Co-crystal synthesis of 2- and 4-mercaptopyridines with thiourea and its analogue, trithiocyanuric acid
Wzgarda-Raj, Kinga; Książkiewicz, Olga; Palusiak, Marcin; CrystEngComm  (2022) –; doi:10.1039/D2CE00592A

data_7245151
_publ_section_title
;
 Co-crystal synthesis of 2- and 4-mercaptopyridines with thiourea and its
 analogue, trithiocyanuric acid
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00592A
_journal_year                    2022
_chemical_formula_moiety         'C3 H3 N3 S3, C5 H5 N S'
_chemical_formula_sum            'C8 H8 N4 S4'
_chemical_formula_weight         288.42
_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             2022-04-08
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-15 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                99.138(2)
_cell_angle_beta                 93.308(2)
_cell_angle_gamma                93.370(2)
_cell_formula_units_Z            2
_cell_length_a                   4.19560(10)
_cell_length_b                   10.8480(3)
_cell_length_c                   13.5301(4)
_cell_measurement_reflns_used    3965
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.8390
_cell_measurement_theta_min      3.2930
_cell_volume                     605.53(3)
_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      air
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_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   -118.00 -80.00   0.50    0.05    --  -47.45-131.00 175.00   76
  2  \w   -139.00-114.00   0.50    0.15    --  -86.25-131.00 175.00   50
  3  \w   -114.00 -64.00   0.50    0.05    --  -47.45-139.00   0.00  100
  4  \w    -99.00 -26.00   0.50    0.05    --  -47.45 -77.00-120.00  146
  5  \w     -5.00  27.00   0.50    0.05    --  -47.45  19.00   0.00   64
  6  \w    -48.00 -14.00   0.50    0.15    --  -86.25  45.00   0.00   68
  7  \w    -46.00 -21.00   0.50    0.15    --  -86.25  45.00  30.00   50
  8  \w    -75.00 -50.00   0.50    0.05    --  -47.45 139.00  61.00   50
  9  \w    -89.00 -64.00   0.50    0.15    --  -86.25 139.00  61.00   50
 10  \w    -78.00 -50.00   0.50    0.05    --  -47.45 131.00-113.00   56
 11  \w    -77.00 -51.00   0.50    0.15    --  -86.25 131.00-113.00   52
 12  \w    -48.00 -15.00   0.50    0.15    --  -86.25  45.00-180.00   66
 13  \w    -49.00 -18.00   0.50    0.15    --  -86.25  45.00-150.00   62
 14  \w   -112.00 -73.00   0.50    0.15    --  -86.25 -15.00  30.00   78
 15  \w   -135.00-110.00   0.50    0.15    --  -86.25-139.00   0.00   50
 16  \w   -160.00-115.00   0.50    0.15    --  -86.25 -15.00  30.00   90
 17  \w    -25.00   1.00   0.50    0.05    --   47.45 -19.00-180.00   52
 18  \w    -14.00  11.00   0.50    0.05    --   47.45 -19.00 -90.00   50
 19  \w     49.00  75.00   0.50    0.15    --  105.86 -61.00 -30.00   52
 20  \w     78.00 105.00   0.50    0.15    --  105.86 -95.00   0.00   54
 21  \w     77.00 120.00   0.50    0.15    --  105.86-139.00   0.00   86
 22  \w     67.00  98.00   0.50    0.05    --   47.45-139.00   0.00   62
 23  \w     40.00  74.00   0.50    0.15    --  105.86 -61.00  60.00   68
 24  \w     34.00  63.00   0.50    0.15    --  105.86 -61.00  30.00   58
 25  \w     35.00  78.00   0.50    0.15    --  105.86-125.00  30.00   86
 26  \w     41.00  75.00   0.50    0.15    --  105.86 -61.00 150.00   68
 27  \w     69.00  94.00   0.50    0.15    --  105.86-131.00 175.00   50
 28  \w     67.00  93.00   0.50    0.05    --   47.45-131.00 175.00   52
 29  \w     93.00 176.00   0.50    0.15    --  105.86  45.00 -60.00  166
 30  \w    106.00 132.00   0.50    0.15    --  105.86 139.00  61.00   52
 31  \w    126.00 175.00   0.50    0.15    --  105.86 131.00-113.00   98
 32  \w    153.00 178.00   0.50    0.15    --  105.86 125.00-180.00   50
 33  \w    119.00 145.00   0.50    0.15    --  105.86 125.00-180.00   52
 34  \w     93.00 121.00   0.50    0.15    --  105.86 131.00-113.00   56
 35  \w    117.00 175.00   0.50    0.15    --  105.86  45.00-180.00  116
 36  \w     96.00 168.00   0.50    0.15    --  105.86  15.00 -90.00  144
 37  \w     72.00 102.00   0.50    0.15    --  105.86-125.00-150.00   60
 38  \w     49.00  74.00   0.50    0.15    --  105.86 -61.00-150.00   50
 39  \w     43.00  69.00   0.50    0.15    --  105.86 -61.00-120.00   52
 40  \w     42.00  75.00   0.50    0.15    --  105.86 -61.00-180.00   66
;
_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      0.0543887000
_diffrn_orient_matrix_UB_12      0.0921182000
_diffrn_orient_matrix_UB_13      0.0994962000
_diffrn_orient_matrix_UB_21      -0.0613745000
_diffrn_orient_matrix_UB_22      -0.1086543000
_diffrn_orient_matrix_UB_23      0.0587633000
_diffrn_orient_matrix_UB_31      0.3594391000
_diffrn_orient_matrix_UB_32      -0.0222963000
_diffrn_orient_matrix_UB_33      0.0030424000
_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  0.0365
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5954
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.481
_diffrn_reflns_theta_min         3.316
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.034
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_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    1.582
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0206(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0312
_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^)+(0.0466P)^2^+0.0050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0832
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1940
_reflns_number_total             2201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00592a2.cif
_cod_data_source_block           structure_IV
_cod_database_code               7245151
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4), C6(H6)
;
_shelx_res_checksum              80649
_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 1.490
_oxdiff_exptl_absorpt_empirical_full_min 0.801