#------------------------------------------------------------------------------
#$Date: 2022-07-23 02:28:40 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/51/7245151.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_7245151
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         '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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -80.00   0.50    0.05    --  -47.45-131.00 175.00   76
  2  ω   -139.00-114.00   0.50    0.15    --  -86.25-131.00 175.00   50
  3  ω   -114.00 -64.00   0.50    0.05    --  -47.45-139.00   0.00  100
  4  ω    -99.00 -26.00   0.50    0.05    --  -47.45 -77.00-120.00  146
  5  ω     -5.00  27.00   0.50    0.05    --  -47.45  19.00   0.00   64
  6  ω    -48.00 -14.00   0.50    0.15    --  -86.25  45.00   0.00   68
  7  ω    -46.00 -21.00   0.50    0.15    --  -86.25  45.00  30.00   50
  8  ω    -75.00 -50.00   0.50    0.05    --  -47.45 139.00  61.00   50
  9  ω    -89.00 -64.00   0.50    0.15    --  -86.25 139.00  61.00   50
 10  ω    -78.00 -50.00   0.50    0.05    --  -47.45 131.00-113.00   56
 11  ω    -77.00 -51.00   0.50    0.15    --  -86.25 131.00-113.00   52
 12  ω    -48.00 -15.00   0.50    0.15    --  -86.25  45.00-180.00   66
 13  ω    -49.00 -18.00   0.50    0.15    --  -86.25  45.00-150.00   62
 14  ω   -112.00 -73.00   0.50    0.15    --  -86.25 -15.00  30.00   78
 15  ω   -135.00-110.00   0.50    0.15    --  -86.25-139.00   0.00   50
 16  ω   -160.00-115.00   0.50    0.15    --  -86.25 -15.00  30.00   90
 17  ω    -25.00   1.00   0.50    0.05    --   47.45 -19.00-180.00   52
 18  ω    -14.00  11.00   0.50    0.05    --   47.45 -19.00 -90.00   50
 19  ω     49.00  75.00   0.50    0.15    --  105.86 -61.00 -30.00   52
 20  ω     78.00 105.00   0.50    0.15    --  105.86 -95.00   0.00   54
 21  ω     77.00 120.00   0.50    0.15    --  105.86-139.00   0.00   86
 22  ω     67.00  98.00   0.50    0.05    --   47.45-139.00   0.00   62
 23  ω     40.00  74.00   0.50    0.15    --  105.86 -61.00  60.00   68
 24  ω     34.00  63.00   0.50    0.15    --  105.86 -61.00  30.00   58
 25  ω     35.00  78.00   0.50    0.15    --  105.86-125.00  30.00   86
 26  ω     41.00  75.00   0.50    0.15    --  105.86 -61.00 150.00   68
 27  ω     69.00  94.00   0.50    0.15    --  105.86-131.00 175.00   50
 28  ω     67.00  93.00   0.50    0.05    --   47.45-131.00 175.00   52
 29  ω     93.00 176.00   0.50    0.15    --  105.86  45.00 -60.00  166
 30  ω    106.00 132.00   0.50    0.15    --  105.86 139.00  61.00   52
 31  ω    126.00 175.00   0.50    0.15    --  105.86 131.00-113.00   98
 32  ω    153.00 178.00   0.50    0.15    --  105.86 125.00-180.00   50
 33  ω    119.00 145.00   0.50    0.15    --  105.86 125.00-180.00   52
 34  ω     93.00 121.00   0.50    0.15    --  105.86 131.00-113.00   56
 35  ω    117.00 175.00   0.50    0.15    --  105.86  45.00-180.00  116
 36  ω     96.00 168.00   0.50    0.15    --  105.86  15.00 -90.00  144
 37  ω     72.00 102.00   0.50    0.15    --  105.86-125.00-150.00   60
 38  ω     49.00  74.00   0.50    0.15    --  105.86 -61.00-150.00   50
 39  ω     43.00  69.00   0.50    0.15    --  105.86 -61.00-120.00   52
 40  ω     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       'ω 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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0466P)²+0.0050P] where P=(Fo²+2Fc²)/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 > 2σ(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'
_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), C5(H5), C4(H4), C6(H6)
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
S16 S 0.95075(12) 0.90900(5) 0.25164(4) 0.04172(17) Uani 1 1 d . . . . .
S12 S 0.19238(13) 0.84319(5) -0.08055(4) 0.04467(18) Uani 1 1 d . . . . .
S14 S 0.25861(13) 0.48141(4) 0.13528(4) 0.04441(18) Uani 1 1 d . . . . .
S2 S 0.84356(14) 0.58823(5) 0.37484(4) 0.04635(18) Uani 1 1 d . . . . .
N13 N 0.2562(4) 0.67497(14) 0.03872(12) 0.0348(4) Uani 1 1 d . . . . .
N15 N 0.5872(4) 0.70063(14) 0.18324(12) 0.0340(4) Uani 1 1 d . . . . .
N11 N 0.5647(4) 0.85758(15) 0.08704(12) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.7576(5) 0.64575(17) 0.56843(13) 0.0442(4) Uani 1 1 d . . . . .
C2 C 0.7082(5) 0.67781(18) 0.47653(15) 0.0363(4) Uani 1 1 d . . . . .
C16 C 0.6915(4) 0.81968(17) 0.17236(14) 0.0317(4) Uani 1 1 d . . . . .
C12 C 0.3451(4) 0.79108(17) 0.01880(14) 0.0320(4) Uani 1 1 d . . . . .
C14 C 0.3719(4) 0.62449(16) 0.11881(14) 0.0319(4) Uani 1 1 d . . . . .
C3 C 0.5430(5) 0.7870(2) 0.47437(17) 0.0470(5) Uani 1 1 d . . . . .
H3 H 0.498500 0.813858 0.413415 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5113(6) 0.8161(2) 0.65271(18) 0.0538(6) Uani 1 1 d . . . . .
H5 H 0.449460 0.862438 0.711495 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4480(6) 0.8533(2) 0.55999(19) 0.0531(6) Uani 1 1 d . . . . .
H4 H 0.338845 0.924924 0.556756 0.064 Uiso 1 1 calc R U . . .
C6 C 0.6652(7) 0.7106(2) 0.65441(18) 0.0558(6) Uani 1 1 d . . . . .
H6 H 0.707819 0.682479 0.714959 0.067 Uiso 1 1 calc R U . . .
H15 H 0.660(5) 0.676(2) 0.237(2) 0.044(6) Uiso 1 1 d . . . . .
H1 H 0.860(6) 0.580(3) 0.571(2) 0.053(7) Uiso 1 1 d . . . . .
H13 H 0.124(6) 0.633(2) -0.0047(19) 0.044(6) Uiso 1 1 d . . . . .
H11 H 0.621(6) 0.929(3) 0.0834(19) 0.045(6) 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
1 0 0 0.2434
-1 0 0 0.2689
0 2 1 0.0373
0 -2 -1 0.0074
0 -1 2 0.0490
0 1 -2 0.0010
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 N13 C14 125.39(17) . . ?
C12 N13 H13 113.9(17) . . ?
C14 N13 H13 120.7(17) . . ?
C16 N15 H15 115.2(17) . . ?
C14 N15 C16 124.97(16) . . ?
C14 N15 H15 119.7(17) . . ?
C16 N11 H11 112.7(18) . . ?
C12 N11 C16 126.12(17) . . ?
C12 N11 H11 120.9(18) . . ?
C2 N1 H1 116.1(18) . . ?
C6 N1 C2 124.92(19) . . ?
C6 N1 H1 118.9(18) . . ?
N1 C2 S2 119.75(15) . . ?
N1 C2 C3 115.02(19) . . ?
C3 C2 S2 125.23(15) . . ?
N15 C16 S16 123.68(14) . . ?
N15 C16 N11 114.06(17) . . ?
N11 C16 S16 122.24(14) . . ?
N13 C12 S12 121.67(15) . . ?
N11 C12 S12 124.04(14) . . ?
N11 C12 N13 114.29(16) . . ?
N13 C14 S14 122.15(15) . . ?
N15 C14 S14 122.74(14) . . ?
N15 C14 N13 115.11(16) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.91(19) . . ?
C4 C3 H3 119.5 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C6 C5 C4 117.8(2) . . ?
C3 C4 C5 121.1(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N1 C6 H6 119.9 . . ?
C5 C6 N1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
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
S16 C16 1.6382(19) . ?
S12 C12 1.6498(19) . ?
S14 C14 1.6493(18) . ?
S2 C2 1.700(2) . ?
N13 C12 1.365(2) . ?
N13 C14 1.367(2) . ?
N13 H13 0.84(3) . ?
N15 C16 1.372(2) . ?
N15 C14 1.361(2) . ?
N15 H15 0.86(3) . ?
N11 C16 1.375(2) . ?
N11 C12 1.354(3) . ?
N11 H11 0.81(3) . ?
N1 C2 1.351(3) . ?
N1 C6 1.350(3) . ?
N1 H1 0.86(3) . ?
C2 C3 1.410(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.394(4) . ?
C5 C6 1.349(4) . ?
C4 H4 0.9300 . ?
C6 H6 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
C6 H6 S14 0.93 2.90 3.794(2) 160.8 2_666 yes
N15 H15 S2 0.86(3) 2.34(3) 3.1937(17) 174(2) . yes
N1 H1 S2 0.86(3) 2.45(3) 3.2867(19) 165(2) 2_766 yes
N13 H13 S14 0.84(3) 2.45(3) 3.2862(18) 178(2) 2_565 yes
N11 H11 S12 0.81(3) 2.56(3) 3.3608(17) 177(2) 2_675 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 -179.08(19) . . . . ?
N1 C2 C3 C4 0.8(3) . . . . ?
C2 N1 C6 C5 0.0(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C16 N15 C14 S14 179.31(15) . . . . ?
C16 N15 C14 N13 -0.4(3) . . . . ?
C16 N11 C12 S12 177.93(15) . . . . ?
C16 N11 C12 N13 -1.9(3) . . . . ?
C12 N13 C14 S14 -178.14(15) . . . . ?
C12 N13 C14 N15 1.6(3) . . . . ?
C12 N11 C16 S16 -178.54(14) . . . . ?
C12 N11 C16 N15 2.9(3) . . . . ?
C14 N13 C12 S12 179.64(15) . . . . ?
C14 N13 C12 N11 -0.5(3) . . . . ?
C14 N15 C16 S16 179.85(14) . . . . ?
C14 N15 C16 N11 -1.6(3) . . . . ?
C4 C5 C6 N1 1.1(4) . . . . ?
C6 N1 C2 S2 178.99(18) . . . . ?
C6 N1 C2 C3 -0.9(3) . . . . ?
C6 C5 C4 C3 -1.1(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
1.0000 -0.0000 -0.0000 0.0544 -0.0614 0.3594
-1.0000 0.0000 0.0000 -0.0544 0.0614 -0.3594
-0.0000 2.0000 1.0000 0.2837 -0.1585 -0.0416
0.0000 -2.0000 -1.0000 -0.2837 0.1585 0.0416
-0.0000 -1.0000 2.0000 0.1069 0.2262 0.0284
0.0000 1.0000 -2.0000 -0.1069 -0.2262 -0.0284
