# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20210428wuzhibing_0m
_database_code_depnum_ccdc_archive 'CCDC 2082767'
loop_
_audit_author_name
_audit_author_address
'shuaitao Hou'
;GuiZhou University
China
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2022-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-05-07
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 Cl N2 O S2'
_chemical_formula_sum            'C16 H11 Cl N2 O S2'
_chemical_formula_weight         346.84
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1736(4)
_cell_length_b                   8.9413(4)
_cell_length_c                   12.3309(6)
_cell_angle_alpha                105.112(2)
_cell_angle_beta                 93.310(2)
_cell_angle_gamma                111.564(2)
_cell_volume                     797.19(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      71.966
_cell_measurement_theta_min      3.768
_shelx_estimated_absorpt_T_max   0.432
_shelx_estimated_absorpt_T_min   0.382
_exptl_absorpt_coefficient_mu    4.585
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.2359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20086
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.569
_diffrn_reflns_theta_min         3.768
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_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             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2825
_reflns_number_total             3126
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.808
_refine_diff_density_min         -1.245
_refine_diff_density_rms         0.328
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0953
_refine_ls_restrained_S_all      1.119
_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)+(0.1729P)²+0.2279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2294
_refine_ls_wR_factor_ref         0.2356
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.70877(17) 1.12972(14) 0.95189(11) 0.0902(5) Uani 1 1 d . . . . .
S1 S 0.72369(11) 0.36634(10) 0.67558(6) 0.0498(3) Uani 1 1 d . . . . .
S2 S 0.73566(10) 0.02744(10) 0.57499(6) 0.0474(3) Uani 1 1 d . . . . .
O1 O 0.7806(5) -0.2695(4) 0.4417(2) 0.0732(8) Uani 1 1 d . . . . .
N1 N 0.7542(4) 0.2306(3) 0.4585(2) 0.0493(6) Uani 1 1 d . . . . .
N2 N 0.7605(4) 0.0897(3) 0.3845(2) 0.0483(6) Uani 1 1 d . . . . .
C1 C 0.7143(5) 0.9528(4) 0.8541(3) 0.0520(7) Uani 1 1 d . . . . .
C2 C 0.8756(4) 0.9424(5) 0.8417(3) 0.0587(8) Uani 1 1 d . . . . .
H2 H 0.980476 1.028377 0.885794 0.070 Uiso 1 1 calc R U . . .
C3 C 0.8814(5) 0.8036(5) 0.7631(3) 0.0580(8) Uani 1 1 d . . . . .
H3 H 0.990622 0.796213 0.754245 0.070 Uiso 1 1 calc R U . . .
C4 C 0.7252(5) 0.6748(4) 0.6973(3) 0.0506(7) Uani 1 1 d . . . . .
C5 C 0.5640(5) 0.6882(4) 0.7124(3) 0.0539(8) Uani 1 1 d . . . . .
H5 H 0.458449 0.601977 0.669347 0.065 Uiso 1 1 calc R U . . .
C6 C 0.5572(4) 0.8270(4) 0.7899(3) 0.0525(7) Uani 1 1 d . . . . .
H6 H 0.448540 0.835687 0.798737 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7321(7) 0.5269(5) 0.6090(3) 0.0672(10) Uani 1 1 d . . . . .
H7A H 0.841472 0.561842 0.577804 0.081 Uiso 1 1 calc R U . . .
H7B H 0.631809 0.482101 0.547151 0.081 Uiso 1 1 calc R U . . .
C8 C 0.7401(4) 0.2140(4) 0.5605(2) 0.0405(6) Uani 1 1 d . . . . .
C9 C 0.7513(4) -0.0261(4) 0.4316(2) 0.0420(6) Uani 1 1 d . . . . .
C10 C 0.7626(4) -0.1914(4) 0.3783(2) 0.0472(7) Uani 1 1 d . . . . .
C11 C 0.7578(4) -0.2545(4) 0.2545(3) 0.0458(7) Uani 1 1 d . . . . .
C12 C 0.6727(4) -0.2114(5) 0.1747(3) 0.0538(8) Uani 1 1 d . . . . .
H12 H 0.619035 -0.135720 0.198116 0.065 Uiso 1 1 calc R U . . .
C13 C 0.6680(5) -0.2822(5) 0.0589(3) 0.0686(11) Uani 1 1 d . . . . .
H13 H 0.609921 -0.255272 0.004500 0.082 Uiso 1 1 calc R U . . .
C14 C 0.7509(6) -0.3933(6) 0.0255(4) 0.0807(14) Uani 1 1 d . . . . .
H14 H 0.748591 -0.440112 -0.051664 0.097 Uiso 1 1 calc R U . . .
C15 C 0.8360(6) -0.4347(5) 0.1047(4) 0.0772(13) Uani 1 1 d . . . . .
H15 H 0.892749 -0.507801 0.081436 0.093 Uiso 1 1 calc R U . . .
C16 C 0.8373(5) -0.3680(5) 0.2187(3) 0.0611(9) Uani 1 1 d . . . . .
H16 H 0.891780 -0.399078 0.272297 0.073 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
Cl1 C1 1.739(3) . ?
S1 C7 1.814(4) . ?
S1 C8 1.742(3) . ?
S2 C8 1.711(3) . ?
S2 C9 1.733(3) . ?
O1 C10 1.211(4) . ?
N1 N2 1.370(4) . ?
N1 C8 1.311(4) . ?
N2 C9 1.294(4) . ?
C1 C2 1.370(5) . ?
C1 C6 1.377(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(5) . ?
C4 C5 1.385(5) . ?
C4 C7 1.500(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.492(4) . ?
C10 C11 1.476(4) . ?
C11 C12 1.384(5) . ?
C11 C16 1.390(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.374(6) . ?
C16 H16 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
C8 S1 C7 100.31(15) . . ?
C8 S2 C9 86.11(14) . . ?
C8 N1 N2 111.2(3) . . ?
C9 N2 N1 113.0(3) . . ?
C2 C1 Cl1 119.1(3) . . ?
C2 C1 C6 121.3(3) . . ?
C6 C1 Cl1 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C7 120.4(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C7 120.8(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
S1 C7 H7A 110.0 . . ?
S1 C7 H7B 110.0 . . ?
C4 C7 S1 108.5(2) . . ?
C4 C7 H7A 110.0 . . ?
C4 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
S2 C8 S1 120.68(16) . . ?
N1 C8 S1 123.9(2) . . ?
N1 C8 S2 115.4(2) . . ?
N2 C9 S2 114.3(2) . . ?
N2 C9 C10 127.5(3) . . ?
C10 C9 S2 118.1(2) . . ?
O1 C10 C9 116.9(3) . . ?
O1 C10 C11 121.5(3) . . ?
C11 C10 C9 121.6(3) . . ?
C12 C11 C10 123.2(3) . . ?
C12 C11 C16 119.8(3) . . ?
C16 C11 C10 116.9(3) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(4) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.8 . . ?

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
Cl1 C1 C2 C3 -179.1(3) . . . . ?
Cl1 C1 C6 C5 179.6(3) . . . . ?
S2 C9 C10 O1 -8.1(4) . . . . ?
S2 C9 C10 C11 173.7(2) . . . . ?
O1 C10 C11 C12 154.3(3) . . . . ?
O1 C10 C11 C16 -22.9(5) . . . . ?
N1 N2 C9 S2 -0.6(3) . . . . ?
N1 N2 C9 C10 -177.0(3) . . . . ?
N2 N1 C8 S1 -178.6(2) . . . . ?
N2 N1 C8 S2 0.6(3) . . . . ?
N2 C9 C10 O1 168.1(3) . . . . ?
N2 C9 C10 C11 -10.0(5) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C2 C1 C6 C5 0.4(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C3 C4 C7 177.8(3) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C3 C4 C7 S1 89.1(4) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C5 C4 C7 S1 -92.9(4) . . . . ?
C6 C1 C2 C3 0.1(6) . . . . ?
C7 S1 C8 S2 -179.1(2) . . . . ?
C7 S1 C8 N1 0.1(3) . . . . ?
C7 C4 C5 C6 -177.2(3) . . . . ?
C8 S1 C7 C4 -178.3(3) . . . . ?
C8 S2 C9 N2 0.8(2) . . . . ?
C8 S2 C9 C10 177.5(2) . . . . ?
C8 N1 N2 C9 0.0(4) . . . . ?
C9 S2 C8 S1 178.44(19) . . . . ?
C9 S2 C8 N1 -0.8(2) . . . . ?
C9 C10 C11 C12 -27.6(4) . . . . ?
C9 C10 C11 C16 155.2(3) . . . . ?
C10 C11 C12 C13 -177.3(3) . . . . ?
C10 C11 C16 C15 179.0(3) . . . . ?
C11 C12 C13 C14 -0.8(5) . . . . ?
C12 C11 C16 C15 1.6(5) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
C14 C15 C16 C11 -2.1(6) . . . . ?
C16 C11 C12 C13 -0.2(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
