# Electronic Supplementary Material (ESI) for ChemComm.
# 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 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_cxy3044_0m
_database_code_depnum_ccdc_archive 'CCDC 2077101'
loop_
_audit_author_name
_audit_author_address
'Lv Jie'
;Chinese academy of medical science
China
;
_audit_update_record             
;
2021-04-13 deposited with the CCDC.	2021-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N2 S'
_chemical_formula_sum            'C22 H16 N2 S'
_chemical_formula_weight         340.43
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.1982(16)
_cell_length_b                   8.3863(11)
_cell_length_c                   17.209(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.749(5)
_cell_angle_gamma                90
_cell_volume                     1676.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9345
_cell_measurement_temperature    298
_cell_measurement_theta_max      72.30
_cell_measurement_theta_min      5.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.743
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0891 before and 0.0526 after correction. The Ratio of minimum to maximum transmission is 0.7811. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41395
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.705
_diffrn_reflns_theta_min         3.805
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3187
_reflns_number_total             3290
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.243
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0040(5)
_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   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.4405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0978
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.45025(3) -0.06968(4) 0.28744(2) 0.04738(14) Uani 1 1 d . . . . .
N2 N 0.31956(13) 0.55378(16) 0.28748(9) 0.0578(4) Uani 1 1 d . . . . .
H2A H 0.388835 0.498491 0.287007 0.069 Uiso 1 1 d GR . . . .
H2B H 0.340333 0.659999 0.296141 0.069 Uiso 1 1 d GR . . . .
N1 N 0.30867(8) 0.22002(13) 0.30762(6) 0.0345(2) Uani 1 1 d . . . . .
C1 C 0.26102(14) 0.0731(2) 0.06520(9) 0.0538(4) Uani 1 1 d . . . . .
H1 H 0.248918 0.039143 0.011786 0.065 Uiso 1 1 calc R . . . .
C2 C 0.34063(13) -0.0027(2) 0.12874(9) 0.0496(3) Uani 1 1 d . . . . .
H2 H 0.383933 -0.086226 0.117911 0.060 Uiso 1 1 calc R . . . .
C3 C 0.35695(11) 0.04436(15) 0.20883(8) 0.0373(3) Uani 1 1 d . . . . .
C4 C 0.29433(10) 0.17172(15) 0.22638(7) 0.0327(3) Uani 1 1 d . . . . .
C5 C 0.22433(10) 0.32578(15) 0.32222(7) 0.0346(3) Uani 1 1 d . . . . .
C6 C 0.13350(10) 0.25918(16) 0.34719(7) 0.0358(3) Uani 1 1 d . . . . .
C7 C 0.12502(12) 0.09380(17) 0.36094(8) 0.0433(3) Uani 1 1 d . . . . .
H7 H 0.179929 0.024513 0.352644 0.052 Uiso 1 1 calc R . . . .
C8 C 0.03721(14) 0.0347(2) 0.38623(10) 0.0569(4) Uani 1 1 d . . . . .
H8 H 0.033880 -0.074008 0.395923 0.068 Uiso 1 1 calc R . . . .
C9 C -0.04800(14) 0.1361(3) 0.39774(11) 0.0651(5) Uani 1 1 d . . . . .
H9 H -0.107736 0.094529 0.414545 0.078 Uiso 1 1 calc R . . . .
C10 C 0.41242(10) 0.19479(14) 0.37107(7) 0.0333(3) Uani 1 1 d . . . . .
C11 C 0.44064(12) 0.28838(17) 0.44094(8) 0.0411(3) Uani 1 1 d . . . . .
H11 H 0.390311 0.368233 0.445941 0.049 Uiso 1 1 calc R . . . .
C12 C 0.54259(13) 0.26496(19) 0.50348(8) 0.0498(4) Uani 1 1 d . . . . .
H12 H 0.558985 0.326717 0.550519 0.060 Uiso 1 1 calc R . . . .
C13 C 0.61953(13) 0.1501(2) 0.49584(10) 0.0558(4) Uani 1 1 d . . . . .
H13 H 0.689073 0.136728 0.536826 0.067 Uiso 1 1 calc R . . . .
C14 C 0.59294(13) 0.05535(18) 0.42720(10) 0.0507(4) Uani 1 1 d . . . . .
H14 H 0.645058 -0.021637 0.421876 0.061 Uiso 1 1 calc R . . . .
C15 C 0.48895(11) 0.07376(15) 0.36586(8) 0.0375(3) Uani 1 1 d . . . . .
C16 C 0.19952(13) 0.1995(2) 0.08150(8) 0.0495(4) Uani 1 1 d . . . . .
H16 H 0.146374 0.252093 0.038756 0.059 Uiso 1 1 calc R . . . .
C17 C 0.21611(11) 0.24924(17) 0.16106(8) 0.0407(3) Uani 1 1 d . . . . .
H17 H 0.174450 0.335570 0.171019 0.049 Uiso 1 1 calc R . . . .
C18 C 0.23212(12) 0.48855(16) 0.31126(8) 0.0409(3) Uani 1 1 d . . . . .
C19 C 0.14567(14) 0.58894(18) 0.32483(9) 0.0516(4) Uani 1 1 d . . . . .
H19 H 0.149925 0.698509 0.317929 0.062 Uiso 1 1 calc R . . . .
C20 C 0.05756(13) 0.5281(2) 0.34755(10) 0.0529(4) Uani 1 1 d . . . . .
H20 H 0.002056 0.596745 0.355473 0.064 Uiso 1 1 calc R . . . .
C21 C 0.04757(11) 0.36203(19) 0.35962(8) 0.0445(3) Uani 1 1 d . . . . .
C22 C -0.04311(13) 0.2952(2) 0.38431(10) 0.0597(4) Uani 1 1 d . . . . .
H22 H -0.100414 0.361405 0.391465 0.072 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.7611(14) . ?
S1 C15 1.7615(14) . ?
N2 H2A 0.9662 . ?
N2 H2B 0.9257 . ?
N2 C18 1.3677(19) . ?
N1 C4 1.4143(15) . ?
N1 C5 1.4372(15) . ?
N1 C10 1.4129(15) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(2) . ?
C1 C16 1.377(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3884(19) . ?
C3 C4 1.3986(17) . ?
C4 C17 1.3937(18) . ?
C5 C6 1.4193(17) . ?
C5 C18 1.3852(19) . ?
C6 C7 1.416(2) . ?
C6 C21 1.4231(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.366(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.403(3) . ?
C9 H9 0.9300 . ?
C9 C22 1.358(3) . ?
C10 C11 1.3885(18) . ?
C10 C15 1.4003(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3884(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.379(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.3858(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.4231(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.351(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.419(2) . ?
C21 C22 1.416(2) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C15 100.21(6) . . ?
H2A N2 H2B 105.4 . . ?
C18 N2 H2A 125.1 . . ?
C18 N2 H2B 122.5 . . ?
C4 N1 C5 118.04(10) . . ?
C10 N1 C4 122.19(10) . . ?
C10 N1 C5 118.53(10) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C16 119.33(13) . . ?
C16 C1 H1 120.3 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.70(14) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 S1 118.15(11) . . ?
C2 C3 C4 120.58(13) . . ?
C4 C3 S1 121.10(10) . . ?
C3 C4 N1 121.40(11) . . ?
C17 C4 N1 120.77(11) . . ?
C17 C4 C3 117.82(12) . . ?
C6 C5 N1 118.46(11) . . ?
C18 C5 N1 120.13(11) . . ?
C18 C5 C6 121.41(11) . . ?
C5 C6 C21 119.06(12) . . ?
C7 C6 C5 122.65(11) . . ?
C7 C6 C21 118.28(12) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.85(14) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.77(17) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.0 . . ?
C22 C9 C8 119.90(15) . . ?
C22 C9 H9 120.0 . . ?
C11 C10 N1 120.78(11) . . ?
C11 C10 C15 118.10(11) . . ?
C15 C10 N1 121.11(11) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.22(13) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.00(14) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.70(13) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.59(14) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 S1 121.05(10) . . ?
C14 C15 S1 118.39(11) . . ?
C14 C15 C10 120.26(13) . . ?
C1 C16 H16 119.7 . . ?
C1 C16 C17 120.57(14) . . ?
C17 C16 H16 119.7 . . ?
C4 C17 H17 119.5 . . ?
C16 C17 C4 120.96(13) . . ?
C16 C17 H17 119.5 . . ?
N2 C18 C5 121.80(12) . . ?
N2 C18 C19 119.80(13) . . ?
C5 C18 C19 118.40(13) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.24(14) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.65(13) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 C6 118.22(13) . . ?
C22 C21 C6 118.92(14) . . ?
C22 C21 C20 122.85(14) . . ?
C9 C22 C21 121.26(15) . . ?
C9 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?

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
S1 C3 C4 N1 3.91(16) . . . . ?
S1 C3 C4 C17 -175.51(9) . . . . ?
N2 C18 C19 C20 179.33(14) . . . . ?
N1 C4 C17 C16 -178.23(12) . . . . ?
N1 C5 C6 C7 2.23(17) . . . . ?
N1 C5 C6 C21 -178.23(10) . . . . ?
N1 C5 C18 N2 -0.77(19) . . . . ?
N1 C5 C18 C19 178.81(11) . . . . ?
N1 C10 C11 C12 -179.73(12) . . . . ?
N1 C10 C15 S1 -9.17(16) . . . . ?
N1 C10 C15 C14 177.11(12) . . . . ?
C1 C2 C3 S1 174.14(11) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C1 C16 C17 C4 -0.7(2) . . . . ?
C2 C1 C16 C17 -0.9(2) . . . . ?
C2 C3 C4 N1 179.16(12) . . . . ?
C2 C3 C4 C17 -0.27(18) . . . . ?
C3 S1 C15 C10 30.93(11) . . . . ?
C3 S1 C15 C14 -155.24(11) . . . . ?
C3 C4 C17 C16 1.20(19) . . . . ?
C4 N1 C5 C6 96.65(13) . . . . ?
C4 N1 C5 C18 -82.82(15) . . . . ?
C4 N1 C10 C11 156.87(12) . . . . ?
C4 N1 C10 C15 -23.94(17) . . . . ?
C5 N1 C4 C3 -166.08(11) . . . . ?
C5 N1 C4 C17 13.33(17) . . . . ?
C5 N1 C10 C11 -10.18(17) . . . . ?
C5 N1 C10 C15 169.02(11) . . . . ?
C5 C6 C7 C8 178.93(13) . . . . ?
C5 C6 C21 C20 -0.91(18) . . . . ?
C5 C6 C21 C22 179.83(12) . . . . ?
C5 C18 C19 C20 -0.3(2) . . . . ?
C6 C5 C18 N2 179.77(12) . . . . ?
C6 C5 C18 C19 -0.65(19) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
C6 C21 C22 C9 1.3(2) . . . . ?
C7 C6 C21 C20 178.65(13) . . . . ?
C7 C6 C21 C22 -0.62(18) . . . . ?
C7 C8 C9 C22 -0.5(3) . . . . ?
C8 C9 C22 C21 -0.7(3) . . . . ?
C10 N1 C4 C3 26.82(17) . . . . ?
C10 N1 C4 C17 -153.77(12) . . . . ?
C10 N1 C5 C6 -95.76(13) . . . . ?
C10 N1 C5 C18 84.76(15) . . . . ?
C10 C11 C12 C13 1.9(2) . . . . ?
C11 C10 C15 S1 170.04(10) . . . . ?
C11 C10 C15 C14 -3.68(18) . . . . ?
C11 C12 C13 C14 -2.2(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 S1 -170.46(12) . . . . ?
C13 C14 C15 C10 3.4(2) . . . . ?
C15 S1 C3 C2 156.34(11) . . . . ?
C15 S1 C3 C4 -28.30(12) . . . . ?
C15 C10 C11 C12 1.05(19) . . . . ?
C16 C1 C2 C3 1.8(2) . . . . ?
C18 C5 C6 C7 -178.30(12) . . . . ?
C18 C5 C6 C21 1.23(18) . . . . ?
C18 C19 C20 C21 0.6(2) . . . . ?
C19 C20 C21 C6 0.0(2) . . . . ?
C19 C20 C21 C22 179.27(15) . . . . ?
C20 C21 C22 C9 -177.93(16) . . . . ?
C21 C6 C7 C8 -0.61(19) . . . . ?

_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_cxy1476
_database_code_depnum_ccdc_archive 'CCDC 2077102'
loop_
_audit_author_name
_audit_author_address
'Lv Jie'
;Chinese academy of medical science
China
;
_audit_update_record             
;
2021-04-13 deposited with the CCDC.	2021-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-10-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H16 N2 S'
_chemical_formula_sum            'C22 H16 N2 S'
_chemical_formula_weight         340.43
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.9618(5)
_cell_length_b                   8.6489(3)
_cell_length_c                   26.7485(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3230.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9139
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0894 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.9547.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            44238
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.535
_diffrn_reflns_theta_min         2.475
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                6888
_reflns_number_total             7433
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(9)
_refine_ls_extinction_coef       0.0022(5)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7433
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.036
_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)+(0.0555P)²+2.9390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1111
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.52(9)
 0.48(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
3.a Riding coordinates:
 N2(H2A,H2B), N4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C22(H22), C21(H21), C17(H17), C18(H18), C8(H8), C7(H7),
 C6(H6), C5(H5), C19(H19), C20(H20), C14(H14), C13(H13), C38(H38), C37(H37),
 C44(H44), C43(H43), C40(H40), C39(H39), C42(H42), C41(H41), C27(H27), C28(H28),
  C29(H29), C30(H30), C36(H36), C35(H35)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.72192(6) 0.54924(10) 0.69927(4) 0.01936(19) Uani 1 1 d . . . . .
N1 N 0.5876(2) 0.3586(3) 0.63185(11) 0.0192(6) Uani 1 1 d . . . . .
N2 N 0.3762(3) -0.0449(4) 0.50723(16) 0.0346(9) Uani 1 1 d . . . . .
H2A H 0.417034 -0.110054 0.492820 0.042 Uiso 1 1 d R U . . .
H2B H 0.334884 -0.099474 0.525290 0.042 Uiso 1 1 d R U . . .
C16 C 0.6203(3) 0.1887(5) 0.45087(16) 0.0314(9) Uani 1 1 d . . . . .
H16 H 0.641238 0.172883 0.417467 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5422(3) 0.1154(5) 0.46805(15) 0.0272(8) Uani 1 1 d . . . . .
H15 H 0.508445 0.047338 0.446436 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5089(2) 0.1368(4) 0.51745(13) 0.0151(6) Uani 1 1 d . . . . .
C10 C 0.5603(3) 0.2388(4) 0.55027(14) 0.0215(8) Uani 1 1 d . . . . .
C9 C 0.5277(3) 0.2662(4) 0.59899(14) 0.0204(7) Uani 1 1 d . . . . .
C2 C 0.5522(3) 0.5033(4) 0.64811(13) 0.0161(7) Uani 1 1 d . . . . .
C1 C 0.6035(2) 0.5953(4) 0.68172(12) 0.0138(6) Uani 1 1 d . . . . .
C22 C 0.5651(3) 0.7332(4) 0.69979(14) 0.0191(7) Uani 1 1 d . . . . .
H22 H 0.597962 0.789147 0.725077 0.023 Uiso 1 1 calc R U . . .
C21 C 0.4791(3) 0.7894(4) 0.68108(14) 0.0210(7) Uani 1 1 d . . . . .
H21 H 0.454075 0.885332 0.692451 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4260(3) 0.0584(4) 0.53729(16) 0.0264(8) Uani 1 1 d . . . . .
C17 C 0.6714(3) 0.2899(4) 0.48293(15) 0.0249(8) Uani 1 1 d . . . . .
H17 H 0.726227 0.341654 0.470194 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6451(3) 0.3160(4) 0.53125(14) 0.0210(7) Uani 1 1 d . . . . .
H18 H 0.681353 0.383185 0.552003 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6567(2) 0.2737(4) 0.65961(12) 0.0143(6) Uani 1 1 d . . . . .
C8 C 0.6651(2) 0.1135(4) 0.65333(13) 0.0181(7) Uani 1 1 d . . . . .
H8 H 0.623321 0.061495 0.630928 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7337(3) 0.0297(4) 0.67932(14) 0.0192(7) Uani 1 1 d . . . . .
H7 H 0.739306 -0.078372 0.673757 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7938(2) 0.1011(4) 0.71313(13) 0.0203(7) Uani 1 1 d . . . . .
H6 H 0.840147 0.043017 0.731095 0.024 Uiso 1 1 calc R U . . .
C5 C 0.7852(3) 0.2602(4) 0.72046(13) 0.0190(7) Uani 1 1 d . . . . .
H5 H 0.825047 0.310386 0.744262 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7193(2) 0.3460(4) 0.69335(12) 0.0144(6) Uani 1 1 d . . . . .
C19 C 0.4652(3) 0.5615(4) 0.62989(14) 0.0204(7) Uani 1 1 d . . . . .
H19 H 0.429453 0.502619 0.606418 0.025 Uiso 1 1 calc R U . . .
C20 C 0.4305(3) 0.7033(4) 0.64554(15) 0.0227(8) Uani 1 1 d . . . . .
H20 H 0.372531 0.742052 0.631749 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4461(3) 0.1939(4) 0.61503(16) 0.0230(8) Uani 1 1 d . . . . .
H14 H 0.423741 0.215556 0.647844 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3933(3) 0.0891(4) 0.58556(15) 0.0225(8) Uani 1 1 d . . . . .
H13 H 0.337092 0.040816 0.598159 0.027 Uiso 1 1 calc R U . . .
S2 S 0.04059(6) 1.07287(9) 0.31683(3) 0.01789(19) Uani 1 1 d . . . . .
N3 N 0.1726(2) 0.8518(3) 0.37261(10) 0.0153(6) Uani 1 1 d . . . . .
N4 N 0.3753(2) 0.4533(4) 0.50327(13) 0.0239(7) Uani 1 1 d . . . . .
H4A H 0.334851 0.392389 0.519385 0.029 Uiso 1 1 d R U . . .
H4B H 0.415451 0.395399 0.485795 0.029 Uiso 1 1 d R U . . .
C38 C 0.1314(3) 0.7001(4) 0.55522(14) 0.0230(8) Uani 1 1 d . . . . .
H38 H 0.111250 0.691473 0.589026 0.028 Uiso 1 1 calc R U . . .
C37 C 0.2109(3) 0.6214(4) 0.53921(13) 0.0193(7) Uani 1 1 d . . . . .
H37 H 0.244847 0.557174 0.561940 0.023 Uiso 1 1 calc R U . . .
C33 C 0.2430(2) 0.6347(4) 0.48918(12) 0.0142(6) Uani 1 1 d . . . . .
C32 C 0.1920(3) 0.7327(4) 0.45575(13) 0.0151(7) Uani 1 1 d . . . . .
C31 C 0.2260(3) 0.7514(4) 0.40583(12) 0.0155(7) Uani 1 1 d . . . . .
C24 C 0.2130(2) 0.9965(4) 0.36001(12) 0.0139(6) Uani 1 1 d . . . . .
C23 C 0.1626(2) 1.1030(4) 0.33026(12) 0.0145(6) Uani 1 1 d . . . . .
C44 C 0.2047(2) 1.2395(4) 0.31440(13) 0.0163(6) Uani 1 1 d . . . . .
H44 H 0.171556 1.305221 0.291810 0.020 Uiso 1 1 calc R U . . .
C43 C 0.2954(3) 1.2806(4) 0.33142(14) 0.0195(7) Uani 1 1 d . . . . .
H43 H 0.324269 1.374712 0.320960 0.023 Uiso 1 1 calc R U . . .
C40 C 0.1088(3) 0.8114(4) 0.47324(13) 0.0175(7) Uani 1 1 d . . . . .
H40 H 0.073704 0.876237 0.451182 0.021 Uiso 1 1 calc R U . . .
C39 C 0.0794(3) 0.7940(4) 0.52170(14) 0.0205(7) Uani 1 1 d . . . . .
H39 H 0.023265 0.845623 0.532905 0.025 Uiso 1 1 calc R U . . .
C25 C 0.1018(2) 0.7814(4) 0.34212(12) 0.0138(6) Uani 1 1 d . . . . .
C26 C 0.0400(2) 0.8696(4) 0.31282(13) 0.0140(6) Uani 1 1 d . . . . .
C42 C 0.3428(3) 1.1822(4) 0.36383(14) 0.0204(7) Uani 1 1 d . . . . .
H42 H 0.402985 1.212176 0.377282 0.024 Uiso 1 1 calc R U . . .
C41 C 0.3038(3) 1.0406(4) 0.37696(14) 0.0188(7) Uani 1 1 d . . . . .
H41 H 0.339175 0.972435 0.397795 0.023 Uiso 1 1 calc R U . . .
C27 C -0.0270(2) 0.8000(4) 0.28141(13) 0.0175(7) Uani 1 1 d . . . . .
H27 H -0.066066 0.862292 0.260460 0.021 Uiso 1 1 calc R U . . .
C28 C -0.0370(3) 0.6401(5) 0.28051(14) 0.0216(7) Uani 1 1 d . . . . .
H28 H -0.083723 0.592650 0.259716 0.026 Uiso 1 1 calc R U . . .
C29 C 0.0224(3) 0.5510(4) 0.31057(14) 0.0207(7) Uani 1 1 d . . . . .
H29 H 0.015522 0.441710 0.310702 0.025 Uiso 1 1 calc R U . . .
C30 C 0.0918(2) 0.6195(4) 0.34044(14) 0.0186(7) Uani 1 1 d . . . . .
H30 H 0.133029 0.556387 0.359980 0.022 Uiso 1 1 calc R U . . .
C36 C 0.3065(3) 0.6756(4) 0.39061(13) 0.0185(7) Uani 1 1 d . . . . .
H36 H 0.329058 0.690708 0.357456 0.022 Uiso 1 1 calc R U . . .
C35 C 0.3573(2) 0.5757(4) 0.42253(14) 0.0178(7) Uani 1 1 d . . . . .
H35 H 0.413269 0.524680 0.410913 0.021 Uiso 1 1 calc R U . . .
C34 C 0.3253(3) 0.5516(4) 0.47111(14) 0.0180(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.764(3) . ?
S1 C4 1.766(3) . ?
N1 C9 1.453(5) . ?
N1 C2 1.415(4) . ?
N1 C3 1.421(4) . ?
N2 H2A 0.8891 . ?
N2 H2B 0.8884 . ?
N2 C12 1.388(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.343(6) . ?
C16 C17 1.417(6) . ?
C15 H15 0.9500 . ?
C15 C11 1.413(5) . ?
C11 C10 1.436(5) . ?
C11 C12 1.443(5) . ?
C10 C9 1.400(5) . ?
C10 C18 1.451(6) . ?
C9 C14 1.369(5) . ?
C2 C1 1.397(5) . ?
C2 C19 1.403(5) . ?
C1 C22 1.395(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.388(5) . ?
C21 H21 0.9500 . ?
C21 C20 1.386(5) . ?
C12 C13 1.395(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.363(6) . ?
C18 H18 0.9500 . ?
C3 C8 1.400(5) . ?
C3 C4 1.403(5) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(5) . ?
C7 H7 0.9500 . ?
C7 C6 1.380(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.395(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(5) . ?
C20 H20 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.410(5) . ?
C13 H13 0.9500 . ?
S2 C23 1.760(3) . ?
S2 C26 1.761(3) . ?
N3 C31 1.449(4) . ?
N3 C24 1.414(4) . ?
N3 C25 1.418(4) . ?
N4 H4A 0.8848 . ?
N4 H4B 0.8852 . ?
N4 C34 1.397(5) . ?
C38 H38 0.9500 . ?
C38 C37 1.371(5) . ?
C38 C39 1.411(5) . ?
C37 H37 0.9500 . ?
C37 C33 1.416(5) . ?
C33 C32 1.423(5) . ?
C33 C34 1.439(5) . ?
C32 C31 1.426(5) . ?
C32 C40 1.425(5) . ?
C31 C36 1.365(5) . ?
C24 C23 1.406(5) . ?
C24 C41 1.399(5) . ?
C23 C44 1.385(5) . ?
C44 H44 0.9500 . ?
C44 C43 1.392(5) . ?
C43 H43 0.9500 . ?
C43 C42 1.383(5) . ?
C40 H40 0.9500 . ?
C40 C39 1.368(5) . ?
C39 H39 0.9500 . ?
C25 C26 1.393(4) . ?
C25 C30 1.408(5) . ?
C26 C27 1.394(5) . ?
C42 H42 0.9500 . ?
C42 C41 1.386(5) . ?
C41 H41 0.9500 . ?
C27 H27 0.9500 . ?
C27 C28 1.390(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.389(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.388(5) . ?
C30 H30 0.9500 . ?
C36 H36 0.9500 . ?
C36 C35 1.406(5) . ?
C35 H35 0.9500 . ?
C35 C34 1.390(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 100.43(16) . . ?
C2 N1 C9 118.1(3) . . ?
C2 N1 C3 122.3(3) . . ?
C3 N1 C9 115.0(3) . . ?
H2A N2 H2B 108.4 . . ?
C12 N2 H2A 109.7 . . ?
C12 N2 H2B 110.6 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C15 H15 119.2 . . ?
C16 C15 C11 121.7(4) . . ?
C11 C15 H15 119.2 . . ?
C15 C11 C10 119.2(3) . . ?
C15 C11 C12 123.1(3) . . ?
C10 C11 C12 117.7(3) . . ?
C11 C10 C18 118.4(3) . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 C18 120.9(3) . . ?
C10 C9 N1 118.0(3) . . ?
C14 C9 N1 122.7(4) . . ?
C14 C9 C10 119.0(4) . . ?
C1 C2 N1 121.5(3) . . ?
C1 C2 C19 117.6(3) . . ?
C19 C2 N1 120.9(3) . . ?
C2 C1 S1 121.5(3) . . ?
C22 C1 S1 117.5(3) . . ?
C22 C1 C2 120.8(3) . . ?
C1 C22 H22 119.8 . . ?
C21 C22 C1 120.5(3) . . ?
C21 C22 H22 119.8 . . ?
C22 C21 H21 120.6 . . ?
C20 C21 C22 118.9(3) . . ?
C20 C21 H21 120.6 . . ?
N2 C12 C11 119.4(4) . . ?
N2 C12 C13 119.6(4) . . ?
C13 C12 C11 120.9(3) . . ?
C16 C17 H17 118.6 . . ?
C18 C17 C16 122.7(4) . . ?
C18 C17 H17 118.6 . . ?
C10 C18 H18 120.8 . . ?
C17 C18 C10 118.4(4) . . ?
C17 C18 H18 120.8 . . ?
C8 C3 N1 120.4(3) . . ?
C8 C3 C4 117.7(3) . . ?
C4 C3 N1 121.9(3) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 C3 121.0(3) . . ?
C7 C8 H8 119.5 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.5 . . ?
C7 C6 H6 120.6 . . ?
C7 C6 C5 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C3 C4 S1 121.0(3) . . ?
C5 C4 S1 118.1(3) . . ?
C5 C4 C3 120.8(3) . . ?
C2 C19 H19 119.4 . . ?
C20 C19 C2 121.1(3) . . ?
C20 C19 H19 119.4 . . ?
C21 C20 H20 119.6 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 H20 119.6 . . ?
C9 C14 H14 118.2 . . ?
C9 C14 C13 123.6(4) . . ?
C13 C14 H14 118.2 . . ?
C12 C13 C14 117.9(4) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C23 S2 C26 99.48(16) . . ?
C24 N3 C31 118.1(3) . . ?
C24 N3 C25 121.4(3) . . ?
C25 N3 C31 117.0(3) . . ?
H4A N4 H4B 108.9 . . ?
C34 N4 H4A 110.1 . . ?
C34 N4 H4B 109.6 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.3(3) . . ?
C39 C38 H38 119.9 . . ?
C38 C37 H37 119.6 . . ?
C38 C37 C33 120.7(3) . . ?
C33 C37 H37 119.6 . . ?
C37 C33 C32 119.0(3) . . ?
C37 C33 C34 122.0(3) . . ?
C32 C33 C34 119.1(3) . . ?
C33 C32 C31 119.3(3) . . ?
C33 C32 C40 119.1(3) . . ?
C40 C32 C31 121.6(3) . . ?
C32 C31 N3 118.1(3) . . ?
C36 C31 N3 122.0(3) . . ?
C36 C31 C32 119.9(3) . . ?
C23 C24 N3 121.0(3) . . ?
C41 C24 N3 121.7(3) . . ?
C41 C24 C23 117.3(3) . . ?
C24 C23 S2 120.2(3) . . ?
C44 C23 S2 118.3(3) . . ?
C44 C23 C24 121.3(3) . . ?
C23 C44 H44 119.9 . . ?
C23 C44 C43 120.3(3) . . ?
C43 C44 H44 119.9 . . ?
C44 C43 H43 120.6 . . ?
C42 C43 C44 118.9(3) . . ?
C42 C43 H43 120.6 . . ?
C32 C40 H40 119.9 . . ?
C39 C40 C32 120.2(3) . . ?
C39 C40 H40 119.9 . . ?
C38 C39 H39 119.6 . . ?
C40 C39 C38 120.7(3) . . ?
C40 C39 H39 119.6 . . ?
C26 C25 N3 121.3(3) . . ?
C26 C25 C30 117.7(3) . . ?
C30 C25 N3 121.0(3) . . ?
C25 C26 S2 120.6(3) . . ?
C25 C26 C27 121.2(3) . . ?
C27 C26 S2 118.1(3) . . ?
C43 C42 H42 119.5 . . ?
C43 C42 C41 121.0(3) . . ?
C41 C42 H42 119.5 . . ?
C24 C41 H41 119.5 . . ?
C42 C41 C24 121.0(3) . . ?
C42 C41 H41 119.5 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 120.6 . . ?
C29 C28 C27 118.8(3) . . ?
C29 C28 H28 120.6 . . ?
C28 C29 H29 119.6 . . ?
C30 C29 C28 120.9(3) . . ?
C30 C29 H29 119.6 . . ?
C25 C30 H30 119.6 . . ?
C29 C30 C25 120.8(3) . . ?
C29 C30 H30 119.6 . . ?
C31 C36 H36 119.0 . . ?
C31 C36 C35 122.0(3) . . ?
C35 C36 H36 119.0 . . ?
C36 C35 H35 120.1 . . ?
C34 C35 C36 119.9(3) . . ?
C34 C35 H35 120.1 . . ?
N4 C34 C33 119.8(3) . . ?
C35 C34 N4 120.4(3) . . ?
C35 C34 C33 119.7(3) . . ?

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
S1 C1 C22 C21 169.2(3) . . . . ?
N1 C9 C14 C13 -172.1(3) . . . . ?
N1 C2 C1 S1 8.7(5) . . . . ?
N1 C2 C1 C22 -176.0(3) . . . . ?
N1 C2 C19 C20 -179.7(3) . . . . ?
N1 C3 C8 C7 178.5(3) . . . . ?
N1 C3 C4 S1 -5.2(5) . . . . ?
N1 C3 C4 C5 179.2(3) . . . . ?
N2 C12 C13 C14 179.6(3) . . . . ?
C16 C15 C11 C10 -0.4(6) . . . . ?
C16 C15 C11 C12 -179.1(4) . . . . ?
C16 C17 C18 C10 -1.1(6) . . . . ?
C15 C16 C17 C18 0.5(6) . . . . ?
C15 C11 C10 C9 178.2(3) . . . . ?
C15 C11 C10 C18 -0.1(5) . . . . ?
C15 C11 C12 N2 0.7(5) . . . . ?
C15 C11 C12 C13 -176.9(4) . . . . ?
C11 C10 C9 N1 174.2(3) . . . . ?
C11 C10 C9 C14 0.1(5) . . . . ?
C11 C10 C18 C17 0.9(5) . . . . ?
C11 C12 C13 C14 -2.8(5) . . . . ?
C10 C11 C12 N2 -178.0(3) . . . . ?
C10 C11 C12 C13 4.4(5) . . . . ?
C10 C9 C14 C13 1.7(6) . . . . ?
C9 N1 C2 C1 176.7(3) . . . . ?
C9 N1 C2 C19 -5.0(5) . . . . ?
C9 N1 C3 C8 1.7(5) . . . . ?
C9 N1 C3 C4 -179.3(3) . . . . ?
C9 C10 C18 C17 -177.4(3) . . . . ?
C9 C14 C13 C12 -0.4(6) . . . . ?
C2 N1 C9 C10 114.9(4) . . . . ?
C2 N1 C9 C14 -71.2(5) . . . . ?
C2 N1 C3 C8 157.1(3) . . . . ?
C2 N1 C3 C4 -23.9(5) . . . . ?
C2 C1 C22 C21 -6.2(5) . . . . ?
C2 C19 C20 C21 -2.3(6) . . . . ?
C1 S1 C4 C3 27.6(3) . . . . ?
C1 S1 C4 C5 -156.7(3) . . . . ?
C1 C2 C19 C20 -1.4(5) . . . . ?
C1 C22 C21 C20 2.4(5) . . . . ?
C22 C21 C20 C19 1.9(5) . . . . ?
C12 C11 C10 C9 -3.1(5) . . . . ?
C12 C11 C10 C18 178.6(3) . . . . ?
C17 C16 C15 C11 0.3(6) . . . . ?
C18 C10 C9 N1 -7.5(5) . . . . ?
C18 C10 C9 C14 178.4(3) . . . . ?
C3 N1 C9 C10 -88.6(4) . . . . ?
C3 N1 C9 C14 85.3(4) . . . . ?
C3 N1 C2 C1 22.1(5) . . . . ?
C3 N1 C2 C19 -159.7(3) . . . . ?
C3 C8 C7 C6 1.8(5) . . . . ?
C8 C3 C4 S1 173.8(3) . . . . ?
C8 C3 C4 C5 -1.8(5) . . . . ?
C8 C7 C6 C5 -0.7(5) . . . . ?
C7 C6 C5 C4 -1.6(5) . . . . ?
C6 C5 C4 S1 -172.8(3) . . . . ?
C6 C5 C4 C3 2.9(5) . . . . ?
C4 S1 C1 C2 -29.5(3) . . . . ?
C4 S1 C1 C22 155.1(3) . . . . ?
C4 C3 C8 C7 -0.5(5) . . . . ?
C19 C2 C1 S1 -169.6(3) . . . . ?
C19 C2 C1 C22 5.6(5) . . . . ?
S2 C23 C44 C43 168.8(3) . . . . ?
S2 C26 C27 C28 -173.6(3) . . . . ?
N3 C31 C36 C35 -178.7(3) . . . . ?
N3 C24 C23 S2 10.8(4) . . . . ?
N3 C24 C23 C44 -174.7(3) . . . . ?
N3 C24 C41 C42 179.3(3) . . . . ?
N3 C25 C26 S2 -5.7(4) . . . . ?
N3 C25 C26 C27 177.5(3) . . . . ?
N3 C25 C30 C29 180.0(3) . . . . ?
C38 C37 C33 C32 0.7(5) . . . . ?
C38 C37 C33 C34 -179.0(3) . . . . ?
C37 C38 C39 C40 -1.9(6) . . . . ?
C37 C33 C32 C31 177.6(3) . . . . ?
C37 C33 C32 C40 -1.6(5) . . . . ?
C37 C33 C34 N4 0.6(5) . . . . ?
C37 C33 C34 C35 -176.2(3) . . . . ?
C33 C32 C31 N3 179.9(3) . . . . ?
C33 C32 C31 C36 0.1(5) . . . . ?
C33 C32 C40 C39 0.7(5) . . . . ?
C32 C33 C34 N4 -179.1(3) . . . . ?
C32 C33 C34 C35 4.1(5) . . . . ?
C32 C31 C36 C35 1.2(5) . . . . ?
C32 C40 C39 C38 1.0(5) . . . . ?
C31 N3 C24 C23 -176.3(3) . . . . ?
C31 N3 C24 C41 2.8(5) . . . . ?
C31 N3 C25 C26 173.3(3) . . . . ?
C31 N3 C25 C30 -6.8(5) . . . . ?
C31 C32 C40 C39 -178.4(3) . . . . ?
C31 C36 C35 C34 0.2(5) . . . . ?
C24 N3 C31 C32 107.5(4) . . . . ?
C24 N3 C31 C36 -72.6(4) . . . . ?
C24 N3 C25 C26 -28.2(5) . . . . ?
C24 N3 C25 C30 151.7(3) . . . . ?
C24 C23 C44 C43 -5.9(5) . . . . ?
C23 S2 C26 C25 32.4(3) . . . . ?
C23 S2 C26 C27 -150.7(3) . . . . ?
C23 C24 C41 C42 -1.5(5) . . . . ?
C23 C44 C43 C42 0.8(5) . . . . ?
C44 C43 C42 C41 3.9(5) . . . . ?
C43 C42 C41 C24 -3.5(6) . . . . ?
C40 C32 C31 N3 -0.9(5) . . . . ?
C40 C32 C31 C36 179.2(3) . . . . ?
C39 C38 C37 C33 1.0(5) . . . . ?
C25 N3 C31 C32 -93.2(4) . . . . ?
C25 N3 C31 C36 86.7(4) . . . . ?
C25 N3 C24 C23 25.4(5) . . . . ?
C25 N3 C24 C41 -155.5(3) . . . . ?
C25 C26 C27 C28 3.3(5) . . . . ?
C26 S2 C23 C24 -34.8(3) . . . . ?
C26 S2 C23 C44 150.5(3) . . . . ?
C26 C25 C30 C29 -0.1(5) . . . . ?
C26 C27 C28 C29 -1.5(5) . . . . ?
C41 C24 C23 S2 -168.5(3) . . . . ?
C41 C24 C23 C44 6.1(5) . . . . ?
C27 C28 C29 C30 -1.0(5) . . . . ?
C28 C29 C30 C25 1.9(6) . . . . ?
C30 C25 C26 S2 174.4(3) . . . . ?
C30 C25 C26 C27 -2.4(5) . . . . ?
C36 C35 C34 N4 -179.7(3) . . . . ?
C36 C35 C34 C33 -2.9(5) . . . . ?
C34 C33 C32 C31 -2.7(5) . . . . ?
C34 C33 C32 C40 178.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.52(9)
2 0.48(9)

