# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20241026c
_database_code_depnum_ccdc_archive 'CCDC 2394783'
loop_
_audit_author_name
_audit_author_address
ljfchem
;Wannan Medical College
China
;
_audit_update_record             
;
2024-10-30 deposited with the CCDC.	2025-05-22 downloaded from the CCDC.
;
_audit_creation_date             2024-10-27
_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         'C11 H10 O2 S'
_chemical_formula_sum            'C11 H10 O2 S'
_chemical_formula_weight         206.25
_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 0.0033 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'
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           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                   5.8934(5)
_cell_length_b                   10.2828(7)
_cell_length_c                   17.2226(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1043.70(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6152
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.017
_cell_measurement_theta_min      3.086
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1151 before and 0.0790 after correction.
The Ratio of minimum to maximum transmission is 0.8054.
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    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26022
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.709
_diffrn_reflns_theta_min         3.086
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1784
_reflns_number_total             2672
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT V8.40B (?, 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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 549 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.014
_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)+(0.0284P)²+0.2074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0919
_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:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C2(H2), C6(H6), C1(H1)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.20411(16) 0.15800(9) 0.22276(5) 0.0658(3) Uani 1 1 d . . . . .
O2 O 0.6733(4) 0.5572(2) 0.45412(12) 0.0696(7) Uani 1 1 d . . . . .
O1 O 0.4007(4) 0.4397(2) 0.51100(11) 0.0684(7) Uani 1 1 d . . . . .
C3 C 0.4426(5) 0.2180(3) 0.34410(16) 0.0473(7) Uani 1 1 d . . . . .
C4 C 0.5012(5) 0.2837(3) 0.41261(17) 0.0526(7) Uani 1 1 d . . . . .
H4 H 0.636054 0.265464 0.438423 0.063 Uiso 1 1 calc R U . . .
C8 C 0.2383(5) 0.2481(3) 0.30704(16) 0.0468(7) Uani 1 1 d . . . . .
C7 C 0.0914(5) 0.3418(3) 0.33656(18) 0.0567(7) Uani 1 1 d . . . . .
H7 H -0.044094 0.361189 0.311398 0.068 Uiso 1 1 calc R U . . .
C9 C 0.5676(5) 0.5307(3) 0.51065(17) 0.0507(7) Uani 1 1 d . . . . .
C5 C 0.3537(5) 0.3756(3) 0.44032(16) 0.0519(8) Uani 1 1 d . . . . .
C2 C 0.5653(6) 0.1197(3) 0.30259(19) 0.0632(9) Uani 1 1 d . . . . .
H2 H 0.704564 0.086801 0.318629 0.076 Uiso 1 1 calc R U . . .
C6 C 0.1513(5) 0.4049(3) 0.4038(2) 0.0573(8) Uani 1 1 d . . . . .
H6 H 0.055373 0.467526 0.424741 0.069 Uiso 1 1 calc R U . . .
C1 C 0.4576(7) 0.0803(3) 0.2381(2) 0.0666(9) Uani 1 1 d . . . . .
H1 H 0.514913 0.016984 0.204970 0.080 Uiso 1 1 calc R U . . .
C10 C 0.5943(7) 0.5885(4) 0.58970(19) 0.0732(10) Uani 1 1 d . . . . .
H10A H 0.625580 0.519294 0.626443 0.088 Uiso 1 1 calc R U . . .
H10B H 0.452132 0.628845 0.604734 0.088 Uiso 1 1 calc R U . . .
C11 C 0.7797(8) 0.6878(4) 0.5948(3) 0.1129(17) Uani 1 1 d . . . . .
H11A H 0.743916 0.760168 0.561802 0.169 Uiso 1 1 calc R U . . .
H11B H 0.920359 0.649516 0.578398 0.169 Uiso 1 1 calc R U . . .
H11C H 0.793705 0.717265 0.647470 0.169 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0707(6) 0.0668(5) 0.0597(4) -0.0080(4) -0.0092(4) -0.0028(5)
O2 0.0703(16) 0.0780(15) 0.0606(13) -0.0006(11) 0.0153(13) -0.0148(13)
O1 0.0776(18) 0.0786(15) 0.0489(12) -0.0104(11) 0.0161(11) -0.0259(13)
C3 0.0432(17) 0.0484(15) 0.0504(16) 0.0060(13) 0.0021(13) 0.0041(14)
C4 0.0476(18) 0.0616(18) 0.0485(16) 0.0095(14) -0.0064(14) 0.0009(15)
C8 0.0455(17) 0.0448(14) 0.0502(14) 0.0041(12) 0.0005(12) -0.0024(13)
C7 0.0397(16) 0.0575(16) 0.073(2) 0.0026(17) -0.0054(14) 0.0026(16)
C9 0.0466(18) 0.0511(17) 0.0544(17) 0.0026(13) 0.0019(15) 0.0016(15)
C5 0.055(2) 0.0561(18) 0.0449(15) -0.0011(13) 0.0094(14) -0.0090(15)
C2 0.056(2) 0.064(2) 0.069(2) 0.0007(16) 0.0048(17) 0.0170(17)
C6 0.047(2) 0.0521(17) 0.073(2) -0.0063(15) 0.0123(16) 0.0061(15)
C1 0.075(2) 0.0575(18) 0.067(2) -0.0096(16) 0.0125(19) 0.0096(18)
C10 0.082(3) 0.077(2) 0.0604(19) -0.0121(18) 0.0027(19) -0.014(2)
C11 0.116(4) 0.120(4) 0.102(3) -0.032(3) 0.001(3) -0.049(3)

_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 1.734(3) . ?
S1 C1 1.714(4) . ?
O2 C9 1.188(3) . ?
O1 C9 1.357(4) . ?
O1 C5 1.412(3) . ?
C3 C4 1.403(4) . ?
C3 C8 1.397(4) . ?
C3 C2 1.434(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(4) . ?
C8 C7 1.391(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.373(4) . ?
C9 C10 1.494(4) . ?
C5 C6 1.383(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.341(4) . ?
C6 H6 0.9300 . ?
C1 H1 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.498(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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 91.05(15) . . ?
C9 O1 C5 117.4(2) . . ?
C4 C3 C2 129.4(3) . . ?
C8 C3 C4 119.3(3) . . ?
C8 C3 C2 111.3(3) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C8 S1 111.3(2) . . ?
C7 C8 S1 127.1(2) . . ?
C7 C8 C3 121.5(3) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 C8 118.4(3) . . ?
C6 C7 H7 120.8 . . ?
O2 C9 O1 122.8(3) . . ?
O2 C9 C10 126.9(3) . . ?
O1 C9 C10 110.3(3) . . ?
C4 C5 O1 119.9(3) . . ?
C4 C5 C6 122.6(3) . . ?
C6 C5 O1 117.4(3) . . ?
C3 C2 H2 123.6 . . ?
C1 C2 C3 112.8(3) . . ?
C1 C2 H2 123.6 . . ?
C7 C6 C5 120.2(3) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
S1 C1 H1 123.2 . . ?
C2 C1 S1 113.5(3) . . ?
C2 C1 H1 123.2 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C9 C10 C11 113.7(3) . . ?
H10A C10 H10B 107.7 . . ?
C11 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 -178.6(2) . . . . ?
O2 C9 C10 C11 -1.3(5) . . . . ?
O1 C9 C10 C11 178.6(3) . . . . ?
O1 C5 C6 C7 -177.3(3) . . . . ?
C3 C4 C5 O1 177.0(2) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C3 C8 C7 C6 -0.1(4) . . . . ?
C3 C2 C1 S1 0.1(4) . . . . ?
C4 C3 C8 S1 178.7(2) . . . . ?
C4 C3 C8 C7 -0.1(4) . . . . ?
C4 C3 C2 C1 -179.0(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C8 S1 C1 C2 -0.5(3) . . . . ?
C8 C3 C4 C5 -0.1(4) . . . . ?
C8 C3 C2 C1 0.4(4) . . . . ?
C8 C7 C6 C5 0.4(4) . . . . ?
C9 O1 C5 C4 73.7(4) . . . . ?
C9 O1 C5 C6 -109.4(3) . . . . ?
C5 O1 C9 O2 -0.1(4) . . . . ?
C5 O1 C9 C10 180.0(3) . . . . ?
C2 C3 C4 C5 179.3(3) . . . . ?
C2 C3 C8 S1 -0.8(3) . . . . ?
C2 C3 C8 C7 -179.5(3) . . . . ?
C1 S1 C8 C3 0.7(2) . . . . ?
C1 S1 C8 C7 179.4(3) . . . . ?

_shelx_res_file                  
;
TITL 20241026c_a.res in P2(1)2(1)2(1)
    20241026c.res
    created by SHELXL-2019/3 at 19:49:23 on 27-Oct-2024
REM Old TITL 20241026c in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1): R1 0.119, Rweak 0.032, Alpha 0.001
REM <I/s> 0.498 for 19 systematic absences, Orientation as input
REM Flack x = -0.010 ( 0.051 ) from 557 Parsons' quotients
REM Formula found by SHELXT: C11 O2 S
CELL 0.71073 5.8934 10.2828 17.2226 90 90 90
ZERR 4 0.0005 0.0007 0.0013 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H O S
UNIT 44 40 8 4

L.S. 10
PLAN  1
SIZE 0.12 0.15 0.45
TEMP 25(2)
CONF
BOND
list 4
fmap 2
MORE -1
BOND $H
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\20241026c.hkl">
REM </olex2.extras>

WGHT    0.028400    0.207400
FVAR       1.31231
S1    4    0.204111    0.157998    0.222759    11.00000    0.07073    0.06682 =
         0.05973   -0.00799   -0.00920   -0.00280
O2    3    0.673325    0.557242    0.454117    11.00000    0.07027    0.07795 =
         0.06063   -0.00057    0.01533   -0.01483
O1    3    0.400702    0.439747    0.511001    11.00000    0.07759    0.07859 =
         0.04891   -0.01038    0.01614   -0.02588
C3    1    0.442560    0.218017    0.344097    11.00000    0.04316    0.04835 =
         0.05036    0.00601    0.00214    0.00411
C4    1    0.501160    0.283732    0.412611    11.00000    0.04764    0.06163 =
         0.04845    0.00946   -0.00644    0.00090
AFIX  43
H4    2    0.636054    0.265464    0.438423    11.00000   -1.20000
AFIX   0
C8    1    0.238291    0.248126    0.307037    11.00000    0.04549    0.04479 =
         0.05018    0.00406    0.00055   -0.00241
C7    1    0.091362    0.341797    0.336564    11.00000    0.03966    0.05745 =
         0.07308    0.00260   -0.00541    0.00263
AFIX  43
H7    2   -0.044094    0.361189    0.311398    11.00000   -1.20000
AFIX   0
C9    1    0.567609    0.530688    0.510648    11.00000    0.04664    0.05105 =
         0.05436    0.00261    0.00186    0.00161
C5    1    0.353749    0.375565    0.440319    11.00000    0.05483    0.05613 =
         0.04488   -0.00105    0.00935   -0.00898
C2    1    0.565262    0.119720    0.302586    11.00000    0.05577    0.06447 =
         0.06924    0.00075    0.00476    0.01697
AFIX  43
H2    2    0.704564    0.086801    0.318629    11.00000   -1.20000
AFIX   0
C6    1    0.151270    0.404885    0.403757    11.00000    0.04663    0.05214 =
         0.07300   -0.00626    0.01227    0.00605
AFIX  43
H6    2    0.055373    0.467526    0.424741    11.00000   -1.20000
AFIX   0
C1    1    0.457582    0.080341    0.238138    11.00000    0.07491    0.05748 =
         0.06748   -0.00963    0.01255    0.00963
AFIX  43
H1    2    0.514913    0.016984    0.204970    11.00000   -1.20000
AFIX   0
C10   1    0.594262    0.588491    0.589695    11.00000    0.08180    0.07749 =
         0.06042   -0.01209    0.00268   -0.01404
AFIX  23
H10A  2    0.625580    0.519294    0.626443    11.00000   -1.20000
H10B  2    0.452132    0.628845    0.604734    11.00000   -1.20000
AFIX   0
C11   1    0.779716    0.687776    0.594800    11.00000    0.11644    0.12047 =
         0.10166   -0.03225    0.00131   -0.04925
AFIX 137
H11A  2    0.743916    0.760168    0.561802    11.00000   -1.50000
H11B  2    0.920359    0.649516    0.578398    11.00000   -1.50000
H11C  2    0.793705    0.717265    0.647470    11.00000   -1.50000
AFIX   0
HKLF 4




REM  20241026c_a.res in P2(1)2(1)2(1)
REM wR2 = 0.0919, GooF = S = 1.014, Restrained GooF = 1.014 for all data
REM R1 = 0.0437 for 1784 Fo > 4sig(Fo) and 0.0852 for all 2672 data
REM 128 parameters refined using 0 restraints

END

WGHT      0.0284      0.2074

REM Highest difference peak  0.136,  deepest hole -0.185,  1-sigma level  0.032
Q1    1   0.5607  0.3904  0.5195  11.00000  0.05    0.14
;
_shelx_res_checksum              20301
_olex2_submission_special_instructions 'No special instructions were received'
