#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/01/2230153.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230153
loop_
_publ_author_name
'Wu, Jing-Min'
'Guo, Wei'
'Li, Cheng-Peng'
_publ_section_title
;
 3,4-Bis(2-pyridyl)-5-(3-pyridyl)-4H-1,2,4-triazole
;
_journal_coeditor_code           SU2269
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1189
_journal_paper_doi               10.1107/S1600536811014140
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H12 N6'
_chemical_formula_moiety         'C17 H12 N6'
_chemical_formula_sum            'C17 H12 N6'
_chemical_formula_weight         300.33
_chemical_name_systematic
;
3,4-Bis(2-pyridyl)-5-(3-pyridyl)-4H-1,2,4-triazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.023(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7621(9)
_cell_length_b                   15.250(3)
_cell_length_c                   16.640(3)
_cell_measurement_reflns_used    1374
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.01
_cell_measurement_theta_min      2.53
_cell_volume                     1412.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6865
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_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          0.20
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.163
_refine_ls_extinction_coef       0.0124(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.6358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1289
_reflns_number_gt                1407
_reflns_number_total             2496
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2269.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230153
_cod_database_fobs_code          2230153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.8676(5) 0.8964(2) 0.69324(16) 0.0620(8) Uani d . 1 . .
N N2 0.6880(5) 0.68510(18) 0.75149(15) 0.0531(7) Uani d . 1 . .
N N3 0.4816(5) 0.63917(17) 0.71292(16) 0.0525(7) Uani d . 1 . .
N N4 0.5220(4) 0.74876(16) 0.63138(13) 0.0402(6) Uani d . 1 . .
N N5 -0.2135(5) 0.57144(18) 0.56487(19) 0.0646(8) Uani d . 1 . .
N N6 0.6492(4) 0.79687(17) 0.51665(15) 0.0527(7) Uani d . 1 . .
C C1 -0.0072(6) 0.6053(2) 0.6135(2) 0.0524(8) Uani d . 1 . .
H H1 0.0195 0.6012 0.6710 0.063 Uiso calc R 1 . .
C C2 -0.2431(6) 0.5784(2) 0.4816(2) 0.0572(9) Uani d . 1 . .
H H2 -0.3822 0.5557 0.4463 0.069 Uiso calc R 1 . .
C C3 -0.0776(6) 0.6174(2) 0.4471(2) 0.0585(9) Uani d . 1 . .
H H3 -0.1055 0.6206 0.3896 0.070 Uiso calc R 1 . .
C C4 0.1285(5) 0.6514(2) 0.49739(19) 0.0479(8) Uani d . 1 . .
H H4 0.2420 0.6781 0.4746 0.057 Uiso calc R 1 . .
C C5 0.1657(5) 0.64570(19) 0.58214(19) 0.0436(8) Uani d . 1 . .
C C6 0.3855(5) 0.6773(2) 0.64142(17) 0.0418(7) Uani d . 1 . .
C C7 0.7095(5) 0.7501(2) 0.70183(18) 0.0438(8) Uani d . 1 . .
C C8 0.9078(5) 0.8133(2) 0.72220(17) 0.0449(8) Uani d . 1 . .
C C9 1.0537(7) 0.9537(2) 0.7146(2) 0.0653(10) Uani d . 1 . .
H H9 1.0303 1.0110 0.6951 0.078 Uiso calc R 1 . .
C C10 1.2745(6) 0.9304(3) 0.7638(2) 0.0680(10) Uani d . 1 . .
H H10 1.3979 0.9715 0.7771 0.082 Uiso calc R 1 . .
C C11 1.3130(6) 0.8464(3) 0.7933(2) 0.0639(10) Uani d . 1 . .
H H11 1.4620 0.8297 0.8268 0.077 Uiso calc R 1 . .
C C12 1.1283(5) 0.7875(2) 0.77272(19) 0.0547(9) Uani d . 1 . .
H H12 1.1503 0.7303 0.7925 0.066 Uiso calc R 1 . .
C C13 0.4854(5) 0.80537(19) 0.55974(17) 0.0395(7) Uani d . 1 . .
C C14 0.2895(6) 0.8593(2) 0.5398(2) 0.0525(9) Uani d . 1 . .
H H14 0.1811 0.8621 0.5726 0.063 Uiso calc R 1 . .
C C15 0.2599(7) 0.9094(2) 0.4689(2) 0.0685(11) Uani d . 1 . .
H H15 0.1300 0.9475 0.4529 0.082 Uiso calc R 1 . .
C C16 0.4233(7) 0.9027(2) 0.4218(2) 0.0689(11) Uani d . 1 . .
H H16 0.4053 0.9358 0.3737 0.083 Uiso calc R 1 . .
C C17 0.6135(6) 0.8462(2) 0.4475(2) 0.0625(10) Uani d . 1 . .
H H17 0.7234 0.8417 0.4154 0.075 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 N1 C9 . . 117.3(3) ?
C7 N2 N3 . . 107.4(2) ?
C6 N3 N2 . . 107.8(2) ?
C7 N4 C6 . . 104.8(2) ?
C7 N4 C13 . . 127.7(2) ?
C6 N4 C13 . . 127.4(2) ?
C2 N5 C1 . . 116.1(3) ?
C13 N6 C17 . . 115.7(3) ?
N5 C1 C5 . . 123.3(3) ?
N5 C1 H1 . . 118.3 ?
C5 C1 H1 . . 118.3 ?
N5 C2 C3 . . 123.1(3) ?
N5 C2 H2 . . 118.5 ?
C3 C2 H2 . . 118.5 ?
C4 C3 C2 . . 119.8(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 118.9(3) ?
C3 C4 H4 . . 120.5 ?
C5 C4 H4 . . 120.5 ?
C4 C5 C1 . . 118.7(3) ?
C4 C5 C6 . . 123.1(3) ?
C1 C5 C6 . . 118.2(3) ?
N3 C6 N4 . . 109.9(3) ?
N3 C6 C5 . . 123.5(3) ?
N4 C6 C5 . . 126.6(3) ?
N2 C7 N4 . . 110.1(3) ?
N2 C7 C8 . . 123.0(3) ?
N4 C7 C8 . . 126.9(3) ?
N1 C8 C12 . . 121.8(3) ?
N1 C8 C7 . . 118.8(3) ?
C12 C8 C7 . . 119.3(3) ?
N1 C9 C10 . . 122.6(3) ?
N1 C9 H9 . . 118.7 ?
C10 C9 H9 . . 118.7 ?
C9 C10 C11 . . 119.7(3) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
C12 C11 C10 . . 118.8(3) ?
C12 C11 H11 . . 120.6 ?
C10 C11 H11 . . 120.6 ?
C11 C12 C8 . . 119.8(3) ?
C11 C12 H12 . . 120.1 ?
C8 C12 H12 . . 120.1 ?
N6 C13 C14 . . 125.8(3) ?
N6 C13 N4 . . 114.5(2) ?
C14 C13 N4 . . 119.7(3) ?
C13 C14 C15 . . 116.9(3) ?
C13 C14 H14 . . 121.6 ?
C15 C14 H14 . . 121.6 ?
C16 C15 C14 . . 119.7(3) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C17 C16 C15 . . 118.6(3) ?
C17 C16 H16 . . 120.7 ?
C15 C16 H16 . . 120.7 ?
N6 C17 C16 . . 123.4(3) ?
N6 C17 H17 . . 118.3 ?
C16 C17 H17 . . 118.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C8 . 1.354(4) ?
N1 C9 . 1.357(4) ?
N2 C7 . 1.316(4) ?
N2 N3 . 1.386(3) ?
N3 C6 . 1.311(3) ?
N4 C7 . 1.373(3) ?
N4 C6 . 1.379(4) ?
N4 C13 . 1.442(3) ?
N5 C2 . 1.355(4) ?
N5 C1 . 1.355(4) ?
N6 C13 . 1.331(3) ?
N6 C17 . 1.345(4) ?
C1 C5 . 1.384(4) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.370(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.366(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.470(4) ?
C7 C8 . 1.467(4) ?
C8 C12 . 1.386(4) ?
C9 C10 . 1.369(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.371(5) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.366(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.367(4) ?
C14 C15 . 1.378(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.376(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.373(5) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C3 H3 Cg2 4_464 0.93 2.94 3.765(4) 149
C4 H4 Cg4 1_555 0.93 2.92 3.616(3) 133
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N2 N3 C6 . . . . 0.2(3) ?
C2 N5 C1 C5 . . . . 0.5(5) ?
C1 N5 C2 C3 . . . . -0.3(5) ?
N5 C2 C3 C4 . . . . 0.0(5) ?
C2 C3 C4 C5 . . . . 0.1(5) ?
C3 C4 C5 C1 . . . . 0.2(4) ?
C3 C4 C5 C6 . . . . 177.6(3) ?
N5 C1 C5 C4 . . . . -0.5(5) ?
N5 C1 C5 C6 . . . . -178.0(3) ?
N2 N3 C6 N4 . . . . -0.7(3) ?
N2 N3 C6 C5 . . . . 178.8(3) ?
C7 N4 C6 N3 . . . . 0.8(3) ?
C13 N4 C6 N3 . . . . 176.5(3) ?
C7 N4 C6 C5 . . . . -178.6(3) ?
C13 N4 C6 C5 . . . . -3.0(4) ?
C4 C5 C6 N3 . . . . -145.5(3) ?
C1 C5 C6 N3 . . . . 31.9(4) ?
C4 C5 C6 N4 . . . . 33.9(5) ?
C1 C5 C6 N4 . . . . -148.7(3) ?
N3 N2 C7 N4 . . . . 0.3(3) ?
N3 N2 C7 C8 . . . . 179.8(3) ?
C6 N4 C7 N2 . . . . -0.7(3) ?
C13 N4 C7 N2 . . . . -176.3(3) ?
C6 N4 C7 C8 . . . . 179.8(3) ?
C13 N4 C7 C8 . . . . 4.2(5) ?
C9 N1 C8 C12 . . . . 1.0(4) ?
C9 N1 C8 C7 . . . . 178.7(3) ?
N2 C7 C8 N1 . . . . -149.0(3) ?
N4 C7 C8 N1 . . . . 30.4(4) ?
N2 C7 C8 C12 . . . . 28.8(4) ?
N4 C7 C8 C12 . . . . -151.7(3) ?
C8 N1 C9 C10 . . . . -0.4(5) ?
N1 C9 C10 C11 . . . . -0.1(5) ?
C9 C10 C11 C12 . . . . 0.0(5) ?
C10 C11 C12 C8 . . . . 0.5(5) ?
N1 C8 C12 C11 . . . . -1.1(5) ?
C7 C8 C12 C11 . . . . -178.8(3) ?
C17 N6 C13 C14 . . . . -0.3(4) ?
C17 N6 C13 N4 . . . . 177.2(3) ?
C7 N4 C13 N6 . . . . 65.1(4) ?
C6 N4 C13 N6 . . . . -109.6(3) ?
C7 N4 C13 C14 . . . . -117.1(3) ?
C6 N4 C13 C14 . . . . 68.2(4) ?
N6 C13 C14 C15 . . . . -0.2(5) ?
N4 C13 C14 C15 . . . . -177.6(3) ?
C13 C14 C15 C16 . . . . 0.5(5) ?
C14 C15 C16 C17 . . . . -0.4(5) ?
C13 N6 C17 C16 . . . . 0.5(5) ?
C15 C16 C17 N6 . . . . -0.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656670
