# Supplementary Information (SI) for Green Chemistry.
# 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. 
# 
#######################################################################

data_a
_audit_block_doi                 10.5517/ccdc.csd.cc2pd87m
_database_code_depnum_ccdc_archive 'CCDC 2484440'
loop_
_audit_author_name
_audit_author_address
'Yirui Chen'
;College of Pharmaceutical Sciences, Zhejiang University of Technology
China
;
_audit_update_record             
;
2025-09-02 deposited with the CCDC.	2026-02-24 downloaded from the CCDC.
;
_audit_creation_date             2025-08-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H10 O3 S'
_chemical_formula_sum            'C14 H10 O3 S'
_chemical_formula_weight         258.28
_chemical_absolute_configuration ad
_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 0.0181 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'
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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   14.9751(5)
_cell_length_b                   6.1259(2)
_cell_length_c                   12.9261(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1185.79(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9810
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      79.45
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    2.411
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5363
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1111 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.7110.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25602
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.475
_diffrn_reflns_theta_min         4.519
_diffrn_ambient_temperature      193.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2524
_reflns_number_total             2549
_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 V2024.9-0 (Bruker, 2024)'
_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  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.050(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.111
_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)+(0.0647P)²+0.3699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1058
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C5(H5), C2(H2), C12(H12), C11(H11), C3(H3), C4(H4), C14(H14),
 C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.33408(4) 0.56348(10) 0.47360(5) 0.0307(2) Uani 1 1 d . . . . .
O1 O 0.24481(13) 0.6288(4) 0.50185(16) 0.0439(6) Uani 1 1 d . . . . .
O2 O 0.35789(19) 0.3380(4) 0.4843(2) 0.0508(6) Uani 1 1 d . . . . .
O3 O 0.49885(12) 0.7166(4) 0.50321(15) 0.0340(5) Uani 1 1 d . . . . .
C1 C 0.35985(18) 0.6687(4) 0.3504(2) 0.0283(5) Uani 1 1 d . . . . .
C2 C 0.32951(19) 0.5888(5) 0.2564(2) 0.0345(6) Uani 1 1 d . . . . .
H2 H 0.297293 0.455541 0.252093 0.041 Uiso 1 1 calc R U . . .
C3 C 0.3482(2) 0.7115(6) 0.1690(2) 0.0402(7) Uani 1 1 d . . . . .
H3 H 0.328916 0.661332 0.103178 0.048 Uiso 1 1 calc R U . . .
C4 C 0.3944(2) 0.9060(6) 0.1765(2) 0.0393(7) Uani 1 1 d . . . . .
H4 H 0.404491 0.990163 0.115922 0.047 Uiso 1 1 calc R U . . .
C5 C 0.42636(19) 0.9809(5) 0.2708(2) 0.0349(6) Uani 1 1 d . . . . .
H5 H 0.459069 1.113568 0.274578 0.042 Uiso 1 1 calc R U . . .
C6 C 0.41002(17) 0.8601(4) 0.35912(19) 0.0284(5) Uani 1 1 d . . . . .
C7 C 0.44420(17) 0.9007(4) 0.46578(19) 0.0288(5) Uani 1 1 d . . . . .
H7 H 0.458767 1.052885 0.488105 0.035 Uiso 1 1 calc R U . . .
C8 C 0.41003(16) 0.7427(4) 0.54167(19) 0.0265(5) Uani 1 1 d . . . . .
C9 C 0.39419(17) 0.7716(5) 0.6541(2) 0.0284(5) Uani 1 1 d . . . . .
C10 C 0.3555(2) 0.9610(5) 0.6911(2) 0.0377(6) Uani 1 1 d . . . . .
H10 H 0.339986 1.075225 0.644755 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3396(2) 0.9833(6) 0.7965(3) 0.0457(7) Uani 1 1 d . . . . .
H11 H 0.314247 1.114397 0.822600 0.055 Uiso 1 1 calc R U . . .
C12 C 0.3603(2) 0.8157(6) 0.8630(2) 0.0418(7) Uani 1 1 d . . . . .
H12 H 0.348468 0.831505 0.934760 0.050 Uiso 1 1 calc R U . . .
C13 C 0.3981(2) 0.6252(6) 0.8271(2) 0.0394(7) Uani 1 1 d . . . . .
H13 H 0.411972 0.510290 0.873753 0.047 Uiso 1 1 calc R U . . .
C14 C 0.41604(19) 0.6021(5) 0.7213(2) 0.0350(6) Uani 1 1 d . . . . .
H14 H 0.442794 0.472312 0.695710 0.042 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 O1 1.443(2) . ?
S1 O2 1.433(2) . ?
S1 C1 1.760(3) . ?
S1 C8 1.809(3) . ?
O3 C7 1.475(3) . ?
O3 C8 1.429(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.397(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9500 . ?
C5 C4 1.387(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(4) . ?
C7 C6 1.492(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.470(3) . ?
C9 C8 1.484(3) . ?
C9 C10 1.382(4) . ?
C9 C14 1.393(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(4) . ?
C11 H11 0.9500 . ?
C12 C11 1.374(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.377(5) . ?
C13 H13 0.9500 . ?
C14 C13 1.400(4) . ?
C14 H14 0.9500 . ?

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
O1 S1 C1 109.30(13) . . ?
O1 S1 C8 106.92(13) . . ?
O2 S1 O1 118.27(16) . . ?
O2 S1 C1 112.67(15) . . ?
O2 S1 C8 112.44(14) . . ?
C1 S1 C8 94.58(12) . . ?
C8 O3 C7 60.78(15) . . ?
C2 C1 S1 126.3(2) . . ?
C2 C1 C6 122.9(2) . . ?
C6 C1 S1 110.63(19) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 113.5(2) . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 127.8(2) . . ?
O3 C7 C6 111.5(2) . . ?
O3 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 O3 58.06(15) . . ?
C8 C7 C6 112.8(2) . . ?
C8 C7 H7 119.8 . . ?
O3 C8 S1 110.36(17) . . ?
O3 C8 C7 61.16(17) . . ?
O3 C8 C9 120.2(2) . . ?
C7 C8 S1 107.09(17) . . ?
C7 C8 C9 129.1(2) . . ?
C9 C8 S1 116.64(19) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 C14 120.6(3) . . ?
C14 C9 C8 119.0(2) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.5(3) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 C13 119.2(3) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?

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 C1 C2 C3 171.9(2) . . . . ?
S1 C1 C6 C5 -171.6(2) . . . . ?
S1 C1 C6 C7 11.7(3) . . . . ?
O1 S1 C1 C2 -76.4(3) . . . . ?
O1 S1 C1 C6 98.4(2) . . . . ?
O1 S1 C8 O3 -169.04(17) . . . . ?
O1 S1 C8 C7 -104.14(19) . . . . ?
O1 S1 C8 C9 49.1(2) . . . . ?
O2 S1 C1 C2 57.3(3) . . . . ?
O2 S1 C1 C6 -128.0(2) . . . . ?
O2 S1 C8 O3 59.6(2) . . . . ?
O2 S1 C8 C7 124.47(19) . . . . ?
O2 S1 C8 C9 -82.3(2) . . . . ?
O3 C7 C6 C1 57.1(3) . . . . ?
O3 C7 C6 C5 -119.1(3) . . . . ?
O3 C7 C8 S1 -104.25(17) . . . . ?
O3 C7 C8 C9 107.0(3) . . . . ?
C1 S1 C8 O3 -57.27(19) . . . . ?
C1 S1 C8 C7 7.64(19) . . . . ?
C1 S1 C8 C9 160.9(2) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C1 C6 C5 3.3(4) . . . . ?
C2 C1 C6 C7 -173.3(2) . . . . ?
C2 C3 C4 C5 2.3(5) . . . . ?
C4 C5 C6 C1 -1.5(4) . . . . ?
C4 C5 C6 C7 174.6(3) . . . . ?
C6 C1 C2 C3 -2.3(5) . . . . ?
C6 C5 C4 C3 -1.2(5) . . . . ?
C6 C7 C8 S1 -2.4(3) . . . . ?
C6 C7 C8 O3 101.9(2) . . . . ?
C6 C7 C8 C9 -151.1(2) . . . . ?
C7 O3 C8 S1 98.83(19) . . . . ?
C7 O3 C8 C9 -120.9(3) . . . . ?
C8 S1 C1 C2 173.9(3) . . . . ?
C8 S1 C1 C6 -11.3(2) . . . . ?
C8 O3 C7 C6 -104.2(2) . . . . ?
C8 C7 C6 C1 -6.0(3) . . . . ?
C8 C7 C6 C5 177.7(3) . . . . ?
C8 C9 C10 C11 178.7(3) . . . . ?
C8 C9 C14 C13 -177.6(3) . . . . ?
C9 C10 C11 C12 -1.4(5) . . . . ?
C9 C14 C13 C12 -0.8(5) . . . . ?
C10 C9 C8 S1 -104.1(3) . . . . ?
C10 C9 C8 O3 118.0(3) . . . . ?
C10 C9 C8 C7 42.2(4) . . . . ?
C10 C9 C14 C13 0.2(4) . . . . ?
C11 C12 C13 C14 0.3(5) . . . . ?
C13 C12 C11 C10 0.8(5) . . . . ?
C14 C9 C8 S1 73.7(3) . . . . ?
C14 C9 C8 O3 -64.2(4) . . . . ?
C14 C9 C8 C7 -139.9(3) . . . . ?
C14 C9 C10 C11 0.9(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
