# 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 
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data_20230507sch_a
_database_code_depnum_ccdc_archive 'CCDC 2370209'
loop_
_audit_author_name
_audit_author_address
'Lu Bin'
;Shandong university
China
;
_audit_update_record             
;
2024-07-12 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_audit_creation_date             2023-05-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H12 S2'
_chemical_formula_sum            'C24 H12 S2'
_chemical_formula_weight         364.46
_chemical_absolute_configuration ?
_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 0.0181 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'
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      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                   4.3795(2)
_cell_length_b                   13.5336(8)
_cell_length_c                   27.4731(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1628.34(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2913
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      73.87
_cell_measurement_theta_min      3.22
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.469
_exptl_absorpt_coefficient_mu    2.974
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1674 before and 0.1125 after correction.
The Ratio of minimum to maximum transmission is 0.6284.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1416
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17958
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.217
_diffrn_ambient_temperature      301.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2014
_reflns_number_total             2959
_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 (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 550 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0837
_refine_ls_restrained_S_all      1.035
_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)+(0.1241P)²+0.7380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2107
_refine_ls_wR_factor_ref         0.2426
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C8(H8), C16(H16), C12(H12), C13(H13), C23(H23),
 C24(H24), C21(H21), C22(H22)
2.b Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C10(C9,C14,C15,C16,C11), C23(C24,C20,C19,C21,C22)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.4064(5) 0.36756(17) 0.27925(9) 0.0705(7) Uani 1 1 d . . . . .
S2 S 0.0660(6) 0.64628(19) 0.24169(10) 0.0768(7) Uani 1 1 d . . . . .
C1 C 1.3916(15) 0.4455(5) 0.5141(2) 0.084(3) Uani 1 1 d G . . . .
H1 H 1.516792 0.432152 0.540626 0.101 Uiso 1 1 calc R U . . .
C2 C 1.3003(15) 0.3692(4) 0.4835(2) 0.079(3) Uani 1 1 d G . . . .
H2 H 1.364270 0.304862 0.489556 0.095 Uiso 1 1 calc R U . . .
C3 C 1.1132(14) 0.3891(4) 0.4438(2) 0.068(2) Uani 1 1 d G . . . .
C4 C 1.0175(13) 0.4853(4) 0.43472(18) 0.065(2) Uani 1 1 d G . . . .
C5 C 1.1089(15) 0.5616(3) 0.4653(2) 0.072(2) Uani 1 1 d G . . . .
C6 C 1.2960(16) 0.5417(4) 0.5050(2) 0.082(3) Uani 1 1 d G . . . .
H6 H 1.357092 0.592682 0.525468 0.099 Uiso 1 1 calc R U . . .
C7 C 1.015(2) 0.3111(7) 0.4117(4) 0.072(2) Uani 1 1 d . . . . .
H7 H 1.08(3) 0.248(8) 0.420(4) 0.087 Uiso 1 1 d . U . . .
C8 C 0.835(2) 0.3294(7) 0.3730(3) 0.066(2) Uani 1 1 d . . . . .
H8 H 0.776155 0.277669 0.352863 0.079 Uiso 1 1 calc R U . . .
C10 C 0.8202(12) 0.5071(4) 0.39313(18) 0.063(2) Uani 1 1 d G . . . .
C9 C 0.7287(14) 0.4313(3) 0.3623(2) 0.066(2) Uani 1 1 d G . . . .
C14 C 0.5409(14) 0.4518(3) 0.32274(19) 0.065(2) Uani 1 1 d G . . . .
C15 C 0.4445(13) 0.5480(4) 0.31410(18) 0.064(2) Uani 1 1 d G . . . .
C16 C 0.5360(13) 0.6238(3) 0.3450(2) 0.068(2) Uani 1 1 d G . . . .
H16 H 0.471458 0.688245 0.339187 0.081 Uiso 1 1 calc R U . . .
C11 C 0.7238(13) 0.6034(4) 0.3845(2) 0.070(2) Uani 1 1 d G . . . .
C12 C 0.825(2) 0.6818(8) 0.4173(4) 0.075(3) Uani 1 1 d . . . . .
H12 H 0.761267 0.746494 0.411797 0.090 Uiso 1 1 calc R U . . .
C13 C 1.010(2) 0.6614(8) 0.4557(4) 0.080(3) Uani 1 1 d . . . . .
H13 H 1.073480 0.712374 0.476062 0.096 Uiso 1 1 calc R U . . .
C17 C 0.218(2) 0.4626(7) 0.2492(3) 0.066(2) Uani 1 1 d . . . . .
C18 C 0.251(2) 0.5524(7) 0.2713(4) 0.072(2) Uani 1 1 d . . . . .
C23 C -0.3489(15) 0.5113(6) 0.1277(2) 0.090(3) Uani 1 1 d G . . . .
H23 H -0.475309 0.526144 0.101477 0.108 Uiso 1 1 calc R U . . .
C24 C -0.2619(16) 0.5853(4) 0.1599(2) 0.077(3) Uani 1 1 d G . . . .
H24 H -0.330126 0.649682 0.155255 0.093 Uiso 1 1 calc R U . . .
C20 C -0.0730(15) 0.5631(4) 0.1990(2) 0.071(2) Uani 1 1 d G . . . .
C19 C 0.0289(14) 0.4668(5) 0.2060(2) 0.073(2) Uani 1 1 d G . . . .
C21 C -0.0580(16) 0.3928(4) 0.1738(2) 0.080(3) Uani 1 1 d G . . . .
H21 H 0.010165 0.328415 0.178399 0.096 Uiso 1 1 calc R U . . .
C22 C -0.2470(17) 0.4150(5) 0.1346(2) 0.087(3) Uani 1 1 d G . . . .
H22 H -0.305161 0.365508 0.113050 0.104 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 C14 1.753(5) . ?
S1 C17 1.737(10) . ?
S2 C18 1.713(11) . ?
S2 C20 1.735(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C3 C7 1.441(12) . ?
C4 C5 1.3900 . ?
C4 C10 1.463(6) . ?
C5 C6 1.3900 . ?
C5 C13 1.444(12) . ?
C6 H6 0.9300 . ?
C7 H7 0.94(11) . ?
C7 C8 1.347(14) . ?
C8 H8 0.9300 . ?
C8 C9 1.485(10) . ?
C10 C9 1.3900 . ?
C10 C11 1.3900 . ?
C9 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C15 C18 1.450(11) . ?
C16 H16 0.9300 . ?
C16 C11 1.3900 . ?
C11 C12 1.461(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.361(15) . ?
C13 H13 0.9300 . ?
C17 C18 1.365(14) . ?
C17 C19 1.449(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.3900 . ?
C23 C22 1.3900 . ?
C24 H24 0.9300 . ?
C24 C20 1.3900 . ?
C20 C19 1.3900 . ?
C19 C21 1.3900 . ?
C21 H21 0.9300 . ?
C21 C22 1.3900 . ?
C22 H22 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
C17 S1 C14 90.1(4) . . ?
C18 S2 C20 90.3(4) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C7 120.9(5) . . ?
C4 C3 C2 120.0 . . ?
C4 C3 C7 119.1(5) . . ?
C3 C4 C10 120.5(4) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 C10 119.5(4) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C13 119.9(6) . . ?
C6 C5 C13 120.1(6) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C3 C7 H7 115(7) . . ?
C8 C7 C3 121.4(8) . . ?
C8 C7 H7 124(7) . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(8) . . ?
C9 C8 H8 119.6 . . ?
C9 C10 C4 119.9(4) . . ?
C9 C10 C11 120.0 . . ?
C11 C10 C4 120.1(4) . . ?
C10 C9 C8 118.2(5) . . ?
C14 C9 C8 121.8(5) . . ?
C14 C9 C10 120.0 . . ?
C9 C14 S1 127.0(3) . . ?
C9 C14 C15 120.0 . . ?
C15 C14 S1 113.0(3) . . ?
C14 C15 C18 110.7(5) . . ?
C16 C15 C14 120.0 . . ?
C16 C15 C18 129.3(5) . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C11 120.0 . . ?
C11 C16 H16 120.0 . . ?
C10 C11 C12 119.0(6) . . ?
C16 C11 C10 120.0 . . ?
C16 C11 C12 121.0(6) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(9) . . ?
C13 C12 H12 119.6 . . ?
C5 C13 H13 119.6 . . ?
C12 C13 C5 120.7(9) . . ?
C12 C13 H13 119.6 . . ?
C18 C17 S1 113.4(7) . . ?
C18 C17 C19 112.9(8) . . ?
C19 C17 S1 133.6(7) . . ?
C15 C18 S2 133.7(7) . . ?
C17 C18 S2 113.5(7) . . ?
C17 C18 C15 112.7(8) . . ?
C24 C23 H23 120.0 . . ?
C24 C23 C22 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C20 120.0 . . ?
C20 C24 H24 120.0 . . ?
C24 C20 S2 126.2(4) . . ?
C19 C20 S2 113.8(4) . . ?
C19 C20 C24 120.0 . . ?
C20 C19 C17 109.4(5) . . ?
C20 C19 C21 120.0 . . ?
C21 C19 C17 130.6(5) . . ?
C19 C21 H21 120.0 . . ?
C22 C21 C19 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?

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 C14 C15 C16 -179.0(4) . . . . ?
S1 C14 C15 C18 1.0(5) . . . . ?
S1 C17 C18 S2 180.0(5) . . . . ?
S1 C17 C18 C15 1.7(10) . . . . ?
S1 C17 C19 C20 178.0(7) . . . . ?
S1 C17 C19 C21 -1.3(13) . . . . ?
S2 C20 C19 C17 2.3(6) . . . . ?
S2 C20 C19 C21 -178.4(5) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C7 -179.9(7) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C2 C3 C4 C10 -179.9(6) . . . . ?
C2 C3 C7 C8 -179.8(7) . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 C13 179.8(7) . . . . ?
C3 C4 C10 C9 -0.3(6) . . . . ?
C3 C4 C10 C11 179.6(4) . . . . ?
C3 C7 C8 C9 -0.3(14) . . . . ?
C4 C3 C7 C8 0.3(12) . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C13 C12 0.8(12) . . . . ?
C4 C10 C9 C8 0.4(7) . . . . ?
C4 C10 C9 C14 179.9(6) . . . . ?
C4 C10 C11 C16 -179.9(6) . . . . ?
C4 C10 C11 C12 0.5(7) . . . . ?
C5 C4 C10 C9 179.8(4) . . . . ?
C5 C4 C10 C11 -0.3(6) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C6 C5 C13 C12 -179.4(8) . . . . ?
C7 C3 C4 C5 179.9(7) . . . . ?
C7 C3 C4 C10 0.0(7) . . . . ?
C7 C8 C9 C10 -0.1(11) . . . . ?
C7 C8 C9 C14 -179.6(7) . . . . ?
C8 C9 C14 S1 -1.6(6) . . . . ?
C8 C9 C14 C15 179.5(7) . . . . ?
C10 C4 C5 C6 179.9(6) . . . . ?
C10 C4 C5 C13 -0.3(8) . . . . ?
C10 C9 C14 S1 178.9(5) . . . . ?
C10 C9 C14 C15 0.0 . . . . ?
C10 C11 C12 C13 0.0(12) . . . . ?
C9 C10 C11 C16 0.0 . . . . ?
C9 C10 C11 C12 -179.6(7) . . . . ?
C9 C14 C15 C16 0.0 . . . . ?
C9 C14 C15 C18 -180.0(6) . . . . ?
C14 S1 C17 C18 -0.9(7) . . . . ?
C14 S1 C17 C19 -179.8(9) . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C14 C15 C18 S2 -179.6(7) . . . . ?
C14 C15 C18 C17 -1.7(9) . . . . ?
C15 C16 C11 C10 0.0 . . . . ?
C15 C16 C11 C12 179.6(7) . . . . ?
C16 C15 C18 S2 0.4(12) . . . . ?
C16 C15 C18 C17 178.3(6) . . . . ?
C16 C11 C12 C13 -179.6(7) . . . . ?
C11 C10 C9 C8 -179.5(6) . . . . ?
C11 C10 C9 C14 0.0 . . . . ?
C11 C12 C13 C5 -0.6(15) . . . . ?
C13 C5 C6 C1 -179.8(7) . . . . ?
C17 S1 C14 C9 -179.0(4) . . . . ?
C17 S1 C14 C15 -0.1(4) . . . . ?
C17 C19 C21 C22 179.2(8) . . . . ?
C18 S2 C20 C24 179.4(5) . . . . ?
C18 S2 C20 C19 -2.4(5) . . . . ?
C18 C15 C16 C11 180.0(7) . . . . ?
C18 C17 C19 C20 -0.9(9) . . . . ?
C18 C17 C19 C21 179.8(6) . . . . ?
C23 C24 C20 S2 178.1(6) . . . . ?
C23 C24 C20 C19 0.0 . . . . ?
C24 C23 C22 C21 0.0 . . . . ?
C24 C20 C19 C17 -179.4(6) . . . . ?
C24 C20 C19 C21 0.0 . . . . ?
C20 S2 C18 C15 179.7(9) . . . . ?
C20 S2 C18 C17 1.8(7) . . . . ?
C20 C19 C21 C22 0.0 . . . . ?
C19 C17 C18 S2 -0.9(10) . . . . ?
C19 C17 C18 C15 -179.2(7) . . . . ?
C19 C21 C22 C23 0.0 . . . . ?
C22 C23 C24 C20 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_liuzq201407_0m
_database_code_depnum_ccdc_archive 'CCDC 2375039'
loop_
_audit_author_name
_audit_author_address
'Wendong Jin'
;Shandong University
China
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_audit_creation_date             2024-08-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        PTBT-H
_chemical_formula_moiety         'C24 H12 S2'
_chemical_formula_sum            'C24 H12 S2'
_chemical_formula_weight         364.46
_chemical_absolute_configuration ?
_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'
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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   4.5998(3)
_cell_length_b                   13.6871(8)
_cell_length_c                   25.8017(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1624.42(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5495
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.96
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX2 Software Suite (Bruker,2009)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull yellowish'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.0595
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            25485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         1.578
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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                   ?
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2650
_reflns_number_total             3707
_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       ?
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.077
_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)+(0.0912P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1643
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C16(H16),
 C17(H17), C21(H21), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.069 
;
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 0.1144(3) -0.05050(9) 0.74446(5) 0.0444(4) Uani 1 1 d . . . . .
S2 S 0.4004(3) 0.23970(8) 0.74727(5) 0.0466(4) Uani 1 1 d . . . . .
C1 C -0.3373(13) 0.0186(4) 0.8736(2) 0.0566(14) Uani 1 1 d . . . . .
H1 H -0.462696 -0.009271 0.897715 0.068 Uiso 1 1 calc R U . . .
C2 C -0.2367(12) -0.0368(4) 0.83340(19) 0.0501(13) Uani 1 1 d . . . . .
H2 H -0.291971 -0.101811 0.829898 0.060 Uiso 1 1 calc R U . . .
C3 C -0.0489(10) 0.0067(4) 0.79768(17) 0.0408(12) Uani 1 1 d . . . . .
C4 C 0.2917(11) 0.0580(3) 0.72822(17) 0.0383(11) Uani 1 1 d . . . . .
C5 C 0.4898(10) 0.0850(3) 0.68793(17) 0.0385(11) Uani 1 1 d . . . . .
C6 C 0.6161(11) 0.0307(4) 0.64682(17) 0.0411(11) Uani 1 1 d . . . . .
C7 C 0.5504(11) -0.0700(4) 0.6380(2) 0.0460(12) Uani 1 1 d . . . . .
H7 H 0.417986 -0.101484 0.659525 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6758(11) -0.1199(4) 0.59934(19) 0.0501(13) Uani 1 1 d . . . . .
H8 H 0.628860 -0.185505 0.594959 0.060 Uiso 1 1 calc R U . . .
C9 C 0.8778(12) -0.0762(4) 0.56487(19) 0.0478(12) Uani 1 1 d . . . . .
C10 C 1.0153(12) -0.1286(5) 0.5252(2) 0.0579(15) Uani 1 1 d . . . . .
H10 H 0.975070 -0.194680 0.520767 0.070 Uiso 1 1 calc R U . . .
C11 C 1.2117(13) -0.0824(5) 0.4924(2) 0.0649(17) Uani 1 1 d . . . . .
H11 H 1.297137 -0.117309 0.465460 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2267(10) 0.1319(4) 0.76175(17) 0.0412(11) Uani 1 1 d . . . . .
C13 C 0.5705(11) 0.1842(4) 0.69392(17) 0.0415(11) Uani 1 1 d . . . . .
C14 C 0.7609(11) 0.2305(4) 0.66041(17) 0.0469(13) Uani 1 1 d . . . . .
H14 H 0.803931 0.296269 0.665142 0.056 Uiso 1 1 calc R U . . .
C15 C 0.8875(11) 0.1798(4) 0.62000(17) 0.0413(11) Uani 1 1 d . . . . .
C16 C 1.0888(12) 0.2226(4) 0.58506(19) 0.0538(13) Uani 1 1 d . . . . .
H16 H 1.135410 0.288268 0.588966 0.065 Uiso 1 1 calc R U . . .
C17 C 1.2146(13) 0.1718(4) 0.5465(2) 0.0575(15) Uani 1 1 d . . . . .
H17 H 1.345656 0.203090 0.524673 0.069 Uiso 1 1 calc R U . . .
C18 C 1.1508(12) 0.0696(4) 0.53829(19) 0.0513(14) Uani 1 1 d . . . . .
C19 C 0.9464(11) 0.0240(4) 0.57223(18) 0.0439(12) Uani 1 1 d . . . . .
C20 C 0.8148(10) 0.0775(4) 0.61315(16) 0.0409(12) Uani 1 1 d . . . . .
C21 C 1.2809(13) 0.0147(5) 0.49924(19) 0.0599(16) Uani 1 1 d . . . . .
H21 H 1.416499 0.043940 0.477481 0.072 Uiso 1 1 calc R U . . .
C22 C 0.0337(11) 0.1051(4) 0.80276(17) 0.0433(12) Uani 1 1 d . . . . .
C23 C -0.0767(11) 0.1600(4) 0.84440(19) 0.0524(14) Uani 1 1 d . . . . .
H23 H -0.028407 0.225569 0.848188 0.063 Uiso 1 1 calc R U . . .
C24 C -0.2564(12) 0.1151(5) 0.87920(19) 0.0559(15) Uani 1 1 d . . . . .
H24 H -0.325988 0.150491 0.907358 0.067 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 C3 1.750(5) . ?
S1 C4 1.745(5) . ?
S2 C12 1.719(5) . ?
S2 C13 1.756(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.366(7) . ?
C1 C24 1.380(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.396(7) . ?
C3 C22 1.407(7) . ?
C4 C5 1.431(7) . ?
C4 C12 1.364(7) . ?
C5 C6 1.420(6) . ?
C5 C13 1.416(7) . ?
C6 C7 1.429(7) . ?
C6 C20 1.414(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.340(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.419(7) . ?
C9 C10 1.401(7) . ?
C9 C19 1.420(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(8) . ?
C11 H11 0.9300 . ?
C11 C21 1.377(9) . ?
C12 C22 1.429(6) . ?
C13 C14 1.384(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(6) . ?
C15 C16 1.419(7) . ?
C15 C20 1.450(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.344(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.444(8) . ?
C18 C19 1.429(7) . ?
C18 C21 1.392(7) . ?
C19 C20 1.421(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.405(7) . ?
C23 H23 0.9300 . ?
C23 C24 1.366(7) . ?
C24 H24 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
C4 S1 C3 90.5(2) . . ?
C12 S2 C13 90.4(2) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C24 121.3(5) . . ?
C24 C1 H1 119.4 . . ?
C1 C2 H2 120.8 . . ?
C1 C2 C3 118.3(5) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 S1 126.4(4) . . ?
C2 C3 C22 120.9(5) . . ?
C22 C3 S1 112.7(4) . . ?
C5 C4 S1 133.8(4) . . ?
C12 C4 S1 112.1(4) . . ?
C12 C4 C5 114.1(4) . . ?
C6 C5 C4 131.9(4) . . ?
C13 C5 C4 109.6(4) . . ?
C13 C5 C6 118.4(4) . . ?
C5 C6 C7 122.5(5) . . ?
C20 C6 C5 119.1(4) . . ?
C20 C6 C7 118.4(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.3(5) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 118.9 . . ?
C7 C8 C9 122.3(5) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 C19 118.0(5) . . ?
C10 C9 C8 122.6(5) . . ?
C10 C9 C19 119.5(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(6) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 119.7 . . ?
C21 C11 C10 120.7(6) . . ?
C21 C11 H11 119.7 . . ?
C4 C12 S2 113.4(4) . . ?
C4 C12 C22 114.6(5) . . ?
C22 C12 S2 132.0(4) . . ?
C5 C13 S2 112.5(4) . . ?
C14 C13 S2 125.0(4) . . ?
C14 C13 C5 122.5(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.5(5) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C16 123.2(5) . . ?
C14 C15 C20 118.7(5) . . ?
C16 C15 C20 118.2(5) . . ?
C15 C16 H16 118.7 . . ?
C17 C16 C15 122.5(5) . . ?
C17 C16 H16 118.7 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.5(5) . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 117.8(5) . . ?
C21 C18 C17 122.8(5) . . ?
C21 C18 C19 119.3(6) . . ?
C9 C19 C18 119.1(5) . . ?
C9 C19 C20 120.2(5) . . ?
C20 C19 C18 120.7(5) . . ?
C6 C20 C15 120.8(4) . . ?
C6 C20 C19 119.9(4) . . ?
C19 C20 C15 119.4(4) . . ?
C11 C21 C18 121.0(6) . . ?
C11 C21 H21 119.5 . . ?
C18 C21 H21 119.5 . . ?
C3 C22 C12 110.2(4) . . ?
C23 C22 C3 119.0(5) . . ?
C23 C22 C12 130.8(5) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.7(5) . . ?
C24 C23 H23 120.6 . . ?
C1 C24 H24 119.2 . . ?
C23 C24 C1 121.7(5) . . ?
C23 C24 H24 119.2 . . ?

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 C3 C22 C12 1.1(5) . . . . ?
S1 C3 C22 C23 -178.9(4) . . . . ?
S1 C4 C5 C6 -1.1(8) . . . . ?
S1 C4 C5 C13 -178.9(4) . . . . ?
S1 C4 C12 S2 179.4(2) . . . . ?
S1 C4 C12 C22 0.7(5) . . . . ?
S2 C12 C22 C3 -179.6(4) . . . . ?
S2 C12 C22 C23 0.5(8) . . . . ?
S2 C13 C14 C15 178.9(4) . . . . ?
C1 C2 C3 S1 178.1(4) . . . . ?
C1 C2 C3 C22 -0.3(7) . . . . ?
C2 C1 C24 C23 1.1(8) . . . . ?
C2 C3 C22 C12 179.8(4) . . . . ?
C2 C3 C22 C23 -0.3(7) . . . . ?
C3 S1 C4 C5 179.3(5) . . . . ?
C3 S1 C4 C12 -0.1(4) . . . . ?
C3 C22 C23 C24 1.3(7) . . . . ?
C4 S1 C3 C2 -179.2(5) . . . . ?
C4 S1 C3 C22 -0.6(4) . . . . ?
C4 C5 C6 C7 1.7(8) . . . . ?
C4 C5 C6 C20 -178.2(4) . . . . ?
C4 C5 C13 S2 -0.6(5) . . . . ?
C4 C5 C13 C14 180.0(4) . . . . ?
C4 C12 C22 C3 -1.2(6) . . . . ?
C4 C12 C22 C23 178.8(5) . . . . ?
C5 C4 C12 S2 -0.1(5) . . . . ?
C5 C4 C12 C22 -178.8(4) . . . . ?
C5 C6 C7 C8 -179.0(5) . . . . ?
C5 C6 C20 C15 -0.6(6) . . . . ?
C5 C6 C20 C19 179.1(4) . . . . ?
C5 C13 C14 C15 -1.8(7) . . . . ?
C6 C5 C13 S2 -178.8(3) . . . . ?
C6 C5 C13 C14 1.8(7) . . . . ?
C6 C7 C8 C9 -0.5(8) . . . . ?
C7 C6 C20 C15 179.5(4) . . . . ?
C7 C6 C20 C19 -0.8(6) . . . . ?
C7 C8 C9 C10 178.3(5) . . . . ?
C7 C8 C9 C19 0.0(7) . . . . ?
C8 C9 C10 C11 180.0(5) . . . . ?
C8 C9 C19 C18 179.5(4) . . . . ?
C8 C9 C19 C20 0.1(7) . . . . ?
C9 C10 C11 C21 2.0(8) . . . . ?
C9 C19 C20 C6 0.4(7) . . . . ?
C9 C19 C20 C15 -179.9(5) . . . . ?
C10 C9 C19 C18 1.1(7) . . . . ?
C10 C9 C19 C20 -178.3(4) . . . . ?
C10 C11 C21 C18 -1.7(9) . . . . ?
C12 S2 C13 C5 0.5(4) . . . . ?
C12 S2 C13 C14 179.9(5) . . . . ?
C12 C4 C5 C6 178.3(5) . . . . ?
C12 C4 C5 C13 0.5(6) . . . . ?
C12 C22 C23 C24 -178.7(5) . . . . ?
C13 S2 C12 C4 -0.2(4) . . . . ?
C13 S2 C12 C22 178.1(5) . . . . ?
C13 C5 C6 C7 179.3(5) . . . . ?
C13 C5 C6 C20 -0.6(7) . . . . ?
C13 C14 C15 C16 -178.6(5) . . . . ?
C13 C14 C15 C20 0.6(7) . . . . ?
C14 C15 C16 C17 178.7(5) . . . . ?
C14 C15 C20 C6 0.6(7) . . . . ?
C14 C15 C20 C19 -179.1(4) . . . . ?
C15 C16 C17 C18 0.2(9) . . . . ?
C16 C15 C20 C6 179.9(4) . . . . ?
C16 C15 C20 C19 0.2(6) . . . . ?
C16 C17 C18 C19 0.6(8) . . . . ?
C16 C17 C18 C21 -179.0(5) . . . . ?
C17 C18 C19 C9 179.6(5) . . . . ?
C17 C18 C19 C20 -1.0(7) . . . . ?
C17 C18 C21 C11 -179.3(5) . . . . ?
C18 C19 C20 C6 -179.1(4) . . . . ?
C18 C19 C20 C15 0.6(7) . . . . ?
C19 C9 C10 C11 -1.7(8) . . . . ?
C19 C18 C21 C11 1.1(8) . . . . ?
C20 C6 C7 C8 0.9(7) . . . . ?
C20 C15 C16 C17 -0.6(8) . . . . ?
C21 C18 C19 C9 -0.8(7) . . . . ?
C21 C18 C19 C20 178.6(5) . . . . ?
C22 C23 C24 C1 -1.7(8) . . . . ?
C24 C1 C2 C3 -0.1(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichlorobenzene'
_chemical_compound_source        'room temperature'
