#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/20/2222036.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_2222036
loop_
_publ_author_name
'Xiao, Hui-Quan'
'Zhang, Ming-Zhu'
'Wang, Wei'
_publ_section_title
;
 2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol
;
_journal_coeditor_code           HG2503
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1256
_journal_paper_doi               10.1107/S1600536809016523
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H14 N2 O2'
_chemical_formula_moiety         'C15 H14 N2 O2'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_systematic
;
2-Methoxy-6-(6-methyl-1H-benzimidazol-2-yl)phenol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 104.216(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.986(3)
_cell_length_b                   11.4452(16)
_cell_length_c                   13.4105(19)
_cell_measurement_reflns_used    2318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.875
_cell_measurement_theta_min      2.346
_cell_volume                     2676.1(7)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6836
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.234
_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     176
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1024
_refine_ls_R_factor_gt           0.0561
_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)+(0.0769P)²+0.8329P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1692
_reflns_number_gt                1441
_reflns_number_total             2531
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2503.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222036
_cod_database_fobs_code          2222036
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_disorder_assembly
_atom_site_disorder_group
O O1 0.34998(10) 0.96117(16) 0.14576(12) 0.0718(6) Uani d . 1 . .
H H1 0.3809 0.9222 0.1879 0.086 Uiso d R 1 . .
O O2 0.23740(12) 1.0753(2) 0.03072(14) 0.0942(7) Uani d . 1 . .
N N1 0.39603(12) 0.94335(19) 0.46813(14) 0.0644(6) Uani d . 1 . .
H H1A 0.3689 0.9806 0.5087 0.077 Uiso d R 1 . .
N N2 0.42667(11) 0.89053(17) 0.32288(14) 0.0568(5) Uani d . 1 . .
C C1 0.31924(14) 1.0273(2) 0.30233(18) 0.0568(6) Uani d . 1 . .
C C2 0.30615(14) 1.0242(2) 0.19534(18) 0.0574(6) Uani d . 1 . .
C C3 0.24529(16) 1.0877(2) 0.1342(2) 0.0691(8) Uani d . 1 . .
C C4 0.20037(17) 1.1559(3) 0.1795(2) 0.0839(9) Uani d . 1 . .
H H4 0.1605 1.1992 0.1389 0.101 Uiso calc R 1 . .
C C5 0.21404(19) 1.1607(3) 0.2856(3) 0.0928(10) Uani d . 1 . .
H H5 0.1834 1.2075 0.3158 0.111 Uiso calc R 1 . .
C C6 0.27225(17) 1.0974(3) 0.3463(2) 0.0797(9) Uani d . 1 . .
H H6 0.2807 1.1009 0.4175 0.096 Uiso calc R 1 . .
C C7 0.38041(14) 0.9559(2) 0.36368(17) 0.0554(6) Uani d . 1 . .
C C8 0.1738(2) 1.1332(4) -0.0374(3) 0.1217(14) Uani d . 1 . .
H H8A 0.1748 1.1176 -0.1074 0.183 Uiso calc R 1 . .
H H8B 0.1776 1.2158 -0.0251 0.183 Uiso calc R 1 . .
H H8C 0.1266 1.1047 -0.0252 0.183 Uiso calc R 1 . .
C C9 0.45596(15) 0.8650(2) 0.49645(19) 0.0659(7) Uani d . 1 C .
C C10 0.47445(14) 0.8322(2) 0.40546(19) 0.0618(7) Uani d . 1 C .
C C11 0.53215(16) 0.7501(3) 0.4079(2) 0.0806(9) Uani d . 1 . .
H H11 0.5454 0.7270 0.3480 0.097 Uiso calc R 1 A 1
C C14 0.49349(18) 0.8175(3) 0.5915(2) 0.0865(10) Uani d . 1 . .
H H14 0.4807 0.8398 0.6519 0.104 Uiso calc R 1 B 1
C C12A 0.56835(19) 0.7052(3) 0.5008(3) 0.1024(16) Uani d PU 0.724(4) C 1
H H12A 0.6072 0.6509 0.5033 0.123 Uiso calc PR 0.724(4) C 1
C C13A 0.55061(19) 0.7359(3) 0.5920(3) 0.0988(17) Uani d PDU 0.724(4) C 1
C C15A 0.5957(3) 0.6706(5) 0.6876(3) 0.1041(15) Uani d PD 0.724(4) C 1
H H15A 0.5797 0.6974 0.7469 0.156 Uiso calc PR 0.724(4) C 1
H H15B 0.6495 0.6854 0.6969 0.156 Uiso calc PR 0.724(4) C 1
H H15C 0.5861 0.5883 0.6788 0.156 Uiso calc PR 0.724(4) C 1
C C13B 0.56835(19) 0.7052(3) 0.5008(3) 0.0988(17) Uani d PD 0.276(4) C 2
C C12B 0.55061(19) 0.7359(3) 0.5920(3) 0.1024(16) Uani d P 0.276(4) C 2
H H12B 0.5769 0.7018 0.6536 0.123 Uiso calc PR 0.276(4) C 2
C C15B 0.6306(6) 0.6287(11) 0.5397(9) 0.1041(15) Uani d PD 0.276(4) C 2
H H15G 0.6498 0.5992 0.4838 0.156 Uiso calc PR 0.276(4) C 2
H H15D 0.6136 0.5648 0.5748 0.156 Uiso calc PR 0.276(4) C 2
H H15E 0.6707 0.6703 0.5868 0.156 Uiso calc PR 0.276(4) C 2
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
C2 O1 H1 . . 109.2 ?
C3 O2 C8 . . 117.7(2) ?
C7 N1 C9 . . 107.4(2) ?
C7 N1 H1A . . 123.5 ?
C9 N1 H1A . . 129.0 ?
C7 N2 C10 . . 105.6(2) ?
C2 C1 C6 . . 118.8(2) ?
C2 C1 C7 . . 118.8(2) ?
C6 C1 C7 . . 122.5(2) ?
O1 C2 C1 . . 123.0(2) ?
O1 C2 C3 . . 117.0(2) ?
C1 C2 C3 . . 120.0(2) ?
O2 C3 C4 . . 125.8(2) ?
O2 C3 C2 . . 114.3(2) ?
C4 C3 C2 . . 119.9(2) ?
C3 C4 C5 . . 120.3(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.5(3) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 120.6(3) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
N2 C7 N1 . . 111.7(2) ?
N2 C7 C1 . . 123.1(2) ?
N1 C7 C1 . . 125.2(2) ?
O2 C8 H8A . . 109.5 ?
O2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 105.8(2) ?
N1 C9 C14 . . 132.3(3) ?
C10 C9 C14 . . 121.9(3) ?
C9 C10 C11 . . 119.8(2) ?
C9 C10 N2 . . 109.5(2) ?
C11 C10 N2 . . 130.7(3) ?
C12A C11 C10 . . 117.6(3) ?
C12A C11 H11 . . 121.2 ?
C10 C11 H11 . . 121.2 ?
C13A C14 C9 . . 117.3(3) ?
C13A C14 H14 . . 121.4 ?
C9 C14 H14 . . 121.4 ?
C11 C12A C13A . . 123.6(3) ?
C11 C12A H12A . . 118.2 ?
C13A C12A H12A . . 118.2 ?
C12A C13A C14 . . 119.8(3) ?
C12A C13A C15A . . 115.3(4) ?
C14 C13A C15A . . 124.9(4) ?
C13A C15A H15A . . 109.5 ?
C13A C15A H15B . . 109.5 ?
H15A C15A H15B . . 109.5 ?
C13A C15A H15C . . 109.5 ?
H15A C15A H15C . . 109.5 ?
H15B C15A H15C . . 109.5 ?
H15G C15B H15D . . 109.5 ?
H15G C15B H15E . . 109.5 ?
H15D C15B H15E . . 109.5 ?
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 C2 . 1.357(3) ?
O1 H1 . 0.8200 ?
O2 C3 . 1.367(3) ?
O2 C8 . 1.438(3) ?
N1 C7 . 1.367(3) ?
N1 C9 . 1.382(3) ?
N1 H1A . 0.9194 ?
N2 C7 . 1.332(3) ?
N2 C10 . 1.394(3) ?
C1 C2 . 1.396(3) ?
C1 C6 . 1.397(4) ?
C1 C7 . 1.453(3) ?
C2 C3 . 1.399(3) ?
C3 C4 . 1.368(4) ?
C4 C5 . 1.384(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.366(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.393(4) ?
C9 C14 . 1.397(3) ?
C10 C11 . 1.394(4) ?
C11 C12A . 1.357(4) ?
C11 H11 . 0.9300 ?
C14 C13A . 1.388(5) ?
C14 H14 . 0.9300 ?
C12A C13A . 1.383(5) ?
C12A H12A . 0.9300 ?
C13A C15A . 1.531(4) ?
C15A H15A . 0.9600 ?
C15A H15B . 0.9600 ?
C15A H15C . 0.9600 ?
C15B H15G . 0.9600 ?
C15B H15D . 0.9600 ?
C15B H15E . 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
O1 H1 N2 . 0.82 1.83 2.567(2) 148.4
N1 H1A O2 6_576 0.92 2.54 3.173(3) 126.7
N1 H1A O1 6_576 0.92 2.06 2.920(3) 154.8
