# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_CHCl3_Hex_0529
_database_code_depnum_ccdc_archive 'CCDC 2477480'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2025-07-31 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C32 H19 Cl3 N4 S2'
_chemical_formula_moiety         'C32 H19 Cl3 N4 S2'
_chemical_formula_weight         630.01
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.29396(7)
_cell_length_b                   23.41077(18)
_cell_length_c                   11.59685(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.6145(6)
_cell_angle_gamma                90.0000
_cell_volume                     2793.61(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11352
_cell_measurement_theta_min      4.68
_cell_measurement_theta_max      72.87
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.001
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1288.00
_exptl_absorpt_coefficient_mu    4.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_T_max  0.995

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            16122
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_min         4.694
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5100
_reflns_number_gt                4786
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0912
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5100
_refine_ls_number_parameters     370
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0438P)²+2.0747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.72
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.77800(6) 0.26699(3) 0.49224(5) 0.04795(16) Uani 1 1 d . . . . .
Cl2 Cl 0.72665(5) 0.22316(2) 0.71698(4) 0.03960(14) Uani 1 1 d . . . . .
Cl3 Cl 0.76461(6) 0.14519(3) 0.52752(6) 0.05389(18) Uani 1 1 d . . . . .
S1 S 0.50494(6) 0.35565(2) 0.76834(4) 0.03525(14) Uani 1 1 d . . . . .
S2 S 0.72366(5) 0.49038(2) 0.34767(4) 0.03007(13) Uani 1 1 d . . . . .
N1 N 0.24006(13) 0.24434(6) 0.39711(12) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.39868(13) 0.20588(6) 0.50882(12) 0.0186(3) Uani 1 1 d . . . . .
N3 N 0.43463(16) 0.31286(7) 0.67648(14) 0.0281(4) Uani 1 1 d . . . . .
N4 N 0.57314(16) 0.40046(7) 0.68347(13) 0.0264(3) Uani 1 1 d . . . . .
C1 C 0.35401(16) 0.25302(7) 0.45982(14) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.31039(16) 0.16426(7) 0.47645(14) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.31629(16) 0.10502(7) 0.50720(14) 0.0183(3) Uani 1 1 d . . . . .
C4 C 0.41476(17) 0.08349(8) 0.58085(15) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.4820 0.1082 0.6084 0.026 Uiso 1 1 calc R U . . .
C5 C 0.41519(18) 0.02713(8) 0.61370(16) 0.0256(4) Uani 1 1 d . . . . .
H5 H 0.4821 0.0128 0.6638 0.031 Uiso 1 1 calc R U . . .
C6 C 0.31586(19) -0.00885(8) 0.57254(17) 0.0285(4) Uani 1 1 d . . . . .
H6 H 0.3144 -0.0477 0.5964 0.034 Uiso 1 1 calc R U . . .
C7 C 0.22016(18) 0.01122(8) 0.49787(16) 0.0257(4) Uani 1 1 d . . . . .
H7 H 0.1549 -0.0143 0.4696 0.031 Uiso 1 1 calc R U . . .
C8 C 0.21673(16) 0.06876(7) 0.46232(14) 0.0193(3) Uani 1 1 d . . . . .
C9 C 0.11492(16) 0.09192(8) 0.38426(14) 0.0196(3) Uani 1 1 d . . . . .
C10 C 0.01901(18) 0.05626(8) 0.33307(16) 0.0250(4) Uani 1 1 d . . . . .
H10 H 0.0203 0.0166 0.3502 0.030 Uiso 1 1 calc R U . . .
C11 C -0.07612(18) 0.07718(9) 0.25921(17) 0.0280(4) Uani 1 1 d . . . . .
H11 H -0.1387 0.0519 0.2256 0.034 Uiso 1 1 calc R U . . .
C12 C -0.08115(18) 0.13540(9) 0.23338(17) 0.0278(4) Uani 1 1 d . . . . .
H12 H -0.1476 0.1498 0.1829 0.033 Uiso 1 1 calc R U . . .
C13 C 0.01034(17) 0.17195(8) 0.28117(16) 0.0241(4) Uani 1 1 d . . . . .
H13 H 0.0065 0.2115 0.2631 0.029 Uiso 1 1 calc R U . . .
C14 C 0.10973(16) 0.15146(7) 0.35653(14) 0.0189(3) Uani 1 1 d . . . . .
C15 C 0.21136(16) 0.18624(7) 0.40700(14) 0.0176(3) Uani 1 1 d . . . . .
C16 C 0.42361(16) 0.30797(7) 0.46383(15) 0.0189(3) Uani 1 1 d . . . . .
C17 C 0.46377(16) 0.33279(7) 0.57139(15) 0.0198(3) Uani 1 1 d . . . . .
C18 C 0.54229(16) 0.38359(7) 0.57525(15) 0.0191(3) Uani 1 1 d . . . . .
C19 C 0.58126(16) 0.41096(7) 0.47087(15) 0.0186(3) Uani 1 1 d . . . . .
C20 C 0.54006(17) 0.38500(8) 0.36992(15) 0.0215(4) Uani 1 1 d . . . . .
H20 H 0.5644 0.4016 0.2990 0.026 Uiso 1 1 calc R U . . .
C21 C 0.46331(17) 0.33482(7) 0.36604(15) 0.0213(4) Uani 1 1 d . . . . .
H21 H 0.4385 0.3192 0.2931 0.026 Uiso 1 1 calc R U . . .
C22 C 0.65645(16) 0.46396(7) 0.47304(15) 0.0199(3) Uani 1 1 d . . . . .
C23 C 0.67936(16) 0.50123(8) 0.56245(16) 0.0228(4) Uani 1 1 d . . . . .
H23 H 0.6507 0.4947 0.6385 0.027 Uiso 1 1 calc R U . . .
C24 C 0.74969(17) 0.55033(8) 0.53053(18) 0.0275(4) Uani 1 1 d . . . . .
H24 H 0.7728 0.5802 0.5826 0.033 Uiso 1 1 calc R U . . .
C25 C 0.78081(19) 0.55032(8) 0.41764(19) 0.0315(4) Uani 1 1 d . . . . .
H25 H 0.8284 0.5799 0.3817 0.038 Uiso 1 1 calc R U . . .
C26 C 0.15658(16) 0.28931(7) 0.35355(15) 0.0186(3) Uani 1 1 d . . . . .
C27 C 0.15844(17) 0.30472(8) 0.23857(16) 0.0252(4) Uani 1 1 d . . . . .
H27 H 0.2150 0.2861 0.1874 0.030 Uiso 1 1 calc R U . . .
C28 C 0.07611(19) 0.34798(9) 0.19913(18) 0.0309(4) Uani 1 1 d . . . . .
H28 H 0.0756 0.3587 0.1201 0.037 Uiso 1 1 calc R U . . .
C29 C -0.00534(18) 0.37555(8) 0.27443(18) 0.0291(4) Uani 1 1 d . . . . .
H29 H -0.0614 0.4051 0.2468 0.035 Uiso 1 1 calc R U . . .
C30 C -0.00526(17) 0.36019(8) 0.38968(18) 0.0268(4) Uani 1 1 d . . . . .
H30 H -0.0606 0.3794 0.4412 0.032 Uiso 1 1 calc R U . . .
C31 C 0.07599(17) 0.31662(8) 0.42996(16) 0.0227(4) Uani 1 1 d . . . . .
H31 H 0.0762 0.3057 0.5089 0.027 Uiso 1 1 calc R U . . .
C37 C 0.70334(19) 0.21183(8) 0.56835(17) 0.0288(4) Uani 1 1 d . . . . .
H37 H 0.6079 0.2127 0.5496 0.035 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cl1 C37 1.754(2) . ?
Cl2 C37 1.754(2) . ?
Cl3 C37 1.753(2) . ?
S1 N4 1.6126(16) . ?
S1 N3 1.6181(16) . ?
S2 C25 1.717(2) . ?
S2 C22 1.7411(18) . ?
N1 C1 1.378(2) . ?
N1 C15 1.397(2) . ?
N1 C26 1.441(2) . ?
N2 C1 1.318(2) . ?
N2 C2 1.377(2) . ?
N3 C17 1.347(2) . ?
N4 C18 1.345(2) . ?
C1 C16 1.473(2) . ?
C2 C15 1.381(2) . ?
C2 C3 1.433(2) . ?
C3 C4 1.401(2) . ?
C3 C8 1.418(2) . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.409(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.469(2) . ?
C9 C10 1.411(2) . ?
C9 C14 1.431(2) . ?
C10 C11 1.373(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.396(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.411(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.437(2) . ?
C16 C21 1.369(2) . ?
C16 C17 1.427(2) . ?
C17 C18 1.438(2) . ?
C18 C19 1.437(2) . ?
C19 C20 1.375(2) . ?
C19 C22 1.462(2) . ?
C20 C21 1.416(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.371(3) . ?
C23 C24 1.413(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.356(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.382(3) . ?
C26 C31 1.387(3) . ?
C27 C28 1.390(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.391(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C37 H37 1.0000 . ?

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
N4 S1 N3 101.26(8) . . ?
C25 S2 C22 91.98(9) . . ?
C1 N1 C15 106.21(14) . . ?
C1 N1 C26 124.58(14) . . ?
C15 N1 C26 127.91(14) . . ?
C1 N2 C2 104.79(14) . . ?
C17 N3 S1 105.93(12) . . ?
C18 N4 S1 106.44(12) . . ?
N2 C1 N1 112.67(14) . . ?
N2 C1 C16 123.66(15) . . ?
N1 C1 C16 123.49(15) . . ?
N2 C2 C15 111.47(15) . . ?
N2 C2 C3 126.43(15) . . ?
C15 C2 C3 122.09(15) . . ?
C4 C3 C8 120.75(16) . . ?
C4 C3 C2 121.66(15) . . ?
C8 C3 C2 117.57(15) . . ?
C5 C4 C3 120.76(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.17(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.86(17) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 121.48(17) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C7 C8 C3 116.93(16) . . ?
C7 C8 C9 123.00(16) . . ?
C3 C8 C9 120.05(15) . . ?
C10 C9 C14 117.41(16) . . ?
C10 C9 C8 121.30(16) . . ?
C14 C9 C8 121.29(15) . . ?
C11 C10 C9 122.00(17) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 120.23(17) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 119.96(17) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.91(17) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C9 119.49(16) . . ?
C13 C14 C15 124.51(16) . . ?
C9 C14 C15 115.98(15) . . ?
C2 C15 N1 104.85(14) . . ?
C2 C15 C14 122.92(15) . . ?
N1 C15 C14 132.16(16) . . ?
C21 C16 C17 116.83(15) . . ?
C21 C16 C1 122.09(16) . . ?
C17 C16 C1 120.81(15) . . ?
N3 C17 C16 125.71(16) . . ?
N3 C17 C18 113.44(15) . . ?
C16 C17 C18 120.85(15) . . ?
N4 C18 C19 126.22(15) . . ?
N4 C18 C17 112.92(15) . . ?
C19 C18 C17 120.85(15) . . ?
C20 C19 C18 115.68(15) . . ?
C20 C19 C22 122.68(16) . . ?
C18 C19 C22 121.62(15) . . ?
C19 C20 C21 123.51(16) . . ?
C19 C20 H20 118.2 . . ?
C21 C20 H20 118.2 . . ?
C16 C21 C20 122.27(16) . . ?
C16 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C23 C22 C19 129.27(16) . . ?
C23 C22 S2 109.98(13) . . ?
C19 C22 S2 120.64(13) . . ?
C22 C23 C24 113.46(17) . . ?
C22 C23 H23 123.3 . . ?
C24 C23 H23 123.3 . . ?
C25 C24 C23 112.92(17) . . ?
C25 C24 H24 123.5 . . ?
C23 C24 H24 123.5 . . ?
C24 C25 S2 111.66(14) . . ?
C24 C25 H25 124.2 . . ?
S2 C25 H25 124.2 . . ?
C27 C26 C31 121.39(16) . . ?
C27 C26 N1 120.29(16) . . ?
C31 C26 N1 118.31(15) . . ?
C26 C27 C28 118.87(17) . . ?
C26 C27 H27 120.6 . . ?
C28 C27 H27 120.6 . . ?
C29 C28 C27 120.39(18) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.21(18) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 119.91(17) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C26 C31 C30 119.22(17) . . ?
C26 C31 H31 120.4 . . ?
C30 C31 H31 120.4 . . ?
Cl3 C37 Cl1 110.68(11) . . ?
Cl3 C37 Cl2 111.09(11) . . ?
Cl1 C37 Cl2 109.48(11) . . ?
Cl3 C37 H37 108.5 . . ?
Cl1 C37 H37 108.5 . . ?
Cl2 C37 H37 108.5 . . ?

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
N4 S1 N3 C17 0.31(15) . . . . ?
N3 S1 N4 C18 0.37(15) . . . . ?
C2 N2 C1 N1 0.26(19) . . . . ?
C2 N2 C1 C16 -175.10(15) . . . . ?
C15 N1 C1 N2 -0.54(19) . . . . ?
C26 N1 C1 N2 167.30(15) . . . . ?
C15 N1 C1 C16 174.83(15) . . . . ?
C26 N1 C1 C16 -17.3(2) . . . . ?
C1 N2 C2 C15 0.12(19) . . . . ?
C1 N2 C2 C3 179.49(16) . . . . ?
N2 C2 C3 C4 2.9(3) . . . . ?
C15 C2 C3 C4 -177.82(16) . . . . ?
N2 C2 C3 C8 -178.48(15) . . . . ?
C15 C2 C3 C8 0.8(2) . . . . ?
C8 C3 C4 C5 -1.7(3) . . . . ?
C2 C3 C4 C5 176.85(16) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C6 C7 C8 C3 -0.1(3) . . . . ?
C6 C7 C8 C9 -178.96(17) . . . . ?
C4 C3 C8 C7 1.7(2) . . . . ?
C2 C3 C8 C7 -176.93(15) . . . . ?
C4 C3 C8 C9 -179.39(15) . . . . ?
C2 C3 C8 C9 2.0(2) . . . . ?
C7 C8 C9 C10 -4.9(3) . . . . ?
C3 C8 C9 C10 176.32(16) . . . . ?
C7 C8 C9 C14 175.60(16) . . . . ?
C3 C8 C9 C14 -3.2(2) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C8 C9 C10 C11 -179.45(17) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C12 C13 C14 C9 -0.4(3) . . . . ?
C12 C13 C14 C15 177.83(17) . . . . ?
C10 C9 C14 C13 0.4(2) . . . . ?
C8 C9 C14 C13 179.99(15) . . . . ?
C10 C9 C14 C15 -177.97(15) . . . . ?
C8 C9 C14 C15 1.6(2) . . . . ?
N2 C2 C15 N1 -0.44(18) . . . . ?
C3 C2 C15 N1 -179.84(14) . . . . ?
N2 C2 C15 C14 176.87(14) . . . . ?
C3 C2 C15 C14 -2.5(3) . . . . ?
C1 N1 C15 C2 0.56(17) . . . . ?
C26 N1 C15 C2 -166.73(16) . . . . ?
C1 N1 C15 C14 -176.39(17) . . . . ?
C26 N1 C15 C14 16.3(3) . . . . ?
C13 C14 C15 C2 -177.07(16) . . . . ?
C9 C14 C15 C2 1.2(2) . . . . ?
C13 C14 C15 N1 -0.6(3) . . . . ?
C9 C14 C15 N1 177.73(16) . . . . ?
N2 C1 C16 C21 118.67(19) . . . . ?
N1 C1 C16 C21 -56.2(2) . . . . ?
N2 C1 C16 C17 -55.1(2) . . . . ?
N1 C1 C16 C17 130.00(18) . . . . ?
S1 N3 C17 C16 179.18(15) . . . . ?
S1 N3 C17 C18 -0.87(19) . . . . ?
C21 C16 C17 N3 179.90(17) . . . . ?
C1 C16 C17 N3 -6.0(3) . . . . ?
C21 C16 C17 C18 0.0(2) . . . . ?
C1 C16 C17 C18 174.07(15) . . . . ?
S1 N4 C18 C19 179.69(14) . . . . ?
S1 N4 C18 C17 -0.91(18) . . . . ?
N3 C17 C18 N4 1.2(2) . . . . ?
C16 C17 C18 N4 -178.83(16) . . . . ?
N3 C17 C18 C19 -179.34(16) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
N4 C18 C19 C20 178.56(17) . . . . ?
C17 C18 C19 C20 -0.8(2) . . . . ?
N4 C18 C19 C22 -3.3(3) . . . . ?
C17 C18 C19 C22 177.38(15) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C22 C19 C20 C21 -177.68(16) . . . . ?
C17 C16 C21 C20 -0.3(3) . . . . ?
C1 C16 C21 C20 -174.33(16) . . . . ?
C19 C20 C21 C16 0.1(3) . . . . ?
C20 C19 C22 C23 163.83(18) . . . . ?
C18 C19 C22 C23 -14.2(3) . . . . ?
C20 C19 C22 S2 -11.9(2) . . . . ?
C18 C19 C22 S2 170.08(13) . . . . ?
C25 S2 C22 C23 0.10(14) . . . . ?
C25 S2 C22 C19 176.57(15) . . . . ?
C19 C22 C23 C24 -175.96(17) . . . . ?
S2 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C23 C24 C25 S2 0.4(2) . . . . ?
C22 S2 C25 C24 -0.30(16) . . . . ?
C1 N1 C26 C27 102.2(2) . . . . ?
C15 N1 C26 C27 -92.7(2) . . . . ?
C1 N1 C26 C31 -77.4(2) . . . . ?
C15 N1 C26 C31 87.8(2) . . . . ?
C31 C26 C27 C28 -0.9(3) . . . . ?
N1 C26 C27 C28 179.56(16) . . . . ?
C26 C27 C28 C29 0.7(3) . . . . ?
C27 C28 C29 C30 0.0(3) . . . . ?
C28 C29 C30 C31 -0.6(3) . . . . ?
C27 C26 C31 C30 0.4(3) . . . . ?
N1 C26 C31 C30 179.93(15) . . . . ?
C29 C30 C31 C26 0.3(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/chloroform'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2477481'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2025-07-31 deposited with the CCDC.	2025-10-21 downloaded from the CCDC.
;
_audit_creation_date             2025-06-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H18 N4 S2'
_chemical_formula_sum            'C31 H18 N4 S2'
_chemical_formula_weight         510.61
_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'
N N 0.0311 0.0180 '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      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                   11.71580(10)
_cell_length_b                   5.86670(10)
_cell_length_c                   17.8200(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.3450(10)
_cell_angle_gamma                90
_cell_volume                     1175.32(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5977
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.79
_cell_measurement_theta_min      5.17
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.262
_exptl_absorpt_coefficient_mu    2.285
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)

Empirical absorption correction using spherical harmonics,

 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.005
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7372
_diffrn_reflns_point_group_measured_fraction_full 0.797
_diffrn_reflns_point_group_measured_fraction_max 0.766
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.213
_diffrn_reflns_theta_min         5.173
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.424
_reflns_Friedel_fraction_full    0.548
_reflns_Friedel_fraction_max     0.508
_reflns_number_gt                3535
_reflns_number_total             3615
_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       ?
_computing_data_reduction        ?
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.021(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     89
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.092
_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)+(0.0516P)²+0.2596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0878
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S2-C21 \\sim S2A-C21
 with sigma of 0.02
 S2-C24 \\sim S2A-C24A
 with sigma of 0.02
 C22-H22 \\sim C22A-H22A
 with sigma of 0.02
 C22-C21 \\sim C22A-C21
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 C23-H23 \\sim C23A-H23A
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C24-H24 \\sim C24A-H24A
 with sigma of 0.02
 S2-C22 \\sim S2A-C22A
 with sigma of 0.04
 S2-C18 \\sim S2A-C18
 with sigma of 0.04
 S2-C23 \\sim S2A-C23A
 with sigma of 0.04
 C22-C18 \\sim C22A-C18
 with sigma of 0.04
 C22-C24 \\sim C22A-C24A
 with sigma of 0.04
 C21-C23 \\sim C21-C23A
 with sigma of 0.04
 C21-C24 \\sim C21-C24A
 with sigma of 0.04
 S2-C22 \\sim C22A-S2A
 with sigma of 0.04
 C21-S2 \\sim C21-C22 \\sim C21-C18 \\sim C21-C22A \\sim C21-S2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C24A) = Uanis(C23A)
4. Rigid body (RIGU) restrains
 S2, H22, C23, H23, C24, H24, C21, C22, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C22A, H22A, C23A, H23A, C24A, H24A, S2A, C21, C18
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(S2A)=1-FVAR(1)
 Sof(S2)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C20(H20), C12(H12), C13(H13), C26(H26), C29(H29), C27(H27),
 C19(H19), C30(H30), C4(H4), C28(H28), C11(H11), C5(H5), C10(H10), C7(H7),
 C23(H23), C6(H6), C24(H24), C22A(H22A), C23A(H23A), C24A(H24A)
;
_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 0.80084(6) 0.40531(14) 0.06014(3) 0.02414(17) Uani 1 1 d . . . . .
S2 S 1.0444(3) 1.0018(3) 0.08837(13) 0.0269(5) Uani 0.826(5) 1 d D . P A 1
C22 C 1.0571(15) 1.250(2) 0.2158(8) 0.025(2) Uani 0.826(5) 1 d D . P A 1
H22 H 1.043793 1.308803 0.262326 0.030 Uiso 0.826(5) 1 calc DR U P A 1
N2 N 0.79628(19) 0.3014(4) 0.37236(12) 0.0212(5) Uani 1 1 d . . . . .
N1 N 0.62434(18) 0.2913(4) 0.27640(12) 0.0190(5) Uani 1 1 d . . . . .
N4 N 0.87405(19) 0.6394(4) 0.08324(13) 0.0228(5) Uani 1 1 d . . . . .
N3 N 0.75724(19) 0.3594(4) 0.13673(12) 0.0226(5) Uani 1 1 d . . . . .
C15 C 0.7906(2) 0.5562(5) 0.26416(15) 0.0197(5) Uani 1 1 d . . . . .
C1 C 0.7371(2) 0.3856(5) 0.30369(14) 0.0199(5) Uani 1 1 d . . . . .
C25 C 0.5414(2) 0.3369(5) 0.20110(14) 0.0185(5) Uani 1 1 d . . . . .
C14 C 0.5169(2) -0.0087(5) 0.33790(14) 0.0193(5) Uani 1 1 d . . . . .
C16 C 0.8012(2) 0.5331(5) 0.18625(14) 0.0183(5) Uani 1 1 d . . . . .
C9 C 0.5452(2) -0.1739(5) 0.39929(15) 0.0208(5) Uani 1 1 d . . . . .
C17 C 0.8691(2) 0.6928(5) 0.15586(15) 0.0186(5) Uani 1 1 d . . . . .
C00F C 0.6133(2) 0.1385(5) 0.33290(15) 0.0183(5) Uani 1 1 d . . . . .
C8 C 0.6631(2) -0.1789(5) 0.45683(15) 0.0210(5) Uani 1 1 d . . . . .
C21 C 1.0059(2) 1.0379(5) 0.17404(14) 0.0205(6) Uani 1 1 d D . . . .
C3 C 0.7488(2) -0.0106(5) 0.45472(14) 0.0205(5) Uani 1 1 d . . . . .
C20 C 0.8505(2) 0.7360(5) 0.30646(15) 0.0229(6) Uani 1 1 d . . . . .
H20 H 0.846766 0.755693 0.358643 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7204(2) 0.1461(5) 0.39041(15) 0.0195(5) Uani 1 1 d . . . . .
C18 C 0.9309(2) 0.8796(5) 0.20192(14) 0.0194(5) Uani 1 1 d D . . . .
C12 C 0.3150(2) -0.1496(5) 0.29486(16) 0.0236(6) Uani 1 1 d . . . . .
H12 H 0.236481 -0.139142 0.260891 0.028 Uiso 1 1 calc R U . . .
C13 C 0.4000(2) 0.0034(5) 0.28765(15) 0.0217(5) Uani 1 1 d . . . . .
H13 H 0.380008 0.118226 0.248551 0.026 Uiso 1 1 calc R U . . .
C26 C 0.4844(2) 0.5442(5) 0.18790(16) 0.0237(6) Uani 1 1 d . . . . .
H26 H 0.497459 0.654865 0.228338 0.028 Uiso 1 1 calc R U . . .
C29 C 0.4473(2) 0.2202(6) 0.07004(16) 0.0272(6) Uani 1 1 d . . . . .
H29 H 0.434075 0.109400 0.029629 0.033 Uiso 1 1 calc R U . . .
C27 C 0.4073(3) 0.5892(6) 0.11431(18) 0.0304(7) Uani 1 1 d . . . . .
H27 H 0.366519 0.730829 0.104559 0.036 Uiso 1 1 calc R U . . .
C19 C 0.9174(2) 0.8937(6) 0.27640(15) 0.0226(5) Uani 1 1 d . . . . .
H19 H 0.955182 1.015815 0.309063 0.027 Uiso 1 1 calc R U . . .
C30 C 0.5234(2) 0.1727(6) 0.14287(16) 0.0233(6) Uani 1 1 d . . . . .
H30 H 0.562897 0.029740 0.152959 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8617(2) -0.0109(6) 0.50940(15) 0.0244(6) Uani 1 1 d . . . . .
H4 H 0.917481 0.105162 0.507859 0.029 Uiso 1 1 calc R U . . .
C28 C 0.3899(2) 0.4295(6) 0.05566(15) 0.0280(6) Uani 1 1 d . . . . .
H28 H 0.338544 0.462399 0.005237 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3429(2) -0.3207(6) 0.35178(17) 0.0268(6) Uani 1 1 d . . . . .
H11 H 0.284604 -0.429761 0.355097 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8913(2) -0.1796(6) 0.56525(15) 0.0280(6) Uani 1 1 d . . . . .
H5 H 0.968288 -0.182291 0.601498 0.034 Uiso 1 1 calc R U . . .
C10 C 0.4556(2) -0.3300(6) 0.40305(16) 0.0243(6) Uani 1 1 d . . . . .
H10 H 0.473359 -0.445231 0.442087 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6959(2) -0.3461(6) 0.51582(16) 0.0268(6) Uani 1 1 d . . . . .
H7 H 0.640229 -0.460214 0.519495 0.032 Uiso 1 1 calc R U . . .
C23 C 1.1297(5) 1.3492(11) 0.1726(3) 0.0213(10) Uani 0.826(5) 1 d D . P A 1
H23 H 1.175590 1.482366 0.190141 0.026 Uiso 0.826(5) 1 calc DR U P A 1
C6 C 0.8082(3) -0.3464(6) 0.56844(17) 0.0308(7) Uani 1 1 d . . . . .
H6 H 0.828850 -0.461852 0.607281 0.037 Uiso 1 1 calc R U . . .
C24 C 1.1301(6) 1.2430(11) 0.1047(4) 0.0249(12) Uani 0.826(5) 1 d D . P A 1
H24 H 1.173097 1.296687 0.070268 0.030 Uiso 0.826(5) 1 calc DR U P A 1
C22A C 1.047(4) 0.982(7) 0.100(2) 0.026(6) Uani 0.174(5) 1 d D . P A 2
H22A H 1.029385 0.853364 0.066597 0.04(6) Uiso 0.174(5) 1 calc DR . P A 2
C23A C 1.119(4) 1.178(6) 0.097(2) 0.036(7) Uani 0.174(5) 1 d D . P A 2
H23A H 1.151479 1.198809 0.054555 0.04(6) Uiso 0.174(5) 1 calc DR . P A 2
C24A C 1.140(4) 1.331(7) 0.1551(19) 0.036(7) Uani 0.174(5) 1 d D . P A 2
H24A H 1.187137 1.464493 0.158633 0.05(7) Uiso 0.174(5) 1 calc DR . P A 2
S2A S 1.070(2) 1.245(4) 0.2213(12) 0.050(5) Uani 0.174(5) 1 d D . P A 2


_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 N4 1.610(3) . ?
S1 N3 1.609(2) . ?
S2 C21 1.722(3) . ?
S2 C24 1.712(6) . ?
C22 H22 0.9500 . ?
C22 C21 1.489(8) . ?
C22 C23 1.422(12) . ?
N2 C1 1.321(3) . ?
N2 C2 1.373(4) . ?
N1 C1 1.388(3) . ?
N1 C25 1.443(3) . ?
N1 C00F 1.381(3) . ?
N4 C17 1.348(3) . ?
N3 C16 1.352(3) . ?
C15 C1 1.463(4) . ?
C15 C16 1.435(4) . ?
C15 C20 1.369(4) . ?
C25 C26 1.375(4) . ?
C25 C30 1.388(4) . ?
C14 C9 1.429(4) . ?
C14 C00F 1.444(4) . ?
C14 C13 1.412(3) . ?
C16 C17 1.430(4) . ?
C9 C8 1.471(3) . ?
C9 C10 1.409(4) . ?
C17 C18 1.437(4) . ?
C00F C2 1.379(3) . ?
C8 C3 1.417(4) . ?
C8 C7 1.410(4) . ?
C21 C18 1.458(4) . ?
C21 C22A 1.556(17) . ?
C21 S2A 1.546(13) . ?
C3 C2 1.433(4) . ?
C3 C4 1.404(4) . ?
C20 H20 0.9500 . ?
C20 C19 1.412(4) . ?
C18 C19 1.382(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(4) . ?
C12 C11 1.398(4) . ?
C13 H13 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.392(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.381(4) . ?
C29 C28 1.388(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.375(5) . ?
C19 H19 0.9500 . ?
C30 H30 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C28 H28 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.379(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(4) . ?
C10 H10 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.384(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.362(5) . ?
C6 H6 0.9500 . ?
C24 H24 0.9500 . ?
C22A H22A 0.9500 . ?
C22A C23A 1.44(3) . ?
C23A H23A 0.9500 . ?
C23A C24A 1.33(2) . ?
C24A H24A 0.9500 . ?
C24A S2A 1.70(2) . ?

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
N3 S1 N4 101.51(12) . . ?
C24 S2 C21 92.0(3) . . ?
C21 C22 H22 126.6 . . ?
C23 C22 H22 126.6 . . ?
C23 C22 C21 106.8(6) . . ?
C1 N2 C2 105.0(2) . . ?
C1 N1 C25 125.3(2) . . ?
C00F N1 C1 106.2(2) . . ?
C00F N1 C25 128.4(2) . . ?
C17 N4 S1 106.25(19) . . ?
C16 N3 S1 105.88(19) . . ?
C16 C15 C1 124.5(2) . . ?
C20 C15 C1 119.0(2) . . ?
C20 C15 C16 115.8(2) . . ?
N2 C1 N1 112.0(2) . . ?
N2 C1 C15 121.2(2) . . ?
N1 C1 C15 126.8(2) . . ?
C26 C25 N1 119.4(2) . . ?
C26 C25 C30 121.4(2) . . ?
C30 C25 N1 119.2(2) . . ?
C9 C14 C00F 115.9(2) . . ?
C13 C14 C9 119.6(2) . . ?
C13 C14 C00F 124.5(2) . . ?
N3 C16 C15 125.6(2) . . ?
N3 C16 C17 113.4(2) . . ?
C17 C16 C15 120.9(2) . . ?
C14 C9 C8 121.1(2) . . ?
C10 C9 C14 117.6(2) . . ?
C10 C9 C8 121.3(2) . . ?
N4 C17 C16 112.9(2) . . ?
N4 C17 C18 125.1(2) . . ?
C16 C17 C18 121.8(2) . . ?
N1 C00F C14 131.9(2) . . ?
C2 C00F N1 105.6(2) . . ?
C2 C00F C14 122.5(2) . . ?
C3 C8 C9 120.1(2) . . ?
C7 C8 C9 122.7(3) . . ?
C7 C8 C3 117.2(2) . . ?
C22 C21 S2 112.1(5) . . ?
C18 C21 S2 123.9(2) . . ?
C18 C21 C22 124.0(5) . . ?
C18 C21 C22A 120.9(12) . . ?
C18 C21 S2A 124.0(7) . . ?
S2A C21 C22A 114.1(12) . . ?
C8 C3 C2 117.5(2) . . ?
C4 C3 C8 121.1(3) . . ?
C4 C3 C2 121.2(3) . . ?
C15 C20 H20 118.4 . . ?
C15 C20 C19 123.3(2) . . ?
C19 C20 H20 118.4 . . ?
N2 C2 C00F 111.2(2) . . ?
N2 C2 C3 126.3(2) . . ?
C00F C2 C3 122.1(2) . . ?
C17 C18 C21 123.1(2) . . ?
C19 C18 C17 114.8(2) . . ?
C19 C18 C21 122.1(2) . . ?
C13 C12 H12 119.7 . . ?
C13 C12 C11 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 H13 119.7 . . ?
C12 C13 C14 120.5(3) . . ?
C12 C13 H13 119.7 . . ?
C25 C26 H26 120.5 . . ?
C25 C26 C27 118.9(3) . . ?
C27 C26 H26 120.5 . . ?
C30 C29 H29 119.9 . . ?
C30 C29 C28 120.2(3) . . ?
C28 C29 H29 119.9 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(3) . . ?
C28 C27 H27 119.8 . . ?
C20 C19 H19 118.3 . . ?
C18 C19 C20 123.4(3) . . ?
C18 C19 H19 118.3 . . ?
C25 C30 H30 120.5 . . ?
C29 C30 C25 119.0(3) . . ?
C29 C30 H30 120.5 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C29 C28 H28 119.9 . . ?
C27 C28 C29 120.1(2) . . ?
C27 C28 H28 119.9 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 H10 119.0 . . ?
C8 C7 H7 119.5 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.5 . . ?
C22 C23 H23 121.7 . . ?
C24 C23 C22 116.5(6) . . ?
C24 C23 H23 121.7 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
S2 C24 H24 123.8 . . ?
C23 C24 S2 112.3(5) . . ?
C23 C24 H24 123.8 . . ?
C21 C22A H22A 129.6 . . ?
C23A C22A C21 100.8(18) . . ?
C23A C22A H22A 129.6 . . ?
C22A C23A H23A 120.3 . . ?
C24A C23A C22A 119(2) . . ?
C24A C23A H23A 120.3 . . ?
C23A C24A H24A 125.8 . . ?
C23A C24A S2A 108(2) . . ?
S2A C24A H24A 125.8 . . ?
C21 S2A C24A 96.3(13) . . ?

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 N4 C17 C16 -1.2(3) . . . . ?
S1 N4 C17 C18 174.7(2) . . . . ?
S1 N3 C16 C15 -176.1(2) . . . . ?
S1 N3 C16 C17 -0.2(3) . . . . ?
S2 C21 C18 C17 -8.2(4) . . . . ?
S2 C21 C18 C19 169.4(3) . . . . ?
C22 C21 C18 C17 171.2(9) . . . . ?
C22 C21 C18 C19 -11.3(10) . . . . ?
C22 C23 C24 S2 -2.2(11) . . . . ?
N1 C25 C26 C27 178.0(3) . . . . ?
N1 C25 C30 C29 -177.7(2) . . . . ?
N1 C00F C2 N2 1.3(3) . . . . ?
N1 C00F C2 C3 -172.0(2) . . . . ?
N4 S1 N3 C16 -0.5(2) . . . . ?
N4 C17 C18 C21 1.0(4) . . . . ?
N4 C17 C18 C19 -176.7(3) . . . . ?
N3 S1 N4 C17 1.0(2) . . . . ?
N3 C16 C17 N4 1.0(3) . . . . ?
N3 C16 C17 C18 -175.1(2) . . . . ?
C15 C16 C17 N4 177.1(2) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C15 C20 C19 C18 -1.2(4) . . . . ?
C1 N2 C2 C00F -1.1(3) . . . . ?
C1 N2 C2 C3 171.9(3) . . . . ?
C1 N1 C25 C26 -73.1(4) . . . . ?
C1 N1 C25 C30 105.1(3) . . . . ?
C1 N1 C00F C14 179.6(3) . . . . ?
C1 N1 C00F C2 -1.0(3) . . . . ?
C1 C15 C16 N3 4.4(4) . . . . ?
C1 C15 C16 C17 -171.3(2) . . . . ?
C1 C15 C20 C19 171.9(3) . . . . ?
C25 N1 C1 N2 -175.7(2) . . . . ?
C25 N1 C1 C15 3.7(4) . . . . ?
C25 N1 C00F C14 -4.6(5) . . . . ?
C25 N1 C00F C2 174.9(3) . . . . ?
C25 C26 C27 C28 -0.8(5) . . . . ?
C14 C9 C8 C3 3.5(4) . . . . ?
C14 C9 C8 C7 -176.8(3) . . . . ?
C14 C9 C10 C11 -2.5(4) . . . . ?
C14 C00F C2 N2 -179.2(2) . . . . ?
C14 C00F C2 C3 7.5(4) . . . . ?
C16 C15 C1 N2 124.8(3) . . . . ?
C16 C15 C1 N1 -54.5(4) . . . . ?
C16 C15 C20 C19 1.0(4) . . . . ?
C16 C17 C18 C21 176.6(2) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
C9 C14 C00F N1 169.4(3) . . . . ?
C9 C14 C00F C2 -10.0(4) . . . . ?
C9 C14 C13 C12 -3.3(4) . . . . ?
C9 C8 C3 C2 -6.3(4) . . . . ?
C9 C8 C3 C4 179.5(3) . . . . ?
C9 C8 C7 C6 179.4(3) . . . . ?
C17 C18 C19 C20 1.1(4) . . . . ?
C00F N1 C1 N2 0.3(3) . . . . ?
C00F N1 C1 C15 179.7(3) . . . . ?
C00F N1 C25 C26 111.8(3) . . . . ?
C00F N1 C25 C30 -70.0(4) . . . . ?
C00F C14 C9 C8 4.5(4) . . . . ?
C00F C14 C9 C10 -176.1(2) . . . . ?
C00F C14 C13 C12 177.5(3) . . . . ?
C8 C9 C10 C11 176.9(3) . . . . ?
C8 C3 C2 N2 -171.2(2) . . . . ?
C8 C3 C2 C00F 1.0(4) . . . . ?
C8 C3 C4 C5 1.4(4) . . . . ?
C8 C7 C6 C5 0.9(5) . . . . ?
C21 S2 C24 C23 -0.3(5) . . . . ?
C21 C22 C23 C24 3.9(15) . . . . ?
C21 C18 C19 C20 -176.6(3) . . . . ?
C21 C22A C23A C24A 6(6) . . . . ?
C3 C8 C7 C6 -1.0(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C20 C15 C1 N2 -45.3(4) . . . . ?
C20 C15 C1 N1 135.4(3) . . . . ?
C20 C15 C16 N3 174.7(2) . . . . ?
C20 C15 C16 C17 -1.0(4) . . . . ?
C2 N2 C1 N1 0.4(3) . . . . ?
C2 N2 C1 C15 -179.0(2) . . . . ?
C2 C3 C4 C5 -172.5(3) . . . . ?
C18 C21 C22A C23A -178(2) . . . . ?
C18 C21 S2A C24A 177.4(17) . . . . ?
C12 C11 C10 C9 -1.1(5) . . . . ?
C13 C14 C9 C8 -174.8(2) . . . . ?
C13 C14 C9 C10 4.7(4) . . . . ?
C13 C14 C00F N1 -11.4(5) . . . . ?
C13 C14 C00F C2 169.2(3) . . . . ?
C13 C12 C11 C10 2.6(4) . . . . ?
C26 C25 C30 C29 0.5(4) . . . . ?
C26 C27 C28 C29 1.4(5) . . . . ?
C30 C25 C26 C27 -0.1(4) . . . . ?
C30 C29 C28 C27 -1.0(4) . . . . ?
C4 C3 C2 N2 3.0(4) . . . . ?
C4 C3 C2 C00F 175.2(3) . . . . ?
C4 C5 C6 C7 0.4(5) . . . . ?
C28 C29 C30 C25 0.0(4) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C10 C9 C8 C3 -175.9(3) . . . . ?
C10 C9 C8 C7 3.8(4) . . . . ?
C7 C8 C3 C2 174.0(3) . . . . ?
C7 C8 C3 C4 -0.2(4) . . . . ?
C23 C22 C21 S2 -3.9(14) . . . . ?
C23 C22 C21 C18 176.7(6) . . . . ?
C24 S2 C21 C22 2.5(9) . . . . ?
C24 S2 C21 C18 -178.1(3) . . . . ?
C22A C21 C18 C17 -14(3) . . . . ?
C22A C21 C18 C19 163(3) . . . . ?
C22A C21 S2A C24A 9(3) . . . . ?
C22A C23A C24A S2A 0(6) . . . . ?
C23A C24A S2A C21 -5(4) . . . . ?
S2A C21 C18 C17 177.8(13) . . . . ?
S2A C21 C18 C19 -4.7(14) . . . . ?
S2A C21 C22A C23A -9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
