#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/78/2237894.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_2237894
loop_
_publ_author_name
'Geiger, David K.'
'Bond, Christopher J.'
_publ_section_title
;
 2-(Pyridin-4-yl)-1H-benzimidazole
;
_journal_coeditor_code           IM2430
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o869
_journal_paper_doi               10.1107/S160053681301252X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H9 N3'
_chemical_formula_moiety         'C12 H9 N3'
_chemical_formula_sum            'C12 H9 N3'
_chemical_formula_weight         195.22
_chemical_name_systematic
;
2-(Pyridin-4-yl)-1H-benzimidazole
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 101.838(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0602(14)
_cell_length_b                   11.610(3)
_cell_length_c                   13.892(4)
_cell_measurement_reflns_used    1098
_cell_measurement_temperature    200.(2)
_cell_measurement_theta_max      24.2128
_cell_measurement_theta_min      2.3035
_cell_volume                     956.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200.(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker SMART X2S CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4809
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2010)'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0462
_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)+(0.0664P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                1125
_reflns_number_total             1699
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2430.cif
_cod_data_source_block           I
_cod_database_code               2237894
_cod_database_fobs_code          2237894
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_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
N N1 0.4979(3) 0.67895(13) 0.38292(14) 0.0331(5) Uani d . 1
H H1 0.618(4) 0.7118(19) 0.3528(19) 0.062(7) Uiso d . 1
N N2 0.2493(3) 0.54899(13) 0.41681(13) 0.0303(5) Uani d . 1
N N3 0.7075(3) 0.30522(13) 0.22238(14) 0.0357(5) Uani d . 1
C C1 0.3669(3) 0.73593(15) 0.43732(16) 0.0294(5) Uani d . 1
C C2 0.2130(3) 0.65460(15) 0.45835(16) 0.0286(5) Uani d . 1
C C3 0.0506(3) 0.68515(17) 0.51158(17) 0.0338(6) Uani d . 1
H H3 -0.0548 0.6305 0.5259 0.041 Uiso calc R 1
C C4 0.0490(3) 0.79775(16) 0.54271(18) 0.0389(6) Uani d . 1
H H4 -0.0594 0.8211 0.5794 0.047 Uiso calc R 1
C C5 0.2039(3) 0.87851(17) 0.52133(19) 0.0412(6) Uani d . 1
H H5 0.1968 0.9556 0.5434 0.049 Uiso calc R 1
C C6 0.3650(4) 0.84967(16) 0.46965(18) 0.0398(6) Uani d . 1
H H6 0.471 0.9046 0.4563 0.048 Uiso calc R 1
C C7 0.4191(3) 0.56767(15) 0.37324(16) 0.0284(5) Uani d . 1
C C8 0.5194(3) 0.47905(15) 0.32041(16) 0.0295(5) Uani d . 1
C C9 0.7077(4) 0.49937(16) 0.28180(18) 0.0368(6) Uani d . 1
H H9 0.7769 0.5732 0.2878 0.044 Uiso calc R 1
C C10 0.7947(4) 0.41118(17) 0.23429(18) 0.0395(6) Uani d . 1
H H10 0.9251 0.4268 0.2084 0.047 Uiso calc R 1
C C11 0.5260(3) 0.28667(16) 0.26116(17) 0.0352(6) Uani d . 1
H H11 0.4609 0.2119 0.2545 0.042 Uiso calc R 1
C C12 0.4278(3) 0.36867(15) 0.30996(17) 0.0336(6) Uani d . 1
H H12 0.2992 0.3503 0.3362 0.04 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
C1 N1 C7 106.18(16)
C1 N1 H1 127.4(13)
C7 N1 H1 126.4(14)
C7 N2 C2 104.53(15)
C10 N3 C11 115.83(18)
N1 C1 C6 132.60(19)
N1 C1 C2 105.96(16)
C6 C1 C2 121.44(19)
N2 C2 C3 129.31(18)
N2 C2 C1 109.83(18)
C3 C2 C1 120.84(18)
C4 C3 C2 117.37(19)
C4 C3 H3 121.3
C2 C3 H3 121.3
C3 C4 C5 121.4(2)
C3 C4 H4 119.3
C5 C4 H4 119.3
C6 C5 C4 121.96(19)
C6 C5 H5 119.0
C4 C5 H5 119.0
C5 C6 C1 117.04(19)
C5 C6 H6 121.5
C1 C6 H6 121.5
N2 C7 N1 113.51(17)
N2 C7 C8 123.97(16)
N1 C7 C8 122.52(18)
C9 C8 C12 117.48(19)
C9 C8 C7 122.43(17)
C12 C8 C7 120.06(19)
C8 C9 C10 119.18(18)
C8 C9 H9 120.4
C10 C9 H9 120.4
N3 C10 C9 124.2(2)
N3 C10 H10 117.9
C9 C10 H10 117.9
N3 C11 C12 124.24(18)
N3 C11 H11 117.9
C12 C11 H11 117.9
C11 C12 C8 119.1(2)
C11 C12 H12 120.5
C8 C12 H12 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.373(3)
N1 C7 1.374(2)
N1 H1 0.99(2)
N2 C7 1.315(3)
N2 C2 1.392(2)
N3 C10 1.336(2)
N3 C11 1.338(3)
C1 C6 1.396(3)
C1 C2 1.399(3)
C2 C3 1.393(3)
C3 C4 1.378(3)
C3 H3 0.95
C4 C5 1.401(3)
C4 H4 0.95
C5 C6 1.367(3)
C5 H5 0.95
C6 H6 0.95
C7 C8 1.466(3)
C8 C9 1.377(3)
C8 C12 1.392(3)
C9 C10 1.380(3)
C9 H9 0.95
C10 H10 0.95
C11 C12 1.373(3)
C11 H11 0.95
C12 H12 0.95
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
_geom_hbond_publ_flag
N1 H1 N3 2_655 0.99(2) 1.96(2) 2.924(2) 165(2) y
