#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:09:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201973 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/76/2207607.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_2207607
loop_
_publ_author_name
'Sławomir Krawczyk'
'Maria Gdaniec'
_publ_section_title
;
 Polymorph β of 1H-benzimidazole
;
_journal_coeditor_code           NC6052
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4116
_journal_page_last               o4118
_journal_paper_doi               10.1107/S1600536805036536
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C7 H6 N2'
_chemical_formula_moiety         'C7 H6 N2'
_chemical_formula_sum            'C7 H6 N2'
_chemical_formula_weight         118.14
_chemical_melting_point          .431E-305
_chemical_name_systematic
;
1H-benzimidazole
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                   9.7257(11)
_cell_length_b                   16.6879(17)
_cell_length_c                   7.6056(11)
_cell_measurement_reflns_used    2816
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      4
_cell_volume                     1234.4(3)
_computing_cell_refinement       'CrysAlis CCD'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2004)'
_computing_molecular_graphics
;
Stereochemical Workstation Operation Manual (Siemens, 1989) and
MERCURY (Version 1.3; Bruno et al.,  2002)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Kuma KM4 CCD κ geometry'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4312
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         4.19
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         1091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.174
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0531
_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)+(0.0569P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                887
_reflns_number_total             1091
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc6052.cif
_cod_data_source_block           I
_cod_database_code               2207607
_cod_database_fobs_code          2207607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
loop_
_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_type_symbol
N1 0.85139(16) 0.47227(8) 0.19758(18) 0.0516(5) Uani d . 1 N
H1 0.7676 0.4887 0.1995 0.068(6) Uiso calc R 1 H
C2 0.95811(19) 0.50402(13) 0.2859(2) 0.0553(5) Uani d . 1 C
H2 0.9494 0.5484 0.3590 0.063(6) Uiso calc R 1 H
N3 1.07556(15) 0.46717(9) 0.26031(18) 0.0559(5) Uani d . 1 N
C4 1.1264(2) 0.34826(11) 0.0648(2) 0.0597(6) Uani d . 1 C
H4 1.2198 0.3455 0.0904 0.074(6) Uiso calc R 1 H
C5 1.0668(2) 0.29575(12) -0.0519(3) 0.0666(6) Uani d . 1 C
H5 1.1210 0.2571 -0.1061 0.077(6) Uiso calc R 1 H
C6 0.9266(2) 0.29926(12) -0.0908(3) 0.0652(6) Uani d . 1 C
H6 0.8898 0.2633 -0.1714 0.077(6) Uiso calc R 1 H
C7 0.8420(2) 0.35477(11) -0.0127(2) 0.0594(6) Uani d . 1 C
H7 0.7482 0.3564 -0.0366 0.063(6) Uiso calc R 1 H
C8 0.90272(17) 0.40831(10) 0.1034(2) 0.0441(5) Uani d . 1 C
C9 1.04281(17) 0.40549(10) 0.1431(2) 0.0457(5) Uani d . 1 C
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0376(10) 0.0607(10) 0.0566(9) 0.0025(8) 0.0029(7) 0.0033(8)
C2 0.0533(13) 0.0633(13) 0.0493(10) 0.0002(10) 0.0039(9) -0.0035(10)
N3 0.0441(10) 0.0676(11) 0.0559(9) -0.0002(8) -0.0025(7) -0.0068(8)
C4 0.0465(13) 0.0631(13) 0.0695(12) 0.0054(9) 0.0008(10) -0.0016(11)
C5 0.0692(15) 0.0547(13) 0.0759(13) 0.0053(11) 0.0066(11) -0.0059(11)
C6 0.0742(15) 0.0525(13) 0.0688(12) -0.0090(11) -0.0079(11) -0.0062(10)
C7 0.0497(13) 0.0564(12) 0.0721(12) -0.0076(10) -0.0090(10) 0.0053(10)
C8 0.0407(11) 0.0456(11) 0.0460(9) -0.0020(8) 0.0029(8) 0.0083(8)
C9 0.0416(12) 0.0493(11) 0.0461(9) -0.0036(8) 0.0026(8) 0.0047(9)
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
C2 N1 C8 106.55(15)
C2 N1 H1 126.7
C8 N1 H1 126.7
N3 C2 N1 114.41(17)
N3 C2 H2 122.8
N1 C2 H2 122.8
C2 N3 C9 103.96(15)
C5 C4 C9 117.90(18)
C5 C4 H4 121.0
C9 C4 H4 121.0
C4 C5 C6 121.47(19)
C4 C5 H5 119.3
C6 C5 H5 119.3
C7 C6 C5 121.44(19)
C7 C6 H6 119.3
C5 C6 H6 119.3
C6 C7 C8 116.97(18)
C6 C7 H7 121.5
C8 C7 H7 121.5
N1 C8 C7 132.41(17)
N1 C8 C9 105.48(14)
C7 C8 C9 122.09(16)
C4 C9 C8 120.11(16)
C4 C9 N3 130.27(16)
C8 C9 N3 109.60(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.345(2)
N1 C8 1.3791(19)
N1 H1 0.8600
C2 N3 1.312(2)
C2 H2 0.9300
N3 C9 1.398(2)
C4 C5 1.376(2)
C4 C9 1.389(2)
C4 H4 0.9300
C5 C6 1.396(3)
C5 H5 0.9300
C6 C7 1.374(3)
C6 H6 0.9300
C7 C8 1.388(2)
C7 H7 0.9300
C8 C9 1.396(2)
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
N1 H1 N3 4_465 0.86 2.03 2.884(2) 172
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5593
