# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_exp_14558_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2kt5k4
_database_code_depnum_ccdc_archive 'CCDC 2377686'
loop_
_audit_author_name
_audit_author_address
'YUKUN XIE'
;GuangXi University
China
;
_audit_update_record             
;
2024-08-15 deposited with the CCDC.	2025-04-09 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            'C27 H17 Cl2 N O S2'
_chemical_formula_weight         506.43

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'
Cl Cl 0.1484 0.1585 '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'
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'

_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                   17.9420(13)
_cell_length_b                   11.8982(8)
_cell_length_c                   22.5176(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4807.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             2080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.465
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35595
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.244
_diffrn_reflns_theta_max         29.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5893
_reflns_number_gt                3649
_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 2018/2 (Sheldrick, 2018)'
_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)+(0.1000P)²] 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         5893
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1659
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
S1 S 0.54399(5) 0.00280(7) 0.27143(3) 0.0565(3) Uani 1 1 d . . . . .
S2 S 0.50006(5) 0.28396(8) 0.59220(4) 0.0671(3) Uani 1 1 d . . . . .
Cl1 Cl 0.30243(6) 0.71947(7) 0.57947(5) 0.0787(3) Uani 1 1 d . . . . .
Cl2 Cl 0.85723(5) 0.23174(8) 0.26362(6) 0.0933(4) Uani 1 1 d . . . . .
O1 O 0.39900(11) -0.07122(17) 0.29985(9) 0.0591(6) Uani 1 1 d . . . . .
N1 N 0.38525(13) -0.00158(17) 0.39351(10) 0.0418(5) Uani 1 1 d . . . . .
C2 C 0.49896(15) 0.03518(19) 0.33853(11) 0.0396(6) Uani 1 1 d . . . . .
C3 C 0.52482(15) 0.0987(2) 0.38348(12) 0.0421(6) Uani 1 1 d . . . . .
H3 H 0.571230 0.132983 0.380137 0.050 Uiso 1 1 calc R U . . .
C1 C 0.42526(15) -0.01687(19) 0.34096(12) 0.0422(6) Uani 1 1 d . . . . .
C9 C 0.41239(15) 0.06168(19) 0.44176(11) 0.0395(6) Uani 1 1 d . . . . .
C4 C 0.48192(15) 0.1142(2) 0.43618(11) 0.0395(6) Uani 1 1 d . . . . .
C5 C 0.50718(15) 0.1822(2) 0.48309(12) 0.0464(7) Uani 1 1 d . . . . .
H5 H 0.552952 0.218339 0.479641 0.056 Uiso 1 1 calc R U . . .
C10 C 0.31140(15) -0.0499(2) 0.39486(12) 0.0427(6) Uani 1 1 d . . . . .
C22 C 0.63011(16) 0.0750(2) 0.27656(11) 0.0455(7) Uani 1 1 d . . . . .
C8 C 0.37143(16) 0.0734(2) 0.49398(13) 0.0497(7) Uani 1 1 d . . . . .
H8 H 0.325997 0.036566 0.498058 0.060 Uiso 1 1 calc R U . . .
C6 C 0.46580(17) 0.1967(2) 0.53403(12) 0.0497(7) Uani 1 1 d . . . . .
C7 C 0.39824(17) 0.1398(3) 0.53990(12) 0.0538(7) Uani 1 1 d . . . . .
H7 H 0.370964 0.146404 0.574846 0.065 Uiso 1 1 calc R U . . .
C27 C 0.63854(17) 0.1800(2) 0.25042(13) 0.0517(7) Uani 1 1 d . . . . .
H27 H 0.597199 0.217096 0.235046 0.062 Uiso 1 1 calc R U . . .
C16 C 0.44530(17) 0.4075(2) 0.58388(12) 0.0518(7) Uani 1 1 d . . . . .
C26 C 0.70828(18) 0.2297(2) 0.24717(14) 0.0547(8) Uani 1 1 d . . . . .
H26 H 0.714085 0.299797 0.229517 0.066 Uiso 1 1 calc R U . . .
C25 C 0.76839(17) 0.1743(2) 0.27023(14) 0.0534(7) Uani 1 1 d . . . . .
C19 C 0.35977(17) 0.6008(2) 0.58047(14) 0.0559(7) Uani 1 1 d . . . . .
C21 C 0.44816(18) 0.4856(3) 0.62905(14) 0.0602(8) Uani 1 1 d . . . . .
H21 H 0.479262 0.472586 0.661364 0.072 Uiso 1 1 calc R U . . .
C20 C 0.40598(19) 0.5826(3) 0.62749(14) 0.0624(8) Uani 1 1 d . . . . .
H20 H 0.409085 0.634813 0.658118 0.075 Uiso 1 1 calc R U . . .
C23 C 0.69181(18) 0.0223(3) 0.30088(15) 0.0617(8) Uani 1 1 d . . . . .
H23 H 0.686492 -0.047149 0.319346 0.074 Uiso 1 1 calc R U . . .
C24 C 0.76087(18) 0.0720(2) 0.29790(15) 0.0653(9) Uani 1 1 d . . . . .
H24 H 0.802169 0.036703 0.314479 0.078 Uiso 1 1 calc R U . . .
C11 C 0.25322(17) 0.0070(3) 0.36961(14) 0.0610(8) Uani 1 1 d . . . . .
H11 H 0.260725 0.077356 0.352597 0.073 Uiso 1 1 calc R U . . .
C15 C 0.30004(19) -0.1531(2) 0.42070(15) 0.0653(9) Uani 1 1 d . . . . .
H15 H 0.339774 -0.191391 0.437831 0.078 Uiso 1 1 calc R U . . .
C13 C 0.1723(2) -0.1452(3) 0.39541(15) 0.0767(11) Uani 1 1 d . . . . .
H13 H 0.125156 -0.177777 0.394962 0.092 Uiso 1 1 calc R U . . .
C12 C 0.18327(19) -0.0412(4) 0.36971(15) 0.0771(11) Uani 1 1 d . . . . .
H12 H 0.143406 -0.003429 0.352401 0.092 Uiso 1 1 calc R U . . .
C14 C 0.2299(2) -0.1997(3) 0.42124(17) 0.0760(11) Uani 1 1 d . . . . .
H14 H 0.222068 -0.268934 0.439405 0.091 Uiso 1 1 calc R U . . .
C18 C 0.3575(2) 0.5268(3) 0.53457(17) 0.0850(12) Uani 1 1 d . . . . .
H18 H 0.326828 0.540916 0.502131 0.102 Uiso 1 1 calc R U . . .
C17 C 0.4006(2) 0.4310(3) 0.53592(16) 0.0879(13) Uani 1 1 d . . . . .
H17 H 0.399329 0.381548 0.503951 0.105 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 C2 1.756(3) . ?
S1 C22 1.772(3) . ?
S2 C16 1.778(3) . ?
S2 C6 1.780(3) . ?
Cl1 C19 1.747(3) . ?
Cl2 C25 1.741(3) . ?
O1 C1 1.223(3) . ?
N1 C1 1.396(3) . ?
N1 C9 1.408(3) . ?
N1 C10 1.445(3) . ?
C2 C3 1.346(3) . ?
C2 C1 1.461(4) . ?
C3 C4 1.426(4) . ?
C9 C8 1.394(4) . ?
C9 C4 1.401(4) . ?
C4 C5 1.406(4) . ?
C5 C6 1.377(4) . ?
C10 C11 1.368(4) . ?
C10 C15 1.374(4) . ?
C22 C23 1.385(4) . ?
C22 C27 1.390(4) . ?
C8 C7 1.387(4) . ?
C6 C7 1.395(4) . ?
C27 C26 1.386(4) . ?
C16 C17 1.374(4) . ?
C16 C21 1.379(4) . ?
C26 C25 1.366(4) . ?
C25 C24 1.374(4) . ?
C19 C18 1.358(4) . ?
C19 C20 1.362(4) . ?
C21 C20 1.381(4) . ?
C23 C24 1.375(4) . ?
C11 C12 1.380(4) . ?
C15 C14 1.376(5) . ?
C13 C14 1.352(5) . ?
C13 C12 1.381(5) . ?
C18 C17 1.377(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 S1 C22 103.82(12) . . ?
C16 S2 C6 102.32(13) . . ?
C1 N1 C9 123.1(2) . . ?
C1 N1 C10 115.9(2) . . ?
C9 N1 C10 120.9(2) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 S1 127.7(2) . . ?
C1 C2 S1 110.82(17) . . ?
C2 C3 C4 120.8(2) . . ?
O1 C1 N1 120.8(2) . . ?
O1 C1 C2 123.0(2) . . ?
N1 C1 C2 116.2(2) . . ?
C8 C9 C4 120.0(2) . . ?
C8 C9 N1 121.5(2) . . ?
C4 C9 N1 118.5(2) . . ?
C9 C4 C5 118.5(2) . . ?
C9 C4 C3 119.8(2) . . ?
C5 C4 C3 121.7(2) . . ?
C6 C5 C4 121.6(3) . . ?
C11 C10 C15 120.4(3) . . ?
C11 C10 N1 119.6(2) . . ?
C15 C10 N1 120.1(3) . . ?
C23 C22 C27 119.2(3) . . ?
C23 C22 S1 120.2(2) . . ?
C27 C22 S1 120.2(2) . . ?
C7 C8 C9 120.2(3) . . ?
C5 C6 C7 119.1(3) . . ?
C5 C6 S2 120.0(2) . . ?
C7 C6 S2 120.9(2) . . ?
C8 C7 C6 120.5(3) . . ?
C26 C27 C22 120.3(3) . . ?
C17 C16 C21 117.6(3) . . ?
C17 C16 S2 125.0(2) . . ?
C21 C16 S2 117.3(2) . . ?
C25 C26 C27 119.1(3) . . ?
C26 C25 C24 121.5(3) . . ?
C26 C25 Cl2 120.1(2) . . ?
C24 C25 Cl2 118.4(2) . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 Cl1 119.8(3) . . ?
C20 C19 Cl1 119.8(2) . . ?
C16 C21 C20 121.6(3) . . ?
C19 C20 C21 119.1(3) . . ?
C24 C23 C22 120.4(3) . . ?
C25 C24 C23 119.5(3) . . ?
C10 C11 C12 119.2(3) . . ?
C10 C15 C14 120.0(3) . . ?
C14 C13 C12 120.1(3) . . ?
C11 C12 C13 120.2(3) . . ?
C13 C14 C15 120.1(3) . . ?
C19 C18 C17 120.2(3) . . ?
C16 C17 C18 120.9(3) . . ?

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.119



