# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_200730_thw_p22_0m
_database_code_depnum_ccdc_archive 'CCDC 2025743'
loop_
_audit_author_name
_audit_author_address
'Ren-Xiao Liang'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;
_audit_creation_date             2020-07-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O2 S'
_chemical_formula_sum            'C18 H16 O2 S'
_chemical_formula_weight         296.37
_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                   7.349(2)
_cell_length_b                   11.275(3)
_cell_length_c                   17.533(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1452.8(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0799 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.9496.
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    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17267
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.036
_diffrn_reflns_theta_min         2.323
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3144
_reflns_number_total             3192
_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
_computing.data_collection       Bruker
_computing.data_reduction        SAINT
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.1810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0748
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C5 \\sim S1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim S1A \\sim C1A \\sim C2A
\\sim C3A \\sim C4A: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C3) = Uanis(C3A)
3. Others
 Sof(H5B)=Sof(S1A)=Sof(C1A)=Sof(H1AA)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=
 Sof(C4A)=1-FVAR(1)
 Sof(H5A)=Sof(S1)=Sof(C1)=Sof(H1A)=Sof(C2)=Sof(H2)=Sof(C3)=Sof(H3)=Sof(C4)=
 FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C5(H5B), C8(H8), C9(H9), C10(H10), C11(H11), C1(H1A), C2(H2), C3(H3),
  C1A(H1AA), C2A(H2A), C3A(H3A)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
4.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.68051(18) 0.31623(11) 0.76712(6) 0.0278(3) Uani 1 1 d . . . . .
H1 H 0.575459 0.344106 0.761194 0.042 Uiso 1 1 calc GR . . . .
O2 O 0.66426(19) -0.05821(12) 0.74469(8) 0.0340(3) Uani 1 1 d . . . . .
C5 C 0.7152(2) 0.44048(14) 0.62383(8) 0.0220(3) Uani 1 1 d . U . . .
H5A H 0.724446 0.478248 0.672115 0.026 Uiso 0.786(3) 1 calc R . P A 1
H5B H 0.716627 0.473651 0.673639 0.026 Uiso 0.214(3) 1 calc R . P A 2
C6 C 0.7188(2) 0.32128(13) 0.62576(8) 0.0190(3) Uani 1 1 d . . . . .
C7 C 0.7049(2) 0.22837(13) 0.56665(8) 0.0183(3) Uani 1 1 d . . . . .
C8 C 0.7444(2) 0.23130(14) 0.48848(8) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.786898 0.302172 0.465202 0.027 Uiso 1 1 calc R . . . .
C9 C 0.7204(2) 0.12867(15) 0.44550(9) 0.0264(3) Uani 1 1 d . . . . .
H9 H 0.745559 0.130004 0.392358 0.032 Uiso 1 1 calc R . . . .
C10 C 0.6601(2) 0.02426(15) 0.47924(9) 0.0270(3) Uani 1 1 d . . . . .
H10 H 0.641730 -0.044231 0.448630 0.032 Uiso 1 1 calc R . . . .
C11 C 0.6261(2) 0.01869(14) 0.55741(9) 0.0241(3) Uani 1 1 d . . . . .
H11 H 0.587263 -0.053114 0.580625 0.029 Uiso 1 1 calc R . . . .
C12 C 0.6506(2) 0.12103(14) 0.60050(8) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.6210(2) 0.13625(14) 0.68615(8) 0.0194(3) Uani 1 1 d . . . . .
C14 C 0.7319(2) 0.25241(14) 0.70088(8) 0.0204(3) Uani 1 1 d . . . . .
C15 C 0.9286(2) 0.20637(16) 0.71513(9) 0.0259(3) Uani 1 1 d . . . . .
H15A H 0.994328 0.196378 0.666266 0.031 Uiso 1 1 calc R . . . .
H15B H 0.997269 0.262582 0.747584 0.031 Uiso 1 1 calc R . . . .
C16 C 0.9063(3) 0.08689(18) 0.75550(11) 0.0351(4) Uani 1 1 d . . . . .
H16A H 1.004245 0.031499 0.740256 0.042 Uiso 1 1 calc R . . . .
H16B H 0.910057 0.097226 0.811544 0.042 Uiso 1 1 calc R . . . .
C17 C 0.7223(2) 0.04027(15) 0.73057(9) 0.0245(3) Uani 1 1 d . . . . .
C18 C 0.4190(2) 0.14242(15) 0.70714(9) 0.0250(3) Uani 1 1 d . . . . .
H18A H 0.361329 0.207663 0.679220 0.037 Uiso 1 1 calc GR . . . .
H18B H 0.406647 0.156065 0.762100 0.037 Uiso 1 1 calc GR . . . .
H18C H 0.359729 0.067487 0.693546 0.037 Uiso 1 1 calc GR . . . .
S1 S 0.79354(17) 0.66186(9) 0.56945(7) 0.0389(3) Uani 0.786(3) 1 d . U P A 1
C1 C 0.7496(7) 0.7004(4) 0.4783(3) 0.0457(12) Uani 0.786(3) 1 d . U P A 1
H1A H 0.783176 0.773878 0.455832 0.055 Uiso 0.786(3) 1 calc R . P A 1
C2 C 0.6572(7) 0.6099(4) 0.4404(3) 0.0396(10) Uani 0.786(3) 1 d . U P A 1
H2 H 0.615054 0.622828 0.389881 0.048 Uiso 0.786(3) 1 calc R . P A 1
C3 C 0.6260(17) 0.5019(11) 0.4749(5) 0.0279(13) Uani 0.786(3) 1 d . U P A 1
H3 H 0.572934 0.432900 0.453093 0.033 Uiso 0.786(3) 1 calc R . P A 1
C4 C 0.6994(12) 0.5195(5) 0.5597(6) 0.0214(9) Uani 0.786(3) 1 d . U P A 1
S1A S 0.6345(17) 0.5129(12) 0.4840(6) 0.045(2) Uani 0.214(3) 1 d . U P A 2
C1A C 0.686(2) 0.6489(13) 0.4456(11) 0.030(3) Uani 0.214(3) 1 d . U P A 2
H1AA H 0.669497 0.678750 0.395429 0.036 Uiso 0.214(3) 1 calc R . P A 2
C2A C 0.757(3) 0.7007(17) 0.5084(9) 0.044(3) Uani 0.214(3) 1 d . U P A 2
H2A H 0.797392 0.780628 0.505073 0.052 Uiso 0.214(3) 1 calc R . P A 2
C3A C 0.774(3) 0.6425(16) 0.5770(10) 0.0279(13) Uani 0.214(3) 1 d . U P A 2
H3A H 0.820405 0.671115 0.624075 0.033 Uiso 0.214(3) 1 calc R . P A 2
C4A C 0.709(5) 0.539(2) 0.561(2) 0.026(3) Uani 0.214(3) 1 d . U P A 2


_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
O1 H1 0.8400 . ?
O1 C14 1.4174(18) . ?
O2 C17 1.215(2) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C5 C6 1.345(2) . ?
C5 C4 1.439(9) . ?
C5 C4A 1.56(3) . ?
C6 C7 1.477(2) . ?
C6 C14 1.532(2) . ?
C7 C8 1.4013(19) . ?
C7 C12 1.406(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(2) . ?
C12 C13 1.527(2) . ?
C13 C14 1.564(2) . ?
C13 C17 1.527(2) . ?
C13 C18 1.531(2) . ?
C14 C15 1.556(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.531(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.515(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
S1 C1 1.688(5) . ?
S1 C4 1.756(6) . ?
C1 H1A 0.9500 . ?
C1 C2 1.394(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.596(12) . ?
S1A C1A 1.717(18) . ?
S1A C4A 1.49(4) . ?
C1A H1AA 0.9500 . ?
C1A C2A 1.35(2) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.38(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.29(3) . ?

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 O1 H1 109.5 . . ?
C6 C5 H5A 115.1 . . ?
C6 C5 H5B 111.7 . . ?
C6 C5 C4 129.8(3) . . ?
C6 C5 C4A 136.5(12) . . ?
C4 C5 H5A 115.1 . . ?
C4A C5 H5B 111.7 . . ?
C5 C6 C7 133.62(14) . . ?
C5 C6 C14 121.96(13) . . ?
C7 C6 C14 104.37(12) . . ?
C8 C7 C6 130.93(14) . . ?
C8 C7 C12 119.48(13) . . ?
C12 C7 C6 109.51(12) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.91(14) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.93(14) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.90(15) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.25(15) . . ?
C12 C11 H11 120.9 . . ?
C7 C12 C13 111.03(13) . . ?
C11 C12 C7 121.44(14) . . ?
C11 C12 C13 127.51(14) . . ?
C12 C13 C14 100.52(11) . . ?
C12 C13 C18 112.29(12) . . ?
C17 C13 C12 110.66(13) . . ?
C17 C13 C14 104.80(12) . . ?
C17 C13 C18 112.46(13) . . ?
C18 C13 C14 115.29(13) . . ?
O1 C14 C6 115.50(13) . . ?
O1 C14 C13 114.95(13) . . ?
O1 C14 C15 106.57(12) . . ?
C6 C14 C13 104.47(11) . . ?
C6 C14 C15 111.42(13) . . ?
C15 C14 C13 103.36(12) . . ?
C14 C15 H15A 110.6 . . ?
C14 C15 H15B 110.6 . . ?
H15A C15 H15B 108.8 . . ?
C16 C15 C14 105.55(13) . . ?
C16 C15 H15A 110.6 . . ?
C16 C15 H15B 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
C17 C16 C15 105.53(14) . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
O2 C17 C13 125.50(16) . . ?
O2 C17 C16 124.86(16) . . ?
C16 C17 C13 109.64(14) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 S1 C4 93.9(4) . . ?
S1 C1 H1A 124.6 . . ?
C2 C1 S1 110.8(4) . . ?
C2 C1 H1A 124.6 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(7) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 128.0 . . ?
C2 C3 C4 104.0(8) . . ?
C4 C3 H3 128.0 . . ?
C5 C4 S1 117.3(6) . . ?
C5 C4 C3 132.7(5) . . ?
C3 C4 S1 109.7(7) . . ?
C4A S1A C1A 95.8(14) . . ?
S1A C1A H1AA 130.6 . . ?
C2A C1A S1A 98.7(14) . . ?
C2A C1A H1AA 130.6 . . ?
C1A C2A H2A 118.7 . . ?
C1A C2A C3A 122.7(18) . . ?
C3A C2A H2A 118.7 . . ?
C2A C3A H3A 129.0 . . ?
C4A C3A C2A 102(2) . . ?
C4A C3A H3A 129.0 . . ?
S1A C4A C5 120.9(18) . . ?
C3A C4A C5 118(3) . . ?
C3A C4A S1A 121(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
