# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2070247'
loop_
_audit_author_name
_audit_author_address
'Xiunan Zhang'
;Tianjin university
China
;
_audit_update_record             
;
2021-04-16 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_audit_creation_date             2021-04-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H14 O2 S2'
_chemical_formula_sum            'C18 H14 O2 S2'
_chemical_formula_weight         326.41
_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'
O O 0.0106 0.0060 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.921(3)
_cell_length_b                   16.888(3)
_cell_length_c                   7.6224(15)
_cell_angle_alpha                90
_cell_angle_beta                 120.00(3)
_cell_angle_gamma                90
_cell_volume                     1551.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1779
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.602
_cell_measurement_theta_min      3.380
_shelx_estimated_absorpt_T_max   0.950
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_correction_T_min  0.9184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7558
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.602
_diffrn_reflns_theta_min         3.380
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1225
_reflns_number_total             1779
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.022
_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)+(0.0692P)²+1.1938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1473
_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 Me refined with riding coordinates:
 C1(H1A,H1B,H1C)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C3(H3), C7(H7), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.04626(5) 0.23589(4) 0.43567(11) 0.0568(3) Uani 1 1 d . . . . .
O1 O 0.27486(16) -0.00349(15) 0.5463(4) 0.0764(7) Uani 1 1 d . . . . .
C5 C 0.05645(19) 0.16651(16) 0.5565(4) 0.0470(6) Uani 1 1 d . . . . .
C6 C 0.02908(19) 0.08153(14) 0.5231(4) 0.0423(6) Uani 1 1 d . . . . .
C2 C 0.0421(2) 0.31344(17) 0.5505(4) 0.0570(7) Uani 1 1 d . . . . .
C8 C 0.10046(18) 0.02388(15) 0.5185(4) 0.0433(6) Uani 1 1 d . . . . .
C9 C 0.2045(2) 0.04366(18) 0.5183(4) 0.0548(7) Uani 1 1 d . . . . .
H9 H 0.215609 0.096023 0.495004 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1454(2) 0.28665(18) 0.6748(5) 0.0660(8) Uani 1 1 d . . . . .
H3 H 0.205429 0.319895 0.750457 0.079 Uiso 1 1 calc R U . . .
C7 C -0.07151(19) 0.05544(15) 0.5013(4) 0.0443(6) Uani 1 1 d . . . . .
H7 H -0.120970 0.092750 0.500144 0.053 Uiso 1 1 calc R U . . .
C1 C 0.0014(3) 0.39734(19) 0.5061(6) 0.0788(10) Uani 1 1 d . . . . .
H1A H -0.076744 0.397662 0.410721 0.118 Uiso 1 1 calc R U . . .
H1B H 0.015140 0.422764 0.629109 0.118 Uiso 1 1 calc R U . . .
H1C H 0.039871 0.425278 0.449857 0.118 Uiso 1 1 calc R U . . .
C4 C 0.1540(2) 0.20343(18) 0.6798(5) 0.0599(8) Uani 1 1 d . . . . .
H4 H 0.220143 0.176477 0.759671 0.072 Uiso 1 1 calc R U . . .


_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 C5 1.717(3) . ?
S1 C2 1.708(3) . ?
O1 C9 1.195(3) . ?
C5 C6 1.474(4) . ?
C5 C4 1.356(3) . ?
C6 C8 1.404(3) . ?
C6 C7 1.397(3) . ?
C2 C3 1.344(4) . ?
C2 C1 1.500(4) . ?
C8 C9 1.488(3) . ?
C8 C7 1.385(4) 5_556 ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.409(4) . ?
C7 H7 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4 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
C2 S1 C5 93.16(14) . . ?
C6 C5 S1 119.85(17) . . ?
C4 C5 S1 109.6(2) . . ?
C4 C5 C6 130.5(2) . . ?
C8 C6 C5 123.7(2) . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 C8 117.3(2) . . ?
C3 C2 S1 110.2(2) . . ?
C3 C2 C1 128.8(3) . . ?
C1 C2 S1 121.0(2) . . ?
C6 C8 C9 123.1(2) . . ?
C7 C8 C6 120.2(2) 5_556 . ?
C7 C8 C9 116.6(2) 5_556 . ?
O1 C9 C8 124.2(3) . . ?
O1 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
C2 C3 H3 123.2 . . ?
C2 C3 C4 113.7(3) . . ?
C4 C3 H3 123.2 . . ?
C6 C7 H7 118.7 . . ?
C8 C7 C6 122.5(2) 5_556 . ?
C8 C7 H7 118.7 5_556 . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C4 C3 113.4(2) . . ?
C5 C4 H4 123.3 . . ?
C3 C4 H4 123.3 . . ?

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 C5 C6 C8 145.3(2) . . . . ?
S1 C5 C6 C7 -36.9(3) . . . . ?
S1 C5 C4 C3 -0.4(3) . . . . ?
S1 C2 C3 C4 -0.4(3) . . . . ?
C5 S1 C2 C3 0.2(2) . . . . ?
C5 S1 C2 C1 179.6(3) . . . . ?
C5 C6 C8 C9 -8.8(4) . . . . ?
C5 C6 C8 C7 176.0(2) . . . 5_556 ?
C5 C6 C7 C8 -176.1(2) . . . 5_556 ?
C6 C5 C4 C3 -177.6(3) . . . . ?
C6 C8 C9 O1 167.8(3) . . . . ?
C2 S1 C5 C6 177.7(2) . . . . ?
C2 S1 C5 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C8 C6 C7 C8 1.8(4) . . . 5_556 ?
C7 C6 C8 C9 173.5(2) . . . . ?
C7 C6 C8 C7 -1.7(4) . . . 5_556 ?
C7 C8 C9 O1 -16.9(4) 5_556 . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C4 C5 C6 C8 -37.7(4) . . . . ?
C4 C5 C6 C7 140.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
