# 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 
# 
# 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_NPH20240125_a
_database_code_depnum_ccdc_archive 'CCDC 2328518'
loop_
_audit_author_name
_audit_author_address
'Ni penghui'
;Hengyang Normal University
China
;
_audit_update_record             
;
2024-01-26 deposited with the CCDC.	2024-05-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N2 S4'
_chemical_formula_weight         386.55

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'

_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'

_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. 
;

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'
'-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                   10.1086(5)
_cell_length_b                   15.8046(8)
_cell_length_c                   22.2013(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3546.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5222
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.57

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.537
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8909
_exptl_absorpt_correction_T_max  0.9095
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22226
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.835
_diffrn_reflns_theta_max         28.864
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4594
_reflns_number_gt                3285
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+1.2314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4594
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
S4 S 0.31986(6) 0.20180(4) 0.51785(2) 0.04909(15) Uani 1 1 d . . . . .
S3 S 0.19404(6) 0.09854(4) 0.51772(3) 0.05740(17) Uani 1 1 d . . . . .
S2 S 0.03557(6) 0.13344(4) 0.46599(3) 0.05535(16) Uani 1 1 d . . . . .
S1 S 0.10479(5) 0.13718(3) 0.37835(3) 0.04694(14) Uani 1 1 d . . . . .
N1 N 0.30571(16) 0.34694(10) 0.35613(7) 0.0412(4) Uani 1 1 d . . . . .
N2 N 0.53642(15) 0.13777(10) 0.45883(7) 0.0384(4) Uani 1 1 d . . . . .
C6 C 0.0148(3) 0.46754(15) 0.30332(10) 0.0602(6) Uani 1 1 d . . . . .
H6 H -0.013107 0.520165 0.289551 0.072 Uiso 1 1 calc R U . . .
C5 C 0.1462(2) 0.45571(13) 0.31675(10) 0.0517(5) Uani 1 1 d . . . . .
H5 H 0.207860 0.498940 0.312252 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1828(2) 0.37560(12) 0.33746(8) 0.0405(4) Uani 1 1 d . . . . .
C1 C 0.29337(19) 0.26472(11) 0.37558(8) 0.0370(4) Uani 1 1 d . . . . .
C11 C 0.40607(18) 0.21671(11) 0.39811(8) 0.0378(4) Uani 1 1 d . . . . .
C12 C 0.52074(19) 0.19125(11) 0.36475(8) 0.0380(4) Uani 1 1 d . . . . .
C13 C 0.59860(18) 0.14206(11) 0.40404(8) 0.0368(4) Uani 1 1 d . . . . .
C14 C 0.7171(2) 0.10513(13) 0.38552(10) 0.0460(5) Uani 1 1 d . . . . .
H14 H 0.767537 0.072352 0.411640 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7562(2) 0.11915(14) 0.32708(10) 0.0534(5) Uani 1 1 d . . . . .
H15 H 0.834735 0.095210 0.313459 0.064 Uiso 1 1 calc R U . . .
C3 C 0.09142(19) 0.31014(11) 0.34455(8) 0.0382(4) Uani 1 1 d . . . . .
C2 C 0.16346(19) 0.23933(11) 0.36870(8) 0.0379(4) Uani 1 1 d . . . . .
C10 C 0.41970(18) 0.18345(12) 0.45530(8) 0.0378(4) Uani 1 1 d . . . . .
C18 C 0.5927(2) 0.09973(13) 0.51273(9) 0.0464(5) Uani 1 1 d . . . . .
H18A H 0.618230 0.042454 0.504244 0.070 Uiso 1 1 calc R U . . .
H18B H 0.528048 0.100159 0.544400 0.070 Uiso 1 1 calc R U . . .
H18C H 0.668955 0.131492 0.525103 0.070 Uiso 1 1 calc R U . . .
C16 C 0.6810(2) 0.16846(16) 0.28759(10) 0.0538(5) Uani 1 1 d . . . . .
H16 H 0.710897 0.177094 0.248458 0.065 Uiso 1 1 calc R U . . .
C17 C 0.5635(2) 0.20446(13) 0.30557(9) 0.0468(5) Uani 1 1 d . . . . .
H17 H 0.513666 0.236854 0.278971 0.056 Uiso 1 1 calc R U . . .
C9 C 0.4228(2) 0.39934(14) 0.36125(12) 0.0577(6) Uani 1 1 d . . . . .
H9A H 0.495615 0.365542 0.375144 0.087 Uiso 1 1 calc R U . . .
H9B H 0.406560 0.444238 0.389407 0.087 Uiso 1 1 calc R U . . .
H9C H 0.443940 0.422932 0.322576 0.087 Uiso 1 1 calc R U . . .
C8 C -0.0415(2) 0.32395(14) 0.33023(9) 0.0462(5) Uani 1 1 d . . . . .
H8 H -0.103781 0.281056 0.334384 0.055 Uiso 1 1 calc R U . . .
C7 C -0.0775(2) 0.40301(15) 0.30977(10) 0.0558(6) Uani 1 1 d . . . . .
H7 H -0.165489 0.413399 0.300073 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
S4 C10 1.7409(19) . ?
S4 S3 2.0690(9) . ?
S3 S2 2.0467(8) . ?
S2 S1 2.0686(8) . ?
S1 C2 1.7332(19) . ?
N1 C1 1.375(2) . ?
N1 C4 1.386(2) . ?
N1 C9 1.449(3) . ?
N2 C13 1.371(2) . ?
N2 C10 1.385(2) . ?
N2 C18 1.455(2) . ?
C6 C5 1.374(3) . ?
C6 C7 1.390(3) . ?
C6 H6 0.9300 . ?
C5 C4 1.397(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.396(3) . ?
C1 C2 1.382(3) . ?
C1 C11 1.457(2) . ?
C11 C10 1.381(3) . ?
C11 C12 1.433(3) . ?
C12 C17 1.399(3) . ?
C12 C13 1.409(2) . ?
C13 C14 1.394(3) . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.398(3) . ?
C15 H15 0.9300 . ?
C3 C8 1.398(3) . ?
C3 C2 1.439(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C16 C17 1.376(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 C7 1.378(3) . ?
C8 H8 0.9300 . ?
C7 H7 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
C10 S4 S3 102.94(7) . . ?
S2 S3 S4 105.63(3) . . ?
S3 S2 S1 105.71(3) . . ?
C2 S1 S2 104.99(7) . . ?
C1 N1 C4 108.75(16) . . ?
C1 N1 C9 126.12(16) . . ?
C4 N1 C9 124.70(16) . . ?
C13 N2 C10 108.34(15) . . ?
C13 N2 C18 124.81(16) . . ?
C10 N2 C18 126.49(16) . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C5 C4 116.8(2) . . ?
C6 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
N1 C4 C3 108.50(16) . . ?
N1 C4 C5 129.18(19) . . ?
C3 C4 C5 122.28(19) . . ?
N1 C1 C2 109.03(16) . . ?
N1 C1 C11 121.94(17) . . ?
C2 C1 C11 129.03(17) . . ?
C10 C11 C12 106.71(16) . . ?
C10 C11 C1 126.28(17) . . ?
C12 C11 C1 126.94(17) . . ?
C17 C12 C13 119.41(18) . . ?
C17 C12 C11 133.91(18) . . ?
C13 C12 C11 106.67(16) . . ?
N2 C13 C14 129.41(17) . . ?
N2 C13 C12 108.69(16) . . ?
C14 C13 C12 121.89(18) . . ?
C15 C14 C13 117.26(19) . . ?
C15 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?
C14 C15 C16 121.7(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C4 C3 C8 119.64(17) . . ?
C4 C3 C2 106.48(16) . . ?
C8 C3 C2 133.85(19) . . ?
C1 C2 C3 107.24(16) . . ?
C1 C2 S1 125.60(14) . . ?
C3 C2 S1 126.68(15) . . ?
C11 C10 N2 109.58(16) . . ?
C11 C10 S4 127.74(15) . . ?
N2 C10 S4 122.38(14) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C16 C15 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 118.53(19) . . ?
C16 C17 H17 120.7 . . ?
C12 C17 H17 120.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C8 C3 118.1(2) . . ?
C7 C8 H8 121.0 . . ?
C3 C8 H8 121.0 . . ?
C8 C7 C6 121.5(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?

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
C7 C6 C5 C4 -0.2(3) . . . . ?
C1 N1 C4 C3 -0.7(2) . . . . ?
C9 N1 C4 C3 -173.46(19) . . . . ?
C1 N1 C4 C5 177.0(2) . . . . ?
C9 N1 C4 C5 4.2(3) . . . . ?
C6 C5 C4 N1 -177.5(2) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C4 N1 C1 C2 1.0(2) . . . . ?
C9 N1 C1 C2 173.63(19) . . . . ?
C4 N1 C1 C11 179.97(17) . . . . ?
C9 N1 C1 C11 -7.4(3) . . . . ?
N1 C1 C11 C10 118.5(2) . . . . ?
C2 C1 C11 C10 -62.8(3) . . . . ?
N1 C1 C11 C12 -64.8(3) . . . . ?
C2 C1 C11 C12 113.9(2) . . . . ?
C10 C11 C12 C17 179.7(2) . . . . ?
C1 C11 C12 C17 2.5(3) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C1 C11 C12 C13 -176.47(17) . . . . ?
C10 N2 C13 C14 -178.81(19) . . . . ?
C18 N2 C13 C14 7.7(3) . . . . ?
C10 N2 C13 C12 0.0(2) . . . . ?
C18 N2 C13 C12 -173.48(17) . . . . ?
C17 C12 C13 N2 -179.63(17) . . . . ?
C11 C12 C13 N2 -0.5(2) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
C11 C12 C13 C14 178.48(17) . . . . ?
N2 C13 C14 C15 179.24(18) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
N1 C4 C3 C8 178.33(17) . . . . ?
C5 C4 C3 C8 0.5(3) . . . . ?
N1 C4 C3 C2 0.1(2) . . . . ?
C5 C4 C3 C2 -177.73(18) . . . . ?
N1 C1 C2 C3 -0.9(2) . . . . ?
C11 C1 C2 C3 -179.77(18) . . . . ?
N1 C1 C2 S1 171.57(14) . . . . ?
C11 C1 C2 S1 -7.3(3) . . . . ?
C4 C3 C2 C1 0.5(2) . . . . ?
C8 C3 C2 C1 -177.4(2) . . . . ?
C4 C3 C2 S1 -171.90(14) . . . . ?
C8 C3 C2 S1 10.3(3) . . . . ?
S2 S1 C2 C1 95.50(17) . . . . ?
S2 S1 C2 C3 -93.49(17) . . . . ?
C12 C11 C10 N2 -0.7(2) . . . . ?
C1 C11 C10 N2 176.50(17) . . . . ?
C12 C11 C10 S4 173.03(14) . . . . ?
C1 C11 C10 S4 -9.8(3) . . . . ?
C13 N2 C10 C11 0.4(2) . . . . ?
C18 N2 C10 C11 173.81(17) . . . . ?
C13 N2 C10 S4 -173.70(13) . . . . ?
C18 N2 C10 S4 -0.3(3) . . . . ?
S3 S4 C10 C11 97.50(18) . . . . ?
S3 S4 C10 N2 -89.49(15) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C12 0.5(3) . . . . ?
C13 C12 C17 C16 0.2(3) . . . . ?
C11 C12 C17 C16 -178.7(2) . . . . ?
C4 C3 C8 C7 -0.4(3) . . . . ?
C2 C3 C8 C7 177.2(2) . . . . ?
C3 C8 C7 C6 0.1(3) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ????????????'
