# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
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# 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_mo_240301a_0m
_database_code_depnum_ccdc_archive 'CCDC 2339912'
loop_
_audit_author_name
_audit_author_address
'Xianggao Meng'
;Central China Normal University
China
;
_audit_update_record             
;
2024-03-13 deposited with the CCDC.	2024-05-22 downloaded from the CCDC.
;
_audit_creation_date             2024-03-06
_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         'C25 H19 N S'
_chemical_formula_sum            'C25 H19 N S'
_chemical_formula_weight         365.47
_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'
N N 0.0061 0.0033 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.9563(16)
_cell_length_b                   5.8840(10)
_cell_length_c                   18.577(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.049(3)
_cell_angle_gamma                90
_cell_volume                     978.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5776
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      30.79
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.950
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10573
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.039
_diffrn_reflns_theta_min         2.507
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.763
_reflns_number_gt                5118
_reflns_number_total             5811
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1957 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         5811
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.046
_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)+(0.0717P)²+0.0836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1245
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All N(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C13(H13) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), 
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), N1(H1) 
2.c : 
 C25(H25) 
;
_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
C1 C 0.5289(2) 0.5755(4) 0.24736(10) 0.0375(4) Uani 1 1 d . . . . .
C2 C 0.5581(3) 0.7343(6) 0.30160(13) 0.0595(7) Uani 1 1 d . . . . .
H2 H 0.6261 0.8506 0.2936 0.071 Uiso 1 1 calc R . . . .
C3 C 0.4874(3) 0.7218(6) 0.36733(12) 0.0596(7) Uani 1 1 d . . . . .
H3 H 0.5087 0.8305 0.4024 0.071 Uiso 1 1 calc R . . . .
C4 C 0.3856(2) 0.5508(4) 0.38198(10) 0.0372(4) Uani 1 1 d . . . . .
C5 C 0.3577(3) 0.3935(4) 0.32765(12) 0.0475(5) Uani 1 1 d . . . . .
H5 H 0.2902 0.2766 0.3357 0.057 Uiso 1 1 calc R . . . .
C6 C 0.4277(3) 0.4054(4) 0.26143(12) 0.0460(5) Uani 1 1 d . . . . .
H6 H 0.4059 0.2973 0.2263 0.055 Uiso 1 1 calc R . . . .
C7 C 0.3058(2) 0.5410(4) 0.45190(10) 0.0414(4) Uani 1 1 d . . . . .
C8 C 0.3261(4) 0.7078(6) 0.50405(14) 0.0660(7) Uani 1 1 d . . . . .
H8 H 0.3916 0.8270 0.4956 0.079 Uiso 1 1 calc R . . . .
C9 C 0.2502(4) 0.7000(7) 0.56869(15) 0.0761(9) Uani 1 1 d . . . . .
H9 H 0.2657 0.8135 0.6029 0.091 Uiso 1 1 calc R . . . .
C10 C 0.1535(3) 0.5270(7) 0.58220(13) 0.0665(8) Uani 1 1 d . . . . .
H10 H 0.1023 0.5227 0.6253 0.080 Uiso 1 1 calc R . . . .
C11 C 0.1326(4) 0.3628(8) 0.53276(18) 0.0847(12) Uani 1 1 d . . . . .
H11 H 0.0662 0.2452 0.5419 0.102 Uiso 1 1 calc R . . . .
C12 C 0.2093(4) 0.3659(6) 0.46764(16) 0.0761(10) Uani 1 1 d . . . . .
H12 H 0.1949 0.2486 0.4347 0.091 Uiso 1 1 calc R . . . .
C13 C 0.6128(2) 0.5886(4) 0.17666(10) 0.0394(4) Uani 1 1 d . . . . .
H13 H 0.6253 0.7493 0.1644 0.047 Uiso 1 1 calc R . . . .
C14 C 0.4116(2) 0.5828(4) 0.08266(9) 0.0386(4) Uani 1 1 d . . . . .
C15 C 0.3491(3) 0.4792(5) 0.02125(12) 0.0504(5) Uani 1 1 d . . . . .
H15 H 0.3891 0.3437 0.0045 0.061 Uiso 1 1 calc R . . . .
C16 C 0.2290(3) 0.5762(7) -0.01454(13) 0.0641(7) Uani 1 1 d . . . . .
H16 H 0.1895 0.5057 -0.0555 0.077 Uiso 1 1 calc R . . . .
C17 C 0.1661(3) 0.7767(6) 0.00938(14) 0.0627(8) Uani 1 1 d . . . . .
H17 H 0.0852 0.8417 -0.0151 0.075 Uiso 1 1 calc R . . . .
C18 C 0.2257(3) 0.8777(5) 0.07009(14) 0.0566(6) Uani 1 1 d . . . . .
H18 H 0.1840 1.0120 0.0869 0.068 Uiso 1 1 calc R . . . .
C19 C 0.3474(3) 0.7826(4) 0.10688(11) 0.0471(5) Uani 1 1 d . . . . .
H19 H 0.3859 0.8535 0.1479 0.057 Uiso 1 1 calc R . . . .
C20 C 0.7661(2) 0.4839(4) 0.18450(10) 0.0392(4) Uani 1 1 d . . . . .
C21 C 0.8980(3) 0.5648(5) 0.16060(14) 0.0520(5) Uani 1 1 d . . . . .
H21 H 0.9068 0.7016 0.1360 0.062 Uiso 1 1 calc R . . . .
C22 C 1.0207(2) 0.4220(5) 0.17658(14) 0.0540(6) Uani 1 1 d . . . . .
H22 H 1.1182 0.4546 0.1636 0.065 Uiso 1 1 calc R . . . .
C23 C 0.9812(2) 0.2322(4) 0.21287(10) 0.0409(4) Uani 1 1 d . . . . .
C24 C 1.0731(2) 0.0533(5) 0.24049(12) 0.0486(5) Uani 1 1 d . . . . .
C25 C 1.1460(3) -0.0955(6) 0.26509(16) 0.0635(7) Uani 1 1 d . . . . .
H25 H 1.2035 -0.2128 0.2845 0.076 Uiso 1 1 calc R . . . .
N1 N 0.5327(2) 0.4785(4) 0.11724(9) 0.0455(4) Uani 1 1 d . . . . .
H1 H 0.5608 0.3463 0.1032 0.055 Uiso 1 1 calc R . . . .
S1 S 0.79121(6) 0.22730(11) 0.22720(3) 0.05202(17) Uani 1 1 d . . . . .


_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
C1 C2 1.396(3) . ?
C1 C6 1.379(3) . ?
C1 C13 1.527(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C4 C5 1.389(3) . ?
C4 C7 1.495(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.389(4) . ?
C7 C12 1.380(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.363(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.344(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9800 . ?
C13 C20 1.509(3) . ?
C13 N1 1.457(3) . ?
C14 C15 1.401(3) . ?
C14 C19 1.387(3) . ?
C14 N1 1.393(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.394(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(3) . ?
C20 S1 1.718(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.410(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.355(4) . ?
C23 C24 1.426(3) . ?
C23 S1 1.7277(19) . ?
C24 C25 1.179(4) . ?
C25 H25 0.9300 . ?
N1 H1 0.8600 . ?

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
C2 C1 C13 119.91(19) . . ?
C6 C1 C2 117.67(18) . . ?
C6 C1 C13 122.37(19) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 116.79(18) . . ?
C3 C4 C7 121.64(19) . . ?
C5 C4 C7 121.54(18) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.04(19) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 120.81(19) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C4 121.3(2) . . ?
C12 C7 C4 121.6(2) . . ?
C12 C7 C8 117.0(2) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.3(3) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 C11 120.7(3) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C1 C13 H13 108.0 . . ?
C20 C13 C1 110.95(16) . . ?
C20 C13 H13 108.0 . . ?
N1 C13 C1 112.70(17) . . ?
N1 C13 H13 108.0 . . ?
N1 C13 C20 109.05(17) . . ?
C19 C14 C15 118.1(2) . . ?
C19 C14 N1 123.19(19) . . ?
N1 C14 C15 118.7(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.1(2) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.5(2) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C14 C19 C18 120.4(2) . . ?
C14 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C13 C20 S1 120.93(15) . . ?
C21 C20 C13 128.5(2) . . ?
C21 C20 S1 110.61(17) . . ?
C20 C21 H21 123.1 . . ?
C20 C21 C22 113.7(2) . . ?
C22 C21 H21 123.1 . . ?
C21 C22 H22 123.6 . . ?
C23 C22 C21 112.7(2) . . ?
C23 C22 H22 123.6 . . ?
C22 C23 C24 129.3(2) . . ?
C22 C23 S1 110.93(17) . . ?
C24 C23 S1 119.72(18) . . ?
C25 C24 C23 177.9(3) . . ?
C24 C25 H25 180.0 . . ?
C13 N1 H1 119.3 . . ?
C14 N1 C13 121.48(18) . . ?
C14 N1 H1 119.3 . . ?
C20 S1 C23 92.01(11) . . ?

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
C1 C2 C3 C4 0.3(5) . . . . ?
C1 C13 C20 C21 -135.6(2) . . . . ?
C1 C13 C20 S1 45.4(2) . . . . ?
C1 C13 N1 C14 77.2(3) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C2 C1 C13 C20 80.6(3) . . . . ?
C2 C1 C13 N1 -156.8(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C2 C3 C4 C7 -178.1(3) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C3 C4 C7 C8 2.5(4) . . . . ?
C3 C4 C7 C12 -177.3(3) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C7 C8 C9 179.1(3) . . . . ?
C4 C7 C12 C11 -178.3(3) . . . . ?
C5 C4 C7 C8 -175.3(3) . . . . ?
C5 C4 C7 C12 4.9(4) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C6 C1 C13 C20 -96.9(2) . . . . ?
C6 C1 C13 N1 25.7(3) . . . . ?
C7 C4 C5 C6 177.8(2) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C7 C12 C11 1.8(5) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C12 0.3(6) . . . . ?
C10 C11 C12 C7 -1.5(6) . . . . ?
C12 C7 C8 C9 -1.1(5) . . . . ?
C13 C1 C2 C3 -177.7(3) . . . . ?
C13 C1 C6 C5 177.4(2) . . . . ?
C13 C20 C21 C22 -179.4(2) . . . . ?
C13 C20 S1 C23 179.58(17) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
C15 C14 N1 C13 173.44(19) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 C14 0.2(4) . . . . ?
C19 C14 C15 C16 1.1(3) . . . . ?
C19 C14 N1 C13 -7.9(3) . . . . ?
C20 C13 N1 C14 -159.11(18) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C20 S1 C23 0.39(19) . . . . ?
C21 C22 C23 C24 -177.5(2) . . . . ?
C21 C22 C23 S1 0.4(3) . . . . ?
C22 C23 S1 C20 -0.43(19) . . . . ?
C24 C23 S1 C20 177.66(18) . . . . ?
N1 C13 C20 C21 99.7(3) . . . . ?
N1 C13 C20 S1 -79.3(2) . . . . ?
N1 C14 C15 C16 179.9(2) . . . . ?
N1 C14 C19 C18 -179.6(2) . . . . ?
S1 C20 C21 C22 -0.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
