# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_a
_database_code_depnum_ccdc_archive 'CCDC 2486964'
loop_
_audit_author_name
_audit_author_address
'Xiaowei Liu'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2025-09-10 deposited with the CCDC.	2025-11-18 downloaded from the CCDC.
;
_audit_creation_date             2025-07-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 Cl N2 O S'
_chemical_formula_sum            'C16 H9 Cl N2 O S'
_chemical_formula_weight         312.76
_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'
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.794(3)
_cell_length_b                   11.032(2)
_cell_length_c                   7.8875(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.768(7)
_cell_angle_gamma                90
_cell_volume                     1430.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4066
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1178 before and 0.0558 after correction.
The Ratio of minimum to maximum transmission is 0.8218.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9917
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.385
_diffrn_reflns_theta_min         2.478
_diffrn_ambient_temperature      293.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Turbo X-Ray Source (TXS)'
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2060
_reflns_number_total             2619
_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 V8.41 (Bruker, 2024)'
_computing_data_collection       'APEX6 V2024.9-1 (Bruker, 2025)'
_computing_data_reduction        'SAINT V8.41 (Bruker, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1494
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
;
_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 0.84757(4) 0.45408(7) 0.83868(9) 0.0702(3) Uani 1 1 d . . . . .
S1 S 0.73533(4) 0.48013(7) 0.29408(8) 0.0581(3) Uani 1 1 d . . . . .
O1 O 0.65700(10) 0.71760(17) 0.5902(2) 0.0618(5) Uani 1 1 d . . . . .
N1 N 0.74157(12) 0.7248(2) 0.6570(3) 0.0635(6) Uani 1 1 d . . . . .
N2 N 0.76395(17) 0.2641(3) 0.4937(4) 0.0864(8) Uani 1 1 d . . . . .
C1 C 0.49873(14) 0.6953(2) 0.4274(3) 0.0569(6) Uani 1 1 d . . . . .
H1 H 0.515173 0.756888 0.507318 0.068 Uiso 1 1 calc R U . . .
C2 C 0.41769(16) 0.6826(3) 0.3521(4) 0.0654(7) Uani 1 1 d . . . . .
H2 H 0.379748 0.736310 0.380243 0.078 Uiso 1 1 calc R U . . .
C3 C 0.39250(15) 0.5908(3) 0.2353(4) 0.0640(7) Uani 1 1 d . . . . .
H3 H 0.337733 0.582356 0.184470 0.077 Uiso 1 1 calc R U . . .
C4 C 0.44850(16) 0.5121(3) 0.1946(4) 0.0658(8) Uani 1 1 d . . . . .
H4 H 0.431389 0.449907 0.116027 0.079 Uiso 1 1 calc R U . . .
C5 C 0.53008(15) 0.5234(2) 0.2680(3) 0.0569(7) Uani 1 1 d . . . . .
H5 H 0.567402 0.468771 0.239410 0.068 Uiso 1 1 calc R U . . .
C6 C 0.55635(13) 0.6161(2) 0.3842(3) 0.0436(5) Uani 1 1 d . . . . .
C7 C 0.64185(14) 0.6316(2) 0.4658(3) 0.0443(5) Uani 1 1 d . . . . .
C8 C 0.71431(12) 0.5822(2) 0.4504(3) 0.0420(5) Uani 1 1 d . . . . .
C9 C 0.77474(14) 0.6440(2) 0.5727(3) 0.0441(5) Uani 1 1 d . . . . .
C10 C 0.86371(13) 0.6291(2) 0.6069(3) 0.0442(5) Uani 1 1 d . . . . .
C11 C 0.91074(15) 0.7017(2) 0.5233(3) 0.0586(7) Uani 1 1 d . . . . .
H11 H 0.885382 0.758463 0.442923 0.070 Uiso 1 1 calc R U . . .
C12 C 0.99412(16) 0.6919(3) 0.5561(4) 0.0677(8) Uani 1 1 d . . . . .
H12 H 1.024736 0.742225 0.499524 0.081 Uiso 1 1 calc R U . . .
C13 C 1.03199(15) 0.6069(3) 0.6737(3) 0.0640(7) Uani 1 1 d . . . . .
H13 H 1.088333 0.599542 0.696321 0.077 Uiso 1 1 calc R U . . .
C14 C 0.98642(15) 0.5328(2) 0.7575(3) 0.0573(7) Uani 1 1 d . . . . .
H14 H 1.011926 0.475113 0.836164 0.069 Uiso 1 1 calc R U . . .
C15 C 0.90333(14) 0.5443(2) 0.7249(3) 0.0454(5) Uani 1 1 d . . . . .
C16 C 0.75181(15) 0.3515(3) 0.4156(4) 0.0636(8) 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
Cl1 C15 1.736(2) . ?
S1 C8 1.758(2) . ?
S1 C16 1.703(3) . ?
O1 N1 1.413(2) . ?
O1 C7 1.351(3) . ?
N1 C9 1.303(3) . ?
N2 C16 1.140(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(4) . ?
C1 C6 1.397(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 C7 1.459(3) . ?
C7 C8 1.361(3) . ?
C8 C9 1.424(3) . ?
C9 C10 1.472(3) . ?
C10 C11 1.383(3) . ?
C10 C15 1.390(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(3) . ?

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
C16 S1 C8 99.87(12) . . ?
C7 O1 N1 109.66(16) . . ?
C9 N1 O1 105.85(18) . . ?
C2 C1 H1 119.9 . . ?
C2 C1 C6 120.3(2) . . ?
C6 C1 H1 119.9 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C7 119.2(2) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 122.1(2) . . ?
O1 C7 C6 115.17(19) . . ?
O1 C7 C8 107.86(19) . . ?
C8 C7 C6 137.0(2) . . ?
C7 C8 S1 129.06(17) . . ?
C7 C8 C9 105.9(2) . . ?
C9 C8 S1 124.38(17) . . ?
N1 C9 C8 110.7(2) . . ?
N1 C9 C10 120.4(2) . . ?
C8 C9 C10 128.8(2) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 C15 117.9(2) . . ?
C15 C10 C9 121.8(2) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.5(2) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 Cl1 119.80(18) . . ?
C14 C15 Cl1 119.03(19) . . ?
C14 C15 C10 121.1(2) . . ?
N2 C16 S1 178.1(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 C8 C9 N1 171.86(18) . . . . ?
S1 C8 C9 C10 -6.4(4) . . . . ?
O1 N1 C9 C8 -0.1(3) . . . . ?
O1 N1 C9 C10 178.4(2) . . . . ?
O1 C7 C8 S1 -171.42(18) . . . . ?
O1 C7 C8 C9 -0.4(2) . . . . ?
N1 O1 C7 C6 -179.2(2) . . . . ?
N1 O1 C7 C8 0.3(3) . . . . ?
N1 C9 C10 C11 -85.1(3) . . . . ?
N1 C9 C10 C15 93.8(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C6 C7 O1 5.5(3) . . . . ?
C1 C6 C7 C8 -173.9(3) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
C2 C1 C6 C7 179.9(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 1.3(4) . . . . ?
C4 C5 C6 C7 179.8(2) . . . . ?
C5 C6 C7 O1 -173.0(2) . . . . ?
C5 C6 C7 C8 7.6(4) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C6 C7 C8 S1 8.0(4) . . . . ?
C6 C7 C8 C9 179.1(3) . . . . ?
C7 O1 N1 C9 -0.2(3) . . . . ?
C7 C8 C9 N1 0.3(3) . . . . ?
C7 C8 C9 C10 -178.0(2) . . . . ?
C8 C9 C10 C11 93.0(3) . . . . ?
C8 C9 C10 C15 -88.1(3) . . . . ?
C9 C10 C11 C12 178.3(2) . . . . ?
C9 C10 C15 Cl1 -0.9(3) . . . . ?
C9 C10 C15 C14 -178.9(2) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C10 C15 Cl1 177.97(18) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 Cl1 -177.4(2) . . . . ?
C13 C14 C15 C10 0.6(4) . . . . ?
C15 C10 C11 C12 -0.6(4) . . . . ?
C16 S1 C8 C7 -106.8(2) . . . . ?
C16 S1 C8 C9 83.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
