# 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_exp_586
_database_code_depnum_ccdc_archive 'CCDC 2370432'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda - Raj'
;Faculty of Chemistry, University of Lodz, Lodz
Poland
;
_audit_update_record             
;
2024-07-13 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_audit_creation_date             2024-07-13
_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         'C12 H8 N2, 2(C3 H3 N3 S3)'
_chemical_formula_sum            'C18 H14 N8 S6'
_chemical_formula_weight         534.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      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                   6.5124(3)
_cell_length_b                   6.7635(2)
_cell_length_c                   13.9013(5)
_cell_angle_alpha                81.841(3)
_cell_angle_beta                 81.532(3)
_cell_angle_gamma                63.930(4)
_cell_volume                     541.95(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    12148
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7410
_cell_measurement_theta_min      3.2180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.058
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             274
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0212
1 0 0 0.0110
0 1 0 0.0320
0 -1 0 0.0249
0 0 1 0.0425
0 0 -1 0.0530
3 4 2 0.0138
-3 -4 -3 0.0396
1 -2 -6 0.0175
2 4 5 0.0214

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.032
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9990 -0.0001 0.0003 -0.2226 -0.1425 -0.0006
0.9990 0.0001 -0.0003 0.2226 0.1425 0.0006
0.0003 0.9995 0.0003 -0.0264 -0.1612 0.1950
-0.0003 -0.9995 -0.0003 0.0264 0.1612 -0.1950
-0.0001 -0.0002 0.9989 0.0372 -0.0778 -0.0720
0.0001 0.0002 -0.9989 -0.0372 0.0778 0.0720
3.3030 3.9453 2.2799 0.7167 -0.3429 0.6073
-3.3941 -3.7924 -3.0927 -0.7713 0.3686 -0.5189
0.8409 -2.4888 -6.1300 0.0248 0.9987 -0.0435
1.9609 3.9772 4.9313 0.5155 -0.7459 0.4217

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15949
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.438
_diffrn_reflns_theta_min         3.226
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -90.00   0.50    0.42    --  -47.48-125.00 -60.00   58
  2  ω    -62.00  25.00   0.50    0.42    --  -47.48  57.00 120.00  174
  3  ω   -120.00 -35.00   0.50    0.42    --  -47.48 -38.00   0.00  170
  4  ω   -120.00 -35.00   0.50    0.42    --  -47.48 -38.00 -90.00  170
  5  ω     92.00 120.00   0.50    0.42    --   47.48  57.00 120.00   56
  6  ω     -1.00  81.00   0.50    0.42    --   47.48 -99.00-180.00  164
  7  ω    -27.00  12.00   0.50    0.42    --   47.48 -19.00-120.00   78
  8  ω   -163.00 -97.00   0.50    1.68    --  -91.75 -61.00 120.00  132
  9  ω    -75.00 -19.00   0.50    1.68    --  -91.75  61.00   0.00  112
 10  ω   -163.00-104.00   0.50    1.68    --  -91.75 -77.00 150.00  118
 11  ω   -163.00-103.00   0.50    1.68    --  -91.75 -95.00 -90.00  120
 12  ω   -163.00 -97.00   0.50    1.68    --  -91.75 -61.00  30.00  132
 13  ω    -75.00 -19.00   0.50    1.68    --  -91.75  61.00  30.00  112
 14  ω   -163.00-104.00   0.50    1.68    --  -91.75 -77.00   0.00  118
 15  ω    -49.00 -20.00   0.50    1.68    --  -91.75  45.00 -30.00   58
 16  ω    -49.00 -20.00   0.50    1.68    --  -91.75  45.00-120.00   58
 17  ω    -49.00 -20.00   0.50    1.68    --  -91.75  45.00  90.00   58
 18  ω    -49.00 -20.00   0.50    1.68    --  -91.75  45.00 -90.00   58
 19  ω    -85.00 -19.00   0.50    1.68    --  -91.75 125.00  90.00  132
 20  ω    -75.00 -19.00   0.50    1.68    --  -91.75  61.00 120.00  112
 21  ω     33.00 105.00   0.50    1.68    --  105.71 -95.00  30.00  144
 22  ω    104.00 177.00   0.50    1.68    --  105.71  77.00-150.00  146
 23  ω     34.00 111.00   0.50    1.68    --  105.71-125.00-150.00  154
 24  ω     33.00  75.00   0.50    1.68    --  105.71 -61.00-180.00   84
 25  ω     33.00 105.00   0.50    1.68    --  105.71 -95.00 -90.00  144
 26  ω     34.00 111.00   0.50    1.68    --  105.71-125.00 120.00  154
 27  ω     33.00 105.00   0.50    1.68    --  105.71 -95.00 -30.00  144
 28  ω     33.00 105.00   0.50    1.68    --  105.71 -95.00-180.00  144
 29  ω     33.00 106.00   0.50    1.68    --  105.71 -97.00-141.58  146
 30  ω   -120.00 -35.00   0.50    0.42    --  -47.48 -38.00  60.00  170
 31  ω    -12.00  28.00   0.50    0.42    --  -47.48  19.00 -30.00   80
 32  ω   -119.00 -92.00   0.50    0.42    --  -47.48 -57.00-180.00   54
 33  ω   -119.00 -29.00   0.50    0.42    --  -47.48 -67.00-131.00  180
 34  ω     34.00 120.00   0.50    0.42    --   47.48  51.00-151.21  172
 35  ω     35.00 120.00   0.50    0.42    --   47.48  38.00-180.00  170
 36  ω     29.00 120.00   0.50    0.42    --   47.48  67.00   2.00  182
 37  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -51.00 -85.03  170
 38  ω   -163.00 -82.00   0.50    1.68    --  -91.75 -53.00-160.72  162
 39  ω   -163.00 -79.00   0.50    1.68    --  -91.75 -47.00 139.04  168
 40  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -51.00 -71.15  170
 41  ω   -163.00 -79.00   0.50    1.68    --  -91.75 -45.00 -30.00  168
 42  ω   -163.00 -73.00   0.50    1.68    --  -91.75 -67.00-131.00  180
 43  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00  22.51  170
 44  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00-123.82  170
 45  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -48.00  83.67  170
 46  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -49.00  64.90  170
 47  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00 171.08  170
 48  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -50.00  -5.62  170
 49  ω   -163.00 -79.00   0.50    1.68    --  -91.75 -45.00  30.00  168
 50  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00 -94.91  170
 51  ω   -163.00 -86.00   0.50    1.68    --  -91.75 -54.00 160.66  154
 52  ω   -163.00 -79.00   0.50    1.68    --  -91.75 -45.00 -60.00  168
 53  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00 116.79  170
 54  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00  52.38  170
 55  ω    -49.00 -20.00   0.50    1.68    --  -91.75  45.00 150.00   58
 56  ω   -163.00 -78.00   0.50    1.68    --  -91.75 -51.00-149.87  170
 57  ω   -163.00 -79.00   0.50    1.68    --  -91.75 -45.00-180.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2228489000
_diffrn_orient_matrix_UB_12      -0.0264485000
_diffrn_orient_matrix_UB_13      0.0372565000
_diffrn_orient_matrix_UB_21      0.1425862000
_diffrn_orient_matrix_UB_22      -0.1612705000
_diffrn_orient_matrix_UB_23      -0.0778915000
_diffrn_orient_matrix_UB_31      0.0005122000
_diffrn_orient_matrix_UB_32      0.1951471000
_diffrn_orient_matrix_UB_33      -0.0720692000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1915
_reflns_number_total             1997
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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         0.262
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.057
_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)+(0.0273P)²+0.3302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0564
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_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
S4 S 0.13940(6) 0.71471(6) -0.08766(2) 0.01403(10) Uani 1 1 d . . . . .
S6 S 0.09599(6) 0.43740(6) 0.28583(2) 0.01521(10) Uani 1 1 d . . . . .
S2 S 0.54933(6) 0.92539(6) 0.15530(2) 0.01524(10) Uani 1 1 d . . . . .
N1 N 0.3241(2) 0.67626(19) 0.20892(9) 0.0124(2) Uani 1 1 d . . . . .
N5 N 0.1473(2) 0.5828(2) 0.10175(8) 0.0133(3) Uani 1 1 d . . . . .
N11 N 0.47727(19) 0.57598(19) 0.39996(8) 0.0122(2) Uani 1 1 d . . . . .
N3 N 0.34040(19) 0.7958(2) 0.04485(9) 0.0120(2) Uani 1 1 d . . . . .
C2 C 0.3994(2) 0.7930(2) 0.13592(10) 0.0124(3) Uani 1 1 d . . . . .
C17 C 0.5836(2) 0.3592(2) 0.42875(10) 0.0122(3) Uani 1 1 d . . . . .
C12 C 0.3947(2) 0.7186(2) 0.46985(10) 0.0122(3) Uani 1 1 d . . . . .
C13 C 0.2866(2) 0.9497(2) 0.44253(10) 0.0138(3) Uani 1 1 d . . . . .
H13 H 0.273088 1.001522 0.377060 0.017 Uiso 1 1 calc R U . . .
C16 C 0.3245(2) 0.7982(2) 0.64226(10) 0.0146(3) Uani 1 1 d . . . . .
H16 H 0.335139 0.750953 0.708259 0.018 Uiso 1 1 calc R U . . .
C4 C 0.2114(2) 0.6963(2) 0.02442(10) 0.0121(3) Uani 1 1 d . . . . .
C14 C 0.2031(2) 1.0943(2) 0.51272(11) 0.0150(3) Uani 1 1 d . . . . .
H14 H 0.133162 1.245275 0.494742 0.018 Uiso 1 1 calc R U . . .
C15 C 0.2212(2) 1.0176(2) 0.61343(11) 0.0159(3) Uani 1 1 d . . . . .
H15 H 0.161387 1.119294 0.660206 0.019 Uiso 1 1 calc R U . . .
C6 C 0.1940(2) 0.5689(2) 0.19680(10) 0.0120(3) Uani 1 1 d . . . . .
H3 H 0.374(3) 0.877(3) -0.0016(14) 0.017(4) Uiso 1 1 d . . . . .
H1 H 0.367(3) 0.663(3) 0.2670(16) 0.026(5) Uiso 1 1 d . . . . .
H5 H 0.069(3) 0.518(3) 0.0929(14) 0.023(5) Uiso 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
S4 C4 1.6649(14) . ?
S6 C6 1.6382(14) . ?
S2 C2 1.6558(14) . ?
N1 C2 1.3640(19) . ?
N1 C6 1.3752(18) . ?
N1 H1 0.87(2) . ?
N5 C4 1.3542(19) . ?
N5 C6 1.3804(18) . ?
N5 H5 0.83(2) . ?
N11 C17 1.3463(19) . ?
N11 C12 1.3488(18) . ?
N3 C2 1.3716(18) . ?
N3 C4 1.3639(18) . ?
N3 H3 0.86(2) . ?
C17 C12 1.437(2) 2_666 ?
C17 C16 1.4249(19) 2_666 ?
C12 C13 1.423(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.361(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.359(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.425(2) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 124.72(12) . . ?
C2 N1 H1 118.0(13) . . ?
C6 N1 H1 117.2(13) . . ?
C4 N5 C6 125.63(12) . . ?
C4 N5 H5 118.7(13) . . ?
C6 N5 H5 115.7(13) . . ?
C17 N11 C12 117.46(12) . . ?
C2 N3 H3 117.6(12) . . ?
C4 N3 C2 124.87(13) . . ?
C4 N3 H3 117.2(12) . . ?
N1 C2 S2 122.66(11) . . ?
N1 C2 N3 115.42(12) . . ?
N3 C2 S2 121.91(11) . . ?
N11 C17 C12 121.49(13) . 2_666 ?
N11 C17 C16 119.70(13) . 2_666 ?
C16 C17 C12 118.81(13) 2_666 2_666 ?
N11 C12 C17 121.04(13) . 2_666 ?
N11 C12 C13 119.38(13) . . ?
C13 C12 C17 119.58(13) . 2_666 ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.65(13) . . ?
C14 C13 H13 120.2 . . ?
C17 C16 H16 120.0 2_666 . ?
C15 C16 C17 119.93(13) . 2_666 ?
C15 C16 H16 120.0 . . ?
N5 C4 S4 123.04(11) . . ?
N5 C4 N3 115.02(12) . . ?
N3 C4 S4 121.94(11) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.90(14) . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 121.13(13) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
N1 C6 S6 124.26(11) . . ?
N1 C6 N5 114.27(12) . . ?
N5 C6 S6 121.46(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C13 H13 S6 0.93 2.83 3.5109(15) 131.0 1_565 yes
C16 H16 S4 0.93 2.96 3.8120(15) 153.5 1_556 yes

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
N11 C12 C13 C14 -179.97(12) . . . . ?
C2 N1 C6 S6 -177.46(10) . . . . ?
C2 N1 C6 N5 1.55(19) . . . . ?
C2 N3 C4 S4 177.80(10) . . . . ?
C2 N3 C4 N5 -2.1(2) . . . . ?
C17 N11 C12 C17 -1.1(2) . . . 2_666 ?
C17 N11 C12 C13 178.30(12) . . . . ?
C17 C12 C13 C14 -0.6(2) 2_666 . . . ?
C17 C16 C15 C14 -0.1(2) 2_666 . . . ?
C12 N11 C17 C12 1.1(2) . . . 2_666 ?
C12 N11 C17 C16 -179.51(12) . . . 2_666 ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C4 N5 C6 S6 176.69(11) . . . . ?
C4 N5 C6 N1 -2.4(2) . . . . ?
C4 N3 C2 S2 -177.85(10) . . . . ?
C4 N3 C2 N1 1.5(2) . . . . ?
C6 N1 C2 S2 178.15(10) . . . . ?
C6 N1 C2 N3 -1.2(2) . . . . ?
C6 N5 C4 S4 -177.31(11) . . . . ?
C6 N5 C4 N3 2.6(2) . . . . ?

_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 1.582
_oxdiff_exptl_absorpt_empirical_full_min 0.682
####################################################################### 
# 
# 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_exp_204
_database_code_depnum_ccdc_archive 'CCDC 2370434'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda - Raj'
;Faculty of Chemistry, University of Lodz, Lodz
Poland
;
_audit_update_record             
;
2024-07-13 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_audit_creation_date             2024-01-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H3 N3 S3, C5 H5 N3 S'
_chemical_formula_sum            'C8 H8 N6 S4'
_chemical_formula_weight         316.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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      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                   8.01570(10)
_cell_length_b                   8.57070(10)
_cell_length_c                   11.04420(10)
_cell_angle_alpha                110.3160(10)
_cell_angle_beta                 106.3480(10)
_cell_angle_gamma                95.8180(10)
_cell_volume                     665.850(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11005
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.7220
_cell_measurement_theta_min      4.5060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.501
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.1245
-1 0 0 0.0702
0 -1 0 0.0174
0 1 0 0.0139
0 0 1 0.0136
0 0 -1 0.0184

_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.031
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.9996 -0.0003 -0.0001 -0.0676 0.1861 0.0542
-0.9996 0.0003 0.0001 0.0676 -0.1861 -0.0542
-0.0003 -0.9995 0.0002 0.0764 -0.0689 0.1673
0.0003 0.9995 -0.0002 -0.0764 0.0689 -0.1673
-0.0001 -0.0001 0.9998 -0.1581 0.0018 -0.0002
0.0001 0.0001 -0.9998 0.1581 -0.0018 0.0002

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20245
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.936
_diffrn_reflns_theta_min         4.539
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 119.00   0.50    0.11    --   47.27  57.00  60.00  174
  2  ω     25.00 119.00   0.50    0.11    --   47.27  77.00  90.00  188
  3  ω     25.00 119.00   0.50    0.11    --   47.27  77.00 -60.00  188
  4  ω     25.00 119.00   0.50    0.11    --   47.27  77.00 -90.00  188
  5  ω     32.00 119.00   0.50    0.11    --   47.27  57.00-120.00  174
  6  ω     25.00 119.00   0.50    0.11    --   47.27  77.00-180.00  188
  7  ω     32.00 119.00   0.50    0.11    --   47.27  57.00-180.00  174
  8  ω    -12.00  28.00   0.50    0.11    --  -47.27  19.00  60.00   80
  9  ω    -12.00  28.00   0.50    0.11    --  -47.27  19.00 150.00   80
 10  ω    -12.00  28.00   0.50    0.11    --  -47.27  19.00 -60.00   80
 11  ω    -12.00  28.00   0.50    0.11    --  -47.27  19.00 -90.00   80
 12  ω     92.00 176.00   0.50    0.45    --  105.67  15.00  30.00  168
 13  ω     89.00 177.00   0.50    0.45    --  105.67 135.00-147.00  176
 14  ω     95.00 177.00   0.50    0.45    --  105.67 125.00 -90.00  164
 15  ω     89.00 177.00   0.50    0.45    --  105.67 135.00  31.00  176
 16  ω     93.00 177.00   0.50    0.45    --  105.67  45.00 -90.00  168
 17  ω    -27.00  12.00   0.50    0.11    --   47.27 -19.00-120.00   78
 18  ω    -27.00  12.00   0.50    0.11    --   47.27 -19.00-150.00   78
 19  ω    -27.00  12.00   0.50    0.11    --   47.27 -19.00 -60.00   78
 20  ω     33.00 128.00   0.50    0.45    --  105.67 -77.00 120.00  190
 21  ω     33.00  75.00   0.50    0.45    --  105.67 -61.00   0.00   84
 22  ω     33.00 105.00   0.50    0.45    --  105.67 -95.00 -30.00  144
 23  ω     40.00 101.00   0.50    0.11    --   47.27-135.00 -33.00  122
 24  ω     40.00 119.00   0.50    0.45    --  105.67-135.00 -33.00  158
 25  ω     34.00 111.00   0.50    0.45    --  105.67-125.00  90.00  154
 26  ω     40.00 119.00   0.50    0.45    --  105.67-135.00 146.00  158
 27  ω     40.00 101.00   0.50    0.11    --   47.27-135.00 146.00  122
 28  ω     33.00 105.00   0.50    0.45    --  105.67 -95.00 -60.00  144
 29  ω     33.00 105.00   0.50    0.45    --  105.67 -95.00-150.00  144
 30  ω    -93.00 -18.00   0.50    0.11    --  -47.27 135.00  31.00  150
 31  ω    -93.00 -19.00   0.50    0.45    --  -91.75 135.00  31.00  148
 32  ω    -93.00 -18.00   0.50    0.11    --  -47.27 135.00-147.00  150
 33  ω    -93.00 -19.00   0.50    0.45    --  -91.75 135.00-147.00  148
 34  ω    -49.00 -20.00   0.50    0.45    --  -91.75  45.00-120.00   58
 35  ω    -49.00 -20.00   0.50    0.45    --  -91.75  45.00 -30.00   58
 36  ω    -49.00 -20.00   0.50    0.45    --  -91.75  45.00   0.00   58
 37  ω    -49.00 -20.00   0.50    0.45    --  -91.75  45.00  30.00   58
 38  ω    -49.00 -20.00   0.50    0.45    --  -91.75  45.00 150.00   58
 39  ω   -166.00 -79.00   0.50    0.45    --  -91.75 -30.00 150.00  174
 40  ω   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00 150.00  188
 41  ω   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00 120.00  188
 42  ω   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00  90.00  188
 43  ω   -163.00 -71.00   0.50    0.45    --  -91.75 -77.00  60.00  184
 44  ω   -119.00 -25.00   0.50    0.11    --  -47.27 -77.00   0.00  188
 45  ω   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00 -30.00  188
 46  ω   -163.00 -75.00   0.50    0.45    --  -91.75 -61.00   0.00  176
 47  ω   -163.00 -75.00   0.50    0.45    --  -91.75 -61.00  30.00  176
 48  ω   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00 -60.00  188
 49  ω   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00-180.00  188
 50  ω   -163.00 -75.00   0.50    0.45    --  -91.75 -61.00-150.00  176
 51  ω   -163.00 -79.00   0.50    0.45    --  -91.75 -45.00-150.00  168
 52  ω   -163.00 -79.00   0.50    0.45    --  -91.75 -45.00-120.00  168
 53  ω   -163.00 -73.00   0.50    0.45    --  -91.75-125.00 120.00  180
 54  ω   -160.00 -67.00   0.50    0.45    --  -91.75-135.00 146.00  186
 55  ω   -119.00 -67.00   0.50    0.11    --  -47.27-135.00 146.00  104
 56  ω   -119.00 -67.00   0.50    0.11    --  -47.27-135.00 -33.00  104
 57  ω   -160.00 -67.00   0.50    0.45    --  -91.75-135.00 -33.00  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0676543000
_diffrn_orient_matrix_UB_12      -0.0764086000
_diffrn_orient_matrix_UB_13      -0.1581220000
_diffrn_orient_matrix_UB_21      0.1861986000
_diffrn_orient_matrix_UB_22      0.0689198000
_diffrn_orient_matrix_UB_23      0.0017981000
_diffrn_orient_matrix_UB_31      0.0541689000
_diffrn_orient_matrix_UB_32      -0.1674541000
_diffrn_orient_matrix_UB_33      -0.0001621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2393
_reflns_number_total             2685
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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         0.206
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.051
_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)+(0.0506P)²+0.1166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0886
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_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
S6 S 0.37445(7) 0.20636(6) 0.50653(4) 0.05962(15) Uani 1 1 d . . . . .
S17 S 0.03065(7) 0.46556(6) 0.23940(4) 0.05859(15) Uani 1 1 d . . . . .
S2 S 0.67710(7) 0.68549(6) 1.00226(4) 0.06371(16) Uani 1 1 d . . . . .
S4 S 0.81300(8) 0.06893(7) 0.89296(5) 0.07197(18) Uani 1 1 d . . . . .
N3 N 0.7299(2) 0.37073(18) 0.93110(15) 0.0516(3) Uani 1 1 d . . . . .
N1 N 0.5321(2) 0.42687(19) 0.76340(14) 0.0491(3) Uani 1 1 d . . . . .
N5 N 0.5994(2) 0.1629(2) 0.71384(15) 0.0533(4) Uani 1 1 d . . . . .
N14 N 0.3466(2) 0.6556(2) 0.68001(15) 0.0556(4) Uani 1 1 d . . . . .
N17 N -0.0371(3) 0.7709(3) 0.32314(19) 0.0721(5) Uani 1 1 d . . . . .
N11 N 0.1312(2) 0.8571(2) 0.59000(16) 0.0619(4) Uani 1 1 d . . . . .
C12 C 0.1454(2) 0.7100(2) 0.50287(17) 0.0474(4) Uani 1 1 d . . . . .
C6 C 0.5077(2) 0.2677(2) 0.66757(17) 0.0475(4) Uani 1 1 d . . . . .
C17 C 0.0413(2) 0.6568(2) 0.35391(17) 0.0485(4) Uani 1 1 d . . . . .
C13 C 0.2513(2) 0.6094(2) 0.54801(17) 0.0515(4) Uani 1 1 d . . . . .
H13 H 0.256042 0.506574 0.484249 0.062 Uiso 1 1 calc R U . . .
C4 C 0.7115(2) 0.2050(2) 0.84500(17) 0.0505(4) Uani 1 1 d . . . . .
C2 C 0.6459(2) 0.4855(2) 0.89570(16) 0.0481(4) Uani 1 1 d . . . . .
C15 C 0.3318(3) 0.8011(3) 0.7665(2) 0.0670(5) Uani 1 1 d . . . . .
H15 H 0.396577 0.838370 0.859481 0.080 Uiso 1 1 calc R U . . .
C16 C 0.2225(4) 0.8992(3) 0.7221(2) 0.0787(7) Uani 1 1 d . . . . .
H16 H 0.212252 0.998349 0.786878 0.094 Uiso 1 1 calc R U . . .
H1 H 0.475(3) 0.505(3) 0.738(2) 0.061(6) Uiso 1 1 d . . . . .
H3 H 0.803(3) 0.401(3) 1.018(2) 0.061(6) Uiso 1 1 d . . . . .
H5 H 0.589(3) 0.065(3) 0.655(3) 0.072(7) Uiso 1 1 d . . . . .
H17A H -0.098(4) 0.743(4) 0.237(3) 0.095(9) Uiso 1 1 d . . . . .
H17B H -0.020(4) 0.862(4) 0.384(3) 0.094(9) Uiso 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
S6 C6 1.6577(17) . ?
S17 C17 1.6624(18) . ?
S2 C2 1.6529(17) . ?
S4 C4 1.6372(18) . ?
N3 C4 1.373(2) . ?
N3 C2 1.352(2) . ?
N3 H3 0.90(2) . ?
N1 C6 1.359(2) . ?
N1 C2 1.366(2) . ?
N1 H1 0.93(2) . ?
N5 C6 1.360(2) . ?
N5 C4 1.369(2) . ?
N5 H5 0.84(3) . ?
N14 C13 1.333(2) . ?
N14 C15 1.323(3) . ?
N17 C17 1.305(2) . ?
N17 H17A 0.87(3) . ?
N17 H17B 0.80(3) . ?
N11 C12 1.333(2) . ?
N11 C16 1.332(2) . ?
C12 C17 1.497(2) . ?
C12 C13 1.386(2) . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N3 H3 114.8(14) . . ?
C2 N3 C4 125.33(14) . . ?
C2 N3 H3 119.8(14) . . ?
C6 N1 C2 124.26(15) . . ?
C6 N1 H1 119.4(14) . . ?
C2 N1 H1 116.2(14) . . ?
C6 N5 C4 125.87(16) . . ?
C6 N5 H5 116.6(17) . . ?
C4 N5 H5 117.5(17) . . ?
C15 N14 C13 116.40(16) . . ?
C17 N17 H17A 116.4(19) . . ?
C17 N17 H17B 117(2) . . ?
H17A N17 H17B 126(3) . . ?
C16 N11 C12 115.94(16) . . ?
N11 C12 C17 117.36(15) . . ?
N11 C12 C13 121.53(15) . . ?
C13 C12 C17 121.11(15) . . ?
N1 C6 S6 122.15(13) . . ?
N1 C6 N5 115.09(15) . . ?
N5 C6 S6 122.76(13) . . ?
N17 C17 S17 123.94(14) . . ?
N17 C17 C12 114.98(16) . . ?
C12 C17 S17 121.08(13) . . ?
N14 C13 C12 122.01(16) . . ?
N14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
N3 C4 S4 123.75(13) . . ?
N5 C4 S4 122.64(14) . . ?
N5 C4 N3 113.61(15) . . ?
N3 C2 S2 123.44(12) . . ?
N3 C2 N1 115.72(15) . . ?
N1 C2 S2 120.84(13) . . ?
N14 C15 H15 119.2 . . ?
N14 C15 C16 121.65(17) . . ?
C16 C15 H15 119.2 . . ?
N11 C16 C15 122.39(19) . . ?
N11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?

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
N14 C15 C16 N11 -2.6(4) . . . . ?
N11 C12 C17 S17 -172.70(14) . . . . ?
N11 C12 C17 N17 7.6(3) . . . . ?
N11 C12 C13 N14 -1.2(3) . . . . ?
C12 N11 C16 C15 2.8(4) . . . . ?
C6 N1 C2 S2 175.81(14) . . . . ?
C6 N1 C2 N3 -3.6(3) . . . . ?
C6 N5 C4 S4 178.38(15) . . . . ?
C6 N5 C4 N3 -1.6(3) . . . . ?
C17 C12 C13 N14 179.19(16) . . . . ?
C13 N14 C15 C16 0.4(3) . . . . ?
C13 C12 C17 S17 7.0(2) . . . . ?
C13 C12 C17 N17 -172.75(18) . . . . ?
C4 N3 C2 S2 -178.20(15) . . . . ?
C4 N3 C2 N1 1.2(3) . . . . ?
C4 N5 C6 S6 179.94(15) . . . . ?
C4 N5 C6 N1 -0.5(3) . . . . ?
C2 N3 C4 S4 -178.78(15) . . . . ?
C2 N3 C4 N5 1.2(3) . . . . ?
C2 N1 C6 S6 -177.16(14) . . . . ?
C2 N1 C6 N5 3.3(3) . . . . ?
C15 N14 C13 C12 1.4(3) . . . . ?
C16 N11 C12 C17 178.7(2) . . . . ?
C16 N11 C12 C13 -1.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.933
_oxdiff_exptl_absorpt_empirical_full_min 0.647
####################################################################### 
# 
# 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_exp_69
_database_code_depnum_ccdc_archive 'CCDC 2370435'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda - Raj'
;Faculty of Chemistry, University of Lodz, Lodz
Poland
;
_audit_update_record             
;
2024-07-13 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_audit_creation_date             2024-07-13
_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         'C3 H3 N3 S3, C4 H4 N2 O'
_chemical_formula_sum            'C7 H7 N5 O S3'
_chemical_formula_weight         273.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   4.49550(10)
_cell_length_b                   16.5288(3)
_cell_length_c                   14.9573(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.579(2)
_cell_angle_gamma                90
_cell_volume                     1104.09(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14763
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      30.9710
_cell_measurement_theta_min      2.4580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 21 8 0.0304
1 -9 18 0.0268
6 -8 -7 0.1079
0 6 -20 0.0225
1 20 10 0.0411
0 -11 18 0.0121
-6 5 4 0.1201
0 -21 -8 0.0244

_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.045
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.3980 21.3288 8.4862 0.6167 0.6534 -0.4390
1.0000 -9.0000 18.0000 -0.6513 0.7024 0.1633
6.0000 -8.0000 -7.0000 0.0535 -0.0688 1.0280
-0.0000 6.0000 -20.0000 0.6143 -0.7741 0.0390
1.0000 20.0000 10.0000 0.5878 0.7807 -0.2282
-0.3120 -11.3609 18.3774 -0.7940 0.6078 0.0090
-6.1954 4.6391 3.8516 -0.1247 -0.1272 -0.9840
0.3980 -21.3288 -8.4862 -0.6167 -0.6534 0.4390

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25107
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.065
_diffrn_reflns_theta_min         2.464
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  26.00   0.50   16.69    --   -5.34 -96.00 -33.00  110
  2  ω    -29.00  37.00   0.50   16.69    --    5.49 -96.00 -33.00  132
  3  ω    -23.00  28.00   0.50   16.69    --   -5.34 -99.00-120.00  102
  4  ω    -23.00  39.00   0.50   16.69    --    5.49 -99.00-150.00  124
  5  ω    -67.00  21.00   0.50   16.69    --    5.49 -57.00 -30.00  176
  6  ω    -23.00  27.00   0.50   16.69    --    5.49 -99.00  60.00  100
  7  ω    -23.00  39.00   0.50   16.69    --    5.49 -99.00 150.00  124
  8  ω    -81.00  -9.00   0.50   16.69    --   -5.34 -19.00 150.00  144
  9  ω    -17.00  78.00   0.50   16.69    --    5.49  77.00   0.00  190
 10  ω    -70.00  -9.00   0.50   16.69    --    5.49 -19.00-120.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0359591000
_diffrn_orient_matrix_UB_12      0.0373472000
_diffrn_orient_matrix_UB_13      -0.0195087000
_diffrn_orient_matrix_UB_21      0.0582374000
_diffrn_orient_matrix_UB_22      0.0145831000
_diffrn_orient_matrix_UB_23      0.0430774000
_diffrn_orient_matrix_UB_31      0.1433029000
_diffrn_orient_matrix_UB_32      -0.0153060000
_diffrn_orient_matrix_UB_33      -0.0065398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2680
_reflns_number_total             3086
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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         0.338
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.108
_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)+(0.0287P)²+0.3155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0646
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: S4(0.5) S1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_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
S6 S 1.03029(6) 0.52301(2) 0.36154(2) 0.01920(8) Uani 1 1 d . . . . .
S2 S 0.21722(8) 0.33208(2) 0.18635(2) 0.02487(9) Uani 1 1 d . . . . .
S4 S 0.463(3) 0.3089(6) 0.5404(6) 0.0261(11) Uani 0.5 1 d . . P . .
O11 O 0.6457(2) 0.51395(5) 0.12900(6) 0.0252(2) Uani 1 1 d . . . . .
N5 N 0.7263(2) 0.41035(6) 0.43789(7) 0.0184(2) Uani 1 1 d . . . . .
N1 N 0.6233(2) 0.42124(6) 0.28404(6) 0.01699(19) Uani 1 1 d . . . . .
N11 N 0.4538(2) 0.57280(6) 0.12997(7) 0.0191(2) Uani 1 1 d . . . . .
N3 N 0.3716(2) 0.32719(6) 0.36213(6) 0.0179(2) Uani 1 1 d . . . . .
N14 N 0.0446(2) 0.69832(6) 0.13271(7) 0.0217(2) Uani 1 1 d . . . . .
C4 C 0.5179(3) 0.35064(7) 0.44327(8) 0.0180(2) Uani 1 1 d . . . . .
C2 C 0.4105(3) 0.36136(7) 0.28092(7) 0.0171(2) Uani 1 1 d . . . . .
C16 C 0.4293(3) 0.61465(7) 0.20697(8) 0.0201(2) Uani 1 1 d . . . . .
H16 H 0.551621 0.602006 0.259510 0.024 Uiso 1 1 calc R U . . .
C6 C 0.7831(2) 0.44825(7) 0.36110(7) 0.0161(2) Uani 1 1 d . . . . .
C15 C 0.2223(3) 0.67575(7) 0.20654(8) 0.0200(2) Uani 1 1 d . . . . .
H15 H 0.204574 0.702835 0.260176 0.024 Uiso 1 1 calc R U . . .
C12 C 0.2773(3) 0.59400(8) 0.05399(8) 0.0245(3) Uani 1 1 d . . . . .
H12 H 0.290962 0.566592 0.000314 0.029 Uiso 1 1 calc R U . . .
C13 C 0.0777(3) 0.65670(8) 0.05751(8) 0.0257(3) Uani 1 1 d . . . . .
H13 H -0.040819 0.671016 0.004813 0.031 Uiso 1 1 calc R U . . .
H5 H 0.821(4) 0.4265(10) 0.4869(12) 0.030(4) Uiso 1 1 d . . . . .
H3 H 0.245(4) 0.2891(11) 0.3611(12) 0.039(5) Uiso 1 1 d . . . . .
H1 H 0.656(3) 0.4462(9) 0.2355(11) 0.025(4) Uiso 1 1 d . . . . .
S1 S 0.438(3) 0.3119(6) 0.5386(6) 0.0243(8) Uani 0.5 1 d . . P . .


_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
S6 C6 1.6614(12) . ?
S2 C2 1.6458(12) . ?
S4 C4 1.652(8) . ?
O11 N11 1.3013(13) . ?
N5 C4 1.3693(15) . ?
N5 C6 1.3580(14) . ?
N5 H5 0.848(18) . ?
N1 C2 1.3735(15) . ?
N1 C6 1.3618(15) . ?
N1 H1 0.862(16) . ?
N11 C16 1.3587(15) . ?
N11 C12 1.3554(16) . ?
N3 C4 1.3685(15) . ?
N3 C2 1.3688(14) . ?
N3 H3 0.848(19) . ?
N14 C15 1.3397(16) . ?
N14 C13 1.3413(16) . ?
C4 S1 1.641(9) . ?
C16 H16 0.9300 . ?
C16 C15 1.3727(17) . ?
C15 H15 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.3758(18) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N5 H5 117.0(11) . . ?
C6 N5 C4 125.34(10) . . ?
C6 N5 H5 117.6(11) . . ?
C2 N1 H1 120.1(10) . . ?
C6 N1 C2 124.25(10) . . ?
C6 N1 H1 115.6(10) . . ?
O11 N11 C16 120.56(10) . . ?
O11 N11 C12 120.60(10) . . ?
C12 N11 C16 118.84(10) . . ?
C4 N3 C2 124.94(10) . . ?
C4 N3 H3 118.6(12) . . ?
C2 N3 H3 116.4(12) . . ?
C15 N14 C13 115.81(11) . . ?
N5 C4 S4 121.6(4) . . ?
N5 C4 S1 123.5(4) . . ?
N3 C4 S4 123.9(4) . . ?
N3 C4 N5 114.49(10) . . ?
N3 C4 S1 121.9(4) . . ?
S1 C4 S4 4.4(10) . . ?
N1 C2 S2 122.56(9) . . ?
N3 C2 S2 122.20(9) . . ?
N3 C2 N1 115.25(10) . . ?
N11 C16 H16 120.3 . . ?
N11 C16 C15 119.44(11) . . ?
C15 C16 H16 120.3 . . ?
N5 C6 S6 122.03(9) . . ?
N5 C6 N1 115.63(10) . . ?
N1 C6 S6 122.34(9) . . ?
N14 C15 C16 123.26(11) . . ?
N14 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
N11 C12 H12 120.5 . . ?
N11 C12 C13 118.98(11) . . ?
C13 C12 H12 120.5 . . ?
N14 C13 C12 123.64(12) . . ?
N14 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?

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
O11 N11 C16 C15 -179.12(11) . . . . ?
O11 N11 C12 C13 -179.80(11) . . . . ?
N11 C16 C15 N14 -1.71(19) . . . . ?
N11 C12 C13 N14 -0.6(2) . . . . ?
C4 N5 C6 S6 177.28(9) . . . . ?
C4 N5 C6 N1 -2.40(17) . . . . ?
C4 N3 C2 S2 -177.71(9) . . . . ?
C4 N3 C2 N1 2.72(17) . . . . ?
C2 N1 C6 S6 -177.95(9) . . . . ?
C2 N1 C6 N5 1.72(16) . . . . ?
C2 N3 C4 S4 179.2(6) . . . . ?
C2 N3 C4 N5 -3.26(17) . . . . ?
C2 N3 C4 S1 174.5(6) . . . . ?
C16 N11 C12 C13 -0.51(18) . . . . ?
C6 N5 C4 S4 -179.4(6) . . . . ?
C6 N5 C4 N3 3.09(17) . . . . ?
C6 N5 C4 S1 -174.7(6) . . . . ?
C6 N1 C2 S2 178.56(9) . . . . ?
C6 N1 C2 N3 -1.88(16) . . . . ?
C15 N14 C13 C12 0.5(2) . . . . ?
C12 N11 C16 C15 1.60(17) . . . . ?
C13 N14 C15 C16 0.62(18) . . . . ?

_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 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.913
####################################################################### 
# 
# 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_exp_19
_database_code_depnum_ccdc_archive 'CCDC 2370433'
loop_
_audit_author_name
_audit_author_address
'Kinga Wzgarda - Raj'
;Faculty of Chemistry, University of Lodz, Lodz
Poland
;
_audit_update_record             
;
2024-07-13 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_exp_19              
;
PROBLEM: Hirshfeld Test Diff for    S2       --C2       .        7.3 s.u.
RESPONSE: The vibration of a sulfur substituent causes it.
;
# Added during the CSD deposition process: Saturday 13 July 2024 01:38 PM
# end Validation Reply Form

_audit_creation_date             2024-01-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 N4 S2, 2(C3 H3 N3 S3)'
_chemical_formula_sum            'C14 H12 N10 S8'
_chemical_formula_weight         576.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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                   19.96872(14)
_cell_length_b                   5.45162(3)
_cell_length_c                   23.70011(17)
_cell_angle_alpha                90
_cell_angle_beta                 111.7533(8)
_cell_angle_gamma                90
_cell_volume                     2396.31(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24710
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.3070
_cell_measurement_theta_min      3.9930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.137
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0670
-1 0 0 0.0228
1 0 0 0.0107
0 0 1 0.0034
0 0 -1 0.0156
-1 -2 1 0.0392

_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.019
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0031 0.9999 -0.0017 0.1620 -0.0135 0.2311
-1.0006 -0.0001 0.0018 -0.0222 0.0775 0.0201
1.0006 0.0001 -0.0018 0.0222 -0.0775 -0.0201
0.0011 0.0001 0.9994 -0.0434 -0.0474 0.0276
-0.0011 -0.0001 -0.9994 0.0434 0.0474 -0.0276
-0.9934 -1.9998 1.0046 -0.3897 0.0571 -0.4144

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            34136
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.539
_diffrn_reflns_theta_min         4.017
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  28.00   0.50    2.00    --  -47.45  19.00  30.00   80
  2  ω    -49.00 -14.00   0.50    6.80    --  -86.25  45.00 -60.00   70
  3  ω    -49.00 -14.00   0.50    6.80    --  -86.25  45.00 -90.00   70
  4  ω    -75.00 -13.00   0.50    6.80    --  -86.25  61.00 -60.00  124
  5  ω    -77.00  25.00   0.50    2.00    --  -47.45  92.00 102.00  204
  6  ω    -19.00  77.00   0.50    2.00    --   47.45 -92.00 -10.00  192
  7  ω     33.00 106.00   0.50    6.80    --  105.86 -92.00 -10.00  146
  8  ω     39.00 118.00   0.50    6.80    --  105.86-133.00-125.28  158
  9  ω     33.00 105.00   0.50    6.80    --  105.86 -95.00-120.00  144
 10  ω     34.00 112.00   0.50    6.80    --  105.86-125.00-150.00  156
 11  ω     33.00 105.00   0.50    6.80    --  105.86 -95.00-180.00  144
 12  ω     33.00 105.00   0.50    6.80    --  105.86 -95.00-150.00  144
 13  ω     33.00  75.00   0.50    6.80    --  105.86 -61.00   0.00   84
 14  ω     33.00 105.00   0.50    6.80    --  105.86 -95.00 -30.00  144
 15  ω     33.00 105.00   0.50    6.80    --  105.86 -95.00  90.00  144
 16  ω     38.00 116.00   0.50    6.80    --  105.86-131.00 150.88  156
 17  ω     33.00 105.00   0.50    6.80    --  105.86 -95.00 120.00  144
 18  ω     92.00 176.00   0.50    6.80    --  105.86  15.00  60.00  168
 19  ω     93.00 178.00   0.50    6.80    --  105.86  30.00 150.00  170
 20  ω     95.00 178.00   0.50    6.80    --  105.86 125.00  60.00  166
 21  ω    102.00 178.00   0.50    6.80    --  105.86  92.00 102.00  152
 22  ω     92.00 176.00   0.50    6.80    --  105.86  15.00   0.00  168
 23  ω     93.00 178.00   0.50    6.80    --  105.86  30.00-120.00  170
 24  ω     33.00 105.00   0.50    6.80    --  105.86 -95.00 -60.00  144
 25  ω     33.00  75.00   0.50    6.80    --  105.86 -61.00 150.00   84
 26  ω    -27.00  12.00   0.50    2.00    --   47.45 -19.00  90.00   78
 27  ω    -27.00  12.00   0.50    2.00    --   47.45 -19.00 120.00   78
 28  ω    -24.00  62.00   0.50    2.00    --   47.45 -57.00   0.00  172
 29  ω    -27.00  12.00   0.50    2.00    --   47.45 -19.00 -90.00   78
 30  ω     25.00 120.00   0.50    2.00    --   47.45  77.00  30.00  190
 31  ω     25.00 120.00   0.50    2.00    --   47.45  77.00-120.00  190
 32  ω     25.00 120.00   0.50    2.00    --   47.45  77.00 -60.00  190
 33  ω     25.00 120.00   0.50    2.00    --   47.45  77.00  90.00  190
 34  ω     25.00 120.00   0.50    2.00    --   47.45  77.00 -30.00  190
 35  ω     25.00 120.00   0.50    2.00    --   47.45  77.00-180.00  190
 36  ω     25.00 120.00   0.50    2.00    --   47.45  77.00 150.00  190
 37  ω    -80.00 -13.00   0.50    6.80    --  -86.25  92.00 102.00  134
 38  ω    -86.00 -13.00   0.50    6.80    --  -86.25 125.00 -30.00  146
 39  ω   -120.00 -32.00   0.50    2.00    --  -47.45 -58.00  76.13  176
 40  ω   -120.00 -73.00   0.50    2.00    --  -47.45-125.00 120.00   94
 41  ω   -159.00 -80.00   0.50    6.80    --  -86.25 -92.00 -10.00  158
 42  ω   -159.00 -65.00   0.50    6.80    --  -86.25 -72.00  61.10  188
 43  ω   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00  23.47  192
 44  ω   -159.00 -70.00   0.50    6.80    --  -86.25 -61.00-180.00  178
 45  ω   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00 -30.00  192
 46  ω   -159.00 -62.00   0.50    6.80    --  -86.25 -80.00-122.96  194
 47  ω   -159.00 -64.00   0.50    6.80    --  -86.25 -75.00 -72.00  190
 48  ω   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00 120.00  192
 49  ω   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00 150.00  192
 50  ω   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00  90.00  192
 51  ω   -159.00 -63.00   0.50    6.80    --  -86.25 -77.00 -90.00  192
 52  ω   -159.00 -64.00   0.50    6.80    --  -86.25 -76.00-176.76  190
 53  ω   -159.00 -63.00   0.50    6.80    --  -86.25 -78.00   6.82  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0220541000
_diffrn_orient_matrix_UB_12      0.1620646000
_diffrn_orient_matrix_UB_13      -0.0434874000
_diffrn_orient_matrix_UB_21      -0.0775319000
_diffrn_orient_matrix_UB_22      -0.0138078000
_diffrn_orient_matrix_UB_23      -0.0473327000
_diffrn_orient_matrix_UB_31      -0.0200936000
_diffrn_orient_matrix_UB_32      0.2310873000
_diffrn_orient_matrix_UB_33      0.0276663000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2384
_reflns_number_total             2490
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.78a (Rigaku OD, 2020)'
_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         0.271
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0226
_refine_ls_restrained_S_all      1.071
_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)+(0.0315P)²+1.3515P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0628
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 S2, S4
 with sigma for 1-2 distances of 0.1 and sigma for 1-3 distances of 0.1
3. Uiso/Uaniso restraints and constraints
S2 \\sim S4: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_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 0.26437(2) 0.00250(6) 0.57347(2) 0.04249(10) Uani 1 1 d . . . . .
S6 S 0.47865(2) 0.58555(7) 0.58113(2) 0.04890(11) Uani 1 1 d . . . . .
S4 S 0.38802(2) -0.09806(9) 0.41239(2) 0.05823(13) Uani 1 1 d . . . . .
S13 S 0.46548(2) 1.10825(7) 0.77272(2) 0.05646(12) Uani 1 1 d . . . . .
N3 N 0.33347(6) -0.0235(2) 0.49725(5) 0.0390(2) Uani 1 1 d . . . . .
N1 N 0.37396(6) 0.2700(2) 0.57181(5) 0.0381(2) Uani 1 1 d . . . . .
N5 N 0.42399(6) 0.2380(2) 0.49894(5) 0.0431(3) Uani 1 1 d . . . . .
N11 N 0.36088(6) 0.5357(2) 0.67004(5) 0.0440(3) Uani 1 1 d . . . . .
C2 C 0.32639(7) 0.0854(2) 0.54615(6) 0.0353(3) Uani 1 1 d . . . . .
N14 N 0.34289(8) 0.8802(3) 0.74958(7) 0.0605(4) Uani 1 1 d . . . . .
C13 C 0.40125(8) 0.8776(3) 0.73534(6) 0.0441(3) Uani 1 1 d . . . . .
C6 C 0.42351(7) 0.3557(3) 0.54929(6) 0.0379(3) Uani 1 1 d . . . . .
C12 C 0.41036(7) 0.7071(3) 0.69553(6) 0.0434(3) Uani 1 1 d . . . . .
H12 H 0.451810 0.712319 0.686420 0.052 Uiso 1 1 calc R U . . .
C4 C 0.38150(7) 0.0432(3) 0.47109(6) 0.0402(3) Uani 1 1 d . . . . .
C16 C 0.30307(9) 0.5346(3) 0.68469(7) 0.0531(4) Uani 1 1 d . . . . .
H16 H 0.267866 0.415318 0.668387 0.064 Uiso 1 1 calc R U . . .
C15 C 0.29429(10) 0.7077(4) 0.72381(9) 0.0655(5) Uani 1 1 d . . . . .
H15 H 0.252546 0.703419 0.732493 0.079 Uiso 1 1 calc R U . . .
H3 H 0.3070(9) -0.138(3) 0.4817(7) 0.049(5) Uiso 1 1 d . . . . .
H1 H 0.3714(8) 0.342(3) 0.6026(8) 0.045(4) Uiso 1 1 d . . . . .
H5 H 0.4530(9) 0.287(4) 0.4836(8) 0.056(5) Uiso 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
S2 C2 1.6589(13) . ?
S6 C6 1.6544(13) . ?
S4 C4 1.6369(14) . ?
S13 S13 2.0399(9) 2_656 ?
S13 C13 1.7803(15) . ?
N3 C2 1.3553(17) . ?
N3 C4 1.3702(17) . ?
N3 H3 0.813(18) . ?
N1 C2 1.3626(16) . ?
N1 C6 1.3688(16) . ?
N1 H1 0.845(17) . ?
N5 C6 1.3578(17) . ?
N5 C4 1.3670(18) . ?
N5 H5 0.834(19) . ?
N11 C12 1.3310(19) . ?
N11 C16 1.323(2) . ?
N14 C13 1.328(2) . ?
N14 C15 1.326(2) . ?
C13 C12 1.384(2) . ?
C12 H12 0.9300 . ?
C16 H16 0.9300 . ?
C16 C15 1.379(3) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S13 S13 103.92(5) . 2_656 ?
C2 N3 C4 125.67(12) . . ?
C2 N3 H3 117.9(12) . . ?
C4 N3 H3 116.5(12) . . ?
C2 N1 C6 124.26(12) . . ?
C2 N1 H1 118.2(11) . . ?
C6 N1 H1 117.5(11) . . ?
C6 N5 C4 125.88(12) . . ?
C6 N5 H5 117.6(13) . . ?
C4 N5 H5 116.5(13) . . ?
C16 N11 C12 117.22(13) . . ?
N3 C2 S2 122.95(10) . . ?
N3 C2 N1 115.40(11) . . ?
N1 C2 S2 121.65(10) . . ?
C15 N14 C13 115.89(14) . . ?
N14 C13 S13 113.84(11) . . ?
N14 C13 C12 122.01(14) . . ?
C12 C13 S13 124.15(12) . . ?
N1 C6 S6 122.39(10) . . ?
N5 C6 S6 122.57(10) . . ?
N5 C6 N1 115.04(12) . . ?
N11 C12 C13 121.19(13) . . ?
N11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
N3 C4 S4 123.32(11) . . ?
N5 C4 S4 123.05(10) . . ?
N5 C4 N3 113.63(12) . . ?
N11 C16 H16 119.5 . . ?
N11 C16 C15 120.92(16) . . ?
C15 C16 H16 119.5 . . ?
N14 C15 C16 122.75(15) . . ?
N14 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?

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
S13 S13 C13 N14 -167.08(11) 2_656 . . . ?
S13 S13 C13 C12 13.71(14) 2_656 . . . ?
S13 C13 C12 N11 178.54(11) . . . . ?
N11 C16 C15 N14 -1.3(3) . . . . ?
C2 N3 C4 S4 179.30(11) . . . . ?
C2 N3 C4 N5 -0.2(2) . . . . ?
C2 N1 C6 S6 178.30(10) . . . . ?
C2 N1 C6 N5 -1.69(19) . . . . ?
N14 C13 C12 N11 -0.6(2) . . . . ?
C13 N14 C15 C16 0.2(3) . . . . ?
C6 N1 C2 S2 -176.13(10) . . . . ?
C6 N1 C2 N3 3.80(19) . . . . ?
C6 N5 C4 S4 -176.83(12) . . . . ?
C6 N5 C4 N3 2.7(2) . . . . ?
C12 N11 C16 C15 1.3(2) . . . . ?
C4 N3 C2 S2 177.15(11) . . . . ?
C4 N3 C2 N1 -2.79(19) . . . . ?
C4 N5 C6 S6 178.20(11) . . . . ?
C4 N5 C6 N1 -1.8(2) . . . . ?
C16 N11 C12 C13 -0.4(2) . . . . ?
C15 N14 C13 S13 -178.52(14) . . . . ?
C15 N14 C13 C12 0.7(2) . . . . ?

_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.872
