# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_daniel_05jan18_monopartial_a
_database_code_depnum_ccdc_archive 'CCDC 1856989'
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H9 N3 O3)'
_chemical_formula_sum            'C18 H18 N6 O6'
_chemical_formula_weight         414.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.595(7)
_cell_length_b                   4.645(4)
_cell_length_c                   22.624(18)
_cell_angle_alpha                90
_cell_angle_beta                 91.293(18)
_cell_angle_gamma                90
_cell_volume                     903.1(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    194
_cell_measurement_temperature    149.61
_cell_measurement_theta_max      16.378
_cell_measurement_theta_min      2.554
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.3836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1709 before and 0.0889 after correction. The Ratio of minimum to maximum transmission is 0.5147. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.017
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2808
_diffrn_reflns_av_unetI/netI     0.2569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8737
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.907
_diffrn_reflns_theta_min         1.801
_diffrn_ambient_temperature      149.61
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                718
_reflns_number_total             1735
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2360
_refine_ls_R_factor_gt           0.0936
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.2091
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C4(H4)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O2 O 0.4543(4) 1.1057(8) 0.34127(15) 0.0287(11) Uani 1 1 d . . . . .
O1 O -0.0753(4) 0.8946(8) 0.29403(16) 0.0290(11) Uani 1 1 d . . . . .
O3 O 0.3536(5) 0.3160(9) 0.50450(17) 0.0398(13) Uani 1 1 d . . . . .
N1 N 0.1388(5) 0.3917(10) 0.4455(2) 0.0242(12) Uani 1 1 d . . . . .
N3 N -0.0655(6) 0.4763(10) 0.3894(2) 0.0277(13) Uani 1 1 d . . . . .
N2 N -0.0161(6) 0.3179(10) 0.4332(2) 0.0290(13) Uani 1 1 d . . . . .
C7 C -0.0716(7) 1.1130(13) 0.2484(2) 0.0323(16) Uani 1 1 d . . . . .
H7A H 0.001805 1.055524 0.218063 0.049 Uiso 1 1 calc GR . . . .
H7B H -0.038468 1.296663 0.265864 0.049 Uiso 1 1 calc GR . . . .
H7C H -0.175768 1.134478 0.230405 0.049 Uiso 1 1 calc GR . . . .
C2 C 0.1980(7) 1.0001(12) 0.3179(2) 0.0232(14) Uani 1 1 d . . . . .
H2 H 0.205663 1.139153 0.287357 0.028 Uiso 1 1 calc R . . . .
C1 C 0.0589(7) 0.8567(12) 0.3257(2) 0.0232(14) Uani 1 1 d . . . . .
C3 C 0.3290(7) 0.9417(12) 0.3551(2) 0.0214(14) Uani 1 1 d . . . . .
C9 C 0.2203(8) 0.2554(13) 0.4920(3) 0.0341(17) Uani 1 1 d . . . . .
H9 H 0.169234 0.111548 0.514219 0.041 Uiso 1 1 calc R . . . .
C4 C 0.3291(6) 0.7435(12) 0.4005(2) 0.0227(14) Uani 1 1 d . . . . .
H4 H 0.417939 0.705435 0.424974 0.027 Uiso 1 1 calc R . . . .
C8 C 0.5930(6) 1.0811(12) 0.3786(3) 0.0319(16) Uani 1 1 d . . . . .
H8A H 0.670504 1.221588 0.365934 0.048 Uiso 1 1 calc GR . . . .
H8B H 0.635750 0.886390 0.375243 0.048 Uiso 1 1 calc GR . . . .
H8C H 0.566370 1.118690 0.419749 0.048 Uiso 1 1 calc GR . . . .
C6 C 0.0558(6) 0.6547(11) 0.3715(2) 0.0192(14) Uani 1 1 d . . . . .
C5 C 0.1874(6) 0.6046(12) 0.4070(2) 0.0210(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C3 1.361(6) . ?
O2 C8 1.449(6) . ?
O1 C7 1.448(6) . ?
O1 C1 1.356(6) . ?
O3 C9 1.208(7) . ?
N1 N2 1.396(6) . ?
N1 C9 1.401(7) . ?
N1 C5 1.388(7) . ?
N3 N2 1.298(6) . ?
N3 C6 1.400(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C1 1.383(8) . ?
C2 C3 1.416(7) . ?
C1 C6 1.398(7) . ?
C3 C4 1.379(7) . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.390(7) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 C5 1.392(7) . ?

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
C3 O2 C8 117.8(4) . . ?
C1 O1 C7 115.9(4) . . ?
N2 N1 C9 119.8(5) . . ?
C5 N1 N2 110.5(5) . . ?
C5 N1 C9 129.8(5) . . ?
N2 N3 C6 108.9(5) . . ?
N3 N2 N1 107.9(4) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.7(5) . . ?
C3 C2 H2 119.7 . . ?
O1 C1 C2 126.7(5) . . ?
O1 C1 C6 116.7(5) . . ?
C2 C1 C6 116.7(5) . . ?
O2 C3 C2 112.3(5) . . ?
O2 C3 C4 123.9(5) . . ?
C4 C3 C2 123.8(5) . . ?
O3 C9 N1 121.8(6) . . ?
O3 C9 H9 119.1 . . ?
N1 C9 H9 119.1 . . ?
C3 C4 H4 123.1 . . ?
C3 C4 C5 113.8(5) . . ?
C5 C4 H4 123.1 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C6 N3 129.7(5) . . ?
C5 C6 N3 109.5(5) . . ?
C5 C6 C1 120.7(5) . . ?
N1 C5 C4 132.5(5) . . ?
N1 C5 C6 103.3(5) . . ?
C4 C5 C6 124.3(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_RINTA01_daniel_05jan18_monopartial_a 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: crystals were very thin and diffracted very weakly at higher angles.
;
_vrf_PLAT020_daniel_05jan18_monopartial_a 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.281 Report
RESPONSE: same as above
;
####################################################################### 
# 
# 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_daniel_cf3_03jan18_0m_a_pl
_database_code_depnum_ccdc_archive 'CCDC 1856993'
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H9 N3 O2'
_chemical_formula_sum            'C8 H9 N3 O2'
_chemical_formula_weight         179.18
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.5266(18)
_cell_length_b                   10.2411(14)
_cell_length_c                   13.4172(17)
_cell_angle_alpha                90
_cell_angle_beta                 116.838(4)
_cell_angle_gamma                90
_cell_volume                     1658.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4055
_cell_measurement_temperature    149.15
_cell_measurement_theta_max      26.459
_cell_measurement_theta_min      2.608
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0907 before and 0.0590 after correction. The Ratio of minimum to maximum transmission is 0.9029. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11936
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.608
_diffrn_ambient_temperature      149.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1315
_reflns_number_total             1900
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+1.1023P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1360
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C4(H4)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O 0.02523(11) 0.44748(13) 0.13612(12) 0.0372(4) Uani 1 1 d . . . . .
O2 O -0.14352(11) 0.02685(13) 0.05208(12) 0.0385(4) Uani 1 1 d . . . . .
N1 N 0.25662(14) 0.10755(16) 0.25184(14) 0.0332(4) Uani 1 1 d . . . . .
H1 H 0.290186 0.031294 0.268575 0.040 Uiso 1 1 calc R . . . .
N3 N 0.23518(13) 0.31575(16) 0.24107(14) 0.0339(4) Uani 1 1 d . . . . .
N2 N 0.30960(13) 0.22394(17) 0.27867(14) 0.0378(4) Uani 1 1 d . . . . .
C8 C -0.13556(18) -0.1112(2) 0.06498(18) 0.0400(5) Uani 1 1 d . . . . .
H8A H -0.209816 -0.149680 0.027687 0.060 Uiso 1 1 calc GR . . . .
H8B H -0.101518 -0.133204 0.144636 0.060 Uiso 1 1 calc GR . . . .
H8C H -0.089872 -0.145934 0.031521 0.060 Uiso 1 1 calc GR . . . .
C2 C -0.06195(15) 0.23209(19) 0.09065(15) 0.0297(4) Uani 1 1 d . . . . .
H2 H -0.134730 0.266989 0.053323 0.036 Uiso 1 1 calc R . . . .
C1 C 0.02703(16) 0.31424(18) 0.13564(15) 0.0286(4) Uani 1 1 d . . . . .
C6 C 0.13328(14) 0.25782(19) 0.18961(14) 0.0274(4) Uani 1 1 d . . . . .
C4 C 0.05607(16) 0.03615(19) 0.15074(15) 0.0295(4) Uani 1 1 d . . . . .
H4 H 0.065463 -0.055949 0.155218 0.035 Uiso 1 1 calc R . . . .
C7 C -0.08116(19) 0.5090(2) 0.0855(2) 0.0437(5) Uani 1 1 d . . . . .
H7A H -0.120108 0.484127 0.006587 0.065 Uiso 1 1 calc GR . . . .
H7B H -0.071812 0.604000 0.091555 0.065 Uiso 1 1 calc GR . . . .
H7C H -0.124440 0.480912 0.123801 0.065 Uiso 1 1 calc GR . . . .
C5 C 0.14545(15) 0.12335(18) 0.19599(14) 0.0269(4) Uani 1 1 d . . . . .
C3 C -0.04610(15) 0.09463(18) 0.09944(15) 0.0286(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.365(2) . ?
O1 C7 1.430(2) . ?
O2 C8 1.423(2) . ?
O2 C3 1.366(2) . ?
N1 N2 1.353(2) . ?
N1 C5 1.353(2) . ?
N3 N2 1.301(2) . ?
N3 C6 1.367(2) . ?
C2 C1 1.366(3) . ?
C2 C3 1.421(3) . ?
C1 C6 1.409(2) . ?
C6 C5 1.385(3) . ?
C4 C5 1.402(3) . ?
C4 C3 1.372(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 117.01(16) . . ?
C3 O2 C8 116.38(16) . . ?
N2 N1 C5 111.38(16) . . ?
N2 N3 C6 108.02(16) . . ?
N3 N2 N1 108.02(15) . . ?
C1 C2 C3 120.25(17) . . ?
O1 C1 C2 127.15(18) . . ?
O1 C1 C6 115.08(17) . . ?
C2 C1 C6 117.76(17) . . ?
N3 C6 C1 130.07(18) . . ?
N3 C6 C5 109.62(16) . . ?
C5 C6 C1 120.32(17) . . ?
C3 C4 C5 114.55(17) . . ?
N1 C5 C6 102.97(16) . . ?
N1 C5 C4 133.56(18) . . ?
C6 C5 C4 123.47(17) . . ?
O2 C3 C2 112.77(17) . . ?
O2 C3 C4 123.58(17) . . ?
C4 C3 C2 123.65(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C6 N3 -1.1(3) . . . . ?
O1 C1 C6 C5 179.01(15) . . . . ?
N3 C6 C5 N1 -0.25(19) . . . . ?
N3 C6 C5 C4 -179.88(15) . . . . ?
N2 N1 C5 C6 0.29(19) . . . . ?
N2 N1 C5 C4 179.86(19) . . . . ?
N2 N3 C6 C1 -179.79(17) . . . . ?
N2 N3 C6 C5 0.1(2) . . . . ?
C8 O2 C3 C2 -175.18(16) . . . . ?
C8 O2 C3 C4 4.4(3) . . . . ?
C2 C1 C6 N3 179.91(17) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C1 C2 C3 O2 178.77(15) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C6 C5 N1 179.68(15) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C6 N3 N2 N1 0.06(19) . . . . ?
C7 O1 C1 C2 0.9(3) . . . . ?
C7 O1 C1 C6 -177.95(16) . . . . ?
C5 N1 N2 N3 -0.2(2) . . . . ?
C5 C4 C3 O2 -178.72(16) . . . . ?
C5 C4 C3 C2 0.8(3) . . . . ?
C3 C2 C1 O1 -178.53(17) . . . . ?
C3 C2 C1 C6 0.3(3) . . . . ?
C3 C4 C5 N1 -179.92(18) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_daniel_oh_07feb18_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1856991'
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H7 N3 O3)'
_chemical_formula_sum            'C16 H14 N6 O6'
_chemical_formula_weight         386.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0180(7)
_cell_length_b                   7.3930(9)
_cell_length_c                   9.3115(10)
_cell_angle_alpha                77.213(7)
_cell_angle_beta                 82.358(7)
_cell_angle_gamma                86.071(8)
_cell_volume                     400.09(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1371
_cell_measurement_temperature    149.61
_cell_measurement_theta_max      26.137
_cell_measurement_theta_min      3.219
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1449 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.6381. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7324
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.684
_diffrn_reflns_theta_min         2.259
_diffrn_ambient_temperature      149.61
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1142
_reflns_number_total             1852
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1852
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.1266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1450
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C4(H4)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O 0.0662(3) 0.8658(3) 0.73995(19) 0.0268(5) Uani 1 1 d . . . . .
H1 H 0.000743 0.924346 0.668359 0.040 Uiso 1 1 calc GR . . . .
O2 O 0.7130(3) 0.4967(3) 0.84814(19) 0.0281(5) Uani 1 1 d . . . . .
H2 H 0.830957 0.449592 0.809892 0.042 Uiso 1 1 calc GR . . . .
O3 O 0.9107(3) 0.6568(3) 0.2833(2) 0.0268(5) Uani 1 1 d . . . . .
N3 N 0.2498(3) 0.9063(3) 0.4116(2) 0.0197(5) Uani 1 1 d . . . . .
N1 N 0.5734(3) 0.7883(3) 0.3397(2) 0.0183(5) Uani 1 1 d . . . . .
N2 N 0.3845(4) 0.8934(3) 0.2939(2) 0.0224(6) Uani 1 1 d . . . . .
C8 C 0.7306(5) 0.8278(4) 0.0766(3) 0.0278(7) Uani 1 1 d . . . . .
H8A H 0.864537 0.791819 0.015419 0.042 Uiso 1 1 calc GR . . . .
H8B H 0.715306 0.963499 0.059383 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.597660 0.779456 0.050023 0.042 Uiso 1 1 calc GR . . . .
C7 C 0.7524(4) 0.7502(4) 0.2355(3) 0.0201(6) Uani 1 1 d . . . . .
C3 C 0.6005(4) 0.6019(4) 0.7388(3) 0.0205(6) Uani 1 1 d . . . . .
C1 C 0.2607(4) 0.7882(3) 0.6880(3) 0.0185(6) Uani 1 1 d . . . . .
C2 C 0.3927(4) 0.6805(3) 0.7870(3) 0.0209(6) Uani 1 1 d . . . . .
H2A H 0.341923 0.659004 0.890185 0.025 Uiso 1 1 calc R . . . .
C4 C 0.6890(4) 0.6277(3) 0.5906(3) 0.0202(6) Uani 1 1 d . . . . .
H4 H 0.831668 0.577123 0.558687 0.024 Uiso 1 1 calc R . . . .
C6 C 0.3425(4) 0.8121(3) 0.5372(3) 0.0182(6) Uani 1 1 d . . . . .
C5 C 0.5504(4) 0.7340(3) 0.4928(3) 0.0177(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.347(3) . ?
O2 C3 1.364(3) . ?
O3 C7 1.213(3) . ?
N3 N2 1.291(3) . ?
N3 C6 1.387(3) . ?
N1 N2 1.393(3) . ?
N1 C7 1.408(3) . ?
N1 C5 1.383(3) . ?
C8 C7 1.483(3) . ?
C3 C2 1.403(3) . ?
C3 C4 1.388(4) . ?
C1 C2 1.377(3) . ?
C1 C6 1.401(4) . ?
C4 C5 1.392(3) . ?
C6 C5 1.392(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
N2 N3 C6 110.1(2) . . ?
N2 N1 C7 120.83(19) . . ?
C5 N1 N2 110.12(19) . . ?
C5 N1 C7 129.0(2) . . ?
N3 N2 N1 107.41(19) . . ?
O3 C7 N1 117.2(2) . . ?
O3 C7 C8 125.7(2) . . ?
N1 C7 C8 117.1(2) . . ?
O2 C3 C2 115.5(2) . . ?
O2 C3 C4 121.3(2) . . ?
C4 C3 C2 123.2(2) . . ?
O1 C1 C2 119.2(2) . . ?
O1 C1 C6 124.1(2) . . ?
C2 C1 C6 116.7(2) . . ?
C1 C2 C3 121.4(2) . . ?
C3 C4 C5 114.1(2) . . ?
N3 C6 C1 130.9(2) . . ?
N3 C6 C5 108.5(2) . . ?
C5 C6 C1 120.6(2) . . ?
N1 C5 C4 132.3(2) . . ?
N1 C5 C6 103.8(2) . . ?
C4 C5 C6 123.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_daniel_withoutome_15may18_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1856994'
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C8 H7 N3 O)'
_chemical_formula_sum            'C16 H14 N6 O2'
_chemical_formula_weight         322.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3151(3)
_cell_length_b                   4.9197(2)
_cell_length_c                   16.7332(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.3560(10)
_cell_angle_gamma                90
_cell_volume                     763.49(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9659
_cell_measurement_temperature    150.02
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      4.319
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1059 before and 0.0490 after correction. The Ratio of minimum to maximum transmission is 0.9046. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.535
_exptl_crystal_size_mid          0.361
_exptl_crystal_size_min          0.167
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15481
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         4.690
_diffrn_ambient_temperature      150.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1590
_reflns_number_total             1710
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0406P)²+0.3022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00B(H00D), C00C(H00E)
2.b Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O001 O 0.60779(9) 0.30647(18) 0.43778(5) 0.0360(2) Uani 1 1 d . . . . .
N002 N 0.43255(10) 0.51110(18) 0.35774(5) 0.0242(2) Uani 1 1 d . . . . .
N003 N 0.25551(10) 0.6799(2) 0.27939(6) 0.0293(2) Uani 1 1 d . . . . .
N004 N 0.39216(10) 0.69834(19) 0.29783(6) 0.0282(2) Uani 1 1 d . . . . .
C005 C 0.31277(11) 0.3693(2) 0.37673(6) 0.0233(2) Uani 1 1 d . . . . .
C006 C 0.19999(12) 0.4798(2) 0.32639(6) 0.0254(3) Uani 1 1 d . . . . .
C007 C 0.29114(13) 0.1608(2) 0.43089(6) 0.0276(3) Uani 1 1 d . . . . .
H007 H 0.368211 0.085151 0.464947 0.033 Uiso 1 1 calc R . . . .
C008 C 0.57802(12) 0.4815(2) 0.38858(7) 0.0260(2) Uani 1 1 d . . . . .
C009 C 0.15079(13) 0.0713(3) 0.43193(7) 0.0331(3) Uani 1 1 d . . . . .
H009 H 0.130884 -0.070521 0.467814 0.040 Uiso 1 1 calc R . . . .
C00A C 0.68234(12) 0.6739(2) 0.35677(7) 0.0304(3) Uani 1 1 d . . . . .
H00A H 0.777708 0.648609 0.385818 0.046 Uiso 1 1 calc GR . . . .
H00B H 0.649909 0.861037 0.364059 0.046 Uiso 1 1 calc GR . . . .
H00C H 0.688012 0.638667 0.299508 0.046 Uiso 1 1 calc GR . . . .
C00B C 0.05856(12) 0.3877(3) 0.32817(7) 0.0316(3) Uani 1 1 d . . . . .
H00D H -0.018652 0.462861 0.294094 0.038 Uiso 1 1 calc R . . . .
C00C C 0.03633(13) 0.1829(3) 0.38165(7) 0.0354(3) Uani 1 1 d . . . . .
H00E H -0.058535 0.115311 0.384694 0.042 Uiso 1 1 calc R . . . .


_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
O001 C008 1.2058(14) . ?
N002 N004 1.3873(12) . ?
N002 C005 1.3781(13) . ?
N002 C008 1.4117(14) . ?
N003 N004 1.2847(14) . ?
N003 C006 1.3896(14) . ?
C005 C006 1.3943(15) . ?
C005 C007 1.3956(15) . ?
C006 C00B 1.3962(15) . ?
C007 H007 0.9500 . ?
C007 C009 1.3812(16) . ?
C008 C00A 1.4899(15) . ?
C009 H009 0.9500 . ?
C009 C00C 1.4066(18) . ?
C00A H00A 0.9800 . ?
C00A H00B 0.9800 . ?
C00A H00C 0.9800 . ?
C00B H00D 0.9500 . ?
C00B C00C 1.3761(18) . ?
C00C H00E 0.9500 . ?

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
N004 N002 C008 121.25(9) . . ?
C005 N002 N004 109.39(9) . . ?
C005 N002 C008 129.33(9) . . ?
N004 N003 C006 109.08(9) . . ?
N003 N004 N002 108.82(9) . . ?
N002 C005 C006 104.11(9) . . ?
N002 C005 C007 133.70(10) . . ?
C006 C005 C007 122.18(10) . . ?
N003 C006 C005 108.60(9) . . ?
N003 C006 C00B 130.08(10) . . ?
C005 C006 C00B 121.32(10) . . ?
C005 C007 H007 122.1 . . ?
C009 C007 C005 115.90(10) . . ?
C009 C007 H007 122.1 . . ?
O001 C008 N002 118.35(10) . . ?
O001 C008 C00A 125.56(10) . . ?
N002 C008 C00A 116.09(9) . . ?
C007 C009 H009 118.9 . . ?
C007 C009 C00C 122.24(11) . . ?
C00C C009 H009 118.9 . . ?
C008 C00A H00A 109.5 . . ?
C008 C00A H00B 109.5 . . ?
C008 C00A H00C 109.5 . . ?
H00A C00A H00B 109.5 . . ?
H00A C00A H00C 109.5 . . ?
H00B C00A H00C 109.5 . . ?
C006 C00B H00D 121.6 . . ?
C00C C00B C006 116.81(11) . . ?
C00C C00B H00D 121.6 . . ?
C009 C00C H00E 119.2 . . ?
C00B C00C C009 121.55(11) . . ?
C00B C00C H00E 119.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_daniel_cl_20feb18_partial_a
_database_code_depnum_ccdc_archive 'CCDC 1856990'
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 Cl N3 O3'
_chemical_formula_sum            'C10 H10 Cl N3 O3'
_chemical_formula_weight         255.66
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   4.669(5)
_cell_length_b                   8.554(8)
_cell_length_c                   28.15(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1124(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3962
_cell_measurement_temperature    149.59
_cell_measurement_theta_max      26.416
_cell_measurement_theta_min      2.485
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.794
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1767 before and 0.0999 after correction. The Ratio of minimum to maximum transmission is 0.5845. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.091
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_unetI/netI     0.1005
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            11920
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         2.489
_diffrn_ambient_temperature      149.59
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                1834
_reflns_number_total             2523
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.714
_refine_diff_density_rms         0.134
_refine_ls_abs_structure_details 
;
 Flack x determined using 540 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0667P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1478
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.9247(4) 0.64204(17) 0.23029(6) 0.0590(5) Uani 1 1 d . . . . .
O1 O -0.1078(7) 0.4166(3) 0.46749(12) 0.0334(8) Uani 1 1 d . . . . .
O2 O -0.2798(7) 0.9428(3) 0.42043(12) 0.0303(8) Uani 1 1 d . . . . .
O3 O 0.5225(7) 0.7947(4) 0.29676(12) 0.0362(8) Uani 1 1 d . . . . .
N3 N 0.3012(8) 0.3939(4) 0.39012(15) 0.0286(9) Uani 1 1 d . . . . .
N1 N 0.4061(8) 0.5858(4) 0.34201(13) 0.0262(8) Uani 1 1 d . . . . .
N2 N 0.4602(8) 0.4301(4) 0.35435(15) 0.0314(9) Uani 1 1 d . . . . .
C9 C 0.5528(9) 0.6572(5) 0.30364(15) 0.0262(9) Uani 1 1 d . . . . .
C2 C -0.1930(9) 0.6864(5) 0.44393(17) 0.0264(10) Uani 1 1 d . . . . .
H2 H -0.327828 0.703723 0.468665 0.032 Uiso 1 1 calc R . . . .
C8 C -0.2434(11) 1.0734(5) 0.3884(2) 0.0384(13) Uani 1 1 d . . . . .
H8A H -0.283811 1.039681 0.355813 0.058 Uiso 1 1 calc GR . . . .
H8B H -0.045970 1.111760 0.390403 0.058 Uiso 1 1 calc GR . . . .
H8C H -0.375774 1.157409 0.397286 0.058 Uiso 1 1 calc GR . . . .
C5 C 0.2029(8) 0.6479(5) 0.37280(16) 0.0231(9) Uani 1 1 d . . . . .
C1 C -0.0649(10) 0.5427(5) 0.43968(17) 0.0263(10) Uani 1 1 d . . . . .
C4 C 0.0738(9) 0.7963(4) 0.37551(16) 0.0257(9) Uani 1 1 d . . . . .
H4 H 0.119656 0.879466 0.354472 0.031 Uiso 1 1 calc R . . . .
C6 C 0.1414(9) 0.5259(5) 0.40278(17) 0.0238(9) Uani 1 1 d . . . . .
C10 C 0.7340(10) 0.5452(6) 0.27560(18) 0.0330(11) Uani 1 1 d . . . . .
H10A H 0.609798 0.464014 0.261300 0.040 Uiso 1 1 calc R . . . .
H10B H 0.870887 0.492550 0.297183 0.040 Uiso 1 1 calc R . . . .
C3 C -0.1270(8) 0.8103(4) 0.41179(17) 0.0231(9) Uani 1 1 d . . . . .
C7 C -0.3142(10) 0.4341(5) 0.50587(18) 0.0325(11) Uani 1 1 d . . . . .
H7A H -0.502136 0.460523 0.492580 0.049 Uiso 1 1 calc GR . . . .
H7B H -0.251547 0.517840 0.527244 0.049 Uiso 1 1 calc GR . . . .
H7C H -0.328020 0.335865 0.523617 0.049 Uiso 1 1 calc GR . . . .


_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
Cl1 C10 1.762(5) . ?
O1 C1 1.348(5) . ?
O1 C7 1.455(6) . ?
O2 C8 1.445(6) . ?
O2 C3 1.362(5) . ?
O3 C9 1.200(5) . ?
N3 N2 1.289(6) . ?
N3 C6 1.399(5) . ?
N1 N2 1.400(5) . ?
N1 C9 1.417(6) . ?
N1 C5 1.390(6) . ?
C9 C10 1.502(6) . ?
C2 H2 0.9500 . ?
C2 C1 1.373(6) . ?
C2 C3 1.427(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 C4 1.407(6) . ?
C5 C6 1.373(6) . ?
C1 C6 1.423(6) . ?
C4 H4 0.9500 . ?
C4 C3 1.391(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 116.5(3) . . ?
C3 O2 C8 118.1(3) . . ?
N2 N3 C6 108.2(4) . . ?
N2 N1 C9 120.8(4) . . ?
C5 N1 N2 109.4(4) . . ?
C5 N1 C9 129.8(4) . . ?
N3 N2 N1 108.6(3) . . ?
O3 C9 N1 119.2(4) . . ?
O3 C9 C10 127.4(4) . . ?
N1 C9 C10 113.4(4) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C5 C4 132.1(4) . . ?
C6 C5 N1 103.6(4) . . ?
C6 C5 C4 124.3(4) . . ?
O1 C1 C2 127.0(4) . . ?
O1 C1 C6 116.3(4) . . ?
C2 C1 C6 116.7(4) . . ?
C5 C4 H4 123.0 . . ?
C3 C4 C5 113.9(4) . . ?
C3 C4 H4 123.0 . . ?
N3 C6 C1 128.9(4) . . ?
C5 C6 N3 110.2(4) . . ?
C5 C6 C1 120.9(4) . . ?
Cl1 C10 H10A 109.4 . . ?
Cl1 C10 H10B 109.4 . . ?
C9 C10 Cl1 111.4(3) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O2 C3 C2 113.1(4) . . ?
O2 C3 C4 123.7(4) . . ?
C4 C3 C2 123.2(4) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_daniel_ome_13march18_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1856992'
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N3 O4'
_chemical_formula_sum            'C10 H11 N3 O4'
_chemical_formula_weight         237.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.073(6)
_cell_length_b                   4.901(2)
_cell_length_c                   16.934(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.837(13)
_cell_angle_gamma                90
_cell_volume                     1038.5(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1377
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      25.290
_cell_measurement_theta_min      2.568
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1564 before and 0.0944 after correction. The Ratio of minimum to maximum transmission is 0.5158. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.065
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1455
_diffrn_reflns_av_unetI/netI     0.1610
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         1.627
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1422
_reflns_number_total             2383
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0880
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0254P)²+0.7284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1914
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O1 O 0.93264(18) 1.0560(5) 0.57028(14) 0.0270(6) Uani 1 1 d . . . . .
O3 O 0.55973(19) 0.4831(5) 0.69456(16) 0.0321(7) Uani 1 1 d . . . . .
O4 O 0.53513(18) 0.2302(5) 0.57917(15) 0.0268(6) Uani 1 1 d . . . . .
O2 O 0.83067(19) 1.2647(5) 0.81101(15) 0.0285(6) Uani 1 1 d . . . . .
N1 N 0.6613(2) 0.5566(6) 0.60867(17) 0.0222(7) Uani 1 1 d . . . . .
N2 N 0.6893(2) 0.4849(6) 0.53717(18) 0.0257(7) Uani 1 1 d . . . . .
N3 N 0.7673(2) 0.6414(6) 0.53317(17) 0.0250(7) Uani 1 1 d . . . . .
C8 C 0.7643(3) 1.2252(8) 0.8643(2) 0.0329(10) Uani 1 1 d . . . . .
H8A H 0.689431 1.257406 0.833257 0.049 Uiso 1 1 calc GR . . . .
H8B H 0.785534 1.353484 0.910561 0.049 Uiso 1 1 calc GR . . . .
H8C H 0.772508 1.037894 0.885394 0.049 Uiso 1 1 calc GR . . . .
C4 C 0.7331(3) 0.9064(7) 0.7229(2) 0.0220(8) Uani 1 1 d . . . . .
H4 H 0.687090 0.869658 0.755979 0.026 Uiso 1 1 calc R . . . .
C7 C 1.0141(3) 1.2632(7) 0.5916(2) 0.0298(9) Uani 1 1 d . . . . .
H7A H 1.052208 1.269144 0.549597 0.045 Uiso 1 1 calc GR . . . .
H7B H 1.064634 1.220644 0.645380 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.980930 1.440881 0.594375 0.045 Uiso 1 1 calc GR . . . .
C6 C 0.7933(3) 0.8147(7) 0.6005(2) 0.0213(8) Uani 1 1 d . . . . .
C3 C 0.8112(3) 1.1027(7) 0.7422(2) 0.0221(8) Uani 1 1 d . . . . .
C2 C 0.8815(3) 1.1605(7) 0.6941(2) 0.0221(8) Uani 1 1 d . . . . .
H2 H 0.934634 1.297663 0.711330 0.026 Uiso 1 1 calc R . . . .
C9 C 0.5805(3) 0.4205(7) 0.6324(2) 0.0240(8) Uani 1 1 d . . . . .
C10 C 0.4529(3) 0.0760(8) 0.6018(2) 0.0315(9) Uani 1 1 d . . . . .
H10A H 0.423856 -0.063678 0.559942 0.047 Uiso 1 1 calc GR . . . .
H10B H 0.395539 0.199548 0.605466 0.047 Uiso 1 1 calc GR . . . .
H10C H 0.484022 -0.011905 0.655434 0.047 Uiso 1 1 calc GR . . . .
C5 C 0.7275(2) 0.7649(7) 0.6496(2) 0.0213(8) Uani 1 1 d . . . . .
C1 C 0.8722(3) 1.0166(7) 0.6221(2) 0.0211(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.440(4) . ?
O1 C1 1.353(4) . ?
O3 C9 1.200(4) . ?
O4 C9 1.314(4) . ?
O4 C10 1.453(4) . ?
O2 C8 1.435(4) . ?
O2 C3 1.371(4) . ?
N1 N2 1.407(4) . ?
N1 C9 1.403(5) . ?
N1 C5 1.386(4) . ?
N2 N3 1.294(4) . ?
N3 C6 1.382(4) . ?
C4 C3 1.372(5) . ?
C4 C5 1.406(5) . ?
C6 C5 1.381(5) . ?
C6 C1 1.400(5) . ?
C3 C2 1.422(5) . ?
C2 C1 1.384(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 117.8(3) . . ?
C9 O4 C10 114.2(3) . . ?
C3 O2 C8 117.3(3) . . ?
C9 N1 N2 122.2(3) . . ?
C5 N1 N2 109.5(3) . . ?
C5 N1 C9 128.2(3) . . ?
N3 N2 N1 107.6(3) . . ?
N2 N3 C6 109.3(3) . . ?
C3 C4 C5 113.7(3) . . ?
N3 C6 C1 129.5(3) . . ?
C5 C6 N3 110.0(3) . . ?
C5 C6 C1 120.6(3) . . ?
O2 C3 C4 123.4(3) . . ?
O2 C3 C2 112.3(3) . . ?
C4 C3 C2 124.3(3) . . ?
C1 C2 C3 119.8(3) . . ?
O3 C9 O4 127.7(3) . . ?
O3 C9 N1 120.7(3) . . ?
O4 C9 N1 111.6(3) . . ?
N1 C5 C4 132.1(3) . . ?
C6 C5 N1 103.7(3) . . ?
C6 C5 C4 124.3(3) . . ?
O1 C1 C6 117.1(3) . . ?
O1 C1 C2 125.4(3) . . ?
C2 C1 C6 117.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_hakan1_0ma
_database_code_depnum_ccdc_archive 'CCDC 1856995'
_audit_update_record             
;
2018-07-20 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C20 H22 N6 O6)'
_chemical_formula_sum            'C10 H11 N3 O3'
_chemical_formula_weight         221.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   9.9817(12)
_cell_length_b                   6.6498(8)
_cell_length_c                   15.4052(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1022.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1577
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      30.681
_cell_measurement_theta_min      3.063
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0558 before and 0.0443 after correction. The Ratio of minimum to maximum transmission is 0.8748. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.022
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2950
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.337
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                835
_reflns_number_total             964
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         964
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H7A-H2
 2.06 with sigma of 0.02
 H0AB-H4
 2.47 with sigma of 0.02
 H10A-N2
 2.47 with sigma of 0.02
3. Others
 Fixed Sof: H7A(0.5) H7B(0.5) H7C(0.5) H10A(0.5) H10B(0.5) H10C(0.5) H0AA(0.5)
 H0AB(0.5) H0AC(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C0AA(H0AA,H0AB,H0AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.54825(15) 0.250000 0.72335(9) 0.0376(4) Uani 1 2 d S T P . .
O3 O 0.55187(15) 0.250000 0.30242(10) 0.0401(4) Uani 1 2 d S T P . .
O2 O 0.17282(14) 0.250000 0.53515(10) 0.0378(4) Uani 1 2 d S T P . .
N3 N 0.71695(17) 0.250000 0.56878(12) 0.0317(5) Uani 1 2 d S T P . .
N1 N 0.64137(16) 0.250000 0.43689(11) 0.0271(4) Uani 1 2 d S T P . .
N2 N 0.75466(17) 0.250000 0.48870(12) 0.0335(5) Uani 1 2 d DS T P . .
C3 C 0.3088(2) 0.250000 0.53983(13) 0.0281(5) Uani 1 2 d S T P . .
C9 C 0.6522(2) 0.250000 0.34555(15) 0.0332(5) Uani 1 2 d S T P . .
C2 C 0.3567(2) 0.250000 0.62614(14) 0.0302(5) Uani 1 2 d S T P . .
H2 H 0.294582 0.250000 0.672871 0.036 Uiso 1 2 calc DRS T P . .
C4 C 0.3919(2) 0.250000 0.46829(13) 0.0261(5) Uani 1 2 d S T P . .
H4 H 0.359059 0.250000 0.410411 0.031 Uiso 1 2 calc DRS T P . .
C7 C 0.4574(3) 0.250000 0.79517(15) 0.0447(6) Uani 1 2 d S T P . .
H7A H 0.390208 0.355746 0.786898 0.067 Uiso 0.5 1 calc DGR . . . .
H7B H 0.507041 0.275182 0.848959 0.067 Uiso 0.5 1 calc GR . . . .
H7C H 0.412679 0.119072 0.798834 0.067 Uiso 0.5 1 calc GR . . . .
C5 C 0.52819(19) 0.250000 0.48812(13) 0.0245(5) Uani 1 2 d S T P . .
C6 C 0.5790(2) 0.250000 0.57183(13) 0.0267(5) Uani 1 2 d S T P . .
C10 C 0.7907(3) 0.250000 0.31001(17) 0.0517(7) Uani 1 2 d S T P . .
H10A H 0.846889 0.159133 0.344387 0.078 Uiso 0.5 1 calc DGR . . . .
H10B H 0.827517 0.386464 0.312691 0.078 Uiso 0.5 1 calc GR . . . .
H10C H 0.788912 0.204402 0.249526 0.078 Uiso 0.5 1 calc GR . . . .
C1 C 0.4921(2) 0.250000 0.64357(13) 0.0286(5) Uani 1 2 d S T P . .
C0AA C 0.1129(2) 0.250000 0.45087(16) 0.0436(6) Uani 1 2 d S T P . .
H0AA H 0.150807 0.140262 0.416220 0.065 Uiso 0.5 1 calc GR . . . .
H0AB H 0.130959 0.378675 0.422143 0.065 Uiso 0.5 1 calc DGR . . . .
H0AC H 0.015942 0.231062 0.456460 0.065 Uiso 0.5 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.431(3) . ?
O1 C1 1.351(3) . ?
O3 C9 1.201(3) . ?
O2 C3 1.359(3) . ?
O2 C0AA 1.429(3) . ?
N3 N2 1.290(3) . ?
N3 C6 1.378(3) . ?
N1 N2 1.384(2) . ?
N1 C9 1.411(3) . ?
N1 C5 1.378(3) . ?
C3 C2 1.413(3) . ?
C3 C4 1.379(3) . ?
C9 C10 1.487(3) . ?
C2 C1 1.378(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.386(3) . ?
C6 C1 1.405(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 116.14(17) . . ?
C3 O2 C0AA 117.76(18) . . ?
N2 N3 C6 108.92(16) . . ?
N2 N1 C9 120.84(17) . . ?
C5 N1 N2 109.85(17) . . ?
C5 N1 C9 129.31(17) . . ?
N3 N2 N1 108.25(16) . . ?
O2 C3 C2 112.82(18) . . ?
O2 C3 C4 123.94(19) . . ?
C4 C3 C2 123.24(19) . . ?
O3 C9 N1 119.2(2) . . ?
O3 C9 C10 124.8(2) . . ?
N1 C9 C10 116.0(2) . . ?
C1 C2 C3 121.0(2) . . ?
C3 C4 C5 114.32(19) . . ?
N1 C5 C4 132.41(19) . . ?
N1 C5 C6 103.49(17) . . ?
C6 C5 C4 124.11(19) . . ?
N3 C6 C5 109.50(18) . . ?
N3 C6 C1 130.06(19) . . ?
C5 C6 C1 120.44(19) . . ?
O1 C1 C2 125.75(19) . . ?
O1 C1 C6 117.37(19) . . ?
C2 C1 C6 116.87(19) . . ?

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
C4 H4 O3 0.95 2.54 3.013(3) 110.7 .
C7 H7B O2 0.98 2.44 3.385(3) 161.8 4_556

_olex2_submission_special_instructions 'No special instructions were received'
