# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_11_a
_database_code_depnum_ccdc_archive 'CCDC 2232818'
loop_
_audit_author_name
_audit_author_address
'Yuwei Song'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-12-26 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 N2 S'
_chemical_formula_weight         254.34

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.9301(7)
_cell_length_b                   7.7862(4)
_cell_length_c                   29.5973(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2518.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7957
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.48

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17370
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.753
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2204
_reflns_number_gt                1938
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.5181P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2204
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65700(15) 0.40535(19) 0.55623(5) 0.0455(4) Uani 1 1 d . . . . .
C2 C 0.68760(17) 0.4330(2) 0.51106(6) 0.0552(4) Uani 1 1 d . . . . .
H2 H 0.752022 0.505124 0.503212 0.066 Uiso 1 1 calc R U . . .
C3 C 0.61983(18) 0.3506(2) 0.47845(6) 0.0594(5) Uani 1 1 d . . . . .
H3 H 0.638894 0.367109 0.448137 0.071 Uiso 1 1 calc R U . . .
C4 C 0.52291(19) 0.2427(2) 0.49012(6) 0.0587(5) Uani 1 1 d . . . . .
H4 H 0.478078 0.188773 0.467500 0.070 Uiso 1 1 calc R U . . .
C5 C 0.49298(16) 0.2153(2) 0.53450(6) 0.0534(4) Uani 1 1 d . . . . .
H5 H 0.428535 0.142728 0.541975 0.064 Uiso 1 1 calc R U . . .
C6 C 0.55980(14) 0.29706(19) 0.56834(5) 0.0435(4) Uani 1 1 d . . . . .
C7 C 0.61597(13) 0.37445(17) 0.63722(5) 0.0396(4) Uani 1 1 d . . . . .
C8 C 0.61978(13) 0.38251(16) 0.68624(5) 0.0386(4) Uani 1 1 d . . . . .
C9 C 0.53192(13) 0.29687(18) 0.71204(5) 0.0415(4) Uani 1 1 d . . . . .
H9 H 0.470151 0.236512 0.697383 0.050 Uiso 1 1 calc R U . . .
C10 C 0.53404(14) 0.29917(19) 0.75830(5) 0.0432(4) Uani 1 1 d . . . . .
H10 H 0.473852 0.240789 0.774339 0.052 Uiso 1 1 calc R U . . .
C11 C 0.62609(13) 0.38869(17) 0.78200(5) 0.0404(4) Uani 1 1 d . . . . .
C12 C 0.71511(14) 0.47424(18) 0.75612(6) 0.0445(4) Uani 1 1 d . . . . .
H12 H 0.777529 0.533820 0.770621 0.053 Uiso 1 1 calc R U . . .
C13 C 0.71129(13) 0.47115(18) 0.70970(6) 0.0434(4) Uani 1 1 d . . . . .
H13 H 0.771093 0.529506 0.693458 0.052 Uiso 1 1 calc R U . . .
N1 N 0.53800(12) 0.28284(16) 0.61426(5) 0.0434(3) Uani 1 1 d . . . . .
N2 N 0.62915(13) 0.38986(18) 0.82832(5) 0.0520(4) Uani 1 1 d . . . . .
C14 C 0.72402(17) 0.4807(2) 0.85285(7) 0.0590(5) Uani 1 1 d . . . . .
H14A H 0.802728 0.448096 0.841291 0.088 Uiso 1 1 calc R U . . .
H14B H 0.719221 0.451984 0.884342 0.088 Uiso 1 1 calc R U . . .
H14C H 0.712926 0.602214 0.849154 0.088 Uiso 1 1 calc R U . . .
C15 C 0.52868(17) 0.3223(3) 0.85465(6) 0.0610(5) Uani 1 1 d . . . . .
H15A H 0.452590 0.358045 0.841460 0.091 Uiso 1 1 calc R U . . .
H15B H 0.533998 0.364864 0.885031 0.091 Uiso 1 1 calc R U . . .
H15C H 0.532740 0.199148 0.854952 0.091 Uiso 1 1 calc R U . . .
S1 S 0.72195(4) 0.49089(5) 0.60441(2) 0.04853(19) 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 1.395(2) . ?
C1 C6 1.403(2) . ?
C1 S1 1.7266(17) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.384(2) . ?
C7 N1 1.3028(19) . ?
C7 C8 1.453(2) . ?
C7 S1 1.7627(14) . ?
C8 C9 1.396(2) . ?
C8 C13 1.400(2) . ?
C9 C10 1.369(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.411(2) . ?
C10 H10 0.9300 . ?
C11 N2 1.371(2) . ?
C11 C12 1.406(2) . ?
C12 C13 1.375(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N2 C15 1.446(2) . ?
N2 C14 1.450(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.29(16) . . ?
C2 C1 S1 129.30(14) . . ?
C6 C1 S1 109.40(12) . . ?
C3 C2 C1 118.12(18) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.07(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 120.81(18) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.53(17) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C5 125.38(15) . . ?
N1 C6 C1 115.43(14) . . ?
C5 C6 C1 119.19(15) . . ?
N1 C7 C8 124.30(13) . . ?
N1 C7 S1 115.09(12) . . ?
C8 C7 S1 120.61(10) . . ?
C9 C8 C13 117.11(15) . . ?
C9 C8 C7 120.38(13) . . ?
C13 C8 C7 122.50(13) . . ?
C10 C9 C8 121.92(14) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 121.05(14) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
N2 C11 C12 121.65(14) . . ?
N2 C11 C10 121.19(14) . . ?
C12 C11 C10 117.16(15) . . ?
C13 C12 C11 121.01(14) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 121.75(14) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
C7 N1 C6 110.85(13) . . ?
C11 N2 C15 121.20(14) . . ?
C11 N2 C14 121.41(14) . . ?
C15 N2 C14 116.79(15) . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 S1 C7 89.23(7) . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_c3
_database_code_depnum_ccdc_archive 'CCDC 2232820'
loop_
_audit_author_name
_audit_author_address
'Yuwei Song'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-12-26 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_audit_creation_date             2022-11-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N2 S2'
_chemical_formula_sum            'C19 H16 N2 S2'
_chemical_formula_weight         336.46
_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 0.0181 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'
S S 0.3331 0.5567 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   25.7622(18)
_cell_length_b                   10.7438(7)
_cell_length_c                   5.8585(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1621.54(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    965
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      64.462
_cell_measurement_theta_min      5.362
_shelx_estimated_absorpt_T_max   0.756
_shelx_estimated_absorpt_T_min   0.682
_exptl_absorpt_coefficient_mu    2.961
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1458 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.7239.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6951
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.274
_diffrn_reflns_theta_min         3.431
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_full    0.802
_reflns_Friedel_fraction_max     0.798
_reflns_number_gt                1826
_reflns_number_total             2662
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 484 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.34(4)
_refine_ls_extinction_coef       0.0033(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2662
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0999
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.011
_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)+(0.0820P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1772
_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), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C13(H13), C14(H14),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.2901(3) 0.6922(8) 0.6510(15) 0.056(2) Uani 1 1 d . . . . .
C2 C 0.2537(3) 0.7133(8) 0.8246(15) 0.064(2) Uani 1 1 d . . . . .
H2 H 0.252734 0.661178 0.955528 0.077 Uiso 1 1 calc R U . . .
C3 C 0.2193(3) 0.8104(8) 0.803(2) 0.071(2) Uani 1 1 d . . . . .
H3 H 0.195126 0.826389 0.921916 0.085 Uiso 1 1 calc R U . . .
C4 C 0.2193(3) 0.8874(8) 0.606(2) 0.070(2) Uani 1 1 d . . . . .
H4 H 0.194711 0.952941 0.591816 0.084 Uiso 1 1 calc R U . . .
C5 C 0.2548(3) 0.8670(9) 0.4345(18) 0.067(2) Uani 1 1 d . . . . .
H5 H 0.255038 0.917690 0.301566 0.081 Uiso 1 1 calc R U . . .
C6 C 0.2906(3) 0.7702(7) 0.4602(16) 0.058(2) Uani 1 1 d . . . . .
C7 C 0.3547(3) 0.6035(7) 0.4612(14) 0.0517(18) Uani 1 1 d . . . . .
C8 C 0.3962(3) 0.5193(7) 0.3953(13) 0.0525(18) Uani 1 1 d . . . . .
C9 C 0.4218(3) 0.5198(8) 0.1913(14) 0.057(2) Uani 1 1 d . . . . .
H9 H 0.414313 0.576479 0.071200 0.068 Uiso 1 1 calc R U . . .
C10 C 0.4603(3) 0.4274(8) 0.1779(14) 0.0545(19) Uani 1 1 d . . . . .
H10 H 0.481655 0.415738 0.047491 0.065 Uiso 1 1 calc R U . . .
C11 C 0.4640(3) 0.3561(7) 0.3694(13) 0.0499(18) Uani 1 1 d . . . . .
C12 C 0.5013(3) 0.2558(7) 0.4136(13) 0.0488(18) Uani 1 1 d . . . . .
C13 C 0.4998(3) 0.1822(7) 0.6083(13) 0.0547(19) Uani 1 1 d . . . . .
H13 H 0.473065 0.195387 0.717139 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5360(3) 0.0908(8) 0.6478(15) 0.061(2) Uani 1 1 d . . . . .
H14 H 0.533752 0.042021 0.782664 0.073 Uiso 1 1 calc R U . . .
C15 C 0.5761(3) 0.0688(8) 0.4926(16) 0.063(2) Uani 1 1 d . . . . .
C16 C 0.5771(3) 0.1390(9) 0.2992(17) 0.064(2) Uani 1 1 d . . . . .
H16 H 0.603546 0.123563 0.189942 0.076 Uiso 1 1 calc R U . . .
C17 C 0.5416(3) 0.2310(7) 0.2551(16) 0.060(2) Uani 1 1 d . . . . .
H17 H 0.544039 0.278106 0.118297 0.072 Uiso 1 1 calc R U . . .
C18 C 0.6559(4) -0.0399(11) 0.373(2) 0.093(3) Uani 1 1 d . . . . .
H18A H 0.642051 -0.076591 0.232572 0.139 Uiso 1 1 calc R U . . .
H18B H 0.681800 -0.095956 0.439466 0.139 Uiso 1 1 calc R U . . .
H18C H 0.672104 0.040390 0.338076 0.139 Uiso 1 1 calc R U . . .
C19 C 0.6128(5) -0.0960(13) 0.728(3) 0.116(5) Uani 1 1 d . . . . .
H19A H 0.612309 -0.043318 0.864794 0.174 Uiso 1 1 calc R U . . .
H19B H 0.643639 -0.149237 0.730976 0.174 Uiso 1 1 calc R U . . .
H19C H 0.581535 -0.147988 0.725295 0.174 Uiso 1 1 calc R U . . .
N1 N 0.3269(2) 0.5956(6) 0.6506(12) 0.0551(16) Uani 1 1 d . . . . .
N2 N 0.6139(3) -0.0213(8) 0.5347(17) 0.085(2) Uani 1 1 d . . . . .
S1 S 0.33968(9) 0.7273(2) 0.2777(4) 0.0635(6) Uani 1 1 d . . . . .
S2 S 0.41930(7) 0.40379(17) 0.5720(3) 0.0532(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.404(12) . ?
C1 C6 1.397(13) . ?
C1 N1 1.405(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.422(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(14) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(12) . ?
C6 S1 1.718(9) . ?
C7 C8 1.453(11) . ?
C7 N1 1.323(10) . ?
C7 S1 1.754(8) . ?
C8 C9 1.364(11) . ?
C8 S2 1.723(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.406(12) . ?
C10 H10 0.9500 . ?
C10 C11 1.362(11) . ?
C11 C12 1.467(11) . ?
C11 S2 1.732(8) . ?
C12 C13 1.389(11) . ?
C12 C17 1.418(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.396(12) . ?
C15 C16 1.362(13) . ?
C15 N2 1.396(11) . ?
C16 H16 0.9500 . ?
C16 C17 1.370(12) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 N2 1.450(13) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 N2 1.389(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 124.9(8) . . ?
C6 C1 C2 119.3(8) . . ?
C6 C1 N1 115.8(7) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(9) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(9) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(8) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.6(9) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 121.8(8) . . ?
C1 C6 S1 110.1(6) . . ?
C5 C6 S1 128.1(7) . . ?
C8 C7 S1 118.1(6) . . ?
N1 C7 C8 125.5(7) . . ?
N1 C7 S1 116.3(6) . . ?
C7 C8 S2 122.9(6) . . ?
C9 C8 C7 125.8(7) . . ?
C9 C8 S2 111.3(6) . . ?
C8 C9 H9 123.6 . . ?
C8 C9 C10 112.8(7) . . ?
C10 C9 H9 123.6 . . ?
C9 C10 H10 123.2 . . ?
C11 C10 C9 113.6(7) . . ?
C11 C10 H10 123.2 . . ?
C10 C11 C12 127.2(7) . . ?
C10 C11 S2 110.6(6) . . ?
C12 C11 S2 122.1(6) . . ?
C13 C12 C11 123.1(7) . . ?
C13 C12 C17 116.8(7) . . ?
C17 C12 C11 120.1(7) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.8(8) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.9(8) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 N2 121.3(8) . . ?
C16 C15 C14 117.5(7) . . ?
C16 C15 N2 121.2(8) . . ?
C15 C16 H16 118.5 . . ?
C15 C16 C17 123.0(9) . . ?
C17 C16 H16 118.5 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.0(8) . . ?
C16 C17 H17 120.0 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
C7 N1 C1 108.6(7) . . ?
C15 N2 C18 120.0(8) . . ?
C19 N2 C15 121.9(9) . . ?
C19 N2 C18 118.0(8) . . ?
C6 S1 C7 89.1(4) . . ?
C8 S2 C11 91.8(4) . . ?

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 1.6(13) . . . . ?
C1 C6 S1 C7 2.4(6) . . . . ?
C2 C1 C6 C5 -1.7(12) . . . . ?
C2 C1 C6 S1 178.5(6) . . . . ?
C2 C1 N1 C7 179.8(7) . . . . ?
C2 C3 C4 C5 -1.5(14) . . . . ?
C3 C4 C5 C6 -0.3(14) . . . . ?
C4 C5 C6 C1 1.9(13) . . . . ?
C4 C5 C6 S1 -178.3(7) . . . . ?
C5 C6 S1 C7 -177.4(8) . . . . ?
C6 C1 C2 C3 -0.1(12) . . . . ?
C6 C1 N1 C7 0.7(10) . . . . ?
C7 C8 C9 C10 179.7(8) . . . . ?
C7 C8 S2 C11 -179.9(7) . . . . ?
C8 C7 N1 C1 -179.0(7) . . . . ?
C8 C7 S1 C6 178.0(6) . . . . ?
C8 C9 C10 C11 0.4(11) . . . . ?
C9 C8 S2 C11 0.3(6) . . . . ?
C9 C10 C11 C12 -177.4(7) . . . . ?
C9 C10 C11 S2 -0.2(9) . . . . ?
C10 C11 C12 C13 -175.3(8) . . . . ?
C10 C11 C12 C17 5.3(12) . . . . ?
C10 C11 S2 C8 -0.1(6) . . . . ?
C11 C12 C13 C14 -178.4(7) . . . . ?
C11 C12 C17 C16 178.6(8) . . . . ?
C12 C11 S2 C8 177.3(6) . . . . ?
C12 C13 C14 C15 0.2(13) . . . . ?
C13 C12 C17 C16 -0.8(11) . . . . ?
C13 C14 C15 C16 -1.5(13) . . . . ?
C13 C14 C15 N2 178.0(9) . . . . ?
C14 C15 C16 C17 1.7(14) . . . . ?
C14 C15 N2 C18 -178.4(10) . . . . ?
C14 C15 N2 C19 2.2(16) . . . . ?
C15 C16 C17 C12 -0.5(14) . . . . ?
C16 C15 N2 C18 1.1(15) . . . . ?
C16 C15 N2 C19 -178.3(12) . . . . ?
C17 C12 C13 C14 1.0(11) . . . . ?
N1 C1 C2 C3 -179.2(8) . . . . ?
N1 C1 C6 C5 177.5(8) . . . . ?
N1 C1 C6 S1 -2.3(9) . . . . ?
N1 C7 C8 C9 173.5(8) . . . . ?
N1 C7 C8 S2 -6.4(11) . . . . ?
N1 C7 S1 C6 -2.3(6) . . . . ?
N2 C15 C16 C17 -177.8(9) . . . . ?
S1 C7 C8 C9 -6.9(11) . . . . ?
S1 C7 C8 S2 173.3(5) . . . . ?
S1 C7 N1 C1 1.3(8) . . . . ?
S2 C8 C9 C10 -0.4(9) . . . . ?
S2 C11 C12 C13 7.8(10) . . . . ?
S2 C11 C12 C17 -171.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

# start Validation Reply Form
_vrf_PLAT340_c3                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01194 Ang.  
RESPONSE:Quality of the data is not enough to get good bond length parameters.
;
####################################################################### 
# 
# 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_cu_20221117_zm_ngd_c4_0m
_database_code_depnum_ccdc_archive 'CCDC 2232821'
loop_
_audit_author_name
_audit_author_address
'Yuwei Song'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-12-26 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_audit_creation_date             2022-11-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 N2 S2'
_chemical_formula_sum            'C21 H18 N2 S2'
_chemical_formula_weight         362.49
_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 0.0181 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'
S S 0.3331 0.5567 '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                   5.95260(10)
_cell_length_b                   7.5011(2)
_cell_length_c                   40.2359(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1796.58(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5081
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.166
_cell_measurement_theta_min      4.396
_shelx_estimated_absorpt_T_max   0.737
_shelx_estimated_absorpt_T_min   0.600
_exptl_absorpt_coefficient_mu    2.713
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0932 before and 0.0584 after correction.
The Ratio of minimum to maximum transmission is 0.6848.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            14181
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.233
_diffrn_reflns_theta_min         4.395
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                2889
_reflns_number_total             3198
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1041 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.240(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.051
_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)+(0.0395P)²+0.4085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0849
_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), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.0327(6) 0.5125(4) 0.45462(8) 0.0400(8) Uani 1 1 d . . . . .
C2 C 0.1769(7) 0.4336(5) 0.47769(8) 0.0492(9) Uani 1 1 d . . . . .
H2 H 0.314897 0.381824 0.470795 0.059 Uiso 1 1 calc R U . . .
C3 C 0.1146(7) 0.4325(5) 0.51077(8) 0.0531(10) Uani 1 1 d . . . . .
H3 H 0.211189 0.379641 0.526785 0.064 Uiso 1 1 calc R U . . .
C4 C -0.0883(8) 0.5080(5) 0.52098(8) 0.0525(10) Uani 1 1 d . . . . .
H4 H -0.127882 0.504743 0.543843 0.063 Uiso 1 1 calc R U . . .
C5 C -0.2325(7) 0.5871(5) 0.49862(8) 0.0473(9) Uani 1 1 d . . . . .
H5 H -0.370115 0.638750 0.505697 0.057 Uiso 1 1 calc R U . . .
C6 C -0.1692(6) 0.5888(4) 0.46523(8) 0.0395(8) Uani 1 1 d . . . . .
C7 C -0.0891(6) 0.6056(4) 0.40565(8) 0.0354(7) Uani 1 1 d . . . . .
C8 C -0.1003(6) 0.6417(4) 0.37050(8) 0.0348(7) Uani 1 1 d . . . . .
C9 C -0.2670(6) 0.7277(4) 0.35354(8) 0.0398(8) Uani 1 1 d . . . . .
H9 H -0.400117 0.771443 0.363682 0.048 Uiso 1 1 calc R U . . .
C10 C -0.2200(6) 0.7445(5) 0.31940(8) 0.0413(8) Uani 1 1 d . . . . .
H10 H -0.318494 0.801657 0.304191 0.050 Uiso 1 1 calc R U . . .
C11 C -0.0202(6) 0.6711(4) 0.31019(7) 0.0358(7) Uani 1 1 d . . . . .
C12 C 0.0726(6) 0.6768(4) 0.27689(7) 0.0377(8) Uani 1 1 d . . . . .
H12 H -0.017975 0.732381 0.260433 0.045 Uiso 1 1 calc R U . . .
C13 C 0.2711(6) 0.6129(4) 0.26656(8) 0.0364(8) Uani 1 1 d . . . . .
H13 H 0.358569 0.548445 0.282228 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3635(6) 0.6343(4) 0.23321(7) 0.0340(7) Uani 1 1 d . . . . .
C15 C 0.2504(6) 0.7237(4) 0.20765(7) 0.0390(8) Uani 1 1 d . . . . .
H15 H 0.108686 0.776516 0.212197 0.047 Uiso 1 1 calc R U . . .
C16 C 0.3385(6) 0.7373(4) 0.17613(8) 0.0388(8) Uani 1 1 d . . . . .
H16 H 0.257492 0.801304 0.159650 0.047 Uiso 1 1 calc R U . . .
C17 C 0.5456(6) 0.6588(4) 0.16772(7) 0.0358(7) Uani 1 1 d . . . . .
C18 C 0.6642(6) 0.5747(4) 0.19360(8) 0.0394(8) Uani 1 1 d . . . . .
H18 H 0.807942 0.524777 0.189303 0.047 Uiso 1 1 calc R U . . .
C19 C 0.5742(6) 0.5638(4) 0.22515(8) 0.0370(8) Uani 1 1 d . . . . .
H19 H 0.658664 0.506116 0.242056 0.044 Uiso 1 1 calc R U . . .
C20 C 0.4911(7) 0.7391(5) 0.10929(8) 0.0555(10) Uani 1 1 d . . . . .
H20A H 0.356319 0.665692 0.106377 0.083 Uiso 1 1 calc R U . . .
H20B H 0.578092 0.739587 0.088610 0.083 Uiso 1 1 calc R U . . .
H20C H 0.446970 0.861278 0.114896 0.083 Uiso 1 1 calc R U . . .
C21 C 0.8287(7) 0.5774(6) 0.12622(9) 0.0547(10) Uani 1 1 d . . . . .
H21A H 0.948182 0.606991 0.142036 0.082 Uiso 1 1 calc R U . . .
H21B H 0.873033 0.615896 0.103883 0.082 Uiso 1 1 calc R U . . .
H21C H 0.803603 0.448301 0.126249 0.082 Uiso 1 1 calc R U . . .
N1 N 0.0751(5) 0.5231(3) 0.42046(6) 0.0393(7) Uani 1 1 d . . . . .
N2 N 0.6260(5) 0.6666(4) 0.13568(7) 0.0458(7) Uani 1 1 d . . . . .
S1 S -0.30947(16) 0.67812(13) 0.43136(2) 0.0460(2) Uani 1 1 d . . . . .
S2 S 0.11609(14) 0.57808(11) 0.34404(2) 0.0365(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.396(5) . ?
C1 C6 1.398(5) . ?
C1 N1 1.400(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(4) . ?
C6 S1 1.733(3) . ?
C7 C8 1.442(4) . ?
C7 N1 1.301(4) . ?
C7 S1 1.757(3) . ?
C8 C9 1.366(5) . ?
C8 S2 1.738(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.407(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.362(5) . ?
C11 C12 1.450(4) . ?
C11 S2 1.732(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.341(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.459(4) . ?
C14 C15 1.400(4) . ?
C14 C19 1.400(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.408(5) . ?
C17 C18 1.407(4) . ?
C17 N2 1.377(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(4) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 N2 1.438(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 N2 1.431(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
C2 C1 C6 119.9(3) . . ?
C2 C1 N1 124.5(3) . . ?
C6 C1 N1 115.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.9(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.2 . . ?
C4 C5 C6 117.7(4) . . ?
C6 C5 H5 121.2 . . ?
C1 C6 S1 109.4(2) . . ?
C5 C6 C1 121.5(3) . . ?
C5 C6 S1 129.1(3) . . ?
C8 C7 S1 119.0(2) . . ?
N1 C7 C8 125.0(3) . . ?
N1 C7 S1 116.0(2) . . ?
C7 C8 S2 121.0(2) . . ?
C9 C8 C7 127.8(3) . . ?
C9 C8 S2 111.2(2) . . ?
C8 C9 H9 123.7 . . ?
C8 C9 C10 112.7(3) . . ?
C10 C9 H9 123.7 . . ?
C9 C10 H10 123.1 . . ?
C11 C10 C9 113.8(3) . . ?
C11 C10 H10 123.1 . . ?
C10 C11 C12 124.9(3) . . ?
C10 C11 S2 111.0(2) . . ?
C12 C11 S2 124.1(3) . . ?
C11 C12 H12 116.2 . . ?
C13 C12 C11 127.7(3) . . ?
C13 C12 H12 116.2 . . ?
C12 C13 H13 117.4 . . ?
C12 C13 C14 125.3(3) . . ?
C14 C13 H13 117.4 . . ?
C15 C14 C13 123.2(3) . . ?
C19 C14 C13 120.6(3) . . ?
C19 C14 C15 116.2(3) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 C14 122.0(3) . . ?
C16 C15 H15 119.0 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 116.7(3) . . ?
N2 C17 C16 120.8(3) . . ?
N2 C17 C18 122.5(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(3) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 118.7 . . ?
C18 C19 C14 122.6(3) . . ?
C18 C19 H19 118.7 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
C7 N1 C1 109.9(3) . . ?
C17 N2 C20 120.9(3) . . ?
C17 N2 C21 121.5(3) . . ?
C21 N2 C20 116.8(3) . . ?
C6 S1 C7 89.06(16) . . ?
C11 S2 C8 91.37(16) . . ?

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 0.2(6) . . . . ?
C1 C6 S1 C7 0.4(2) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C1 C6 S1 179.2(3) . . . . ?
C2 C1 N1 C7 -179.3(3) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 S1 -179.4(3) . . . . ?
C5 C6 S1 C7 -180.0(3) . . . . ?
C6 C1 C2 C3 0.3(5) . . . . ?
C6 C1 N1 C7 0.3(4) . . . . ?
C7 C8 C9 C10 178.1(3) . . . . ?
C7 C8 S2 C11 -178.3(3) . . . . ?
C8 C7 N1 C1 179.5(3) . . . . ?
C8 C7 S1 C6 -179.7(3) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C8 S2 C11 0.6(3) . . . . ?
C9 C10 C11 C12 -177.2(3) . . . . ?
C9 C10 C11 S2 0.1(4) . . . . ?
C10 C11 C12 C13 177.4(3) . . . . ?
C10 C11 S2 C8 -0.4(3) . . . . ?
C11 C12 C13 C14 -175.1(3) . . . . ?
C12 C11 S2 C8 176.9(3) . . . . ?
C12 C13 C14 C15 -1.1(5) . . . . ?
C12 C13 C14 C19 179.2(3) . . . . ?
C13 C14 C15 C16 -178.0(3) . . . . ?
C13 C14 C19 C18 177.4(3) . . . . ?
C14 C15 C16 C17 1.3(5) . . . . ?
C15 C14 C19 C18 -2.4(5) . . . . ?
C15 C16 C17 C18 -3.6(5) . . . . ?
C15 C16 C17 N2 176.9(3) . . . . ?
C16 C17 C18 C19 2.9(5) . . . . ?
C16 C17 N2 C20 -6.3(5) . . . . ?
C16 C17 N2 C21 -175.8(3) . . . . ?
C17 C18 C19 C14 0.0(5) . . . . ?
C18 C17 N2 C20 174.2(3) . . . . ?
C18 C17 N2 C21 4.8(5) . . . . ?
C19 C14 C15 C16 1.7(5) . . . . ?
N1 C1 C2 C3 179.9(3) . . . . ?
N1 C1 C6 C5 179.9(3) . . . . ?
N1 C1 C6 S1 -0.5(4) . . . . ?
N1 C7 C8 C9 -179.8(3) . . . . ?
N1 C7 C8 S2 -1.1(4) . . . . ?
N1 C7 S1 C6 -0.2(3) . . . . ?
N2 C17 C18 C19 -177.6(3) . . . . ?
S1 C7 C8 C9 -0.4(4) . . . . ?
S1 C7 C8 S2 178.37(17) . . . . ?
S1 C7 N1 C1 0.0(3) . . . . ?
S2 C8 C9 C10 -0.7(4) . . . . ?
S2 C11 C12 C13 0.5(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_c2
_database_code_depnum_ccdc_archive 'CCDC 2232819'
loop_
_audit_author_name
_audit_author_address
'Yuwei Song'
;Nanjing Tech University
China
;
_audit_update_record             
;
2022-12-26 deposited with the CCDC.	2023-03-30 downloaded from the CCDC.
;
_audit_creation_date             2022-11-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 S2'
_chemical_formula_sum            'C13 H12 N2 S2'
_chemical_formula_weight         260.37
_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 0.0181 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'
S S 0.3331 0.5567 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   19.7351(8)
_cell_length_b                   10.4230(4)
_cell_length_c                   5.9647(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1226.93(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5606
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      68.084
_cell_measurement_theta_min      4.481
_shelx_estimated_absorpt_T_max   0.663
_shelx_estimated_absorpt_T_min   0.604
_exptl_absorpt_coefficient_mu    3.737
_exptl_absorpt_correction_T_max  0.3200
_exptl_absorpt_correction_T_min  0.1976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0788 after correction.
The Ratio of minimum to maximum transmission is 0.6175.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8938
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.078
_diffrn_reflns_theta_min         4.481
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.853
_reflns_number_gt                1987
_reflns_number_total             2086
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.059(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.0585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0839
_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), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.29957(15) 0.3712(3) 0.5787(6) 0.0327(7) Uani 1 1 d . . . . .
C2 C 0.25167(17) 0.2735(3) 0.6137(6) 0.0388(8) Uani 1 1 d . . . . .
H2 H 0.251300 0.225267 0.748832 0.047 Uiso 1 1 calc R U . . .
C3 C 0.20534(17) 0.2498(3) 0.4466(7) 0.0415(10) Uani 1 1 d . . . . .
H3 H 0.172456 0.184221 0.466893 0.050 Uiso 1 1 calc R U . . .
C4 C 0.20579(15) 0.3203(3) 0.2478(7) 0.0404(7) Uani 1 1 d . . . . .
H4 H 0.173924 0.300651 0.133508 0.048 Uiso 1 1 calc R U . . .
C5 C 0.25220(16) 0.4190(3) 0.2144(6) 0.0367(7) Uani 1 1 d . . . . .
H5 H 0.251649 0.468104 0.080219 0.044 Uiso 1 1 calc R U . . .
C6 C 0.29954(14) 0.4442(3) 0.3823(6) 0.0325(6) Uani 1 1 d . . . . .
C7 C 0.38551(14) 0.5387(3) 0.5543(5) 0.0296(6) Uani 1 1 d . . . . .
C8 C 0.44141(15) 0.6241(3) 0.5987(6) 0.0302(6) Uani 1 1 d . . . . .
C9 C 0.48291(16) 0.6292(3) 0.7844(6) 0.0358(7) Uani 1 1 d . . . . .
H9 H 0.477004 0.574930 0.910816 0.043 Uiso 1 1 calc R U . . .
C10 C 0.53406(15) 0.7203(3) 0.7711(7) 0.0385(8) Uani 1 1 d . . . . .
H10 H 0.566327 0.734842 0.886534 0.046 Uiso 1 1 calc R U . . .
C11 C 0.53291(14) 0.7872(3) 0.5728(7) 0.0346(7) Uani 1 1 d . . . . .
C12 C 0.5658(2) 0.9494(4) 0.3002(8) 0.0587(11) Uani 1 1 d . . . . .
H12A H 0.541128 0.895150 0.193795 0.088 Uiso 1 1 calc R U . . .
H12B H 0.609791 0.973174 0.236042 0.088 Uiso 1 1 calc R U . . .
H12C H 0.539482 1.027114 0.330831 0.088 Uiso 1 1 calc R U . . .
C13 C 0.63189(18) 0.9159(3) 0.6483(8) 0.0500(10) Uani 1 1 d . . . . .
H13A H 0.614111 0.954703 0.785971 0.075 Uiso 1 1 calc R U . . .
H13B H 0.661154 0.977730 0.571171 0.075 Uiso 1 1 calc R U . . .
H13C H 0.658162 0.839132 0.686191 0.075 Uiso 1 1 calc R U . . .
N1 N 0.34823(11) 0.5399(2) 0.3719(5) 0.0301(5) Uani 1 1 d . . . . .
N2 N 0.57617(16) 0.8808(3) 0.5032(6) 0.0498(8) Uani 1 1 d . . . . .
S1 S 0.36427(4) 0.42109(7) 0.75451(16) 0.0352(2) Uani 1 1 d . . . . .
S2 S 0.46634(3) 0.73655(7) 0.40096(15) 0.0348(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.405(4) . ?
C1 C6 1.397(5) . ?
C1 S1 1.732(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(5) . ?
C6 N1 1.386(4) . ?
C7 C8 1.442(4) . ?
C7 N1 1.314(4) . ?
C7 S1 1.762(3) . ?
C8 C9 1.378(5) . ?
C8 S2 1.734(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(5) . ?
C11 N2 1.361(4) . ?
C11 S2 1.748(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 N2 1.421(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 N2 1.447(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
C2 C1 S1 128.6(3) . . ?
C6 C1 C2 121.3(3) . . ?
C6 C1 S1 110.1(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 120.0(3) . . ?
N1 C6 C1 115.4(3) . . ?
N1 C6 C5 124.6(3) . . ?
C8 C7 S1 119.2(2) . . ?
N1 C7 C8 125.1(3) . . ?
N1 C7 S1 115.8(2) . . ?
C7 C8 S2 120.6(2) . . ?
C9 C8 C7 128.7(3) . . ?
C9 C8 S2 110.6(2) . . ?
C8 C9 H9 122.8 . . ?
C8 C9 C10 114.4(3) . . ?
C10 C9 H9 122.8 . . ?
C9 C10 H10 123.7 . . ?
C11 C10 C9 112.6(3) . . ?
C11 C10 H10 123.7 . . ?
C10 C11 S2 111.4(2) . . ?
N2 C11 C10 128.0(3) . . ?
N2 C11 S2 120.6(3) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
C7 N1 C6 110.1(3) . . ?
C11 N2 C12 122.0(3) . . ?
C11 N2 C13 118.4(3) . . ?
C12 N2 C13 119.4(3) . . ?
C1 S1 C7 88.50(15) . . ?
C8 S2 C11 91.07(16) . . ?

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 0.1(5) . . . . ?
C1 C6 N1 C7 1.1(3) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C1 C6 N1 178.2(3) . . . . ?
C2 C1 S1 C7 -178.6(3) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C3 C4 C5 C6 1.5(5) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 N1 -179.6(3) . . . . ?
C5 C6 N1 C7 -179.4(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C6 C1 S1 C7 1.2(2) . . . . ?
C7 C8 C9 C10 177.7(3) . . . . ?
C7 C8 S2 C11 -177.6(2) . . . . ?
C8 C7 N1 C6 179.2(3) . . . . ?
C8 C7 S1 C1 180.0(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C8 S2 C11 0.5(2) . . . . ?
C9 C10 C11 N2 -178.6(3) . . . . ?
C9 C10 C11 S2 0.6(4) . . . . ?
C10 C11 N2 C12 -174.9(4) . . . . ?
C10 C11 N2 C13 1.3(6) . . . . ?
C10 C11 S2 C8 -0.6(3) . . . . ?
N1 C7 C8 C9 -180.0(3) . . . . ?
N1 C7 C8 S2 -2.2(4) . . . . ?
N1 C7 S1 C1 -0.6(2) . . . . ?
N2 C11 S2 C8 178.6(3) . . . . ?
S1 C1 C2 C3 -179.0(3) . . . . ?
S1 C1 C6 C5 178.9(2) . . . . ?
S1 C1 C6 N1 -1.6(3) . . . . ?
S1 C7 C8 C9 -0.6(4) . . . . ?
S1 C7 C8 S2 177.19(16) . . . . ?
S1 C7 N1 C6 -0.2(3) . . . . ?
S2 C8 C9 C10 -0.3(3) . . . . ?
S2 C11 N2 C12 6.0(5) . . . . ?
S2 C11 N2 C13 -177.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
