# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_tx16308_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2pxyq9
_database_code_depnum_ccdc_archive 'CCDC 2500482'
loop_
_audit_author_name
_audit_author_address
'Zhihao Meng'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2025-11-05 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2024-07-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 S2'
_chemical_formula_sum            'C16 H14 S2'
_chemical_formula_weight         270.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHS
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.2878(2)
_cell_length_b                   7.3416(2)
_cell_length_c                   28.6215(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.767(2)
_cell_angle_gamma                90
_cell_volume                     1316.67(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4674
_cell_measurement_temperature    170.0(2)
_cell_measurement_theta_max      76.0700
_cell_measurement_theta_min      3.0710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7680
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.067
_diffrn_reflns_theta_min         3.099
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00 102.00   0.50    0.28    --  105.35-125.00 120.00  128
  2  ω    -25.00  34.00   0.50    0.06    --   46.19 -87.00-143.00  118
  3  ω     39.00  75.00   0.50    0.06    --   46.19 -87.00-143.00   72
  4  ω     90.00 127.00   0.50    0.28    --  105.35 -87.00-143.00   74
  5  ω     35.00  79.00   0.50    0.28    --  105.35 -87.00-143.00   88
  6  ω     43.00  74.00   0.50    0.28    --  105.35 -61.00 -60.00   62
  7  ω     33.00  62.00   0.50    0.28    --  105.35 -61.00 -90.00   58
  8  ω     34.00  71.00   0.50    0.28    --  105.35 -61.00-120.00   74
  9  ω     33.00  58.00   0.50    0.28    --  105.35 -61.00   0.00   50
 10  ω     36.00  70.00   0.50    0.28    --  105.35 -61.00  30.00   68
 11  ω     97.00 176.00   0.50    0.28    --  105.35  30.00 -30.00  158
 12  ω    121.00 154.00   0.50    0.28    --  105.35  87.00 -26.00   66
 13  ω     93.00 120.00   0.50    0.28    --  105.35  87.00 -26.00   54
 14  ω     31.00 119.00   0.50    0.06    --   46.19  57.00 -30.00  176
 15  ω    -23.00  27.00   0.50    0.06    --  -46.19  19.00 -30.00  100
 16  ω    -27.00  28.00   0.50    0.06    --  -46.19  38.00 -90.00  110
 17  ω    -97.00 -39.00   0.50    0.28    -- -104.50  77.00-180.00  116
 18  ω    -66.00 -31.00   0.50    0.28    -- -104.50  61.00-180.00   70
 19  ω    -67.00 -32.00   0.50    0.28    -- -104.50  61.00 -90.00   70
 20  ω    -92.00 -65.00   0.50    0.28    -- -104.50  87.00 -26.00   54
 21  ω    -75.00 -38.00   0.50    0.28    -- -104.50 125.00 120.00   74
 22  ω    -46.00 -20.00   0.50    0.06    --  -46.19  87.00 -26.00   52
 23  ω   -151.00-126.00   0.50    0.28    -- -104.50 -87.00-143.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0437612000
_diffrn_orient_matrix_UB_12      -0.0166317000
_diffrn_orient_matrix_UB_13      0.0520085000
_diffrn_orient_matrix_UB_21      0.1039259000
_diffrn_orient_matrix_UB_22      0.1875786000
_diffrn_orient_matrix_UB_23      0.0099048000
_diffrn_orient_matrix_UB_31      -0.2185193000
_diffrn_orient_matrix_UB_32      0.0924340000
_diffrn_orient_matrix_UB_33      -0.0107138000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2212
_reflns_number_total             2600
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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         0.553
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.4377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1238
_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:
 C13(H13), C6(H6), C11(H11), C1(H1), C8(H8), C4(H4), C9(H9), C2(H2)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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
S2 S 0.25626(8) 0.31556(7) 0.53968(2) 0.03740(18) Uani 1 1 d . . . . .
S1 S 0.24906(8) 0.31598(8) 0.92033(2) 0.04117(19) Uani 1 1 d . . . . .
C14 C 0.1153(3) 0.2373(2) 0.76166(6) 0.0236(4) Uani 1 1 d . . . . .
C5 C 0.3158(3) 0.3155(2) 0.77903(6) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.4178(3) 0.3332(2) 0.69884(6) 0.0237(4) Uani 1 1 d . . . . .
C13 C 0.0710(3) 0.2082(2) 0.71368(6) 0.0248(4) Uani 1 1 d . . . . .
H13 H -0.060580 0.153364 0.702713 0.030 Uiso 1 1 calc R U . . .
C12 C 0.2157(3) 0.2579(2) 0.68124(6) 0.0240(4) Uani 1 1 d . . . . .
C6 C 0.4635(3) 0.3604(2) 0.74675(6) 0.0246(4) Uani 1 1 d . . . . .
H6 H 0.597581 0.410557 0.757817 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1639(3) 0.2454(3) 0.63200(6) 0.0272(4) Uani 1 1 d . . . . .
H11 H 0.030999 0.194735 0.620313 0.033 Uiso 1 1 calc R U . . .
C1 C -0.0347(3) 0.1929(2) 0.79490(7) 0.0281(4) Uani 1 1 d . . . . .
H1 H -0.168687 0.141783 0.784139 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5644(3) 0.3847(2) 0.66534(6) 0.0276(4) Uani 1 1 d . . . . .
H8 H 0.702129 0.428367 0.676076 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3591(3) 0.3452(2) 0.82819(6) 0.0273(4) Uani 1 1 d . . . . .
H4 H 0.490959 0.398046 0.839813 0.033 Uiso 1 1 calc R U . . .
C9 C 0.5097(3) 0.3721(3) 0.61867(7) 0.0301(4) Uani 1 1 d . . . . .
H9 H 0.609245 0.407726 0.597172 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2115(3) 0.2979(3) 0.85879(6) 0.0295(4) Uani 1 1 d . . . . .
C2 C 0.0108(3) 0.2223(3) 0.84150(7) 0.0306(4) Uani 1 1 d . . . . .
H2 H -0.091828 0.192373 0.862817 0.037 Uiso 1 1 calc R U . . .
C10 C 0.3043(3) 0.3059(2) 0.60131(6) 0.0289(4) Uani 1 1 d . . . . .
C15 C 0.5330(4) 0.3417(3) 0.93181(7) 0.0448(5) Uani 1 1 d . . . . .
H15A H 0.605521 0.240097 0.917620 0.067 Uiso 1 1 calc R U . . .
H15B H 0.570210 0.342342 0.965747 0.067 Uiso 1 1 calc R U . . .
H15C H 0.577998 0.456758 0.918328 0.067 Uiso 1 1 calc R U . . .
C16 C -0.0234(4) 0.2674(4) 0.52982(8) 0.0491(6) Uani 1 1 d . . . . .
H16A H -0.067192 0.276423 0.496230 0.074 Uiso 1 1 calc R U . . .
H16B H -0.104160 0.355547 0.547022 0.074 Uiso 1 1 calc R U . . .
H16C H -0.051663 0.144061 0.540808 0.074 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
S2 C10 1.7661(19) . ?
S2 C16 1.793(2) . ?
S1 C3 1.7625(18) . ?
S1 C15 1.798(2) . ?
C14 C5 1.436(2) . ?
C14 C13 1.395(2) . ?
C14 C1 1.432(2) . ?
C5 C6 1.402(2) . ?
C5 C4 1.428(3) . ?
C7 C12 1.438(2) . ?
C7 C6 1.392(3) . ?
C7 C8 1.435(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.401(2) . ?
C12 C11 1.423(2) . ?
C6 H6 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.370(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.358(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.355(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.373(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.430(3) . ?
C3 C2 1.429(3) . ?
C2 H2 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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 S2 C16 103.51(10) . . ?
C3 S1 C15 103.84(10) . . ?
C13 C14 C5 119.98(15) . . ?
C13 C14 C1 122.05(16) . . ?
C1 C14 C5 117.97(16) . . ?
C6 C5 C14 118.43(16) . . ?
C6 C5 C4 122.08(16) . . ?
C4 C5 C14 119.49(16) . . ?
C6 C7 C12 120.30(15) . . ?
C6 C7 C8 121.91(16) . . ?
C8 C7 C12 117.75(16) . . ?
C14 C13 H13 119.2 . . ?
C14 C13 C12 121.68(16) . . ?
C12 C13 H13 119.2 . . ?
C13 C12 C7 118.13(16) . . ?
C13 C12 C11 122.14(16) . . ?
C11 C12 C7 119.64(16) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.43(16) . . ?
C7 C6 H6 119.3 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.50(17) . . ?
C10 C11 H11 119.8 . . ?
C14 C1 H1 119.3 . . ?
C2 C1 C14 121.31(17) . . ?
C2 C1 H1 119.3 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.07(16) . . ?
C9 C8 H8 119.5 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.43(17) . . ?
C3 C4 H4 119.8 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.92(16) . . ?
C10 C9 H9 119.5 . . ?
C4 C3 S1 125.22(15) . . ?
C4 C3 C2 120.13(17) . . ?
C2 C3 S1 114.62(14) . . ?
C1 C2 C3 120.65(17) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C11 C10 S2 125.97(15) . . ?
C11 C10 C9 119.93(16) . . ?
C9 C10 S2 114.09(13) . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S2 C16 H16A 109.5 . . ?
S2 C16 H16B 109.5 . . ?
S2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
S1 C3 C2 C1 -176.89(14) . . . . ?
C14 C5 C6 C7 1.0(3) . . . . ?
C14 C5 C4 C3 0.6(3) . . . . ?
C14 C13 C12 C7 2.7(3) . . . . ?
C14 C13 C12 C11 -173.73(16) . . . . ?
C14 C1 C2 C3 -0.4(3) . . . . ?
C5 C14 C13 C12 -1.7(3) . . . . ?
C5 C14 C1 C2 -0.5(3) . . . . ?
C5 C4 C3 S1 176.60(13) . . . . ?
C5 C4 C3 C2 -1.5(3) . . . . ?
C7 C12 C11 C10 -0.6(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C13 C14 C5 C6 -0.2(2) . . . . ?
C13 C14 C5 C4 179.78(16) . . . . ?
C13 C14 C1 C2 -179.88(17) . . . . ?
C13 C12 C11 C10 175.87(17) . . . . ?
C12 C7 C6 C5 0.1(3) . . . . ?
C12 C7 C8 C9 3.5(3) . . . . ?
C12 C11 C10 S2 -175.02(13) . . . . ?
C12 C11 C10 C9 3.8(3) . . . . ?
C6 C5 C4 C3 -179.37(17) . . . . ?
C6 C7 C12 C13 -2.0(2) . . . . ?
C6 C7 C12 C11 174.59(16) . . . . ?
C6 C7 C8 C9 -174.08(17) . . . . ?
C1 C14 C5 C6 -179.66(15) . . . . ?
C1 C14 C5 C4 0.3(2) . . . . ?
C1 C14 C13 C12 177.74(16) . . . . ?
C8 C7 C12 C13 -179.62(16) . . . . ?
C8 C7 C12 C11 -3.1(2) . . . . ?
C8 C7 C6 C5 177.69(16) . . . . ?
C8 C9 C10 S2 175.56(14) . . . . ?
C8 C9 C10 C11 -3.4(3) . . . . ?
C4 C5 C6 C7 -179.05(15) . . . . ?
C4 C3 C2 C1 1.4(3) . . . . ?
C15 S1 C3 C4 -16.20(19) . . . . ?
C15 S1 C3 C2 161.97(15) . . . . ?
C16 S2 C10 C11 9.6(2) . . . . ?
C16 S2 C10 C9 -169.29(16) . . . . ?

_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 1.305
_oxdiff_exptl_absorpt_empirical_full_min 0.754
####################################################################### 
# 
# 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_tx16299_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2pxyrb
_database_code_depnum_ccdc_archive 'CCDC 2500483'
loop_
_audit_author_name
_audit_author_address
'Zhihao Meng'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2025-11-05 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2024-07-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 S4'
_chemical_formula_sum            'C18 H18 S4'
_chemical_formula_weight         362.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHS
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.2342(3)
_cell_length_b                   7.7893(2)
_cell_length_c                   15.6425(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.315(2)
_cell_angle_gamma                90
_cell_volume                     1687.73(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5643
_cell_measurement_temperature    170.1(4)
_cell_measurement_theta_max      75.5570
_cell_measurement_theta_min      3.7870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11494
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.722
_diffrn_reflns_theta_min         3.788
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.1(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  29.00   0.50    0.13    --  -46.44  19.00   0.00  102
  2  ω    -23.00  26.00   0.50    0.13    --  -46.44  19.00  60.00   98
  3  ω    -20.00   6.00   0.50    0.13    --  -46.44  19.00-120.00   52
  4  ω    -24.00  72.00   0.50    0.13    --   46.44 -86.00-129.00  192
  5  ω     60.00 132.00   0.50    0.74    --  105.35 -86.00-129.00  144
  6  ω     36.00  71.00   0.50    0.74    --  105.35 -61.00-120.00   70
  7  ω     37.00  72.00   0.50    0.74    --  105.35 -61.00-150.00   70
  8  ω     42.00  75.00   0.50    0.74    --  105.35 -61.00  30.00   66
  9  ω     37.00  75.00   0.50    0.74    --  105.35 -61.00  90.00   76
 10  ω     35.00  64.00   0.50    0.74    --  105.35 -61.00 150.00   58
 11  ω    -25.00  47.00   0.50    0.13    --   46.44 -38.00 120.00  144
 12  ω     94.00 168.00   0.50    0.74    --  105.35  86.00 -12.00  148
 13  ω     88.00 177.00   0.50    0.74    --  105.35  61.00 -60.00  178
 14  ω    102.00 152.00   0.50    0.74    --  105.35  30.00 -60.00  100
 15  ω    135.00 171.00   0.50    0.74    --  105.35  30.00 -90.00   72
 16  ω    -65.00 -33.00   0.50    0.74    -- -104.50  61.00  60.00   64
 17  ω    -68.00 -43.00   0.50    0.74    -- -104.50  61.00  30.00   50
 18  ω    -67.00 -33.00   0.50    0.74    -- -104.50  61.00   0.00   68
 19  ω    -65.00 -33.00   0.50    0.74    -- -104.50  61.00-180.00   64
 20  ω    -66.00 -34.00   0.50    0.74    -- -104.50  61.00-150.00   64
 21  ω    -66.00 -34.00   0.50    0.74    -- -104.50  61.00 -90.00   64
 22  ω   -132.00 -59.00   0.50    0.74    -- -104.50  86.00 -12.00  146
 23  ω     -9.00  18.00   0.50    0.13    --  -46.44  86.00 -12.00   54
 24  ω    -51.00 -23.00   0.50    0.13    --  -46.44  86.00 -12.00   56
 25  ω   -174.00-141.00   0.50    0.74    -- -104.50 -86.00-129.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0326865000
_diffrn_orient_matrix_UB_12      -0.0569404000
_diffrn_orient_matrix_UB_13      -0.0829621000
_diffrn_orient_matrix_UB_21      -0.0414061000
_diffrn_orient_matrix_UB_22      0.1668935000
_diffrn_orient_matrix_UB_23      -0.0467476000
_diffrn_orient_matrix_UB_31      0.0978715000
_diffrn_orient_matrix_UB_32      0.0895622000
_diffrn_orient_matrix_UB_33      0.0343033000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2850
_reflns_number_total             3334
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+0.6833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1017
_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:
 C1(H1), C8(H8), C4(H4), C3(H3), C11(H11), C10(H10)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C15(H15A,H15B,
 H15C)
;
_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
S001 S 0.67257(3) 0.73260(5) 0.42463(3) 0.02454(13) Uani 1 1 d . . . . .
S002 S 0.65273(3) 0.27898(6) 0.76083(3) 0.02796(14) Uani 1 1 d . . . . .
S003 S 0.35101(4) 0.75450(7) 0.70242(3) 0.03710(15) Uani 1 1 d . . . . .
S004 S 0.96071(4) 0.23979(7) 0.46893(4) 0.03779(15) Uani 1 1 d . . . . .
C5 C 0.59046(11) 0.6303(2) 0.55977(10) 0.0210(3) Uani 1 1 d . . . . .
C1 C 0.50857(12) 0.5637(2) 0.67909(11) 0.0243(4) Uani 1 1 d . . . . .
H1 H 0.503096 0.495512 0.728069 0.029 Uiso 1 1 calc R U . . .
C7 C 0.73231(12) 0.4680(2) 0.54292(10) 0.0216(3) Uani 1 1 d . . . . .
C12 C 0.72815(12) 0.3692(2) 0.61950(10) 0.0223(3) Uani 1 1 d . . . . .
C6 C 0.66384(12) 0.5992(2) 0.51510(10) 0.0213(3) Uani 1 1 d . . . . .
C8 C 0.80548(12) 0.4312(2) 0.49658(11) 0.0249(4) Uani 1 1 d . . . . .
H8 H 0.808548 0.496746 0.446076 0.030 Uiso 1 1 calc R U . . .
C14 C 0.58467(12) 0.5287(2) 0.63513(10) 0.0212(3) Uani 1 1 d . . . . .
C2 C 0.44406(12) 0.6929(2) 0.65178(11) 0.0256(4) Uani 1 1 d . . . . .
C4 C 0.52012(13) 0.7624(2) 0.53299(12) 0.0246(4) Uani 1 1 d . . . . .
H4 H 0.522620 0.830476 0.483193 0.029 Uiso 1 1 calc R U . . .
C13 C 0.65483(12) 0.4008(2) 0.66452(10) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.44960(13) 0.7932(2) 0.57690(12) 0.0275(4) Uani 1 1 d . . . . .
H3 H 0.403891 0.881957 0.557518 0.033 Uiso 1 1 calc R U . . .
C9 C 0.87124(12) 0.3029(2) 0.52392(12) 0.0272(4) Uani 1 1 d . . . . .
C11 C 0.80090(14) 0.2406(2) 0.64723(12) 0.0269(4) Uani 1 1 d . . . . .
H11 H 0.801243 0.175961 0.698813 0.032 Uiso 1 1 calc R U . . .
C10 C 0.86912(13) 0.2091(2) 0.60149(12) 0.0293(4) Uani 1 1 d . . . . .
H10 H 0.916336 0.123048 0.621549 0.035 Uiso 1 1 calc R U . . .
C16 C 0.59595(14) 0.0841(3) 0.71077(13) 0.0355(4) Uani 1 1 d . . . . .
H16A H 0.635064 0.034286 0.673026 0.053 Uiso 1 1 calc R U . . .
H16B H 0.531355 0.110787 0.675410 0.053 Uiso 1 1 calc R U . . .
H16C H 0.590705 0.001680 0.756789 0.053 Uiso 1 1 calc R U . . .
C17 C 0.75974(14) 0.8847(3) 0.48431(13) 0.0360(4) Uani 1 1 d . . . . .
H17A H 0.769473 0.976994 0.444637 0.054 Uiso 1 1 calc R U . . .
H17B H 0.821209 0.826025 0.507598 0.054 Uiso 1 1 calc R U . . .
H17C H 0.735711 0.933439 0.532968 0.054 Uiso 1 1 calc R U . . .
C18 C 0.93771(16) 0.3739(3) 0.37289(14) 0.0442(5) Uani 1 1 d . . . . .
H18A H 0.979235 0.338183 0.334084 0.066 Uiso 1 1 calc R U . . .
H18B H 0.951468 0.493702 0.390433 0.066 Uiso 1 1 calc R U . . .
H18C H 0.869864 0.362803 0.341766 0.066 Uiso 1 1 calc R U . . .
C15 C 0.34865(17) 0.5858(4) 0.77997(15) 0.0507(6) Uani 1 1 d . . . . .
H15A H 0.346054 0.474400 0.750353 0.076 Uiso 1 1 calc R U . . .
H15B H 0.291579 0.598985 0.804442 0.076 Uiso 1 1 calc R U . . .
H15C H 0.407033 0.591700 0.827469 0.076 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
S001 C6 1.7829(17) . ?
S001 C17 1.812(2) . ?
S002 C13 1.7865(17) . ?
S002 C16 1.811(2) . ?
S003 C2 1.7593(18) . ?
S003 C15 1.794(2) . ?
S004 C9 1.7629(18) . ?
S004 C18 1.797(2) . ?
C5 C6 1.405(2) . ?
C5 C14 1.438(2) . ?
C5 C4 1.429(2) . ?
C1 H1 0.9500 . ?
C1 C14 1.436(2) . ?
C1 C2 1.363(3) . ?
C7 C12 1.436(2) . ?
C7 C6 1.410(2) . ?
C7 C8 1.428(2) . ?
C12 C13 1.409(2) . ?
C12 C11 1.434(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.369(2) . ?
C14 C13 1.411(2) . ?
C2 C3 1.425(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.362(3) . ?
C3 H3 0.9500 . ?
C9 C10 1.422(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.355(3) . ?
C10 H10 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C6 S001 C17 97.87(8) . . ?
C13 S002 C16 99.97(9) . . ?
C2 S003 C15 103.77(10) . . ?
C9 S004 C18 103.47(10) . . ?
C6 C5 C14 120.16(15) . . ?
C6 C5 C4 121.95(15) . . ?
C4 C5 C14 117.89(15) . . ?
C14 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C14 121.18(16) . . ?
C6 C7 C12 119.16(15) . . ?
C6 C7 C8 121.44(15) . . ?
C8 C7 C12 119.40(15) . . ?
C13 C12 C7 120.06(15) . . ?
C13 C12 C11 122.50(16) . . ?
C11 C12 C7 117.44(16) . . ?
C5 C6 S001 119.34(13) . . ?
C5 C6 C7 120.77(15) . . ?
C7 C6 S001 119.85(13) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.93(16) . . ?
C9 C8 H8 119.5 . . ?
C1 C14 C5 118.69(15) . . ?
C13 C14 C5 119.07(15) . . ?
C13 C14 C1 122.22(15) . . ?
C1 C2 S003 125.64(14) . . ?
C1 C2 C3 120.10(16) . . ?
C3 C2 S003 114.25(13) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 C5 121.81(16) . . ?
C3 C4 H4 119.1 . . ?
C12 C13 S002 119.14(13) . . ?
C12 C13 C14 120.73(15) . . ?
C14 C13 S002 120.12(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.31(16) . . ?
C4 C3 H3 119.8 . . ?
C8 C9 S004 124.75(15) . . ?
C8 C9 C10 119.60(17) . . ?
C10 C9 S004 115.64(14) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 C12 121.46(17) . . ?
C10 C11 H11 119.3 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.09(17) . . ?
C11 C10 H10 119.5 . . ?
S002 C16 H16A 109.5 . . ?
S002 C16 H16B 109.5 . . ?
S002 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S001 C17 H17A 109.5 . . ?
S001 C17 H17B 109.5 . . ?
S001 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S004 C18 H18A 109.5 . . ?
S004 C18 H18B 109.5 . . ?
S004 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S003 C15 H15A 109.5 . . ?
S003 C15 H15B 109.5 . . ?
S003 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
S003 C2 C3 C4 178.12(14) . . . . ?
S004 C9 C10 C11 -177.00(14) . . . . ?
C5 C14 C13 S002 177.21(12) . . . . ?
C5 C14 C13 C12 -1.7(2) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C1 C14 C13 S002 -1.4(2) . . . . ?
C1 C14 C13 C12 179.61(15) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C7 C12 C13 S002 -178.77(12) . . . . ?
C7 C12 C13 C14 0.2(2) . . . . ?
C7 C12 C11 C10 -2.1(3) . . . . ?
C7 C8 C9 S004 176.82(13) . . . . ?
C7 C8 C9 C10 -2.5(3) . . . . ?
C12 C7 C6 S001 175.85(12) . . . . ?
C12 C7 C6 C5 -1.9(2) . . . . ?
C12 C7 C8 C9 0.3(2) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
C6 C5 C14 C1 -179.83(14) . . . . ?
C6 C5 C14 C13 1.5(2) . . . . ?
C6 C5 C4 C3 -179.40(16) . . . . ?
C6 C7 C12 C13 1.6(2) . . . . ?
C6 C7 C12 C11 -178.09(15) . . . . ?
C6 C7 C8 C9 -179.64(16) . . . . ?
C8 C7 C12 C13 -178.28(15) . . . . ?
C8 C7 C12 C11 2.0(2) . . . . ?
C8 C7 C6 S001 -4.2(2) . . . . ?
C8 C7 C6 C5 178.01(15) . . . . ?
C8 C9 C10 C11 2.3(3) . . . . ?
C14 C5 C6 S001 -177.42(12) . . . . ?
C14 C5 C6 C7 0.4(2) . . . . ?
C14 C5 C4 C3 0.3(2) . . . . ?
C14 C1 C2 S003 -177.22(13) . . . . ?
C14 C1 C2 C3 1.8(3) . . . . ?
C2 C1 C14 C5 -1.5(2) . . . . ?
C2 C1 C14 C13 177.11(16) . . . . ?
C4 C5 C6 S001 2.2(2) . . . . ?
C4 C5 C6 C7 -179.97(15) . . . . ?
C4 C5 C14 C1 0.5(2) . . . . ?
C4 C5 C14 C13 -178.20(15) . . . . ?
C13 C12 C11 C10 178.13(17) . . . . ?
C11 C12 C13 S002 1.0(2) . . . . ?
C11 C12 C13 C14 179.92(15) . . . . ?
C16 S002 C13 C12 -80.72(15) . . . . ?
C16 S002 C13 C14 100.31(14) . . . . ?
C17 S001 C6 C5 94.20(14) . . . . ?
C17 S001 C6 C7 -83.60(15) . . . . ?
C18 S004 C9 C8 -2.61(19) . . . . ?
C18 S004 C9 C10 176.70(15) . . . . ?
C15 S003 C2 C1 -10.73(19) . . . . ?
C15 S003 C2 C3 170.21(15) . . . . ?

_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 1.388
_oxdiff_exptl_absorpt_empirical_full_min 0.541
####################################################################### 
# 
# 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_fx1166_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2pxyvf
_database_code_depnum_ccdc_archive 'CCDC 2500486'
loop_
_audit_author_name
_audit_author_address
'Zhihao Meng'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2025-11-05 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2025-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 S2, C6 H2 N2'
_chemical_formula_sum            'C15 H11 N2 S2'
_chemical_formula_weight         283.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNS
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.8023(12)
_cell_length_b                   6.9926(6)
_cell_length_c                   17.9206(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.382(5)
_cell_angle_gamma                90
_cell_volume                     2720.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4187
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.6180
_cell_measurement_theta_min      2.5040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.424
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.114a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8608
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.093
_diffrn_reflns_theta_min         4.073
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    117.00 144.00   0.50    0.60    --  103.77  95.00-128.00   54
  2  ω     93.00 118.00   0.50    0.60    --  103.77  15.00-150.00   50
  3  ω     31.00  72.00   0.50    0.60    --  103.77 -61.00 -90.00   82
  4  ω     33.00  74.00   0.50    0.60    --  103.77 -61.00 -60.00   82
  5  ω     35.00  71.00   0.50    0.60    --  103.77 -61.00 -30.00   72
  6  ω     42.00 110.00   0.50    0.60    --  103.77-125.00  90.00  136
  7  ω     32.00 102.00   0.50    0.60    --  103.77 -95.00 122.00  140
  8  ω    -11.00  73.00   0.50    0.40    --   46.79 -95.00 122.00  168
  9  ω    -22.00  21.00   0.50    0.40    --  -46.79  19.00 -30.00   86
 10  ω    -21.00  29.00   0.50    0.40    --  -46.79  19.00-150.00  100
 11  ω    -18.00  14.00   0.50    0.40    --  -46.79  19.00-180.00   64
 12  ω     -5.00  25.00   0.50    0.40    --  -46.79  95.00-128.00   60
 13  ω    -61.00 -25.00   0.50    0.40    --  -46.79 125.00-120.00   72
 14  ω    -66.00 -40.00   0.50    0.40    --  -46.79  95.00-128.00   52
 15  ω    -89.00 -62.00   0.50    0.60    -- -103.77  95.00-128.00   54
 16  ω    -96.00 -36.00   0.50    0.60    -- -103.77  77.00-120.00  120
 17  ω    -68.00 -33.00   0.50    0.60    -- -103.77  61.00-150.00   70
 18  ω    -78.00 -49.00   0.50    0.60    -- -103.77  77.00 -30.00   58
 19  ω    -61.00 -36.00   0.50    0.60    -- -103.77  61.00  90.00   50
 20  ω    -67.00 -32.00   0.50    0.60    -- -103.77  61.00 120.00   70
 21  ω   -174.00 -98.00   0.50    0.60    -- -103.77 -95.00 122.00  152
 22  ω   -173.00-108.00   0.50    0.60    -- -103.77 -61.00-180.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0147194000
_diffrn_orient_matrix_UB_12      -0.2048771000
_diffrn_orient_matrix_UB_13      -0.0280610000
_diffrn_orient_matrix_UB_21      0.0537216000
_diffrn_orient_matrix_UB_22      0.0102740000
_diffrn_orient_matrix_UB_23      -0.0498464000
_diffrn_orient_matrix_UB_31      0.0440686000
_diffrn_orient_matrix_UB_32      -0.0805779000
_diffrn_orient_matrix_UB_33      0.0645934000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2143
_reflns_number_total             2710
_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 1.171.43.114a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.114a 64-bit (release 14-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.114a (Rigaku OD, 2024)'
_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         0.442
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.099
_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)+(0.0936P)²+1.8131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1766
_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:
 C6(H6), C3(H3), C13(H13), C14(H14), C4(H4)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S8 S 0.11079(3) 0.37707(11) 0.40513(3) 0.0271(3) Uani 1 1 d . . . . .
S10 S 0.20660(3) 0.52552(16) 0.69746(4) 0.0465(3) Uani 1 1 d . . . . .
C7 C 0.06153(12) 0.4919(4) 0.53484(14) 0.0223(6) Uani 1 1 d . . . . .
C1 C 0.04918(12) 0.4492(4) 0.45784(14) 0.0222(6) Uani 1 1 d . . . . .
C2 C -0.01125(12) 0.4586(4) 0.42277(14) 0.0218(6) Uani 1 1 d . . . . .
C6 C 0.12258(13) 0.4853(4) 0.57119(14) 0.0257(6) Uani 1 1 d . . . . .
H6 H 0.155934 0.452807 0.543115 0.031 Uiso 1 1 calc R U . . .
C3 C 0.02536(13) 0.5796(5) 0.65543(14) 0.0305(7) Uani 1 1 d . . . . .
H3 H -0.007167 0.611197 0.684964 0.037 Uiso 1 1 calc R U . . .
C13 C 0.51048(15) 0.4653(4) 0.42489(16) 0.0323(7) Uani 1 1 d . . . . .
H13 H 0.516843 0.441487 0.373995 0.039 Uiso 1 1 calc R U . . .
C5 C 0.13377(13) 0.5256(5) 0.64649(15) 0.0294(7) Uani 1 1 d . . . . .
C12 C 0.44904(14) 0.4913(4) 0.44540(16) 0.0303(7) Uani 1 1 d . . . . .
C14 C 0.55912(15) 0.4740(5) 0.47646(17) 0.0331(7) Uani 1 1 d . . . . .
H14 H 0.599448 0.457140 0.461554 0.040 Uiso 1 1 calc R U . . .
C15 C 0.39871(16) 0.4855(5) 0.39269(19) 0.0388(8) Uani 1 1 d . . . . .
C4 C 0.08398(14) 0.5719(5) 0.68862(15) 0.0323(7) Uani 1 1 d . . . . .
H4 H 0.091657 0.598002 0.740687 0.039 Uiso 1 1 calc R U . . .
N19 N 0.4108(2) 0.4385(5) 0.25230(18) 0.0648(11) Uani 1 1 d . . . . .
C9 C 0.14357(14) 0.6060(5) 0.38517(17) 0.0365(7) Uani 1 1 d . . . . .
H9A H 0.177743 0.587591 0.354060 0.055 Uiso 1 1 calc R U . . .
H9B H 0.158823 0.668347 0.432254 0.055 Uiso 1 1 calc R U . . .
H9C H 0.111953 0.686377 0.358333 0.055 Uiso 1 1 calc R U . . .
N17 N 0.28907(16) 0.5232(6) 0.4335(2) 0.0673(11) Uani 1 1 d . . . . .
C11 C 0.25880(15) 0.4723(6) 0.62939(19) 0.0438(9) Uani 1 1 d . . . . .
H11A H 0.254154 0.567498 0.589123 0.066 Uiso 1 1 calc R U . . .
H11B H 0.249787 0.344780 0.608483 0.066 Uiso 1 1 calc R U . . .
H11C H 0.301141 0.475405 0.653173 0.066 Uiso 1 1 calc R U . . .
C18 C 0.40568(19) 0.4570(5) 0.3143(2) 0.0476(9) Uani 1 1 d . . . . .
C16 C 0.33726(18) 0.5076(6) 0.4141(2) 0.0481(9) 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
S8 C1 1.786(3) . ?
S8 C9 1.802(4) . ?
S10 C5 1.756(3) . ?
S10 C11 1.784(4) . ?
C7 C1 1.413(4) . ?
C7 C2 1.433(4) 5_566 ?
C7 C6 1.427(4) . ?
C1 C2 1.407(4) . ?
C2 C3 1.431(3) 5_566 ?
C6 H6 0.9500 . ?
C6 C5 1.378(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.359(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.434(4) . ?
C13 C14 1.341(4) . ?
C5 C4 1.417(4) . ?
C12 C14 1.448(4) 5_666 ?
C12 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C18 1.440(5) . ?
C15 C16 1.436(6) . ?
C4 H4 0.9500 . ?
N19 C18 1.135(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N17 C16 1.143(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C1 S8 C9 100.73(14) . . ?
C5 S10 C11 104.36(14) . . ?
C1 C7 C2 118.9(2) . 5_566 ?
C1 C7 C6 121.6(2) . . ?
C6 C7 C2 119.5(2) . 5_566 ?
C7 C1 S8 119.49(19) . . ?
C2 C1 S8 119.8(2) . . ?
C2 C1 C7 120.7(2) . . ?
C1 C2 C7 120.3(2) . 5_566 ?
C1 C2 C3 122.3(3) . 5_566 ?
C3 C2 C7 117.3(2) 5_566 5_566 ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C2 C3 H3 119.1 5_566 . ?
C4 C3 C2 121.9(3) . 5_566 ?
C4 C3 H3 119.1 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C14 C13 C12 121.0(3) . . ?
C6 C5 S10 125.3(2) . . ?
C6 C5 C4 119.6(2) . . ?
C4 C5 S10 115.1(2) . . ?
C13 C12 C14 118.1(3) . 5_666 ?
C15 C12 C13 121.5(3) . . ?
C15 C12 C14 120.3(3) . 5_666 ?
C13 C14 C12 120.9(3) . 5_666 ?
C13 C14 H14 119.6 . . ?
C12 C14 H14 119.6 5_666 . ?
C12 C15 C18 121.4(3) . . ?
C12 C15 C16 121.1(3) . . ?
C16 C15 C18 117.5(3) . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
S8 C9 H9A 109.5 . . ?
S8 C9 H9B 109.5 . . ?
S8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S10 C11 H11A 109.5 . . ?
S10 C11 H11B 109.5 . . ?
S10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N19 C18 C15 178.5(4) . . ?
N17 C16 C15 177.7(4) . . ?

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
S8 C1 C2 C7 177.2(2) . . . 5_566 ?
S8 C1 C2 C3 -2.9(4) . . . 5_566 ?
S10 C5 C4 C3 179.0(3) . . . . ?
C7 C1 C2 C7 -1.3(5) . . . 5_566 ?
C7 C1 C2 C3 178.6(3) . . . 5_566 ?
C7 C6 C5 S10 -179.1(2) . . . . ?
C7 C6 C5 C4 0.7(5) . . . . ?
C1 C7 C6 C5 -179.4(3) . . . . ?
C2 C7 C1 S8 -177.3(2) 5_566 . . . ?
C2 C7 C1 C2 1.3(5) 5_566 . . . ?
C2 C7 C6 C5 0.1(4) 5_566 . . . ?
C2 C3 C4 C5 0.1(5) 5_566 . . . ?
C6 C7 C1 S8 2.2(4) . . . . ?
C6 C7 C1 C2 -179.3(3) . . . . ?
C6 C5 C4 C3 -0.8(5) . . . . ?
C13 C12 C15 C18 -1.3(5) . . . . ?
C13 C12 C15 C16 178.6(3) . . . . ?
C12 C13 C14 C12 0.4(5) . . . 5_666 ?
C14 C13 C12 C14 -0.4(5) . . . 5_666 ?
C14 C13 C12 C15 179.0(3) . . . . ?
C14 C12 C15 C18 178.1(3) 5_666 . . . ?
C14 C12 C15 C16 -1.9(5) 5_666 . . . ?
C9 S8 C1 C7 -81.4(2) . . . . ?
C9 S8 C1 C2 100.1(2) . . . . ?
C11 S10 C5 C6 2.1(3) . . . . ?
C11 S10 C5 C4 -177.8(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 4.106
_oxdiff_exptl_absorpt_empirical_full_min 0.363
####################################################################### 
# 
# 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_tx16503_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2pxysc
_database_code_depnum_ccdc_archive 'CCDC 2500484'
loop_
_audit_author_name
_audit_author_address
'Zhihao Meng'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2025-11-05 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2024-09-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 S2'
_chemical_formula_sum            'C16 H14 S2'
_chemical_formula_weight         270.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHS
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1736(2)
_cell_length_b                   7.4523(4)
_cell_length_c                   8.9865(3)
_cell_angle_alpha                74.087(4)
_cell_angle_beta                 73.812(4)
_cell_angle_gamma                89.790(4)
_cell_volume                     318.99(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2850
_cell_measurement_temperature    170.0(2)
_cell_measurement_theta_max      75.3650
_cell_measurement_theta_min      5.3110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.96a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             142
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3484
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.536
_diffrn_reflns_theta_min         5.346
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   9.00   0.50    0.05    --  -46.39  19.00-120.00   58
  2  ω    -61.00 -13.00   0.50    0.05    --  -46.39  56.00  50.00   96
  3  ω     41.00  67.00   0.50    0.05    --  105.35 -61.00 -30.00   52
  4  ω     43.00 104.00   0.50    0.05    --  105.35 -94.00 -30.00  122
  5  ω    -25.00  44.00   0.50    0.05    --   46.39 -56.00 -91.00  138
  6  ω     33.00  64.00   0.50    0.05    --  105.35 -56.00 -91.00   62
  7  ω     41.00  67.00   0.50    0.05    --  105.35 -61.00  30.00   52
  8  ω     33.00  62.00   0.50    0.05    --  105.35 -61.00  90.00   58
  9  ω     34.00  61.00   0.50    0.05    --  105.35 -61.00 120.00   54
 10  ω    -23.00  29.00   0.50    0.05    --   46.39 -19.00 120.00  104
 11  ω     99.00 126.00   0.50    0.05    --  105.35  61.00 -30.00   54
 12  ω    143.00 176.00   0.50    0.05    --  105.35  56.00  50.00   66
 13  ω     97.00 170.00   0.50    0.05    --  105.35  45.00  90.00  146
 14  ω    135.00 175.00   0.50    0.05    --  105.35  61.00 -30.00   80
 15  ω     35.00 118.00   0.50    0.05    --   46.39  56.00  50.00  166
 16  ω    -82.00 -56.00   0.50    0.05    -- -104.50  77.00-150.00   52
 17  ω    -61.00 -36.00   0.50    0.05    -- -104.50  56.00  50.00   50
 18  ω    -60.00 -35.00   0.50    0.05    -- -104.50  61.00  60.00   50
 19  ω    -63.00 -38.00   0.50    0.05    -- -104.50  61.00 -30.00   50
 20  ω   -169.00-124.00   0.50    0.05    -- -104.50 -45.00   0.00   90
 21  ω    -99.00 -74.00   0.50    0.05    --  -46.39 -56.00 -91.00   50
 22  ω   -169.00 -92.00   0.50    0.05    -- -104.50 -56.00 -91.00  154
 23  ω   -110.00 -47.00   0.50    0.05    -- -104.50 125.00 150.00  126
 24  ω     73.00  99.00   0.50    0.05    --   46.64-136.00-143.00   52
 25  ω    -39.00  15.00   0.50    0.05    --  -46.64  38.00-180.00  108
 26  ω    -67.00 -42.00   0.50    0.05    -- -104.50 125.00  90.00   50
 27  ω    -63.00 -37.00   0.50    0.05    -- -104.50  61.00 -30.00   52
 28  ω    -62.00 -36.00   0.50    0.05    -- -104.50  61.00-150.00   52
 29  ω   -111.00 -71.00   0.50    0.05    -- -104.50 125.00 120.00   80
 30  ω   -171.00-116.00   0.50    0.05    -- -104.50 -30.00-150.00  110
 31  ω   -109.00 -83.00   0.50    0.05    -- -104.50 125.00  90.00   52
 32  ω     86.00 111.00   0.50    0.05    --  105.35-125.00   0.00   50
 33  ω     38.00  76.00   0.50    0.05    --  105.35-125.00   0.00   76
 34  ω     92.00 118.00   0.50    0.05    --  105.35  45.00-180.00   52
 35  ω     69.00 104.00   0.50    0.05    --  105.35 -94.00-120.00   70
 36  ω    135.00 173.00   0.50    0.05    --  105.35 125.00 150.00   76
 37  ω     42.00  69.00   0.50    0.05    --  105.35 -61.00-120.00   54
 38  ω     79.00 105.00   0.50    0.05    --  105.35 -94.00-180.00   52
 39  ω    146.00 172.00   0.50    0.05    --  105.35  45.00-180.00   52
 40  ω     63.00  91.00   0.50    0.05    --  105.35 -94.00  60.00   56
 41  ω     36.00  79.00   0.50    0.05    --  105.35-125.00 -90.00   86
 42  ω   -119.00 -60.00   0.50    0.05    --  -46.64 -57.00 -60.00  118
 43  ω   -119.00 -30.00   0.50    0.05    --  -46.64 -57.00-180.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1535053000
_diffrn_orient_matrix_UB_12      -0.1210053000
_diffrn_orient_matrix_UB_13      -0.0668500000
_diffrn_orient_matrix_UB_21      0.1573599000
_diffrn_orient_matrix_UB_22      0.1109839000
_diffrn_orient_matrix_UB_23      -0.1737774000
_diffrn_orient_matrix_UB_31      0.2200455000
_diffrn_orient_matrix_UB_32      -0.1397668000
_diffrn_orient_matrix_UB_33      0.0016150000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1223
_reflns_number_total             1263
_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 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.96a (Rigaku OD, 2023)'
_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         0.285
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.091
_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)+(0.0576P)²+0.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0962
_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:
 C4(H4), C1(H1), C2(H2), C3(H3)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_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 0.19394(7) 0.17277(5) 0.81656(4) 0.02810(18) Uani 1 1 d . . . . .
C7 C 0.5626(3) 0.4799(2) 0.64754(18) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.3011(3) 0.3733(2) 0.49452(18) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.1001(3) 0.2506(2) 0.4825(2) 0.0269(3) Uani 1 1 d . . . . .
H4 H 0.007222 0.152848 0.575215 0.032 Uiso 1 1 calc R U . . .
C6 C 0.3664(3) 0.3545(2) 0.63956(18) 0.0224(3) Uani 1 1 d . . . . .
C1 C 0.3671(3) 0.5348(2) 0.20685(19) 0.0277(4) Uani 1 1 d . . . . .
H1 H 0.456567 0.630572 0.111660 0.033 Uiso 1 1 calc R U . . .
C2 C 0.1750(3) 0.4144(2) 0.2017(2) 0.0320(4) Uani 1 1 d . . . . .
H2 H 0.131937 0.427063 0.103401 0.038 Uiso 1 1 calc R U . . .
C3 C 0.0393(3) 0.2711(2) 0.3412(2) 0.0320(4) Uani 1 1 d . . . . .
H3 H -0.095491 0.188269 0.336598 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4352(3) -0.0037(2) 0.8078(2) 0.0308(4) Uani 1 1 d . . . . .
H8A H 0.483969 -0.023438 0.700237 0.046 Uiso 1 1 calc R U . . .
H8B H 0.354750 -0.121376 0.889491 0.046 Uiso 1 1 calc R U . . .
H8C H 0.597480 0.038135 0.828794 0.046 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 C6 1.7879(16) . ?
S1 C8 1.8125(17) . ?
C7 C5 1.436(2) 2_666 ?
C7 C6 1.412(2) . ?
C7 C1 1.429(2) 2_666 ?
C5 C4 1.433(2) . ?
C5 C6 1.406(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.360(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.360(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.409(3) . ?
C3 H3 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C6 S1 C8 100.11(7) . . ?
C6 C7 C5 119.56(14) . 2_666 ?
C6 C7 C1 122.10(14) . 2_666 ?
C1 C7 C5 118.33(14) 2_666 2_666 ?
C4 C5 C7 117.99(14) . 2_666 ?
C6 C5 C7 119.76(14) . 2_666 ?
C6 C5 C4 122.25(14) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.44(15) . . ?
C3 C4 H4 119.3 . . ?
C7 C6 S1 119.74(12) . . ?
C5 C6 S1 119.57(12) . . ?
C5 C6 C7 120.67(14) . . ?
C7 C1 H1 119.3 2_666 . ?
C2 C1 C7 121.40(15) . 2_666 ?
C2 C1 H1 119.3 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.42(15) . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.42(15) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
S1 C8 H8A 109.5 . . ?
S1 C8 H8B 109.5 . . ?
S1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C7 C5 C4 C3 0.2(2) 2_666 . . . ?
C7 C5 C6 S1 179.45(10) 2_666 . . . ?
C7 C5 C6 C7 0.7(2) 2_666 . . . ?
C7 C1 C2 C3 0.0(2) 2_666 . . . ?
C5 C7 C6 S1 -179.44(10) 2_666 . . . ?
C5 C7 C6 C5 -0.7(2) 2_666 . . . ?
C5 C4 C3 C2 0.3(2) . . . . ?
C4 C5 C6 S1 -0.3(2) . . . . ?
C4 C5 C6 C7 -178.99(13) . . . . ?
C6 C5 C4 C3 179.91(14) . . . . ?
C1 C7 C6 S1 1.0(2) 2_666 . . . ?
C1 C7 C6 C5 179.71(14) 2_666 . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C8 S1 C6 C7 -84.46(13) . . . . ?
C8 S1 C6 C5 96.82(13) . . . . ?

_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 1.620
_oxdiff_exptl_absorpt_empirical_full_min 0.582
####################################################################### 
# 
# 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_fx1162_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2pxytd
_database_code_depnum_ccdc_archive 'CCDC 2500485'
loop_
_audit_author_name
_audit_author_address
'Zhihao Meng'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2025-11-05 deposited with the CCDC.	2026-02-15 downloaded from the CCDC.
;
_audit_creation_date             2025-02-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 S2, C12 H4 N4'
_chemical_formula_sum            'C28 H18 N4 S2'
_chemical_formula_weight         474.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHONS
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8599(5)
_cell_length_b                   12.6918(9)
_cell_length_c                   13.5240(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.072(7)
_cell_angle_gamma                90
_cell_volume                     1159.31(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3526
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      76.0340
_cell_measurement_theta_min      4.8040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.114a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7721
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.453
_diffrn_reflns_theta_min         4.814
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00 -49.00   0.50    0.89    --  -46.79 -64.00 -83.00   52
  2  ω    -45.00 -18.00   0.50    0.89    --  -46.79  64.00  52.00   54
  3  ω     34.00  62.00   0.50    0.89    --   46.79  64.00  52.00   56
  4  ω    -24.00  37.00   0.50    0.89    --   46.79 -64.00 -83.00  122
  5  ω   -154.00-129.00   0.50    3.10    -- -103.77 -64.00 -83.00   50
  6  ω    -69.00 -43.00   0.50    3.10    -- -103.77  64.00  52.00   52
  7  ω     32.00  79.00   0.50    3.10    --  103.77 -64.00 -83.00   94
  8  ω     97.00 168.00   0.50    3.10    --  103.77  64.00  52.00  142
  9  ω    -21.00  28.00   0.50    0.89    --  -46.79  19.00  60.00   98
 10  ω    -28.00  29.00   0.50    0.89    --   46.79 -19.00 120.00  114
 11  ω     69.00 117.00   0.50    0.89    --   46.79  64.00  52.00   96
 12  ω    -59.00 -34.00   0.50    3.10    -- -103.77  61.00-180.00   50
 13  ω    -67.00 -32.00   0.50    3.10    -- -103.77  61.00 -30.00   70
 14  ω    -68.00 -42.00   0.50    3.10    -- -103.77  61.00  30.00   52
 15  ω    -68.00 -31.00   0.50    3.10    -- -103.77  61.00 -90.00   74
 16  ω     87.00 174.00   0.50    3.10    --  103.77  61.00 -60.00  174
 17  ω    141.00 173.00   0.50    3.10    --  103.77 125.00 -30.00   64
 18  ω     98.00 157.00   0.50    3.10    --  103.77  61.00 -30.00  118
 19  ω     32.00  74.00   0.50    3.10    --  103.77 -61.00   0.00   84
 20  ω     87.00 118.00   0.50    3.10    --  103.77  61.00 150.00   62
 21  ω    134.00 164.00   0.50    3.10    --  103.77  61.00 150.00   60
 22  ω     32.00 105.00   0.50    3.10    --  103.77 -77.00-180.00  146
 23  ω     31.00  75.00   0.50    3.10    --  103.77 -61.00  60.00   88
 24  ω     81.00 122.00   0.50    3.10    --  103.77 125.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1057154000
_diffrn_orient_matrix_UB_12      0.0870192000
_diffrn_orient_matrix_UB_13      -0.0687208000
_diffrn_orient_matrix_UB_21      0.1320992000
_diffrn_orient_matrix_UB_22      -0.0242873000
_diffrn_orient_matrix_UB_23      -0.0782557000
_diffrn_orient_matrix_UB_31      -0.1531339000
_diffrn_orient_matrix_UB_32      -0.0810701000
_diffrn_orient_matrix_UB_33      -0.0502788000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1862
_reflns_number_total             2330
_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 1.171.43.114a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.114a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.114a (Rigaku OD, 2024)'
_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         0.471
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1297P)²+0.1731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1818
_refine_ls_wR_factor_ref         0.2027
_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:
 C006(H006), C008(H008), C009(H009), C00A(H00E), C00D(H00D), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00C)
;
_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
S001 S 0.27611(11) 1.08587(6) 0.10141(5) 0.0433(3) Uani 1 1 d . . . . .
N002 N 0.8109(4) 0.2621(2) 0.7296(2) 0.0517(7) Uani 1 1 d . . . . .
N003 N 0.8524(4) 0.5907(2) 0.65679(19) 0.0487(7) Uani 1 1 d . . . . .
C004 C 0.5546(4) 0.90734(19) 0.5551(2) 0.0315(6) Uani 1 1 d . . . . .
C005 C 0.9471(3) 0.4740(2) 0.89716(18) 0.0323(5) Uani 1 1 d . . . . .
C006 C 0.4028(4) 0.9903(2) 0.28716(18) 0.0329(6) Uani 1 1 d . . . . .
H006 H 0.407859 0.925026 0.253233 0.039 Uiso 1 1 calc R U . . .
C007 C 0.4524(3) 0.99405(19) 0.39372(19) 0.0316(5) Uani 1 1 d . . . . .
C008 C 0.5081(4) 0.90334(19) 0.45072(19) 0.0319(6) Uani 1 1 d . . . . .
H008 H 0.514424 0.837791 0.417502 0.038 Uiso 1 1 calc R U . . .
C009 C 0.9553(4) 0.3938(2) 0.97305(19) 0.0336(6) Uani 1 1 d . . . . .
H009 H 0.926431 0.322767 0.953853 0.040 Uiso 1 1 calc R U . . .
C00A C 1.0037(4) 0.4189(2) 1.0713(2) 0.0349(6) Uani 1 1 d . . . . .
H00E H 1.005398 0.365361 1.120553 0.042 Uiso 1 1 calc R U . . .
C00B C 0.8932(4) 0.4502(2) 0.79680(19) 0.0338(6) Uani 1 1 d . . . . .
C00C C 0.8737(4) 0.5287(2) 0.71987(19) 0.0378(6) Uani 1 1 d . . . . .
C00D C 0.6125(4) 0.8157(2) 0.6147(2) 0.0355(6) Uani 1 1 d . . . . .
H00D H 0.618648 0.749611 0.582455 0.043 Uiso 1 1 calc R U . . .
C00E C 0.8470(4) 0.3448(2) 0.76088(19) 0.0379(6) Uani 1 1 d . . . . .
C00F C 0.3477(4) 1.0802(2) 0.2330(2) 0.0357(6) Uani 1 1 d . . . . .
C00G C 0.6589(4) 0.8212(2) 0.7163(2) 0.0376(6) Uani 1 1 d . . . . .
H00G H 0.696054 0.759110 0.754157 0.045 Uiso 1 1 calc R U . . .
C00H C 0.2913(5) 0.9505(3) 0.0640(2) 0.0474(7) Uani 1 1 d . . . . .
H00A H 0.246921 0.944476 -0.008700 0.071 Uiso 1 1 calc R U . . .
H00B H 0.206535 0.907056 0.098904 0.071 Uiso 1 1 calc R U . . .
H00C H 0.428584 0.926181 0.081419 0.071 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
S001 C00F 1.763(3) . ?
S001 C00H 1.799(3) . ?
N002 C00E 1.143(4) . ?
N003 C00C 1.151(4) . ?
C004 C007 1.435(4) 3_676 ?
C004 C008 1.393(4) . ?
C004 C00D 1.431(4) . ?
C005 C009 1.439(4) . ?
C005 C00A 1.446(4) 3_767 ?
C005 C00B 1.376(4) . ?
C006 H006 0.9500 . ?
C006 C007 1.422(3) . ?
C006 C00F 1.373(4) . ?
C007 C008 1.401(4) . ?
C008 H008 0.9500 . ?
C009 H009 0.9500 . ?
C009 C00A 1.350(4) . ?
C00A H00E 0.9500 . ?
C00B C00C 1.430(4) . ?
C00B C00E 1.440(4) . ?
C00D H00D 0.9500 . ?
C00D C00G 1.357(4) . ?
C00F C00G 1.432(4) 3_676 ?
C00G H00G 0.9500 . ?
C00H H00A 0.9800 . ?
C00H H00B 0.9800 . ?
C00H H00C 0.9800 . ?

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
C00F S001 C00H 103.00(13) . . ?
C008 C004 C007 120.0(2) . 3_676 ?
C008 C004 C00D 122.2(2) . . ?
C00D C004 C007 117.8(2) . 3_676 ?
C009 C005 C00A 118.4(2) . 3_767 ?
C00B C005 C009 121.2(2) . . ?
C00B C005 C00A 120.3(2) . 3_767 ?
C007 C006 H006 119.8 . . ?
C00F C006 H006 119.8 . . ?
C00F C006 C007 120.5(2) . . ?
C006 C007 C004 119.7(2) . 3_676 ?
C008 C007 C004 118.7(2) . 3_676 ?
C008 C007 C006 121.6(2) . . ?
C004 C008 C007 121.3(2) . . ?
C004 C008 H008 119.3 . . ?
C007 C008 H008 119.3 . . ?
C005 C009 H009 119.8 . . ?
C00A C009 C005 120.5(2) . . ?
C00A C009 H009 119.8 . . ?
C005 C00A H00E 119.5 3_767 . ?
C009 C00A C005 121.1(2) . 3_767 ?
C009 C00A H00E 119.5 . . ?
C005 C00B C00C 122.7(2) . . ?
C005 C00B C00E 122.8(2) . . ?
C00C C00B C00E 114.5(2) . . ?
N003 C00C C00B 177.9(3) . . ?
C004 C00D H00D 119.3 . . ?
C00G C00D C004 121.4(2) . . ?
C00G C00D H00D 119.3 . . ?
N002 C00E C00B 178.0(3) . . ?
C006 C00F S001 125.1(2) . . ?
C006 C00F C00G 120.0(2) . 3_676 ?
C00G C00F S001 114.89(19) 3_676 . ?
C00D C00G C00F 120.6(2) . 3_676 ?
C00D C00G H00G 119.7 . . ?
C00F C00G H00G 119.7 3_676 . ?
S001 C00H H00A 109.5 . . ?
S001 C00H H00B 109.5 . . ?
S001 C00H H00C 109.5 . . ?
H00A C00H H00B 109.5 . . ?
H00A C00H H00C 109.5 . . ?
H00B C00H H00C 109.5 . . ?

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
C004 C007 C008 C004 0.6(4) 3_676 . . . ?
C004 C00D C00G C00F -0.4(4) . . . 3_676 ?
C005 C009 C00A C005 -1.5(4) . . . 3_767 ?
C006 C007 C008 C004 -179.3(2) . . . . ?
C007 C004 C008 C007 -0.6(4) 3_676 . . . ?
C007 C004 C00D C00G 0.2(4) 3_676 . . . ?
C007 C006 C00F S001 -178.11(18) . . . . ?
C007 C006 C00F C00G 0.4(4) . . . 3_676 ?
C008 C004 C00D C00G 179.4(2) . . . . ?
C009 C005 C00B C00C 176.7(2) . . . . ?
C009 C005 C00B C00E -1.7(4) . . . . ?
C00A C005 C009 C00A 1.4(4) 3_767 . . . ?
C00A C005 C00B C00C -3.1(4) 3_767 . . . ?
C00A C005 C00B C00E 178.5(2) 3_767 . . . ?
C00B C005 C009 C00A -178.4(2) . . . . ?
C00D C004 C008 C007 -179.8(2) . . . . ?
C00F C006 C007 C004 -0.2(4) . . . 3_676 ?
C00F C006 C007 C008 179.7(2) . . . . ?
C00H S001 C00F C006 1.0(3) . . . . ?
C00H S001 C00F C00G -177.6(2) . . . 3_676 ?

_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 2.330
_oxdiff_exptl_absorpt_empirical_full_min 0.145
