# Supplementary Information (SI) for ChemComm.
# 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_exp_9937
_audit_block_doi                 10.5517/ccdc.csd.cc2pwp2c
_database_code_depnum_ccdc_archive 'CCDC 2499253'
loop_
_audit_author_name
_audit_author_address
'Lianhui Wang'
;Huaqiao University
China
;
_audit_update_record             
;
2025-10-31 deposited with the CCDC.	2026-06-11 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.06.29 svn.r12e2184c for OlexSys, GUI svn.r6374)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 O S'
_chemical_formula_sum            'C10 H8 O S'
_chemical_formula_weight         176.22
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.1246(11)
_cell_length_b                   6.4322(6)
_cell_length_c                   16.443(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.607(12)
_cell_angle_gamma                90
_cell_volume                     855.18(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    771
_cell_measurement_temperature    296.00(10)
_cell_measurement_theta_max      22.3470
_cell_measurement_theta_min      4.0440
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.896
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83438
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.097
_diffrn_reflns_theta_min         3.403
_diffrn_ambient_temperature      296.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  74.00   1.00    7.50    --   15.65  19.00  90.00   88
  2  ω    -53.00  45.00   1.00    7.50    --   15.65 -19.00-120.00   98
  3  ω     -8.00  23.00   1.00    7.50    --  -16.43 -99.00 -90.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0353442000
_diffrn_orient_matrix_UB_12      -0.0013302000
_diffrn_orient_matrix_UB_13      -0.0377708000
_diffrn_orient_matrix_UB_21      -0.0747371000
_diffrn_orient_matrix_UB_22      -0.0408311000
_diffrn_orient_matrix_UB_23      -0.0195661000
_diffrn_orient_matrix_UB_31      -0.0293486000
_diffrn_orient_matrix_UB_32      0.1024392000
_diffrn_orient_matrix_UB_33      -0.0082756000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1220
_reflns_number_total             1955
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0631
_refine_ls_restrained_S_all      1.065
_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)+(0.0414P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10)
;
_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 0.64233(10) 0.70034(11) 0.30124(5) 0.0612(3) Uani 1 1 d . . . . .
O1 O 0.5199(3) 1.0370(3) 0.36542(12) 0.0707(6) Uani 1 1 d . . . . .
C1 C 0.7680(3) 0.4678(3) 0.53028(16) 0.0417(6) Uani 1 1 d . . . . .
C2 C 0.8350(3) 0.2701(4) 0.5219(2) 0.0574(8) Uani 1 1 d . . . . .
H2 H 0.839117 0.213720 0.470056 0.069 Uiso 1 1 calc R U . . .
C3 C 0.8953(4) 0.1573(4) 0.5900(2) 0.0699(9) Uani 1 1 d . . . . .
H3 H 0.938654 0.025160 0.583607 0.084 Uiso 1 1 calc R U . . .
C4 C 0.8917(4) 0.2385(5) 0.6671(2) 0.0675(9) Uani 1 1 d . . . . .
H4 H 0.933952 0.163022 0.712618 0.081 Uiso 1 1 calc R U . . .
C5 C 0.8248(4) 0.4336(5) 0.67619(18) 0.0639(8) Uani 1 1 d . . . . .
H5 H 0.820931 0.489095 0.728194 0.077 Uiso 1 1 calc R U . . .
C6 C 0.7640(3) 0.5458(4) 0.60888(17) 0.0523(7) Uani 1 1 d . . . . .
H6 H 0.719075 0.676744 0.616015 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7058(3) 0.5890(3) 0.45764(15) 0.0390(6) Uani 1 1 d . . . . .
C8 C 0.7239(4) 0.5083(3) 0.37342(17) 0.0535(7) Uani 1 1 d . . . . .
H8A H 0.663750 0.378676 0.364513 0.064 Uiso 1 1 calc R U . . .
H8B H 0.839530 0.482586 0.366958 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5848(3) 0.8684(4) 0.37910(17) 0.0500(7) Uani 1 1 d . . . . .
C10 C 0.6306(3) 0.7738(4) 0.45837(16) 0.0474(7) Uani 1 1 d . . . . .
H10 H 0.608763 0.838135 0.506822 0.057 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 0.0823(6) 0.0633(5) 0.0385(4) 0.0001(4) 0.0081(4) -0.0006(4)
O1 0.0987(17) 0.0548(11) 0.0548(14) 0.0044(10) -0.0109(12) 0.0131(11)
C1 0.0367(15) 0.0433(14) 0.0456(17) 0.0014(12) 0.0062(12) -0.0025(11)
C2 0.0642(19) 0.0496(15) 0.059(2) 0.0008(14) 0.0091(16) 0.0058(14)
C3 0.065(2) 0.0562(18) 0.089(3) 0.0147(18) 0.008(2) 0.0110(15)
C4 0.0537(19) 0.079(2) 0.069(2) 0.0297(18) 0.0031(17) 0.0011(16)
C5 0.063(2) 0.085(2) 0.0438(19) 0.0096(16) 0.0030(15) 0.0094(17)
C6 0.0549(18) 0.0565(16) 0.0452(18) 0.0022(13) 0.0034(14) 0.0071(13)
C7 0.0382(15) 0.0393(13) 0.0399(15) -0.0036(11) 0.0052(12) -0.0080(11)
C8 0.067(2) 0.0510(14) 0.0436(18) -0.0033(13) 0.0118(15) 0.0007(13)
C9 0.0552(18) 0.0478(15) 0.0456(18) -0.0009(13) -0.0025(14) -0.0064(13)
C10 0.0554(17) 0.0513(14) 0.0345(16) -0.0048(12) -0.0002(13) 0.0014(13)

_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 1.795(3) . ?
S1 C9 1.773(3) . ?
O1 C9 1.217(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.390(3) . ?
C1 C7 1.474(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.500(3) . ?
C7 C10 1.337(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.453(3) . ?
C10 H10 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
C9 S1 C8 92.78(13) . . ?
C2 C1 C7 120.5(3) . . ?
C6 C1 C2 117.8(3) . . ?
C6 C1 C7 121.7(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C1 C7 C8 120.5(2) . . ?
C10 C7 C1 125.7(2) . . ?
C10 C7 C8 113.7(2) . . ?
S1 C8 H8A 110.1 . . ?
S1 C8 H8B 110.1 . . ?
C7 C8 S1 108.00(16) . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
O1 C9 S1 123.4(2) . . ?
O1 C9 C10 127.3(3) . . ?
C10 C9 S1 109.28(19) . . ?
C7 C10 C9 116.2(2) . . ?
C7 C10 H10 121.9 . . ?
C9 C10 H10 121.9 . . ?

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 C9 C10 C7 1.0(3) . . . . ?
O1 C9 C10 C7 -177.9(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C7 C8 S1 -177.70(18) . . . . ?
C1 C7 C10 C9 177.8(2) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C2 C1 C7 C8 -4.2(4) . . . . ?
C2 C1 C7 C10 175.8(2) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C6 C1 C7 C8 175.1(2) . . . . ?
C6 C1 C7 C10 -4.9(4) . . . . ?
C7 C1 C2 C3 179.2(2) . . . . ?
C7 C1 C6 C5 -178.8(2) . . . . ?
C8 S1 C9 O1 179.3(2) . . . . ?
C8 S1 C9 C10 0.4(2) . . . . ?
C8 C7 C10 C9 -2.1(3) . . . . ?
C9 S1 C8 C7 -1.4(2) . . . . ?
C10 C7 C8 S1 2.3(3) . . . . ?

_shelx_res_file                  
;
TITL exp_9937_a.res in P2(1)/n
    exp_9937.res
    created by SHELXL-2018/1 at 10:29:04 on 09-Sep-2021
REM Old TITL exp_9937 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.209, Rweak 0.695, Alpha 0.032, Orientation as input
REM Formula found by SHELXT: C9 N O Cl
CELL 0.71073 8.1246 6.4322 16.443 90 95.607 90
ZERR 4 0.0011 0.0006 0.0022 0 0.012 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H O S
UNIT 40 32 4 4

L.S. 4 0 0
PLAN  1
SIZE 0.18 0.2 0.35
TEMP 22.85(10)
CONF
BOND $H
list 4
fmap 2 53
MORE -1
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\exp_9937.hkl">
REM </olex2.extras>

WGHT    0.041400
FVAR       0.77538
S1    4    0.642330    0.700340    0.301237    11.00000    0.08226    0.06328 =
         0.03851    0.00013    0.00811   -0.00063
O1    3    0.519860    1.036957    0.365422    11.00000    0.09874    0.05483 =
         0.05476    0.00437   -0.01090    0.01311
C1    1    0.767980    0.467797    0.530278    11.00000    0.03670    0.04325 =
         0.04559    0.00137    0.00618   -0.00254
C2    1    0.834963    0.270142    0.521890    11.00000    0.06420    0.04955 =
         0.05916    0.00078    0.00914    0.00579
AFIX  43
H2    2    0.839117    0.213720    0.470056    11.00000   -1.20000
AFIX   0
C3    1    0.895289    0.157288    0.590043    11.00000    0.06474    0.05615 =
         0.08887    0.01475    0.00827    0.01100
AFIX  43
H3    2    0.938654    0.025160    0.583607    11.00000   -1.20000
AFIX   0
C4    1    0.891719    0.238545    0.667050    11.00000    0.05365    0.07910 =
         0.06927    0.02974    0.00308    0.00106
AFIX  43
H4    2    0.933952    0.163022    0.712618    11.00000   -1.20000
AFIX   0
C5    1    0.824786    0.433571    0.676192    11.00000    0.06280    0.08477 =
         0.04384    0.00960    0.00305    0.00937
AFIX  43
H5    2    0.820931    0.489095    0.728194    11.00000   -1.20000
AFIX   0
C6    1    0.763951    0.545759    0.608880    11.00000    0.05486    0.05647 =
         0.04525    0.00220    0.00343    0.00706
AFIX  43
H6    2    0.719075    0.676744    0.616015    11.00000   -1.20000
AFIX   0
C7    1    0.705764    0.589025    0.457642    11.00000    0.03816    0.03926 =
         0.03992   -0.00364    0.00517   -0.00801
C8    1    0.723884    0.508259    0.373423    11.00000    0.06724    0.05096 =
         0.04356   -0.00334    0.01182    0.00072
AFIX  23
H8A   2    0.663750    0.378676    0.364513    11.00000   -1.20000
H8B   2    0.839530    0.482586    0.366958    11.00000   -1.20000
AFIX   0
C9    1    0.584822    0.868367    0.379095    11.00000    0.05518    0.04784 =
         0.04561   -0.00091   -0.00252   -0.00640
C10   1    0.630560    0.773801    0.458370    11.00000    0.05542    0.05126 =
         0.03452   -0.00480   -0.00020    0.00142
AFIX  43
H10   2    0.608763    0.838135    0.506822    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_9937_a.res in P2(1)/n
REM R1 =  0.0631 for    1220 Fo > 4sig(Fo)  and  0.1073 for all    1955 data
REM    109 parameters refined using      0 restraints

END

WGHT      0.0414      0.0000

REM Highest difference peak  0.182,  deepest hole -0.321,  1-sigma level  0.057
Q1    1   0.6459  0.2183  0.6753  11.00000  0.05    0.18
;
_shelx_res_checksum              45336
_olex2_date_sample_data_collection 2021-07-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.182
_oxdiff_exptl_absorpt_empirical_full_min 0.920
