# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_liuyi-3-28_auto
_database_code_depnum_ccdc_archive 'CCDC 2183505'
loop_
_audit_author_name
_audit_author_address
'Jian Huang'
;Jiangxi Normal University
China
;
_audit_update_record             
;
2022-07-02 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2022-07-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N2 S'
_chemical_formula_sum            'C20 H16 N2 S'
_chemical_formula_weight         316.41
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   8.3581(7)
_cell_length_b                   15.8178(11)
_cell_length_c                   24.7199(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3268.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2663
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.5990
_cell_measurement_theta_min      3.7080
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9778
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.315
_diffrn_reflns_theta_min         3.296
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  -5.00   1.00   20.31    --  -15.76  77.00 120.00   37
  2  ω    -29.00   2.00   1.00   20.31    --  -15.76  77.00-180.00   31
  3  ω      6.00  40.00   1.00   20.31    --  -15.76  77.00-180.00   34
  4  ω     -8.00  39.00   1.00   20.31    --   16.70  77.00   0.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0578133000
_diffrn_orient_matrix_UB_12      -0.0053963000
_diffrn_orient_matrix_UB_13      -0.0207071000
_diffrn_orient_matrix_UB_21      0.0434148000
_diffrn_orient_matrix_UB_22      -0.0281133000
_diffrn_orient_matrix_UB_23      0.0168794000
_diffrn_orient_matrix_UB_31      -0.0442837000
_diffrn_orient_matrix_UB_32      -0.0345790000
_diffrn_orient_matrix_UB_33      -0.0104568000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2517
_reflns_number_total             3757
_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       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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         0.176
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.080
_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)+(0.0435P)²+0.7753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1286
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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 0.50153(8) 0.37128(4) 0.67587(3) 0.0674(2) Uani 1 1 d . . . . .
N1 N 0.16771(19) 0.33856(10) 0.54199(6) 0.0435(4) Uani 1 1 d . . . . .
N2 N 0.36182(19) 0.25053(10) 0.61925(6) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.1582(2) 0.24873(12) 0.54706(7) 0.0405(4) Uani 1 1 d . . . . .
C2 C 0.0681(3) 0.19956(14) 0.51215(9) 0.0553(6) Uani 1 1 d . . . . .
H2 H 0.011417 0.225155 0.484224 0.066 Uiso 1 1 calc R U . . .
C3 C 0.0616(3) 0.11270(15) 0.51841(10) 0.0664(7) Uani 1 1 d . . . . .
H3 H 0.001046 0.080391 0.494550 0.080 Uiso 1 1 calc R U . . .
C4 C 0.1435(3) 0.07398(14) 0.55946(10) 0.0615(6) Uani 1 1 d . . . . .
H4 H 0.135211 0.015863 0.564429 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2381(2) 0.12153(12) 0.59331(8) 0.0477(5) Uani 1 1 d . . . . .
H5 H 0.296849 0.094902 0.620331 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2471(2) 0.20902(12) 0.58769(7) 0.0380(4) Uani 1 1 d . . . . .
C7 C 0.3421(2) 0.32427(12) 0.63901(7) 0.0427(5) Uani 1 1 d . . . . .
C8 C 0.1964(2) 0.37725(11) 0.63655(7) 0.0441(5) Uani 1 1 d . . . . .
C9 C 0.1431(3) 0.42190(14) 0.68159(8) 0.0597(6) Uani 1 1 d . . . . .
H9 H 0.200360 0.418726 0.713779 0.072 Uiso 1 1 calc R U . . .
C10 C 0.0069(3) 0.47068(15) 0.67920(11) 0.0724(8) Uani 1 1 d . . . . .
H10 H -0.027997 0.499845 0.709662 0.087 Uiso 1 1 calc R U . . .
C11 C -0.0766(3) 0.47599(15) 0.63188(12) 0.0726(7) Uani 1 1 d . . . . .
H11 H -0.167700 0.509634 0.630099 0.087 Uiso 1 1 calc R U . . .
C12 C -0.0272(3) 0.43189(13) 0.58653(10) 0.0577(6) Uani 1 1 d . . . . .
H12 H -0.086346 0.435269 0.554730 0.069 Uiso 1 1 calc R U . . .
C13 C 0.1101(2) 0.38262(12) 0.58824(8) 0.0423(5) Uani 1 1 d . . . . .
C14 C 0.1229(3) 0.37373(15) 0.48949(8) 0.0662(7) Uani 1 1 d . . . . .
H14A H 0.179603 0.344518 0.461366 0.099 Uiso 1 1 calc R U . . .
H14B H 0.149735 0.432717 0.488471 0.099 Uiso 1 1 calc R U . . .
H14C H 0.009814 0.367066 0.484126 0.099 Uiso 1 1 calc R U . . .
C15 C 0.6334(3) 0.28449(14) 0.68337(8) 0.0528(6) Uani 1 1 d . . . . .
C16 C 0.7351(3) 0.26029(16) 0.64205(9) 0.0646(7) Uani 1 1 d . . . . .
H16 H 0.737133 0.290923 0.609943 0.078 Uiso 1 1 calc R U . . .
C17 C 0.8332(3) 0.1912(2) 0.64818(11) 0.0745(7) Uani 1 1 d . . . . .
H17 H 0.900547 0.174893 0.620119 0.089 Uiso 1 1 calc R U . . .
C18 C 0.8317(3) 0.14623(19) 0.69571(12) 0.0778(8) Uani 1 1 d . . . . .
H18 H 0.897126 0.099073 0.699674 0.093 Uiso 1 1 calc R U . . .
C19 C 0.7337(3) 0.17093(18) 0.73735(11) 0.0779(8) Uani 1 1 d . . . . .
H19 H 0.734295 0.141073 0.769760 0.093 Uiso 1 1 calc R U . . .
C20 C 0.6343(3) 0.23988(16) 0.73129(9) 0.0610(6) Uani 1 1 d . . . . .
H20 H 0.567840 0.256315 0.759563 0.073 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 C7 1.777(2) . ?
S1 C15 1.770(2) . ?
N1 C1 1.429(2) . ?
N1 C13 1.423(2) . ?
N1 C14 1.461(2) . ?
N2 C6 1.400(2) . ?
N2 C7 1.275(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C7 C8 1.480(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.398(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.383(3) . ?
C15 C20 1.379(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C20 H20 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
C15 S1 C7 101.31(9) . . ?
C1 N1 C14 116.26(16) . . ?
C13 N1 C1 113.45(14) . . ?
C13 N1 C14 116.14(16) . . ?
C7 N2 C6 123.65(17) . . ?
C2 C1 N1 122.29(17) . . ?
C2 C1 C6 118.97(18) . . ?
C6 C1 N1 118.71(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.93(19) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 N2 123.60(17) . . ?
C5 C6 N2 116.60(17) . . ?
C5 C6 C1 119.28(17) . . ?
N2 C7 S1 118.83(15) . . ?
N2 C7 C8 127.49(18) . . ?
C8 C7 S1 113.65(14) . . ?
C9 C8 C7 121.20(19) . . ?
C9 C8 C13 119.2(2) . . ?
C13 C8 C7 119.61(17) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 N1 118.83(17) . . ?
C12 C13 N1 122.03(19) . . ?
C12 C13 C8 119.13(19) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S1 121.32(18) . . ?
C20 C15 S1 119.36(18) . . ?
C20 C15 C16 119.3(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.1(2) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 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 C7 C8 C9 -41.1(2) . . . . ?
S1 C7 C8 C13 139.02(16) . . . . ?
S1 C15 C16 C17 -178.10(17) . . . . ?
S1 C15 C20 C19 178.52(17) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
N1 C1 C6 N2 -9.0(3) . . . . ?
N1 C1 C6 C5 179.55(17) . . . . ?
N2 C7 C8 C9 137.0(2) . . . . ?
N2 C7 C8 C13 -42.8(3) . . . . ?
C1 N1 C13 C8 68.2(2) . . . . ?
C1 N1 C13 C12 -113.0(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C1 C6 N2 169.11(18) . . . . ?
C2 C1 C6 C5 -2.4(3) . . . . ?
C2 C3 C4 C5 -2.7(4) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C4 C5 C6 N2 -171.96(19) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C6 N2 C7 S1 -177.25(13) . . . . ?
C6 N2 C7 C8 4.7(3) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
C7 S1 C15 C16 80.68(19) . . . . ?
C7 S1 C15 C20 -99.05(17) . . . . ?
C7 N2 C6 C1 42.5(3) . . . . ?
C7 N2 C6 C5 -145.77(19) . . . . ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C7 C8 C13 N1 -1.8(3) . . . . ?
C7 C8 C13 C12 179.43(17) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C8 C13 N1 178.36(17) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 C13 -1.2(4) . . . . ?
C11 C12 C13 N1 -177.88(19) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C13 N1 C1 C2 119.3(2) . . . . ?
C13 N1 C1 C6 -62.7(2) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C14 N1 C1 C2 -19.3(3) . . . . ?
C14 N1 C1 C6 158.72(18) . . . . ?
C14 N1 C13 C8 -153.23(19) . . . . ?
C14 N1 C13 C12 25.6(3) . . . . ?
C15 S1 C7 N2 -10.70(18) . . . . ?
C15 S1 C7 C8 167.62(14) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C16 C15 C20 C19 -1.2(3) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C20 C15 C16 C17 1.6(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.405
_oxdiff_exptl_absorpt_empirical_full_min 0.451
