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_7245152
_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      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 90.3200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.11400(10)
_cell_length_b                   12.37150(10)
_cell_length_c                   23.8214(2)
_cell_measurement_reflns_used    24921
_cell_measurement_temperature    298
_cell_measurement_theta_max      76.2770
_cell_measurement_theta_min      3.7170
_cell_volume                     1212.40(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_temperature      298
_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 1.000
_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    -12.00  28.00   0.50    1.28    --  -47.64  19.00-180.00   80
  2  \w    -39.00  25.00   0.50    1.28    --  -47.64  38.00 -60.00  128
  3  \w    -62.00  25.00   0.50    1.28    --  -47.64  57.00 150.00  174
  4  \w   -120.00 -35.00   0.50    1.28    --  -47.64 -38.00   0.00  170
  5  \w     34.00  95.00   0.50    1.28    --   47.64-125.00  30.00  122
  6  \w    -75.00 -19.00   0.50    5.13    --  -91.75  61.00 -30.00  112
  7  \w   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00-120.00  168
  8  \w    -49.00 -20.00   0.50    5.13    --  -91.75  45.00 -30.00   58
  9  \w    -49.00 -20.00   0.50    5.13    --  -91.75  45.00   0.00   58
 10  \w   -114.00 -19.00   0.50    5.13    --  -91.75  77.00 -30.00  190
 11  \w    -49.00 -20.00   0.50    5.13    --  -91.75  45.00-180.00   58
 12  \w   -114.00 -19.00   0.50    5.13    --  -91.75  77.00 150.00  190
 13  \w   -166.00 -79.00   0.50    5.13    --  -91.75 -30.00   0.00  174
 14  \w    -49.00 -20.00   0.50    5.13    --  -91.75  45.00-120.00   58
 15  \w     33.00 105.00   0.50    5.13    --  105.80 -95.00 120.00  144
 16  \w     92.00 176.00   0.50    5.13    --  105.80  15.00 120.00  168
 17  \w     33.00  75.00   0.50    5.13    --  105.80 -61.00-180.00   84
 18  \w     33.00  75.00   0.50    5.13    --  105.80 -61.00 -30.00   84
 19  \w     33.00 105.00   0.50    5.13    --  105.80 -95.00 -30.00  144
 20  \w     34.00 112.00   0.50    5.13    --  105.80-125.00 120.00  156
 21  \w     34.00 112.00   0.50    5.13    --  105.80-125.00-180.00  156
 22  \w     33.00  75.00   0.50    5.13    --  105.80 -61.00 150.00   84
 23  \w     33.00  75.00   0.50    5.13    --  105.80 -61.00   0.00   84
 24  \w     92.00 176.00   0.50    5.13    --  105.80  15.00  90.00  168
 25  \w     92.00 176.00   0.50    5.13    --  105.80  15.00-180.00  168
 26  \w     33.00  75.00   0.50    5.13    --  105.80 -61.00-150.00   84
 27  \w     33.00 105.00   0.50    5.13    --  105.80 -95.00  30.00  144
 28  \w   -120.00 -35.00   0.50    1.28    --  -47.64 -38.00 -60.00  170
 29  \w   -120.00 -25.00   0.50    1.28    --  -47.64 -77.00 -60.00  190
 30  \w     25.00 120.00   0.50    1.28    --   47.64  77.00  60.00  190
 31  \w     25.00 120.00   0.50    1.28    --   47.64  77.00-150.00  190
 32  \w     25.00 120.00   0.50    1.28    --   47.64  77.00 150.00  190
 33  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00-150.00  176
 34  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00-180.00  188
 35  \w   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00 -60.00  168
 36  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 150.00  188
 37  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00  30.00  176
 38  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00 120.00  176
 39  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00-120.00  176
 40  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00  60.00  188
 41  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 120.00  188
 42  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00   0.00  188
 43  \w    -49.00 -20.00   0.50    5.13    --  -91.75  45.00  60.00   58
 44  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00 -30.00  176
 45  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 -60.00  188
 46  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00-150.00  188
 47  \w   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00  90.00  168
 48  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00-180.00  176
 49  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00 -90.00  176
 50  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00  30.00  188
 51  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00-120.00  188
 52  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00  90.00  188
 53  \w   -120.00 -35.00   0.50    1.28    --  -47.64 -38.00 150.00  170
 54  \w    -12.00  28.00   0.50    1.28    --  -47.64  19.00  30.00   80
 55  \w   -120.00 -25.00   0.50    1.28    --  -47.64 -77.00 -30.00  190
 56  \w     25.00 120.00   0.50    1.28    --   47.64  77.00   0.00  190
 57  \w     25.00 120.00   0.50    1.28    --   47.64  77.00 120.00  190
 58  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 -90.00  188
 59  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00  90.00  176
 60  \w   -163.00 -83.00   0.50    5.13    --  -91.75 -95.00   0.00  160
 61  \w    -49.00 -20.00   0.50    5.13    --  -91.75  45.00  30.00   58
 62  \w    -49.00 -20.00   0.50    5.13    --  -91.75  45.00 -60.00   58
 63  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00 150.00  176
 64  \w   -163.00 -69.00   0.50    5.13    --  -91.75 -77.00 -30.00  188
 65  \w   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00 150.00  168
 66  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00   0.00  176
 67  \w   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00   0.00  168
 68  \w   -163.00 -79.00   0.50    5.13    --  -91.75 -45.00-150.00  168
 69  \w   -163.00 -75.00   0.50    5.13    --  -91.75 -61.00  60.00  176
 70  \w     33.00  75.00   0.50    5.13    --  105.80 -61.00  60.00   84
 71  \w     33.00  94.00   0.50    5.13    --  105.80 -77.00 -30.00  122
 72  \w     33.00 129.00   0.50    5.13    --  105.80 -77.00 -60.00  192
 73  \w     33.00 129.00   0.50    5.13    --  105.80 -77.00 -90.00  192
 74  \w     33.00 129.00   0.50    5.13    --  105.80 -77.00-120.00  192
 75  \w     33.00 129.00   0.50    5.13    --  105.80 -77.00-150.00  192
 76  \w     33.00 129.00   0.50    5.13    --  105.80 -77.00-180.00  192
 77  \w     83.00 178.00   0.50    5.13    --  105.80  77.00 -60.00  190
;
_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      -0.0640778000
_diffrn_orient_matrix_UB_12      -0.0305131000
_diffrn_orient_matrix_UB_13      0.0616391000
_diffrn_orient_matrix_UB_21      -0.1604611000
_diffrn_orient_matrix_UB_22      -0.1063130000
_diffrn_orient_matrix_UB_23      -0.0193136000
_diffrn_orient_matrix_UB_31      0.3322753000
_diffrn_orient_matrix_UB_32      -0.0572219000
_diffrn_orient_matrix_UB_33      0.0029686000
_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  0.0524
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            52585
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.500
_diffrn_reflns_theta_min         3.711
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.026
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.78a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0260
_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^)+(0.0260P)^2^+0.5741P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0635
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2076
_reflns_number_total             2210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00592a2.cif
_cod_data_source_block           structure_III
_cod_database_code               7245152
_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:
 C5(H5), C3(H3), C6(H6), C2(H2)
;
_shelx_res_checksum              771
_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 2.308
_oxdiff_exptl_absorpt_empirical_full_min 0.645