#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/96/2209645.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_2209645
loop_
_publ_author_name
'Moreno-Diaz, Hermenegilda'
'Navarrete-Vázquez, Gabriel'
'Estrada-Soto, Samuel'
'Tlahuext, Hugo'
_publ_section_title
;
 2-(4-Methoxyphenyl)-1H-benzimidazole
;
_journal_coeditor_code           SA2009
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2601
_journal_page_last               o2602
_journal_paper_doi               10.1107/S1600536806020435
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H12 N2 O'
_chemical_formula_moiety         'C14 H12 N2 O'
_chemical_formula_sum            'C14 H12 N2 O'
_chemical_formula_weight         224.26
_chemical_melting_point          502.3
_chemical_name_common            2-(4-Methoxyphenyl)-1H-benzimidazole
_chemical_name_systematic
;
2-(4-Methoxyphenyl)-1H-benzimidazole
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.22(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.354(2)
_cell_length_b                   10.562(2)
_cell_length_c                   9.868(2)
_cell_measurement_reflns_used    81
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.98
_cell_measurement_theta_min      1.94
_cell_volume                     1095.5(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5998
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.294
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0492
_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)+(0.0431P)²+0.5933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2033
_reflns_number_total             2245
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sa2009.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209645
_cod_database_fobs_code          2209645
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
C C1 0.15935(15) 0.91320(15) 0.79747(17) 0.0153(3) Uani d . 1
C C2 0.11643(16) 1.00463(16) 0.68776(18) 0.0185(4) Uani d . 1
H H2 0.1128 0.9889 0.5935 0.022 Uiso calc R 1
C C3 0.07942(16) 1.12013(16) 0.72566(19) 0.0191(4) Uani d . 1
H H3 0.0499 1.1834 0.6553 0.023 Uiso calc R 1
C C4 0.08576(16) 1.14330(16) 0.86839(19) 0.0193(4) Uani d . 1
H H4 0.0597 1.2215 0.8902 0.023 Uiso calc R 1
C C5 0.12976(16) 1.05296(15) 0.97731(18) 0.0184(4) Uani d . 1
H H5 0.1342 1.0698 1.0717 0.022 Uiso calc R 1
C C6 0.16739(15) 0.93549(15) 0.94180(17) 0.0155(3) Uani d . 1
C C7 0.23540(15) 0.74578(15) 0.93696(17) 0.0142(3) Uani d . 1
C C8 0.28847(16) 0.61830(15) 0.97758(17) 0.0151(3) Uani d . 1
C C9 0.25118(16) 0.51959(15) 0.87640(18) 0.0178(4) Uani d . 1
H H9 0.1896 0.5343 0.7838 0.021 Uiso calc R 1
C C10 0.30433(16) 0.39983(15) 0.91132(19) 0.0190(4) Uani d . 1
H H10 0.2779 0.3345 0.8433 0.023 Uiso calc R 1
C C11 0.39753(16) 0.37876(15) 1.04915(18) 0.0175(4) Uani d . 1
C C12 0.43465(16) 0.47655(15) 1.15220(18) 0.0175(4) Uani d . 1
H H12 0.4962 0.4618 1.2448 0.021 Uiso calc R 1
C C13 0.38020(16) 0.59476(15) 1.11689(17) 0.0165(4) Uani d . 1
H H13 0.4046 0.6593 1.1862 0.020 Uiso calc R 1
C C14 0.44328(18) 0.17162(16) 0.9852(2) 0.0227(4) Uani d . 1
H H14A 0.3591 0.1368 0.9544 0.034 Uiso calc R 1
H H14B 0.5047 0.1056 1.0254 0.034 Uiso calc R 1
H H14C 0.4554 0.2089 0.9027 0.034 Uiso calc R 1
N N1 0.20305(13) 0.79120(12) 0.79831(14) 0.0153(3) Uani d D 1
H H1 0.2088 0.7513 0.7251 0.030(6) Uiso calc RD 1
N N2 0.21575(14) 0.82823(12) 1.02777(15) 0.0167(3) Uani d . 1
O O1 0.45909(12) 0.26644(11) 1.09424(13) 0.0226(3) Uani d . 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'
O O 0.0106 0.0060 '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
N1 C1 C2 132.14(15)
N1 C1 C6 105.29(14)
C2 C1 C6 122.56(15)
C3 C2 C1 116.91(15)
C3 C2 H2 121.5
C1 C2 H2 121.5
C2 C3 C4 121.19(15)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 121.75(15)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 118.18(15)
C4 C5 H5 120.9
C6 C5 H5 120.9
N2 C6 C5 130.84(15)
N2 C6 C1 109.75(14)
C5 C6 C1 119.41(15)
N2 C7 N1 113.36(14)
N2 C7 C8 125.02(14)
N1 C7 C8 121.61(14)
C9 C8 C13 118.88(15)
C9 C8 C7 120.55(15)
C13 C8 C7 120.54(14)
C10 C9 C8 121.20(15)
C10 C9 H9 119.4
C8 C9 H9 119.4
C9 C10 C11 119.20(15)
C9 C10 H10 120.4
C11 C10 H10 120.4
O1 C11 C10 124.44(15)
O1 C11 C12 115.41(15)
C10 C11 C12 120.14(15)
C13 C12 C11 120.16(15)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C8 120.40(15)
C12 C13 H13 119.8
C8 C13 H13 119.8
O1 C14 H14A 109.5
O1 C14 H14B 109.5
H14A C14 H14B 109.5
O1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C7 N1 C1 107.13(13)
C7 N1 H1 126.4
C1 N1 H1 126.4
C7 N2 C6 104.46(13)
C11 O1 C14 117.43(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.380(2) yes
C1 C2 1.394(2) ?
C1 C6 1.412(2) ?
C2 C3 1.387(2) ?
C2 H2 0.9300 ?
C3 C4 1.404(2) ?
C3 H3 0.9300 ?
C4 C5 1.382(2) ?
C4 H4 0.9300 ?
C5 C6 1.399(2) ?
C5 H5 0.9300 ?
C6 N2 1.397(2) yes
C7 N2 1.328(2) yes
C7 N1 1.363(2) yes
C7 C8 1.468(2) ?
C8 C9 1.394(2) ?
C8 C13 1.398(2) ?
C9 C10 1.388(2) ?
C9 H9 0.9300 ?
C10 C11 1.390(2) ?
C10 H10 0.9300 ?
C11 O1 1.363(2) yes
C11 C12 1.398(2) ?
C12 C13 1.378(2) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 O1 1.430(2) ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
N1 H1 0.8600 ?
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
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.65(16) ?
C6 C1 C2 C3 -0.9(2) ?
C1 C2 C3 C4 0.3(2) ?
C2 C3 C4 C5 0.5(3) ?
C3 C4 C5 C6 -0.6(3) ?
C4 C5 C6 N2 179.50(16) ?
C4 C5 C6 C1 0.0(2) ?
N1 C1 C6 N2 0.21(18) ?
C2 C1 C6 N2 -178.82(15) ?
N1 C1 C6 C5 179.80(14) ?
C2 C1 C6 C5 0.8(2) ?
N2 C7 C8 C9 148.18(17) ?
N1 C7 C8 C9 -32.9(2) yes
N2 C7 C8 C13 -33.8(2) ?
N1 C7 C8 C13 145.09(16) ?
C13 C8 C9 C10 -0.7(2) ?
C7 C8 C9 C10 177.35(15) ?
C8 C9 C10 C11 -0.8(3) ?
C9 C10 C11 O1 -177.99(16) ?
C9 C10 C11 C12 1.6(3) ?
O1 C11 C12 C13 178.73(15) ?
C10 C11 C12 C13 -0.9(2) ?
C11 C12 C13 C8 -0.6(2) ?
C9 C8 C13 C12 1.4(2) ?
C7 C8 C13 C12 -176.63(15) ?
N2 C7 N1 C1 0.36(18) ?
C8 C7 N1 C1 -178.69(14) ?
C2 C1 N1 C7 178.57(17) ?
C6 C1 N1 C7 -0.33(17) ?
N1 C7 N2 C6 -0.22(18) ?
C8 C7 N2 C6 178.79(15) ?
C5 C6 N2 C7 -179.53(17) ?
C1 C6 N2 C7 0.00(17) ?
C10 C11 O1 C14 11.6(2) yes
C12 C11 O1 C14 -167.99(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 306596
