#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/07/2230723.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_2230723
loop_
_publ_author_name
'Ouzidan, Younes'
'Essassi, El Mokhtar'
'Luis, Santiago V.'
'Bolte, Michael'
'El Ammari, Lahcen'
_publ_section_title
;
 1-Benzyl-1H-benzimidazol-2(3H)-one
;
_journal_coeditor_code           IM2298
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1822
_journal_paper_doi               10.1107/S160053681102455X
_journal_volume                  67
_journal_year                    2011
_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_name_systematic
;
1-Benzyl-1H-benzimidazol-2(3H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.5346(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8652(7)
_cell_length_b                   5.7975(3)
_cell_length_c                   14.9337(7)
_cell_measurement_reflns_used    3392
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      1.74
_cell_volume                     1131.33(10)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker  CCD three-circle'
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9007
_diffrn_reflns_theta_full        30.49
_diffrn_reflns_theta_max         30.49
_diffrn_reflns_theta_min         1.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.9588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0445
_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)+(0.0584P)²+0.1866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                2514
_reflns_number_total             3392
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2298.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230723
_cod_database_fobs_code          2230723
loop_
_symmetry_equiv_pos_as_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
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.59908(7) 0.79068(16) 0.53088(6) 0.0462(2) Uani d . 1 1 . .
N N1 0.46509(7) 0.82117(17) 0.38695(7) 0.0391(2) Uani d . 1 1 . .
H H1 0.4387 0.9497 0.3958 0.066(5) Uiso calc R 1 1 . .
C C1 0.54932(8) 0.72077(19) 0.45072(8) 0.0354(2) Uani d . 1 1 . .
N N2 0.56888(7) 0.52373(16) 0.40851(7) 0.0350(2) Uani d . 1 1 . .
C C2 0.49440(8) 0.49698(19) 0.31953(8) 0.0343(2) Uani d . 1 1 . .
C C3 0.47930(10) 0.3259(2) 0.25181(9) 0.0429(3) Uani d . 1 1 . .
H H3 0.5232 0.2003 0.2611 0.050(4) Uiso calc R 1 1 . .
C C4 0.39558(11) 0.3498(3) 0.16918(9) 0.0513(3) Uani d . 1 1 . .
H H4 0.3834 0.2382 0.1220 0.060(4) Uiso calc R 1 1 . .
C C5 0.32981(10) 0.5368(3) 0.15565(9) 0.0510(3) Uani d . 1 1 . .
H H5 0.2745 0.5477 0.0995 0.058(4) Uiso calc R 1 1 . .
C C6 0.34472(10) 0.7081(2) 0.22409(9) 0.0455(3) Uani d . 1 1 . .
H H6 0.3002 0.8326 0.2151 0.056(4) Uiso calc R 1 1 . .
C C7 0.42820(9) 0.68586(19) 0.30576(8) 0.0357(2) Uani d . 1 1 . .
C C8 0.64791(9) 0.3581(2) 0.45689(8) 0.0378(2) Uani d . 1 1 . .
H H8A 0.6173 0.2060 0.4513 0.044(4) Uiso calc R 1 1 . .
H H8B 0.6744 0.3968 0.5239 0.041(3) Uiso calc R 1 1 . .
C C11 0.73601(8) 0.34906(19) 0.41875(8) 0.0354(2) Uani d . 1 1 . .
C C12 0.75053(11) 0.1565(2) 0.36992(10) 0.0491(3) Uani d . 1 1 . .
H H12 0.7048 0.0339 0.3591 0.061(5) Uiso calc R 1 1 . .
C C13 0.83286(13) 0.1452(3) 0.33705(12) 0.0638(4) Uani d . 1 1 . .
H H13 0.8416 0.0160 0.3036 0.088(6) Uiso calc R 1 1 . .
C C14 0.90122(13) 0.3235(3) 0.35368(12) 0.0659(4) Uani d . 1 1 . .
H H14 0.9569 0.3145 0.3324 0.085(6) Uiso calc R 1 1 . .
C C15 0.88757(11) 0.5165(3) 0.40199(12) 0.0597(4) Uani d . 1 1 . .
H H15 0.9338 0.6382 0.4129 0.068(5) Uiso calc R 1 1 . .
C C16 0.80491(10) 0.5294(2) 0.43437(10) 0.0459(3) Uani d . 1 1 . .
H H16 0.7958 0.6601 0.4668 0.054(4) Uiso calc R 1 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C7 . . 110.31(9) ?
C1 N1 H1 . . 124.8 ?
C7 N1 H1 . . 124.8 ?
O1 C1 N1 . . 127.38(11) ?
O1 C1 N2 . . 125.88(11) ?
N1 C1 N2 . . 106.74(10) ?
C1 N2 C2 . . 109.46(9) ?
C1 N2 C8 . . 123.52(10) ?
C2 N2 C8 . . 126.56(9) ?
C3 C2 N2 . . 131.39(10) ?
C3 C2 C7 . . 121.52(11) ?
N2 C2 C7 . . 107.09(9) ?
C2 C3 C4 . . 117.10(11) ?
C2 C3 H3 . . 121.5 ?
C4 C3 H3 . . 121.5 ?
C5 C4 C3 . . 121.38(12) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
C4 C5 C6 . . 121.48(12) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C7 C6 C5 . . 117.27(11) ?
C7 C6 H6 . . 121.4 ?
C5 C6 H6 . . 121.4 ?
C6 C7 N1 . . 132.40(11) ?
C6 C7 C2 . . 121.25(11) ?
N1 C7 C2 . . 106.35(10) ?
N2 C8 C11 . . 113.90(9) ?
N2 C8 H8A . . 108.8 ?
C11 C8 H8A . . 108.8 ?
N2 C8 H8B . . 108.8 ?
C11 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C16 C11 C12 . . 119.00(11) ?
C16 C11 C8 . . 120.68(11) ?
C12 C11 C8 . . 120.30(11) ?
C11 C12 C13 . . 120.43(14) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.16(14) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 120.03(14) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C14 C15 C16 . . 120.02(14) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C11 C16 C15 . . 120.36(13) ?
C11 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
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
O1 C1 . 1.2332(14) ?
N1 C1 . 1.3660(15) ?
N1 C7 . 1.3901(15) ?
N1 H1 . 0.8600 ?
C1 N2 . 1.3749(14) ?
N2 C2 . 1.3922(14) ?
N2 C8 . 1.4546(14) ?
C2 C3 . 1.3815(16) ?
C2 C7 . 1.3991(15) ?
C3 C4 . 1.3897(19) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.387(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.3902(19) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.3783(17) ?
C6 H6 . 0.9300 ?
C8 C11 . 1.5114(15) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C11 C16 . 1.3824(17) ?
C11 C12 . 1.3845(17) ?
C12 C13 . 1.387(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.368(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.379(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.3869(19) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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 O1 3_676 0.86 2.03 2.8450(10) 158
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 643626
