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_7249781
_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         'C3 H3 N3 S3, C5 H5 N3 S'
_chemical_formula_sum            'C8 H8 N6 S4'
_chemical_formula_weight         316.44
_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             2024-01-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-07-13 deposited with the CCDC.	2024-12-27 downloaded from the CCDC.
;
_cell_angle_alpha                110.3160(10)
_cell_angle_beta                 106.3480(10)
_cell_angle_gamma                95.8180(10)
_cell_formula_units_Z            2
_cell_length_a                   8.01570(10)
_cell_length_b                   8.57070(10)
_cell_length_c                   11.04420(10)
_cell_measurement_reflns_used    11005
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.7220
_cell_measurement_theta_min      4.5060
_cell_volume                     665.851(15)
_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_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  t~exp~   \w     \q     \k     \f   Frames
  1  \w     32.00 119.00   0.50    0.11    --   47.27  57.00  60.00  174
  2  \w     25.00 119.00   0.50    0.11    --   47.27  77.00  90.00  188
  3  \w     25.00 119.00   0.50    0.11    --   47.27  77.00 -60.00  188
  4  \w     25.00 119.00   0.50    0.11    --   47.27  77.00 -90.00  188
  5  \w     32.00 119.00   0.50    0.11    --   47.27  57.00-120.00  174
  6  \w     25.00 119.00   0.50    0.11    --   47.27  77.00-180.00  188
  7  \w     32.00 119.00   0.50    0.11    --   47.27  57.00-180.00  174
  8  \w    -12.00  28.00   0.50    0.11    --  -47.27  19.00  60.00   80
  9  \w    -12.00  28.00   0.50    0.11    --  -47.27  19.00 150.00   80
 10  \w    -12.00  28.00   0.50    0.11    --  -47.27  19.00 -60.00   80
 11  \w    -12.00  28.00   0.50    0.11    --  -47.27  19.00 -90.00   80
 12  \w     92.00 176.00   0.50    0.45    --  105.67  15.00  30.00  168
 13  \w     89.00 177.00   0.50    0.45    --  105.67 135.00-147.00  176
 14  \w     95.00 177.00   0.50    0.45    --  105.67 125.00 -90.00  164
 15  \w     89.00 177.00   0.50    0.45    --  105.67 135.00  31.00  176
 16  \w     93.00 177.00   0.50    0.45    --  105.67  45.00 -90.00  168
 17  \w    -27.00  12.00   0.50    0.11    --   47.27 -19.00-120.00   78
 18  \w    -27.00  12.00   0.50    0.11    --   47.27 -19.00-150.00   78
 19  \w    -27.00  12.00   0.50    0.11    --   47.27 -19.00 -60.00   78
 20  \w     33.00 128.00   0.50    0.45    --  105.67 -77.00 120.00  190
 21  \w     33.00  75.00   0.50    0.45    --  105.67 -61.00   0.00   84
 22  \w     33.00 105.00   0.50    0.45    --  105.67 -95.00 -30.00  144
 23  \w     40.00 101.00   0.50    0.11    --   47.27-135.00 -33.00  122
 24  \w     40.00 119.00   0.50    0.45    --  105.67-135.00 -33.00  158
 25  \w     34.00 111.00   0.50    0.45    --  105.67-125.00  90.00  154
 26  \w     40.00 119.00   0.50    0.45    --  105.67-135.00 146.00  158
 27  \w     40.00 101.00   0.50    0.11    --   47.27-135.00 146.00  122
 28  \w     33.00 105.00   0.50    0.45    --  105.67 -95.00 -60.00  144
 29  \w     33.00 105.00   0.50    0.45    --  105.67 -95.00-150.00  144
 30  \w    -93.00 -18.00   0.50    0.11    --  -47.27 135.00  31.00  150
 31  \w    -93.00 -19.00   0.50    0.45    --  -91.75 135.00  31.00  148
 32  \w    -93.00 -18.00   0.50    0.11    --  -47.27 135.00-147.00  150
 33  \w    -93.00 -19.00   0.50    0.45    --  -91.75 135.00-147.00  148
 34  \w    -49.00 -20.00   0.50    0.45    --  -91.75  45.00-120.00   58
 35  \w    -49.00 -20.00   0.50    0.45    --  -91.75  45.00 -30.00   58
 36  \w    -49.00 -20.00   0.50    0.45    --  -91.75  45.00   0.00   58
 37  \w    -49.00 -20.00   0.50    0.45    --  -91.75  45.00  30.00   58
 38  \w    -49.00 -20.00   0.50    0.45    --  -91.75  45.00 150.00   58
 39  \w   -166.00 -79.00   0.50    0.45    --  -91.75 -30.00 150.00  174
 40  \w   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00 150.00  188
 41  \w   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00 120.00  188
 42  \w   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00  90.00  188
 43  \w   -163.00 -71.00   0.50    0.45    --  -91.75 -77.00  60.00  184
 44  \w   -119.00 -25.00   0.50    0.11    --  -47.27 -77.00   0.00  188
 45  \w   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00 -30.00  188
 46  \w   -163.00 -75.00   0.50    0.45    --  -91.75 -61.00   0.00  176
 47  \w   -163.00 -75.00   0.50    0.45    --  -91.75 -61.00  30.00  176
 48  \w   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00 -60.00  188
 49  \w   -163.00 -69.00   0.50    0.45    --  -91.75 -77.00-180.00  188
 50  \w   -163.00 -75.00   0.50    0.45    --  -91.75 -61.00-150.00  176
 51  \w   -163.00 -79.00   0.50    0.45    --  -91.75 -45.00-150.00  168
 52  \w   -163.00 -79.00   0.50    0.45    --  -91.75 -45.00-120.00  168
 53  \w   -163.00 -73.00   0.50    0.45    --  -91.75-125.00 120.00  180
 54  \w   -160.00 -67.00   0.50    0.45    --  -91.75-135.00 146.00  186
 55  \w   -119.00 -67.00   0.50    0.11    --  -47.27-135.00 146.00  104
 56  \w   -119.00 -67.00   0.50    0.11    --  -47.27-135.00 -33.00  104
 57  \w   -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       '\w 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_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_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_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_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.042
_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_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0506P)^2^+0.1166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2393
_reflns_number_total             2685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce01153h2.cif
_cod_data_source_block           exp_204
_cod_depositor_comments
'Adding full bibliography for 7249780--7249783.cif.'
_cod_original_cell_volume        665.850(14)
_cod_database_code               7249781
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 100.00
_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), C15(H15), C16(H16)
;
_shelx_res_checksum              68241
_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