# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_0107_8393_0m
_database_code_depnum_ccdc_archive 'CCDC 2346234'
loop_
_audit_author_name
_audit_author_address
'Jin Zhang'
;Shaanxi University of Science and Technology
China
;
_audit_update_record             
;
2024-04-07 deposited with the CCDC.	2025-02-21 downloaded from the CCDC.
;
_audit_creation_date             2024-01-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        (Z)-3-hydroxy-1,3-diphenylprop-2-ene-1-thione
_chemical_formula_moiety         'C15 H12 O S'
_chemical_formula_sum            'C15 H12 O S'
_chemical_formula_weight         240.31
_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/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                   12.5206(13)
_cell_length_b                   7.4108(8)
_cell_length_c                   13.2690(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.254(3)
_cell_angle_gamma                90
_cell_volume                     1218.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7019
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      24.890
_cell_measurement_theta_min      3.156
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0521 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.8914.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            RED
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_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  0.0317
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14813
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.065
_diffrn_reflns_theta_max         25.065
_diffrn_reflns_theta_min         3.157
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1725
_reflns_number_total             2126
_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       ?
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.067
_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)+(0.0288P)²+0.4633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0856
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C5(H5), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13),
  C14(H14), C15(H15)
2.b 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
S1 S 0.69695(4) 0.40909(8) 0.82612(4) 0.05949(19) Uani 1 1 d . . . . .
O1 O 0.48354(10) 0.4505(2) 0.71629(9) 0.0590(4) Uani 1 1 d . . . . .
H1 H 0.537486 0.457658 0.761725 0.088 Uiso 1 1 calc R U . . .
C1 C 0.60976(13) 0.2825(2) 0.63861(12) 0.0395(4) Uani 1 1 d . . . . .
H1A H 0.620539 0.215331 0.579934 0.047 Uiso 1 1 calc R U . . .
C2 C 0.97418(15) 0.0816(3) 0.75454(18) 0.0599(5) Uani 1 1 d . . . . .
H2 H 1.022123 0.028478 0.808371 0.072 Uiso 1 1 calc R U . . .
C3 C 0.34110(15) 0.2115(3) 0.39440(16) 0.0603(5) Uani 1 1 d . . . . .
H3 H 0.351178 0.160531 0.330734 0.072 Uiso 1 1 calc R U . . .
C4 C 0.69939(13) 0.3017(2) 0.71494(12) 0.0406(4) Uani 1 1 d . . . . .
C5 C 1.00292(15) 0.0909(3) 0.65886(18) 0.0630(6) Uani 1 1 d . . . . .
H5 H 1.071392 0.047670 0.646838 0.076 Uiso 1 1 calc R U . . .
C6 C 0.80373(12) 0.2235(2) 0.69464(12) 0.0395(4) Uani 1 1 d . . . . .
C7 C 0.22475(15) 0.3263(3) 0.50499(17) 0.0628(6) Uani 1 1 d . . . . .
H7 H 0.154131 0.354629 0.518377 0.075 Uiso 1 1 calc R U . . .
C8 C 0.50790(13) 0.3515(2) 0.64050(12) 0.0402(4) Uani 1 1 d . . . . .
C9 C 0.31252(14) 0.3616(3) 0.57780(15) 0.0533(5) Uani 1 1 d . . . . .
H9 H 0.301900 0.415000 0.640696 0.064 Uiso 1 1 calc R U . . .
C10 C 0.41628(12) 0.3197(2) 0.55983(12) 0.0389(4) Uani 1 1 d . . . . .
C11 C 0.23865(15) 0.2511(3) 0.41385(17) 0.0606(5) Uani 1 1 d . . . . .
H11 H 0.177949 0.226255 0.364150 0.073 Uiso 1 1 calc R U . . .
C12 C 0.83279(13) 0.2271(2) 0.59769(13) 0.0463(4) Uani 1 1 d . . . . .
H12 H 0.783818 0.274075 0.542604 0.056 Uiso 1 1 calc R U . . .
C13 C 0.93231(15) 0.1632(3) 0.58033(16) 0.0578(5) Uani 1 1 d . . . . .
H13 H 0.951936 0.169146 0.513857 0.069 Uiso 1 1 calc R U . . .
C14 C 0.87615(14) 0.1487(2) 0.77334(14) 0.0498(5) Uani 1 1 d . . . . .
H14 H 0.857831 0.144038 0.840331 0.060 Uiso 1 1 calc R U . . .
C15 C 0.42899(14) 0.2453(3) 0.46675(13) 0.0494(5) Uani 1 1 d . . . . .
H15 H 0.499349 0.217098 0.452570 0.059 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 C4 1.6804(17) . ?
O1 H1 0.8400 . ?
O1 C8 1.3153(19) . ?
C1 H1A 0.9500 . ?
C1 C4 1.407(2) . ?
C1 C8 1.378(2) . ?
C2 H2 0.9500 . ?
C2 C5 1.370(3) . ?
C2 C14 1.380(3) . ?
C3 H3 0.9500 . ?
C3 C11 1.376(3) . ?
C3 C15 1.375(2) . ?
C4 C6 1.489(2) . ?
C5 H5 0.9500 . ?
C5 C13 1.375(3) . ?
C6 C12 1.386(2) . ?
C6 C14 1.396(2) . ?
C7 H7 0.9500 . ?
C7 C9 1.380(3) . ?
C7 C11 1.365(3) . ?
C8 C10 1.471(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(2) . ?
C10 C15 1.383(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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
C8 O1 H1 109.5 . . ?
C4 C1 H1A 116.8 . . ?
C8 C1 H1A 116.8 . . ?
C8 C1 C4 126.46(16) . . ?
C5 C2 H2 119.7 . . ?
C5 C2 C14 120.54(18) . . ?
C14 C2 H2 119.7 . . ?
C11 C3 H3 119.9 . . ?
C15 C3 H3 119.9 . . ?
C15 C3 C11 120.28(19) . . ?
C1 C4 S1 124.52(13) . . ?
C1 C4 C6 117.43(14) . . ?
C6 C4 S1 118.05(12) . . ?
C2 C5 H5 120.1 . . ?
C2 C5 C13 119.75(18) . . ?
C13 C5 H5 120.1 . . ?
C12 C6 C4 120.96(15) . . ?
C12 C6 C14 118.24(16) . . ?
C14 C6 C4 120.79(16) . . ?
C9 C7 H7 119.7 . . ?
C11 C7 H7 119.7 . . ?
C11 C7 C9 120.50(18) . . ?
O1 C8 C1 122.53(15) . . ?
O1 C8 C10 113.80(14) . . ?
C1 C8 C10 123.66(15) . . ?
C7 C9 H9 119.7 . . ?
C7 C9 C10 120.51(18) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C8 119.33(16) . . ?
C15 C10 C8 122.43(15) . . ?
C15 C10 C9 118.23(16) . . ?
C3 C11 H11 120.2 . . ?
C7 C11 C3 119.61(18) . . ?
C7 C11 H11 120.2 . . ?
C6 C12 H12 119.6 . . ?
C13 C12 C6 120.70(17) . . ?
C13 C12 H12 119.6 . . ?
C5 C13 C12 120.26(19) . . ?
C5 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C2 C14 C6 120.47(18) . . ?
C2 C14 H14 119.8 . . ?
C6 C14 H14 119.8 . . ?
C3 C15 C10 120.86(17) . . ?
C3 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?

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 C4 C6 C12 -142.92(14) . . . . ?
S1 C4 C6 C14 35.4(2) . . . . ?
O1 C8 C10 C9 -12.5(2) . . . . ?
O1 C8 C10 C15 168.99(16) . . . . ?
C1 C4 C6 C12 36.2(2) . . . . ?
C1 C4 C6 C14 -145.48(16) . . . . ?
C1 C8 C10 C9 166.51(17) . . . . ?
C1 C8 C10 C15 -12.0(3) . . . . ?
C2 C5 C13 C12 0.3(3) . . . . ?
C4 C1 C8 O1 1.7(3) . . . . ?
C4 C1 C8 C10 -177.23(16) . . . . ?
C4 C6 C12 C13 176.49(17) . . . . ?
C4 C6 C14 C2 -177.98(16) . . . . ?
C5 C2 C14 C6 1.5(3) . . . . ?
C6 C12 C13 C5 1.6(3) . . . . ?
C7 C9 C10 C8 -177.37(17) . . . . ?
C7 C9 C10 C15 1.2(3) . . . . ?
C8 C1 C4 S1 2.1(3) . . . . ?
C8 C1 C4 C6 -176.94(16) . . . . ?
C8 C10 C15 C3 177.67(17) . . . . ?
C9 C7 C11 C3 -0.5(3) . . . . ?
C9 C10 C15 C3 -0.8(3) . . . . ?
C11 C3 C15 C10 -0.1(3) . . . . ?
C11 C7 C9 C10 -0.6(3) . . . . ?
C12 C6 C14 C2 0.4(3) . . . . ?
C14 C2 C5 C13 -1.8(3) . . . . ?
C14 C6 C12 C13 -1.9(3) . . . . ?
C15 C3 C11 C7 0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: PE/Et2O'
