# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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. 
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#######################################################################

data_1_a
_database_code_depnum_ccdc_archive 'CCDC 2369815'
loop_
_audit_author_name
_audit_author_address
Li
;Huaibei Normal University
China
;
_audit_update_record             
;
2024-07-11 deposited with the CCDC.	2026-02-25 downloaded from the CCDC.
;
_audit_creation_date             2024-06-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O S'
_chemical_formula_sum            'C23 H21 N O S'
_chemical_formula_weight         359.47
_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'
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      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                   9.1818(4)
_cell_length_b                   10.1332(4)
_cell_length_c                   11.5335(5)
_cell_angle_alpha                106.9430(10)
_cell_angle_beta                 106.269(2)
_cell_angle_gamma                97.7560(10)
_cell_volume                     957.60(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9046
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0946 before and 0.0531 after correction.
The Ratio of minimum to maximum transmission is 0.9662.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33550
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.162
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3731
_reflns_number_total             4243
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.023
_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)+(0.0657P)²+0.1729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1289
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C18(H18), C11(H11), C1(H1), C14(H14), C4(H4), C13(H13), C5(H5),
 C12(H12), C7(H7), C6(H6)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C16(H16A,H16B,H16C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S1 S 0.21826(5) 0.03435(5) 0.00948(4) 0.07034(17) Uani 1 1 d . . . . .
O1 O 0.76325(13) 0.49111(12) 0.55793(10) 0.0607(3) Uani 1 1 d . . . . .
N1 N 0.66712(14) 0.64133(13) 0.13749(12) 0.0543(3) Uani 1 1 d . . . . .
C9 C 0.56110(14) 0.33507(13) 0.31360(12) 0.0433(3) Uani 1 1 d . . . . .
H9 H 0.523779 0.382000 0.383018 0.052 Uiso 1 1 calc R U . . .
C3 C 0.34882(15) 0.10755(14) 0.25649(13) 0.0446(3) Uani 1 1 d . . . . .
C2 C 0.42995(15) 0.21098(14) 0.21800(12) 0.0440(3) Uani 1 1 d . . . . .
C17 C 0.60099(14) 0.44410(13) 0.25297(12) 0.0431(3) Uani 1 1 d . . . . .
C10 C 0.70735(15) 0.28996(14) 0.37494(12) 0.0446(3) Uani 1 1 d . . . . .
C21 C 0.68853(15) 0.42227(15) 0.17152(14) 0.0482(3) Uani 1 1 d . . . . .
H21 H 0.726284 0.340603 0.154073 0.058 Uiso 1 1 calc R U . . .
C15 C 0.80992(16) 0.37550(15) 0.49703(13) 0.0485(3) Uani 1 1 d . . . . .
C18 C 0.54704(16) 0.56676(15) 0.27421(14) 0.0502(3) Uani 1 1 d . . . . .
H18 H 0.487857 0.585307 0.328061 0.060 Uiso 1 1 calc R U . . .
C20 C 0.71953(15) 0.52280(16) 0.11618(13) 0.0501(3) Uani 1 1 d . . . . .
C8 C 0.23008(17) 0.00428(15) 0.15158(15) 0.0531(3) Uani 1 1 d . . . . .
C19 C 0.58133(18) 0.66223(15) 0.21505(15) 0.0549(3) Uani 1 1 d . . . . .
C11 C 0.74617(18) 0.16938(16) 0.30971(15) 0.0545(3) Uani 1 1 d . . . . .
H11 H 0.678106 0.110437 0.228866 0.065 Uiso 1 1 calc R U . . .
C1 C 0.37027(17) 0.18368(17) 0.09015(14) 0.0562(4) Uani 1 1 d . . . . .
H1 H 0.407598 0.240169 0.049119 0.067 Uiso 1 1 calc R U . . .
C14 C 0.94972(18) 0.34193(18) 0.55004(16) 0.0593(4) Uani 1 1 d . . . . .
H14 H 1.018518 0.400075 0.630882 0.071 Uiso 1 1 calc R U . . .
C4 C 0.37166(19) 0.09978(17) 0.37935(15) 0.0559(3) Uani 1 1 d . . . . .
H4 H 0.450144 0.166288 0.450787 0.067 Uiso 1 1 calc R U . . .
C13 C 0.98555(19) 0.2219(2) 0.48193(18) 0.0671(4) Uani 1 1 d . . . . .
H13 H 1.079171 0.199663 0.517190 0.081 Uiso 1 1 calc R U . . .
C5 C 0.2759(2) -0.0081(2) 0.39298(19) 0.0695(5) Uani 1 1 d . . . . .
H5 H 0.290570 -0.013556 0.474418 0.083 Uiso 1 1 calc R U . . .
C12 C 0.8850(2) 0.13492(19) 0.36291(18) 0.0660(4) Uani 1 1 d . . . . .
H12 H 0.909490 0.053492 0.318142 0.079 Uiso 1 1 calc R U . . .
C7 C 0.13424(19) -0.10435(17) 0.16634(19) 0.0668(4) Uani 1 1 d . . . . .
H7 H 0.056050 -0.172148 0.095618 0.080 Uiso 1 1 calc R U . . .
C23 C 0.8166(2) 0.5043(2) 0.03000(18) 0.0715(5) Uani 1 1 d . . . . .
H23A H 0.770446 0.531787 -0.042312 0.107 Uiso 1 1 calc R U . . .
H23B H 0.821339 0.406661 0.000040 0.107 Uiso 1 1 calc R U . . .
H23C H 0.920232 0.562771 0.077130 0.107 Uiso 1 1 calc R U . . .
C16 C 0.8598(2) 0.5784(2) 0.68483(17) 0.0761(5) Uani 1 1 d . . . . .
H16A H 0.960936 0.616647 0.684080 0.114 Uiso 1 1 calc R U . . .
H16B H 0.870374 0.522863 0.740101 0.114 Uiso 1 1 calc R U . . .
H16C H 0.813421 0.654691 0.716091 0.114 Uiso 1 1 calc R U . . .
C6 C 0.1584(2) -0.1084(2) 0.2875(2) 0.0742(5) Uani 1 1 d . . . . .
H6 H 0.095160 -0.179430 0.299530 0.089 Uiso 1 1 calc R U . . .
C22 C 0.5234(3) 0.7959(2) 0.2340(2) 0.0858(6) Uani 1 1 d . . . . .
H22A H 0.610727 0.876728 0.275278 0.129 Uiso 1 1 calc R U . . .
H22B H 0.458825 0.798634 0.286869 0.129 Uiso 1 1 calc R U . . .
H22C H 0.463560 0.797978 0.151887 0.129 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 C8 1.7295(15) . ?
S1 C1 1.7278(16) . ?
O1 C15 1.3689(18) . ?
O1 C16 1.420(2) . ?
N1 C20 1.3360(19) . ?
N1 C19 1.340(2) . ?
C9 H9 0.9800 . ?
C9 C2 1.5120(18) . ?
C9 C17 1.5259(17) . ?
C9 C10 1.5279(17) . ?
C3 C2 1.4478(17) . ?
C3 C8 1.401(2) . ?
C3 C4 1.4004(19) . ?
C2 C1 1.3489(19) . ?
C17 C21 1.3884(19) . ?
C17 C18 1.3809(19) . ?
C10 C15 1.3951(19) . ?
C10 C11 1.385(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.3887(19) . ?
C15 C14 1.392(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.387(2) . ?
C20 C23 1.500(2) . ?
C8 C7 1.395(2) . ?
C19 C22 1.501(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(2) . ?
C1 H1 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.379(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.371(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(3) . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.366(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C6 H6 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C1 S1 C8 91.12(7) . . ?
C15 O1 C16 118.10(13) . . ?
C20 N1 C19 118.03(12) . . ?
C2 C9 H9 107.2 . . ?
C2 C9 C17 111.39(10) . . ?
C2 C9 C10 113.00(11) . . ?
C17 C9 H9 107.2 . . ?
C17 C9 C10 110.49(10) . . ?
C10 C9 H9 107.2 . . ?
C8 C3 C2 112.05(12) . . ?
C4 C3 C2 129.50(13) . . ?
C4 C3 C8 118.44(13) . . ?
C3 C2 C9 122.44(11) . . ?
C1 C2 C9 126.03(12) . . ?
C1 C2 C3 111.50(12) . . ?
C21 C17 C9 121.57(11) . . ?
C18 C17 C9 121.00(12) . . ?
C18 C17 C21 117.40(12) . . ?
C15 C10 C9 119.76(12) . . ?
C11 C10 C9 121.72(12) . . ?
C11 C10 C15 118.43(12) . . ?
C17 C21 H21 120.1 . . ?
C17 C21 C20 119.77(13) . . ?
C20 C21 H21 120.1 . . ?
O1 C15 C10 115.69(12) . . ?
O1 C15 C14 123.81(13) . . ?
C14 C15 C10 120.50(14) . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.83(13) . . ?
C19 C18 H18 120.1 . . ?
N1 C20 C21 122.41(13) . . ?
N1 C20 C23 116.32(13) . . ?
C21 C20 C23 121.26(14) . . ?
C3 C8 S1 111.35(10) . . ?
C7 C8 S1 126.60(13) . . ?
C7 C8 C3 122.03(15) . . ?
N1 C19 C18 122.54(13) . . ?
N1 C19 C22 115.80(14) . . ?
C18 C19 C22 121.66(15) . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.16(15) . . ?
C12 C11 H11 119.4 . . ?
S1 C1 H1 123.0 . . ?
C2 C1 S1 113.97(11) . . ?
C2 C1 H1 123.0 . . ?
C15 C14 H14 120.2 . . ?
C13 C14 C15 119.56(15) . . ?
C13 C14 H14 120.2 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.08(15) . . ?
C5 C4 H4 120.5 . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.86(14) . . ?
C12 C13 H13 119.6 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.28(16) . . ?
C6 C5 H5 119.4 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.46(15) . . ?
C13 C12 H12 120.3 . . ?
C8 C7 H7 120.9 . . ?
C6 C7 C8 118.18(16) . . ?
C6 C7 H7 120.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.98(15) . . ?
C7 C6 H6 119.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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 C7 C6 -177.96(13) . . . . ?
O1 C15 C14 C13 179.08(14) . . . . ?
C9 C2 C1 S1 -178.85(10) . . . . ?
C9 C17 C21 C20 178.66(12) . . . . ?
C9 C17 C18 C19 -178.19(12) . . . . ?
C9 C10 C15 O1 5.02(17) . . . . ?
C9 C10 C15 C14 -174.88(12) . . . . ?
C9 C10 C11 C12 175.40(13) . . . . ?
C3 C2 C1 S1 -0.79(16) . . . . ?
C3 C8 C7 C6 0.1(2) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C2 C9 C17 C21 -77.39(15) . . . . ?
C2 C9 C17 C18 100.64(14) . . . . ?
C2 C9 C10 C15 -153.33(11) . . . . ?
C2 C9 C10 C11 30.22(17) . . . . ?
C2 C3 C8 S1 -0.26(15) . . . . ?
C2 C3 C8 C7 -178.58(13) . . . . ?
C2 C3 C4 C5 178.30(14) . . . . ?
C17 C9 C2 C3 -167.37(11) . . . . ?
C17 C9 C2 C1 10.49(19) . . . . ?
C17 C9 C10 C15 81.10(14) . . . . ?
C17 C9 C10 C11 -95.35(14) . . . . ?
C17 C21 C20 N1 -0.5(2) . . . . ?
C17 C21 C20 C23 178.65(14) . . . . ?
C17 C18 C19 N1 -0.6(2) . . . . ?
C17 C18 C19 C22 179.19(16) . . . . ?
C10 C9 C2 C3 67.55(15) . . . . ?
C10 C9 C2 C1 -114.59(15) . . . . ?
C10 C9 C17 C21 49.08(16) . . . . ?
C10 C9 C17 C18 -132.89(13) . . . . ?
C10 C15 C14 C13 -1.0(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C21 C17 C18 C19 -0.1(2) . . . . ?
C15 C10 C11 C12 -1.1(2) . . . . ?
C15 C14 C13 C12 -0.3(2) . . . . ?
C18 C17 C21 C20 0.56(19) . . . . ?
C20 N1 C19 C18 0.7(2) . . . . ?
C20 N1 C19 C22 -179.07(15) . . . . ?
C8 S1 C1 C2 0.56(13) . . . . ?
C8 C3 C2 C9 178.81(11) . . . . ?
C8 C3 C2 C1 0.67(17) . . . . ?
C8 C3 C4 C5 -0.6(2) . . . . ?
C8 C7 C6 C5 -0.6(3) . . . . ?
C19 N1 C20 C21 -0.2(2) . . . . ?
C19 N1 C20 C23 -179.32(14) . . . . ?
C11 C10 C15 O1 -178.41(12) . . . . ?
C11 C10 C15 C14 1.69(19) . . . . ?
C1 S1 C8 C3 -0.15(11) . . . . ?
C1 S1 C8 C7 178.08(15) . . . . ?
C14 C13 C12 C11 0.9(3) . . . . ?
C4 C3 C2 C9 -0.1(2) . . . . ?
C4 C3 C2 C1 -178.27(14) . . . . ?
C4 C3 C8 S1 178.81(10) . . . . ?
C4 C3 C8 C7 0.5(2) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C16 O1 C15 C10 177.23(14) . . . . ?
C16 O1 C15 C14 -2.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
