#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/18/2221856.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_2221856
loop_
_publ_author_name
'Happ, Bobby'
'Hoogenboom, Richard'
'Winter, Andreas'
'Hager, Martin D.'
'Baumann, Stefan O.'
'Kickelbick, Guido'
'Schubert, Ulrich S.'
_publ_section_title
;
 2-[1-(1-Naphthyl)-1H-1,2,3-triazol-4-yl]pyridine
;
_journal_coeditor_code           WN2322
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1146
_journal_paper_doi               10.1107/S160053680901407X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H12 N4'
_chemical_formula_moiety         'C17 H12 N4'
_chemical_formula_sum            'C17 H12 N4'
_chemical_formula_weight         272.31
_chemical_name_systematic
;
2-[1-(1-Naphthyl)-1H-1,2,3-triazol-4-yl]pyridine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.6378(4)
_cell_length_b                   9.3228(4)
_cell_length_c                   25.0592(9)
_cell_measurement_reflns_used    4456
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.931
_cell_measurement_theta_min      2.388
_cell_volume                     2718.85(18)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'CARINE (Boudias & Monceau, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14517
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.63
_diffrn_standards_interval_time  15
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0350
_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)+(0.0842P)²+0.1848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1196
_reflns_number_gt                1934
_reflns_number_total             2391
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2322.cif
_cod_data_source_block           I
_cod_original_cell_volume        2718.84(18)
_cod_database_code               2221856
_cod_database_fobs_code          2221856
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
N N1 0.20019(9) 0.39250(12) 0.37942(4) 0.0428(3) Uani d . 1 . .
N N2 0.31490(10) 0.36728(14) 0.37933(5) 0.0509(3) Uani d . 1 . .
N N3 0.35790(10) 0.43998(13) 0.33925(5) 0.0489(3) Uani d . 1 . .
C C4 0.27219(11) 0.51071(14) 0.31370(5) 0.0403(3) Uani d . 1 . .
C C5 0.17170(12) 0.48053(15) 0.33923(5) 0.0450(4) Uani d . 1 . .
H H5 0.0987 0.5139 0.3306 0.054 Uiso calc R 1 . .
N N6 0.19978(11) 0.66666(14) 0.24668(5) 0.0530(4) Uani d . 1 . .
C C7 0.29352(12) 0.60832(15) 0.26887(5) 0.0411(3) Uani d . 1 . .
C C8 0.40394(13) 0.64153(17) 0.25220(5) 0.0495(4) Uani d . 1 . .
H H8 0.4672 0.5971 0.2678 0.059 Uiso calc R 1 . .
C C9 0.41850(15) 0.74114(18) 0.21229(6) 0.0590(4) Uani d . 1 . .
H H9 0.4918 0.7662 0.2008 0.071 Uiso calc R 1 . .
C C10 0.32349(16) 0.80283(19) 0.18976(7) 0.0635(5) Uani d . 1 . .
H H10 0.3310 0.8711 0.1629 0.076 Uiso calc R 1 . .
C C11 0.21677(15) 0.76197(19) 0.20758(7) 0.0619(5) Uani d . 1 . .
H H11 0.1526 0.8030 0.1915 0.074 Uiso calc R 1 . .
C C12 0.12717(11) 0.32768(14) 0.41875(5) 0.0420(3) Uani d . 1 . .
C C13 0.13387(11) 0.37575(14) 0.47248(5) 0.0405(3) Uani d . 1 . .
C C14 0.20520(12) 0.48862(16) 0.48997(6) 0.0482(4) Uani d . 1 . .
H H14 0.2525 0.5357 0.4657 0.058 Uiso calc R 1 . .
C C15 0.20518(14) 0.52911(18) 0.54222(7) 0.0573(4) Uani d . 1 . .
H H15 0.2519 0.6044 0.5532 0.069 Uiso calc R 1 . .
C C16 0.13572(14) 0.4588(2) 0.57950(6) 0.0607(4) Uani d . 1 . .
H H16 0.1381 0.4860 0.6152 0.073 Uiso calc R 1 . .
C C17 0.06506(14) 0.35138(18) 0.56387(6) 0.0552(4) Uani d . 1 . .
H H17 0.0187 0.3060 0.5890 0.066 Uiso calc R 1 . .
C C18 0.06071(12) 0.30717(15) 0.50993(5) 0.0445(4) Uani d . 1 . .
C C19 -0.01489(14) 0.19830(16) 0.49262(7) 0.0554(4) Uani d . 1 . .
H H19 -0.0625 0.1532 0.5173 0.066 Uiso calc R 1 . .
C C20 -0.01924(15) 0.15834(17) 0.44059(7) 0.0587(4) Uani d . 1 . .
H H20 -0.0703 0.0872 0.4298 0.070 Uiso calc R 1 . .
C C21 0.05301(13) 0.22392(16) 0.40296(6) 0.0523(4) Uani d . 1 . .
H H21 0.0500 0.1963 0.3673 0.063 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
C5 N1 N2 . . 110.40(11) ?
C5 N1 C12 . . 128.86(11) ?
N2 N1 C12 . . 120.75(11) ?
N3 N2 N1 . . 106.70(11) ?
N2 N3 C4 . . 109.41(11) ?
N3 C4 C5 . . 108.01(12) ?
N3 C4 C7 . . 122.59(12) ?
C5 C4 C7 . . 129.27(12) ?
N1 C5 C4 . . 105.48(12) ?
N1 C5 H5 . . 127.3 ?
C4 C5 H5 . . 127.3 ?
C11 N6 C7 . . 116.96(13) ?
N6 C7 C8 . . 122.62(13) ?
N6 C7 C4 . . 115.59(12) ?
C8 C7 C4 . . 121.75(13) ?
C9 C8 C7 . . 118.96(15) ?
C9 C8 H8 . . 120.5 ?
C7 C8 H8 . . 120.5 ?
C10 C9 C8 . . 118.97(15) ?
C10 C9 H9 . . 120.5 ?
C8 C9 H9 . . 120.5 ?
C9 C10 C11 . . 118.68(16) ?
C9 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
N6 C11 C10 . . 123.78(16) ?
N6 C11 H11 . . 118.1 ?
C10 C11 H11 . . 118.1 ?
C21 C12 C13 . . 122.44(13) ?
C21 C12 N1 . . 118.51(13) ?
C13 C12 N1 . . 119.05(12) ?
C14 C13 C12 . . 124.20(12) ?
C14 C13 C18 . . 118.92(13) ?
C12 C13 C18 . . 116.84(13) ?
C15 C14 C13 . . 120.35(14) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 120.81(16) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C17 C16 C15 . . 120.30(15) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C18 . . 120.93(14) ?
C16 C17 H17 . . 119.5 ?
C18 C17 H17 . . 119.5 ?
C19 C18 C17 . . 121.72(13) ?
C19 C18 C13 . . 119.63(13) ?
C17 C18 C13 . . 118.64(14) ?
C20 C19 C18 . . 121.07(14) ?
C20 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C19 C20 C21 . . 120.23(15) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C12 C21 C20 . . 119.76(14) ?
C12 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
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 C5 . 1.3408(17) ?
N1 N2 . 1.3556(16) ?
N1 C12 . 1.4348(17) ?
N2 N3 . 1.3110(16) ?
N3 C4 . 1.3563(18) ?
C4 C5 . 1.3623(19) ?
C4 C7 . 1.4669(19) ?
C5 H5 . 0.9300 ?
N6 C11 . 1.337(2) ?
N6 C7 . 1.3398(19) ?
C7 C8 . 1.386(2) ?
C8 C9 . 1.375(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.368(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.374(2) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C21 . 1.355(2) ?
C12 C13 . 1.4212(19) ?
C13 C14 . 1.410(2) ?
C13 C18 . 1.4195(19) ?
C14 C15 . 1.363(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.398(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.354(2) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.414(2) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.411(2) ?
C19 C20 . 1.357(2) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.403(2) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
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
C5 N1 N2 N3 . . . . 0.24(15) ?
C12 N1 N2 N3 . . . . 179.90(12) ?
N1 N2 N3 C4 . . . . -0.21(15) ?
N2 N3 C4 C5 . . . . 0.12(16) ?
N2 N3 C4 C7 . . . . 176.41(12) ?
N2 N1 C5 C4 . . . . -0.16(15) ?
C12 N1 C5 C4 . . . . -179.79(13) ?
N3 C4 C5 N1 . . . . 0.03(16) ?
C7 C4 C5 N1 . . . . -175.93(13) ?
C11 N6 C7 C8 . . . . -1.1(2) ?
C11 N6 C7 C4 . . . . 176.54(13) ?
N3 C4 C7 N6 . . . . 177.95(12) ?
C5 C4 C7 N6 . . . . -6.6(2) ?
N3 C4 C7 C8 . . . . -4.4(2) ?
C5 C4 C7 C8 . . . . 171.04(14) ?
N6 C7 C8 C9 . . . . 1.8(2) ?
C4 C7 C8 C9 . . . . -175.67(13) ?
C7 C8 C9 C10 . . . . -0.9(2) ?
C8 C9 C10 C11 . . . . -0.5(3) ?
C7 N6 C11 C10 . . . . -0.5(3) ?
C9 C10 C11 N6 . . . . 1.3(3) ?
C5 N1 C12 C21 . . . . 69.54(19) ?
N2 N1 C12 C21 . . . . -110.05(15) ?
C5 N1 C12 C13 . . . . -109.53(16) ?
N2 N1 C12 C13 . . . . 70.88(16) ?
C21 C12 C13 C14 . . . . -176.38(14) ?
N1 C12 C13 C14 . . . . 2.65(19) ?
C21 C12 C13 C18 . . . . 1.60(19) ?
N1 C12 C13 C18 . . . . -179.37(12) ?
C12 C13 C14 C15 . . . . 179.13(13) ?
C18 C13 C14 C15 . . . . 1.2(2) ?
C13 C14 C15 C16 . . . . 0.7(2) ?
C14 C15 C16 C17 . . . . -1.7(2) ?
C15 C16 C17 C18 . . . . 0.6(2) ?
C16 C17 C18 C19 . . . . -178.08(14) ?
C16 C17 C18 C13 . . . . 1.3(2) ?
C14 C13 C18 C19 . . . . 177.22(13) ?
C12 C13 C18 C19 . . . . -0.87(18) ?
C14 C13 C18 C17 . . . . -2.18(19) ?
C12 C13 C18 C17 . . . . 179.73(12) ?
C17 C18 C19 C20 . . . . 179.09(14) ?
C13 C18 C19 C20 . . . . -0.3(2) ?
C18 C19 C20 C21 . . . . 0.8(2) ?
C13 C12 C21 C20 . . . . -1.1(2) ?
N1 C12 C21 C20 . . . . 179.83(13) ?
C19 C20 C21 C12 . . . . -0.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742187
