The N–H⋯S hydrogen bonding pattern in trithiocyanuric acid in crystalline state: geometric, topological, and energetic analysis of trithiocyanuric acid cocrystals
Wzgarda-Raj, Kinga; Rybarczyk-Pirek, Agnieszka J.; Palusiak, Marcin; CrystEngComm 27 (2025) 784–794; doi:10.1039/D4CE01153H

data_7249780
_publ_section_title
;
 The N--H&#x22EF;S hydrogen bonding pattern in trithiocyanuric acid in
 crystalline state: geometric, topological, and energetic analysis of
 trithiocyanuric acid cocrystals
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              784
_journal_page_last               794
_journal_paper_doi               10.1039/D4CE01153H
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C12 H8 N2, 2(C3 H3 N3 S3)'
_chemical_formula_sum            'C18 H14 N8 S6'
_chemical_formula_weight         534.73
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-13
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-07-13 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                81.841(3)
_cell_angle_beta                 81.532(3)
_cell_angle_gamma                63.930(4)
_cell_formula_units_Z            1
_cell_length_a                   6.5124(3)
_cell_length_b                   6.7635(2)
_cell_length_c                   13.9013(5)
_cell_measurement_reflns_used    12148
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7410
_cell_measurement_theta_min      3.2180
_cell_volume                     541.95(4)
_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)'
_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -119.00 -90.00   0.50    0.42    --  -47.48-125.00 -60.00   58
  2  \w    -62.00  25.00   0.50    0.42    --  -47.48  57.00 120.00  174
  3  \w   -120.00 -35.00   0.50    0.42    --  -47.48 -38.00   0.00  170
  4  \w   -120.00 -35.00   0.50    0.42    --  -47.48 -38.00 -90.00  170
  5  \w     92.00 120.00   0.50    0.42    --   47.48  57.00 120.00   56
  6  \w     -1.00  81.00   0.50    0.42    --   47.48 -99.00-180.00  164
  7  \w    -27.00  12.00   0.50    0.42    --   47.48 -19.00-120.00   78
  8  \w   -163.00 -97.00   0.50    1.68    --  -91.75 -61.00 120.00  132
  9  \w    -75.00 -19.00   0.50    1.68    --  -91.75  61.00   0.00  112
 10  \w   -163.00-104.00   0.50    1.68    --  -91.75 -77.00 150.00  118
 11  \w   -163.00-103.00   0.50    1.68    --  -91.75 -95.00 -90.00  120
 12  \w   -163.00 -97.00   0.50    1.68    --  -91.75 -61.00  30.00  132
 13  \w    -75.00 -19.00   0.50    1.68    --  -91.75  61.00  30.00  112
 14  \w   -163.00-104.00   0.50    1.68    --  -91.75 -77.00   0.00  118
 15  \w    -49.00 -20.00   0.50    1.68    --  -91.75  45.00 -30.00   58
 16  \w    -49.00 -20.00   0.50    1.68    --  -91.75  45.00-120.00   58
 17  \w    -49.00 -20.00   0.50    1.68    --  -91.75  45.00  90.00   58
 18  \w    -49.00 -20.00   0.50    1.68    --  -91.75  45.00 -90.00   58
 19  \w    -85.00 -19.00   0.50    1.68    --  -91.75 125.00  90.00  132
 20  \w    -75.00 -19.00   0.50    1.68    --  -91.75  61.00 120.00  112
 21  \w     33.00 105.00   0.50    1.68    --  105.71 -95.00  30.00  144
 22  \w    104.00 177.00   0.50    1.68    --  105.71  77.00-150.00  146
 23  \w     34.00 111.00   0.50    1.68    --  105.71-125.00-150.00  154
 24  \w     33.00  75.00   0.50    1.68    --  105.71 -61.00-180.00   84
 25  \w     33.00 105.00   0.50    1.68    --  105.71 -95.00 -90.00  144
 26  \w     34.00 111.00   0.50    1.68    --  105.71-125.00 120.00  154
 27  \w     33.00 105.00   0.50    1.68    --  105.71 -95.00 -30.00  144
 28  \w     33.00 105.00   0.50    1.68    --  105.71 -95.00-180.00  144
 29  \w     33.00 106.00   0.50    1.68    --  105.71 -97.00-141.58  146
 30  \w   -120.00 -35.00   0.50    0.42    --  -47.48 -38.00  60.00  170
 31  \w    -12.00  28.00   0.50    0.42    --  -47.48  19.00 -30.00   80
 32  \w   -119.00 -92.00   0.50    0.42    --  -47.48 -57.00-180.00   54
 33  \w   -119.00 -29.00   0.50    0.42    --  -47.48 -67.00-131.00  180
 34  \w     34.00 120.00   0.50    0.42    --   47.48  51.00-151.21  172
 35  \w     35.00 120.00   0.50    0.42    --   47.48  38.00-180.00  170
 36  \w     29.00 120.00   0.50    0.42    --   47.48  67.00   2.00  182
 37  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -51.00 -85.03  170
 38  \w   -163.00 -82.00   0.50    1.68    --  -91.75 -53.00-160.72  162
 39  \w   -163.00 -79.00   0.50    1.68    --  -91.75 -47.00 139.04  168
 40  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -51.00 -71.15  170
 41  \w   -163.00 -79.00   0.50    1.68    --  -91.75 -45.00 -30.00  168
 42  \w   -163.00 -73.00   0.50    1.68    --  -91.75 -67.00-131.00  180
 43  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00  22.51  170
 44  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00-123.82  170
 45  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -48.00  83.67  170
 46  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -49.00  64.90  170
 47  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00 171.08  170
 48  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -50.00  -5.62  170
 49  \w   -163.00 -79.00   0.50    1.68    --  -91.75 -45.00  30.00  168
 50  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00 -94.91  170
 51  \w   -163.00 -86.00   0.50    1.68    --  -91.75 -54.00 160.66  154
 52  \w   -163.00 -79.00   0.50    1.68    --  -91.75 -45.00 -60.00  168
 53  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00 116.79  170
 54  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -52.00  52.38  170
 55  \w    -49.00 -20.00   0.50    1.68    --  -91.75  45.00 150.00   58
 56  \w   -163.00 -78.00   0.50    1.68    --  -91.75 -51.00-149.87  170
 57  \w   -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       '\w 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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_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_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             274
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_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_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0214
_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/[\s^2^(Fo^2^)+(0.0273P)^2^+0.3302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1915
_reflns_number_total             1997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01153h2.cif
_cod_data_source_block           exp_586
_cod_depositor_comments
'Adding full bibliography for 7249780--7249783.cif.'
_cod_database_code               7249780
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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)
;
_shelx_res_checksum              88097
_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