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_7245150
_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         'C5 H5 N S, C H4 N2 S'
_chemical_formula_sum            'C6 H9 N3 S2'
_chemical_formula_weight         187.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 107.920(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5170(2)
_cell_length_b                   10.86720(10)
_cell_length_c                   8.42870(10)
_cell_measurement_reflns_used    3668
_cell_measurement_temperature    298
_cell_measurement_theta_max      75.5100
_cell_measurement_theta_min      5.9890
_cell_volume                     916.59(2)
_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      298
_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 0.993
_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     92.00 127.00   0.50    0.12    --  105.67  15.00  30.00   70
  2  \w    100.00 126.00   0.50    0.12    --  105.67  15.00 -30.00   52
  3  \w    144.00 169.00   0.50    0.12    --  105.67  15.00 -30.00   50
  4  \w    148.00 176.00   0.50    0.12    --  105.67  15.00  30.00   56
  5  \w    113.00 139.00   0.50    0.12    --  105.67 115.00  38.00   52
  6  \w     34.00  60.00   0.50    0.12    --  105.67 -61.00 -60.00   52
  7  \w     34.00  59.00   0.50    0.05    --   47.52-115.00 -51.00   50
  8  \w     48.00 108.00   0.50    0.12    --  105.67-115.00 -51.00  120
  9  \w     61.00 102.00   0.50    0.12    --  105.67 -95.00 -30.00   82
 10  \w     94.00 146.00   0.50    0.12    --  105.67-174.00 169.00  104
 11  \w     -3.00  25.00   0.50    0.05    --  -47.52  19.00-150.00   56
 12  \w     -6.00  21.00   0.50    0.05    --  -47.52  19.00-120.00   54
 13  \w     -6.00  23.00   0.50    0.05    --  -47.52  19.00 -90.00   58
 14  \w     -8.00  21.00   0.50    0.05    --  -47.52  19.00 -60.00   58
 15  \w    -10.00  16.00   0.50    0.05    --  -47.52  19.00 -30.00   52
 16  \w    -49.00 -21.00   0.50    0.12    --  -91.75  45.00 -90.00   56
 17  \w    -70.00 -40.00   0.50    0.12    --  -91.75  61.00-120.00   60
 18  \w    -49.00 -20.00   0.50    0.12    --  -91.75  45.00-180.00   58
 19  \w    -48.00 -23.00   0.50    0.12    --  -91.75  45.00-120.00   50
 20  \w    -71.00 -31.00   0.50    0.12    --  -91.75  61.00  30.00   80
 21  \w    -72.00 -19.00   0.50    0.12    --  -91.75  61.00  60.00  106
 22  \w    -48.00 -20.00   0.50    0.12    --  -91.75  45.00  60.00   56
 23  \w   -140.00 -85.00   0.50    0.12    --  -91.75-115.00 -51.00  110
 24  \w    -71.00 -45.00   0.50    0.05    --  -47.52-174.00 169.00   52
 25  \w    -48.00 -17.00   0.50    0.05    --  -47.52 115.00  38.00   62
 26  \w    -81.00 -54.00   0.50    0.05    --  -47.52 115.00  38.00   54
;
_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      0.0137904000
_diffrn_orient_matrix_UB_12      0.1389261000
_diffrn_orient_matrix_UB_13      -0.0273080000
_diffrn_orient_matrix_UB_21      0.1526332000
_diffrn_orient_matrix_UB_22      -0.0148725000
_diffrn_orient_matrix_UB_23      0.0442585000
_diffrn_orient_matrix_UB_31      -0.0147008000
_diffrn_orient_matrix_UB_32      -0.0240215000
_diffrn_orient_matrix_UB_33      -0.1848979000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5349
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.494
_diffrn_reflns_theta_min         4.418
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.802
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.428
_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            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.355
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0051(10)
_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   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0673P)^2^+0.1610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1528
_reflns_number_total             1685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00592a2.cif
_cod_data_source_block           strucutre_II
_cod_database_code               7245150
_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), C6(H6), C4(H4), C5(H5)
;
_shelx_res_checksum              38978
_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 1.986
_oxdiff_exptl_absorpt_empirical_full_min 0.666