# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_202507203_auto
_database_code_depnum_ccdc_archive 'CCDC 2470543'
loop_
_audit_author_name
_audit_author_address
LLZ
;zhengzhou university
China
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2026-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Cl N O S'
_chemical_formula_weight         287.75

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'

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

_cell_length_a                   12.4025(2)
_cell_length_b                   8.06004(14)
_cell_length_c                   25.3975(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2538.85(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(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    1.506
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.110
_shelx_estimated_absorpt_T_min   0.525
_shelx_estimated_absorpt_T_max   0.853
_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      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8772
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.480
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_full        67.052
_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             2267
_reflns_number_gt                1859
_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    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0942P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2267
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1480
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
Cl1 Cl 0.68941(8) 0.48978(16) 0.52809(4) 0.1017(4) Uani 1 1 d . . . . .
S1 S 0.50929(5) 0.43092(8) 0.71674(3) 0.0571(2) Uani 1 1 d . . . . .
O1 O 0.3181(2) 0.0998(2) 0.59880(9) 0.0758(6) Uani 1 1 d . . . . .
N1 N 0.2425(2) 0.1909(3) 0.67994(12) 0.0696(7) Uani 1 1 d . . . . .
H1 H 0.212(3) 0.119(6) 0.6983(16) 0.092(12) Uiso 1 1 d . . . . .
C1 C 0.5393(2) 0.4026(4) 0.59973(12) 0.0619(6) Uani 1 1 d . . . . .
H1A H 0.571961 0.481720 0.621067 0.074 Uiso 1 1 calc R U . . .
C2 C 0.5779(3) 0.3765(4) 0.54969(13) 0.0741(8) Uani 1 1 d . . . . .
C3 C 0.5325(3) 0.2617(5) 0.51633(14) 0.0871(10) Uani 1 1 d . . . . .
H3 H 0.560840 0.243168 0.482936 0.105 Uiso 1 1 calc R U . . .
C4 C 0.4440(3) 0.1753(4) 0.53391(13) 0.0821(9) Uani 1 1 d . . . . .
H4 H 0.410493 0.100075 0.511454 0.098 Uiso 1 1 calc R U . . .
C5 C 0.4034(2) 0.1974(3) 0.58432(12) 0.0657(7) Uani 1 1 d . . . . .
C6 C 0.4512(2) 0.3116(3) 0.61917(11) 0.0553(6) Uani 1 1 d . . . . .
C7 C 0.41898(19) 0.3289(3) 0.67418(11) 0.0516(6) Uani 1 1 d . . . . .
C8 C 0.33228(18) 0.2673(3) 0.70175(12) 0.0536(6) Uani 1 1 d . . . . .
C9 C 0.34014(18) 0.2921(3) 0.75761(11) 0.0527(6) Uani 1 1 d . . . . .
C10 C 0.43363(19) 0.3795(3) 0.77165(11) 0.0532(6) Uani 1 1 d . . . . .
C11 C 0.4587(2) 0.4146(3) 0.82382(13) 0.0644(7) Uani 1 1 d . . . . .
H11 H 0.520717 0.473333 0.832527 0.077 Uiso 1 1 calc R U . . .
C12 C 0.3890(3) 0.3599(4) 0.86213(14) 0.0757(8) Uani 1 1 d . . . . .
H12 H 0.404266 0.381636 0.897305 0.091 Uiso 1 1 calc R U . . .
C13 C 0.2957(3) 0.2724(4) 0.84917(14) 0.0755(8) Uani 1 1 d . . . . .
H13 H 0.250012 0.236490 0.875877 0.091 Uiso 1 1 calc R U . . .
C14 C 0.2702(2) 0.2385(3) 0.79797(14) 0.0650(7) Uani 1 1 d . . . . .
H14 H 0.207442 0.180671 0.789814 0.078 Uiso 1 1 calc R U . . .
C15 C 0.2311(2) 0.1861(3) 0.62497(14) 0.0731(9) Uani 1 1 d . . . . .
H15A H 0.227553 0.298813 0.611703 0.088 Uiso 1 1 calc R U . . .
H15B H 0.163493 0.131887 0.616343 0.088 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 C2 1.746(4) . ?
S1 C10 1.731(3) . ?
S1 C7 1.760(2) . ?
O1 C5 1.369(4) . ?
O1 C15 1.446(4) . ?
N1 C8 1.388(3) . ?
N1 C15 1.404(5) . ?
N1 H1 0.83(4) . ?
C1 C2 1.374(5) . ?
C1 C6 1.405(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.375(5) . ?
C3 C4 1.375(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.408(4) . ?
C6 C7 1.460(4) . ?
C7 C8 1.376(4) . ?
C8 C9 1.436(4) . ?
C9 C10 1.403(3) . ?
C9 C14 1.411(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.374(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

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
C10 S1 C7 92.17(12) . . ?
C5 O1 C15 115.1(2) . . ?
C8 N1 C15 119.4(3) . . ?
C8 N1 H1 117(3) . . ?
C15 N1 H1 119(3) . . ?
C2 C1 C6 121.1(3) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C1 C2 C3 122.0(3) . . ?
C1 C2 Cl1 119.1(3) . . ?
C3 C2 Cl1 118.9(3) . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C3 C4 C5 121.6(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
O1 C5 C4 117.0(3) . . ?
O1 C5 C6 122.2(3) . . ?
C4 C5 C6 120.8(3) . . ?
C1 C6 C5 116.6(3) . . ?
C1 C6 C7 120.0(2) . . ?
C5 C6 C7 123.3(3) . . ?
C8 C7 C6 131.8(2) . . ?
C8 C7 S1 110.7(2) . . ?
C6 C7 S1 117.26(18) . . ?
C7 C8 N1 125.7(3) . . ?
C7 C8 C9 113.5(2) . . ?
N1 C8 C9 120.7(2) . . ?
C10 C9 C14 118.5(3) . . ?
C10 C9 C8 112.2(2) . . ?
C14 C9 C8 129.3(2) . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 S1 126.7(2) . . ?
C9 C10 S1 111.3(2) . . ?
C12 C11 C10 118.0(3) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C11 C12 C13 121.1(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 119.2(3) . . ?
C13 C14 H14 120.4 . . ?
C9 C14 H14 120.4 . . ?
N1 C15 O1 113.3(2) . . ?
N1 C15 H15A 108.9 . . ?
O1 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
O1 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?

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
C6 C1 C2 C3 0.3(4) . . . . ?
C6 C1 C2 Cl1 -178.6(2) . . . . ?
C1 C2 C3 C4 1.9(5) . . . . ?
Cl1 C2 C3 C4 -179.3(3) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
C15 O1 C5 C4 -134.4(3) . . . . ?
C15 O1 C5 C6 47.8(3) . . . . ?
C3 C4 C5 O1 -177.0(3) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C2 C1 C6 C5 -1.9(4) . . . . ?
C2 C1 C6 C7 173.5(2) . . . . ?
O1 C5 C6 C1 179.1(2) . . . . ?
C4 C5 C6 C1 1.4(4) . . . . ?
O1 C5 C6 C7 3.8(4) . . . . ?
C4 C5 C6 C7 -173.8(3) . . . . ?
C1 C6 C7 C8 173.6(2) . . . . ?
C5 C6 C7 C8 -11.3(4) . . . . ?
C1 C6 C7 S1 -12.8(3) . . . . ?
C5 C6 C7 S1 162.31(19) . . . . ?
C10 S1 C7 C8 3.21(18) . . . . ?
C10 S1 C7 C6 -171.73(19) . . . . ?
C6 C7 C8 N1 -11.0(4) . . . . ?
S1 C7 C8 N1 175.0(2) . . . . ?
C6 C7 C8 C9 170.5(2) . . . . ?
S1 C7 C8 C9 -3.5(2) . . . . ?
C15 N1 C8 C7 -6.1(4) . . . . ?
C15 N1 C8 C9 172.4(2) . . . . ?
C7 C8 C9 C10 2.0(3) . . . . ?
N1 C8 C9 C10 -176.6(2) . . . . ?
C7 C8 C9 C14 -176.3(2) . . . . ?
N1 C8 C9 C14 5.1(4) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C8 C9 C10 C11 -178.7(2) . . . . ?
C14 C9 C10 S1 179.01(18) . . . . ?
C8 C9 C10 S1 0.5(2) . . . . ?
C7 S1 C10 C11 177.1(2) . . . . ?
C7 S1 C10 C9 -2.08(18) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
S1 C10 C11 C12 -178.6(2) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C9 0.5(4) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C8 C9 C14 C13 178.0(2) . . . . ?
C8 N1 C15 O1 60.4(3) . . . . ?
C5 O1 C15 N1 -90.4(3) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.056



