#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/72/2237238.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_2237238
loop_
_publ_author_name
'Belaziz, Dounia'
'Kandri Rodi, Youssef'
'Ouazzani Chahdi, Fouad'
'Essassi, El Mokhtar'
'Saadi, Mohamed'
'El Ammari, Lahcen'
_publ_section_title
;
 1-(4-Methylbenzyl)-1H-benzimidazol-2(3H)-one
;
_journal_coeditor_code           TK5182
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o122
_journal_paper_doi               10.1107/S1600536812050726
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H14 N2 O'
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.28
_chemical_melting_point          456
_chemical_name_systematic
;
1-(4-Methylbenzyl)-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                 95.277(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5585(5)
_cell_length_b                   5.7181(2)
_cell_length_c                   17.4153(7)
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.70
_cell_measurement_theta_min      3.26
_cell_volume                     1245.31(8)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and publCIF (Westrip,2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 APEXII'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16486
_diffrn_reflns_theta_full        28.70
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         3.26
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.150
_refine_ls_extinction_coef       0.0047(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0444
_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)+(0.0511P)²+0.2271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                2157
_reflns_number_total             3211
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5182.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               2237238
_cod_database_fobs_code          2237238
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
O O1 0.40817(8) 0.80403(18) 0.04185(6) 0.0541(3) Uani d . 1 1
N N1 0.59419(10) 0.8138(2) 0.06169(7) 0.0456(3) Uani d . 1 1
H H1N1 0.6036 0.9478 0.0317 0.055 Uiso d R 1 1
C C6 0.67241(12) 0.6686(2) 0.09809(7) 0.0416(3) Uani d . 1 1
N N2 0.50984(9) 0.51864(19) 0.10975(6) 0.0425(3) Uani d . 1 1
C C9 0.41188(10) 0.3448(2) 0.21353(8) 0.0399(3) Uani d . 1 1
C C5 0.61861(11) 0.4813(2) 0.12841(7) 0.0405(3) Uani d . 1 1
C C8 0.42295(12) 0.3671(2) 0.12812(8) 0.0475(4) Uani d . 1 1
H H8A 0.4343 0.2127 0.1073 0.057 Uiso calc R 1 1
H H8B 0.3565 0.4273 0.1029 0.057 Uiso calc R 1 1
C C4 0.67330(13) 0.3032(3) 0.16849(8) 0.0498(4) Uani d . 1 1
H H4 0.6375 0.1783 0.1886 0.060 Uiso calc R 1 1
C C14 0.44588(12) 0.5170(2) 0.26587(8) 0.0498(4) Uani d . 1 1
H H14 0.4778 0.6517 0.2487 0.060 Uiso calc R 1 1
C C10 0.36386(12) 0.1473(3) 0.24098(9) 0.0500(4) Uani d . 1 1
H H10 0.3403 0.0291 0.2069 0.060 Uiso calc R 1 1
C C7 0.49498(12) 0.7221(2) 0.06784(8) 0.0425(3) Uani d . 1 1
C C1 0.78212(12) 0.6843(3) 0.10756(9) 0.0518(4) Uani d . 1 1
H H1 0.8181 0.8099 0.0879 0.062 Uiso calc R 1 1
C C3 0.78367(13) 0.3187(3) 0.17738(9) 0.0568(4) Uani d . 1 1
H H3 0.8228 0.2012 0.2039 0.068 Uiso calc R 1 1
C C12 0.38486(12) 0.2947(3) 0.37129(9) 0.0568(4) Uani d . 1 1
C C2 0.83703(13) 0.5043(3) 0.14782(9) 0.0581(4) Uani d . 1 1
H H2 0.9113 0.5093 0.1550 0.070 Uiso calc R 1 1
C C11 0.35059(12) 0.1242(3) 0.31856(9) 0.0582(4) Uani d . 1 1
H H11 0.3178 -0.0095 0.3356 0.070 Uiso calc R 1 1
C C13 0.43294(13) 0.4911(3) 0.34360(9) 0.0580(4) Uani d . 1 1
H H13 0.4571 0.6084 0.3779 0.070 Uiso calc R 1 1
C C15 0.37084(17) 0.2654(5) 0.45607(11) 0.0944(7) Uani d . 1 1
H H15A 0.3991 0.4000 0.4839 0.142 Uiso calc R 1 1
H H15B 0.4084 0.1281 0.4753 0.142 Uiso calc R 1 1
H H15C 0.2962 0.2495 0.4628 0.142 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
C7 N1 C6 110.24(11)
C7 N1 H1N1 121.3
C6 N1 H1N1 128.2
C1 C6 N1 132.24(13)
C1 C6 C5 121.27(13)
N1 C6 C5 106.49(12)
C7 N2 C5 109.63(11)
C7 N2 C8 123.58(12)
C5 N2 C8 126.76(11)
C14 C9 C10 118.08(13)
C14 C9 C8 122.55(12)
C10 C9 C8 119.36(12)
C4 C5 N2 131.55(13)
C4 C5 C6 121.43(14)
N2 C5 C6 107.02(11)
N2 C8 C9 113.95(11)
N2 C8 H8A 108.8
C9 C8 H8A 108.8
N2 C8 H8B 108.8
C9 C8 H8B 108.8
H8A C8 H8B 107.7
C5 C4 C3 117.12(14)
C5 C4 H4 121.4
C3 C4 H4 121.4
C9 C14 C13 120.74(14)
C9 C14 H14 119.6
C13 C14 H14 119.6
C11 C10 C9 120.69(14)
C11 C10 H10 119.7
C9 C10 H10 119.7
O1 C7 N1 127.42(13)
O1 C7 N2 125.97(13)
N1 C7 N2 106.61(12)
C6 C1 C2 117.16(14)
C6 C1 H1 121.4
C2 C1 H1 121.4
C2 C3 C4 121.57(14)
C2 C3 H3 119.2
C4 C3 H3 119.2
C11 C12 C13 117.44(15)
C11 C12 C15 120.94(18)
C13 C12 C15 121.61(17)
C3 C2 C1 121.44(15)
C3 C2 H2 119.3
C1 C2 H2 119.3
C12 C11 C10 121.61(15)
C12 C11 H11 119.2
C10 C11 H11 119.2
C12 C13 C14 121.43(15)
C12 C13 H13 119.3
C14 C13 H13 119.3
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2338(16)
N1 C7 1.3649(18)
N1 C6 1.3933(17)
N1 H1N1 0.9411
C6 C1 1.375(2)
C6 C5 1.3959(19)
N2 C7 1.3770(16)
N2 C5 1.3913(17)
N2 C8 1.4521(17)
C9 C14 1.3822(19)
C9 C10 1.3857(19)
C9 C8 1.5120(19)
C5 C4 1.3811(18)
C8 H8A 0.9700
C8 H8B 0.9700
C4 C3 1.383(2)
C4 H4 0.9300
C14 C13 1.386(2)
C14 H14 0.9300
C10 C11 1.383(2)
C10 H10 0.9300
C1 C2 1.392(2)
C1 H1 0.9300
C3 C2 1.380(2)
C3 H3 0.9300
C12 C11 1.381(2)
C12 C13 1.383(2)
C12 C15 1.512(2)
C2 H2 0.9300
C11 H11 0.9300
C13 H13 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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 H1N1 O1 3_675 0.94 1.91 2.8317(15) 166
C15 H15C O1 2_545 0.96 2.58 3.514(2) 165
C8 H8A O1 1_545 0.97 2.61 3.5504(18) 164
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
C7 N1 C6 C1 -179.97(14)
C7 N1 C6 C5 -0.56(15)
C7 N2 C5 C4 -179.25(14)
C8 N2 C5 C4 -1.2(2)
C7 N2 C5 C6 0.82(14)
C8 N2 C5 C6 178.83(12)
C1 C6 C5 C4 -0.6(2)
N1 C6 C5 C4 179.90(12)
C1 C6 C5 N2 179.33(12)
N1 C6 C5 N2 -0.16(14)
C7 N2 C8 C9 -117.18(14)
C5 N2 C8 C9 65.08(17)
C14 C9 C8 N2 26.23(19)
C10 C9 C8 N2 -155.20(13)
N2 C5 C4 C3 -179.82(14)
C6 C5 C4 C3 0.1(2)
C10 C9 C14 C13 0.5(2)
C8 C9 C14 C13 179.13(14)
C14 C9 C10 C11 0.0(2)
C8 C9 C10 C11 -178.65(14)
C6 N1 C7 O1 -179.46(13)
C6 N1 C7 N2 1.05(15)
C5 N2 C7 O1 179.35(13)
C8 N2 C7 O1 1.3(2)
C5 N2 C7 N1 -1.15(15)
C8 N2 C7 N1 -179.24(12)
N1 C6 C1 C2 -179.93(14)
C5 C6 C1 C2 0.7(2)
C5 C4 C3 C2 0.3(2)
C4 C3 C2 C1 -0.1(2)
C6 C1 C2 C3 -0.4(2)
C13 C12 C11 C10 0.2(2)
C15 C12 C11 C10 -179.31(17)
C9 C10 C11 C12 -0.4(2)
C11 C12 C13 C14 0.3(2)
C15 C12 C13 C14 179.84(16)
C9 C14 C13 C12 -0.7(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 621277
