 N2 H5 118.9(12) . . ?
C8 N1 C13 121.67(7) . . ?
C8 N1 H1 117.1(9) . . ?
C13 N1 H1 121.2(9) . . ?
C12 C10 C9 119.42(7) . . ?
C12 C10 C11 117.55(6) . . ?
C9 C10 C11 122.90(6) . . ?
O7 C11 N2 123.82(7) . . ?
O7 C11 C10 118.52(6) . . ?
N2 C11 C10 117.64(6) . . ?
N1 C8 C9 120.63(7) . . ?
N1 C8 H7 115.9(8) . . ?
C9 C8 H7 123.5(8) . . ?
C8 C9 C10 118.82(7) . . ?
C8 C9 H6 120.8(8) . . ?
C10 C9 H6 120.2(7) . . ?
N1 C13 C12 120.29(7) . . ?
N1 C13 H2 116.7(7) . . ?
C12 C13 H2 123.0(7) . . ?
C13 C12 C10 119.15(7) . . ?
C13 C12 H3 120.1(7) . . ?
C10 C12 H3 120.7(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H8 O6 0.913(13) 2.597(13) 3.4589(10) 157.7(11) 3_757 yes
C6 H9 O4 0.946(14) 2.547(14) 3.3201(10) 139.0(11) 2_756 yes
N2 H4 O7 0.978(16) 1.872(16) 2.8413(9) 170.7(14) 3_565 yes
N2 H5 O2 0.868(14) 1.962(14) 2.8002(9) 162.1(12) 2_655 yes
C9 H6 O2 0.976(12) 2.385(13) 3.3238(9) 161.0(10) 2_655 yes
N1 H1 O1 1.046(18) 1.572(18) 2.6000(8) 166.2(15) . yes
N1 H1 O2 1.046(18) 2.544(17) 3.1150(9) 113.7(11) . yes
C8 H7 O5 0.940(13) 2.649(13) 3.4727(10) 146.7(11) 2_756 yes
C4 H8 O6 0.913(13) 2.597(13) 3.4589(10) 157.7(11) 3_757 yes
C6 H9 O4 0.946(14) 2.547(14) 3.3201(10) 139.0(11) 2_756 yes
N2 H4 O7 0.978(16) 1.872(16) 2.8413(9) 170.7(14) 3_565 yes
N2 H5 O2 0.868(14) 1.962(14) 2.8002(9) 162.1(12) 2_655 yes
C9 H6 O2 0.976(12) 2.385(13) 3.3238(9) 161.0(10) 2_655 yes
N1 H1 O1 1.046(18) 1.572(18) 2.6000(8) 166.2(15) . yes
N1 H1 O2 1.046(18) 2.544(17) 3.1150(9) 113.7(11) . yes

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.062


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_300K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922006'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_5_300K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.46 %     
RESPONSE:  Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_300K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.17 Ang.  
RESPONSE: The long N-H distance is characteristic of H3 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_weight         410.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0100 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2267(3)
_cell_length_b                   14.3176(6)
_cell_length_c                   18.3746(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.5051(19)
_cell_angle_gamma                90
_cell_volume                     1899.38(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    300
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      43.77

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.143
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35041
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         41.366
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6548
_reflns_number_gt                4628
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.67 command used to make multi_T datasets comparable: 0.67 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0674P)²+0.2306P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6548
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 1.126(2) 0.6667(12) 0.3959(9) 0.064(5) Uiso 1 1 d . . . . .
H8 H 1.060(2) 0.5629(13) 0.1887(9) 0.063(5) Uiso 1 1 d . . . . .
H7 H 1.100(2) 0.6921(13) 0.2705(10) 0.066(5) Uiso 1 1 d . . . . .
H5 H 1.126(2) 0.5145(11) 0.4429(9) 0.056(4) Uiso 1 1 d . . . . .
H1 H 1.109(3) 0.2779(16) 0.4615(12) 0.096(7) Uiso 1 1 d . . . . .
O3 O 0.89663(14) 0.33996(6) 0.21644(5) 0.0443(2) Uani 1 1 d . . . . .
O1 O 1.08011(16) 0.34544(7) 0.44406(5) 0.0512(2) Uani 1 1 d . . . . .
O2 O 1.14919(17) 0.28409(6) 0.33686(5) 0.0558(3) Uani 1 1 d . . . . .
O4 O 1.17225(16) 0.36636(7) 0.17050(5) 0.0599(3) Uani 1 1 d . . . . .
C4 C 1.09809(16) 0.44753(7) 0.34385(6) 0.0346(2) Uani 1 1 d . . . . .
C2 C 1.05297(19) 0.38243(8) 0.21468(6) 0.0394(2) Uani 1 1 d . . . . .
C1 C 1.11172(17) 0.35079(8) 0.37374(6) 0.0376(2) Uani 1 1 d . . . . .
C7 C 1.0962(2) 0.62876(8) 0.28811(9) 0.0532(3) Uani 1 1 d . . . . .
C3 C 1.07918(16) 0.46159(7) 0.26845(6) 0.0346(2) Uani 1 1 d . . . . .
C5 C 1.11327(19) 0.52467(9) 0.39034(7) 0.0443(3) Uani 1 1 d . . . . .
C6 C 1.1133(2) 0.61456(9) 0.36225(9) 0.0523(3) Uani 1 1 d . . . . .
C8 C 1.0777(2) 0.55260(8) 0.24143(7) 0.0455(3) Uani 1 1 d . . . . .
H20 H 1.197(2) 0.0239(11) 0.6274(9) 0.054(4) Uiso 1 1 d . . . . .
H19 H 1.116(2) 0.1803(12) 0.5964(9) 0.057(4) Uiso 1 1 d . . . . .
H18 H 1.206(2) 0.1376(12) 0.3927(9) 0.058(5) Uiso 1 1 d . . . . .
H2A H 1.341(2) -0.1580(12) 0.4468(10) 0.061(5) Uiso 1 1 d . . . . .
H17 H 1.286(2) -0.0189(12) 0.4102(9) 0.063(5) Uiso 1 1 d . . . . .
H2B H 1.366(2) -0.2323(13) 0.5060(10) 0.065(5) Uiso 1 1 d . . . . .
O5 O 1.29118(18) -0.13618(6) 0.60901(5) 0.0575(3) Uani 1 1 d . . . . .
N1 N 1.15476(15) 0.16989(7) 0.49234(6) 0.0418(2) Uani 1 1 d . . . . .
N2 N 1.33611(18) -0.17444(8) 0.49235(6) 0.0462(3) Uani 1 1 d . . . . .
C15 C 1.29414(17) -0.11443(8) 0.54428(6) 0.0384(2) Uani 1 1 d . . . . .
C20 C 1.1996(2) 0.04565(8) 0.57763(6) 0.0429(3) Uani 1 1 d . . . . .
C16 C 1.24788(15) -0.01524(7) 0.52316(6) 0.0342(2) Uani 1 1 d . . . . .
C19 C 1.1525(2) 0.13668(8) 0.55982(7) 0.0445(3) Uani 1 1 d . . . . .
C17 C 1.25053(19) 0.01891(9) 0.45281(6) 0.0431(3) Uani 1 1 d . . . . .
C18 C 1.2041(2) 0.11151(9) 0.44009(7) 0.0455(3) Uani 1 1 d . . . . .
H11 H 0.870(2) 0.0354(11) 0.0336(9) 0.057(4) Uiso 1 1 d . . . . .
H13 H 0.939(3) 0.1298(13) 0.2752(10) 0.069(5) Uiso 1 1 d . . . . .
H12 H 0.877(2) 0.1977(12) 0.0703(9) 0.057(4) Uiso 1 1 d . . . . .
H14 H 0.938(2) -0.0325(13) 0.2509(9) 0.064(5) Uiso 1 1 d . . . . .
H4A H 0.828(2) -0.2413(13) 0.1460(9) 0.063(5) Uiso 1 1 d . . . . .
H4B H 0.786(2) -0.1582(11) 0.2035(9) 0.054(4) Uiso 1 1 d . . . . .
H3 H 0.906(3) 0.2491(15) 0.1922(11) 0.087(6) Uiso 1 1 d . . . . .
O6 O 0.94322(18) -0.13707(7) 0.05292(5) 0.0603(3) Uani 1 1 d . . . . .
N4 N 0.83907(18) -0.17838(7) 0.16226(6) 0.0478(3) Uani 1 1 d . . . . .
N3 N 0.90570(15) 0.17007(7) 0.17508(6) 0.0428(2) Uani 1 1 d . . . . .
C9 C 0.89513(18) -0.11665(8) 0.11430(6) 0.0400(2) Uani 1 1 d . . . . .
C11 C 0.88340(18) 0.05281(8) 0.08486(6) 0.0393(2) Uani 1 1 d . . . . .
C10 C 0.89911(16) -0.01561(7) 0.13807(6) 0.0352(2) Uani 1 1 d . . . . .
C14 C 0.9214(2) 0.01131(9) 0.21037(7) 0.0482(3) Uani 1 1 d . . . . .
C12 C 0.88738(18) 0.14510(8) 0.10522(7) 0.0420(3) Uani 1 1 d . . . . .
C13 C 0.9237(2) 0.10546(9) 0.22713(7) 0.0513(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.2847(16) . ?
O1 C1 1.3242(14) . ?
O2 C1 1.2085(14) . ?
O4 C2 1.2313(15) . ?
C4 C5 1.3976(15) . ?
C4 C3 1.4008(15) . ?
C4 C1 1.4917(15) . ?
C2 C3 1.5100(15) . ?
C7 C6 1.378(2) . ?
C7 C8 1.3901(19) . ?
C3 C8 1.3944(15) . ?
C5 C6 1.3867(19) . ?
O5 C15 1.2305(14) . ?
N1 C19 1.3288(16) . ?
N1 C18 1.3332(16) . ?
N2 C15 1.3289(16) . ?
C15 C16 1.5059(15) . ?
C20 C19 1.3826(16) . ?
C20 C16 1.3836(16) . ?
C16 C17 1.3828(15) . ?
C17 C18 1.3850(16) . ?
O6 C9 1.2298(14) . ?
N4 C9 1.3240(15) . ?
N3 C13 1.3329(18) . ?
N3 C12 1.3334(16) . ?
C9 C10 1.5111(15) . ?
C11 C12 1.3733(16) . ?
C11 C10 1.3852(16) . ?
C10 C14 1.3858(16) . ?
C14 C13 1.3826(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 C3 119.52(10) . . ?
C5 C4 C1 120.43(10) . . ?
C3 C4 C1 119.97(9) . . ?
O4 C2 O3 124.74(11) . . ?
O4 C2 C3 120.02(12) . . ?
O3 C2 C3 115.09(10) . . ?
O2 C1 O1 123.63(11) . . ?
O2 C1 C4 122.69(10) . . ?
O1 C1 C4 113.68(10) . . ?
C6 C7 C8 119.77(12) . . ?
C8 C3 C4 119.04(10) . . ?
C8 C3 C2 118.01(10) . . ?
C4 C3 C2 122.92(9) . . ?
C6 C5 C4 120.48(12) . . ?
C7 C6 C5 120.23(12) . . ?
C7 C8 C3 120.95(12) . . ?
C19 N1 C18 117.52(10) . . ?
O5 C15 N2 122.99(11) . . ?
O5 C15 C16 118.34(10) . . ?
N2 C15 C16 118.67(10) . . ?
C19 C20 C16 119.34(11) . . ?
C17 C16 C20 117.88(10) . . ?
C17 C16 C15 124.22(10) . . ?
C20 C16 C15 117.90(10) . . ?
N1 C19 C20 123.04(11) . . ?
C16 C17 C18 118.89(11) . . ?
N1 C18 C17 123.31(11) . . ?
C13 N3 C12 120.48(11) . . ?
O6 C9 N4 123.96(11) . . ?
O6 C9 C10 119.35(10) . . ?
N4 C9 C10 116.69(10) . . ?
C12 C11 C10 119.21(11) . . ?
C11 C10 C14 118.84(10) . . ?
C11 C10 C9 118.23(10) . . ?
C14 C10 C9 122.91(11) . . ?
C13 C14 C10 118.98(12) . . ?
N3 C12 C11 121.35(11) . . ?
N3 C13 C14 121.12(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.04(2) 1.68(2) 2.7117(13) 178(2) . yes
C18 H18 O2 0.949(17) 2.363(17) 3.1297(15) 137.6(14) . yes
N2 H2A O4 0.872(18) 2.181(18) 3.0468(15) 171.9(16) 2_745 yes
C17 H17 O4 0.994(17) 2.243(17) 3.2135(16) 165.1(14) 2_745 yes
N2 H2B O6 0.889(19) 2.124(19) 3.0076(14) 172.2(16) 4_656 yes
C11 H11 O6 0.975(16) 2.580(16) 3.1163(15) 114.7(11) 3_755 yes
N4 H4A O5 0.952(18) 1.895(19) 2.8456(14) 176.0(16) 4 yes
N4 H4B O3 0.912(17) 2.017(17) 2.8758(14) 156.2(15) 2_645 yes
N3 H3 O3 1.17(2) 1.38(2) 2.5501(12) 175.3(18) . yes
N3 H3 O4 1.17(2) 2.60(2) 3.4103(15) 125.2(13) . yes

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_7_100K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922010'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_7_100K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.41 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT430_complex_7_100K_shelxl 
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.76 Ang.  
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi-pi interaction.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'isonicotinamide 2,4-dinitrobenzoate/benzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_weight         668.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6450(4)
_cell_length_b                   10.2722(4)
_cell_length_c                   15.2241(6)
_cell_angle_alpha                79.3772(18)
_cell_angle_beta                 72.0170(17)
_cell_angle_gamma                77.3694(18)
_cell_volume                     1388.80(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      43.79

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21882
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         35.633
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6582
_reflns_number_gt                5677
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.76 command used to make multi_T datasets comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.3175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6582
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1033
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H19 H 1.4729(16) 0.7992(15) 0.1180(10) 0.020(4) Uiso 1 1 d . . . . .
H5 H 0.8025(17) 0.6644(15) 0.1705(10) 0.018(3) Uiso 1 1 d . . . . .
H10 H -0.0293(16) 0.3491(14) 0.6767(10) 0.016(3) Uiso 1 1 d . . . . .
H4 H 0.6132(16) 0.5796(16) 0.2916(10) 0.021(4) Uiso 1 1 d . . . . .
H18 H 1.2930(17) 0.6575(15) 0.1880(11) 0.022(4) Uiso 1 1 d . . . . .
H20 H 1.4907(17) 0.7308(15) -0.1405(11) 0.021(4) Uiso 1 1 d . . . . .
H3 H 0.4129(17) 0.9419(15) 0.3485(11) 0.022(4) Uiso 1 1 d . . . . .
H6 H 0.5959(16) 1.0425(15) 0.2301(10) 0.021(4) Uiso 1 1 d . . . . .
H17 H 1.0896(18) 0.0788(16) 0.1653(11) 0.024(4) Uiso 1 1 d . . . . .
H15 H 0.9046(16) -0.0273(15) 0.2797(10) 0.020(4) Uiso 1 1 d . . . . .
H11 H 0.0797(17) 0.1758(15) 0.4379(11) 0.023(4) Uiso 1 1 d . . . . .
H9 H 0.1494(17) 0.4858(15) 0.6077(11) 0.024(4) Uiso 1 1 d . . . . .
H13 H 0.482(2) 0.1229(17) 0.4868(12) 0.033(4) Uiso 1 1 d . . . . .
H7 H 1.034(2) 0.8803(18) 0.0370(13) 0.036(5) Uiso 1 1 d . . . . .
H12 H 0.5387(18) 0.2456(18) 0.4352(11) 0.026(4) Uiso 1 1 d . . . . .
H14 H 0.7353(19) 0.3358(17) 0.3762(11) 0.030(4) Uiso 1 1 d . . . . .
H1 H 0.429(2) 0.7128(18) 0.3773(12) 0.038(5) Uiso 1 1 d . . . . .
H8 H 0.9904(19) 0.7666(18) 0.1089(12) 0.033(4) Uiso 1 1 d . . . . .
H16 H 0.9254(18) 0.4256(18) 0.2574(12) 0.033(4) Uiso 1 1 d . . . . .
H2 H 1.096(2) 0.313(2) 0.1617(15) 0.062(6) Uiso 1 1 d . . . . .
O2 O 1.62871(10) 0.90210(9) -0.13984(6) 0.02153(19) Uani 1 1 d . . . . .
O1 O 1.66106(11) 0.89720(10) -0.00511(6) 0.0266(2) Uani 1 1 d . . . . .
O3 O 1.36720(12) 0.56404(12) -0.17257(7) 0.0364(3) Uani 1 1 d . . . . .
O4 O 1.15819(11) 0.56095(11) -0.06635(7) 0.0294(2) Uani 1 1 d . . . . .
O5 O 1.20769(9) 0.39557(8) 0.09873(6) 0.01742(18) Uani 1 1 d . . . . .
O6 O 1.05524(9) 0.57122(8) 0.16568(6) 0.01853(18) Uani 1 1 d . . . . .
N8 N 1.60233(11) 0.86419(10) -0.05640(7) 0.0162(2) Uani 1 1 d . . . . .
N7 N 1.28565(12) 0.58138(10) -0.09469(7) 0.0201(2) Uani 1 1 d . . . . .
C5 C 1.49319(12) 0.77432(11) -0.01473(8) 0.0138(2) Uani 1 1 d . . . . .
C3 C 1.34340(12) 0.63385(11) -0.03210(8) 0.0138(2) Uani 1 1 d . . . . .
C4 C 1.44938(12) 0.71492(11) -0.07351(8) 0.0141(2) Uani 1 1 d . . . . .
C2 C 1.28484(12) 0.60808(11) 0.06392(8) 0.0139(2) Uani 1 1 d . . . . .
C1 C 1.17104(12) 0.51811(11) 0.11252(8) 0.0141(2) Uani 1 1 d . . . . .
C7 C 1.33356(13) 0.67057(12) 0.11983(8) 0.0172(2) Uani 1 1 d . . . . .
C6 C 1.43745(13) 0.75485(12) 0.08103(8) 0.0169(2) Uani 1 1 d . . . . .
C10 C 0.72661(13) 0.72333(12) 0.20552(8) 0.0168(2) Uani 1 1 d . . . . .
C13 C 0.49530(13) 0.88905(12) 0.31043(8) 0.0175(2) Uani 1 1 d . . . . .
C11 C 0.61545(13) 0.67231(12) 0.27658(8) 0.0165(2) Uani 1 1 d . . . . .
C8 C 0.84076(12) 0.92657(11) 0.11261(8) 0.0154(2) Uani 1 1 d . . . . .
C12 C 0.60403(13) 0.94512(12) 0.24071(8) 0.0164(2) Uani 1 1 d . . . . .
C9 C 0.72245(12) 0.86199(11) 0.18818(8) 0.0141(2) Uani 1 1 d . . . . .
O12 O 0.81335(9) 1.04677(8) 0.08362(6) 0.01889(18) Uani 1 1 d . . . . .
N3 N 0.97022(12) 0.84744(11) 0.08338(8) 0.0218(2) Uani 1 1 d . . . . .
N2 N 0.50452(11) 0.75501(10) 0.32742(7) 0.0156(2) Uani 1 1 d . . . . .
C17 C 0.79749(12) 0.14316(11) 0.34102(8) 0.0137(2) Uani 1 1 d . . . . .
C16 C 0.67622(12) 0.07736(11) 0.41158(8) 0.0143(2) Uani 1 1 d . . . . .
C18 C 0.90503(13) 0.06660(12) 0.27808(9) 0.0179(2) Uani 1 1 d . . . . .
C15 C 0.80369(14) 0.27798(13) 0.33634(9) 0.0214(3) Uani 1 1 d . . . . .
C14 C 0.91561(14) 0.33164(12) 0.26771(9) 0.0211(3) Uani 1 1 d . . . . .
C19 C 1.01530(13) 0.12593(12) 0.21131(9) 0.0196(2) Uani 1 1 d . . . . .
O8 O 0.46957(9) 0.43913(8) 0.40457(6) 0.02080(19) Uani 1 1 d . . . . .
O11 O -0.16991(10) 0.16956(9) 0.68911(6) 0.0238(2) Uani 1 1 d . . . . .
O9 O 0.30503(9) 0.62280(8) 0.44742(6) 0.01726(18) Uani 1 1 d . . . . .
O10 O -0.12743(10) 0.09542(9) 0.55721(7) 0.0252(2) Uani 1 1 d . . . . .
N5 N 0.28116(11) 0.31593(10) 0.33575(7) 0.0192(2) Uani 1 1 d . . . . .
N6 N -0.10445(11) 0.16599(10) 0.60604(7) 0.0179(2) Uani 1 1 d . . . . .
O13 O 0.33598(13) 0.20502(10) 0.31141(7) 0.0362(3) Uani 1 1 d . . . . .
O14 O 0.28917(12) 0.42197(10) 0.28439(6) 0.0291(2) Uani 1 1 d . . . . .
O7 O 0.69481(9) -0.04647(8) 0.42810(6) 0.01949(19) Uani 1 1 d . . . . .
N1 N 1.01796(11) 0.25658(10) 0.20730(7) 0.0157(2) Uani 1 1 d . . . . .
N4 N 0.55428(12) 0.15883(11) 0.45063(8) 0.0194(2) Uani 1 1 d . . . . .
C21 C 0.22162(12) 0.41455(11) 0.48180(8) 0.0136(2) Uani 1 1 d . . . . .
C20 C 0.34370(12) 0.49893(11) 0.44014(8) 0.0140(2) Uani 1 1 d . . . . .
C24 C 0.00885(12) 0.25191(11) 0.56303(8) 0.0151(2) Uani 1 1 d . . . . .
C25 C 0.02771(13) 0.34032(12) 0.61503(8) 0.0173(2) Uani 1 1 d . . . . .
C22 C 0.19700(12) 0.32277(11) 0.43388(8) 0.0141(2) Uani 1 1 d . . . . .
C23 C 0.09289(13) 0.23961(11) 0.47229(8) 0.0150(2) Uani 1 1 d . . . . .
C26 C 0.13474(13) 0.42123(12) 0.57310(8) 0.0174(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N8 1.2212(13) . ?
O1 N8 1.2249(13) . ?
O3 N7 1.2235(14) . ?
O4 N7 1.2221(14) . ?
O5 C1 1.2691(14) . ?
O6 C1 1.2402(14) . ?
N8 C5 1.4696(14) . ?
N7 C3 1.4688(15) . ?
C5 C4 1.3782(16) . ?
C5 C6 1.3820(16) . ?
C3 C4 1.3844(15) . ?
C3 C2 1.3924(16) . ?
C4 H20 0.970(15) . ?
C2 C7 1.3920(17) . ?
C2 C1 1.5154(15) . ?
C7 C6 1.3885(16) . ?
C7 H18 0.984(15) . ?
C6 H19 0.960(15) . ?
C10 C11 1.3838(16) . ?
C10 C9 1.3938(16) . ?
C10 H5 0.933(15) . ?
C13 N2 1.3416(15) . ?
C13 C12 1.3819(16) . ?
C13 H3 0.951(16) . ?
C11 N2 1.3413(15) . ?
C11 H4 0.941(15) . ?
C8 O12 1.2319(14) . ?
C8 N3 1.3283(16) . ?
C8 C9 1.5181(15) . ?
C12 C9 1.3909(16) . ?
C12 H6 0.973(15) . ?
N3 H7 0.854(19) . ?
N3 H8 0.858(18) . ?
N2 H1 0.985(18) . ?
C17 C18 1.3856(16) . ?
C17 C15 1.3870(16) . ?
C17 C16 1.5104(15) . ?
C16 O7 1.2343(14) . ?
C16 N4 1.3260(15) . ?
C18 C19 1.3869(16) . ?
C18 H15 0.961(15) . ?
C15 C14 1.3828(16) . ?
C15 H14 0.933(17) . ?
C14 N1 1.3352(15) . ?
C14 H16 0.969(17) . ?
C19 N1 1.3377(15) . ?
C19 H17 0.949(16) . ?
O8 C20 1.2389(14) . ?
O11 N6 1.2301(14) . ?
O9 C20 1.2607(14) . ?
O10 N6 1.2240(14) . ?
N5 O13 1.2190(14) . ?
N5 O14 1.2204(14) . ?
N5 C22 1.4699(14) . ?
N6 C24 1.4727(14) . ?
N1 H2 1.05(2) . ?
N4 H13 0.854(18) . ?
N4 H12 0.871(17) . ?
C21 C26 1.3891(16) . ?
C21 C22 1.3913(16) . ?
C21 C20 1.5239(15) . ?
C24 C23 1.3819(16) . ?
C24 C25 1.3823(17) . ?
C25 C26 1.3916(16) . ?
C25 H10 0.940(14) . ?
C22 C23 1.3814(15) . ?
C23 H11 0.961(16) . ?
C26 H9 0.976(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N8 O1 123.83(10) . . ?
O2 N8 C5 118.26(10) . . ?
O1 N8 C5 117.91(9) . . ?
O4 N7 O3 124.31(11) . . ?
O4 N7 C3 117.86(10) . . ?
O3 N7 C3 117.81(10) . . ?
C4 C5 C6 123.02(10) . . ?
C4 C5 N8 118.14(10) . . ?
C6 C5 N8 118.83(10) . . ?
C4 C3 C2 123.18(10) . . ?
C4 C3 N7 116.75(10) . . ?
C2 C3 N7 119.95(10) . . ?
C5 C4 C3 116.65(10) . . ?
C5 C4 H20 120.9(9) . . ?
C3 C4 H20 122.4(9) . . ?
C7 C2 C3 117.59(10) . . ?
C7 C2 C1 117.28(10) . . ?
C3 C2 C1 125.13(10) . . ?
O6 C1 O5 127.13(10) . . ?
O6 C1 C2 115.95(10) . . ?
O5 C1 C2 116.78(9) . . ?
C6 C7 C2 121.05(11) . . ?
C6 C7 H18 118.5(9) . . ?
C2 C7 H18 120.4(9) . . ?
C5 C6 C7 118.48(11) . . ?
C5 C6 H19 118.8(9) . . ?
C7 C6 H19 122.8(9) . . ?
C11 C10 C9 118.99(11) . . ?
C11 C10 H5 119.4(9) . . ?
C9 C10 H5 121.6(9) . . ?
N2 C13 C12 120.02(11) . . ?
N2 C13 H3 117.4(9) . . ?
C12 C13 H3 122.6(9) . . ?
N2 C11 C10 120.56(11) . . ?
N2 C11 H4 116.9(9) . . ?
C10 C11 H4 122.5(9) . . ?
O12 C8 N3 124.30(11) . . ?
O12 C8 C9 119.38(10) . . ?
N3 C8 C9 116.31(10) . . ?
C13 C12 C9 119.68(11) . . ?
C13 C12 H6 118.7(9) . . ?
C9 C12 H6 121.6(9) . . ?
C12 C9 C10 118.98(10) . . ?
C12 C9 C8 118.43(10) . . ?
C10 C9 C8 122.57(10) . . ?
C8 N3 H7 117.1(12) . . ?
C8 N3 H8 122.8(11) . . ?
H7 N3 H8 120.2(16) . . ?
C11 N2 C13 121.72(10) . . ?
C11 N2 H1 116.9(10) . . ?
C13 N2 H1 121.4(10) . . ?
C18 C17 C15 118.94(10) . . ?
C18 C17 C16 118.84(10) . . ?
C15 C17 C16 122.22(10) . . ?
O7 C16 N4 124.41(10) . . ?
O7 C16 C17 119.02(10) . . ?
N4 C16 C17 116.55(10) . . ?
C17 C18 C19 119.72(11) . . ?
C17 C18 H15 121.1(9) . . ?
C19 C18 H15 119.1(9) . . ?
C14 C15 C17 118.64(11) . . ?
C14 C15 H14 117.5(10) . . ?
C17 C15 H14 123.8(10) . . ?
N1 C14 C15 121.65(11) . . ?
N1 C14 H16 114.2(10) . . ?
C15 C14 H16 124.2(10) . . ?
N1 C19 C18 120.32(11) . . ?
N1 C19 H17 116.5(9) . . ?
C18 C19 H17 123.1(9) . . ?
O13 N5 O14 124.86(11) . . ?
O13 N5 C22 117.75(10) . . ?
O14 N5 C22 117.38(10) . . ?
O10 N6 O11 124.10(10) . . ?
O10 N6 C24 118.16(10) . . ?
O11 N6 C24 117.74(10) . . ?
C14 N1 C19 120.72(10) . . ?
C14 N1 H2 111.1(12) . . ?
C19 N1 H2 128.2(12) . . ?
C16 N4 H13 117.6(12) . . ?
C16 N4 H12 124.0(11) . . ?
H13 N4 H12 117.7(15) . . ?
C26 C21 C22 116.90(10) . . ?
C26 C21 C20 120.25(10) . . ?
C22 C21 C20 122.74(10) . . ?
O8 C20 O9 127.10(10) . . ?
O8 C20 C21 117.20(10) . . ?
O9 C20 C21 115.68(10) . . ?
C23 C24 C25 122.78(10) . . ?
C23 C24 N6 118.33(10) . . ?
C25 C24 N6 118.89(10) . . ?
C24 C25 C26 118.11(11) . . ?
C24 C25 H10 123.1(9) . . ?
C26 C25 H10 118.8(9) . . ?
C23 C22 C21 123.65(10) . . ?
C23 C22 N5 117.17(10) . . ?
C21 C22 N5 119.13(10) . . ?
C22 C23 C24 116.74(11) . . ?
C22 C23 H11 121.9(9) . . ?
C24 C23 H11 121.4(9) . . ?
C21 C26 C25 121.81(11) . . ?
C21 C26 H9 118.2(9) . . ?
C25 C26 H9 120.0(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H5 O6 0.933(15) 2.399(15) 3.1388(14) 136.0(12) . yes
C25 H10 O6 0.940(14) 2.598(14) 3.4298(15) 147.7(11) 2_666 yes
C11 H4 O3 0.941(15) 2.480(15) 3.0831(16) 122.0(11) 2_765 yes
C11 H4 O8 0.941(15) 2.334(15) 3.0942(14) 137.6(12) . yes
C13 H3 O13 0.951(16) 2.645(15) 3.2739(16) 124.1(11) 1_565 yes
N4 H13 O7 0.854(18) 2.010(19) 2.8637(13) 177.4(17) 2_656 yes
N3 H7 O12 0.854(19) 2.097(19) 2.9494(13) 175.4(17) 2_775 yes
N4 H12 O8 0.871(17) 1.971(17) 2.8338(14) 170.7(15) . yes
C15 H14 O8 0.933(17) 2.486(17) 3.2308(15) 136.9(13) . yes
N2 H1 O9 0.985(18) 1.660(19) 2.6347(12) 169.5(16) . yes
N3 H8 O6 0.858(18) 2.076(18) 2.9324(14) 175.9(16) . yes
C14 H16 O6 0.969(17) 2.174(17) 3.0052(14) 143.0(14) . yes
N1 H2 O5 1.05(2) 1.50(2) 2.5542(12) 178(2) . yes
N1 H2 O6 1.05(2) 2.60(2) 3.2541(13) 119.8(15) . yes

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.059

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_7_300K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922012'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_7_300K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.50 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_7_300K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.10 Ang.  
RESPONSE: The long N-H distance is characteristic of H2 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT430_complex_7_300K_shelxl 
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.84 Ang.  
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi-pi interaction.
;
_vrf_PLAT772_complex_7_300K_shelxl 
;
PROBLEM: Suspect O-H Bond in CIF: O5       --H2        ..       1.47 Ang.  
RESPONSE: The short H...O distance is characteristic of H2 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'isonicotinamide 2,4-dinitrobenzoate/benzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_weight         668.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7819(4)
_cell_length_b                   10.3742(4)
_cell_length_c                   15.4651(7)
_cell_angle_alpha                78.774(2)
_cell_angle_beta                 71.008(2)
_cell_angle_gamma                77.449(2)
_cell_volume                     1435.37(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    300
_cell_measurement_reflns_used    8114
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      40.76

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_T_max  0.7481
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23053
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.529
_diffrn_reflns_theta_max         35.632
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6832
_reflns_number_gt                4338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.76 command used to make multi_T datasets comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+0.1584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6832
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H19 H 1.474(2) 0.787(2) 0.1126(16) 0.072(7) Uiso 1 1 d . . . . .
H5 H 0.800(2) 0.662(2) 0.1664(15) 0.065(6) Uiso 1 1 d . . . . .
H10 H -0.020(2) 0.343(2) 0.6745(15) 0.062(6) Uiso 1 1 d . . . . .
H4 H 0.617(2) 0.578(2) 0.2848(14) 0.061(6) Uiso 1 1 d . . . . .
H18 H 1.300(2) 0.653(2) 0.1847(16) 0.066(6) Uiso 1 1 d . . . . .
H20 H 1.482(2) 0.7307(19) -0.1359(15) 0.055(5) Uiso 1 1 d . . . . .
H3 H 0.409(2) 0.933(2) 0.3444(15) 0.066(6) Uiso 1 1 d . . . . .
H6 H 0.596(2) 1.031(2) 0.2250(15) 0.074(7) Uiso 1 1 d . . . . .
H17 H 1.080(3) 0.089(2) 0.1615(17) 0.085(7) Uiso 1 1 d . . . . .
H15 H 0.895(2) -0.015(2) 0.2723(15) 0.071(6) Uiso 1 1 d . . . . .
H11 H 0.085(2) 0.174(2) 0.4457(14) 0.058(6) Uiso 1 1 d . . . . .
H9 H 0.150(2) 0.482(2) 0.6024(15) 0.065(6) Uiso 1 1 d . . . . .
H13 H 0.480(3) 0.123(2) 0.4920(15) 0.068(6) Uiso 1 1 d . . . . .
H7 H 1.037(3) 0.879(2) 0.0352(17) 0.079(7) Uiso 1 1 d . . . . .
H12 H 0.539(2) 0.248(3) 0.4409(16) 0.075(7) Uiso 1 1 d . . . . .
H14 H 0.744(3) 0.331(2) 0.3839(16) 0.078(7) Uiso 1 1 d . . . . .
H1 H 0.428(3) 0.703(2) 0.3702(16) 0.077(7) Uiso 1 1 d . . . . .
H8 H 0.995(2) 0.767(3) 0.1052(16) 0.077(7) Uiso 1 1 d . . . . .
H16 H 0.926(3) 0.420(3) 0.2681(17) 0.093(8) Uiso 1 1 d . . . . .
H2 H 1.103(3) 0.316(3) 0.1636(18) 0.097(8) Uiso 1 1 d . . . . .
O2 O 1.63125(16) 0.89771(15) -0.14013(10) 0.0689(4) Uani 1 1 d . . . . .
O1 O 1.66325(19) 0.89007(19) -0.00944(12) 0.0880(6) Uani 1 1 d . . . . .
O3 O 1.3581(2) 0.5728(3) -0.16707(14) 0.1280(9) Uani 1 1 d . . . . .
O4 O 1.1560(2) 0.5702(2) -0.06153(12) 0.0960(6) Uani 1 1 d . . . . .
O5 O 1.20686(13) 0.40089(12) 0.10114(9) 0.0549(3) Uani 1 1 d . . . . .
O6 O 1.05644(13) 0.57222(12) 0.16720(10) 0.0606(4) Uani 1 1 d . . . . .
N8 N 1.60417(16) 0.85979(15) -0.05835(12) 0.0516(4) Uani 1 1 d . . . . .
N7 N 1.2814(2) 0.58826(19) -0.09049(13) 0.0652(5) Uani 1 1 d . . . . .
C5 C 1.49365(17) 0.77170(16) -0.01581(12) 0.0405(4) Uani 1 1 d . . . . .
C3 C 1.34102(17) 0.63756(16) -0.03031(12) 0.0403(4) Uani 1 1 d . . . . .
C4 C 1.44711(18) 0.71700(17) -0.07213(12) 0.0418(4) Uani 1 1 d . . . . .
C2 C 1.28447(17) 0.61023(16) 0.06454(12) 0.0410(4) Uani 1 1 d . . . . .
C1 C 1.17096(18) 0.52128(17) 0.11422(12) 0.0448(4) Uani 1 1 d . . . . .
C7 C 1.3359(2) 0.6686(2) 0.11814(14) 0.0545(5) Uani 1 1 d . . . . .
C6 C 1.4400(2) 0.7507(2) 0.07827(14) 0.0538(5) Uani 1 1 d . . . . .
C10 C 0.7286(2) 0.71992(19) 0.20342(14) 0.0517(5) Uani 1 1 d . . . . .
C13 C 0.4961(2) 0.87931(19) 0.30510(14) 0.0536(5) Uani 1 1 d . . . . .
C11 C 0.6169(2) 0.6682(2) 0.27279(14) 0.0516(5) Uani 1 1 d . . . . .
C8 C 0.84085(18) 0.92263(17) 0.11096(12) 0.0464(4) Uani 1 1 d . . . . .
C12 C 0.60473(19) 0.93643(19) 0.23667(13) 0.0500(5) Uani 1 1 d . . . . .
C9 C 0.72310(18) 0.85653(17) 0.18580(12) 0.0426(4) Uani 1 1 d . . . . .
O12 O 0.81403(14) 1.04078(12) 0.08276(10) 0.0600(4) Uani 1 1 d . . . . .
N3 N 0.96857(19) 0.84729(19) 0.08224(15) 0.0744(6) Uani 1 1 d . . . . .
N2 N 0.50567(16) 0.74761(15) 0.32184(11) 0.0480(4) Uani 1 1 d . . . . .
C17 C 0.79533(17) 0.14726(16) 0.34127(11) 0.0406(4) Uani 1 1 d . . . . .
C16 C 0.67438(18) 0.08065(16) 0.41058(12) 0.0431(4) Uani 1 1 d . . . . .
C18 C 0.8977(2) 0.0759(2) 0.27597(15) 0.0557(5) Uani 1 1 d . . . . .
C15 C 0.8073(2) 0.2764(2) 0.34067(16) 0.0681(7) Uani 1 1 d . . . . .
C14 C 0.9190(2) 0.3308(2) 0.27317(16) 0.0693(7) Uani 1 1 d . . . . .
C19 C 1.0076(2) 0.1366(2) 0.21046(16) 0.0620(6) Uani 1 1 d . . . . .
O8 O 0.47043(14) 0.43783(12) 0.40626(11) 0.0677(4) Uani 1 1 d . . . . .
O11 O -0.16338(17) 0.16854(16) 0.69177(12) 0.0806(5) Uani 1 1 d . . . . .
O9 O 0.30457(13) 0.61773(12) 0.43951(10) 0.0570(4) Uani 1 1 d . . . . .
O10 O -0.12337(18) 0.09600(16) 0.56325(14) 0.0851(5) Uani 1 1 d . . . . .
N5 N 0.2850(2) 0.3085(2) 0.33877(12) 0.0641(5) Uani 1 1 d . . . . .
N6 N -0.09916(17) 0.16484(16) 0.61018(14) 0.0602(5) Uani 1 1 d . . . . .
O13 O 0.3365(3) 0.1992(2) 0.31675(13) 0.1194(8) Uani 1 1 d . . . . .
O14 O 0.2989(2) 0.4113(2) 0.28671(11) 0.1023(6) Uani 1 1 d . . . . .
O7 O 0.68978(14) -0.04125(12) 0.42370(10) 0.0628(4) Uani 1 1 d . . . . .
N1 N 1.01564(16) 0.26212(14) 0.21015(10) 0.0480(4) Uani 1 1 d . . . . .
N4 N 0.55672(18) 0.15907(17) 0.45345(13) 0.0610(5) Uani 1 1 d . . . . .
C21 C 0.22471(17) 0.41005(16) 0.48054(12) 0.0410(4) Uani 1 1 d . . . . .
C20 C 0.34483(18) 0.49524(16) 0.43763(12) 0.0442(4) Uani 1 1 d . . . . .
C24 C 0.01388(18) 0.25010(17) 0.56531(13) 0.0466(4) Uani 1 1 d . . . . .
C25 C 0.0325(2) 0.3380(2) 0.61395(14) 0.0557(5) Uani 1 1 d . . . . .
C22 C 0.20076(18) 0.31851(16) 0.43543(11) 0.0429(4) Uani 1 1 d . . . . .
C23 C 0.09648(19) 0.23685(18) 0.47602(13) 0.0464(4) Uani 1 1 d . . . . .
C26 C 0.1385(2) 0.4173(2) 0.57061(14) 0.0545(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N8 1.207(2) . ?
O1 N8 1.209(2) . ?
O3 N7 1.198(2) . ?
O4 N7 1.205(2) . ?
O5 C1 1.259(2) . ?
O5 H2 1.47(3) . ?
O6 C1 1.233(2) . ?
N8 C5 1.473(2) . ?
N7 C3 1.461(2) . ?
C5 C4 1.360(2) . ?
C5 C6 1.367(3) . ?
C3 C4 1.379(2) . ?
C3 C2 1.384(2) . ?
C4 H20 0.93(2) . ?
C2 C7 1.381(3) . ?
C2 C1 1.513(2) . ?
C7 C6 1.381(3) . ?
C7 H18 0.97(2) . ?
C6 H19 0.88(2) . ?
C10 C11 1.379(2) . ?
C10 C9 1.383(2) . ?
C10 H5 0.93(2) . ?
C13 N2 1.328(2) . ?
C13 C12 1.378(2) . ?
C13 H3 1.00(2) . ?
C11 N2 1.325(2) . ?
C11 H4 0.92(2) . ?
C8 O12 1.220(2) . ?
C8 N3 1.311(2) . ?
C8 C9 1.518(2) . ?
C12 C9 1.375(3) . ?
C12 H6 0.96(2) . ?
N3 H7 0.88(3) . ?
N3 H8 0.86(2) . ?
N2 H1 1.00(2) . ?
C17 C15 1.368(3) . ?
C17 C18 1.372(3) . ?
C17 C16 1.506(2) . ?
C16 O7 1.225(2) . ?
C16 N4 1.316(2) . ?
C18 C19 1.384(3) . ?
C18 H15 0.96(2) . ?
C15 C14 1.378(3) . ?
C15 H14 0.94(2) . ?
C14 N1 1.315(2) . ?
C14 H16 0.92(3) . ?
C19 N1 1.321(2) . ?
C19 H17 0.98(3) . ?
O8 C20 1.227(2) . ?
O11 N6 1.217(2) . ?
O9 C20 1.249(2) . ?
O10 N6 1.217(2) . ?
N5 O13 1.203(2) . ?
N5 O14 1.208(2) . ?
N5 C22 1.465(2) . ?
N6 C24 1.474(2) . ?
N1 H2 1.10(3) . ?
N4 H13 0.90(2) . ?
N4 H12 0.89(2) . ?
C21 C22 1.380(2) . ?
C21 C26 1.380(2) . ?
C21 C20 1.522(2) . ?
C24 C25 1.363(3) . ?
C24 C23 1.371(3) . ?
C25 C26 1.381(3) . ?
C25 H10 0.92(2) . ?
C22 C23 1.380(2) . ?
C23 H11 0.91(2) . ?
C26 H9 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O5 H2 113.3(10) . . ?
O2 N8 O1 123.46(16) . . ?
O2 N8 C5 118.40(16) . . ?
O1 N8 C5 118.14(16) . . ?
O3 N7 O4 123.6(2) . . ?
O3 N7 C3 118.23(17) . . ?
O4 N7 C3 118.16(18) . . ?
C4 C5 C6 122.86(16) . . ?
C4 C5 N8 118.39(15) . . ?
C6 C5 N8 118.73(16) . . ?
C4 C3 C2 122.89(16) . . ?
C4 C3 N7 117.19(15) . . ?
C2 C3 N7 119.81(15) . . ?
C5 C4 C3 117.04(16) . . ?
C5 C4 H20 123.6(12) . . ?
C3 C4 H20 119.3(12) . . ?
C7 C2 C3 117.42(15) . . ?
C7 C2 C1 117.35(15) . . ?
C3 C2 C1 125.23(16) . . ?
O6 C1 O5 126.69(15) . . ?
O6 C1 C2 116.72(15) . . ?
O5 C1 C2 116.45(14) . . ?
C6 C7 C2 121.03(17) . . ?
C6 C7 H18 118.3(13) . . ?
C2 C7 H18 120.7(13) . . ?
C5 C6 C7 118.74(19) . . ?
C5 C6 H19 120.4(15) . . ?
C7 C6 H19 120.8(15) . . ?
C11 C10 C9 118.93(18) . . ?
C11 C10 H5 118.6(13) . . ?
C9 C10 H5 122.2(13) . . ?
N2 C13 C12 120.13(17) . . ?
N2 C13 H3 117.4(12) . . ?
C12 C13 H3 122.4(12) . . ?
N2 C11 C10 120.77(18) . . ?
N2 C11 H4 118.7(13) . . ?
C10 C11 H4 120.5(13) . . ?
O12 C8 N3 123.98(16) . . ?
O12 C8 C9 119.50(15) . . ?
N3 C8 C9 116.49(15) . . ?
C9 C12 C13 119.71(17) . . ?
C9 C12 H6 120.9(14) . . ?
C13 C12 H6 119.4(14) . . ?
C12 C9 C10 118.89(15) . . ?
C12 C9 C8 118.38(15) . . ?
C10 C9 C8 122.72(16) . . ?
C8 N3 H7 119.8(15) . . ?
C8 N3 H8 126.5(16) . . ?
H7 N3 H8 114(2) . . ?
C11 N2 C13 121.54(16) . . ?
C11 N2 H1 116.3(13) . . ?
C13 N2 H1 122.1(13) . . ?
C15 C17 C18 118.52(16) . . ?
C15 C17 C16 122.64(16) . . ?
C18 C17 C16 118.84(15) . . ?
O7 C16 N4 123.91(16) . . ?
O7 C16 C17 119.16(15) . . ?
N4 C16 C17 116.93(15) . . ?
C17 C18 C19 119.57(18) . . ?
C17 C18 H15 122.6(13) . . ?
C19 C18 H15 117.8(13) . . ?
C17 C15 C14 118.89(18) . . ?
C17 C15 H14 123.9(14) . . ?
C14 C15 H14 117.2(14) . . ?
N1 C14 C15 122.13(19) . . ?
N1 C14 H16 116.9(16) . . ?
C15 C14 H16 120.9(16) . . ?
N1 C19 C18 120.90(18) . . ?
N1 C19 H17 117.6(14) . . ?
C18 C19 H17 121.4(14) . . ?
O13 N5 O14 124.5(2) . . ?
O13 N5 C22 118.00(18) . . ?
O14 N5 C22 117.48(18) . . ?
O10 N6 O11 124.04(17) . . ?
O10 N6 C24 118.04(18) . . ?
O11 N6 C24 117.91(19) . . ?
C14 N1 C19 119.96(16) . . ?
C14 N1 H2 114.2(13) . . ?
C19 N1 H2 125.6(13) . . ?
C16 N4 H13 119.1(14) . . ?
C16 N4 H12 125.4(15) . . ?
H13 N4 H12 115(2) . . ?
C22 C21 C26 116.78(15) . . ?
C22 C21 C20 123.28(14) . . ?
C26 C21 C20 119.85(16) . . ?
O8 C20 O9 126.60(15) . . ?
O8 C20 C21 117.61(15) . . ?
O9 C20 C21 115.78(14) . . ?
C25 C24 C23 122.77(16) . . ?
C25 C24 N6 119.06(17) . . ?
C23 C24 N6 118.17(18) . . ?
C24 C25 C26 118.19(18) . . ?
C24 C25 H10 122.0(13) . . ?
C26 C25 H10 119.8(13) . . ?
C23 C22 C21 123.18(16) . . ?
C23 C22 N5 117.13(17) . . ?
C21 C22 N5 119.66(15) . . ?
C24 C23 C22 116.99(18) . . ?
C24 C23 H11 121.2(13) . . ?
C22 C23 H11 121.7(13) . . ?
C21 C26 C25 122.08(19) . . ?
C21 C26 H9 118.7(13) . . ?
C25 C26 H9 119.2(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H5 O6 0.93(2) 2.48(2) 3.158(2) 129.8(17) . yes
C25 H10 O6 0.92(2) 2.65(2) 3.470(3) 149.2(17) 2_666 yes
C11 H4 O3 0.92(2) 2.55(2) 3.170(3) 125.7(16) 2_765 yes
C11 H4 O8 0.92(2) 2.41(2) 3.109(2) 133.5(16) . yes
C13 H3 O13 1.00(2) 2.68(2) 3.358(3) 125.5(15) 1_565 yes
N4 H13 O7 0.90(2) 1.99(2) 2.883(2) 179(2) 2_656 yes
N3 H7 O12 0.88(3) 2.09(3) 2.961(2) 175(2) 2_775 yes
N4 H12 O8 0.89(2) 1.97(3) 2.851(2) 169(2) . yes
C15 H14 O8 0.94(2) 2.60(2) 3.284(3) 130.0(17) . yes
N2 H1 O9 1.00(2) 1.63(2) 2.6199(18) 173(2) . yes
N3 H8 O6 0.86(2) 2.11(3) 2.969(2) 177(2) . yes
C14 H16 O6 0.92(3) 2.28(3) 3.032(2) 138(2) . yes
N1 H2 O5 1.10(3) 1.47(3) 2.5664(17) 174(2) . yes
N1 H2 O6 1.10(3) 2.61(3) 3.2408(19) 115.8(16) . yes

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_7_350K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922013'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_7_350K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.53 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_7_350K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.12 Ang.  
RESPONSE: The long N-H distance is characteristic of H2 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT430_complex_7_350K_shelxl 
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.87 Ang.  
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi-pi interaction.
;
_vrf_PLAT772_complex_7_350K_shelxl 
;
PROBLEM: Suspect O-H Bond in CIF: O5       --H2        ..       1.45 Ang.  
RESPONSE: The short H...O distance is characteristic of H2 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'isonicotinamide 2,4-dinitrobenzoate/benzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_weight         668.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8448(6)
_cell_length_b                   10.3745(6)
_cell_length_c                   15.5573(9)
_cell_angle_alpha                79.023(4)
_cell_angle_beta                 70.556(3)
_cell_angle_gamma                77.704(4)
_cell_volume                     1451.58(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    350
_cell_measurement_reflns_used    6180
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      34.96

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      350
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23376
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         35.631
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6895
_reflns_number_gt                3558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.76 command used to make multi_T datasets comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0760P)²+0.1848P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6895
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1639
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H19 H 1.472(3) 0.784(3) 0.1121(19) 0.083(9) Uiso 1 1 d . . . . .
H5 H 0.801(3) 0.662(3) 0.1684(19) 0.088(9) Uiso 1 1 d . . . . .
H10 H -0.023(3) 0.345(2) 0.6739(19) 0.080(8) Uiso 1 1 d . . . . .
H4 H 0.619(3) 0.578(3) 0.2854(17) 0.075(8) Uiso 1 1 d . . . . .
H18 H 1.307(3) 0.651(3) 0.182(2) 0.083(8) Uiso 1 1 d . . . . .
H20 H 1.480(2) 0.733(2) -0.1328(17) 0.058(6) Uiso 1 1 d . . . . .
H3 H 0.408(3) 0.933(3) 0.342(2) 0.101(9) Uiso 1 1 d . . . . .
H6 H 0.597(3) 1.030(3) 0.2251(18) 0.084(8) Uiso 1 1 d . . . . .
H17 H 1.084(3) 0.088(3) 0.160(2) 0.108(10) Uiso 1 1 d . . . . .
H15 H 0.894(3) -0.013(3) 0.2751(19) 0.094(9) Uiso 1 1 d . . . . .
H11 H 0.084(3) 0.173(3) 0.4456(17) 0.076(8) Uiso 1 1 d . . . . .
H9 H 0.149(3) 0.480(3) 0.6004(17) 0.074(8) Uiso 1 1 d . . . . .
H13 H 0.478(3) 0.121(3) 0.4932(18) 0.076(7) Uiso 1 1 d . . . . .
H7 H 1.039(3) 0.882(3) 0.035(2) 0.104(10) Uiso 1 1 d . . . . .
H12 H 0.543(3) 0.245(3) 0.4406(19) 0.083(9) Uiso 1 1 d . . . . .
H14 H 0.740(3) 0.333(3) 0.383(2) 0.105(10) Uiso 1 1 d . . . . .
H1 H 0.428(3) 0.700(3) 0.371(2) 0.100(9) Uiso 1 1 d . . . . .
H8 H 0.993(3) 0.772(3) 0.102(2) 0.094(10) Uiso 1 1 d . . . . .
H16 H 0.924(4) 0.422(3) 0.266(2) 0.121(11) Uiso 1 1 d . . . . .
H2 H 1.102(4) 0.318(3) 0.162(2) 0.122(11) Uiso 1 1 d . . . . .
O2 O 1.6311(2) 0.89731(19) -0.13935(14) 0.0876(6) Uani 1 1 d . . . . .
O1 O 1.6635(2) 0.8889(2) -0.01011(16) 0.1074(8) Uani 1 1 d . . . . .
O3 O 1.3564(3) 0.5736(4) -0.16507(19) 0.1595(13) Uani 1 1 d . . . . .
O4 O 1.1564(3) 0.5711(3) -0.05999(16) 0.1201(9) Uani 1 1 d . . . . .
O5 O 1.20627(16) 0.40184(16) 0.10171(12) 0.0695(5) Uani 1 1 d . . . . .
O6 O 1.05669(17) 0.57281(16) 0.16758(13) 0.0774(5) Uani 1 1 d . . . . .
N8 N 1.6043(2) 0.8592(2) -0.05832(17) 0.0652(6) Uani 1 1 d . . . . .
N7 N 1.2807(3) 0.5890(2) -0.08910(18) 0.0831(7) Uani 1 1 d . . . . .
C5 C 1.4937(2) 0.7715(2) -0.01546(15) 0.0506(5) Uani 1 1 d . . . . .
C3 C 1.3406(2) 0.6383(2) -0.02930(15) 0.0503(5) Uani 1 1 d . . . . .
C4 C 1.4464(2) 0.7176(2) -0.07105(17) 0.0522(6) Uani 1 1 d . . . . .
C2 C 1.2843(2) 0.6105(2) 0.06483(15) 0.0505(5) Uani 1 1 d . . . . .
C1 C 1.1708(2) 0.5224(2) 0.11455(16) 0.0571(6) Uani 1 1 d . . . . .
C7 C 1.3368(3) 0.6678(3) 0.11754(18) 0.0687(7) Uani 1 1 d . . . . .
C6 C 1.4412(3) 0.7492(3) 0.07766(19) 0.0682(7) Uani 1 1 d . . . . .
C10 C 0.7292(3) 0.7202(2) 0.20361(19) 0.0660(7) Uani 1 1 d . . . . .
C13 C 0.4964(3) 0.8776(3) 0.30374(19) 0.0682(7) Uani 1 1 d . . . . .
C11 C 0.6179(3) 0.6681(3) 0.27232(18) 0.0671(7) Uani 1 1 d . . . . .
C8 C 0.8410(2) 0.9219(2) 0.11103(16) 0.0593(6) Uani 1 1 d . . . . .
C12 C 0.6043(3) 0.9353(2) 0.23577(18) 0.0639(7) Uani 1 1 d . . . . .
C9 C 0.7235(2) 0.8561(2) 0.18573(15) 0.0539(6) Uani 1 1 d . . . . .
O12 O 0.81503(17) 1.03960(16) 0.08333(12) 0.0767(5) Uani 1 1 d . . . . .
N3 N 0.9670(3) 0.8478(3) 0.0815(2) 0.0975(10) Uani 1 1 d . . . . .
N2 N 0.5059(2) 0.7469(2) 0.32098(14) 0.0612(5) Uani 1 1 d . . . . .
C17 C 0.7943(2) 0.1479(2) 0.34096(15) 0.0510(5) Uani 1 1 d . . . . .
C16 C 0.6736(2) 0.0813(2) 0.41015(16) 0.0551(6) Uani 1 1 d . . . . .
C18 C 0.8976(3) 0.0773(3) 0.2769(2) 0.0731(8) Uani 1 1 d . . . . .
C15 C 0.8050(3) 0.2772(3) 0.3395(2) 0.0879(10) Uani 1 1 d . . . . .
C14 C 0.9167(3) 0.3318(3) 0.2726(2) 0.0884(10) Uani 1 1 d . . . . .
C19 C 1.0076(3) 0.1380(3) 0.2114(2) 0.0782(8) Uani 1 1 d . . . . .
O8 O 0.46955(18) 0.43791(16) 0.40645(14) 0.0882(6) Uani 1 1 d . . . . .
O11 O -0.1622(2) 0.1690(2) 0.69171(16) 0.1028(7) Uani 1 1 d . . . . .
O9 O 0.30486(17) 0.61708(15) 0.43768(13) 0.0735(5) Uani 1 1 d . . . . .
O10 O -0.1232(2) 0.0968(2) 0.56354(19) 0.1083(8) Uani 1 1 d . . . . .
N5 N 0.2851(3) 0.3075(3) 0.33875(16) 0.0826(7) Uani 1 1 d . . . . .
N6 N -0.0987(2) 0.1648(2) 0.61026(19) 0.0766(7) Uani 1 1 d . . . . .
O13 O 0.3359(4) 0.1982(3) 0.31690(17) 0.1486(12) Uani 1 1 d . . . . .
O14 O 0.3009(3) 0.4090(3) 0.28740(15) 0.1303(10) Uani 1 1 d . . . . .
O7 O 0.68887(18) -0.04023(15) 0.42306(13) 0.0800(6) Uani 1 1 d . . . . .
N1 N 1.0145(2) 0.26318(19) 0.21066(14) 0.0615(5) Uani 1 1 d . . . . .
N4 N 0.5563(2) 0.1588(2) 0.45303(17) 0.0766(7) Uani 1 1 d . . . . .
C21 C 0.2251(2) 0.4098(2) 0.47979(15) 0.0516(5) Uani 1 1 d . . . . .
C20 C 0.3450(2) 0.4945(2) 0.43671(16) 0.0574(6) Uani 1 1 d . . . . .
C24 C 0.0148(2) 0.2506(2) 0.56503(17) 0.0587(6) Uani 1 1 d . . . . .
C25 C 0.0337(3) 0.3382(3) 0.61297(19) 0.0704(7) Uani 1 1 d . . . . .
C22 C 0.2006(2) 0.3182(2) 0.43529(15) 0.0533(5) Uani 1 1 d . . . . .
C23 C 0.0970(3) 0.2366(2) 0.47613(18) 0.0589(6) Uani 1 1 d . . . . .
C26 C 0.1386(3) 0.4172(3) 0.56953(18) 0.0693(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N8 1.203(3) . ?
O1 N8 1.205(3) . ?
O3 N7 1.188(3) . ?
O4 N7 1.197(3) . ?
O5 C1 1.260(3) . ?
O5 H2 1.45(4) . ?
O6 C1 1.230(3) . ?
N8 C5 1.471(3) . ?
N7 C3 1.466(3) . ?
C5 C4 1.357(3) . ?
C5 C6 1.358(3) . ?
C3 C4 1.376(3) . ?
C3 C2 1.379(3) . ?
C4 H20 0.90(2) . ?
C2 C7 1.375(3) . ?
C2 C1 1.508(3) . ?
C7 C6 1.379(3) . ?
C7 H18 0.94(3) . ?
C6 H19 0.86(3) . ?
C10 C11 1.374(3) . ?
C10 C9 1.376(3) . ?
C10 H5 0.92(3) . ?
C13 N2 1.321(3) . ?
C13 C12 1.373(3) . ?
C13 H3 1.01(3) . ?
C11 N2 1.324(3) . ?
C11 H4 0.91(3) . ?
C8 O12 1.218(3) . ?
C8 N3 1.300(3) . ?
C8 C9 1.514(3) . ?
C12 C9 1.373(3) . ?
C12 H6 0.96(3) . ?
N3 H7 0.91(3) . ?
N3 H8 0.82(3) . ?
N2 H1 1.02(3) . ?
C17 C18 1.361(3) . ?
C17 C15 1.363(3) . ?
C17 C16 1.504(3) . ?
C16 O7 1.223(3) . ?
C16 N4 1.312(3) . ?
C18 C19 1.385(3) . ?
C18 H15 0.95(3) . ?
C15 C14 1.376(3) . ?
C15 H14 0.96(3) . ?
C14 N1 1.309(3) . ?
C14 H16 0.94(3) . ?
C19 N1 1.313(3) . ?
C19 H17 1.03(3) . ?
O8 C20 1.218(3) . ?
O11 N6 1.217(3) . ?
O9 C20 1.250(3) . ?
O10 N6 1.212(3) . ?
N5 O14 1.199(3) . ?
N5 O13 1.202(3) . ?
N5 C22 1.467(3) . ?
N6 C24 1.483(3) . ?
N1 H2 1.12(4) . ?
N4 H13 0.92(3) . ?
N4 H12 0.87(3) . ?
C21 C22 1.378(3) . ?
C21 C26 1.379(3) . ?
C21 C20 1.518(3) . ?
C24 C25 1.356(4) . ?
C24 C23 1.367(3) . ?
C25 C26 1.372(3) . ?
C25 H10 0.93(3) . ?
C22 C23 1.376(3) . ?
C23 H11 0.93(3) . ?
C26 H9 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O5 H2 113.5(12) . . ?
O2 N8 O1 123.4(2) . . ?
O2 N8 C5 118.6(2) . . ?
O1 N8 C5 118.0(2) . . ?
O3 N7 O4 123.4(3) . . ?
O3 N7 C3 118.3(2) . . ?
O4 N7 C3 118.3(2) . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 N8 118.4(2) . . ?
C6 C5 N8 119.1(2) . . ?
C4 C3 C2 123.0(2) . . ?
C4 C3 N7 117.3(2) . . ?
C2 C3 N7 119.61(19) . . ?
C5 C4 C3 117.2(2) . . ?
C5 C4 H20 122.8(14) . . ?
C3 C4 H20 119.9(14) . . ?
C7 C2 C3 117.05(19) . . ?
C7 C2 C1 117.5(2) . . ?
C3 C2 C1 125.5(2) . . ?
O6 C1 O5 126.36(19) . . ?
O6 C1 C2 117.1(2) . . ?
O5 C1 C2 116.35(19) . . ?
C2 C7 C6 121.2(2) . . ?
C2 C7 H18 122.2(16) . . ?
C6 C7 H18 116.5(17) . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H19 121.8(19) . . ?
C7 C6 H19 119.3(19) . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H5 117.8(18) . . ?
C9 C10 H5 122.8(18) . . ?
N2 C13 C12 120.7(2) . . ?
N2 C13 H3 117.9(17) . . ?
C12 C13 H3 121.4(17) . . ?
N2 C11 C10 120.8(2) . . ?
N2 C11 H4 118.1(16) . . ?
C10 C11 H4 121.1(16) . . ?
O12 C8 N3 123.6(2) . . ?
O12 C8 C9 119.6(2) . . ?
N3 C8 C9 116.8(2) . . ?
C9 C12 C13 119.6(2) . . ?
C9 C12 H6 120.6(16) . . ?
C13 C12 H6 119.8(16) . . ?
C12 C9 C10 118.6(2) . . ?
C12 C9 C8 118.6(2) . . ?
C10 C9 C8 122.7(2) . . ?
C8 N3 H7 119.7(19) . . ?
C8 N3 H8 127(2) . . ?
H7 N3 H8 113(3) . . ?
C13 N2 C11 121.1(2) . . ?
C13 N2 H1 123.0(16) . . ?
C11 N2 H1 115.9(16) . . ?
C18 C17 C15 118.1(2) . . ?
C18 C17 C16 119.2(2) . . ?
C15 C17 C16 122.7(2) . . ?
O7 C16 N4 123.7(2) . . ?
O7 C16 C17 119.2(2) . . ?
N4 C16 C17 117.1(2) . . ?
C17 C18 C19 120.0(2) . . ?
C17 C18 H15 120.9(18) . . ?
C19 C18 H15 119.1(18) . . ?
C17 C15 C14 119.1(2) . . ?
C17 C15 H14 124.1(18) . . ?
C14 C15 H14 116.8(18) . . ?
N1 C14 C15 122.1(2) . . ?
N1 C14 H16 116(2) . . ?
C15 C14 H16 122(2) . . ?
N1 C19 C18 120.8(3) . . ?
N1 C19 H17 117.9(17) . . ?
C18 C19 H17 121.2(17) . . ?
O14 N5 O13 124.5(3) . . ?
O14 N5 C22 117.5(3) . . ?
O13 N5 C22 118.0(2) . . ?
O10 N6 O11 124.5(2) . . ?
O10 N6 C24 118.0(2) . . ?
O11 N6 C24 117.5(3) . . ?
C14 N1 C19 119.8(2) . . ?
C14 N1 H2 114.7(16) . . ?
C19 N1 H2 125.4(16) . . ?
C16 N4 H13 119.1(15) . . ?
C16 N4 H12 123.3(18) . . ?
H13 N4 H12 117(2) . . ?
C22 C21 C26 116.4(2) . . ?
C22 C21 C20 123.39(19) . . ?
C26 C21 C20 120.2(2) . . ?
O8 C20 O9 126.4(2) . . ?
O8 C20 C21 117.96(19) . . ?
O9 C20 C21 115.63(19) . . ?
C25 C24 C23 122.9(2) . . ?
C25 C24 N6 119.2(2) . . ?
C23 C24 N6 117.9(2) . . ?
C24 C25 C26 118.2(2) . . ?
C24 C25 H10 121.1(16) . . ?
C26 C25 H10 120.6(16) . . ?
C23 C22 C21 123.3(2) . . ?
C23 C22 N5 117.1(2) . . ?
C21 C22 N5 119.6(2) . . ?
C24 C23 C22 116.8(2) . . ?
C24 C23 H11 121.1(16) . . ?
C22 C23 H11 122.1(16) . . ?
C25 C26 C21 122.4(3) . . ?
C25 C26 H9 118.8(16) . . ?
C21 C26 H9 118.8(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H5 O6 0.92(3) 2.49(3) 3.173(3) 131(2) . yes
C25 H10 O6 0.93(3) 2.66(3) 3.483(4) 148(2) 2_666 yes
C11 H4 O3 0.91(3) 2.59(2) 3.190(4) 124(2) 2_765 yes
C11 H4 O8 0.91(3) 2.42(3) 3.122(3) 134(2) . yes
C13 H3 O13 1.01(3) 2.68(3) 3.377(4) 127(2) 1_565 yes
N4 H13 O7 0.92(3) 1.96(3) 2.884(3) 179(2) 2_656 yes
N3 H7 O12 0.91(3) 2.07(3) 2.968(3) 172(3) 2_775 yes
N4 H12 O8 0.87(3) 2.01(3) 2.864(3) 166(3) . yes
C15 H14 O8 0.96(3) 2.59(3) 3.286(3) 130(2) . yes
N2 H1 O9 1.02(3) 1.60(3) 2.615(2) 172(3) . yes
N3 H8 O6 0.82(3) 2.18(3) 2.995(3) 176(3) . yes
C14 H16 O6 0.94(3) 2.26(4) 3.038(3) 139(3) . yes
N1 H2 O5 1.12(4) 1.45(4) 2.570(2) 175(3) . yes
N1 H2 O6 1.12(4) 2.59(3) 3.241(2) 116(2) . yes

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_6_300K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922008'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_6_300K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      48.76 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N2 O1, C7 H3 N2 O6'
_chemical_formula_sum            'C13 H10 N4 O7'
_chemical_formula_weight         334.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.22350(8)
_cell_length_b                   11.66850(7)
_cell_length_c                   11.95710(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.9360(6)
_cell_angle_gamma                90
_cell_volume                     1481.174(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    11445
_cell_measurement_theta_max      35.068261595
_cell_measurement_theta_min      1.85093292802

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.999382801018
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.067: AIMLESS, version 0.7.3 : 15/08/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32404
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.859
_diffrn_reflns_theta_max         36.080
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7216
_reflns_number_gt                4275
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'

_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'

_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
 Peak Q1 is likely to be water solvent. It is not possible to fully resolve
 the water structure. An isotropic refinement is the most stable. It's refined
 occupancy is 9 % and so it has been left out of the structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0910P)²+0.0119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7216
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1857
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.4804(13) 0.2999(13) 0.4121(14) 0.062(4) Uiso 1 1 d . . . . .
H10 H 0.9868(15) 0.4211(14) 0.6838(14) 0.064(4) Uiso 1 1 d . . . . .
H7 H 0.5701(14) 0.6097(13) 0.3273(14) 0.057(4) Uiso 1 1 d . . . . .
H3 H 0.2848(15) 0.3084(14) 0.2570(14) 0.064(4) Uiso 1 1 d . . . . .
H8 H 0.9286(14) 0.0970(14) 0.8948(14) 0.060(4) Uiso 1 1 d . . . . .
H9 H 1.1456(17) 0.3652(13) 0.8540(15) 0.070(4) Uiso 1 1 d . . . . .
H4 H 0.0742(18) 0.5630(14) -0.0217(16) 0.072(4) Uiso 1 1 d . . . . .
H5 H 0.2072(15) 0.6149(13) 0.0251(14) 0.058(4) Uiso 1 1 d . . . . .
H6 H 0.3757(14) 0.6284(13) 0.1721(14) 0.056(4) Uiso 1 1 d . . . . .
H1 H 0.621(2) 0.4574(17) 0.437(2) 0.091(6) Uiso 1 1 d . . . . .
O1 O 0.73588(9) 0.43535(7) 0.55880(7) 0.0588(2) Uani 1 1 d . . . . .
O2 O 0.71243(9) 0.25521(9) 0.49702(8) 0.0725(3) Uani 1 1 d . . . . .
O3 O 0.63050(9) 0.18574(10) 0.69161(12) 0.0778(3) Uani 1 1 d . . . . .
O5 O 1.25961(9) 0.22671(11) 1.00455(9) 0.0778(3) Uani 1 1 d . . . . .
O6 O 1.13234(11) 0.11362(11) 1.05173(9) 0.0829(3) Uani 1 1 d . . . . .
O4 O 0.73609(11) 0.02885(9) 0.71557(12) 0.0791(3) Uani 1 1 d . . . . .
N3 N 0.72904(9) 0.13305(9) 0.71541(10) 0.0532(2) Uani 1 1 d . . . . .
C1 C 0.76039(9) 0.33035(9) 0.57049(8) 0.0436(2) Uani 1 1 d . . . . .
N4 N 1.15509(10) 0.18444(10) 0.98784(9) 0.0579(3) Uani 1 1 d . . . . .
C5 C 1.05174(10) 0.22312(10) 0.88312(9) 0.0457(2) Uani 1 1 d . . . . .
C2 C 0.85884(9) 0.29463(8) 0.68502(8) 0.03919(19) Uani 1 1 d . . . . .
C7 C 0.97152(10) 0.35493(9) 0.72509(10) 0.0454(2) Uani 1 1 d . . . . .
C3 C 0.84680(9) 0.19838(8) 0.74944(9) 0.0413(2) Uani 1 1 d . . . . .
C4 C 0.94105(11) 0.16152(9) 0.84941(9) 0.0454(2) Uani 1 1 d . . . . .
C6 C 1.06924(10) 0.31957(10) 0.82347(10) 0.0480(2) Uani 1 1 d . . . . .
O7 O 0.10139(7) 0.40304(8) 0.11478(9) 0.0608(2) Uani 1 1 d . . . . .
N2 N 0.15307(9) 0.56053(9) 0.03205(9) 0.0518(2) Uani 1 1 d . . . . .
N1 N 0.53606(9) 0.45990(9) 0.37538(8) 0.0488(2) Uani 1 1 d . . . . .
C10 C 0.30919(8) 0.47160(8) 0.19924(9) 0.0399(2) Uani 1 1 d . . . . .
C11 C 0.17857(9) 0.47645(9) 0.11004(9) 0.0427(2) Uani 1 1 d . . . . .
C8 C 0.50857(10) 0.55225(11) 0.30697(10) 0.0510(3) Uani 1 1 d . . . . .
C9 C 0.39545(9) 0.56058(10) 0.21667(10) 0.0463(2) Uani 1 1 d . . . . .
C13 C 0.45579(11) 0.37161(11) 0.35889(11) 0.0526(3) Uani 1 1 d . . . . .
C12 C 0.34118(10) 0.37538(10) 0.27094(10) 0.0487(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2534(14) . ?
O2 C1 1.2342(14) . ?
O3 N3 1.2157(14) . ?
O5 N4 1.2277(16) . ?
O6 N4 1.2076(16) . ?
O4 N3 1.2184(14) . ?
N3 C3 1.4643(14) . ?
C1 C2 1.5126(13) . ?
N4 C5 1.4746(13) . ?
C5 C4 1.3774(16) . ?
C5 C6 1.3801(16) . ?
C2 C7 1.3896(14) . ?
C2 C3 1.3930(14) . ?
C7 C6 1.3854(14) . ?
C7 H10 0.961(16) . ?
C3 C4 1.3828(14) . ?
C4 H8 0.965(16) . ?
C6 H9 0.974(17) . ?
O7 C11 1.2325(13) . ?
N2 C11 1.3194(14) . ?
N2 H4 0.910(19) . ?
N2 H5 0.900(16) . ?
N1 C8 1.3273(15) . ?
N1 C13 1.3404(16) . ?
N1 H1 0.99(2) . ?
C10 C12 1.3873(14) . ?
C10 C9 1.3884(14) . ?
C10 C11 1.5084(13) . ?
C8 C9 1.3775(14) . ?
C8 H7 0.936(15) . ?
C9 H6 0.939(15) . ?
C13 C12 1.3727(15) . ?
C13 H2 1.033(15) . ?
C12 H3 0.985(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N3 O4 123.97(11) . . ?
O3 N3 C3 118.18(10) . . ?
O4 N3 C3 117.82(10) . . ?
O2 C1 O1 125.86(9) . . ?
O2 C1 C2 118.05(10) . . ?
O1 C1 C2 116.09(9) . . ?
O6 N4 O5 123.98(11) . . ?
O6 N4 C5 118.50(11) . . ?
O5 N4 C5 117.52(11) . . ?
C4 C5 C6 122.71(9) . . ?
C4 C5 N4 118.36(10) . . ?
C6 C5 N4 118.93(10) . . ?
C7 C2 C3 117.28(9) . . ?
C7 C2 C1 119.23(9) . . ?
C3 C2 C1 123.33(9) . . ?
C6 C7 C2 121.54(10) . . ?
C6 C7 H10 116.8(10) . . ?
C2 C7 H10 121.6(10) . . ?
C4 C3 C2 122.99(10) . . ?
C4 C3 N3 116.53(9) . . ?
C2 C3 N3 120.45(9) . . ?
C5 C4 C3 117.07(10) . . ?
C5 C4 H8 121.6(9) . . ?
C3 C4 H8 121.3(9) . . ?
C5 C6 C7 118.39(10) . . ?
C5 C6 H9 120.5(10) . . ?
C7 C6 H9 120.9(10) . . ?
C11 N2 H4 117.4(11) . . ?
C11 N2 H5 126.2(10) . . ?
H4 N2 H5 116.3(14) . . ?
C8 N1 C13 121.51(9) . . ?
C8 N1 H1 116.9(11) . . ?
C13 N1 H1 121.5(11) . . ?
C12 C10 C9 118.98(9) . . ?
C12 C10 C11 117.68(9) . . ?
C9 C10 C11 123.26(9) . . ?
O7 C11 N2 123.70(9) . . ?
O7 C11 C10 118.54(9) . . ?
N2 C11 C10 117.76(9) . . ?
N1 C8 C9 120.74(11) . . ?
N1 C8 H7 114.6(9) . . ?
C9 C8 H7 124.6(9) . . ?
C8 C9 C10 119.03(10) . . ?
C8 C9 H6 119.4(9) . . ?
C10 C9 H6 121.4(9) . . ?
N1 C13 C12 120.40(10) . . ?
N1 C13 H2 120.0(8) . . ?
C12 C13 H2 119.6(8) . . ?
C13 C12 C10 119.31(10) . . ?
C13 C12 H3 119.7(9) . . ?
C10 C12 H3 120.9(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H8 O6 0.965(16) 2.683(16) 3.6076(16) 160.7(12) 3_757 yes
C6 H9 O4 0.974(17) 2.611(17) 3.4084(17) 139.2(13) 2_756 yes
N2 H4 O7 0.910(19) 1.964(19) 2.8574(12) 166.9(16) 3_565 yes
N2 H5 O2 0.900(16) 1.929(16) 2.8107(13) 166.0(14) 2_655 yes
C9 H6 O2 0.939(15) 2.441(16) 3.3383(14) 159.7(12) 2_655 yes
N1 H1 O1 0.99(2) 1.63(2) 2.5941(12) 163.2(18) . yes
N1 H1 O2 0.99(2) 2.58(2) 3.1417(13) 115.6(14) . yes
C8 H7 O5 0.936(15) 2.658(16) 3.4909(15) 148.5(12) 2_756 yes
C4 H8 O6 0.965(16) 2.683(16) 3.6076(16) 160.7(12) 3_757 yes
C6 H9 O4 0.974(17) 2.611(17) 3.4084(17) 139.2(13) 2_756 yes
N2 H4 O7 0.910(19) 1.964(19) 2.8574(12) 166.9(16) 3_565 yes
N2 H5 O2 0.900(16) 1.929(16) 2.8107(13) 166.0(14) 2_655 yes
C9 H6 O2 0.939(15) 2.441(16) 3.3383(14) 159.7(12) 2_655 yes
N1 H1 O1 0.99(2) 1.63(2) 2.5941(12) 163.2(18) . yes
N1 H1 O2 0.99(2) 2.58(2) 3.1417(13) 115.6(14) . yes

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_6_200K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922009'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_6_200K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      49.64 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N2 O1, C7 H3 N2 O6'
_chemical_formula_sum            'C13 H10 N4 O7'
_chemical_formula_weight         334.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.11940(5)
_cell_length_b                   11.56830(5)
_cell_length_c                   11.89730(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.2370(4)
_cell_angle_gamma                90
_cell_volume                     1453.509(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    15464
_cell_measurement_theta_max      35.9408992799
_cell_measurement_theta_min      1.86468299248

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.034
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.999203086273
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.067: AIMLESS, version 0.7.3 : 15/08/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31718
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.442
_diffrn_reflns_theta_max         36.135
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7061
_reflns_number_gt                5374
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'

_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'

_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
 Peak Q1 is likely to be water solvent. It is not possible to fully resolve
 the water structure. An isotropic refinement is the most stable. It's refined
 occupancy is 9% so it has been left out of the structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²+0.0943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7061
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H2 H 0.4808(13) 0.3012(12) 0.4154(13) 0.040(3) Uiso 1 1 d . . . . .
H10 H 0.9816(14) 0.4243(12) 0.6838(13) 0.041(3) Uiso 1 1 d . . . . .
H7 H 0.5705(13) 0.6125(12) 0.3260(13) 0.038(3) Uiso 1 1 d . . . . .
H3 H 0.2831(13) 0.3083(13) 0.2585(13) 0.041(3) Uiso 1 1 d . . . . .
H8 H 0.9246(13) 0.0999(12) 0.8966(12) 0.034(3) Uiso 1 1 d . . . . .
H9 H 1.1426(15) 0.3649(12) 0.8543(14) 0.045(4) Uiso 1 1 d . . . . .
H4 H 0.0716(15) 0.5679(12) -0.0245(14) 0.045(4) Uiso 1 1 d . . . . .
H5 H 0.2069(14) 0.6114(12) 0.0224(13) 0.039(3) Uiso 1 1 d . . . . .
H6 H 0.3775(13) 0.6275(11) 0.1669(12) 0.034(3) Uiso 1 1 d . . . . .
H1 H 0.6199(19) 0.4560(16) 0.4422(18) 0.070(5) Uiso 1 1 d . . . . .
O1 O 0.73603(7) 0.43803(6) 0.55893(6) 0.03620(16) Uani 1 1 d . . . . .
O2 O 0.70995(8) 0.25459(7) 0.49909(7) 0.0451(2) Uani 1 1 d . . . . .
O3 O 0.62683(7) 0.18478(7) 0.69360(9) 0.0479(2) Uani 1 1 d . . . . .
O5 O 1.25908(7) 0.22721(8) 1.00505(7) 0.0469(2) Uani 1 1 d . . . . .
O6 O 1.12991(9) 0.11281(8) 1.05335(7) 0.0497(2) Uani 1 1 d . . . . .
O4 O 0.73486(8) 0.02616(7) 0.71570(9) 0.0481(2) Uani 1 1 d . . . . .
N3 N 0.72631(8) 0.13184(7) 0.71658(8) 0.03238(16) Uani 1 1 d . . . . .
C1 C 0.75895(8) 0.33131(7) 0.57187(7) 0.02691(15) Uani 1 1 d . . . . .
N4 N 1.15379(8) 0.18500(8) 0.98886(7) 0.03486(17) Uani 1 1 d . . . . .
C5 C 1.05040(8) 0.22367(7) 0.88460(7) 0.02778(15) Uani 1 1 d . . . . .
C2 C 0.85726(7) 0.29585(7) 0.68667(7) 0.02450(14) Uani 1 1 d . . . . .
C7 C 0.97034(8) 0.35739(7) 0.72669(7) 0.02799(15) Uani 1 1 d . . . . .
C3 C 0.84493(7) 0.19844(7) 0.75100(7) 0.02571(14) Uani 1 1 d . . . . .
C4 C 0.93902(8) 0.16081(7) 0.85092(7) 0.02806(15) Uani 1 1 d . . . . .
C6 C 1.06834(8) 0.32152(8) 0.82476(8) 0.02928(16) Uani 1 1 d . . . . .
O7 O 0.09990(6) 0.40085(6) 0.11518(7) 0.03736(16) Uani 1 1 d . . . . .
N2 N 0.15379(7) 0.55897(7) 0.03004(7) 0.03223(16) Uani 1 1 d . . . . .
N1 N 0.53519(7) 0.46003(7) 0.37609(7) 0.03048(15) Uani 1 1 d . . . . .
C10 C 0.30896(7) 0.47028(7) 0.19874(7) 0.02508(14) Uani 1 1 d . . . . .
C11 C 0.17840(7) 0.47469(7) 0.10945(7) 0.02640(15) Uani 1 1 d . . . . .
C8 C 0.50826(8) 0.55323(8) 0.30707(8) 0.03153(17) Uani 1 1 d . . . . .
C9 C 0.39518(8) 0.56097(7) 0.21591(8) 0.02897(16) Uani 1 1 d . . . . .
C13 C 0.45489(9) 0.37019(8) 0.35968(8) 0.03296(18) Uani 1 1 d . . . . .
C12 C 0.34030(8) 0.37335(8) 0.27110(8) 0.03024(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2602(11) . ?
O2 C1 1.2405(11) . ?
O3 N3 1.2182(11) . ?
O5 N4 1.2268(12) . ?
O6 N4 1.2183(12) . ?
O4 N3 1.2265(11) . ?
N3 C3 1.4707(11) . ?
C1 C2 1.5147(11) . ?
N4 C5 1.4723(11) . ?
C5 C4 1.3829(13) . ?
C5 C6 1.3846(12) . ?
C2 C3 1.3929(11) . ?
C2 C7 1.3929(12) . ?
C7 C6 1.3875(12) . ?
C7 H10 0.956(14) . ?
C3 C4 1.3852(11) . ?
C4 H8 0.934(14) . ?
C6 H9 0.936(15) . ?
O7 C11 1.2383(10) . ?
N2 C11 1.3253(11) . ?
N2 H4 0.947(16) . ?
N2 H5 0.871(15) . ?
N1 C8 1.3313(12) . ?
N1 C13 1.3440(13) . ?
N1 H1 1.02(2) . ?
C10 C12 1.3900(12) . ?
C10 C9 1.3925(12) . ?
C10 C11 1.5077(11) . ?
C8 C9 1.3827(11) . ?
C8 H7 0.950(14) . ?
C9 H6 0.948(13) . ?
C13 C12 1.3767(13) . ?
C13 H2 1.020(14) . ?
C12 H3 0.966(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N3 O4 124.50(9) . . ?
O3 N3 C3 118.13(8) . . ?
O4 N3 C3 117.35(8) . . ?
O2 C1 O1 126.00(8) . . ?
O2 C1 C2 118.10(8) . . ?
O1 C1 C2 115.90(7) . . ?
O6 N4 O5 124.00(8) . . ?
O6 N4 C5 118.18(9) . . ?
O5 N4 C5 117.81(8) . . ?
C4 C5 C6 122.75(7) . . ?
C4 C5 N4 118.47(8) . . ?
C6 C5 N4 118.77(8) . . ?
C3 C2 C7 117.33(7) . . ?
C3 C2 C1 123.18(7) . . ?
C7 C2 C1 119.30(7) . . ?
C6 C7 C2 121.47(8) . . ?
C6 C7 H10 119.4(9) . . ?
C2 C7 H10 119.1(9) . . ?
C4 C3 C2 123.24(8) . . ?
C4 C3 N3 116.42(7) . . ?
C2 C3 N3 120.31(7) . . ?
C5 C4 C3 116.79(7) . . ?
C5 C4 H8 122.0(8) . . ?
C3 C4 H8 121.0(8) . . ?
C5 C6 C7 118.37(8) . . ?
C5 C6 H9 119.8(9) . . ?
C7 C6 H9 121.6(9) . . ?
C11 N2 H4 120.6(9) . . ?
C11 N2 H5 126.3(10) . . ?
H4 N2 H5 113.1(13) . . ?
C8 N1 C13 121.72(8) . . ?
C8 N1 H1 119.1(10) . . ?
C13 N1 H1 119.1(10) . . ?
C12 C10 C9 119.29(7) . . ?
C12 C10 C11 117.59(7) . . ?
C9 C10 C11 123.01(7) . . ?
O7 C11 N2 123.70(7) . . ?
O7 C11 C10 118.54(7) . . ?
N2 C11 C10 117.75(7) . . ?
N1 C8 C9 120.66(8) . . ?
N1 C8 H7 115.6(9) . . ?
C9 C8 H7 123.8(9) . . ?
C8 C9 C10 118.79(8) . . ?
C8 C9 H6 119.9(8) . . ?
C10 C9 H6 121.3(8) . . ?
N1 C13 C12 120.29(8) . . ?
N1 C13 H2 118.1(8) . . ?
C12 C13 H2 121.6(8) . . ?
C13 C12 C10 119.22(8) . . ?
C13 C12 H3 120.3(8) . . ?
C10 C12 H3 120.4(8) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H8 O6 0.934(14) 2.646(14) 3.5285(12) 157.8(11) 3_757 yes
C6 H9 O4 0.936(15) 2.596(15) 3.3591(13) 139.0(12) 2_756 yes
N2 H4 O7 0.947(16) 1.909(16) 2.8475(10) 171.0(14) 3_565 yes
N2 H5 O2 0.871(15) 1.953(15) 2.8046(11) 165.7(13) 2_655 yes
C9 H6 O2 0.948(13) 2.410(14) 3.3249(11) 162.2(11) 2_655 yes
N1 H1 O1 1.02(2) 1.59(2) 2.5968(10) 168.9(17) . yes
N1 H1 O2 1.02(2) 2.543(19) 3.1282(11) 116.0(13) . yes
C8 H7 O5 0.950(14) 2.647(14) 3.4814(12) 146.8(11) 2_756 yes
C4 H8 O6 0.934(14) 2.646(14) 3.5285(12) 157.8(11) 3_757 yes
C6 H9 O4 0.936(15) 2.596(15) 3.3591(13) 139.0(12) 2_756 yes
N2 H4 O7 0.947(16) 1.909(16) 2.8475(10) 171.0(14) 3_565 yes
N2 H5 O2 0.871(15) 1.953(15) 2.8046(11) 165.7(13) 2_655 yes
C9 H6 O2 0.948(13) 2.410(14) 3.3249(11) 162.2(11) 2_655 yes
N1 H1 O1 1.02(2) 1.59(2) 2.5968(10) 168.9(17) . yes
N1 H1 O2 1.02(2) 2.543(19) 3.1282(11) 116.0(13) . yes

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_250K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922003'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_5_250K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.62 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_250K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.14 Ang.  
RESPONSE: The long N-H distance is characteristic of H3 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_weight         410.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0100 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1747(3)
_cell_length_b                   14.3223(6)
_cell_length_c                   18.3518(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.6162(19)
_cell_angle_gamma                90
_cell_volume                     1883.83(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    250
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      43.75

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34716
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         41.368
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6517
_reflns_number_gt                5015
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.67 command used to make multi_T datasets comparable: 0.67 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0695P)²+0.2788P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6517
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 1.128(2) 0.6667(12) 0.3972(9) 0.057(5) Uiso 1 1 d . . . . .
H8 H 1.061(2) 0.5625(12) 0.1887(9) 0.050(4) Uiso 1 1 d . . . . .
H7 H 1.100(2) 0.6928(13) 0.2702(10) 0.059(5) Uiso 1 1 d . . . . .
H5 H 1.126(2) 0.5151(11) 0.4439(8) 0.044(4) Uiso 1 1 d . . . . .
H1 H 1.108(3) 0.2780(16) 0.4630(12) 0.089(7) Uiso 1 1 d . . . . .
O3 O 0.89350(12) 0.34005(5) 0.21596(4) 0.03538(18) Uani 1 1 d . . . . .
O1 O 1.07795(14) 0.34505(6) 0.44436(4) 0.0410(2) Uani 1 1 d . . . . .
O2 O 1.14760(15) 0.28364(6) 0.33675(4) 0.0444(2) Uani 1 1 d . . . . .
O4 O 1.17220(14) 0.36599(7) 0.17023(5) 0.0474(2) Uani 1 1 d . . . . .
C4 C 1.09735(14) 0.44728(7) 0.34393(5) 0.02804(19) Uani 1 1 d . . . . .
C2 C 1.05157(17) 0.38222(7) 0.21436(5) 0.0315(2) Uani 1 1 d . . . . .
C1 C 1.11002(15) 0.35038(7) 0.37383(5) 0.0301(2) Uani 1 1 d . . . . .
C7 C 1.09711(19) 0.62868(8) 0.28808(8) 0.0427(3) Uani 1 1 d . . . . .
C3 C 1.07871(15) 0.46138(7) 0.26841(5) 0.02782(19) Uani 1 1 d . . . . .
C5 C 1.11326(17) 0.52436(8) 0.39058(6) 0.0356(2) Uani 1 1 d . . . . .
C6 C 1.11423(18) 0.61437(8) 0.36253(8) 0.0418(3) Uani 1 1 d . . . . .
C8 C 1.07828(18) 0.55235(7) 0.24121(7) 0.0364(2) Uani 1 1 d . . . . .
H20 H 1.199(2) 0.0240(11) 0.6282(9) 0.044(4) Uiso 1 1 d . . . . .
H19 H 1.115(2) 0.1802(11) 0.5961(9) 0.049(4) Uiso 1 1 d . . . . .
H18 H 1.202(2) 0.1381(12) 0.3918(9) 0.051(4) Uiso 1 1 d . . . . .
H2A H 1.338(2) -0.1584(12) 0.4457(10) 0.054(5) Uiso 1 1 d . . . . .
H17 H 1.286(2) -0.0192(12) 0.4104(9) 0.054(5) Uiso 1 1 d . . . . .
H2B H 1.368(2) -0.2333(13) 0.5065(9) 0.058(5) Uiso 1 1 d . . . . .
O5 O 1.29240(16) -0.13631(6) 0.60915(5) 0.0457(2) Uani 1 1 d . . . . .
N1 N 1.15353(14) 0.16974(6) 0.49218(5) 0.03349(19) Uani 1 1 d . . . . .
N2 N 1.33765(16) -0.17477(7) 0.49211(6) 0.0371(2) Uani 1 1 d . . . . .
C15 C 1.29518(16) -0.11468(7) 0.54426(6) 0.0307(2) Uani 1 1 d . . . . .
C20 C 1.20025(18) 0.04543(7) 0.57779(6) 0.0343(2) Uani 1 1 d . . . . .
C16 C 1.24858(14) -0.01541(7) 0.52294(5) 0.02733(19) Uani 1 1 d . . . . .
C19 C 1.15221(18) 0.13662(7) 0.56002(6) 0.0354(2) Uani 1 1 d . . . . .
C17 C 1.25010(17) 0.01867(8) 0.45235(6) 0.0342(2) Uani 1 1 d . . . . .
C18 C 1.20316(18) 0.11136(8) 0.43959(6) 0.0364(2) Uani 1 1 d . . . . .
H11 H 0.870(2) 0.0354(11) 0.0329(9) 0.047(4) Uiso 1 1 d . . . . .
H13 H 0.941(3) 0.1299(13) 0.2755(10) 0.060(5) Uiso 1 1 d . . . . .
H12 H 0.874(2) 0.1977(11) 0.0696(9) 0.046(4) Uiso 1 1 d . . . . .
H14 H 0.943(2) -0.0322(12) 0.2510(9) 0.055(5) Uiso 1 1 d . . . . .
H4A H 0.829(2) -0.2415(13) 0.1451(9) 0.059(5) Uiso 1 1 d . . . . .
H4B H 0.787(2) -0.1589(12) 0.2038(9) 0.052(5) Uiso 1 1 d . . . . .
H3 H 0.904(3) 0.2468(14) 0.1922(10) 0.071(6) Uiso 1 1 d . . . . .
O6 O 0.94615(16) -0.13709(6) 0.05296(5) 0.0484(2) Uani 1 1 d . . . . .
N4 N 0.84026(16) -0.17861(7) 0.16246(6) 0.0382(2) Uani 1 1 d . . . . .
N3 N 0.90443(14) 0.17011(7) 0.17510(5) 0.0344(2) Uani 1 1 d . . . . .
C9 C 0.89682(16) -0.11674(7) 0.11444(6) 0.0321(2) Uani 1 1 d . . . . .
C11 C 0.88304(16) 0.05266(7) 0.08463(6) 0.0315(2) Uani 1 1 d . . . . .
C10 C 0.89982(14) -0.01567(7) 0.13817(5) 0.02830(19) Uani 1 1 d . . . . .
C14 C 0.92220(19) 0.01132(8) 0.21069(6) 0.0384(3) Uani 1 1 d . . . . .
C12 C 0.88611(16) 0.14517(7) 0.10491(6) 0.0334(2) Uani 1 1 d . . . . .
C13 C 0.9233(2) 0.10557(8) 0.22749(7) 0.0410(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.2864(14) . ?
O1 C1 1.3270(13) . ?
O2 C1 1.2110(13) . ?
O4 C2 1.2341(13) . ?
C4 C5 1.3985(14) . ?
C4 C3 1.4008(14) . ?
C4 C1 1.4937(14) . ?
C2 C3 1.5132(14) . ?
C7 C6 1.382(2) . ?
C7 C8 1.3938(17) . ?
C3 C8 1.3952(14) . ?
C5 C6 1.3883(17) . ?
O5 C15 1.2315(13) . ?
N1 C19 1.3327(14) . ?
N1 C18 1.3375(15) . ?
N2 C15 1.3327(14) . ?
C15 C16 1.5081(14) . ?
C20 C19 1.3859(15) . ?
C20 C16 1.3874(14) . ?
C16 C17 1.3849(14) . ?
C17 C18 1.3868(15) . ?
O6 C9 1.2327(13) . ?
N4 C9 1.3264(14) . ?
N3 C13 1.3362(16) . ?
N3 C12 1.3375(15) . ?
C9 C10 1.5115(14) . ?
C11 C12 1.3762(14) . ?
C11 C10 1.3881(14) . ?
C10 C14 1.3882(14) . ?
C14 C13 1.3847(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 C3 119.56(9) . . ?
C5 C4 C1 120.43(9) . . ?
C3 C4 C1 119.93(9) . . ?
O4 C2 O3 124.89(10) . . ?
O4 C2 C3 119.88(10) . . ?
O3 C2 C3 115.08(9) . . ?
O2 C1 O1 123.76(10) . . ?
O2 C1 C4 122.57(9) . . ?
O1 C1 C4 113.67(9) . . ?
C6 C7 C8 119.72(11) . . ?
C8 C3 C4 119.15(9) . . ?
C8 C3 C2 117.84(9) . . ?
C4 C3 C2 122.97(9) . . ?
C6 C5 C4 120.50(11) . . ?
C7 C6 C5 120.18(11) . . ?
C7 C8 C3 120.87(11) . . ?
C19 N1 C18 117.71(9) . . ?
O5 C15 N2 123.11(10) . . ?
O5 C15 C16 118.35(10) . . ?
N2 C15 C16 118.54(9) . . ?
C19 C20 C16 119.27(10) . . ?
C17 C16 C20 118.05(9) . . ?
C17 C16 C15 124.33(9) . . ?
C20 C16 C15 117.63(9) . . ?
N1 C19 C20 122.89(10) . . ?
C16 C17 C18 118.89(10) . . ?
N1 C18 C17 123.18(10) . . ?
C13 N3 C12 120.70(10) . . ?
O6 C9 N4 124.02(10) . . ?
O6 C9 C10 119.29(9) . . ?
N4 C9 C10 116.69(9) . . ?
C12 C11 C10 119.18(10) . . ?
C11 C10 C14 119.01(9) . . ?
C11 C10 C9 118.14(9) . . ?
C14 C10 C9 122.84(10) . . ?
C13 C14 C10 118.95(11) . . ?
N3 C12 C11 121.15(10) . . ?
N3 C13 C14 120.99(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.04(2) 1.67(2) 2.7065(12) 179(2) . yes
C18 H18 O2 0.956(17) 2.343(17) 3.1210(14) 138.2(13) . yes
N2 H2A O4 0.883(18) 2.154(18) 3.0334(14) 173.5(16) 2_745 yes
C17 H17 O4 0.986(17) 2.242(17) 3.2043(14) 165.1(14) 2_745 yes
N2 H2B O6 0.902(18) 2.108(18) 3.0058(13) 172.9(16) 4_656 yes
C11 H11 O6 0.982(16) 2.556(16) 3.1019(14) 115.1(11) 3_755 yes
N4 H4A O5 0.958(19) 1.884(19) 2.8410(13) 176.6(16) 4 yes
N4 H4B O3 0.910(17) 2.004(18) 2.8642(13) 157.1(15) 2_645 yes
N3 H3 O3 1.14(2) 1.41(2) 2.5490(11) 176.0(18) . yes
N3 H3 O4 1.14(2) 2.62(2) 3.4036(14) 125.2(12) . yes

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_7_250K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922011'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_7_250K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.33 %     
RESPONSE:Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_7_250K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.08 Ang.  
RESPONSE: The long N-H distance is characteristic of H2 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT430_complex_7_250K_shelxl 
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.82 Ang.  
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi-pi interaction.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'isonicotinamide 2,4-dinitrobenzoate/benzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_weight         668.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7313(4)
_cell_length_b                   10.3587(4)
_cell_length_c                   15.3935(6)
_cell_angle_alpha                78.736(2)
_cell_angle_beta                 71.341(2)
_cell_angle_gamma                77.307(2)
_cell_volume                     1421.05(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    250
_cell_measurement_reflns_used    9351
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      43.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22770
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         35.633
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6755
_reflns_number_gt                4801
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.76 command used to make multi_T datasets comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+0.1501P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6755
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H19 H 1.475(2) 0.792(2) 0.1134(14) 0.063(6) Uiso 1 1 d . . . . .
H5 H 0.799(2) 0.6649(18) 0.1706(13) 0.049(5) Uiso 1 1 d . . . . .
H10 H -0.024(2) 0.3444(17) 0.6759(13) 0.049(5) Uiso 1 1 d . . . . .
H4 H 0.614(2) 0.5793(19) 0.2875(13) 0.051(5) Uiso 1 1 d . . . . .
H18 H 1.298(2) 0.6541(18) 0.1870(14) 0.052(5) Uiso 1 1 d . . . . .
H20 H 1.4835(19) 0.7309(17) -0.1381(13) 0.045(5) Uiso 1 1 d . . . . .
H3 H 0.411(2) 0.9342(19) 0.3448(13) 0.055(5) Uiso 1 1 d . . . . .
H6 H 0.5957(19) 1.0337(19) 0.2280(12) 0.048(5) Uiso 1 1 d . . . . .
H17 H 1.079(2) 0.088(2) 0.1630(14) 0.059(6) Uiso 1 1 d . . . . .
H15 H 0.894(2) -0.017(2) 0.2747(13) 0.055(5) Uiso 1 1 d . . . . .
H11 H 0.0842(19) 0.1760(18) 0.4457(12) 0.046(5) Uiso 1 1 d . . . . .
H9 H 0.151(2) 0.4811(19) 0.6025(13) 0.054(5) Uiso 1 1 d . . . . .
H13 H 0.482(2) 0.123(2) 0.4901(15) 0.067(6) Uiso 1 1 d . . . . .
H7 H 1.039(2) 0.879(2) 0.0359(16) 0.070(6) Uiso 1 1 d . . . . .
H12 H 0.540(2) 0.248(2) 0.4381(13) 0.055(5) Uiso 1 1 d . . . . .
H14 H 0.747(2) 0.328(2) 0.3840(14) 0.063(6) Uiso 1 1 d . . . . .
H1 H 0.429(2) 0.705(2) 0.3716(14) 0.061(6) Uiso 1 1 d . . . . .
H8 H 0.993(2) 0.765(2) 0.1054(15) 0.066(6) Uiso 1 1 d . . . . .
H16 H 0.931(2) 0.422(2) 0.2656(14) 0.066(6) Uiso 1 1 d . . . . .
H2 H 1.100(3) 0.315(2) 0.1622(17) 0.086(7) Uiso 1 1 d . . . . .
O2 O 1.63102(14) 0.89840(13) -0.14043(8) 0.0544(3) Uani 1 1 d . . . . .
O1 O 1.66284(16) 0.89154(16) -0.00872(10) 0.0706(4) Uani 1 1 d . . . . .
O3 O 1.3599(2) 0.5713(2) -0.16882(11) 0.1014(7) Uani 1 1 d . . . . .
O4 O 1.15610(17) 0.56837(18) -0.06292(10) 0.0772(5) Uani 1 1 d . . . . .
O5 O 1.20725(11) 0.39958(10) 0.10039(8) 0.0435(3) Uani 1 1 d . . . . .
O6 O 1.05616(11) 0.57180(11) 0.16693(8) 0.0471(3) Uani 1 1 d . . . . .
N8 N 1.60404(14) 0.86032(13) -0.05825(10) 0.0407(3) Uani 1 1 d . . . . .
N7 N 1.28220(17) 0.58690(16) -0.09183(11) 0.0518(4) Uani 1 1 d . . . . .
C5 C 1.49357(15) 0.77222(14) -0.01573(10) 0.0325(3) Uani 1 1 d . . . . .
C3 C 1.34166(15) 0.63666(14) -0.03112(10) 0.0323(3) Uani 1 1 d . . . . .
C4 C 1.44773(16) 0.71652(14) -0.07273(11) 0.0328(3) Uani 1 1 d . . . . .
C2 C 1.28473(15) 0.60972(14) 0.06435(10) 0.0325(3) Uani 1 1 d . . . . .
C1 C 1.17110(15) 0.52047(14) 0.11375(11) 0.0351(3) Uani 1 1 d . . . . .
C7 C 1.33530(18) 0.66893(17) 0.11844(11) 0.0429(4) Uani 1 1 d . . . . .
C6 C 1.43966(19) 0.75124(18) 0.07889(12) 0.0426(4) Uani 1 1 d . . . . .
C10 C 0.72755(18) 0.72048(16) 0.20347(12) 0.0404(4) Uani 1 1 d . . . . .
C13 C 0.49584(18) 0.88086(16) 0.30627(12) 0.0423(4) Uani 1 1 d . . . . .
C11 C 0.61650(17) 0.66864(16) 0.27312(12) 0.0407(4) Uani 1 1 d . . . . .
C8 C 0.84084(16) 0.92310(15) 0.11097(11) 0.0371(3) Uani 1 1 d . . . . .
C12 C 0.60456(17) 0.93791(16) 0.23743(11) 0.0393(4) Uani 1 1 d . . . . .
C9 C 0.72308(15) 0.85750(14) 0.18609(10) 0.0338(3) Uani 1 1 d . . . . .
O12 O 0.81356(12) 1.04193(11) 0.08235(8) 0.0468(3) Uani 1 1 d . . . . .
N3 N 0.96933(16) 0.84699(16) 0.08243(12) 0.0574(5) Uani 1 1 d . . . . .
N2 N 0.50539(14) 0.74889(13) 0.32295(9) 0.0382(3) Uani 1 1 d . . . . .
C17 C 0.79616(15) 0.14612(14) 0.34130(10) 0.0327(3) Uani 1 1 d . . . . .
C16 C 0.67486(15) 0.07988(14) 0.41097(10) 0.0338(3) Uani 1 1 d . . . . .
C18 C 0.89866(18) 0.07435(17) 0.27570(12) 0.0431(4) Uani 1 1 d . . . . .
C15 C 0.8081(2) 0.27602(17) 0.34048(13) 0.0533(5) Uani 1 1 d . . . . .
C14 C 0.9195(2) 0.33068(18) 0.27288(13) 0.0537(5) Uani 1 1 d . . . . .
C19 C 1.00846(19) 0.13486(17) 0.21003(13) 0.0481(4) Uani 1 1 d . . . . .
O8 O 0.47067(12) 0.43783(11) 0.40598(9) 0.0530(3) Uani 1 1 d . . . . .
O11 O -0.16459(14) 0.16843(14) 0.69181(10) 0.0634(4) Uani 1 1 d . . . . .
O9 O 0.30442(12) 0.61904(10) 0.44136(8) 0.0444(3) Uani 1 1 d . . . . .
O10 O -0.12398(15) 0.09542(13) 0.56265(11) 0.0666(4) Uani 1 1 d . . . . .
N5 N 0.28429(17) 0.31013(16) 0.33847(10) 0.0505(4) Uani 1 1 d . . . . .
N6 N -0.10027(15) 0.16477(13) 0.60970(11) 0.0469(4) Uani 1 1 d . . . . .
O13 O 0.3371(2) 0.20041(17) 0.31589(11) 0.0948(6) Uani 1 1 d . . . . .
O14 O 0.2967(2) 0.41388(16) 0.28631(9) 0.0792(5) Uani 1 1 d . . . . .
O7 O 0.69084(12) -0.04283(10) 0.42424(9) 0.0493(3) Uani 1 1 d . . . . .
N1 N 1.01677(14) 0.26076(13) 0.20954(9) 0.0383(3) Uani 1 1 d . . . . .
N4 N 0.55687(16) 0.15900(15) 0.45346(11) 0.0481(4) Uani 1 1 d . . . . .
C21 C 0.22437(15) 0.41103(14) 0.48095(10) 0.0326(3) Uani 1 1 d . . . . .
C20 C 0.34458(16) 0.49581(14) 0.43816(10) 0.0346(3) Uani 1 1 d . . . . .
C24 C 0.01294(16) 0.25001(14) 0.56501(11) 0.0371(3) Uani 1 1 d . . . . .
C25 C 0.03160(18) 0.33823(17) 0.61441(12) 0.0441(4) Uani 1 1 d . . . . .
C22 C 0.20020(16) 0.31920(14) 0.43532(10) 0.0342(3) Uani 1 1 d . . . . .
C23 C 0.09593(17) 0.23733(15) 0.47560(11) 0.0366(3) Uani 1 1 d . . . . .
C26 C 0.13775(19) 0.41785(17) 0.57149(12) 0.0437(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N8 1.2094(18) . ?
O1 N8 1.2125(19) . ?
O3 N7 1.204(2) . ?
O4 N7 1.2089(19) . ?
O5 C1 1.2628(18) . ?
O6 C1 1.2356(17) . ?
N8 C5 1.4712(18) . ?
N7 C3 1.463(2) . ?
C5 C4 1.365(2) . ?
C5 C6 1.372(2) . ?
C3 C4 1.3803(19) . ?
C3 C2 1.390(2) . ?
C4 H20 0.947(18) . ?
C2 C7 1.381(2) . ?
C2 C1 1.5140(19) . ?
C7 C6 1.382(2) . ?
C7 H18 0.993(19) . ?
C6 H19 0.92(2) . ?
C10 C11 1.376(2) . ?
C10 C9 1.386(2) . ?
C10 H5 0.885(18) . ?
C13 N2 1.329(2) . ?
C13 C12 1.380(2) . ?
C13 H3 0.975(19) . ?
C11 N2 1.331(2) . ?
C11 H4 0.911(19) . ?
C8 O12 1.2244(18) . ?
C8 N3 1.315(2) . ?
C8 C9 1.5163(19) . ?
C12 C9 1.379(2) . ?
C12 H6 0.963(19) . ?
N3 H7 0.88(2) . ?
N3 H8 0.86(2) . ?
N2 H1 0.99(2) . ?
C17 C15 1.373(2) . ?
C17 C18 1.375(2) . ?
C17 C16 1.5076(19) . ?
C16 O7 1.2304(17) . ?
C16 N4 1.317(2) . ?
C18 C19 1.383(2) . ?
C18 H15 0.96(2) . ?
C15 C14 1.377(2) . ?
C15 H14 0.91(2) . ?
C14 N1 1.325(2) . ?
C14 H16 0.95(2) . ?
C19 N1 1.323(2) . ?
C19 H17 0.95(2) . ?
O8 C20 1.2308(18) . ?
O11 N6 1.2219(19) . ?
O9 C20 1.2561(17) . ?
O10 N6 1.215(2) . ?
N5 O13 1.208(2) . ?
N5 O14 1.213(2) . ?
N5 C22 1.463(2) . ?
N6 C24 1.4737(19) . ?
N1 H2 1.08(3) . ?
N4 H13 0.87(2) . ?
N4 H12 0.90(2) . ?
C21 C22 1.385(2) . ?
C21 C26 1.385(2) . ?
C21 C20 1.5185(19) . ?
C24 C23 1.370(2) . ?
C24 C25 1.371(2) . ?
C25 C26 1.381(2) . ?
C25 H10 0.934(18) . ?
C22 C23 1.380(2) . ?
C23 H11 0.899(19) . ?
C26 H9 0.934(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N8 O1 123.39(13) . . ?
O2 N8 C5 118.54(13) . . ?
O1 N8 C5 118.07(13) . . ?
O3 N7 O4 123.77(17) . . ?
O3 N7 C3 118.14(15) . . ?
O4 N7 C3 118.04(15) . . ?
C4 C5 C6 122.95(14) . . ?
C4 C5 N8 118.18(13) . . ?
C6 C5 N8 118.86(14) . . ?
C4 C3 C2 122.72(14) . . ?
C4 C3 N7 117.23(13) . . ?
C2 C3 N7 119.93(13) . . ?
C5 C4 C3 117.01(14) . . ?
C5 C4 H20 123.7(10) . . ?
C3 C4 H20 119.3(10) . . ?
C7 C2 C3 117.62(13) . . ?
C7 C2 C1 117.38(13) . . ?
C3 C2 C1 125.00(14) . . ?
O6 C1 O5 126.80(13) . . ?
O6 C1 C2 116.51(13) . . ?
O5 C1 C2 116.55(12) . . ?
C2 C7 C6 121.08(15) . . ?
C2 C7 H18 121.0(11) . . ?
C6 C7 H18 117.9(11) . . ?
C5 C6 C7 118.60(16) . . ?
C5 C6 H19 118.6(13) . . ?
C7 C6 H19 122.8(13) . . ?
C11 C10 C9 119.22(15) . . ?
C11 C10 H5 118.7(12) . . ?
C9 C10 H5 122.1(12) . . ?
N2 C13 C12 120.09(15) . . ?
N2 C13 H3 117.7(11) . . ?
C12 C13 H3 122.2(11) . . ?
N2 C11 C10 120.58(15) . . ?
N2 C11 H4 116.7(12) . . ?
C10 C11 H4 122.7(12) . . ?
O12 C8 N3 124.05(14) . . ?
O12 C8 C9 119.43(13) . . ?
N3 C8 C9 116.50(13) . . ?
C9 C12 C13 119.76(15) . . ?
C9 C12 H6 122.1(11) . . ?
C13 C12 H6 118.1(11) . . ?
C12 C9 C10 118.68(13) . . ?
C12 C9 C8 118.54(13) . . ?
C10 C9 C8 122.75(14) . . ?
C8 N3 H7 119.7(14) . . ?
C8 N3 H8 125.1(14) . . ?
H7 N3 H8 115.2(19) . . ?
C13 N2 C11 121.62(13) . . ?
C13 N2 H1 122.1(11) . . ?
C11 N2 H1 116.2(11) . . ?
C15 C17 C18 118.50(14) . . ?
C15 C17 C16 122.50(13) . . ?
C18 C17 C16 118.99(13) . . ?
O7 C16 N4 124.19(14) . . ?
O7 C16 C17 118.90(13) . . ?
N4 C16 C17 116.90(13) . . ?
C17 C18 C19 119.59(15) . . ?
C17 C18 H15 120.7(11) . . ?
C19 C18 H15 119.7(11) . . ?
C17 C15 C14 119.05(15) . . ?
C17 C15 H14 123.2(13) . . ?
C14 C15 H14 117.7(13) . . ?
N1 C14 C15 121.82(15) . . ?
N1 C14 H16 114.5(12) . . ?
C15 C14 H16 123.7(12) . . ?
N1 C19 C18 120.98(15) . . ?
N1 C19 H17 117.9(12) . . ?
C18 C19 H17 121.1(12) . . ?
O13 N5 O14 124.45(16) . . ?
O13 N5 C22 118.06(15) . . ?
O14 N5 C22 117.49(15) . . ?
O10 N6 O11 124.09(14) . . ?
O10 N6 C24 118.04(15) . . ?
O11 N6 C24 117.87(15) . . ?
C19 N1 C14 120.04(14) . . ?
C19 N1 H2 126.1(12) . . ?
C14 N1 H2 113.8(12) . . ?
C16 N4 H13 118.5(14) . . ?
C16 N4 H12 123.9(12) . . ?
H13 N4 H12 116.2(18) . . ?
C22 C21 C26 116.61(13) . . ?
C22 C21 C20 123.11(13) . . ?
C26 C21 C20 120.18(14) . . ?
O8 C20 O9 126.65(13) . . ?
O8 C20 C21 117.57(13) . . ?
O9 C20 C21 115.76(12) . . ?
C23 C24 C25 122.60(14) . . ?
C23 C24 N6 118.48(15) . . ?
C25 C24 N6 118.92(14) . . ?
C24 C25 C26 118.27(15) . . ?
C24 C25 H10 122.0(11) . . ?
C26 C25 H10 119.8(11) . . ?
C23 C22 C21 123.27(13) . . ?
C23 C22 N5 117.26(14) . . ?
C21 C22 N5 119.43(13) . . ?
C24 C23 C22 117.18(15) . . ?
C24 C23 H11 120.7(11) . . ?
C22 C23 H11 122.1(11) . . ?
C25 C26 C21 122.06(16) . . ?
C25 C26 H9 120.4(11) . . ?
C21 C26 H9 117.5(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H5 O6 0.885(18) 2.463(19) 3.152(2) 135.1(15) . yes
C25 H10 O6 0.934(18) 2.630(18) 3.459(2) 148.2(14) 2_666 yes
C11 H4 O3 0.911(19) 2.546(18) 3.143(2) 123.6(14) 2_765 yes
C11 H4 O8 0.911(19) 2.378(19) 3.1043(19) 136.6(15) . yes
C13 H3 O13 0.975(19) 2.678(19) 3.341(2) 125.6(14) 1_565 yes
N4 H13 O7 0.87(2) 2.01(2) 2.8790(18) 179(2) 2_656 yes
N3 H7 O12 0.88(2) 2.07(2) 2.9531(18) 173(2) 2_775 yes
N4 H12 O8 0.90(2) 1.96(2) 2.8431(18) 170.7(18) . yes
C15 H14 O8 0.91(2) 2.62(2) 3.276(2) 129.0(16) . yes
N2 H1 O9 0.99(2) 1.64(2) 2.6218(15) 172.2(18) . yes
N3 H8 O6 0.86(2) 2.09(2) 2.9544(19) 176(2) . yes
C14 H16 O6 0.95(2) 2.22(2) 3.0245(19) 141.1(16) . yes
N1 H2 O5 1.08(3) 1.48(3) 2.5616(15) 176(2) . yes
N1 H2 O6 1.08(3) 2.61(2) 3.2426(16) 116.8(15) . yes

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.051

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_7_200K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922014'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_7_200K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.68 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT430_complex_7_200K_shelxl 
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.79 Ang.  
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi-pi interaction.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'isonicotinamide 2,4-dinitrobenzoate/benzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_weight         668.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6926(4)
_cell_length_b                   10.3369(4)
_cell_length_c                   15.3321(6)
_cell_angle_alpha                78.854(2)
_cell_angle_beta                 71.624(2)
_cell_angle_gamma                77.257(2)
_cell_volume                     1409.14(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    200
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      43.75

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.178
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22472
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.540
_diffrn_reflns_theta_max         35.633
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6692
_reflns_number_gt                5283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.76 command used to make multi_T datasets for complex 5 comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+0.2569P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6692
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H19 H 1.4718(18) 0.7974(17) 0.1165(12) 0.039(4) Uiso 1 1 d . . . . .
H5 H 0.802(2) 0.6630(18) 0.1682(12) 0.044(5) Uiso 1 1 d . . . . .
H10 H -0.0247(18) 0.3458(16) 0.6753(12) 0.040(4) Uiso 1 1 d . . . . .
H4 H 0.6147(19) 0.5784(19) 0.2890(12) 0.044(5) Uiso 1 1 d . . . . .
H18 H 1.2948(19) 0.6568(17) 0.1867(12) 0.040(4) Uiso 1 1 d . . . . .
H20 H 1.4857(18) 0.7312(16) -0.1385(12) 0.037(4) Uiso 1 1 d . . . . .
H3 H 0.408(2) 0.9368(18) 0.3455(12) 0.045(5) Uiso 1 1 d . . . . .
H6 H 0.5955(19) 1.0359(18) 0.2276(12) 0.044(5) Uiso 1 1 d . . . . .
H17 H 1.082(2) 0.0859(19) 0.1628(13) 0.050(5) Uiso 1 1 d . . . . .
H15 H 0.899(2) -0.0218(19) 0.2753(12) 0.047(5) Uiso 1 1 d . . . . .
H11 H 0.0838(18) 0.1756(17) 0.4403(11) 0.037(4) Uiso 1 1 d . . . . .
H9 H 0.1517(18) 0.4832(17) 0.6040(12) 0.041(4) Uiso 1 1 d . . . . .
H13 H 0.478(2) 0.121(2) 0.4902(14) 0.055(5) Uiso 1 1 d . . . . .
H7 H 1.037(2) 0.880(2) 0.0362(14) 0.058(6) Uiso 1 1 d . . . . .
H12 H 0.540(2) 0.244(2) 0.4378(13) 0.048(5) Uiso 1 1 d . . . . .
H14 H 0.744(2) 0.3290(19) 0.3848(13) 0.056(5) Uiso 1 1 d . . . . .
H1 H 0.428(2) 0.709(2) 0.3728(14) 0.058(5) Uiso 1 1 d . . . . .
H8 H 0.995(2) 0.766(2) 0.1083(13) 0.051(5) Uiso 1 1 d . . . . .
H16 H 0.928(2) 0.423(2) 0.2656(13) 0.056(5) Uiso 1 1 d . . . . .
H2 H 1.100(3) 0.313(2) 0.1623(16) 0.079(7) Uiso 1 1 d . . . . .
O2 O 1.63045(12) 0.89932(11) -0.14047(7) 0.0419(3) Uani 1 1 d . . . . .
O1 O 1.66241(14) 0.89322(14) -0.00775(8) 0.0542(3) Uani 1 1 d . . . . .
O3 O 1.36203(17) 0.56921(18) -0.17017(9) 0.0769(5) Uani 1 1 d . . . . .
O4 O 1.15616(14) 0.56616(15) -0.06413(9) 0.0589(4) Uani 1 1 d . . . . .
O5 O 1.20752(10) 0.39824(9) 0.09989(7) 0.0330(2) Uani 1 1 d . . . . .
O6 O 1.05581(10) 0.57134(9) 0.16656(7) 0.0357(2) Uani 1 1 d . . . . .
N8 N 1.60348(12) 0.86143(12) -0.05783(8) 0.0312(3) Uani 1 1 d . . . . .
N7 N 1.28283(15) 0.58536(13) -0.09280(9) 0.0399(3) Uani 1 1 d . . . . .
C5 C 1.49363(13) 0.77283(12) -0.01564(9) 0.0253(3) Uani 1 1 d . . . . .
C3 C 1.34203(13) 0.63590(13) -0.03142(9) 0.0250(3) Uani 1 1 d . . . . .
C4 C 1.44820(14) 0.71592(13) -0.07312(9) 0.0253(3) Uani 1 1 d . . . . .
C2 C 1.28464(13) 0.60886(12) 0.06415(9) 0.0252(3) Uani 1 1 d . . . . .
C1 C 1.17117(14) 0.51952(13) 0.11338(9) 0.0268(3) Uani 1 1 d . . . . .
C7 C 1.33491(16) 0.66941(15) 0.11879(10) 0.0327(3) Uani 1 1 d . . . . .
C6 C 1.43904(16) 0.75240(15) 0.07938(10) 0.0325(3) Uani 1 1 d . . . . .
C10 C 0.72746(15) 0.72089(14) 0.20381(10) 0.0308(3) Uani 1 1 d . . . . .
C13 C 0.49550(15) 0.88347(14) 0.30753(10) 0.0327(3) Uani 1 1 d . . . . .
C11 C 0.61604(15) 0.66944(14) 0.27404(10) 0.0313(3) Uani 1 1 d . . . . .
C8 C 0.84065(14) 0.92413(13) 0.11139(9) 0.0285(3) Uani 1 1 d . . . . .
C12 C 0.60429(15) 0.94019(14) 0.23865(10) 0.0301(3) Uani 1 1 d . . . . .
C9 C 0.72284(14) 0.85877(13) 0.18656(9) 0.0261(3) Uani 1 1 d . . . . .
O12 O 0.81328(11) 1.04346(9) 0.08245(7) 0.0356(2) Uani 1 1 d . . . . .
N3 N 0.96999(14) 0.84687(14) 0.08268(10) 0.0436(4) Uani 1 1 d . . . . .
N2 N 0.50512(12) 0.75039(11) 0.32424(8) 0.0295(3) Uani 1 1 d . . . . .
C17 C 0.79688(14) 0.14514(12) 0.34132(9) 0.0250(3) Uani 1 1 d . . . . .
C16 C 0.67550(14) 0.07908(13) 0.41108(9) 0.0258(3) Uani 1 1 d . . . . .
C18 C 0.90038(15) 0.07204(14) 0.27597(10) 0.0328(3) Uani 1 1 d . . . . .
C15 C 0.80756(18) 0.27653(15) 0.33960(11) 0.0414(4) Uani 1 1 d . . . . .
C14 C 0.91919(18) 0.33068(15) 0.27149(11) 0.0416(4) Uani 1 1 d . . . . .
C19 C 1.01043(16) 0.13206(15) 0.20986(11) 0.0367(3) Uani 1 1 d . . . . .
O8 O 0.47081(11) 0.43824(10) 0.40567(8) 0.0403(3) Uani 1 1 d . . . . .
O11 O -0.16608(12) 0.16862(12) 0.69128(8) 0.0477(3) Uani 1 1 d . . . . .
O9 O 0.30428(10) 0.62014(9) 0.44314(7) 0.0335(2) Uani 1 1 d . . . . .
O10 O -0.12495(13) 0.09544(11) 0.56110(9) 0.0501(3) Uani 1 1 d . . . . .
N5 N 0.28350(14) 0.31172(13) 0.33760(8) 0.0380(3) Uani 1 1 d . . . . .
N6 N -0.10140(13) 0.16520(12) 0.60882(9) 0.0354(3) Uani 1 1 d . . . . .
O13 O 0.33658(18) 0.20185(14) 0.31464(9) 0.0728(5) Uani 1 1 d . . . . .
O14 O 0.29439(16) 0.41643(13) 0.28563(8) 0.0600(4) Uani 1 1 d . . . . .
O7 O 0.69198(11) -0.04421(9) 0.42531(8) 0.0377(3) Uani 1 1 d . . . . .
N1 N 1.01715(12) 0.25937(11) 0.20875(8) 0.0294(3) Uani 1 1 d . . . . .
N4 N 0.55610(14) 0.15894(13) 0.45280(9) 0.0372(3) Uani 1 1 d . . . . .
C21 C 0.22356(14) 0.41220(12) 0.48135(9) 0.0254(3) Uani 1 1 d . . . . .
C20 C 0.34458(14) 0.49670(13) 0.43886(9) 0.0262(3) Uani 1 1 d . . . . .
C24 C 0.01166(14) 0.25045(13) 0.56474(10) 0.0287(3) Uani 1 1 d . . . . .
C25 C 0.03090(16) 0.33864(15) 0.61481(10) 0.0337(3) Uani 1 1 d . . . . .
C22 C 0.19920(14) 0.32018(13) 0.43506(9) 0.0261(3) Uani 1 1 d . . . . .
C23 C 0.09522(15) 0.23786(13) 0.47469(10) 0.0281(3) Uani 1 1 d . . . . .
C26 C 0.13725(16) 0.41862(15) 0.57218(10) 0.0331(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N8 1.2131(16) . ?
O1 N8 1.2169(16) . ?
O3 N7 1.2125(17) . ?
O4 N7 1.2139(17) . ?
O5 C1 1.2641(16) . ?
O6 C1 1.2377(16) . ?
N8 C5 1.4689(16) . ?
N7 C3 1.4664(18) . ?
C5 C4 1.3697(19) . ?
C5 C6 1.3753(19) . ?
C3 C4 1.3814(17) . ?
C3 C2 1.3896(18) . ?
C4 H20 0.947(17) . ?
C2 C7 1.388(2) . ?
C2 C1 1.5124(17) . ?
C7 C6 1.3846(19) . ?
C7 H18 0.983(17) . ?
C6 H19 0.961(18) . ?
C10 C11 1.3810(18) . ?
C10 C9 1.3917(19) . ?
C10 H5 0.932(18) . ?
C13 N2 1.3375(18) . ?
C13 C12 1.3792(18) . ?
C13 H3 0.984(18) . ?
C11 N2 1.3337(18) . ?
C11 H4 0.927(18) . ?
C8 O12 1.2277(16) . ?
C8 N3 1.3227(18) . ?
C8 C9 1.5159(17) . ?
C12 C9 1.3860(19) . ?
C12 H6 0.960(18) . ?
N3 H7 0.87(2) . ?
N3 H8 0.87(2) . ?
N2 H1 0.98(2) . ?
C17 C15 1.3793(19) . ?
C17 C18 1.3806(19) . ?
C17 C16 1.5077(17) . ?
C16 O7 1.2337(16) . ?
C16 N4 1.3213(18) . ?
C18 C19 1.3846(19) . ?
C18 H15 0.974(18) . ?
C15 C14 1.3796(19) . ?
C15 H14 0.94(2) . ?
C14 N1 1.3265(18) . ?
C14 H16 0.96(2) . ?
C19 N1 1.3285(18) . ?
C19 H17 0.949(19) . ?
O8 C20 1.2335(16) . ?
O11 N6 1.2249(17) . ?
O9 C20 1.2575(15) . ?
O10 N6 1.2204(17) . ?
N5 O13 1.2087(17) . ?
N5 O14 1.2172(17) . ?
N5 C22 1.4689(17) . ?
N6 C24 1.4708(16) . ?
N1 H2 1.07(2) . ?
N4 H13 0.91(2) . ?
N4 H12 0.86(2) . ?
C21 C26 1.3857(18) . ?
C21 C22 1.3892(19) . ?
C21 C20 1.5210(17) . ?
C24 C25 1.375(2) . ?
C24 C23 1.3774(19) . ?
C25 C26 1.3840(19) . ?
C25 H10 0.922(17) . ?
C22 C23 1.3789(18) . ?
C23 H11 0.950(17) . ?
C26 H9 0.956(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N8 O1 123.45(12) . . ?
O2 N8 C5 118.47(12) . . ?
O1 N8 C5 118.07(12) . . ?
O3 N7 O4 123.96(14) . . ?
O3 N7 C3 117.93(12) . . ?
O4 N7 C3 118.07(12) . . ?
C4 C5 C6 122.88(12) . . ?
C4 C5 N8 118.28(11) . . ?
C6 C5 N8 118.83(12) . . ?
C4 C3 C2 123.12(12) . . ?
C4 C3 N7 117.01(11) . . ?
C2 C3 N7 119.76(11) . . ?
C5 C4 C3 116.88(12) . . ?
C5 C4 H20 122.3(10) . . ?
C3 C4 H20 120.8(10) . . ?
C7 C2 C3 117.32(11) . . ?
C7 C2 C1 117.38(11) . . ?
C3 C2 C1 125.29(12) . . ?
O6 C1 O5 126.88(12) . . ?
O6 C1 C2 116.39(11) . . ?
O5 C1 C2 116.60(11) . . ?
C6 C7 C2 121.14(13) . . ?
C6 C7 H18 118.2(10) . . ?
C2 C7 H18 120.7(10) . . ?
C5 C6 C7 118.61(13) . . ?
C5 C6 H19 119.6(10) . . ?
C7 C6 H19 121.7(10) . . ?
C11 C10 C9 118.94(13) . . ?
C11 C10 H5 119.4(11) . . ?
C9 C10 H5 121.6(11) . . ?
N2 C13 C12 120.01(13) . . ?
N2 C13 H3 117.1(10) . . ?
C12 C13 H3 122.9(10) . . ?
N2 C11 C10 120.67(13) . . ?
N2 C11 H4 117.0(11) . . ?
C10 C11 H4 122.4(11) . . ?
O12 C8 N3 124.06(12) . . ?
O12 C8 C9 119.52(12) . . ?
N3 C8 C9 116.40(12) . . ?
C13 C12 C9 119.72(13) . . ?
C13 C12 H6 118.9(11) . . ?
C9 C12 H6 121.4(11) . . ?
C12 C9 C10 118.88(12) . . ?
C12 C9 C8 118.46(11) . . ?
C10 C9 C8 122.64(12) . . ?
C8 N3 H7 118.4(13) . . ?
C8 N3 H8 124.8(12) . . ?
H7 N3 H8 116.8(18) . . ?
C11 N2 C13 121.73(12) . . ?
C11 N2 H1 117.6(12) . . ?
C13 N2 H1 120.7(12) . . ?
C15 C17 C18 118.65(12) . . ?
C15 C17 C16 122.48(12) . . ?
C18 C17 C16 118.87(12) . . ?
O7 C16 N4 124.07(12) . . ?
O7 C16 C17 119.05(11) . . ?
N4 C16 C17 116.88(11) . . ?
C17 C18 C19 119.68(13) . . ?
C17 C18 H15 121.8(11) . . ?
C19 C18 H15 118.5(11) . . ?
C17 C15 C14 118.79(13) . . ?
C17 C15 H14 122.2(12) . . ?
C14 C15 H14 119.0(12) . . ?
N1 C14 C15 121.81(13) . . ?
N1 C14 H16 116.2(11) . . ?
C15 C14 H16 121.9(11) . . ?
N1 C19 C18 120.57(13) . . ?
N1 C19 H17 117.2(11) . . ?
C18 C19 H17 122.2(11) . . ?
O13 N5 O14 124.71(14) . . ?
O13 N5 C22 117.95(12) . . ?
O14 N5 C22 117.34(12) . . ?
O10 N6 O11 124.05(12) . . ?
O10 N6 C24 118.07(12) . . ?
O11 N6 C24 117.88(13) . . ?
C14 N1 C19 120.48(12) . . ?
C14 N1 H2 113.3(12) . . ?
C19 N1 H2 126.1(12) . . ?
C16 N4 H13 118.1(12) . . ?
C16 N4 H12 123.9(12) . . ?
H13 N4 H12 116.5(17) . . ?
C26 C21 C22 116.65(12) . . ?
C26 C21 C20 120.22(12) . . ?
C22 C21 C20 123.01(11) . . ?
O8 C20 O9 126.90(12) . . ?
O8 C20 C21 117.59(11) . . ?
O9 C20 C21 115.50(11) . . ?
C25 C24 C23 122.51(12) . . ?
C25 C24 N6 119.07(12) . . ?
C23 C24 N6 118.42(12) . . ?
C24 C25 C26 118.36(13) . . ?
C24 C25 H10 122.0(11) . . ?
C26 C25 H10 119.6(11) . . ?
C23 C22 C21 123.50(12) . . ?
C23 C22 N5 117.14(12) . . ?
C21 C22 N5 119.32(11) . . ?
C24 C23 C22 116.98(12) . . ?
C24 C23 H11 122.7(10) . . ?
C22 C23 H11 120.3(10) . . ?
C25 C26 C21 121.99(13) . . ?
C25 C26 H9 120.9(10) . . ?
C21 C26 H9 117.1(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H5 O6 0.932(18) 2.424(18) 3.1416(17) 133.7(14) . yes
C25 H10 O6 0.922(17) 2.633(17) 3.4486(18) 147.9(14) 2_666 yes
C11 H4 O3 0.927(18) 2.522(18) 3.121(2) 122.6(13) 2_765 yes
C11 H4 O8 0.927(18) 2.358(18) 3.0975(16) 136.6(14) . yes
C13 H3 O13 0.984(18) 2.660(18) 3.318(2) 124.5(13) 1_565 yes
N4 H13 O7 0.91(2) 1.96(2) 2.8721(15) 177.6(18) 2_656 yes
N3 H7 O12 0.87(2) 2.08(2) 2.9488(16) 174.7(19) 2_775 yes
N4 H12 O8 0.86(2) 1.99(2) 2.8386(16) 171.3(18) . yes
C15 H14 O8 0.94(2) 2.58(2) 3.2613(19) 129.3(15) . yes
N2 H1 O9 0.98(2) 1.65(2) 2.6259(14) 170.5(18) . yes
N3 H8 O6 0.87(2) 2.07(2) 2.9446(16) 178.9(18) . yes
C14 H16 O6 0.96(2) 2.22(2) 3.0155(17) 139.2(15) . yes
N1 H2 O5 1.07(2) 1.49(2) 2.5596(14) 176(2) . yes
N1 H2 O6 1.07(2) 2.62(2) 3.2454(15) 117.1(15) . yes

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.053

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_4_200K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922000'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_4_200K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.09 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT230_complex_4_200K_shelxl 
;
PROBLEM: Hirshfeld Test Diff for    O6       --N2       .        7.9 s.u.  
RESPONSE: Atoms O6 and N2 are different atom types.
;
_vrf_PLAT414_complex_4_200K_shelxl 
;
PROBLEM: Short Intra D-H..H-X       H6       ..H9A              1.85 Ang.  
RESPONSE: H6 and H9A are in the same N,N-dimethylurea molecule and are
geometrically close being 'cis' to one another in the molecule.
;
_vrf_PLAT772_complex_4_200K_shelxl 
;
PROBLEM: Suspect O-H Bond in CIF: O14      --H13       ..       1.48 Ang.  
RESPONSE: Short H...O distance is charactersitic of H13 being part of a strong 
O-H...O hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'N,N-dimethylurea 3,5-dinitrobenzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H4 N2 O6, C3 H8 N2 O1)'
_chemical_formula_sum            'C20 H24 N8 O14'
_chemical_formula_weight         600.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.48730(16)
_cell_length_b                   6.09630(4)
_cell_length_c                   30.29390(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.3750(5)
_cell_angle_gamma                90
_cell_volume                     5256.54(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    23916
_cell_measurement_theta_max      35.9150195464
_cell_measurement_theta_min      1.29957873843

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             2496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.014
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.995951233724
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.067: AIMLESS, version 0.7.3 : 15/08/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

_diffrn_radiation_wavelength     0.6889
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Photon counting pixel'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38334
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.304
_diffrn_reflns_theta_max         27.337
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6495
_reflns_number_gt                5606
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
 Methyl H-atoms are placed geometrically for C19, C20 using HFIX 137.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+1.5371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6495
_refine_ls_number_parameters     431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H3 H 0.3035(7) 0.556(3) 0.4799(6) 0.069(5) Uiso 1 1 d . . . . .
O8 O 0.39185(3) 0.65556(16) 0.24761(3) 0.0479(2) Uani 1 1 d . . . . .
O9 O 0.34071(3) 0.37997(17) 0.23851(4) 0.0560(3) Uani 1 1 d . . . . .
O12 O 0.28730(4) 1.28503(17) 0.37276(3) 0.0554(2) Uani 1 1 d . . . . .
O13 O 0.35541(4) 1.25872(18) 0.34489(4) 0.0581(3) Uani 1 1 d . . . . .
O10 O 0.19165(4) 0.42173(19) 0.31045(4) 0.0594(3) Uani 1 1 d . . . . .
O11 O 0.17767(4) 0.6843(2) 0.35527(4) 0.0635(3) Uani 1 1 d . . . . .
N6 N 0.31589(4) 1.19088(17) 0.35052(3) 0.0429(2) Uani 1 1 d . . . . .
N5 N 0.20204(4) 0.59405(19) 0.32869(3) 0.0440(2) Uani 1 1 d . . . . .
C17 C 0.33226(4) 0.88333(19) 0.30108(4) 0.0371(2) Uani 1 1 d . . . . .
C13 C 0.27568(4) 0.59277(19) 0.28975(4) 0.0362(2) Uani 1 1 d . . . . .
C12 C 0.31920(4) 0.68481(19) 0.28146(4) 0.0359(2) Uani 1 1 d . . . . .
C16 C 0.30156(4) 0.98413(18) 0.32869(4) 0.0365(2) Uani 1 1 d . . . . .
C14 C 0.24670(4) 0.69940(19) 0.31804(4) 0.0368(2) Uani 1 1 d . . . . .
C11 C 0.35175(4) 0.5590(2) 0.25325(4) 0.0407(2) Uani 1 1 d . . . . .
C15 C 0.25828(4) 0.8960(2) 0.33823(4) 0.0378(2) Uani 1 1 d . . . . .
O14 O 0.45056(3) 0.46275(17) 0.20416(4) 0.0565(3) Uani 1 1 d . . . . .
N8 N 0.49706(4) 0.1802(2) 0.18720(5) 0.0580(3) Uani 1 1 d . . . . .
N7 N 0.42313(5) 0.1195(2) 0.21434(5) 0.0623(3) Uani 1 1 d . . . . .
C18 C 0.45665(4) 0.2579(2) 0.20189(4) 0.0482(3) Uani 1 1 d . . . . .
C20 C 0.53283(6) 0.3350(4) 0.17462(7) 0.0745(5) Uani 1 1 d . . . . .
H20A H 0.522485 0.409479 0.148033 0.112 Uiso 1 1 calc R U . . .
H20B H 0.561490 0.257789 0.169630 0.112 Uiso 1 1 calc R U . . .
H20C H 0.538162 0.440245 0.197865 0.112 Uiso 1 1 calc R U . . .
C19 C 0.50662(7) -0.0535(3) 0.18359(7) 0.0742(5) Uani 1 1 d . . . . .
H19A H 0.510100 -0.116130 0.212617 0.111 Uiso 1 1 calc R U . . .
H19B H 0.535056 -0.074805 0.168213 0.111 Uiso 1 1 calc R U . . .
H19C H 0.481002 -0.123622 0.167571 0.111 Uiso 1 1 calc R U . . .
C8 C 0.55199(4) -0.32426(19) 0.42651(4) 0.0399(2) Uani 1 1 d . . . . .
C10 C 0.62018(5) -0.3153(2) 0.38145(5) 0.0522(3) Uani 1 1 d . . . . .
H10A H 0.613041 -0.361607 0.351638 0.078 Uiso 1 1 calc R U . . .
H10B H 0.652267 -0.350524 0.389425 0.078 Uiso 1 1 calc R U . . .
H10C H 0.615626 -0.159723 0.383699 0.078 Uiso 1 1 calc R U . . .
C9 C 0.59728(8) -0.6592(3) 0.41849(7) 0.0780(6) Uani 1 1 d . . . . .
H9A H 0.583694 -0.702593 0.445623 0.117 Uiso 1 1 calc R U . . .
H9B H 0.630455 -0.687506 0.420271 0.117 Uiso 1 1 calc R U . . .
H9C H 0.583026 -0.741271 0.394441 0.117 Uiso 1 1 calc R U . . .
N4 N 0.58924(4) -0.42759(17) 0.41118(4) 0.0461(2) Uani 1 1 d . . . . .
N3 N 0.52105(5) -0.4345(2) 0.45031(5) 0.0554(3) Uani 1 1 d . . . . .
O7 O 0.54674(3) -0.12226(15) 0.41979(3) 0.0509(2) Uani 1 1 d . . . . .
O1 O 0.47775(3) 0.10095(15) 0.43503(3) 0.0496(2) Uani 1 1 d . . . . .
O2 O 0.44712(4) -0.14783(15) 0.48002(3) 0.0489(2) Uani 1 1 d . . . . .
O6 O 0.38795(4) 0.74093(19) 0.39141(4) 0.0642(3) Uani 1 1 d . . . . .
O5 O 0.32433(5) 0.82499(19) 0.42395(4) 0.0695(3) Uani 1 1 d . . . . .
N2 N 0.35796(5) 0.70523(19) 0.41808(4) 0.0532(3) Uani 1 1 d . . . . .
O3 O 0.29755(5) 0.0305(3) 0.54610(5) 0.0964(5) Uani 1 1 d . . . . .
O4 O 0.27186(6) 0.3635(3) 0.54267(5) 0.1000(5) Uani 1 1 d . . . . .
N1 N 0.29839(5) 0.2182(3) 0.53187(5) 0.0718(4) Uani 1 1 d . . . . .
C2 C 0.40541(4) 0.18253(19) 0.46577(4) 0.0399(2) Uani 1 1 d . . . . .
C7 C 0.40083(5) 0.3721(2) 0.44034(4) 0.0417(3) Uani 1 1 d . . . . .
C1 C 0.44582(4) 0.02912(19) 0.46093(4) 0.0408(3) Uani 1 1 d . . . . .
C6 C 0.36265(5) 0.5062(2) 0.44578(4) 0.0443(3) Uani 1 1 d . . . . .
C3 C 0.37136(5) 0.1316(2) 0.49565(4) 0.0456(3) Uani 1 1 d . . . . .
C4 C 0.33416(5) 0.2722(3) 0.49993(5) 0.0524(3) Uani 1 1 d . . . . .
C5 C 0.32868(5) 0.4631(3) 0.47559(5) 0.0518(3) Uani 1 1 d . . . . .
H16 H 0.3612(6) 0.945(3) 0.2957(5) 0.047(4) Uiso 1 1 d . . . . .
H2 H 0.3737(6) 0.006(3) 0.5138(5) 0.054(4) Uiso 1 1 d . . . . .
H15 H 0.2392(5) 0.968(3) 0.3564(5) 0.050(4) Uiso 1 1 d . . . . .
H14 H 0.2666(5) 0.458(3) 0.2768(5) 0.041(3) Uiso 1 1 d . . . . .
H5 H 0.4971(7) -0.358(3) 0.4600(6) 0.064(5) Uiso 1 1 d . . . . .
H4 H 0.4225(6) 0.404(3) 0.4199(6) 0.054(4) Uiso 1 1 d . . . . .
H6 H 0.5266(8) -0.568(4) 0.4537(8) 0.090(7) Uiso 1 1 d . . . . .
H17 H 0.3937(8) 0.183(4) 0.2214(8) 0.094(7) Uiso 1 1 d . . . . .
H18 H 0.4273(7) -0.032(4) 0.2111(7) 0.080(6) Uiso 1 1 d . . . . .
H13 H 0.4139(8) 0.566(4) 0.2304(7) 0.085(6) Uiso 1 1 d . . . . .
H1 H 0.5046(8) -0.011(4) 0.4298(7) 0.087(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O8 C11 1.3026(15) . ?
O8 H13 1.00(2) . ?
O9 C11 1.2156(16) . ?
O12 N6 1.2216(15) . ?
O13 N6 1.2179(15) . ?
O10 N5 1.2177(15) . ?
O11 N5 1.2163(15) . ?
N6 C16 1.4732(15) . ?
N5 C14 1.4729(14) . ?
C17 C16 1.3793(17) . ?
C17 C12 1.3921(16) . ?
C17 H16 0.926(16) . ?
C13 C14 1.3774(16) . ?
C13 C12 1.3930(15) . ?
C13 H14 0.940(15) . ?
C12 C11 1.4981(16) . ?
C16 C15 1.3862(16) . ?
C14 C15 1.3795(17) . ?
C15 H15 0.904(16) . ?
O14 C18 1.2632(18) . ?
O14 H13 1.48(2) . ?
N8 C18 1.3378(17) . ?
N8 C20 1.451(2) . ?
N8 C19 1.455(2) . ?
N7 C18 1.340(2) . ?
N7 H17 0.96(2) . ?
N7 H18 0.94(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C8 O7 1.2561(15) . ?
C8 N4 1.3340(17) . ?
C8 N3 1.3418(16) . ?
C10 N4 1.4569(16) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 N4 1.4460(18) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N3 H5 0.89(2) . ?
N3 H6 0.83(3) . ?
O7 H1 1.42(2) . ?
O1 C1 1.3014(15) . ?
O1 H1 1.04(2) . ?
O2 C1 1.2239(15) . ?
O6 N2 1.2196(18) . ?
O5 N2 1.2234(17) . ?
N2 C6 1.4781(16) . ?
O3 N1 1.224(2) . ?
O4 N1 1.218(2) . ?
N1 C4 1.471(2) . ?
C2 C3 1.3888(18) . ?
C2 C7 1.3919(17) . ?
C2 C1 1.4953(18) . ?
C7 C6 1.3763(19) . ?
C7 H4 0.913(17) . ?
C6 C5 1.376(2) . ?
C3 C4 1.373(2) . ?
C3 H2 0.941(17) . ?
C4 C5 1.383(2) . ?
C5 H3 0.93(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O8 H13 113.3(13) . . ?
O13 N6 O12 123.98(11) . . ?
O13 N6 C16 117.93(10) . . ?
O12 N6 C16 118.09(10) . . ?
O11 N5 O10 123.80(11) . . ?
O11 N5 C14 118.00(11) . . ?
O10 N5 C14 118.20(10) . . ?
C16 C17 C12 118.76(10) . . ?
C16 C17 H16 121.1(10) . . ?
C12 C17 H16 120.2(9) . . ?
C14 C13 C12 118.87(11) . . ?
C14 C13 H14 120.5(9) . . ?
C12 C13 H14 120.6(9) . . ?
C17 C12 C13 119.83(11) . . ?
C17 C12 C11 121.85(10) . . ?
C13 C12 C11 118.24(10) . . ?
C17 C16 C15 123.06(11) . . ?
C17 C16 N6 118.85(10) . . ?
C15 C16 N6 118.05(10) . . ?
C13 C14 C15 123.19(10) . . ?
C13 C14 N5 118.42(10) . . ?
C15 C14 N5 118.34(10) . . ?
O9 C11 O8 124.91(11) . . ?
O9 C11 C12 120.83(11) . . ?
O8 C11 C12 114.23(11) . . ?
C14 C15 C16 116.27(11) . . ?
C14 C15 H15 123.6(10) . . ?
C16 C15 H15 120.1(10) . . ?
C18 O14 H13 123.4(8) . . ?
C18 N8 C20 118.71(14) . . ?
C18 N8 C19 122.52(15) . . ?
C20 N8 C19 118.77(14) . . ?
C18 N7 H17 116.7(14) . . ?
C18 N7 H18 119.7(13) . . ?
H17 N7 H18 122.7(19) . . ?
O14 C18 N8 119.34(13) . . ?
O14 C18 N7 120.40(13) . . ?
N8 C18 N7 120.26(14) . . ?
N8 C20 H20A 109.5 . . ?
N8 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N8 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N8 C19 H19A 109.5 . . ?
N8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O7 C8 N4 119.84(11) . . ?
O7 C8 N3 120.10(12) . . ?
N4 C8 N3 120.02(11) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 N4 C9 122.07(11) . . ?
C8 N4 C10 120.24(11) . . ?
C9 N4 C10 117.23(12) . . ?
C8 N3 H5 116.5(12) . . ?
C8 N3 H6 115.4(16) . . ?
H5 N3 H6 128.0(19) . . ?
C8 O7 H1 121.8(9) . . ?
C1 O1 H1 113.9(12) . . ?
O6 N2 O5 124.34(13) . . ?
O6 N2 C6 118.25(12) . . ?
O5 N2 C6 117.40(14) . . ?
O4 N1 O3 124.34(16) . . ?
O4 N1 C4 117.95(16) . . ?
O3 N1 C4 117.71(15) . . ?
C3 C2 C7 119.63(12) . . ?
C3 C2 C1 119.05(11) . . ?
C7 C2 C1 121.31(11) . . ?
C6 C7 C2 118.90(12) . . ?
C6 C7 H4 120.8(11) . . ?
C2 C7 H4 120.3(11) . . ?
O2 C1 O1 124.99(12) . . ?
O2 C1 C2 120.88(11) . . ?
O1 C1 C2 114.13(10) . . ?
C5 C6 C7 123.10(12) . . ?
C5 C6 N2 118.68(12) . . ?
C7 C6 N2 118.22(12) . . ?
C4 C3 C2 118.99(12) . . ?
C4 C3 H2 119.1(10) . . ?
C2 C3 H2 121.9(10) . . ?
C3 C4 C5 123.05(13) . . ?
C3 C4 N1 118.74(13) . . ?
C5 C4 N1 118.21(14) . . ?
C6 C5 C4 116.33(13) . . ?
C6 C5 H3 122.9(12) . . ?
C4 C5 H3 120.7(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20B O13 0.96 2.43 3.2952(19) 150.5 2_645 yes
C10 H10A O14 0.96 2.65 3.4909(19) 146.2 2_645 yes
C9 H9A O2 0.96 2.62 3.5718(18) 174.3 5_646 yes
C9 H9B O11 0.96 2.55 3.1916(19) 124.1 3_535 yes
N3 H5 O2 0.89(2) 2.03(2) 2.9079(17) 172.5(17) . yes
N3 H6 O1 0.83(3) 2.50(2) 3.1162(15) 131(2) 1_545 yes
N7 H17 O9 0.96(2) 2.01(2) 2.9516(18) 167(2) . yes
N7 H18 O8 0.94(2) 2.44(2) 3.1440(17) 131.5(17) 1_545 yes
O8 H13 O14 1.00(2) 1.48(2) 2.4687(13) 172(2) . yes
O14 H13 O9 1.48(2) 2.39(2) 3.3764(13) 119.5(12) . yes
O7 H1 O2 1.42(2) 2.43(2) 3.4404(13) 124.6(13) . yes
O1 H1 N3 1.04(2) 2.69(2) 3.5132(17) 135.7(15) . yes
O1 H1 O7 1.04(2) 1.42(2) 2.4500(14) 167(2) . yes

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 4 degreesC'

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_7_150K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922015'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_7_150K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.28 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_7_150K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.08 Ang.  
RESPONSE: The long N-H distance is characteristic of H2 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT430_complex_7_150K_shelxl 
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.77 Ang.  
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi-pi interaction.
;
_vrf_PLAT772_complex_7_150K_shelxl 
;
PROBLEM: Suspect O-H Bond in CIF: O5       --H2        ..       1.48 Ang.  
RESPONSE: The shorter O...H distance is characteristic of H2 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'isonicotinamide 2,4-dinitrobenzoate/benzoic acid 2:2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_weight         668.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0056 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0104 0.0054 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0177 0.0098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6632(4)
_cell_length_b                   10.3059(4)
_cell_length_c                   15.2750(6)
_cell_angle_alpha                79.0739(18)
_cell_angle_beta                 71.8454(18)
_cell_angle_gamma                77.2714(19)
_cell_volume                     1397.91(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      43.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22262
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.546
_diffrn_reflns_theta_max         35.634
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6629
_reflns_number_gt                5418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.76 command used to make multi_T datasets comparable: 0.76 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.2769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6629
_refine_ls_number_parameters     513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H19 H 1.4736(18) 0.7975(16) 0.1182(11) 0.031(4) Uiso 1 1 d . . . . .
H5 H 0.8023(18) 0.6615(16) 0.1709(11) 0.026(4) Uiso 1 1 d . . . . .
H10 H -0.0263(18) 0.3471(15) 0.6760(11) 0.029(4) Uiso 1 1 d . . . . .
H4 H 0.6133(17) 0.5793(17) 0.2904(11) 0.027(4) Uiso 1 1 d . . . . .
H18 H 1.2928(17) 0.6547(15) 0.1870(11) 0.028(4) Uiso 1 1 d . . . . .
H20 H 1.4870(17) 0.7308(15) -0.1389(11) 0.024(4) Uiso 1 1 d . . . . .
H3 H 0.4107(19) 0.9390(17) 0.3462(12) 0.036(4) Uiso 1 1 d . . . . .
H6 H 0.5955(17) 1.0401(17) 0.2287(11) 0.029(4) Uiso 1 1 d . . . . .
H17 H 1.0859(19) 0.0822(17) 0.1648(12) 0.033(4) Uiso 1 1 d . . . . .
H15 H 0.9018(18) -0.0265(17) 0.2779(11) 0.032(4) Uiso 1 1 d . . . . .
H11 H 0.0815(18) 0.1751(16) 0.4402(11) 0.030(4) Uiso 1 1 d . . . . .
H9 H 0.1523(19) 0.4831(17) 0.6069(12) 0.038(5) Uiso 1 1 d . . . . .
H13 H 0.480(2) 0.1215(19) 0.4895(13) 0.044(5) Uiso 1 1 d . . . . .
H7 H 1.037(2) 0.8813(19) 0.0369(13) 0.044(5) Uiso 1 1 d . . . . .
H12 H 0.537(2) 0.248(2) 0.4363(13) 0.043(5) Uiso 1 1 d . . . . .
H14 H 0.739(2) 0.3324(19) 0.3809(13) 0.046(5) Uiso 1 1 d . . . . .
H1 H 0.426(2) 0.7086(19) 0.3768(13) 0.048(5) Uiso 1 1 d . . . . .
H8 H 0.996(2) 0.7652(19) 0.1085(12) 0.041(5) Uiso 1 1 d . . . . .
H16 H 0.929(2) 0.4256(19) 0.2617(13) 0.046(5) Uiso 1 1 d . . . . .
H2 H 1.098(2) 0.315(2) 0.1602(15) 0.066(6) Uiso 1 1 d . . . . .
O2 O 1.62972(11) 0.90054(10) -0.14021(7) 0.0316(2) Uani 1 1 d . . . . .
O1 O 1.66168(13) 0.89521(12) -0.00647(8) 0.0400(3) Uani 1 1 d . . . . .
O3 O 1.36453(15) 0.56671(15) -0.17145(8) 0.0558(4) Uani 1 1 d . . . . .
O4 O 1.15722(13) 0.56342(13) -0.06521(8) 0.0440(3) Uani 1 1 d . . . . .
O5 O 1.20760(10) 0.39692(9) 0.09927(6) 0.0252(2) Uani 1 1 d . . . . .
O6 O 1.05552(10) 0.57126(9) 0.16613(7) 0.0270(2) Uani 1 1 d . . . . .
N8 N 1.60291(12) 0.86272(11) -0.05714(8) 0.0237(2) Uani 1 1 d . . . . .
N7 N 1.28403(14) 0.58350(12) -0.09374(8) 0.0300(3) Uani 1 1 d . . . . .
C5 C 1.49337(13) 0.77351(12) -0.01531(9) 0.0197(3) Uani 1 1 d . . . . .
C3 C 1.34255(13) 0.63490(12) -0.03183(9) 0.0195(3) Uani 1 1 d . . . . .
C4 C 1.44890(14) 0.71535(12) -0.07345(9) 0.0199(3) Uani 1 1 d . . . . .
C2 C 1.28472(13) 0.60862(12) 0.06401(9) 0.0198(3) Uani 1 1 d . . . . .
C1 C 1.17092(14) 0.51868(13) 0.11298(9) 0.0209(3) Uani 1 1 d . . . . .
C7 C 1.33430(15) 0.66992(14) 0.11920(9) 0.0248(3) Uani 1 1 d . . . . .
C6 C 1.43832(15) 0.75354(14) 0.08013(9) 0.0245(3) Uani 1 1 d . . . . .
C10 C 0.72698(15) 0.72206(13) 0.20448(10) 0.0238(3) Uani 1 1 d . . . . .
C13 C 0.49561(15) 0.88610(14) 0.30889(10) 0.0249(3) Uani 1 1 d . . . . .
C11 C 0.61587(15) 0.67080(14) 0.27515(10) 0.0240(3) Uani 1 1 d . . . . .
C8 C 0.84081(14) 0.92531(13) 0.11193(9) 0.0218(3) Uani 1 1 d . . . . .
C12 C 0.60408(14) 0.94255(13) 0.23957(9) 0.0232(3) Uani 1 1 d . . . . .
C9 C 0.72268(14) 0.86033(13) 0.18721(9) 0.0202(3) Uani 1 1 d . . . . .
O12 O 0.81312(10) 1.04506(9) 0.08292(7) 0.0272(2) Uani 1 1 d . . . . .
N3 N 0.97023(13) 0.84704(13) 0.08301(9) 0.0324(3) Uani 1 1 d . . . . .
N2 N 0.50473(12) 0.75248(11) 0.32580(8) 0.0227(2) Uani 1 1 d . . . . .
C17 C 0.79736(14) 0.14404(12) 0.34127(9) 0.0197(3) Uani 1 1 d . . . . .
C16 C 0.67601(14) 0.07809(12) 0.41131(9) 0.0201(3) Uani 1 1 d . . . . .
C18 C 0.90252(15) 0.06932(14) 0.27686(10) 0.0253(3) Uani 1 1 d . . . . .
C15 C 0.80617(17) 0.27690(14) 0.33820(10) 0.0311(3) Uani 1 1 d . . . . .
C14 C 0.91778(17) 0.33102(14) 0.26987(10) 0.0313(3) Uani 1 1 d . . . . .
C19 C 1.01220(15) 0.12902(14) 0.21047(10) 0.0277(3) Uani 1 1 d . . . . .
O8 O 0.47048(10) 0.43866(9) 0.40521(7) 0.0304(2) Uani 1 1 d . . . . .
O11 O -0.16792(11) 0.16901(11) 0.69022(7) 0.0354(3) Uani 1 1 d . . . . .
O9 O 0.30461(10) 0.62159(9) 0.44527(7) 0.0250(2) Uani 1 1 d . . . . .
O10 O -0.12607(12) 0.09524(10) 0.55939(8) 0.0373(3) Uani 1 1 d . . . . .
N5 N 0.28222(13) 0.31385(12) 0.33677(8) 0.0287(3) Uani 1 1 d . . . . .
N6 N -0.10279(12) 0.16561(11) 0.60759(9) 0.0268(3) Uani 1 1 d . . . . .
O13 O 0.33622(16) 0.20339(12) 0.31309(8) 0.0544(4) Uani 1 1 d . . . . .
O14 O 0.29176(14) 0.41922(12) 0.28512(7) 0.0438(3) Uani 1 1 d . . . . .
O7 O 0.69334(10) -0.04544(9) 0.42653(7) 0.0286(2) Uani 1 1 d . . . . .
N1 N 1.01774(12) 0.25803(11) 0.20796(8) 0.0226(2) Uani 1 1 d . . . . .
N4 N 0.55534(13) 0.15882(12) 0.45188(9) 0.0282(3) Uani 1 1 d . . . . .
C21 C 0.22257(13) 0.41318(12) 0.48161(9) 0.0196(3) Uani 1 1 d . . . . .
C20 C 0.34436(14) 0.49774(12) 0.43959(9) 0.0205(3) Uani 1 1 d . . . . .
C24 C 0.01050(14) 0.25104(12) 0.56393(9) 0.0218(3) Uani 1 1 d . . . . .
C25 C 0.02939(15) 0.33942(14) 0.61508(10) 0.0255(3) Uani 1 1 d . . . . .
C22 C 0.19806(14) 0.32159(12) 0.43455(9) 0.0203(3) Uani 1 1 d . . . . .
C23 C 0.09413(14) 0.23866(13) 0.47362(9) 0.0217(3) Uani 1 1 d . . . . .
C26 C 0.13631(15) 0.41959(14) 0.57276(9) 0.0252(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N8 1.2170(15) . ?
O1 N8 1.2206(15) . ?
O3 N7 1.2195(16) . ?
O4 N7 1.2162(15) . ?
O5 C1 1.2655(15) . ?
O5 H2 1.48(2) . ?
O6 C1 1.2380(15) . ?
N8 C5 1.4692(15) . ?
N7 C3 1.4662(17) . ?
C5 C4 1.3733(18) . ?
C5 C6 1.3791(18) . ?
C3 C4 1.3842(17) . ?
C3 C2 1.3912(17) . ?
C4 H20 0.947(16) . ?
C2 C7 1.3879(19) . ?
C2 C1 1.5172(16) . ?
C7 C6 1.3864(18) . ?
C7 H18 0.983(16) . ?
C6 H19 0.975(17) . ?
C10 C11 1.3816(17) . ?
C10 C9 1.3929(18) . ?
C10 H5 0.933(16) . ?
C13 N2 1.3404(17) . ?
C13 C12 1.3790(17) . ?
C13 H3 0.961(18) . ?
C11 N2 1.3383(18) . ?
C11 H4 0.931(16) . ?
C8 O12 1.2296(15) . ?
C8 N3 1.3252(18) . ?
C8 C9 1.5168(16) . ?
C12 C9 1.3889(19) . ?
C12 H6 0.977(16) . ?
N3 H7 0.87(2) . ?
N3 H8 0.877(19) . ?
N2 H1 1.02(2) . ?
C17 C15 1.3816(18) . ?
C17 C18 1.3830(19) . ?
C17 C16 1.5084(16) . ?
C16 O7 1.2333(15) . ?
C16 N4 1.3242(17) . ?
C18 C19 1.3824(18) . ?
C18 H15 0.986(17) . ?
C15 C14 1.3808(18) . ?
C15 H14 0.942(19) . ?
C14 N1 1.3316(18) . ?
C14 H16 0.985(19) . ?
C19 N1 1.3353(17) . ?
C19 H17 0.945(17) . ?
O8 C20 1.2358(16) . ?
O11 N6 1.2258(15) . ?
O9 C20 1.2607(15) . ?
O10 N6 1.2231(16) . ?
N5 O13 1.2148(16) . ?
N5 O14 1.2183(16) . ?
N5 C22 1.4691(16) . ?
N6 C24 1.4716(16) . ?
N1 H2 1.08(2) . ?
N4 H13 0.89(2) . ?
N4 H12 0.899(19) . ?
C21 C26 1.3876(18) . ?
C21 C22 1.3876(18) . ?
C21 C20 1.5250(16) . ?
C24 C23 1.3780(18) . ?
C24 C25 1.3803(19) . ?
C25 C26 1.3876(18) . ?
C25 H10 0.927(16) . ?
C22 C23 1.3808(17) . ?
C23 H11 0.952(17) . ?
C26 H9 0.974(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O5 H2 112.1(8) . . ?
O2 N8 O1 123.59(11) . . ?
O2 N8 C5 118.33(11) . . ?
O1 N8 C5 118.08(11) . . ?
O4 N7 O3 124.14(13) . . ?
O4 N7 C3 117.99(12) . . ?
O3 N7 C3 117.84(11) . . ?
C4 C5 C6 123.02(11) . . ?
C4 C5 N8 118.25(11) . . ?
C6 C5 N8 118.73(11) . . ?
C4 C3 C2 123.07(12) . . ?
C4 C3 N7 116.89(11) . . ?
C2 C3 N7 119.93(11) . . ?
C5 C4 C3 116.72(11) . . ?
C5 C4 H20 122.0(9) . . ?
C3 C4 H20 121.3(9) . . ?
C7 C2 C3 117.54(11) . . ?
C7 C2 C1 117.39(11) . . ?
C3 C2 C1 125.07(11) . . ?
O6 C1 O5 127.18(11) . . ?
O6 C1 C2 116.02(11) . . ?
O5 C1 C2 116.66(11) . . ?
C6 C7 C2 121.14(12) . . ?
C6 C7 H18 120.0(9) . . ?
C2 C7 H18 118.8(9) . . ?
C5 C6 C7 118.48(12) . . ?
C5 C6 H19 119.7(10) . . ?
C7 C6 H19 121.8(10) . . ?
C11 C10 C9 119.00(12) . . ?
C11 C10 H5 117.8(10) . . ?
C9 C10 H5 123.2(10) . . ?
N2 C13 C12 120.17(12) . . ?
N2 C13 H3 117.2(10) . . ?
C12 C13 H3 122.7(10) . . ?
N2 C11 C10 120.70(12) . . ?
N2 C11 H4 116.4(10) . . ?
C10 C11 H4 122.9(10) . . ?
O12 C8 N3 124.30(12) . . ?
O12 C8 C9 119.36(11) . . ?
N3 C8 C9 116.33(11) . . ?
C13 C12 C9 119.70(12) . . ?
C13 C12 H6 118.8(9) . . ?
C9 C12 H6 121.5(9) . . ?
C12 C9 C10 118.87(11) . . ?
C12 C9 C8 118.48(11) . . ?
C10 C9 C8 122.63(12) . . ?
C8 N3 H7 117.3(12) . . ?
C8 N3 H8 125.4(12) . . ?
H7 N3 H8 117.2(17) . . ?
C11 N2 C13 121.52(11) . . ?
C11 N2 H1 116.9(11) . . ?
C13 N2 H1 121.6(11) . . ?
C15 C17 C18 118.75(12) . . ?
C15 C17 C16 122.44(12) . . ?
C18 C17 C16 118.81(11) . . ?
O7 C16 N4 124.18(12) . . ?
O7 C16 C17 119.09(11) . . ?
N4 C16 C17 116.73(11) . . ?
C19 C18 C17 119.66(12) . . ?
C19 C18 H15 119.1(10) . . ?
C17 C18 H15 121.2(10) . . ?
C14 C15 C17 118.86(13) . . ?
C14 C15 H14 118.4(11) . . ?
C17 C15 H14 122.8(11) . . ?
N1 C14 C15 121.70(13) . . ?
N1 C14 H16 114.7(11) . . ?
C15 C14 H16 123.6(11) . . ?
N1 C19 C18 120.67(13) . . ?
N1 C19 H17 116.7(10) . . ?
C18 C19 H17 122.7(10) . . ?
O13 N5 O14 124.77(12) . . ?
O13 N5 C22 117.91(11) . . ?
O14 N5 C22 117.32(11) . . ?
O10 N6 O11 123.93(11) . . ?
O10 N6 C24 118.10(11) . . ?
O11 N6 C24 117.96(12) . . ?
C14 N1 C19 120.34(11) . . ?
C14 N1 H2 112.5(11) . . ?
C19 N1 H2 127.2(11) . . ?
C16 N4 H13 117.7(12) . . ?
C16 N4 H12 124.7(12) . . ?
H13 N4 H12 116.6(16) . . ?
C26 C21 C22 116.86(11) . . ?
C26 C21 C20 120.08(11) . . ?
C22 C21 C20 122.93(11) . . ?
O8 C20 O9 127.01(11) . . ?
O8 C20 C21 117.42(11) . . ?
O9 C20 C21 115.56(11) . . ?
C23 C24 C25 122.73(12) . . ?
C23 C24 N6 118.44(12) . . ?
C25 C24 N6 118.84(11) . . ?
C24 C25 C26 118.10(12) . . ?
C24 C25 H10 122.6(10) . . ?
C26 C25 H10 119.3(10) . . ?
C23 C22 C21 123.58(11) . . ?
C23 C22 N5 117.09(11) . . ?
C21 C22 N5 119.29(11) . . ?
C24 C23 C22 116.83(12) . . ?
C24 C23 H11 121.5(10) . . ?
C22 C23 H11 121.7(10) . . ?
C21 C26 C25 121.89(13) . . ?
C21 C26 H9 118.0(10) . . ?
C25 C26 H9 120.1(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H5 O6 0.933(16) 2.401(16) 3.1383(16) 135.8(12) . yes
C25 H10 O6 0.927(16) 2.616(16) 3.4372(17) 148.0(13) 2_666 yes
C11 H4 O3 0.931(16) 2.502(16) 3.1009(19) 122.2(12) 2_765 yes
C11 H4 O8 0.931(16) 2.344(16) 3.0958(16) 137.6(13) . yes
C13 H3 O13 0.961(18) 2.653(17) 3.2965(19) 124.7(12) 1_565 yes
N4 H13 O7 0.89(2) 1.98(2) 2.8676(15) 177.6(18) 2_656 yes
N3 H7 O12 0.87(2) 2.08(2) 2.9487(15) 173.6(18) 2_775 yes
N4 H12 O8 0.899(19) 1.94(2) 2.8357(15) 172.2(17) . yes
C15 H14 O8 0.942(19) 2.527(19) 3.2472(18) 133.5(15) . yes
N2 H1 O9 1.02(2) 1.62(2) 2.6281(13) 170.2(17) . yes
N3 H8 O6 0.877(19) 2.059(19) 2.9362(16) 178.6(17) . yes
C14 H16 O6 0.985(19) 2.178(19) 3.0105(16) 141.3(15) . yes
N1 H2 O5 1.08(2) 1.48(2) 2.5553(13) 177(2) . yes
N1 H2 O6 1.08(2) 2.60(2) 3.2487(14) 118.0(14) . yes

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.056

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_100K_har
_database_code_depnum_ccdc_archive 'CCDC 1922020'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_100K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.71 %     
RESPONSE: Related to the use of a non-standard diffraction wavelength. 
;
_vrf_PLAT211_complex_2_100K_har  
;
PROBLEM: ADP of Atom H1        is N.P.D. or (nearly) 2D .     Please Check 
RESPONSE: The HAR method is not yet optimised for the anisotropic refinement of H-atom thermal parameters.
;
_vrf_PLAT230_complex_2_100K_har  
;
PROBLEM: Hirshfeld Test Diff for    O5       --N3       .        8.3 s.u.  
RESPONSE: O5 and N3 are not the same atom type.
;
# end Validation Reply Form
_audit_creation_date             2018-12-20
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            100K
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_moiety         'C3 H9 N2 O1, C7 H3 N2 O6'
_chemical_formula_weight         300.2297
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       156
_QCr_calc_unit_n_alpha_electrons 78
_QCr_calc_unit_n_beta_electrons  78

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.986942279488
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;


# ========
# Symmetry
# ========

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'p b c a'
_symmetry_space_group_name_Hall  '-p 2ac 2ab'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, -y, +z+1/2'
'+x+1/2, -y+1/2, -z'
'+x+1/2, +y, -z+1/2'
'-x+1/2, +y+1/2, +z'
'-x, +y+1/2, -z+1/2'
'+x, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    100
_cell_measurement_reflns_used    22150
_cell_measurement_theta_max      35.801330704
_cell_measurement_theta_min      1.7132182364

_cell_length_a                   22.95610(12)
_cell_length_b                   19.16910(11)
_cell_length_c                   5.80590(3)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 90.000000(0)
_cell_angle_gamma                90.000000(0)
_cell_volume                     2554.87(2)

_cell_formula_units_Z            8.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            3283
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.004
_diffrn_reflns_theta_max         27.739
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .


# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            334.287202

_reflns_d_resolution_high        9.847648
_reflns_d_resolution_low         0.740049
_reflns_limit_h_max              30
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                2813
_reflns_number_total             2813
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0173
_refine_ls_R_factor_all          0.0173
_refine_ls_wR_factor_gt          0.0169
_refine_ls_wR_factor_all         0.0169
_refine_ls_R_Fsqd_factor         0.0211
_refine_ls_goodness_of_fit_gt    1.3675
_refine_ls_goodness_of_fit_all   1.3675
_refine_ls_number_reflns         2813
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0042
_refine_ls_shift/su_max_mean     0.0003
_refine_ls_shift/su_max_par      'H3A Uxz'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.0747
_refine_diff_density_min         -0.0616
_refine_diff_density_rms         0.0135
_refine_diff_density_max_atom    0.0215
_refine_diff_density_max_atom_tag H7
_refine_diff_density_min_atom    -0.0213
_refine_diff_density_min_atom_tag O2
_refine_diff_density_rms_atom    0.0093

_refine_special_details          
;
  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Hart with the following options:
  -shelx-f2 100K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.00285 0.00150 N 0.00565 0.00308 O 0.01010 0.00566"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  100K.cif
  
  The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

100k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 0.107345 0.692501 1.529802 0.040334 Uani 1.000000 0 0.000315 0.000369
0.001294 0.005225
H7 0.194419 0.715172 1.764323 0.040544 Uani 1.000000 0 0.000318 0.000424
0.001405 0.005459
H9 0.295276 0.593252 1.289848 0.037645 Uani 1.000000 0 0.000356 0.000413
0.001235 0.005196
H1A -0.042863 0.520655 0.775449 0.046542 Uani 1.000000 0 0.000406 0.000504
0.001436 0.006426
H1B 0.006682 0.566899 0.951323 0.031595 Uani 1.000000 0 0.000407 0.000415
0.001542 0.005949
H2A -0.106136 0.564329 0.246363 0.059117 Uani 1.000000 0 0.000385 0.000435
0.001505 0.006653
H2B -0.067043 0.511125 0.431782 0.057271 Uani 1.000000 0 0.000362 0.000431
0.001523 0.006017
H3A -0.056449 0.667902 0.161707 0.075845 Uani 1.000000 0 0.000492 0.000467
0.001599 0.007965
H2C -0.129572 0.555417 0.528957 0.069874 Uani 1.000000 0 0.000392 0.000448
0.001699 0.007181
H3B -0.103289 0.704043 0.357291 0.084009 Uani 1.000000 0 0.000465 0.000504
0.001849 0.008405
H3C -0.030173 0.718807 0.387726 0.087115 Uani 1.000000 0 0.000489 0.000538
0.001815 0.008192
H1 0.044740 0.666181 0.848527 0.019061 Uani 1.000000 0 0.000444 0.000481
0.001640 0.006882
O1 0.008608 0.673382 0.714058 0.018886 Uani 1.000000 0 0.000019 0.000020
0.000073 0.000214
N2 -0.056099 0.619346 0.482266 0.016798 Uani 1.000000 0 0.000020 0.000023
0.000081 0.000242
N1 -0.019552 0.562951 0.804806 0.020719 Uani 1.000000 0 0.000025 0.000029
0.000104 0.000291
C1 -0.022178 0.618764 0.667364 0.015197 Uani 1.000000 0 0.000023 0.000028
0.000096 0.000276
C2 -0.091916 0.559469 0.422760 0.021316 Uani 1.000000 0 0.000030 0.000035
0.000132 0.000336
C3 -0.061300 0.681550 0.339937 0.023311 Uani 1.000000 0 0.000035 0.000037
0.000128 0.000357
O2 0.090909 0.667319 0.979731 0.018945 Uani 1.000000 0 0.000017 0.000020
0.000068 0.000213
O3 0.058048 0.579176 1.197135 0.020274 Uani 1.000000 0 0.000017 0.000020
0.000068 0.000214
C5 0.150397 0.629909 1.280938 0.013836 Uani 1.000000 0 0.000023 0.000027
0.000094 0.000266
C10 0.204560 0.602640 1.218419 0.013661 Uani 1.000000 0 0.000023 0.000027
0.000093 0.000264
O5 0.258830 0.547033 0.937449 0.020060 Uani 1.000000 0 0.000017 0.000021
0.000067 0.000216
C8 0.249928 0.655617 1.540219 0.014427 Uani 1.000000 0 0.000023 0.000028
0.000093 0.000275
C4 0.095104 0.622700 1.140574 0.014567 Uani 1.000000 0 0.000023 0.000028
0.000093 0.000269
N3 0.210073 0.557991 1.014271 0.016082 Uani 1.000000 0 0.000020 0.000023
0.000080 0.000247
N4 0.302651 0.669454 1.676498 0.016986 Uani 1.000000 0 0.000021 0.000025
0.000082 0.000251
C9 0.254980 0.615069 1.344067 0.014446 Uani 1.000000 0 0.000025 0.000029
0.000099 0.000282
C6 0.147565 0.670462 1.480838 0.016074 Uani 1.000000 0 0.000026 0.000030
0.000098 0.000287
O6 0.348716 0.645249 1.608183 0.025136 Uani 1.000000 0 0.000018 0.000023
0.000074 0.000237
O7 0.297472 0.704116 1.852263 0.025903 Uani 1.000000 0 0.000019 0.000022
0.000071 0.000242
C7 0.197013 0.683251 1.611996 0.016456 Uani 1.000000 0 0.000026 0.000031
0.000106 0.000289
O4 0.165548 0.534086 0.930879 0.030174 Uani 1.000000 0 0.000018 0.000024
0.000079 0.000253

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 0.1073(3) 0.6925(4) 1.5298(13) 0.040(5) Uani 1.000000 0
H7 0.1944(3) 0.7152(4) 1.7643(14) 0.041(5) Uani 1.000000 0
H9 0.2953(4) 0.5933(4) 1.2898(12) 0.038(5) Uani 1.000000 0
H1A -0.0429(4) 0.5207(5) 0.7754(14) 0.047(6) Uani 1.000000 0
H1B 0.0067(4) 0.5669(4) 0.9513(15) 0.032(6) Uani 1.000000 0
H2A -0.1061(4) 0.5643(4) 0.2464(15) 0.059(7) Uani 1.000000 0
H2B -0.0670(4) 0.5111(4) 0.4318(15) 0.057(6) Uani 1.000000 0
H3A -0.0564(5) 0.6679(5) 0.1617(16) 0.076(8) Uani 1.000000 0
H2C -0.1296(4) 0.5554(4) 0.5290(17) 0.070(7) Uani 1.000000 0
H3B -0.1033(5) 0.7040(5) 0.3573(18) 0.084(8) Uani 1.000000 0
H3C -0.0302(5) 0.7188(5) 0.3877(18) 0.087(8) Uani 1.000000 0
H1 0.0447(4) 0.6662(5) 0.8485(16) 0.019(7) Uani 1.000000 0
O1 0.008608(19) 0.67338(2) 0.71406(7) 0.0189(2) Uani 1.000000 0
N2 -0.05610(2) 0.61935(2) 0.48227(8) 0.0168(2) Uani 1.000000 0
N1 -0.01955(3) 0.56295(3) 0.80481(10) 0.0207(3) Uani 1.000000 0
C1 -0.02218(2) 0.61876(3) 0.66736(10) 0.0152(3) Uani 1.000000 0
C2 -0.09192(3) 0.55947(3) 0.42276(13) 0.0213(3) Uani 1.000000 0
C3 -0.06130(3) 0.68155(4) 0.33994(13) 0.0233(4) Uani 1.000000 0
O2 0.090909(17) 0.66732(2) 0.97973(7) 0.0189(2) Uani 1.000000 0
O3 0.058048(17) 0.57918(2) 1.19713(7) 0.0203(2) Uani 1.000000 0
C5 0.15040(2) 0.62991(3) 1.28094(9) 0.0138(3) Uani 1.000000 0
C10 0.20456(2) 0.60264(3) 1.21842(9) 0.0137(3) Uani 1.000000 0
O5 0.258830(17) 0.54703(2) 0.93745(7) 0.0201(2) Uani 1.000000 0
C8 0.24993(2) 0.65562(3) 1.54022(9) 0.0144(3) Uani 1.000000 0
C4 0.09510(2) 0.62270(3) 1.14057(9) 0.0146(3) Uani 1.000000 0
N3 0.21007(2) 0.55799(2) 1.01427(8) 0.0161(2) Uani 1.000000 0
N4 0.30265(2) 0.66945(2) 1.67650(8) 0.0170(3) Uani 1.000000 0
C9 0.25498(3) 0.61507(3) 1.34407(10) 0.0144(3) Uani 1.000000 0
C6 0.14757(3) 0.67046(3) 1.48084(10) 0.0161(3) Uani 1.000000 0
O6 0.348716(18) 0.64525(2) 1.60818(7) 0.0251(2) Uani 1.000000 0
O7 0.297472(19) 0.70412(2) 1.85226(7) 0.0259(2) Uani 1.000000 0
C7 0.19701(3) 0.68325(3) 1.61200(11) 0.0165(3) Uani 1.000000 0
O4 0.165548(18) 0.53409(2) 0.93088(8) 0.0302(3) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.036444 0.038583 0.045974 0.000976 -0.002527 -0.012003 0.005104 0.005189
0.005381 0.004178 0.004092 0.003993
H7 0.027803 0.049564 0.044265 0.009773 -0.004236 -0.000627 0.005074 0.005895
0.005408 0.004274 0.003917 0.004336
H9 0.040134 0.041593 0.031208 -0.009881 0.002302 -0.002547 0.005342 0.005286
0.004959 0.004475 0.003995 0.003896
H1A 0.044992 0.046038 0.048596 -0.002559 -0.008778 0.003546 0.006673 0.006234
0.006371 0.005411 0.004941 0.004893
H1B 0.035934 0.022748 0.036101 0.001415 -0.017458 0.001177 0.006136 0.005476
0.006235 0.004447 0.004993 0.004552
H2A 0.062212 0.051584 0.063554 -0.021846 -0.035707 0.006810 0.006986 0.006302
0.006669 0.004961 0.005474 0.004953
H2B 0.046053 0.040257 0.085503 0.003878 -0.022283 -0.011865 0.005529 0.005532
0.006990 0.004802 0.005136 0.005001
H3A 0.123415 0.054396 0.049723 0.011517 -0.004852 0.016151 0.010600 0.006698
0.006597 0.006274 0.006334 0.004971
H2C 0.048759 0.071100 0.089762 -0.027724 0.018680 -0.032661 0.006370 0.007428
0.007746 0.005269 0.005729 0.005733
H3B 0.073674 0.068364 0.109991 0.020456 0.016842 0.047124 0.008192 0.007731
0.009293 0.006451 0.006627 0.006394
H3C 0.099487 0.068100 0.093758 -0.040674 -0.047453 0.036249 0.009199 0.007339
0.008038 0.007173 0.006874 0.006076
H1 -0.002502 0.043016 0.016670 0.003681 -0.022959 -0.016567 0.006844 0.007090
0.006713 0.005428 0.005997 0.005116
O1 0.016838 0.015007 0.024813 -0.001671 -0.004609 0.001844 0.000208 0.000203
0.000230 0.000161 0.000182 0.000172
N2 0.012734 0.018173 0.019486 -0.000299 -0.001140 0.000685 0.000230 0.000248
0.000249 0.000184 0.000193 0.000191
N1 0.019405 0.016608 0.026143 -0.003148 -0.006741 0.004339 0.000286 0.000271
0.000316 0.000219 0.000238 0.000243
C1 0.012068 0.013712 0.019812 -0.000571 -0.002225 0.001501 0.000256 0.000274
0.000297 0.000208 0.000214 0.000219
C2 0.016575 0.021311 0.026061 -0.001969 -0.004264 -0.002436 0.000320 0.000329
0.000360 0.000257 0.000290 0.000283
C3 0.024261 0.022784 0.022889 -0.000745 -0.004640 0.004793 0.000356 0.000348
0.000367 0.000283 0.000297 0.000277
O2 0.016196 0.019914 0.020725 -0.004855 -0.003677 0.005196 0.000211 0.000209
0.000218 0.000163 0.000170 0.000165
O3 0.016105 0.019779 0.024938 -0.005174 -0.003687 0.006160 0.000205 0.000214
0.000223 0.000164 0.000172 0.000172
C5 0.011214 0.014590 0.015703 0.000432 -0.000683 -0.000911 0.000262 0.000257
0.000279 0.000205 0.000216 0.000210
C10 0.011970 0.013731 0.015281 0.000868 -0.000902 -0.001624 0.000265 0.000255
0.000274 0.000209 0.000211 0.000214
O5 0.019143 0.021299 0.019738 0.002004 0.001230 -0.005270 0.000214 0.000218
0.000216 0.000166 0.000171 0.000172
C8 0.013357 0.015263 0.014660 0.000117 -0.000709 -0.000691 0.000273 0.000269
0.000284 0.000200 0.000209 0.000213
C4 0.011458 0.014531 0.017713 -0.002044 -0.000623 0.002389 0.000257 0.000264
0.000286 0.000209 0.000215 0.000220
N3 0.014305 0.016372 0.017569 0.001443 -0.001404 -0.005253 0.000249 0.000241
0.000252 0.000186 0.000194 0.000192
N4 0.014732 0.020163 0.016064 -0.000058 -0.003385 -0.002640 0.000246 0.000252
0.000254 0.000195 0.000196 0.000200
C9 0.011607 0.016239 0.015491 0.001561 -0.000496 -0.002726 0.000275 0.000279
0.000293 0.000220 0.000223 0.000221
C6 0.012666 0.018954 0.016603 0.002199 0.000815 -0.002170 0.000282 0.000287
0.000291 0.000231 0.000233 0.000227
O6 0.015063 0.037702 0.022642 0.001140 -0.004232 -0.004889 0.000214 0.000260
0.000236 0.000185 0.000179 0.000194
O7 0.024045 0.028990 0.024674 0.001404 -0.007774 -0.008877 0.000243 0.000244
0.000240 0.000192 0.000179 0.000189
C7 0.015282 0.018489 0.015597 0.001642 -0.000197 -0.003979 0.000287 0.000286
0.000296 0.000224 0.000235 0.000240
O4 0.019052 0.034290 0.037180 0.001577 -0.004999 -0.021232 0.000227 0.000262
0.000272 0.000192 0.000196 0.000211

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 . N3 . 1.2230(6) yes
O6 . N4 . 1.2210(6) yes
O7 . N4 . 1.2235(6) yes
O4 . N3 . 1.2203(6) yes
O1 . C1 . 1.2919(7) yes
O2 . C4 . 1.2700(7) yes
O3 . C4 . 1.2359(7) yes
O1 . H1 . 1.147(11) yes
O2 . H1 . 1.305(11) yes
N2 . C1 . 1.3272(7) yes
N2 . C2 . 1.4535(7) yes
N2 . C3 . 1.4557(8) yes
N1 . C1 . 1.3361(8) yes
N3 . C10 . 1.4674(7) yes
N4 . C8 . 1.4701(7) yes
N1 . H1A . 0.986(9) yes
N1 . H1B . 1.045(9) yes
C5 . C10 . 1.3968(7) yes
C5 . C4 . 1.5147(7) yes
C5 . C6 . 1.3984(8) yes
C10 . C9 . 1.3887(8) yes
C8 . C9 . 1.3837(8) yes
C8 . C7 . 1.3892(8) yes
C6 . C7 . 1.3887(8) yes
C2 . H2A . 1.079(8) yes
C2 . H2B . 1.090(8) yes
C2 . H2C . 1.065(9) yes
C3 . H3A . 1.073(9) yes
C3 . H3B . 1.061(10) yes
C3 . H3C . 1.048(10) yes
C9 . H9 . 1.063(8) yes
C6 . H6 . 1.054(7) yes
C7 . H7 . 1.077(8) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 . N3 . O4 . 123.87(5) yes
O6 . N4 . O7 . 124.16(5) yes
O5 . N3 . C10 . 118.27(4) yes
O6 . N4 . C8 . 118.01(5) yes
O7 . N4 . C8 . 117.83(5) yes
O4 . N3 . C10 . 117.86(5) yes
O2 . C4 . O3 . 126.71(5) yes
O1 . C1 . N2 . 118.95(5) yes
O1 . C1 . N1 . 119.93(5) yes
O2 . C4 . C5 . 113.43(5) yes
O3 . C4 . C5 . 119.70(5) yes
O1 . H1 . O2 . 169.1(9) yes
N2 . C1 . N1 . 121.12(5) yes
N3 . C10 . C5 . 120.33(5) yes
N3 . C10 . C9 . 116.90(5) yes
N4 . C8 . C9 . 118.38(5) yes
N4 . C8 . C7 . 119.32(5) yes
N2 . C2 . H2A . 109.2(4) yes
N2 . C2 . H2B . 111.3(4) yes
N2 . C2 . H2C . 112.3(4) yes
N2 . C3 . H3A . 109.8(5) yes
N2 . C3 . H3B . 110.7(5) yes
N2 . C3 . H3C . 110.6(5) yes
C1 . O1 . H1 . 116.2(5) yes
C4 . O2 . H1 . 118.6(4) yes
C1 . N2 . C2 . 121.18(5) yes
C1 . N2 . C3 . 120.98(5) yes
C2 . N2 . C3 . 117.74(5) yes
C1 . N1 . H1A . 122.0(5) yes
C1 . N1 . H1B . 117.0(4) yes
C5 . C10 . C9 . 122.77(5) yes
C5 . C6 . C7 . 121.01(6) yes
C10 . C5 . C4 . 124.89(5) yes
C10 . C5 . C6 . 117.72(5) yes
C10 . C9 . C8 . 117.31(5) yes
C8 . C7 . C6 . 118.88(6) yes
C4 . C5 . C6 . 117.28(5) yes
C9 . C8 . C7 . 122.30(5) yes
C5 . C6 . H6 . 119.2(4) yes
C10 . C9 . H9 . 120.2(4) yes
C8 . C9 . H9 . 122.5(4) yes
C8 . C7 . H7 . 120.8(4) yes
C6 . C7 . H7 . 120.4(4) yes
C7 . C6 . H6 . 119.8(4) yes
H1A . N1 . H1B . 120.9(6) yes
H2A . C2 . H2B . 106.1(6) yes
H2A . C2 . H2C . 108.1(7) yes
H2B . C2 . H2C . 109.6(7) yes
H3A . C3 . H3B . 106.6(8) yes
H3A . C3 . H3C . 110.5(8) yes
H3B . C3 . H3C . 108.5(8) yes
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate 1:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_8_350K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922017'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_8_350K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      48.33 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_8_350K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H1       .       1.09 Ang.  
RESPONSE: Characteristic of H1 forming a short strong charge assisted
N+-H...O- hydrogen bond.
;
_vrf_PLAT772_complex_8_350K_shelxl 
;
PROBLEM: Suspect O-H Bond in CIF: O1       --H1        ..       1.48 Ang.  
RESPONSE: Characteristic of H1 forming a short strong charge assisted
N+-H...O- hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide 3,5-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 N2 O6, C6 H7 N2 O1'
_chemical_formula_sum            'C13 H10 N4 O7'
_chemical_formula_weight         334.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.52240(7)
_cell_length_b                   9.00890(6)
_cell_length_c                   10.84300(8)
_cell_angle_alpha                88.0720(7)
_cell_angle_beta                 76.8850(7)
_cell_angle_gamma                87.7960(7)
_cell_volume                     714.884(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    350(2)
_cell_measurement_reflns_used    8951
_cell_measurement_theta_max      35.1433976236
_cell_measurement_theta_min      1.86115928367

_exptl_crystal_description       'triangular block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      350(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24632
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.870
_diffrn_reflns_theta_max         36.157
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6918
_reflns_number_gt                4002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0949P)²+0.0270P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6918
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1935
_refine_ls_wR_factor_gt          0.1639
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.51734(16) 0.20291(10) -0.00415(9) 0.0651(3) Uani 1 1 d . . . . .
N2 N 0.60201(16) 0.04185(11) 0.13686(10) 0.0530(3) Uani 1 1 d . . . . .
N1 N 0.70202(17) 0.54854(11) 0.28359(10) 0.0545(3) Uani 1 1 d . . . . .
C13 C 0.57816(15) 0.17744(12) 0.09098(10) 0.0453(2) Uani 1 1 d . . . . .
C11 C 0.6670(2) 0.43975(13) 0.09664(12) 0.0566(3) Uani 1 1 d . . . . .
C10 C 0.62569(15) 0.30623(11) 0.16139(10) 0.0432(2) Uani 1 1 d . . . . .
C8 C 0.6633(2) 0.42134(13) 0.34762(11) 0.0573(3) Uani 1 1 d . . . . .
C12 C 0.7059(2) 0.55966(14) 0.16078(13) 0.0619(3) Uani 1 1 d . . . . .
C9 C 0.6251(2) 0.29702(13) 0.28914(11) 0.0533(3) Uani 1 1 d . . . . .
O5 O 0.8788(2) 1.33903(12) 0.79784(12) 0.0857(4) Uani 1 1 d . . . . .
O2 O 0.69903(18) 0.95717(12) 0.37336(10) 0.0737(3) Uani 1 1 d . . . . .
O4 O 0.95314(19) 0.83988(13) 0.95767(10) 0.0762(3) Uani 1 1 d . . . . .
O3 O 0.9057(2) 0.65541(12) 0.85184(12) 0.0826(4) Uani 1 1 d . . . . .
O1 O 0.7537(2) 0.73051(12) 0.44386(11) 0.0922(5) Uani 1 1 d . . . . .
O6 O 0.7392(3) 1.37440(12) 0.64699(15) 0.1038(5) Uani 1 1 d . . . . .
N3 N 0.91242(15) 0.78817(12) 0.86601(10) 0.0531(2) Uani 1 1 d . . . . .
N4 N 0.81029(19) 1.29439(11) 0.71550(12) 0.0625(3) Uani 1 1 d . . . . .
C4 C 0.86812(15) 0.89052(12) 0.76838(10) 0.0436(2) Uani 1 1 d . . . . .
C3 C 0.82672(16) 0.83191(12) 0.66206(10) 0.0453(2) Uani 1 1 d . . . . .
C5 C 0.86607(16) 1.04134(12) 0.78842(11) 0.0466(2) Uani 1 1 d . . . . .
C6 C 0.81504(17) 1.13302(11) 0.69778(11) 0.0473(2) Uani 1 1 d . . . . .
C7 C 0.76942(17) 1.08070(12) 0.59072(11) 0.0477(2) Uani 1 1 d . . . . .
C2 C 0.77818(15) 0.92822(11) 0.57169(10) 0.0444(2) Uani 1 1 d . . . . .
C1 C 0.73751(19) 0.86934(13) 0.45193(11) 0.0514(3) Uani 1 1 d . . . . .
H10 H 0.739(2) 1.1442(19) 0.5272(17) 0.067(4) Uiso 1 1 d . . . . .
H9 H 0.896(2) 1.0834(18) 0.8612(15) 0.060(4) Uiso 1 1 d . . . . .
H8 H 0.831(2) 0.7297(17) 0.6541(14) 0.055(4) Uiso 1 1 d . . . . .
H3 H 0.595(2) 0.208(2) 0.3424(17) 0.073(5) Uiso 1 1 d . . . . .
H4 H 0.737(2) 0.660(2) 0.1163(17) 0.076(5) Uiso 1 1 d . . . . .
H6 H 0.643(2) 0.0217(19) 0.2111(18) 0.069(5) Uiso 1 1 d . . . . .
H5 H 0.675(3) 0.454(2) 0.016(2) 0.086(5) Uiso 1 1 d . . . . .
H2 H 0.658(3) 0.422(2) 0.433(2) 0.086(6) Uiso 1 1 d . . . . .
H7 H 0.572(2) -0.0399(19) 0.0926(16) 0.070(5) Uiso 1 1 d . . . . .
H1 H 0.729(3) 0.643(2) 0.336(2) 0.106(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 C13 1.2313(14) . ?
N2 C13 1.3246(15) . ?
N2 H6 0.937(18) . ?
N2 H7 0.953(18) . ?
N1 C12 1.3256(16) . ?
N1 C8 1.3268(17) . ?
N1 H1 1.09(2) . ?
C13 C10 1.5074(13) . ?
C11 C12 1.3798(16) . ?
C11 C10 1.3818(17) . ?
C11 H5 0.87(2) . ?
C10 C9 1.3840(16) . ?
C8 C9 1.3762(15) . ?
C8 H2 0.92(2) . ?
C12 H4 1.016(18) . ?
C9 H3 0.978(18) . ?
O5 N4 1.2137(15) . ?
O2 C1 1.2184(16) . ?
O4 N3 1.2161(14) . ?
O3 N3 1.2154(14) . ?
O1 C1 1.2560(15) . ?
O1 H1 1.48(2) . ?
O6 N4 1.2134(17) . ?
N3 C4 1.4671(16) . ?
N4 C6 1.4709(14) . ?
C4 C5 1.3821(15) . ?
C4 C3 1.3862(14) . ?
C3 C2 1.3882(17) . ?
C3 H8 0.927(15) . ?
C5 C6 1.3740(17) . ?
C5 H9 0.962(17) . ?
C6 C7 1.3847(15) . ?
C7 C2 1.3929(14) . ?
C7 H10 0.944(17) . ?
C2 C1 1.5166(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N2 H6 124.0(11) . . ?
C13 N2 H7 117.8(10) . . ?
H6 N2 H7 118.2(14) . . ?
C12 N1 C8 120.93(10) . . ?
C12 N1 H1 121.7(12) . . ?
C8 N1 H1 117.3(12) . . ?
O7 C13 N2 123.49(10) . . ?
O7 C13 C10 118.98(10) . . ?
N2 C13 C10 117.52(10) . . ?
C12 C11 C10 119.31(11) . . ?
C12 C11 H5 116.0(13) . . ?
C10 C11 H5 124.7(13) . . ?
C11 C10 C9 118.70(9) . . ?
C11 C10 C13 118.74(10) . . ?
C9 C10 C13 122.54(10) . . ?
N1 C8 C9 121.24(11) . . ?
N1 C8 H2 116.5(13) . . ?
C9 C8 H2 122.2(13) . . ?
N1 C12 C11 120.81(12) . . ?
N1 C12 H4 117.7(10) . . ?
C11 C12 H4 121.5(10) . . ?
C8 C9 C10 118.99(11) . . ?
C8 C9 H3 116.9(11) . . ?
C10 C9 H3 124.0(11) . . ?
C1 O1 H1 126.1(9) . . ?
O3 N3 O4 122.99(12) . . ?
O3 N3 C4 118.41(10) . . ?
O4 N3 C4 118.60(11) . . ?
O6 N4 O5 124.14(12) . . ?
O6 N4 C6 118.23(11) . . ?
O5 N4 C6 117.62(12) . . ?
C5 C4 C3 123.13(11) . . ?
C5 C4 N3 118.12(9) . . ?
C3 C4 N3 118.74(10) . . ?
C4 C3 C2 118.93(10) . . ?
C4 C3 H8 119.0(9) . . ?
C2 C3 H8 122.1(9) . . ?
C6 C5 C4 116.24(9) . . ?
C6 C5 H9 119.9(9) . . ?
C4 C5 H9 123.9(9) . . ?
C5 C6 C7 123.15(10) . . ?
C5 C6 N4 118.09(9) . . ?
C7 C6 N4 118.76(11) . . ?
C6 C7 C2 119.06(11) . . ?
C6 C7 H10 122.9(11) . . ?
C2 C7 H10 117.9(11) . . ?
C3 C2 C7 119.45(9) . . ?
C3 C2 C1 120.74(9) . . ?
C7 C2 C1 119.80(10) . . ?
O2 C1 O1 126.81(11) . . ?
O2 C1 C2 119.03(11) . . ?
O1 C1 C2 114.12(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H9 O4 0.962(17) 2.605(17) 3.5474(14) 166.7(12) 2_777 yes
C9 H3 O2 0.978(18) 2.399(18) 3.2293(16) 142.4(14) 1_545 yes
C12 H4 O4 1.016(18) 2.645(18) 3.5791(19) 152.8(13) 1_554 yes
N2 H6 O2 0.937(18) 1.963(19) 2.8923(15) 171.0(15) 1_545 yes
C11 H5 O5 0.87(2) 2.72(2) 3.4062(19) 136.5(16) 1_544 yes
C8 H2 O6 0.92(2) 2.55(2) 3.4310(18) 161.6(16) 1_545 yes
N2 H7 O7 0.953(18) 1.999(19) 2.9480(12) 173.9(15) 2_655 yes
N1 H1 O1 1.09(2) 1.48(2) 2.5310(13) 160(2) . yes

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.043

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_8_100K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922016'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_8_100K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      49.57 %     
RESPONSE: ata collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'isonicotinamide 3,5-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 N2 O6, C6 H7 N2 O1'
_chemical_formula_sum            'C13 H10 N4 O7'
_chemical_formula_weight         334.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.24910(3)
_cell_length_b                   9.00520(4)
_cell_length_c                   10.79980(4)
_cell_angle_alpha                87.8510(4)
_cell_angle_beta                 76.1640(3)
_cell_angle_gamma                86.9090(3)
_cell_volume                     683.334(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10759
_cell_measurement_theta_max      35.8117587841
_cell_measurement_theta_min      1.87889419168

_exptl_crystal_description       'triangular block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15124
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.883
_diffrn_reflns_theta_max         36.085
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6229
_reflns_number_gt                5605
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²+0.0764P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6229
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.51313(7) 0.20333(5) -0.00432(4) 0.01576(9) Uani 1 1 d . . . . .
N2 N 0.60624(8) 0.03965(6) 0.13626(5) 0.01368(9) Uani 1 1 d . . . . .
N1 N 0.70831(8) 0.54620(6) 0.28350(5) 0.01403(9) Uani 1 1 d . . . . .
C13 C 0.57785(8) 0.17663(6) 0.09116(5) 0.01182(9) Uani 1 1 d . . . . .
C11 C 0.66882(9) 0.43938(6) 0.09524(6) 0.01417(10) Uani 1 1 d . . . . .
C10 C 0.62678(8) 0.30504(6) 0.16145(5) 0.01156(9) Uani 1 1 d . . . . .
C8 C 0.66821(9) 0.41808(7) 0.34938(6) 0.01460(10) Uani 1 1 d . . . . .
C12 C 0.71101(9) 0.55887(7) 0.15923(6) 0.01532(10) Uani 1 1 d . . . . .
C9 C 0.62779(9) 0.29400(6) 0.29076(6) 0.01371(10) Uani 1 1 d . . . . .
O5 O 0.87954(8) 1.33608(5) 0.80244(5) 0.02000(10) Uani 1 1 d . . . . .
O2 O 0.69682(8) 0.95808(6) 0.37518(5) 0.01909(10) Uani 1 1 d . . . . .
O4 O 0.95325(8) 0.83557(6) 0.96466(5) 0.01800(9) Uani 1 1 d . . . . .
O3 O 0.90490(8) 0.64914(5) 0.85643(5) 0.01820(9) Uani 1 1 d . . . . .
O1 O 0.76539(10) 0.72749(6) 0.44317(5) 0.02356(11) Uani 1 1 d . . . . .
O6 O 0.72665(9) 1.37366(6) 0.65332(6) 0.02382(11) Uani 1 1 d . . . . .
N3 N 0.91274(7) 0.78253(6) 0.87173(5) 0.01271(9) Uani 1 1 d . . . . .
N4 N 0.80588(8) 1.29223(6) 0.72082(5) 0.01498(9) Uani 1 1 d . . . . .
C4 C 0.86907(8) 0.88628(6) 0.77302(5) 0.01136(9) Uani 1 1 d . . . . .
C3 C 0.82911(8) 0.82812(6) 0.66547(5) 0.01203(9) Uani 1 1 d . . . . .
C5 C 0.86599(8) 1.03747(6) 0.79383(5) 0.01223(9) Uani 1 1 d . . . . .
C6 C 0.81223(8) 1.13082(6) 0.70210(5) 0.01202(9) Uani 1 1 d . . . . .
C7 C 0.76636(8) 1.07901(6) 0.59451(5) 0.01268(9) Uani 1 1 d . . . . .
C2 C 0.77890(8) 0.92616(6) 0.57470(5) 0.01183(9) Uani 1 1 d . . . . .
C1 C 0.74179(9) 0.86736(7) 0.45347(5) 0.01344(10) Uani 1 1 d . . . . .
H10 H 0.7301(17) 1.1462(14) 0.5330(12) 0.027(3) Uiso 1 1 d . . . . .
H9 H 0.9005(16) 1.0804(13) 0.8669(11) 0.023(3) Uiso 1 1 d . . . . .
H8 H 0.8374(17) 0.7250(13) 0.6542(12) 0.025(3) Uiso 1 1 d . . . . .
H3 H 0.5992(17) 0.2019(14) 0.3428(12) 0.026(3) Uiso 1 1 d . . . . .
H4 H 0.7418(16) 0.6562(13) 0.1186(11) 0.023(3) Uiso 1 1 d . . . . .
H6 H 0.6524(17) 0.0217(14) 0.2095(12) 0.028(3) Uiso 1 1 d . . . . .
H5 H 0.6758(18) 0.4513(14) 0.0080(12) 0.028(3) Uiso 1 1 d . . . . .
H2 H 0.6669(19) 0.4186(15) 0.4375(13) 0.031(3) Uiso 1 1 d . . . . .
H7 H 0.5726(18) -0.0410(14) 0.0947(12) 0.027(3) Uiso 1 1 d . . . . .
H1 H 0.7343(19) 0.6333(15) 0.3340(14) 0.038(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 C13 1.2417(7) . ?
N2 C13 1.3330(8) . ?
N2 H6 0.935(12) . ?
N2 H7 0.941(12) . ?
N1 C12 1.3382(8) . ?
N1 C8 1.3408(8) . ?
N1 H1 1.023(14) . ?
C13 C10 1.5093(8) . ?
C11 C12 1.3861(8) . ?
C11 C10 1.3923(8) . ?
C11 H5 0.934(13) . ?
C10 C9 1.3980(8) . ?
C8 C9 1.3828(8) . ?
C8 H2 0.950(13) . ?
C12 H4 0.978(12) . ?
C9 H3 0.987(13) . ?
O5 N4 1.2215(7) . ?
O2 C1 1.2409(8) . ?
O4 N3 1.2303(7) . ?
O3 N3 1.2249(7) . ?
O1 C1 1.2674(8) . ?
O6 N4 1.2304(7) . ?
N3 C4 1.4712(8) . ?
N4 C6 1.4718(8) . ?
C4 C5 1.3864(8) . ?
C4 C3 1.3894(8) . ?
C3 C2 1.3943(8) . ?
C3 H8 0.938(12) . ?
C5 C6 1.3881(8) . ?
C5 H9 0.981(12) . ?
C6 C7 1.3859(8) . ?
C7 C2 1.3957(8) . ?
C7 H10 0.956(12) . ?
C2 C1 1.5175(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N2 H6 122.4(8) . . ?
C13 N2 H7 118.2(7) . . ?
H6 N2 H7 119.3(11) . . ?
C12 N1 C8 121.50(5) . . ?
C12 N1 H1 122.4(8) . . ?
C8 N1 H1 116.1(8) . . ?
O7 C13 N2 123.55(5) . . ?
O7 C13 C10 118.93(5) . . ?
N2 C13 C10 117.52(5) . . ?
C12 C11 C10 119.11(5) . . ?
C12 C11 H5 118.2(8) . . ?
C10 C11 H5 122.6(8) . . ?
C11 C10 C9 119.25(5) . . ?
C11 C10 C13 118.55(5) . . ?
C9 C10 C13 122.19(5) . . ?
N1 C8 C9 120.87(5) . . ?
N1 C8 H2 116.4(8) . . ?
C9 C8 H2 122.7(8) . . ?
N1 C12 C11 120.51(5) . . ?
N1 C12 H4 116.1(7) . . ?
C11 C12 H4 123.4(7) . . ?
C8 C9 C10 118.73(5) . . ?
C8 C9 H3 118.2(7) . . ?
C10 C9 H3 123.1(7) . . ?
O3 N3 O4 124.34(5) . . ?
O3 N3 C4 117.83(5) . . ?
O4 N3 C4 117.82(5) . . ?
O5 N4 O6 124.52(5) . . ?
O5 N4 C6 117.70(5) . . ?
O6 N4 C6 117.79(5) . . ?
C5 C4 C3 123.44(5) . . ?
C5 C4 N3 117.99(5) . . ?
C3 C4 N3 118.55(5) . . ?
C4 C3 C2 118.62(5) . . ?
C4 C3 H8 120.3(7) . . ?
C2 C3 H8 121.1(7) . . ?
C4 C5 C6 115.94(5) . . ?
C4 C5 H9 124.4(7) . . ?
C6 C5 H9 119.6(7) . . ?
C7 C6 C5 123.12(5) . . ?
C7 C6 N4 119.13(5) . . ?
C5 C6 N4 117.75(5) . . ?
C6 C7 C2 119.03(5) . . ?
C6 C7 H10 121.1(7) . . ?
C2 C7 H10 119.9(7) . . ?
C3 C2 C7 119.78(5) . . ?
C3 C2 C1 120.21(5) . . ?
C7 C2 C1 120.00(5) . . ?
O2 C1 O1 127.18(6) . . ?
O2 C1 C2 118.30(5) . . ?
O1 C1 C2 114.50(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H9 O4 0.981(12) 2.473(12) 3.4419(7) 169.2(9) 2_777
C9 H3 O2 0.987(13) 2.310(12) 3.1750(8) 145.7(10) 1_545
C12 H4 O4 0.978(12) 2.563(12) 3.4673(8) 153.8(9) 1_554
N2 H6 O2 0.935(12) 1.953(13) 2.8713(7) 166.9(11) 1_545
C11 H5 O5 0.934(13) 2.574(12) 3.3099(8) 136.0(10) 1_544
C8 H2 O6 0.950(13) 2.485(13) 3.4151(8) 166.2(11) 1_545
N2 H7 O7 0.941(12) 1.992(12) 2.9317(7) 176.2(11) 2_655
N1 H1 O1 1.023(14) 1.543(14) 2.5368(7) 162.3(13) .

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol at 30 degreesC'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_300K_har
_database_code_depnum_ccdc_archive 'CCDC 1922022'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_300K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      45.98 %     
RESPONSE: Related to the use of a non-standard diffraction wavelength. 
;
_vrf_PLAT230_complex_2_300K_har  
;
PROBLEM: Hirshfeld Test Diff for    O2       --C4       .        9.3 s.u.  
RESPONSE: O2 and C4 are not the same atom type.
;
# end Validation Reply Form

_audit_creation_date             2019-1-7
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            300K
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_moiety         'C3 H8 N2 O1, C7 H4 N2 O6'
_chemical_formula_weight         300.2297
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       156
_QCr_calc_unit_n_alpha_electrons 78
_QCr_calc_unit_n_beta_electrons  78

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008


# ==============
# Absortion data
# ==============
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.994646578694
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'p b c a'
_symmetry_space_group_name_Hall  '-p 2ac 2ab'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, -y, +z+1/2'
'+x+1/2, -y+1/2, -z'
'+x+1/2, +y, -z+1/2'
'-x+1/2, +y+1/2, +z'
'-x, +y+1/2, -z+1/2'
'+x, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    300
_cell_measurement_reflns_used    16293
_cell_measurement_theta_min      1.69764954856
_cell_measurement_theta_max      34.2644147636

_cell_length_a                   23.1543(2)
_cell_length_b                   19.32370(17)
_cell_length_c                   5.95150(6)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 90.000000(0)
_cell_angle_gamma                90.000000(0)
_cell_volume                     2662.86(4)

_cell_formula_units_Z            8.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'


# ================
# Diffraction data
# ================

_diffrn_reflns_number            3429
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.988
_diffrn_reflns_theta_max         27.740
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            333.608145

_reflns_d_resolution_high        9.931193
_reflns_d_resolution_low         0.740070
_reflns_limit_h_max              31
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                2372
_reflns_number_total             2372
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0366
_refine_ls_R_factor_all          0.0366
_refine_ls_wR_factor_gt          0.0332
_refine_ls_wR_factor_all         0.0332
_refine_ls_R_Fsqd_factor         0.0343
_refine_ls_goodness_of_fit_gt    3.0181
_refine_ls_goodness_of_fit_all   3.0181
_refine_ls_number_reflns         2372
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_number_constraints    72
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0062
_refine_ls_shift/su_max_mean     0.0005
_refine_ls_shift/su_max_par      'C2 Uzz'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1155
_refine_diff_density_min         -0.1094
_refine_diff_density_rms         0.0161
_refine_diff_density_max_atom    0.0285
_refine_diff_density_max_atom_tag C2
_refine_diff_density_min_atom    -0.0514
_refine_diff_density_min_atom_tag H3A
_refine_diff_density_rms_atom    0.0202

_refine_special_details          
;

  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 300K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.00285 0.00150 N 0.00565 0.00308 O 0.01010 0.00566"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps f
  -scf rhf
  300K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

300k.cif obtained from res in _shelx_res_file    
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 0.106690 0.691192 1.517325 0.076000 Uani 1.000000 0 0.000663 0.000764
0.002479 0.000000
H7 0.191344 0.712530 1.737178 0.080000 Uani 1.000000 0 0.000654 0.000852
0.002816 0.000000
H9 0.289408 0.593008 1.288730 0.059000 Uani 1.000000 0 0.000639 0.000736
0.002268 0.000000
H1A -0.041509 0.520178 0.767488 0.088000 Uani 1.000000 0 0.000825 0.001062
0.002917 0.000000
H1B 0.004490 0.567880 0.946034 0.075000 Uani 1.000000 0 0.000873 0.000917
0.003275 0.000000
H1 0.044789 0.665842 0.875151 0.123000 Uani 1.000000 0 0.001425 0.001330
0.005126 0.000000
O1 0.006978 0.671566 0.719986 0.065445 Uani 1.000000 0 0.000044 0.000052
0.000175 0.000709
N2 -0.058091 0.619050 0.499039 0.058579 Uani 1.000000 0 0.000051 0.000063
0.000201 0.000792
N1 -0.019818 0.562593 0.805474 0.072807 Uani 1.000000 0 0.000065 0.000074
0.000255 0.000984
C1 -0.023450 0.618050 0.675541 0.052003 Uani 1.000000 0 0.000061 0.000077
0.000253 0.000934
C2 -0.093759 0.560429 0.438165 0.079982 Uani 1.000000 0 0.000084 0.000108
0.000374 0.001352
H2A -0.069784 0.512479 0.429176 0.121000 Uani 1.000000 0 0.000854 0.001095
0.003461 0.000000
H2B -0.105879 0.567383 0.266111 0.121000 Uani 1.000000 0 0.000906 0.001090
0.003443 0.000000
H2C -0.125168 0.553301 0.544725 0.121000 Uani 1.000000 0 0.000923 0.001043
0.003500 0.000000
C3 -0.063213 0.680988 0.362705 0.085058 Uani 1.000000 0 0.000098 0.000109
0.000351 0.001463
H3A -0.106563 0.702543 0.376530 0.128000 Uani 1.000000 0 0.000917 0.001069
0.003526 0.000000
H3B -0.061541 0.667737 0.199450 0.128000 Uani 1.000000 0 0.000918 0.001126
0.003471 0.000000
H3C -0.034032 0.713615 0.404734 0.128000 Uani 1.000000 0 0.000943 0.001138
0.003764 0.000000
O2 0.089245 0.666049 0.978394 0.065117 Uani 1.000000 0 0.000045 0.000054
0.000173 0.000706
O3 0.056865 0.580138 1.189717 0.071179 Uani 1.000000 0 0.000046 0.000056
0.000175 0.000737
C5 0.147975 0.630194 1.272777 0.044596 Uani 1.000000 0 0.000058 0.000068
0.000225 0.000812
C10 0.201538 0.602620 1.214121 0.042960 Uani 1.000000 0 0.000058 0.000065
0.000212 0.000789
O5 0.254903 0.547142 0.943422 0.071941 Uani 1.000000 0 0.000052 0.000055
0.000181 0.000782
C8 0.245780 0.655627 1.527553 0.046676 Uani 1.000000 0 0.000059 0.000070
0.000217 0.000834
C4 0.093635 0.622494 1.134382 0.049314 Uani 1.000000 0 0.000061 0.000072
0.000243 0.000889
N3 0.207477 0.558321 1.017381 0.054870 Uani 1.000000 0 0.000062 0.000062
0.000202 0.000820
N4 0.297657 0.669973 1.661307 0.059335 Uani 1.000000 0 0.000060 0.000070
0.000223 0.000888
C9 0.250852 0.615100 1.338303 0.046383 Uani 1.000000 0 0.000061 0.000070
0.000228 0.000841
C6 0.144964 0.670354 1.466548 0.052756 Uani 1.000000 0 0.000065 0.000078
0.000241 0.000924
O6 0.343074 0.646751 1.596439 0.087744 Uani 1.000000 0 0.000054 0.000072
0.000202 0.000908
O7 0.292354 0.703463 1.831471 0.089849 Uani 1.000000 0 0.000052 0.000065
0.000209 0.000940
C7 0.193469 0.682988 1.594522 0.053507 Uani 1.000000 0 0.000067 0.000077
0.000254 0.000955
O4 0.164355 0.534399 0.936190 0.104323 Uani 1.000000 0 0.000057 0.000075
0.000231 0.001041

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 0.1067(7) 0.6912(8) 1.517(2) 0.07600000(0) Uani 1.000000 0
H7 0.1913(7) 0.7125(9) 1.737(3) 0.08000000(0) Uani 1.000000 0
H9 0.2894(6) 0.5930(7) 1.289(2) 0.05900000(0) Uani 1.000000 0
H1A -0.0415(8) 0.5202(11) 0.767(3) 0.08800000(0) Uani 1.000000 0
H1B 0.0045(9) 0.5679(9) 0.946(3) 0.07500000(0) Uani 1.000000 0
H1 0.0448(14) 0.6658(13) 0.875(5) 0.12300000(0) Uani 1.000000 0
O1 0.00698(4) 0.67157(5) 0.71999(17) 0.0654(7) Uani 1.000000 0
N2 -0.05809(5) 0.61905(6) 0.4990(2) 0.0586(8) Uani 1.000000 0
N1 -0.01982(6) 0.56259(7) 0.8055(3) 0.0728(10) Uani 1.000000 0
C1 -0.02345(6) 0.61805(8) 0.6755(3) 0.0520(9) Uani 1.000000 0
C2 -0.09376(8) 0.56043(11) 0.4382(4) 0.0800(14) Uani 1.000000 0
H2A -0.0698(9) 0.5125(11) 0.429(3) 0.12100000(0) Uani 1.000000 0
H2B -0.1059(9) 0.5674(11) 0.266(3) 0.12100000(0) Uani 1.000000 0
H2C -0.1252(9) 0.5533(10) 0.545(4) 0.12100000(0) Uani 1.000000 0
C3 -0.06321(10) 0.68099(11) 0.3627(4) 0.0851(15) Uani 1.000000 0
H3A -0.1066(9) 0.7025(11) 0.377(4) 0.12800000(0) Uani 1.000000 0
H3B -0.0615(9) 0.6677(11) 0.199(3) 0.12800000(0) Uani 1.000000 0
H3C -0.0340(9) 0.7136(11) 0.405(4) 0.12800000(0) Uani 1.000000 0
O2 0.08924(5) 0.66605(5) 0.97839(17) 0.0651(7) Uani 1.000000 0
O3 0.05686(5) 0.58014(6) 1.18972(17) 0.0712(7) Uani 1.000000 0
C5 0.14798(6) 0.63019(7) 1.2728(2) 0.0446(8) Uani 1.000000 0
C10 0.20154(6) 0.60262(7) 1.2141(2) 0.0430(8) Uani 1.000000 0
O5 0.25490(5) 0.54714(6) 0.94342(18) 0.0719(8) Uani 1.000000 0
C8 0.24578(6) 0.65563(7) 1.5276(2) 0.0467(8) Uani 1.000000 0
C4 0.09364(6) 0.62249(7) 1.1344(2) 0.0493(9) Uani 1.000000 0
N3 0.20748(6) 0.55832(6) 1.0174(2) 0.0549(8) Uani 1.000000 0
N4 0.29766(6) 0.66997(7) 1.6613(2) 0.0593(9) Uani 1.000000 0
C9 0.25085(6) 0.61510(7) 1.3383(2) 0.0464(8) Uani 1.000000 0
C6 0.14496(6) 0.67035(8) 1.4665(2) 0.0528(9) Uani 1.000000 0
O6 0.34307(5) 0.64675(7) 1.5964(2) 0.0877(9) Uani 1.000000 0
O7 0.29235(5) 0.70346(7) 1.8315(2) 0.0898(9) Uani 1.000000 0
C7 0.19347(7) 0.68299(8) 1.5945(3) 0.0535(10) Uani 1.000000 0
O4 0.16436(6) 0.53440(8) 0.9362(2) 0.1043(10) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.076000 0.076000 0.076000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H7 0.080000 0.080000 0.080000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H9 0.059000 0.059000 0.059000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H1A 0.088000 0.088000 0.088000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H1B 0.075000 0.075000 0.075000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H1 0.123000 0.123000 0.123000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
O1 0.062699 0.052465 0.081172 -0.006595 -0.015110 0.008981 0.000698 0.000659
0.000769 0.000534 0.000570 0.000552
N2 0.047753 0.065811 0.062172 0.001290 -0.003746 0.001338 0.000721 0.000866
0.000788 0.000647 0.000637 0.000667
N1 0.072714 0.057458 0.088249 -0.014672 -0.027671 0.015744 0.001030 0.000881
0.001040 0.000735 0.000776 0.000823
C1 0.043891 0.049672 0.062446 -0.001745 -0.007138 0.006644 0.000855 0.000965
0.000983 0.000732 0.000733 0.000775
C2 0.067457 0.084411 0.088077 -0.010574 -0.017353 -0.004666 0.001308 0.001355
0.001394 0.001052 0.001054 0.001171
H2A 0.121000 0.121000 0.121000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H2B 0.121000 0.121000 0.121000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H2C 0.121000 0.121000 0.121000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
C3 0.092898 0.083966 0.078310 -0.000642 -0.022959 0.018809 0.001587 0.001510
0.001293 0.001119 0.001224 0.001157
H3A 0.128000 0.128000 0.128000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H3B 0.128000 0.128000 0.128000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H3C 0.128000 0.128000 0.128000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
O2 0.060412 0.065743 0.069196 -0.017587 -0.014439 0.017039 0.000701 0.000715
0.000703 0.000555 0.000531 0.000555
O3 0.061439 0.069163 0.082935 -0.020254 -0.015078 0.022474 0.000710 0.000754
0.000748 0.000582 0.000558 0.000595
C5 0.042416 0.041771 0.049599 0.000026 -0.000507 0.000011 0.000839 0.000752
0.000843 0.000627 0.000649 0.000633
C10 0.045674 0.038551 0.044654 0.000915 -0.001841 -0.002896 0.000857 0.000729
0.000782 0.000618 0.000642 0.000608
O5 0.077238 0.074160 0.064425 0.008024 0.006669 -0.021491 0.000843 0.000809
0.000693 0.000628 0.000596 0.000569
C8 0.050629 0.045257 0.044143 -0.000468 -0.001979 -0.000294 0.000883 0.000821
0.000797 0.000658 0.000676 0.000630
C4 0.045907 0.044249 0.057788 -0.008419 -0.003968 0.011367 0.000899 0.000841
0.000928 0.000721 0.000713 0.000741
N3 0.054454 0.052569 0.057588 0.004714 -0.005274 -0.015418 0.000864 0.000780
0.000815 0.000672 0.000697 0.000624
N4 0.056604 0.066755 0.054645 -0.000644 -0.010987 -0.006148 0.000903 0.000892
0.000869 0.000708 0.000691 0.000698
C9 0.043416 0.047442 0.048289 0.005016 0.001095 -0.004847 0.000873 0.000831
0.000819 0.000666 0.000686 0.000652
C6 0.047807 0.056698 0.053762 0.007247 0.004229 -0.005376 0.000920 0.000935
0.000916 0.000758 0.000744 0.000733
O6 0.058036 0.126905 0.078291 0.002747 -0.015481 -0.015070 0.000746 0.001138
0.000841 0.000742 0.000639 0.000775
O7 0.092423 0.097952 0.079173 0.005443 -0.028005 -0.031614 0.000971 0.000969
0.000878 0.000743 0.000678 0.000720
C7 0.058428 0.055016 0.047078 0.004483 0.000634 -0.011799 0.001032 0.000946
0.000886 0.000756 0.000765 0.000724
O4 0.079630 0.115812 0.117527 0.007008 -0.015530 -0.070012 0.000924 0.001127
0.001073 0.000810 0.000797 0.000913

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 . N3 . 1.2026(15) yes
O6 . N4 . 1.2068(16) yes
O7 . N4 . 1.2081(16) yes
O4 . N3 . 1.2017(16) yes
O1 . C1 . 1.2790(16) yes
O2 . C4 . 1.2572(16) yes
O3 . C4 . 1.2261(16) yes
O1 . H1 . 1.28(4) yes
O2 . H1 . 1.20(4) yes
N2 . C1 . 1.3218(18) yes
N2 . C2 . 1.448(2) yes
N2 . C3 . 1.451(2) yes
N1 . C1 . 1.3242(19) yes
N3 . C10 . 1.4569(17) yes
N4 . C8 . 1.4674(18) yes
N1 . H1A . 0.99(2) yes
N1 . H1B . 1.01(2) yes
C5 . C10 . 1.3942(18) yes
C5 . C4 . 1.5112(19) yes
C5 . C6 . 1.3918(19) yes
C10 . C9 . 1.3814(18) yes
C8 . C9 . 1.3768(19) yes
C8 . C7 . 1.3804(19) yes
C6 . C7 . 1.379(2) yes
C2 . H2A . 1.08(2) yes
C2 . H2B . 1.07(2) yes
C2 . H2C . 0.97(2) yes
C3 . H3A . 1.09(2) yes
C3 . H3B . 1.01(2) yes
C3 . H3C . 0.96(2) yes
C9 . H9 . 1.033(14) yes
C6 . H6 . 1.019(15) yes
C7 . H7 . 1.024(16) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 . N3 . O4 . 122.85(13) yes
O6 . N4 . O7 . 123.78(14) yes
O5 . N3 . C10 . 119.07(13) yes
O6 . N4 . C8 . 118.00(13) yes
O7 . N4 . C8 . 118.21(14) yes
O4 . N3 . C10 . 118.08(14) yes
O2 . C4 . O3 . 126.09(14) yes
O1 . C1 . N2 . 119.13(14) yes
O1 . C1 . N1 . 119.91(14) yes
O2 . C4 . C5 . 113.82(12) yes
O3 . C4 . C5 . 119.83(13) yes
O1 . H1 . O2 . 163(2) yes
N2 . C1 . N1 . 120.96(14) yes
N3 . C10 . C5 . 120.64(12) yes
N3 . C10 . C9 . 117.04(12) yes
N4 . C8 . C9 . 118.78(13) yes
N4 . C8 . C7 . 119.29(13) yes
N2 . C2 . H2A . 112.9(11) yes
N2 . C2 . H2B . 106.9(12) yes
N2 . C2 . H2C . 111.9(12) yes
N2 . C3 . H3A . 110.4(11) yes
N2 . C3 . H3B . 109.1(13) yes
N2 . C3 . H3C . 109.8(14) yes
C1 . O1 . H1 . 117.2(12) yes
C4 . O2 . H1 . 116.5(13) yes
C1 . N2 . C2 . 122.24(14) yes
C1 . N2 . C3 . 120.40(14) yes
C2 . N2 . C3 . 117.31(14) yes
C1 . N1 . H1A . 120.4(11) yes
C1 . N1 . H1B . 115.8(10) yes
C5 . C10 . C9 . 122.32(13) yes
C5 . C6 . C7 . 121.04(14) yes
C10 . C5 . C4 . 124.51(13) yes
C10 . C5 . C6 . 117.72(13) yes
C10 . C9 . C8 . 117.80(13) yes
C8 . C7 . C6 . 119.17(14) yes
C4 . C5 . C6 . 117.70(12) yes
C9 . C8 . C7 . 121.93(13) yes
C5 . C6 . H6 . 120.6(9) yes
C10 . C9 . H9 . 119.3(8) yes
C8 . C9 . H9 . 122.9(8) yes
C8 . C7 . H7 . 119.7(9) yes
C6 . C7 . H7 . 121.2(9) yes
C7 . C6 . H6 . 118.3(9) yes
H1A . N1 . H1B . 123.7(15) yes
H2A . C2 . H2B . 101.2(16) yes
H2A . C2 . H2C . 107.1(17) yes
H2B . C2 . H2C . 116.4(18) yes
H3A . C3 . H3B . 101.9(17) yes
H3A . C3 . H3C . 112.2(18) yes
H3B . C3 . H3C . 113.1(19) yes
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate 1:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_150K_har
_database_code_depnum_ccdc_archive 'CCDC 1922024'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_150K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      47.30 %     
RESPONSE: Related to the use of a non-standard diffraction wavelength. 
;
_vrf_PLAT230_complex_2_150K_har  
;
PROBLEM: Hirshfeld Test Diff for    O5       --N3       .        7.8 s.u.  
RESPONSE: O5 and N3 are not the same atom type.
;
# end Validation Reply Form

_audit_creation_date             2018-12-20
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            150K
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_moiety         'C3 H9 N2 O1, C7 H3 N2 O6'
_chemical_formula_weight         300.2297
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       156
_QCr_calc_unit_n_alpha_electrons 78
_QCr_calc_unit_n_beta_electrons  78

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.993692626842
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;


# ========
# Symmetry
# ========

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'p b c a'
_symmetry_space_group_name_Hall  '-p 2ac 2ab'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, -y, +z+1/2'
'+x+1/2, -y+1/2, -z'
'+x+1/2, +y, -z+1/2'
'-x+1/2, +y+1/2, +z'
'-x, +y+1/2, -z+1/2'
'+x, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    150
_cell_measurement_reflns_used    29069
_cell_measurement_theta_min      1.71120705438
_cell_measurement_theta_max      36.0673892193

_cell_length_a                   22.97700(7)
_cell_length_b                   19.20650(6)
_cell_length_c                   5.83570(2)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 90.000000(0)
_cell_angle_gamma                90.000000(0)
_cell_volume                     2575.340(14)

_cell_formula_units_Z            8.000000

_atom_sites_solution_hydrogens   HAR


# ===========
# Device data
# ===========

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            3313
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.718
_diffrn_reflns_theta_max         27.740
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            333.467098

_reflns_d_resolution_high        11.488500
_reflns_d_resolution_low         0.740029
_reflns_limit_h_max              30
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                2927
_reflns_number_total             2927
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0206
_refine_ls_R_factor_all          0.0206
_refine_ls_wR_factor_gt          0.0225
_refine_ls_wR_factor_all         0.0225
_refine_ls_R_Fsqd_factor         0.0345
_refine_ls_goodness_of_fit_gt    1.3916
_refine_ls_goodness_of_fit_all   1.3916
_refine_ls_number_reflns         2927
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0050
_refine_ls_shift/su_max_mean     0.0003
_refine_ls_shift/su_max_par      'H3A Uxz'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.0841
_refine_diff_density_min         -0.0900
_refine_diff_density_rms         0.0189
_refine_diff_density_max_atom    0.0294
_refine_diff_density_max_atom_tag H7
_refine_diff_density_min_atom    -0.0274
_refine_diff_density_min_atom_tag C9
_refine_diff_density_rms_atom    0.0146

_refine_special_details          
;
  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run Hart with the following options:
  -shelx-f2 150K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.00285 0.00150 N 0.00565 0.00308 O 0.01010 0.00566"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  150K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

150k.cif obtained from res in _shelx_res_file
;



# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 0.106197 0.692134 1.529494 0.048857 Uani 1.000000 0 0.000367 0.000429
0.001415 0.005637
H7 0.193593 0.714812 1.760549 0.051780 Uani 1.000000 0 0.000350 0.000496
0.001623 0.005983
H9 0.294768 0.592871 1.291503 0.045879 Uani 1.000000 0 0.000368 0.000462
0.001396 0.005701
H1A -0.042432 0.520582 0.771906 0.055977 Uani 1.000000 0 0.000421 0.000540
0.001644 0.007011
H1B 0.006005 0.567242 0.950426 0.040618 Uani 1.000000 0 0.000447 0.000472
0.001832 0.006529
H2A -0.105757 0.563930 0.251620 0.087414 Uani 1.000000 0 0.000501 0.000548
0.001907 0.008700
H2B -0.067842 0.512051 0.432950 0.080964 Uani 1.000000 0 0.000466 0.000515
0.001904 0.007755
H3A -0.058177 0.668774 0.173538 0.108890 Uani 1.000000 0 0.000672 0.000628
0.001959 0.010593
H2C -0.129007 0.555042 0.534016 0.092243 Uani 1.000000 0 0.000473 0.000559
0.002107 0.009011
H3B -0.103371 0.704776 0.363112 0.110239 Uani 1.000000 0 0.000564 0.000633
0.002513 0.010574
H3C -0.031821 0.717708 0.392079 0.122114 Uani 1.000000 0 0.000673 0.000663
0.002367 0.011135
H1 0.043595 0.666272 0.847613 0.033652 Uani 1.000000 0 0.000552 0.000540
0.001928 0.008254
O1 0.007799 0.673156 0.716485 0.027274 Uani 1.000000 0 0.000020 0.000022
0.000082 0.000235
N2 -0.056852 0.619230 0.486676 0.024173 Uani 1.000000 0 0.000021 0.000025
0.000086 0.000260
N1 -0.019706 0.562921 0.805862 0.029836 Uani 1.000000 0 0.000027 0.000031
0.000111 0.000318
C1 -0.022773 0.618628 0.670171 0.021676 Uani 1.000000 0 0.000024 0.000030
0.000099 0.000284
C2 -0.092405 0.559612 0.426663 0.031390 Uani 1.000000 0 0.000033 0.000038
0.000148 0.000373
C3 -0.061946 0.681225 0.345696 0.033979 Uani 1.000000 0 0.000039 0.000041
0.000143 0.000401
O2 0.090205 0.667054 0.980649 0.027267 Uani 1.000000 0 0.000018 0.000022
0.000072 0.000232
O3 0.057348 0.579441 1.197195 0.029234 Uani 1.000000 0 0.000019 0.000022
0.000074 0.000236
C5 0.149557 0.629990 1.280689 0.019183 Uani 1.000000 0 0.000024 0.000028
0.000095 0.000270
C10 0.203617 0.602616 1.219138 0.018897 Uani 1.000000 0 0.000023 0.000028
0.000095 0.000268
O5 0.257760 0.547088 0.940060 0.029364 Uani 1.000000 0 0.000019 0.000022
0.000073 0.000239
C8 0.248776 0.655647 1.538984 0.020252 Uani 1.000000 0 0.000024 0.000029
0.000094 0.000280
C4 0.094374 0.622683 1.140753 0.020683 Uani 1.000000 0 0.000024 0.000029
0.000098 0.000275
N3 0.209193 0.557962 1.016556 0.023383 Uani 1.000000 0 0.000022 0.000025
0.000085 0.000261
N4 0.301393 0.669579 1.674706 0.025110 Uani 1.000000 0 0.000022 0.000027
0.000087 0.000268
C9 0.253883 0.615007 1.344323 0.020314 Uani 1.000000 0 0.000026 0.000030
0.000099 0.000288
C6 0.146620 0.670541 1.479102 0.022553 Uani 1.000000 0 0.000027 0.000031
0.000101 0.000298
O6 0.347395 0.645773 1.606570 0.037185 Uani 1.000000 0 0.000020 0.000027
0.000083 0.000272
O7 0.296138 0.703927 1.849181 0.038082 Uani 1.000000 0 0.000021 0.000026
0.000078 0.000281
C7 0.195946 0.683277 1.609826 0.023061 Uani 1.000000 0 0.000026 0.000032
0.000109 0.000297
O4 0.164905 0.533937 0.933951 0.044847 Uani 1.000000 0 0.000021 0.000028
0.000094 0.000300

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 0.1062(4) 0.6921(4) 1.5295(14) 0.049(6) Uani 1.000000 0
H7 0.1936(3) 0.7148(5) 1.7605(16) 0.052(6) Uani 1.000000 0
H9 0.2948(4) 0.5929(5) 1.2915(14) 0.046(6) Uani 1.000000 0
H1A -0.0424(4) 0.5206(5) 0.7719(16) 0.056(7) Uani 1.000000 0
H1B 0.0060(4) 0.5672(5) 0.9504(18) 0.041(7) Uani 1.000000 0
H2A -0.1058(5) 0.5639(5) 0.2516(19) 0.087(9) Uani 1.000000 0
H2B -0.0678(5) 0.5121(5) 0.4329(19) 0.081(8) Uani 1.000000 0
H3A -0.0582(7) 0.6688(6) 0.174(2) 0.109(11) Uani 1.000000 0
H2C -0.1290(5) 0.5550(6) 0.534(2) 0.092(9) Uani 1.000000 0
H3B -0.1034(6) 0.7048(6) 0.363(3) 0.110(11) Uani 1.000000 0
H3C -0.0318(7) 0.7177(7) 0.392(2) 0.122(11) Uani 1.000000 0
H1 0.0436(6) 0.6663(5) 0.8476(19) 0.034(8) Uani 1.000000 0
O1 0.00780(2) 0.67316(2) 0.71649(8) 0.0273(2) Uani 1.000000 0
N2 -0.05685(2) 0.61923(3) 0.48668(9) 0.0242(3) Uani 1.000000 0
N1 -0.01971(3) 0.56292(3) 0.80586(11) 0.0298(3) Uani 1.000000 0
C1 -0.02277(2) 0.61863(3) 0.67017(10) 0.0217(3) Uani 1.000000 0
C2 -0.09240(3) 0.55961(4) 0.42666(15) 0.0314(4) Uani 1.000000 0
C3 -0.06195(4) 0.68122(4) 0.34570(14) 0.0340(4) Uani 1.000000 0
O2 0.090205(18) 0.66705(2) 0.98065(7) 0.0273(2) Uani 1.000000 0
O3 0.057348(19) 0.57944(2) 1.19719(7) 0.0292(2) Uani 1.000000 0
C5 0.14956(2) 0.62999(3) 1.28069(10) 0.0192(3) Uani 1.000000 0
C10 0.20362(2) 0.60262(3) 1.21914(9) 0.0189(3) Uani 1.000000 0
O5 0.257760(19) 0.54709(2) 0.94006(7) 0.0294(2) Uani 1.000000 0
C8 0.24878(2) 0.65565(3) 1.53898(9) 0.0203(3) Uani 1.000000 0
C4 0.09437(2) 0.62268(3) 1.14075(10) 0.0207(3) Uani 1.000000 0
N3 0.20919(2) 0.55796(2) 1.01656(8) 0.0234(3) Uani 1.000000 0
N4 0.30139(2) 0.66958(3) 1.67471(9) 0.0251(3) Uani 1.000000 0
C9 0.25388(3) 0.61501(3) 1.34432(10) 0.0203(3) Uani 1.000000 0
C6 0.14662(3) 0.67054(3) 1.47910(10) 0.0226(3) Uani 1.000000 0
O6 0.34739(2) 0.64577(3) 1.60657(8) 0.0372(3) Uani 1.000000 0
O7 0.29614(2) 0.70393(3) 1.84918(8) 0.0381(3) Uani 1.000000 0
C7 0.19595(3) 0.68328(3) 1.60983(11) 0.0231(3) Uani 1.000000 0
O4 0.16491(2) 0.53394(3) 0.93395(9) 0.0448(3) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.047890 0.047618 0.051062 0.002515 -0.000105 -0.015431 0.005562 0.005642
0.005706 0.004674 0.004343 0.004271
H7 0.027313 0.070406 0.057620 0.001499 -0.006963 -0.004972 0.004969 0.007056
0.005925 0.004587 0.004263 0.004994
H9 0.041836 0.054586 0.041215 0.004053 -0.000878 -0.002805 0.005600 0.005982
0.005521 0.004804 0.004113 0.004276
H1A 0.053091 0.047286 0.067555 -0.010882 -0.015891 0.006845 0.007131 0.006462
0.007442 0.005735 0.005619 0.005330
H1B 0.039355 0.034200 0.048300 -0.002289 -0.010241 0.004839 0.006470 0.006086
0.007030 0.004868 0.005217 0.005185
H2A 0.099155 0.076838 0.086248 -0.023813 -0.059770 -0.007164 0.009572 0.008372
0.008154 0.006521 0.007354 0.006364
H2B 0.076791 0.048798 0.117304 0.002839 -0.043584 -0.010194 0.007556 0.006411
0.009298 0.005971 0.006911 0.006188
H3A 0.179632 0.094618 0.052421 0.011846 0.013120 0.021763 0.014449 0.009613
0.007718 0.008951 0.007978 0.006014
H2C 0.065724 0.099938 0.111067 -0.042073 0.031356 -0.049676 0.007602 0.009732
0.009699 0.006681 0.006993 0.007353
H3B 0.088778 0.085082 0.156858 0.035399 0.036798 0.054681 0.009786 0.009326
0.012609 0.007895 0.008596 0.008520
H3C 0.154057 0.085851 0.126434 -0.065465 -0.079637 0.065115 0.013893 0.008996
0.010516 0.009745 0.010107 0.007997
H1 0.030218 0.046227 0.024511 -0.005849 -0.009457 -0.007776 0.009216 0.007850
0.007696 0.006613 0.007224 0.005596
O1 0.025096 0.021347 0.035378 -0.002495 -0.006919 0.002917 0.000227 0.000220
0.000257 0.000171 0.000193 0.000183
N2 0.019537 0.025903 0.027078 0.000059 -0.002022 0.001001 0.000244 0.000270
0.000266 0.000193 0.000201 0.000197
N1 0.029381 0.023303 0.036824 -0.004858 -0.010584 0.006415 0.000315 0.000290
0.000349 0.000236 0.000259 0.000260
C1 0.017401 0.020046 0.027582 -0.000401 -0.002703 0.001767 0.000264 0.000281
0.000309 0.000207 0.000222 0.000228
C2 0.025171 0.031246 0.037751 -0.003265 -0.007456 -0.003169 0.000347 0.000371
0.000402 0.000279 0.000320 0.000313
C3 0.036995 0.032955 0.031987 -0.000512 -0.007113 0.006560 0.000408 0.000387
0.000408 0.000319 0.000326 0.000304
O2 0.024004 0.028457 0.029340 -0.007593 -0.006115 0.007760 0.000229 0.000231
0.000237 0.000171 0.000181 0.000174
O3 0.023942 0.028299 0.035460 -0.008014 -0.005280 0.009239 0.000221 0.000235
0.000251 0.000174 0.000180 0.000185
C5 0.016380 0.019544 0.021624 0.000427 -0.000442 -0.000530 0.000265 0.000263
0.000282 0.000199 0.000216 0.000210
C10 0.018044 0.018074 0.020572 0.000943 -0.001389 -0.001637 0.000272 0.000259
0.000273 0.000208 0.000206 0.000210
O5 0.029740 0.030776 0.027576 0.003603 0.002108 -0.008564 0.000237 0.000242
0.000237 0.000180 0.000185 0.000181
C8 0.020095 0.021081 0.019579 0.000178 -0.001176 -0.001192 0.000278 0.000277
0.000286 0.000207 0.000211 0.000212
C4 0.017188 0.019804 0.025056 -0.002623 -0.001678 0.003311 0.000264 0.000269
0.000292 0.000208 0.000218 0.000223
N3 0.022346 0.022519 0.025284 0.002532 -0.002452 -0.007167 0.000266 0.000251
0.000265 0.000192 0.000203 0.000200
N4 0.023388 0.029131 0.022811 -0.000536 -0.005431 -0.002769 0.000266 0.000275
0.000263 0.000204 0.000204 0.000210
C9 0.017695 0.021804 0.021442 0.002434 -0.001151 -0.002868 0.000284 0.000284
0.000296 0.000221 0.000223 0.000221
C6 0.019553 0.025434 0.022672 0.003111 0.001695 -0.002187 0.000294 0.000303
0.000296 0.000235 0.000234 0.000229
O6 0.022175 0.056519 0.032862 0.001694 -0.006204 -0.006925 0.000232 0.000319
0.000266 0.000208 0.000193 0.000225
O7 0.037057 0.042567 0.034622 0.002014 -0.011984 -0.013608 0.000286 0.000291
0.000265 0.000217 0.000201 0.000213
C7 0.023491 0.025188 0.020505 0.002156 -0.000321 -0.004711 0.000305 0.000293
0.000293 0.000231 0.000239 0.000243
O4 0.029537 0.050755 0.054249 0.002558 -0.007870 -0.032263 0.000260 0.000311
0.000330 0.000221 0.000230 0.000253

# ====
# ADPs
# ====


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 . N3 . 1.2199(6) yes
O6 . N4 . 1.2184(7) yes
O7 . N4 . 1.2192(7) yes
O4 . N3 . 1.2169(7) yes
O1 . C1 . 1.2897(7) yes
O2 . C4 . 1.2682(7) yes
O3 . C4 . 1.2337(7) yes
O1 . H1 . 1.131(13) yes
N2 . C1 . 1.3266(8) yes
N2 . C2 . 1.4495(8) yes
N2 . C3 . 1.4520(9) yes
N1 . C1 . 1.3329(8) yes
N3 . C10 . 1.4662(7) yes
N4 . C8 . 1.4699(7) yes
N1 . H1A . 0.987(10) yes
N1 . H1B . 1.033(11) yes
C5 . C10 . 1.3958(8) yes
C5 . C4 . 1.5147(8) yes
C5 . C6 . 1.3971(8) yes
C10 . C9 . 1.3872(8) yes
C8 . C9 . 1.3833(8) yes
C8 . C7 . 1.3878(8) yes
C6 . C7 . 1.3879(9) yes
C2 . H2A . 1.070(10) yes
C2 . H2B . 1.074(10) yes
C2 . H2C . 1.052(11) yes
C3 . H3A . 1.036(12) yes
C3 . H3B . 1.059(12) yes
C3 . H3C . 1.021(12) yes
C9 . H9 . 1.076(8) yes
C6 . H6 . 1.059(8) yes
C7 . H7 . 1.069(9) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 . N3 . O4 . 123.72(5) yes
O6 . N4 . O7 . 124.16(5) yes
O5 . N3 . C10 . 118.37(5) yes
O6 . N4 . C8 . 117.99(5) yes
O7 . N4 . C8 . 117.84(5) yes
O4 . N3 . C10 . 117.92(5) yes
O2 . C4 . O3 . 126.65(5) yes
O1 . C1 . N2 . 118.92(5) yes
O1 . C1 . N1 . 119.90(6) yes
O2 . C4 . C5 . 113.46(5) yes
O3 . C4 . C5 . 119.71(5) yes
N2 . C1 . N1 . 121.18(6) yes
N3 . C10 . C5 . 120.37(5) yes
N3 . C10 . C9 . 116.89(5) yes
N4 . C8 . C9 . 118.39(5) yes
N4 . C8 . C7 . 119.29(5) yes
N2 . C2 . H2A . 109.3(6) yes
N2 . C2 . H2B . 111.6(5) yes
N2 . C2 . H2C . 111.9(5) yes
N2 . C3 . H3A . 110.7(6) yes
N2 . C3 . H3B . 111.6(6) yes
N2 . C3 . H3C . 111.0(6) yes
C1 . O1 . H1 . 116.3(5) yes
C1 . N2 . C2 . 121.38(5) yes
C1 . N2 . C3 . 120.80(5) yes
C2 . N2 . C3 . 117.74(6) yes
C1 . N1 . H1A . 121.0(5) yes
C1 . N1 . H1B . 116.8(5) yes
C5 . C10 . C9 . 122.74(5) yes
C5 . C6 . C7 . 120.95(6) yes
C10 . C5 . C4 . 124.84(5) yes
C10 . C5 . C6 . 117.79(5) yes
C10 . C9 . C8 . 117.30(5) yes
C8 . C7 . C6 . 118.89(6) yes
C4 . C5 . C6 . 117.26(5) yes
C9 . C8 . C7 . 122.32(5) yes
C5 . C6 . H6 . 119.4(4) yes
C10 . C9 . H9 . 120.5(4) yes
C8 . C9 . H9 . 122.2(4) yes
C8 . C7 . H7 . 120.4(4) yes
C6 . C7 . H7 . 120.7(4) yes
C7 . C6 . H6 . 119.6(4) yes
H1A . N1 . H1B . 122.2(7) yes
H2A . C2 . H2B . 104.4(8) yes
H2A . C2 . H2C . 110.2(9) yes
H2B . C2 . H2C . 109.2(9) yes
H3A . C3 . H3B . 105.5(11) yes
H3A . C3 . H3C . 111.0(11) yes
H3B . C3 . H3C . 106.9(11) yes
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate 1:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_8_200K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922018'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_8_200K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      49.13 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide 3,5-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 N2 O6, C6 H7 N2 O1'
_chemical_formula_sum            'C13 H10 N4 O7'
_chemical_formula_weight         334.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.33360(4)
_cell_length_b                   9.01180(4)
_cell_length_c                   10.81310(5)
_cell_angle_alpha                87.9490(4)
_cell_angle_beta                 76.4520(4)
_cell_angle_gamma                87.1840(4)
_cell_volume                     693.685(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    13442
_cell_measurement_theta_max      35.6591229731
_cell_measurement_theta_min      1.87098518611

_exptl_crystal_description       'triangular block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6850
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23674
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.878
_diffrn_reflns_theta_max         36.015
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6677
_reflns_number_gt                5415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0790P)²+0.0533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6677
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.51480(10) 0.20298(7) -0.00446(6) 0.03035(13) Uani 1 1 d . . . . .
N2 N 0.60496(10) 0.04034(7) 0.13637(7) 0.02563(13) Uani 1 1 d . . . . .
N1 N 0.70585(11) 0.54690(7) 0.28336(6) 0.02639(13) Uani 1 1 d . . . . .
C13 C 0.57817(10) 0.17687(8) 0.09095(7) 0.02196(12) Uani 1 1 d . . . . .
C11 C 0.66844(13) 0.43922(8) 0.09549(7) 0.02704(15) Uani 1 1 d . . . . .
C10 C 0.62696(10) 0.30531(7) 0.16124(7) 0.02127(12) Uani 1 1 d . . . . .
C8 C 0.66657(13) 0.41911(8) 0.34880(7) 0.02770(15) Uani 1 1 d . . . . .
C12 C 0.70917(14) 0.55905(8) 0.15955(8) 0.02937(16) Uani 1 1 d . . . . .
C9 C 0.62707(12) 0.29490(8) 0.29021(7) 0.02584(14) Uani 1 1 d . . . . .
O5 O 0.87989(12) 1.33650(7) 0.80110(7) 0.03997(17) Uani 1 1 d . . . . .
O2 O 0.69774(11) 0.95829(8) 0.37443(6) 0.03631(15) Uani 1 1 d . . . . .
O4 O 0.95322(11) 0.83657(8) 0.96235(6) 0.03527(15) Uani 1 1 d . . . . .
O3 O 0.90463(11) 0.65094(7) 0.85480(7) 0.03674(15) Uani 1 1 d . . . . .
O1 O 0.76007(15) 0.72873(8) 0.44343(7) 0.0466(2) Uani 1 1 d . . . . .
O6 O 0.73069(14) 1.37362(8) 0.65147(8) 0.0485(2) Uani 1 1 d . . . . .
N3 N 0.91231(10) 0.78398(7) 0.86984(6) 0.02460(12) Uani 1 1 d . . . . .
N4 N 0.80775(11) 1.29261(7) 0.71923(7) 0.02924(14) Uani 1 1 d . . . . .
C4 C 0.86860(10) 0.88744(7) 0.77148(7) 0.02089(12) Uani 1 1 d . . . . .
C3 C 0.82791(10) 0.82931(8) 0.66432(7) 0.02208(12) Uani 1 1 d . . . . .
C5 C 0.86621(11) 1.03837(8) 0.79219(7) 0.02237(13) Uani 1 1 d . . . . .
C6 C 0.81341(11) 1.13139(7) 0.70067(7) 0.02267(13) Uani 1 1 d . . . . .
C7 C 0.76728(11) 1.07955(8) 0.59316(7) 0.02364(13) Uani 1 1 d . . . . .
C2 C 0.77842(10) 0.92689(8) 0.57358(7) 0.02166(12) Uani 1 1 d . . . . .
C1 C 0.73982(12) 0.86825(8) 0.45295(7) 0.02529(14) Uani 1 1 d . . . . .
H10 H 0.7321(19) 1.1481(16) 0.5301(13) 0.041(3) Uiso 1 1 d . . . . .
H9 H 0.8978(17) 1.0817(14) 0.8656(12) 0.032(3) Uiso 1 1 d . . . . .
H8 H 0.8342(18) 0.7246(14) 0.6538(12) 0.034(3) Uiso 1 1 d . . . . .
H3 H 0.5971(18) 0.2036(15) 0.3428(12) 0.034(3) Uiso 1 1 d . . . . .
H4 H 0.7390(18) 0.6583(15) 0.1191(13) 0.037(3) Uiso 1 1 d . . . . .
H6 H 0.6481(18) 0.0220(14) 0.2093(13) 0.036(3) Uiso 1 1 d . . . . .
H5 H 0.678(2) 0.4501(17) 0.0095(14) 0.045(4) Uiso 1 1 d . . . . .
H2 H 0.660(2) 0.4211(17) 0.4368(15) 0.051(4) Uiso 1 1 d . . . . .
H7 H 0.572(2) -0.0416(16) 0.0935(13) 0.041(3) Uiso 1 1 d . . . . .
H1 H 0.733(2) 0.6331(18) 0.3363(16) 0.059(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 C13 1.2378(9) . ?
N2 C13 1.3311(10) . ?
N2 H6 0.923(13) . ?
N2 H7 0.955(14) . ?
N1 C12 1.3340(10) . ?
N1 C8 1.3374(10) . ?
N1 H1 1.034(16) . ?
C13 C10 1.5089(9) . ?
C11 C12 1.3846(10) . ?
C11 C10 1.3884(10) . ?
C11 H5 0.918(15) . ?
C10 C9 1.3945(10) . ?
C8 C9 1.3809(10) . ?
C8 H2 0.942(16) . ?
C12 H4 0.993(13) . ?
C9 H3 0.987(13) . ?
O5 N4 1.2186(10) . ?
O2 C1 1.2342(10) . ?
O4 N3 1.2263(9) . ?
O3 N3 1.2215(9) . ?
O1 C1 1.2638(10) . ?
O6 N4 1.2264(10) . ?
N3 C4 1.4705(10) . ?
N4 C6 1.4710(9) . ?
C4 C5 1.3850(9) . ?
C4 C3 1.3882(10) . ?
C3 C2 1.3934(10) . ?
C3 H8 0.952(13) . ?
C5 C6 1.3856(11) . ?
C5 H9 0.977(13) . ?
C6 C7 1.3867(10) . ?
C7 C2 1.3949(9) . ?
C7 H10 0.974(14) . ?
C2 C1 1.5159(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N2 H6 122.9(8) . . ?
C13 N2 H7 118.1(8) . . ?
H6 N2 H7 118.9(11) . . ?
C12 N1 C8 121.45(6) . . ?
C12 N1 H1 123.8(10) . . ?
C8 N1 H1 114.7(10) . . ?
O7 C13 N2 123.46(6) . . ?
O7 C13 C10 119.02(6) . . ?
N2 C13 C10 117.52(6) . . ?
C12 C11 C10 119.18(7) . . ?
C12 C11 H5 118.2(9) . . ?
C10 C11 H5 122.5(9) . . ?
C11 C10 C9 119.18(6) . . ?
C11 C10 C13 118.56(6) . . ?
C9 C10 C13 122.23(6) . . ?
N1 C8 C9 120.92(7) . . ?
N1 C8 H2 116.3(10) . . ?
C9 C8 H2 122.7(10) . . ?
N1 C12 C11 120.51(7) . . ?
N1 C12 H4 115.7(8) . . ?
C11 C12 H4 123.7(8) . . ?
C8 C9 C10 118.74(7) . . ?
C8 C9 H3 117.9(8) . . ?
C10 C9 H3 123.3(8) . . ?
O3 N3 O4 123.98(7) . . ?
O3 N3 C4 118.02(6) . . ?
O4 N3 C4 118.00(6) . . ?
O5 N4 O6 124.48(7) . . ?
O5 N4 C6 117.67(7) . . ?
O6 N4 C6 117.86(7) . . ?
C5 C4 C3 123.38(7) . . ?
C5 C4 N3 118.02(6) . . ?
C3 C4 N3 118.59(6) . . ?
C4 C3 C2 118.74(6) . . ?
C4 C3 H8 120.0(8) . . ?
C2 C3 H8 121.2(8) . . ?
C4 C5 C6 116.00(6) . . ?
C4 C5 H9 124.7(7) . . ?
C6 C5 H9 119.3(7) . . ?
C5 C6 C7 123.13(6) . . ?
C5 C6 N4 117.84(6) . . ?
C7 C6 N4 119.02(7) . . ?
C6 C7 C2 118.99(7) . . ?
C6 C7 H10 121.0(8) . . ?
C2 C7 H10 119.9(8) . . ?
C3 C2 C7 119.69(6) . . ?
C3 C2 C1 120.39(6) . . ?
C7 C2 C1 119.91(7) . . ?
O2 C1 O1 127.09(7) . . ?
O2 C1 C2 118.46(7) . . ?
O1 C1 C2 114.43(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H9 O4 0.977(13) 2.515(13) 3.4751(9) 167.5(10) 2_777 yes
C9 H3 O2 0.987(13) 2.335(13) 3.1888(10) 144.3(10) 1_545 yes
C12 H4 O4 0.993(13) 2.593(13) 3.5036(11) 152.3(10) 1_554 yes
N2 H6 O2 0.923(13) 1.965(14) 2.8759(9) 168.9(12) 1_545 yes
C11 H5 O5 0.918(15) 2.603(15) 3.3395(11) 137.7(12) 1_544 yes
C8 H2 O6 0.942(16) 2.513(16) 3.4215(11) 162.1(13) 1_545 yes
N2 H7 O7 0.955(14) 1.982(14) 2.9349(8) 175.4(13) 2_655 yes
N1 H1 O1 1.034(16) 1.524(17) 2.5354(9) 164.4(16) . yes

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.054

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_250K_har
_database_code_depnum_ccdc_archive 'CCDC 1922021'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_250K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      46.02 %     
RESPONSE: Related to the use of a non-standard diffraction wavelength. 
;
_vrf_PLAT230_complex_2_250K_har  
;
PROBLEM: Hirshfeld Test Diff for    O2       --C4       .        8.3 s.u.  
RESPONSE: O2 and C4 are not the same atom type.
;
_vrf_PLAT355_complex_2_250K_har  
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O2       - H1       .       1.10 Ang.  
RESPONSE: The long O-H distance is characteristic of H1 forming a short O-H...O hydrogen bond.
;
# end Validation Reply Form

_audit_creation_date             2018-12-21
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            250K
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_moiety         'C3 H8 N2 O1, C7 H4 N2 O6'
_chemical_formula_weight         300.2297
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       156
_QCr_calc_unit_n_alpha_electrons 78
_QCr_calc_unit_n_beta_electrons  78

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.993008074575
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;


# ========
# Symmetry
# ========

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'p b c a'
_symmetry_space_group_name_Hall  '-p 2ac 2ab'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, -y, +z+1/2'
'+x+1/2, -y+1/2, -z'
'+x+1/2, +y, -z+1/2'
'-x+1/2, +y+1/2, +z'
'-x, +y+1/2, -z+1/2'
'+x, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    250
_cell_measurement_reflns_used    20082
_cell_measurement_theta_min      0.848883432955
_cell_measurement_theta_max      35.6819203977

_cell_length_a                   23.08380(11)
_cell_length_b                   19.28500(10)
_cell_length_c                   5.90710(3)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 90.000000(0)
_cell_angle_gamma                90.000000(0)
_cell_volume                     2629.67(2)

_cell_formula_units_Z            8.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========

_diffrn_ambient_temperature      250
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            3387
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         27.740
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .


# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            325.564145

_reflns_d_resolution_high        11.541900
_reflns_d_resolution_low         0.741454
_reflns_limit_h_max              30
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                1015
_reflns_number_total             1015
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0192
_refine_ls_R_factor_all          0.0192
_refine_ls_wR_factor_gt          0.0019
_refine_ls_wR_factor_all         0.0019
_refine_ls_R_Fsqd_factor         0.0166
_refine_ls_goodness_of_fit_gt    0.6453
_refine_ls_goodness_of_fit_all   0.6453
_refine_ls_number_reflns         1015
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0079
_refine_ls_shift/su_max_mean     0.0007
_refine_ls_shift/su_max_par      'H1 pz'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.0636
_refine_diff_density_min         -0.0654
_refine_diff_density_rms         0.0109
_refine_diff_density_max_atom    0.0232
_refine_diff_density_max_atom_tag C7
_refine_diff_density_min_atom    -0.0497
_refine_diff_density_min_atom_tag C1
_refine_diff_density_rms_atom    0.0151

_refine_special_details          
;

  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.
   
. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 250K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.00285 0.00150 N 0.00565 0.00308 O 0.01010 0.00566"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  250K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

250k.cif obtained from res in _shelx_res_file  
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 0.104880 0.694379 1.516380 0.083618 Uani 1.000000 0 0.000756 0.001079
0.003291 0.017883
H7 0.191064 0.717214 1.756212 0.077145 Uani 1.000000 0 0.000942 0.000839
0.003528 0.017001
H9 0.293098 0.594075 1.291744 0.063923 Uani 1.000000 0 0.000769 0.000861
0.003226 0.015292
H1A -0.036733 0.517095 0.764263 0.107375 Uani 1.000000 0 0.001292 0.001091
0.005633 0.024083
H1B 0.008266 0.562986 0.942985 0.074378 Uani 1.000000 0 0.000960 0.001502
0.004074 0.020729
H3A -0.055331 0.669096 0.196215 0.148314 Uani 1.000000 0 0.001983 0.001837
0.004950 0.032655
H3B -0.102915 0.703427 0.357406 0.176469 Uani 1.000000 0 0.000968 0.001613
0.007087 0.030304
H3C -0.033693 0.722479 0.418894 0.164900 Uani 1.000000 0 0.001373 0.001397
0.005919 0.030983
H1 0.046188 0.669080 0.904366 0.284574 Uani 1.000000 0 0.001399 0.001634
0.011201 0.057487
O1 0.007072 0.672070 0.719575 0.050626 Uani 1.000000 0 0.000059 0.000065
0.000230 0.000837
N2 -0.057648 0.619108 0.495361 0.045692 Uani 1.000000 0 0.000064 0.000083
0.000315 0.001023
N1 -0.020035 0.562630 0.807255 0.054753 Uani 1.000000 0 0.000086 0.000112
0.000430 0.001386
C1 -0.023581 0.618229 0.674746 0.039349 Uani 1.000000 0 0.000078 0.000097
0.000380 0.001217
C2 -0.092779 0.559907 0.435401 0.059147 Uani 1.000000 0 0.000130 0.000195
0.000720 0.001818
H2A -0.066275 0.509187 0.445584 0.151410 Uani 1.000000 0 0.001064 0.001270
0.006069 0.029726
H2B -0.109648 0.559609 0.294842 0.125522 Uani 1.000000 0 0.001770 0.001696
0.004898 0.024501
H2C -0.129030 0.549576 0.555482 0.117282 Uani 1.000000 0 0.001110 0.001632
0.005003 0.023851
C3 -0.062586 0.681474 0.358062 0.063010 Uani 1.000000 0 0.000163 0.000150
0.000634 0.001953
O2 0.089471 0.666278 0.979330 0.049991 Uani 1.000000 0 0.000054 0.000079
0.000253 0.000877
O3 0.056939 0.579603 1.193762 0.054894 Uani 1.000000 0 0.000053 0.000053
0.000262 0.000869
C5 0.148176 0.630198 1.276002 0.033432 Uani 1.000000 0 0.000075 0.000075
0.000348 0.001063
C10 0.202065 0.602671 1.216769 0.034127 Uani 1.000000 0 0.000081 0.000075
0.000322 0.001078
O5 0.255728 0.547020 0.943303 0.054476 Uani 1.000000 0 0.000055 0.000065
0.000210 0.000868
C8 0.246930 0.655851 1.532835 0.036347 Uani 1.000000 0 0.000075 0.000092
0.000314 0.001087
C4 0.093778 0.622452 1.138530 0.037625 Uani 1.000000 0 0.000080 0.000098
0.000340 0.001143
N3 0.207718 0.558140 1.018354 0.042431 Uani 1.000000 0 0.000067 0.000081
0.000289 0.000925
N4 0.298798 0.670032 1.666814 0.045736 Uani 1.000000 0 0.000079 0.000078
0.000284 0.001069
C9 0.252004 0.614796 1.341161 0.035608 Uani 1.000000 0 0.000086 0.000094
0.000346 0.001113
C6 0.145341 0.670901 1.472345 0.041155 Uani 1.000000 0 0.000088 0.000115
0.000397 0.001268
O6 0.344232 0.646918 1.599711 0.069473 Uani 1.000000 0 0.000055 0.000085
0.000264 0.001026
O7 0.293613 0.703960 1.838215 0.069515 Uani 1.000000 0 0.000066 0.000071
0.000244 0.000992
C7 0.194443 0.683330 1.603615 0.040547 Uani 1.000000 0 0.000087 0.000100
0.000375 0.001318
O4 0.164311 0.534311 0.936415 0.080813 Uani 1.000000 0 0.000061 0.000079
0.000303 0.001205

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 0.1049(8) 0.6944(11) 1.516(3) 0.084(18) Uani 1.000000 0
H7 0.1911(9) 0.7172(8) 1.756(4) 0.077(17) Uani 1.000000 0
H9 0.2931(8) 0.5941(9) 1.292(3) 0.064(15) Uani 1.000000 0
H1A -0.0367(13) 0.5171(11) 0.764(6) 0.11(2) Uani 1.000000 0
H1B 0.0083(10) 0.5630(15) 0.943(4) 0.07(2) Uani 1.000000 0
H3A -0.055(2) 0.6691(18) 0.196(5) 0.15(3) Uani 1.000000 0
H3B -0.1029(10) 0.7034(16) 0.357(7) 0.18(3) Uani 1.000000 0
H3C -0.0337(14) 0.7225(14) 0.419(6) 0.16(3) Uani 1.000000 0
H1 0.0462(14) 0.6691(16) 0.904(11) 0.28(6) Uani 1.000000 0
O1 0.00707(6) 0.67207(7) 0.7196(2) 0.0506(8) Uani 1.000000 0
N2 -0.05765(6) 0.61911(8) 0.4954(3) 0.0457(10) Uani 1.000000 0
N1 -0.02003(9) 0.56263(11) 0.8073(4) 0.0548(14) Uani 1.000000 0
C1 -0.02358(8) 0.61823(10) 0.6747(4) 0.0393(12) Uani 1.000000 0
C2 -0.09278(13) 0.55991(19) 0.4354(7) 0.0591(18) Uani 1.000000 0
H2A -0.0663(11) 0.5092(13) 0.446(6) 0.15(3) Uani 1.000000 0
H2B -0.1096(18) 0.5596(17) 0.295(5) 0.13(2) Uani 1.000000 0
H2C -0.1290(11) 0.5496(16) 0.555(5) 0.12(2) Uani 1.000000 0
C3 -0.06259(16) 0.68147(15) 0.3581(6) 0.063(2) Uani 1.000000 0
O2 0.08947(5) 0.66628(8) 0.9793(3) 0.0500(9) Uani 1.000000 0
O3 0.05694(5) 0.57960(5) 1.1938(3) 0.0549(9) Uani 1.000000 0
C5 0.14818(8) 0.63020(8) 1.2760(3) 0.0334(11) Uani 1.000000 0
C10 0.20206(8) 0.60267(8) 1.2168(3) 0.0341(11) Uani 1.000000 0
O5 0.25573(6) 0.54702(7) 0.9433(2) 0.0545(9) Uani 1.000000 0
C8 0.24693(8) 0.65585(9) 1.5328(3) 0.0363(11) Uani 1.000000 0
C4 0.09378(8) 0.62245(10) 1.1385(3) 0.0376(11) Uani 1.000000 0
N3 0.20772(7) 0.55814(8) 1.0184(3) 0.0424(9) Uani 1.000000 0
N4 0.29880(8) 0.67003(8) 1.6668(3) 0.0457(11) Uani 1.000000 0
C9 0.25200(9) 0.61480(9) 1.3412(3) 0.0356(11) Uani 1.000000 0
C6 0.14534(9) 0.67090(11) 1.4723(4) 0.0412(13) Uani 1.000000 0
O6 0.34423(6) 0.64692(9) 1.5997(3) 0.0695(10) Uani 1.000000 0
O7 0.29361(7) 0.70396(7) 1.8382(2) 0.0695(10) Uani 1.000000 0
C7 0.19444(9) 0.68333(10) 1.6036(4) 0.0405(13) Uani 1.000000 0
O4 0.16431(6) 0.53431(8) 0.9364(3) 0.0808(12) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.073012 0.106019 0.071822 -0.039759 0.009350 0.000696 0.014374 0.020278
0.018996 0.014833 0.015282 0.016024
H7 0.121701 0.011339 0.098393 -0.011635 0.012393 -0.011514 0.018847 0.011164
0.020993 0.012941 0.017796 0.013574
H9 0.051164 0.103060 0.037545 0.001626 0.018003 0.007125 0.013657 0.017939
0.014281 0.012946 0.013398 0.012737
H1A 0.161209 0.049638 0.111278 0.030411 -0.090743 -0.059407 0.030851 0.015437
0.025961 0.018063 0.020172 0.017793
H1B 0.081103 0.125119 0.016914 0.000107 0.000987 0.034741 0.021123 0.023439
0.017624 0.021721 0.016654 0.017728
H3A 0.165141 0.214936 0.064864 0.063583 -0.021081 0.075446 0.040289 0.037180
0.020497 0.035978 0.025802 0.028316
H3B 0.097119 0.129721 0.302567 0.045389 -0.044573 0.138591 0.022546 0.023240
0.045126 0.020080 0.028073 0.025197
H3C 0.212329 0.108907 0.173464 -0.093268 -0.164556 0.054662 0.032810 0.024843
0.035296 0.023386 0.025523 0.019874
H1 0.070990 0.113128 0.669605 0.082536 0.193432 0.211416 0.025399 0.031677
0.115384 0.028863 0.046902 0.049258
O1 0.049316 0.039315 0.063248 -0.003968 -0.009685 0.006481 0.000762 0.000707
0.001043 0.000793 0.000845 0.000766
N2 0.035230 0.051467 0.050378 0.003049 -0.002388 -0.001958 0.000880 0.000984
0.001206 0.000863 0.000947 0.000983
N1 0.056476 0.042359 0.065425 -0.006501 -0.018246 0.010442 0.001217 0.001126
0.001816 0.001066 0.001104 0.001340
C1 0.034159 0.034917 0.048971 -0.005157 -0.011520 0.005589 0.001012 0.001137
0.001503 0.000977 0.001096 0.001156
C2 0.046265 0.067047 0.064129 -0.007353 -0.017647 -0.005934 0.001484 0.001801
0.002168 0.001543 0.001623 0.001963
H2A 0.114848 0.089419 0.249964 0.020910 -0.072146 0.065403 0.023817 0.020767
0.044596 0.018679 0.027867 0.023435
H2B 0.160757 0.077907 0.137901 -0.064092 -0.080872 -0.008497 0.027341 0.017802
0.028360 0.019316 0.029716 0.021987
H2C 0.037921 0.170827 0.143096 -0.010524 0.026680 -0.099248 0.013432 0.026645
0.031476 0.018356 0.018766 0.021762
C3 0.072940 0.056854 0.059237 0.003806 -0.014748 0.013498 0.002122 0.001710
0.002027 0.001781 0.001918 0.001615
O2 0.043600 0.050328 0.056045 -0.011527 -0.008095 0.011925 0.000770 0.000881
0.000981 0.000801 0.000862 0.000942
O3 0.045275 0.052356 0.067051 -0.015587 -0.010446 0.018603 0.000713 0.000758
0.001135 0.000822 0.000881 0.000807
C5 0.031322 0.032309 0.036663 0.000130 0.001110 -0.003791 0.000961 0.000924
0.001305 0.000805 0.000931 0.000925
C10 0.036564 0.030912 0.034905 0.002067 -0.003624 -0.004483 0.001081 0.000921
0.001233 0.000792 0.001097 0.000888
O5 0.058178 0.055194 0.050058 0.006104 0.004645 -0.014911 0.000802 0.000859
0.000941 0.000790 0.000869 0.000782
C8 0.037255 0.037574 0.034213 -0.003586 -0.000615 0.000681 0.000985 0.001023
0.001254 0.000976 0.001032 0.000940
C4 0.035374 0.034220 0.043282 -0.007297 -0.005718 0.010048 0.000972 0.001056
0.001400 0.000902 0.001106 0.001066
N3 0.041178 0.040833 0.045282 0.004246 -0.005111 -0.011899 0.000866 0.000783
0.001125 0.000954 0.001020 0.000902
N4 0.042565 0.052513 0.042129 -0.001124 -0.009983 -0.008171 0.000977 0.001053
0.001179 0.000987 0.000966 0.000922
C9 0.032055 0.037920 0.036849 0.006486 0.001146 -0.002964 0.000995 0.001017
0.001327 0.000979 0.001170 0.000883
C6 0.037533 0.045349 0.040583 0.000415 0.007889 -0.007625 0.001178 0.001059
0.001567 0.001096 0.001168 0.001159
O6 0.044431 0.103540 0.060448 0.000180 -0.010623 -0.013045 0.000716 0.001243
0.001121 0.000952 0.000949 0.000987
O7 0.073242 0.074007 0.061296 0.003112 -0.024106 -0.021654 0.001053 0.000911
0.001013 0.000992 0.000974 0.000946
C7 0.042142 0.044753 0.034746 0.004925 0.000342 -0.007593 0.001246 0.001287
0.001421 0.001058 0.001135 0.001066
O4 0.059598 0.089086 0.093754 0.004977 -0.012770 -0.055210 0.000842 0.001286
0.001489 0.000838 0.001117 0.001125

# ====
# ADPs
# ====


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 . N3 . 1.2127(16) yes
O6 . N4 . 1.2066(18) yes
O7 . N4 . 1.2114(17) yes
O4 . N3 . 1.2039(18) yes
O1 . C1 . 1.284(2) yes
O2 . C4 . 1.268(2) yes
O3 . C4 . 1.2298(19) yes
O2 . H1 . 1.09(5) yes
N2 . C1 . 1.320(2) yes
N2 . C2 . 1.444(3) yes
N2 . C3 . 1.455(3) yes
N1 . C1 . 1.330(3) yes
N3 . C10 . 1.459(2) yes
N4 . C8 . 1.461(2) yes
N1 . H1A . 0.99(2) yes
N1 . H1B . 1.03(2) yes
C5 . C10 . 1.397(2) yes
C5 . C4 . 1.503(2) yes
C5 . C6 . 1.402(3) yes
C10 . C9 . 1.387(3) yes
C8 . C9 . 1.387(2) yes
C8 . C7 . 1.387(2) yes
C6 . C7 . 1.394(3) yes
C2 . H2A . 1.16(2) yes
C2 . H2B . 0.92(2) yes
C2 . H2C . 1.11(2) yes
C3 . H3A . 1.00(3) yes
C3 . H3B . 1.02(2) yes
C3 . H3C . 1.10(2) yes
C9 . H9 . 1.070(17) yes
C6 . H6 . 1.070(19) yes
C7 . H7 . 1.116(18) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 . N3 . O4 . 123.10(18) yes
O6 . N4 . O7 . 124.05(19) yes
O5 . N3 . C10 . 118.66(16) yes
O6 . N4 . C8 . 117.72(16) yes
O7 . N4 . C8 . 118.22(18) yes
O4 . N3 . C10 . 118.24(16) yes
O2 . C4 . O3 . 126.18(18) yes
O1 . C1 . N2 . 118.92(19) yes
O1 . C1 . N1 . 119.8(2) yes
O2 . C4 . C5 . 113.57(17) yes
O3 . C4 . C5 . 120.08(18) yes
N2 . C1 . N1 . 121.3(2) yes
N3 . C10 . C5 . 120.30(17) yes
N3 . C10 . C9 . 116.78(17) yes
N4 . C8 . C9 . 118.68(17) yes
N4 . C8 . C7 . 118.75(17) yes
N2 . C2 . H2A . 111.0(12) yes
N2 . C2 . H2B . 118(2) yes
N2 . C2 . H2C . 114.0(15) yes
N2 . C3 . H3A . 108.8(19) yes
N2 . C3 . H3B . 114.6(16) yes
N2 . C3 . H3C . 111.5(15) yes
C4 . O2 . H1 . 113.9(18) yes
C1 . N2 . C2 . 121.4(2) yes
C1 . N2 . C3 . 120.3(2) yes
C2 . N2 . C3 . 118.2(2) yes
C1 . N1 . H1A . 122.6(18) yes
C1 . N1 . H1B . 119.3(16) yes
C5 . C10 . C9 . 122.91(17) yes
C5 . C6 . C7 . 121.2(2) yes
C10 . C5 . C4 . 124.81(18) yes
C10 . C5 . C6 . 117.48(19) yes
C10 . C9 . C8 . 117.30(18) yes
C8 . C7 . C6 . 118.48(19) yes
C4 . C5 . C6 . 117.62(18) yes
C9 . C8 . C7 . 122.56(18) yes
C5 . C6 . H6 . 118.6(11) yes
C10 . C9 . H9 . 122.0(11) yes
C8 . C9 . H9 . 120.7(11) yes
C8 . C7 . H7 . 121.9(12) yes
C6 . C7 . H7 . 119.5(12) yes
C7 . C6 . H6 . 120.1(11) yes
H1A . N1 . H1B . 117(2) yes
H3A . C3 . H3B . 104(2) yes
H3A . C3 . H3C . 113(2) yes
H3B . C3 . H3C . 105(2) yes
H2A . C2 . H2B . 105(3) yes
H2A . C2 . H2C . 102(2) yes
H2B . C2 . H2C . 105(2) yes
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate 1:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_200K_har
_database_code_depnum_ccdc_archive 'CCDC 1922023'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_200K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      47.66 %     
RESPONSE: Related to the use of a non-standard diffraction wavelength.
;
_vrf_PLAT211_complex_2_200K_har  
;
PROBLEM: ADP of Atom H1        is N.P.D. or (nearly) 2D .     Please Check 
RESPONSE: The HAR method is not yet optimised for the anisotropic refinement of H-atom thermal parameters.
;
_vrf_PLAT230_complex_2_200K_har  
;
PROBLEM: Hirshfeld Test Diff for    O4       --N3       .        9.2 s.u.  
RESPONSE: O5 and N3 are not the same atom type.
;
# end Validation Reply Form

_audit_creation_date             2018-12-21
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto


# ========
# Chemical
# ========

_chemical_name_common            200K
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_moiety         'C3 H9 N2 O1, C7 H3 N2 O6'
_chemical_formula_weight         300.2297
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       156
_QCr_calc_unit_n_alpha_electrons 78
_QCr_calc_unit_n_beta_electrons  78

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008


# ==============
# Absortion data
# ==============
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.994890606381
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   
;
 CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
 Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;


# ========
# Symmetry
# ========

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'p b c a'
_symmetry_space_group_name_Hall  '-p 2ac 2ab'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, -y, +z+1/2'
'+x+1/2, -y+1/2, -z'
'+x+1/2, +y, -z+1/2'
'-x+1/2, +y+1/2, +z'
'-x, +y+1/2, -z+1/2'
'+x, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    200
_cell_measurement_reflns_used    25459
_cell_measurement_theta_min      1.70419623743
_cell_measurement_theta_max      36.0064993709

_cell_length_a                   23.02270(8)
_cell_length_b                   19.24130(7)
_cell_length_c                   5.87020(2)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 90.000000(0)
_cell_angle_gamma                90.000000(0)
_cell_volume                     2600.420(17)

_cell_formula_units_Z            8.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========

_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            3351
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.998
_diffrn_reflns_theta_max         27.740
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            333.034166

_reflns_d_resolution_high        9.878465
_reflns_d_resolution_low         0.740031
_reflns_limit_h_max              30
_reflns_limit_h_min              0
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                2895
_reflns_number_total             2895
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0231
_refine_ls_R_factor_all          0.0231
_refine_ls_wR_factor_gt          0.0232
_refine_ls_wR_factor_all         0.0232
_refine_ls_R_Fsqd_factor         0.0332
_refine_ls_goodness_of_fit_gt    1.6355
_refine_ls_goodness_of_fit_all   1.6355
_refine_ls_number_reflns         2895
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0036
_refine_ls_shift/su_max_mean     0.0002
_refine_ls_shift/su_max_par      'H3A px'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.0933
_refine_diff_density_min         -0.0938
_refine_diff_density_rms         0.0179
_refine_diff_density_max_atom    0.0434
_refine_diff_density_max_atom_tag O4
_refine_diff_density_min_atom    -0.0342
_refine_diff_density_min_atom_tag C10
_refine_diff_density_rms_atom    0.0176

_refine_special_details          
;
   HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.
  
. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  run Hart with the following options:
  -shelx-f2 200K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.00285 0.00150 N 0.00565 0.00308 O 0.01010 0.00566"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  200K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

200k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 0.106087 0.691899 1.525194 0.060326 Uani 1.000000 0 0.000398 0.000469
0.001527 0.006469
H7 0.192695 0.713957 1.757611 0.060102 Uani 1.000000 0 0.000367 0.000526
0.001666 0.006776
H9 0.292862 0.592339 1.290604 0.054077 Uani 1.000000 0 0.000403 0.000495
0.001425 0.006276
H1A -0.042719 0.519951 0.773363 0.075213 Uani 1.000000 0 0.000491 0.000616
0.001896 0.008759
H1B 0.005567 0.567975 0.948357 0.055774 Uani 1.000000 0 0.000516 0.000527
0.002037 0.007747
H2A -0.107617 0.563497 0.261518 0.116480 Uani 1.000000 0 0.000622 0.000646
0.002383 0.011651
H2B -0.068842 0.512183 0.425984 0.106858 Uani 1.000000 0 0.000527 0.000558
0.002435 0.009738
H3A -0.060473 0.667014 0.182019 0.137394 Uani 1.000000 0 0.000800 0.000756
0.002275 0.013623
H2C -0.126971 0.554048 0.538902 0.122519 Uani 1.000000 0 0.000601 0.000702
0.002644 0.012026
H3B -0.102458 0.704154 0.369731 0.139338 Uani 1.000000 0 0.000646 0.000688
0.003139 0.012996
H3C -0.031513 0.715103 0.395367 0.145680 Uani 1.000000 0 0.000703 0.000741
0.002998 0.013333
H1 0.044193 0.665058 0.847536 0.036494 Uani 1.000000 0 0.000523 0.000573
0.002076 0.008458
O1 0.007330 0.672814 0.718312 0.037932 Uani 1.000000 0 0.000024 0.000025
0.000092 0.000291
N2 -0.057400 0.619179 0.490913 0.033773 Uani 1.000000 0 0.000024 0.000030
0.000099 0.000318
N1 -0.019846 0.562819 0.806408 0.041569 Uani 1.000000 0 0.000034 0.000038
0.000137 0.000413
C1 -0.023104 0.618422 0.672361 0.030049 Uani 1.000000 0 0.000027 0.000035
0.000116 0.000351
C2 -0.092778 0.559750 0.430361 0.044607 Uani 1.000000 0 0.000043 0.000050
0.000197 0.000519
C3 -0.062408 0.681033 0.351086 0.047435 Uani 1.000000 0 0.000051 0.000053
0.000182 0.000551
O2 0.089704 0.666731 0.980520 0.037764 Uani 1.000000 0 0.000021 0.000026
0.000083 0.000286
O3 0.056889 0.579693 1.196086 0.040711 Uani 1.000000 0 0.000022 0.000026
0.000086 0.000293
C5 0.148843 0.630064 1.279275 0.026157 Uani 1.000000 0 0.000027 0.000032
0.000108 0.000329
C10 0.202746 0.602613 1.218679 0.025774 Uani 1.000000 0 0.000027 0.000032
0.000106 0.000326
O5 0.256717 0.547121 0.941826 0.041140 Uani 1.000000 0 0.000023 0.000026
0.000085 0.000305
C8 0.247765 0.655660 1.536540 0.027818 Uani 1.000000 0 0.000028 0.000034
0.000107 0.000340
C4 0.093940 0.622699 1.139657 0.028427 Uani 1.000000 0 0.000028 0.000033
0.000112 0.000340
N3 0.208449 0.557999 1.017530 0.032364 Uani 1.000000 0 0.000026 0.000029
0.000098 0.000328
N4 0.300127 0.669679 1.671197 0.034945 Uani 1.000000 0 0.000026 0.000032
0.000102 0.000340
C9 0.252856 0.614986 1.343396 0.027582 Uani 1.000000 0 0.000030 0.000035
0.000115 0.000353
C6 0.145875 0.670544 1.476117 0.031053 Uani 1.000000 0 0.000032 0.000037
0.000118 0.000375
O6 0.346010 0.646174 1.603920 0.051447 Uani 1.000000 0 0.000024 0.000033
0.000099 0.000349
O7 0.294899 0.703804 1.844591 0.052977 Uani 1.000000 0 0.000025 0.000030
0.000094 0.000364
C7 0.195037 0.683320 1.606275 0.031549 Uani 1.000000 0 0.000031 0.000038
0.000130 0.000372
O4 0.164495 0.533892 0.935712 0.062282 Uani 1.000000 0 0.000026 0.000035
0.000112 0.000396

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 0.1061(4) 0.6919(5) 1.5252(15) 0.060(6) Uani 1.000000 0
H7 0.1927(4) 0.7140(5) 1.7576(17) 0.060(7) Uani 1.000000 0
H9 0.2929(4) 0.5923(5) 1.2906(14) 0.054(6) Uani 1.000000 0
H1A -0.0427(5) 0.5200(6) 0.7734(19) 0.075(9) Uani 1.000000 0
H1B 0.0056(5) 0.5680(5) 0.948(2) 0.056(8) Uani 1.000000 0
H2A -0.1076(6) 0.5635(6) 0.262(2) 0.116(12) Uani 1.000000 0
H2B -0.0688(5) 0.5122(6) 0.426(2) 0.107(10) Uani 1.000000 0
H3A -0.0605(8) 0.6670(8) 0.182(2) 0.137(14) Uani 1.000000 0
H2C -0.1270(6) 0.5540(7) 0.539(3) 0.123(12) Uani 1.000000 0
H3B -0.1025(6) 0.7042(7) 0.370(3) 0.139(13) Uani 1.000000 0
H3C -0.0315(7) 0.7151(7) 0.395(3) 0.146(13) Uani 1.000000 0
H1 0.0442(5) 0.6651(6) 0.848(2) 0.036(8) Uani 1.000000 0
O1 0.00733(2) 0.67281(3) 0.71831(9) 0.0379(3) Uani 1.000000 0
N2 -0.05740(2) 0.61918(3) 0.49091(10) 0.0338(3) Uani 1.000000 0
N1 -0.01985(3) 0.56282(4) 0.80641(14) 0.0416(4) Uani 1.000000 0
C1 -0.02310(3) 0.61842(3) 0.67236(12) 0.0300(4) Uani 1.000000 0
C2 -0.09278(4) 0.55975(5) 0.4304(2) 0.0446(5) Uani 1.000000 0
C3 -0.06241(5) 0.68103(5) 0.35109(18) 0.0474(6) Uani 1.000000 0
O2 0.08970(2) 0.66673(3) 0.98052(8) 0.0378(3) Uani 1.000000 0
O3 0.05689(2) 0.57969(3) 1.19609(9) 0.0407(3) Uani 1.000000 0
C5 0.14884(3) 0.63006(3) 1.27928(11) 0.0262(3) Uani 1.000000 0
C10 0.20275(3) 0.60261(3) 1.21868(11) 0.0258(3) Uani 1.000000 0
O5 0.25672(2) 0.54712(3) 0.94183(9) 0.0411(3) Uani 1.000000 0
C8 0.24777(3) 0.65566(3) 1.53654(11) 0.0278(3) Uani 1.000000 0
C4 0.09394(3) 0.62270(3) 1.13966(11) 0.0284(3) Uani 1.000000 0
N3 0.20845(3) 0.55800(3) 1.01753(10) 0.0324(3) Uani 1.000000 0
N4 0.30013(3) 0.66968(3) 1.67120(10) 0.0349(3) Uani 1.000000 0
C9 0.25286(3) 0.61499(4) 1.34340(11) 0.0276(4) Uani 1.000000 0
C6 0.14588(3) 0.67054(4) 1.47612(12) 0.0311(4) Uani 1.000000 0
O6 0.34601(2) 0.64617(3) 1.60392(10) 0.0514(3) Uani 1.000000 0
O7 0.29490(2) 0.70380(3) 1.84459(9) 0.0530(4) Uani 1.000000 0
C7 0.19504(3) 0.68332(4) 1.60628(13) 0.0315(4) Uani 1.000000 0
O4 0.16450(3) 0.53389(3) 0.93571(11) 0.0623(4) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.053510 0.062068 0.065402 0.007849 -0.001969 -0.009289 0.006141 0.006622
0.006642 0.005374 0.004939 0.004879
H7 0.041467 0.078429 0.060409 0.008273 -0.005702 -0.008276 0.005850 0.007916
0.006563 0.005189 0.004730 0.005415
H9 0.052163 0.069636 0.040432 -0.004468 0.004867 -0.007590 0.006234 0.006932
0.005662 0.005461 0.004512 0.004678
H1A 0.071627 0.057532 0.096481 -0.022108 -0.024944 0.013536 0.008934 0.007679
0.009662 0.006874 0.006945 0.006737
H1B 0.058046 0.049072 0.060203 -0.014874 -0.024894 0.010692 0.007938 0.007284
0.008018 0.005910 0.006229 0.006090
H2A 0.135468 0.096191 0.117782 -0.034329 -0.077817 0.001503 0.013115 0.010609
0.011229 0.008400 0.010318 0.008286
H2B 0.095123 0.043950 0.181503 0.015763 -0.051794 -0.018527 0.009206 0.006794
0.013213 0.006903 0.009156 0.007669
H3A 0.223605 0.122358 0.066219 0.006162 -0.021134 0.026055 0.019243 0.012242
0.009382 0.011838 0.010222 0.007833
H2C 0.095391 0.134018 0.138147 -0.059027 0.037032 -0.060188 0.010376 0.012889
0.012814 0.009109 0.009209 0.009754
H3B 0.108445 0.089204 0.220366 0.058271 0.069809 0.061473 0.011397 0.010280
0.017312 0.009326 0.011093 0.010385
H3C 0.143842 0.097896 0.195303 -0.070925 -0.093855 0.076141 0.014035 0.010392
0.015572 0.010844 0.012748 0.010261
H1 0.011929 0.059226 0.038326 -0.002273 -0.023638 0.005975 0.008307 0.008574
0.008494 0.006633 0.007432 0.006280
O1 0.035773 0.030054 0.047970 -0.003693 -0.009681 0.004773 0.000288 0.000270
0.000315 0.000216 0.000242 0.000230
N2 0.027537 0.037235 0.036546 0.000159 -0.002729 0.001693 0.000296 0.000335
0.000322 0.000247 0.000245 0.000253
N1 0.041458 0.032724 0.050527 -0.007404 -0.014795 0.009309 0.000416 0.000374
0.000450 0.000309 0.000336 0.000348
C1 0.025143 0.028234 0.036770 -0.000525 -0.003951 0.002394 0.000324 0.000353
0.000376 0.000266 0.000277 0.000291
C2 0.036891 0.045123 0.051806 -0.005082 -0.011082 -0.004442 0.000479 0.000519
0.000558 0.000391 0.000431 0.000436
C3 0.051694 0.046150 0.044461 0.000369 -0.011459 0.009819 0.000573 0.000537
0.000544 0.000449 0.000447 0.000415
O2 0.034604 0.038739 0.039948 -0.010279 -0.008171 0.010940 0.000285 0.000286
0.000287 0.000218 0.000223 0.000223
O3 0.034282 0.039455 0.048396 -0.011503 -0.007550 0.012920 0.000278 0.000292
0.000309 0.000220 0.000225 0.000238
C5 0.024533 0.025392 0.028546 0.000301 -0.000879 -0.000655 0.000325 0.000318
0.000343 0.000247 0.000261 0.000256
C10 0.025955 0.023937 0.027431 0.001422 -0.001847 -0.002406 0.000335 0.000312
0.000330 0.000254 0.000251 0.000256
O5 0.042559 0.042993 0.037870 0.005152 0.003233 -0.012248 0.000313 0.000309
0.000292 0.000235 0.000234 0.000227
C8 0.028825 0.028318 0.026310 0.000291 -0.001917 -0.001207 0.000341 0.000339
0.000340 0.000258 0.000260 0.000259
C4 0.024695 0.027210 0.033375 -0.003509 -0.002428 0.004651 0.000324 0.000331
0.000366 0.000265 0.000265 0.000285
N3 0.032444 0.030735 0.033914 0.003243 -0.003908 -0.009575 0.000343 0.000312
0.000329 0.000245 0.000256 0.000250
N4 0.034094 0.039474 0.031269 -0.001015 -0.007497 -0.003764 0.000347 0.000345
0.000328 0.000265 0.000257 0.000271
C9 0.025298 0.029249 0.028198 0.003053 -0.001094 -0.003951 0.000348 0.000352
0.000360 0.000280 0.000282 0.000272
C6 0.027764 0.034288 0.031106 0.004451 0.002412 -0.003491 0.000372 0.000383
0.000369 0.000302 0.000297 0.000294
O6 0.032045 0.076951 0.045346 0.002215 -0.008693 -0.009503 0.000290 0.000423
0.000334 0.000274 0.000244 0.000294
O7 0.052986 0.058307 0.047637 0.003013 -0.017335 -0.019348 0.000371 0.000379
0.000342 0.000286 0.000260 0.000279
C7 0.033624 0.033944 0.027079 0.003582 0.000409 -0.006487 0.000392 0.000371
0.000352 0.000297 0.000302 0.000307
O4 0.043049 0.069975 0.073822 0.003649 -0.010757 -0.044349 0.000342 0.000416
0.000431 0.000296 0.000306 0.000345

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 . N3 . 1.2150(7) yes
O6 . N4 . 1.2151(8) yes
O7 . N4 . 1.2172(8) yes
O4 . N3 . 1.2124(8) yes
O1 . C1 . 1.2880(8) yes
O2 . C4 . 1.2649(8) yes
O3 . C4 . 1.2337(8) yes
O1 . H1 . 1.148(13) yes
O2 . H1 . 1.307(13) yes
N2 . C1 . 1.3260(9) yes
N2 . C2 . 1.4482(10) yes
N2 . C3 . 1.4503(10) yes
N1 . C1 . 1.3302(10) yes
N3 . C10 . 1.4657(8) yes
N4 . C8 . 1.4666(9) yes
N1 . H1A . 0.998(11) yes
N1 . H1B . 1.023(12) yes
C5 . C10 . 1.3948(9) yes
C5 . C4 . 1.5131(9) yes
C5 . C6 . 1.3952(9) yes
C10 . C9 . 1.3870(9) yes
C8 . C9 . 1.3827(9) yes
C8 . C7 . 1.3873(10) yes
C6 . C7 . 1.3875(10) yes
C2 . H2A . 1.051(12) yes
C2 . H2B . 1.069(11) yes
C2 . H2C . 1.019(13) yes
C3 . H3A . 1.029(14) yes
C3 . H3B . 1.030(12) yes
C3 . H3C . 1.002(13) yes
C9 . H9 . 1.065(9) yes
C6 . H6 . 1.044(9) yes
C7 . H7 . 1.068(10) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 . N3 . O4 . 123.55(6) yes
O6 . N4 . O7 . 123.95(6) yes
O5 . N3 . C10 . 118.52(6) yes
O6 . N4 . C8 . 118.10(6) yes
O7 . N4 . C8 . 117.95(6) yes
O4 . N3 . C10 . 117.93(6) yes
O2 . C4 . O3 . 126.46(6) yes
O1 . C1 . N2 . 118.90(6) yes
O1 . C1 . N1 . 119.93(7) yes
O2 . C4 . C5 . 113.68(5) yes
O3 . C4 . C5 . 119.67(6) yes
O1 . H1 . O2 . 169.8(10) yes
N2 . C1 . N1 . 121.17(7) yes
N3 . C10 . C5 . 120.46(6) yes
N3 . C10 . C9 . 116.82(6) yes
N4 . C8 . C9 . 118.45(6) yes
N4 . C8 . C7 . 119.32(6) yes
N2 . C2 . H2A . 111.1(7) yes
N2 . C2 . H2B . 113.1(6) yes
N2 . C2 . H2C . 111.5(7) yes
N2 . C3 . H3A . 109.1(8) yes
N2 . C3 . H3B . 111.4(7) yes
N2 . C3 . H3C . 109.5(7) yes
C1 . O1 . H1 . 115.8(5) yes
C4 . O2 . H1 . 119.1(5) yes
C1 . N2 . C2 . 121.56(7) yes
C1 . N2 . C3 . 120.73(7) yes
C2 . N2 . C3 . 117.67(7) yes
C1 . N1 . H1A . 121.3(6) yes
C1 . N1 . H1B . 115.9(6) yes
C5 . C10 . C9 . 122.71(6) yes
C5 . C6 . C7 . 121.00(7) yes
C10 . C5 . C4 . 124.72(6) yes
C10 . C5 . C6 . 117.79(6) yes
C10 . C9 . C8 . 117.36(6) yes
C8 . C7 . C6 . 118.90(7) yes
C4 . C5 . C6 . 117.39(6) yes
C9 . C8 . C7 . 122.23(6) yes
C5 . C6 . H6 . 119.4(5) yes
C10 . C9 . H9 . 119.7(5) yes
C8 . C9 . H9 . 122.9(5) yes
C8 . C7 . H7 . 120.1(5) yes
C6 . C7 . H7 . 121.0(5) yes
C7 . C6 . H6 . 119.6(5) yes
H1A . N1 . H1B . 122.7(8) yes
H2A . C2 . H2B . 101.8(10) yes
H2A . C2 . H2C . 110.2(11) yes
H2B . C2 . H2C . 108.7(11) yes
H3A . C3 . H3B . 104.7(13) yes
H3A . C3 . H3C . 113.0(13) yes
H3B . C3 . H3C . 109.0(13) yes

_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate 1:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_300K_har
_database_code_depnum_ccdc_archive 'CCDC 1922026'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT353_complex_5_300K_har  
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.15 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a  very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT919_complex_5_300K_har  
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: Reflections used in the refinement are taken from the fcf from a SHELXL refinement using the LIST 4FVAR^2 command. HAR applies its own rejection criteria during the initial stages of refinement. Reflection was not rejected. 
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-3
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            300K
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_weight         410.3897
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       214
_QCr_calc_unit_n_alpha_electrons 107
_QCr_calc_unit_n_beta_electrons  107

# =======
# Crystal
# =======

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             856

# ==============
# Absortion data
# ==============

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6949
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/n 1'
_symmetry_space_group_name_Hall  '-p 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, +y+1/2, -z+1/2'
'+x+1/2, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    300
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      43.77

_cell_length_a                   7.2267(3)
_cell_length_b                   14.3176(6)
_cell_length_c                   18.3746(7)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 92.5051(19)
_cell_angle_gamma                90.000000(0)
_cell_volume                     1899.38(13)

_cell_formula_units_Z            4.000000

_atom_sites_solution_hydrogens   HAR


# ===========
# Device data
# ===========

_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6549
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         41.366
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            326.759618

_reflns_d_resolution_high        9.178520
_reflns_d_resolution_low         0.670330
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                4973
_reflns_number_total             4973
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0337
_refine_ls_R_factor_all          0.0337
_refine_ls_wR_factor_gt          0.0196
_refine_ls_wR_factor_all         0.0196
_refine_ls_R_Fsqd_factor         0.0284
_refine_ls_goodness_of_fit_gt    1.6232
_refine_ls_goodness_of_fit_all   1.6232
_refine_ls_number_reflns         4973
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0066
_refine_ls_shift/su_max_mean     0.0009
_refine_ls_shift/su_max_par      'H7 Uxx'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1178
_refine_diff_density_min         -0.1587
_refine_diff_density_rms         0.0289
_refine_diff_density_max_atom    0.0450
_refine_diff_density_max_atom_tag O2
_refine_diff_density_min_atom    -0.0358
_refine_diff_density_min_atom_tag H1
_refine_diff_density_rms_atom    0.0206

_refine_special_details          
;

  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 300K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  300K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

300k.cif obtained from res in _shelx_res_file
;

# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 1.129595 0.675014 0.399614 0.088984 Uani 1.000000 0 0.001246 0.000514
0.000435 0.006750
H8 1.058223 0.563369 0.183997 0.081810 Uani 1.000000 0 0.001238 0.000510
0.000437 0.006341
H7 1.095685 0.698557 0.265367 0.093994 Uani 1.000000 0 0.001269 0.000552
0.000471 0.006950
H5 1.125345 0.512824 0.448647 0.081903 Uani 1.000000 0 0.001226 0.000539
0.000425 0.006351
H1 1.103051 0.277018 0.461782 0.057652 Uani 1.000000 0 0.001335 0.000733
0.000460 0.007007
O3 0.896857 0.339897 0.216392 0.042375 Uani 1.000000 0 0.000064 0.000028
0.000022 0.000259
O1 1.080337 0.345186 0.443940 0.049189 Uani 1.000000 0 0.000078 0.000034
0.000025 0.000301
O2 1.149171 0.284314 0.336911 0.053878 Uani 1.000000 0 0.000073 0.000030
0.000023 0.000290
O4 1.171771 0.366517 0.170549 0.057704 Uani 1.000000 0 0.000076 0.000032
0.000025 0.000311
C4 1.097824 0.447486 0.343947 0.033260 Uani 1.000000 0 0.000079 0.000038
0.000031 0.000313
C2 1.052862 0.382607 0.214695 0.037304 Uani 1.000000 0 0.000097 0.000039
0.000031 0.000340
C1 1.111585 0.350858 0.373997 0.036310 Uani 1.000000 0 0.000088 0.000040
0.000032 0.000331
C7 1.095962 0.628975 0.287812 0.051722 Uani 1.000000 0 0.000106 0.000047
0.000045 0.000436
C3 1.079283 0.461572 0.268447 0.033259 Uani 1.000000 0 0.000082 0.000036
0.000031 0.000310
C5 1.113046 0.524509 0.390463 0.042891 Uani 1.000000 0 0.000098 0.000046
0.000039 0.000385
C6 1.113328 0.614822 0.362707 0.050644 Uani 1.000000 0 0.000099 0.000048
0.000044 0.000437
C8 1.077609 0.552389 0.241361 0.044289 Uani 1.000000 0 0.000105 0.000044
0.000042 0.000388
H20 1.197550 0.020227 0.633645 0.080880 Uani 1.000000 0 0.001329 0.000478
0.000418 0.006252
H19 1.111329 0.186261 0.600718 0.083468 Uani 1.000000 0 0.001299 0.000508
0.000392 0.006357
H18 1.208541 0.141751 0.386884 0.092129 Uani 1.000000 0 0.001400 0.000497
0.000406 0.006800
H2A 1.334747 -0.156960 0.440442 0.070985 Uani 1.000000 0 0.001401 0.000556
0.000502 0.006694
H17 1.287801 -0.022932 0.407555 0.092290 Uani 1.000000 0 0.001294 0.000516
0.000383 0.006793
H2B 1.369216 -0.241056 0.509275 0.064911 Uani 1.000000 0 0.001257 0.000568
0.000440 0.006260
O5 1.291320 -0.136138 0.608856 0.055451 Uani 1.000000 0 0.000077 0.000028
0.000023 0.000300
N1 1.154411 0.169806 0.492355 0.040421 Uani 1.000000 0 0.000074 0.000033
0.000027 0.000299
N2 1.336517 -0.174898 0.492337 0.044759 Uani 1.000000 0 0.000097 0.000045
0.000036 0.000354
C15 1.294199 -0.114314 0.544197 0.036673 Uani 1.000000 0 0.000087 0.000039
0.000033 0.000334
C20 1.199444 0.045560 0.577859 0.041498 Uani 1.000000 0 0.000100 0.000042
0.000036 0.000370
C16 1.248222 -0.015368 0.523198 0.032536 Uani 1.000000 0 0.000078 0.000037
0.000030 0.000307
C19 1.152203 0.136786 0.560006 0.043442 Uani 1.000000 0 0.000103 0.000045
0.000037 0.000388
C17 1.250373 0.018769 0.452602 0.041579 Uani 1.000000 0 0.000098 0.000045
0.000036 0.000377
C18 1.204168 0.111679 0.439959 0.044297 Uani 1.000000 0 0.000101 0.000045
0.000037 0.000389
H11 0.871118 0.033293 0.027915 0.076421 Uani 1.000000 0 0.001227 0.000509
0.000402 0.006203
H13 0.939317 0.130573 0.280824 0.096770 Uani 1.000000 0 0.001428 0.000555
0.000461 0.007185
H12 0.877882 0.203290 0.066730 0.078298 Uani 1.000000 0 0.001232 0.000527
0.000408 0.006114
H14 0.941700 -0.039510 0.253583 0.094745 Uani 1.000000 0 0.001434 0.000502
0.000411 0.006866
H4A 0.826876 -0.246600 0.144782 0.068633 Uani 1.000000 0 0.001266 0.000564
0.000424 0.006552
H4B 0.774770 -0.159021 0.205372 0.064910 Uani 1.000000 0 0.001363 0.000552
0.000447 0.006586
H3 0.905217 0.247093 0.192163 0.059688 Uani 1.000000 0 0.001244 0.000752
0.000467 0.007874
O6 0.943147 -0.137075 0.053080 0.058161 Uani 1.000000 0 0.000077 0.000030
0.000024 0.000311
N4 0.838558 -0.178715 0.162175 0.046293 Uani 1.000000 0 0.000100 0.000044
0.000035 0.000369
N3 0.905878 0.170047 0.175047 0.041709 Uani 1.000000 0 0.000077 0.000039
0.000030 0.000319
C9 0.894960 -0.116663 0.114462 0.038648 Uani 1.000000 0 0.000089 0.000040
0.000033 0.000344
C11 0.883353 0.052710 0.084748 0.037945 Uani 1.000000 0 0.000094 0.000042
0.000037 0.000351
C10 0.899023 -0.015859 0.138089 0.033923 Uani 1.000000 0 0.000080 0.000038
0.000031 0.000315
C14 0.921423 0.011088 0.210595 0.046626 Uani 1.000000 0 0.000107 0.000047
0.000037 0.000393
C12 0.887376 0.145265 0.105164 0.040557 Uani 1.000000 0 0.000094 0.000044
0.000037 0.000371
C13 0.923926 0.105492 0.227323 0.049991 Uani 1.000000 0 0.000113 0.000048
0.000042 0.000429

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 1.1296(12) 0.6750(5) 0.3996(4) 0.089(7) Uani 1.000000 0
H8 1.0582(12) 0.5634(5) 0.1840(4) 0.082(6) Uani 1.000000 0
H7 1.0957(13) 0.6986(6) 0.2654(5) 0.094(7) Uani 1.000000 0
H5 1.1253(12) 0.5128(5) 0.4486(4) 0.082(6) Uani 1.000000 0
H1 1.1031(13) 0.2770(7) 0.4618(5) 0.058(7) Uani 1.000000 0
O3 0.89686(6) 0.33990(3) 0.21639(2) 0.0424(3) Uani 1.000000 0
O1 1.08034(8) 0.34519(3) 0.44394(2) 0.0492(3) Uani 1.000000 0
O2 1.14917(7) 0.28431(3) 0.33691(2) 0.0539(3) Uani 1.000000 0
O4 1.17177(8) 0.36652(3) 0.17055(2) 0.0577(3) Uani 1.000000 0
C4 1.09782(8) 0.44749(4) 0.34395(3) 0.0333(3) Uani 1.000000 0
C2 1.05286(10) 0.38261(4) 0.21469(3) 0.0373(3) Uani 1.000000 0
C1 1.11158(9) 0.35086(4) 0.37400(3) 0.0363(3) Uani 1.000000 0
C7 1.09596(11) 0.62897(5) 0.28781(4) 0.0517(4) Uani 1.000000 0
C3 1.07928(8) 0.46157(4) 0.26845(3) 0.0333(3) Uani 1.000000 0
C5 1.11305(10) 0.52451(5) 0.39046(4) 0.0429(4) Uani 1.000000 0
C6 1.11333(10) 0.61482(5) 0.36271(4) 0.0506(4) Uani 1.000000 0
C8 1.07761(11) 0.55239(4) 0.24136(4) 0.0443(4) Uani 1.000000 0
H20 1.1975(13) 0.0202(5) 0.6336(4) 0.081(6) Uani 1.000000 0
H19 1.1113(13) 0.1863(5) 0.6007(4) 0.083(6) Uani 1.000000 0
H18 1.2085(14) 0.1418(5) 0.3869(4) 0.092(7) Uani 1.000000 0
H2A 1.3347(14) -0.1570(6) 0.4404(5) 0.071(7) Uani 1.000000 0
H17 1.2878(13) -0.0229(5) 0.4076(4) 0.092(7) Uani 1.000000 0
H2B 1.3692(13) -0.2411(6) 0.5093(4) 0.065(6) Uani 1.000000 0
O5 1.29132(8) -0.13614(3) 0.60886(2) 0.0555(3) Uani 1.000000 0
N1 1.15441(7) 0.16981(3) 0.49236(3) 0.0404(3) Uani 1.000000 0
N2 1.33652(10) -0.17490(4) 0.49234(4) 0.0448(4) Uani 1.000000 0
C15 1.29420(9) -0.11431(4) 0.54420(3) 0.0367(3) Uani 1.000000 0
C20 1.19944(10) 0.04556(4) 0.57786(4) 0.0415(4) Uani 1.000000 0
C16 1.24822(8) -0.01537(4) 0.52320(3) 0.0325(3) Uani 1.000000 0
C19 1.15220(10) 0.13679(4) 0.56001(4) 0.0434(4) Uani 1.000000 0
C17 1.25037(10) 0.01877(5) 0.45260(4) 0.0416(4) Uani 1.000000 0
C18 1.20417(10) 0.11168(5) 0.43996(4) 0.0443(4) Uani 1.000000 0
H11 0.8711(12) 0.0333(5) 0.0279(4) 0.076(6) Uani 1.000000 0
H13 0.9393(14) 0.1306(6) 0.2808(5) 0.097(7) Uani 1.000000 0
H12 0.8779(12) 0.2033(5) 0.0667(4) 0.078(6) Uani 1.000000 0
H14 0.9417(14) -0.0395(5) 0.2536(4) 0.095(7) Uani 1.000000 0
H4A 0.8269(13) -0.2466(6) 0.1448(4) 0.069(7) Uani 1.000000 0
H4B 0.7748(14) -0.1590(6) 0.2054(4) 0.065(7) Uani 1.000000 0
H3 0.9052(12) 0.2471(8) 0.1922(5) 0.060(8) Uani 1.000000 0
O6 0.94315(8) -0.13707(3) 0.05308(2) 0.0582(3) Uani 1.000000 0
N4 0.83856(10) -0.17871(4) 0.16218(4) 0.0463(4) Uani 1.000000 0
N3 0.90588(8) 0.17005(4) 0.17505(3) 0.0417(3) Uani 1.000000 0
C9 0.89496(9) -0.11666(4) 0.11446(3) 0.0386(3) Uani 1.000000 0
C11 0.88335(9) 0.05271(4) 0.08475(4) 0.0379(4) Uani 1.000000 0
C10 0.89902(8) -0.01586(4) 0.13809(3) 0.0339(3) Uani 1.000000 0
C14 0.92142(11) 0.01109(5) 0.21059(4) 0.0466(4) Uani 1.000000 0
C12 0.88738(9) 0.14526(4) 0.10516(4) 0.0406(4) Uani 1.000000 0
C13 0.92393(11) 0.10549(5) 0.22732(4) 0.0500(4) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.116444 0.058327 0.091403 -0.013309 -0.004328 -0.024965 0.007867 0.005589
0.006796 0.005143 0.005875 0.004950
H8 0.111133 0.052739 0.081094 -0.005550 -0.001110 0.014030 0.007474 0.005419
0.006121 0.004726 0.005956 0.004721
H7 0.123569 0.053185 0.105741 0.002061 0.010875 0.003302 0.007988 0.005586
0.007326 0.005429 0.006042 0.005109
H5 0.104470 0.067949 0.071601 0.009322 -0.015430 -0.012225 0.007225 0.005923
0.005884 0.004981 0.005795 0.004819
H1 0.078220 0.056970 0.037738 0.010672 0.002216 0.000226 0.007528 0.007500
0.006037 0.006510 0.005346 0.005543
O3 0.060017 0.032289 0.034989 -0.004011 0.004035 -0.006190 0.000310 0.000230
0.000236 0.000205 0.000217 0.000179
O1 0.077588 0.039344 0.030802 0.009043 0.004273 0.002583 0.000376 0.000280
0.000249 0.000257 0.000239 0.000213
O2 0.094953 0.033104 0.033819 0.018072 0.005569 0.003655 0.000389 0.000242
0.000242 0.000238 0.000245 0.000190
O4 0.083018 0.047442 0.044987 -0.002432 0.029470 -0.002389 0.000377 0.000279
0.000284 0.000247 0.000276 0.000213
C4 0.040364 0.027829 0.031266 0.002003 -0.002095 -0.001107 0.000341 0.000285
0.000311 0.000237 0.000264 0.000230
C2 0.057255 0.028952 0.026348 0.000119 0.009163 0.001134 0.000430 0.000289
0.000303 0.000280 0.000294 0.000226
C1 0.050851 0.029830 0.028069 0.006348 -0.000322 0.001775 0.000378 0.000308
0.000307 0.000258 0.000274 0.000239
C7 0.063695 0.024914 0.066351 -0.000955 0.000472 0.002192 0.000465 0.000326
0.000516 0.000316 0.000392 0.000334
C3 0.044193 0.024514 0.031110 -0.000365 0.002096 0.002128 0.000346 0.000272
0.000313 0.000234 0.000262 0.000222
C5 0.052263 0.035095 0.040530 0.002602 -0.006919 -0.008880 0.000417 0.000348
0.000388 0.000283 0.000342 0.000302
C6 0.058353 0.030533 0.062318 0.000080 -0.005661 -0.010854 0.000454 0.000348
0.000506 0.000306 0.000381 0.000328
C8 0.060395 0.027872 0.044632 -0.000844 0.002666 0.007257 0.000442 0.000317
0.000405 0.000281 0.000368 0.000300
H20 0.145834 0.048251 0.049446 0.013114 0.014447 0.003258 0.008466 0.005244
0.005075 0.005096 0.005529 0.004180
H19 0.134901 0.061788 0.054012 0.012263 0.007499 0.001709 0.008010 0.005706
0.005386 0.005276 0.005320 0.004321
H18 0.168702 0.053551 0.055447 0.029836 0.019885 0.017015 0.009724 0.005290
0.005457 0.005489 0.005900 0.004437
H2A 0.085803 0.054737 0.072524 0.001776 0.004701 0.000174 0.007588 0.006136
0.006403 0.004838 0.006317 0.005174
H17 0.153428 0.070948 0.054784 0.041797 0.030699 0.013894 0.008945 0.005977
0.005550 0.005704 0.005913 0.004408
H2B 0.099052 0.042642 0.053904 0.001911 0.013218 0.008587 0.007689 0.005392
0.005757 0.005187 0.005152 0.004510
O5 0.100283 0.031475 0.034465 0.008863 0.001459 0.005982 0.000412 0.000234
0.000253 0.000240 0.000257 0.000193
N1 0.054336 0.027666 0.039045 0.003790 -0.000423 0.004010 0.000343 0.000256
0.000297 0.000227 0.000256 0.000218
N2 0.060785 0.032885 0.041022 0.007417 0.006984 0.002890 0.000396 0.000310
0.000358 0.000280 0.000331 0.000285
C15 0.050741 0.027324 0.031787 0.001476 -0.000101 0.003810 0.000378 0.000289
0.000335 0.000259 0.000284 0.000238
C20 0.065750 0.029798 0.028826 0.001555 0.000684 0.001064 0.000448 0.000319
0.000341 0.000288 0.000323 0.000262
C16 0.041134 0.026599 0.029711 -0.000294 -0.000320 0.002155 0.000332 0.000274
0.000315 0.000242 0.000259 0.000229
C19 0.067017 0.028803 0.034444 0.003730 0.001522 -0.001385 0.000471 0.000326
0.000367 0.000306 0.000331 0.000269
C17 0.060374 0.033185 0.031520 0.008526 0.005895 0.004764 0.000434 0.000339
0.000361 0.000296 0.000320 0.000261
C18 0.065704 0.034110 0.033287 0.009526 0.004573 0.008052 0.000455 0.000345
0.000369 0.000305 0.000341 0.000277
H11 0.111518 0.065185 0.052020 0.001892 -0.002599 0.002023 0.007459 0.005859
0.005289 0.004750 0.005385 0.004433
H13 0.160946 0.064389 0.065112 -0.010564 0.006516 -0.012569 0.009638 0.005911
0.006050 0.005718 0.006421 0.004838
H12 0.115369 0.054561 0.065699 -0.005815 0.012330 0.005888 0.007304 0.005405
0.005686 0.005132 0.005191 0.004352
H14 0.187271 0.054031 0.042324 -0.006426 -0.001928 0.008315 0.010065 0.005619
0.004902 0.005663 0.005810 0.004148
H4A 0.108849 0.036368 0.061705 -0.003097 0.015419 -0.007875 0.008044 0.005380
0.006305 0.005114 0.005650 0.004485
H4B 0.089470 0.054938 0.050659 -0.001279 0.006905 0.001676 0.007866 0.006016
0.005950 0.004927 0.005418 0.004620
H3 0.068288 0.050493 0.061455 -0.009338 0.016211 -0.023732 0.007179 0.009538
0.006992 0.006216 0.005645 0.006228
O6 0.097915 0.035982 0.042992 -0.012704 0.030553 -0.009929 0.000410 0.000252
0.000277 0.000242 0.000277 0.000204
N4 0.070015 0.029570 0.040413 -0.004794 0.015203 -0.001973 0.000444 0.000297
0.000371 0.000292 0.000320 0.000267
N3 0.049591 0.029178 0.046766 -0.004855 0.006759 -0.007921 0.000338 0.000279
0.000341 0.000245 0.000267 0.000256
C9 0.055453 0.027974 0.033544 -0.005553 0.013664 -0.004704 0.000400 0.000294
0.000340 0.000265 0.000300 0.000243
C11 0.050707 0.031270 0.032058 -0.001648 0.004078 -0.001044 0.000392 0.000316
0.000347 0.000265 0.000306 0.000267
C10 0.044414 0.027624 0.030238 -0.004952 0.007417 -0.002805 0.000339 0.000283
0.000324 0.000245 0.000261 0.000234
C14 0.076862 0.033054 0.030294 -0.006410 0.006125 -0.002886 0.000485 0.000342
0.000356 0.000328 0.000340 0.000278
C12 0.052030 0.029038 0.040916 -0.000728 0.005616 0.000079 0.000404 0.000325
0.000387 0.000281 0.000319 0.000283
C13 0.078942 0.035943 0.035245 -0.007246 0.004289 -0.009751 0.000521 0.000372
0.000398 0.000334 0.000379 0.000309

# ====
# ADPs
# ====


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 . C2 . 1.2841(8) yes
O1 . C1 . 1.3171(7) yes
O2 . C1 . 1.2092(7) yes
O4 . C2 . 1.2290(7) yes
O5 . C15 . 1.2295(7) yes
O6 . C9 . 1.2301(7) yes
O1 . H1 . 1.040(10) yes
N1 . C19 . 1.3307(8) yes
N1 . C18 . 1.3338(8) yes
N2 . C15 . 1.3340(8) yes
N4 . C9 . 1.3249(8) yes
N3 . C12 . 1.3333(8) yes
N3 . C13 . 1.3353(9) yes
N2 . H2A . 0.987(9) yes
N2 . H2B . 1.022(8) yes
N4 . H4A . 1.025(8) yes
N4 . H4B . 0.977(8) yes
N3 . H3 . 1.147(10) yes
C4 . C1 . 1.4913(8) yes
C4 . C3 . 1.4025(8) yes
C4 . C5 . 1.3966(8) yes
C2 . C3 . 1.5079(8) yes
C7 . C6 . 1.3912(10) yes
C7 . C8 . 1.3923(10) yes
C3 . C8 . 1.3921(8) yes
C5 . C6 . 1.3900(9) yes
C15 . C16 . 1.5017(7) yes
C20 . C16 . 1.3874(8) yes
C20 . C19 . 1.3858(9) yes
C16 . C17 . 1.3869(8) yes
C17 . C18 . 1.3886(9) yes
C9 . C10 . 1.5071(8) yes
C11 . C10 . 1.3884(8) yes
C11 . C12 . 1.3772(8) yes
C10 . C14 . 1.3896(8) yes
C14 . C13 . 1.3861(9) yes
C7 . H7 . 1.078(8) yes
C5 . H5 . 1.082(8) yes
C6 . H6 . 1.100(7) yes
C8 . H8 . 1.069(8) yes
C20 . H20 . 1.088(7) yes
C19 . H19 . 1.081(7) yes
C17 . H17 . 1.065(7) yes
C18 . H18 . 1.068(7) yes
C11 . H11 . 1.081(7) yes
C14 . H14 . 1.077(7) yes
C12 . H12 . 1.091(7) yes
C13 . H13 . 1.048(8) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 . C2 . O4 . 124.52(6) yes
O1 . C1 . O2 . 123.62(6) yes
O5 . C15 . N2 . 122.62(6) yes
O6 . C9 . N4 . 123.71(6) yes
O3 . C2 . C3 . 115.30(5) yes
O1 . C1 . C4 . 114.02(5) yes
O2 . C1 . C4 . 122.36(5) yes
O4 . C2 . C3 . 120.05(6) yes
O5 . C15 . C16 . 118.37(5) yes
O6 . C9 . C10 . 119.27(5) yes
N1 . C19 . C20 . 122.90(6) yes
N1 . C18 . C17 . 123.19(6) yes
N2 . C15 . C16 . 119.01(6) yes
N4 . C9 . C10 . 117.02(6) yes
N3 . C12 . C11 . 121.23(6) yes
N3 . C13 . C14 . 121.03(7) yes
N1 . C19 . H19 . 115.4(4) yes
N1 . C18 . H18 . 115.3(4) yes
N3 . C12 . H12 . 114.9(4) yes
N3 . C13 . H13 . 116.1(5) yes
C1 . O1 . H1 . 109.5(5) yes
C19 . N1 . C18 . 117.85(5) yes
C12 . N3 . C13 . 120.74(6) yes
C15 . N2 . H2A . 121.8(5) yes
C15 . N2 . H2B . 116.3(5) yes
C9 . N4 . H4A . 116.9(4) yes
C9 . N4 . H4B . 120.9(5) yes
C12 . N3 . H3 . 121.2(4) yes
C13 . N3 . H3 . 118.0(4) yes
C4 . C3 . C2 . 122.96(5) yes
C4 . C3 . C8 . 119.14(5) yes
C4 . C5 . C6 . 120.75(7) yes
C2 . C3 . C8 . 117.86(5) yes
C1 . C4 . C3 . 120.10(5) yes
C1 . C4 . C5 . 120.25(6) yes
C7 . C6 . C5 . 119.79(7) yes
C7 . C8 . C3 . 121.15(7) yes
C3 . C4 . C5 . 119.56(5) yes
C6 . C7 . C8 . 119.59(6) yes
C15 . C16 . C20 . 117.87(5) yes
C15 . C16 . C17 . 124.15(5) yes
C20 . C16 . C17 . 117.98(6) yes
C16 . C20 . C19 . 119.28(6) yes
C16 . C17 . C18 . 118.79(6) yes
C9 . C10 . C11 . 118.28(5) yes
C9 . C10 . C14 . 122.82(5) yes
C11 . C10 . C14 . 118.88(6) yes
C10 . C11 . C12 . 119.21(6) yes
C10 . C14 . C13 . 118.89(6) yes
C4 . C5 . H5 . 118.9(4) yes
C7 . C6 . H6 . 119.9(4) yes
C7 . C8 . H8 . 119.6(4) yes
C3 . C8 . H8 . 119.3(4) yes
C5 . C6 . H6 . 120.3(4) yes
C6 . C7 . H7 . 120.8(5) yes
C6 . C5 . H5 . 120.3(4) yes
C8 . C7 . H7 . 119.6(5) yes
C20 . C19 . H19 . 121.7(4) yes
C16 . C20 . H20 . 119.1(4) yes
C16 . C17 . H17 . 122.9(4) yes
C19 . C20 . H20 . 121.6(4) yes
C17 . C18 . H18 . 121.5(4) yes
C18 . C17 . H17 . 118.3(4) yes
C11 . C12 . H12 . 123.8(4) yes
C10 . C11 . H11 . 120.1(4) yes
C10 . C14 . H14 . 121.5(4) yes
C14 . C13 . H13 . 122.8(5) yes
C12 . C11 . H11 . 120.7(4) yes
C13 . C14 . H14 . 119.6(4) yes
H2A . N2 . H2B . 121.9(7) yes
H4A . N4 . H4B . 119.4(7) yes
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_2_350K_har
_database_code_depnum_ccdc_archive 'CCDC 1922025'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_2_350K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      47.69 %     
RESPONSE: Related to the use of a non-standard diffraction wavelength. 
;
_vrf_PLAT230_complex_2_350K_har  
;
PROBLEM: Hirshfeld Test Diff for    O3       --C4       .        7.8 s.u.  
RESPONSE:  O3 and C4 are not the same atom type.
;
_vrf_PLAT355_complex_2_350K_har  
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O2       - H1       .       1.10 Ang.  
RESPONSE: The long O-H distance is characteristic of H1 forming a short O-H...O hydrogen bond.
;
_vrf_PLAT391_complex_2_350K_har  
;
PROBLEM: Deviating Methyl C2        H-C-H Bond Angle ....         96 Degree
RESPONSE: The methyl C2 undergoes some thermal motion at the high temperature. The methyl
H-atoms have been placed on C2 geometically using HFIX137, aiming to reduce the deviation
of the H-C-H bond angle.
;
# end Validation Reply Form

_audit_creation_date             2019-1-7
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            350K
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_moiety         'C3 H8 N2 O1, C7 H4 N2 O6'
_chemical_formula_weight         300.2297
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       156
_QCr_calc_unit_n_alpha_electrons 78
_QCr_calc_unit_n_beta_electrons  78

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.008


# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_min  0.991418910165
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'p b c a'
_symmetry_space_group_name_Hall  '-p 2ac 2ab'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, -y, +z+1/2'
'+x+1/2, -y+1/2, -z'
'+x+1/2, +y, -z+1/2'
'-x+1/2, +y+1/2, +z'
'-x, +y+1/2, -z+1/2'
'+x, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    350
_cell_measurement_reflns_used    11423
_cell_measurement_theta_max      35.4051469394
_cell_measurement_theta_min      1.69380406263

_cell_length_a                   23.2312(3)
_cell_length_b                   19.3458(3)
_cell_length_c                   6.00460(9)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 90.000000(0)
_cell_angle_gamma                90.000000(0)
_cell_volume                     2698.62(6)

_cell_formula_units_Z            8.000000

_atom_sites_solution_hydrogens   HAR


# ===========
# Device data
# ===========

_diffrn_ambient_temperature      350
_diffrn_radiation_wavelength     0.6889
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            3476
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         27.739
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            332.875175

_reflns_d_resolution_high        9.958450
_reflns_d_resolution_low         0.741865
_reflns_limit_h_max              29
_reflns_limit_h_min              0
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                1795
_reflns_number_total             1795
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0379
_refine_ls_R_factor_all          0.0379
_refine_ls_wR_factor_gt          0.0305
_refine_ls_wR_factor_all         0.0305
_refine_ls_R_Fsqd_factor         0.0346
_refine_ls_goodness_of_fit_gt    3.0443
_refine_ls_goodness_of_fit_all   3.0443
_refine_ls_number_reflns         1795
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_number_constraints    72
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0081
_refine_ls_shift/su_max_mean     0.0007
_refine_ls_shift/su_max_par      'C3 px'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.0828
_refine_diff_density_min         -0.0816
_refine_diff_density_rms         0.0149
_refine_diff_density_max_atom    0.0386
_refine_diff_density_max_atom_tag C3
_refine_diff_density_min_atom    -0.0380
_refine_diff_density_min_atom_tag C10
_refine_diff_density_rms_atom    0.0156

_refine_special_details          
;

  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 350K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.00285 0.00150 N 0.00565 0.00308 O 0.01010 0.00566"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps f
  -scf rhf
  350K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

350k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 0.106809 0.691629 1.509427 0.094000 Uani 1.000000 0 0.000778 0.000921
0.003034 0.000000
H7 0.190169 0.712007 1.724653 0.086000 Uani 1.000000 0 0.000748 0.000965
0.003066 0.000000
H9 0.287915 0.593421 1.285636 0.070000 Uani 1.000000 0 0.000744 0.000864
0.002657 0.000000
H1A -0.042548 0.521389 0.765350 0.124000 Uani 1.000000 0 0.001104 0.001378
0.003873 0.000000
H1B 0.005144 0.567078 0.950894 0.112000 Uani 1.000000 0 0.001184 0.001200
0.004276 0.000000
H1 0.047329 0.665370 0.891235 0.146000 Uani 1.000000 0 0.001628 0.001618
0.005894 0.000000
O1 0.007292 0.670818 0.720090 0.085383 Uani 1.000000 0 0.000057 0.000068
0.000218 0.000987
N2 -0.058300 0.619214 0.502757 0.077280 Uani 1.000000 0 0.000068 0.000085
0.000270 0.001158
N1 -0.019630 0.562438 0.804838 0.095001 Uani 1.000000 0 0.000085 0.000100
0.000340 0.001415
C1 -0.023405 0.617886 0.676405 0.067765 Uani 1.000000 0 0.000084 0.000108
0.000350 0.001393
C2 -0.094146 0.561102 0.441393 0.106075 Uani 1.000000 0 0.000114 0.000146
0.000485 0.002067
H2A -0.072430 0.512029 0.447358 0.160000 Uani 1.000000 0 0.001108 0.001396
0.004606 0.000000
H2B -0.107542 0.571016 0.279511 0.160000 Uani 1.000000 0 0.001208 0.001433
0.004372 0.000000
H2C -0.122577 0.549660 0.555487 0.160000 Uani 1.000000 0 0.001204 0.001417
0.004534 0.000000
C3 -0.062853 0.680923 0.367621 0.112774 Uani 1.000000 0 0.000134 0.000145
0.000482 0.002194
H3A -0.037571 0.717017 0.417504 0.170000 Uani 1.000000 0 0.001223 0.001514
0.004937 0.000000
H3B -0.104622 0.702844 0.379491 0.170000 Uani 1.000000 0 0.001135 0.001389
0.004523 0.000000
H3C -0.060963 0.668398 0.203492 0.170000 Uani 1.000000 0 0.001266 0.001527
0.004417 0.000000
O2 0.089368 0.665571 0.976416 0.083744 Uani 1.000000 0 0.000056 0.000071
0.000226 0.000982
O3 0.057002 0.580330 1.185567 0.092715 Uani 1.000000 0 0.000059 0.000075
0.000224 0.001034
C5 0.147545 0.630237 1.268017 0.057745 Uani 1.000000 0 0.000077 0.000086
0.000286 0.001159
C10 0.200879 0.602771 1.210318 0.055573 Uani 1.000000 0 0.000081 0.000081
0.000268 0.001115
O5 0.254110 0.547220 0.943584 0.093590 Uani 1.000000 0 0.000071 0.000070
0.000236 0.001104
C8 0.244806 0.655707 1.521305 0.060157 Uani 1.000000 0 0.000079 0.000090
0.000286 0.001213
C4 0.093602 0.622333 1.131095 0.065226 Uani 1.000000 0 0.000083 0.000102
0.000331 0.001324
N3 0.207080 0.558581 1.016438 0.071443 Uani 1.000000 0 0.000086 0.000079
0.000269 0.001191
N4 0.296323 0.670102 1.654778 0.077517 Uani 1.000000 0 0.000084 0.000094
0.000306 0.001290
C9 0.249847 0.615154 1.334264 0.060121 Uani 1.000000 0 0.000082 0.000092
0.000302 0.001222
C6 0.144491 0.670075 1.459644 0.067910 Uani 1.000000 0 0.000086 0.000100
0.000321 0.001324
O6 0.341534 0.647249 1.591369 0.112028 Uani 1.000000 0 0.000072 0.000093
0.000257 0.001295
O7 0.291079 0.703333 1.822916 0.115337 Uani 1.000000 0 0.000069 0.000083
0.000278 0.001341
C7 0.192784 0.682709 1.586761 0.069910 Uani 1.000000 0 0.000094 0.000101
0.000325 0.001410
O4 0.164516 0.534808 0.934746 0.129982 Uani 1.000000 0 0.000074 0.000092
0.000290 0.001455

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 0.1068(8) 0.6916(9) 1.509(3) 0.09400000(0) Uani 1.000000 0
H7 0.1902(7) 0.7120(10) 1.725(3) 0.08600000(0) Uani 1.000000 0
H9 0.2879(7) 0.5934(9) 1.286(3) 0.07000000(0) Uani 1.000000 0
H1A -0.0425(11) 0.5214(14) 0.765(4) 0.12400000(0) Uani 1.000000 0
H1B 0.0051(12) 0.5671(12) 0.951(4) 0.11200000(0) Uani 1.000000 0
H1 0.0473(16) 0.6654(16) 0.891(6) 0.14600000(0) Uani 1.000000 0
O1 0.00729(6) 0.67082(7) 0.7201(2) 0.0854(10) Uani 1.000000 0
N2 -0.05830(7) 0.61921(8) 0.5028(3) 0.0773(12) Uani 1.000000 0
N1 -0.01963(8) 0.56244(10) 0.8048(3) 0.0950(14) Uani 1.000000 0
C1 -0.02341(8) 0.61789(11) 0.6764(3) 0.0678(14) Uani 1.000000 0
C2 -0.09415(11) 0.56110(15) 0.4414(5) 0.106(2) Uani 1.000000 0
H2A -0.0724(11) 0.5120(14) 0.447(5) 0.16000000(0) Uani 1.000000 0
H2B -0.1075(12) 0.5710(14) 0.280(4) 0.16000000(0) Uani 1.000000 0
H2C -0.1226(12) 0.5497(14) 0.555(5) 0.16000000(0) Uani 1.000000 0
C3 -0.06285(13) 0.68092(14) 0.3676(5) 0.113(2) Uani 1.000000 0
H3A -0.0376(12) 0.7170(15) 0.418(5) 0.17000000(0) Uani 1.000000 0
H3B -0.1046(11) 0.7028(14) 0.379(5) 0.17000000(0) Uani 1.000000 0
H3C -0.0610(13) 0.6684(15) 0.203(4) 0.17000000(0) Uani 1.000000 0
O2 0.08937(6) 0.66557(7) 0.9764(2) 0.0837(10) Uani 1.000000 0
O3 0.05700(6) 0.58033(7) 1.1856(2) 0.0927(10) Uani 1.000000 0
C5 0.14754(8) 0.63024(9) 1.2680(3) 0.0577(12) Uani 1.000000 0
C10 0.20088(8) 0.60277(8) 1.2103(3) 0.0556(11) Uani 1.000000 0
O5 0.25411(7) 0.54722(7) 0.9436(2) 0.0936(11) Uani 1.000000 0
C8 0.24481(8) 0.65571(9) 1.5213(3) 0.0602(12) Uani 1.000000 0
C4 0.09360(8) 0.62233(10) 1.1311(3) 0.0652(13) Uani 1.000000 0
N3 0.20708(9) 0.55858(8) 1.0164(3) 0.0714(12) Uani 1.000000 0
N4 0.29632(8) 0.67010(9) 1.6548(3) 0.0775(13) Uani 1.000000 0
C9 0.24985(8) 0.61515(9) 1.3343(3) 0.0601(12) Uani 1.000000 0
C6 0.14449(9) 0.67008(10) 1.4596(3) 0.0679(13) Uani 1.000000 0
O6 0.34153(7) 0.64725(9) 1.5914(3) 0.1120(13) Uani 1.000000 0
O7 0.29108(7) 0.70333(8) 1.8229(3) 0.1153(13) Uani 1.000000 0
C7 0.19278(9) 0.68271(10) 1.5868(3) 0.0699(14) Uani 1.000000 0
O4 0.16452(7) 0.53481(9) 0.9347(3) 0.1300(15) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.094000 0.094000 0.094000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H7 0.086000 0.086000 0.086000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H9 0.070000 0.070000 0.070000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H1A 0.124000 0.124000 0.124000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H1B 0.112000 0.112000 0.112000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H1 0.146000 0.146000 0.146000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
O1 0.081883 0.067967 0.106300 -0.009461 -0.018108 0.012255 0.000972 0.000899
0.001091 0.000776 0.000810 0.000771
N2 0.060429 0.086276 0.085134 0.002745 -0.004088 0.001330 0.001026 0.001279
0.001171 0.000956 0.000943 0.001029
N1 0.094174 0.075546 0.115283 -0.019566 -0.032617 0.021270 0.001484 0.001285
0.001475 0.001035 0.001079 0.001196
C1 0.054962 0.065122 0.083210 -0.002150 -0.009412 0.009171 0.001235 0.001459
0.001484 0.001108 0.001084 0.001196
C2 0.091824 0.109800 0.116599 -0.016511 -0.025774 -0.001709 0.002033 0.002005
0.002164 0.001640 0.001582 0.001858
H2A 0.160000 0.160000 0.160000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H2B 0.160000 0.160000 0.160000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H2C 0.160000 0.160000 0.160000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
C3 0.126500 0.105352 0.106470 0.005434 -0.027635 0.025231 0.002443 0.002253
0.001887 0.001699 0.001948 0.001837
H3A 0.170000 0.170000 0.170000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H3B 0.170000 0.170000 0.170000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
H3C 0.170000 0.170000 0.170000 0.000000 0.000000 0.000000 0.000000 0.000000
0.000000 0.000000 0.000000 0.000000
O2 0.075587 0.082455 0.093191 -0.021117 -0.016924 0.022156 0.000979 0.000967
0.000999 0.000790 0.000738 0.000793
O3 0.079742 0.089054 0.109347 -0.027122 -0.019126 0.028634 0.001002 0.001052
0.001049 0.000856 0.000800 0.000827
C5 0.054999 0.052307 0.065929 -0.000330 0.000586 -0.000354 0.001222 0.001027
0.001226 0.000916 0.000991 0.000927
C10 0.059709 0.048299 0.058713 0.001535 -0.002850 -0.002559 0.001237 0.001022
0.001085 0.000897 0.000989 0.000870
O5 0.099232 0.094948 0.086591 0.009882 0.009580 -0.027782 0.001168 0.001135
0.001010 0.000910 0.000862 0.000792
C8 0.063783 0.055729 0.060959 0.000069 -0.001970 0.000431 0.001312 0.001134
0.001194 0.000960 0.001037 0.000918
C4 0.059208 0.056459 0.080011 -0.012642 -0.005602 0.014904 0.001359 0.001226
0.001388 0.001071 0.001078 0.001093
N3 0.069869 0.067194 0.077265 0.006857 -0.005845 -0.018998 0.001257 0.001100
0.001217 0.001010 0.001063 0.000904
N4 0.072316 0.083702 0.076534 0.000485 -0.013414 -0.007329 0.001329 0.001275
0.001266 0.001083 0.001126 0.001010
C9 0.056194 0.058749 0.065419 0.007396 0.003955 -0.005303 0.001293 0.001157
0.001217 0.000950 0.001032 0.000945
C6 0.060377 0.070489 0.072865 0.007591 0.006429 -0.006931 0.001349 0.001296
0.001327 0.001081 0.001119 0.001089
O6 0.075419 0.156132 0.104532 0.002687 -0.020607 -0.018233 0.001069 0.001610
0.001205 0.001064 0.000917 0.001093
O7 0.118945 0.121900 0.105167 0.006725 -0.034388 -0.039692 0.001413 0.001360
0.001250 0.001044 0.000985 0.001005
C7 0.075126 0.069749 0.064856 0.006049 0.001740 -0.014532 0.001519 0.001359
0.001353 0.001132 0.001199 0.000987
O4 0.101301 0.141167 0.147477 0.008125 -0.019771 -0.083963 0.001307 0.001541
0.001517 0.001122 0.001101 0.001259

# ====
# ADPs
# ====


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 . N3 . 1.1972(18) yes
O6 . N4 . 1.2015(19) yes
O7 . N4 . 1.2031(19) yes
O4 . N3 . 1.1958(19) yes
O1 . C1 . 1.275(2) yes
O2 . C4 . 1.254(2) yes
O3 . C4 . 1.221(2) yes
O2 . H1 . 1.10(4) yes
N2 . C1 . 1.321(2) yes
N2 . C2 . 1.447(3) yes
N2 . C3 . 1.447(3) yes
N1 . C1 . 1.324(2) yes
N3 . C10 . 1.452(2) yes
N4 . C8 . 1.467(2) yes
N1 . H1A . 0.99(3) yes
N1 . H1B . 1.05(3) yes
C5 . C10 . 1.392(2) yes
C5 . C4 . 1.507(2) yes
C5 . C6 . 1.387(2) yes
C10 . C9 . 1.380(2) yes
C8 . C9 . 1.375(2) yes
C8 . C7 . 1.374(2) yes
C6 . C7 . 1.379(2) yes
C2 . H2A . 1.08(3) yes
C2 . H2B . 1.04(3) yes
C2 . H2C . 0.98(3) yes
C3 . H3A . 0.96(3) yes
C3 . H3B . 1.06(3) yes
C3 . H3C . 1.02(3) yes
C9 . H9 . 1.022(17) yes
C6 . H6 . 1.015(17) yes
C7 . H7 . 1.005(18) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 . N3 . O4 . 122.29(18) yes
O6 . N4 . O7 . 123.4(2) yes
O5 . N3 . C10 . 119.46(18) yes
O6 . N4 . C8 . 118.05(19) yes
O7 . N4 . C8 . 118.51(19) yes
O4 . N3 . C10 . 118.26(19) yes
O2 . C4 . O3 . 126.01(19) yes
O1 . C1 . N2 . 119.34(19) yes
O1 . C1 . N1 . 119.6(2) yes
O2 . C4 . C5 . 113.69(17) yes
O3 . C4 . C5 . 120.05(18) yes
N2 . C1 . N1 . 121.1(2) yes
N3 . C10 . C5 . 120.85(17) yes
N3 . C10 . C9 . 116.93(17) yes
N4 . C8 . C9 . 119.02(18) yes
N4 . C8 . C7 . 119.28(18) yes
N2 . C2 . H2A . 114.0(15) yes
N2 . C2 . H2B . 105.5(16) yes
N2 . C2 . H2C . 112.7(17) yes
N2 . C3 . H3A . 112.3(18) yes
N2 . C3 . H3B . 111.0(15) yes
N2 . C3 . H3C . 110.1(17) yes
C4 . O2 . H1 . 114.3(17) yes
C1 . N2 . C2 . 122.6(2) yes
C1 . N2 . C3 . 120.23(19) yes
C2 . N2 . C3 . 117.13(19) yes
C1 . N1 . H1A . 118.5(15) yes
C1 . N1 . H1B . 116.9(13) yes
C5 . C10 . C9 . 122.22(17) yes
C5 . C6 . C7 . 121.08(18) yes
C10 . C5 . C4 . 124.46(17) yes
C10 . C5 . C6 . 117.66(17) yes
C10 . C9 . C8 . 117.98(17) yes
C8 . C7 . C6 . 119.34(19) yes
C4 . C5 . C6 . 117.82(17) yes
C9 . C8 . C7 . 121.70(18) yes
C5 . C6 . H6 . 121.1(11) yes
C10 . C9 . H9 . 119.2(9) yes
C8 . C9 . H9 . 122.8(9) yes
C8 . C7 . H7 . 120.2(11) yes
C6 . C7 . H7 . 120.4(11) yes
C7 . C6 . H6 . 117.8(11) yes
H1A . N1 . H1B . 124.4(19) yes
H2A . C2 . H2B . 110(2) yes
H2A . C2 . H2C . 95(2) yes
H2B . C2 . H2C . 120(2) yes
H3A . C3 . H3B . 104(2) yes
H3A . C3 . H3C . 117(3) yes
H3B . C3 . H3C . 102(2) yes
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoic acid 1:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex7_200K_har
_database_code_depnum_ccdc_archive 'CCDC 1922034'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex7_200K_har   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.68 %
RESPONSE:  Data collection at non-standard wavelength. Fprime used for anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex7_200K_har   
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.21 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT230_complex7_200K_har   
;
PROBLEM: Hirshfeld Test Diff for    O10      --N6       .        8.3 s.u.
RESPONSE: O10 and N6 are not the same atom type.
;
_vrf_PLAT230_complex7_200K_har_2 
;
PROBLEM: Hirshfeld Test Diff for    O14      --N5       .        7.6 s.u.
RESPONSE: O10 and N6 are not the same atom type.
;
_vrf_PLAT353_complex7_200K_har_2 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H1       .       1.10 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT430_complex7_200K_har   
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.80 Ang.
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi
;
_vrf_PLAT230_complex7_200K_har_3 
;
PROBLEM: Hirshfeld Test Diff for    O4       --N7       .        5.4 s.u.
RESPONSE: O10 and N6 are not the same atom type.
;
_vrf_PLAT230_complex7_200K_har_4 
;
PROBLEM: Hirshfeld Test Diff for    O13      --N5       .        6.6 s.u.
RESPONSE: O10 and N6 are not the same atom type.
;
_vrf_PLAT353_complex7_200K_har_3 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N4       - H12      .       1.03 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT353_complex7_200K_har_4 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H8       .       1.04 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-5
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            200K
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_weight         668.4945
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       344
_QCr_calc_unit_n_alpha_electrons 172
_QCr_calc_unit_n_beta_electrons  172

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             688

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'p -1'
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'

# =========
# Unit cell
# =========

_cell_measurement_temperature    200
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      43.75

_cell_length_a                   9.6926(4)
_cell_length_b                   10.3369(4)
_cell_length_c                   15.3321(6)
_cell_angle_alpha                78.854(2)
_cell_angle_beta                 71.624(2)
_cell_angle_gamma                77.257(2)
_cell_volume                     1409.14(10)

_cell_formula_units_Z            2.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========
_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6697
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.540
_diffrn_reflns_theta_max         35.633
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            216.124501

_reflns_d_resolution_high        9.991752
_reflns_d_resolution_low         0.760089
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                5425
_reflns_number_total             5425
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;



# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0282
_refine_ls_R_factor_all          0.0282
_refine_ls_wR_factor_gt          0.0241
_refine_ls_wR_factor_all         0.0241
_refine_ls_R_Fsqd_factor         0.0435
_refine_ls_goodness_of_fit_gt    1.4040
_refine_ls_goodness_of_fit_all   1.4040
_refine_ls_number_reflns         5425
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0039
_refine_ls_shift/su_max_mean     0.0003
_refine_ls_shift/su_max_par      'H18 Uyy'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.2130
_refine_diff_density_min         -0.2501
_refine_diff_density_rms         0.0401
_refine_diff_density_max_atom    0.0373
_refine_diff_density_max_atom_tag H3
_refine_diff_density_min_atom    -0.1029
_refine_diff_density_min_atom_tag C26
_refine_diff_density_rms_atom    0.0325

_refine_special_details          
;
  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 200K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  200K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

200k.cif obtained from res in _shelx_res_file

;



# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H19 1.474683 0.801401 0.123170 0.061407 Uani 1.000000 0 0.001210 0.001151
0.000720 0.008391
H5 0.814711 0.653256 0.162814 0.065588 Uani 1.000000 0 0.001265 0.001059
0.000797 0.008567
H10 -0.032815 0.345213 0.683907 0.071931 Uani 1.000000 0 0.001295 0.001106
0.000839 0.009156
H4 0.611302 0.564083 0.293354 0.058679 Uani 1.000000 0 0.001188 0.001095
0.000753 0.008103
H18 1.290806 0.651634 0.193619 0.068674 Uani 1.000000 0 0.001359 0.001115
0.000826 0.008787
H20 1.491295 0.734091 -0.148516 0.049794 Uani 1.000000 0 0.001131 0.001042
0.000741 0.007463
H3 0.397488 0.942018 0.347987 0.071406 Uani 1.000000 0 0.001309 0.001051
0.000818 0.009009
H6 0.595995 1.047401 0.224887 0.057749 Uani 1.000000 0 0.001112 0.001028
0.000766 0.007862
H17 1.095262 0.080040 0.159161 0.087502 Uani 1.000000 0 0.001442 0.001120
0.000962 0.010248
H15 0.894925 -0.033372 0.277115 0.067354 Uani 1.000000 0 0.001236 0.001060
0.000807 0.008608
H11 0.083049 0.167103 0.435733 0.054535 Uani 1.000000 0 0.001146 0.001125
0.000734 0.008079
H9 0.153424 0.491325 0.608886 0.061998 Uani 1.000000 0 0.001203 0.001073
0.000708 0.008064
H13 0.470510 0.117262 0.493684 0.055495 Uani 1.000000 0 0.001347 0.001173
0.000878 0.008978
H7 1.046430 0.886254 0.028891 0.065703 Uani 1.000000 0 0.001390 0.001205
0.000922 0.009752
H12 0.539373 0.260700 0.432630 0.058628 Uani 1.000000 0 0.001321 0.001320
0.000899 0.009482
H14 0.729902 0.337003 0.390748 0.086994 Uani 1.000000 0 0.001415 0.001110
0.000901 0.010271
H1 0.419626 0.702560 0.378977 0.048283 Uani 1.000000 0 0.001536 0.001249
0.000988 0.010082
H8 0.991520 0.747750 0.113027 0.059871 Uani 1.000000 0 0.001280 0.001197
0.000902 0.009554
H16 0.933675 0.432868 0.264582 0.084127 Uani 1.000000 0 0.001331 0.001203
0.000807 0.009727
H2 1.110511 0.318526 0.154277 0.047110 Uani 1.000000 0 0.001694 0.001354
0.000959 0.010779
O2 1.630536 0.899281 -0.140249 0.039243 Uani 1.000000 0 0.000070 0.000063
0.000044 0.000396
O1 1.662216 0.893037 -0.007749 0.051494 Uani 1.000000 0 0.000080 0.000075
0.000049 0.000457
O3 1.361547 0.569148 -0.169860 0.073665 Uani 1.000000 0 0.000094 0.000092
0.000054 0.000593
O4 1.156616 0.566314 -0.064122 0.055601 Uani 1.000000 0 0.000082 0.000079
0.000050 0.000485
O5 1.207325 0.398425 0.099916 0.030437 Uani 1.000000 0 0.000063 0.000057
0.000041 0.000349
O6 1.055945 0.571412 0.166515 0.033422 Uani 1.000000 0 0.000062 0.000055
0.000042 0.000354
N8 1.603622 0.861404 -0.057753 0.028437 Uani 1.000000 0 0.000079 0.000071
0.000054 0.000429
N7 1.282686 0.585597 -0.092742 0.036610 Uani 1.000000 0 0.000093 0.000078
0.000055 0.000484
C5 1.494060 0.773352 -0.015804 0.022987 Uani 1.000000 0 0.000087 0.000077
0.000056 0.000443
C3 1.341830 0.635642 -0.031614 0.022736 Uani 1.000000 0 0.000087 0.000078
0.000056 0.000440
C4 1.448248 0.715967 -0.073540 0.023220 Uani 1.000000 0 0.000094 0.000083
0.000064 0.000464
C2 1.284646 0.608787 0.064012 0.022719 Uani 1.000000 0 0.000085 0.000077
0.000056 0.000440
C1 1.171332 0.519719 0.113372 0.024653 Uani 1.000000 0 0.000089 0.000082
0.000057 0.000458
C7 1.334851 0.669405 0.119088 0.030527 Uani 1.000000 0 0.000105 0.000095
0.000068 0.000525
C6 1.439261 0.752595 0.079696 0.030485 Uani 1.000000 0 0.000105 0.000097
0.000065 0.000540
C10 0.727708 0.720700 0.203744 0.028815 Uani 1.000000 0 0.000103 0.000091
0.000065 0.000514
C13 0.495271 0.883619 0.307701 0.030688 Uani 1.000000 0 0.000106 0.000096
0.000067 0.000534
C11 0.615950 0.669256 0.274193 0.029253 Uani 1.000000 0 0.000100 0.000099
0.000066 0.000515
C8 0.840588 0.923933 0.111501 0.026160 Uani 1.000000 0 0.000091 0.000083
0.000059 0.000470
C12 0.604162 0.940697 0.238554 0.027967 Uani 1.000000 0 0.000097 0.000096
0.000063 0.000498
C9 0.723138 0.858880 0.186398 0.024140 Uani 1.000000 0 0.000088 0.000080
0.000057 0.000448
O12 0.813472 1.043199 0.082492 0.032923 Uani 1.000000 0 0.000063 0.000055
0.000041 0.000358
N3 0.970601 0.846356 0.082516 0.041095 Uani 1.000000 0 0.000096 0.000097
0.000068 0.000558
N2 0.504896 0.750395 0.324300 0.027827 Uani 1.000000 0 0.000086 0.000078
0.000054 0.000439
C17 0.796632 0.144957 0.341454 0.022859 Uani 1.000000 0 0.000087 0.000078
0.000055 0.000440
C16 0.675546 0.079240 0.411075 0.024080 Uani 1.000000 0 0.000090 0.000081
0.000057 0.000454
C18 0.900683 0.071550 0.275873 0.030847 Uani 1.000000 0 0.000098 0.000096
0.000065 0.000517
C15 0.807268 0.276748 0.339834 0.039372 Uani 1.000000 0 0.000115 0.000098
0.000072 0.000592
C14 0.919116 0.330722 0.271551 0.039821 Uani 1.000000 0 0.000113 0.000101
0.000071 0.000591
C19 1.010646 0.132148 0.209770 0.034905 Uani 1.000000 0 0.000109 0.000100
0.000071 0.000564
O8 0.470698 0.438275 0.405691 0.037928 Uani 1.000000 0 0.000064 0.000056
0.000045 0.000378
O11 -0.165752 0.168461 0.691024 0.044914 Uani 1.000000 0 0.000072 0.000065
0.000047 0.000427
O9 0.304463 0.619948 0.443117 0.031114 Uani 1.000000 0 0.000062 0.000054
0.000041 0.000347
O10 -0.124686 0.095488 0.561297 0.047736 Uani 1.000000 0 0.000073 0.000065
0.000052 0.000438
N5 0.283591 0.311846 0.337595 0.035463 Uani 1.000000 0 0.000088 0.000085
0.000052 0.000471
N6 -0.101399 0.165144 0.608919 0.032532 Uani 1.000000 0 0.000081 0.000073
0.000059 0.000456
O13 0.336142 0.202432 0.314447 0.069852 Uani 1.000000 0 0.000099 0.000078
0.000051 0.000568
O14 0.294509 0.415847 0.285850 0.057476 Uani 1.000000 0 0.000090 0.000075
0.000046 0.000501
O7 0.691892 -0.043952 0.425341 0.035149 Uani 1.000000 0 0.000064 0.000055
0.000043 0.000367
N1 1.017332 0.259399 0.208712 0.027398 Uani 1.000000 0 0.000084 0.000073
0.000053 0.000425
N4 0.555692 0.159247 0.452825 0.034695 Uani 1.000000 0 0.000097 0.000096
0.000064 0.000512
C21 0.223771 0.412170 0.481270 0.022945 Uani 1.000000 0 0.000087 0.000078
0.000056 0.000439
C20 0.344331 0.496764 0.438922 0.024128 Uani 1.000000 0 0.000092 0.000081
0.000056 0.000455
C24 0.011263 0.250097 0.564998 0.025907 Uani 1.000000 0 0.000089 0.000079
0.000060 0.000463
C25 0.030836 0.338535 0.615097 0.031824 Uani 1.000000 0 0.000107 0.000096
0.000069 0.000534
C22 0.199492 0.320232 0.434673 0.023691 Uani 1.000000 0 0.000089 0.000079
0.000054 0.000443
C23 0.095157 0.237726 0.474469 0.026359 Uani 1.000000 0 0.000100 0.000091
0.000066 0.000505
C26 0.137346 0.419037 0.572513 0.030645 Uani 1.000000 0 0.000103 0.000095
0.000063 0.000527

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H19 1.4747(12) 0.8014(12) 0.1232(7) 0.061(8) Uani 1.000000 0
H5 0.8147(13) 0.6533(11) 0.1628(8) 0.066(9) Uani 1.000000 0
H10 -0.0328(13) 0.3452(11) 0.6839(8) 0.072(9) Uani 1.000000 0
H4 0.6113(12) 0.5641(11) 0.2934(8) 0.059(8) Uani 1.000000 0
H18 1.2908(14) 0.6516(11) 0.1936(8) 0.069(9) Uani 1.000000 0
H20 1.4913(11) 0.7341(10) -0.1485(7) 0.050(7) Uani 1.000000 0
H3 0.3975(13) 0.9420(11) 0.3480(8) 0.071(9) Uani 1.000000 0
H6 0.5960(11) 1.0474(10) 0.2249(8) 0.058(8) Uani 1.000000 0
H17 1.0953(14) 0.0800(11) 0.1592(10) 0.088(10) Uani 1.000000 0
H15 0.8949(12) -0.0334(11) 0.2771(8) 0.067(9) Uani 1.000000 0
H11 0.0830(11) 0.1671(11) 0.4357(7) 0.055(8) Uani 1.000000 0
H9 0.1534(12) 0.4913(11) 0.6089(7) 0.062(8) Uani 1.000000 0
H13 0.4705(13) 0.1173(12) 0.4937(9) 0.055(9) Uani 1.000000 0
H7 1.0464(14) 0.8863(12) 0.0289(9) 0.066(10) Uani 1.000000 0
H12 0.5394(13) 0.2607(13) 0.4326(9) 0.059(9) Uani 1.000000 0
H14 0.7299(14) 0.3370(11) 0.3907(9) 0.087(10) Uani 1.000000 0
H1 0.4196(15) 0.7026(12) 0.3790(10) 0.048(10) Uani 1.000000 0
H8 0.9915(13) 0.7478(12) 0.1130(9) 0.060(10) Uani 1.000000 0
H16 0.9337(13) 0.4329(12) 0.2646(8) 0.084(10) Uani 1.000000 0
H2 1.1105(17) 0.3185(14) 0.1543(10) 0.047(11) Uani 1.000000 0
O2 1.63054(7) 0.89928(6) -0.14025(4) 0.0392(4) Uani 1.000000 0
O1 1.66222(8) 0.89304(7) -0.00775(5) 0.0515(5) Uani 1.000000 0
O3 1.36155(9) 0.56915(9) -0.16986(5) 0.0737(6) Uani 1.000000 0
O4 1.15662(8) 0.56631(8) -0.06412(5) 0.0556(5) Uani 1.000000 0
O5 1.20732(6) 0.39843(6) 0.09992(4) 0.0304(3) Uani 1.000000 0
O6 1.05594(6) 0.57141(5) 0.16652(4) 0.0334(4) Uani 1.000000 0
N8 1.60362(8) 0.86140(7) -0.05775(5) 0.0284(4) Uani 1.000000 0
N7 1.28269(9) 0.58560(8) -0.09274(6) 0.0366(5) Uani 1.000000 0
C5 1.49406(9) 0.77335(8) -0.01580(6) 0.0230(4) Uani 1.000000 0
C3 1.34183(9) 0.63564(8) -0.03161(6) 0.0227(4) Uani 1.000000 0
C4 1.44825(9) 0.71597(8) -0.07354(6) 0.0232(5) Uani 1.000000 0
C2 1.28465(9) 0.60879(8) 0.06401(6) 0.0227(4) Uani 1.000000 0
C1 1.17133(9) 0.51972(8) 0.11337(6) 0.0247(5) Uani 1.000000 0
C7 1.33485(10) 0.66941(9) 0.11909(7) 0.0305(5) Uani 1.000000 0
C6 1.43926(10) 0.75259(10) 0.07970(7) 0.0305(5) Uani 1.000000 0
C10 0.72771(10) 0.72070(9) 0.20374(7) 0.0288(5) Uani 1.000000 0
C13 0.49527(11) 0.88362(10) 0.30770(7) 0.0307(5) Uani 1.000000 0
C11 0.61595(10) 0.66926(10) 0.27419(7) 0.0293(5) Uani 1.000000 0
C8 0.84059(9) 0.92393(8) 0.11150(6) 0.0262(5) Uani 1.000000 0
C12 0.60416(10) 0.94070(10) 0.23855(6) 0.0280(5) Uani 1.000000 0
C9 0.72314(9) 0.85888(8) 0.18640(6) 0.0241(4) Uani 1.000000 0
O12 0.81347(6) 1.04320(6) 0.08249(4) 0.0329(4) Uani 1.000000 0
N3 0.97060(10) 0.84636(10) 0.08252(7) 0.0411(6) Uani 1.000000 0
N2 0.50490(9) 0.75040(8) 0.32430(5) 0.0278(4) Uani 1.000000 0
C17 0.79663(9) 0.14496(8) 0.34145(6) 0.0229(4) Uani 1.000000 0
C16 0.67555(9) 0.07924(8) 0.41107(6) 0.0241(5) Uani 1.000000 0
C18 0.90068(10) 0.07155(10) 0.27587(7) 0.0308(5) Uani 1.000000 0
C15 0.80727(11) 0.27675(10) 0.33983(7) 0.0394(6) Uani 1.000000 0
C14 0.91912(11) 0.33072(10) 0.27155(7) 0.0398(6) Uani 1.000000 0
C19 1.01065(11) 0.13215(10) 0.20977(7) 0.0349(6) Uani 1.000000 0
O8 0.47070(6) 0.43827(6) 0.40569(4) 0.0379(4) Uani 1.000000 0
O11 -0.16575(7) 0.16846(6) 0.69102(5) 0.0449(4) Uani 1.000000 0
O9 0.30446(6) 0.61995(5) 0.44312(4) 0.0311(3) Uani 1.000000 0
O10 -0.12469(7) 0.09549(6) 0.56130(5) 0.0477(4) Uani 1.000000 0
N5 0.28359(9) 0.31185(8) 0.33759(5) 0.0355(5) Uani 1.000000 0
N6 -0.10140(8) 0.16514(7) 0.60892(6) 0.0325(5) Uani 1.000000 0
O13 0.33614(10) 0.20243(8) 0.31445(5) 0.0699(6) Uani 1.000000 0
O14 0.29451(9) 0.41585(8) 0.28585(5) 0.0575(5) Uani 1.000000 0
O7 0.69189(6) -0.04395(6) 0.42534(4) 0.0351(4) Uani 1.000000 0
N1 1.01733(8) 0.25940(7) 0.20871(5) 0.0274(4) Uani 1.000000 0
N4 0.55569(10) 0.15925(10) 0.45282(6) 0.0347(5) Uani 1.000000 0
C21 0.22377(9) 0.41217(8) 0.48127(6) 0.0229(4) Uani 1.000000 0
C20 0.34433(9) 0.49676(8) 0.43892(6) 0.0241(5) Uani 1.000000 0
C24 0.01126(9) 0.25010(8) 0.56500(6) 0.0259(5) Uani 1.000000 0
C25 0.03084(11) 0.33853(10) 0.61510(7) 0.0318(5) Uani 1.000000 0
C22 0.19949(9) 0.32023(8) 0.43467(5) 0.0237(4) Uani 1.000000 0
C23 0.09516(10) 0.23773(9) 0.47447(7) 0.0264(5) Uani 1.000000 0
C26 0.13735(10) 0.41904(10) 0.57251(6) 0.0306(5) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H19 0.066459 0.087334 0.040098 -0.040633 -0.013053 -0.003332 0.007239 0.010239
0.007934 0.007025 0.006267 0.006949
H5 0.054901 0.045457 0.073095 -0.015011 0.015738 -0.003033 0.008143 0.007762
0.008569 0.006376 0.006634 0.006444
H10 0.072124 0.066835 0.071885 -0.028620 0.002299 -0.016921 0.008545 0.009266
0.009391 0.006984 0.007613 0.007671
H4 0.055953 0.050917 0.058791 -0.014841 0.004129 -0.010936 0.007671 0.007817
0.008435 0.006485 0.006410 0.006612
H18 0.080255 0.073913 0.062411 -0.038104 -0.023499 -0.000013 0.007788 0.009569
0.009349 0.006847 0.007467 0.007922
H20 0.040801 0.063884 0.044340 -0.020692 -0.005550 -0.004035 0.006343 0.008366
0.007594 0.005642 0.005944 0.006595
H3 0.063111 0.047162 0.079960 -0.013898 0.015605 -0.007670 0.008911 0.007818
0.009040 0.006636 0.007115 0.006762
H6 0.039539 0.036930 0.077544 -0.007498 0.008408 -0.003638 0.007075 0.006857
0.008533 0.005811 0.006173 0.006310
H17 0.081982 0.052875 0.116179 -0.032184 0.014942 -0.033442 0.009832 0.008841
0.011333 0.007509 0.008336 0.007880
H15 0.065082 0.037652 0.086443 -0.025041 0.012435 -0.016718 0.008254 0.007518
0.009257 0.006642 0.006917 0.006733
H11 0.043535 0.065687 0.049998 -0.016875 -0.002053 -0.007800 0.006952 0.008772
0.008078 0.006238 0.005975 0.006566
H9 0.071161 0.068904 0.048834 -0.034834 0.009657 -0.033602 0.007730 0.008865
0.007892 0.006819 0.006185 0.006588
H13 0.037631 0.051666 0.062707 -0.003865 -0.005409 0.007079 0.007715 0.008482
0.009693 0.006454 0.006951 0.007165
H7 0.048103 0.054160 0.067635 -0.007828 0.014162 0.003090 0.009201 0.008892
0.009246 0.007077 0.007514 0.007443
H12 0.046453 0.034050 0.076475 -0.011048 -0.000970 0.013942 0.008371 0.008521
0.010157 0.007369 0.007105 0.007786
H14 0.086200 0.052596 0.112136 -0.052601 0.027742 -0.035070 0.009874 0.009161
0.010958 0.007836 0.008190 0.008062
H1 0.042016 0.037005 0.061386 -0.003685 -0.011444 -0.005214 0.009100 0.008544
0.012577 0.007086 0.008981 0.008602
H8 0.047146 0.019819 0.081608 0.009299 0.005440 0.008853 0.009199 0.007132
0.010349 0.006826 0.007684 0.007064
H16 0.084516 0.071175 0.074517 -0.054374 0.052761 -0.037663 0.010092 0.009753
0.008510 0.008242 0.007139 0.007349
H2 0.056538 0.040394 0.035034 -0.003559 -0.000294 -0.009978 0.011040 0.009481
0.012521 0.008459 0.010456 0.009056
O2 0.038042 0.043688 0.034133 -0.024998 -0.002815 0.007245 0.000353 0.000431
0.000384 0.000314 0.000297 0.000316
O1 0.055078 0.067891 0.043587 -0.044740 -0.012031 -0.000003 0.000378 0.000562
0.000462 0.000386 0.000354 0.000395
O3 0.073492 0.118154 0.045702 -0.049970 0.000004 -0.039534 0.000511 0.000784
0.000547 0.000513 0.000440 0.000531
O4 0.050421 0.084704 0.046030 -0.041280 -0.021861 0.005293 0.000362 0.000625
0.000494 0.000385 0.000358 0.000434
O5 0.023609 0.022671 0.036229 -0.008331 0.005997 -0.002716 0.000318 0.000336
0.000366 0.000262 0.000280 0.000278
O6 0.021401 0.021953 0.044599 -0.005769 0.006352 0.000302 0.000310 0.000328
0.000379 0.000259 0.000281 0.000280
N8 0.025489 0.029715 0.030069 -0.015176 -0.003422 0.000505 0.000369 0.000432
0.000465 0.000321 0.000337 0.000349
N7 0.038595 0.046824 0.030919 -0.022637 -0.009179 -0.004144 0.000427 0.000525
0.000513 0.000384 0.000393 0.000408
C5 0.020307 0.023703 0.023336 -0.008126 -0.002496 -0.000622 0.000387 0.000445
0.000475 0.000339 0.000352 0.000362
C3 0.020012 0.023058 0.023559 -0.008126 -0.002178 -0.001107 0.000385 0.000441
0.000477 0.000336 0.000353 0.000365
C4 0.021666 0.025048 0.020480 -0.009134 -0.000404 -0.000803 0.000418 0.000458
0.000488 0.000348 0.000384 0.000395
C2 0.018540 0.022212 0.024180 -0.008351 -0.000985 0.001457 0.000386 0.000431
0.000470 0.000331 0.000350 0.000357
C1 0.017112 0.019543 0.030004 -0.005777 0.002471 0.001398 0.000402 0.000457
0.000477 0.000350 0.000360 0.000378
C7 0.032231 0.037500 0.021170 -0.017999 -0.001221 0.000712 0.000479 0.000564
0.000514 0.000415 0.000423 0.000450
C6 0.033795 0.038082 0.022238 -0.019834 -0.003803 -0.001636 0.000480 0.000575
0.000541 0.000426 0.000412 0.000431
C10 0.022263 0.021500 0.034646 -0.007200 0.002102 0.001888 0.000445 0.000504
0.000544 0.000387 0.000396 0.000424
C13 0.023214 0.027190 0.034420 -0.008662 0.003038 -0.001077 0.000464 0.000543
0.000559 0.000407 0.000413 0.000442
C11 0.023967 0.022437 0.034701 -0.009842 0.000683 0.003317 0.000445 0.000525
0.000547 0.000410 0.000396 0.000443
C8 0.019318 0.021258 0.030980 -0.006037 -0.001707 0.006522 0.000405 0.000481
0.000490 0.000360 0.000364 0.000391
C12 0.022236 0.021593 0.034064 -0.006941 -0.000545 0.001457 0.000429 0.000500
0.000537 0.000391 0.000388 0.000432
C9 0.018492 0.021857 0.027404 -0.007429 -0.001578 0.003876 0.000382 0.000466
0.000474 0.000342 0.000353 0.000376
O12 0.025227 0.022734 0.039521 -0.006545 0.000707 0.008431 0.000319 0.000340
0.000372 0.000266 0.000283 0.000284
N3 0.024834 0.028131 0.049584 -0.003514 0.007402 0.012031 0.000479 0.000514
0.000571 0.000408 0.000413 0.000445
N2 0.021718 0.028502 0.029250 -0.011063 -0.000800 0.002436 0.000371 0.000458
0.000457 0.000331 0.000336 0.000384
C17 0.020616 0.019736 0.024986 -0.009197 -0.000440 0.001001 0.000386 0.000450
0.000464 0.000339 0.000349 0.000368
C16 0.020325 0.017778 0.028966 -0.007141 -0.001162 0.003604 0.000398 0.000459
0.000473 0.000345 0.000356 0.000376
C18 0.024565 0.022741 0.039790 -0.010792 0.004046 -0.005919 0.000452 0.000507
0.000560 0.000398 0.000404 0.000441
C15 0.039484 0.024851 0.041082 -0.017822 0.017612 -0.009461 0.000578 0.000559
0.000575 0.000471 0.000464 0.000456
C14 0.039407 0.024598 0.042679 -0.018536 0.017677 -0.008987 0.000578 0.000565
0.000575 0.000471 0.000456 0.000470
C19 0.026893 0.028398 0.041073 -0.012065 0.010141 -0.010022 0.000494 0.000559
0.000596 0.000430 0.000437 0.000461
O8 0.023883 0.021007 0.054041 -0.005197 0.006484 0.001811 0.000337 0.000333
0.000407 0.000272 0.000302 0.000290
O11 0.035667 0.044811 0.044159 -0.020801 0.003774 0.008234 0.000375 0.000442
0.000414 0.000325 0.000317 0.000339
O9 0.022764 0.020095 0.042223 -0.006936 0.002826 -0.001369 0.000307 0.000330
0.000376 0.000257 0.000280 0.000275
O10 0.036304 0.034054 0.068538 -0.019166 0.002893 -0.011698 0.000371 0.000404
0.000512 0.000327 0.000357 0.000362
N5 0.043747 0.036881 0.021658 -0.013844 0.002023 -0.005428 0.000450 0.000507
0.000451 0.000387 0.000369 0.000403
N6 0.023863 0.024018 0.042978 -0.010409 0.000795 0.001208 0.000386 0.000417
0.000517 0.000331 0.000357 0.000364
O13 0.097428 0.053622 0.041886 -0.020706 0.019808 -0.025254 0.000666 0.000519
0.000485 0.000477 0.000455 0.000410
O14 0.078087 0.058846 0.024885 -0.022113 0.000205 0.006185 0.000539 0.000531
0.000406 0.000429 0.000381 0.000379
O7 0.025430 0.020091 0.047633 -0.007269 0.002998 0.005642 0.000325 0.000336
0.000393 0.000267 0.000291 0.000287
N1 0.023973 0.025343 0.027698 -0.010233 0.002612 -0.001287 0.000377 0.000429
0.000436 0.000322 0.000332 0.000359
N4 0.026017 0.022149 0.042787 -0.007982 0.006072 0.004196 0.000463 0.000477
0.000538 0.000399 0.000386 0.000414
C21 0.022218 0.021196 0.022044 -0.008966 0.000906 -0.001085 0.000402 0.000430
0.000459 0.000341 0.000353 0.000355
C20 0.019972 0.017755 0.028759 -0.005665 0.000646 0.000758 0.000408 0.000454
0.000473 0.000357 0.000361 0.000368
C24 0.021347 0.020441 0.030643 -0.006751 0.000075 0.000049 0.000413 0.000438
0.000494 0.000347 0.000368 0.000372
C25 0.030466 0.034045 0.025287 -0.014880 0.007260 -0.005524 0.000491 0.000550
0.000524 0.000417 0.000429 0.000449
C22 0.024119 0.022432 0.021737 -0.007272 -0.001460 -0.001191 0.000413 0.000438
0.000459 0.000349 0.000359 0.000360
C23 0.026366 0.022707 0.028864 -0.009010 -0.002774 -0.003844 0.000450 0.000489
0.000547 0.000375 0.000400 0.000408
C26 0.032961 0.031992 0.025052 -0.016675 0.004395 -0.007867 0.000484 0.000547
0.000522 0.000420 0.000406 0.000425

# ====
# ADPs
# ====


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 . N8 . 1.2111(9) yes
O1 . N8 . 1.2127(9) yes
O3 . N7 . 1.2090(10) yes
O4 . N7 . 1.2087(10) yes
O11 . N6 . 1.2195(10) yes
O10 . N6 . 1.2171(10) yes
O13 . N5 . 1.2048(10) yes
O14 . N5 . 1.2099(10) yes
O5 . C1 . 1.2641(9) yes
O6 . C1 . 1.2371(9) yes
O12 . C8 . 1.2270(9) yes
O8 . C20 . 1.2346(9) yes
O9 . C20 . 1.2545(9) yes
O7 . C16 . 1.2328(9) yes
N8 . C5 . 1.4626(10) yes
N7 . C3 . 1.4600(11) yes
N3 . C8 . 1.3295(11) yes
N2 . C13 . 1.3389(12) yes
N2 . C11 . 1.3348(12) yes
N5 . C22 . 1.4632(11) yes
N6 . C24 . 1.4655(11) yes
N1 . C14 . 1.3284(12) yes
N1 . C19 . 1.3279(12) yes
N4 . C16 . 1.3249(11) yes
N3 . H7 . 1.004(12) yes
N3 . H8 . 1.041(12) yes
N2 . H1 . 1.102(15) yes
N1 . H2 . 1.207(17) yes
N4 . H13 . 0.995(13) yes
N4 . H12 . 1.026(13) yes
C5 . C4 . 1.3783(12) yes
C5 . C6 . 1.3822(12) yes
C3 . C4 . 1.3856(11) yes
C3 . C2 . 1.3900(11) yes
C2 . C1 . 1.5097(11) yes
C2 . C7 . 1.3931(13) yes
C7 . C6 . 1.3879(13) yes
C10 . C11 . 1.3846(12) yes
C10 . C9 . 1.3948(12) yes
C13 . C12 . 1.3833(12) yes
C8 . C9 . 1.5105(11) yes
C12 . C9 . 1.3908(12) yes
C17 . C16 . 1.5033(11) yes
C17 . C18 . 1.3863(12) yes
C17 . C15 . 1.3836(12) yes
C18 . C19 . 1.3869(12) yes
C15 . C14 . 1.3813(13) yes
C21 . C20 . 1.5181(11) yes
C21 . C22 . 1.3914(11) yes
C21 . C26 . 1.3918(12) yes
C24 . C25 . 1.3790(13) yes
C24 . C23 . 1.3839(12) yes
C25 . C26 . 1.3887(13) yes
C22 . C23 . 1.3830(12) yes
C4 . H20 . 1.086(10) yes
C7 . H18 . 1.081(12) yes
C6 . H19 . 1.080(11) yes
C10 . H5 . 1.080(11) yes
C13 . H3 . 1.080(11) yes
C11 . H4 . 1.077(11) yes
C12 . H6 . 1.072(10) yes
C18 . H15 . 1.094(10) yes
C15 . H14 . 1.083(12) yes
C14 . H16 . 1.076(11) yes
C19 . H17 . 1.063(12) yes
C25 . H10 . 1.048(11) yes
C23 . H11 . 1.072(11) yes
C26 . H9 . 1.077(10) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . N8 . O1 . 123.52(8) yes
O3 . N7 . O4 . 123.87(9) yes
O11 . N6 . O10 . 124.08(8) yes
O13 . N5 . O14 . 124.50(8) yes
O2 . N8 . C5 . 118.43(7) yes
O1 . N8 . C5 . 118.05(7) yes
O3 . N7 . C3 . 118.01(8) yes
O4 . N7 . C3 . 118.09(8) yes
O11 . N6 . C24 . 117.90(8) yes
O10 . N6 . C24 . 118.02(8) yes
O13 . N5 . C22 . 118.07(8) yes
O14 . N5 . C22 . 117.43(8) yes
O5 . C1 . O6 . 126.69(8) yes
O8 . C20 . O9 . 126.74(8) yes
O12 . C8 . N3 . 123.90(8) yes
O7 . C16 . N4 . 123.98(8) yes
O5 . C1 . C2 . 116.65(7) yes
O6 . C1 . C2 . 116.55(7) yes
O12 . C8 . C9 . 119.59(7) yes
O8 . C20 . C21 . 117.49(7) yes
O9 . C20 . C21 . 115.76(7) yes
O7 . C16 . C17 . 119.03(7) yes
N8 . C5 . C4 . 118.39(7) yes
N8 . C5 . C6 . 118.86(8) yes
N7 . C3 . C4 . 116.92(7) yes
N7 . C3 . C2 . 119.91(7) yes
N3 . C8 . C9 . 116.49(8) yes
N2 . C13 . C12 . 120.05(9) yes
N2 . C11 . C10 . 120.67(9) yes
N5 . C22 . C21 . 119.41(7) yes
N5 . C22 . C23 . 117.24(8) yes
N6 . C24 . C25 . 119.18(8) yes
N6 . C24 . C23 . 118.49(8) yes
N1 . C14 . C15 . 121.99(9) yes
N1 . C19 . C18 . 120.76(9) yes
N4 . C16 . C17 . 116.98(8) yes
N2 . C13 . H3 . 116.9(6) yes
N2 . C11 . H4 . 115.2(6) yes
N1 . C14 . H16 . 114.8(6) yes
N1 . C19 . H17 . 116.4(6) yes
C13 . N2 . C11 . 121.84(9) yes
C14 . N1 . C19 . 120.45(9) yes
C13 . N2 . H1 . 121.4(6) yes
C11 . N2 . H1 . 116.7(6) yes
C8 . N3 . H7 . 117.1(7) yes
C8 . N3 . H8 . 121.3(6) yes
C16 . N4 . H13 . 117.7(7) yes
C16 . N4 . H12 . 121.8(7) yes
C14 . N1 . H2 . 114.9(6) yes
C19 . N1 . H2 . 124.6(6) yes
C5 . C4 . C3 . 116.90(8) yes
C5 . C6 . C7 . 118.60(9) yes
C3 . C2 . C1 . 125.29(8) yes
C3 . C2 . C7 . 117.62(8) yes
C4 . C5 . C6 . 122.74(8) yes
C4 . C3 . C2 . 123.05(8) yes
C2 . C7 . C6 . 121.06(9) yes
C1 . C2 . C7 . 117.09(7) yes
C10 . C9 . C8 . 122.64(8) yes
C10 . C9 . C12 . 118.90(8) yes
C13 . C12 . C9 . 119.58(9) yes
C11 . C10 . C9 . 118.91(9) yes
C8 . C9 . C12 . 118.44(7) yes
C17 . C18 . C19 . 119.49(9) yes
C17 . C15 . C14 . 118.62(9) yes
C16 . C17 . C18 . 118.97(8) yes
C16 . C17 . C15 . 122.35(8) yes
C18 . C17 . C15 . 118.69(8) yes
C21 . C22 . C23 . 123.32(8) yes
C21 . C26 . C25 . 121.61(9) yes
C20 . C21 . C22 . 122.95(7) yes
C20 . C21 . C26 . 119.92(8) yes
C24 . C25 . C26 . 118.62(9) yes
C24 . C23 . C22 . 117.10(9) yes
C25 . C24 . C23 . 122.33(8) yes
C22 . C21 . C26 . 117.02(8) yes
C5 . C4 . H20 . 122.0(6) yes
C5 . C6 . H19 . 121.1(6) yes
C3 . C4 . H20 . 121.1(6) yes
C2 . C7 . H18 . 119.2(6) yes
C7 . C6 . H19 . 120.3(6) yes
C6 . C7 . H18 . 119.8(6) yes
C10 . C11 . H4 . 124.1(6) yes
C13 . C12 . H6 . 120.1(5) yes
C11 . C10 . H5 . 119.3(6) yes
C12 . C13 . H3 . 123.0(6) yes
C9 . C10 . H5 . 121.8(6) yes
C9 . C12 . H6 . 120.4(5) yes
C17 . C18 . H15 . 119.5(6) yes
C17 . C15 . H14 . 121.1(6) yes
C18 . C19 . H17 . 122.8(6) yes
C15 . C14 . H16 . 123.3(6) yes
C14 . C15 . H14 . 120.3(6) yes
C19 . C18 . H15 . 121.0(6) yes
C21 . C26 . H9 . 117.7(5) yes
C24 . C25 . H10 . 121.1(6) yes
C24 . C23 . H11 . 122.8(6) yes
C25 . C26 . H9 . 120.6(5) yes
C22 . C23 . H11 . 120.1(6) yes
C26 . C25 . H10 . 120.3(6) yes
H13 . N4 . H12 . 118.8(9) yes
H7 . N3 . H8 . 121.6(9) yes
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate 2:2'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_8_300K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922019'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_8_300K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      50.03 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide 3,5-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 N2 O6, C6 H7 N2 O1'
_chemical_formula_sum            'C13 H10 N4 O7'
_chemical_formula_weight         334.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0057 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.44850(5)
_cell_length_b                   9.01200(5)
_cell_length_c                   10.83100(6)
_cell_angle_alpha                88.0350(5)
_cell_angle_beta                 76.7370(5)
_cell_angle_gamma                87.5550(5)
_cell_volume                     706.780(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    10334
_cell_measurement_theta_max      35.1315985013
_cell_measurement_theta_min      1.86558985161

_exptl_crystal_description       'triangular block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6755
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24234
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.873
_diffrn_reflns_theta_max         36.113
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6827
_reflns_number_gt                4605
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'General Data Aquisition Software, Diamond Light Source'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.12.4-ga5a83653b-release+d6bf05'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.12.4-ga5a83653b-release+d6bf05 (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.769-ga0b6e151-dials-1.12 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0862P)²+0.0371P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6827
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1686
_refine_ls_wR_factor_gt          0.1491
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O7 O 0.51645(14) 0.20277(9) -0.00435(8) 0.0512(2) Uani 1 1 d . . . . .
N2 N 0.60312(14) 0.04127(9) 0.13676(9) 0.0415(2) Uani 1 1 d . . . . .
N1 N 0.70336(14) 0.54785(9) 0.28358(9) 0.0433(2) Uani 1 1 d . . . . .
C13 C 0.57835(13) 0.17720(10) 0.09080(9) 0.03577(19) Uani 1 1 d . . . . .
C11 C 0.66781(18) 0.43941(11) 0.09606(10) 0.0443(2) Uani 1 1 d . . . . .
C10 C 0.62618(13) 0.30582(10) 0.16136(9) 0.03436(18) Uani 1 1 d . . . . .
C8 C 0.66439(18) 0.42061(11) 0.34821(10) 0.0452(2) Uani 1 1 d . . . . .
C12 C 0.7073(2) 0.55924(11) 0.16017(11) 0.0488(3) Uani 1 1 d . . . . .
C9 C 0.62565(17) 0.29609(11) 0.28951(9) 0.0421(2) Uani 1 1 d . . . . .
O5 O 0.87948(17) 1.33774(10) 0.79912(10) 0.0669(3) Uani 1 1 d . . . . .
O2 O 0.69877(16) 0.95762(10) 0.37359(8) 0.0591(2) Uani 1 1 d . . . . .
O4 O 0.95296(16) 0.83843(11) 0.95957(9) 0.0594(2) Uani 1 1 d . . . . .
O3 O 0.90537(17) 0.65357(10) 0.85282(10) 0.0635(3) Uani 1 1 d . . . . .
O1 O 0.7555(2) 0.72996(10) 0.44378(9) 0.0746(4) Uani 1 1 d . . . . .
O6 O 0.7358(2) 1.37407(10) 0.64886(12) 0.0813(4) Uani 1 1 d . . . . .
N3 N 0.91215(13) 0.78623(10) 0.86756(9) 0.04131(19) Uani 1 1 d . . . . .
N4 N 0.80943(16) 1.29345(10) 0.71700(10) 0.0488(2) Uani 1 1 d . . . . .
C4 C 0.86806(13) 0.88909(10) 0.76976(9) 0.03398(18) Uani 1 1 d . . . . .
C3 C 0.82697(14) 0.83090(10) 0.66285(9) 0.03569(18) Uani 1 1 d . . . . .
C5 C 0.86620(14) 1.04015(10) 0.78988(9) 0.03661(19) Uani 1 1 d . . . . .
C6 C 0.81435(14) 1.13237(10) 0.69887(9) 0.03695(19) Uani 1 1 d . . . . .
C7 C 0.76855(15) 1.08035(10) 0.59162(9) 0.03798(19) Uani 1 1 d . . . . .
C2 C 0.77808(13) 0.92777(10) 0.57236(8) 0.03525(18) Uani 1 1 d . . . . .
C1 C 0.73821(16) 0.86904(11) 0.45231(9) 0.0411(2) Uani 1 1 d . . . . .
H10 H 0.732(2) 1.1444(18) 0.5299(15) 0.056(4) Uiso 1 1 d . . . . .
H9 H 0.8977(18) 1.0820(15) 0.8641(13) 0.045(3) Uiso 1 1 d . . . . .
H8 H 0.8339(19) 0.7254(16) 0.6519(13) 0.048(4) Uiso 1 1 d . . . . .
H3 H 0.597(2) 0.2048(18) 0.3435(15) 0.054(4) Uiso 1 1 d . . . . .
H4 H 0.742(2) 0.6597(19) 0.1148(16) 0.067(5) Uiso 1 1 d . . . . .
H6 H 0.648(2) 0.0237(17) 0.2087(15) 0.053(4) Uiso 1 1 d . . . . .
H5 H 0.678(2) 0.4530(19) 0.0113(18) 0.066(4) Uiso 1 1 d . . . . .
H2 H 0.660(2) 0.423(2) 0.4365(18) 0.072(5) Uiso 1 1 d . . . . .
H7 H 0.572(2) -0.0404(18) 0.0935(15) 0.060(4) Uiso 1 1 d . . . . .
H1 H 0.724(3) 0.638(2) 0.340(2) 0.088(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 C13 1.2330(12) . ?
N2 C13 1.3280(13) . ?
N2 H6 0.922(16) . ?
N2 H7 0.951(17) . ?
N1 C8 1.3302(14) . ?
N1 C12 1.3306(14) . ?
N1 H1 1.07(2) . ?
C13 C10 1.5085(11) . ?
C11 C12 1.3812(13) . ?
C11 C10 1.3851(14) . ?
C11 H5 0.908(18) . ?
C10 C9 1.3869(13) . ?
C8 C9 1.3812(13) . ?
C8 H2 0.951(19) . ?
C12 H4 1.029(17) . ?
C9 H3 0.995(16) . ?
O5 N4 1.2155(13) . ?
O2 C1 1.2242(14) . ?
O4 N3 1.2208(12) . ?
O3 N3 1.2163(12) . ?
O1 C1 1.2588(13) . ?
O6 N4 1.2201(15) . ?
N3 C4 1.4681(13) . ?
N4 C6 1.4693(12) . ?
C4 C5 1.3851(12) . ?
C4 C3 1.3883(12) . ?
C3 C2 1.3905(14) . ?
C3 H8 0.960(14) . ?
C5 C6 1.3794(14) . ?
C5 H9 0.979(14) . ?
C6 C7 1.3850(13) . ?
C7 C2 1.3942(12) . ?
C7 H10 0.947(16) . ?
C2 C1 1.5155(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N2 H6 122.7(9) . . ?
C13 N2 H7 118.0(9) . . ?
H6 N2 H7 119.4(13) . . ?
C8 N1 C12 121.17(8) . . ?
C8 N1 H1 114.3(11) . . ?
C12 N1 H1 124.5(11) . . ?
O7 C13 N2 123.49(8) . . ?
O7 C13 C10 119.08(9) . . ?
N2 C13 C10 117.42(8) . . ?
C12 C11 C10 119.22(9) . . ?
C12 C11 H5 116.4(11) . . ?
C10 C11 H5 124.3(11) . . ?
C11 C10 C9 118.99(8) . . ?
C11 C10 C13 118.57(8) . . ?
C9 C10 C13 122.42(9) . . ?
N1 C8 C9 121.05(9) . . ?
N1 C8 H2 115.6(11) . . ?
C9 C8 H2 123.3(11) . . ?
N1 C12 C11 120.71(10) . . ?
N1 C12 H4 117.6(10) . . ?
C11 C12 H4 121.7(10) . . ?
C8 C9 C10 118.86(9) . . ?
C8 C9 H3 116.9(9) . . ?
C10 C9 H3 124.2(9) . . ?
O3 N3 O4 123.50(10) . . ?
O3 N3 C4 118.25(8) . . ?
O4 N3 C4 118.25(9) . . ?
O5 N4 O6 124.22(10) . . ?
O5 N4 C6 117.68(10) . . ?
O6 N4 C6 118.10(9) . . ?
C5 C4 C3 123.06(9) . . ?
C5 C4 N3 118.19(8) . . ?
C3 C4 N3 118.74(8) . . ?
C4 C3 C2 118.93(8) . . ?
C4 C3 H8 119.9(8) . . ?
C2 C3 H8 121.1(8) . . ?
C6 C5 C4 116.19(8) . . ?
C6 C5 H9 120.3(8) . . ?
C4 C5 H9 123.5(8) . . ?
C5 C6 C7 123.18(8) . . ?
C5 C6 N4 117.93(8) . . ?
C7 C6 N4 118.89(9) . . ?
C6 C7 C2 119.02(9) . . ?
C6 C7 H10 122.7(10) . . ?
C2 C7 H10 118.3(10) . . ?
C3 C2 C7 119.56(8) . . ?
C3 C2 C1 120.58(8) . . ?
C7 C2 C1 119.86(9) . . ?
O2 C1 O1 126.85(9) . . ?
O2 C1 C2 118.86(9) . . ?
O1 C1 C2 114.25(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H9 O4 0.979(14) 2.556(14) 3.5189(12) 167.6(11) 2_777 yes
C9 H3 O2 0.995(16) 2.359(16) 3.2133(14) 143.4(12) 1_545 yes
C12 H4 O4 1.029(17) 2.591(17) 3.5486(16) 154.7(13) 1_554 yes
N2 H6 O2 0.922(16) 1.977(16) 2.8837(13) 167.7(13) 1_545 yes
C11 H5 O5 0.908(18) 2.657(18) 3.3795(15) 137.2(14) 1_544 yes
C8 H2 O6 0.951(19) 2.511(19) 3.4269(15) 161.8(15) 1_545 yes
N2 H7 O7 0.951(17) 1.994(17) 2.9422(11) 174.9(14) 2_655 yes
N1 H1 O1 1.07(2) 1.49(2) 2.5326(11) 164.4(19) . yes

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex7_350K_har
_database_code_depnum_ccdc_archive 'CCDC 1922033'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex7_350K_har   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.53 %
RESPONSE: Related to the use of a non-standard diffraction wavelength.
;
_vrf_PLAT353_complex7_350K_har   
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.26 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT230_complex7_350K_har   
;
PROBLEM: Hirshfeld Test Diff for    O4       --N7       .        7.5 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_350K_har_2 
;
PROBLEM: Hirshfeld Test Diff for    O8       --C20      .        7.8 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_350K_har_3 
;
PROBLEM: Hirshfeld Test Diff for    O13      --N5       .        9.0 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT250_complex7_350K_har   
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.3 Note
RESPONSE: Related to the use of HAR method.
;
_vrf_PLAT353_complex7_350K_har_2 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H1       .       1.12 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT430_complex7_350K_har   
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.86 Ang.
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi
;
_vrf_PLAT919_complex7_350K_har   
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: Reflections used in the refinement are taken from the fcf from a SHELXL refinement using the LIST 4FVAR^2 command. HAR applies its own rejection criteria during the initial stages of refinement. Reflection was not rejected.
;
_vrf_PLAT230_complex7_350K_har_4 
;
PROBLEM: Hirshfeld Test Diff for    O1       --N8       .        5.1 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_350K_har_5 
;
PROBLEM: Hirshfeld Test Diff for    O10      --N6       .        5.2 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_350K_har_6 
;
PROBLEM: Hirshfeld Test Diff for    O11      --N6       .        6.2 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_350K_har_7 
;
PROBLEM: Hirshfeld Test Diff for    O14      --N5       .        7.0 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT250_complex7_350K_har_2 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.5 Note
RESPONSE: Related to the use of HAR method.
;
_vrf_PLAT250_complex7_350K_har_3 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.6 Note
RESPONSE: Related to the use of HAR method.
;
_vrf_PLAT250_complex7_350K_har_4 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.8 Note
RESPONSE: Related to the use of HAR method.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-5
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            350K
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_weight         668.4945
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       344
_QCr_calc_unit_n_alpha_electrons 172
_QCr_calc_unit_n_beta_electrons  172

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             688

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'p -1'
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'

# =========
# Unit cell
# =========

_cell_measurement_temperature    350
_cell_measurement_reflns_used    6180
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      34.96

_cell_length_a                   9.8448(6)
_cell_length_b                   10.3745(6)
_cell_length_c                   15.5573(9)
_cell_angle_alpha                79.023(4)
_cell_angle_beta                 70.556(3)
_cell_angle_gamma                77.704(4)
_cell_volume                     1451.58(15)

_cell_formula_units_Z            2.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========
_diffrn_ambient_temperature      350
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6895
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         35.631
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            212.096502

_reflns_d_resolution_high        10.050856
_reflns_d_resolution_low         0.760219
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                3849
_reflns_number_total             3849
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0498
_refine_ls_R_factor_all          0.0498
_refine_ls_wR_factor_gt          0.0279
_refine_ls_wR_factor_all         0.0279
_refine_ls_R_Fsqd_factor         0.0390
_refine_ls_goodness_of_fit_gt    1.9836
_refine_ls_goodness_of_fit_all   1.9836
_refine_ls_number_reflns         3849
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0054
_refine_ls_shift/su_max_mean     0.0004
_refine_ls_shift/su_max_par      'H2 px'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.2194
_refine_diff_density_min         -0.2659
_refine_diff_density_rms         0.0434
_refine_diff_density_max_atom    0.1073
_refine_diff_density_max_atom_tag O11
_refine_diff_density_min_atom    -0.0688
_refine_diff_density_min_atom_tag H17
_refine_diff_density_rms_atom    0.0397

_refine_special_details          
;

  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.
   
. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 350K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  350K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

350k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H19 1.478646 0.794028 0.120317 0.108857 Uani 1.000000 0 0.002554 0.002479
0.001510 0.021102
H5 0.824969 0.648946 0.163846 0.127301 Uani 1.000000 0 0.002466 0.001914
0.001789 0.021499
H10 -0.033797 0.346129 0.681459 0.126725 Uani 1.000000 0 0.002674 0.002301
0.001457 0.021188
H4 0.615242 0.564936 0.289604 0.096522 Uani 1.000000 0 0.002242 0.001984
0.001451 0.017575
H18 1.301457 0.644654 0.189921 0.120301 Uani 1.000000 0 0.002841 0.002294
0.001477 0.020058
H20 1.487302 0.735569 -0.146018 0.086808 Uani 1.000000 0 0.002169 0.002088
0.001404 0.016388
H3 0.401977 0.934900 0.345265 0.118821 Uani 1.000000 0 0.002552 0.002114
0.001606 0.021273
H6 0.598254 1.044750 0.223519 0.101529 Uani 1.000000 0 0.002141 0.002027
0.001488 0.017742
H17 1.095184 0.087396 0.158864 0.185510 Uani 1.000000 0 0.002728 0.002305
0.002204 0.028696
H15 0.892763 -0.023946 0.281455 0.125603 Uani 1.000000 0 0.002522 0.002344
0.001822 0.021018
H11 0.082793 0.166860 0.436967 0.094203 Uani 1.000000 0 0.002474 0.002307
0.001415 0.019477
H9 0.155096 0.490425 0.604647 0.119833 Uani 1.000000 0 0.002626 0.002235
0.001510 0.020780
H13 0.477097 0.116456 0.492082 0.078944 Uani 1.000000 0 0.002505 0.002227
0.001746 0.019515
H7 1.044622 0.887325 0.029950 0.118979 Uani 1.000000 0 0.002882 0.002441
0.001869 0.024357
H12 0.546007 0.257489 0.433075 0.100248 Uani 1.000000 0 0.002941 0.002444
0.001985 0.022559
H14 0.721636 0.337583 0.390704 0.190861 Uani 1.000000 0 0.002593 0.002236
0.001975 0.027651
H1 0.419253 0.695124 0.374365 0.091979 Uani 1.000000 0 0.002945 0.002475
0.001728 0.023544
H8 0.982501 0.752320 0.100564 0.141609 Uani 1.000000 0 0.002887 0.002170
0.002250 0.026065
H16 0.936503 0.426959 0.266151 0.180259 Uani 1.000000 0 0.003095 0.002860
0.002130 0.028881
H2 1.112398 0.324901 0.153861 0.088567 Uani 1.000000 0 0.003299 0.002729
0.001917 0.026297
O2 1.631053 0.897311 -0.138657 0.083335 Uani 1.000000 0 0.000148 0.000137
0.000109 0.001140
O1 1.662956 0.888699 -0.010608 0.103641 Uani 1.000000 0 0.000180 0.000165
0.000114 0.001339
O3 1.355172 0.573784 -0.164267 0.152924 Uani 1.000000 0 0.000218 0.000222
0.000135 0.001862
O4 1.157718 0.571076 -0.060287 0.114552 Uani 1.000000 0 0.000201 0.000178
0.000113 0.001405
O5 1.206190 0.402071 0.101713 0.065833 Uani 1.000000 0 0.000138 0.000141
0.000093 0.000997
O6 1.057203 0.572632 0.167231 0.074788 Uani 1.000000 0 0.000135 0.000115
0.000093 0.000985
N8 1.604259 0.858920 -0.058257 0.059924 Uani 1.000000 0 0.000183 0.000162
0.000147 0.001286
N7 1.280799 0.589034 -0.088654 0.078002 Uani 1.000000 0 0.000235 0.000189
0.000143 0.001485
C5 1.494372 0.772012 -0.015877 0.047879 Uani 1.000000 0 0.000186 0.000171
0.000142 0.001268
C3 1.340409 0.637808 -0.029465 0.047149 Uani 1.000000 0 0.000189 0.000166
0.000130 0.001241
C4 1.446711 0.717737 -0.071993 0.048936 Uani 1.000000 0 0.000222 0.000200
0.000157 0.001381
C2 1.284181 0.610149 0.064848 0.047436 Uani 1.000000 0 0.000181 0.000169
0.000135 0.001258
C1 1.170964 0.522375 0.114577 0.054339 Uani 1.000000 0 0.000205 0.000209
0.000133 0.001360
C7 1.336547 0.667873 0.118056 0.065172 Uani 1.000000 0 0.000253 0.000238
0.000168 0.001637
C6 1.441464 0.749935 0.078339 0.065619 Uani 1.000000 0 0.000276 0.000253
0.000168 0.001832
C10 0.729868 0.719527 0.203050 0.063224 Uani 1.000000 0 0.000233 0.000223
0.000151 0.001596
C13 0.495779 0.878196 0.303745 0.064930 Uani 1.000000 0 0.000255 0.000254
0.000165 0.001733
C11 0.617931 0.667605 0.272686 0.064648 Uani 1.000000 0 0.000259 0.000245
0.000172 0.001623
C8 0.840740 0.921648 0.111165 0.056400 Uani 1.000000 0 0.000221 0.000212
0.000129 0.001389
C12 0.604129 0.936101 0.235846 0.060161 Uani 1.000000 0 0.000238 0.000224
0.000156 0.001476
C9 0.723855 0.856145 0.185536 0.050978 Uani 1.000000 0 0.000190 0.000189
0.000121 0.001258
O12 0.815614 1.039310 0.083355 0.072410 Uani 1.000000 0 0.000130 0.000129
0.000088 0.000987
N3 0.968083 0.847174 0.081269 0.091580 Uani 1.000000 0 0.000270 0.000249
0.000185 0.001865
N2 0.505172 0.746619 0.321132 0.058029 Uani 1.000000 0 0.000201 0.000190
0.000128 0.001306
C17 0.793690 0.147677 0.341196 0.047741 Uani 1.000000 0 0.000189 0.000181
0.000121 0.001215
C16 0.673974 0.081644 0.410195 0.051897 Uani 1.000000 0 0.000208 0.000205
0.000127 0.001316
C18 0.897951 0.077282 0.276334 0.072150 Uani 1.000000 0 0.000281 0.000239
0.000192 0.001705
C15 0.804365 0.277879 0.339589 0.084135 Uani 1.000000 0 0.000269 0.000234
0.000166 0.001832
C14 0.916176 0.331880 0.272153 0.087993 Uani 1.000000 0 0.000327 0.000262
0.000207 0.001958
C19 1.007855 0.137599 0.211359 0.074461 Uani 1.000000 0 0.000261 0.000264
0.000168 0.001787
O8 0.468798 0.438294 0.406675 0.084286 Uani 1.000000 0 0.000147 0.000121
0.000099 0.001064
O11 -0.161382 0.168628 0.690956 0.098628 Uani 1.000000 0 0.000166 0.000150
0.000119 0.001264
O9 0.304778 0.617133 0.437393 0.070265 Uani 1.000000 0 0.000130 0.000129
0.000092 0.000972
O10 -0.122490 0.097101 0.564125 0.104353 Uani 1.000000 0 0.000173 0.000156
0.000133 0.001389
N5 0.284468 0.308118 0.338946 0.078648 Uani 1.000000 0 0.000212 0.000228
0.000127 0.001506
N6 -0.098472 0.165001 0.609962 0.071807 Uani 1.000000 0 0.000194 0.000181
0.000159 0.001463
O13 0.334509 0.200021 0.316697 0.143187 Uani 1.000000 0 0.000235 0.000208
0.000118 0.001773
O14 0.301168 0.407776 0.287548 0.126470 Uani 1.000000 0 0.000210 0.000194
0.000108 0.001581
O7 0.688824 -0.039884 0.423455 0.076086 Uani 1.000000 0 0.000131 0.000127
0.000092 0.001009
N1 1.015012 0.263114 0.210363 0.059370 Uani 1.000000 0 0.000195 0.000184
0.000126 0.001271
N4 0.556027 0.159584 0.453043 0.073838 Uani 1.000000 0 0.000272 0.000237
0.000172 0.001725
C21 0.224916 0.409993 0.479747 0.049001 Uani 1.000000 0 0.000188 0.000170
0.000129 0.001243
C20 0.344219 0.494929 0.437026 0.054251 Uani 1.000000 0 0.000217 0.000202
0.000127 0.001358
C24 0.014019 0.250076 0.565309 0.055509 Uani 1.000000 0 0.000197 0.000184
0.000150 0.001385
C25 0.033421 0.338440 0.613849 0.067632 Uani 1.000000 0 0.000249 0.000236
0.000172 0.001650
C22 0.201122 0.318267 0.434880 0.050492 Uani 1.000000 0 0.000195 0.000184
0.000124 0.001271
C23 0.097015 0.235855 0.475912 0.055082 Uani 1.000000 0 0.000252 0.000219
0.000171 0.001615
C26 0.139010 0.417867 0.570031 0.065303 Uani 1.000000 0 0.000256 0.000230
0.000156 0.001682

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H19 1.479(3) 0.794(2) 0.1203(15) 0.11(2) Uani 1.000000 0
H5 0.825(2) 0.6489(19) 0.1638(18) 0.13(2) Uani 1.000000 0
H10 -0.034(3) 0.346(2) 0.6815(15) 0.13(2) Uani 1.000000 0
H4 0.615(2) 0.565(2) 0.2896(15) 0.097(18) Uani 1.000000 0
H18 1.301(3) 0.645(2) 0.1899(15) 0.12(2) Uani 1.000000 0
H20 1.487(2) 0.736(2) -0.1460(14) 0.087(16) Uani 1.000000 0
H3 0.402(3) 0.935(2) 0.3453(16) 0.12(2) Uani 1.000000 0
H6 0.598(2) 1.045(2) 0.2235(15) 0.102(18) Uani 1.000000 0
H17 1.095(3) 0.087(2) 0.159(2) 0.19(3) Uani 1.000000 0
H15 0.893(3) -0.024(2) 0.2815(18) 0.13(2) Uani 1.000000 0
H11 0.083(2) 0.167(2) 0.4370(14) 0.094(19) Uani 1.000000 0
H9 0.155(3) 0.490(2) 0.6046(15) 0.12(2) Uani 1.000000 0
H13 0.477(3) 0.116(2) 0.4921(17) 0.08(2) Uani 1.000000 0
H7 1.045(3) 0.887(2) 0.0299(19) 0.12(2) Uani 1.000000 0
H12 0.546(3) 0.257(2) 0.433(2) 0.10(2) Uani 1.000000 0
H14 0.722(3) 0.338(2) 0.391(2) 0.19(3) Uani 1.000000 0
H1 0.419(3) 0.695(2) 0.3744(17) 0.09(2) Uani 1.000000 0
H8 0.983(3) 0.752(2) 0.101(2) 0.14(3) Uani 1.000000 0
H16 0.937(3) 0.427(3) 0.266(2) 0.18(3) Uani 1.000000 0
H2 1.112(3) 0.325(3) 0.1539(19) 0.09(3) Uani 1.000000 0
O2 1.63105(15) 0.89731(14) -0.13866(11) 0.0833(11) Uani 1.000000 0
O1 1.66296(18) 0.88870(16) -0.01061(11) 0.1036(13) Uani 1.000000 0
O3 1.3552(2) 0.5738(2) -0.16427(13) 0.1529(19) Uani 1.000000 0
O4 1.1577(2) 0.57108(18) -0.06029(11) 0.1146(14) Uani 1.000000 0
O5 1.20619(14) 0.40207(14) 0.10171(9) 0.0658(10) Uani 1.000000 0
O6 1.05720(13) 0.57263(11) 0.16723(9) 0.0748(10) Uani 1.000000 0
N8 1.60426(18) 0.85892(16) -0.05826(15) 0.0599(13) Uani 1.000000 0
N7 1.2808(2) 0.58903(19) -0.08865(14) 0.0780(15) Uani 1.000000 0
C5 1.49437(19) 0.77201(17) -0.01588(14) 0.0479(13) Uani 1.000000 0
C3 1.34041(19) 0.63781(17) -0.02946(13) 0.0471(12) Uani 1.000000 0
C4 1.4467(2) 0.7177(2) -0.07199(16) 0.0489(14) Uani 1.000000 0
C2 1.28418(18) 0.61015(17) 0.06485(13) 0.0474(13) Uani 1.000000 0
C1 1.1710(2) 0.5224(2) 0.11458(13) 0.0543(14) Uani 1.000000 0
C7 1.3365(3) 0.6679(2) 0.11806(17) 0.0652(16) Uani 1.000000 0
C6 1.4415(3) 0.7499(3) 0.07834(17) 0.0656(18) Uani 1.000000 0
C10 0.7299(2) 0.7195(2) 0.20305(15) 0.0632(16) Uani 1.000000 0
C13 0.4958(3) 0.8782(3) 0.30374(16) 0.0649(17) Uani 1.000000 0
C11 0.6179(3) 0.6676(2) 0.27269(17) 0.0646(16) Uani 1.000000 0
C8 0.8407(2) 0.9216(2) 0.11117(13) 0.0564(14) Uani 1.000000 0
C12 0.6041(2) 0.9361(2) 0.23585(16) 0.0602(15) Uani 1.000000 0
C9 0.72385(19) 0.85614(19) 0.18554(12) 0.0510(13) Uani 1.000000 0
O12 0.81561(13) 1.03931(13) 0.08335(9) 0.0724(10) Uani 1.000000 0
N3 0.9681(3) 0.8472(2) 0.08127(19) 0.0916(19) Uani 1.000000 0
N2 0.5052(2) 0.74662(19) 0.32113(13) 0.0580(13) Uani 1.000000 0
C17 0.79369(19) 0.14768(18) 0.34120(12) 0.0477(12) Uani 1.000000 0
C16 0.6740(2) 0.0816(2) 0.41020(13) 0.0519(13) Uani 1.000000 0
C18 0.8980(3) 0.0773(2) 0.27633(19) 0.0722(17) Uani 1.000000 0
C15 0.8044(3) 0.2779(2) 0.33959(17) 0.0841(18) Uani 1.000000 0
C14 0.9162(3) 0.3319(3) 0.2722(2) 0.088(2) Uani 1.000000 0
C19 1.0079(3) 0.1376(3) 0.21136(17) 0.0745(18) Uani 1.000000 0
O8 0.46880(15) 0.43829(12) 0.40668(10) 0.0843(11) Uani 1.000000 0
O11 -0.16138(17) 0.16863(15) 0.69096(12) 0.0986(13) Uani 1.000000 0
O9 0.30478(13) 0.61713(13) 0.43739(9) 0.0703(10) Uani 1.000000 0
O10 -0.12249(17) 0.09710(16) 0.56413(13) 0.1044(14) Uani 1.000000 0
N5 0.2845(2) 0.3081(2) 0.33895(13) 0.0786(15) Uani 1.000000 0
N6 -0.09847(19) 0.16500(18) 0.60996(16) 0.0718(15) Uani 1.000000 0
O13 0.3345(2) 0.2000(2) 0.31670(12) 0.1432(18) Uani 1.000000 0
O14 0.3012(2) 0.40778(19) 0.28755(11) 0.1265(16) Uani 1.000000 0
O7 0.68882(13) -0.03988(13) 0.42345(9) 0.0761(10) Uani 1.000000 0
N1 1.0150(2) 0.26311(18) 0.21036(13) 0.0594(13) Uani 1.000000 0
N4 0.5560(3) 0.1596(2) 0.45304(17) 0.0738(17) Uani 1.000000 0
C21 0.22492(19) 0.40999(17) 0.47975(13) 0.0490(12) Uani 1.000000 0
C20 0.3442(2) 0.4949(2) 0.43703(13) 0.0543(14) Uani 1.000000 0
C24 0.0140(2) 0.25008(18) 0.56531(15) 0.0555(14) Uani 1.000000 0
C25 0.0334(2) 0.3384(2) 0.61385(17) 0.0676(16) Uani 1.000000 0
C22 0.2011(2) 0.31827(18) 0.43488(12) 0.0505(13) Uani 1.000000 0
C23 0.0970(3) 0.2359(2) 0.47591(17) 0.0551(16) Uani 1.000000 0
C26 0.1390(3) 0.4179(2) 0.57003(16) 0.0653(17) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H19 0.110179 0.150631 0.083676 -0.067607 -0.029957 -0.004758 0.017375 0.025016
0.020217 0.015648 0.014296 0.016308
H5 0.081734 0.045224 0.202278 -0.000274 0.005607 0.009026 0.018861 0.015185
0.025258 0.013158 0.016654 0.014996
H10 0.148524 0.147826 0.065534 -0.069942 0.028964 -0.030726 0.021817 0.023858
0.016776 0.017135 0.015931 0.016654
H4 0.088417 0.068517 0.093714 -0.028042 0.026481 0.000604 0.017297 0.016722
0.016828 0.014268 0.012719 0.013744
H18 0.172956 0.134106 0.072228 -0.076342 -0.040822 0.007092 0.019555 0.023032
0.019057 0.015824 0.017749 0.018359
H20 0.076031 0.121700 0.072548 -0.053912 -0.007134 -0.021638 0.013445 0.019636
0.016338 0.012146 0.013734 0.015789
H3 0.105541 0.092803 0.130363 -0.029561 0.016564 -0.028817 0.020332 0.019546
0.021853 0.015231 0.015597 0.015715
H6 0.066403 0.074478 0.114060 -0.007203 0.025966 0.003848 0.016470 0.015972
0.017786 0.013995 0.012863 0.014573
H17 0.101173 0.108776 0.285594 -0.023019 0.057665 -0.085933 0.024529 0.021873
0.033427 0.017334 0.022180 0.021454
H15 0.074034 0.111139 0.146550 -0.032887 0.025270 0.003500 0.018036 0.021762
0.020621 0.016931 0.014430 0.018679
H11 0.089512 0.119657 0.070364 -0.024090 -0.006954 -0.028609 0.017260 0.022189
0.018144 0.014267 0.013174 0.015244
H9 0.134834 0.124702 0.101784 -0.075419 0.018471 -0.057076 0.019389 0.023357
0.019618 0.016477 0.014087 0.016300
H13 0.062233 0.059726 0.107964 -0.019236 -0.004382 -0.023131 0.016945 0.016502
0.023115 0.012718 0.014108 0.016003
H7 0.090179 0.082604 0.117220 -0.003121 0.024207 0.032491 0.024464 0.019914
0.020595 0.016108 0.016922 0.016703
H12 0.083683 0.070087 0.131961 -0.028205 -0.004244 -0.011749 0.018040 0.023181
0.026412 0.018896 0.016738 0.019324
H14 0.117114 0.108285 0.265470 -0.099969 0.136804 -0.093100 0.025547 0.023002
0.026227 0.019725 0.021123 0.019387
H1 0.075231 0.079888 0.078140 -0.015883 0.023931 0.008935 0.023017 0.020640
0.023147 0.017180 0.019040 0.018742
H8 0.076262 0.033371 0.226364 -0.012554 0.074265 -0.020501 0.023732 0.017292
0.029374 0.018836 0.020277 0.017973
H16 0.122303 0.165721 0.188970 -0.091359 0.077654 -0.022445 0.025127 0.032693
0.024173 0.022877 0.018237 0.022698
H2 0.090765 0.089062 0.077305 0.002476 -0.026284 -0.008299 0.025276 0.023240
0.030741 0.019274 0.024016 0.023201
O2 0.077137 0.088327 0.076292 -0.049256 -0.005080 0.015967 0.000995 0.001251
0.001056 0.000816 0.000852 0.000918
O1 0.101011 0.132661 0.094788 -0.081765 -0.018984 -0.005552 0.001046 0.001670
0.001340 0.001105 0.000964 0.001082
O3 0.140814 0.254139 0.094172 -0.103031 0.000941 -0.081747 0.001508 0.002668
0.001655 0.001582 0.001291 0.001709
O4 0.101205 0.172713 0.094779 -0.080035 -0.040305 0.007160 0.000985 0.001896
0.001429 0.001143 0.001015 0.001266
O5 0.047544 0.048280 0.080590 -0.018348 0.012516 -0.004606 0.000863 0.000984
0.000999 0.000713 0.000733 0.000781
O6 0.044641 0.048901 0.100526 -0.012903 0.015086 0.000660 0.000847 0.000892
0.001016 0.000681 0.000757 0.000772
N8 0.052746 0.059995 0.065048 -0.030359 -0.006636 -0.000104 0.001110 0.001216
0.001389 0.000917 0.001070 0.001024
N7 0.073589 0.107696 0.061821 -0.049253 -0.010357 -0.012459 0.001278 0.001665
0.001550 0.001198 0.001232 0.001246
C5 0.040781 0.047289 0.049421 -0.016663 -0.002546 -0.001309 0.001083 0.001210
0.001411 0.000929 0.001012 0.000997
C3 0.040499 0.046675 0.049228 -0.014882 -0.004325 -0.002426 0.001077 0.001197
0.001391 0.000906 0.001036 0.001005
C4 0.045904 0.051577 0.043167 -0.018020 -0.001252 -0.002519 0.001238 0.001313
0.001437 0.001001 0.001275 0.001205
C2 0.037016 0.047161 0.049549 -0.016948 -0.001462 0.004196 0.001068 0.001200
0.001384 0.000912 0.000980 0.000977
C1 0.034693 0.042288 0.066629 -0.012661 0.008066 0.003551 0.001153 0.001368
0.001356 0.001034 0.000994 0.001147
C7 0.066926 0.080234 0.045108 -0.036495 -0.004871 0.005033 0.001452 0.001757
0.001576 0.001258 0.001415 0.001436
C6 0.070333 0.081358 0.049963 -0.041632 -0.008280 -0.005210 0.001620 0.001819
0.001821 0.001323 0.001352 0.001317
C10 0.044181 0.045315 0.079682 -0.013817 0.003369 0.007554 0.001344 0.001600
0.001643 0.001151 0.001152 0.001307
C13 0.049460 0.055269 0.071879 -0.017848 0.008126 -0.002894 0.001440 0.001857
0.001761 0.001279 0.001239 0.001380
C11 0.050175 0.045422 0.080224 -0.019842 0.001373 0.009913 0.001321 0.001722
0.001808 0.001323 0.001235 0.001500
C8 0.041621 0.045584 0.065155 -0.012299 -0.002319 0.013383 0.001196 0.001442
0.001402 0.001082 0.001050 0.001196
C12 0.046632 0.045066 0.072495 -0.015486 0.001750 0.003976 0.001225 0.001555
0.001618 0.001246 0.001146 0.001391
C9 0.040017 0.044935 0.058085 -0.016212 -0.004296 0.007977 0.001038 0.001325
0.001304 0.000963 0.000950 0.001114
O12 0.054191 0.053033 0.084122 -0.015848 0.003161 0.016633 0.000875 0.000944
0.000960 0.000712 0.000729 0.000778
N3 0.053346 0.058096 0.114295 -0.008499 0.018624 0.024417 0.001543 0.001764
0.001817 0.001499 0.001347 0.001656
N2 0.045398 0.056935 0.061360 -0.022198 -0.001236 0.005338 0.001045 0.001421
0.001320 0.000992 0.000940 0.001256
C17 0.042462 0.039543 0.052445 -0.019427 -0.001065 0.004900 0.001037 0.001251
0.001254 0.000943 0.000923 0.001069
C16 0.040304 0.038311 0.064246 -0.015448 -0.003188 0.010897 0.001113 0.001352
0.001361 0.001023 0.000996 0.001156
C18 0.055824 0.052434 0.090406 -0.024976 0.010962 -0.009228 0.001444 0.001769
0.001900 0.001359 0.001313 0.001617
C15 0.075591 0.054091 0.088902 -0.034501 0.035991 -0.012959 0.001716 0.001785
0.001691 0.001430 0.001352 0.001338
C14 0.080713 0.053004 0.097458 -0.039112 0.034634 -0.012369 0.001927 0.001878
0.001900 0.001471 0.001500 0.001614
C19 0.054687 0.060024 0.089578 -0.025631 0.016828 -0.016535 0.001493 0.001860
0.001829 0.001346 0.001296 0.001456
O8 0.050711 0.045103 0.123283 -0.013311 0.010771 0.007786 0.000921 0.000902
0.001130 0.000726 0.000832 0.000802
O11 0.076735 0.096058 0.096008 -0.043148 0.010045 0.018566 0.001088 0.001317
0.001152 0.000894 0.000921 0.001009
O9 0.046394 0.044177 0.097820 -0.013604 0.007036 -0.001657 0.000835 0.000900
0.001056 0.000682 0.000732 0.000761
O10 0.079699 0.071270 0.149248 -0.040159 0.005151 -0.025209 0.001166 0.001235
0.001606 0.000937 0.001035 0.001052
N5 0.099276 0.079044 0.045437 -0.030859 0.006084 -0.011809 0.001397 0.001664
0.001420 0.001265 0.001093 0.001288
N6 0.052784 0.053976 0.089301 -0.021645 0.006124 0.000832 0.001240 0.001318
0.001559 0.000973 0.001170 0.001178
O13 0.187428 0.120243 0.087804 -0.041078 0.032418 -0.049526 0.002074 0.001639
0.001450 0.001530 0.001289 0.001303
O14 0.170161 0.130372 0.053352 -0.050099 0.002398 0.011453 0.001743 0.001740
0.001156 0.001354 0.001154 0.001128
O7 0.055029 0.044163 0.101994 -0.017950 0.004524 0.014292 0.000877 0.000913
0.001039 0.000698 0.000752 0.000778
N1 0.048586 0.052163 0.062199 -0.021550 0.008044 -0.001652 0.001065 0.001311
0.001260 0.000956 0.000906 0.001151
N4 0.053397 0.048922 0.091268 -0.020504 0.010800 0.011306 0.001530 0.001691
0.001750 0.001444 0.001163 0.001474
C21 0.046570 0.043662 0.048080 -0.018331 0.000719 -0.000430 0.001105 0.001192
0.001333 0.000949 0.000988 0.000989
C20 0.039242 0.037028 0.067345 -0.008892 0.006316 0.000763 0.001226 0.001342
0.001331 0.001072 0.001027 0.001122
C24 0.044002 0.043408 0.064441 -0.013282 0.001294 0.002475 0.001178 0.001271
0.001517 0.000995 0.001073 0.001126
C25 0.064428 0.069068 0.054776 -0.030864 0.015060 -0.011160 0.001477 0.001656
0.001597 0.001259 0.001373 0.001424
C22 0.049368 0.047857 0.048315 -0.016316 -0.003386 -0.003541 0.001130 0.001240
0.001368 0.000974 0.001019 0.001029
C23 0.051575 0.049490 0.061161 -0.019052 -0.006487 -0.007224 0.001358 0.001490
0.001824 0.001082 0.001236 0.001293
C26 0.069040 0.065456 0.053302 -0.035904 0.010635 -0.013560 0.001539 0.001732
0.001622 0.001245 0.001220 0.001283

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 . N8 . 1.1950(19) yes
O1 . N8 . 1.1947(19) yes
O3 . N7 . 1.180(2) yes
O4 . N7 . 1.186(2) yes
O11 . N6 . 1.209(2) yes
O10 . N6 . 1.198(2) yes
O13 . N5 . 1.191(2) yes
O14 . N5 . 1.186(2) yes
O5 . C1 . 1.258(2) yes
O6 . C1 . 1.225(2) yes
O12 . C8 . 1.2165(19) yes
O8 . C20 . 1.2188(19) yes
O9 . C20 . 1.245(2) yes
O7 . C16 . 1.2231(19) yes
N8 . C5 . 1.460(2) yes
N7 . C3 . 1.453(2) yes
N3 . C8 . 1.312(3) yes
N2 . C13 . 1.329(3) yes
N2 . C11 . 1.328(3) yes
N5 . C22 . 1.456(2) yes
N6 . C24 . 1.469(2) yes
N1 . C14 . 1.312(3) yes
N1 . C19 . 1.316(3) yes
N4 . C16 . 1.318(3) yes
N3 . H7 . 0.99(2) yes
N3 . H8 . 0.97(2) yes
N2 . H1 . 1.12(3) yes
N1 . H2 . 1.26(4) yes
N4 . H13 . 0.95(2) yes
N4 . H12 . 1.00(2) yes
C5 . C4 . 1.368(3) yes
C5 . C6 . 1.374(3) yes
C3 . C4 . 1.386(2) yes
C3 . C2 . 1.381(2) yes
C2 . C1 . 1.503(2) yes
C2 . C7 . 1.383(3) yes
C7 . C6 . 1.387(3) yes
C10 . C11 . 1.383(3) yes
C10 . C9 . 1.384(2) yes
C13 . C12 . 1.377(3) yes
C8 . C9 . 1.507(2) yes
C12 . C9 . 1.381(3) yes
C17 . C16 . 1.494(2) yes
C17 . C18 . 1.370(3) yes
C17 . C15 . 1.372(3) yes
C18 . C19 . 1.380(3) yes
C15 . C14 . 1.377(3) yes
C21 . C20 . 1.515(2) yes
C21 . C22 . 1.380(2) yes
C21 . C26 . 1.385(3) yes
C24 . C25 . 1.372(3) yes
C24 . C23 . 1.376(3) yes
C25 . C26 . 1.380(3) yes
C22 . C23 . 1.385(3) yes
C4 . H20 . 1.079(19) yes
C7 . H18 . 1.05(2) yes
C6 . H19 . 1.06(2) yes
C10 . H5 . 1.13(2) yes
C13 . H3 . 1.06(2) yes
C11 . H4 . 1.051(19) yes
C12 . H6 . 1.099(19) yes
C18 . H15 . 1.05(2) yes
C15 . H14 . 1.10(2) yes
C14 . H16 . 1.03(3) yes
C19 . H17 . 1.09(2) yes
C25 . H10 . 1.047(19) yes
C23 . H11 . 1.08(2) yes
C26 . H9 . 1.07(2) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . N8 . O1 . 123.03(19) yes
O3 . N7 . O4 . 122.6(2) yes
O11 . N6 . O10 . 124.2(2) yes
O13 . N5 . O14 . 123.5(2) yes
O2 . N8 . C5 . 118.7(2) yes
O1 . N8 . C5 . 118.2(2) yes
O3 . N7 . C3 . 118.6(2) yes
O4 . N7 . C3 . 118.7(2) yes
O11 . N6 . C24 . 117.5(2) yes
O10 . N6 . C24 . 118.3(2) yes
O13 . N5 . C22 . 118.2(2) yes
O14 . N5 . C22 . 118.3(2) yes
O5 . C1 . O6 . 126.30(17) yes
O8 . C20 . O9 . 126.17(18) yes
O12 . C8 . N3 . 123.12(19) yes
O7 . C16 . N4 . 123.53(19) yes
O5 . C1 . C2 . 116.32(18) yes
O6 . C1 . C2 . 117.25(18) yes
O12 . C8 . C9 . 119.88(18) yes
O8 . C20 . C21 . 117.72(17) yes
O9 . C20 . C21 . 116.11(17) yes
O7 . C16 . C17 . 119.31(18) yes
N8 . C5 . C4 . 118.40(19) yes
N8 . C5 . C6 . 118.8(2) yes
N7 . C3 . C4 . 116.99(19) yes
N7 . C3 . C2 . 119.66(18) yes
N3 . C8 . C9 . 116.97(19) yes
N2 . C13 . C12 . 120.8(2) yes
N2 . C11 . C10 . 121.1(2) yes
N5 . C22 . C21 . 119.81(18) yes
N5 . C22 . C23 . 117.0(2) yes
N6 . C24 . C25 . 119.4(2) yes
N6 . C24 . C23 . 117.8(2) yes
N1 . C14 . C15 . 122.7(2) yes
N1 . C19 . C18 . 121.0(2) yes
N4 . C16 . C17 . 117.15(19) yes
N2 . C13 . H3 . 116.7(12) yes
N2 . C11 . H4 . 116.1(11) yes
N1 . C14 . H16 . 112.1(16) yes
N1 . C19 . H17 . 114.8(13) yes
C13 . N2 . C11 . 121.0(2) yes
C14 . N1 . C19 . 119.5(2) yes
C13 . N2 . H1 . 123.4(12) yes
C11 . N2 . H1 . 115.5(12) yes
C8 . N3 . H7 . 118.0(15) yes
C8 . N3 . H8 . 121.3(16) yes
C16 . N4 . H13 . 116.1(15) yes
C16 . N4 . H12 . 119.1(16) yes
C14 . N1 . H2 . 115.7(11) yes
C19 . N1 . H2 . 124.8(11) yes
C5 . C4 . C3 . 116.9(2) yes
C5 . C6 . C7 . 118.5(2) yes
C3 . C2 . C1 . 125.5(2) yes
C3 . C2 . C7 . 117.30(19) yes
C4 . C5 . C6 . 122.8(2) yes
C4 . C3 . C2 . 123.2(2) yes
C2 . C7 . C6 . 121.4(2) yes
C1 . C2 . C7 . 117.22(18) yes
C10 . C9 . C8 . 122.48(18) yes
C10 . C9 . C12 . 118.98(18) yes
C13 . C12 . C9 . 119.4(2) yes
C11 . C10 . C9 . 118.7(2) yes
C8 . C9 . C12 . 118.50(18) yes
C17 . C18 . C19 . 120.3(2) yes
C17 . C15 . C14 . 118.8(2) yes
C16 . C17 . C18 . 119.70(18) yes
C16 . C17 . C15 . 122.58(19) yes
C18 . C17 . C15 . 117.72(19) yes
C21 . C22 . C23 . 123.13(19) yes
C21 . C26 . C25 . 122.0(2) yes
C20 . C21 . C22 . 123.35(17) yes
C20 . C21 . C26 . 119.44(18) yes
C24 . C25 . C26 . 118.2(2) yes
C24 . C23 . C22 . 116.8(2) yes
C25 . C24 . C23 . 122.8(2) yes
C22 . C21 . C26 . 117.11(18) yes
C5 . C4 . H20 . 123.0(11) yes
C5 . C6 . H19 . 121.5(13) yes
C3 . C4 . H20 . 120.2(11) yes
C2 . C7 . H18 . 119.6(13) yes
C7 . C6 . H19 . 120.0(13) yes
C6 . C7 . H18 . 118.9(13) yes
C10 . C11 . H4 . 122.8(12) yes
C13 . C12 . H6 . 120.6(11) yes
C11 . C10 . H5 . 119.0(11) yes
C12 . C13 . H3 . 122.6(12) yes
C9 . C10 . H5 . 122.2(11) yes
C9 . C12 . H6 . 120.0(10) yes
C17 . C18 . H15 . 116.8(14) yes
C17 . C15 . H14 . 119.5(11) yes
C18 . C19 . H17 . 124.3(14) yes
C15 . C14 . H16 . 125.1(16) yes
C14 . C15 . H14 . 121.7(11) yes
C19 . C18 . H15 . 122.8(14) yes
C21 . C26 . H9 . 117.5(12) yes
C24 . C25 . H10 . 119.7(13) yes
C24 . C23 . H11 . 123.5(12) yes
C25 . C26 . H9 . 120.5(12) yes
C22 . C23 . H11 . 119.6(12) yes
C26 . C25 . H10 . 122.1(13) yes
H13 . N4 . H12 . 123(2) yes
H7 . N3 . H8 . 120(2) yes
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate 2:2'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_150K_har
_database_code_depnum_ccdc_archive 'CCDC 1922029'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex_5_150K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.59 %
RESPONSE: Data collection at non-standard wavelength. Fprime used for anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_150K_har  
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.14 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT919_complex_5_150K_har  
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: Reflections used in the refinement are taken from the fcf from a SHELXL refinement using the LIST 4FVAR^2 command. HAR applies its own rejection criteria during the initial stages of refinement. Reflection was not rejected.
;
_vrf_PLAT353_complex_5_150K_har_2 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H2B      .       1.03 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT353_complex_5_150K_har_3 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N4       - H4A      .       1.02 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-3
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            150K
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_weight         410.3897
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       214
_QCr_calc_unit_n_alpha_electrons 107
_QCr_calc_unit_n_beta_electrons  107

# =======
# Crystal
# =======

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             856

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7014
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/n 1'
_symmetry_space_group_name_Hall  '-p 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, +y+1/2, -z+1/2'
'+x+1/2, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    150
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      43.82

_cell_length_a                   7.0883(3)
_cell_length_b                   14.3309(6)
_cell_length_c                   18.3184(7)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 92.8585(18)
_cell_angle_gamma                90.000000(0)
_cell_volume                     1858.50(13)

_cell_formula_units_Z            4.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6417
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         41.365
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .


# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            333.538007

_reflns_d_resolution_high        9.147804
_reflns_d_resolution_low         0.670048
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                5468
_reflns_number_total             5468
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0220
_refine_ls_R_factor_all          0.0220
_refine_ls_wR_factor_gt          0.0176
_refine_ls_wR_factor_all         0.0176
_refine_ls_R_Fsqd_factor         0.0273
_refine_ls_goodness_of_fit_gt    1.4863
_refine_ls_goodness_of_fit_all   1.4863
_refine_ls_number_reflns         5468
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0092
_refine_ls_shift/su_max_mean     0.0011
_refine_ls_shift/su_max_par      'H17 Uxx'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1045
_refine_diff_density_min         -0.1145
_refine_diff_density_rms         0.0255
_refine_diff_density_max_atom    0.0325
_refine_diff_density_max_atom_tag N1
_refine_diff_density_min_atom    -0.0522
_refine_diff_density_min_atom_tag C11
_refine_diff_density_rms_atom    0.0238

_refine_special_details          
;

   HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 150K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  150K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

150k.cif obtained from res in _shelx_res_file
;



# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 1.132437 0.673746 0.400294 0.052572 Uani 1.000000 0 0.000986 0.000407
0.000338 0.004813
H8 1.063033 0.563298 0.182880 0.047495 Uani 1.000000 0 0.000940 0.000400
0.000333 0.004487
H7 1.103626 0.698471 0.265492 0.053052 Uani 1.000000 0 0.000952 0.000426
0.000353 0.004706
H5 1.126006 0.512332 0.449574 0.047943 Uani 1.000000 0 0.000936 0.000427
0.000325 0.004544
H1 1.097156 0.275799 0.463110 0.031389 Uani 1.000000 0 0.001040 0.000579
0.000380 0.005202
O3 0.889588 0.340227 0.215185 0.019389 Uani 1.000000 0 0.000045 0.000021
0.000017 0.000163
O1 1.074443 0.344274 0.444499 0.022765 Uani 1.000000 0 0.000052 0.000024
0.000018 0.000178
O2 1.145576 0.283153 0.336596 0.024508 Uani 1.000000 0 0.000051 0.000022
0.000017 0.000176
O4 1.172112 0.365245 0.169891 0.026266 Uani 1.000000 0 0.000051 0.000023
0.000018 0.000184
C4 1.096520 0.446871 0.344162 0.016071 Uani 1.000000 0 0.000060 0.000029
0.000024 0.000204
C2 1.049952 0.381968 0.214000 0.017483 Uani 1.000000 0 0.000067 0.000029
0.000023 0.000211
C1 1.107662 0.349923 0.374150 0.017375 Uani 1.000000 0 0.000064 0.000030
0.000023 0.000209
C7 1.099802 0.628577 0.287675 0.024273 Uani 1.000000 0 0.000071 0.000033
0.000029 0.000248
C3 1.079056 0.461007 0.268136 0.015907 Uani 1.000000 0 0.000061 0.000029
0.000024 0.000202
C5 1.112997 0.523838 0.391044 0.020568 Uani 1.000000 0 0.000068 0.000032
0.000027 0.000232
C6 1.115889 0.614384 0.363128 0.024011 Uani 1.000000 0 0.000069 0.000033
0.000029 0.000248
C8 1.079879 0.551960 0.240778 0.020903 Uani 1.000000 0 0.000071 0.000031
0.000029 0.000232
H20 1.203249 0.020769 0.634699 0.041582 Uani 1.000000 0 0.000959 0.000388
0.000321 0.004199
H19 1.110141 0.186519 0.601246 0.045955 Uani 1.000000 0 0.000959 0.000390
0.000320 0.004350
H18 1.200086 0.141360 0.384696 0.047598 Uani 1.000000 0 0.001014 0.000407
0.000321 0.004417
H2A 1.338287 -0.158504 0.439106 0.045274 Uani 1.000000 0 0.001066 0.000462
0.000382 0.004943
H17 1.283499 -0.023982 0.406298 0.052317 Uani 1.000000 0 0.000959 0.000414
0.000312 0.004606
H2B 1.375356 -0.242156 0.508836 0.040309 Uani 1.000000 0 0.001013 0.000448
0.000372 0.004756
O5 1.295223 -0.136409 0.609399 0.025393 Uani 1.000000 0 0.000053 0.000022
0.000017 0.000180
N1 1.151094 0.169316 0.491695 0.018873 Uani 1.000000 0 0.000054 0.000025
0.000021 0.000188
N2 1.340741 -0.175509 0.491979 0.020917 Uani 1.000000 0 0.000062 0.000030
0.000024 0.000209
C15 1.297459 -0.114771 0.544066 0.017308 Uani 1.000000 0 0.000064 0.000029
0.000024 0.000210
C20 1.201722 0.045298 0.578133 0.019410 Uani 1.000000 0 0.000068 0.000031
0.000026 0.000227
C16 1.249692 -0.015780 0.522800 0.015784 Uani 1.000000 0 0.000058 0.000029
0.000023 0.000203
C19 1.151787 0.136562 0.560134 0.020183 Uani 1.000000 0 0.000069 0.000032
0.000026 0.000228
C17 1.248919 0.018021 0.451505 0.019448 Uani 1.000000 0 0.000067 0.000032
0.000025 0.000227
C18 1.200531 0.111093 0.438725 0.020646 Uani 1.000000 0 0.000070 0.000032
0.000026 0.000231
H11 0.870770 0.033421 0.027327 0.043350 Uani 1.000000 0 0.000941 0.000398
0.000322 0.004342
H13 0.937924 0.132094 0.282676 0.052238 Uani 1.000000 0 0.001029 0.000420
0.000350 0.004735
H12 0.871403 0.202336 0.065614 0.043880 Uani 1.000000 0 0.000946 0.000415
0.000319 0.004285
H14 0.942387 -0.039417 0.254588 0.052278 Uani 1.000000 0 0.001052 0.000392
0.000327 0.004658
H4A 0.830972 -0.246463 0.144996 0.039743 Uani 1.000000 0 0.001007 0.000453
0.000351 0.004720
H4B 0.775886 -0.160009 0.207884 0.039064 Uani 1.000000 0 0.001034 0.000423
0.000364 0.004662
H3 0.897963 0.247256 0.190713 0.024474 Uani 1.000000 0 0.000968 0.000551
0.000370 0.005204
O6 0.950610 -0.137412 0.053188 0.026702 Uani 1.000000 0 0.000052 0.000023
0.000018 0.000185
N4 0.842322 -0.179137 0.163037 0.021467 Uani 1.000000 0 0.000065 0.000030
0.000024 0.000210
N3 0.901568 0.170119 0.174767 0.019601 Uani 1.000000 0 0.000054 0.000028
0.000021 0.000196
C9 0.899512 -0.117044 0.114855 0.018389 Uani 1.000000 0 0.000065 0.000030
0.000025 0.000214
C11 0.882715 0.052177 0.084060 0.018017 Uani 1.000000 0 0.000066 0.000031
0.000026 0.000219
C10 0.900820 -0.015974 0.138212 0.016464 Uani 1.000000 0 0.000061 0.000029
0.000023 0.000206
C14 0.922291 0.011488 0.211288 0.021815 Uani 1.000000 0 0.000072 0.000033
0.000026 0.000234
C12 0.883650 0.145164 0.104245 0.019353 Uani 1.000000 0 0.000066 0.000032
0.000026 0.000224
C13 0.921631 0.106015 0.227914 0.023410 Uani 1.000000 0 0.000075 0.000033
0.000028 0.000248

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 1.1324(10) 0.6737(4) 0.4003(3) 0.053(5) Uani 1.000000 0
H8 1.0630(9) 0.5633(4) 0.1829(3) 0.047(4) Uani 1.000000 0
H7 1.1036(10) 0.6985(4) 0.2655(4) 0.053(5) Uani 1.000000 0
H5 1.1260(9) 0.5123(4) 0.4496(3) 0.048(5) Uani 1.000000 0
H1 1.0972(10) 0.2758(6) 0.4631(4) 0.031(5) Uani 1.000000 0
O3 0.88959(5) 0.34023(2) 0.215185(17) 0.01939(16) Uani 1.000000 0
O1 1.07444(5) 0.34427(2) 0.444499(18) 0.02277(18) Uani 1.000000 0
O2 1.14558(5) 0.28315(2) 0.336596(17) 0.02451(18) Uani 1.000000 0
O4 1.17211(5) 0.36524(2) 0.169891(18) 0.02627(18) Uani 1.000000 0
C4 1.09652(6) 0.44687(3) 0.34416(2) 0.0161(2) Uani 1.000000 0
C2 1.04995(7) 0.38197(3) 0.21400(2) 0.0175(2) Uani 1.000000 0
C1 1.10766(6) 0.34992(3) 0.37415(2) 0.0174(2) Uani 1.000000 0
C7 1.09980(7) 0.62858(3) 0.28767(3) 0.0243(2) Uani 1.000000 0
C3 1.07906(6) 0.46101(3) 0.26814(2) 0.0159(2) Uani 1.000000 0
C5 1.11300(7) 0.52384(3) 0.39104(3) 0.0206(2) Uani 1.000000 0
C6 1.11589(7) 0.61438(3) 0.36313(3) 0.0240(2) Uani 1.000000 0
C8 1.07988(7) 0.55196(3) 0.24078(3) 0.0209(2) Uani 1.000000 0
H20 1.2032(10) 0.0208(4) 0.6347(3) 0.042(4) Uani 1.000000 0
H19 1.1101(10) 0.1865(4) 0.6012(3) 0.046(4) Uani 1.000000 0
H18 1.2001(10) 0.1414(4) 0.3847(3) 0.048(4) Uani 1.000000 0
H2A 1.3383(11) -0.1585(5) 0.4391(4) 0.045(5) Uani 1.000000 0
H17 1.2835(10) -0.0240(4) 0.4063(3) 0.052(5) Uani 1.000000 0
H2B 1.3754(10) -0.2422(4) 0.5088(4) 0.040(5) Uani 1.000000 0
O5 1.29522(5) -0.13641(2) 0.609399(17) 0.02539(18) Uani 1.000000 0
N1 1.15109(5) 0.16932(2) 0.49169(2) 0.01887(19) Uani 1.000000 0
N2 1.34074(6) -0.17551(3) 0.49198(2) 0.0209(2) Uani 1.000000 0
C15 1.29746(6) -0.11477(3) 0.54407(2) 0.0173(2) Uani 1.000000 0
C20 1.20172(7) 0.04530(3) 0.57813(3) 0.0194(2) Uani 1.000000 0
C16 1.24969(6) -0.01578(3) 0.52280(2) 0.0158(2) Uani 1.000000 0
C19 1.15179(7) 0.13656(3) 0.56013(3) 0.0202(2) Uani 1.000000 0
C17 1.24892(7) 0.01802(3) 0.45151(3) 0.0194(2) Uani 1.000000 0
C18 1.20053(7) 0.11109(3) 0.43873(3) 0.0206(2) Uani 1.000000 0
H11 0.8708(9) 0.0334(4) 0.0273(3) 0.043(4) Uani 1.000000 0
H13 0.9379(10) 0.1321(4) 0.2827(3) 0.052(5) Uani 1.000000 0
H12 0.8714(9) 0.2023(4) 0.0656(3) 0.044(4) Uani 1.000000 0
H14 0.9424(11) -0.0394(4) 0.2546(3) 0.052(5) Uani 1.000000 0
H4A 0.8310(10) -0.2465(5) 0.1450(4) 0.040(5) Uani 1.000000 0
H4B 0.7759(10) -0.1600(4) 0.2079(4) 0.039(5) Uani 1.000000 0
H3 0.8980(10) 0.2473(6) 0.1907(4) 0.024(5) Uani 1.000000 0
O6 0.95061(5) -0.13741(2) 0.053188(18) 0.02670(19) Uani 1.000000 0
N4 0.84232(6) -0.17914(3) 0.16304(2) 0.0215(2) Uani 1.000000 0
N3 0.90157(5) 0.17012(3) 0.17477(2) 0.0196(2) Uani 1.000000 0
C9 0.89951(6) -0.11704(3) 0.11485(2) 0.0184(2) Uani 1.000000 0
C11 0.88272(7) 0.05218(3) 0.08406(3) 0.0180(2) Uani 1.000000 0
C10 0.90082(6) -0.01597(3) 0.13821(2) 0.0165(2) Uani 1.000000 0
C14 0.92229(7) 0.01149(3) 0.21129(3) 0.0218(2) Uani 1.000000 0
C12 0.88365(7) 0.14516(3) 0.10424(3) 0.0194(2) Uani 1.000000 0
C13 0.92163(7) 0.10601(3) 0.22791(3) 0.0234(2) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.076027 0.030147 0.050638 -0.007168 -0.005881 -0.005665 0.005658 0.004144
0.004627 0.003588 0.004105 0.003399
H8 0.063348 0.029253 0.049571 -0.001749 -0.000320 0.009719 0.005008 0.003992
0.004457 0.003336 0.003953 0.003278
H7 0.071897 0.028727 0.058258 -0.001102 0.000489 0.000330 0.005340 0.003962
0.004823 0.003636 0.004000 0.003430
H5 0.061636 0.043917 0.038218 0.003259 0.001917 -0.002943 0.005058 0.004433
0.004171 0.003610 0.003913 0.003377
H1 0.037760 0.029666 0.026482 0.006280 -0.000981 0.003043 0.005299 0.005457
0.004877 0.004301 0.004088 0.004058
O3 0.026707 0.015364 0.016143 -0.002070 0.001530 -0.002638 0.000180 0.000154
0.000156 0.000126 0.000131 0.000120
O1 0.034571 0.019165 0.014673 0.003973 0.002361 0.001156 0.000203 0.000173
0.000160 0.000149 0.000141 0.000132
O2 0.042070 0.015587 0.015997 0.007352 0.002747 0.001450 0.000207 0.000159
0.000162 0.000142 0.000145 0.000125
O4 0.036332 0.022839 0.020747 -0.000837 0.012619 -0.001176 0.000206 0.000174
0.000176 0.000145 0.000154 0.000136
C4 0.019271 0.013585 0.015179 0.000788 -0.000915 -0.000477 0.000213 0.000194
0.000206 0.000155 0.000165 0.000154
C2 0.025561 0.014401 0.012787 -0.000456 0.003955 0.000307 0.000241 0.000192
0.000201 0.000167 0.000173 0.000153
C1 0.023987 0.014555 0.013528 0.002935 0.000383 0.000787 0.000224 0.000202
0.000202 0.000165 0.000168 0.000158
C7 0.028909 0.012501 0.031311 -0.000350 0.000511 0.001039 0.000258 0.000210
0.000275 0.000186 0.000209 0.000194
C3 0.020883 0.011793 0.015059 -0.000489 0.001044 0.000896 0.000212 0.000189
0.000204 0.000155 0.000162 0.000153
C5 0.024735 0.017225 0.019366 0.001019 -0.002660 -0.004372 0.000242 0.000220
0.000232 0.000176 0.000188 0.000183
C6 0.026933 0.015018 0.029685 0.000016 -0.002542 -0.005422 0.000253 0.000216
0.000274 0.000184 0.000207 0.000192
C8 0.027399 0.013735 0.021594 -0.000722 0.001416 0.003372 0.000246 0.000207
0.000243 0.000172 0.000199 0.000180
H20 0.067475 0.030347 0.027416 0.006774 0.007286 0.005624 0.004971 0.003927
0.003715 0.003438 0.003613 0.003100
H19 0.073702 0.026783 0.037546 0.005567 0.004439 0.002959 0.005147 0.003850
0.004072 0.003440 0.003737 0.003134
H18 0.080269 0.034372 0.028306 0.009236 0.004257 0.005544 0.005452 0.003985
0.003840 0.003595 0.003809 0.003169
H2A 0.051862 0.047230 0.037178 0.005657 0.006687 0.002517 0.005414 0.005066
0.004381 0.003741 0.004151 0.003760
H17 0.081133 0.043845 0.033151 0.014215 0.014624 0.004428 0.005565 0.004277
0.004022 0.003816 0.003987 0.003292
H2B 0.057858 0.024520 0.039200 0.009403 0.008942 0.005902 0.005510 0.004137
0.004658 0.003707 0.004043 0.003477
O5 0.044893 0.015165 0.016023 0.004125 0.000520 0.002685 0.000219 0.000158
0.000162 0.000144 0.000151 0.000126
N1 0.024606 0.013429 0.018494 0.001816 0.000181 0.001917 0.000200 0.000176
0.000188 0.000145 0.000153 0.000143
N2 0.027275 0.016212 0.019451 0.003135 0.003049 0.000812 0.000224 0.000193
0.000210 0.000163 0.000177 0.000164
C15 0.023262 0.013068 0.015519 0.000964 0.000208 0.001784 0.000223 0.000193
0.000214 0.000163 0.000169 0.000157
C20 0.029293 0.014489 0.014383 0.000968 0.000448 0.000596 0.000251 0.000207
0.000221 0.000174 0.000185 0.000166
C16 0.019363 0.013044 0.014874 0.000004 0.000157 0.001022 0.000211 0.000188
0.000209 0.000155 0.000165 0.000156
C19 0.030235 0.013679 0.016601 0.001610 0.000809 -0.000779 0.000254 0.000207
0.000223 0.000180 0.000186 0.000170
C17 0.027439 0.015986 0.015054 0.004011 0.002389 0.001676 0.000248 0.000212
0.000222 0.000176 0.000185 0.000168
C18 0.029955 0.016311 0.015760 0.004364 0.002039 0.002996 0.000252 0.000214
0.000227 0.000179 0.000192 0.000172
H11 0.061860 0.033606 0.034809 -0.003190 0.004670 0.003453 0.004957 0.004058
0.004036 0.003299 0.003782 0.003190
H13 0.083212 0.034581 0.039596 0.000942 0.009798 -0.010458 0.005789 0.004122
0.004340 0.003634 0.004164 0.003384
H12 0.067314 0.031235 0.033511 0.003567 0.006733 0.000513 0.004966 0.003976
0.003939 0.003478 0.003620 0.003142
H14 0.100365 0.027986 0.028235 0.001720 0.000738 0.002062 0.006095 0.004032
0.003849 0.003746 0.004001 0.003110
H4A 0.056518 0.026695 0.036719 -0.001802 0.009339 -0.004767 0.005284 0.004332
0.004595 0.003685 0.004019 0.003485
H4B 0.050191 0.032663 0.035179 0.003251 0.010541 -0.000925 0.005105 0.004480
0.004460 0.003587 0.003952 0.003506
H3 0.030394 0.013161 0.029985 -0.011228 0.002674 -0.013350 0.004852 0.005970
0.004823 0.003949 0.003910 0.004046
O6 0.043818 0.017119 0.020425 -0.005662 0.014145 -0.004355 0.000216 0.000166
0.000176 0.000145 0.000158 0.000132
N4 0.031118 0.014523 0.019343 -0.002011 0.007072 -0.000371 0.000233 0.000186
0.000213 0.000169 0.000172 0.000161
N3 0.022757 0.014055 0.022218 -0.002007 0.003385 -0.003411 0.000201 0.000183
0.000205 0.000150 0.000158 0.000154
C9 0.025869 0.013743 0.016119 -0.002493 0.006691 -0.002041 0.000231 0.000197
0.000215 0.000167 0.000177 0.000160
C11 0.023560 0.015270 0.015339 -0.000336 0.002165 -0.000621 0.000231 0.000208
0.000219 0.000166 0.000178 0.000168
C10 0.021329 0.013588 0.014736 -0.002059 0.003491 -0.001159 0.000213 0.000193
0.000212 0.000160 0.000166 0.000159
C14 0.034324 0.016165 0.015132 -0.002885 0.003009 -0.001264 0.000266 0.000215
0.000221 0.000189 0.000194 0.000177
C12 0.024112 0.014089 0.020026 -0.000066 0.002794 0.000313 0.000233 0.000209
0.000231 0.000174 0.000183 0.000177
C13 0.035853 0.017221 0.017241 -0.003001 0.002159 -0.004316 0.000276 0.000228
0.000239 0.000191 0.000203 0.000180

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 . C2 . 1.2856(5) yes
O1 . C1 . 1.3240(5) yes
O2 . C1 . 1.2164(5) yes
O4 . C2 . 1.2369(5) yes
O5 . C15 . 1.2372(5) yes
O6 . C9 . 1.2383(5) yes
O1 . H1 . 1.049(8) yes
N1 . C19 . 1.3385(6) yes
N1 . C18 . 1.3396(6) yes
N2 . C15 . 1.3384(6) yes
N4 . C9 . 1.3307(6) yes
N3 . C12 . 1.3404(6) yes
N3 . C13 . 1.3410(6) yes
N2 . H2A . 0.998(7) yes
N2 . H2B . 1.030(6) yes
N4 . H4A . 1.022(6) yes
N4 . H4B . 1.005(6) yes
N3 . H3 . 1.144(8) yes
C4 . C1 . 1.4946(6) yes
C4 . C3 . 1.4067(6) yes
C4 . C5 . 1.3992(6) yes
C2 . C3 . 1.5128(6) yes
C7 . C6 . 1.3961(7) yes
C7 . C8 . 1.3969(7) yes
C3 . C8 . 1.3966(6) yes
C5 . C6 . 1.3953(7) yes
C15 . C16 . 1.5052(6) yes
C20 . C16 . 1.3941(6) yes
C20 . C19 . 1.3903(6) yes
C16 . C17 . 1.3927(6) yes
C17 . C18 . 1.3941(6) yes
C9 . C10 . 1.5102(6) yes
C11 . C10 . 1.3934(6) yes
C11 . C12 . 1.3829(6) yes
C10 . C14 . 1.3963(6) yes
C14 . C13 . 1.3885(7) yes
C7 . H7 . 1.082(6) yes
C5 . H5 . 1.084(6) yes
C6 . H6 . 1.092(6) yes
C8 . H8 . 1.074(6) yes
C20 . H20 . 1.094(6) yes
C19 . H19 . 1.090(6) yes
C17 . H17 . 1.062(6) yes
C18 . H18 . 1.080(6) yes
C11 . H11 . 1.073(6) yes
C14 . H14 . 1.082(6) yes
C12 . H12 . 1.083(6) yes
C13 . H13 . 1.071(6) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 . C2 . O4 . 124.70(4) yes
O1 . C1 . O2 . 123.88(4) yes
O5 . C15 . N2 . 122.76(4) yes
O6 . C9 . N4 . 124.06(4) yes
O3 . C2 . C3 . 115.41(4) yes
O1 . C1 . C4 . 113.95(4) yes
O2 . C1 . C4 . 122.17(4) yes
O4 . C2 . C3 . 119.75(4) yes
O5 . C15 . C16 . 118.23(4) yes
O6 . C9 . C10 . 119.12(4) yes
N1 . C19 . C20 . 122.75(4) yes
N1 . C18 . C17 . 123.05(4) yes
N2 . C15 . C16 . 119.01(4) yes
N4 . C9 . C10 . 116.82(4) yes
N3 . C12 . C11 . 120.92(4) yes
N3 . C13 . C14 . 120.70(5) yes
N1 . C19 . H19 . 115.4(3) yes
N1 . C18 . H18 . 115.1(3) yes
N3 . C12 . H12 . 115.4(3) yes
N3 . C13 . H13 . 116.3(3) yes
C1 . O1 . H1 . 110.0(4) yes
C19 . N1 . C18 . 118.11(4) yes
C12 . N3 . C13 . 121.23(4) yes
C15 . N2 . H2A . 122.7(4) yes
C15 . N2 . H2B . 116.7(4) yes
C9 . N4 . H4A . 116.0(4) yes
C9 . N4 . H4B . 122.0(4) yes
C12 . N3 . H3 . 120.1(3) yes
C13 . N3 . H3 . 118.7(3) yes
C4 . C3 . C2 . 122.93(4) yes
C4 . C3 . C8 . 119.21(4) yes
C4 . C5 . C6 . 120.70(5) yes
C2 . C3 . C8 . 117.80(4) yes
C1 . C4 . C3 . 119.88(4) yes
C1 . C4 . C5 . 120.39(4) yes
C7 . C6 . C5 . 119.76(4) yes
C7 . C8 . C3 . 121.00(5) yes
C3 . C4 . C5 . 119.65(4) yes
C6 . C7 . C8 . 119.68(4) yes
C15 . C16 . C20 . 117.61(4) yes
C15 . C16 . C17 . 124.11(4) yes
C20 . C16 . C17 . 118.28(4) yes
C16 . C20 . C19 . 119.12(4) yes
C16 . C17 . C18 . 118.66(4) yes
C9 . C10 . C11 . 118.13(4) yes
C9 . C10 . C14 . 122.74(4) yes
C11 . C10 . C14 . 119.12(4) yes
C10 . C11 . C12 . 119.08(4) yes
C10 . C14 . C13 . 118.94(4) yes
C4 . C5 . H5 . 119.2(3) yes
C7 . C6 . H6 . 120.3(3) yes
C7 . C8 . H8 . 119.4(3) yes
C3 . C8 . H8 . 119.6(3) yes
C5 . C6 . H6 . 119.9(3) yes
C6 . C7 . H7 . 120.3(3) yes
C6 . C5 . H5 . 120.1(3) yes
C8 . C7 . H7 . 120.0(3) yes
C20 . C19 . H19 . 121.9(3) yes
C16 . C20 . H20 . 119.7(3) yes
C16 . C17 . H17 . 122.9(3) yes
C19 . C20 . H20 . 121.2(3) yes
C17 . C18 . H18 . 121.8(3) yes
C18 . C17 . H17 . 118.4(3) yes
C11 . C12 . H12 . 123.7(3) yes
C10 . C11 . H11 . 120.9(3) yes
C10 . C14 . H14 . 121.1(3) yes
C14 . C13 . H13 . 123.0(3) yes
C12 . C11 . H11 . 120.0(3) yes
C13 . C14 . H14 . 119.9(3) yes
H2A . N2 . H2B . 120.7(5) yes
H4A . N4 . H4B . 119.3(5) yes
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex7_150K_har
_database_code_depnum_ccdc_archive 'CCDC 1922037'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex7_150K_har   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.28 %
RESPONSE: Data collection at non-standard wavelength. Fprime used for anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex7_150K_har   
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.21 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a  very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT353_complex7_150K_har_2 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H1       .       1.14 Ang.
RESPONSE: The long N-H distance is characteristic of H1 being in a  very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT430_complex7_150K_har   
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.78 Ang.
RESPONSE: Atoms O9 and N6 are in different layers of the crystal structure even though they are close in distance.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-5
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            150K
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_weight         668.4945
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       344
_QCr_calc_unit_n_alpha_electrons 172
_QCr_calc_unit_n_beta_electrons  172

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_F_000             688

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'p -1'
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'

# =========
# Unit cell
# =========

_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      43.82

_cell_length_a                   9.6632(4)
_cell_length_b                   10.3059(4)
_cell_length_c                   15.2750(6)
_cell_angle_alpha                79.0739(18)
_cell_angle_beta                 71.8454(18)
_cell_angle_gamma                77.2714(19)
_cell_volume                     1397.91(10)

_cell_formula_units_Z            2.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6632
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.546
_diffrn_reflns_theta_max         35.634
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            215.278547

_reflns_d_resolution_high        9.966755
_reflns_d_resolution_low         0.760099
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                5555
_reflns_number_total             5555
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0286
_refine_ls_R_factor_all          0.0286
_refine_ls_wR_factor_gt          0.0275
_refine_ls_wR_factor_all         0.0275
_refine_ls_R_Fsqd_factor         0.0446
_refine_ls_goodness_of_fit_gt    1.1839
_refine_ls_goodness_of_fit_all   1.1839
_refine_ls_number_reflns         5555
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0034
_refine_ls_shift/su_max_mean     0.0004
_refine_ls_shift/su_max_par      'H10 Uyy'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1881
_refine_diff_density_min         -0.2216
_refine_diff_density_rms         0.0450
_refine_diff_density_max_atom    0.0747
_refine_diff_density_max_atom_tag H19
_refine_diff_density_min_atom    -0.1035
_refine_diff_density_min_atom_tag N1
_refine_diff_density_rms_atom    0.0379

_refine_special_details          
;
  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 150K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  150K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

150k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H19 1.478273 0.803228 0.123130 0.051273 Uani 1.000000 0 0.001252 0.001168
0.000731 0.008086
H5 0.814896 0.652998 0.163909 0.049328 Uani 1.000000 0 0.001206 0.001066
0.000786 0.007860
H10 -0.034425 0.344519 0.684224 0.057473 Uani 1.000000 0 0.001306 0.001068
0.000850 0.008640
H4 0.611928 0.564981 0.294148 0.044843 Uani 1.000000 0 0.001148 0.001122
0.000762 0.007511
H18 1.288235 0.652530 0.193466 0.053923 Uani 1.000000 0 0.001314 0.001098
0.000800 0.008098
H20 1.494538 0.731132 -0.148484 0.043444 Uani 1.000000 0 0.001171 0.001078
0.000762 0.007489
H3 0.399349 0.942990 0.350364 0.053993 Uani 1.000000 0 0.001254 0.001099
0.000806 0.008279
H6 0.598077 1.050236 0.225650 0.046262 Uani 1.000000 0 0.001155 0.001088
0.000751 0.007639
H17 1.098063 0.076972 0.158018 0.060175 Uani 1.000000 0 0.001327 0.001114
0.000869 0.008629
H15 0.897970 -0.037463 0.279149 0.050820 Uani 1.000000 0 0.001203 0.001108
0.000803 0.008074
H11 0.079461 0.166693 0.435506 0.041175 Uani 1.000000 0 0.001169 0.001121
0.000692 0.007439
H9 0.153128 0.492388 0.610313 0.054164 Uani 1.000000 0 0.001236 0.001133
0.000749 0.008186
H13 0.468135 0.115187 0.494296 0.046117 Uani 1.000000 0 0.001393 0.001135
0.000899 0.008692
H7 1.048442 0.887910 0.029249 0.044591 Uani 1.000000 0 0.001290 0.001150
0.000859 0.008349
H12 0.537365 0.262813 0.431489 0.046553 Uani 1.000000 0 0.001373 0.001270
0.000906 0.009055
H14 0.726437 0.337704 0.387841 0.073754 Uani 1.000000 0 0.001447 0.001143
0.000879 0.009886
H1 0.417697 0.702088 0.382500 0.032036 Uani 1.000000 0 0.001573 0.001205
0.000964 0.009240
H8 0.995900 0.750019 0.112153 0.045102 Uani 1.000000 0 0.001286 0.001233
0.000871 0.008826
H16 0.931805 0.434828 0.260315 0.071964 Uani 1.000000 0 0.001388 0.001256
0.000850 0.009661
H2 1.109489 0.318338 0.152424 0.034331 Uani 1.000000 0 0.001654 0.001381
0.000969 0.010229
O2 1.629777 0.900434 -0.140019 0.029060 Uani 1.000000 0 0.000068 0.000060
0.000042 0.000354
O1 1.661602 0.894918 -0.006524 0.037757 Uani 1.000000 0 0.000076 0.000070
0.000046 0.000400
O3 1.364110 0.566765 -0.171156 0.053058 Uani 1.000000 0 0.000087 0.000083
0.000050 0.000497
O4 1.157446 0.563633 -0.065171 0.041234 Uani 1.000000 0 0.000077 0.000073
0.000047 0.000424
O5 1.207499 0.397084 0.099310 0.022632 Uani 1.000000 0 0.000063 0.000055
0.000040 0.000326
O6 1.055519 0.571244 0.166133 0.024553 Uani 1.000000 0 0.000062 0.000054
0.000041 0.000326
N8 1.602979 0.862647 -0.057055 0.021190 Uani 1.000000 0 0.000077 0.000068
0.000050 0.000389
N7 1.283801 0.583625 -0.093714 0.027255 Uani 1.000000 0 0.000087 0.000074
0.000053 0.000432
C5 1.493901 0.773933 -0.015410 0.017391 Uani 1.000000 0 0.000086 0.000076
0.000055 0.000418
C3 1.342509 0.634658 -0.032043 0.017094 Uani 1.000000 0 0.000087 0.000077
0.000055 0.000412
C4 1.448810 0.715396 -0.073700 0.017827 Uani 1.000000 0 0.000092 0.000081
0.000062 0.000433
C2 1.284668 0.608427 0.063817 0.017255 Uani 1.000000 0 0.000085 0.000076
0.000055 0.000412
C1 1.171213 0.518957 0.112904 0.018927 Uani 1.000000 0 0.000089 0.000081
0.000056 0.000431
C7 1.334459 0.670031 0.119431 0.022650 Uani 1.000000 0 0.000100 0.000088
0.000065 0.000474
C6 1.438330 0.753712 0.080398 0.022523 Uani 1.000000 0 0.000098 0.000090
0.000062 0.000479
C10 0.727135 0.721831 0.204410 0.021809 Uani 1.000000 0 0.000101 0.000089
0.000063 0.000471
C13 0.495354 0.886192 0.309130 0.022990 Uani 1.000000 0 0.000105 0.000091
0.000064 0.000485
C11 0.615712 0.670610 0.275218 0.021933 Uani 1.000000 0 0.000096 0.000095
0.000062 0.000468
C8 0.840800 0.924914 0.112106 0.019673 Uani 1.000000 0 0.000090 0.000081
0.000057 0.000435
C12 0.603908 0.942821 0.239526 0.021265 Uani 1.000000 0 0.000095 0.000092
0.000061 0.000461
C9 0.723029 0.860432 0.187054 0.018179 Uani 1.000000 0 0.000088 0.000079
0.000056 0.000421
O12 0.813311 1.044819 0.082957 0.024548 Uani 1.000000 0 0.000063 0.000054
0.000040 0.000332
N3 0.970762 0.846720 0.082815 0.029944 Uani 1.000000 0 0.000090 0.000091
0.000063 0.000486
N2 0.504571 0.752519 0.325832 0.020947 Uani 1.000000 0 0.000082 0.000073
0.000051 0.000395
C17 0.797110 0.143864 0.341364 0.017665 Uani 1.000000 0 0.000088 0.000078
0.000055 0.000418
C16 0.676127 0.078300 0.411262 0.018191 Uani 1.000000 0 0.000089 0.000079
0.000057 0.000423
C18 0.902882 0.068897 0.276709 0.023383 Uani 1.000000 0 0.000096 0.000093
0.000063 0.000477
C15 0.806114 0.277082 0.338330 0.029342 Uani 1.000000 0 0.000111 0.000093
0.000069 0.000528
C14 0.917798 0.331051 0.269952 0.029624 Uani 1.000000 0 0.000107 0.000097
0.000067 0.000525
C19 1.012611 0.129058 0.210318 0.025868 Uani 1.000000 0 0.000104 0.000093
0.000068 0.000504
O8 0.470393 0.438666 0.405118 0.028112 Uani 1.000000 0 0.000063 0.000055
0.000043 0.000348
O11 -0.167747 0.168914 0.689992 0.032668 Uani 1.000000 0 0.000068 0.000062
0.000044 0.000378
O9 0.304816 0.621340 0.445273 0.022789 Uani 1.000000 0 0.000062 0.000054
0.000040 0.000322
O10 -0.125977 0.095339 0.559576 0.034876 Uani 1.000000 0 0.000071 0.000062
0.000049 0.000385
N5 0.282298 0.313940 0.336701 0.026113 Uani 1.000000 0 0.000084 0.000078
0.000050 0.000423
N6 -0.102836 0.165629 0.607666 0.024080 Uani 1.000000 0 0.000078 0.000070
0.000054 0.000409
O13 0.336037 0.203793 0.312961 0.051637 Uani 1.000000 0 0.000093 0.000071
0.000049 0.000487
O14 0.291805 0.418732 0.285213 0.041585 Uani 1.000000 0 0.000084 0.000068
0.000043 0.000430
O7 0.693225 -0.045242 0.426653 0.026253 Uani 1.000000 0 0.000064 0.000054
0.000042 0.000340
N1 1.017897 0.258010 0.207882 0.020460 Uani 1.000000 0 0.000082 0.000070
0.000051 0.000391
N4 0.554708 0.159096 0.451951 0.025916 Uani 1.000000 0 0.000089 0.000090
0.000059 0.000455
C21 0.222783 0.413401 0.481604 0.017364 Uani 1.000000 0 0.000087 0.000078
0.000056 0.000414
C20 0.344005 0.497781 0.439607 0.018444 Uani 1.000000 0 0.000092 0.000080
0.000055 0.000425
C24 0.009859 0.250764 0.564182 0.019275 Uani 1.000000 0 0.000087 0.000078
0.000058 0.000427
C25 0.029332 0.339432 0.615242 0.023830 Uani 1.000000 0 0.000104 0.000093
0.000067 0.000485
C22 0.198332 0.321551 0.434198 0.017932 Uani 1.000000 0 0.000088 0.000078
0.000054 0.000418
C23 0.093918 0.238576 0.473437 0.020027 Uani 1.000000 0 0.000095 0.000087
0.000063 0.000461
C26 0.136312 0.419903 0.572985 0.023078 Uani 1.000000 0 0.000100 0.000092
0.000062 0.000481

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H19 1.4783(13) 0.8032(12) 0.1231(7) 0.051(8) Uani 1.000000 0
H5 0.8149(12) 0.6530(11) 0.1639(8) 0.049(8) Uani 1.000000 0
H10 -0.0344(13) 0.3445(11) 0.6842(9) 0.057(9) Uani 1.000000 0
H4 0.6119(11) 0.5650(11) 0.2941(8) 0.045(8) Uani 1.000000 0
H18 1.2882(13) 0.6525(11) 0.1935(8) 0.054(8) Uani 1.000000 0
H20 1.4945(12) 0.7311(11) -0.1485(8) 0.043(7) Uani 1.000000 0
H3 0.3993(13) 0.9430(11) 0.3504(8) 0.054(8) Uani 1.000000 0
H6 0.5981(12) 1.0502(11) 0.2256(8) 0.046(8) Uani 1.000000 0
H17 1.0981(13) 0.0770(11) 0.1580(9) 0.060(9) Uani 1.000000 0
H15 0.8980(12) -0.0375(11) 0.2791(8) 0.051(8) Uani 1.000000 0
H11 0.0795(12) 0.1667(11) 0.4355(7) 0.041(7) Uani 1.000000 0
H9 0.1531(12) 0.4924(11) 0.6103(7) 0.054(8) Uani 1.000000 0
H13 0.4681(14) 0.1152(11) 0.4943(9) 0.046(9) Uani 1.000000 0
H7 1.0484(13) 0.8879(11) 0.0292(9) 0.045(8) Uani 1.000000 0
H12 0.5374(14) 0.2628(13) 0.4315(9) 0.047(9) Uani 1.000000 0
H14 0.7264(14) 0.3377(11) 0.3878(9) 0.074(10) Uani 1.000000 0
H1 0.4177(16) 0.7021(12) 0.3825(10) 0.032(9) Uani 1.000000 0
H8 0.9959(13) 0.7500(12) 0.1122(9) 0.045(9) Uani 1.000000 0
H16 0.9318(14) 0.4348(13) 0.2603(9) 0.072(10) Uani 1.000000 0
H2 1.1095(17) 0.3183(14) 0.1524(10) 0.034(10) Uani 1.000000 0
O2 1.62978(7) 0.90043(6) -0.14002(4) 0.0291(4) Uani 1.000000 0
O1 1.66160(8) 0.89492(7) -0.00652(5) 0.0378(4) Uani 1.000000 0
O3 1.36411(9) 0.56677(8) -0.17116(5) 0.0531(5) Uani 1.000000 0
O4 1.15745(8) 0.56363(7) -0.06517(5) 0.0412(4) Uani 1.000000 0
O5 1.20750(6) 0.39708(6) 0.09931(4) 0.0226(3) Uani 1.000000 0
O6 1.05552(6) 0.57124(5) 0.16613(4) 0.0246(3) Uani 1.000000 0
N8 1.60298(8) 0.86265(7) -0.05706(5) 0.0212(4) Uani 1.000000 0
N7 1.28380(9) 0.58363(7) -0.09371(5) 0.0273(4) Uani 1.000000 0
C5 1.49390(9) 0.77393(8) -0.01541(6) 0.0174(4) Uani 1.000000 0
C3 1.34251(9) 0.63466(8) -0.03204(5) 0.0171(4) Uani 1.000000 0
C4 1.44881(9) 0.71540(8) -0.07370(6) 0.0178(4) Uani 1.000000 0
C2 1.28467(9) 0.60843(8) 0.06382(6) 0.0173(4) Uani 1.000000 0
C1 1.17121(9) 0.51896(8) 0.11290(6) 0.0189(4) Uani 1.000000 0
C7 1.33446(10) 0.67003(9) 0.11943(6) 0.0226(5) Uani 1.000000 0
C6 1.43833(10) 0.75371(9) 0.08040(6) 0.0225(5) Uani 1.000000 0
C10 0.72714(10) 0.72183(9) 0.20441(6) 0.0218(5) Uani 1.000000 0
C13 0.49535(10) 0.88619(9) 0.30913(6) 0.0230(5) Uani 1.000000 0
C11 0.61571(10) 0.67061(9) 0.27522(6) 0.0219(5) Uani 1.000000 0
C8 0.84080(9) 0.92491(8) 0.11211(6) 0.0197(4) Uani 1.000000 0
C12 0.60391(10) 0.94282(9) 0.23953(6) 0.0213(5) Uani 1.000000 0
C9 0.72303(9) 0.86043(8) 0.18705(6) 0.0182(4) Uani 1.000000 0
O12 0.81331(6) 1.04482(5) 0.08296(4) 0.0245(3) Uani 1.000000 0
N3 0.97076(9) 0.84672(9) 0.08281(6) 0.0299(5) Uani 1.000000 0
N2 0.50457(8) 0.75252(7) 0.32583(5) 0.0209(4) Uani 1.000000 0
C17 0.79711(9) 0.14386(8) 0.34136(5) 0.0177(4) Uani 1.000000 0
C16 0.67613(9) 0.07830(8) 0.41126(6) 0.0182(4) Uani 1.000000 0
C18 0.90288(10) 0.06890(9) 0.27671(6) 0.0234(5) Uani 1.000000 0
C15 0.80611(11) 0.27708(9) 0.33833(7) 0.0293(5) Uani 1.000000 0
C14 0.91780(11) 0.33105(10) 0.26995(7) 0.0296(5) Uani 1.000000 0
C19 1.01261(10) 0.12906(9) 0.21032(7) 0.0259(5) Uani 1.000000 0
O8 0.47039(6) 0.43867(6) 0.40512(4) 0.0281(3) Uani 1.000000 0
O11 -0.16775(7) 0.16891(6) 0.68999(4) 0.0327(4) Uani 1.000000 0
O9 0.30482(6) 0.62134(5) 0.44527(4) 0.0228(3) Uani 1.000000 0
O10 -0.12598(7) 0.09534(6) 0.55958(5) 0.0349(4) Uani 1.000000 0
N5 0.28230(8) 0.31394(8) 0.33670(5) 0.0261(4) Uani 1.000000 0
N6 -0.10284(8) 0.16563(7) 0.60767(5) 0.0241(4) Uani 1.000000 0
O13 0.33604(9) 0.20379(7) 0.31296(5) 0.0516(5) Uani 1.000000 0
O14 0.29181(8) 0.41873(7) 0.28521(4) 0.0416(4) Uani 1.000000 0
O7 0.69322(6) -0.04524(5) 0.42665(4) 0.0263(3) Uani 1.000000 0
N1 1.01790(8) 0.25801(7) 0.20788(5) 0.0205(4) Uani 1.000000 0
N4 0.55471(9) 0.15910(9) 0.45195(6) 0.0259(5) Uani 1.000000 0
C21 0.22278(9) 0.41340(8) 0.48160(6) 0.0174(4) Uani 1.000000 0
C20 0.34400(9) 0.49778(8) 0.43961(6) 0.0184(4) Uani 1.000000 0
C24 0.00986(9) 0.25076(8) 0.56418(6) 0.0193(4) Uani 1.000000 0
C25 0.02933(10) 0.33943(9) 0.61524(7) 0.0238(5) Uani 1.000000 0
C22 0.19833(9) 0.32155(8) 0.43420(5) 0.0179(4) Uani 1.000000 0
C23 0.09392(10) 0.23858(9) 0.47344(6) 0.0200(5) Uani 1.000000 0
C26 0.13631(10) 0.41990(9) 0.57299(6) 0.0231(5) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H19 0.057736 0.074048 0.031648 -0.037565 -0.013763 0.002621 0.007018 0.010049
0.007731 0.007078 0.006144 0.006807
H5 0.032109 0.040785 0.057625 -0.019660 0.018082 -0.000991 0.006942 0.007763
0.007889 0.005986 0.005963 0.006226
H10 0.060557 0.041370 0.067447 -0.018905 -0.005585 -0.009109 0.008059 0.008228
0.009548 0.006495 0.007476 0.007304
H4 0.033963 0.046914 0.053398 -0.015141 -0.003758 -0.010909 0.006394 0.007785
0.008356 0.005895 0.005904 0.006593
H18 0.061788 0.059014 0.044887 -0.039253 -0.007816 0.005268 0.007297 0.009043
0.008062 0.006553 0.006403 0.006959
H20 0.033108 0.056072 0.039113 -0.022526 -0.003576 0.004826 0.006235 0.008526
0.007548 0.005696 0.005751 0.006485
H3 0.040007 0.050760 0.063053 -0.014851 0.000823 -0.005671 0.007260 0.008136
0.008891 0.006246 0.006494 0.006858
H6 0.034560 0.038904 0.051911 -0.007414 0.009499 -0.009268 0.007015 0.007275
0.007942 0.005913 0.005947 0.006225
H17 0.054791 0.047819 0.075792 -0.031144 0.011620 -0.027876 0.007947 0.008385
0.009398 0.006752 0.006973 0.007174
H15 0.039463 0.039922 0.066919 -0.016183 0.006257 -0.017347 0.007084 0.007771
0.008932 0.006191 0.006349 0.006696
H11 0.038063 0.057328 0.026977 -0.012726 -0.003674 -0.006799 0.006595 0.008411
0.007329 0.006093 0.005625 0.006144
H9 0.053011 0.062353 0.043655 -0.033406 0.014028 -0.018102 0.007589 0.009193
0.007729 0.007002 0.006059 0.006644
H13 0.035088 0.031756 0.057858 0.005276 -0.005610 0.001315 0.007782 0.007711
0.009799 0.006256 0.007152 0.006863
H7 0.025061 0.040751 0.049507 -0.002490 0.009759 0.000308 0.007404 0.007992
0.008465 0.006144 0.006544 0.006672
H12 0.048088 0.015655 0.063942 0.002758 -0.001367 -0.010572 0.008775 0.007329
0.010343 0.006918 0.007509 0.007369
H14 0.074198 0.044913 0.080171 -0.038562 0.034032 -0.016999 0.010011 0.008948
0.009526 0.007712 0.007718 0.007341
H1 0.039708 0.016977 0.043919 -0.012729 -0.015182 0.000164 0.008495 0.008046
0.011933 0.006705 0.008594 0.007851
H8 0.034209 0.025117 0.059058 0.011091 -0.008377 0.008120 0.008012 0.007437
0.009823 0.006519 0.007097 0.007072
H16 0.072601 0.061150 0.066300 -0.041007 0.032315 -0.023912 0.009783 0.009639
0.008925 0.008102 0.007322 0.007426
H2 0.036085 0.032959 0.030042 0.005294 -0.006469 -0.012731 0.009954 0.009138
0.012661 0.007939 0.010127 0.008805
O2 0.028919 0.031698 0.026029 -0.018701 -0.002079 0.003657 0.000315 0.000387
0.000351 0.000285 0.000268 0.000289
O1 0.040702 0.049041 0.032484 -0.032582 -0.008661 -0.000589 0.000336 0.000480
0.000412 0.000337 0.000309 0.000346
O3 0.053863 0.082160 0.034058 -0.034993 0.000540 -0.028555 0.000438 0.000626
0.000469 0.000428 0.000374 0.000438
O4 0.038620 0.061152 0.034671 -0.031659 -0.015489 0.003666 0.000326 0.000530
0.000434 0.000339 0.000309 0.000377
O5 0.017330 0.016531 0.027473 -0.006282 0.005276 -0.002861 0.000292 0.000323
0.000341 0.000248 0.000256 0.000262
O6 0.016752 0.015157 0.032823 -0.004758 0.005533 -0.000595 0.000288 0.000311
0.000347 0.000243 0.000257 0.000260
N8 0.020434 0.021394 0.021804 -0.011533 -0.002160 -0.000139 0.000339 0.000401
0.000415 0.000297 0.000303 0.000319
N7 0.029510 0.033073 0.023812 -0.016983 -0.006331 -0.003302 0.000382 0.000467
0.000457 0.000347 0.000342 0.000363
C5 0.015996 0.017111 0.017796 -0.006391 -0.001217 -0.001112 0.000364 0.000429
0.000444 0.000322 0.000324 0.000342
C3 0.015588 0.017075 0.017478 -0.006380 -0.000966 -0.001620 0.000360 0.000425
0.000442 0.000318 0.000324 0.000342
C4 0.017442 0.018270 0.016057 -0.007556 0.000493 -0.001745 0.000385 0.000437
0.000456 0.000329 0.000347 0.000367
C2 0.015133 0.015687 0.018416 -0.006460 0.000196 -0.000063 0.000362 0.000412
0.000438 0.000315 0.000326 0.000337
C1 0.013899 0.014899 0.023080 -0.004313 0.001828 -0.000509 0.000372 0.000445
0.000450 0.000331 0.000334 0.000358
C7 0.025382 0.026184 0.015986 -0.013280 -0.000362 -0.000753 0.000431 0.000505
0.000475 0.000375 0.000373 0.000402
C6 0.024780 0.026440 0.018174 -0.014151 -0.002574 -0.001825 0.000423 0.000509
0.000491 0.000380 0.000368 0.000389
C10 0.017396 0.016647 0.025685 -0.005747 0.001950 0.000595 0.000408 0.000483
0.000491 0.000363 0.000359 0.000393
C13 0.017972 0.019078 0.025990 -0.006529 0.003498 -0.001252 0.000425 0.000497
0.000507 0.000374 0.000374 0.000403
C11 0.018384 0.015498 0.026524 -0.007198 0.001597 0.001763 0.000406 0.000484
0.000490 0.000372 0.000355 0.000398
C8 0.015324 0.015270 0.022779 -0.004362 -0.000165 0.004264 0.000378 0.000453
0.000450 0.000337 0.000334 0.000362
C12 0.017648 0.015579 0.026187 -0.005870 0.000319 0.000282 0.000399 0.000476
0.000491 0.000362 0.000352 0.000397
C9 0.014421 0.015919 0.020782 -0.006236 -0.000185 0.001933 0.000358 0.000451
0.000439 0.000324 0.000325 0.000355
O12 0.019308 0.016904 0.029455 -0.004956 0.000919 0.005059 0.000294 0.000327
0.000348 0.000252 0.000260 0.000266
N3 0.017682 0.020403 0.037429 -0.002332 0.005322 0.007294 0.000415 0.000471
0.000503 0.000365 0.000361 0.000394
N2 0.016982 0.020337 0.022438 -0.008573 0.000651 0.000344 0.000336 0.000420
0.000414 0.000303 0.000304 0.000343
C17 0.016558 0.014763 0.019008 -0.007238 0.000662 -0.000126 0.000365 0.000440
0.000436 0.000327 0.000325 0.000350
C16 0.016339 0.012438 0.022278 -0.005999 -0.000872 0.002542 0.000370 0.000442
0.000439 0.000325 0.000329 0.000351
C18 0.019327 0.015971 0.030274 -0.007990 0.003894 -0.004722 0.000416 0.000478
0.000511 0.000371 0.000367 0.000403
C15 0.029535 0.017862 0.030948 -0.012991 0.013877 -0.007552 0.000504 0.000515
0.000520 0.000420 0.000410 0.000420
C14 0.029989 0.017135 0.032013 -0.013725 0.013837 -0.006850 0.000501 0.000516
0.000515 0.000420 0.000402 0.000419
C19 0.020109 0.020159 0.030911 -0.008559 0.008260 -0.008181 0.000438 0.000506
0.000534 0.000384 0.000390 0.000418
O8 0.018429 0.014973 0.040004 -0.004071 0.005778 0.000278 0.000311 0.000321
0.000372 0.000256 0.000275 0.000271
O11 0.025909 0.031767 0.033481 -0.015251 0.003059 0.004803 0.000332 0.000394
0.000374 0.000290 0.000282 0.000302
O9 0.017129 0.014814 0.030580 -0.005295 0.002865 -0.002227 0.000284 0.000317
0.000346 0.000243 0.000255 0.000259
O10 0.026667 0.024546 0.050642 -0.014046 0.002760 -0.010170 0.000327 0.000366
0.000446 0.000292 0.000310 0.000321
N5 0.032383 0.026047 0.016723 -0.009835 0.001966 -0.004624 0.000395 0.000460
0.000410 0.000344 0.000326 0.000358
N6 0.018057 0.017140 0.032065 -0.007253 0.000910 0.000147 0.000346 0.000386
0.000462 0.000302 0.000318 0.000329
O13 0.072721 0.036840 0.032080 -0.014720 0.015998 -0.018708 0.000554 0.000450
0.000437 0.000406 0.000393 0.000358
O14 0.057224 0.040724 0.019202 -0.015084 -0.000128 0.004046 0.000448 0.000453
0.000373 0.000363 0.000331 0.000331
O7 0.019932 0.013750 0.035877 -0.005454 0.002939 0.003505 0.000302 0.000322
0.000366 0.000253 0.000267 0.000268
N1 0.018065 0.018325 0.021383 -0.007973 0.002314 -0.001639 0.000344 0.000405
0.000404 0.000301 0.000302 0.000330
N4 0.019782 0.015618 0.033222 -0.005710 0.004729 0.001134 0.000403 0.000448
0.000475 0.000354 0.000341 0.000371
C21 0.016495 0.016445 0.016856 -0.006882 0.001251 -0.002038 0.000371 0.000419
0.000432 0.000321 0.000324 0.000336
C20 0.015957 0.012457 0.022590 -0.004762 0.001066 -0.000219 0.000378 0.000439
0.000442 0.000335 0.000332 0.000346
C24 0.015868 0.015405 0.023461 -0.005526 -0.000095 -0.001050 0.000374 0.000422
0.000458 0.000326 0.000336 0.000349
C25 0.022916 0.024686 0.019935 -0.011191 0.005582 -0.004863 0.000438 0.000506
0.000481 0.000379 0.000385 0.000411
C22 0.018275 0.016050 0.017131 -0.005117 -0.000371 -0.001864 0.000385 0.000420
0.000430 0.000328 0.000330 0.000340
C23 0.020161 0.016898 0.022002 -0.006978 -0.001043 -0.003979 0.000404 0.000461
0.000495 0.000349 0.000360 0.000376
C26 0.024824 0.023677 0.019409 -0.012638 0.003455 -0.006196 0.000433 0.000510
0.000478 0.000382 0.000367 0.000392

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 . N8 . 1.2155(9) yes
O1 . N8 . 1.2166(9) yes
O3 . N7 . 1.2158(9) yes
O4 . N7 . 1.2118(9) yes
O11 . N6 . 1.2212(9) yes
O10 . N6 . 1.2206(9) yes
O13 . N5 . 1.2119(9) yes
O14 . N5 . 1.2124(9) yes
O5 . C1 . 1.2661(9) yes
O6 . C1 . 1.2391(9) yes
O12 . C8 . 1.2314(9) yes
O8 . C20 . 1.2382(10) yes
O9 . C20 . 1.2575(9) yes
O7 . C16 . 1.2336(9) yes
N8 . C5 . 1.4622(10) yes
N7 . C3 . 1.4623(11) yes
N3 . C8 . 1.3294(11) yes
N2 . C13 . 1.3408(11) yes
N2 . C11 . 1.3395(11) yes
N5 . C22 . 1.4648(10) yes
N6 . C24 . 1.4650(10) yes
N1 . C14 . 1.3339(11) yes
N1 . C19 . 1.3342(11) yes
N4 . C16 . 1.3295(11) yes
N3 . H7 . 1.019(12) yes
N3 . H8 . 1.022(12) yes
N2 . H1 . 1.137(15) yes
N1 . H2 . 1.210(17) yes
N4 . H13 . 1.021(13) yes
N4 . H12 . 1.047(12) yes
C5 . C4 . 1.3812(12) yes
C5 . C6 . 1.3847(12) yes
C3 . C4 . 1.3860(11) yes
C3 . C2 . 1.3914(11) yes
C2 . C1 . 1.5118(11) yes
C2 . C7 . 1.3964(12) yes
C7 . C6 . 1.3857(12) yes
C10 . C11 . 1.3842(12) yes
C10 . C9 . 1.3965(12) yes
C13 . C12 . 1.3824(12) yes
C8 . C9 . 1.5101(11) yes
C12 . C9 . 1.3931(12) yes
C17 . C16 . 1.5033(11) yes
C17 . C18 . 1.3890(12) yes
C17 . C15 . 1.3859(12) yes
C18 . C19 . 1.3851(12) yes
C15 . C14 . 1.3809(12) yes
C21 . C20 . 1.5196(11) yes
C21 . C22 . 1.3933(11) yes
C21 . C26 . 1.3911(11) yes
C24 . C25 . 1.3843(12) yes
C24 . C23 . 1.3843(12) yes
C25 . C26 . 1.3900(12) yes
C22 . C23 . 1.3848(11) yes
C4 . H20 . 1.083(11) yes
C7 . H18 . 1.074(11) yes
C6 . H19 . 1.098(11) yes
C10 . H5 . 1.086(11) yes
C13 . H3 . 1.066(11) yes
C11 . H4 . 1.078(11) yes
C12 . H6 . 1.079(11) yes
C18 . H15 . 1.101(11) yes
C15 . H14 . 1.077(12) yes
C14 . H16 . 1.084(12) yes
C19 . H17 . 1.079(12) yes
C25 . H10 . 1.046(12) yes
C23 . H11 . 1.078(11) yes
C26 . H9 . 1.087(11) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . N8 . O1 . 123.62(7) yes
O3 . N7 . O4 . 124.23(8) yes
O11 . N6 . O10 . 123.89(7) yes
O13 . N5 . O14 . 124.63(8) yes
O2 . N8 . C5 . 118.34(7) yes
O1 . N8 . C5 . 118.05(7) yes
O3 . N7 . C3 . 117.74(7) yes
O4 . N7 . C3 . 118.01(7) yes
O11 . N6 . C24 . 118.02(7) yes
O10 . N6 . C24 . 118.10(7) yes
O13 . N5 . C22 . 117.94(7) yes
O14 . N5 . C22 . 117.42(7) yes
O5 . C1 . O6 . 126.82(7) yes
O8 . C20 . O9 . 126.79(7) yes
O12 . C8 . N3 . 123.99(8) yes
O7 . C16 . N4 . 123.92(8) yes
O5 . C1 . C2 . 116.73(7) yes
O6 . C1 . C2 . 116.33(7) yes
O12 . C8 . C9 . 119.38(7) yes
O8 . C20 . C21 . 117.42(7) yes
O9 . C20 . C21 . 115.78(7) yes
O7 . C16 . C17 . 119.14(7) yes
N8 . C5 . C4 . 118.38(7) yes
N8 . C5 . C6 . 118.89(7) yes
N7 . C3 . C4 . 116.94(7) yes
N7 . C3 . C2 . 119.89(7) yes
N3 . C8 . C9 . 116.62(7) yes
N2 . C13 . C12 . 120.08(9) yes
N2 . C11 . C10 . 120.68(9) yes
N5 . C22 . C21 . 119.35(7) yes
N5 . C22 . C23 . 117.21(7) yes
N6 . C24 . C25 . 119.05(7) yes
N6 . C24 . C23 . 118.54(7) yes
N1 . C14 . C15 . 121.79(9) yes
N1 . C19 . C18 . 120.76(9) yes
N4 . C16 . C17 . 116.92(7) yes
N2 . C13 . H3 . 116.1(6) yes
N2 . C11 . H4 . 115.6(6) yes
N1 . C14 . H16 . 113.8(6) yes
N1 . C19 . H17 . 115.7(6) yes
C13 . N2 . C11 . 121.70(8) yes
C14 . N1 . C19 . 120.41(8) yes
C13 . N2 . H1 . 122.2(6) yes
C11 . N2 . H1 . 116.1(6) yes
C8 . N3 . H7 . 117.0(6) yes
C8 . N3 . H8 . 123.3(7) yes
C16 . N4 . H13 . 117.2(6) yes
C16 . N4 . H12 . 122.3(7) yes
C14 . N1 . H2 . 114.5(6) yes
C19 . N1 . H2 . 125.1(6) yes
C5 . C4 . C3 . 116.88(8) yes
C5 . C6 . C7 . 118.62(9) yes
C3 . C2 . C1 . 125.24(7) yes
C3 . C2 . C7 . 117.62(7) yes
C4 . C5 . C6 . 122.72(8) yes
C4 . C3 . C2 . 123.04(8) yes
C2 . C7 . C6 . 121.09(8) yes
C1 . C2 . C7 . 117.14(7) yes
C10 . C9 . C8 . 122.62(7) yes
C10 . C9 . C12 . 118.75(8) yes
C13 . C12 . C9 . 119.73(8) yes
C11 . C10 . C9 . 119.01(8) yes
C8 . C9 . C12 . 118.61(7) yes
C17 . C18 . C19 . 119.54(8) yes
C17 . C15 . C14 . 118.82(9) yes
C16 . C17 . C18 . 118.95(7) yes
C16 . C17 . C15 . 122.38(8) yes
C18 . C17 . C15 . 118.67(8) yes
C21 . C22 . C23 . 123.40(7) yes
C21 . C26 . C25 . 121.76(9) yes
C20 . C21 . C22 . 122.78(7) yes
C20 . C21 . C26 . 120.11(7) yes
C24 . C25 . C26 . 118.42(8) yes
C24 . C23 . C22 . 117.00(8) yes
C25 . C24 . C23 . 122.42(8) yes
C22 . C21 . C26 . 117.00(7) yes
C5 . C4 . H20 . 121.8(6) yes
C5 . C6 . H19 . 119.4(6) yes
C3 . C4 . H20 . 121.3(6) yes
C2 . C7 . H18 . 118.2(6) yes
C7 . C6 . H19 . 122.0(6) yes
C6 . C7 . H18 . 120.7(6) yes
C10 . C11 . H4 . 123.7(6) yes
C13 . C12 . H6 . 120.8(5) yes
C11 . C10 . H5 . 119.0(5) yes
C12 . C13 . H3 . 123.8(6) yes
C9 . C10 . H5 . 122.0(5) yes
C9 . C12 . H6 . 119.5(5) yes
C17 . C18 . H15 . 119.3(6) yes
C17 . C15 . H14 . 120.5(6) yes
C18 . C19 . H17 . 123.5(6) yes
C15 . C14 . H16 . 124.4(6) yes
C14 . C15 . H14 . 120.7(6) yes
C19 . C18 . H15 . 121.1(6) yes
C21 . C26 . H9 . 117.7(5) yes
C24 . C25 . H10 . 120.5(6) yes
C24 . C23 . H11 . 121.3(5) yes
C25 . C26 . H9 . 120.6(5) yes
C22 . C23 . H11 . 121.7(5) yes
C26 . C25 . H10 . 121.1(6) yes
H13 . N4 . H12 . 119.2(9) yes
H7 . N3 . H8 . 119.7(9) yes
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate 2:2'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex7_100K_har
_database_code_depnum_ccdc_archive 'CCDC 1922035'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex7_100K_har   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.41 %
RESPONSE:  Data collection at non-standard wavelength. Fprime used for anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex7_100K_har   
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.20 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a  very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT353_complex7_100K_har_2 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H1       .       1.12 Ang.
RESPONSE: The long N-H distance is characteristic of H1 being in a  very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT430_complex7_100K_har   
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.76 Ang.
RESPONSE: O9 and N6 are in different layers of the crystal structure. 
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-5
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            100K
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_weight         668.4945
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       344
_QCr_calc_unit_n_alpha_electrons 172
_QCr_calc_unit_n_beta_electrons  172

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             688

# ==============
# Absortion data
# ==============
_exptl_absorpt_coefficient_mu    0.181
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;


# ========
# Symmetry
# ========

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'p -1'
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'

# =========
# Unit cell
# =========

_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      43.79

_cell_length_a                   9.6450(4)
_cell_length_b                   10.2722(4)
_cell_length_c                   15.2241(6)
_cell_angle_alpha                79.3772(18)
_cell_angle_beta                 72.0170(17)
_cell_angle_gamma                77.3694(18)
_cell_volume                     1388.79(10)

_cell_formula_units_Z            2.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'


# ================
# Diffraction data
# ================

_diffrn_reflns_number            21882
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         35.633
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            215.183535

_reflns_d_resolution_high        9.943881
_reflns_d_resolution_low         0.760057
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                5773
_reflns_number_total             5773
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0241
_refine_ls_R_factor_all          0.0241
_refine_ls_wR_factor_gt          0.0251
_refine_ls_wR_factor_all         0.0251
_refine_ls_R_Fsqd_factor         0.0433
_refine_ls_goodness_of_fit_gt    1.1765
_refine_ls_goodness_of_fit_all   1.1765
_refine_ls_number_reflns         5773
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0043
_refine_ls_shift/su_max_mean     0.0004
_refine_ls_shift/su_max_par      'H13 Uyy'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1759
_refine_diff_density_min         -0.2009
_refine_diff_density_rms         0.0448
_refine_diff_density_max_atom    0.0550
_refine_diff_density_max_atom_tag H5
_refine_diff_density_min_atom    -0.0967
_refine_diff_density_min_atom_tag O2
_refine_diff_density_rms_atom    0.0360

_refine_special_details          
;
  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field
   
. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 100K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  100K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

100k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H19 1.477859 0.805689 0.122857 0.039394 Uani 1.000000 0 0.001103 0.001001
0.000605 0.006719
H5 0.814170 0.655071 0.164702 0.037025 Uani 1.000000 0 0.001062 0.000911
0.000676 0.006445
H10 -0.037610 0.347209 0.685358 0.039298 Uani 1.000000 0 0.001037 0.000940
0.000662 0.006660
H4 0.609610 0.567218 0.295381 0.034397 Uani 1.000000 0 0.001033 0.000984
0.000623 0.006353
H18 1.290440 0.653975 0.194517 0.038819 Uani 1.000000 0 0.001093 0.000933
0.000682 0.006519
H20 1.496697 0.730932 -0.149076 0.038220 Uani 1.000000 0 0.001102 0.000996
0.000674 0.006698
H3 0.398961 0.948093 0.352790 0.042307 Uani 1.000000 0 0.001119 0.000891
0.000684 0.006865
H6 0.597798 1.054610 0.226227 0.035167 Uani 1.000000 0 0.001037 0.000919
0.000653 0.006422
H17 1.103500 0.071778 0.159972 0.044320 Uani 1.000000 0 0.001137 0.000921
0.000711 0.006944
H15 0.902349 -0.038237 0.281370 0.044750 Uani 1.000000 0 0.001093 0.001008
0.000714 0.007027
H11 0.077527 0.168125 0.433351 0.036431 Uani 1.000000 0 0.000991 0.000994
0.000659 0.006662
H9 0.150981 0.493936 0.611664 0.037360 Uani 1.000000 0 0.001011 0.000967
0.000632 0.006510
H13 0.469285 0.116352 0.493382 0.040001 Uani 1.000000 0 0.001286 0.001049
0.000792 0.007662
H7 1.047673 0.886900 0.029149 0.042262 Uani 1.000000 0 0.001257 0.001061
0.000790 0.007756
H12 0.537024 0.262417 0.429611 0.035617 Uani 1.000000 0 0.001197 0.001097
0.000799 0.007515
H14 0.723909 0.341842 0.383929 0.054057 Uani 1.000000 0 0.001203 0.000966
0.000727 0.007732
H1 0.416953 0.705988 0.382687 0.024856 Uani 1.000000 0 0.001312 0.001126
0.000825 0.007809
H8 0.990453 0.750067 0.114132 0.037267 Uani 1.000000 0 0.001201 0.001109
0.000735 0.007656
H16 0.927723 0.438495 0.255770 0.052846 Uani 1.000000 0 0.001204 0.000981
0.000702 0.007748
H2 1.108448 0.318698 0.153056 0.027835 Uani 1.000000 0 0.001451 0.001229
0.000869 0.008891
O2 1.628547 0.902075 -0.139589 0.019137 Uani 1.000000 0 0.000057 0.000051
0.000035 0.000277
O1 1.660963 0.897063 -0.005194 0.024545 Uani 1.000000 0 0.000061 0.000056
0.000037 0.000304
O3 1.366807 0.564015 -0.172286 0.033961 Uani 1.000000 0 0.000068 0.000065
0.000039 0.000353
O4 1.158477 0.561092 -0.066377 0.027090 Uani 1.000000 0 0.000061 0.000059
0.000039 0.000318
O5 1.207633 0.395752 0.098781 0.015080 Uani 1.000000 0 0.000054 0.000047
0.000034 0.000261
O6 1.055246 0.571200 0.165670 0.016415 Uani 1.000000 0 0.000053 0.000047
0.000035 0.000263
N8 1.602389 0.864193 -0.056309 0.013951 Uani 1.000000 0 0.000065 0.000058
0.000042 0.000306
N7 1.285614 0.581342 -0.094651 0.017700 Uani 1.000000 0 0.000070 0.000061
0.000043 0.000332
C5 1.493529 0.774761 -0.014894 0.011886 Uani 1.000000 0 0.000073 0.000066
0.000047 0.000341
C3 1.343262 0.633593 -0.032266 0.011701 Uani 1.000000 0 0.000074 0.000067
0.000047 0.000337
C4 1.449337 0.714955 -0.073696 0.012323 Uani 1.000000 0 0.000078 0.000069
0.000052 0.000349
C2 1.284922 0.607950 0.063778 0.011803 Uani 1.000000 0 0.000074 0.000066
0.000047 0.000334
C1 1.171374 0.518180 0.112465 0.012433 Uani 1.000000 0 0.000076 0.000069
0.000048 0.000341
C7 1.333683 0.670624 0.119957 0.015144 Uani 1.000000 0 0.000083 0.000074
0.000054 0.000370
C6 1.437505 0.755079 0.081187 0.015016 Uani 1.000000 0 0.000082 0.000075
0.000052 0.000374
C10 0.726719 0.723164 0.205504 0.014928 Uani 1.000000 0 0.000083 0.000076
0.000052 0.000370
C13 0.494995 0.889099 0.310667 0.015755 Uani 1.000000 0 0.000085 0.000076
0.000053 0.000377
C11 0.615332 0.672299 0.276572 0.014425 Uani 1.000000 0 0.000081 0.000079
0.000052 0.000366
C8 0.840682 0.926297 0.112722 0.013490 Uani 1.000000 0 0.000076 0.000069
0.000048 0.000349
C12 0.604018 0.945435 0.240670 0.014384 Uani 1.000000 0 0.000079 0.000076
0.000051 0.000365
C9 0.722686 0.862072 0.188042 0.012294 Uani 1.000000 0 0.000075 0.000068
0.000047 0.000340
O12 0.813444 1.046529 0.083647 0.016448 Uani 1.000000 0 0.000054 0.000047
0.000034 0.000265
N3 0.970747 0.847140 0.083135 0.020018 Uani 1.000000 0 0.000075 0.000074
0.000052 0.000372
N2 0.504488 0.754959 0.327523 0.013932 Uani 1.000000 0 0.000069 0.000062
0.000043 0.000314
C17 0.797312 0.143075 0.341126 0.011754 Uani 1.000000 0 0.000075 0.000067
0.000047 0.000338
C16 0.676358 0.077658 0.411478 0.012438 Uani 1.000000 0 0.000075 0.000069
0.000048 0.000341
C18 0.905312 0.066356 0.277958 0.015833 Uani 1.000000 0 0.000081 0.000079
0.000052 0.000376
C15 0.803712 0.278114 0.336398 0.019832 Uani 1.000000 0 0.000090 0.000079
0.000056 0.000404
C14 0.915681 0.331768 0.267684 0.019296 Uani 1.000000 0 0.000086 0.000080
0.000054 0.000396
C19 1.015592 0.125991 0.211147 0.017705 Uani 1.000000 0 0.000086 0.000077
0.000056 0.000389
O8 0.469621 0.439140 0.404477 0.018539 Uani 1.000000 0 0.000053 0.000048
0.000036 0.000274
O11 -0.169720 0.169557 0.688846 0.021382 Uani 1.000000 0 0.000056 0.000051
0.000036 0.000291
O9 0.305076 0.622708 0.447382 0.015020 Uani 1.000000 0 0.000053 0.000047
0.000034 0.000259
O10 -0.127256 0.095406 0.557441 0.022845 Uani 1.000000 0 0.000059 0.000052
0.000039 0.000294
N5 0.281276 0.315991 0.335678 0.016772 Uani 1.000000 0 0.000068 0.000062
0.000041 0.000324
N6 -0.104535 0.165997 0.606163 0.015752 Uani 1.000000 0 0.000066 0.000059
0.000044 0.000317
O13 0.335837 0.205355 0.311393 0.033974 Uani 1.000000 0 0.000073 0.000057
0.000039 0.000352
O14 0.289065 0.421605 0.284567 0.026844 Uani 1.000000 0 0.000066 0.000055
0.000036 0.000316
O7 0.694775 -0.046309 0.428124 0.017398 Uani 1.000000 0 0.000053 0.000047
0.000035 0.000271
N1 1.018113 0.256558 0.207197 0.013894 Uani 1.000000 0 0.000069 0.000060
0.000043 0.000312
N4 0.553686 0.159053 0.450805 0.017658 Uani 1.000000 0 0.000075 0.000075
0.000049 0.000357
C21 0.221683 0.414654 0.481731 0.011705 Uani 1.000000 0 0.000074 0.000067
0.000047 0.000337
C20 0.343415 0.499070 0.440214 0.012234 Uani 1.000000 0 0.000077 0.000068
0.000047 0.000340
C24 0.008406 0.251595 0.563318 0.013100 Uani 1.000000 0 0.000075 0.000068
0.000049 0.000344
C25 0.027685 0.340198 0.615222 0.015593 Uani 1.000000 0 0.000083 0.000074
0.000054 0.000373
C22 0.197221 0.322810 0.433548 0.012006 Uani 1.000000 0 0.000075 0.000067
0.000046 0.000339
C23 0.092751 0.239488 0.472200 0.013374 Uani 1.000000 0 0.000080 0.000074
0.000052 0.000364
C26 0.134815 0.421328 0.573264 0.015672 Uani 1.000000 0 0.000083 0.000077
0.000052 0.000377

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H19 1.4779(11) 0.8057(10) 0.1229(6) 0.039(7) Uani 1.000000 0
H5 0.8142(11) 0.6551(9) 0.1647(7) 0.037(6) Uani 1.000000 0
H10 -0.0376(10) 0.3472(9) 0.6854(7) 0.039(7) Uani 1.000000 0
H4 0.6096(10) 0.5672(10) 0.2954(6) 0.034(6) Uani 1.000000 0
H18 1.2904(11) 0.6540(9) 0.1945(7) 0.039(7) Uani 1.000000 0
H20 1.4967(11) 0.7309(10) -0.1491(7) 0.038(7) Uani 1.000000 0
H3 0.3990(11) 0.9481(9) 0.3528(7) 0.042(7) Uani 1.000000 0
H6 0.5978(10) 1.0546(9) 0.2262(7) 0.035(6) Uani 1.000000 0
H17 1.1035(11) 0.0718(9) 0.1600(7) 0.044(7) Uani 1.000000 0
H15 0.9023(11) -0.0382(10) 0.2814(7) 0.045(7) Uani 1.000000 0
H11 0.0775(10) 0.1681(10) 0.4334(7) 0.036(7) Uani 1.000000 0
H9 0.1510(10) 0.4939(10) 0.6117(6) 0.037(7) Uani 1.000000 0
H13 0.4693(13) 0.1164(10) 0.4934(8) 0.040(8) Uani 1.000000 0
H7 1.0477(13) 0.8869(11) 0.0291(8) 0.042(8) Uani 1.000000 0
H12 0.5370(12) 0.2624(11) 0.4296(8) 0.036(8) Uani 1.000000 0
H14 0.7239(12) 0.3418(10) 0.3839(7) 0.054(8) Uani 1.000000 0
H1 0.4170(13) 0.7060(11) 0.3827(8) 0.025(8) Uani 1.000000 0
H8 0.9905(12) 0.7501(11) 0.1141(7) 0.037(8) Uani 1.000000 0
H16 0.9277(12) 0.4385(10) 0.2558(7) 0.053(8) Uani 1.000000 0
H2 1.1084(15) 0.3187(12) 0.1531(9) 0.028(9) Uani 1.000000 0
O2 1.62855(6) 0.90208(5) -0.13959(3) 0.0191(3) Uani 1.000000 0
O1 1.66096(6) 0.89706(6) -0.00519(4) 0.0245(3) Uani 1.000000 0
O3 1.36681(7) 0.56402(6) -0.17229(4) 0.0340(4) Uani 1.000000 0
O4 1.15848(6) 0.56109(6) -0.06638(4) 0.0271(3) Uani 1.000000 0
O5 1.20763(5) 0.39575(5) 0.09878(3) 0.0151(3) Uani 1.000000 0
O6 1.05525(5) 0.57120(5) 0.16567(3) 0.0164(3) Uani 1.000000 0
N8 1.60239(6) 0.86419(6) -0.05631(4) 0.0140(3) Uani 1.000000 0
N7 1.28561(7) 0.58134(6) -0.09465(4) 0.0177(3) Uani 1.000000 0
C5 1.49353(7) 0.77476(7) -0.01489(5) 0.0119(3) Uani 1.000000 0
C3 1.34326(7) 0.63359(7) -0.03227(5) 0.0117(3) Uani 1.000000 0
C4 1.44934(8) 0.71495(7) -0.07370(5) 0.0123(3) Uani 1.000000 0
C2 1.28492(7) 0.60795(7) 0.06378(5) 0.0118(3) Uani 1.000000 0
C1 1.17137(8) 0.51818(7) 0.11247(5) 0.0124(3) Uani 1.000000 0
C7 1.33368(8) 0.67062(7) 0.11996(5) 0.0151(4) Uani 1.000000 0
C6 1.43750(8) 0.75508(8) 0.08119(5) 0.0150(4) Uani 1.000000 0
C10 0.72672(8) 0.72316(8) 0.20550(5) 0.0149(4) Uani 1.000000 0
C13 0.49499(8) 0.88910(8) 0.31067(5) 0.0158(4) Uani 1.000000 0
C11 0.61533(8) 0.67230(8) 0.27657(5) 0.0144(4) Uani 1.000000 0
C8 0.84068(8) 0.92630(7) 0.11272(5) 0.0135(3) Uani 1.000000 0
C12 0.60402(8) 0.94543(8) 0.24067(5) 0.0144(4) Uani 1.000000 0
C9 0.72269(7) 0.86207(7) 0.18804(5) 0.0123(3) Uani 1.000000 0
O12 0.81344(5) 1.04653(5) 0.08365(3) 0.0164(3) Uani 1.000000 0
N3 0.97075(7) 0.84714(7) 0.08314(5) 0.0200(4) Uani 1.000000 0
N2 0.50449(7) 0.75496(6) 0.32752(4) 0.0139(3) Uani 1.000000 0
C17 0.79731(7) 0.14307(7) 0.34113(5) 0.0118(3) Uani 1.000000 0
C16 0.67636(8) 0.07766(7) 0.41148(5) 0.0124(3) Uani 1.000000 0
C18 0.90531(8) 0.06636(8) 0.27796(5) 0.0158(4) Uani 1.000000 0
C15 0.80371(9) 0.27811(8) 0.33640(6) 0.0198(4) Uani 1.000000 0
C14 0.91568(9) 0.33177(8) 0.26768(5) 0.0193(4) Uani 1.000000 0
C19 1.01559(9) 0.12599(8) 0.21115(6) 0.0177(4) Uani 1.000000 0
O8 0.46962(5) 0.43914(5) 0.40448(4) 0.0185(3) Uani 1.000000 0
O11 -0.16972(6) 0.16956(5) 0.68885(4) 0.0214(3) Uani 1.000000 0
O9 0.30508(5) 0.62271(5) 0.44738(3) 0.0150(3) Uani 1.000000 0
O10 -0.12726(6) 0.09541(5) 0.55744(4) 0.0228(3) Uani 1.000000 0
N5 0.28128(7) 0.31599(6) 0.33568(4) 0.0168(3) Uani 1.000000 0
N6 -0.10453(7) 0.16600(6) 0.60616(4) 0.0158(3) Uani 1.000000 0
O13 0.33584(7) 0.20535(6) 0.31139(4) 0.0340(4) Uani 1.000000 0
O14 0.28907(7) 0.42160(5) 0.28457(4) 0.0268(3) Uani 1.000000 0
O7 0.69478(5) -0.04631(5) 0.42812(4) 0.0174(3) Uani 1.000000 0
N1 1.01811(7) 0.25656(6) 0.20720(4) 0.0139(3) Uani 1.000000 0
N4 0.55369(7) 0.15905(7) 0.45080(5) 0.0177(4) Uani 1.000000 0
C21 0.22168(7) 0.41465(7) 0.48173(5) 0.0117(3) Uani 1.000000 0
C20 0.34342(8) 0.49907(7) 0.44021(5) 0.0122(3) Uani 1.000000 0
C24 0.00841(7) 0.25159(7) 0.56332(5) 0.0131(3) Uani 1.000000 0
C25 0.02768(8) 0.34020(7) 0.61522(5) 0.0156(4) Uani 1.000000 0
C22 0.19722(7) 0.32281(7) 0.43355(5) 0.0120(3) Uani 1.000000 0
C23 0.09275(8) 0.23949(7) 0.47220(5) 0.0134(4) Uani 1.000000 0
C26 0.13481(8) 0.42133(8) 0.57326(5) 0.0157(4) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H19 0.048623 0.055974 0.012563 -0.028948 0.001926 0.003845 0.006298 0.008127
0.005841 0.005861 0.005000 0.005309
H5 0.028814 0.027734 0.043465 -0.004774 0.002589 0.000796 0.005743 0.006237
0.006842 0.004806 0.005176 0.005212
H10 0.032596 0.044275 0.039300 -0.018544 0.005606 -0.013892 0.005760 0.007230
0.006956 0.005077 0.005281 0.005682
H4 0.033118 0.039661 0.025941 -0.000783 -0.001029 -0.012162 0.005903 0.006544
0.006605 0.005077 0.005066 0.005324
H18 0.041244 0.038593 0.037466 -0.022534 -0.001468 -0.004737 0.005857 0.006913
0.006778 0.005053 0.005224 0.005579
H20 0.038760 0.049660 0.028524 -0.018591 -0.007714 -0.000451 0.005917 0.007582
0.006689 0.005210 0.005256 0.005696
H3 0.045673 0.022651 0.046420 0.001217 0.001406 -0.007437 0.006833 0.005952
0.007345 0.005137 0.005760 0.005328
H6 0.034668 0.023608 0.037664 -0.005528 0.007151 -0.009480 0.006232 0.005976
0.006641 0.004981 0.005156 0.005125
H17 0.045760 0.027184 0.051168 -0.019496 0.010859 -0.009524 0.006710 0.006560
0.007165 0.005403 0.005670 0.005510
H15 0.035258 0.037306 0.052009 -0.015720 0.008994 -0.007061 0.006307 0.007000
0.007271 0.005472 0.005397 0.005743
H11 0.016110 0.046189 0.037876 0.000986 0.004812 -0.011716 0.005592 0.006989
0.006977 0.004985 0.005061 0.005538
H9 0.028841 0.049446 0.028580 -0.020274 0.011137 -0.009044 0.005745 0.007437
0.006168 0.005351 0.004793 0.005320
H13 0.042326 0.033383 0.042653 -0.007019 -0.010435 -0.002684 0.006999 0.007425
0.008442 0.005754 0.006268 0.006262
H7 0.036290 0.033869 0.042839 -0.003457 0.004668 -0.001034 0.007328 0.007361
0.007782 0.005795 0.006293 0.006140
H12 0.039461 0.010495 0.057526 -0.000444 -0.018782 -0.001461 0.006777 0.006420
0.009142 0.005584 0.006364 0.006401
H14 0.059773 0.031199 0.060178 -0.031920 0.021590 -0.016129 0.007758 0.007162
0.007784 0.006101 0.006158 0.006007
H1 0.018340 0.024216 0.030317 -0.005832 -0.004740 -0.000248 0.006840 0.007359
0.009390 0.005647 0.006695 0.006732
H8 0.040750 0.024083 0.036672 0.007631 -0.009662 0.003842 0.007390 0.006789
0.008186 0.005881 0.006249 0.006203
H16 0.068276 0.028429 0.046244 -0.024606 0.024690 -0.017139 0.008493 0.006872
0.007256 0.006332 0.006188 0.005633
H2 0.026585 0.025408 0.025435 0.002924 -0.001341 -0.007291 0.008525 0.008100
0.010716 0.006775 0.008530 0.007588
O2 0.019267 0.021235 0.016598 -0.012280 -0.001673 0.003081 0.000245 0.000299
0.000280 0.000219 0.000212 0.000227
O1 0.026847 0.031463 0.021192 -0.020555 -0.006701 0.000640 0.000256 0.000350
0.000321 0.000245 0.000236 0.000261
O3 0.035069 0.051872 0.022037 -0.021671 -0.001206 -0.017062 0.000313 0.000423
0.000345 0.000295 0.000271 0.000306
O4 0.025308 0.040366 0.022936 -0.020721 -0.010918 0.003008 0.000251 0.000383
0.000331 0.000247 0.000233 0.000278
O5 0.012397 0.011158 0.017764 -0.004147 0.002488 -0.001196 0.000234 0.000260
0.000280 0.000199 0.000207 0.000214
O6 0.011417 0.010732 0.021575 -0.002986 0.002620 0.000394 0.000231 0.000261
0.000283 0.000195 0.000206 0.000212
N8 0.013802 0.014491 0.014257 -0.008222 -0.002201 0.000375 0.000266 0.000316
0.000332 0.000232 0.000241 0.000253
N7 0.019195 0.021734 0.015355 -0.010638 -0.004856 -0.001712 0.000293 0.000355
0.000355 0.000259 0.000262 0.000277
C5 0.010767 0.012302 0.012181 -0.003947 -0.001814 -0.000618 0.000295 0.000350
0.000373 0.000258 0.000265 0.000282
C3 0.010805 0.011452 0.012515 -0.004504 -0.001706 -0.000303 0.000294 0.000343
0.000370 0.000256 0.000267 0.000281
C4 0.012323 0.013529 0.010762 -0.005482 -0.000826 -0.000934 0.000307 0.000356
0.000378 0.000263 0.000279 0.000296
C2 0.011048 0.011305 0.011804 -0.004831 -0.000683 0.000753 0.000293 0.000337
0.000363 0.000254 0.000267 0.000277
C1 0.009510 0.009760 0.015299 -0.002781 0.000315 -0.000035 0.000295 0.000352
0.000367 0.000262 0.000269 0.000286
C7 0.016882 0.017903 0.010443 -0.008715 -0.000606 -0.000029 0.000330 0.000391
0.000387 0.000286 0.000292 0.000315
C6 0.017227 0.017576 0.012131 -0.009896 -0.002482 -0.001129 0.000329 0.000392
0.000397 0.000292 0.000293 0.000307
C10 0.011895 0.011417 0.017517 -0.003474 0.000859 0.001111 0.000321 0.000383
0.000395 0.000286 0.000287 0.000312
C13 0.012599 0.013293 0.017676 -0.004397 0.001565 -0.000250 0.000327 0.000389
0.000406 0.000291 0.000294 0.000319
C11 0.012607 0.010485 0.016892 -0.004835 0.000637 0.001576 0.000316 0.000383
0.000394 0.000289 0.000281 0.000314
C8 0.010540 0.010947 0.015651 -0.003332 -0.000763 0.003316 0.000302 0.000365
0.000370 0.000267 0.000270 0.000294
C12 0.012223 0.011358 0.016807 -0.003869 -0.000116 0.000431 0.000316 0.000383
0.000390 0.000285 0.000280 0.000312
C9 0.010007 0.010421 0.014030 -0.003736 -0.000603 0.002044 0.000292 0.000361
0.000362 0.000261 0.000266 0.000287
O12 0.013029 0.011668 0.019367 -0.002925 0.000047 0.004146 0.000234 0.000265
0.000284 0.000201 0.000209 0.000215
N3 0.013136 0.014025 0.024063 -0.001961 0.002605 0.005496 0.000321 0.000367
0.000394 0.000279 0.000281 0.000310
N2 0.011304 0.013994 0.014719 -0.005408 -0.000129 0.000371 0.000270 0.000330
0.000339 0.000238 0.000246 0.000272
C17 0.011318 0.008956 0.013205 -0.004617 -0.000290 0.001004 0.000295 0.000350
0.000363 0.000260 0.000266 0.000283
C16 0.010878 0.009098 0.015100 -0.003930 -0.001047 0.002179 0.000298 0.000358
0.000363 0.000260 0.000267 0.000285
C18 0.013066 0.010907 0.020737 -0.004609 0.001244 -0.002391 0.000324 0.000381
0.000414 0.000292 0.000292 0.000321
C15 0.020363 0.012832 0.020477 -0.007940 0.007515 -0.004513 0.000375 0.000403
0.000416 0.000317 0.000319 0.000333
C14 0.019479 0.011738 0.020100 -0.008658 0.008513 -0.002925 0.000366 0.000400
0.000400 0.000313 0.000305 0.000322
C19 0.013988 0.013239 0.021407 -0.004982 0.004507 -0.004310 0.000339 0.000389
0.000423 0.000296 0.000308 0.000327
O8 0.012405 0.010460 0.026246 -0.003030 0.002965 0.000573 0.000241 0.000265
0.000297 0.000201 0.000216 0.000218
O11 0.017019 0.021624 0.021468 -0.009552 0.000883 0.003856 0.000255 0.000305
0.000294 0.000221 0.000219 0.000235
O9 0.011807 0.010649 0.019400 -0.003956 0.000855 -0.000584 0.000229 0.000259
0.000280 0.000197 0.000205 0.000211
O10 0.017664 0.016852 0.032691 -0.009416 0.000825 -0.005771 0.000250 0.000287
0.000338 0.000221 0.000236 0.000247
N5 0.022026 0.016035 0.010306 -0.006092 0.000640 -0.002422 0.000300 0.000345
0.000330 0.000259 0.000254 0.000273
N6 0.012070 0.011980 0.020539 -0.005271 -0.000073 0.000599 0.000270 0.000308
0.000357 0.000235 0.000248 0.000259
O13 0.048596 0.023658 0.020632 -0.009084 0.009690 -0.010551 0.000379 0.000330
0.000335 0.000287 0.000289 0.000266
O14 0.036627 0.026383 0.012496 -0.008790 -0.000680 0.003274 0.000312 0.000334
0.000295 0.000258 0.000246 0.000249
O7 0.012515 0.010023 0.023882 -0.003336 0.000781 0.003663 0.000236 0.000265
0.000297 0.000200 0.000213 0.000217
N1 0.012350 0.012740 0.014343 -0.005439 0.001264 -0.000884 0.000274 0.000325
0.000329 0.000240 0.000244 0.000265
N4 0.014047 0.011473 0.021834 -0.003964 0.002049 0.001688 0.000315 0.000356
0.000379 0.000272 0.000269 0.000292
C21 0.011399 0.011698 0.010957 -0.005316 0.000295 -0.000762 0.000299 0.000344
0.000361 0.000258 0.000264 0.000278
C20 0.010783 0.009357 0.014336 -0.003308 -0.000143 0.000061 0.000301 0.000356
0.000360 0.000267 0.000268 0.000281
C24 0.011264 0.011143 0.014995 -0.003738 -0.000522 -0.000245 0.000302 0.000344
0.000373 0.000261 0.000271 0.000283
C25 0.014979 0.016724 0.012959 -0.007640 0.002897 -0.002551 0.000332 0.000385
0.000389 0.000287 0.000295 0.000315
C22 0.012559 0.011366 0.010933 -0.004067 -0.000561 -0.000860 0.000307 0.000345
0.000356 0.000263 0.000267 0.000279
C23 0.014024 0.011481 0.014282 -0.004943 -0.001352 -0.002042 0.000320 0.000365
0.000397 0.000276 0.000288 0.000300
C26 0.017477 0.016562 0.012357 -0.008952 0.001711 -0.003293 0.000336 0.000398
0.000386 0.000298 0.000294 0.000311

# ====
# ADPs
# ====


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 . N8 . 1.2190(7) yes
O1 . N8 . 1.2209(8) yes
O3 . N7 . 1.2194(8) yes
O4 . N7 . 1.2185(8) yes
O11 . N6 . 1.2245(8) yes
O10 . N6 . 1.2216(8) yes
O13 . N5 . 1.2159(8) yes
O14 . N5 . 1.2151(8) yes
O5 . C1 . 1.2675(8) yes
O6 . C1 . 1.2421(8) yes
O12 . C8 . 1.2323(8) yes
O8 . C20 . 1.2424(8) yes
O9 . C20 . 1.2579(8) yes
O7 . C16 . 1.2358(8) yes
N8 . C5 . 1.4640(9) yes
N7 . C3 . 1.4642(9) yes
N3 . C8 . 1.3333(9) yes
N2 . C13 . 1.3423(9) yes
N2 . C11 . 1.3414(9) yes
N5 . C22 . 1.4663(9) yes
N6 . C24 . 1.4676(9) yes
N1 . C14 . 1.3370(9) yes
N1 . C19 . 1.3367(9) yes
N4 . C16 . 1.3311(9) yes
N3 . H7 . 1.012(11) yes
N3 . H8 . 1.026(11) yes
N2 . H1 . 1.124(13) yes
N1 . H2 . 1.205(15) yes
N4 . H13 . 1.000(11) yes
N4 . H12 . 1.043(11) yes
C5 . C4 . 1.3832(10) yes
C5 . C6 . 1.3868(10) yes
C3 . C4 . 1.3872(9) yes
C3 . C2 . 1.3924(9) yes
C2 . C1 . 1.5125(9) yes
C2 . C7 . 1.3968(10) yes
C7 . C6 . 1.3892(10) yes
C10 . C11 . 1.3846(10) yes
C10 . C9 . 1.3966(10) yes
C13 . C12 . 1.3867(10) yes
C8 . C9 . 1.5129(9) yes
C12 . C9 . 1.3940(10) yes
C17 . C16 . 1.5052(9) yes
C17 . C18 . 1.3902(10) yes
C17 . C15 . 1.3896(10) yes
C18 . C19 . 1.3887(10) yes
C15 . C14 . 1.3837(10) yes
C21 . C20 . 1.5215(9) yes
C21 . C22 . 1.3940(9) yes
C21 . C26 . 1.3920(10) yes
C24 . C25 . 1.3847(10) yes
C24 . C23 . 1.3871(10) yes
C25 . C26 . 1.3939(10) yes
C22 . C23 . 1.3855(10) yes
C4 . H20 . 1.092(9) yes
C7 . H18 . 1.077(10) yes
C6 . H19 . 1.089(10) yes
C10 . H5 . 1.079(9) yes
C13 . H3 . 1.080(9) yes
C11 . H4 . 1.074(10) yes
C12 . H6 . 1.094(9) yes
C18 . H15 . 1.072(10) yes
C15 . H14 . 1.075(10) yes
C14 . H16 . 1.103(9) yes
C19 . H17 . 1.087(10) yes
C25 . H10 . 1.065(9) yes
C23 . H11 . 1.081(10) yes
C26 . H9 . 1.091(9) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . N8 . O1 . 123.88(6) yes
O3 . N7 . O4 . 124.29(6) yes
O11 . N6 . O10 . 124.12(6) yes
O13 . N5 . O14 . 124.91(6) yes
O2 . N8 . C5 . 118.14(6) yes
O1 . N8 . C5 . 117.98(6) yes
O3 . N7 . C3 . 117.84(6) yes
O4 . N7 . C3 . 117.85(6) yes
O11 . N6 . C24 . 117.74(6) yes
O10 . N6 . C24 . 118.15(6) yes
O13 . N5 . C22 . 117.74(6) yes
O14 . N5 . C22 . 117.34(6) yes
O5 . C1 . O6 . 126.88(6) yes
O8 . C20 . O9 . 126.98(6) yes
O12 . C8 . N3 . 124.05(7) yes
O7 . C16 . N4 . 124.11(7) yes
O5 . C1 . C2 . 116.89(6) yes
O6 . C1 . C2 . 116.11(6) yes
O12 . C8 . C9 . 119.41(6) yes
O8 . C20 . C21 . 117.13(6) yes
O9 . C20 . C21 . 115.88(6) yes
O7 . C16 . C17 . 119.05(6) yes
N8 . C5 . C4 . 118.35(6) yes
N8 . C5 . C6 . 118.85(6) yes
N7 . C3 . C4 . 116.80(6) yes
N7 . C3 . C2 . 120.05(6) yes
N3 . C8 . C9 . 116.53(6) yes
N2 . C13 . C12 . 119.92(7) yes
N2 . C11 . C10 . 120.66(7) yes
N5 . C22 . C21 . 119.22(6) yes
N5 . C22 . C23 . 117.30(6) yes
N6 . C24 . C25 . 119.05(6) yes
N6 . C24 . C23 . 118.40(6) yes
N1 . C14 . C15 . 121.64(7) yes
N1 . C19 . C18 . 120.36(7) yes
N4 . C16 . C17 . 116.83(6) yes
N2 . C13 . H3 . 116.8(5) yes
N2 . C11 . H4 . 115.1(5) yes
N1 . C14 . H16 . 113.9(5) yes
N1 . C19 . H17 . 116.2(5) yes
C13 . N2 . C11 . 121.82(7) yes
C14 . N1 . C19 . 120.82(7) yes
C13 . N2 . H1 . 121.8(5) yes
C11 . N2 . H1 . 116.3(5) yes
C8 . N3 . H7 . 117.2(6) yes
C8 . N3 . H8 . 120.7(6) yes
C16 . N4 . H13 . 117.4(6) yes
C16 . N4 . H12 . 122.0(6) yes
C14 . N1 . H2 . 112.9(5) yes
C19 . N1 . H2 . 126.3(5) yes
C5 . C4 . C3 . 116.84(7) yes
C5 . C6 . C7 . 118.53(7) yes
C3 . C2 . C1 . 125.13(6) yes
C3 . C2 . C7 . 117.76(6) yes
C4 . C5 . C6 . 122.79(7) yes
C4 . C3 . C2 . 123.02(6) yes
C2 . C7 . C6 . 121.03(7) yes
C1 . C2 . C7 . 117.11(6) yes
C10 . C9 . C8 . 122.58(6) yes
C10 . C9 . C12 . 118.94(6) yes
C13 . C12 . C9 . 119.63(7) yes
C11 . C10 . C9 . 118.98(7) yes
C8 . C9 . C12 . 118.47(6) yes
C17 . C18 . C19 . 119.68(7) yes
C17 . C15 . C14 . 118.68(7) yes
C16 . C17 . C18 . 118.96(6) yes
C16 . C17 . C15 . 122.21(6) yes
C18 . C17 . C15 . 118.82(7) yes
C21 . C22 . C23 . 123.44(6) yes
C21 . C26 . C25 . 121.72(7) yes
C20 . C21 . C22 . 122.69(6) yes
C20 . C21 . C26 . 120.12(6) yes
C24 . C25 . C26 . 118.30(7) yes
C24 . C23 . C22 . 116.91(7) yes
C25 . C24 . C23 . 122.55(7) yes
C22 . C21 . C26 . 117.08(6) yes
C5 . C4 . H20 . 121.2(5) yes
C5 . C6 . H19 . 118.5(5) yes
C3 . C4 . H20 . 121.9(5) yes
C2 . C7 . H18 . 120.0(5) yes
C7 . C6 . H19 . 123.0(5) yes
C6 . C7 . H18 . 119.0(5) yes
C10 . C11 . H4 . 124.3(5) yes
C13 . C12 . H6 . 120.7(5) yes
C11 . C10 . H5 . 119.5(5) yes
C12 . C13 . H3 . 123.3(5) yes
C9 . C10 . H5 . 121.5(5) yes
C9 . C12 . H6 . 119.7(5) yes
C17 . C18 . H15 . 119.6(5) yes
C17 . C15 . H14 . 122.0(5) yes
C18 . C19 . H17 . 123.4(5) yes
C15 . C14 . H16 . 124.5(5) yes
C14 . C15 . H14 . 119.3(5) yes
C19 . C18 . H15 . 120.8(5) yes
C21 . C26 . H9 . 118.1(5) yes
C24 . C25 . H10 . 121.3(5) yes
C24 . C23 . H11 . 121.4(5) yes
C25 . C26 . H9 . 120.2(5) yes
C22 . C23 . H11 . 121.7(5) yes
C26 . C25 . H10 . 120.4(5) yes
H13 . N4 . H12 . 119.6(9) yes
H7 . N3 . H8 . 122.1(8) yes
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate 2:2'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_100K_har
_database_code_depnum_ccdc_archive 'CCDC 1922028'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex_5_100K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.44 %
RESPONSE: Data collection at non-standard wavelength. Fprime used for anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_100K_har  
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.14 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT353_complex_5_100K_har_2 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H2B      .       1.03 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT353_complex_5_100K_har_3 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N4       - H4A      .       1.02 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-3
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            100K
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_weight         410.3897
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       214
_QCr_calc_unit_n_alpha_electrons 107
_QCr_calc_unit_n_beta_electrons  107

# =======
# Crystal
# =======

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             856

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.147
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6859
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/n 1'
_symmetry_space_group_name_Hall  '-p 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, +y+1/2, -z+1/2'
'+x+1/2, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    100
_cell_measurement_reflns_used    9832
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      43.78

_cell_length_a                   7.0539(3)
_cell_length_b                   14.3314(6)
_cell_length_c                   18.3058(8)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 92.9626(19)
_cell_angle_gamma                90.000000(0)
_cell_volume                     1848.10(14)

_cell_formula_units_Z            4.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6367
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         41.364
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            335.240878

_reflns_d_resolution_high        9.140667
_reflns_d_resolution_low         0.670058
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                5516
_reflns_number_total             5516
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0221
_refine_ls_R_factor_all          0.0221
_refine_ls_wR_factor_gt          0.0194
_refine_ls_wR_factor_all         0.0194
_refine_ls_R_Fsqd_factor         0.0280
_refine_ls_goodness_of_fit_gt    1.4057
_refine_ls_goodness_of_fit_all   1.4057
_refine_ls_number_reflns         5516
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0081
_refine_ls_shift/su_max_mean     0.0010
_refine_ls_shift/su_max_par      'H8 Uxx'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1169
_refine_diff_density_min         -0.1341
_refine_diff_density_rms         0.0277
_refine_diff_density_max_atom    0.0705
_refine_diff_density_max_atom_tag H6
_refine_diff_density_min_atom    -0.0475
_refine_diff_density_min_atom_tag N3
_refine_diff_density_rms_atom    0.0246

_refine_special_details          
;

  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 100K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  100K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

100k.cif obtained from res in _shelx_res_file
;



# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 1.133444 0.673764 0.400543 0.036651 Uani 1.000000 0 0.000976 0.000421
0.000334 0.004481
H8 1.061633 0.563249 0.182896 0.041035 Uani 1.000000 0 0.000981 0.000426
0.000351 0.004647
H7 1.105717 0.697976 0.265593 0.044932 Uani 1.000000 0 0.001012 0.000452
0.000365 0.004857
H5 1.124680 0.512233 0.449199 0.039596 Uani 1.000000 0 0.000978 0.000441
0.000344 0.004608
H1 1.098977 0.275889 0.463112 0.028239 Uani 1.000000 0 0.001157 0.000611
0.000401 0.005553
O3 0.888002 0.340363 0.214902 0.013601 Uani 1.000000 0 0.000047 0.000021
0.000017 0.000159
O1 1.072754 0.344156 0.444597 0.015852 Uani 1.000000 0 0.000052 0.000024
0.000018 0.000171
O2 1.144876 0.282984 0.336552 0.017036 Uani 1.000000 0 0.000051 0.000022
0.000017 0.000169
O4 1.172536 0.364900 0.169747 0.018247 Uani 1.000000 0 0.000050 0.000023
0.000018 0.000176
C4 1.096309 0.446808 0.344178 0.011621 Uani 1.000000 0 0.000062 0.000030
0.000024 0.000202
C2 1.049694 0.381851 0.213845 0.012403 Uani 1.000000 0 0.000068 0.000030
0.000024 0.000205
C1 1.106722 0.349791 0.374157 0.012162 Uani 1.000000 0 0.000065 0.000030
0.000024 0.000203
C7 1.101252 0.628629 0.287619 0.017159 Uani 1.000000 0 0.000071 0.000033
0.000029 0.000232
C3 1.079237 0.460982 0.268022 0.011643 Uani 1.000000 0 0.000064 0.000030
0.000024 0.000200
C5 1.113012 0.523865 0.391106 0.014670 Uani 1.000000 0 0.000069 0.000032
0.000027 0.000220
C6 1.116725 0.614395 0.363119 0.016943 Uani 1.000000 0 0.000069 0.000033
0.000028 0.000231
C8 1.080903 0.551931 0.240576 0.014778 Uani 1.000000 0 0.000070 0.000032
0.000028 0.000220
H20 1.204421 0.020777 0.635089 0.032834 Uani 1.000000 0 0.000979 0.000422
0.000336 0.004237
H19 1.109370 0.186122 0.601246 0.035542 Uani 1.000000 0 0.000976 0.000423
0.000320 0.004322
H18 1.196192 0.142111 0.384018 0.036931 Uani 1.000000 0 0.001040 0.000422
0.000333 0.004433
H2A 1.340902 -0.158799 0.438721 0.036456 Uani 1.000000 0 0.001121 0.000480
0.000393 0.004998
H17 1.281618 -0.025000 0.405936 0.041471 Uani 1.000000 0 0.000993 0.000439
0.000334 0.004579
H2B 1.377837 -0.242032 0.509485 0.031629 Uani 1.000000 0 0.001059 0.000471
0.000371 0.004748
O5 1.296556 -0.136377 0.609575 0.017587 Uani 1.000000 0 0.000053 0.000022
0.000018 0.000172
N1 1.150040 0.169259 0.491502 0.013296 Uani 1.000000 0 0.000056 0.000025
0.000021 0.000183
N2 1.342096 -0.175588 0.491940 0.014809 Uani 1.000000 0 0.000062 0.000029
0.000024 0.000199
C15 1.298476 -0.114844 0.544129 0.012371 Uani 1.000000 0 0.000065 0.000030
0.000024 0.000205
C20 1.202481 0.045342 0.578173 0.013765 Uani 1.000000 0 0.000069 0.000031
0.000025 0.000217
C16 1.250034 -0.015828 0.522707 0.011273 Uani 1.000000 0 0.000060 0.000030
0.000024 0.000200
C19 1.151624 0.136577 0.560109 0.014042 Uani 1.000000 0 0.000070 0.000032
0.000026 0.000218
C17 1.248313 0.017877 0.451224 0.013731 Uani 1.000000 0 0.000067 0.000033
0.000025 0.000218
C18 1.199324 0.110901 0.438431 0.014516 Uani 1.000000 0 0.000069 0.000032
0.000026 0.000217
H11 0.869388 0.033432 0.026742 0.036959 Uani 1.000000 0 0.000992 0.000426
0.000340 0.004527
H13 0.936230 0.132662 0.282474 0.040761 Uani 1.000000 0 0.001040 0.000438
0.000354 0.004665
H12 0.868706 0.201782 0.064960 0.033957 Uani 1.000000 0 0.000971 0.000441
0.000330 0.004264
H14 0.943187 -0.039172 0.254254 0.039975 Uani 1.000000 0 0.001040 0.000418
0.000339 0.004557
H4A 0.832644 -0.246933 0.145819 0.030935 Uani 1.000000 0 0.001028 0.000467
0.000372 0.004663
H4B 0.777526 -0.159973 0.208174 0.030721 Uani 1.000000 0 0.001061 0.000445
0.000381 0.004684
H3 0.894777 0.247176 0.190168 0.016926 Uani 1.000000 0 0.000999 0.000585
0.000383 0.005223
O6 0.952692 -0.137591 0.053282 0.018567 Uani 1.000000 0 0.000053 0.000023
0.000018 0.000176
N4 0.843541 -0.179261 0.163282 0.015195 Uani 1.000000 0 0.000064 0.000030
0.000024 0.000200
N3 0.900101 0.170192 0.174476 0.013842 Uani 1.000000 0 0.000057 0.000028
0.000022 0.000190
C9 0.900762 -0.117170 0.114954 0.013027 Uani 1.000000 0 0.000065 0.000030
0.000025 0.000207
C11 0.882484 0.051959 0.083771 0.012812 Uani 1.000000 0 0.000067 0.000031
0.000026 0.000212
C10 0.901123 -0.015996 0.138183 0.011818 Uani 1.000000 0 0.000063 0.000030
0.000024 0.000203
C14 0.922035 0.011678 0.211364 0.015436 Uani 1.000000 0 0.000071 0.000033
0.000026 0.000222
C12 0.882658 0.145103 0.103842 0.013560 Uani 1.000000 0 0.000068 0.000032
0.000026 0.000214
C13 0.920399 0.106283 0.227871 0.016373 Uani 1.000000 0 0.000073 0.000033
0.000027 0.000230

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 1.1334(10) 0.6738(4) 0.4005(3) 0.037(4) Uani 1.000000 0
H8 1.0616(10) 0.5632(4) 0.1829(4) 0.041(5) Uani 1.000000 0
H7 1.1057(10) 0.6980(5) 0.2656(4) 0.045(5) Uani 1.000000 0
H5 1.1247(10) 0.5122(4) 0.4492(3) 0.040(5) Uani 1.000000 0
H1 1.0990(12) 0.2759(6) 0.4631(4) 0.028(6) Uani 1.000000 0
O3 0.88800(5) 0.34036(2) 0.214902(17) 0.01360(16) Uani 1.000000 0
O1 1.07275(5) 0.34416(2) 0.444597(18) 0.01585(17) Uani 1.000000 0
O2 1.14488(5) 0.28298(2) 0.336552(17) 0.01704(17) Uani 1.000000 0
O4 1.17254(5) 0.36490(2) 0.169747(18) 0.01825(18) Uani 1.000000 0
C4 1.09631(6) 0.44681(3) 0.34418(2) 0.0116(2) Uani 1.000000 0
C2 1.04969(7) 0.38185(3) 0.21385(2) 0.0124(2) Uani 1.000000 0
C1 1.10672(7) 0.34979(3) 0.37416(2) 0.0122(2) Uani 1.000000 0
C7 1.10125(7) 0.62863(3) 0.28762(3) 0.0172(2) Uani 1.000000 0
C3 1.07924(6) 0.46098(3) 0.26802(2) 0.0116(2) Uani 1.000000 0
C5 1.11301(7) 0.52387(3) 0.39111(3) 0.0147(2) Uani 1.000000 0
C6 1.11672(7) 0.61439(3) 0.36312(3) 0.0169(2) Uani 1.000000 0
C8 1.08090(7) 0.55193(3) 0.24058(3) 0.0148(2) Uani 1.000000 0
H20 1.2044(10) 0.0208(4) 0.6351(3) 0.033(4) Uani 1.000000 0
H19 1.1094(10) 0.1861(4) 0.6012(3) 0.036(4) Uani 1.000000 0
H18 1.1962(10) 0.1421(4) 0.3840(3) 0.037(4) Uani 1.000000 0
H2A 1.3409(11) -0.1588(5) 0.4387(4) 0.036(5) Uani 1.000000 0
H17 1.2816(10) -0.0250(4) 0.4059(3) 0.041(5) Uani 1.000000 0
H2B 1.3778(11) -0.2420(5) 0.5095(4) 0.032(5) Uani 1.000000 0
O5 1.29656(5) -0.13638(2) 0.609575(18) 0.01759(17) Uani 1.000000 0
N1 1.15004(6) 0.16926(3) 0.49150(2) 0.01330(18) Uani 1.000000 0
N2 1.34210(6) -0.17559(3) 0.49194(2) 0.0148(2) Uani 1.000000 0
C15 1.29848(7) -0.11484(3) 0.54413(2) 0.0124(2) Uani 1.000000 0
C20 1.20248(7) 0.04534(3) 0.57817(3) 0.0138(2) Uani 1.000000 0
C16 1.25003(6) -0.01583(3) 0.52271(2) 0.0113(2) Uani 1.000000 0
C19 1.15162(7) 0.13658(3) 0.56011(3) 0.0140(2) Uani 1.000000 0
C17 1.24831(7) 0.01788(3) 0.45122(3) 0.0137(2) Uani 1.000000 0
C18 1.19932(7) 0.11090(3) 0.43843(3) 0.0145(2) Uani 1.000000 0
H11 0.8694(10) 0.0334(4) 0.0267(3) 0.037(5) Uani 1.000000 0
H13 0.9362(10) 0.1327(4) 0.2825(4) 0.041(5) Uani 1.000000 0
H12 0.8687(10) 0.2018(4) 0.0650(3) 0.034(4) Uani 1.000000 0
H14 0.9432(10) -0.0392(4) 0.2543(3) 0.040(5) Uani 1.000000 0
H4A 0.8326(10) -0.2469(5) 0.1458(4) 0.031(5) Uani 1.000000 0
H4B 0.7775(11) -0.1600(4) 0.2082(4) 0.031(5) Uani 1.000000 0
H3 0.8948(10) 0.2472(6) 0.1902(4) 0.017(5) Uani 1.000000 0
O6 0.95269(5) -0.13759(2) 0.053282(18) 0.01857(18) Uani 1.000000 0
N4 0.84354(6) -0.17926(3) 0.16328(2) 0.0152(2) Uani 1.000000 0
N3 0.90010(6) 0.17019(3) 0.17448(2) 0.01384(19) Uani 1.000000 0
C9 0.90076(7) -0.11717(3) 0.11495(2) 0.0130(2) Uani 1.000000 0
C11 0.88248(7) 0.05196(3) 0.08377(3) 0.0128(2) Uani 1.000000 0
C10 0.90112(6) -0.01600(3) 0.13818(2) 0.0118(2) Uani 1.000000 0
C14 0.92204(7) 0.01168(3) 0.21136(3) 0.0154(2) Uani 1.000000 0
C12 0.88266(7) 0.14510(3) 0.10384(3) 0.0136(2) Uani 1.000000 0
C13 0.92040(7) 0.10628(3) 0.22787(3) 0.0164(2) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.047202 0.027082 0.035298 -0.008828 -0.001452 -0.003884 0.004989 0.004101
0.004348 0.003425 0.003791 0.003338
H8 0.053424 0.026975 0.042135 0.008138 -0.003018 0.010185 0.005181 0.004179
0.004555 0.003540 0.004009 0.003411
H7 0.059605 0.028343 0.047243 0.004727 0.006582 0.001604 0.005475 0.004217
0.004900 0.003737 0.004130 0.003492
H5 0.051364 0.034140 0.032627 0.001448 -0.004164 -0.006812 0.005219 0.004391
0.004211 0.003701 0.003890 0.003402
H1 0.036793 0.030106 0.017354 0.007575 -0.003080 0.001290 0.005898 0.005885
0.004879 0.004738 0.004282 0.004260
O3 0.018883 0.010820 0.011206 -0.001338 0.001810 -0.001727 0.000177 0.000147
0.000152 0.000124 0.000127 0.000119
O1 0.024006 0.013626 0.010092 0.002761 0.002488 0.000597 0.000194 0.000162
0.000157 0.000140 0.000134 0.000127
O2 0.029064 0.010986 0.011225 0.004781 0.002662 0.000863 0.000196 0.000153
0.000158 0.000134 0.000136 0.000121
O4 0.025129 0.016161 0.014295 -0.000495 0.009172 -0.000785 0.000198 0.000164
0.000167 0.000138 0.000143 0.000129
C4 0.014160 0.009853 0.010794 0.000496 0.000096 -0.000071 0.000213 0.000189
0.000204 0.000157 0.000161 0.000154
C2 0.018077 0.010239 0.009165 -0.000258 0.003328 0.000296 0.000232 0.000184
0.000198 0.000163 0.000166 0.000151
C1 0.016947 0.010290 0.009264 0.001851 0.000826 0.000518 0.000220 0.000193
0.000196 0.000161 0.000161 0.000155
C7 0.020579 0.009371 0.021489 -0.000265 0.000706 0.000839 0.000246 0.000200
0.000250 0.000179 0.000191 0.000183
C3 0.015837 0.008596 0.010537 -0.000361 0.001096 0.000722 0.000214 0.000186
0.000200 0.000154 0.000159 0.000152
C5 0.018187 0.012236 0.013354 0.000751 -0.001439 -0.002805 0.000233 0.000204
0.000221 0.000171 0.000176 0.000173
C6 0.019808 0.010738 0.020069 0.000126 -0.001038 -0.003428 0.000242 0.000202
0.000247 0.000176 0.000190 0.000181
C8 0.019630 0.009928 0.014819 -0.000279 0.001291 0.002490 0.000235 0.000198
0.000225 0.000167 0.000182 0.000171
H20 0.048796 0.028446 0.021547 0.003647 0.004589 0.004578 0.004857 0.004101
0.003750 0.003548 0.003586 0.003205
H19 0.052515 0.032799 0.021947 -0.000319 0.008050 0.003091 0.004927 0.004224
0.003840 0.003544 0.003604 0.003190
H18 0.061851 0.026492 0.022701 0.010186 0.004604 0.002794 0.005310 0.004097
0.003918 0.003600 0.003757 0.003221
H2A 0.041450 0.036938 0.031350 0.005886 0.005445 0.000748 0.005545 0.005018
0.004452 0.003837 0.004155 0.003777
H17 0.059091 0.035681 0.029918 0.009475 0.004972 0.002969 0.005293 0.004328
0.004123 0.003799 0.003898 0.003388
H2B 0.046319 0.024722 0.024356 0.006485 0.006740 0.006899 0.005590 0.004323
0.004347 0.003877 0.003934 0.003512
O5 0.031068 0.010689 0.010996 0.002810 0.000998 0.001717 0.000203 0.000153
0.000157 0.000137 0.000140 0.000124
N1 0.017673 0.009458 0.012735 0.001450 0.000572 0.001456 0.000198 0.000170
0.000181 0.000142 0.000147 0.000140
N2 0.019227 0.011843 0.013535 0.002132 0.002559 0.000449 0.000216 0.000184
0.000198 0.000156 0.000164 0.000155
C15 0.017027 0.009532 0.010564 0.000873 0.000793 0.001455 0.000218 0.000188
0.000207 0.000161 0.000163 0.000155
C20 0.021090 0.010313 0.009885 0.000804 0.000729 0.000326 0.000241 0.000198
0.000212 0.000169 0.000175 0.000161
C16 0.014317 0.009290 0.010218 0.000268 0.000691 0.000675 0.000212 0.000183
0.000205 0.000156 0.000159 0.000154
C19 0.021456 0.009785 0.010952 0.001122 0.001491 -0.000357 0.000244 0.000196
0.000213 0.000172 0.000174 0.000162
C17 0.019437 0.011299 0.010580 0.002713 0.001973 0.001292 0.000238 0.000201
0.000214 0.000171 0.000174 0.000163
C18 0.021236 0.011320 0.011101 0.002909 0.001880 0.002157 0.000237 0.000200
0.000214 0.000171 0.000178 0.000166
H11 0.048885 0.034201 0.027722 -0.003582 0.001306 0.000339 0.005129 0.004348
0.004099 0.003553 0.003812 0.003369
H13 0.063571 0.028878 0.029589 -0.007407 0.000062 -0.002268 0.005558 0.004238
0.004207 0.003629 0.003976 0.003311
H12 0.048077 0.032408 0.022012 0.003098 0.007858 -0.000075 0.004817 0.004211
0.003791 0.003505 0.003505 0.003156
H14 0.069186 0.024748 0.025352 0.004063 -0.003722 -0.002256 0.005551 0.004114
0.003983 0.003620 0.003885 0.003227
H4A 0.038427 0.020000 0.034980 0.002852 0.007711 -0.003283 0.005056 0.004231
0.004732 0.003658 0.003934 0.003610
H4B 0.036695 0.024844 0.031116 0.000187 0.006513 -0.006262 0.005092 0.004450
0.004554 0.003583 0.003976 0.003599
H3 0.017284 0.013718 0.019399 -0.010199 -0.002692 -0.008256 0.004834 0.006193
0.004633 0.004171 0.003797 0.004206
O6 0.030411 0.011978 0.014252 -0.003652 0.010232 -0.002993 0.000202 0.000158
0.000169 0.000138 0.000146 0.000127
N4 0.021939 0.010644 0.013447 -0.001026 0.005228 -0.000083 0.000222 0.000178
0.000201 0.000162 0.000162 0.000152
N3 0.016683 0.009895 0.015150 -0.001221 0.002768 -0.002463 0.000198 0.000177
0.000194 0.000147 0.000151 0.000149
C9 0.018522 0.010014 0.010985 -0.001581 0.005023 -0.001959 0.000224 0.000190
0.000207 0.000163 0.000169 0.000157
C11 0.016886 0.011027 0.010646 -0.000391 0.001876 -0.000571 0.000225 0.000198
0.000212 0.000163 0.000168 0.000163
C10 0.016044 0.009350 0.010275 -0.001647 0.002745 -0.000652 0.000214 0.000188
0.000207 0.000160 0.000162 0.000156
C14 0.024261 0.011456 0.010741 -0.001689 0.002357 -0.000696 0.000251 0.000202
0.000212 0.000180 0.000180 0.000170
C12 0.017787 0.009827 0.013224 0.000185 0.002315 0.000450 0.000227 0.000197
0.000216 0.000169 0.000172 0.000169
C13 0.025406 0.012177 0.011630 -0.001955 0.001869 -0.003140 0.000255 0.000211
0.000223 0.000179 0.000186 0.000172

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 . C2 . 1.2873(6) yes
O1 . C1 . 1.3261(5) yes
O2 . C1 . 1.2174(5) yes
O4 . C2 . 1.2385(5) yes
O5 . C15 . 1.2379(5) yes
O6 . C9 . 1.2398(5) yes
O1 . H1 . 1.049(9) yes
N1 . C19 . 1.3399(6) yes
N1 . C18 . 1.3413(6) yes
N2 . C15 . 1.3400(6) yes
N4 . C9 . 1.3320(6) yes
N3 . C12 . 1.3416(6) yes
N3 . C13 . 1.3417(6) yes
N2 . H2A . 1.003(7) yes
N2 . H2B . 1.032(7) yes
N4 . H4A . 1.023(7) yes
N4 . H4B . 1.004(7) yes
N3 . H3 . 1.141(8) yes
C4 . C1 . 1.4952(6) yes
C4 . C3 . 1.4078(6) yes
C4 . C5 . 1.4003(6) yes
C2 . C3 . 1.5138(6) yes
C7 . C6 . 1.3957(7) yes
C7 . C8 . 1.3992(7) yes
C3 . C8 . 1.3972(6) yes
C5 . C6 . 1.3957(7) yes
C15 . C16 . 1.5068(6) yes
C20 . C16 . 1.3954(6) yes
C20 . C19 . 1.3912(6) yes
C16 . C17 . 1.3943(6) yes
C17 . C18 . 1.3940(6) yes
C9 . C10 . 1.5110(6) yes
C11 . C10 . 1.3944(6) yes
C11 . C12 . 1.3845(6) yes
C10 . C14 . 1.3976(6) yes
C14 . C13 . 1.3893(6) yes
C7 . H7 . 1.074(6) yes
C5 . H5 . 1.075(6) yes
C6 . H6 . 1.095(6) yes
C8 . H8 . 1.070(6) yes
C20 . H20 . 1.099(6) yes
C19 . H19 . 1.088(6) yes
C17 . H17 . 1.068(6) yes
C18 . H18 . 1.091(6) yes
C11 . H11 . 1.077(6) yes
C14 . H14 . 1.076(6) yes
C12 . H12 . 1.081(6) yes
C13 . H13 . 1.069(6) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 . C2 . O4 . 124.72(4) yes
O1 . C1 . O2 . 123.94(4) yes
O5 . C15 . N2 . 122.85(4) yes
O6 . C9 . N4 . 124.13(4) yes
O3 . C2 . C3 . 115.36(4) yes
O1 . C1 . C4 . 113.93(4) yes
O2 . C1 . C4 . 122.13(4) yes
O4 . C2 . C3 . 119.78(4) yes
O5 . C15 . C16 . 118.23(4) yes
O6 . C9 . C10 . 119.11(4) yes
N1 . C19 . C20 . 122.74(4) yes
N1 . C18 . C17 . 123.09(4) yes
N2 . C15 . C16 . 118.92(4) yes
N4 . C9 . C10 . 116.76(4) yes
N3 . C12 . C11 . 120.86(4) yes
N3 . C13 . C14 . 120.63(5) yes
N1 . C19 . H19 . 115.6(3) yes
N1 . C18 . H18 . 114.3(3) yes
N3 . C12 . H12 . 115.7(3) yes
N3 . C13 . H13 . 116.2(3) yes
C1 . O1 . H1 . 109.5(4) yes
C19 . N1 . C18 . 118.10(4) yes
C12 . N3 . C13 . 121.34(4) yes
C15 . N2 . H2A . 123.1(4) yes
C15 . N2 . H2B . 116.0(4) yes
C9 . N4 . H4A . 116.5(4) yes
C9 . N4 . H4B . 121.9(4) yes
C12 . N3 . H3 . 119.9(4) yes
C13 . N3 . H3 . 118.7(4) yes
C4 . C3 . C2 . 122.85(4) yes
C4 . C3 . C8 . 119.26(4) yes
C4 . C5 . C6 . 120.70(4) yes
C2 . C3 . C8 . 117.82(4) yes
C1 . C4 . C3 . 119.85(4) yes
C1 . C4 . C5 . 120.48(4) yes
C7 . C6 . C5 . 119.83(4) yes
C7 . C8 . C3 . 120.93(5) yes
C3 . C4 . C5 . 119.60(4) yes
C6 . C7 . C8 . 119.67(4) yes
C15 . C16 . C20 . 117.52(4) yes
C15 . C16 . C17 . 124.15(4) yes
C20 . C16 . C17 . 118.33(4) yes
C16 . C20 . C19 . 119.09(4) yes
C16 . C17 . C18 . 118.62(4) yes
C9 . C10 . C11 . 118.06(4) yes
C9 . C10 . C14 . 122.73(4) yes
C11 . C10 . C14 . 119.20(4) yes
C10 . C11 . C12 . 119.02(4) yes
C10 . C14 . C13 . 118.93(4) yes
C4 . C5 . H5 . 119.0(3) yes
C7 . C6 . H6 . 120.4(3) yes
C7 . C8 . H8 . 119.5(3) yes
C3 . C8 . H8 . 119.6(3) yes
C5 . C6 . H6 . 119.7(3) yes
C6 . C7 . H7 . 120.3(4) yes
C6 . C5 . H5 . 120.3(3) yes
C8 . C7 . H7 . 120.0(4) yes
C20 . C19 . H19 . 121.7(3) yes
C16 . C20 . H20 . 119.8(3) yes
C16 . C17 . H17 . 122.5(3) yes
C19 . C20 . H20 . 121.1(3) yes
C17 . C18 . H18 . 122.6(3) yes
C18 . C17 . H17 . 118.8(3) yes
C11 . C12 . H12 . 123.4(3) yes
C10 . C11 . H11 . 121.4(3) yes
C10 . C14 . H14 . 120.7(3) yes
C14 . C13 . H13 . 123.1(3) yes
C12 . C11 . H11 . 119.6(3) yes
C13 . C14 . H14 . 120.3(3) yes
H2A . N2 . H2B . 120.9(5) yes
H4A . N4 . H4B . 119.1(5) yes
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_250K_har
_database_code_depnum_ccdc_archive 'CCDC 1922030'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT353_complex_5_250K_har  
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.15 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT919_complex_5_250K_har  
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: Reflections used in the refinement are taken from the fcf from a SHELXL refinement using the LIST 4FVAR^2 command. HAR applies its own rejection criteria during the initial stages of refinement. Reflection was not rejected.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-3
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            250K
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_weight         410.3897
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       214
_QCr_calc_unit_n_alpha_electrons 107
_QCr_calc_unit_n_beta_electrons  107

# =======
# Crystal
# =======

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             856

# ==============
# Absortion data
# ==============

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/n 1'
_symmetry_space_group_name_Hall  '-p 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, +y+1/2, -z+1/2'
'+x+1/2, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    250
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      43.75

_cell_length_a                   7.1747(3)
_cell_length_b                   14.3223(6)
_cell_length_c                   18.3518(7)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 92.6162(19)
_cell_angle_gamma                90.000000(0)
_cell_volume                     1883.83(13)

_cell_formula_units_Z            4.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========

_diffrn_ambient_temperature      250
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6521
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         41.368
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            329.611482

_reflns_d_resolution_high        9.166336
_reflns_d_resolution_low         0.670003
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                5280
_reflns_number_total             5280
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0289
_refine_ls_R_factor_all          0.0289
_refine_ls_wR_factor_gt          0.0194
_refine_ls_wR_factor_all         0.0194
_refine_ls_R_Fsqd_factor         0.0309
_refine_ls_goodness_of_fit_gt    1.6276
_refine_ls_goodness_of_fit_all   1.6276
_refine_ls_number_reflns         5280
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0078
_refine_ls_shift/su_max_mean     0.0010
_refine_ls_shift/su_max_par      'H8 Uyy'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1068
_refine_diff_density_min         -0.1539
_refine_diff_density_rms         0.0264
_refine_diff_density_max_atom    0.0505
_refine_diff_density_max_atom_tag H5
_refine_diff_density_min_atom    -0.0509
_refine_diff_density_min_atom_tag O3
_refine_diff_density_rms_atom    0.0267

_refine_special_details          
;
  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 250K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  250K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

250k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 1.130075 0.674341 0.399885 0.076954 Uani 1.000000 0 0.001151 0.000493
0.000406 0.006095
H8 1.059745 0.563230 0.183642 0.067982 Uani 1.000000 0 0.001117 0.000468
0.000393 0.005527
H7 1.098225 0.698621 0.265490 0.081898 Uani 1.000000 0 0.001155 0.000498
0.000438 0.006230
H5 1.124914 0.512515 0.449000 0.069057 Uani 1.000000 0 0.001125 0.000499
0.000385 0.005621
H1 1.104952 0.276816 0.462843 0.047470 Uani 1.000000 0 0.001192 0.000688
0.000431 0.006238
O3 0.893959 0.340015 0.215898 0.033758 Uani 1.000000 0 0.000056 0.000025
0.000020 0.000216
O1 1.078211 0.344788 0.444190 0.039363 Uani 1.000000 0 0.000066 0.000030
0.000022 0.000248
O2 1.147712 0.283804 0.336756 0.042888 Uani 1.000000 0 0.000064 0.000027
0.000021 0.000241
O4 1.171725 0.366103 0.170254 0.045941 Uani 1.000000 0 0.000064 0.000029
0.000022 0.000258
C4 1.097316 0.447185 0.344055 0.026893 Uani 1.000000 0 0.000071 0.000034
0.000028 0.000264
C2 1.051450 0.382338 0.214399 0.029779 Uani 1.000000 0 0.000084 0.000035
0.000028 0.000280
C1 1.109913 0.350423 0.374118 0.029291 Uani 1.000000 0 0.000077 0.000036
0.000028 0.000277
C7 1.097045 0.628846 0.287793 0.041621 Uani 1.000000 0 0.000090 0.000041
0.000038 0.000355
C3 1.078849 0.461348 0.268373 0.026910 Uani 1.000000 0 0.000073 0.000033
0.000028 0.000262
C5 1.112990 0.524185 0.390682 0.034608 Uani 1.000000 0 0.000085 0.000040
0.000035 0.000319
C6 1.114186 0.614620 0.362904 0.040715 Uani 1.000000 0 0.000087 0.000042
0.000038 0.000355
C8 1.078077 0.552210 0.241140 0.035525 Uani 1.000000 0 0.000090 0.000039
0.000037 0.000319
H20 1.200110 0.020940 0.634239 0.066026 Uani 1.000000 0 0.001197 0.000445
0.000386 0.005377
H19 1.110192 0.186468 0.600771 0.072358 Uani 1.000000 0 0.001179 0.000478
0.000372 0.005666
H18 1.205403 0.141842 0.385997 0.075424 Uani 1.000000 0 0.001252 0.000474
0.000385 0.005893
H2A 1.335394 -0.157637 0.439064 0.064144 Uani 1.000000 0 0.001302 0.000528
0.000462 0.006133
H17 1.284901 -0.023232 0.407372 0.074496 Uani 1.000000 0 0.001156 0.000474
0.000353 0.005712
H2B 1.372249 -0.241694 0.508856 0.058375 Uani 1.000000 0 0.001144 0.000543
0.000428 0.005837
O5 1.292557 -0.136325 0.609013 0.044305 Uani 1.000000 0 0.000068 0.000026
0.000021 0.000249
N1 1.153331 0.169592 0.492146 0.032315 Uani 1.000000 0 0.000066 0.000029
0.000025 0.000249
N2 1.337956 -0.175108 0.492079 0.035829 Uani 1.000000 0 0.000081 0.000038
0.000031 0.000289
C15 1.295332 -0.114557 0.544142 0.029698 Uani 1.000000 0 0.000078 0.000035
0.000030 0.000280
C20 1.200198 0.045366 0.577962 0.033139 Uani 1.000000 0 0.000087 0.000037
0.000032 0.000306
C16 1.248734 -0.015559 0.523041 0.026266 Uani 1.000000 0 0.000069 0.000034
0.000028 0.000261
C19 1.152040 0.136695 0.560146 0.034800 Uani 1.000000 0 0.000089 0.000039
0.000032 0.000316
C17 1.250148 0.018535 0.452246 0.033228 Uani 1.000000 0 0.000085 0.000040
0.000032 0.000308
C18 1.203124 0.111451 0.439525 0.035421 Uani 1.000000 0 0.000088 0.000040
0.000033 0.000320
H11 0.871761 0.033691 0.027931 0.063878 Uani 1.000000 0 0.001130 0.000462
0.000374 0.005406
H13 0.940771 0.131108 0.281423 0.081217 Uani 1.000000 0 0.001289 0.000513
0.000423 0.006211
H12 0.874265 0.203379 0.066455 0.061592 Uani 1.000000 0 0.001089 0.000469
0.000370 0.005186
H14 0.944440 -0.038843 0.254184 0.078416 Uani 1.000000 0 0.001291 0.000455
0.000388 0.005946
H4A 0.828723 -0.246562 0.144897 0.057053 Uani 1.000000 0 0.001149 0.000515
0.000395 0.005697
H4B 0.774841 -0.159490 0.206426 0.056337 Uani 1.000000 0 0.001222 0.000505
0.000420 0.005799
H3 0.904238 0.247273 0.191825 0.044439 Uani 1.000000 0 0.001116 0.000663
0.000426 0.006592
O6 0.945932 -0.137078 0.053091 0.046590 Uani 1.000000 0 0.000067 0.000027
0.000021 0.000259
N4 0.839763 -0.178813 0.162455 0.037049 Uani 1.000000 0 0.000084 0.000038
0.000031 0.000295
N3 0.904553 0.170028 0.175088 0.033471 Uani 1.000000 0 0.000067 0.000034
0.000027 0.000264
C9 0.896698 -0.116777 0.114568 0.031329 Uani 1.000000 0 0.000079 0.000036
0.000030 0.000289
C11 0.883133 0.052556 0.084583 0.030584 Uani 1.000000 0 0.000082 0.000037
0.000032 0.000294
C10 0.899873 -0.015856 0.138163 0.027505 Uani 1.000000 0 0.000072 0.000035
0.000028 0.000268
C14 0.922251 0.011129 0.210921 0.037447 Uani 1.000000 0 0.000093 0.000042
0.000032 0.000325
C12 0.886263 0.145298 0.104930 0.032639 Uani 1.000000 0 0.000081 0.000039
0.000033 0.000304
C13 0.923392 0.105602 0.227660 0.040268 Uani 1.000000 0 0.000098 0.000042
0.000036 0.000351

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 1.1301(12) 0.6743(5) 0.3999(4) 0.077(6) Uani 1.000000 0
H8 1.0597(11) 0.5632(5) 0.1836(4) 0.068(6) Uani 1.000000 0
H7 1.0982(12) 0.6986(5) 0.2655(4) 0.082(6) Uani 1.000000 0
H5 1.1249(11) 0.5125(5) 0.4490(4) 0.069(6) Uani 1.000000 0
H1 1.1050(12) 0.2768(7) 0.4628(4) 0.047(6) Uani 1.000000 0
O3 0.89396(6) 0.34001(3) 0.21590(2) 0.0338(2) Uani 1.000000 0
O1 1.07821(7) 0.34479(3) 0.44419(2) 0.0394(2) Uani 1.000000 0
O2 1.14771(6) 0.28380(3) 0.33676(2) 0.0429(2) Uani 1.000000 0
O4 1.17173(6) 0.36610(3) 0.17025(2) 0.0459(3) Uani 1.000000 0
C4 1.09732(7) 0.44718(3) 0.34405(3) 0.0269(3) Uani 1.000000 0
C2 1.05145(8) 0.38234(3) 0.21440(3) 0.0298(3) Uani 1.000000 0
C1 1.10991(8) 0.35042(4) 0.37412(3) 0.0293(3) Uani 1.000000 0
C7 1.09704(9) 0.62885(4) 0.28779(4) 0.0416(4) Uani 1.000000 0
C3 1.07885(7) 0.46135(3) 0.26837(3) 0.0269(3) Uani 1.000000 0
C5 1.11299(9) 0.52419(4) 0.39068(3) 0.0346(3) Uani 1.000000 0
C6 1.11419(9) 0.61462(4) 0.36290(4) 0.0407(4) Uani 1.000000 0
C8 1.07808(9) 0.55221(4) 0.24114(4) 0.0355(3) Uani 1.000000 0
H20 1.2001(12) 0.0209(4) 0.6342(4) 0.066(5) Uani 1.000000 0
H19 1.1102(12) 0.1865(5) 0.6008(4) 0.072(6) Uani 1.000000 0
H18 1.2054(13) 0.1418(5) 0.3860(4) 0.075(6) Uani 1.000000 0
H2A 1.3354(13) -0.1576(5) 0.4391(5) 0.064(6) Uani 1.000000 0
H17 1.2849(12) -0.0232(5) 0.4074(4) 0.074(6) Uani 1.000000 0
H2B 1.3722(11) -0.2417(5) 0.5089(4) 0.058(6) Uani 1.000000 0
O5 1.29256(7) -0.13632(3) 0.60901(2) 0.0443(2) Uani 1.000000 0
N1 1.15333(7) 0.16959(3) 0.49215(2) 0.0323(2) Uani 1.000000 0
N2 1.33796(8) -0.17511(4) 0.49208(3) 0.0358(3) Uani 1.000000 0
C15 1.29533(8) -0.11456(3) 0.54414(3) 0.0297(3) Uani 1.000000 0
C20 1.20020(9) 0.04537(4) 0.57796(3) 0.0331(3) Uani 1.000000 0
C16 1.24873(7) -0.01556(3) 0.52304(3) 0.0263(3) Uani 1.000000 0
C19 1.15204(9) 0.13669(4) 0.56015(3) 0.0348(3) Uani 1.000000 0
C17 1.25015(9) 0.01854(4) 0.45225(3) 0.0332(3) Uani 1.000000 0
C18 1.20312(9) 0.11145(4) 0.43952(3) 0.0354(3) Uani 1.000000 0
H11 0.8718(11) 0.0337(5) 0.0279(4) 0.064(5) Uani 1.000000 0
H13 0.9408(13) 0.1311(5) 0.2814(4) 0.081(6) Uani 1.000000 0
H12 0.8743(11) 0.2034(5) 0.0665(4) 0.062(5) Uani 1.000000 0
H14 0.9444(13) -0.0388(5) 0.2542(4) 0.078(6) Uani 1.000000 0
H4A 0.8287(11) -0.2466(5) 0.1449(4) 0.057(6) Uani 1.000000 0
H4B 0.7748(12) -0.1595(5) 0.2064(4) 0.056(6) Uani 1.000000 0
H3 0.9042(11) 0.2473(7) 0.1918(4) 0.044(7) Uani 1.000000 0
O6 0.94593(7) -0.13708(3) 0.05309(2) 0.0466(3) Uani 1.000000 0
N4 0.83976(8) -0.17881(4) 0.16246(3) 0.0370(3) Uani 1.000000 0
N3 0.90455(7) 0.17003(3) 0.17509(3) 0.0335(3) Uani 1.000000 0
C9 0.89670(8) -0.11678(4) 0.11457(3) 0.0313(3) Uani 1.000000 0
C11 0.88313(8) 0.05256(4) 0.08458(3) 0.0306(3) Uani 1.000000 0
C10 0.89987(7) -0.01586(3) 0.13816(3) 0.0275(3) Uani 1.000000 0
C14 0.92225(9) 0.01113(4) 0.21092(3) 0.0374(3) Uani 1.000000 0
C12 0.88626(8) 0.14530(4) 0.10493(3) 0.0326(3) Uani 1.000000 0
C13 0.92339(10) 0.10560(4) 0.22766(4) 0.0403(4) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.102152 0.053249 0.074296 -0.011367 -0.008704 -0.012780 0.007067 0.005238
0.005968 0.004646 0.005245 0.004424
H8 0.093160 0.044992 0.065698 -0.000723 0.002593 0.013737 0.006422 0.004827
0.005341 0.004191 0.005072 0.004073
H7 0.109878 0.038350 0.097837 -0.002086 0.008807 0.004735 0.007127 0.004862
0.006738 0.004650 0.005473 0.004494
H5 0.092063 0.058969 0.055633 0.011952 -0.002141 -0.014366 0.006414 0.005330
0.005141 0.004478 0.005037 0.004195
H1 0.059246 0.048370 0.034075 0.009500 -0.005723 0.001624 0.006420 0.006789
0.005518 0.005524 0.004774 0.004959
O3 0.047718 0.025793 0.027900 -0.003539 0.003212 -0.004828 0.000251 0.000198
0.000200 0.000168 0.000180 0.000153
O1 0.061616 0.031904 0.024743 0.007305 0.003870 0.002105 0.000300 0.000233
0.000211 0.000210 0.000199 0.000175
O2 0.075328 0.026411 0.027161 0.013468 0.004901 0.002579 0.000311 0.000205
0.000209 0.000196 0.000207 0.000162
O4 0.065357 0.038415 0.035972 -0.001649 0.023313 -0.001974 0.000301 0.000237
0.000241 0.000202 0.000224 0.000183
C4 0.032451 0.022479 0.025479 0.001522 -0.001614 -0.000966 0.000281 0.000245
0.000267 0.000199 0.000223 0.000196
C2 0.045197 0.023356 0.021299 -0.000122 0.007163 0.000990 0.000338 0.000243
0.000260 0.000228 0.000241 0.000193
C1 0.040804 0.024114 0.022818 0.005017 -0.000036 0.001460 0.000307 0.000262
0.000262 0.000216 0.000228 0.000203
C7 0.050191 0.020932 0.053565 -0.000996 0.000463 0.000973 0.000375 0.000281
0.000411 0.000254 0.000315 0.000269
C3 0.035830 0.020008 0.024920 -0.000717 0.001705 0.001792 0.000284 0.000236
0.000267 0.000198 0.000219 0.000191
C5 0.041863 0.028477 0.032885 0.001819 -0.004838 -0.007452 0.000339 0.000292
0.000323 0.000234 0.000275 0.000250
C6 0.046473 0.024682 0.050401 -0.000023 -0.004228 -0.008986 0.000363 0.000290
0.000409 0.000251 0.000308 0.000267
C8 0.047970 0.022550 0.036121 -0.001150 0.002621 0.005943 0.000352 0.000269
0.000337 0.000232 0.000293 0.000244
H20 0.114455 0.042085 0.042374 0.008607 0.012699 0.001659 0.006893 0.004697
0.004574 0.004451 0.004807 0.003827
H19 0.117082 0.050824 0.050513 0.010413 0.018506 0.005070 0.007021 0.005038
0.005001 0.004587 0.004887 0.003906
H18 0.128963 0.050566 0.047658 0.020182 0.014026 0.012605 0.007800 0.005026
0.004912 0.004773 0.005042 0.004064
H2A 0.079442 0.053079 0.059762 0.004359 0.001549 -0.002473 0.006881 0.005860
0.005681 0.004589 0.005507 0.004679
H17 0.122893 0.056585 0.045821 0.026135 0.023643 0.009586 0.007241 0.005115
0.004852 0.004810 0.005001 0.003872
H2B 0.078901 0.041553 0.055886 0.005550 0.016371 0.004754 0.006618 0.005232
0.005733 0.004720 0.004874 0.004399
O5 0.079966 0.025204 0.027642 0.006959 0.001317 0.004782 0.000329 0.000203
0.000215 0.000200 0.000214 0.000165
N1 0.042840 0.022676 0.031298 0.003027 0.000265 0.003315 0.000275 0.000222
0.000250 0.000190 0.000212 0.000185
N2 0.047816 0.026692 0.033297 0.005808 0.005316 0.001712 0.000317 0.000259
0.000293 0.000226 0.000262 0.000228
C15 0.040571 0.022076 0.026327 0.001549 0.000209 0.003045 0.000308 0.000247
0.000286 0.000216 0.000237 0.000202
C20 0.052081 0.023647 0.023594 0.001213 0.000709 0.000832 0.000362 0.000267
0.000290 0.000236 0.000266 0.000217
C16 0.032893 0.021447 0.024323 -0.000012 -0.000160 0.001715 0.000276 0.000235
0.000272 0.000202 0.000220 0.000196
C19 0.053237 0.023030 0.028079 0.002700 0.001278 -0.001139 0.000370 0.000272
0.000308 0.000249 0.000269 0.000225
C17 0.047907 0.026384 0.025678 0.006784 0.004786 0.003379 0.000347 0.000279
0.000300 0.000243 0.000264 0.000222
C18 0.052218 0.027234 0.027022 0.007735 0.004128 0.006094 0.000365 0.000286
0.000310 0.000248 0.000278 0.000229
H11 0.097652 0.048702 0.045161 0.001757 0.001984 0.004229 0.006499 0.004996
0.004736 0.004171 0.004796 0.003850
H13 0.130806 0.056697 0.056330 -0.006715 0.006263 -0.012277 0.007981 0.005319
0.005383 0.004951 0.005529 0.004391
H12 0.091971 0.038856 0.054582 0.000246 0.010251 0.001620 0.006052 0.004578
0.004974 0.004230 0.004451 0.003748
H14 0.152072 0.039524 0.043127 -0.008106 -0.001274 0.006680 0.008288 0.004864
0.004682 0.004842 0.005179 0.003772
H4A 0.089740 0.029298 0.052470 -0.002144 0.007053 -0.002490 0.006740 0.004831
0.005570 0.004491 0.004918 0.004046
H4B 0.073583 0.051092 0.044596 -0.006722 0.005532 -0.003736 0.006625 0.005562
0.005270 0.004473 0.004737 0.004258
H3 0.055140 0.031443 0.047590 -0.006970 0.011687 -0.021737 0.006101 0.007766
0.005978 0.005161 0.004824 0.005195
O6 0.077561 0.029208 0.035031 -0.010169 0.024751 -0.007853 0.000324 0.000218
0.000239 0.000202 0.000229 0.000175
N4 0.055456 0.023875 0.032762 -0.003462 0.012346 -0.001158 0.000343 0.000248
0.000299 0.000235 0.000254 0.000217
N3 0.039243 0.023601 0.037932 -0.003594 0.005744 -0.006185 0.000271 0.000238
0.000285 0.000201 0.000219 0.000210
C9 0.044591 0.022974 0.027316 -0.004378 0.011428 -0.003548 0.000324 0.000253
0.000292 0.000219 0.000250 0.000205
C11 0.040557 0.025543 0.025867 -0.000916 0.003864 -0.000917 0.000320 0.000271
0.000294 0.000221 0.000250 0.000222
C10 0.035841 0.022354 0.024709 -0.003806 0.005646 -0.002008 0.000283 0.000245
0.000277 0.000206 0.000221 0.000201
C14 0.060895 0.026487 0.025245 -0.005103 0.005092 -0.002274 0.000389 0.000288
0.000299 0.000266 0.000282 0.000233
C12 0.041428 0.023044 0.033706 0.000237 0.004574 0.000154 0.000324 0.000273
0.000318 0.000233 0.000258 0.000237
C13 0.062720 0.029330 0.028867 -0.005942 0.003322 -0.008333 0.000412 0.000311
0.000332 0.000272 0.000305 0.000251

# ====
# ADPs
# ====





# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 . C2 . 1.2837(7) yes
O1 . C1 . 1.3186(6) yes
O2 . C1 . 1.2129(6) yes
O4 . C2 . 1.2324(6) yes
O5 . C15 . 1.2317(6) yes
O6 . C9 . 1.2323(6) yes
O1 . H1 . 1.047(10) yes
N1 . C19 . 1.3343(7) yes
N1 . C18 . 1.3361(7) yes
N2 . C15 . 1.3361(7) yes
N4 . C9 . 1.3272(7) yes
N3 . C12 . 1.3360(7) yes
N3 . C13 . 1.3374(8) yes
N2 . H2A . 1.004(8) yes
N2 . H2B . 1.029(8) yes
N4 . H4A . 1.024(7) yes
N4 . H4B . 0.989(8) yes
N3 . H3 . 1.148(9) yes
C4 . C1 . 1.4928(7) yes
C4 . C3 . 1.4039(7) yes
C4 . C5 . 1.3972(7) yes
C2 . C3 . 1.5108(7) yes
C7 . C6 . 1.3933(9) yes
C7 . C8 . 1.3949(9) yes
C3 . C8 . 1.3939(7) yes
C5 . C6 . 1.3921(8) yes
C15 . C16 . 1.5034(7) yes
C20 . C16 . 1.3895(7) yes
C20 . C19 . 1.3881(8) yes
C16 . C17 . 1.3884(7) yes
C17 . C18 . 1.3900(8) yes
C9 . C10 . 1.5088(7) yes
C11 . C10 . 1.3894(7) yes
C11 . C12 . 1.3797(7) yes
C10 . C14 . 1.3923(8) yes
C14 . C13 . 1.3875(8) yes
C7 . H7 . 1.080(7) yes
C5 . H5 . 1.083(7) yes
C6 . H6 . 1.095(7) yes
C8 . H8 . 1.069(7) yes
C20 . H20 . 1.090(7) yes
C19 . H19 . 1.084(7) yes
C17 . H17 . 1.057(6) yes
C18 . H18 . 1.075(7) yes
C11 . H11 . 1.074(7) yes
C14 . H14 . 1.075(7) yes
C12 . H12 . 1.092(7) yes
C13 . H13 . 1.054(7) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 . C2 . O4 . 124.64(5) yes
O1 . C1 . O2 . 123.79(5) yes
O5 . C15 . N2 . 122.77(5) yes
O6 . C9 . N4 . 123.92(5) yes
O3 . C2 . C3 . 115.34(5) yes
O1 . C1 . C4 . 114.02(5) yes
O2 . C1 . C4 . 122.19(5) yes
O4 . C2 . C3 . 119.88(5) yes
O5 . C15 . C16 . 118.32(5) yes
O6 . C9 . C10 . 119.18(5) yes
N1 . C19 . C20 . 122.73(5) yes
N1 . C18 . C17 . 123.10(5) yes
N2 . C15 . C16 . 118.91(5) yes
N4 . C9 . C10 . 116.90(5) yes
N3 . C12 . C11 . 121.05(6) yes
N3 . C13 . C14 . 120.91(6) yes
N1 . C19 . H19 . 115.2(4) yes
N1 . C18 . H18 . 115.1(4) yes
N3 . C12 . H12 . 115.0(4) yes
N3 . C13 . H13 . 116.1(4) yes
C1 . O1 . H1 . 109.8(4) yes
C19 . N1 . C18 . 118.00(5) yes
C12 . N3 . C13 . 120.97(5) yes
C15 . N2 . H2A . 122.5(4) yes
C15 . N2 . H2B . 116.6(4) yes
C9 . N4 . H4A . 116.6(4) yes
C9 . N4 . H4B . 121.6(4) yes
C12 . N3 . H3 . 120.8(4) yes
C13 . N3 . H3 . 118.2(4) yes
C4 . C3 . C2 . 122.95(4) yes
C4 . C3 . C8 . 119.23(5) yes
C4 . C5 . C6 . 120.78(6) yes
C2 . C3 . C8 . 117.77(5) yes
C1 . C4 . C3 . 120.08(4) yes
C1 . C4 . C5 . 120.30(5) yes
C7 . C6 . C5 . 119.78(6) yes
C7 . C8 . C3 . 121.06(6) yes
C3 . C4 . C5 . 119.55(5) yes
C6 . C7 . C8 . 119.60(6) yes
C15 . C16 . C20 . 117.75(5) yes
C15 . C16 . C17 . 124.17(5) yes
C20 . C16 . C17 . 118.08(5) yes
C16 . C20 . C19 . 119.26(5) yes
C16 . C17 . C18 . 118.80(5) yes
C9 . C10 . C11 . 118.21(5) yes
C9 . C10 . C14 . 122.73(5) yes
C11 . C10 . C14 . 119.04(5) yes
C10 . C11 . C12 . 119.18(5) yes
C10 . C14 . C13 . 118.84(6) yes
C4 . C5 . H5 . 118.9(4) yes
C7 . C6 . H6 . 120.1(4) yes
C7 . C8 . H8 . 119.6(4) yes
C3 . C8 . H8 . 119.3(4) yes
C5 . C6 . H6 . 120.1(4) yes
C6 . C7 . H7 . 120.6(4) yes
C6 . C5 . H5 . 120.3(4) yes
C8 . C7 . H7 . 119.8(4) yes
C20 . C19 . H19 . 122.1(4) yes
C16 . C20 . H20 . 119.8(3) yes
C16 . C17 . H17 . 122.8(4) yes
C19 . C20 . H20 . 121.0(3) yes
C17 . C18 . H18 . 121.8(4) yes
C18 . C17 . H17 . 118.4(4) yes
C11 . C12 . H12 . 124.0(4) yes
C10 . C11 . H11 . 120.5(4) yes
C10 . C14 . H14 . 122.0(4) yes
C14 . C13 . H13 . 123.0(4) yes
C12 . C11 . H11 . 120.3(4) yes
C13 . C14 . H14 . 119.1(4) yes
H2A . N2 . H2B . 121.0(6) yes
H4A . N4 . H4B . 119.3(6) yes
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex7_300K_har
_database_code_depnum_ccdc_archive 'CCDC 1922032'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex7_300K_har   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.50 %
RESPONSE: Related to the use of a non-standard diffraction wavelength.
;
_vrf_PLAT353_complex7_300K_har   
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.24 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT230_complex7_300K_har   
;
PROBLEM: Hirshfeld Test Diff for    O4       --N7       .        7.8 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_300K_har_2 
;
PROBLEM: Hirshfeld Test Diff for    O13      --N5       .        7.8 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_300K_har_3 
;
PROBLEM: Hirshfeld Test Diff for    O14      --N5       .        9.0 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT353_complex7_300K_har_2 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H1       .       1.11 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT430_complex7_300K_har   
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.84 Ang.
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi
;
_vrf_PLAT919_complex7_300K_har   
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: Reflections used in the refinement are taken from the fcf from a SHELXL refinement using the LIST 4FVAR^2 command. HAR applies its own rejection criteria during the initial stages of refinement. Reflection was not rejected.
;
_vrf_PLAT230_complex7_300K_har_4 
;
PROBLEM: Hirshfeld Test Diff for    O1       --N8       .        5.3 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_300K_har_5 
;
PROBLEM: Hirshfeld Test Diff for    O6       --C1       .        5.1 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_300K_har_6 
;
PROBLEM: Hirshfeld Test Diff for    O8       --C20      .        7.0 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_300K_har_7 
;
PROBLEM: Hirshfeld Test Diff for    O10      --N6       .        5.9 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT230_complex7_300K_har_8 
;
PROBLEM: Hirshfeld Test Diff for    O11      --N6       .        6.5 s.u.
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT353_complex7_300K_har_3 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N4       - H12      .       1.03 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT353_complex7_300K_har_4 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H8       .       1.03 Ang.
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong charge assisted N+-H...O- hydrogen bond.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-5
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            300K
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_weight         668.4945
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       344
_QCr_calc_unit_n_alpha_electrons 172
_QCr_calc_unit_n_beta_electrons  172

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             688

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_T_max  0.7481
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'p -1'
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'

# =========
# Unit cell
# =========

_cell_measurement_temperature    300
_cell_measurement_reflns_used    8114
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      40.76

_cell_length_a                   9.7819(4)
_cell_length_b                   10.3742(4)
_cell_length_c                   15.4651(7)
_cell_angle_alpha                78.774(2)
_cell_angle_beta                 71.008(2)
_cell_angle_gamma                77.449(2)
_cell_volume                     1435.37(11)

_cell_formula_units_Z            2.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========
_diffrn_ambient_temperature      300
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6833
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.529
_diffrn_reflns_theta_max         35.632
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .



# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            214.218294

_reflns_d_resolution_high        10.034543
_reflns_d_resolution_low         0.760081
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4560
_reflns_number_total             4560
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0373
_refine_ls_R_factor_all          0.0373
_refine_ls_wR_factor_gt          0.0239
_refine_ls_wR_factor_all         0.0239
_refine_ls_R_Fsqd_factor         0.0383
_refine_ls_goodness_of_fit_gt    1.7798
_refine_ls_goodness_of_fit_all   1.7798
_refine_ls_number_reflns         4560
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0016
_refine_ls_shift/su_max_mean     0.0002
_refine_ls_shift/su_max_par      'C7 pz'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.2117
_refine_diff_density_min         -0.2220
_refine_diff_density_rms         0.0364
_refine_diff_density_max_atom    0.0868
_refine_diff_density_max_atom_tag O11
_refine_diff_density_min_atom    -0.0840
_refine_diff_density_min_atom_tag C3
_refine_diff_density_rms_atom    0.0348

_refine_special_details          
;

  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 300K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  300K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

300k.cif obtained from res in _shelx_res_file
;



# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H19 1.478693 0.797081 0.121531 0.095050 Uani 1.000000 0 0.001719 0.001706
0.001058 0.014215
H5 0.820747 0.650282 0.161813 0.098443 Uani 1.000000 0 0.001739 0.001390
0.001142 0.013565
H10 -0.034269 0.344855 0.682584 0.098356 Uani 1.000000 0 0.001828 0.001518
0.001062 0.013570
H4 0.614851 0.562902 0.290313 0.084601 Uani 1.000000 0 0.001587 0.001464
0.001034 0.012272
H18 1.297786 0.646350 0.191342 0.100987 Uani 1.000000 0 0.001913 0.001573
0.001112 0.013518
H20 1.488625 0.733910 -0.145886 0.073327 Uani 1.000000 0 0.001565 0.001402
0.001013 0.011082
H3 0.399723 0.936514 0.347243 0.093568 Uani 1.000000 0 0.001717 0.001439
0.001086 0.013398
H6 0.597819 1.045075 0.223512 0.084432 Uani 1.000000 0 0.001524 0.001439
0.001028 0.011973
H17 1.089216 0.087351 0.159151 0.140160 Uani 1.000000 0 0.001953 0.001557
0.001460 0.017673
H15 0.892712 -0.028557 0.277751 0.112435 Uani 1.000000 0 0.001685 0.001562
0.001222 0.014468
H11 0.084500 0.164824 0.438392 0.079475 Uani 1.000000 0 0.001643 0.001496
0.001029 0.012652
H9 0.153859 0.489160 0.607446 0.096679 Uani 1.000000 0 0.001708 0.001493
0.001062 0.013375
H13 0.474764 0.116628 0.492903 0.066262 Uani 1.000000 0 0.001767 0.001453
0.001138 0.012640
H7 1.042796 0.885225 0.029496 0.095681 Uani 1.000000 0 0.001985 0.001604
0.001244 0.015538
H12 0.541211 0.261382 0.432932 0.090526 Uani 1.000000 0 0.001947 0.001800
0.001347 0.015495
H14 0.725393 0.337790 0.391434 0.156335 Uani 1.000000 0 0.001955 0.001609
0.001349 0.018611
H1 0.417543 0.697027 0.374384 0.067782 Uani 1.000000 0 0.002011 0.001650
0.001184 0.014740
H8 0.990619 0.748085 0.109559 0.092593 Uani 1.000000 0 0.001720 0.001624
0.001330 0.015268
H16 0.936300 0.429121 0.267228 0.135148 Uani 1.000000 0 0.002002 0.001710
0.001236 0.016487
H2 1.113750 0.319955 0.153401 0.068037 Uani 1.000000 0 0.002158 0.001904
0.001322 0.016513
O2 1.631303 0.897770 -0.139656 0.065717 Uani 1.000000 0 0.000100 0.000093
0.000070 0.000709
O1 1.662952 0.889849 -0.009761 0.084142 Uani 1.000000 0 0.000120 0.000112
0.000075 0.000834
O3 1.357332 0.572827 -0.166703 0.122226 Uani 1.000000 0 0.000145 0.000146
0.000088 0.001132
O4 1.156989 0.570054 -0.061815 0.091677 Uani 1.000000 0 0.000131 0.000120
0.000075 0.000877
O5 1.206765 0.400989 0.101054 0.051357 Uani 1.000000 0 0.000093 0.000090
0.000061 0.000616
O6 1.056837 0.572059 0.167007 0.057477 Uani 1.000000 0 0.000090 0.000079
0.000063 0.000609
N8 1.604249 0.859604 -0.058344 0.047116 Uani 1.000000 0 0.000120 0.000107
0.000093 0.000780
N7 1.281310 0.588352 -0.090350 0.060594 Uani 1.000000 0 0.000151 0.000122
0.000091 0.000890
C5 1.494327 0.772422 -0.016147 0.037839 Uani 1.000000 0 0.000125 0.000115
0.000087 0.000772
C3 1.340793 0.637231 -0.030444 0.037092 Uani 1.000000 0 0.000126 0.000113
0.000084 0.000762
C4 1.447287 0.716957 -0.072730 0.038696 Uani 1.000000 0 0.000148 0.000134
0.000100 0.000838
C2 1.284480 0.609988 0.064521 0.037676 Uani 1.000000 0 0.000123 0.000114
0.000086 0.000773
C1 1.171208 0.521515 0.114125 0.041714 Uani 1.000000 0 0.000133 0.000131
0.000087 0.000826
C7 1.335741 0.668688 0.118390 0.051500 Uani 1.000000 0 0.000168 0.000156
0.000107 0.000985
C6 1.440489 0.750858 0.078744 0.051240 Uani 1.000000 0 0.000174 0.000161
0.000106 0.001056
C10 0.729075 0.719460 0.203139 0.048973 Uani 1.000000 0 0.000155 0.000144
0.000100 0.000952
C13 0.495524 0.879754 0.305060 0.050662 Uani 1.000000 0 0.000165 0.000156
0.000107 0.001012
C11 0.617011 0.667625 0.273046 0.049189 Uani 1.000000 0 0.000162 0.000156
0.000109 0.000947
C8 0.840607 0.922300 0.111030 0.043597 Uani 1.000000 0 0.000139 0.000132
0.000087 0.000839
C12 0.604329 0.937202 0.236732 0.046495 Uani 1.000000 0 0.000152 0.000147
0.000102 0.000895
C9 0.723528 0.856785 0.185643 0.039984 Uani 1.000000 0 0.000128 0.000121
0.000082 0.000774
O12 0.814408 1.040536 0.082638 0.056470 Uani 1.000000 0 0.000090 0.000084
0.000060 0.000617
N3 0.969257 0.846541 0.081877 0.070716 Uani 1.000000 0 0.000164 0.000159
0.000114 0.001095
N2 0.505071 0.747665 0.321941 0.045674 Uani 1.000000 0 0.000131 0.000120
0.000084 0.000791
C17 0.794891 0.146980 0.341446 0.037618 Uani 1.000000 0 0.000126 0.000117
0.000081 0.000759
C16 0.674512 0.080920 0.410533 0.040523 Uani 1.000000 0 0.000136 0.000128
0.000085 0.000802
C18 0.898054 0.075639 0.275716 0.053478 Uani 1.000000 0 0.000163 0.000153
0.000108 0.000967
C15 0.806645 0.277113 0.340693 0.065410 Uani 1.000000 0 0.000180 0.000152
0.000111 0.001102
C14 0.918656 0.331053 0.272888 0.067078 Uani 1.000000 0 0.000189 0.000164
0.000119 0.001118
C19 1.007737 0.136561 0.210505 0.058783 Uani 1.000000 0 0.000174 0.000172
0.000114 0.001095
O8 0.470055 0.437894 0.406416 0.065081 Uani 1.000000 0 0.000097 0.000083
0.000067 0.000658
O11 -0.162684 0.168115 0.691441 0.077063 Uani 1.000000 0 0.000110 0.000100
0.000077 0.000777
O9 0.304501 0.617737 0.439249 0.053890 Uani 1.000000 0 0.000088 0.000083
0.000062 0.000604
O10 -0.122994 0.096210 0.563698 0.081584 Uani 1.000000 0 0.000112 0.000104
0.000086 0.000826
N5 0.284693 0.308912 0.338707 0.060763 Uani 1.000000 0 0.000138 0.000145
0.000082 0.000886
N6 -0.099050 0.164720 0.610153 0.055861 Uani 1.000000 0 0.000125 0.000118
0.000100 0.000868
O13 0.335472 0.200299 0.316395 0.114187 Uani 1.000000 0 0.000155 0.000133
0.000077 0.001081
O14 0.299197 0.410384 0.286964 0.098585 Uani 1.000000 0 0.000138 0.000125
0.000070 0.000952
O7 0.689696 -0.041131 0.423716 0.059175 Uani 1.000000 0 0.000090 0.000084
0.000063 0.000633
N1 1.015926 0.262212 0.209959 0.045654 Uani 1.000000 0 0.000128 0.000116
0.000081 0.000764
N4 0.556062 0.159657 0.453375 0.057444 Uani 1.000000 0 0.000159 0.000149
0.000104 0.000979
C21 0.224693 0.410359 0.480367 0.038187 Uani 1.000000 0 0.000126 0.000115
0.000084 0.000758
C20 0.344416 0.495196 0.437607 0.041357 Uani 1.000000 0 0.000141 0.000128
0.000084 0.000820
C24 0.013290 0.249728 0.565531 0.043036 Uani 1.000000 0 0.000130 0.000121
0.000093 0.000826
C25 0.032517 0.338142 0.614451 0.053030 Uani 1.000000 0 0.000166 0.000155
0.000111 0.000993
C22 0.200975 0.318431 0.435078 0.039735 Uani 1.000000 0 0.000131 0.000121
0.000082 0.000777
C23 0.096489 0.236474 0.475622 0.043568 Uani 1.000000 0 0.000159 0.000144
0.000106 0.000942
C26 0.138598 0.417742 0.571051 0.051647 Uani 1.000000 0 0.000167 0.000153
0.000101 0.001007

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H19 1.4787(17) 0.7971(17) 0.1215(11) 0.095(14) Uani 1.000000 0
H5 0.8207(17) 0.6503(14) 0.1618(11) 0.098(14) Uani 1.000000 0
H10 -0.0343(18) 0.3449(15) 0.6826(11) 0.098(14) Uani 1.000000 0
H4 0.6149(16) 0.5629(15) 0.2903(10) 0.085(12) Uani 1.000000 0
H18 1.2978(19) 0.6464(16) 0.1913(11) 0.101(14) Uani 1.000000 0
H20 1.4886(16) 0.7339(14) -0.1459(10) 0.073(11) Uani 1.000000 0
H3 0.3997(17) 0.9365(14) 0.3472(11) 0.094(13) Uani 1.000000 0
H6 0.5978(15) 1.0451(14) 0.2235(10) 0.084(12) Uani 1.000000 0
H17 1.089(2) 0.0874(16) 0.1592(15) 0.140(18) Uani 1.000000 0
H15 0.8927(17) -0.0286(16) 0.2778(12) 0.112(14) Uani 1.000000 0
H11 0.0845(16) 0.1648(15) 0.4384(10) 0.079(13) Uani 1.000000 0
H9 0.1539(17) 0.4892(15) 0.6074(11) 0.097(13) Uani 1.000000 0
H13 0.4748(18) 0.1166(15) 0.4929(11) 0.066(13) Uani 1.000000 0
H7 1.043(2) 0.8852(16) 0.0295(12) 0.096(16) Uani 1.000000 0
H12 0.5412(19) 0.2614(18) 0.4329(13) 0.091(15) Uani 1.000000 0
H14 0.725(2) 0.3378(16) 0.3914(13) 0.156(19) Uani 1.000000 0
H1 0.418(2) 0.6970(17) 0.3744(12) 0.068(15) Uani 1.000000 0
H8 0.9906(17) 0.7481(16) 0.1096(13) 0.093(15) Uani 1.000000 0
H16 0.936(2) 0.4291(17) 0.2672(12) 0.135(16) Uani 1.000000 0
H2 1.114(2) 0.3200(19) 0.1534(13) 0.068(17) Uani 1.000000 0
O2 1.63130(10) 0.89777(9) -0.13966(7) 0.0657(7) Uani 1.000000 0
O1 1.66295(12) 0.88985(11) -0.00976(8) 0.0841(8) Uani 1.000000 0
O3 1.35733(15) 0.57283(15) -0.16670(9) 0.1222(11) Uani 1.000000 0
O4 1.15699(13) 0.57005(12) -0.06182(8) 0.0917(9) Uani 1.000000 0
O5 1.20676(9) 0.40099(9) 0.10105(6) 0.0514(6) Uani 1.000000 0
O6 1.05684(9) 0.57206(8) 0.16701(6) 0.0575(6) Uani 1.000000 0
N8 1.60425(12) 0.85960(11) -0.05834(9) 0.0471(8) Uani 1.000000 0
N7 1.28131(15) 0.58835(12) -0.09035(9) 0.0606(9) Uani 1.000000 0
C5 1.49433(13) 0.77242(11) -0.01615(9) 0.0378(8) Uani 1.000000 0
C3 1.34079(13) 0.63723(11) -0.03044(8) 0.0371(8) Uani 1.000000 0
C4 1.44729(15) 0.71696(13) -0.07273(10) 0.0387(8) Uani 1.000000 0
C2 1.28448(12) 0.60999(11) 0.06452(9) 0.0377(8) Uani 1.000000 0
C1 1.17121(13) 0.52151(13) 0.11413(9) 0.0417(8) Uani 1.000000 0
C7 1.33574(17) 0.66869(16) 0.11839(11) 0.0515(10) Uani 1.000000 0
C6 1.44049(17) 0.75086(16) 0.07874(11) 0.0512(11) Uani 1.000000 0
C10 0.72907(15) 0.71946(14) 0.20314(10) 0.0490(10) Uani 1.000000 0
C13 0.49552(16) 0.87975(16) 0.30506(11) 0.0507(10) Uani 1.000000 0
C11 0.61701(16) 0.66763(16) 0.27305(11) 0.0492(9) Uani 1.000000 0
C8 0.84061(14) 0.92230(13) 0.11103(9) 0.0436(8) Uani 1.000000 0
C12 0.60433(15) 0.93720(15) 0.23673(10) 0.0465(9) Uani 1.000000 0
C9 0.72353(13) 0.85679(12) 0.18564(8) 0.0400(8) Uani 1.000000 0
O12 0.81441(9) 1.04054(8) 0.08264(6) 0.0565(6) Uani 1.000000 0
N3 0.96926(16) 0.84654(16) 0.08188(11) 0.0707(11) Uani 1.000000 0
N2 0.50507(13) 0.74767(12) 0.32194(8) 0.0457(8) Uani 1.000000 0
C17 0.79489(13) 0.14698(12) 0.34145(8) 0.0376(8) Uani 1.000000 0
C16 0.67451(14) 0.08092(13) 0.41053(9) 0.0405(8) Uani 1.000000 0
C18 0.89805(16) 0.07564(15) 0.27572(11) 0.0535(10) Uani 1.000000 0
C15 0.80665(18) 0.27711(15) 0.34069(11) 0.0654(11) Uani 1.000000 0
C14 0.91866(19) 0.33105(16) 0.27289(12) 0.0671(11) Uani 1.000000 0
C19 1.00774(17) 0.13656(17) 0.21051(11) 0.0588(11) Uani 1.000000 0
O8 0.47005(10) 0.43789(8) 0.40642(7) 0.0651(7) Uani 1.000000 0
O11 -0.16268(11) 0.16812(10) 0.69144(8) 0.0771(8) Uani 1.000000 0
O9 0.30450(9) 0.61774(8) 0.43925(6) 0.0539(6) Uani 1.000000 0
O10 -0.12299(11) 0.09621(10) 0.56370(9) 0.0816(8) Uani 1.000000 0
N5 0.28469(14) 0.30891(14) 0.33871(8) 0.0608(9) Uani 1.000000 0
N6 -0.09905(13) 0.16472(12) 0.61015(10) 0.0559(9) Uani 1.000000 0
O13 0.33547(15) 0.20030(13) 0.31640(8) 0.1142(11) Uani 1.000000 0
O14 0.29920(14) 0.41038(13) 0.28696(7) 0.0986(10) Uani 1.000000 0
O7 0.68970(9) -0.04113(8) 0.42372(6) 0.0592(6) Uani 1.000000 0
N1 1.01593(13) 0.26221(12) 0.20996(8) 0.0457(8) Uani 1.000000 0
N4 0.55606(16) 0.15966(15) 0.45338(10) 0.0574(10) Uani 1.000000 0
C21 0.22469(13) 0.41036(11) 0.48037(8) 0.0382(8) Uani 1.000000 0
C20 0.34442(14) 0.49520(13) 0.43761(8) 0.0414(8) Uani 1.000000 0
C24 0.01329(13) 0.24973(12) 0.56553(9) 0.0430(8) Uani 1.000000 0
C25 0.03252(17) 0.33814(16) 0.61445(11) 0.0530(10) Uani 1.000000 0
C22 0.20098(13) 0.31843(12) 0.43508(8) 0.0397(8) Uani 1.000000 0
C23 0.09649(16) 0.23647(14) 0.47562(11) 0.0436(9) Uani 1.000000 0
C26 0.13860(17) 0.41774(15) 0.57105(10) 0.0516(10) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H19 0.091021 0.132343 0.073029 -0.067857 -0.023007 0.013193 0.011324 0.017652
0.012877 0.010840 0.009441 0.011162
H5 0.080833 0.046101 0.127785 -0.009225 0.015800 0.000499 0.012893 0.010757
0.014319 0.009199 0.010513 0.009499
H10 0.118587 0.096906 0.074308 -0.052625 0.005992 -0.020119 0.013531 0.014408
0.012501 0.010658 0.011039 0.011230
H4 0.079513 0.067821 0.083366 -0.016511 0.018281 -0.025031 0.011982 0.011645
0.012581 0.009926 0.009438 0.009872
H18 0.126791 0.106697 0.085357 -0.060695 -0.036522 0.005409 0.012190 0.015238
0.013713 0.010373 0.011846 0.012626
H20 0.070655 0.079139 0.069904 -0.032096 -0.011607 -0.003208 0.009747 0.011985
0.011226 0.008121 0.009452 0.010225
H3 0.081955 0.072182 0.102943 -0.025895 0.009652 -0.006215 0.012504 0.012554
0.013493 0.009644 0.009931 0.010011
H6 0.063269 0.066186 0.090583 -0.009450 0.008761 0.010793 0.010978 0.011227
0.011886 0.009420 0.008757 0.009746
H17 0.102579 0.070936 0.210900 -0.039933 0.036455 -0.049930 0.015803 0.014069
0.020270 0.011500 0.013789 0.012795
H15 0.071586 0.072982 0.143693 -0.017599 0.040754 -0.019976 0.013521 0.012527
0.014555 0.010838 0.010669 0.011371
H11 0.075673 0.076671 0.081337 -0.015103 -0.005337 -0.027809 0.011421 0.012912
0.012929 0.009130 0.009244 0.009885
H9 0.098810 0.092163 0.093036 -0.056130 0.024440 -0.044789 0.012380 0.014473
0.012728 0.010404 0.009364 0.010328
H13 0.059045 0.044575 0.080149 -0.010714 -0.001575 -0.004007 0.011735 0.010768
0.013817 0.008749 0.009393 0.009748
H7 0.083363 0.056903 0.091854 0.009099 0.017493 0.019335 0.016332 0.012127
0.013376 0.010486 0.011457 0.010728
H12 0.077832 0.057471 0.127975 -0.027889 -0.016650 0.001657 0.012532 0.015112
0.018088 0.012323 0.011460 0.013396
H14 0.124402 0.088569 0.196264 -0.088178 0.102688 -0.061207 0.018261 0.015930
0.017072 0.013843 0.014055 0.012900
H1 0.064281 0.055939 0.057627 -0.007122 0.010483 -0.000908 0.014522 0.012834
0.015611 0.010827 0.012569 0.011921
H8 0.046867 0.037637 0.141352 -0.005768 0.030933 0.005546 0.013029 0.012124
0.016512 0.011136 0.011423 0.011123
H16 0.134214 0.101060 0.129030 -0.079466 0.070783 -0.042696 0.016907 0.016704
0.014063 0.013622 0.011548 0.012133
H2 0.061187 0.080063 0.062765 0.005592 -0.018718 -0.028113 0.015111 0.015267
0.020234 0.012291 0.015214 0.015115
O2 0.061375 0.071678 0.058828 -0.040082 -0.004494 0.013050 0.000619 0.000784
0.000663 0.000529 0.000522 0.000560
O1 0.085246 0.110258 0.073391 -0.069942 -0.016359 -0.002722 0.000654 0.001072
0.000817 0.000699 0.000611 0.000692
O3 0.115098 0.201535 0.075642 -0.083219 0.002030 -0.066757 0.000930 0.001602
0.001006 0.000965 0.000796 0.001022
O4 0.081125 0.139306 0.075931 -0.065436 -0.033442 0.006496 0.000619 0.001187
0.000878 0.000701 0.000640 0.000786
O5 0.037760 0.038357 0.062055 -0.014141 0.010146 -0.004142 0.000545 0.000609
0.000613 0.000446 0.000468 0.000475
O6 0.035125 0.037336 0.077143 -0.010162 0.012254 0.000068 0.000527 0.000559
0.000628 0.000433 0.000474 0.000479
N8 0.041624 0.047660 0.051054 -0.024582 -0.004801 -0.000455 0.000673 0.000768
0.000841 0.000566 0.000622 0.000621
N7 0.059099 0.080605 0.050272 -0.037096 -0.010742 -0.008676 0.000765 0.000991
0.000933 0.000706 0.000737 0.000746
C5 0.031972 0.038107 0.039137 -0.013230 -0.002040 -0.001555 0.000659 0.000766
0.000828 0.000584 0.000612 0.000616
C3 0.031901 0.036666 0.039013 -0.011558 -0.002980 -0.002910 0.000662 0.000752
0.000834 0.000569 0.000623 0.000620
C4 0.036439 0.041531 0.034180 -0.014953 -0.001336 -0.002193 0.000748 0.000828
0.000864 0.000619 0.000742 0.000737
C2 0.030250 0.036893 0.039763 -0.013141 -0.001728 0.002639 0.000664 0.000752
0.000828 0.000572 0.000607 0.000607
C1 0.027525 0.032407 0.051456 -0.009438 0.005250 0.002039 0.000706 0.000831
0.000828 0.000622 0.000620 0.000686
C7 0.053818 0.063574 0.035298 -0.030086 -0.002850 0.002482 0.000890 0.001083
0.000924 0.000778 0.000824 0.000851
C6 0.055179 0.063692 0.038913 -0.033223 -0.006957 -0.002210 0.000931 0.001101
0.001028 0.000802 0.000786 0.000782
C10 0.035318 0.036348 0.059943 -0.011472 0.003664 0.004590 0.000801 0.000945
0.000982 0.000696 0.000702 0.000773
C13 0.037282 0.042654 0.058145 -0.014041 0.006647 -0.002083 0.000857 0.001049
0.001028 0.000747 0.000743 0.000803
C11 0.038825 0.034997 0.061771 -0.015179 0.000019 0.005702 0.000790 0.000982
0.001028 0.000769 0.000725 0.000863
C8 0.031295 0.035164 0.051556 -0.009174 -0.001918 0.010099 0.000716 0.000865
0.000848 0.000643 0.000640 0.000703
C12 0.035982 0.035461 0.056396 -0.011925 0.000377 0.003327 0.000746 0.000926
0.000963 0.000728 0.000694 0.000803
C9 0.031101 0.035327 0.045566 -0.013057 -0.002490 0.006211 0.000646 0.000815
0.000797 0.000592 0.000594 0.000662
O12 0.042965 0.039684 0.066866 -0.012175 0.002428 0.012746 0.000548 0.000591
0.000607 0.000449 0.000471 0.000487
N3 0.041488 0.046279 0.086290 -0.006344 0.014196 0.021332 0.000887 0.001004
0.001097 0.000833 0.000807 0.000912
N2 0.036074 0.045339 0.048094 -0.017927 -0.000576 0.003167 0.000648 0.000849
0.000796 0.000596 0.000579 0.000720
C17 0.033700 0.031274 0.041898 -0.015002 -0.001358 0.002760 0.000652 0.000781
0.000779 0.000579 0.000585 0.000645
C16 0.033279 0.028643 0.050189 -0.011849 -0.002783 0.007672 0.000686 0.000817
0.000825 0.000612 0.000619 0.000683
C18 0.043234 0.039400 0.066548 -0.018345 0.007729 -0.009588 0.000837 0.000984
0.001044 0.000769 0.000750 0.000876
C15 0.062383 0.040854 0.069535 -0.027536 0.027299 -0.012695 0.001050 0.001052
0.001042 0.000863 0.000838 0.000810
C14 0.063939 0.041418 0.072310 -0.031309 0.029227 -0.013087 0.001092 0.001090
0.001059 0.000879 0.000844 0.000915
C19 0.044580 0.049032 0.069082 -0.020899 0.015118 -0.016776 0.000919 0.001140
0.001118 0.000827 0.000807 0.000874
O8 0.039812 0.035193 0.094314 -0.009258 0.009242 0.004635 0.000573 0.000566
0.000699 0.000461 0.000520 0.000501
O11 0.060788 0.075198 0.075289 -0.034625 0.007937 0.013770 0.000674 0.000811
0.000723 0.000565 0.000562 0.000615
O9 0.036440 0.033549 0.075041 -0.010646 0.005740 -0.001672 0.000523 0.000565
0.000647 0.000427 0.000467 0.000467
O10 0.062419 0.057716 0.116202 -0.032968 0.004721 -0.020280 0.000691 0.000764
0.000946 0.000592 0.000642 0.000652
N5 0.075462 0.061928 0.036937 -0.024591 0.004347 -0.009671 0.000836 0.000974
0.000827 0.000742 0.000662 0.000760
N6 0.040994 0.042025 0.070728 -0.016972 0.003212 0.001729 0.000732 0.000790
0.000947 0.000604 0.000683 0.000688
O13 0.154290 0.092168 0.069903 -0.033553 0.027966 -0.041179 0.001273 0.001000
0.000880 0.000916 0.000805 0.000769
O14 0.132124 0.103095 0.041981 -0.040352 0.001434 0.009688 0.001043 0.001049
0.000702 0.000820 0.000693 0.000693
O7 0.042935 0.034460 0.079049 -0.013143 0.004812 0.009368 0.000554 0.000578
0.000649 0.000443 0.000484 0.000486
N1 0.038031 0.042019 0.047330 -0.017811 0.005473 -0.002548 0.000656 0.000785
0.000758 0.000575 0.000562 0.000668
N4 0.041440 0.037519 0.071526 -0.014940 0.009605 0.007322 0.000864 0.000921
0.001017 0.000784 0.000689 0.000813
C21 0.035791 0.034418 0.037278 -0.014232 0.002056 -0.001219 0.000682 0.000741
0.000787 0.000591 0.000607 0.000604
C20 0.031687 0.028570 0.050826 -0.007856 0.002989 0.001766 0.000732 0.000818
0.000816 0.000641 0.000633 0.000664
C24 0.034779 0.035042 0.049186 -0.010870 0.000217 0.001648 0.000710 0.000787
0.000876 0.000613 0.000640 0.000668
C25 0.050683 0.054141 0.043610 -0.024094 0.012100 -0.009651 0.000901 0.001006
0.000953 0.000765 0.000815 0.000847
C22 0.039212 0.037551 0.037316 -0.012180 -0.001921 -0.002874 0.000706 0.000773
0.000804 0.000610 0.000625 0.000624
C23 0.042323 0.037200 0.048459 -0.014903 -0.004182 -0.006128 0.000812 0.000910
0.001026 0.000672 0.000728 0.000756
C26 0.053990 0.051572 0.043899 -0.027513 0.008543 -0.012541 0.000919 0.001049
0.000973 0.000770 0.000738 0.000780

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 . N8 . 1.2013(13) yes
O1 . N8 . 1.2015(13) yes
O3 . N7 . 1.1932(14) yes
O4 . N7 . 1.1950(14) yes
O11 . N6 . 1.2114(14) yes
O10 . N6 . 1.2070(15) yes
O13 . N5 . 1.1967(15) yes
O14 . N5 . 1.1965(14) yes
O5 . C1 . 1.2605(14) yes
O6 . C1 . 1.2296(13) yes
O12 . C8 . 1.2206(13) yes
O8 . C20 . 1.2267(13) yes
O9 . C20 . 1.2488(13) yes
O7 . C16 . 1.2265(13) yes
N8 . C5 . 1.4616(15) yes
N7 . C3 . 1.4547(16) yes
N3 . C8 . 1.3204(19) yes
N2 . C13 . 1.3325(18) yes
N2 . C11 . 1.3307(18) yes
N5 . C22 . 1.4592(16) yes
N6 . C24 . 1.4670(16) yes
N1 . C14 . 1.3172(18) yes
N1 . C19 . 1.3215(18) yes
N4 . C16 . 1.3223(18) yes
N3 . H7 . 0.977(16) yes
N3 . H8 . 1.032(16) yes
N2 . H1 . 1.116(19) yes
N1 . H2 . 1.24(2) yes
N4 . H13 . 0.968(15) yes
N4 . H12 . 1.033(17) yes
C5 . C4 . 1.3718(18) yes
C5 . C6 . 1.3789(18) yes
C3 . C4 . 1.3847(17) yes
C3 . C2 . 1.3855(16) yes
C2 . C1 . 1.5077(16) yes
C2 . C7 . 1.3851(19) yes
C7 . C6 . 1.386(2) yes
C10 . C11 . 1.3850(18) yes
C10 . C9 . 1.3898(17) yes
C13 . C12 . 1.3795(19) yes
C8 . C9 . 1.5093(16) yes
C12 . C9 . 1.3835(18) yes
C17 . C16 . 1.4982(16) yes
C17 . C18 . 1.3784(18) yes
C17 . C15 . 1.3771(18) yes
C18 . C19 . 1.382(2) yes
C15 . C14 . 1.380(2) yes
C21 . C20 . 1.5168(16) yes
C21 . C22 . 1.3842(16) yes
C21 . C26 . 1.3882(17) yes
C24 . C25 . 1.3736(19) yes
C24 . C23 . 1.3798(19) yes
C25 . C26 . 1.383(2) yes
C22 . C23 . 1.3834(18) yes
C4 . H20 . 1.063(14) yes
C7 . H18 . 1.062(15) yes
C6 . H19 . 1.082(15) yes
C10 . H5 . 1.120(15) yes
C13 . H3 . 1.078(15) yes
C11 . H4 . 1.070(14) yes
C12 . H6 . 1.089(14) yes
C18 . H15 . 1.087(15) yes
C15 . H14 . 1.101(16) yes
C14 . H16 . 1.051(15) yes
C19 . H17 . 1.047(17) yes
C25 . H10 . 1.050(15) yes
C23 . H11 . 1.071(15) yes
C26 . H9 . 1.074(14) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . N8 . O1 . 123.20(12) yes
O3 . N7 . O4 . 123.12(14) yes
O11 . N6 . O10 . 123.98(13) yes
O13 . N5 . O14 . 124.02(13) yes
O2 . N8 . C5 . 118.58(13) yes
O1 . N8 . C5 . 118.22(12) yes
O3 . N7 . C3 . 118.43(13) yes
O4 . N7 . C3 . 118.40(13) yes
O11 . N6 . C24 . 117.88(14) yes
O10 . N6 . C24 . 118.14(13) yes
O13 . N5 . C22 . 118.08(13) yes
O14 . N5 . C22 . 117.90(13) yes
O5 . C1 . O6 . 126.41(11) yes
O8 . C20 . O9 . 126.38(12) yes
O12 . C8 . N3 . 123.61(12) yes
O7 . C16 . N4 . 123.79(12) yes
O5 . C1 . C2 . 116.50(11) yes
O6 . C1 . C2 . 116.96(12) yes
O12 . C8 . C9 . 119.72(11) yes
O8 . C20 . C21 . 117.68(11) yes
O9 . C20 . C21 . 115.92(11) yes
O7 . C16 . C17 . 119.17(12) yes
N8 . C5 . C4 . 118.56(12) yes
N8 . C5 . C6 . 118.77(13) yes
N7 . C3 . C4 . 116.98(12) yes
N7 . C3 . C2 . 119.96(12) yes
N3 . C8 . C9 . 116.65(12) yes
N2 . C13 . C12 . 120.30(15) yes
N2 . C11 . C10 . 120.74(14) yes
N5 . C22 . C21 . 119.66(11) yes
N5 . C22 . C23 . 117.09(13) yes
N6 . C24 . C25 . 119.21(13) yes
N6 . C24 . C23 . 118.17(14) yes
N1 . C14 . C15 . 122.53(15) yes
N1 . C19 . C18 . 121.24(15) yes
N4 . C16 . C17 . 117.04(12) yes
N2 . C13 . H3 . 116.3(8) yes
N2 . C11 . H4 . 116.7(8) yes
N1 . C14 . H16 . 113.7(9) yes
N1 . C19 . H17 . 115.8(9) yes
C13 . N2 . C11 . 121.61(14) yes
C14 . N1 . C19 . 119.73(14) yes
C13 . N2 . H1 . 122.8(8) yes
C11 . N2 . H1 . 115.5(8) yes
C8 . N3 . H7 . 117.4(10) yes
C8 . N3 . H8 . 122.2(9) yes
C16 . N4 . H13 . 116.5(9) yes
C16 . N4 . H12 . 121.0(10) yes
C14 . N1 . H2 . 117.1(8) yes
C19 . N1 . H2 . 123.2(8) yes
C5 . C4 . C3 . 117.00(13) yes
C5 . C6 . C7 . 118.54(15) yes
C3 . C2 . C1 . 125.15(12) yes
C3 . C2 . C7 . 117.63(12) yes
C4 . C5 . C6 . 122.67(13) yes
C4 . C3 . C2 . 122.95(13) yes
C2 . C7 . C6 . 121.19(14) yes
C1 . C2 . C7 . 117.22(12) yes
C10 . C9 . C8 . 122.55(12) yes
C10 . C9 . C12 . 118.96(12) yes
C13 . C12 . C9 . 119.58(14) yes
C11 . C10 . C9 . 118.77(14) yes
C8 . C9 . C12 . 118.46(11) yes
C17 . C18 . C19 . 119.58(14) yes
C17 . C15 . C14 . 118.58(14) yes
C16 . C17 . C18 . 119.15(12) yes
C16 . C17 . C15 . 122.51(12) yes
C18 . C17 . C15 . 118.34(13) yes
C21 . C22 . C23 . 123.21(12) yes
C21 . C26 . C25 . 121.84(15) yes
C20 . C21 . C22 . 123.19(11) yes
C20 . C21 . C26 . 119.65(12) yes
C24 . C25 . C26 . 118.33(14) yes
C24 . C23 . C22 . 116.94(14) yes
C25 . C24 . C23 . 122.62(13) yes
C22 . C21 . C26 . 117.06(12) yes
C5 . C4 . H20 . 122.6(8) yes
C5 . C6 . H19 . 121.0(8) yes
C3 . C4 . H20 . 120.4(8) yes
C2 . C7 . H18 . 119.2(9) yes
C7 . C6 . H19 . 120.5(8) yes
C6 . C7 . H18 . 119.5(9) yes
C10 . C11 . H4 . 122.6(8) yes
C13 . C12 . H6 . 120.5(8) yes
C11 . C10 . H5 . 119.5(7) yes
C12 . C13 . H3 . 123.4(8) yes
C9 . C10 . H5 . 121.8(7) yes
C9 . C12 . H6 . 119.9(8) yes
C17 . C18 . H15 . 118.9(8) yes
C17 . C15 . H14 . 120.5(8) yes
C18 . C19 . H17 . 123.0(9) yes
C15 . C14 . H16 . 123.8(9) yes
C14 . C15 . H14 . 120.9(8) yes
C19 . C18 . H15 . 121.5(8) yes
C21 . C26 . H9 . 118.5(8) yes
C24 . C25 . H10 . 119.6(9) yes
C24 . C23 . H11 . 122.6(8) yes
C25 . C26 . H9 . 119.6(8) yes
C22 . C23 . H11 . 120.4(8) yes
C26 . C25 . H10 . 122.0(9) yes
H13 . N4 . H12 . 120.7(14) yes
H7 . N3 . H8 . 120.3(14) yes
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate 2:2'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_200K_har
_database_code_depnum_ccdc_archive 'CCDC 1922038'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT051_complex_5_200K_har  
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.65 %
RESPONSE: Data collection at non-standard wavelength. Fprime used for anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_200K_har  
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.14 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a  very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT919_complex_5_200K_har  
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: Reflections used in the refinement are taken from the fcf from a SHELXL refinement using the LIST 4FVAR^2 command. HAR applies its own rejection criteria during the initial stages of refinement. Reflection was not rejected.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form


_audit_creation_date             2019-1-3
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            200K
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_weight         410.3897
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       214
_QCr_calc_unit_n_alpha_electrons 107
_QCr_calc_unit_n_beta_electrons  107

# =======
# Crystal
# =======

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             856

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/n 1'
_symmetry_space_group_name_Hall  '-p 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, +y+1/2, -z+1/2'
'+x+1/2, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      43.82

_cell_length_a                   7.1282(3)
_cell_length_b                   14.3290(6)
_cell_length_c                   18.3340(7)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 92.7370(18)
_cell_angle_gamma                90.000000(0)
_cell_volume                     1870.50(13)

_cell_formula_units_Z            4.000000

_atom_sites_solution_hydrogens   HAR

# ===========
# Device data
# ===========

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6458
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         41.363
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .


# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            332.158334

_reflns_d_resolution_high        9.156543
_reflns_d_resolution_low         0.670076
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                5411
_reflns_number_total             5411
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;


# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0253
_refine_ls_R_factor_all          0.0253
_refine_ls_wR_factor_gt          0.0196
_refine_ls_wR_factor_all         0.0196
_refine_ls_R_Fsqd_factor         0.0330
_refine_ls_goodness_of_fit_gt    1.5468
_refine_ls_goodness_of_fit_all   1.5468
_refine_ls_number_reflns         5411
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0079
_refine_ls_shift/su_max_mean     0.0010
_refine_ls_shift/su_max_par      'H8 Uyy'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1262
_refine_diff_density_min         -0.1337
_refine_diff_density_rms         0.0277
_refine_diff_density_max_atom    0.0536
_refine_diff_density_max_atom_tag H4B
_refine_diff_density_min_atom    -0.0571
_refine_diff_density_min_atom_tag H1
_refine_diff_density_rms_atom    0.0260

_refine_special_details          
;

  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field
   
. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 200K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  200K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

200k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 1.132002 0.674454 0.400070 0.063083 Uani 1.000000 0 0.001106 0.000458
0.000377 0.005449
H8 1.061079 0.563720 0.183203 0.056996 Uani 1.000000 0 0.001035 0.000446
0.000363 0.005074
H7 1.100318 0.698355 0.265676 0.066887 Uani 1.000000 0 0.001089 0.000475
0.000408 0.005540
H5 1.126199 0.512811 0.449373 0.056747 Uani 1.000000 0 0.001047 0.000475
0.000363 0.005113
H1 1.100261 0.275639 0.462699 0.043579 Uani 1.000000 0 0.001223 0.000634
0.000427 0.006130
O3 0.891505 0.340094 0.215508 0.026064 Uani 1.000000 0 0.000051 0.000023
0.000018 0.000189
O1 1.076370 0.344452 0.444346 0.030483 Uani 1.000000 0 0.000059 0.000027
0.000020 0.000210
O2 1.146572 0.283417 0.336682 0.032989 Uani 1.000000 0 0.000059 0.000024
0.000019 0.000209
O4 1.171826 0.365664 0.170046 0.035527 Uani 1.000000 0 0.000059 0.000026
0.000020 0.000223
C4 1.096912 0.446977 0.344119 0.021259 Uani 1.000000 0 0.000066 0.000032
0.000026 0.000232
C2 1.050593 0.382105 0.214220 0.023213 Uani 1.000000 0 0.000076 0.000032
0.000026 0.000243
C1 1.108721 0.350092 0.374074 0.022965 Uani 1.000000 0 0.000072 0.000033
0.000026 0.000240
C7 1.098402 0.628688 0.287759 0.032436 Uani 1.000000 0 0.000082 0.000037
0.000034 0.000298
C3 1.078874 0.461124 0.268248 0.021133 Uani 1.000000 0 0.000068 0.000031
0.000026 0.000229
C5 1.113067 0.523963 0.390883 0.027310 Uani 1.000000 0 0.000077 0.000036
0.000031 0.000271
C6 1.115059 0.614439 0.363019 0.031934 Uani 1.000000 0 0.000079 0.000037
0.000034 0.000298
C8 1.078825 0.552060 0.240953 0.027807 Uani 1.000000 0 0.000081 0.000035
0.000033 0.000271
H20 1.201662 0.020896 0.634395 0.052977 Uani 1.000000 0 0.001105 0.000422
0.000356 0.004805
H19 1.110861 0.186079 0.601080 0.059111 Uani 1.000000 0 0.001097 0.000442
0.000356 0.005135
H18 1.201815 0.141712 0.385161 0.058978 Uani 1.000000 0 0.001144 0.000453
0.000365 0.005126
H2A 1.336637 -0.158250 0.438633 0.050334 Uani 1.000000 0 0.001176 0.000488
0.000419 0.005376
H17 1.283549 -0.024088 0.406978 0.063910 Uani 1.000000 0 0.001087 0.000454
0.000347 0.005293
H2B 1.374934 -0.241709 0.508698 0.048241 Uani 1.000000 0 0.001108 0.000490
0.000404 0.005334
O5 1.293948 -0.136420 0.609210 0.034323 Uani 1.000000 0 0.000062 0.000024
0.000019 0.000214
N1 1.152321 0.169444 0.491948 0.025023 Uani 1.000000 0 0.000061 0.000027
0.000023 0.000216
N2 1.339423 -0.175324 0.491986 0.027780 Uani 1.000000 0 0.000071 0.000033
0.000027 0.000243
C15 1.296400 -0.114737 0.544070 0.023137 Uani 1.000000 0 0.000071 0.000032
0.000027 0.000243
C20 1.200990 0.045266 0.578042 0.026155 Uani 1.000000 0 0.000079 0.000034
0.000029 0.000264
C16 1.249328 -0.015738 0.522906 0.020826 Uani 1.000000 0 0.000064 0.000031
0.000026 0.000232
C19 1.151919 0.136558 0.560132 0.027018 Uani 1.000000 0 0.000081 0.000035
0.000030 0.000269
C17 1.249452 0.018237 0.451795 0.025932 Uani 1.000000 0 0.000077 0.000036
0.000029 0.000264
C18 1.201916 0.111281 0.439083 0.027641 Uani 1.000000 0 0.000080 0.000036
0.000030 0.000272
H11 0.869555 0.033769 0.027303 0.053294 Uani 1.000000 0 0.001063 0.000446
0.000352 0.004957
H13 0.939096 0.132217 0.282097 0.063880 Uani 1.000000 0 0.001165 0.000465
0.000393 0.005478
H12 0.871529 0.202603 0.066173 0.054035 Uani 1.000000 0 0.001066 0.000460
0.000361 0.004907
H14 0.943370 -0.039231 0.253964 0.064026 Uani 1.000000 0 0.001192 0.000433
0.000363 0.005333
H4A 0.830514 -0.245743 0.144952 0.048952 Uani 1.000000 0 0.001116 0.000490
0.000395 0.005289
H4B 0.774019 -0.159328 0.207004 0.047474 Uani 1.000000 0 0.001162 0.000474
0.000397 0.005283
H3 0.901112 0.246510 0.191314 0.033649 Uani 1.000000 0 0.001086 0.000600
0.000406 0.005835
O6 0.948385 -0.137216 0.053143 0.036159 Uani 1.000000 0 0.000062 0.000025
0.000020 0.000223
N4 0.841143 -0.178953 0.162768 0.028661 Uani 1.000000 0 0.000074 0.000033
0.000027 0.000247
N3 0.903045 0.170043 0.175015 0.026196 Uani 1.000000 0 0.000062 0.000031
0.000024 0.000227
C9 0.898107 -0.116919 0.114691 0.024550 Uani 1.000000 0 0.000073 0.000033
0.000027 0.000249
C11 0.882893 0.052384 0.084319 0.023911 Uani 1.000000 0 0.000074 0.000034
0.000029 0.000252
C10 0.900293 -0.015951 0.138210 0.021622 Uani 1.000000 0 0.000067 0.000032
0.000026 0.000235
C14 0.922339 0.011348 0.211125 0.029189 Uani 1.000000 0 0.000083 0.000037
0.000030 0.000276
C12 0.884833 0.145239 0.104648 0.025716 Uani 1.000000 0 0.000076 0.000036
0.000030 0.000262
C13 0.922675 0.105782 0.227859 0.031388 Uani 1.000000 0 0.000087 0.000037
0.000032 0.000293

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 1.1320(11) 0.6745(5) 0.4001(4) 0.063(5) Uani 1.000000 0
H8 1.0611(10) 0.5637(4) 0.1832(4) 0.057(5) Uani 1.000000 0
H7 1.1003(11) 0.6984(5) 0.2657(4) 0.067(6) Uani 1.000000 0
H5 1.1262(10) 0.5128(5) 0.4494(4) 0.057(5) Uani 1.000000 0
H1 1.1003(12) 0.2756(6) 0.4627(4) 0.044(6) Uani 1.000000 0
O3 0.89150(5) 0.34009(2) 0.215508(18) 0.02606(19) Uani 1.000000 0
O1 1.07637(6) 0.34445(3) 0.44435(2) 0.0305(2) Uani 1.000000 0
O2 1.14657(6) 0.28342(2) 0.336682(19) 0.0330(2) Uani 1.000000 0
O4 1.17183(6) 0.36566(3) 0.17005(2) 0.0355(2) Uani 1.000000 0
C4 1.09691(7) 0.44698(3) 0.34412(3) 0.0213(2) Uani 1.000000 0
C2 1.05059(8) 0.38210(3) 0.21422(3) 0.0232(2) Uani 1.000000 0
C1 1.10872(7) 0.35009(3) 0.37407(3) 0.0230(2) Uani 1.000000 0
C7 1.09840(8) 0.62869(4) 0.28776(3) 0.0324(3) Uani 1.000000 0
C3 1.07887(7) 0.46112(3) 0.26825(3) 0.0211(2) Uani 1.000000 0
C5 1.11307(8) 0.52396(4) 0.39088(3) 0.0273(3) Uani 1.000000 0
C6 1.11506(8) 0.61444(4) 0.36302(3) 0.0319(3) Uani 1.000000 0
C8 1.07882(8) 0.55206(3) 0.24095(3) 0.0278(3) Uani 1.000000 0
H20 1.2017(11) 0.0209(4) 0.6344(4) 0.053(5) Uani 1.000000 0
H19 1.1109(11) 0.1861(4) 0.6011(4) 0.059(5) Uani 1.000000 0
H18 1.2018(11) 0.1417(5) 0.3852(4) 0.059(5) Uani 1.000000 0
H2A 1.3366(12) -0.1583(5) 0.4386(4) 0.050(5) Uani 1.000000 0
H17 1.2835(11) -0.0241(5) 0.4070(3) 0.064(5) Uani 1.000000 0
H2B 1.3749(11) -0.2417(5) 0.5087(4) 0.048(5) Uani 1.000000 0
O5 1.29395(6) -0.13642(2) 0.609210(19) 0.0343(2) Uani 1.000000 0
N1 1.15232(6) 0.16944(3) 0.49195(2) 0.0250(2) Uani 1.000000 0
N2 1.33942(7) -0.17532(3) 0.49199(3) 0.0278(2) Uani 1.000000 0
C15 1.29640(7) -0.11474(3) 0.54407(3) 0.0231(2) Uani 1.000000 0
C20 1.20099(8) 0.04527(3) 0.57804(3) 0.0262(3) Uani 1.000000 0
C16 1.24933(6) -0.01574(3) 0.52291(3) 0.0208(2) Uani 1.000000 0
C19 1.15192(8) 0.13656(4) 0.56013(3) 0.0270(3) Uani 1.000000 0
C17 1.24945(8) 0.01824(4) 0.45180(3) 0.0259(3) Uani 1.000000 0
C18 1.20192(8) 0.11128(4) 0.43908(3) 0.0276(3) Uani 1.000000 0
H11 0.8696(11) 0.0338(4) 0.0273(4) 0.053(5) Uani 1.000000 0
H13 0.9391(12) 0.1322(5) 0.2821(4) 0.064(5) Uani 1.000000 0
H12 0.8715(11) 0.2026(5) 0.0662(4) 0.054(5) Uani 1.000000 0
H14 0.9434(12) -0.0392(4) 0.2540(4) 0.064(5) Uani 1.000000 0
H4A 0.8305(11) -0.2457(5) 0.1450(4) 0.049(5) Uani 1.000000 0
H4B 0.7740(12) -0.1593(5) 0.2070(4) 0.047(5) Uani 1.000000 0
H3 0.9011(11) 0.2465(6) 0.1913(4) 0.034(6) Uani 1.000000 0
O6 0.94839(6) -0.13722(3) 0.05314(2) 0.0362(2) Uani 1.000000 0
N4 0.84114(7) -0.17895(3) 0.16277(3) 0.0287(2) Uani 1.000000 0
N3 0.90305(6) 0.17004(3) 0.17502(2) 0.0262(2) Uani 1.000000 0
C9 0.89811(7) -0.11692(3) 0.11469(3) 0.0245(2) Uani 1.000000 0
C11 0.88289(7) 0.05238(3) 0.08432(3) 0.0239(3) Uani 1.000000 0
C10 0.90029(7) -0.01595(3) 0.13821(3) 0.0216(2) Uani 1.000000 0
C14 0.92234(8) 0.01135(4) 0.21113(3) 0.0292(3) Uani 1.000000 0
C12 0.88483(8) 0.14524(4) 0.10465(3) 0.0257(3) Uani 1.000000 0
C13 0.92268(9) 0.10578(4) 0.22786(3) 0.0314(3) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.084584 0.042766 0.060934 -0.006314 -0.006595 -0.012692 0.006335 0.004690
0.005315 0.004127 0.004658 0.003978
H8 0.076049 0.040698 0.054451 -0.001686 0.005293 0.011669 0.005758 0.004562
0.004916 0.003875 0.004509 0.003761
H7 0.084585 0.036055 0.079896 0.005837 0.002628 0.002556 0.006162 0.004520
0.005952 0.004224 0.004785 0.004053
H5 0.068433 0.055816 0.045980 0.008144 0.002599 -0.003963 0.005584 0.005030
0.004752 0.004121 0.004407 0.003856
H1 0.062885 0.034336 0.033217 0.000664 -0.000817 0.011434 0.006766 0.006096
0.005550 0.005152 0.004861 0.004588
O3 0.036509 0.020384 0.021383 -0.002855 0.002264 -0.003642 0.000216 0.000172
0.000179 0.000145 0.000156 0.000135
O1 0.047038 0.025437 0.019104 0.005386 0.002931 0.001588 0.000249 0.000197
0.000185 0.000175 0.000169 0.000150
O2 0.057246 0.020744 0.021147 0.010275 0.003639 0.001897 0.000260 0.000179
0.000187 0.000168 0.000176 0.000141
O4 0.049854 0.030540 0.027690 -0.001308 0.017563 -0.001408 0.000259 0.000203
0.000211 0.000174 0.000189 0.000157
C4 0.025251 0.017873 0.020444 0.001008 -0.001082 -0.000647 0.000244 0.000214
0.000237 0.000176 0.000192 0.000173
C2 0.034598 0.018375 0.017052 -0.000224 0.005257 0.000581 0.000286 0.000212
0.000232 0.000193 0.000204 0.000170
C1 0.031648 0.019209 0.017948 0.003754 0.000259 0.000979 0.000264 0.000225
0.000231 0.000187 0.000197 0.000177
C7 0.038832 0.016463 0.041857 -0.000697 0.000292 0.000993 0.000314 0.000238
0.000343 0.000218 0.000260 0.000224
C3 0.027850 0.015688 0.019892 -0.000516 0.001458 0.001403 0.000247 0.000206
0.000234 0.000175 0.000190 0.000169
C5 0.032427 0.022685 0.026308 0.001303 -0.003934 -0.005766 0.000287 0.000248
0.000278 0.000204 0.000229 0.000211
C6 0.036083 0.019788 0.039464 0.000059 -0.003089 -0.007032 0.000307 0.000246
0.000340 0.000213 0.000254 0.000226
C8 0.036707 0.017852 0.028904 -0.000811 0.002001 0.004698 0.000295 0.000231
0.000288 0.000200 0.000242 0.000207
H20 0.090088 0.037328 0.031719 0.003027 0.005036 0.008121 0.005983 0.004334
0.004108 0.004027 0.004188 0.003464
H19 0.092446 0.040044 0.045311 0.008434 0.008178 0.002816 0.006226 0.004506
0.004701 0.004139 0.004366 0.003627
H18 0.091499 0.046107 0.040223 0.012501 0.012498 0.010309 0.006230 0.004641
0.004556 0.004127 0.004443 0.003690
H2A 0.059376 0.046697 0.045562 0.008259 0.009119 0.000584 0.005983 0.005253
0.004932 0.004067 0.004685 0.004127
H17 0.099121 0.051305 0.042905 0.020560 0.020125 0.002722 0.006503 0.004764
0.004672 0.004439 0.004639 0.003741
H2B 0.069273 0.029818 0.046159 0.005910 0.008253 0.006797 0.006270 0.004531
0.005240 0.004208 0.004562 0.003835
O5 0.061236 0.019909 0.021705 0.005223 0.000744 0.003648 0.000272 0.000178
0.000192 0.000171 0.000184 0.000143
N1 0.032932 0.017692 0.024334 0.002364 0.000211 0.002654 0.000237 0.000195
0.000216 0.000167 0.000179 0.000162
N2 0.036939 0.021082 0.025576 0.004509 0.004170 0.001309 0.000267 0.000217
0.000247 0.000192 0.000214 0.000189
C15 0.031271 0.017886 0.020183 0.001077 0.000483 0.002535 0.000263 0.000216
0.000249 0.000186 0.000200 0.000177
C20 0.040738 0.019044 0.018596 0.001267 0.000488 0.000776 0.000307 0.000231
0.000253 0.000205 0.000222 0.000187
C16 0.025962 0.017199 0.019224 0.000064 0.000098 0.001411 0.000245 0.000209
0.000240 0.000178 0.000192 0.000172
C19 0.040904 0.018344 0.021773 0.002249 0.001149 -0.000992 0.000311 0.000232
0.000264 0.000211 0.000225 0.000192
C17 0.036730 0.020845 0.020433 0.005131 0.003579 0.002416 0.000292 0.000239
0.000260 0.000207 0.000220 0.000192
C18 0.040220 0.021593 0.021283 0.005716 0.003292 0.004647 0.000305 0.000243
0.000268 0.000211 0.000232 0.000196
H11 0.076011 0.047406 0.035872 -0.000341 -0.003512 0.002347 0.005740 0.004736
0.004392 0.003900 0.004257 0.003597
H13 0.101637 0.040935 0.049353 -0.004382 0.006590 -0.013064 0.006874 0.004615
0.004982 0.004232 0.004879 0.003831
H12 0.077829 0.039115 0.045819 -0.002067 0.009818 0.000013 0.005646 0.004462
0.004648 0.004041 0.004151 0.003565
H14 0.123062 0.034837 0.034471 -0.006052 0.006821 0.003462 0.007214 0.004460
0.004339 0.004363 0.004589 0.003465
H4A 0.068024 0.027637 0.051783 0.000488 0.008996 -0.005779 0.005949 0.004522
0.005444 0.004100 0.004567 0.003888
H4B 0.062446 0.041327 0.039428 -0.004943 0.010552 -0.002226 0.005949 0.005008
0.004959 0.004104 0.004470 0.003953
H3 0.044287 0.019324 0.037888 -0.007560 0.007738 -0.017975 0.005620 0.006484
0.005448 0.004602 0.004432 0.004551
O6 0.060058 0.022654 0.027413 -0.007656 0.019316 -0.005987 0.000273 0.000188
0.000211 0.000172 0.000195 0.000152
N4 0.042312 0.018873 0.025527 -0.002667 0.009234 -0.000787 0.000282 0.000210
0.000252 0.000200 0.000210 0.000184
N3 0.030341 0.018849 0.029701 -0.002747 0.004580 -0.004722 0.000234 0.000205
0.000244 0.000174 0.000187 0.000180
C9 0.034534 0.018477 0.021378 -0.003356 0.009059 -0.003023 0.000275 0.000219
0.000253 0.000192 0.000210 0.000180
C11 0.030944 0.020233 0.020711 -0.000900 0.002854 -0.000618 0.000269 0.000231
0.000255 0.000191 0.000210 0.000191
C10 0.027792 0.017894 0.019504 -0.003165 0.004525 -0.001902 0.000246 0.000214
0.000245 0.000181 0.000192 0.000177
C14 0.046736 0.021201 0.019872 -0.003958 0.004120 -0.001468 0.000326 0.000243
0.000259 0.000225 0.000236 0.000201
C12 0.032142 0.018486 0.026747 0.000205 0.003783 0.000577 0.000277 0.000233
0.000276 0.000201 0.000220 0.000203
C13 0.048658 0.022783 0.022827 -0.004127 0.002800 -0.006241 0.000338 0.000259
0.000283 0.000229 0.000248 0.000211

# ====
# ADPs
# ====


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 . C2 . 1.2851(6) yes
O1 . C1 . 1.3221(6) yes
O2 . C1 . 1.2138(6) yes
O4 . C2 . 1.2349(6) yes
O5 . C15 . 1.2350(6) yes
O6 . C9 . 1.2349(6) yes
O1 . H1 . 1.053(9) yes
N1 . C19 . 1.3361(7) yes
N1 . C18 . 1.3385(6) yes
N2 . C15 . 1.3370(6) yes
N4 . C9 . 1.3289(6) yes
N3 . C12 . 1.3385(7) yes
N3 . C13 . 1.3391(7) yes
N2 . H2A . 1.008(7) yes
N2 . H2B . 1.027(7) yes
N4 . H4A . 1.013(7) yes
N4 . H4B . 1.001(7) yes
N3 . H3 . 1.136(8) yes
C4 . C1 . 1.4939(6) yes
C4 . C3 . 1.4055(6) yes
C4 . C5 . 1.3985(7) yes
C2 . C3 . 1.5116(6) yes
C7 . C6 . 1.3943(8) yes
C7 . C8 . 1.3964(8) yes
C3 . C8 . 1.3958(6) yes
C5 . C6 . 1.3938(7) yes
C15 . C16 . 1.5043(6) yes
C20 . C16 . 1.3921(7) yes
C20 . C19 . 1.3894(7) yes
C16 . C17 . 1.3917(7) yes
C17 . C18 . 1.3925(7) yes
C9 . C10 . 1.5095(6) yes
C11 . C10 . 1.3924(7) yes
C11 . C12 . 1.3816(7) yes
C10 . C14 . 1.3945(7) yes
C14 . C13 . 1.3875(7) yes
C7 . H7 . 1.078(7) yes
C5 . H5 . 1.084(7) yes
C6 . H6 . 1.099(6) yes
C8 . H8 . 1.073(6) yes
C20 . H20 . 1.090(6) yes
C19 . H19 . 1.083(6) yes
C17 . H17 . 1.059(6) yes
C18 . H18 . 1.080(6) yes
C11 . H11 . 1.079(6) yes
C14 . H14 . 1.074(6) yes
C12 . H12 . 1.084(7) yes
C13 . H13 . 1.065(7) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 . C2 . O4 . 124.64(5) yes
O1 . C1 . O2 . 123.79(4) yes
O5 . C15 . N2 . 122.80(5) yes
O6 . C9 . N4 . 124.04(5) yes
O3 . C2 . C3 . 115.41(4) yes
O1 . C1 . C4 . 113.93(4) yes
O2 . C1 . C4 . 122.28(4) yes
O4 . C2 . C3 . 119.81(5) yes
O5 . C15 . C16 . 118.25(4) yes
O6 . C9 . C10 . 119.16(4) yes
N1 . C19 . C20 . 122.78(5) yes
N1 . C18 . C17 . 123.06(5) yes
N2 . C15 . C16 . 118.95(4) yes
N4 . C9 . C10 . 116.80(5) yes
N3 . C12 . C11 . 121.00(5) yes
N3 . C13 . C14 . 120.77(5) yes
N1 . C19 . H19 . 115.5(3) yes
N1 . C18 . H18 . 115.0(4) yes
N3 . C12 . H12 . 115.3(4) yes
N3 . C13 . H13 . 115.7(4) yes
C1 . O1 . H1 . 109.6(4) yes
C19 . N1 . C18 . 118.06(4) yes
C12 . N3 . C13 . 121.11(5) yes
C15 . N2 . H2A . 122.8(4) yes
C15 . N2 . H2B . 116.7(4) yes
C9 . N4 . H4A . 116.0(4) yes
C9 . N4 . H4B . 121.5(4) yes
C12 . N3 . H3 . 120.5(4) yes
C13 . N3 . H3 . 118.4(4) yes
C4 . C3 . C2 . 122.93(4) yes
C4 . C3 . C8 . 119.20(5) yes
C4 . C5 . C6 . 120.73(5) yes
C2 . C3 . C8 . 117.81(4) yes
C1 . C4 . C3 . 119.92(4) yes
C1 . C4 . C5 . 120.41(5) yes
C7 . C6 . C5 . 119.81(5) yes
C7 . C8 . C3 . 121.02(5) yes
C3 . C4 . C5 . 119.60(4) yes
C6 . C7 . C8 . 119.62(5) yes
C15 . C16 . C20 . 117.69(4) yes
C15 . C16 . C17 . 124.15(4) yes
C20 . C16 . C17 . 118.15(5) yes
C16 . C20 . C19 . 119.20(5) yes
C16 . C17 . C18 . 118.73(5) yes
C9 . C10 . C11 . 118.16(4) yes
C9 . C10 . C14 . 122.81(5) yes
C11 . C10 . C14 . 119.02(5) yes
C10 . C11 . C12 . 119.10(5) yes
C10 . C14 . C13 . 118.98(5) yes
C4 . C5 . H5 . 119.4(4) yes
C7 . C6 . H6 . 119.9(4) yes
C7 . C8 . H8 . 119.2(4) yes
C3 . C8 . H8 . 119.8(4) yes
C5 . C6 . H6 . 120.3(4) yes
C6 . C7 . H7 . 120.4(4) yes
C6 . C5 . H5 . 119.9(4) yes
C8 . C7 . H7 . 120.0(4) yes
C20 . C19 . H19 . 121.7(3) yes
C16 . C20 . H20 . 119.8(3) yes
C16 . C17 . H17 . 122.5(3) yes
C19 . C20 . H20 . 121.0(3) yes
C17 . C18 . H18 . 121.9(4) yes
C18 . C17 . H17 . 118.8(4) yes
C11 . C12 . H12 . 123.7(4) yes
C10 . C11 . H11 . 121.0(3) yes
C10 . C14 . H14 . 121.1(4) yes
C14 . C13 . H13 . 123.5(4) yes
C12 . C11 . H11 . 119.9(3) yes
C13 . C14 . H14 . 119.9(4) yes
H2A . N2 . H2B . 120.5(6) yes
H4A . N4 . H4B . 119.7(6) yes

_chemical_name_systematic        'isonicotinamide phthalate 2:1'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex7_250K_har
_database_code_depnum_ccdc_archive 'CCDC 1922031'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex7_250K_har   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      25.33 %     
RESPONSE: Related to the use of a non-standard diffraction wavelength. 
;
_vrf_PLAT353_complex7_250K_har   
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H2       .       1.23 Ang.  
RESPONSE: The long N-H distance is characteristic of H2 being in a short strong
charge assisted N+-H...O- hydrogen bond.
;
_vrf_PLAT230_complex7_250K_har   
;
PROBLEM: Hirshfeld Test Diff for    O4       --N7       .        7.9 s.u.  
RESPONSE: O4 and N7 are not the same atom type.
;
_vrf_PLAT430_complex7_250K_har   
;
PROBLEM: Short Inter D...A Contact  O9       ..N6       .       2.82 Ang.  
RESPONSE: O9 and N6 are in different layers of the crystal packing and form a pi-pi interaction.
;
# end Validation Reply Form

_audit_creation_date             2019-1-5
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            250K
_chemical_formula_sum            'C26 H20 N8 O14'
_chemical_formula_moiety         '2(C6 H7 N2 O1), 2(C7 H3 N2 O6)'
_chemical_formula_weight         668.4945
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       344
_QCr_calc_unit_n_alpha_electrons 172
_QCr_calc_unit_n_beta_electrons  172

# =======
# Crystal
# =======

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             688

# ==============
# Absortion data
# ==============

_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'p -1'
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'

# =========
# Unit cell
# =========

_cell_measurement_temperature    250
_cell_measurement_reflns_used    9351
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      43.63

_cell_length_a                   9.7313(4)
_cell_length_b                   10.3587(4)
_cell_length_c                   15.3935(6)
_cell_angle_alpha                78.736(2)
_cell_angle_beta                 71.341(2)
_cell_angle_gamma                77.307(2)
_cell_volume                     1421.05(10)

_cell_formula_units_Z            2.000000

_atom_sites_solution_hydrogens   HAR


# ===========
# Device data
# ===========
_diffrn_ambient_temperature      250
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6756
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         35.633
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========

_shelx_F_calc_maximum            215.586741

_reflns_d_resolution_high        10.012660
_reflns_d_resolution_low         0.760150
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                4979
_reflns_number_total             4979
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0329
_refine_ls_R_factor_all          0.0329
_refine_ls_wR_factor_gt          0.0229
_refine_ls_wR_factor_all         0.0229
_refine_ls_R_Fsqd_factor         0.0413
_refine_ls_goodness_of_fit_gt    1.5505
_refine_ls_goodness_of_fit_all   1.5505
_refine_ls_number_reflns         4979
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0028
_refine_ls_shift/su_max_mean     0.0003
_refine_ls_shift/su_max_par      'C25 pz'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.2016
_refine_diff_density_min         -0.2232
_refine_diff_density_rms         0.0399
_refine_diff_density_max_atom    0.0838
_refine_diff_density_max_atom_tag H10
_refine_diff_density_min_atom    -0.1043
_refine_diff_density_min_atom_tag C14
_refine_diff_density_rms_atom    0.0368

_refine_special_details          
;
  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field.

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 250K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  250K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

250k.cif obtained from res in _shelx_res_file
  
;




# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H19 1.477721 0.798217 0.121940 0.080936 Uani 1.000000 0 0.001440 0.001328
0.000870 0.010792
H5 0.817641 0.652286 0.163247 0.080009 Uani 1.000000 0 0.001379 0.001123
0.000962 0.010358
H10 -0.033265 0.344408 0.683127 0.086085 Uani 1.000000 0 0.001476 0.001260
0.000919 0.010899
H4 0.611959 0.564693 0.292212 0.072729 Uani 1.000000 0 0.001324 0.001254
0.000858 0.009805
H18 1.294692 0.648663 0.192756 0.087224 Uani 1.000000 0 0.001574 0.001302
0.000930 0.010830
H20 1.489665 0.734527 -0.147131 0.059903 Uani 1.000000 0 0.001255 0.001159
0.000889 0.008769
H3 0.400042 0.939988 0.347836 0.083478 Uani 1.000000 0 0.001485 0.001191
0.000889 0.010675
H6 0.595602 1.045105 0.225709 0.067990 Uani 1.000000 0 0.001261 0.001201
0.000838 0.009264
H17 1.090829 0.083307 0.158324 0.110009 Uani 1.000000 0 0.001608 0.001294
0.001146 0.012972
H15 0.891954 -0.029104 0.277117 0.083895 Uani 1.000000 0 0.001371 0.001259
0.000934 0.010549
H11 0.082777 0.166363 0.438679 0.066643 Uani 1.000000 0 0.001341 0.001278
0.000818 0.009691
H9 0.156170 0.488728 0.607809 0.080321 Uani 1.000000 0 0.001390 0.001267
0.000860 0.010339
H13 0.472113 0.116899 0.493001 0.067237 Uani 1.000000 0 0.001633 0.001323
0.001013 0.011196
H7 1.046881 0.884834 0.028415 0.080095 Uani 1.000000 0 0.001535 0.001343
0.001040 0.011808
H12 0.539267 0.261849 0.433255 0.065659 Uani 1.000000 0 0.001496 0.001461
0.000991 0.011029
H14 0.727920 0.337194 0.392464 0.116220 Uani 1.000000 0 0.001601 0.001263
0.001028 0.013110
H1 0.417176 0.700208 0.377383 0.053896 Uani 1.000000 0 0.001631 0.001380
0.001047 0.011444
H8 0.991685 0.748218 0.110537 0.076543 Uani 1.000000 0 0.001428 0.001423
0.001081 0.012016
H16 0.936481 0.431911 0.265433 0.103851 Uani 1.000000 0 0.001562 0.001381
0.000954 0.012024
H2 1.112360 0.319844 0.153373 0.061586 Uani 1.000000 0 0.001953 0.001582
0.001090 0.013680
O2 1.631062 0.898337 -0.140101 0.051554 Uani 1.000000 0 0.000082 0.000074
0.000055 0.000520
O1 1.662673 0.891260 -0.008845 0.067077 Uani 1.000000 0 0.000096 0.000088
0.000059 0.000605
O3 1.359275 0.571233 -0.168352 0.096748 Uani 1.000000 0 0.000114 0.000112
0.000068 0.000806
O4 1.156672 0.568381 -0.062990 0.073295 Uani 1.000000 0 0.000103 0.000095
0.000060 0.000644
O5 1.207141 0.399785 0.100439 0.040413 Uani 1.000000 0 0.000076 0.000070
0.000050 0.000460
O6 1.056443 0.571722 0.166815 0.044495 Uani 1.000000 0 0.000074 0.000063
0.000050 0.000456
N8 1.604155 0.860349 -0.058180 0.036976 Uani 1.000000 0 0.000095 0.000084
0.000069 0.000569
N7 1.281929 0.587110 -0.091660 0.047881 Uani 1.000000 0 0.000117 0.000095
0.000069 0.000649
C5 1.494199 0.772856 -0.016030 0.029858 Uani 1.000000 0 0.000102 0.000091
0.000068 0.000575
C3 1.341317 0.636461 -0.031190 0.029519 Uani 1.000000 0 0.000103 0.000091
0.000066 0.000574
C4 1.447866 0.716532 -0.073193 0.030809 Uani 1.000000 0 0.000120 0.000105
0.000078 0.000622
C2 1.284602 0.609518 0.064178 0.029588 Uani 1.000000 0 0.000100 0.000091
0.000067 0.000574
C1 1.171363 0.520555 0.113692 0.032530 Uani 1.000000 0 0.000107 0.000101
0.000069 0.000609
C7 1.335114 0.669049 0.118708 0.040071 Uani 1.000000 0 0.000129 0.000116
0.000084 0.000703
C6 1.439726 0.751539 0.079257 0.040137 Uani 1.000000 0 0.000131 0.000121
0.000081 0.000743
C10 0.728064 0.720046 0.203243 0.038270 Uani 1.000000 0 0.000126 0.000112
0.000079 0.000694
C13 0.495392 0.881295 0.306316 0.040032 Uani 1.000000 0 0.000130 0.000118
0.000083 0.000727
C11 0.616445 0.668361 0.273397 0.038555 Uani 1.000000 0 0.000125 0.000121
0.000084 0.000691
C8 0.840600 0.922934 0.111201 0.034380 Uani 1.000000 0 0.000111 0.000102
0.000070 0.000624
C12 0.604271 0.938545 0.237495 0.036720 Uani 1.000000 0 0.000121 0.000116
0.000079 0.000662
C9 0.723385 0.857668 0.185951 0.031427 Uani 1.000000 0 0.000104 0.000095
0.000067 0.000581
O12 0.813864 1.041770 0.082383 0.043757 Uani 1.000000 0 0.000073 0.000066
0.000049 0.000460
N3 0.969942 0.846493 0.082135 0.054616 Uani 1.000000 0 0.000123 0.000120
0.000087 0.000768
N2 0.504992 0.748737 0.323076 0.035910 Uani 1.000000 0 0.000104 0.000092
0.000066 0.000576
C17 0.795875 0.145903 0.341435 0.029852 Uani 1.000000 0 0.000103 0.000093
0.000065 0.000571
C16 0.675210 0.079975 0.410854 0.031519 Uani 1.000000 0 0.000108 0.000099
0.000068 0.000593
C18 0.899047 0.073998 0.275571 0.041267 Uani 1.000000 0 0.000124 0.000119
0.000082 0.000700
C15 0.807459 0.276554 0.340760 0.050852 Uani 1.000000 0 0.000139 0.000115
0.000086 0.000786
C14 0.919371 0.330780 0.272710 0.051764 Uani 1.000000 0 0.000141 0.000124
0.000088 0.000795
C19 1.008787 0.134639 0.209845 0.045738 Uani 1.000000 0 0.000136 0.000127
0.000088 0.000776
O8 0.470551 0.437967 0.406104 0.050370 Uani 1.000000 0 0.000077 0.000066
0.000053 0.000488
O11 -0.164090 0.168174 0.691466 0.060012 Uani 1.000000 0 0.000087 0.000078
0.000059 0.000568
O9 0.304458 0.618815 0.441206 0.041435 Uani 1.000000 0 0.000073 0.000065
0.000049 0.000448
O10 -0.123678 0.095619 0.562822 0.063633 Uani 1.000000 0 0.000088 0.000080
0.000065 0.000588
N5 0.284269 0.310243 0.338311 0.047014 Uani 1.000000 0 0.000107 0.000109
0.000064 0.000634
N6 -0.100197 0.164800 0.609670 0.043234 Uani 1.000000 0 0.000098 0.000090
0.000075 0.000618
O13 0.336067 0.201188 0.315661 0.091114 Uani 1.000000 0 0.000120 0.000099
0.000061 0.000773
O14 0.296828 0.413103 0.286416 0.076361 Uani 1.000000 0 0.000109 0.000094
0.000055 0.000675
O7 0.690747 -0.042579 0.424298 0.046104 Uani 1.000000 0 0.000074 0.000066
0.000051 0.000473
N1 1.016898 0.260840 0.209427 0.036003 Uani 1.000000 0 0.000101 0.000090
0.000065 0.000567
N4 0.556129 0.159349 0.453338 0.045099 Uani 1.000000 0 0.000120 0.000120
0.000081 0.000701
C21 0.224351 0.411053 0.480839 0.030206 Uani 1.000000 0 0.000103 0.000091
0.000067 0.000568
C20 0.344411 0.495953 0.438311 0.032073 Uani 1.000000 0 0.000112 0.000099
0.000067 0.000604
C24 0.012330 0.249704 0.565318 0.034066 Uani 1.000000 0 0.000106 0.000095
0.000072 0.000610
C25 0.031696 0.338178 0.614860 0.041864 Uani 1.000000 0 0.000131 0.000118
0.000086 0.000719
C22 0.200350 0.319193 0.434987 0.031260 Uani 1.000000 0 0.000107 0.000095
0.000065 0.000578
C23 0.096002 0.236933 0.475313 0.034542 Uani 1.000000 0 0.000124 0.000111
0.000082 0.000684
C26 0.137982 0.418262 0.571882 0.040534 Uani 1.000000 0 0.000130 0.000118
0.000079 0.000726

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H19 1.4777(14) 0.7982(13) 0.1219(9) 0.081(11) Uani 1.000000 0
H5 0.8176(14) 0.6523(11) 0.1632(10) 0.080(10) Uani 1.000000 0
H10 -0.0333(15) 0.3444(13) 0.6831(9) 0.086(11) Uani 1.000000 0
H4 0.6120(13) 0.5647(13) 0.2922(9) 0.073(10) Uani 1.000000 0
H18 1.2947(16) 0.6487(13) 0.1928(9) 0.087(11) Uani 1.000000 0
H20 1.4897(13) 0.7345(12) -0.1471(9) 0.060(9) Uani 1.000000 0
H3 0.4000(15) 0.9400(12) 0.3478(9) 0.083(11) Uani 1.000000 0
H6 0.5956(13) 1.0451(12) 0.2257(8) 0.068(9) Uani 1.000000 0
H17 1.0908(16) 0.0833(13) 0.1583(11) 0.110(13) Uani 1.000000 0
H15 0.8920(14) -0.0291(13) 0.2771(9) 0.084(11) Uani 1.000000 0
H11 0.0828(13) 0.1664(13) 0.4387(8) 0.067(10) Uani 1.000000 0
H9 0.1562(14) 0.4887(13) 0.6078(9) 0.080(10) Uani 1.000000 0
H13 0.4721(16) 0.1169(13) 0.4930(10) 0.067(11) Uani 1.000000 0
H7 1.0469(15) 0.8848(13) 0.0284(10) 0.080(12) Uani 1.000000 0
H12 0.5393(15) 0.2618(15) 0.4333(10) 0.066(11) Uani 1.000000 0
H14 0.7279(16) 0.3372(13) 0.3925(10) 0.116(13) Uani 1.000000 0
H1 0.4172(16) 0.7002(14) 0.3774(10) 0.054(11) Uani 1.000000 0
H8 0.9917(14) 0.7482(14) 0.1105(11) 0.077(12) Uani 1.000000 0
H16 0.9365(16) 0.4319(14) 0.2654(10) 0.104(12) Uani 1.000000 0
H2 1.112(2) 0.3198(16) 0.1534(11) 0.062(14) Uani 1.000000 0
O2 1.63106(8) 0.89834(7) -0.14010(5) 0.0516(5) Uani 1.000000 0
O1 1.66267(10) 0.89126(9) -0.00884(6) 0.0671(6) Uani 1.000000 0
O3 1.35927(11) 0.57123(11) -0.16835(7) 0.0967(8) Uani 1.000000 0
O4 1.15667(10) 0.56838(10) -0.06299(6) 0.0733(6) Uani 1.000000 0
O5 1.20714(8) 0.39979(7) 0.10044(5) 0.0404(5) Uani 1.000000 0
O6 1.05644(7) 0.57172(6) 0.16681(5) 0.0445(5) Uani 1.000000 0
N8 1.60416(9) 0.86035(8) -0.05818(7) 0.0370(6) Uani 1.000000 0
N7 1.28193(12) 0.58711(9) -0.09166(7) 0.0479(6) Uani 1.000000 0
C5 1.49420(10) 0.77286(9) -0.01603(7) 0.0299(6) Uani 1.000000 0
C3 1.34132(10) 0.63646(9) -0.03119(7) 0.0295(6) Uani 1.000000 0
C4 1.44787(12) 0.71653(11) -0.07319(8) 0.0308(6) Uani 1.000000 0
C2 1.28460(10) 0.60952(9) 0.06418(7) 0.0296(6) Uani 1.000000 0
C1 1.17136(11) 0.52055(10) 0.11369(7) 0.0325(6) Uani 1.000000 0
C7 1.33511(13) 0.66905(12) 0.11871(8) 0.0401(7) Uani 1.000000 0
C6 1.43973(13) 0.75154(12) 0.07926(8) 0.0401(7) Uani 1.000000 0
C10 0.72806(13) 0.72005(11) 0.20324(8) 0.0383(7) Uani 1.000000 0
C13 0.49539(13) 0.88130(12) 0.30632(8) 0.0400(7) Uani 1.000000 0
C11 0.61645(13) 0.66836(12) 0.27340(8) 0.0386(7) Uani 1.000000 0
C8 0.84060(11) 0.92293(10) 0.11120(7) 0.0344(6) Uani 1.000000 0
C12 0.60427(12) 0.93855(12) 0.23749(8) 0.0367(7) Uani 1.000000 0
C9 0.72339(10) 0.85767(10) 0.18595(7) 0.0314(6) Uani 1.000000 0
O12 0.81386(7) 1.04177(7) 0.08238(5) 0.0438(5) Uani 1.000000 0
N3 0.96994(12) 0.84649(12) 0.08214(9) 0.0546(8) Uani 1.000000 0
N2 0.50499(10) 0.74874(9) 0.32308(7) 0.0359(6) Uani 1.000000 0
C17 0.79588(10) 0.14590(9) 0.34143(7) 0.0299(6) Uani 1.000000 0
C16 0.67521(11) 0.07998(10) 0.41085(7) 0.0315(6) Uani 1.000000 0
C18 0.89905(12) 0.07400(12) 0.27557(8) 0.0413(7) Uani 1.000000 0
C15 0.80746(14) 0.27655(12) 0.34076(9) 0.0509(8) Uani 1.000000 0
C14 0.91937(14) 0.33078(12) 0.27271(9) 0.0518(8) Uani 1.000000 0
C19 1.00879(14) 0.13464(13) 0.20984(9) 0.0457(8) Uani 1.000000 0
O8 0.47055(8) 0.43797(7) 0.40610(5) 0.0504(5) Uani 1.000000 0
O11 -0.16409(9) 0.16817(8) 0.69147(6) 0.0600(6) Uani 1.000000 0
O9 0.30446(7) 0.61881(7) 0.44121(5) 0.0414(4) Uani 1.000000 0
O10 -0.12368(9) 0.09562(8) 0.56282(6) 0.0636(6) Uani 1.000000 0
N5 0.28427(11) 0.31024(11) 0.33831(6) 0.0470(6) Uani 1.000000 0
N6 -0.10020(10) 0.16480(9) 0.60967(8) 0.0432(6) Uani 1.000000 0
O13 0.33607(12) 0.20119(10) 0.31566(6) 0.0911(8) Uani 1.000000 0
O14 0.29683(11) 0.41310(9) 0.28642(6) 0.0764(7) Uani 1.000000 0
O7 0.69075(7) -0.04258(7) 0.42430(5) 0.0461(5) Uani 1.000000 0
N1 1.01690(10) 0.26084(9) 0.20943(6) 0.0360(6) Uani 1.000000 0
N4 0.55613(12) 0.15935(12) 0.45334(8) 0.0451(7) Uani 1.000000 0
C21 0.22435(10) 0.41105(9) 0.48084(7) 0.0302(6) Uani 1.000000 0
C20 0.34441(11) 0.49595(10) 0.43831(7) 0.0321(6) Uani 1.000000 0
C24 0.01233(11) 0.24970(9) 0.56532(7) 0.0341(6) Uani 1.000000 0
C25 0.03170(13) 0.33818(12) 0.61486(9) 0.0419(7) Uani 1.000000 0
C22 0.20035(11) 0.31919(9) 0.43499(7) 0.0313(6) Uani 1.000000 0
C23 0.09600(12) 0.23693(11) 0.47531(8) 0.0345(7) Uani 1.000000 0
C26 0.13798(13) 0.41826(12) 0.57188(8) 0.0405(7) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H19 0.088132 0.103159 0.064575 -0.060245 -0.013809 -0.005917 0.009337 0.012767
0.010383 0.008748 0.007864 0.008665
H5 0.052697 0.038037 0.118943 -0.007371 0.008445 0.003082 0.009268 0.008207
0.011661 0.006874 0.008029 0.007581
H10 0.091013 0.086997 0.072085 -0.047553 0.010500 -0.012893 0.010500 0.011550
0.010171 0.008498 0.008674 0.009005
H4 0.064023 0.067614 0.070193 -0.021186 0.013259 -0.015391 0.009248 0.009712
0.010038 0.007960 0.007504 0.008042
H18 0.101890 0.099373 0.069475 -0.048612 -0.029095 0.010506 0.009744 0.012209
0.010871 0.008431 0.009139 0.009790
H20 0.043489 0.067177 0.074152 -0.023906 -0.015381 -0.007775 0.007079 0.009343
0.009893 0.006199 0.007501 0.008404
H3 0.078720 0.064735 0.081598 -0.017988 0.019240 -0.016300 0.010778 0.009594
0.010383 0.007936 0.008208 0.007959
H6 0.051832 0.058160 0.073080 -0.009288 0.004634 0.001125 0.008525 0.008679
0.009571 0.007327 0.007018 0.007706
H17 0.086750 0.071503 0.159056 -0.040580 0.018886 -0.047661 0.011587 0.011187
0.015086 0.008986 0.010273 0.010125
H15 0.066988 0.060328 0.101613 -0.021149 0.019835 -0.021375 0.009982 0.009526
0.011075 0.008162 0.008090 0.008537
H11 0.064743 0.080451 0.056854 -0.028922 -0.004254 -0.018027 0.008602 0.010752
0.009566 0.007510 0.007064 0.007841
H9 0.077596 0.092184 0.072286 -0.043268 0.011914 -0.037992 0.009349 0.011550
0.010149 0.008191 0.007448 0.008415
H13 0.064547 0.054422 0.072219 -0.012213 -0.009560 0.000941 0.010473 0.009992
0.012173 0.008081 0.008564 0.008755
H7 0.047627 0.062148 0.083132 0.004968 0.021846 0.014965 0.011217 0.010182
0.010645 0.008089 0.008679 0.008565
H12 0.059050 0.040675 0.081708 -0.017220 -0.004102 0.010160 0.009818 0.010303
0.011899 0.008874 0.008215 0.009289
H14 0.106107 0.068275 0.135867 -0.066336 0.072146 -0.047976 0.013454 0.011238
0.012334 0.009996 0.010079 0.009497
H1 0.038291 0.049042 0.061333 -0.008510 0.000868 -0.001875 0.010243 0.010106
0.013508 0.008168 0.009761 0.009802
H8 0.040377 0.038319 0.113313 0.003193 0.012820 0.006526 0.010340 0.009598
0.013365 0.008710 0.009146 0.009094
H16 0.103342 0.084169 0.095097 -0.059539 0.056906 -0.040696 0.012422 0.011939
0.010749 0.009940 0.008708 0.009094
H2 0.074299 0.060325 0.041608 0.012896 -0.009509 -0.026882 0.014242 0.011624
0.016164 0.010592 0.013391 0.011796
O2 0.049426 0.056457 0.045915 -0.032366 -0.004064 0.009687 0.000462 0.000561
0.000507 0.000398 0.000389 0.000413
O1 0.070229 0.088789 0.057270 -0.057608 -0.014780 -0.001152 0.000491 0.000759
0.000607 0.000511 0.000459 0.000516
O3 0.093994 0.156838 0.060209 -0.066689 0.001953 -0.052728 0.000689 0.001090
0.000740 0.000694 0.000585 0.000728
O4 0.066254 0.111654 0.059792 -0.053894 -0.027596 0.006798 0.000476 0.000843
0.000652 0.000517 0.000476 0.000576
O5 0.030544 0.030015 0.048757 -0.011307 0.007857 -0.003428 0.000414 0.000443
0.000475 0.000335 0.000360 0.000361
O6 0.028085 0.029067 0.059537 -0.008186 0.008779 0.000412 0.000400 0.000416
0.000484 0.000330 0.000359 0.000362
N8 0.033568 0.038142 0.038678 -0.019887 -0.003902 0.000568 0.000498 0.000564
0.000616 0.000422 0.000448 0.000457
N7 0.048752 0.062601 0.040058 -0.029375 -0.010485 -0.006444 0.000571 0.000701
0.000693 0.000513 0.000534 0.000548
C5 0.026447 0.029439 0.031056 -0.011170 -0.002213 -0.001058 0.000502 0.000565
0.000622 0.000439 0.000455 0.000465
C3 0.026080 0.029135 0.030660 -0.009795 -0.002617 -0.001508 0.000507 0.000562
0.000628 0.000435 0.000461 0.000469
C4 0.029633 0.032825 0.026770 -0.011923 -0.000621 -0.001881 0.000570 0.000607
0.000646 0.000463 0.000540 0.000545
C2 0.023818 0.028845 0.031497 -0.010805 -0.001266 0.002365 0.000502 0.000553
0.000617 0.000428 0.000452 0.000459
C1 0.022267 0.025486 0.040147 -0.007433 0.003425 0.000773 0.000533 0.000602
0.000629 0.000461 0.000470 0.000508
C7 0.042756 0.048212 0.028281 -0.024598 -0.001788 0.001773 0.000646 0.000753
0.000682 0.000556 0.000579 0.000606
C6 0.043288 0.049371 0.030999 -0.025663 -0.004791 -0.002933 0.000659 0.000776
0.000742 0.000573 0.000556 0.000574
C10 0.028643 0.028051 0.046911 -0.009149 0.002530 0.003043 0.000603 0.000674
0.000731 0.000518 0.000524 0.000568
C13 0.030742 0.034969 0.044539 -0.012287 0.004577 -0.001142 0.000627 0.000747
0.000751 0.000547 0.000544 0.000592
C11 0.030413 0.028071 0.047620 -0.012664 0.001092 0.004812 0.000591 0.000702
0.000748 0.000556 0.000527 0.000610
C8 0.025681 0.028185 0.040402 -0.008087 -0.002428 0.007853 0.000540 0.000637
0.000646 0.000479 0.000480 0.000522
C12 0.028779 0.028300 0.044401 -0.009115 -0.000129 0.002346 0.000566 0.000666
0.000717 0.000536 0.000512 0.000593
C9 0.023667 0.028331 0.036257 -0.010196 -0.001762 0.004461 0.000493 0.000600
0.000613 0.000443 0.000451 0.000494
O12 0.033298 0.030699 0.051939 -0.009092 0.001862 0.010107 0.000413 0.000435
0.000469 0.000339 0.000359 0.000366
N3 0.031269 0.036595 0.067434 -0.004637 0.010911 0.015301 0.000646 0.000700
0.000787 0.000580 0.000560 0.000627
N2 0.027637 0.035995 0.038630 -0.014507 -0.000573 0.002674 0.000483 0.000604
0.000594 0.000435 0.000429 0.000514
C17 0.027388 0.025124 0.032740 -0.011816 -0.000861 0.001126 0.000504 0.000576
0.000599 0.000439 0.000449 0.000483
C16 0.026125 0.022674 0.038111 -0.009512 -0.001059 0.005765 0.000519 0.000597
0.000613 0.000452 0.000459 0.000498
C18 0.033549 0.030937 0.051251 -0.014562 0.006441 -0.008266 0.000619 0.000694
0.000756 0.000550 0.000540 0.000620
C15 0.049906 0.031547 0.053464 -0.022358 0.022649 -0.011063 0.000761 0.000738
0.000759 0.000615 0.000602 0.000594
C14 0.050588 0.032123 0.055280 -0.024042 0.022540 -0.010654 0.000781 0.000763
0.000773 0.000629 0.000605 0.000651
C19 0.036115 0.037485 0.053371 -0.016533 0.011858 -0.012765 0.000675 0.000772
0.000810 0.000589 0.000585 0.000624
O8 0.031660 0.027288 0.072613 -0.007284 0.007529 0.002886 0.000437 0.000419
0.000528 0.000347 0.000391 0.000373
O11 0.047337 0.059531 0.058686 -0.027343 0.005679 0.010683 0.000499 0.000585
0.000549 0.000421 0.000415 0.000452
O9 0.029045 0.026378 0.056964 -0.009000 0.004424 -0.001696 0.000398 0.000418
0.000485 0.000323 0.000355 0.000350
O10 0.048540 0.045721 0.090793 -0.026187 0.004097 -0.016204 0.000500 0.000538
0.000683 0.000432 0.000471 0.000477
N5 0.058147 0.048836 0.028646 -0.018662 0.002540 -0.007410 0.000606 0.000683
0.000606 0.000522 0.000485 0.000550
N6 0.031610 0.032070 0.056382 -0.013369 0.001430 0.001411 0.000525 0.000557
0.000702 0.000441 0.000484 0.000493
O13 0.124570 0.072160 0.055097 -0.027125 0.025042 -0.033339 0.000916 0.000700
0.000649 0.000642 0.000599 0.000553
O14 0.103649 0.079297 0.032220 -0.030647 0.000415 0.007881 0.000744 0.000718
0.000526 0.000580 0.000504 0.000507
O7 0.033583 0.026531 0.061874 -0.010053 0.004278 0.006868 0.000421 0.000426
0.000498 0.000337 0.000369 0.000364
N1 0.030329 0.033851 0.036692 -0.013928 0.003886 -0.001621 0.000493 0.000576
0.000574 0.000423 0.000428 0.000494
N4 0.033059 0.029492 0.055723 -0.010880 0.007553 0.005497 0.000625 0.000645
0.000745 0.000554 0.000506 0.000577
C21 0.028799 0.026895 0.029878 -0.011169 0.001209 -0.001268 0.000523 0.000546
0.000601 0.000443 0.000459 0.000459
C20 0.025071 0.022302 0.039952 -0.007086 0.001763 0.000979 0.000544 0.000596
0.000620 0.000472 0.000472 0.000490
C24 0.027936 0.027206 0.039508 -0.008480 0.000333 0.000213 0.000544 0.000569
0.000654 0.000457 0.000480 0.000493
C25 0.040159 0.043147 0.033887 -0.019377 0.010125 -0.007102 0.000669 0.000720
0.000699 0.000556 0.000584 0.000611
C22 0.032119 0.029619 0.028388 -0.010115 -0.001516 -0.002183 0.000541 0.000568
0.000600 0.000458 0.000467 0.000468
C23 0.034099 0.030112 0.037954 -0.012185 -0.003946 -0.004569 0.000606 0.000650
0.000747 0.000497 0.000534 0.000550
C26 0.042630 0.041493 0.034184 -0.021864 0.006073 -0.009933 0.000668 0.000742
0.000718 0.000562 0.000544 0.000573

# ====
# ADPs
# ====



# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 . N8 . 1.2057(10) yes
O1 . N8 . 1.2064(11) yes
O3 . N7 . 1.2001(12) yes
O4 . N7 . 1.2018(11) yes
O11 . N6 . 1.2165(11) yes
O10 . N6 . 1.2104(12) yes
O13 . N5 . 1.2012(11) yes
O14 . N5 . 1.2044(11) yes
O5 . C1 . 1.2612(11) yes
O6 . C1 . 1.2345(11) yes
O12 . C8 . 1.2246(11) yes
O8 . C20 . 1.2314(11) yes
O9 . C20 . 1.2516(11) yes
O7 . C16 . 1.2290(11) yes
N8 . C5 . 1.4627(12) yes
N7 . C3 . 1.4566(13) yes
N3 . C8 . 1.3234(14) yes
N2 . C13 . 1.3347(14) yes
N2 . C11 . 1.3325(14) yes
N5 . C22 . 1.4605(13) yes
N6 . C24 . 1.4660(13) yes
N1 . C14 . 1.3253(14) yes
N1 . C19 . 1.3255(14) yes
N4 . C16 . 1.3240(14) yes
N3 . H7 . 1.004(14) yes
N3 . H8 . 1.031(14) yes
N2 . H1 . 1.118(16) yes
N1 . H2 . 1.23(2) yes
N4 . H13 . 0.984(15) yes
N4 . H12 . 1.038(14) yes
C5 . C4 . 1.3741(14) yes
C5 . C6 . 1.3815(14) yes
C3 . C4 . 1.3858(14) yes
C3 . C2 . 1.3881(13) yes
C2 . C1 . 1.5096(13) yes
C2 . C7 . 1.3878(15) yes
C7 . C6 . 1.3854(15) yes
C10 . C11 . 1.3827(15) yes
C10 . C9 . 1.3915(14) yes
C13 . C12 . 1.3817(15) yes
C8 . C9 . 1.5091(13) yes
C12 . C9 . 1.3854(14) yes
C17 . C16 . 1.5005(13) yes
C17 . C18 . 1.3805(14) yes
C17 . C15 . 1.3803(14) yes
C18 . C19 . 1.3834(16) yes
C15 . C14 . 1.3813(15) yes
C21 . C20 . 1.5180(13) yes
C21 . C22 . 1.3870(13) yes
C21 . C26 . 1.3913(14) yes
C24 . C25 . 1.3777(15) yes
C24 . C23 . 1.3793(15) yes
C25 . C26 . 1.3858(16) yes
C22 . C23 . 1.3830(14) yes
C4 . H20 . 1.072(12) yes
C7 . H18 . 1.074(13) yes
C6 . H19 . 1.077(12) yes
C10 . H5 . 1.090(12) yes
C13 . H3 . 1.079(12) yes
C11 . H4 . 1.063(12) yes
C12 . H6 . 1.072(12) yes
C18 . H15 . 1.080(12) yes
C15 . H14 . 1.102(13) yes
C14 . H16 . 1.075(13) yes
C19 . H17 . 1.059(14) yes
C25 . H10 . 1.045(13) yes
C23 . H11 . 1.057(12) yes
C26 . H9 . 1.071(12) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 . N8 . O1 . 123.44(9) yes
O3 . N7 . O4 . 123.56(11) yes
O11 . N6 . O10 . 124.06(10) yes
O13 . N5 . O14 . 124.27(10) yes
O2 . N8 . C5 . 118.46(9) yes
O1 . N8 . C5 . 118.10(9) yes
O3 . N7 . C3 . 118.21(10) yes
O4 . N7 . C3 . 118.19(10) yes
O11 . N6 . C24 . 117.84(10) yes
O10 . N6 . C24 . 118.10(10) yes
O13 . N5 . C22 . 118.08(10) yes
O14 . N5 . C22 . 117.65(10) yes
O5 . C1 . O6 . 126.59(9) yes
O8 . C20 . O9 . 126.58(9) yes
O12 . C8 . N3 . 123.66(10) yes
O7 . C16 . N4 . 123.88(10) yes
O5 . C1 . C2 . 116.63(9) yes
O6 . C1 . C2 . 116.65(9) yes
O12 . C8 . C9 . 119.66(9) yes
O8 . C20 . C21 . 117.49(9) yes
O9 . C20 . C21 . 115.92(8) yes
O7 . C16 . C17 . 119.10(9) yes
N8 . C5 . C4 . 118.43(9) yes
N8 . C5 . C6 . 118.90(10) yes
N7 . C3 . C4 . 117.07(9) yes
N7 . C3 . C2 . 119.98(9) yes
N3 . C8 . C9 . 116.66(10) yes
N2 . C13 . C12 . 120.15(12) yes
N2 . C11 . C10 . 120.76(11) yes
N5 . C22 . C21 . 119.52(9) yes
N5 . C22 . C23 . 117.23(10) yes
N6 . C24 . C25 . 119.14(10) yes
N6 . C24 . C23 . 118.44(10) yes
N1 . C14 . C15 . 122.17(12) yes
N1 . C19 . C18 . 120.94(12) yes
N4 . C16 . C17 . 117.01(10) yes
N2 . C13 . H3 . 117.4(7) yes
N2 . C11 . H4 . 115.1(6) yes
N1 . C14 . H16 . 113.5(7) yes
N1 . C19 . H17 . 116.7(7) yes
C13 . N2 . C11 . 121.63(11) yes
C14 . N1 . C19 . 120.07(11) yes
C13 . N2 . H1 . 121.5(7) yes
C11 . N2 . H1 . 116.9(7) yes
C8 . N3 . H7 . 118.3(7) yes
C8 . N3 . H8 . 122.1(7) yes
C16 . N4 . H13 . 117.1(8) yes
C16 . N4 . H12 . 121.9(7) yes
C14 . N1 . H2 . 116.0(6) yes
C19 . N1 . H2 . 124.0(6) yes
C5 . C4 . C3 . 117.02(10) yes
C5 . C6 . C7 . 118.60(11) yes
C3 . C2 . C1 . 125.13(9) yes
C3 . C2 . C7 . 117.77(9) yes
C4 . C5 . C6 . 122.67(10) yes
C4 . C3 . C2 . 122.83(10) yes
C2 . C7 . C6 . 121.08(11) yes
C1 . C2 . C7 . 117.10(9) yes
C10 . C9 . C8 . 122.64(9) yes
C10 . C9 . C12 . 118.81(10) yes
C13 . C12 . C9 . 119.67(11) yes
C11 . C10 . C9 . 118.93(11) yes
C8 . C9 . C12 . 118.52(9) yes
C17 . C18 . C19 . 119.67(11) yes
C17 . C15 . C14 . 118.58(11) yes
C16 . C17 . C18 . 119.13(9) yes
C16 . C17 . C15 . 122.33(9) yes
C18 . C17 . C15 . 118.55(10) yes
C21 . C22 . C23 . 123.22(9) yes
C21 . C26 . C25 . 121.65(11) yes
C20 . C21 . C22 . 123.16(9) yes
C20 . C21 . C26 . 119.69(9) yes
C24 . C25 . C26 . 118.50(11) yes
C24 . C23 . C22 . 117.16(11) yes
C25 . C24 . C23 . 122.41(10) yes
C22 . C21 . C26 . 117.06(9) yes
C5 . C4 . H20 . 122.2(6) yes
C5 . C6 . H19 . 120.7(7) yes
C3 . C4 . H20 . 120.7(6) yes
C2 . C7 . H18 . 119.5(7) yes
C7 . C6 . H19 . 120.7(7) yes
C6 . C7 . H18 . 119.4(7) yes
C10 . C11 . H4 . 124.1(7) yes
C13 . C12 . H6 . 119.1(6) yes
C11 . C10 . H5 . 119.4(6) yes
C12 . C13 . H3 . 122.4(7) yes
C9 . C10 . H5 . 121.7(6) yes
C9 . C12 . H6 . 121.2(6) yes
C17 . C18 . H15 . 118.7(7) yes
C17 . C15 . H14 . 120.9(6) yes
C18 . C19 . H17 . 122.4(7) yes
C15 . C14 . H16 . 124.3(7) yes
C14 . C15 . H14 . 120.5(6) yes
C19 . C18 . H15 . 121.7(7) yes
C21 . C26 . H9 . 117.5(7) yes
C24 . C25 . H10 . 120.2(7) yes
C24 . C23 . H11 . 121.8(7) yes
C25 . C26 . H9 . 120.9(7) yes
C22 . C23 . H11 . 121.0(7) yes
C26 . C25 . H10 . 121.3(7) yes
H13 . N4 . H12 . 118.9(11) yes
H7 . N3 . H8 . 119.5(11) yes
_chemical_name_systematic        'isonicotinamide 2,4-dinitrobenzoate 2:2'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_200K_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1922036'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_complex_5_200K_shelxl 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      27.65 %     
RESPONSE: Data collection at non-standard wavelength. Fprime used for
anomalous dispersion and absorption coefficients.
;
_vrf_PLAT353_complex_5_200K_shelxl 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.12 Ang.  
RESPONSE: The long N-H distance is characteristic of H3 being in a 
very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_weight         410.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0100 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0180 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1282(3)
_cell_length_b                   14.3290(6)
_cell_length_c                   18.3340(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.7370(18)
_cell_angle_gamma                90
_cell_volume                     1870.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    200
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      43.82

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34324
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         41.363
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6455
_reflns_number_gt                5213
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 
SHEL 1000 0.67 command used to make multi_T datasets comparable: 0.67 Angstroms
is the maximum diffraction resolution of high T (350 K) data set.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0697P)²+0.2762P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6455
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H6 H 1.132(2) 0.6671(12) 0.3976(9) 0.048(4) Uiso 1 1 d . . . . .
H8 H 1.064(2) 0.5623(11) 0.1885(8) 0.040(4) Uiso 1 1 d . . . . .
H7 H 1.103(2) 0.6923(12) 0.2697(9) 0.050(5) Uiso 1 1 d . . . . .
H5 H 1.127(2) 0.5148(10) 0.4440(8) 0.037(4) Uiso 1 1 d . . . . .
H1 H 1.107(3) 0.2763(17) 0.4638(13) 0.091(7) Uiso 1 1 d . . . . .
O3 O 0.89111(11) 0.34013(5) 0.21556(4) 0.02741(15) Uani 1 1 d . . . . .
O1 O 1.07613(12) 0.34473(5) 0.44446(4) 0.03205(17) Uani 1 1 d . . . . .
O2 O 1.14655(13) 0.28324(5) 0.33660(4) 0.03452(18) Uani 1 1 d . . . . .
O4 O 1.17223(13) 0.36562(6) 0.17002(4) 0.03703(19) Uani 1 1 d . . . . .
C4 C 1.09694(13) 0.44704(6) 0.34401(5) 0.02223(17) Uani 1 1 d . . . . .
C2 C 1.05060(15) 0.38198(6) 0.21417(5) 0.02459(18) Uani 1 1 d . . . . .
C1 C 1.10866(14) 0.35005(6) 0.37387(5) 0.02379(17) Uani 1 1 d . . . . .
C7 C 1.09832(17) 0.62854(7) 0.28804(7) 0.0334(2) Uani 1 1 d . . . . .
C3 C 1.07866(13) 0.46118(6) 0.26823(5) 0.02185(16) Uani 1 1 d . . . . .
C5 C 1.11321(15) 0.52405(7) 0.39082(6) 0.02823(19) Uani 1 1 d . . . . .
C6 C 1.11526(16) 0.61425(7) 0.36271(7) 0.0331(2) Uani 1 1 d . . . . .
C8 C 1.07903(15) 0.55209(7) 0.24103(6) 0.0288(2) Uani 1 1 d . . . . .
H20 H 1.199(2) 0.0240(10) 0.6278(8) 0.038(4) Uiso 1 1 d . . . . .
H19 H 1.114(2) 0.1795(10) 0.5966(8) 0.036(4) Uiso 1 1 d . . . . .
H18 H 1.199(2) 0.1374(11) 0.3902(9) 0.044(4) Uiso 1 1 d . . . . .
H2A H 1.340(2) -0.1590(11) 0.4454(9) 0.044(4) Uiso 1 1 d . . . . .
H17 H 1.283(2) -0.0207(11) 0.4099(8) 0.044(4) Uiso 1 1 d . . . . .
H2B H 1.371(2) -0.2339(12) 0.5067(9) 0.045(4) Uiso 1 1 d . . . . .
O5 O 1.29382(14) -0.13645(5) 0.60937(4) 0.03582(19) Uani 1 1 d . . . . .
N1 N 1.15247(12) 0.16962(6) 0.49193(5) 0.02615(17) Uani 1 1 d . . . . .
N2 N 1.33931(14) -0.17507(6) 0.49205(5) 0.02885(18) Uani 1 1 d . . . . .
C15 C 1.29633(14) -0.11482(6) 0.54417(5) 0.02408(17) Uani 1 1 d . . . . .
C20 C 1.20110(15) 0.04537(7) 0.57787(5) 0.02718(19) Uani 1 1 d . . . . .
C16 C 1.24909(13) -0.01560(6) 0.52289(5) 0.02183(16) Uani 1 1 d . . . . .
C19 C 1.15219(16) 0.13652(7) 0.56000(5) 0.0279(2) Uani 1 1 d . . . . .
C17 C 1.24954(15) 0.01833(7) 0.45187(5) 0.02684(19) Uani 1 1 d . . . . .
C18 C 1.20186(16) 0.11120(7) 0.43906(5) 0.02842(19) Uani 1 1 d . . . . .
H11 H 0.871(2) 0.0359(10) 0.0320(8) 0.036(4) Uiso 1 1 d . . . . .
H13 H 0.938(2) 0.1312(11) 0.2760(9) 0.043(4) Uiso 1 1 d . . . . .
H12 H 0.871(2) 0.1964(11) 0.0690(8) 0.038(4) Uiso 1 1 d . . . . .
H14 H 0.945(2) -0.0327(11) 0.2514(9) 0.043(4) Uiso 1 1 d . . . . .
H4A H 0.832(2) -0.2409(12) 0.1460(9) 0.047(4) Uiso 1 1 d . . . . .
H4B H 0.784(2) -0.1584(11) 0.2041(9) 0.042(4) Uiso 1 1 d . . . . .
H3 H 0.900(3) 0.2451(13) 0.1911(10) 0.061(5) Uiso 1 1 d . . . . .
O6 O 0.94867(14) -0.13723(5) 0.05302(4) 0.0377(2) Uani 1 1 d . . . . .
N4 N 0.84168(14) -0.17874(6) 0.16280(5) 0.02976(18) Uani 1 1 d . . . . .
N3 N 0.90298(12) 0.17013(6) 0.17499(5) 0.02715(17) Uani 1 1 d . . . . .
C9 C 0.89825(14) -0.11686(6) 0.11455(5) 0.02551(18) Uani 1 1 d . . . . .
C11 C 0.88283(14) 0.05240(7) 0.08430(5) 0.02486(18) Uani 1 1 d . . . . .
C10 C 0.90024(13) -0.01585(6) 0.13824(5) 0.02247(17) Uani 1 1 d . . . . .
C14 C 0.92225(17) 0.01145(7) 0.21095(5) 0.0299(2) Uani 1 1 d . . . . .
C12 C 0.88476(14) 0.14513(6) 0.10466(6) 0.02647(18) Uani 1 1 d . . . . .
C13 C 0.92249(17) 0.10575(7) 0.22774(6) 0.0323(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C2 1.2867(13) . ?
O1 C1 1.3279(11) . ?
O2 C1 1.2140(12) . ?
O4 C2 1.2365(12) . ?
C4 C5 1.3994(12) . ?
C4 C3 1.4040(12) . ?
C4 C1 1.4945(12) . ?
C2 C3 1.5136(12) . ?
C7 C6 1.3838(17) . ?
C7 C8 1.3966(15) . ?
C3 C8 1.3949(12) . ?
C5 C6 1.3918(15) . ?
O5 C15 1.2358(12) . ?
N1 C19 1.3352(13) . ?
N1 C18 1.3405(13) . ?
N2 C15 1.3342(12) . ?
C15 C16 1.5081(12) . ?
C20 C19 1.3870(13) . ?
C20 C16 1.3889(13) . ?
C16 C17 1.3901(12) . ?
C17 C18 1.3906(13) . ?
O6 C9 1.2352(12) . ?
N4 C9 1.3287(12) . ?
N3 C12 1.3386(13) . ?
N3 C13 1.3390(14) . ?
C9 C10 1.5110(12) . ?
C11 C12 1.3801(13) . ?
C11 C10 1.3922(13) . ?
C10 C14 1.3909(13) . ?
C14 C13 1.3859(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C4 C3 119.62(8) . . ?
C5 C4 C1 120.47(8) . . ?
C3 C4 C1 119.84(8) . . ?
O4 C2 O3 124.92(9) . . ?
O4 C2 C3 119.73(9) . . ?
O3 C2 C3 115.20(8) . . ?
O2 C1 O1 123.85(9) . . ?
O2 C1 C4 122.50(8) . . ?
O1 C1 C4 113.64(8) . . ?
C6 C7 C8 119.72(9) . . ?
C8 C3 C4 119.13(8) . . ?
C8 C3 C2 117.94(8) . . ?
C4 C3 C2 122.88(8) . . ?
C6 C5 C4 120.48(9) . . ?
C7 C6 C5 120.12(9) . . ?
C3 C8 C7 120.92(10) . . ?
C19 N1 C18 117.79(8) . . ?
O5 C15 N2 123.02(9) . . ?
O5 C15 C16 118.25(9) . . ?
N2 C15 C16 118.74(8) . . ?
C19 C20 C16 119.26(9) . . ?
C20 C16 C17 118.13(8) . . ?
C20 C16 C15 117.71(8) . . ?
C17 C16 C15 124.16(8) . . ?
N1 C19 C20 122.94(9) . . ?
C16 C17 C18 118.78(9) . . ?
N1 C18 C17 123.09(9) . . ?
C12 N3 C13 120.89(9) . . ?
O6 C9 N4 124.14(9) . . ?
O6 C9 C10 119.32(8) . . ?
N4 C9 C10 116.54(8) . . ?
C12 C11 C10 119.00(9) . . ?
C14 C10 C11 119.04(8) . . ?
C14 C10 C9 122.95(9) . . ?
C11 C10 C9 118.00(8) . . ?
C13 C14 C10 119.07(9) . . ?
N3 C12 C11 121.16(9) . . ?
N3 C13 C14 120.83(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.06(2) 1.64(2) 2.7027(11) 179(2) . yes
C18 H18 O2 0.971(16) 2.331(16) 3.1129(12) 137.0(13) . yes
N2 H2A O4 0.886(16) 2.143(17) 3.0254(12) 173.9(15) 2_745 yes
C17 H17 O4 0.990(16) 2.225(16) 3.1956(13) 166.7(13) 2_745 yes
N2 H2B O6 0.911(17) 2.095(17) 3.0013(12) 173.1(14) 4_656 yes
C11 H11 O6 0.987(15) 2.528(15) 3.0899(12) 115.9(10) 3_755 yes
N4 H4A O5 0.944(17) 1.897(17) 2.8384(11) 175.5(15) 4 yes
N4 H4B O3 0.927(16) 1.974(16) 2.8553(11) 158.1(14) 2_645 yes
N3 H3 O3 1.115(19) 1.436(19) 2.5495(10) 176.6(17) . yes
N3 H3 O4 1.115(19) 2.638(18) 3.3992(12) 124.8(12) . yes

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.049

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_complex_5_350K_har
_database_code_depnum_ccdc_archive 'CCDC 1922027'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2019-06-10 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT353_complex_5_350K_har  
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N3       - H3       .       1.18 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT230_complex_5_350K_har  
;
PROBLEM: Hirshfeld Test Diff for    O2       --C1       .        7.5 s.u.
RESPONSE: May be due to an increased thermal motion of O2 at higher temperature. Difference expected where O2 and C1 are not the same atom type.
;
_vrf_PLAT919_complex_5_350K_har  
;
PROBLEM: Reflection # Likely Affected by the Beamstop ...          1 Check
RESPONSE: Reflections used in the refinement are taken from the fcf from a SHELXL refinement using the LIST 4FVAR^2 command. HAR applies its own rejection criteria during the initial stages of refinement. Reflection was not rejected.
;
_vrf_PLAT230_complex_5_350K_har_2 
;
PROBLEM: Hirshfeld Test Diff for    O1       --C1       .        5.3 s.u.
RESPONSE: May be due to an increased thermal motion of O2 at higher temperature. Difference expected where O2 and C1 are not the same atom type.
;
_vrf_PLAT230_complex_5_350K_har_3 
;
PROBLEM: Hirshfeld Test Diff for    O4       --C2       .        6.7 s.u.
RESPONSE: May be due to an increased thermal motion of O2 at higher temperature. Difference expected where O2 and C1 are not the same atom type.
;
_vrf_PLAT230_complex_5_350K_har_4 
;
PROBLEM: Hirshfeld Test Diff for    N4       --C9       .        6.6 s.u.
RESPONSE: May be due to an increased thermal motion of O2 at higher temperature. Difference expected where O2 and C1 are not the same atom type.
;
_vrf_PLAT353_complex_5_350K_har_2 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N2       - H2B      .       1.01 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
_vrf_PLAT353_complex_5_350K_har_3 
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N4       - H4A      .       1.01 Ang.
RESPONSE: The long N-H distance is characteristic of H3 being in a very short charge-assisted N(+)-H...O(-) hydrogen bond.
;
# Added during the CSD deposition process: Monday 10 June 2019 02:03 PM
# end Validation Reply Form




_audit_creation_date             2019-1-3
_audit_creation_method           'Tonto 18.05.31 github v. c4e213d'

# ============
# QCr software
# ============

_QCr_software                    Tonto
_QCr_software_version            '18.05.31 v. c4e213d'
_QCr_software_platform           Linux-4.13.0-41-generic
_QCr_software_build_date         '2018-05-31 11:32'
_QCr_software_website            https://github.com/dylan-jayatilaka/tonto

# ========
# Chemical
# ========

_chemical_name_common            350K
_chemical_formula_sum            'C20 H18 N4 O6'
_chemical_formula_moiety         'C8 H5 O4, C6 H7 N2 O1, C6 H6 N2 O1'
_chemical_formula_weight         410.3897
_chemical_compound_source        'see text'
_chemical_absolute_configuration unk

# ==========
# QCr method
# ==========

_QCr_calc_method                 Hartree-Fock
_QCr_calc_spinorbital_kind       restricted
_QCr_calc_gaussian_basis_set     def2-TZVP
_QCr_calc_gaussian_basis_set_kind cartesian
_QCr_calc_basis_max_l            3

_QCr_calc_unit                   'See _atom_site_* in tonto.cif2'
_QCr_calc_unit_spin_multiplicity 1
_QCr_calc_unit_n_electrons       214
_QCr_calc_unit_n_alpha_electrons 107
_QCr_calc_unit_n_beta_electrons  107

# =======
# Crystal
# =======

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             856

# ==============
# Absortion data
# ==============

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_T_max  0.7486
_exptl_absorpt_process_details   
;
 SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;

# ========
# Symmetry
# ========

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/n 1'
_symmetry_space_group_name_Hall  '-p 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, +y+1/2, -z+1/2'
'+x+1/2, -y+1/2, +z+1/2'

# =========
# Unit cell
# =========

_cell_measurement_temperature    350
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      43.79

_cell_length_a                   7.2897(3)
_cell_length_b                   14.3165(6)
_cell_length_c                   18.4105(7)
_cell_angle_alpha                90.000000(0)
_cell_angle_beta                 92.410(2)
_cell_angle_gamma                90.000000(0)
_cell_volume                     1919.68(13)

_cell_formula_units_Z            4.000000

_atom_sites_solution_hydrogens   HAR



# ===========
# Device data
# ===========

_diffrn_ambient_temperature      350
_diffrn_radiation_wavelength     0.8856
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source Beamline 11.3.1'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS Detector'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

# ================
# Diffraction data
# ================

_diffrn_reflns_number            6610
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         41.361
_diffrn_reflns_theta_full        32.097
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

# ===========
# Reflections
# ===========


_shelx_F_calc_maximum            323.574922

_reflns_d_resolution_high        9.197108
_reflns_d_resolution_low         0.670097
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                4527
_reflns_number_total             4527
_reflns_threshold_expression     'F>0 & F/u(F)>3.0 & |F_calc|>10^-3'

_reflns_special_details          
;
* Specify symmetry and Friedel pair averaging *

. Only reflections which satisfy the threshold expression
  are listed below, and only they are considered observed,
  thus the *_gt, *_all, & *_total data are always the same
;

# ===============
# Refinement data
# ===============

_refine_ls_kind                  'Hirshfeld atom refinement (HAR)'
_refine_ls_method_description    
;
   S.C. Capelli, H.-B. Burgi, B. Dittrich, S.Grabowsky
   and Dylan Jayatilaka, IUCrJ (2014). 1, 361-379
;
_refine_QCr_Psi_constraint       none

_refine_ls_SVD_threshold         0.1E-02
_refine_ls_coordinate_system     cartesian
_refine_ls_structure_factor_coeff F
_refine_ls_matrix_type           full
_refine_ls_R_factor_gt           0.0436
_refine_ls_R_factor_all          0.0436
_refine_ls_wR_factor_gt          0.0230
_refine_ls_wR_factor_all         0.0230
_refine_ls_R_Fsqd_factor         0.0289
_refine_ls_goodness_of_fit_gt    1.8009
_refine_ls_goodness_of_fit_all   1.8009
_refine_ls_number_reflns         4527
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_shift/su_conv_tol     0.0100
_refine_ls_shift/su_max          0.0055
_refine_ls_shift/su_max_mean     0.0007
_refine_ls_shift/su_max_par      'H8 Uyy'
_refine_ls_extinction_method     none

_refine_diff_density_max         0.1629
_refine_diff_density_min         -0.1547
_refine_diff_density_rms         0.0365
_refine_diff_density_max_atom    0.0866
_refine_diff_density_max_atom_tag H2B
_refine_diff_density_min_atom    -0.0715
_refine_diff_density_min_atom_tag C13
_refine_diff_density_rms_atom    0.0402

_refine_special_details          
;
  HAR makes use of tailor-made aspherical atomic form factors calculated
   on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
   spherical-atom form factors.
 
  The ED is calculated from a gaussian basis set single determinant SCF
   wavefunction - either SCF or DFT - for a fragment of the crystal embedded in
   an electrostatic crystal field

. If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
  
  Run hart with the following options:
  -shelx-f2 350K.hkl
  -basis def2-TZVP
  -fos 3
  -dtol 0.0001
  -cluster-radius 0
  -dispersion "H 0.0 0.0 C 0.006 0.003 N 0.01 0.005 O 0.0018 0.01"
  -extinction False
  -complete-mol f
  -basis-dir /dls/i19-1/data/2017/nr18193-1/processing/hart/basis_sets
  -h-adps t
  -scf rhf
  350K.cif

The hart program version is:

Version: 18.05.31 v. c4e213d
Platform: Linux-4.13.0-41-generic
Build-date: 2018-05-31 11:32

350k.cif obtained from res in _shelx_res_file
;


# =====================================
# Precise fractional system coordinates
# =====================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Please keep for a better refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_label
_atom_site_Cryst_x
_atom_site_Cryst_y
_atom_site_Cryst_z
_atom_site_Cryst_U_iso_or_equiv
_atom_site_Cryst_adp_type
_atom_site_Cryst_occupancy
_atom_site_Cryst_disorder_group
_atom_site_Cryst_x_esu
_atom_site_Cryst_y_esu
_atom_site_Cryst_z_esu
_atom_site_Cryst_U_iso_or_equiv_esu
H6 1.128372 0.676353 0.398838 0.106643 Uani 1.000000 0 0.001588 0.000669
0.000564 0.009133
H8 1.058563 0.563288 0.184895 0.094448 Uani 1.000000 0 0.001575 0.000646
0.000544 0.008195
H7 1.095427 0.699045 0.265086 0.112781 Uani 1.000000 0 0.001635 0.000689
0.000630 0.009348
H5 1.123909 0.513837 0.447702 0.096019 Uani 1.000000 0 0.001611 0.000699
0.000544 0.008341
H1 1.109012 0.277572 0.461905 0.072226 Uani 1.000000 0 0.001745 0.000960
0.000585 0.009468
O3 0.900722 0.339847 0.216978 0.053454 Uani 1.000000 0 0.000085 0.000038
0.000028 0.000358
O1 1.082659 0.345627 0.443620 0.061589 Uani 1.000000 0 0.000104 0.000045
0.000033 0.000423
O2 1.150982 0.284940 0.337122 0.067620 Uani 1.000000 0 0.000095 0.000039
0.000029 0.000402
O4 1.172135 0.366977 0.170975 0.072526 Uani 1.000000 0 0.000100 0.000042
0.000032 0.000432
C4 1.098570 0.447845 0.343882 0.041346 Uani 1.000000 0 0.000101 0.000049
0.000039 0.000422
C2 1.054765 0.382868 0.215093 0.046572 Uani 1.000000 0 0.000131 0.000051
0.000039 0.000474
C1 1.113390 0.351403 0.373988 0.045339 Uani 1.000000 0 0.000114 0.000053
0.000040 0.000459
C7 1.094892 0.629139 0.287870 0.063963 Uani 1.000000 0 0.000137 0.000061
0.000060 0.000620
C3 1.079901 0.461791 0.268575 0.041819 Uani 1.000000 0 0.000105 0.000047
0.000040 0.000428
C5 1.113088 0.524915 0.390169 0.053451 Uani 1.000000 0 0.000133 0.000061
0.000052 0.000548
C6 1.112459 0.615116 0.362516 0.062732 Uani 1.000000 0 0.000132 0.000063
0.000060 0.000620
C8 1.077327 0.552517 0.241560 0.055433 Uani 1.000000 0 0.000142 0.000059
0.000056 0.000545
H20 1.197945 0.020934 0.633153 0.096798 Uani 1.000000 0 0.001742 0.000613
0.000534 0.008319
H19 1.114753 0.186503 0.600812 0.100880 Uani 1.000000 0 0.001690 0.000632
0.000513 0.008609
H18 1.207750 0.141649 0.386374 0.108277 Uani 1.000000 0 0.001789 0.000639
0.000504 0.009039
H2A 1.335330 -0.155983 0.441232 0.083433 Uani 1.000000 0 0.001842 0.000726
0.000621 0.008793
H17 1.287768 -0.023719 0.408740 0.113058 Uani 1.000000 0 0.001755 0.000657
0.000487 0.009299
H2B 1.364359 -0.240332 0.509808 0.078875 Uani 1.000000 0 0.001607 0.000748
0.000593 0.008388
O5 1.289929 -0.135828 0.608738 0.069559 Uani 1.000000 0 0.000100 0.000037
0.000029 0.000418
N1 1.155733 0.170007 0.492504 0.050660 Uani 1.000000 0 0.000098 0.000042
0.000036 0.000405
N2 1.334573 -0.174518 0.492569 0.056000 Uani 1.000000 0 0.000134 0.000061
0.000048 0.000502
C15 1.293044 -0.114033 0.544270 0.046110 Uani 1.000000 0 0.000113 0.000051
0.000044 0.000465
C20 1.198821 0.045793 0.577724 0.052007 Uani 1.000000 0 0.000133 0.000056
0.000048 0.000511
C16 1.247617 -0.015039 0.523333 0.040664 Uani 1.000000 0 0.000101 0.000048
0.000039 0.000420
C19 1.152599 0.136991 0.559860 0.054796 Uani 1.000000 0 0.000138 0.000060
0.000048 0.000552
C17 1.250742 0.018951 0.453013 0.052030 Uani 1.000000 0 0.000130 0.000059
0.000047 0.000528
C18 1.205273 0.111892 0.440334 0.055434 Uani 1.000000 0 0.000131 0.000059
0.000049 0.000543
H11 0.871552 0.033375 0.028391 0.092132 Uani 1.000000 0 0.001654 0.000643
0.000503 0.008190
H13 0.942045 0.130230 0.280384 0.111548 Uani 1.000000 0 0.001812 0.000697
0.000579 0.009359
H12 0.877900 0.203017 0.067661 0.091833 Uani 1.000000 0 0.001578 0.000656
0.000503 0.007855
H14 0.941925 -0.038948 0.252537 0.116203 Uani 1.000000 0 0.001910 0.000633
0.000532 0.009370
H4A 0.824672 -0.245224 0.144727 0.082021 Uani 1.000000 0 0.001611 0.000735
0.000538 0.008605
H4B 0.777327 -0.159250 0.205976 0.080493 Uani 1.000000 0 0.001851 0.000718
0.000562 0.008781
H3 0.907171 0.249307 0.192161 0.070737 Uani 1.000000 0 0.001537 0.001017
0.000586 0.010558
O6 0.939538 -0.137087 0.053084 0.072971 Uani 1.000000 0 0.000103 0.000039
0.000031 0.000432
N4 0.836921 -0.178493 0.161841 0.058311 Uani 1.000000 0 0.000135 0.000059
0.000048 0.000528
N3 0.907322 0.170068 0.174873 0.052184 Uani 1.000000 0 0.000101 0.000052
0.000041 0.000445
C9 0.892827 -0.116499 0.114252 0.048131 Uani 1.000000 0 0.000116 0.000052
0.000043 0.000475
C11 0.883685 0.052760 0.084847 0.047002 Uani 1.000000 0 0.000122 0.000056
0.000048 0.000480
C10 0.898041 -0.015857 0.137891 0.042178 Uani 1.000000 0 0.000104 0.000049
0.000040 0.000429
C14 0.920375 0.011118 0.210083 0.058402 Uani 1.000000 0 0.000143 0.000063
0.000048 0.000560
C12 0.888935 0.145158 0.105270 0.050448 Uani 1.000000 0 0.000123 0.000059
0.000049 0.000520
C13 0.923978 0.105440 0.226847 0.062536 Uani 1.000000 0 0.000150 0.000065
0.000055 0.000610

# ======================
# Fractional coordinates
# ======================

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_disorder_group
H6 1.1284(16) 0.6764(7) 0.3988(6) 0.107(9) Uani 1.000000 0
H8 1.0586(16) 0.5633(6) 0.1849(5) 0.094(8) Uani 1.000000 0
H7 1.0954(16) 0.6990(7) 0.2651(6) 0.113(9) Uani 1.000000 0
H5 1.1239(16) 0.5138(7) 0.4477(5) 0.096(8) Uani 1.000000 0
H1 1.1090(17) 0.2776(10) 0.4619(6) 0.072(9) Uani 1.000000 0
O3 0.90072(8) 0.33985(4) 0.21698(3) 0.0535(4) Uani 1.000000 0
O1 1.08266(10) 0.34563(4) 0.44362(3) 0.0616(4) Uani 1.000000 0
O2 1.15098(9) 0.28494(4) 0.33712(3) 0.0676(4) Uani 1.000000 0
O4 1.17214(10) 0.36698(4) 0.17097(3) 0.0725(4) Uani 1.000000 0
C4 1.09857(10) 0.44784(5) 0.34388(4) 0.0413(4) Uani 1.000000 0
C2 1.05476(13) 0.38287(5) 0.21509(4) 0.0466(5) Uani 1.000000 0
C1 1.11339(11) 0.35140(5) 0.37399(4) 0.0453(5) Uani 1.000000 0
C7 1.09489(14) 0.62914(6) 0.28787(6) 0.0640(6) Uani 1.000000 0
C3 1.07990(10) 0.46179(5) 0.26857(4) 0.0418(4) Uani 1.000000 0
C5 1.11309(13) 0.52492(6) 0.39017(5) 0.0535(5) Uani 1.000000 0
C6 1.11246(13) 0.61512(6) 0.36252(6) 0.0627(6) Uani 1.000000 0
C8 1.07733(14) 0.55252(6) 0.24156(6) 0.0554(5) Uani 1.000000 0
H20 1.1979(17) 0.0209(6) 0.6332(5) 0.097(8) Uani 1.000000 0
H19 1.1148(17) 0.1865(6) 0.6008(5) 0.101(9) Uani 1.000000 0
H18 1.2078(18) 0.1416(6) 0.3864(5) 0.108(9) Uani 1.000000 0
H2A 1.3353(18) -0.1560(7) 0.4412(6) 0.083(9) Uani 1.000000 0
H17 1.2878(18) -0.0237(7) 0.4087(5) 0.113(9) Uani 1.000000 0
H2B 1.3644(16) -0.2403(7) 0.5098(6) 0.079(8) Uani 1.000000 0
O5 1.28993(10) -0.13583(4) 0.60874(3) 0.0696(4) Uani 1.000000 0
N1 1.15573(10) 0.17001(4) 0.49250(4) 0.0507(4) Uani 1.000000 0
N2 1.33457(13) -0.17452(6) 0.49257(5) 0.0560(5) Uani 1.000000 0
C15 1.29304(11) -0.11403(5) 0.54427(4) 0.0461(5) Uani 1.000000 0
C20 1.19882(13) 0.04579(6) 0.57772(5) 0.0520(5) Uani 1.000000 0
C16 1.24762(10) -0.01504(5) 0.52333(4) 0.0407(4) Uani 1.000000 0
C19 1.15260(14) 0.13699(6) 0.55986(5) 0.0548(6) Uani 1.000000 0
C17 1.25074(13) 0.01895(6) 0.45301(5) 0.0520(5) Uani 1.000000 0
C18 1.20527(13) 0.11189(6) 0.44033(5) 0.0554(5) Uani 1.000000 0
H11 0.8716(17) 0.0334(6) 0.0284(5) 0.092(8) Uani 1.000000 0
H13 0.9420(18) 0.1302(7) 0.2804(6) 0.112(9) Uani 1.000000 0
H12 0.8779(16) 0.2030(7) 0.0677(5) 0.092(8) Uani 1.000000 0
H14 0.9419(19) -0.0389(6) 0.2525(5) 0.116(9) Uani 1.000000 0
H4A 0.8247(16) -0.2452(7) 0.1447(5) 0.082(9) Uani 1.000000 0
H4B 0.7773(19) -0.1593(7) 0.2060(6) 0.080(9) Uani 1.000000 0
H3 0.9072(15) 0.2493(10) 0.1922(6) 0.071(11) Uani 1.000000 0
O6 0.93954(10) -0.13709(4) 0.05308(3) 0.0730(4) Uani 1.000000 0
N4 0.83692(13) -0.17849(6) 0.16184(5) 0.0583(5) Uani 1.000000 0
N3 0.90732(10) 0.17007(5) 0.17487(4) 0.0522(4) Uani 1.000000 0
C9 0.89283(12) -0.11650(5) 0.11425(4) 0.0481(5) Uani 1.000000 0
C11 0.88368(12) 0.05276(6) 0.08485(5) 0.0470(5) Uani 1.000000 0
C10 0.89804(10) -0.01586(5) 0.13789(4) 0.0422(4) Uani 1.000000 0
C14 0.92037(14) 0.01112(6) 0.21008(5) 0.0584(6) Uani 1.000000 0
C12 0.88894(12) 0.14516(6) 0.10527(5) 0.0504(5) Uani 1.000000 0
C13 0.92398(15) 0.10544(6) 0.22685(6) 0.0625(6) Uani 1.000000 0

# ==================================
# Precise cartesian axis system ADPs
# ==================================

# . These precise data use non-standard CIF tags
# . Non-standard tags shadow standard tags to avoid duplication
# . Keep these for a refinement restart
# . Better yet, use the refined cartesian parameters

loop_
_atom_site_Cryst_ADP2_U_label
_atom_site_Cryst_ADP2_U_11
_atom_site_Cryst_ADP2_U_22
_atom_site_Cryst_ADP2_U_33
_atom_site_Cryst_ADP2_U_12
_atom_site_Cryst_ADP2_U_13
_atom_site_Cryst_ADP2_U_23
_atom_site_Cryst_ADP2_U_11_esu
_atom_site_Cryst_ADP2_U_22_esu
_atom_site_Cryst_ADP2_U_33_esu
_atom_site_Cryst_ADP2_U_12_esu
_atom_site_Cryst_ADP2_U_13_esu
_atom_site_Cryst_ADP2_U_23_esu
H6 0.130240 0.072501 0.115366 -0.011150 -0.016450 -0.028611 0.010295 0.007696
0.009362 0.006781 0.007767 0.006781
H8 0.128256 0.064090 0.091541 0.006491 0.011049 0.018599 0.009571 0.007086
0.007972 0.006063 0.007869 0.006251
H7 0.145401 0.053974 0.140064 -0.002561 0.019009 0.008233 0.010758 0.006979
0.010385 0.006811 0.008232 0.006929
H5 0.118712 0.085735 0.081883 0.014662 -0.016285 -0.020785 0.009508 0.007975
0.007505 0.006343 0.007778 0.006449
H1 0.100176 0.070989 0.044824 0.019191 -0.005120 -0.006368 0.010177 0.010272
0.007975 0.008986 0.007097 0.007584
O3 0.075716 0.040331 0.044547 -0.004872 0.005294 -0.007913 0.000433 0.000318
0.000324 0.000290 0.000300 0.000248
O1 0.097499 0.048917 0.038514 0.011692 0.004810 0.002848 0.000534 0.000392
0.000344 0.000365 0.000327 0.000293
O2 0.118803 0.041943 0.042437 0.022688 0.007211 0.004883 0.000548 0.000333
0.000326 0.000330 0.000339 0.000263
O4 0.105494 0.058429 0.056488 -0.003140 0.037042 -0.003135 0.000536 0.000389
0.000380 0.000342 0.000393 0.000292
C4 0.050287 0.034210 0.039163 0.002547 -0.002623 -0.000785 0.000452 0.000384
0.000431 0.000321 0.000361 0.000312
C2 0.072102 0.035349 0.033067 0.000475 0.011728 0.001484 0.000611 0.000398
0.000415 0.000393 0.000419 0.000311
C1 0.064835 0.036477 0.034509 0.008598 -0.000236 0.001658 0.000531 0.000424
0.000421 0.000358 0.000382 0.000332
C7 0.079061 0.030813 0.081824 -0.001135 0.001121 0.002829 0.000658 0.000456
0.000747 0.000440 0.000562 0.000479
C3 0.055922 0.030474 0.039141 -0.000063 0.002958 0.003011 0.000474 0.000374
0.000439 0.000318 0.000364 0.000300
C5 0.065602 0.043372 0.050443 0.002932 -0.008664 -0.011177 0.000593 0.000498
0.000548 0.000389 0.000500 0.000433
C6 0.073407 0.037142 0.076749 -0.000031 -0.007520 -0.012642 0.000640 0.000489
0.000729 0.000427 0.000543 0.000470
C8 0.076729 0.034361 0.055280 -0.000662 0.003625 0.009146 0.000620 0.000437
0.000580 0.000396 0.000539 0.000429
H20 0.171507 0.062196 0.057545 0.008234 0.014959 0.004716 0.011432 0.006918
0.006647 0.006698 0.007388 0.005610
H19 0.166944 0.063487 0.073279 0.012551 0.017738 0.008107 0.011118 0.007266
0.007506 0.006689 0.007345 0.005717
H18 0.198029 0.066675 0.061907 0.033431 0.026593 0.021871 0.013282 0.007085
0.006857 0.007181 0.007721 0.005855
H2A 0.104919 0.068848 0.076747 0.004907 0.006368 -0.004892 0.010109 0.008210
0.008144 0.006457 0.008365 0.006871
H17 0.199482 0.081750 0.060859 0.038298 0.040100 0.009935 0.013006 0.007870
0.007151 0.007749 0.008067 0.005732
H2B 0.108929 0.055913 0.072965 -0.000673 0.017843 0.007958 0.009742 0.007356
0.008144 0.007009 0.006805 0.006352
O5 0.126338 0.039203 0.043031 0.010894 0.002310 0.007054 0.000596 0.000319
0.000341 0.000330 0.000358 0.000265
N1 0.068593 0.034835 0.048298 0.004835 -0.000532 0.005053 0.000464 0.000349
0.000403 0.000313 0.000351 0.000301
N2 0.077659 0.040407 0.050428 0.008667 0.008577 0.003541 0.000559 0.000435
0.000515 0.000407 0.000482 0.000418
C15 0.064731 0.033851 0.039607 0.001600 0.000522 0.004734 0.000533 0.000399
0.000464 0.000351 0.000395 0.000332
C20 0.083596 0.037084 0.035208 0.001534 0.000916 0.000797 0.000621 0.000440
0.000473 0.000407 0.000462 0.000364
C16 0.051762 0.033435 0.036629 -0.000288 -0.000085 0.002591 0.000460 0.000370
0.000430 0.000324 0.000357 0.000314
C19 0.085134 0.035624 0.043507 0.004523 0.001232 -0.002254 0.000682 0.000453
0.000520 0.000431 0.000473 0.000382
C17 0.076866 0.040951 0.038725 0.010392 0.007789 0.005954 0.000620 0.000471
0.000495 0.000410 0.000451 0.000366
C18 0.082738 0.041660 0.042203 0.012505 0.006182 0.009512 0.000640 0.000478
0.000513 0.000422 0.000484 0.000389
H11 0.143650 0.072252 0.060525 0.002160 0.004659 0.001094 0.010278 0.007434
0.006873 0.006222 0.007204 0.005753
H13 0.187972 0.076714 0.070287 -0.016533 0.009320 -0.014802 0.012988 0.007696
0.007450 0.007429 0.008322 0.006282
H12 0.142042 0.062931 0.070842 -0.005799 0.008218 0.013098 0.009824 0.006893
0.006882 0.006571 0.006613 0.005603
H14 0.237335 0.058335 0.052116 -0.014842 -0.003683 0.010382 0.014479 0.007195
0.006407 0.007617 0.007868 0.005330
H4A 0.129074 0.047638 0.069902 0.002282 0.010719 -0.012174 0.010578 0.007165
0.008128 0.006890 0.007123 0.005956
H4B 0.121431 0.065518 0.054576 -0.009238 0.004260 0.001608 0.011231 0.007870
0.007343 0.006802 0.007261 0.006144
H3 0.075849 0.072758 0.065050 -0.002740 0.020115 -0.012004 0.009182 0.013711
0.008883 0.008564 0.007027 0.008715
O6 0.123598 0.044319 0.053873 -0.016086 0.037891 -0.012328 0.000580 0.000346
0.000377 0.000336 0.000383 0.000280
N4 0.089891 0.036060 0.050263 -0.006275 0.018149 -0.002564 0.000641 0.000415
0.000535 0.000417 0.000466 0.000388
N3 0.063248 0.036383 0.057412 -0.005962 0.008359 -0.009662 0.000468 0.000385
0.000486 0.000342 0.000369 0.000364
C9 0.070262 0.034680 0.040669 -0.006656 0.016799 -0.005027 0.000561 0.000408
0.000459 0.000359 0.000419 0.000335
C11 0.063451 0.038646 0.039160 -0.001865 0.005146 -0.001560 0.000532 0.000436
0.000475 0.000368 0.000428 0.000374
C10 0.055562 0.034348 0.037196 -0.006112 0.008740 -0.003550 0.000472 0.000383
0.000435 0.000328 0.000362 0.000322
C14 0.097190 0.040644 0.037711 -0.007630 0.006878 -0.003385 0.000704 0.000478
0.000501 0.000459 0.000486 0.000389
C12 0.066239 0.035503 0.050014 0.000010 0.007356 0.000300 0.000565 0.000453
0.000545 0.000391 0.000447 0.000395
C13 0.099985 0.045278 0.042456 -0.009803 0.004322 -0.012163 0.000752 0.000534
0.000547 0.000473 0.000543 0.000443

# ====
# ADPs
# ====


# ============
# Bond lengths
# ============

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O3 . C2 . 1.2825(10) yes
O1 . C1 . 1.3132(9) yes
O2 . C1 . 1.2070(9) yes
O4 . C2 . 1.2256(9) yes
O5 . C15 . 1.2283(9) yes
O6 . C9 . 1.2261(9) yes
O1 . H1 . 1.046(14) yes
N1 . C19 . 1.3282(10) yes
N1 . C18 . 1.3320(10) yes
N2 . C15 . 1.3311(11) yes
N4 . C9 . 1.3234(11) yes
N3 . C12 . 1.3315(11) yes
N3 . C13 . 1.3329(12) yes
N2 . H2A . 0.982(11) yes
N2 . H2B . 1.015(11) yes
N4 . H4A . 1.009(10) yes
N4 . H4B . 0.977(11) yes
N3 . H3 . 1.178(14) yes
C4 . C1 . 1.4900(10) yes
C4 . C3 . 1.4017(10) yes
C4 . C5 . 1.3954(11) yes
C2 . C3 . 1.5048(10) yes
C7 . C6 . 1.3894(14) yes
C7 . C8 . 1.3919(13) yes
C3 . C8 . 1.3907(10) yes
C5 . C6 . 1.3880(12) yes
C15 . C16 . 1.5020(10) yes
C20 . C16 . 1.3848(11) yes
C20 . C19 . 1.3846(11) yes
C16 . C17 . 1.3841(10) yes
C17 . C18 . 1.3886(11) yes
C9 . C10 . 1.5052(10) yes
C11 . C10 . 1.3860(10) yes
C11 . C12 . 1.3753(11) yes
C10 . C14 . 1.3871(11) yes
C14 . C13 . 1.3852(12) yes
C7 . H7 . 1.085(10) yes
C5 . H5 . 1.071(10) yes
C6 . H6 . 1.106(9) yes
C8 . H8 . 1.058(9) yes
C20 . H20 . 1.081(9) yes
C19 . H19 . 1.079(9) yes
C17 . H17 . 1.063(9) yes
C18 . H18 . 1.082(9) yes
C11 . H11 . 1.076(9) yes
C14 . H14 . 1.067(9) yes
C12 . H12 . 1.080(9) yes
C13 . H13 . 1.051(10) yes

# ===========
# Bond Angles
# ===========

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 . C2 . O4 . 124.42(7) yes
O1 . C1 . O2 . 123.46(7) yes
O5 . C15 . N2 . 122.66(8) yes
O6 . C9 . N4 . 123.50(8) yes
O3 . C2 . C3 . 115.19(7) yes
O1 . C1 . C4 . 114.13(7) yes
O2 . C1 . C4 . 122.41(7) yes
O4 . C2 . C3 . 120.25(8) yes
O5 . C15 . C16 . 118.35(7) yes
O6 . C9 . C10 . 119.41(7) yes
N1 . C19 . C20 . 122.94(8) yes
N1 . C18 . C17 . 123.18(8) yes
N2 . C15 . C16 . 118.99(7) yes
N4 . C9 . C10 . 117.08(7) yes
N3 . C12 . C11 . 121.42(9) yes
N3 . C13 . C14 . 121.10(9) yes
N1 . C19 . H19 . 115.7(5) yes
N1 . C18 . H18 . 115.6(5) yes
N3 . C12 . H12 . 114.4(5) yes
N3 . C13 . H13 . 116.3(6) yes
C1 . O1 . H1 . 109.6(6) yes
C19 . N1 . C18 . 117.82(7) yes
C12 . N3 . C13 . 120.49(8) yes
C15 . N2 . H2A . 121.5(6) yes
C15 . N2 . H2B . 115.6(6) yes
C9 . N4 . H4A . 117.0(6) yes
C9 . N4 . H4B . 121.4(6) yes
C12 . N3 . H3 . 121.1(5) yes
C13 . N3 . H3 . 118.4(5) yes
C4 . C3 . C2 . 122.98(6) yes
C4 . C3 . C8 . 119.08(7) yes
C4 . C5 . C6 . 120.84(9) yes
C2 . C3 . C8 . 117.89(7) yes
C1 . C4 . C3 . 120.16(6) yes
C1 . C4 . C5 . 120.20(7) yes
C7 . C6 . C5 . 119.73(9) yes
C7 . C8 . C3 . 121.16(9) yes
C3 . C4 . C5 . 119.55(7) yes
C6 . C7 . C8 . 119.62(9) yes
C15 . C16 . C20 . 117.93(7) yes
C15 . C16 . C17 . 124.03(7) yes
C20 . C16 . C17 . 118.04(7) yes
C16 . C20 . C19 . 119.25(8) yes
C16 . C17 . C18 . 118.74(8) yes
C9 . C10 . C11 . 118.33(7) yes
C9 . C10 . C14 . 122.96(7) yes
C11 . C10 . C14 . 118.70(7) yes
C10 . C11 . C12 . 119.25(8) yes
C10 . C14 . C13 . 119.03(9) yes
C4 . C5 . H5 . 119.2(6) yes
C7 . C6 . H6 . 119.1(6) yes
C7 . C8 . H8 . 119.6(5) yes
C3 . C8 . H8 . 119.2(5) yes
C5 . C6 . H6 . 121.1(6) yes
C6 . C7 . H7 . 120.9(6) yes
C6 . C5 . H5 . 120.0(5) yes
C8 . C7 . H7 . 119.5(6) yes
C20 . C19 . H19 . 121.3(5) yes
C16 . C20 . H20 . 119.2(5) yes
C16 . C17 . H17 . 122.0(5) yes
C19 . C20 . H20 . 121.6(5) yes
C17 . C18 . H18 . 121.2(5) yes
C18 . C17 . H17 . 119.2(5) yes
C11 . C12 . H12 . 124.2(5) yes
C10 . C11 . H11 . 119.9(5) yes
C10 . C14 . H14 . 121.5(5) yes
C14 . C13 . H13 . 122.6(6) yes
C12 . C11 . H11 . 120.8(5) yes
C13 . C14 . H14 . 119.4(5) yes
H2A . N2 . H2B . 122.8(9) yes
H4A . N4 . H4B . 119.4(9) yes
_chemical_name_systematic        'isonicotinamide phthalate 2:1'
