#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2221988.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_2221988
loop_
_publ_author_name
'Eltayeb, Naser Eltaher'
'Teoh, Siang Guan'
'Fun, Hoong-Kun'
'Jebas, Samuel Robinson'
'Adnan, Rohana'
_publ_section_title
;
 3-[1-(3-Hydroxybenzyl)-1<i>H</i>-benzimidazol-2-yl]phenol
;
_journal_coeditor_code           CV2563
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1374
_journal_page_last               o1375
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H16 N2 O2'
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_chemical_name_common
;
3-[1-(3-Hydroxybenzyl)-1<i>H</i>-benzimidazol-2-yl]phenol
;
_chemical_name_systematic
;
3-[1-(3-Hydroxybenzyl)-1<i>H</i>-benzimidazol-2-yl]phenol
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9480(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5128(2)
_cell_length_b                   12.1096(2)
_cell_length_c                   12.5235(2)
_cell_measurement_reflns_used    8327
_cell_measurement_temperature    100
_cell_measurement_theta_max      37.16
_cell_measurement_theta_min      2.39
_cell_volume                     1582.61(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_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  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34106
_diffrn_reflns_theta_full        36.00
_diffrn_reflns_theta_max         36.00
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         7426
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0482
_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/[\s^2^(Fo^2^)+(0.0723P)^2^+0.2344P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                6004
_reflns_number_total             7426
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    cv2563.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               2221988
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
O O1 0.60369(7) 0.60548(5) 0.04595(5) 0.01932(13) Uani d . 1
O O2 0.21201(7) 0.70928(6) 0.49193(6) 0.02850(16) Uani d . 1
N N1 0.36876(7) 0.35014(5) 0.31082(5) 0.01366(12) Uani d . 1
N N2 0.55084(7) 0.30903(6) 0.41524(5) 0.01468(12) Uani d . 1
C C1 0.34113(8) 0.26119(6) 0.37376(6) 0.01385(13) Uani d . 1
C C2 0.22644(8) 0.20556(7) 0.38301(6) 0.01625(14) Uani d . 1
H H2A 0.1502 0.2247 0.3415 0.019 Uiso calc R 1
C C3 0.23254(9) 0.12006(7) 0.45759(7) 0.01787(15) Uani d . 1
H H3A 0.1581 0.0820 0.4676 0.021 Uiso calc R 1
C C4 0.34872(9) 0.08978(7) 0.51829(7) 0.01903(16) Uani d . 1
H H4A 0.3497 0.0308 0.5659 0.023 Uiso calc R 1
C C5 0.46206(9) 0.14602(7) 0.50872(7) 0.01765(15) Uani d . 1
H H5A 0.5388 0.1255 0.5486 0.021 Uiso calc R 1
C C6 0.45615(8) 0.23468(6) 0.43671(6) 0.01408(13) Uani d . 1
C C7 0.49493(8) 0.37658(6) 0.34028(6) 0.01328(13) Uani d . 1
C C8 0.55758(8) 0.47449(6) 0.29966(6) 0.01346(13) Uani d . 1
C C9 0.55681(8) 0.49315(6) 0.18938(6) 0.01442(13) Uani d . 1
H H9A 0.5214 0.4411 0.1398 0.017 Uiso calc R 1
C C10 0.60956(8) 0.59058(6) 0.15413(6) 0.01466(14) Uani d . 1
C C11 0.66423(8) 0.66833(7) 0.22849(6) 0.01679(15) Uani d . 1
H H11A 0.6988 0.7333 0.2049 0.020 Uiso calc R 1
C C12 0.66666(9) 0.64783(7) 0.33810(7) 0.01769(15) Uani d . 1
H H12A 0.7041 0.6990 0.3876 0.021 Uiso calc R 1
C C13 0.61356(8) 0.55155(7) 0.37433(6) 0.01600(14) Uani d . 1
H H13A 0.6153 0.5385 0.4477 0.019 Uiso calc R 1
C C14 0.27189(8) 0.40916(7) 0.23858(6) 0.01493(14) Uani d . 1
H H14A 0.2199 0.3560 0.1948 0.018 Uiso calc R 1
H H14B 0.3144 0.4556 0.1907 0.018 Uiso calc R 1
C C15 0.18581(8) 0.47993(7) 0.29866(6) 0.01546(14) Uani d . 1
C C16 0.05416(9) 0.46392(8) 0.28541(7) 0.02214(17) Uani d . 1
H H16A 0.0182 0.4078 0.2409 0.027 Uiso calc R 1
C C17 -0.02425(10) 0.53232(10) 0.33909(9) 0.0298(2) Uani d . 1
H H17A -0.1126 0.5226 0.3289 0.036 Uiso calc R 1
C C18 0.02893(10) 0.61473(9) 0.40753(8) 0.0276(2) Uani d . 1
H H18A -0.0235 0.6601 0.4432 0.033 Uiso calc R 1
C C19 0.16150(9) 0.62907(8) 0.42254(7) 0.02011(16) Uani d . 1
C C20 0.23951(8) 0.56315(7) 0.36681(6) 0.01647(14) Uani d . 1
H H20A 0.3276 0.5746 0.3750 0.020 Uiso calc R 1
H H1O1 0.6430(17) 0.6716(15) 0.0307(14) 0.053(5) Uiso d . 1
H H1O2 0.3026(18) 0.6952(15) 0.5216(14) 0.055(5) Uiso d . 1
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
O1 0.0266(3) 0.0181(3) 0.0133(2) -0.0054(2) 0.0028(2) 0.00132(19)
O2 0.0206(3) 0.0285(3) 0.0336(4) 0.0103(3) -0.0083(3) -0.0167(3)
N1 0.0134(3) 0.0145(3) 0.0127(3) 0.0004(2) 0.0002(2) 0.0011(2)
N2 0.0139(3) 0.0155(3) 0.0144(3) 0.0006(2) 0.0007(2) 0.0009(2)
C1 0.0148(3) 0.0135(3) 0.0131(3) -0.0001(2) 0.0012(3) -0.0002(2)
C2 0.0151(3) 0.0170(3) 0.0162(3) -0.0022(3) 0.0003(3) -0.0013(2)
C3 0.0204(4) 0.0161(3) 0.0173(3) -0.0041(3) 0.0029(3) -0.0011(2)
C4 0.0242(4) 0.0149(3) 0.0181(3) -0.0023(3) 0.0027(3) 0.0015(3)
C5 0.0197(4) 0.0158(3) 0.0169(3) 0.0008(3) 0.0001(3) 0.0024(2)
C6 0.0147(3) 0.0136(3) 0.0137(3) 0.0002(2) 0.0008(3) -0.0003(2)
C7 0.0131(3) 0.0143(3) 0.0124(3) 0.0001(2) 0.0013(2) -0.0007(2)
C8 0.0122(3) 0.0142(3) 0.0140(3) 0.0001(2) 0.0018(2) -0.0003(2)
C9 0.0159(3) 0.0142(3) 0.0131(3) -0.0019(2) 0.0018(3) -0.0008(2)
C10 0.0154(3) 0.0151(3) 0.0138(3) -0.0006(3) 0.0026(3) -0.0001(2)
C11 0.0183(4) 0.0148(3) 0.0173(3) -0.0026(3) 0.0023(3) -0.0013(2)
C12 0.0186(4) 0.0180(3) 0.0165(3) -0.0035(3) 0.0021(3) -0.0036(2)
C13 0.0161(4) 0.0180(3) 0.0138(3) -0.0011(3) 0.0016(3) -0.0019(2)
C14 0.0145(3) 0.0177(3) 0.0120(3) 0.0020(3) -0.0010(3) 0.0002(2)
C15 0.0148(3) 0.0176(3) 0.0136(3) 0.0022(3) 0.0000(3) 0.0002(2)
C16 0.0145(4) 0.0283(4) 0.0229(4) 0.0005(3) -0.0007(3) -0.0069(3)
C17 0.0133(4) 0.0409(6) 0.0349(5) 0.0020(4) 0.0017(4) -0.0144(4)
C18 0.0162(4) 0.0369(5) 0.0292(5) 0.0071(4) 0.0002(3) -0.0126(4)
C19 0.0174(4) 0.0217(4) 0.0200(4) 0.0057(3) -0.0028(3) -0.0053(3)
C20 0.0137(3) 0.0178(3) 0.0172(3) 0.0026(3) -0.0006(3) -0.0017(3)
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
C10 O1 H1O1 110.5(11)
C19 O2 H1O2 113.3(10)
C7 N1 C1 106.91(6)
C7 N1 C14 129.07(7)
C1 N1 C14 123.56(7)
C7 N2 C6 105.62(7)
N1 C1 C2 131.58(8)
N1 C1 C6 105.82(7)
C2 C1 C6 122.56(7)
C3 C2 C1 116.37(8)
C3 C2 H2A 121.8
C1 C2 H2A 121.8
C2 C3 C4 121.56(8)
C2 C3 H3A 119.2
C4 C3 H3A 119.2
C5 C4 C3 121.52(8)
C5 C4 H4A 119.2
C3 C4 H4A 119.2
C4 C5 C6 117.39(8)
C4 C5 H5A 121.3
C6 C5 H5A 121.3
N2 C6 C1 109.41(7)
N2 C6 C5 130.08(8)
C1 C6 C5 120.50(7)
N2 C7 N1 112.19(7)
N2 C7 C8 124.10(7)
N1 C7 C8 123.52(7)
C9 C8 C13 120.26(7)
C9 C8 C7 121.37(7)
C13 C8 C7 118.31(7)
C10 C9 C8 119.55(7)
C10 C9 H9A 120.2
C8 C9 H9A 120.2
O1 C10 C9 117.03(7)
O1 C10 C11 122.64(7)
C9 C10 C11 120.33(7)
C12 C11 C10 119.59(7)
C12 C11 H11A 120.2
C10 C11 H11A 120.2
C11 C12 C13 120.69(8)
C11 C12 H12A 119.7
C13 C12 H12A 119.7
C12 C13 C8 119.56(7)
C12 C13 H13A 120.2
C8 C13 H13A 120.2
N1 C14 C15 112.50(6)
N1 C14 H14A 109.1
C15 C14 H14A 109.1
N1 C14 H14B 109.1
C15 C14 H14B 109.1
H14A C14 H14B 107.8
C16 C15 C20 119.87(7)
C16 C15 C14 120.66(7)
C20 C15 C14 119.46(7)
C15 C16 C17 119.85(9)
C15 C16 H16A 120.1
C17 C16 H16A 120.1
C18 C17 C16 120.42(9)
C18 C17 H17A 119.8
C16 C17 H17A 119.8
C17 C18 C19 119.60(8)
C17 C18 H18A 120.2
C19 C18 H18A 120.2
O2 C19 C20 121.29(8)
O2 C19 C18 118.63(8)
C20 C19 C18 120.08(8)
C19 C20 C15 120.13(8)
C19 C20 H20A 119.9
C15 C20 H20A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.3607(10)
O1 H1O1 0.931(19)
O2 C19 1.3671(11)
O2 H1O2 0.994(19)
N1 C7 1.3709(10)
N1 C1 1.3861(10)
N1 C14 1.4641(11)
N2 C7 1.3275(10)
N2 C6 1.3923(10)
C1 C2 1.3981(11)
C1 C6 1.3986(12)
C2 C3 1.3906(11)
C2 H2A 0.9300
C3 C4 1.4070(13)
C3 H3A 0.9300
C4 C5 1.3901(12)
C4 H4A 0.9300
C5 C6 1.3987(11)
C5 H5A 0.9300
C7 C8 1.4763(10)
C8 C9 1.3985(10)
C8 C13 1.3995(11)
C9 C10 1.3977(11)
C9 H9A 0.9300
C10 C11 1.3980(11)
C11 C12 1.3922(11)
C11 H11A 0.9300
C12 C13 1.3922(11)
C12 H12A 0.9300
C13 H13A 0.9300
C14 C15 1.5114(11)
C14 H14A 0.9700
C14 H14B 0.9700
C15 C16 1.3874(13)
C15 C20 1.3951(11)
C16 C17 1.3970(13)
C16 H16A 0.9300
C17 C18 1.3882(14)
C17 H17A 0.9300
C18 C19 1.3944(14)
C18 H18A 0.9300
C19 C20 1.3911(11)
C20 H20A 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
O1 H1O1 O2 4_675 0.931(19) 1.712(19) 2.6406(9) 175.4(17)
O2 H1O2 N2 3_666 0.994(19) 1.646(19) 2.6297(10) 169.7(16)
C3 H3A O1 4_566 0.93 2.57 3.2987(10) 136.1
C9 H9A O1 3_665 0.93 2.59 3.4287(10) 149.9
C12 H12A Cg1 3_666 0.93 2.67 3.4521(9) 142
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 C1 C2 175.17(8)
C14 N1 C1 C2 2.30(12)
C7 N1 C1 C6 -2.40(8)
C14 N1 C1 C6 -175.27(6)
N1 C1 C2 C3 -178.27(8)
C6 C1 C2 C3 -1.05(11)
C1 C2 C3 C4 -1.54(12)
C2 C3 C4 C5 1.89(13)
C3 C4 C5 C6 0.40(12)
C7 N2 C6 C1 -1.16(8)
C7 N2 C6 C5 180.00(8)
N1 C1 C6 N2 2.23(8)
C2 C1 C6 N2 -175.61(7)
N1 C1 C6 C5 -178.80(7)
C2 C1 C6 C5 3.37(11)
C4 C5 C6 N2 175.81(8)
C4 C5 C6 C1 -2.93(11)
C6 N2 C7 N1 -0.41(8)
C6 N2 C7 C8 174.77(7)
C1 N1 C7 N2 1.81(8)
C14 N1 C7 N2 174.16(7)
C1 N1 C7 C8 -173.40(7)
C14 N1 C7 C8 -1.05(11)
N2 C7 C8 C9 130.08(8)
N1 C7 C8 C9 -55.28(11)
N2 C7 C8 C13 -52.67(10)
N1 C7 C8 C13 121.97(8)
C13 C8 C9 C10 -1.55(12)
C7 C8 C9 C10 175.65(7)
C8 C9 C10 O1 -178.61(7)
C8 C9 C10 C11 0.81(12)
O1 C10 C11 C12 179.82(8)
C9 C10 C11 C12 0.44(13)
C10 C11 C12 C13 -0.95(13)
C11 C12 C13 C8 0.22(13)
C9 C8 C13 C12 1.04(12)
C7 C8 C13 C12 -176.24(8)
C7 N1 C14 C15 -98.85(9)
C1 N1 C14 C15 72.35(9)
N1 C14 C15 C16 -121.88(9)
N1 C14 C15 C20 59.08(10)
C20 C15 C16 C17 0.98(14)
C14 C15 C16 C17 -178.05(9)
C15 C16 C17 C18 -1.43(17)
C16 C17 C18 C19 0.02(18)
C17 C18 C19 O2 -178.72(10)
C17 C18 C19 C20 1.83(16)
O2 C19 C20 C15 178.29(8)
C18 C19 C20 C15 -2.28(14)
C16 C15 C20 C19 0.86(13)
C14 C15 C20 C19 179.91(8)