# Supplementary Information (SI) for ChemComm.
# 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. 
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data_231012_y1_0m
_database_code_depnum_ccdc_archive 'CCDC 2308326'
loop_
_audit_author_name
_audit_author_address
'Kelu Yan'
;Qufu Normal University
China
;
_audit_update_record             
;
2023-11-16 deposited with the CCDC.	2025-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 O S'
_chemical_formula_sum            'C23 H16 O S'
_chemical_formula_weight         340.42
_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                   12.7462(15)
_cell_length_b                   9.1384(10)
_cell_length_c                   15.0589(17)
_cell_angle_alpha                90
_cell_angle_beta                 95.183(4)
_cell_angle_gamma                90
_cell_volume                     1746.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0909 before and 0.0470 after correction. The Ratio of minimum to maximum transmission is 0.8963. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blcok
_exptl_crystal_F_000             712
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28047
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.677
_diffrn_reflns_theta_min         2.194
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4254
_reflns_number_total             5329
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1182
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(S1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C13(H13), C6(H6), C22(H22), C20(H20), C10(H10), C21(H21), C8(H8),
 C2(H2), C14(H14), C17(H17), C7(H7), C1(H1), C15(H15), C9(H9), C16(H16)
;
_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 0.51005(3) 0.70962(3) 0.66655(2) 0.04636(10) Uani 1 1 d . U . . .
O1 O 0.35071(9) 0.83866(12) 0.74636(9) 0.0700(3) Uani 1 1 d . . . . .
C11 C 0.64848(9) 0.49936(11) 0.61665(7) 0.0365(2) Uani 1 1 d . . . . .
C23 C 0.50317(9) 0.41346(12) 0.70921(7) 0.0388(2) Uani 1 1 d . . . . .
C18 C 0.58991(9) 0.38472(11) 0.65917(7) 0.0373(2) Uani 1 1 d . . . . .
C5 C 0.67364(9) 0.76400(12) 0.57448(7) 0.0383(2) Uani 1 1 d . . . . .
C12 C 0.74146(9) 0.45490(12) 0.56914(8) 0.0392(2) Uani 1 1 d . . . . .
C3 C 0.46043(9) 0.56093(12) 0.72166(8) 0.0398(2) Uani 1 1 d . . . . .
C4 C 0.61831(9) 0.64117(12) 0.61647(7) 0.0377(2) Uani 1 1 d . . . . .
C19 C 0.62015(11) 0.23775(13) 0.64840(8) 0.0454(3) Uani 1 1 d . . . . .
H19 H 0.6761 0.2174 0.6148 0.055 Uiso 1 1 calc R . . . .
C13 C 0.73822(11) 0.46631(15) 0.47683(8) 0.0491(3) Uani 1 1 d . . . . .
H13 H 0.6786 0.5044 0.4448 0.059 Uiso 1 1 calc R . . . .
C6 C 0.62204(11) 0.84448(14) 0.50593(9) 0.0491(3) Uani 1 1 d . . . . .
H6 H 0.5536 0.8198 0.4846 0.059 Uiso 1 1 calc R . . . .
C22 C 0.45394(12) 0.29333(14) 0.74686(9) 0.0520(3) Uani 1 1 d . . . . .
H22 H 0.3975 0.3106 0.7804 0.062 Uiso 1 1 calc R . . . .
C20 C 0.56954(12) 0.12373(13) 0.68601(9) 0.0526(3) Uani 1 1 d . . . . .
H20 H 0.5915 0.0280 0.6779 0.063 Uiso 1 1 calc R . . . .
C10 C 0.77538(11) 0.80309(15) 0.60602(10) 0.0552(3) Uani 1 1 d . . . . .
H10 H 0.8110 0.7501 0.6521 0.066 Uiso 1 1 calc R . . . .
C21 C 0.48636(13) 0.15146(14) 0.73575(10) 0.0574(3) Uani 1 1 d . . . . .
H21 H 0.4522 0.0747 0.7617 0.069 Uiso 1 1 calc R . . . .
C8 C 0.77222(13) 1.00022(15) 0.50038(10) 0.0608(4) Uani 1 1 d . . . . .
H8 H 0.8052 1.0793 0.4757 0.073 Uiso 1 1 calc R . . . .
C2 C 0.38040(11) 0.58782(15) 0.77455(10) 0.0550(3) Uani 1 1 d . . . . .
H2 H 0.3556 0.5091 0.8057 0.066 Uiso 1 1 calc R . . . .
C14 C 0.82295(13) 0.42152(17) 0.43208(10) 0.0620(4) Uani 1 1 d . . . . .
H14 H 0.8197 0.4297 0.3703 0.074 Uiso 1 1 calc R . . . .
C17 C 0.83154(10) 0.39810(15) 0.61509(10) 0.0518(3) Uani 1 1 d . . . . .
H17 H 0.8353 0.3898 0.6768 0.062 Uiso 1 1 calc R . . . .
C7 C 0.67197(13) 0.96206(15) 0.46873(9) 0.0586(4) Uani 1 1 d . . . . .
H7 H 0.6371 1.0148 0.4222 0.070 Uiso 1 1 calc R . . . .
C1 C 0.33210(12) 0.72700(17) 0.78564(12) 0.0633(4) Uani 1 1 d . . . . .
H1 H 0.2819 0.7325 0.8266 0.076 Uiso 1 1 calc R . . . .
C15 C 0.91156(12) 0.36528(17) 0.47815(12) 0.0653(4) Uani 1 1 d . . . . .
H15 H 0.9682 0.3352 0.4479 0.078 Uiso 1 1 calc R . . . .
C9 C 0.82420(13) 0.92114(18) 0.56891(12) 0.0679(4) Uani 1 1 d . . . . .
H9 H 0.8924 0.9471 0.5904 0.081 Uiso 1 1 calc R . . . .
C16 C 0.91605(11) 0.35357(18) 0.56983(13) 0.0647(4) Uani 1 1 d . . . . .
H16 H 0.9760 0.3156 0.6014 0.078 Uiso 1 1 calc R . . . .


_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 C3 1.7406(11) . ?
S1 C4 1.7470(12) . ?
O1 C1 1.2135(19) . ?
C11 C18 1.4667(14) . ?
C11 C12 1.4950(15) . ?
C11 C4 1.3517(15) . ?
C23 C18 1.4176(16) . ?
C23 C3 1.4719(16) . ?
C23 C22 1.4087(15) . ?
C18 C19 1.4107(16) . ?
C5 C4 1.4959(14) . ?
C5 C6 1.3844(17) . ?
C5 C10 1.3869(18) . ?
C12 C13 1.3909(17) . ?
C12 C17 1.3867(18) . ?
C3 C2 1.3719(17) . ?
C19 C20 1.3743(17) . ?
C13 C14 1.3854(19) . ?
C6 C7 1.3921(18) . ?
C22 C21 1.3755(19) . ?
C20 C21 1.376(2) . ?
C10 C9 1.3878(19) . ?
C8 C7 1.368(2) . ?
C8 C9 1.379(2) . ?
C2 C1 1.429(2) . ?
C14 C15 1.371(2) . ?
C17 C16 1.387(2) . ?
C15 C16 1.381(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
C3 S1 C4 105.16(5) . . ?
C18 C11 C12 118.14(9) . . ?
C4 C11 C18 121.99(10) . . ?
C4 C11 C12 119.82(10) . . ?
C18 C23 C3 123.55(10) . . ?
C22 C23 C18 117.82(11) . . ?
C22 C23 C3 118.60(11) . . ?
C23 C18 C11 123.50(10) . . ?
C19 C18 C11 118.34(10) . . ?
C19 C18 C23 118.15(10) . . ?
C6 C5 C4 120.22(11) . . ?
C6 C5 C10 119.02(11) . . ?
C10 C5 C4 120.70(11) . . ?
C13 C12 C11 120.31(11) . . ?
C17 C12 C11 121.29(11) . . ?
C17 C12 C13 118.37(12) . . ?
C23 C3 S1 119.96(8) . . ?
C2 C3 S1 117.28(9) . . ?
C2 C3 C23 122.76(10) . . ?
C11 C4 S1 125.31(8) . . ?
C11 C4 C5 125.12(10) . . ?
C5 C4 S1 109.56(8) . . ?
C20 C19 C18 122.09(12) . . ?
C14 C13 C12 120.66(13) . . ?
C5 C6 C7 120.42(13) . . ?
C21 C22 C23 122.41(13) . . ?
C19 C20 C21 119.88(12) . . ?
C5 C10 C9 120.11(13) . . ?
C22 C21 C20 119.64(12) . . ?
C7 C8 C9 119.83(12) . . ?
C3 C2 C1 125.30(12) . . ?
C15 C14 C13 120.48(14) . . ?
C12 C17 C16 120.63(14) . . ?
C8 C7 C6 120.21(13) . . ?
O1 C1 C2 125.88(14) . . ?
C14 C15 C16 119.53(13) . . ?
C8 C9 C10 120.40(14) . . ?
C15 C16 C17 120.32(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
