# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_fl230331
_database_code_depnum_ccdc_archive 'CCDC 2326446'
loop_
_audit_author_name
_audit_author_address
'Lu Yang'
;Southwest Minzu university
China
;
_audit_update_record             
;
2024-01-18 deposited with the CCDC.	2024-04-05 downloaded from the CCDC.
;
_audit_creation_date             2023-12-03
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 O2 S'
_chemical_formula_sum            'C13 H12 O2 S'
_chemical_formula_weight         232.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.0408(8)
_cell_length_b                   7.8341(5)
_cell_length_c                   11.5786(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.948(6)
_cell_angle_gamma                90
_cell_volume                     1176.54(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5078
_cell_measurement_temperature    295.64(10)
_cell_measurement_theta_max      76.9840
_cell_measurement_theta_min      3.2850
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.710
_exptl_absorpt_coefficient_mu    2.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7411
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         6.601
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.64(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00 -21.00   0.50    0.36    --  -91.75  45.00 120.00   50
  2  ω    -56.00 -21.00   0.50    0.36    --  -91.75  61.00 120.00   70
  3  ω    -64.00 -20.00   0.50    0.36    --  -91.75  61.00  90.00   88
  4  ω    -49.00 -21.00   0.50    0.36    --  -91.75  45.00  30.00   56
  5  ω    -50.00 -25.00   0.50    0.36    --  -91.75  45.00   0.00   50
  6  ω    -88.00 -25.00   0.50    0.36    --  -91.75 125.00 -90.00  126
  7  ω    -72.00 -41.00   0.50    0.36    --  -91.75 125.00 120.00   62
  8  ω   -131.00 -74.00   0.50    0.36    --  -91.75 -14.00-122.00  114
  9  ω   -154.00-101.00   0.50    0.36    --  -91.75 -94.00-150.00  106
 10  ω   -122.00 -30.00   0.50    0.09    --  -47.39 -14.00-122.00  184
 11  ω    -26.00  14.00   0.50    0.09    --  -47.39  19.00 -90.00   80
 12  ω    -20.00  23.00   0.50    0.09    --  -47.39  19.00-180.00   86
 13  ω    -24.00  29.00   0.50    0.09    --  -47.39  14.00  48.00  106
 14  ω     38.00  95.00   0.50    0.09    --   47.39  14.00  48.00  114
 15  ω     92.00 176.00   0.50    0.36    --  108.42  14.00  48.00  168
 16  ω     38.00  64.00   0.50    0.36    --  108.42 -61.00 150.00   52
 17  ω     37.00  71.00   0.50    0.36    --  108.42 -61.00  60.00   68
 18  ω    -28.00  24.00   0.50    0.09    --   47.39 -14.00-122.00  104
 19  ω     33.00  59.00   0.50    0.09    --   47.39-125.00-180.00   52
 20  ω     41.00  98.00   0.50    0.36    --  108.42-125.00-120.00  114
 21  ω     60.00 112.00   0.50    0.36    --  108.42-125.00 150.00  104
 22  ω     40.00 106.00   0.50    0.36    --  108.42 -94.00 150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0369658000
_diffrn_orient_matrix_UB_12      -0.0291531000
_diffrn_orient_matrix_UB_13      -0.1205866000
_diffrn_orient_matrix_UB_21      -0.1113211000
_diffrn_orient_matrix_UB_22      0.0226402000
_diffrn_orient_matrix_UB_23      -0.0568323000
_diffrn_orient_matrix_UB_31      0.0185595000
_diffrn_orient_matrix_UB_32      0.1931562000
_diffrn_orient_matrix_UB_33      -0.0113627000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1757
_reflns_number_total             2068
_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 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0.0052(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0981
_refine_ls_restrained_S_all      1.945
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2493
_refine_ls_wR_factor_ref         0.2639
_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 Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.26998(6) 0.33270(11) 0.68067(8) 0.0659(5) Uani 1 1 d . . . . .
O1 O 0.2265(2) 0.1685(3) 0.6500(4) 0.0957(12) Uani 1 1 d . . . . .
O2 O 0.2693(2) 0.3918(5) 0.7983(2) 0.0939(10) Uani 1 1 d . . . . .
C1 C 0.2064(2) 0.4858(4) 0.5871(3) 0.0562(8) Uani 1 1 d . . . . .
C2 C 0.2058(3) 0.6545(4) 0.6205(3) 0.0644(10) Uani 1 1 d . . . . .
H2 H 0.239322 0.687839 0.691758 0.077 Uiso 1 1 calc R U . . .
C3 C 0.1552(3) 0.7733(5) 0.5481(4) 0.0718(11) Uani 1 1 d . . . . .
H3 H 0.154486 0.886873 0.571429 0.086 Uiso 1 1 calc R U . . .
C4 C 0.1057(3) 0.7281(5) 0.4420(3) 0.0658(9) Uani 1 1 d . . . . .
C5 C 0.1096(3) 0.5593(6) 0.4094(4) 0.0778(11) Uani 1 1 d . . . . .
H5 H 0.077616 0.526807 0.337276 0.093 Uiso 1 1 calc R U . . .
C6 C 0.1596(3) 0.4366(5) 0.4804(4) 0.0724(10) Uani 1 1 d . . . . .
H6 H 0.161444 0.323453 0.456495 0.087 Uiso 1 1 calc R U . . .
C7 C 0.0486(4) 0.8584(7) 0.3642(5) 0.1038(18) Uani 1 1 d . . . . .
H7A H -0.016915 0.881862 0.391766 0.156 Uiso 1 1 calc R U . . .
H7B H 0.037985 0.814583 0.286472 0.156 Uiso 1 1 calc R U . . .
H7C H 0.088277 0.961613 0.364876 0.156 Uiso 1 1 calc R U . . .
C8 C 0.3984(2) 0.3334(3) 0.6454(3) 0.0516(8) Uani 1 1 d . . . . .
C9 C 0.4719(3) 0.4223(4) 0.7153(3) 0.0614(9) Uani 1 1 d . . . . .
H9 H 0.453424 0.484060 0.778558 0.074 Uiso 1 1 calc R U . . .
C10 C 0.5730(3) 0.4189(4) 0.6906(4) 0.0702(10) Uani 1 1 d . . . . .
H10 H 0.623471 0.477301 0.737721 0.084 Uiso 1 1 calc R U . . .
C11 C 0.5989(3) 0.3290(4) 0.5962(4) 0.0685(10) Uani 1 1 d . . . . .
H11 H 0.667067 0.326519 0.579203 0.082 Uiso 1 1 calc R U . . .
C12 C 0.5250(3) 0.2432(5) 0.5272(3) 0.0741(11) Uani 1 1 d . . . . .
H12 H 0.543367 0.183639 0.462960 0.089 Uiso 1 1 calc R U . . .
C13 C 0.4247(3) 0.2430(4) 0.5505(3) 0.0659(9) Uani 1 1 d . . . . .
H13 H 0.374909 0.183144 0.503396 0.079 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 1.435(3) . ?
S1 O2 1.439(3) . ?
S1 C1 1.764(3) . ?
S1 C8 1.764(3) . ?
C1 C2 1.378(5) . ?
C1 C6 1.375(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(6) . ?
C4 C5 1.378(6) . ?
C4 C7 1.506(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(6) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.378(5) . ?
C8 C13 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.363(5) . ?
C13 H13 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
O1 S1 O2 118.8(2) . . ?
O1 S1 C1 108.00(17) . . ?
O1 S1 C8 107.77(17) . . ?
O2 S1 C1 108.31(17) . . ?
O2 S1 C8 108.48(17) . . ?
C8 S1 C1 104.62(14) . . ?
C2 C1 S1 119.7(3) . . ?
C6 C1 S1 119.9(3) . . ?
C6 C1 C2 120.4(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C7 121.2(4) . . ?
C5 C4 C7 121.1(4) . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.2(4) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 119.0(3) . . ?
C9 C8 C13 120.8(3) . . ?
C13 C8 S1 120.2(2) . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.4 . . ?
C8 C13 H13 120.7 . . ?
C12 C13 C8 118.7(3) . . ?
C12 C13 H13 120.7 . . ?

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 -179.3(3) . . . . ?
S1 C1 C6 C5 179.5(3) . . . . ?
S1 C8 C9 C10 177.9(3) . . . . ?
S1 C8 C13 C12 -178.6(3) . . . . ?
O1 S1 C1 C2 157.4(3) . . . . ?
O1 S1 C1 C6 -23.9(4) . . . . ?
O1 S1 C8 C9 -145.1(3) . . . . ?
O1 S1 C8 C13 33.5(3) . . . . ?
O2 S1 C1 C2 27.5(4) . . . . ?
O2 S1 C1 C6 -153.7(3) . . . . ?
O2 S1 C8 C9 -15.3(3) . . . . ?
O2 S1 C8 C13 163.3(3) . . . . ?
C1 S1 C8 C9 100.1(3) . . . . ?
C1 S1 C8 C13 -81.2(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C2 C3 C4 C7 178.7(4) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C6 C1 C2 C3 2.0(6) . . . . ?
C7 C4 C5 C6 -178.5(4) . . . . ?
C8 S1 C1 C2 -88.0(3) . . . . ?
C8 S1 C1 C6 90.7(3) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C9 C8 C13 C12 0.1(5) . . . . ?
C9 C10 C11 C12 -0.1(6) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C11 C12 C13 C8 0.7(6) . . . . ?
C13 C8 C9 C10 -0.8(5) . . . . ?

_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 3.043
_oxdiff_exptl_absorpt_empirical_full_min 0.496
