#------------------------------------------------------------------------------
#$Date: 2022-07-23 02:28:40 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245150.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245150
loop_
_publ_author_name
'Wzgarda-Raj, Kinga'
'Książkiewicz, Olga'
'Palusiak, Marcin'
_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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 127.00   0.50    0.12    --  105.67  15.00  30.00   70
  2  ω    100.00 126.00   0.50    0.12    --  105.67  15.00 -30.00   52
  3  ω    144.00 169.00   0.50    0.12    --  105.67  15.00 -30.00   50
  4  ω    148.00 176.00   0.50    0.12    --  105.67  15.00  30.00   56
  5  ω    113.00 139.00   0.50    0.12    --  105.67 115.00  38.00   52
  6  ω     34.00  60.00   0.50    0.12    --  105.67 -61.00 -60.00   52
  7  ω     34.00  59.00   0.50    0.05    --   47.52-115.00 -51.00   50
  8  ω     48.00 108.00   0.50    0.12    --  105.67-115.00 -51.00  120
  9  ω     61.00 102.00   0.50    0.12    --  105.67 -95.00 -30.00   82
 10  ω     94.00 146.00   0.50    0.12    --  105.67-174.00 169.00  104
 11  ω     -3.00  25.00   0.50    0.05    --  -47.52  19.00-150.00   56
 12  ω     -6.00  21.00   0.50    0.05    --  -47.52  19.00-120.00   54
 13  ω     -6.00  23.00   0.50    0.05    --  -47.52  19.00 -90.00   58
 14  ω     -8.00  21.00   0.50    0.05    --  -47.52  19.00 -60.00   58
 15  ω    -10.00  16.00   0.50    0.05    --  -47.52  19.00 -30.00   52
 16  ω    -49.00 -21.00   0.50    0.12    --  -91.75  45.00 -90.00   56
 17  ω    -70.00 -40.00   0.50    0.12    --  -91.75  61.00-120.00   60
 18  ω    -49.00 -20.00   0.50    0.12    --  -91.75  45.00-180.00   58
 19  ω    -48.00 -23.00   0.50    0.12    --  -91.75  45.00-120.00   50
 20  ω    -71.00 -31.00   0.50    0.12    --  -91.75  61.00  30.00   80
 21  ω    -72.00 -19.00   0.50    0.12    --  -91.75  61.00  60.00  106
 22  ω    -48.00 -20.00   0.50    0.12    --  -91.75  45.00  60.00   56
 23  ω   -140.00 -85.00   0.50    0.12    --  -91.75-115.00 -51.00  110
 24  ω    -71.00 -45.00   0.50    0.05    --  -47.52-174.00 169.00   52
 25  ω    -48.00 -17.00   0.50    0.05    --  -47.52 115.00  38.00   62
 26  ω    -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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0673P)²+0.1610P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S12 S -0.02732(6) 0.53881(5) 0.23781(6) 0.0535(2) Uani 1 1 d . . . . .
S2 S 0.64401(5) 0.85056(5) 0.58475(8) 0.0563(2) Uani 1 1 d . . . . .
N11 N 0.1384(2) 0.38308(18) 0.4397(2) 0.0502(5) Uani 1 1 d . . . . .
N13 N 0.1364(2) 0.37702(19) 0.1706(2) 0.0559(5) Uani 1 1 d . . . . .
N1 N 0.38533(19) 0.85845(18) 0.5531(3) 0.0561(5) Uani 1 1 d . . . . .
C12 C 0.08891(19) 0.42610(16) 0.2858(2) 0.0380(4) Uani 1 1 d . . . . .
C2 C 0.4950(2) 0.78768(17) 0.5840(3) 0.0454(5) Uani 1 1 d . . . . .
C3 C 0.4768(3) 0.6639(2) 0.6188(4) 0.0670(7) Uani 1 1 d . . . . .
H3 H 0.548454 0.609732 0.638952 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2649(3) 0.8184(3) 0.5590(4) 0.0746(8) Uani 1 1 d . . . . .
H6 H 0.193411 0.872817 0.538371 0.089 Uiso 1 1 calc R U . . .
C4 C 0.3566(3) 0.6217(3) 0.6238(4) 0.0868(10) Uani 1 1 d . . . . .
H4 H 0.346951 0.539205 0.647075 0.104 Uiso 1 1 calc R U . . .
C5 C 0.2490(3) 0.6998(3) 0.5946(5) 0.0868(10) Uani 1 1 d . . . . .
H5 H 0.166920 0.671237 0.599464 0.104 Uiso 1 1 calc R U . . .
H11A H 0.106(2) 0.412(2) 0.515(3) 0.044(6) Uiso 1 1 d . . . . .
H11B H 0.193(3) 0.325(2) 0.457(3) 0.053(7) Uiso 1 1 d . . . . .
H1 H 0.390(3) 0.933(3) 0.534(3) 0.065(8) Uiso 1 1 d . . . . .
H13A H 0.102(3) 0.397(3) 0.072(3) 0.056(7) Uiso 1 1 d . . . . .
H13B H 0.193(3) 0.318(3) 0.197(3) 0.064(8) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1431
0 2 1 0.1107
1 1 -2 0.1612
1 2 -1 0.1193
0 -1 -1 0.2066
0 1 1 0.0805
0 -5 -4 0.1998
-3 -6 1 0.1265
-3 -4 4 0.1437
3 6 -1 0.1293
-7 -1 1 0.0562
7 1 0 0.0524
1 1 5 0.1196
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 H11A 117.8(15) . . ?
C12 N11 H11B 118.8(17) . . ?
H11A N11 H11B 123(2) . . ?
C12 N13 H13A 118.6(18) . . ?
C12 N13 H13B 120.0(18) . . ?
H13A N13 H13B 121(3) . . ?
C2 N1 C6 124.5(2) . . ?
C2 N1 H1 120(2) . . ?
C6 N1 H1 116(2) . . ?
N11 C12 S12 121.80(14) . . ?
N11 C12 N13 116.74(18) . . ?
N13 C12 S12 121.45(15) . . ?
N1 C2 S2 120.26(15) . . ?
N1 C2 C3 115.2(2) . . ?
C3 C2 S2 124.56(18) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
N1 C6 H6 120.1 . . ?
C5 C6 N1 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S12 C12 1.6893(19) . ?
S2 C2 1.708(2) . ?
N11 C12 1.326(2) . ?
N11 H11A 0.87(2) . ?
N11 H11B 0.84(3) . ?
N13 C12 1.332(2) . ?
N13 H13A 0.82(3) . ?
N13 H13B 0.86(3) . ?
N1 C2 1.343(3) . ?
N1 C6 1.354(3) . ?
N1 H1 0.83(3) . ?
C2 C3 1.402(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.346(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(5) . ?
C5 H5 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N11 H11A S12 0.87(2) 2.52(2) 3.3804(18) 170(2) 3_566 yes
N11 H11B S2 0.84(3) 2.66(3) 3.467(2) 163(2) 3_666 yes
N1 H1 S2 0.83(3) 2.54(3) 3.350(2) 166(3) 3_676 yes
N13 H13A S12 0.82(3) 2.58(3) 3.402(2) 172(2) 3_565 yes
N13 H13B S2 0.86(3) 2.78(3) 3.574(2) 154(2) 3_666 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C2 C3 C4 176.8(2) . . . . ?
N1 C2 C3 C4 -1.3(4) . . . . ?
N1 C6 C5 C4 -0.3(5) . . . . ?
C2 N1 C6 C5 -1.3(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C6 N1 C2 S2 -176.2(2) . . . . ?
C6 N1 C2 C3 2.0(4) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -1.0000 0.0000 -0.1389 0.0149 0.0240
-0.0000 2.0000 1.0000 0.2505 0.0145 -0.2329
1.0000 1.0000 -2.0000 0.2073 0.0492 0.3311
1.0000 2.0000 -1.0000 0.3190 0.0786 0.1222
0.0000 -1.0000 -1.0000 -0.1116 -0.0294 0.2089
-0.0000 1.0000 1.0000 0.1116 0.0294 -0.2089
0.0000 -5.0000 -4.0000 -0.5854 -0.1027 0.8597
-3.0000 -6.0000 1.0000 -0.9022 -0.3244 0.0033
-3.0000 -4.0000 4.0000 -0.7063 -0.2214 -0.5994
3.0000 6.0000 -1.0000 0.9022 0.3244 -0.0033
-7.0000 -1.0000 1.0000 -0.2628 -1.0093 -0.0580
7.0000 1.0000 0.0000 0.2355 1.0536 -0.1269
1.0000 1.0000 5.0000 0.0162 0.3591 -0.9632
