#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/78/2017882.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_2017882
loop_
_publ_author_name
'Danielraj, Paulraj'
'Varghese, Babu'
'Sankararaman, S.'
_publ_section_title
;
 2,6-Bis(1-benzyl-1H-1,2,3-triazol-4-yl)pyridine and its
 octahedral copper complex
;
_journal_coeditor_code           FG3196
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m366
_journal_page_last               m370
_journal_paper_doi               10.1107/S010827011004223X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C23 H19 N7'
_chemical_formula_moiety         'C23 H19 N7'
_chemical_formula_sum            'C23 H19 N7'
_chemical_formula_weight         393.45
_chemical_name_systematic
;
2,6-bis(1-benzyl-1H-1,2,3-triazol-4-yl)pyridine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                103.53(3)
_cell_angle_beta                 99.31(3)
_cell_angle_gamma                104.61(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8800(12)
_cell_length_b                   11.460(2)
_cell_length_c                   16.140(3)
_cell_measurement_reflns_used    7794
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.94
_cell_measurement_theta_min      2.8
_cell_volume                     994.6(4)
_computing_cell_refinement
;
APEX2 (Bruker, 2004) and SAINT (Bruker, 2004)
;
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction
;
SAINT (Bruker, 2004) and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP3 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker Kappa APEX2 CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10767
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.33
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.249
_refine_ls_extinction_coef       0.007(2)
_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   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0543
_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)+(0.0791P)²+0.3737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1849
_reflns_number_gt                1811
_reflns_number_total             3417
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3196.cif
_cod_data_source_block           I
_cod_original_cell_volume        994.6(3)
_cod_database_code               2017882
_cod_database_fobs_code          2017882
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.3432(7) 1.0200(3) 0.3308(2) 0.0693(10) Uani d . 1 . .
H H1 0.3505 1.0847 0.3047 0.083 Uiso calc R 1 . .
C C2 0.1824(8) 0.9972(4) 0.3818(3) 0.0791(11) Uani d . 1 . .
H H2 0.0777 1.0455 0.3895 0.095 Uiso calc R 1 . .
C C3 0.1752(6) 0.9035(3) 0.4215(2) 0.0681(10) Uani d . 1 . .
H H3 0.0650 0.8889 0.4560 0.082 Uiso calc R 1 . .
C C4 0.3277(5) 0.8307(3) 0.41135(18) 0.0497(8) Uani d . 1 . .
C C5 0.4858(6) 0.8533(3) 0.3587(2) 0.0627(9) Uani d . 1 . .
H H5 0.5895 0.8046 0.3501 0.075 Uiso calc R 1 . .
C C6 0.4924(7) 0.9473(3) 0.3184(2) 0.0701(10) Uani d . 1 . .
H H6 0.5995 0.9612 0.2827 0.084 Uiso calc R 1 . .
C C7 0.3192(6) 0.7354(3) 0.4612(2) 0.0632(9) Uani d . 1 . .
H H7A 0.3800 0.7796 0.5231 0.076 Uiso calc R 1 . .
H H7B 0.1517 0.6870 0.4525 0.076 Uiso calc R 1 . .
C C9 0.5882(5) 0.5004(3) 0.37662(19) 0.0505(8) Uani d . 1 . .
C C8 0.4044(6) 0.5510(3) 0.3657(2) 0.0558(9) Uani d . 1 . .
H H8 0.2707 0.5234 0.3186 0.067 Uiso calc R 1 . .
C C10 0.6303(5) 0.3921(3) 0.3188(2) 0.0507(8) Uani d U 1 . .
C C11 0.8216(6) 0.3492(3) 0.3448(2) 0.0607(9) Uani d . 1 . .
H H11 0.9241 0.3870 0.4003 0.073 Uiso calc R 1 . .
C C12 0.8590(6) 0.2495(3) 0.2875(2) 0.0655(10) Uani d . 1 . .
H H12 0.9855 0.2187 0.3046 0.079 Uiso calc R 1 . .
C C13 0.7100(6) 0.1964(3) 0.2057(2) 0.0610(9) Uani d . 1 . .
H H13 0.7350 0.1293 0.1669 0.073 Uiso calc R 1 . .
C C14 0.5212(6) 0.2423(3) 0.1804(2) 0.0511(8) Uani d . 1 . .
C C15 0.3671(6) 0.1939(3) 0.0921(2) 0.0493(8) Uani d . 1 . .
C C16 0.1439(6) 0.1987(3) 0.0590(2) 0.0565(9) Uani d . 1 . .
H H16 0.0462 0.2347 0.0899 0.068 Uiso calc R 1 . .
C C17 -0.1106(6) 0.1312(3) -0.0951(2) 0.0630(9) Uani d . 1 . .
H H17A -0.2584 0.1132 -0.0746 0.076 Uiso calc R 1 . .
H H17B -0.1267 0.0623 -0.1460 0.076 Uiso calc R 1 . .
C C18 -0.0732(6) 0.2524(3) -0.1202(2) 0.0573(9) Uani d . 1 . .
C C19 0.0978(7) 0.2868(4) -0.1645(2) 0.0797(11) Uani d . 1 . .
H H19 0.1874 0.2331 -0.1817 0.096 Uiso calc R 1 . .
C C20 0.1412(8) 0.3988(4) -0.1843(3) 0.0938(13) Uani d . 1 . .
H H20 0.2588 0.4203 -0.2149 0.113 Uiso calc R 1 . .
C C21 0.0135(8) 0.4784(4) -0.1596(3) 0.0831(12) Uani d . 1 . .
H H21 0.0464 0.5555 -0.1719 0.100 Uiso calc R 1 . .
C C22 -0.1617(8) 0.4461(4) -0.1171(3) 0.0892(13) Uani d . 1 . .
H H22 -0.2534 0.4995 -0.1017 0.107 Uiso calc R 1 . .
C C23 -0.2041(7) 0.3319(3) -0.0963(2) 0.0778(11) Uani d . 1 . .
H H23 -0.3224 0.3101 -0.0660 0.093 Uiso calc R 1 . .
N N1 0.4558(5) 0.6490(2) 0.43693(17) 0.0546(7) Uani d . 1 . .
N N2 0.6644(5) 0.6605(3) 0.49136(18) 0.0652(8) Uani d . 1 . .
N N3 0.7433(5) 0.5690(3) 0.45419(18) 0.0640(8) Uani d . 1 . .
N N4 0.4445(6) 0.1332(3) 0.0247(2) 0.0686(8) Uani d . 1 . .
N N5 0.2767(6) 0.1020(3) -0.04726(19) 0.0706(9) Uani d . 1 . .
N N6 0.0928(5) 0.1417(2) -0.02644(17) 0.0555(7) Uani d . 1 . .
N N7 0.4806(5) 0.3394(2) 0.23758(17) 0.0573(7) Uani d U 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
C6 C1 C2 . . 119.5(3) ?
C6 C1 H1 . . 120.2 ?
C2 C1 H1 . . 120.2 ?
C1 C2 C3 . . 120.1(4) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C2 C3 C4 . . 121.3(3) ?
C2 C3 H3 . . 119.4 ?
C4 C3 H3 . . 119.4 ?
C3 C4 C5 . . 117.9(3) ?
C3 C4 C7 . . 118.1(3) ?
C5 C4 C7 . . 124.0(3) ?
C4 C5 C6 . . 120.8(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 120.3(3) ?
C1 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
N1 C7 C4 . . 114.9(3) ?
N1 C7 H7A . . 108.5 ?
C4 C7 H7A . . 108.5 ?
N1 C7 H7B . . 108.5 ?
C4 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
N3 C9 C8 . . 107.8(3) ?
N3 C9 C10 . . 122.2(3) ?
C8 C9 C10 . . 129.9(3) ?
N1 C8 C9 . . 105.5(3) ?
N1 C8 H8 . . 127.3 ?
C9 C8 H8 . . 127.3 ?
N7 C10 C11 . . 121.3(3) ?
N7 C10 C9 . . 117.5(3) ?
C11 C10 C9 . . 121.1(3) ?
C10 C11 C12 . . 119.3(3) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
C13 C12 C11 . . 119.8(3) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C12 C13 C14 . . 120.0(3) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
N7 C14 C13 . . 120.4(3) ?
N7 C14 C15 . . 117.6(3) ?
C13 C14 C15 . . 121.9(3) ?
C16 C15 N4 . . 107.6(3) ?
C16 C15 C14 . . 132.0(3) ?
N4 C15 C14 . . 120.4(3) ?
N6 C16 C15 . . 106.2(3) ?
N6 C16 H16 . . 126.9 ?
C15 C16 H16 . . 126.9 ?
N6 C17 C18 . . 110.1(3) ?
N6 C17 H17A . . 109.6 ?
C18 C17 H17A . . 109.6 ?
N6 C17 H17B . . 109.6 ?
C18 C17 H17B . . 109.6 ?
H17A C17 H17B . . 108.2 ?
C19 C18 C23 . . 118.4(3) ?
C19 C18 C17 . . 120.7(3) ?
C23 C18 C17 . . 120.9(3) ?
C18 C19 C20 . . 121.4(4) ?
C18 C19 H19 . . 119.3 ?
C20 C19 H19 . . 119.3 ?
C21 C20 C19 . . 120.2(4) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C22 C21 C20 . . 120.1(4) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C21 C22 C23 . . 119.5(4) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
C18 C23 C22 . . 120.4(4) ?
C18 C23 H23 . . 119.8 ?
C22 C23 H23 . . 119.8 ?
C8 N1 N2 . . 110.7(3) ?
C8 N1 C7 . . 129.5(3) ?
N2 N1 C7 . . 119.8(3) ?
N3 N2 N1 . . 106.5(2) ?
N2 N3 C9 . . 109.5(3) ?
N5 N4 C15 . . 108.5(3) ?
N4 N5 N6 . . 107.7(3) ?
C16 N6 N5 . . 110.0(3) ?
C16 N6 C17 . . 129.6(3) ?
N5 N6 C17 . . 120.0(3) ?
C10 N7 C14 . . 119.2(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
C1 C6 . 1.361(5) ?
C1 C2 . 1.366(5) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.369(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(4) ?
C4 C7 . 1.495(4) ?
C5 C6 . 1.377(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.450(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C9 N3 . 1.351(4) ?
C9 C8 . 1.356(4) ?
C9 C10 . 1.470(4) ?
C8 N1 . 1.336(4) ?
C8 H8 . 0.9300 ?
C10 N7 . 1.359(4) ?
C10 C11 . 1.380(4) ?
C11 C12 . 1.381(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.364(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.388(4) ?
C13 H13 . 0.9300 ?
C14 N7 . 1.369(4) ?
C14 C15 . 1.455(4) ?
C15 C16 . 1.354(4) ?
C15 N4 . 1.356(4) ?
C16 N6 . 1.329(4) ?
C16 H16 . 0.9300 ?
C17 N6 . 1.452(4) ?
C17 C18 . 1.510(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.358(5) ?
C18 C23 . 1.363(5) ?
C19 C20 . 1.367(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.352(6) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.351(6) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.399(5) ?
C22 H22 . 0.9300 ?
C23 H23 . 0.9300 ?
N1 N2 . 1.345(3) ?
N2 N3 . 1.310(4) ?
N4 N5 . 1.307(4) ?
N5 N6 . 1.335(4) ?
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
C7 H7B N3 1_455 0.97 2.45 3.411(5) 171
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
C6 C1 C2 C3 . . . . 1.3(6) ?
C1 C2 C3 C4 . . . . 0.0(6) ?
C2 C3 C4 C5 . . . . -1.1(5) ?
C2 C3 C4 C7 . . . . 176.4(3) ?
C3 C4 C5 C6 . . . . 0.8(5) ?
C7 C4 C5 C6 . . . . -176.5(3) ?
C2 C1 C6 C5 . . . . -1.5(6) ?
C4 C5 C6 C1 . . . . 0.4(5) ?
C3 C4 C7 N1 . . . . 170.7(3) ?
C5 C4 C7 N1 . . . . -12.0(5) ?
N3 C9 C8 N1 . . . . 0.3(3) ?
C10 C9 C8 N1 . . . . -179.1(3) ?
N3 C9 C10 N7 . . . . -171.8(3) ?
C8 C9 C10 N7 . . . . 7.6(5) ?
N3 C9 C10 C11 . . . . 5.4(4) ?
C8 C9 C10 C11 . . . . -175.2(3) ?
N7 C10 C11 C12 . . . . -1.0(4) ?
C9 C10 C11 C12 . . . . -178.1(3) ?
C10 C11 C12 C13 . . . . 1.2(5) ?
C11 C12 C13 C14 . . . . -0.1(5) ?
C12 C13 C14 N7 . . . . -1.1(4) ?
C12 C13 C14 C15 . . . . 176.1(3) ?
N7 C14 C15 C16 . . . . -22.2(5) ?
C13 C14 C15 C16 . . . . 160.5(3) ?
N7 C14 C15 N4 . . . . 156.2(3) ?
C13 C14 C15 N4 . . . . -21.1(4) ?
N4 C15 C16 N6 . . . . -0.1(3) ?
C14 C15 C16 N6 . . . . 178.5(3) ?
N6 C17 C18 C19 . . . . 70.5(4) ?
N6 C17 C18 C23 . . . . -107.2(4) ?
C23 C18 C19 C20 . . . . 0.6(6) ?
C17 C18 C19 C20 . . . . -177.1(3) ?
C18 C19 C20 C21 . . . . 0.2(6) ?
C19 C20 C21 C22 . . . . -1.7(7) ?
C20 C21 C22 C23 . . . . 2.2(6) ?
C19 C18 C23 C22 . . . . -0.1(5) ?
C17 C18 C23 C22 . . . . 177.6(3) ?
C21 C22 C23 C18 . . . . -1.3(6) ?
C9 C8 N1 N2 . . . . -0.1(3) ?
C9 C8 N1 C7 . . . . -178.4(3) ?
C4 C7 N1 C8 . . . . -74.7(4) ?
C4 C7 N1 N2 . . . . 107.1(3) ?
C8 N1 N2 N3 . . . . -0.3(3) ?
C7 N1 N2 N3 . . . . 178.3(3) ?
N1 N2 N3 C9 . . . . 0.5(3) ?
C8 C9 N3 N2 . . . . -0.5(4) ?
C10 C9 N3 N2 . . . . 179.0(3) ?
C16 C15 N4 N5 . . . . 0.2(4) ?
C14 C15 N4 N5 . . . . -178.5(3) ?
C15 N4 N5 N6 . . . . -0.2(3) ?
C15 C16 N6 N5 . . . . -0.1(3) ?
C15 C16 N6 C17 . . . . -172.9(3) ?
N4 N5 N6 C16 . . . . 0.2(3) ?
N4 N5 N6 C17 . . . . 173.8(3) ?
C18 C17 N6 C16 . . . . 78.2(4) ?
C18 C17 N6 N5 . . . . -94.0(3) ?
C11 C10 N7 C14 . . . . -0.2(4) ?
C9 C10 N7 C14 . . . . 176.9(2) ?
C13 C14 N7 C10 . . . . 1.3(4) ?
C15 C14 N7 C10 . . . . -176.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654269
