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#$Date: 2022-06-14 11:59:24 +0300 (Tue, 14 Jun 2022) $
#$Revision: 276019 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105408.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_8105408
loop_
_publ_author_name
'Sun, Hongtao'
'Wu, Hao'
'Zhang, Lili'
_publ_section_title
;
 Crystal structure of
 2-(5-(pyridin-3-yl)-4-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)pyridine,
 C17H12N6
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1161
_journal_page_last               1162
_journal_paper_doi               10.1515/ncrs-2020-0223
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C17 H12 N6'
_chemical_formula_sum            'C17 H12 N6'
_chemical_formula_weight         300.33
_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   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 92.650(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8617(14)
_cell_length_b                   15.845(4)
_cell_length_c                   15.326(4)
_cell_measurement_reflns_used    1804
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.81
_cell_measurement_theta_min      2.66
_cell_volume                     1421.9(6)
_computing_cell_refinement       'Bruker SMART [1]'
_computing_data_collection       'Bruker SMART [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [4]'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8438
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.265
_diffrn_reflns_theta_min         1.850
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0449
_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)+(0.0489P)²+0.1847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2081
_reflns_number_total             3172
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0223_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1422.0(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105408
_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.
;
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.975
_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), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.6869(3) 0.18375(10) 0.64504(11) 0.0402(4) Uani 1 1 d . . . . .
C2 C 0.8608(3) 0.15050(10) 0.58826(12) 0.0411(4) Uani 1 1 d . . . . .
C3 C 1.0435(3) 0.10567(11) 0.62556(13) 0.0486(4) Uani 1 1 d . . . . .
H3 H 1.055098 0.096400 0.685516 0.058 Uiso 1 1 calc R U . . .
C4 C 1.2069(3) 0.07522(12) 0.57262(13) 0.0547(5) Uani 1 1 d . . . . .
H4 H 1.330716 0.044788 0.596178 0.066 Uiso 1 1 calc R U . . .
C5 C 1.1857(3) 0.09008(12) 0.48528(15) 0.0606(5) Uani 1 1 d . . . . .
H5 H 1.296304 0.070839 0.448515 0.073 Uiso 1 1 calc R U . . .
C6 C 0.9993(4) 0.13378(13) 0.45191(14) 0.0618(5) Uani 1 1 d . . . . .
H6 H 0.985343 0.142715 0.391922 0.074 Uiso 1 1 calc R U . . .
C7 C 0.4221(3) 0.25962(10) 0.70225(11) 0.0397(4) Uani 1 1 d . . . . .
C8 C 0.2531(3) 0.32541(11) 0.71940(10) 0.0402(4) Uani 1 1 d . . . . .
C9 C 0.2797(3) 0.40879(11) 0.69625(11) 0.0445(4) Uani 1 1 d . . . . .
H9 H 0.407345 0.426029 0.667090 0.053 Uiso 1 1 calc R U . . .
C10 C 0.1145(3) 0.46604(12) 0.71698(12) 0.0526(5) Uani 1 1 d . . . . .
H10 H 0.129643 0.522686 0.702474 0.063 Uiso 1 1 calc R U . . .
C11 C -0.0728(3) 0.43868(13) 0.75929(13) 0.0563(5) Uani 1 1 d . . . . .
H11 H -0.184716 0.477897 0.771824 0.068 Uiso 1 1 calc R U . . .
C12 C 0.0613(3) 0.30276(12) 0.76390(12) 0.0494(5) Uani 1 1 d . . . . .
H12 H 0.045600 0.246790 0.780894 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5516(3) 0.31017(9) 0.55640(10) 0.0348(4) Uani 1 1 d . . . . .
C14 C 0.3629(3) 0.31396(11) 0.49954(11) 0.0432(4) Uani 1 1 d . . . . .
H14 H 0.234639 0.280970 0.508129 0.052 Uiso 1 1 calc R U . . .
C15 C 0.3705(3) 0.36842(12) 0.42931(12) 0.0516(5) Uani 1 1 d . . . . .
H15 H 0.243724 0.370706 0.390574 0.062 Uiso 1 1 calc R U . . .
C16 C 0.7243(3) 0.41275(12) 0.47062(13) 0.0584(5) Uani 1 1 d . . . . .
H16 H 0.849753 0.446973 0.461287 0.070 Uiso 1 1 calc R U . . .
C17 C 0.7354(3) 0.36066(11) 0.54244(12) 0.0463(4) Uani 1 1 d . . . . .
H17 H 0.864011 0.359794 0.580335 0.056 Uiso 1 1 calc R U . . .
N1 N 0.5533(2) 0.25411(8) 0.63046(8) 0.0368(3) Uani 1 1 d . . . . .
N2 N 0.6390(2) 0.14924(9) 0.71981(10) 0.0491(4) Uani 1 1 d . . . . .
N3 N 0.4711(3) 0.19719(9) 0.75618(10) 0.0490(4) Uani 1 1 d . . . . .
N4 N 0.8348(3) 0.16448(10) 0.50231(11) 0.0580(4) Uani 1 1 d . . . . .
N5 N -0.1031(3) 0.35806(11) 0.78359(11) 0.0622(5) Uani 1 1 d . . . . .
N6 N 0.5470(3) 0.41764(10) 0.41361(10) 0.0586(4) Uani 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 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N1 C1 C2 126.91(15) . .
N2 C1 C2 123.43(15) . .
N2 C1 N1 109.66(15) . .
C3 C2 C1 118.93(16) . .
N4 C2 C1 118.27(15) . .
N4 C2 C3 122.80(17) . .
C2 C3 H3 120.5 . .
C4 C3 C2 118.94(18) . .
C4 C3 H3 120.5 . .
C3 C4 H4 120.4 . .
C5 C4 C3 119.13(18) . .
C5 C4 H4 120.4 . .
C4 C5 H5 120.3 . .
C4 C5 C6 119.3(2) . .
C6 C5 H5 120.3 . .
C5 C6 H6 118.5 . .
N4 C6 C5 123.0(2) . .
N4 C6 H6 118.5 . .
N1 C7 C8 126.52(14) . .
N3 C7 C8 123.48(15) . .
N3 C7 N1 110.00(15) . .
C9 C8 C7 123.24(15) . .
C9 C8 C12 118.55(17) . .
C12 C8 C7 118.17(15) . .
C8 C9 H9 120.5 . .
C10 C9 C8 118.91(16) . .
C10 C9 H9 120.5 . .
C9 C10 H10 120.4 . .
C11 C10 C9 119.26(18) . .
C11 C10 H10 120.4 . .
C10 C11 H11 118.3 . .
N5 C11 C10 123.37(19) . .
N5 C11 H11 118.3 . .
C8 C12 H12 118.5 . .
N5 C12 C8 123.06(17) . .
N5 C12 H12 118.5 . .
C14 C13 N1 120.09(14) . .
C17 C13 C14 119.43(15) . .
C17 C13 N1 120.48(14) . .
C13 C14 H14 121.1 . .
C13 C14 C15 117.79(16) . .
C15 C14 H14 121.1 . .
C14 C15 H15 117.9 . .
N6 C15 C14 124.18(17) . .
N6 C15 H15 117.9 . .
C17 C16 H16 117.7 . .
N6 C16 H16 117.7 . .
N6 C16 C17 124.62(17) . .
C13 C17 C16 117.90(16) . .
C13 C17 H17 121.0 . .
C16 C17 H17 121.0 . .
C1 N1 C13 127.66(14) . .
C7 N1 C1 104.91(13) . .
C7 N1 C13 127.43(13) . .
C1 N2 N3 107.99(13) . .
C7 N3 N2 107.44(14) . .
C2 N4 C6 116.80(17) . .
C11 N5 C12 116.82(16) . .
C15 N6 C16 116.06(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.468(2) .
C1 N1 1.375(2) .
C1 N2 1.312(2) .
C2 C3 1.386(2) .
C2 N4 1.337(2) .
C3 H3 0.9300 .
C3 C4 1.371(3) .
C4 H4 0.9300 .
C4 C5 1.359(3) .
C5 H5 0.9300 .
C5 C6 1.372(3) .
C6 H6 0.9300 .
C6 N4 1.353(3) .
C7 C8 1.470(2) .
C7 N1 1.374(2) .
C7 N3 1.313(2) .
C8 C9 1.379(2) .
C8 C12 1.389(2) .
C9 H9 0.9300 .
C9 C10 1.375(2) .
C10 H10 0.9300 .
C10 C11 1.371(3) .
C11 H11 0.9300 .
C11 N5 1.345(3) .
C12 H12 0.9300 .
C12 N5 1.347(2) .
C13 C14 1.377(2) .
C13 C17 1.367(2) .
C13 N1 1.4411(19) .
C14 H14 0.9300 .
C14 C15 1.382(2) .
C15 H15 0.9300 .
C15 N6 1.327(2) .
C16 H16 0.9300 .
C16 C17 1.375(2) .
C16 N6 1.329(2) .
C17 H17 0.9300 .
N2 N3 1.381(2) .
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
C1 C2 C3 C4 -179.47(15) . . . .
C1 C2 N4 C6 179.32(15) . . . .
C1 N2 N3 C7 -0.03(18) . . . .
C2 C1 N1 C7 -178.96(15) . . . .
C2 C1 N1 C13 0.8(2) . . . .
C2 C1 N2 N3 179.11(14) . . . .
C2 C3 C4 C5 0.2(3) . . . .
C3 C2 N4 C6 -1.1(3) . . . .
C3 C4 C5 C6 -1.2(3) . . . .
C4 C5 C6 N4 1.1(3) . . . .
C5 C6 N4 C2 0.1(3) . . . .
C7 C8 C9 C10 -178.47(15) . . . .
C7 C8 C12 N5 179.49(16) . . . .
C8 C7 N1 C1 178.66(14) . . . .
C8 C7 N1 C13 -1.1(2) . . . .
C8 C7 N3 N2 -178.79(14) . . . .
C8 C9 C10 C11 -0.6(3) . . . .
C8 C12 N5 C11 -1.1(3) . . . .
C9 C8 C12 N5 1.7(3) . . . .
C9 C10 C11 N5 1.3(3) . . . .
C10 C11 N5 C12 -0.5(3) . . . .
C12 C8 C9 C10 -0.8(2) . . . .
C13 C14 C15 N6 -0.5(3) . . . .
C14 C13 C17 C16 -0.9(2) . . . .
C14 C13 N1 C1 112.92(18) . . . .
C14 C13 N1 C7 -67.4(2) . . . .
C14 C15 N6 C16 -0.2(3) . . . .
C17 C13 C14 C15 1.1(2) . . . .
C17 C13 N1 C1 -67.8(2) . . . .
C17 C13 N1 C7 111.82(19) . . . .
C17 C16 N6 C15 0.5(3) . . . .
N1 C1 C2 C3 151.59(16) . . . .
N1 C1 C2 N4 -28.8(2) . . . .
N1 C1 N2 N3 -0.16(18) . . . .
N1 C7 C8 C9 -35.7(2) . . . .
N1 C7 C8 C12 146.62(16) . . . .
N1 C7 N3 N2 0.22(18) . . . .
N1 C13 C14 C15 -179.66(15) . . . .
N1 C13 C17 C16 179.88(16) . . . .
N2 C1 C2 C3 -27.6(2) . . . .
N2 C1 C2 N4 152.02(16) . . . .
N2 C1 N1 C7 0.29(17) . . . .
N2 C1 N1 C13 180.00(14) . . . .
N3 C7 C8 C9 143.10(17) . . . .
N3 C7 C8 C12 -34.5(2) . . . .
N3 C7 N1 C1 -0.31(17) . . . .
N3 C7 N1 C13 179.97(14) . . . .
N4 C2 C3 C4 1.0(3) . . . .
N6 C16 C17 C13 0.1(3) . . . .
