# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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 
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data_mo_zhy20250827_0m
_database_code_depnum_ccdc_archive 'CCDC 2522354'
loop_
_audit_author_name
_audit_author_address
P
;Hebei University
China
;
_audit_update_record             
;
2026-01-13 deposited with the CCDC.	2026-04-20 downloaded from the CCDC.
;
_audit_creation_date             2025-08-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N2 O3 S'
_chemical_formula_sum            'C21 H14 N2 O3 S'
_chemical_formula_weight         374.40
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   15.719(4)
_cell_length_b                   10.479(3)
_cell_length_c                   21.491(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3540.3(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9248
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.080
_cell_measurement_theta_min      2.521
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1053 before and 0.0599 after correction.
The Ratio of minimum to maximum transmission is 0.9423.
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    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            50126
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.588
_diffrn_reflns_theta_min         1.895
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2721
_reflns_number_total             4064
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4064
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.035
_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)+(0.0457P)²+1.4203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1216
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
S1 S 0.64150(4) 0.43122(6) 0.58091(3) 0.06096(19) Uani 1 1 d . . . . .
O1 O 0.69348(10) 0.75736(15) 0.75787(7) 0.0614(4) Uani 1 1 d . . . . .
O2 O 0.46757(10) 0.69907(15) 0.54826(7) 0.0595(4) Uani 1 1 d . . . . .
O3 O 0.54333(13) 0.35967(15) 0.72410(8) 0.0777(6) Uani 1 1 d . . . . .
N1 N 0.55317(11) 0.74899(15) 0.63181(7) 0.0436(4) Uani 1 1 d . . . . .
N2 N 0.67331(16) 0.6470(3) 0.50642(12) 0.0909(8) Uani 1 1 d . . . . .
C1 C 0.58862(13) 0.87188(19) 0.62511(9) 0.0427(4) Uani 1 1 d . . . . .
C2 C 0.57664(15) 0.9593(2) 0.57826(10) 0.0531(5) Uani 1 1 d . . . . .
H2 H 0.542006 0.942274 0.544178 0.064 Uiso 1 1 calc R U . . .
C3 C 0.61919(17) 1.0745(2) 0.58477(11) 0.0606(6) Uani 1 1 d . . . . .
H3 H 0.613122 1.135996 0.553872 0.073 Uiso 1 1 calc R U . . .
C4 C 0.67024(16) 1.1014(2) 0.63544(12) 0.0622(6) Uani 1 1 d . . . . .
H4 H 0.696223 1.180846 0.638572 0.075 Uiso 1 1 calc R U . . .
C5 C 0.68314(15) 1.0114(2) 0.68155(10) 0.0543(5) Uani 1 1 d . . . . .
H5 H 0.718231 1.028477 0.715378 0.065 Uiso 1 1 calc R U . . .
C6 C 0.64188(13) 0.89429(18) 0.67573(9) 0.0436(5) Uani 1 1 d . . . . .
C7 C 0.64616(13) 0.77917(19) 0.71496(9) 0.0432(5) Uani 1 1 d . . . . .
C8 C 0.58239(13) 0.68829(18) 0.68588(8) 0.0399(4) Uani 1 1 d . . . . .
C9 C 0.54851(13) 0.57032(18) 0.69096(8) 0.0428(5) Uani 1 1 d . . . . .
C10 C 0.49349(14) 0.54622(19) 0.63362(9) 0.0463(5) Uani 1 1 d . . . . .
C11 C 0.50033(13) 0.6722(2) 0.59728(9) 0.0458(5) Uani 1 1 d . . . . .
C12 C 0.39939(15) 0.5216(3) 0.64860(11) 0.0665(7) Uani 1 1 d . . . . .
H12A H 0.393848 0.441167 0.669585 0.100 Uiso 1 1 calc R U . . .
H12B H 0.367186 0.519732 0.610653 0.100 Uiso 1 1 calc R U . . .
H12C H 0.378301 0.588528 0.674914 0.100 Uiso 1 1 calc R U . . .
C13 C 0.52711(15) 0.4370(2) 0.59238(9) 0.0530(5) Uani 1 1 d . . . . .
H13A H 0.500186 0.443667 0.551895 0.064 Uiso 1 1 calc R U . . .
H13B H 0.509235 0.356682 0.610608 0.064 Uiso 1 1 calc R U . . .
C14 C 0.65831(15) 0.5600(3) 0.53621(11) 0.0603(6) Uani 1 1 d . . . . .
C15 C 0.56166(14) 0.46976(19) 0.73808(9) 0.0489(5) Uani 1 1 d . . . . .
C16 C 0.59633(13) 0.49774(18) 0.80072(8) 0.0411(4) Uani 1 1 d . . . . .
C17 C 0.64746(14) 0.4061(2) 0.82862(10) 0.0525(5) Uani 1 1 d . . . . .
H17 H 0.659135 0.330341 0.807789 0.063 Uiso 1 1 calc R U . . .
C18 C 0.68102(15) 0.4268(2) 0.88699(11) 0.0621(6) Uani 1 1 d . . . . .
H18 H 0.715185 0.365180 0.905597 0.074 Uiso 1 1 calc R U . . .
C19 C 0.66362(15) 0.5392(2) 0.91756(10) 0.0606(6) Uani 1 1 d . . . . .
H19 H 0.687124 0.554073 0.956602 0.073 Uiso 1 1 calc R U . . .
C20 C 0.61203(15) 0.6292(2) 0.89102(10) 0.0562(6) Uani 1 1 d . . . . .
H20 H 0.599791 0.704034 0.912474 0.067 Uiso 1 1 calc R U . . .
C21 C 0.57790(14) 0.6093(2) 0.83228(9) 0.0480(5) Uani 1 1 d . . . . .
H21 H 0.542905 0.670638 0.814274 0.058 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 C13 1.816(2) . ?
S1 C14 1.677(3) . ?
O1 C7 1.207(2) . ?
O2 C11 1.206(2) . ?
O3 C15 1.226(2) . ?
N1 C1 1.411(3) . ?
N1 C8 1.402(2) . ?
N1 C11 1.374(2) . ?
N2 C14 1.139(3) . ?
C1 C2 1.374(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(3) . ?
C6 C7 1.473(3) . ?
C7 C8 1.517(3) . ?
C8 C9 1.351(3) . ?
C9 C10 1.526(3) . ?
C9 C15 1.476(3) . ?
C10 C11 1.538(3) . ?
C10 C12 1.536(3) . ?
C10 C13 1.541(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.482(3) . ?
C16 C17 1.388(3) . ?
C16 C21 1.383(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.369(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9300 . ?

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
C14 S1 C13 101.94(11) . . ?
C8 N1 C1 111.68(15) . . ?
C11 N1 C1 135.91(17) . . ?
C11 N1 C8 112.33(16) . . ?
C2 C1 N1 129.01(19) . . ?
C2 C1 C6 122.8(2) . . ?
C6 C1 N1 108.16(17) . . ?
C1 C2 H2 121.9 . . ?
C1 C2 C3 116.1(2) . . ?
C3 C2 H2 121.9 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.5(2) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.9(2) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C5 119.90(19) . . ?
C1 C6 C7 109.65(17) . . ?
C5 C6 C7 130.42(19) . . ?
O1 C7 C6 128.35(18) . . ?
O1 C7 C8 127.09(19) . . ?
C6 C7 C8 104.37(16) . . ?
N1 C8 C7 105.84(15) . . ?
C9 C8 N1 110.68(16) . . ?
C9 C8 C7 143.31(18) . . ?
C8 C9 C10 108.04(16) . . ?
C8 C9 C15 130.82(18) . . ?
C15 C9 C10 121.00(17) . . ?
C9 C10 C11 103.20(15) . . ?
C9 C10 C12 113.85(17) . . ?
C9 C10 C13 113.13(18) . . ?
C11 C10 C13 108.75(16) . . ?
C12 C10 C11 108.55(18) . . ?
C12 C10 C13 109.03(17) . . ?
O2 C11 N1 126.4(2) . . ?
O2 C11 C10 127.91(19) . . ?
N1 C11 C10 105.71(16) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
S1 C13 H13A 108.2 . . ?
S1 C13 H13B 108.2 . . ?
C10 C13 S1 116.26(14) . . ?
C10 C13 H13A 108.2 . . ?
C10 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
N2 C14 S1 177.1(2) . . ?
O3 C15 C9 118.07(18) . . ?
O3 C15 C16 119.68(19) . . ?
C9 C15 C16 122.25(17) . . ?
C17 C16 C15 117.94(18) . . ?
C21 C16 C15 122.42(18) . . ?
C21 C16 C17 119.63(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(2) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.5(2) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.3(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.5(2) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?

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
O1 C7 C8 N1 -170.4(2) . . . . ?
O1 C7 C8 C9 3.8(4) . . . . ?
O3 C15 C16 C17 33.4(3) . . . . ?
O3 C15 C16 C21 -145.1(2) . . . . ?
N1 C1 C2 C3 178.9(2) . . . . ?
N1 C1 C6 C5 -177.97(18) . . . . ?
N1 C1 C6 C7 3.9(2) . . . . ?
N1 C8 C9 C10 2.3(2) . . . . ?
N1 C8 C9 C15 178.0(2) . . . . ?
C1 N1 C8 C7 -2.9(2) . . . . ?
C1 N1 C8 C9 -179.24(17) . . . . ?
C1 N1 C11 O2 -2.1(4) . . . . ?
C1 N1 C11 C10 177.0(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C6 C7 O1 169.9(2) . . . . ?
C1 C6 C7 C8 -5.5(2) . . . . ?
C2 C1 C6 C5 2.5(3) . . . . ?
C2 C1 C6 C7 -175.67(19) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 176.7(2) . . . . ?
C5 C6 C7 O1 -8.1(4) . . . . ?
C5 C6 C7 C8 176.6(2) . . . . ?
C6 C1 C2 C3 -1.7(3) . . . . ?
C6 C7 C8 N1 5.0(2) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 C10 -171.7(3) . . . . ?
C7 C8 C9 C15 3.9(5) . . . . ?
C8 N1 C1 C2 179.0(2) . . . . ?
C8 N1 C1 C6 -0.5(2) . . . . ?
C8 N1 C11 O2 -178.5(2) . . . . ?
C8 N1 C11 C10 0.6(2) . . . . ?
C8 C9 C10 C11 -1.8(2) . . . . ?
C8 C9 C10 C12 -119.3(2) . . . . ?
C8 C9 C10 C13 115.50(19) . . . . ?
C8 C9 C15 O3 -159.7(2) . . . . ?
C8 C9 C15 C16 20.0(4) . . . . ?
C9 C10 C11 O2 179.8(2) . . . . ?
C9 C10 C11 N1 0.7(2) . . . . ?
C9 C10 C13 S1 -41.3(2) . . . . ?
C9 C15 C16 C17 -146.2(2) . . . . ?
C9 C15 C16 C21 35.3(3) . . . . ?
C10 C9 C15 O3 15.5(3) . . . . ?
C10 C9 C15 C16 -164.85(19) . . . . ?
C11 N1 C1 C2 2.6(4) . . . . ?
C11 N1 C1 C6 -176.9(2) . . . . ?
C11 N1 C8 C7 174.38(16) . . . . ?
C11 N1 C8 C9 -1.9(2) . . . . ?
C11 C10 C13 S1 72.75(19) . . . . ?
C12 C10 C11 O2 -59.1(3) . . . . ?
C12 C10 C11 N1 121.83(18) . . . . ?
C12 C10 C13 S1 -169.06(15) . . . . ?
C13 C10 C11 O2 59.4(3) . . . . ?
C13 C10 C11 N1 -119.67(18) . . . . ?
C14 S1 C13 C10 -69.63(18) . . . . ?
C15 C9 C10 C11 -178.02(18) . . . . ?
C15 C9 C10 C12 64.5(3) . . . . ?
C15 C9 C10 C13 -60.7(2) . . . . ?
C15 C16 C17 C18 -179.6(2) . . . . ?
C15 C16 C21 C20 179.6(2) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C16 C21 C20 1.1(3) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C21 C16 C17 C18 -1.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
