# 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_TCNB-H2Q
_database_code_depnum_ccdc_archive 'CCDC 1994293'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;

_audit_update_record             
;
2020-04-01 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_publcif_datablock.id            {0bb0e9a7-9b7e-4a94-8f6c-62024d4e67ff}

# publcif _publ_body_element loop start

# publcif _publ_body_element loop end
_audit_creation_date             2019-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H2 N4, C6 H6 O2'
_chemical_formula_sum            'C16 H8 N4 O2'
_chemical_formula_weight         288.26
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   6.3120(4)
_cell_length_b                   7.4057(5)
_cell_length_c                   8.1661(5)
_cell_angle_alpha                108.309(5)
_cell_angle_beta                 109.791(4)
_cell_angle_gamma                92.810(5)
_cell_volume                     335.79(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1700
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      66.59
_cell_measurement_theta_min      6.15
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  0.9287
_exptl_absorpt_correction_T_min  0.7394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0720 after correction.
The Ratio of minimum to maximum transmission is 0.7962.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             148
_exptl_crystal_recrystallization_method 
'The material was recrystallised by sublimation'
_exptl_crystal_size_max          0.158
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.061
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2906
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.706
_diffrn_reflns_theta_max         66.706
_diffrn_reflns_theta_min         6.153
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'QUAZAR MX multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'high brilliance microfocus sealed tube, Cu'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                927
_reflns_number_total             1163
_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 V8.40A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 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 (Sheldrick, 2015)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0934
_refine_ls_restrained_S_all      1.290
_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)+0.9100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1831
_refine_ls_wR_factor_ref         0.1915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C1(H1)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_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 0.1688(5) 0.3875(5) 0.1172(5) 0.0301(8) Uani 1 1 d . . . . .
H1A H 0.185578 0.463717 0.223347 0.045 Uiso 1 1 calc GR . . . .
C6 C 0.5300(7) 0.5853(6) 0.1860(6) 0.0234(10) Uani 1 1 d . . . . .
H6 H 0.548905 0.645633 0.312543 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3352(7) 0.4474(6) 0.0638(6) 0.0220(10) Uani 1 1 d . . . . .
C8 C 0.3041(7) 0.3653(7) -0.1239(6) 0.0250(10) Uani 1 1 d . . . . .
H8 H 0.169270 0.275597 -0.209014 0.030 Uiso 1 1 calc R . . . .
N1 N 0.2146(7) 0.6324(6) 0.4801(6) 0.0307(10) Uani 1 1 d . . . . .
N2 N 0.7980(7) 0.9585(6) 0.6344(6) 0.0340(11) Uani 1 1 d . . . . .
C1 C 0.2869(8) 0.8852(6) 0.9452(7) 0.0252(10) Uani 1 1 d . . . . .
H1 H 0.142580 0.807905 0.908293 0.030 Uiso 1 1 calc R . . . .
C2 C 0.3919(8) 0.8725(6) 0.8182(6) 0.0230(10) Uani 1 1 d . . . . .
C3 C 0.6041(7) 0.9875(7) 0.8732(7) 0.0236(10) Uani 1 1 d . . . . .
C4 C 0.2873(8) 0.7402(7) 0.6297(7) 0.0270(11) Uani 1 1 d . . . . .
C5 C 0.7129(8) 0.9741(7) 0.7403(7) 0.0264(10) 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 H1A 0.8400 . ?
O1 C7 1.370(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.399(6) . ?
C6 C8 1.388(6) 2_665 ?
C7 C8 1.399(6) . ?
C8 H8 0.9500 . ?
N1 C4 1.145(6) . ?
N2 C5 1.143(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(7) . ?
C1 C3 1.388(7) 2_677 ?
C2 C3 1.400(6) . ?
C2 C4 1.438(7) . ?
C3 C5 1.450(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
C7 O1 H1A 109.5 . . ?
C7 C6 H6 119.7 . . ?
C8 C6 H6 119.7 2_665 . ?
C8 C6 C7 120.5(4) 2_665 . ?
O1 C7 C6 123.5(4) . . ?
O1 C7 C8 117.2(4) . . ?
C8 C7 C6 119.4(4) . . ?
C6 C8 C7 120.1(4) 2_665 . ?
C6 C8 H8 120.0 2_665 . ?
C7 C8 H8 120.0 . . ?
C2 C1 H1 120.5 . . ?
C3 C1 H1 120.5 2_677 . ?
C3 C1 C2 119.0(4) 2_677 . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 C4 121.0(4) . . ?
C3 C2 C4 118.8(4) . . ?
C1 C3 C2 120.7(4) 2_677 . ?
C1 C3 C5 119.2(4) 2_677 . ?
C2 C3 C5 120.1(4) . . ?
N1 C4 C2 176.5(5) . . ?
N2 C5 C3 178.3(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N1 0.84 2.02 2.854(5) 176.2 . yes

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 C7 C8 C6 -177.8(4) . . . 2_665 ?
C6 C7 C8 C6 2.6(7) . . . 2_665 ?
C8 C6 C7 O1 177.8(4) 2_665 . . . ?
C8 C6 C7 C8 -2.7(7) 2_665 . . . ?
C1 C2 C3 C1 0.3(7) . . . 2_677 ?
C1 C2 C3 C5 -179.9(4) . . . . ?
C3 C1 C2 C3 -0.3(7) 2_677 . . . ?
C3 C1 C2 C4 178.8(4) 2_677 . . . ?
C4 C2 C3 C1 -178.9(4) . . . 2_677 ?
C4 C2 C3 C5 0.9(7) . . . . ?



_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_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_TCNB-(H2QOMe)2
_database_code_depnum_ccdc_archive 'CCDC 2063384'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2021-02-17 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H8 O3), C10 H2 N4'
_chemical_formula_sum            'C24 H18 N4 O6'
_chemical_formula_weight         458.42
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.0977(3)
_cell_length_b                   7.7054(4)
_cell_length_c                   10.1834(5)
_cell_angle_alpha                79.516(2)
_cell_angle_beta                 85.590(3)
_cell_angle_gamma                70.030(3)
_cell_volume                     514.64(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7283
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      66.63
_cell_measurement_theta_min      6.20
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.630
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.6710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1405 before and 0.1049 after correction.
The Ratio of minimum to maximum transmission is 0.7764.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             238
_exptl_crystal_recrystallization_method 
'The material was recrystallised by sublimation'
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.089
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11444
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.792
_diffrn_reflns_theta_max         66.792
_diffrn_reflns_theta_min         4.416
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture (Cu)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1358
_reflns_number_total             1824
_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 V8.40B (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.1137
_refine_ls_restrained_S_all      1.125
_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)+(0.1306P)²+1.2491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2756
_refine_ls_wR_factor_ref         0.2917
_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:
 C12(H12), C9(H9), C10(H10), C1(H1)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_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
O2 O 0.0814(6) 1.0116(5) 0.1748(3) 0.0421(10) Uani 1 1 d . . . . .
H2 H 0.111956 1.054335 0.237208 0.063 Uiso 1 1 calc R U . . .
O1 O 0.1818(6) 0.8560(5) 0.4271(3) 0.0406(10) Uani 1 1 d . . . . .
O3 O 0.2116(6) 0.2537(5) 0.3279(3) 0.0406(10) Uani 1 1 d . . . . .
H3 H 0.237654 0.219352 0.409588 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1978(8) 0.5483(8) 0.3864(5) 0.0397(13) Uani 1 1 d . . . . .
H12 H 0.233975 0.490247 0.475677 0.048 Uiso 1 1 calc R U . . .
C8 C 0.1097(9) 0.8268(8) 0.2138(6) 0.0422(13) Uani 1 1 d . . . . .
C7 C 0.1669(8) 0.7383(8) 0.3462(5) 0.0377(13) Uani 1 1 d . . . . .
C9 C 0.0863(8) 0.7217(8) 0.1270(5) 0.0395(13) Uani 1 1 d . . . . .
H9 H 0.049109 0.779496 0.037803 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2460(9) 0.7721(8) 0.5613(5) 0.0391(13) Uani 1 1 d . . . . .
H6A H 0.378828 0.676513 0.559006 0.059 Uiso 1 1 calc R U . . .
H6B H 0.150196 0.713926 0.606522 0.059 Uiso 1 1 calc R U . . .
H6C H 0.252706 0.868599 0.609737 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1751(8) 0.4447(8) 0.2943(5) 0.0383(13) Uani 1 1 d . . . . .
C10 C 0.1154(8) 0.5298(9) 0.1652(5) 0.0416(14) Uani 1 1 d . . . . .
H10 H 0.094447 0.459524 0.103516 0.050 Uiso 1 1 calc R U . . .
N2 N 0.3465(7) 0.1594(6) 0.6172(4) 0.0392(11) Uani 1 1 d . . . . .
N1 N 0.3680(7) 0.5365(7) 0.8367(4) 0.0406(12) Uani 1 1 d . . . . .
C2 C 0.4428(8) 0.0573(7) 0.8671(5) 0.0356(12) Uani 1 1 d . . . . .
C5 C 0.3872(8) 0.1176(8) 0.7280(5) 0.0405(13) Uani 1 1 d . . . . .
C3 C 0.4563(8) 0.1869(8) 0.9422(5) 0.0373(13) Uani 1 1 d . . . . .
C1 C 0.4846(8) -0.1299(8) 0.9236(5) 0.0391(13) Uani 1 1 d . . . . .
H1 H 0.473525 -0.217662 0.872600 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4089(8) 0.3830(8) 0.8833(5) 0.0391(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8400 . ?
O2 C8 1.356(6) . ?
O1 C7 1.366(6) . ?
O1 C6 1.437(6) . ?
O3 H3 0.8400 . ?
O3 C11 1.386(6) . ?
C12 H12 0.9500 . ?
C12 C7 1.391(7) . ?
C12 C11 1.388(8) . ?
C8 C7 1.417(8) . ?
C8 C9 1.357(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.405(8) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C11 C10 1.386(8) . ?
C10 H10 0.9500 . ?
N2 C5 1.147(7) . ?
N1 C4 1.136(7) . ?
C2 C5 1.449(7) . ?
C2 C3 1.394(7) . ?
C2 C1 1.390(7) . ?
C3 C1 1.408(8) 2_657 ?
C3 C4 1.453(8) . ?
C1 H1 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
C8 O2 H2 109.5 . . ?
C7 O1 C6 116.4(4) . . ?
C11 O3 H3 109.5 . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C7 119.1(5) . . ?
O2 C8 C7 120.7(5) . . ?
O2 C8 C9 120.9(5) . . ?
C9 C8 C7 118.4(5) . . ?
O1 C7 C12 124.9(5) . . ?
O1 C7 C8 114.2(5) . . ?
C12 C7 C8 120.9(5) . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 121.9(5) . . ?
C10 C9 H9 119.0 . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C11 C12 121.4(5) . . ?
C10 C11 O3 117.9(5) . . ?
C10 C11 C12 120.8(5) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.9(5) . . ?
C11 C10 H10 120.6 . . ?
C3 C2 C5 119.7(5) . . ?
C1 C2 C5 119.4(5) . . ?
C1 C2 C3 120.8(5) . . ?
N2 C5 C2 177.7(6) . . ?
C2 C3 C1 120.6(5) . 2_657 ?
C2 C3 C4 120.6(5) . . ?
C1 C3 C4 118.9(5) 2_657 . ?
C2 C1 C3 118.6(5) . 2_657 ?
C2 C1 H1 120.7 . . ?
C3 C1 H1 120.7 2_657 . ?
N1 C4 C3 178.6(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O3 0.84 2.25 3.037(5) 155.6 1_565 yes
O3 H3 N2 0.84 2.22 3.050(6) 169.1 . yes

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
O2 C8 C7 O1 2.3(8) . . . . ?
O2 C8 C7 C12 -179.4(5) . . . . ?
O2 C8 C9 C10 179.8(5) . . . . ?
O3 C11 C10 C9 -177.2(5) . . . . ?
C12 C11 C10 C9 2.7(8) . . . . ?
C8 C9 C10 C11 -1.8(8) . . . . ?
C7 C12 C11 O3 177.5(5) . . . . ?
C7 C12 C11 C10 -2.3(8) . . . . ?
C7 C8 C9 C10 0.6(8) . . . . ?
C9 C8 C7 O1 -178.4(5) . . . . ?
C9 C8 C7 C12 -0.2(9) . . . . ?
C6 O1 C7 C12 3.9(8) . . . . ?
C6 O1 C7 C8 -178.0(5) . . . . ?
C11 C12 C7 O1 179.1(5) . . . . ?
C11 C12 C7 C8 1.1(8) . . . . ?
C5 C2 C3 C1 -178.2(5) . . . 2_657 ?
C5 C2 C3 C4 2.0(8) . . . . ?
C5 C2 C1 C3 178.3(5) . . . 2_657 ?
C3 C2 C1 C3 -0.9(9) . . . 2_657 ?
C1 C2 C3 C1 0.9(9) . . . 2_657 ?
C1 C2 C3 C4 -178.9(5) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_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_TCNB-(H2Q(OMe)2)2
_database_code_depnum_ccdc_archive 'CCDC 1994294'
loop_
_audit_author_name
_audit_author_address
'Yoann Rousselin'
;Universite de Bourgogne
France
;
_audit_update_record             
;
2020-04-01 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_publcif_datablock.id            {604b314a-6c85-4b0f-9866-8b31093311dd}

_audit_creation_date             2020-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H2 N4, 2(C8 H10 O4)'
_chemical_formula_sum            'C26 H22 N4 O8'
_chemical_formula_weight         518.47
_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                   18.7810(12)
_cell_length_b                   7.6668(5)
_cell_length_c                   17.9141(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.728(3)
_cell_angle_gamma                90
_cell_volume                     2379.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2695
_cell_measurement_temperature    115.0(1)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by sublimation'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4818
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_min         2.351
_diffrn_ambient_temperature      115.0(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2129
_reflns_number_total             2698
_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       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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    'SIR92 (Altomare et al., 1993)'
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.104
_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)+(0.0140P)²+6.4975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1134
_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(H2), C6(H6), C11(H11)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_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
C1 C 0.92582(12) -0.0893(3) 0.65140(12) 0.0182(4) Uani 1 1 d . . . . .
C2 C 0.96718(11) 0.0434(3) 0.63392(12) 0.0187(4) Uani 1 1 d . . . . .
H2 H 1.006657 0.017616 0.614791 0.022 Uiso 1 1 calc R . . . .
C3 C 0.94942(11) 0.2155(3) 0.64509(12) 0.0165(4) Uani 1 1 d . . . . .
C4 C 0.89127(11) 0.2550(3) 0.67282(11) 0.0156(4) Uani 1 1 d . . . . .
C5 C 0.84994(11) 0.1194(3) 0.68833(11) 0.0164(4) Uani 1 1 d . . . . .
C6 C 0.86709(11) -0.0544(3) 0.67799(12) 0.0176(4) Uani 1 1 d . . . . .
H6 H 0.838924 -0.146925 0.689003 0.021 Uiso 1 1 calc R . . . .
C7 C 1.05137(12) 0.3257(3) 0.61011(14) 0.0230(5) Uani 1 1 d . . . . .
H7A H 1.089529 0.259778 0.654459 0.034 Uiso 1 1 calc GR . . . .
H7B H 1.073871 0.437065 0.603459 0.034 Uiso 1 1 calc GR . . . .
H7C H 1.036299 0.258250 0.559887 0.034 Uiso 1 1 calc GR . . . .
C8 C 0.75157(12) 0.0318(3) 0.73441(13) 0.0224(5) Uani 1 1 d . . . . .
H8A H 0.726560 -0.043804 0.687395 0.034 Uiso 1 1 calc GR . . . .
H8B H 0.712329 0.082523 0.751403 0.034 Uiso 1 1 calc GR . . . .
H8C H 0.788024 -0.036914 0.778920 0.034 Uiso 1 1 calc GR . . . .
C9 C 0.86786(12) 0.2352(3) 0.43830(12) 0.0195(4) Uani 1 1 d . . . . .
C10 C 0.80799(11) 0.2426(3) 0.47023(12) 0.0167(4) Uani 1 1 d . . . . .
C11 C 0.78803(12) 0.4029(3) 0.49267(12) 0.0167(4) Uani 1 1 d . . . . .
H11 H 0.813830 0.506182 0.487751 0.020 Uiso 1 1 calc R . . . .
C12 C 0.77029(11) 0.0897(3) 0.47752(12) 0.0159(4) Uani 1 1 d . . . . .
C13 C 0.79160(12) -0.0756(3) 0.45389(12) 0.0187(4) Uani 1 1 d . . . . .
N1 N 0.91491(11) 0.2327(2) 0.41258(11) 0.0247(4) Uani 1 1 d . . . . .
N2 N 0.80966(11) -0.2054(2) 0.43476(12) 0.0249(4) Uani 1 1 d . . . . .
O1 O 0.94106(9) -0.26277(19) 0.64231(10) 0.0263(4) Uani 1 1 d . . . . .
H1 H 0.979621 -0.269897 0.629667 0.039 Uiso 1 1 calc GR . . . .
O2 O 0.98450(8) 0.35809(19) 0.62849(9) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.87315(8) 0.42431(19) 0.68372(9) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.904163 0.492404 0.675064 0.030 Uiso 1 1 calc GR . . . .
O4 O 0.79226(8) 0.16888(19) 0.71320(9) 0.0196(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(3) . ?
C1 C6 1.386(3) . ?
C1 O1 1.383(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(3) . ?
C3 C4 1.397(3) . ?
C3 O2 1.367(2) . ?
C4 C5 1.388(3) . ?
C4 O3 1.375(2) . ?
C5 C6 1.400(3) . ?
C5 O4 1.374(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 O2 1.438(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 O4 1.434(2) . ?
C9 C10 1.446(3) . ?
C9 N1 1.144(3) . ?
C10 C11 1.389(3) . ?
C10 C12 1.402(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(3) 7_656 ?
C12 C13 1.441(3) . ?
C13 N2 1.145(3) . ?
O1 H1 0.8400 . ?
O3 H3 0.8400 . ?

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
C6 C1 C2 121.70(19) . . ?
O1 C1 C2 121.28(18) . . ?
O1 C1 C6 117.01(18) . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.41(19) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 121.29(19) . . ?
O2 C3 C2 124.28(18) . . ?
O2 C3 C4 114.41(18) . . ?
C5 C4 C3 118.91(19) . . ?
O3 C4 C3 121.70(18) . . ?
O3 C4 C5 119.38(17) . . ?
C4 C5 C6 120.76(18) . . ?
O4 C5 C4 115.45(18) . . ?
O4 C5 C6 123.79(18) . . ?
C1 C6 C5 118.91(18) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
N1 C9 C10 178.7(2) . . ?
C11 C10 C9 119.16(19) . . ?
C11 C10 C12 120.71(18) . . ?
C12 C10 C9 120.13(19) . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.15(19) . 7_656 ?
C12 C11 H11 120.4 7_656 . ?
C10 C12 C13 120.05(18) . . ?
C11 C12 C10 120.14(19) 7_656 . ?
C11 C12 C13 119.81(18) 7_656 . ?
N2 C13 C12 178.6(2) . . ?
C1 O1 H1 109.5 . . ?
C3 O2 C7 116.68(16) . . ?
C4 O3 H3 109.5 . . ?
C5 O4 C8 116.81(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11 N2 0.95 2.40 3.254(3) 150.0 1_565 yes
O1 H1 N1 0.84 2.40 3.224(2) 169.1 5_756 yes
O3 H3 O1 0.84 2.16 2.943(2) 155.3 1_565 yes

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
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 O2 -178.49(19) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 O3 -179.74(18) . . . . ?
C2 C3 O2 C7 -9.7(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C3 C4 C5 O4 -178.20(17) . . . . ?
C4 C3 O2 C7 172.00(17) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 O4 C8 -176.34(17) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C6 C5 O4 C8 4.2(3) . . . . ?
C9 C10 C11 C12 179.21(18) . . . 7_656 ?
C9 C10 C12 C11 -179.21(18) . . . 7_656 ?
C9 C10 C12 C13 0.6(3) . . . . ?
C11 C10 C12 C11 0.2(3) . . . 7_656 ?
C11 C10 C12 C13 179.93(19) . . . . ?
C12 C10 C11 C12 -0.2(3) . . . 7_656 ?
O1 C1 C2 C3 -179.42(19) . . . . ?
O1 C1 C6 C5 179.75(18) . . . . ?
O2 C3 C4 C5 177.46(17) . . . . ?
O2 C3 C4 O3 -1.4(3) . . . . ?
O3 C4 C5 C6 -179.87(18) . . . . ?
O3 C4 C5 O4 0.7(3) . . . . ?
O4 C5 C6 C1 179.00(18) . . . . ?



_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a mylar loop with grease'
_olex2_submission_special_instructions 'No special instructions were received'



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