# Electronic Supplementary Material (ESI) for Organic 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_WQ20220727
_database_code_depnum_ccdc_archive 'CCDC 2225617'
loop_
_audit_author_name
_audit_author_address
'Lei Wang'
;Yangzhou University
China
;
_audit_update_record             
;
2022-12-10 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 Cl O S'
_chemical_formula_sum            'C15 H13 Cl O S'
_chemical_formula_weight         276.76

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'
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'
Cl Cl 0.1484 0.1585 '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                   11.6365(7)
_cell_length_b                   8.5993(5)
_cell_length_c                   27.6425(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2766.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6192
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.412
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6677
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_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            24408
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2724
_reflns_number_gt                1776
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0435P)²+1.3865P] 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         2724
_refine_ls_number_parameters     164
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_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 0.4321(2) 0.8482(3) 0.30016(9) 0.0541(6) Uani 1 1 d . . . . .
H1 H 0.4082 0.9480 0.2920 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3836(2) 0.7208(3) 0.27766(9) 0.0621(7) Uani 1 1 d . . . . .
C3 C 0.4176(3) 0.5723(3) 0.28850(12) 0.0726(8) Uani 1 1 d . . . . .
H3 H 0.3853 0.4874 0.2727 0.087 Uiso 1 1 calc R U . . .
C4 C 0.5000(3) 0.5518(4) 0.32304(13) 0.0800(9) Uani 1 1 d . . . . .
H4 H 0.5239 0.4517 0.3309 0.096 Uiso 1 1 calc R U . . .
C5 C 0.5478(2) 0.6759(3) 0.34610(11) 0.0648(7) Uani 1 1 d . . . . .
H5 H 0.6028 0.6587 0.3699 0.078 Uiso 1 1 calc R U . . .
C6 C 0.5167(2) 0.8267(3) 0.33500(8) 0.0478(6) Uani 1 1 d . . . . .
C7 C 0.5711(2) 0.9581(3) 0.36008(9) 0.0549(6) Uani 1 1 d . U . . .
C8 C 0.6779(2) 0.9644(4) 0.37593(10) 0.0742(8) Uani 1 1 d . U . . .
H8A H 0.7266 0.8798 0.3716 0.089 Uiso 1 1 calc R U . . .
H8B H 0.7044 1.0533 0.3915 0.089 Uiso 1 1 calc R U . . .
C9 C 0.38192(19) 1.0390(3) 0.40998(8) 0.0439(6) Uani 1 1 d . . . . .
C10 C 0.2669(2) 1.0650(3) 0.40196(9) 0.0563(7) Uani 1 1 d . . . . .
H10 H 0.2432 1.1239 0.3756 0.068 Uiso 1 1 calc R U . . .
C11 C 0.1870(2) 1.0031(3) 0.43327(10) 0.0631(7) Uani 1 1 d . . . . .
H11 H 0.1092 1.0191 0.4273 0.076 Uiso 1 1 calc R U . . .
C12 C 0.2192(2) 0.9184(3) 0.47324(9) 0.0518(6) Uani 1 1 d . . . . .
C13 C 0.1316(3) 0.8534(4) 0.50778(11) 0.0819(9) Uani 1 1 d . . . . .
H13A H 0.1111 0.9316 0.5310 0.123 Uiso 1 1 calc R U . . .
H13B H 0.1634 0.7651 0.5242 0.123 Uiso 1 1 calc R U . . .
H13C H 0.0644 0.8221 0.4901 0.123 Uiso 1 1 calc R U . . .
C14 C 0.3348(2) 0.8937(3) 0.48081(9) 0.0540(6) Uani 1 1 d . . . . .
H14 H 0.3585 0.8367 0.5076 0.065 Uiso 1 1 calc R U . . .
C15 C 0.4157(2) 0.9521(3) 0.44948(9) 0.0527(6) Uani 1 1 d . . . . .
H15 H 0.4933 0.9330 0.4549 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.27678(9) 0.74822(12) 0.23464(3) 0.1131(4) Uani 1 1 d . . . . .
O1 O 0.55593(17) 1.2366(2) 0.39998(7) 0.0756(6) Uani 1 1 d . . . . .
S1 S 0.48424(6) 1.12822(7) 0.37072(2) 0.0553(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 1.380(4) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(4) . ?
C2 Cl1 1.736(3) . ?
C3 C4 1.365(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.469(3) . ?
C7 C8 1.318(4) . ?
C7 S1 1.802(3) . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 C10 1.375(3) . ?
C9 C15 1.380(3) . ?
C9 S1 1.784(2) . ?
C10 C11 1.377(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.377(3) . ?
C12 C13 1.504(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
O1 S1 1.4896(19) . ?

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 119.8(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 Cl1 118.9(2) . . ?
C1 C2 Cl1 119.6(2) . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 117.7(2) . . ?
C5 C6 C7 120.3(2) . . ?
C1 C6 C7 122.0(2) . . ?
C8 C7 C6 126.5(3) . . ?
C8 C7 S1 116.2(2) . . ?
C6 C7 S1 117.37(18) . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C10 C9 C15 119.5(2) . . ?
C10 C9 S1 118.80(18) . . ?
C15 C9 S1 121.62(18) . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C14 118.0(2) . . ?
C11 C12 C13 121.4(2) . . ?
C14 C12 C13 120.5(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C12 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C12 C14 H14 119.4 . . ?
C14 C15 C9 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C9 C15 H15 119.9 . . ?
O1 S1 C9 108.20(11) . . ?
O1 S1 C7 106.41(12) . . ?
C9 S1 C7 97.16(11) . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.040

