# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_system_2_XD
_database_code_depnum_ccdc_archive 'CCDC 2068354'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_system_2_XD         
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      51.88 %     
RESPONSE: Mu(CIF) value was obtained using the CALC Mu function in Wingx and then supplied to SORTAV for
scaling. 
;
_vrf_PLAT355_system_2_XD         
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H1       .       1.16 Ang.  
RESPONSE: Due to H1 being involved in the formation of a short strong hydrogen bond. O1-H1 distance
is that obtained from the 100 K neutron structure.
;
_vrf_PLAT927_system_2_XD         
;
PROBLEM: Reported and Calculated  wR2 Differ by .........    -0.0716 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
_vrf_PLAT997_system_2_XD         
;
PROBLEM: Unsuitable CIF/FCF File Combination with SHELXL CIF       ! Error 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
_vrf_PLAT920_system_2_XD         
;
PROBLEM: Theta(Max)  in CIF and FCF Differ by ...........       1.46 Degree
RESPONSE: Theta(Max) in CIF includes data pre sinTh/L cut-off used in XDLSM refinement.
Reflections rejected based on SINTHL    =   881
;
_vrf_PLAT926_system_2_XD         
;
PROBLEM: Reported and Calculated   R1 Differ by .........    -0.0197 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
_vrf_PLAT928_system_2_XD         
;
PROBLEM: Reported and Calculated    S value   Differ by .     -1.692 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;


# 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 H3 N2 O6, C3 H9 N2 O1'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.24


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#


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_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2-X,1/2+Y,+Z
7 +X,1/2-Y,1/2+Z
8 1/2+X,+Y,1/2-Z

_cell_length_a                   19.17290(10)
_cell_length_b                   5.81570(10)
_cell_length_c                   22.95360(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2559.41(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    66838
_cell_measurement_theta_min      1.712512902041655
_cell_measurement_theta_max      46.29531120516937


#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plank
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.055
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_special_details   ?
_exptl_sortav_scale_factor_max   1.771
_exptl_sortav_scale_factor_min   0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_T_max  1.082

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_source                   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_monochromator  'Silicon 111'
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12379
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_theta_min         1.720
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_theta_max         46.351
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12379
_reflns_number_gt                9192
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
 
 Pre sintheta/lambda cut-off: _reflns_number_gt                 9637
 
 Reflections were merged by SORTAV according to the crystal
class
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------# 
_computing_data_collection       'GDA - generic data acquisition software'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.14.9-g0c59d74b8-release'
_computing.data_reduction        
'DIALS 2.2.2-ga00882522-release (Winter, G. et al., 2018)'

_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    MercuryTM
_computing_publication_material  ?

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap


#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.019
_refine_ls_R_factor_all          0.039
_refine_ls_R_Fsqd_factor         0.019
_refine_ls_wR_factor_ref         0.042
_refine_ls_hydrogen_treatment    ?
_refine_ls_number_reflns         9192
_refine_ls_number_parameters     439
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w2 = 1/[s²(Fo²)]
;
_refine_ls_shift/su_max          0.01225
_refine_ls_extinction_method     none
_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.,multipole refinement
;

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.026


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_U_iso_or_equiv
O(3) 0.420744(16) 0.30213(5) 0.057682(15) 1 8 0.022
O(2) 0.33241(3) 0.52006(10) 0.09083(3) 1 8 0.021
O(4) 0.45305(2) 0.56221(7) 0.25886(3) 1 8 0.022
O(6) 0.354757(14) -0.10752(4) 0.348717(15) 1 8 0.027
O(7) 0.29582(3) -0.35274(11) 0.297239(19) 1 8 0.028
O(5) 0.46595(3) 0.56818(9) 0.16514(3) 1 8 0.033
O(1) 0.326526(18) 0.78545(5) 0.008406(13) 1 8 0.021
N(3) 0.441916(10) 0.48540(4) 0.209879(8) 1 8 0.018
N(4) 0.330556(11) -0.17609(3) 0.302505(10) 1 8 0.019
N(2) 0.380601(15) 1.01718(5) -0.056267(10) 1 8 0.019
N(1) 0.437002(15) 0.69512(5) -0.019686(10) 1 8 0.023
C(2) 0.369995(11) 0.21888(4) 0.150188(10) 1 8 0.015
C(7) 0.397303(11) 0.28138(4) 0.204418(9) 1 8 0.015
C(1) 0.377257(12) 0.35892(4) 0.094945(10) 1 8 0.017
C(5) 0.344338(11) -0.03999(4) 0.249816(10) 1 8 0.016
C(6) 0.384907(11) 0.15602(4) 0.254911(10) 1 8 0.016
C(3) 0.329483(12) 0.01918(4) 0.147294(11) 1 8 0.018
C(4) 0.316659(12) -0.11211(4) 0.196863(12) 1 8 0.018
C(8) 0.381106(14) 0.83190(4) -0.022312(10) 1 8 0.017
C(10) 0.440600(15) 1.07698(5) -0.091962(11) 1 8 0.023
C(9) 0.318406(16) 1.15880(5) -0.061502(12) 1 8 0.026
H(3) 0.308172 -0.036177 0.105564 1 8 0.041
H(6) 0.405996 0.207546 0.296048 1 8 0.028
H(4) 0.284719 -0.268276 0.192485 1 8 0.031
H(1B) 0.482828 0.721768 -0.042968 1 8 0.040
H(1A) 0.432894 0.54712 0.00308 1 8 0.026
H(10C) 0.445385 0.961686 -0.128629 1 8 0.046
H(10B) 0.433557 1.250666 -0.107541 1 8 0.050
H(9B) 0.329062 1.327125 -0.052755 1 8 0.057
H(10A) 0.487943 1.069762 -0.066531 1 8 0.048
H(9C) 0.298462 1.151391 -0.102656 1 8 0.072
H(9A) 0.281364 1.11929 -0.028713 1 8 0.055
H(1) 0.333443 0.649742 0.044988 1 8 0.027
loop_
_atom_local_dummy_label
_atom_local_dummy_fract_x
_atom_local_dummy_fract_y
_atom_local_dummy_fract_z
DUM0 0 0 0
DUM1 0.365403 0.10712 0.216447

_atom_site_anharm_details        
;
The atomic anharmonic pdf is approximated by a Gram-Charlier expansion
about the harmonic pdf, according to the expression :
      P(u) = (1 + Cijk*Hijk/3! + Dijkl*Hijkl/4!)*P(0)
The coefficients Cijk and Dijkl are refined in the least squares procedure.
The reported coefficients Cijk are multiplied by 1000 and Dijkl by 10000.
;
loop_
_atom_site_anharm_GC_C_label
_atom_site_anharm_GC_C_111
_atom_site_anharm_GC_C_222
_atom_site_anharm_GC_C_333
_atom_site_anharm_GC_C_112
_atom_site_anharm_GC_C_122
_atom_site_anharm_GC_C_113
_atom_site_anharm_GC_C_133
_atom_site_anharm_GC_C_223
_atom_site_anharm_GC_C_233
_atom_site_anharm_GC_C_123
O(2) 0.000006(7) 0.0001(2) -0.000008(4) 0.000034(12) -0.00013(4) 0.000007(3)
-0.000003(2) -0.00004(3) -0.000020(8) -0.000010(6)
O(4) -0.000003(6) 0.0000(2) 0.000005(4) -0.000064(11) 0.00029(4) 0.000004(3)
0.000008(2) 0.00013(3) 0.000022(8) 0.000018(6)
O(7) 0.000006(9) -0.0011(3) -0.000016(4) 0.000049(15) -0.00039(5) 0.000007(4)
-0.000005(3) 0.00008(4) -0.000042(10) -0.000019(8)
O(5) 0.000043(10) -0.0075(4) -0.000013(4) -0.00039(2) 0.00198(7) -0.000007(4)
-0.000012(3) 0.00003(5) 0.000049(10) -0.000013(11)

#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(3) C(1) 1.2393(4) 1_555 1_555 yes
O(2) C(1) 1.2754(7) 1_555 1_555 yes
O(4) N(3) 1.2284(7) 1_555 1_555 yes
O(6) N(4) 1.2245(4) 1_555 1_555 yes
O(7) N(4) 1.2303(7) 1_555 1_555 yes
O(5) N(3) 1.2242(7) 1_555 1_555 yes
O(1) C(8) 1.2904(4) 1_555 1_555 yes
N(3) C(7) 1.4680(3) 1_555 1_555 yes
N(4) C(5) 1.4693(3) 1_555 1_555 yes
N(2) C(8) 1.3299(4) 1_555 1_555 yes
N(2) C(10) 1.4545(4) 1_555 1_555 yes
N(2) C(9) 1.4542(4) 1_555 1_555 yes
N(1) C(8) 1.3360(4) 1_555 1_555 yes
N(1) H(1B) 1.0400(3) 1_555 1_555 yes
N(1) H(1A) 1.0100(2) 1_555 1_555 yes
C(2) C(7) 1.3985(3) 1_555 1_555 yes
C(2) C(1) 1.5135(3) 1_555 1_555 yes
C(2) C(3) 1.3988(3) 1_555 1_555 yes
C(7) C(6) 1.3897(3) 1_555 1_555 yes
C(5) C(6) 1.3850(3) 1_555 1_555 yes
C(5) C(4) 1.3910(3) 1_555 1_555 yes
C(6) H(6) 1.0700(2) 1_555 1_555 yes
C(3) C(4) 1.3921(4) 1_555 1_555 yes
C(3) H(3) 1.0900(3) 1_555 1_555 yes
C(4) H(4) 1.1000(3) 1_555 1_555 yes
C(10) H(10C) 1.0800(3) 1_555 1_555 yes
C(10) H(10B) 1.0800(3) 1_555 1_555 yes
C(10) H(10A) 1.0800(3) 1_555 1_555 yes
C(9) H(9B) 1.0200(3) 1_555 1_555 yes
C(9) H(9C) 1.0200(3) 1_555 1_555 yes
C(9) H(9A) 1.0600(3) 1_555 1_555 yes
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(4) N(3) O(5) 124.01(3) 1_555 1_555 1_555 yes
O(4) N(3) C(7) 118.25(2) 1_555 1_555 1_555 yes
O(5) N(3) C(7) 117.74(3) 1_555 1_555 1_555 yes
O(6) N(4) O(7) 124.20(3) 1_555 1_555 1_555 yes
O(6) N(4) C(5) 117.998(19) 1_555 1_555 1_555 yes
O(7) N(4) C(5) 117.80(3) 1_555 1_555 1_555 yes
C(8) N(2) C(10) 121.21(3) 1_555 1_555 1_555 yes
C(8) N(2) C(9) 120.88(3) 1_555 1_555 1_555 yes
C(10) N(2) C(9) 117.81(3) 1_555 1_555 1_555 yes
C(8) N(1) H(1B) 124.46(2) 1_555 1_555 1_555 yes
C(8) N(1) H(1A) 117.92(2) 1_555 1_555 1_555 yes
H(1B) N(1) H(1A) 117.31(3) 1_555 1_555 1_555 yes
C(7) C(2) C(1) 124.85(2) 1_555 1_555 1_555 yes
C(7) C(2) C(3) 117.77(2) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 117.26(2) 1_555 1_555 1_555 yes
N(3) C(7) C(2) 120.279(19) 1_555 1_555 1_555 yes
N(3) C(7) C(6) 116.901(19) 1_555 1_555 1_555 yes
C(2) C(7) C(6) 122.82(2) 1_555 1_555 1_555 yes
O(3) C(1) O(2) 126.75(5) 1_555 1_555 1_555 yes
O(3) C(1) C(2) 119.78(3) 1_555 1_555 1_555 yes
O(2) C(1) C(2) 113.30(4) 1_555 1_555 1_555 yes
N(4) C(5) C(6) 118.35(2) 1_555 1_555 1_555 yes
N(4) C(5) C(4) 119.22(2) 1_555 1_555 1_555 yes
C(6) C(5) C(4) 122.43(2) 1_555 1_555 1_555 yes
C(7) C(6) C(5) 117.22(2) 1_555 1_555 1_555 yes
C(7) C(6) H(6) 121.63(2) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 121.15(2) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 120.97(2) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 119.68(2) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 119.34(2) 1_555 1_555 1_555 yes
C(5) C(4) C(3) 118.78(2) 1_555 1_555 1_555 yes
C(5) C(4) H(4) 122.76(2) 1_555 1_555 1_555 yes
C(3) C(4) H(4) 118.46(2) 1_555 1_555 1_555 yes
O(1) C(8) N(2) 118.94(3) 1_555 1_555 1_555 yes
O(1) C(8) N(1) 120.08(3) 1_555 1_555 1_555 yes
N(2) C(8) N(1) 120.98(3) 1_555 1_555 1_555 yes
N(2) C(10) H(10C) 110.96(2) 1_555 1_555 1_555 yes
N(2) C(10) H(10B) 108.14(2) 1_555 1_555 1_555 yes
N(2) C(10) H(10A) 110.55(2) 1_555 1_555 1_555 yes
H(10C) C(10) H(10B) 109.47(2) 1_555 1_555 1_555 yes
H(10C) C(10) H(10A) 109.01(2) 1_555 1_555 1_555 yes
H(10B) C(10) H(10A) 108.69(2) 1_555 1_555 1_555 yes
N(2) C(9) H(9B) 111.29(3) 1_555 1_555 1_555 yes
N(2) C(9) H(9C) 111.10(2) 1_555 1_555 1_555 yes
N(2) C(9) H(9A) 111.59(2) 1_555 1_555 1_555 yes
H(9B) C(9) H(9C) 107.33(2) 1_555 1_555 1_555 yes
H(9B) C(9) H(9A) 101.68(3) 1_555 1_555 1_555 yes
H(9C) C(9) H(9A) 113.41(3) 1_555 1_555 1_555 yes

#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(3) 6.22(2) 0 -0.000(8) -0.010(7) 0 -0.002(7) 0 0 -0.048(6) -0.001(6) 0
0.037(5) -0.010(5) 0 0 0.047(4) -0.005(4) 0.022(6) 0 0 0.008(5) 0.007(5) 0 0
0.000(4) 0.003(4) 0.9739(16) 1.105075 1.105075 1.105075 1.105075 1.105075 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 6.2167 0 -0.0001 -0.0101 0 -0.0016 0 0 -0.0483 -0.0005 0 0.0373 -0.0103 0
0 0.0465 -0.0046 0.0218 0 0 0.0079 0.0073 0 0 0.0003 0.0026 0.9739(16) 1.105075
1.105075 1.105075 1.105075 1.105075 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(4) 6.036(15) 0 0 0 -0.036(9) -0.075(6) 0 0 -0.109(5) 0 0.037(5) 0 0 0.011(4)
0 0 0 0.013(5) 0 0 0.008(4) 0 0 0 -0.000(4) 0 0.9864(14) 1.037783 1.037783
1.037783 1.037783 1.037783 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(6) 6.0357 0 0 0 -0.0359 -0.0749 0 0 -0.1092 0 0.0369 0 0 0.0106 0 0 0 0.0125
0 0 0.0077 0 0 0 -0.0002 0 0.9864(14) 1.037783 1.037783 1.037783 1.037783
1.037783 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(7) 6.0357 0 0 0 -0.0359 -0.0749 0 0 -0.1092 0 0.0369 0 0 0.0106 0 0 0 0.0125
0 0 0.0077 0 0 0 -0.0002 0 0.9864(14) 1.037783 1.037783 1.037783 1.037783
1.037783 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(5) 6.0357 0 0 0 -0.0359 -0.0749 0 0 -0.1092 0 0.0369 0 0 0.0106 0 0 0 0.0125
0 0 0.0077 0 0 0 -0.0002 0 0.9864(14) 1.037783 1.037783 1.037783 1.037783
1.037783 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(1) 6.09(3) 0 -0.046(8) -0.002(7) 0 0.028(9) 0 0 -0.074(8) -0.010(8) 0
0.027(6) -0.011(6) 0 0 0.062(5) -0.001(5) 0.033(8) 0 0 0.005(7) 0.018(7) 0 0
0.004(6) 0.017(6) 0.982(2) 1.113461 1.113461 1.113461 1.113461 1.113461 2 4.466
2 4.466 2 4.466 3 4.466 4 4.466
N(3) 4.95(3) 0 0 0 0.019(8) 0.080(7) 0 0 -0.172(9) 0 0.269(9) 0 0 0.221(9) 0 0
0 0.025(9) 0 0 -0.021(8) 0 0 0 0.006(8) 0 0.988(3) 0.839998 0.839998 0.839998
0.839998 0.839998 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(4) 4.9523 0 0 0 0.019 0.0802 0 0 -0.1718 0 0.2688 0 0 0.2214 0 0 0 0.0248 0 0
-0.0209 0 0 0 0.0059 0 0.988(3) 0.839998 0.839998 0.839998 0.839998 0.839998 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(2) 4.68(4) 0 0.044(8) 0.028(7) 0 0.063(8) 0 0 0.016(8) 0.026(7) 0 0.024(6)
0.013(6) 0 0 0.112(7) -0.020(6) 0.046(8) 0 0 -0.009(8) 0.010(7) 0 0 0.001(8)
0.011(7) 1.005(3) 1.094502 1.094502 1.094502 1.094502 1.094502 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(1) 5.08(4) 0 0 0 -0.030(10) -0.047(9) 0 0 -0.018(9) -0.010(7) 0.155(8) 0 0
0.112(8) 0.017(6) 0 0 -0.004(9) 0 0 -0.015(9) 0.007(8) 0 0 0.038(8) 0.056(8)
0.975(3) 1.041506 1.041506 1.041506 1.041506 1.041506 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
C(2) 3.97(4) 0 -0.014(10) 0.074(10) 0 -0.228(9) 0 0 -0.025(8) -0.040(9) 0
0.022(8) 0.004(9) 0 0 0.223(10) -0.070(9) 0.027(11) 0 0 0.017(10) -0.003(11) 0
0 -0.032(11) 0.009(11) 1.006(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(7) 3.93(4) 0 0 0 -0.133(10) -0.035(9) 0 0 -0.141(8) 0 0.230(10) 0 0 0.153(9)
0 0 0 0.013(12) 0 0 -0.028(11) 0 0 0 -0.001(10) 0 1.009(3) 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
C(1) 3.98(4) 0 0.006(8) 0.022(9) 0 -0.226(9) 0 0 0.037(8) -0.029(8) 0 0.010(8)
-0.008(8) 0 0 0.318(11) 0.039(7) 0.041(12) 0 0 0.024(10) -0.010(10) 0 0
-0.036(9) 0.005(13) 0.987(5) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(5) 3.97(4) 0 0 0 -0.121(10) -0.033(9) 0 0 -0.158(9) 0 0.217(10) 0 0 0.134(9)
0 0 0 -0.001(12) 0 0 -0.034(11) 0 0 0 0.001(10) 0 1.009(3) 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
C(6) 3.88(4) 0 0 0 0.006(10) 0.083(8) 0 0 -0.167(8) 0 -0.206(9) 0 0 -0.128(8) 0
0 0 0.033(11) 0 0 0.013(10) 0 0 0 0.004(10) 0 1.008(4) 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
C(3) 3.97(3) 0 0.061(11) -0.028(11) 0 -0.201(9) 0 0 0.035(10) 0.017(10) 0
-0.011(9) 0.070(8) 0 0 0.276(10) 0.012(10) 0.024(12) 0 0 -0.012(11) -0.032(11)
0 0 0.010(12) -0.039(12) 1.002(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(4) 3.90(3) 0 0.032(10) -0.016(11) 0 -0.195(9) 0 0 -0.018(9) -0.008(9) 0
0.024(8) 0.038(9) 0 0 0.216(10) -0.010(9) -0.011(11) 0 0 0.001(10) 0.024(11) 0
0 0.031(11) -0.031(11) 1.002(3) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(8) 4.06(5) 0 -0.038(10) 0.004(11) 0 -0.262(10) 0 0 -0.012(9) -0.033(9) 0
-0.051(8) 0.009(9) 0 0 0.371(12) -0.038(9) 0.014(12) 0 0 -0.016(11) 0.010(11) 0
0 -0.001(12) 0.001(13) 0.979(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(10) 4.33(6) 0 0 0 -0.051(7) -0.048(7) 0 0 0 0 0.315(9) 0 0 0 0 0 -0.147(7)
0.118(9) 0 0 0 0 0 0.038(8) 0 0 0.941(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(9) 4.3266 0 0 0 -0.0505 -0.048 0 0 0 0 0.3152 0 0 0 0 0 -0.1473 0.1183 0 0 0
0 0 0.0384 0 0 0.941(4) 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(3) 0.900(10) 0 0 0 0.159(7) 0.082(8) 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0
0 0 0 0 0 1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.9 0 0 0 0.1588 0.0817 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0 0 0 0 0
1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(4) 0.9 0 0 0 0.1588 0.0817 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0 0 0 0 0
1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(1B) 0.826(12) 0 0 0 0.148(8) 0.103(9) 0 0 0 0 0.0151 0 0 0 0 0 0 -0.0083 0 0
0 0 0 0 0 0 1.110704 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(1A) 0.8258 0 0 0 0.1479 0.1032 0 0 0 0 0.0151 0 0 0 0 0 0 -0.0083 0 0 0 0 0 0
0 0 1.110704 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10C) 0.890(13) 0 0 0 0.113(6) 0.057(7) 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0
0 0 0 0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10B) 0.8902 0 0 0 0.1129 0.0574 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9B) 0.8902 0 0 0 0.1129 0.0574 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0
0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10A) 0.8902 0 0 0 0.1129 0.0574 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9C) 0.8902 0 0 0 0.1129 0.0574 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0
0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9A) 0.8902 0 0 0 0.1129 0.0574 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0
0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(1) 0.680(11) 0 0 0 0.044(8) 0.158(13) 0 0 0 0 0.0171 0 0 0 0 0 0 -0.0278 0 0
0 0 0 0 0 0 1.119673 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(3) C(1) X O(3) O(2) Y
O(2) C(1) X O(2) O(3) Y
O(4) N(3) Z O(4) O(5) Y
O(6) N(4) Z O(6) O(7) Y
O(7) N(4) Z O(7) O(6) Y
O(5) N(3) Z O(5) O(4) Y
O(1) C(8) X O(1) H(1) Y
N(3) C(7) Z N(3) O(5) Y
N(4) C(5) Z N(4) O(6) Y
N(2) C(8) X N(2) C(10) Y
N(1) C(8) Z N(1) H(1B) Y
C(2) C(7) X C(2) C(3) Y
C(7) N(3) Z C(7) C(6) Y
C(1) O(3) X C(1) O(2) Y
C(5) N(4) Z C(5) C(6) Y
C(6) DUM1 Z C(6) C(5) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(5) X C(4) C(3) Y
C(8) O(1) X C(8) N(2) Y
C(10) N(2) Z C(10) H(10A) Y
C(9) N(2) Z C(9) H(9A) Y
H(3) C(3) Z H(3) C(4) Y
H(6) C(6) Z H(6) C(5) Y
H(4) C(4) Z H(4) C(5) Y
H(1B) N(1) Z H(1B) H(1A) Y
H(1A) N(1) Z H(1A) H(1B) Y
H(10C) C(10) Z H(10C) N(2) Y
H(10B) C(10) Z H(10B) N(2) Y
H(9B) C(9) Z H(9B) N(2) Y
H(10A) C(10) Z H(10A) N(2) Y
H(9C) C(9) Z H(9C) N(2) Y
H(9A) C(9) Z H(9A) N(2) Y
H(1) O(1) Z H(1) C(8) Y


#----------------------------------------------------------------------------#
#                   STRUCTURE FACTOR INFORMATION                             #
#----------------------------------------------------------------------------#

#
#  Unique observations used in XD refinement
#  F^2(calc) includes anomalous dispersion and is corrected for extinction
#  if the latter is included in the model.
#


_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_system2_NEUT
_database_code_depnum_ccdc_archive 'CCDC 2068355'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_TYPE036_system2_NEUT        
;
PROBLEM: _exptl_absorpt_coefficient_mu is not of type numb.
RESPONSE: This is due to use of time-of-flight LAUE diffraction.
;
_vrf_DIFMN02_system2_NEUT        
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: Q1 is at 1.3 and appears to be a spurious peak, not within
a sensible atomic location. 
;
_vrf_PLAT088_system2_NEUT        
;
PROBLEM: Poor Data / Parameter Ratio ....................       4.56 Note  
RESPONSE: The diffraction intensity was limited by the needle morpholpogy of
these crystals and weaker than optimal. However, due to available time on the instrument,
this was the best data set available. The aim of this measurement was to improve on the
hydrogen atom positions obtained by X-ray diffraction. 
;
_vrf_PLAT183_system2_NEUT        
;
PROBLEM: Missing _cell_measurement_reflns_used Value ....     Please Do !  
RESPONSE: Not computed in the treatment here of the neutron data.
;
_vrf_PLAT184_system2_NEUT        
;
PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do !  
RESPONSE: Not computed in the treatment here of the neutron data.
;
_vrf_PLAT185_system2_NEUT        
;
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do !  
RESPONSE: Not computed in the treatment here of the neutron data.
;
_vrf_PLAT881_system2_NEUT        
;
PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do !  
RESPONSE: Not computed in the treatment here of the neutron data.
;
_vrf_PLAT340_system2_NEUT        
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01371 Ang.  
RESPONSE: The diffraction intensity was limited by the needle morpholpogy of
these crystals and weaker than optimal. However, due to available time on the instrument,
this was the best data set available. The aim of this measurement was to improve on the
hydrogen atom positions obtained by X-ray diffraction. 
 
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        'N,N-dimethylurea 2,4-dinitrobenzoate 1:1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 N2 O6, C3 H9 N2 O1'
_chemical_formula_sum            'C10 H12 N4 O7'
_chemical_formula_weight         300.23

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.157(6)
_cell_length_b                   5.791(2)
_cell_length_c                   22.956(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2546.9(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             797
_exptl_crystal_size_max          7.000
_exptl_crystal_size_mid          1.500
_exptl_crystal_size_min          1.500

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_T_max  0.2330
_exptl_absorpt_correction_T_min  0.1238
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_process_details   'Gauss integration'
_exptl_absorpt_special_details   ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_exptl_absorpt_coefficient_mu    '0.3505 + 0.0020 * lambda'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.25
##### Wavelength range = 0.25 \^a\/E? 8.8 
_diffrn_source                   'ISIS spallation source'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4992
_diffrn_reflns_av_unetI/netI     0.1417
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         10.367
_diffrn_reflns_theta_max         86.131
_diffrn_reflns_theta_full        25.481
_diffrn_measured_fraction_theta_max 0.136
_diffrn_measured_fraction_theta_full 0.466
_diffrn_reflns_Laue_measured_fraction_max 0.136
_diffrn_reflns_Laue_measured_fraction_full 0.466
_diffrn_reflns_point_group_measured_fraction_max 0.136
_diffrn_reflns_point_group_measured_fraction_full 0.466
_reflns_number_total             4992
_reflns_number_gt                4558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;

 _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.

For peak integration a local UB matrix refined for each frame, using approximately 
40 reflections from each of the 11 detectors. Hence _cell_measurement_reflns_used 
440 For final cell dimensions a weighted average of all local cells was calculated 
Because of the nature of the experiment, it is not possible to give values of theta_min 
and theta_max for the cell determination. The same applies for the wavelength used for 
the experiment. The range of wavelengths used was 0.48-7.0 Angstroms, BUT the bulk of
 the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms. 
 The data collection procedures on the SXD instrument used for the single crystal neutron 
 data collection are most recently summarised in the Appendix to the following paper 
 Wilson, C.C. (1997). J. Mol. Struct. 405, 207-217 .
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#  
_computing_cell_refinement       'SXD2001 (Gutmann, 2005)'
_computing_data_collection       'SXD2001 (Gutmann, 2005)'
_computing_data_reduction        'SXD2001 (Gutmann, 2005)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
; 
The variable wavelength nature of the data collection procedure means that sensible values 
of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given instead the following limits are given 
_diffrn_reflns_sin(theta)/lambda_min 0.05 _diffrn_reflns_sin(theta)/lambda_max 1.31 _refine_diff_density_max/min 
is given in Fermi per per angstrom cubed not electons per angstrom cubed. Another way to consider the 
_refine_diff_density_ is as a percentage of the diffracted intensity of a given atom: 
_refine_diff_density_max = 5% of Carbon _refine_diff_density_min = -4% of Carbon 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 > 2sigma(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)+(0.1569P)²] where P=(Fo²+2Fc²)/3'

_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.00049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4992
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2274
_refine_ls_wR_factor_gt          0.2142
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_refine_diff_density_max         1.462
_refine_diff_density_min         -1.300
_refine_diff_density_rms         0.299
#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0.3066(10) -0.027(6) 0.1054(8) 0.051(9) Uani 1 1 d . . . . .
H6 H 0.4075(9) 0.209(4) 0.2961(7) 0.032(6) Uani 1 1 d . . . . .
H4 H 0.2842(10) -0.267(5) 0.1943(8) 0.036(6) Uani 1 1 d . . . . .
H1B H 0.4815(8) 0.733(6) -0.0434(8) 0.049(8) Uani 1 1 d . . . . .
H1A H 0.4335(9) 0.555(5) 0.0068(9) 0.029(5) Uani 1 1 d . . . . .
H10C H 0.4438(12) 0.973(6) -0.1304(10) 0.057(9) Uani 1 1 d . . . . .
H10B H 0.4353(13) 1.255(7) -0.1073(12) 0.064(9) Uani 1 1 d . . . . .
H9B H 0.3318(15) 1.332(7) -0.0569(16) 0.073(11) Uani 1 1 d . . . . .
H10A H 0.4886(11) 1.064(6) -0.0681(10) 0.060(9) Uani 1 1 d . . . . .
H9C H 0.2957(12) 1.139(8) -0.1031(12) 0.095(15) Uani 1 1 d . . . . .
H9A H 0.2810(12) 1.119(5) -0.0299(12) 0.070(10) Uani 1 1 d . . . . .
H1 H 0.3334(9) 0.652(4) 0.0449(8) 0.030(6) Uani 1 1 d . . . . .
C2 C 0.3698(4) 0.2192(19) 0.1503(3) 0.011(2) Uani 1 1 d . . . . .
O3 O 0.4204(5) 0.306(3) 0.0581(4) 0.024(4) Uani 1 1 d . . . . .
O2 O 0.3330(5) 0.520(3) 0.0910(5) 0.023(3) Uani 1 1 d . . . . .
N3 N 0.4418(3) 0.4880(15) 0.2100(3) 0.0189(18) Uani 1 1 d . . . . .
C7 C 0.3974(4) 0.281(2) 0.2046(4) 0.016(2) Uani 1 1 d . . . . .
N4 N 0.3306(3) -0.1769(15) 0.3025(3) 0.0196(19) Uani 1 1 d . . . . .
C1 C 0.3773(4) 0.361(2) 0.0952(4) 0.017(3) Uani 1 1 d . . . . .
C5 C 0.3448(4) -0.041(2) 0.2496(4) 0.017(3) Uani 1 1 d . . . . .
O4 O 0.4528(5) 0.562(3) 0.2591(5) 0.026(4) Uani 1 1 d . . . . .
C6 C 0.3846(4) 0.158(2) 0.2555(4) 0.020(3) Uani 1 1 d . . . . .
C3 C 0.3290(4) 0.017(2) 0.1475(4) 0.017(3) Uani 1 1 d . . . . .
C4 C 0.3167(4) -0.111(2) 0.1968(4) 0.021(3) Uani 1 1 d . . . . .
O6 O 0.3545(6) -0.108(3) 0.3485(4) 0.027(3) Uani 1 1 d . . . . .
O7 O 0.2966(5) -0.353(3) 0.2980(5) 0.027(3) Uani 1 1 d . . . . .
O5 O 0.4654(6) 0.569(3) 0.1655(5) 0.030(4) Uani 1 1 d . . . . .
O1 O 0.3267(5) 0.788(3) 0.0084(4) 0.020(3) Uani 1 1 d . . . . .
N2 N 0.3806(3) 1.0168(15) -0.0559(3) 0.021(2) Uani 1 1 d . . . . .
C8 C 0.3812(4) 0.833(2) -0.0222(4) 0.020(3) Uani 1 1 d . . . . .
N1 N 0.4371(3) 0.6949(17) -0.0192(3) 0.0196(19) Uani 1 1 d . . . . .
C10 C 0.4403(5) 1.079(3) -0.0920(5) 0.020(3) Uani 1 1 d . . . . .
C9 C 0.3189(5) 1.163(3) -0.0616(5) 0.023(3) Uani 1 1 d . . . . .


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C2 C7 1.401(12) . ?
C2 C3 1.408(14) . ?
C2 C1 1.516(12) . ?
O3 C1 1.229(13) . ?
O2 C1 1.257(16) . ?
N3 O5 1.212(13) . ?
N3 O4 1.225(13) . ?
N3 C7 1.477(13) . ?
C7 C6 1.388(14) . ?
N4 O7 1.216(15) . ?
N4 O6 1.217(13) . ?
N4 C5 1.472(12) . ?
C5 C4 1.387(14) . ?
C5 C6 1.390(15) . ?
C3 C4 1.376(14) . ?
O1 C8 1.287(13) . ?
N2 C8 1.316(13) . ?
N2 C10 1.458(12) . ?
N2 C9 1.460(13) . ?
C8 N1 1.336(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
C7 C2 C3 117.5(9) . . ?
C7 C2 C1 124.7(10) . . ?
C3 C2 C1 117.7(8) . . ?
O5 N3 O4 125.2(11) . . ?
O5 N3 C7 117.3(9) . . ?
O4 N3 C7 117.5(9) . . ?
C6 C7 C2 123.6(10) . . ?
C6 C7 N3 116.5(8) . . ?
C2 C7 N3 119.9(8) . . ?
O7 N4 O6 123.4(11) . . ?
O7 N4 C5 118.5(9) . . ?
O6 N4 C5 118.1(10) . . ?
O3 C1 O2 126.2(11) . . ?
O3 C1 C2 120.1(11) . . ?
O2 C1 C2 113.5(9) . . ?
C4 C5 C6 122.7(10) . . ?
C4 C5 N4 119.5(10) . . ?
C6 C5 N4 117.7(8) . . ?
C7 C6 C5 116.0(8) . . ?
C4 C3 C2 120.4(9) . . ?
C3 C4 C5 119.7(11) . . ?
C8 N2 C10 121.8(8) . . ?
C8 N2 C9 122.0(7) . . ?
C10 N2 C9 116.2(9) . . ?
O1 C8 N2 118.5(10) . . ?
O1 C8 N1 120.0(11) . . ?
N2 C8 N1 121.4(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
O1 H1 O3 1.16(3) 2.62(3) 3.506(19) 132.4(12) .
O1 H1 O3 1.16(3) 2.62(3) 3.506(19) 132.4(12) .




_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_system1_HAR
_database_code_depnum_ccdc_archive 'CCDC 2068358'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_system1_HAR         
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      52.20 %     
RESPONSE: Mu(CIF) value was obtained using the CALC Mu function in Wingx and then supplied to SORTAV for
scaling. 
;
_vrf_PLAT355_system1_HAR         
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H1       .       1.18 Ang.  
RESPONSE: Due to H1 being involved in the formation of a short strong hydrogen bond. 
;
_vrf_PLAT926_system1_HAR         
;
PROBLEM: Reported and Calculated   R1 Differ by .........    -0.0131 Check 
RESPONSE: Due to application of non-standard Hirshfeld Atom Refinement.
;
_vrf_PLAT927_system1_HAR         
;
PROBLEM: Reported and Calculated  wR2 Differ by .........    -0.0454 Check 
RESPONSE: Due to application of non-standard Hirshfeld Atom Refinement.
;
_vrf_PLAT928_system1_HAR         
;
PROBLEM: Reported and Calculated    S value   Differ by .     -0.586 Check 
RESPONSE: Due to application of non-standard Hirshfeld Atom Refinement.
;

_vrf_PLAT992_system1_HAR         
;
PROBLEM: Repd & Actual _reflns_number_gt Values Differ by        150 Check 
RESPONSE: Related to _reflns_threshold_expression       I>=2u(I) used.
;
_vrf_PLAT998_system1_HAR         
;
PROBLEM: SHELXL LIST 3 Fo/Fc Unsuitable for FCF-Validation         ! Error 
RESPONSE: Due to application of non-standard Hirshfeld Atom Refinement.
;
_vrf_PLAT934_system1_HAR         
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          2 Check 
RESPONSE: Despite this, refinement still converged.
;
# end Validation Reply Form

_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.05.22 svn.r1d9e7f8d for OlexSys, GUI svn.r6115)
;

_chemical_formula_moiety         'C1 H1 O2, C3 H8 N2 O1'
_chemical_formula_sum            'C4 H9 N2 O3'
_chemical_formula_weight         133.128
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.00285 0.00150 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.01010 0.00566 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.00565 0.00308 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   3.81790(10)
_cell_length_b                   13.2171(2)
_cell_length_c                   12.4080(1)
_cell_angle_alpha                90
_cell_angle_beta                 94.614(1)
_cell_angle_gamma                90
_cell_volume                     624.098(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23721
_cell_measurement_theta_min      2.1789248764459797
_cell_measurement_theta_max      56.35681599534807

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.057
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.028

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#


_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_special_details   ?
_exptl_sortav_scale_factor_max   2.381
_exptl_sortav_scale_factor_min   0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  1.132


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_source                   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_monochromator  'Silicon 111'
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.9982
_diffrn_reflns_Laue_measured_fraction_max 0.9773
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9067
_diffrn_reflns_point_group_measured_fraction_full 0.9982
_diffrn_reflns_point_group_measured_fraction_max 0.9773
_diffrn_reflns_theta_full        24.4148
_diffrn_reflns_theta_max         56.50
_diffrn_reflns_theta_min         2.19
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9773
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              -7
_reflns_number_gt                6439
_reflns_number_total             9065
_reflns_threshold_expression     I>=2u(I)


#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------# 

_computing_data_collection       'GDA - generic data acquisition software'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.14.9-g0c59d74b8-release'
_computing_data_reduction        
;
DIALS 1.14.9-g0c59d74b8-release (Winter, G. et al., 2018)
;
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'


_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_diff_density_max         0.3540
_refine_diff_density_min         -0.3670
_refine_diff_density_rms         0.0566
_refine_ls_d_res_high            0.4130
_refine_ls_d_res_low             9.0307
_refine_ls_goodness_of_fit_ref   0.8748
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     163
_refine_ls_number_reflns         9065
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      0.8748
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+0.0085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0678
_refine_special_details          
;Refinement using NoSpherA2, an implementation of
 NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss, H. Puschmann, O. Dolomanov, S.Grabowsky - to be published - 2020
NoSpherA2 implementation of 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 Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fregment can be embedded in an electrostatic crystal field by employing cluster charges.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         PBE
   BASIS SET:      def2-TZVPP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2020-06-04_16-04-50,Hirshfeld atom refinement
;
_olex2_refinement_description    
;
Initial refinement with olex2.refine G-N. 

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

;
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_refinement_flags_posn
C1 C 0.90610(5) 0.038567(13) 0.960777(14) 0.01398(2) Uani 1.000000 .
O1 O 0.73447(5) 0.107206(11) 1.008248(12) 0.01687(2) Uani 1.000000 .
O2 O 0.93037(5) 0.030233(13) 0.863233(12) 0.01965(3) Uani 1.000000 .
C2 C 0.47646(5) 0.264022(14) 0.805555(14) 0.01440(3) Uani 1.000000 .
C3 C 0.21194(7) 0.428529(17) 0.83040(2) 0.02089(4) Uani 1.000000 .
C4 C 0.66351(6) 0.207564(19) 0.629312(16) 0.02000(3) Uani 1.000000 .
O3 O 0.46127(5) 0.249132(12) 0.906658(12) 0.01787(3) Uani 1.000000 .
N1 N 0.34704(5) 0.350552(14) 0.762482(14) 0.01724(3) Uani 1.000000 .
N2 N 0.61561(5) 0.194424(14) 0.743207(13) 0.01737(3) Uani 1.000000 .
H1 H 0.606(2) 0.1705(7) 0.9510(7) 0.045(3) Uani 1.000000 .
H3a H 0.077(2) 0.4841(6) 0.7802(6) 0.070(2) Uani 1.000000 .
H3b H 0.4216(18) 0.4652(6) 0.8818(6) 0.058(2) Uani 1.000000 .
H3c H 0.0351(17) 0.3975(5) 0.8856(5) 0.0464(17) Uani 1.000000 .
H4a H 0.8270(19) 0.1456(5) 0.6042(5) 0.0470(18) Uani 1.000000 .
H4b H 0.7998(17) 0.2779(5) 0.6140(5) 0.0448(16) Uani 1.000000 .
H4c H 0.4144(17) 0.2062(6) 0.5798(5) 0.0455(16) Uani 1.000000 .
H2 H 0.7235(18) 0.1338(5) 0.7834(5) 0.0327(15) Uani 1.000000 .
H1a H 0.3755(18) 0.3675(5) 0.6846(5) 0.0394(16) Uani 1.000000 .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

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
C1 C1 1.5455(4) 3_757 ?
C1 O1 1.2890(2) . ?
C1 O2 1.2262(2) . ?
C2 O3 1.2757(2) . ?
C2 N1 1.3399(2) . ?
C2 N2 1.3390(3) . ?
C3 N1 1.4520(3) . ?
C4 N2 1.4499(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
O2 C1 O1 126.570(17) . . ?
N1 C2 O3 118.648(17) . . ?
N2 C2 O3 120.908(17) . . ?
N2 C2 N1 120.441(17) . . ?
C3 N1 C2 120.740(17) . . ?
C4 N2 C2 124.599(17) . . ?
O3 H1 O1 168.4(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
O1 H1 O3 1.177(10) 1.281(11) 2.4463(2) 168.4(7) .
O3 H1 O1 1.281(11) 1.177(10) 2.4463(2) 168.4(7) .
N2 H2 O2 1.013(6) 1.831(6) 2.8432(2) 176.1(6) .


_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        "N,N'-dimethylurea oxalic acid 2:1"
_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_system_1_XD
_database_code_depnum_ccdc_archive 'CCDC 2068359'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_system_1_XD         
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      52.20 %     
RESPONSE: Related to the choice of Z versus the calculated Z. 
;
_vrf_PLAT355_system_1_XD         
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H1       .       1.18 Ang.  
RESPONSE:Due to H1 being involved in the formation of a short strong hydrogen bond. O1-H1 distance
is that obtained from Hirshfeld atom refinement.
;
_vrf_PLAT927_system_1_XD         
;
PROBLEM: Reported and Calculated  wR2 Differ by .........    -0.0606 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
_vrf_PLAT997_system_1_XD         
;
PROBLEM: Unsuitable CIF/FCF File Combination with SHELXL CIF       ! Error 
RESPONSE: This is an XD output .cif (combined xd_geo, xd_fft and xd_lsm .cifs) .fco file.
;
_vrf_PLAT920_system_1_XD         
;
PROBLEM: Theta(Max)  in CIF and FCF Differ by ...........      11.60 Degree
RESPONSE: Theta(Max) in CIF includes data pre sinTh/L cut-off used in XDLSM refinement.
Reflections rejected based on SINTHL    =   3453
;
_vrf_PLAT926_system_1_XD         
;
PROBLEM: Reported and Calculated   R1 Differ by .........    -0.0176 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
_vrf_PLAT928_system_1_XD         
;
PROBLEM: Reported and Calculated    S value   Differ by .     -1.421 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        "N,N'-dimethylurea oxalic acid 2:1"
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C1 H1 O2, C3 H8 N2 O1'
_chemical_formula_sum            'C4 H9 N2 O3'
_chemical_formula_weight         133.13



#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_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_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
_cell_length_a                   3.81790(10)
_cell_length_b                   13.2171(2)
_cell_length_c                   12.40800(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.6140(10)
_cell_angle_gamma                90
_cell_volume                     624.10(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23721
_cell_measurement_theta_min      2.1789248764459797
_cell_measurement_theta_max      56.35681599534807

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.057
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.028

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_special_details   ?
_exptl_sortav_scale_factor_max   2.381
_exptl_sortav_scale_factor_min   0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  1.132

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_source                   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_monochromator  'Silicon 111'
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9065
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         56.505
_diffrn_reflns_theta_full        24.415
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9065
_reflns_number_gt                4702
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
 
 Pre sintheta/lambda cut-off: _reflns_number_gt                 6439
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------# 

_computing_data_collection       'GDA - generic data acquisition software'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.14.9-g0c59d74b8-release'
_computing_data_reduction        
;
DIALS 1.14.9-g0c59d74b8-release (Winter, G. et al., 2018)
;
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    MercuryTM
_computing_publication_material  ?

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.019
_refine_ls_R_factor_all          0.055
_refine_ls_R_Fsqd_factor         0.026
_refine_ls_wR_factor_ref         0.046
_refine_ls_hydrogen_treatment    ?
_refine_ls_number_reflns         4702
_refine_ls_number_parameters     200
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w2 = 1/[s²(Fo²)]
;
_refine_ls_shift/su_max          0
_refine_ls_extinction_method     none
_refine_special_details          
;Reflections were merged by SORTAV according to the crystal
class.

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.,multipole refinement
;

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.030

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_U_iso_or_equiv
O(1) 0.73443(6) 0.107208(18) 1.00833(2) 1 4 0.017
O(2) 0.93048(5) 0.030209(13) 0.86318(2) 1 4 0.019
O(3) 0.46109(5) 0.249167(13) 0.90678(2) 1 4 0.018
N(1) 0.34702(5) 0.350486(18) 0.76245(2) 1 4 0.017
N(2) 0.61574(7) 0.194357(19) 0.743211(19) 1 4 0.017
C(1) 0.90613(5) 0.038548(15) 0.960819(16) 1 4 0.014
C(2) 0.47645(5) 0.263999(16) 0.805580(17) 1 4 0.014
C(3) 0.21186(6) 0.428530(17) 0.83043(2) 1 4 0.021
C(4) 0.66348(6) 0.207560(18) 0.629352(18) 1 4 0.020
H(1) 0.606002 0.1705 0.951 1 4 0.045
H(3C) 0.078433 0.484206 0.778156 1 4 0.070
H(3A) 0.413759 0.463971 0.881786 1 4 0.058
H(3B) 0.031745 0.397389 0.886389 1 4 0.046
H(4A) 0.826316 0.145313 0.604635 1 4 0.047
H(4C) 0.800294 0.278098 0.615113 1 4 0.045
H(4B) 0.412767 0.203695 0.581037 1 4 0.045
H(2A) 0.718506 0.132694 0.782774 1 4 0.033
H(1A) 0.383062 0.368576 0.685366 1 4 0.039
loop_
_atom_local_dummy_label
_atom_local_dummy_fract_x
_atom_local_dummy_fract_y
_atom_local_dummy_fract_z
DUM0 0 0 0

#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.2896(3) 1_555 1_555 yes
O(2) C(1) 1.2275(3) 1_555 1_555 yes
O(3) C(2) 1.2769(3) 1_555 1_555 yes
N(1) C(2) 1.3397(3) 1_555 1_555 yes
N(1) C(3) 1.4532(4) 1_555 1_555 yes
N(1) H(1A) 1.0060(2) 1_555 1_555 yes
N(2) C(2) 1.3398(3) 1_555 1_555 yes
N(2) C(4) 1.4495(3) 1_555 1_555 yes
N(2) H(2A) 1.0140(2) 1_555 1_555 yes
C(3) H(3C) 1.0810(2) 1_555 1_555 yes
C(3) H(3A) 1.0680(3) 1_555 1_555 yes
C(3) H(3B) 1.0960(2) 1_555 1_555 yes
C(4) H(4A) 1.0900(2) 1_555 1_555 yes
C(4) H(4C) 1.0900(2) 1_555 1_555 yes
C(4) H(4B) 1.0890(2) 1_555 1_555 yes
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(2) N(1) C(3) 120.70(2) 1_555 1_555 1_555 yes
C(2) N(1) H(1A) 120.55(2) 1_555 1_555 1_555 yes
C(3) N(1) H(1A) 117.73(2) 1_555 1_555 1_555 yes
C(2) N(2) C(4) 124.55(2) 1_555 1_555 1_555 yes
C(2) N(2) H(2A) 115.38(2) 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 119.64(2) 1_555 1_555 1_555 yes
O(1) C(1) O(2) 126.58(2) 1_555 1_555 1_555 yes
O(3) C(2) N(1) 118.63(2) 1_555 1_555 1_555 yes
O(3) C(2) N(2) 120.95(2) 1_555 1_555 1_555 yes
N(1) C(2) N(2) 120.41(2) 1_555 1_555 1_555 yes
N(1) C(3) H(3C) 107.89(2) 1_555 1_555 1_555 yes
N(1) C(3) H(3A) 112.63(2) 1_555 1_555 1_555 yes
N(1) C(3) H(3B) 111.80(2) 1_555 1_555 1_555 yes
H(3C) C(3) H(3A) 110.00(2) 1_555 1_555 1_555 yes
H(3C) C(3) H(3B) 110.26(2) 1_555 1_555 1_555 yes
H(3A) C(3) H(3B) 104.25(2) 1_555 1_555 1_555 yes
N(2) C(4) H(4A) 107.62(2) 1_555 1_555 1_555 yes
N(2) C(4) H(4C) 111.13(2) 1_555 1_555 1_555 yes
N(2) C(4) H(4B) 110.92(2) 1_555 1_555 1_555 yes
H(4A) C(4) H(4C) 107.962(19) 1_555 1_555 1_555 yes
H(4A) C(4) H(4B) 107.80(2) 1_555 1_555 1_555 yes
H(4C) C(4) H(4B) 111.24(2) 1_555 1_555 1_555 yes

#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(1) 6.173(14) 0 -0.050(6) -0.014(6) 0 -0.022(8) 0 0 -0.040(7) 0.014(7) 0
0.016(5) -0.013(5) 0 0 0.047(5) -0.009(5) 0.024(7) 0 0 0.023(7) 0.014(7) 0 0
-0.014(6) -0.001(6) 1.001632 1.113461 1.113461 1.113461 1.113461 1.113461 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 6.153(14) 0 0 0 -0.064(6) -0.011(8) 0 0 -0.084(8) 0 0.004(6) 0 0 0.037(6)
0 0 0 0.013(8) 0 0 0.011(7) 0 0 0 0.023(7) 0 1.003017 1.109004 1.109004
1.109004 1.109004 1.109004 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(3) 6.166(14) 0 0 0 -0.035(6) -0.014(7) 0 0 -0.058(7) 0 0.045(6) 0 0 0.035(5)
0 0 0 0.039(7) 0 0 -0.005(7) 0 0 0 0.000(6) 0 1.003017 1.109004 1.109004
1.109004 1.109004 1.109004 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
N(1) 4.944(16) 0 -0.023(7) 0.015(7) 0 -0.009(7) 0 0 -0.003(7) 0.018(7) 0
0.007(6) 0.004(6) 0 0 0.149(6) 0.003(6) 0.046(9) 0 0 0.006(8) -0.023(8) 0 0
-0.021(7) -0.020(8) 1.006323 1.062557 1.062557 1.062557 1.062557 1.062557 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(2) 4.955(17) 0 -0.015(7) 0.019(7) -0.018(8) -0.009(8) -0.004(6) 0.005(7)
0.004(7) 0.015(6) 0.160(7) -0.007(6) -0.023(7) 0.082(7) 0.004(6) -0.027(6)
0.024(7) 0.043(9) 0.025(8) -0.002(8) 0.002(8) -0.009(8) 0.003(8) -0.016(9)
0.020(8) -0.004(7) 1.010014 1.028362 1.028362 1.028362 1.028362 1.028362 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
C(1) 4.004(19) 0 0.083(9) 0.006(8) 0 -0.298(8) 0 0 0.077(8) -0.033(7) 0
0.003(8) -0.015(8) 0 0 0.322(9) 0.035(9) 0.044(11) 0 0 0.013(11) -0.011(10) 0 0
-0.010(13) -0.007(10) 1.015931 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(2) 3.93(2) 0 -0.007(9) -0.042(9) 0 -0.275(8) 0 0 0.017(9) -0.001(8) 0
-0.021(9) 0.013(9) 0 0 0.339(10) 0.028(9) 0.020(12) 0 0 -0.027(11) -0.026(11) 0
0 0.006(13) -0.074(12) 1.016311 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(3) 3.92(2) 0 0 0 -0.043(7) -0.035(6) 0 0 0 0 0.263(7) 0 0 0 0 0 -0.165(7)
0.054(9) 0 0 0 0 0 0.059(8) 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(4) 3.9202 0 0 0 -0.0428 -0.0345 0 0 0 0 0.2634 0 0 0 0 0 -0.1648 0.0539 0 0 0
0 0 0.0587 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(1) 0.808(14) 0 0 0 0.037(11) 0.085(18) 0 0 0 0 0.0171 0 0 0 0 0 0 -0.0278 0 0
0 0 0 0 0 0 1.119673 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3C) 1.032(8) 0 0 0 0.157(5) 0.073(7) 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0
0 0 0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0
0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3B) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0
0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(4A) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0
0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(4C) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0
0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(4B) 1.0319 0 0 0 0.1572 0.073 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0 0
0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2A) 0.918(10) 0 0 0 0.192(8) 0.129(10) 0 0 0 0 0.0172 0 0 0 0 0 0 -0.0115 0 0
0 0 0 0 0 0 1.140452 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(1A) 0.918 0 0 0 0.1915 0.1291 0 0 0 0 0.0172 0 0 0 0 0 0 -0.0115 0 0 0 0 0 0
0 0 1.140452 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(1) X O(1) H(1) Y
O(2) C(1) Z O(2) O(1) Y
O(3) C(2) Z O(3) N(2) Y
N(1) C(2) X N(1) C(3) Y
N(2) H(2A) Z N(2) C(2) Y
C(1) O(2) X C(1) O(1) Y
C(2) O(3) X C(2) N(2) Y
C(3) N(1) Z C(3) H(3C) Y
C(4) N(2) Z C(4) H(4B) Y
H(1) O(1) Z H(1) C(1) Y
H(3C) C(3) Z H(3C) N(1) Y
H(3A) C(3) Z H(3A) N(1) Y
H(3B) C(3) Z H(3B) N(1) Y
H(4A) C(4) Z H(4A) N(2) Y
H(4C) C(4) Z H(4C) N(2) Y
H(4B) C(4) Z H(4B) N(2) Y
H(2A) N(2) Z H(2A) C(2) Y
H(1A) N(1) Z H(1A) C(2) Y





#----------------------------------------------------------------------------#
#                   STRUCTURE FACTOR INFORMATION                             #
#----------------------------------------------------------------------------#

#
#  Unique observations used in XD refinement
#  F^2(calc) includes anomalous dispersion and is corrected for extinction
#  if the latter is included in the model.
#

_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_system3_HAR
_database_code_depnum_ccdc_archive 'CCDC 2068357'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_SHFSU01_system3_HAR         
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.20
RESPONSE: This is related to the methyl H-atoms showing a slight disorder
in their postions on C17.
Shifts: xyz: 0.0322 for H17c, U: 0.0293 for H17c, Max/esd = 1.0669 for H17c.z
;
_vrf_PLAT051_system3_HAR         
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      50.88 %     
RESPONSE: Mu(CIF) value was obtained using the CALC Mu function in Wingx and then supplied to SORTAV for
scaling. 
;
_vrf_PLAT080_system3_HAR         
;
PROBLEM: Maximum Shift/Error ............................       1.07 Why ? 
RESPONSE: This is related to the methyl H-atoms showing a slight disorder
in their postions on C17.
Shifts: xyz: 0.0322 for H17c, U: 0.0293 for H17c, Max/esd = 1.0669 for H17c.z
;
_vrf_PLAT355_system3_HAR         
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O9       - H9       .       1.14 Ang.  
RESPONSE: Elongated distance is due to H1 being involved in the formation of a short strong hydrogen bond. 
;
_vrf_PLAT992_system3_HAR         
;
PROBLEM: Repd & Actual _reflns_number_gt Values Differ by        444 Check 
RESPONSE: Related to _reflns_threshold_expression       I>=2u(I) used.
;
_vrf_PLAT998_system3_HAR         
;
PROBLEM: SHELXL LIST 3 Fo/Fc Unsuitable for FCF-Validation         ! Error 
RESPONSE: Due to application of non-standard Hirshfeld Atom Refinement.
;
_vrf_PLAT430_system3_HAR         
;
PROBLEM: Short Inter D...A Contact  O2       ..N2       .       2.86 Ang.  
RESPONSE: O2 and N2 are in different layers of the crystal structure and
form and edge to face type interaction.
;
_vrf_PLAT922_system3_HAR         
;
PROBLEM: wR2 in the CIF and FCF Differ by ...............     0.0298 Check 
RESPONSE: Due to application of non-standard Hirshfeld Atom Refinement.
;
# end Validation Reply Form


_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.05.22 svn.r1d9e7f8d for OlexSys, GUI svn.r6115)
;
_chemical_formula_moiety         '2(C10 H12 N4 O7)'
_chemical_formula_sum            'C20 H24 N8 O14'
_chemical_formula_weight         600.459
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.00285 0.00150 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.01010 0.00566 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.00565 0.00308 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   28.3783(1)
_cell_length_b                   6.0988(3)
_cell_length_c                   29.7998(1)
_cell_angle_alpha                90
_cell_angle_beta                 92.5110(4)
_cell_angle_gamma                90
_cell_volume                     5152.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    69509
_cell_measurement_theta_min      1.3196843649799979
_cell_measurement_theta_max      46.27331728763817

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             2496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.055
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.025


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.998
_exptl_sortav_scale_factor_max   1.952
_exptl_sortav_scale_factor_min   0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  1.069



#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_source                   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_monochromator  'Silicon 111'
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       59
_diffrn_reflns_limit_h_min       -59
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            24743
_diffrn_reflns_point_group_measured_fraction_full 0.9998
_diffrn_reflns_point_group_measured_fraction_max 0.9890
_diffrn_reflns_theta_full        24.4148
_diffrn_reflns_theta_max         46.35
_diffrn_reflns_theta_min         1.33
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_measured_fraction_theta_max 0.9890
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              59
_reflns_limit_h_min              -59
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              62
_reflns_limit_l_min              0
_reflns_number_gt                17697
_reflns_number_total             24742
_reflns_threshold_expression     I>=2u(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------# 

_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_diff_density_max         0.2464
_refine_diff_density_min         -0.3705
_refine_diff_density_rms         0.0530
_refine_ls_d_res_high            0.4761
_refine_ls_d_res_low             14.8856
_refine_ls_goodness_of_fit_ref   0.7239
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     595
_refine_ls_number_reflns         24742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      0.7239
_refine_ls_shift/su_max          1.0669
_refine_ls_shift/su_mean         0.0789
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+0.1103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0963
_refine_special_details          
;Refinement using NoSpherA2, an implementation of
 NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss, H. Puschmann, O. Dolomanov, S.Grabowsky - to be published - 2020
NoSpherA2 implementation of 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 Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fregment can be embedded in an electrostatic crystal field by employing cluster charges.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         PBE
   BASIS SET:      def2-TZVPP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2020-06-04_16-27-24,Hirshfeld atom refinement
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
  Initial refinement with olex2.refine G-N. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_refinement_flags_posn
H5 H 0.1328(3) 0.4533(14) 0.2048(3) 0.039(2) Uani 1.000000 .
H7 H 0.2350(3) -0.0644(13) 0.2250(3) 0.047(2) Uani 1.000000 .
H12 H 0.1261(3) 0.4845(14) -0.0160(3) 0.047(2) Uani 1.000000 .
H3 H 0.2659(3) 0.4800(15) 0.1391(3) 0.045(2) Uani 1.000000 .
H14 H 0.0719(3) 0.9212(15) 0.0843(3) 0.044(2) Uani 1.000000 .
H8a H 0.0077(4) 0.1588(16) 0.0382(4) 0.050(3) Uani 1.000000 .
H10 H 0.2023(3) 1.0751(15) 0.0216(3) 0.051(2) Uani 1.000000 .
H5a H 0.0748(4) -0.5538(14) 0.2870(4) 0.059(3) Uani 1.000000 .
H5b H 0.1094(3) -0.3174(16) 0.2785(4) 0.051(3) Uani 1.000000 .
H20a H -0.1176(5) 0.3533(15) 0.1171(5) 0.091(5) Uani 1.000000 .
H19a H -0.0829(4) -0.2150(15) 0.0495(3) 0.058(3) Uani 1.000000 .
H8b H -0.0180(4) -0.0980(14) 0.0499(4) 0.059(3) Uani 1.000000 .
H20b H -0.1572(3) 0.141(2) 0.1092(4) 0.075(4) Uani 1.000000 .
H19b H -0.0798(5) -0.2604(18) 0.1086(4) 0.090(4) Uani 1.000000 .
H19c H -0.1343(4) -0.1957(17) 0.0805(5) 0.081(4) Uani 1.000000 .
H20c H -0.1167(5) 0.119(2) 0.1514(3) 0.090(5) Uani 1.000000 .
H1 H 0.0825(4) 0.044(2) 0.2710(4) 0.045(3) Uani 1.000000 .
H16a H 0.0233(4) -0.6517(19) 0.3324(5) 0.092(4) Uani 1.000000 .
H16b H -0.0337(6) -0.600(3) 0.3368(8) 0.137(7) Uani 1.000000 .
H16c H -0.0113(10) -0.644(2) 0.2863(5) 0.156(10) Uani 1.000000 .
H9 H -0.0100(5) 0.487(2) 0.0694(4) 0.057(4) Uani 1.000000 .
C6 C 0.180611(10) 0.18228(5) 0.218607(10) 0.01652(4) Uani 1.000000 .
C4 C 0.198555(11) 0.48545(5) 0.171405(10) 0.01677(4) Uani 1.000000 .
N2 N 0.298576(10) 0.09437(5) 0.170851(10) 0.01994(4) Uani 1.000000 .
C5 C 0.167296(11) 0.38233(5) 0.199121(11) 0.01712(4) Uani 1.000000 .
C3 C 0.242118(11) 0.39786(5) 0.161683(11) 0.01779(4) Uani 1.000000 .
O1 O 0.107178(9) 0.14807(4) 0.252375(10) 0.02155(4) Uani 1.000000 .
O2 O 0.159274(10) -0.12560(5) 0.261683(11) 0.02581(5) Uani 1.000000 .
C2 C 0.253863(10) 0.19912(5) 0.181822(10) 0.01686(4) Uani 1.000000 .
C1 C 0.147783(11) 0.05450(5) 0.246781(11) 0.01823(4) Uani 1.000000 .
N1 N 0.184357(11) 0.69311(4) 0.149634(10) 0.01920(4) Uani 1.000000 .
O5 O 0.308761(11) -0.07968(5) 0.189177(11) 0.02734(5) Uani 1.000000 .
O3 O 0.213194(11) 0.78801(5) 0.127373(10) 0.02481(5) Uani 1.000000 .
C7 C 0.224415(11) 0.09072(5) 0.210363(10) 0.01699(4) Uani 1.000000 .
O6 O 0.322915(11) 0.18632(6) 0.143940(12) 0.02867(6) Uani 1.000000 .
O4 O 0.144480(11) 0.76094(5) 0.155368(11) 0.02615(5) Uani 1.000000 .
O9 O 0.020990(10) 0.60426(4) 0.065044(10) 0.02203(4) Uani 1.000000 .
O10 O 0.052843(11) 0.35370(4) 0.020326(10) 0.02253(4) Uani 1.000000 .
C14 C 0.098211(12) 0.87719(5) 0.060092(11) 0.01855(4) Uani 1.000000 .
N3 N 0.141199(12) 1.21204(5) 0.082232(11) 0.02293(5) Uani 1.000000 .
C12 C 0.128683(12) 0.63287(6) 0.004519(11) 0.01996(5) Uani 1.000000 .
C8 C 0.053429(11) 0.53220(5) 0.039421(11) 0.01807(4) Uani 1.000000 .
C9 C 0.136819(12) 1.01251(5) 0.054692(11) 0.01946(5) Uani 1.000000 .
O8 O 0.111004(12) 1.24779(5) 0.109371(11) 0.02893(6) Uani 1.000000 .
C13 C 0.094139(11) 0.68616(5) 0.034528(11) 0.01765(4) Uani 1.000000 .
C10 C 0.171531(13) 0.96784(6) 0.024704(12) 0.02262(5) Uani 1.000000 .
C11 C 0.166280(12) 0.77520(6) 0.000153(12) 0.02223(5) Uani 1.000000 .
O7 O 0.174683(13) 1.33352(5) 0.076076(12) 0.03022(6) Uani 1.000000 .
N4 N 0.202248(13) 0.71920(8) -0.031919(14) 0.03076(7) Uani 1.000000 .
O12 O 0.229316(15) 0.86449(9) -0.042569(15) 0.04136(9) Uani 1.000000 .
O11 O 0.203017(14) 0.53187(8) -0.046319(16) 0.04141(9) Uani 1.000000 .
O14 O -0.048319(10) 0.38127(4) 0.079219(11) 0.02285(5) Uani 1.000000 .
N7 N -0.089713(11) 0.07044(4) 0.088287(10) 0.02042(4) Uani 1.000000 .
C18 C -0.052164(11) 0.17605(5) 0.073218(11) 0.01748(4) Uani 1.000000 .
N8 N -0.019569(13) 0.06648(5) 0.050764(13) 0.02554(6) Uani 1.000000 .
C20 C -0.121367(14) 0.17926(6) 0.118456(13) 0.02310(6) Uani 1.000000 .
C19 C -0.09640(2) -0.16281(6) 0.081377(18) 0.03498(11) Uani 1.000000 .
O13 O 0.049095(10) -0.04809(5) 0.296317(11) 0.02456(5) Uani 1.000000 .
N5 N 0.077739(12) -0.38945(6) 0.284784(14) 0.02690(6) Uani 1.000000 .
C15 C 0.043666(12) -0.25376(6) 0.298184(12) 0.02069(5) Uani 1.000000 .
N6 N 0.003592(12) -0.33575(6) 0.313526(14) 0.02644(6) Uani 1.000000 .
C16 C -0.005249(18) -0.56955(8) 0.317045(18) 0.03234(8) Uani 1.000000 .
C17 C -0.033095(16) -0.18442(9) 0.326145(19) 0.03285(9) Uani 1.000000 .
H17a H -0.0201(6) -0.069(3) 0.3534(6) 0.126(7) Uani 1.000000 .
H17b H -0.0427(7) -0.082(3) 0.3021(5) 0.152(9) Uani 1.000000 .
H17c H -0.0615(6) -0.258(2) 0.3382(10) 0.182(11) Uani 1.000000 .


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

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
C6 C5 1.3962(4) . ?
C6 C1 1.4996(4) . ?
C6 C7 1.3943(4) . ?
C4 C5 1.3888(4) . ?
C4 C3 1.3889(4) . ?
C4 N1 1.4711(4) . ?
N2 C2 1.4702(4) . ?
N2 O5 1.2226(4) . ?
N2 O6 1.2179(4) . ?
C3 C2 1.3867(4) . ?
O1 C1 1.3031(4) . ?
O2 C1 1.2237(4) . ?
C2 C7 1.3860(4) . ?
N1 O3 1.2216(4) . ?
N1 O4 1.2239(4) . ?
O9 C8 1.2982(4) . ?
O10 C8 1.2281(4) . ?
C14 C9 1.3867(5) . ?
C14 C13 1.3940(4) . ?
N3 C9 1.4700(4) . ?
N3 O8 1.2233(5) . ?
N3 O7 1.2251(5) . ?
C12 C13 1.3940(5) . ?
C12 C11 1.3860(5) . ?
C8 C13 1.5008(4) . ?
C9 C10 1.3858(5) . ?
C10 C11 1.3886(5) . ?
C11 N4 1.4688(5) . ?
N4 O12 1.2237(6) . ?
N4 O11 1.2209(6) . ?
O14 C18 1.2684(4) . ?
N7 C18 1.3394(4) . ?
N7 C20 1.4582(4) . ?
N7 C19 1.4486(5) . ?
C18 N8 1.3431(4) . ?
O13 C15 1.2653(4) . ?
N5 C15 1.3465(5) . ?
C15 N6 1.3409(5) . ?
N6 C16 1.4524(6) . ?
N6 C17 1.4530(6) . ?

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
O13 H1 O1 169.6(11) . . ?
O14 H9 O9 169.5(10) . . ?
C1 C6 C5 121.57(3) . . ?
C7 C6 C5 120.25(3) . . ?
C7 C6 C1 118.10(3) . . ?
C3 C4 C5 123.19(3) . . ?
N1 C4 C5 118.84(3) . . ?
N1 C4 C3 117.92(3) . . ?
O5 N2 C2 117.87(3) . . ?
O6 N2 C2 117.79(3) . . ?
O6 N2 O5 124.34(3) . . ?
C4 C5 C6 118.34(3) . . ?
C2 C3 C4 116.44(3) . . ?
C3 C2 N2 118.49(3) . . ?
C7 C2 N2 118.60(3) . . ?
C7 C2 C3 122.86(3) . . ?
O1 C1 C6 114.74(3) . . ?
O2 C1 C6 120.49(3) . . ?
O2 C1 O1 124.74(3) . . ?
O3 N1 C4 118.06(3) . . ?
O4 N1 C4 117.80(3) . . ?
O4 N1 O3 124.14(3) . . ?
C2 C7 C6 118.90(3) . . ?
C13 C14 C9 118.75(3) . . ?
O8 N3 C9 118.17(3) . . ?
O7 N3 C9 117.66(4) . . ?
O7 N3 O8 124.17(3) . . ?
C11 C12 C13 118.69(3) . . ?
O10 C8 O9 125.24(3) . . ?
C13 C8 O9 114.46(3) . . ?
C13 C8 O10 120.29(3) . . ?
N3 C9 C14 118.41(3) . . ?
C10 C9 C14 123.06(3) . . ?
C10 C9 N3 118.53(3) . . ?
C12 C13 C14 120.11(3) . . ?
C8 C13 C14 121.03(3) . . ?
C8 C13 C12 118.85(3) . . ?
C11 C10 C9 116.31(3) . . ?
C10 C11 C12 123.08(3) . . ?
N4 C11 C12 118.37(3) . . ?
N4 C11 C10 118.55(3) . . ?
O12 N4 C11 117.54(4) . . ?
O11 N4 C11 118.03(4) . . ?
O11 N4 O12 124.43(4) . . ?
C20 N7 C18 120.56(3) . . ?
C19 N7 C18 121.72(3) . . ?
C19 N7 C20 117.01(3) . . ?
N7 C18 O14 119.48(3) . . ?
N8 C18 O14 120.28(3) . . ?
N8 C18 N7 120.21(3) . . ?
N5 C15 O13 120.39(3) . . ?
N6 C15 O13 119.43(3) . . ?
N6 C15 N5 120.18(3) . . ?
C16 N6 C15 122.85(4) . . ?
C17 N6 C15 118.65(3) . . ?
C17 N6 C16 118.48(4) . . ?



_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        'N,N-dimethylurea 3,5-dinitrobenzoic acid 2:2'
_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_system3_XD
_database_code_depnum_ccdc_archive 'CCDC 2068356'
loop_
_audit_author_name
_audit_author_address
'Lucy Saunders'
;Diamond Light Source
United Kingdom
;
_audit_update_record             
;
2021-03-05 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT051_system3_XD          
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      50.88 %     
RESPONSE: Mu(CIF) value was obtained using the CALC Mu function in Wingx and then supplied to SORTAV for
scaling. 
;
_vrf_PLAT355_system3_XD          
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O9       - H9       .       1.15 Ang.  
RESPONSE: Due to H1 being involved in the formation of a short strong hydrogen bond. O1-H1 distance
is that obtained from Hirshfeld atom refinement.
;
_vrf_PLAT927_system3_XD          
;
PROBLEM: Reported and Calculated  wR2 Differ by .........    -0.0580 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
_vrf_PLAT997_system3_XD          
;
PROBLEM: Unsuitable CIF/FCF File Combination with SHELXL CIF       ! Error 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
_vrf_PLAT430_system3_XD          
;
PROBLEM: Short Inter D...A Contact  O2       ..N2       .       2.86 Ang.  
RESPONSE: O2 and N2 are in different layers of the crystal structure and
form and edge to face type interaction.
;
_vrf_PLAT920_system3_XD          
;
PROBLEM: Theta(Max)  in CIF and FCF Differ by ...........       1.52 Degree
RESPONSE: Theta(Max) in CIF includes data pre sinTh/L cut-off used in XDLSM refinement.
Reflections rejected based on SINTHL    =   1757
;
_vrf_PLAT926_system3_XD          
;
PROBLEM: Reported and Calculated   R1 Differ by .........    -0.0180 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
_vrf_PLAT928_system3_XD          
;
PROBLEM: Reported and Calculated    S value   Differ by .     -1.122 Check 
RESPONSE: CIF and FCO both originate from the last XDLSM refinement cycle.
This is a false alert as PLATON cannot handle the XDLSM output fco file.
;
# 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), 2(C3 H8 N2 O1)'
_chemical_formula_sum            'C20 H24 N8 O14'
_chemical_formula_weight         600.47


#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#


_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_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-Y,1/2+Z
5 1/2+X,1/2+Y,+Z
6 1/2-X,1/2-Y,-Z
7 1/2-X,1/2+Y,1/2-Z
8 1/2+X,1/2-Y,1/2+Z

_cell_length_a                   28.37830(10)
_cell_length_b                   6.0988(3)
_cell_length_c                   29.79980(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.5110(4)
_cell_angle_gamma                90
_cell_volume                     5152.6(3
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    69509
_cell_measurement_theta_min      1.3196843649799979
_cell_measurement_theta_max      46.27331728763817


#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             2496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.055
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.025

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.998
_exptl_sortav_scale_factor_max   1.952
_exptl_sortav_scale_factor_min   0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  1.069

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_source                   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_monochromator  'Silicon 111'
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24742
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_min       -59
_diffrn_reflns_limit_h_max       59
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       62
_diffrn_reflns_theta_min         1.326
_diffrn_reflns_theta_max         46.348
_diffrn_reflns_theta_full        24.415
_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_number_total             24742
_reflns_number_gt                17021
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
 
  Pre sintheta/lambda cut-off: _reflns_number_gt                 17697
 
 Reflections were merged by SORTAV according to the crystal
class.
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------# 

_computing_data_collection       'GDA - generic data acquisition software'
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.14.9-g0c59d74b8-release'
_computing_data_reduction        
;
DIALS 1.14.9-g0c59d74b8-release (Winter, G. et al., 2018)
;
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    MercuryTM
_computing_publication_material  ?

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.025
_refine_ls_R_factor_all          0.054
_refine_ls_R_Fsqd_factor         0.025
_refine_ls_wR_factor_ref         0.053
_refine_ls_hydrogen_treatment    ?
_refine_ls_number_reflns         17021
_refine_ls_number_parameters     660
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w2 = 1/[s²(Fo²)]
;
_refine_ls_shift/su_max          0
_refine_ls_extinction_method     none

_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.

HFIX 137 used for the initial geometric placement of H-atoms on C17 
 where this group showed a slight disorder of the H-atom positions.
 
Bond distances involving H-atom distances and H-atom ADPs were fixed during the 
refinement to those extracted from Hirshfeld atom refinement.,multipole refinement
;

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.032

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#


_atom_site_anharm_details        
;
The atomic anharmonic pdf is approximated by a Gram-Charlier expansion
about the harmonic pdf, according to the expression :
      P(u) = (1 + Cijk*Hijk/3! + Dijkl*Hijkl/4!)*P(0)
The coefficients Cijk and Dijkl are refined in the least squares procedure.
The reported coefficients Cijk are multiplied by 1000 and Dijkl by 10000.
;
loop_
_atom_site_anharm_GC_C_label
_atom_site_anharm_GC_C_111
_atom_site_anharm_GC_C_222
_atom_site_anharm_GC_C_333
_atom_site_anharm_GC_C_112
_atom_site_anharm_GC_C_122
_atom_site_anharm_GC_C_113
_atom_site_anharm_GC_C_133
_atom_site_anharm_GC_C_223
_atom_site_anharm_GC_C_233
_atom_site_anharm_GC_C_123
O(12) -0.000041(4) -0.0067(7) -0.000002(4) 0.000206(14) -0.00061(8)
-0.000021(2) -0.000012(2) -0.00046(7) 0.000094(13) 0.000127(10)

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_U_iso_or_equiv
O(1) 0.107164(17) 0.14802(8) 0.252379(12) 1 8 0.021
O(2) 0.159302(10) -0.12599(8) 0.261719(11) 1 8 0.026
O(5) 0.308768(10) -0.08006(5) 0.189186(10) 1 8 0.027
O(3) 0.213245(11) 0.78823(4) 0.127335(9) 1 8 0.025
O(6) 0.322960(10) 0.18655(5) 0.143874(11) 1 8 0.028
O(4) 0.144393(11) 0.76108(4) 0.155388(10) 1 8 0.026
O(9) 0.020985(17) 0.60447(7) 0.065085(13) 1 8 0.022
O(10) 0.052835(9) 0.35365(7) 0.020331(11) 1 8 0.022
O(8) 0.110930(12) 1.24796(5) 0.109430(11) 1 8 0.029
O(7) 0.174738(12) 1.33367(5) 0.076064(10) 1 8 0.030
O(12) 0.22918(2) 0.86478(13) -0.04271(2) 1 8 0.041
O(11) 0.203039(12) 0.53135(7) -0.046310(13) 1 8 0.041
O(14) -0.048335(9) 0.38142(7) 0.079254(9) 1 8 0.023
O(13) 0.049078(9) -0.04811(9) 0.296330(10) 1 8 0.024
N(2) 0.298567(10) 0.09432(4) 0.170848(9) 1 8 0.020
N(1) 0.184342(10) 0.69324(4) 0.149631(9) 1 8 0.019
N(3) 0.141199(11) 1.21203(5) 0.082235(10) 1 8 0.023
N(4) 0.202274(12) 0.71911(6) -0.031954(12) 1 8 0.031
N(7) -0.089728(13) 0.07035(5) 0.088264(10) 1 8 0.020
N(8) -0.019514(13) 0.06639(5) 0.050685(12) 1 8 0.025
N(5) 0.077810(13) -0.38964(6) 0.284733(13) 1 8 0.027
N(6) 0.003604(14) -0.33580(7) 0.313512(13) 1 8 0.026
C(6) 0.180618(12) 0.18224(5) 0.218613(11) 1 8 0.016
C(4) 0.198542(10) 0.48567(5) 0.171386(10) 1 8 0.017
C(5) 0.167274(11) 0.38240(5) 0.199121(10) 1 8 0.017
C(3) 0.242126(11) 0.39788(5) 0.161671(10) 1 8 0.018
C(2) 0.253904(10) 0.19906(5) 0.181805(10) 1 8 0.017
C(1) 0.147802(12) 0.05457(6) 0.246764(11) 1 8 0.018
C(7) 0.224422(11) 0.09061(5) 0.210374(10) 1 8 0.017
C(14) 0.098193(13) 0.87723(5) 0.060114(11) 1 8 0.018
C(12) 0.128682(12) 0.63276(5) 0.004502(11) 1 8 0.020
C(8) 0.053443(13) 0.53218(5) 0.039421(11) 1 8 0.018
C(9) 0.136813(11) 1.01262(5) 0.054724(10) 1 8 0.019
C(13) 0.094138(13) 0.68615(5) 0.034525(11) 1 8 0.018
C(10) 0.171567(12) 0.96790(6) 0.024708(11) 1 8 0.023
C(11) 0.166298(12) 0.77509(6) 0.000114(11) 1 8 0.022
C(18) -0.052147(13) 0.17609(5) 0.073213(10) 1 8 0.017
C(20) -0.121383(12) 0.17943(5) 0.118454(12) 1 8 0.023
C(19) -0.096401(18) -0.16291(6) 0.081412(15) 1 8 0.035
C(15) 0.043677(13) -0.25386(7) 0.298197(12) 1 8 0.021
C(16) -0.005296(15) -0.56961(7) 0.317035(15) 1 8 0.032
C(17) -0.033126(14) -0.18419(8) 0.326120(16) 1 8 0.033
H(5) 0.132849 0.454783 0.204452 1 8 0.040
H(7) 0.235117 -0.061619 0.22621 1 8 0.047
H(12) 0.125499 0.484932 -0.016145 1 8 0.046
H(3) 0.265211 0.482221 0.138761 1 8 0.044
H(14) 0.072282 0.921611 0.084193 1 8 0.044
H(8A) 0.007943 0.160295 0.038937 1 8 0.050
H(10) 0.201699 1.07841 0.021041 1 8 0.051
H(5B) 0.074755 -0.556718 0.286934 1 8 0.059
H(5A) 0.108977 -0.320187 0.2781 1 8 0.051
H(20B) -0.115964 0.352448 0.116669 1 8 0.091
H(19A) -0.082886 -0.21744 0.049603 1 8 0.058
H(8B) -0.019105 -0.098176 0.049927 1 8 0.059
H(20A) -0.157342 0.144851 0.108957 1 8 0.075
H(19C) -0.080333 -0.260968 0.108568 1 8 0.090
H(19B) -0.134545 -0.195835 0.080316 1 8 0.081
H(20C) -0.114865 0.124453 0.151572 1 8 0.089
H(1) 0.082522 0.044095 0.270983 1 8 0.045
H(16C) 0.022964 -0.650735 0.332219 1 8 0.092
H(16B) -0.033819 -0.600128 0.336883 1 8 0.137
H(16A) -0.011361 -0.644753 0.285989 1 8 0.157
H(9) -0.010113 0.486571 0.069416 1 8 0.057
H(17A) -0.020153 -0.069471 0.353288 1 8 0.126
H(17B) -0.060915 -0.256476 0.337755 1 8 0.182
H(17C) -0.04291 -0.079761 0.301573 1 8 0.152
loop_
_atom_local_dummy_label
_atom_local_dummy_fract_x
_atom_local_dummy_fract_y
_atom_local_dummy_fract_z
DUM0 0 0 0
DUM1 0.220329 0.321889 0.182128
DUM2 0.144202 0.866543 0.028412
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O(1) 0.01701(13) 0.01882(13) 0.02870(16) 0.00072(13) 0.00431(12) 0.00093(12)
O(2) 0.01933(14) 0.02544(14) 0.03299(18) 0.00379(10) 0.00579(13) 0.01256(15)
O(5) 0.02335(11) 0.02875(11) 0.03003(13) 0.00955(9) 0.00635(10) 0.00636(10)
O(3) 0.03034(12) 0.01906(9) 0.02456(11) -0.00190(9) 0.00225(9) 0.00441(8)
O(6) 0.02510(11) 0.03077(12) 0.03063(13) 0.00396(10) 0.01283(10) 0.00407(11)
O(4) 0.02556(11) 0.02275(10) 0.02956(13) 0.00624(9) 0.00029(9) 0.00552(10)
O(9) 0.02130(13) 0.01658(12) 0.02802(15) -0.00073(13) 0.00489(14) -0.00490(12)
O(10) 0.02746(15) 0.01665(11) 0.02361(13) -0.00250(9) 0.00590(13) -0.00494(12)
O(8) 0.03342(13) 0.02517(11) 0.02745(12) 0.00084(10) -0.00356(11) -0.00945(10)
O(7) 0.03652(14) 0.02291(10) 0.03024(13) -0.00897(10) -0.00707(11) -0.00189(10)
O(12) 0.03358(15) 0.0567(2) 0.03495(16) -0.01403(15) 0.01267(13) -0.00708(15)
O(11) 0.02997(14) 0.0505(2) 0.04457(18) -0.00404(13) 0.01192(14) -0.02196(15)
O(14) 0.02254(13) 0.01389(13) 0.03242(17) 0.00008(7) 0.00611(15) -0.00294(8)
O(13) 0.02034(14) 0.02056(17) 0.0332(2) -0.00088(8) 0.00953(14) -0.00174(8)
N(2) 0.01754(10) 0.02238(10) 0.01960(10) 0.00259(8) 0.00355(8) -0.00013(9)
N(1) 0.02279(11) 0.01577(8) 0.01839(10) 0.00064(7) -0.00119(8) 0.00090(7)
N(3) 0.02745(12) 0.01823(9) 0.02183(11) -0.00129(9) -0.00755(10) -0.00225(8)
N(4) 0.02297(12) 0.04258(18) 0.02675(14) -0.00501(12) 0.00510(11) -0.00866(12)
N(7) 0.02677(12) 0.01355(10) 0.02123(13) -0.00070(10) 0.00755(11) -0.00129(8)
N(8) 0.02973(14) 0.01495(10) 0.03221(16) 0.00157(10) 0.01335(14) -0.00155(11)
N(5) 0.02113(12) 0.02191(12) 0.0372(2) 0.00264(11) 0.00352(13) -0.00179(12)
N(6) 0.01994(13) 0.02407(14) 0.03540(18) -0.00274(11) 0.00509(12) 0.00389(11)
C(6) 0.01544(10) 0.01689(10) 0.01700(11) 0.00028(9) 0.00113(9) 0.00091(9)
C(4) 0.01770(10) 0.01558(9) 0.01661(10) -0.00015(7) -0.00017(8) 0.00051(8)
C(5) 0.01612(10) 0.01689(9) 0.01806(11) 0.00100(8) 0.00051(8) 0.00069(8)
C(3) 0.01775(10) 0.01736(9) 0.01787(11) -0.00060(9) 0.00166(8) 0.00081(8)
C(2) 0.01603(10) 0.01740(9) 0.01692(10) 0.00059(8) 0.00156(8) -0.00010(8)
C(1) 0.01568(11) 0.01899(11) 0.01990(12) 0.00058(10) 0.00158(9) 0.00255(10)
C(7) 0.01612(10) 0.01687(9) 0.01758(11) 0.00089(8) 0.00111(8) 0.00085(8)
C(14) 0.02001(12) 0.01662(10) 0.01843(11) 0.00032(9) -0.00126(10) -0.00235(10)
C(12) 0.01963(11) 0.02107(11) 0.01891(11) -0.00042(9) 0.00027(9) -0.00355(9)
C(8) 0.02041(12) 0.01497(10) 0.01859(11) 0.00014(9) 0.00077(10) -0.00192(9)
C(9) 0.02060(11) 0.01792(10) 0.01915(11) -0.00119(8) -0.00366(9) -0.00136(9)
C(13) 0.01861(11) 0.01636(10) 0.01753(11) 0.00020(9) -0.00056(10) -0.00150(9)
C(10) 0.02067(12) 0.02506(12) 0.02169(13) -0.00444(10) -0.00158(10)
-0.00176(11)
C(11) 0.01937(11) 0.02665(13) 0.02026(12) -0.00260(10) 0.00030(10) -0.00320(10)
C(18) 0.02108(12) 0.01255(10) 0.01869(12) 0.00147(9) 0.00280(10) -0.00024(8)
C(20) 0.02451(13) 0.01964(11) 0.02531(14) 0.00256(9) 0.00682(11) -0.00164(10)
C(19) 0.0530(2) 0.01677(12) 0.03695(19) -0.00872(13) 0.02531(18) -0.00692(12)
C(15) 0.01714(12) 0.02043(13) 0.02489(15) -0.00081(10) 0.00240(10) 0.00004(10)
C(16) 0.03358(18) 0.02734(15) 0.03533(19) -0.00838(13) -0.00159(14) 0.00710(13)
C(17) 0.02282(14) 0.03975(19) 0.0365(2) 0.00342(13) 0.01116(13) 0.00658(15)
H(5) 0.024 0.044 0.052 0.019 0.009 0.007
H(7) 0.045 0.027 0.07 0.006 0.006 0.031
H(12) 0.056 0.035 0.049 0 0.009 -0.025
H(3) 0.047 0.043 0.045 -0.005 0.027 0.012
H(14) 0.035 0.049 0.049 0.002 0.015 -0.017
H(8A) 0.044 0.039 0.067 -0.012 0.019 0.012
H(10) 0.028 0.054 0.071 -0.027 0.002 0
H(5B) 0.076 0.019 0.081 0.006 -0.002 0.012
H(5A) 0.021 0.05 0.083 -0.008 0.01 -0.006
H(20B) 0.1 0.023 0.156 0.004 0.08 -0.019
H(19A) 0.084 0.041 0.051 -0.017 0.03 -0.021
H(8B) 0.075 0.018 0.088 0.016 0.039 0.013
H(20A) 0.03 0.119 0.077 -0.006 0.01 -0.023
H(19C) 0.157 0.042 0.072 0.026 0.021 0.018
H(19B) 0.059 0.046 0.142 -0.032 0.062 -0.028
H(20C) 0.111 0.132 0.027 0.063 0.027 0.021
H(1) 0.042 0.041 0.051 0.011 -0.008 0.004
H(16C) 0.059 0.064 0.149 -0.003 -0.042 0.042
H(16B) 0.085 0.085 0.25 -0.025 0.098 0.02
H(16A) 0.33 0.084 0.053 -0.047 -0.038 -0.018
H(9) 0.081 0.044 0.043 0.021 -0.018 -0.021
H(17A) 0.1 0.155 0.124 0.033 0.005 -0.08
H(17B) 0.085 0.055 0.42 -0.006 0.155 -0.024
H(17C) 0.175 0.201 0.083 0.159 0.05 0.05

#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.3037(6) 1_555 1_555 yes
O(2) C(1) 1.2268(6) 1_555 1_555 yes
O(5) N(2) 1.2246(4) 1_555 1_555 yes
O(3) N(1) 1.2238(4) 1_555 1_555 yes
O(6) N(2) 1.2209(4) 1_555 1_555 yes
O(4) N(1) 1.2259(4) 1_555 1_555 yes
O(9) C(8) 1.2998(6) 1_555 1_555 yes
O(10) C(8) 1.2283(6) 1_555 1_555 yes
O(8) N(3) 1.2262(5) 1_555 1_555 yes
O(7) N(3) 1.2270(4) 1_555 1_555 yes
O(12) N(4) 1.2232(8) 1_555 1_555 yes
O(11) N(4) 1.2230(5) 1_555 1_555 yes
O(14) C(18) 1.2691(5) 1_555 1_555 yes
O(13) C(15) 1.2657(6) 1_555 1_555 yes
N(2) C(2) 1.4688(4) 1_555 1_555 yes
N(3) C(9) 1.4689(4) 1_555 1_555 yes
N(4) C(11) 1.4689(5) 1_555 1_555 yes
N(7) C(18) 1.3403(5) 1_555 1_555 yes
N(7) C(20) 1.4594(5) 1_555 1_555 yes
N(7) C(19) 1.4484(5) 1_555 1_555 yes
N(8) C(18) 1.3455(5) 1_555 1_555 yes
N(8) H(8A) 1.0400(3) 1_555 1_555 yes
N(8) H(8B) 1.0040(3) 1_555 1_555 yes
N(5) C(15) 1.3487(6) 1_555 1_555 yes
N(5) H(5B) 1.0250(3) 1_555 1_555 yes
N(5) H(5A) 1.0080(3) 1_555 1_555 yes
N(6) C(15) 1.3404(5) 1_555 1_555 yes
N(6) C(16) 1.4528(6) 1_555 1_555 yes
N(6) C(17) 1.4550(6) 1_555 1_555 yes
C(6) C(5) 1.3970(4) 1_555 1_555 yes
C(6) C(1) 1.4986(5) 1_555 1_555 yes
C(6) C(7) 1.3945(5) 1_555 1_555 yes
C(4) C(5) 1.3897(4) 1_555 1_555 yes
C(4) C(3) 1.3898(4) 1_555 1_555 yes
C(5) H(5) 1.0900(3) 1_555 1_555 yes
C(3) C(2) 1.3873(4) 1_555 1_555 yes
C(3) H(3) 1.0950(3) 1_555 1_555 yes
C(2) C(7) 1.3873(4) 1_555 1_555 yes
C(7) H(7) 1.0790(3) 1_555 1_555 yes
C(14) C(9) 1.3871(5) 1_555 1_555 yes
C(14) C(13) 1.3947(5) 1_555 1_555 yes
C(14) H(14) 1.0840(4) 1_555 1_555 yes
C(12) C(13) 1.3944(5) 1_555 1_555 yes
C(12) C(11) 1.3865(5) 1_555 1_555 yes
C(12) H(12) 1.0930(3) 1_555 1_555 yes
C(8) C(13) 1.5005(5) 1_555 1_555 yes
C(9) C(10) 1.3873(5) 1_555 1_555 yes
C(10) C(11) 1.3902(5) 1_555 1_555 yes
C(10) H(10) 1.0980(4) 1_555 1_555 yes
C(20) H(20B) 1.0680(3) 1_555 1_555 yes
C(20) H(20A) 1.0680(4) 1_555 1_555 yes
C(20) H(20C) 1.0510(4) 1_555 1_555 yes
C(19) H(19A) 1.0900(4) 1_555 1_555 yes
C(19) H(19C) 1.0900(5) 1_555 1_555 yes
C(19) H(19B) 1.1000(5) 1_555 1_555 yes
C(16) H(16C) 1.0300(4) 1_555 1_555 yes
C(16) H(16B) 1.0400(4) 1_555 1_555 yes
C(16) H(16A) 1.0400(5) 1_555 1_555 yes
C(17) H(17A) 1.1200(5) 1_555 1_555 yes
C(17) H(17B) 0.9800(4) 1_555 1_555 yes
C(17) H(17C) 1.0000(4) 1_555 1_555 yes
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(5) N(2) O(6) 124.35(3) 1_555 1_555 1_555 yes
O(5) N(2) C(2) 117.90(3) 1_555 1_555 1_555 yes
O(6) N(2) C(2) 117.75(3) 1_555 1_555 1_555 yes
O(3) N(1) O(4) 124.20(3) 1_555 1_555 1_555 yes
O(8) N(3) O(7) 124.16(3) 1_555 1_555 1_555 yes
O(8) N(3) C(9) 118.17(3) 1_555 1_555 1_555 yes
O(7) N(3) C(9) 117.66(3) 1_555 1_555 1_555 yes
O(12) N(4) O(11) 124.58(5) 1_555 1_555 1_555 yes
O(12) N(4) C(11) 117.47(5) 1_555 1_555 1_555 yes
O(11) N(4) C(11) 117.95(3) 1_555 1_555 1_555 yes
C(18) N(7) C(20) 120.48(3) 1_555 1_555 1_555 yes
C(18) N(7) C(19) 121.77(3) 1_555 1_555 1_555 yes
C(20) N(7) C(19) 117.03(3) 1_555 1_555 1_555 yes
C(18) N(8) H(8A) 115.87(3) 1_555 1_555 1_555 yes
C(18) N(8) H(8B) 121.14(3) 1_555 1_555 1_555 yes
H(8A) N(8) H(8B) 122.23(4) 1_555 1_555 1_555 yes
C(15) N(5) H(5B) 121.84(3) 1_555 1_555 1_555 yes
C(15) N(5) H(5A) 116.62(3) 1_555 1_555 1_555 yes
H(5B) N(5) H(5A) 120.51(4) 1_555 1_555 1_555 yes
C(15) N(6) C(16) 122.91(4) 1_555 1_555 1_555 yes
C(15) N(6) C(17) 118.62(4) 1_555 1_555 1_555 yes
C(16) N(6) C(17) 118.45(4) 1_555 1_555 1_555 yes
C(5) C(6) C(1) 121.53(3) 1_555 1_555 1_555 yes
C(5) C(6) C(7) 120.30(3) 1_555 1_555 1_555 yes
C(1) C(6) C(7) 118.10(3) 1_555 1_555 1_555 yes
C(5) C(4) C(3) 123.13(3) 1_555 1_555 1_555 yes
C(6) C(5) C(4) 118.34(3) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 121.44(3) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 120.19(3) 1_555 1_555 1_555 yes
C(4) C(3) C(2) 116.51(3) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 120.74(3) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 122.74(3) 1_555 1_555 1_555 yes
N(2) C(2) C(3) 118.55(3) 1_555 1_555 1_555 yes
N(2) C(2) C(7) 118.59(3) 1_555 1_555 1_555 yes
C(3) C(2) C(7) 122.81(3) 1_555 1_555 1_555 yes
O(1) C(1) O(2) 124.65(4) 1_555 1_555 1_555 yes
O(1) C(1) C(6) 114.81(4) 1_555 1_555 1_555 yes
O(2) C(1) C(6) 120.52(3) 1_555 1_555 1_555 yes
C(6) C(7) C(2) 118.89(3) 1_555 1_555 1_555 yes
C(6) C(7) H(7) 120.24(3) 1_555 1_555 1_555 yes
C(2) C(7) H(7) 120.86(3) 1_555 1_555 1_555 yes
C(9) C(14) C(13) 118.74(4) 1_555 1_555 1_555 yes
C(9) C(14) H(14) 119.36(3) 1_555 1_555 1_555 yes
C(13) C(14) H(14) 121.90(4) 1_555 1_555 1_555 yes
C(13) C(12) C(11) 118.69(3) 1_555 1_555 1_555 yes
C(13) C(12) H(12) 120.71(3) 1_555 1_555 1_555 yes
C(11) C(12) H(12) 120.55(3) 1_555 1_555 1_555 yes
O(9) C(8) O(10) 125.26(4) 1_555 1_555 1_555 yes
O(9) C(8) C(13) 114.41(4) 1_555 1_555 1_555 yes
O(10) C(8) C(13) 120.33(3) 1_555 1_555 1_555 yes
N(3) C(9) C(14) 118.44(3) 1_555 1_555 1_555 yes
N(3) C(9) C(10) 118.52(3) 1_555 1_555 1_555 yes
C(14) C(9) C(10) 123.04(3) 1_555 1_555 1_555 yes
C(14) C(13) C(12) 120.16(3) 1_555 1_555 1_555 yes
C(14) C(13) C(8) 121.01(4) 1_555 1_555 1_555 yes
C(12) C(13) C(8) 118.81(3) 1_555 1_555 1_555 yes
C(9) C(10) C(11) 116.31(3) 1_555 1_555 1_555 yes
C(9) C(10) H(10) 121.48(3) 1_555 1_555 1_555 yes
C(11) C(10) H(10) 122.21(3) 1_555 1_555 1_555 yes
N(4) C(11) C(12) 118.41(3) 1_555 1_555 1_555 yes
N(4) C(11) C(10) 118.54(3) 1_555 1_555 1_555 yes
C(12) C(11) C(10) 123.05(3) 1_555 1_555 1_555 yes
O(14) C(18) N(7) 119.44(3) 1_555 1_555 1_555 yes
O(14) C(18) N(8) 120.34(3) 1_555 1_555 1_555 yes
N(7) C(18) N(8) 120.19(3) 1_555 1_555 1_555 yes
N(7) C(20) H(20B) 109.02(3) 1_555 1_555 1_555 yes
N(7) C(20) H(20A) 110.70(3) 1_555 1_555 1_555 yes
N(7) C(20) H(20C) 110.22(3) 1_555 1_555 1_555 yes
H(20B) C(20) H(20A) 108.66(3) 1_555 1_555 1_555 yes
H(20B) C(20) H(20C) 110.01(3) 1_555 1_555 1_555 yes
H(20A) C(20) H(20C) 108.22(3) 1_555 1_555 1_555 yes
N(7) C(19) H(19A) 111.93(3) 1_555 1_555 1_555 yes
N(7) C(19) H(19C) 112.73(4) 1_555 1_555 1_555 yes
N(7) C(19) H(19B) 107.81(4) 1_555 1_555 1_555 yes
H(19A) C(19) H(19C) 109.06(4) 1_555 1_555 1_555 yes
H(19A) C(19) H(19B) 107.56(4) 1_555 1_555 1_555 yes
H(19C) C(19) H(19B) 107.52(3) 1_555 1_555 1_555 yes
O(13) C(15) N(5) 120.38(3) 1_555 1_555 1_555 yes
O(13) C(15) N(6) 119.39(4) 1_555 1_555 1_555 yes
N(5) C(15) N(6) 120.23(4) 1_555 1_555 1_555 yes
N(6) C(16) H(16C) 111.64(4) 1_555 1_555 1_555 yes
N(6) C(16) H(16B) 111.03(4) 1_555 1_555 1_555 yes
N(6) C(16) H(16A) 113.00(4) 1_555 1_555 1_555 yes
H(16C) C(16) H(16B) 105.94(4) 1_555 1_555 1_555 yes
H(16C) C(16) H(16A) 105.93(4) 1_555 1_555 1_555 yes
H(16B) C(16) H(16A) 108.93(4) 1_555 1_555 1_555 yes
N(6) C(17) H(17A) 111.54(4) 1_555 1_555 1_555 yes
N(6) C(17) H(17B) 113.71(4) 1_555 1_555 1_555 yes
N(6) C(17) H(17C) 113.26(4) 1_555 1_555 1_555 yes
H(17A) C(17) H(17B) 105.63(4) 1_555 1_555 1_555 yes
H(17A) C(17) H(17C) 101.70(4) 1_555 1_555 1_555 yes
H(17B) C(17) H(17C) 110.08(4) 1_555 1_555 1_555 yes

#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(1) 6.053(18) 0 -0.054(10) -0.062(10) 0 -0.037(12) 0 0 -0.057(11) 0.036(11) 0
0.024(8) -0.021(7) 0 0 0.055(7) -0.012(7) 0.022(10) 0 0 -0.003(10) 0.002(10) 0
0 -0.005(8) 0.007(8) 1.001632 1.113461 1.113461 1.113461 1.113461 1.113461 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 6.118(19) 0 0 0 -0.022(11) 0.003(14) 0 0 -0.102(12) 0 -0.001(9) 0 0
0.035(8) 0 0 0 -0.033(11) 0 0 0.005(11) 0 0 0 0.001(10) 0 1.003017 1.109004
1.109004 1.109004 1.109004 1.109004 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(5) 6.107(7) 0 0 0 -0.046(5) -0.077(6) 0 0 -0.119(5) 0 0.062(4) 0 0 0.029(4) 0
0 0 0.027(5) 0 0 -0.003(4) 0 0 0 0.006(4) 0 1.000254 1.037783 1.037783 1.037783
1.037783 1.037783 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(3) 6.107 0 0 0 -0.0459 -0.0767 0 0 -0.1191 0 0.0618 0 0 0.0293 0 0 0 0.0267 0
0 -0.003 0 0 0 0.0063 0 1.000254 1.037783 1.037783 1.037783 1.037783 1.037783 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(6) 6.107 0 0 0 -0.0459 -0.0767 0 0 -0.1191 0 0.0618 0 0 0.0293 0 0 0 0.0267 0
0 -0.003 0 0 0 0.0063 0 1.000254 1.037783 1.037783 1.037783 1.037783 1.037783 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(4) 6.107 0 0 0 -0.0459 -0.0767 0 0 -0.1191 0 0.0618 0 0 0.0293 0 0 0 0.0267 0
0 -0.003 0 0 0 0.0063 0 1.000254 1.037783 1.037783 1.037783 1.037783 1.037783 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(9) 6.107(18) 0 -0.038(11) -0.009(10) 0 -0.023(13) 0 0 -0.043(11) 0.012(11) 0
0.033(8) -0.017(7) 0 0 0.058(7) 0.002(7) -0.018(11) 0 0 0.013(10) 0.013(10) 0 0
-0.005(9) 0.009(9) 1.001632 1.113461 1.113461 1.113461 1.113461 1.113461 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(10) 6.091(18) 0 0 0 -0.074(10) 0.007(12) 0 0 -0.086(12) 0 0.029(8) 0 0
0.047(8) 0 0 0 -0.004(10) 0 0 0.010(10) 0 0 0 0.011(9) 0 1.003017 1.109004
1.109004 1.109004 1.109004 1.109004 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(8) 6.107 0 0 0 -0.0459 -0.0767 0 0 -0.1191 0 0.0618 0 0 0.0293 0 0 0 0.0267 0
0 -0.003 0 0 0 0.0063 0 1.000254 1.037783 1.037783 1.037783 1.037783 1.037783 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(7) 6.107 0 0 0 -0.0459 -0.0767 0 0 -0.1191 0 0.0618 0 0 0.0293 0 0 0 0.0267 0
0 -0.003 0 0 0 0.0063 0 1.000254 1.037783 1.037783 1.037783 1.037783 1.037783 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(12) 6.107 0 0 0 -0.0459 -0.0767 0 0 -0.1191 0 0.0618 0 0 0.0293 0 0 0 0.0267
0 0 -0.003 0 0 0 0.0063 0 1.000254 1.037783 1.037783 1.037783 1.037783 1.037783
2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(11) 6.107 0 0 0 -0.0459 -0.0767 0 0 -0.1191 0 0.0618 0 0 0.0293 0 0 0 0.0267
0 0 -0.003 0 0 0 0.0063 0 1.000254 1.037783 1.037783 1.037783 1.037783 1.037783
2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(14) 6.114(16) 0 0 0 -0.063(9) -0.048(11) 0 0 -0.026(12) 0 -0.001(8) 0 0
0.060(8) 0 0 0 -0.003(10) 0 0 0.006(10) 0 0 0 0.027(9) 0 1.003017 1.109004
1.109004 1.109004 1.109004 1.109004 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(13) 6.052(17) 0 0 0 -0.095(11) -0.054(13) 0 0 -0.044(12) 0 -0.002(9) 0 0
0.051(8) 0 0 0 -0.007(11) 0 0 0.002(10) 0 0 0 0.023(9) 0 1.003017 1.109004
1.109004 1.109004 1.109004 1.109004 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
N(2) 4.952(11) 0 0 0 0.049(7) 0.100(6) 0 0 -0.163(7) 0 0.261(8) 0 0 0.178(8) 0
0 0 0.090(9) 0 0 0.028(8) 0 0 0 0.024(8) 0 0.998662 0.839998 0.839998 0.839998
0.839998 0.839998 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(1) 4.9515 0 0 0 0.0488 0.0998 0 0 -0.1628 0 0.2611 0 0 0.1778 0 0 0 0.09 0 0
0.0281 0 0 0 0.0236 0 0.998662 0.839998 0.839998 0.839998 0.839998 0.839998 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(3) 4.9515 0 0 0 0.0488 0.0998 0 0 -0.1628 0 0.2611 0 0 0.1778 0 0 0 0.09 0 0
0.0281 0 0 0 0.0236 0 0.998662 0.839998 0.839998 0.839998 0.839998 0.839998 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(4) 4.9515 0 0 0 0.0488 0.0998 0 0 -0.1628 0 0.2611 0 0 0.1778 0 0 0 0.09 0 0
0.0281 0 0 0 0.0236 0 0.998662 0.839998 0.839998 0.839998 0.839998 0.839998 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(7) 5.024(15) 0 0.005(8) -0.034(6) 0 0.005(8) 0 0 -0.010(7) -0.018(7) 0
0.015(7) 0.010(6) 0 0 0.128(6) 0.002(6) 0.054(9) 0 0 -0.003(8) 0.008(8) 0 0
-0.002(7) -0.020(7) 1.006078 1.094502 1.094502 1.094502 1.094502 1.094502 2
3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(8) 4.74(2) 0 0 0 0.046(9) -0.010(9) 0 0 -0.000(8) 0.008(7) 0.099(8) 0 0
0.129(7) 0.009(6) 0 0 -0.033(9) 0 0 -0.024(8) 0.000(8) 0 0 0.024(8) 0.014(7)
1.015331 1.041506 1.041506 1.041506 1.041506 1.041506 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
N(5) 4.7431 0 0 0 0.0462 -0.0096 0 0 -0.0001 0.0079 0.0987 0 0 0.129 0.0089 0 0
-0.033 0 0 -0.024 0.0002 0 0 0.0244 0.0141 1.015331 1.041506 1.041506 1.041506
1.041506 1.041506 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(6) 5.0244 0 0.0051 -0.0336 0 0.0048 0 0 -0.0102 -0.0181 0 0.0151 0.0096 0 0
0.1282 0.0019 0.054 0 0 -0.003 0.0078 0 0 -0.0022 -0.0199 1.006078 1.094502
1.094502 1.094502 1.094502 1.094502 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4
3.83936
C(6) 4.01(3) 0 -0.011(10) 0.036(12) 0 -0.171(11) 0 0 0.001(10) -0.002(11) 0
0.011(10) 0.016(10) 0 0 0.215(13) 0.002(10) 0.001(14) 0 0 0.009(12) 0.002(14) 0
0 0.023(13) 0.015(15) 1.014566 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(4) 3.981(16) 0 0 0 -0.155(8) -0.058(6) 0 0 -0.160(7) 0 0.218(7) 0 0 0.130(7)
0 0 0 -0.013(9) 0 0 -0.029(9) 0 0 0 0.007(8) 0 1.01374 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
C(5) 3.934(17) 0 -0.016(7) 0.025(8) 0 -0.212(7) 0 0 -0.012(7) -0.011(7) 0
0.022(6) 0.045(6) 0 0 0.239(7) -0.006(7) 0.029(8) 0 0 0.013(8) -0.028(8) 0 0
-0.020(8) -0.022(8) 1.02002 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(3) 3.926(19) 0 0 0 -0.006(10) 0.116(8) 0 0 -0.160(8) 0 -0.200(8) 0 0
-0.103(8) 0 0 0 0.054(11) 0 0 -0.010(10) 0 0 0 0.017(9) 0 1.019947 1 1 1 1 1 2
3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(2) 3.9807 0 0 0 -0.1548 -0.0577 0 0 -0.1602 0 0.2181 0 0 0.1302 0 0 0 -0.0125
0 0 -0.0294 0 0 0 0.0068 0 1.01374 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(1) 3.98(2) 0 0.054(14) 0.025(12) 0 -0.296(12) 0 0 0.084(13) -0.006(11) 0
0.018(12) -0.022(11) 0 0 0.338(14) 0.050(12) 0.029(15) 0 0 0.007(15) -0.012(13)
0 0 -0.056(18) 0.007(15) 1.015931 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(7) 3.9339 0 -0.0162 0.0246 0 -0.2117 0 0 -0.0121 -0.0108 0 0.0224 0.0451 0 0
0.2394 -0.0055 0.0289 0 0 0.0126 -0.0277 0 0 -0.02 -0.0219 1.02002 1 1 1 1 1 2
3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(14) 3.90(3) 0 -0.019(12) 0.031(12) 0 -0.243(11) 0 0 -0.039(11) -0.014(12) 0
0.002(10) 0.031(11) 0 0 0.243(12) -0.030(11) 0.028(14) 0 0 0.020(13) -0.036(13)
0 0 -0.005(14) 0.002(14) 1.02002 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(12) 3.9339 0 -0.0162 0.0246 0 -0.2117 0 0 -0.0121 -0.0108 0 0.0224 0.0451 0 0
0.2394 -0.0055 0.0289 0 0 0.0126 -0.0277 0 0 -0.02 -0.0219 1.02002 1 1 1 1 1 2
3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(8) 3.95(2) 0 0.063(13) 0.020(12) 0 -0.281(12) 0 0 0.079(13) -0.033(11) 0
0.009(12) -0.004(11) 0 0 0.308(14) 0.034(12) 0.052(15) 0 0 0.019(14) 0.004(14)
0 0 -0.022(18) 0.014(16) 1.015931 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762
4 3.1762
C(9) 3.9807 0 0 0 -0.1548 -0.0577 0 0 -0.1602 0 0.2181 0 0 0.1302 0 0 0 -0.0125
0 0 -0.0294 0 0 0 0.0068 0 1.01374 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(13) 3.99(3) 0 0.001(13) -0.011(14) 0 -0.149(11) 0 0 0.021(12) -0.004(12) 0
0.000(11) 0.004(11) 0 0 0.236(13) 0.031(13) 0.006(14) 0 0 -0.002(14) -0.021(14)
0 0 -0.016(16) -0.007(16) 1.014566 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(10) 3.9258 0 0 0 -0.0058 0.1163 0 0 -0.1597 0 -0.2004 0 0 -0.1034 0 0 0
0.0536 0 0 -0.0101 0 0 0 0.0173 0 1.019947 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762
3 3.1762 4 3.1762
C(11) 3.9807 0 0 0 -0.1548 -0.0577 0 0 -0.1602 0 0.2181 0 0 0.1302 0 0 0
-0.0125 0 0 -0.0294 0 0 0 0.0068 0 1.01374 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762
3 3.1762 4 3.1762
C(18) 3.93(2) 0 0.021(11) 0.025(11) 0 -0.273(11) 0 0 0.041(11) -0.009(10) 0
-0.044(11) 0.017(11) 0 0 0.371(12) -0.041(10) 0.016(14) 0 0 -0.024(13)
-0.003(13) 0 0 -0.061(15) -0.027(13) 1.016311 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(20) 3.72(2) 0 0 0 -0.017(6) -0.050(6) 0 0 0 0 0.244(7) 0 0 0 0 0 -0.131(6)
0.060(8) 0 0 0 0 0 0.053(7) 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(19) 3.7152 0 0 0 -0.0173 -0.0495 0 0 0 0 0.2444 0 0 0 0 0 -0.1313 0.0602 0 0
0 0 0 0.0531 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(15) 3.98(2) 0 0.045(12) 0.010(11) 0 -0.279(12) 0 0 0.079(12) -0.028(11) 0
-0.053(12) 0.026(11) 0 0 0.348(13) 0.000(10) 0.014(15) 0 0 -0.006(14)
-0.027(13) 0 0 -0.040(15) 0.014(14) 1.016311 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(16) 3.7152 0 0 0 -0.0173 -0.0495 0 0 0 0 0.2444 0 0 0 0 0 -0.1313 0.0602 0 0
0 0 0 0.0531 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(17) 3.7152 0 0 0 -0.0173 -0.0495 0 0 0 0 0.2444 0 0 0 0 0 -0.1313 0.0602 0 0
0 0 0 0.0531 0 0 1.009611 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
H(5) 0.999(9) 0 0 0 0.166(6) 0.103(8) 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0
0 0 0 0 1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(7) 0.9992 0 0 0 0.1659 0.1026 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0 0 0 0
0 1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(12) 0.9992 0 0 0 0.1659 0.1026 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0 0 0
0 0 1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.9992 0 0 0 0.1659 0.1026 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0 0 0 0
0 1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(14) 0.9992 0 0 0 0.1659 0.1026 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0 0 0
0 0 1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(8A) 1.044(10) 0 0 0 0.227(7) 0.191(9) 0 0 0 0 0.0151 0 0 0 0 0 0 -0.0083 0 0
0 0 0 0 0 0 1.110704 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10) 0.9992 0 0 0 0.1659 0.1026 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0 0 0
0 0 1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5B) 1.0441 0 0 0 0.2267 0.1906 0 0 0 0 0.0151 0 0 0 0 0 0 -0.0083 0 0 0 0 0 0
0 0 1.110704 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5A) 1.0441 0 0 0 0.2267 0.1906 0 0 0 0 0.0151 0 0 0 0 0 0 -0.0083 0 0 0 0 0 0
0 0 1.110704 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(20B) 1.107(8) 0 0 0 0.184(5) 0.145(7) 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0
0 0 0 0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(19A) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(8B) 1.0441 0 0 0 0.2267 0.1906 0 0 0 0 0.0151 0 0 0 0 0 0 -0.0083 0 0 0 0 0 0
0 0 1.110704 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(20A) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(19C) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(19B) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(20C) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(1) 0.831(15) 0 0 0 0.090(13) 0.19(2) 0 0 0 0 0.0171 0 0 0 0 0 0 -0.0278 0 0 0
0 0 0 0 0 1.119673 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16C) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16B) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16A) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9) 0.820(16) 0 0 0 0.055(15) 0.12(2) 0 0 0 0 0.0171 0 0 0 0 0 0 -0.0278 0 0 0
0 0 0 0 0 1.119673 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17A) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17B) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(17C) 1.1065 0 0 0 0.1843 0.1445 0 0 0 0 0.0313 0 0 0 0 0 0 0.017 0 0 0 0 0 0
0 0 1.112822 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(1) X O(1) H(1) Y
O(2) C(1) Z O(2) O(1) Y
O(5) N(2) Z O(5) O(6) Y
O(3) N(1) Z O(3) O(4) Y
O(6) N(2) Z O(6) O(5) Y
O(4) N(1) Z O(4) O(3) Y
O(9) C(8) X O(9) H(9) Y
O(10) C(8) Z O(10) O(9) Y
O(8) N(3) Z O(8) O(7) Y
O(7) N(3) Z O(7) O(8) Y
O(12) N(4) Z O(12) O(11) Y
O(11) N(4) Z O(11) O(12) Y
O(14) C(18) Z O(14) N(7) Y
O(13) C(15) Z O(13) N(6) Y
N(2) C(2) Z N(2) O(6) Y
N(1) C(4) Z N(1) O(3) Y
N(3) C(9) Z N(3) O(8) Y
N(4) C(11) Z N(4) O(11) Y
N(7) C(18) X N(7) C(19) Y
N(8) C(18) Z N(8) H(8B) Y
N(5) C(15) Z N(5) H(5A) Y
N(6) C(15) X N(6) C(16) Y
C(6) C(7) X C(6) C(5) Y
C(4) N(1) Z C(4) C(5) Y
C(5) C(4) X C(5) C(6) Y
C(3) DUM1 Z C(3) C(2) Y
C(2) N(2) Z C(2) C(7) Y
C(1) O(2) X C(1) O(1) Y
C(7) C(2) X C(7) C(6) Y
C(14) C(9) X C(14) C(13) Y
C(12) C(11) X C(12) C(13) Y
C(8) O(10) X C(8) O(9) Y
C(9) N(3) Z C(9) C(10) Y
C(13) C(12) X C(13) C(14) Y
C(10) DUM2 Z C(10) C(9) Y
C(11) N(4) Z C(11) C(12) Y
C(18) O(14) X C(18) N(7) Y
C(20) N(7) Z C(20) H(20B) Y
C(19) N(7) Z C(19) H(19A) Y
C(15) O(13) X C(15) N(6) Y
C(16) N(6) Z C(16) H(16C) Y
C(17) N(6) Z C(17) H(17C) Y
H(5) C(5) Z H(5) C(4) Y
H(7) C(7) Z H(7) C(2) Y
H(12) C(12) Z H(12) C(11) Y
H(3) C(3) Z H(3) C(2) Y
H(14) C(14) Z H(14) C(9) Y
H(8A) N(8) Z H(8A) H(8B) Y
H(10) C(10) Z H(10) C(9) Y
H(5B) N(5) Z H(5B) H(5A) Y
H(5A) N(5) Z H(5A) H(5B) Y
H(20B) C(20) Z H(20B) N(7) Y
H(19A) C(19) Z H(19A) N(7) Y
H(8B) N(8) Z H(8B) H(8A) Y
H(20A) C(20) Z H(20A) N(7) Y
H(19C) C(19) Z H(19C) N(7) Y
H(19B) C(19) Z H(19B) N(7) Y
H(20C) C(20) Z H(20C) N(7) Y
H(1) O(1) Z H(1) C(1) Y
H(16C) C(16) Z H(16C) N(6) Y
H(16B) C(16) Z H(16B) N(6) Y
H(16A) C(16) Z H(16A) N(6) Y
H(9) O(9) Z H(9) C(8) Y
H(17A) C(17) Z H(17A) N(6) Y
H(17B) C(17) Z H(17B) N(6) Y
H(17C) C(17) Z H(17C) N(6) Y



#----------------------------------------------------------------------------#
#                   STRUCTURE FACTOR INFORMATION                             #
#----------------------------------------------------------------------------#

#
#  Unique observations used in XD refinement
#  F^2(calc) includes anomalous dispersion and is corrected for extinction
#  if the latter is included in the model.
#
#


