#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/90/2239005.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2239005
loop_
_publ_author_name
'Rivera, Augusto'
'Jiménez-Cruz, Leonardo'
'Bolte, Michael'
_publ_section_title
;
 2-[(1H-Benzimidazol-1-yl)methyl]phenol benzene hemisolvate
;
_journal_coeditor_code           SJ5381
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o177
_journal_paper_doi               10.1107/S1600536814000841
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C14 H12 N2 O, 0.5C6 H6'
_chemical_formula_moiety         'C14 H12 N2 O, 0.5(C6 H6)'
_chemical_formula_sum            'C17 H15 N2 O'
_chemical_formula_weight         263.31
_chemical_name_systematic
;
2-[(1H-Benzimidazol-1-yl)methyl]phenol benzene hemisolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                73.098(8)
_cell_angle_beta                 69.124(8)
_cell_angle_gamma                62.148(8)
_cell_formula_units_Z            2
_cell_length_a                   8.9351(11)
_cell_length_b                   9.3268(10)
_cell_length_c                   9.9579(11)
_cell_measurement_reflns_used    14234
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      3.58
_cell_volume                     677.75(15)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8981
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.847
_diffrn_reflns_theta_min         3.890
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(X-AREA; Stoe & Cie, 2001)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       needle
_exptl_crystal_F_000             278
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.166
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0390P)²+0.2380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                2314
_reflns_number_total             2591
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5381sup1.cif
_cod_data_source_block           I
_cod_database_code               2239005
_cod_database_fobs_code          2239005
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.990
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
O O1 0.26163(13) 0.72436(14) 0.00166(12) 0.0358(3) Uani d 1
H H1 0.155(3) 0.706(3) 0.023(2) 0.064(6) Uiso d 1
N N1 0.72313(15) 0.66159(14) 0.07264(13) 0.0272(3) Uani d 1
N N2 0.96889(15) 0.66557(15) 0.07838(14) 0.0323(3) Uani d 1
C C1 0.84911(18) 0.71998(18) 0.00788(16) 0.0298(3) Uani d 1
H H1A 0.8506 0.7939 -0.0809 0.036 Uiso calc 1
C C2 0.91796(18) 0.56313(17) 0.20031(15) 0.0286(3) Uani d 1
C C3 0.76391(18) 0.55998(16) 0.19817(15) 0.0274(3) Uani d 1
C C4 0.6810(2) 0.46847(19) 0.30695(17) 0.0383(4) Uani d 1
H H4 0.5766 0.4670 0.3040 0.046 Uiso calc 1
C C5 0.7585(3) 0.3802(2) 0.41906(19) 0.0478(4) Uani d 1
H H5 0.7057 0.3167 0.4963 0.057 Uiso calc 1
C C6 0.9130(3) 0.3812(2) 0.42267(18) 0.0487(5) Uani d 1
H H6 0.9627 0.3176 0.5018 0.058 Uiso calc 1
C C7 0.9953(2) 0.47195(19) 0.31466(18) 0.0397(4) Uani d 1
H H7 1.1000 0.4723 0.3180 0.048 Uiso calc 1
C C8 0.57443(18) 0.69824(19) 0.02012(16) 0.0313(3) Uani d 1
H H8A 0.5715 0.5940 0.0184 0.038 Uiso calc 1
H H8B 0.5908 0.7566 -0.0808 0.038 Uiso calc 1
C C11 0.40093(17) 0.80188(16) 0.11250(15) 0.0270(3) Uani d 1
C C12 0.24639(18) 0.80968(17) 0.09924(15) 0.0274(3) Uani d 1
C C13 0.08497(18) 0.90253(18) 0.18424(16) 0.0322(3) Uani d 1
H H13 -0.0200 0.9101 0.1733 0.039 Uiso calc 1
C C14 0.0764(2) 0.98409(18) 0.28484(16) 0.0341(3) Uani d 1
H H14 -0.0341 1.0448 0.3444 0.041 Uiso calc 1
C C15 0.2284(2) 0.97727(18) 0.29875(16) 0.0344(3) Uani d 1
H H15 0.2228 1.0335 0.3673 0.041 Uiso calc 1
C C16 0.38896(19) 0.88763(17) 0.21170(16) 0.0309(3) Uani d 1
H H16 0.4930 0.8848 0.2201 0.037 Uiso calc 1
C C21 0.4166(2) 0.9279(2) 0.62694(19) 0.0456(4) Uani d 1
H H21 0.3596 0.8781 0.7143 0.055 Uiso calc 1
C C22 0.6494(2) 0.9049(2) 0.4094(2) 0.0455(4) Uani d 1
H H22 0.7529 0.8387 0.3470 0.055 Uiso calc 1
C C23 0.5668(2) 0.8322(2) 0.5354(2) 0.0474(4) Uani d 1
H H23 0.6131 0.7161 0.5595 0.057 Uiso calc 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
C12 O1 H1 . 111.1(12)
C1 N1 C3 . 106.30(12)
C1 N1 C8 . 126.83(12)
C3 N1 C8 . 126.86(12)
C1 N2 C2 . 104.48(11)
N2 C1 N1 . 114.07(13)
N2 C1 H1A . 123.0
N1 C1 H1A . 123.0
N2 C2 C7 . 130.19(14)
N2 C2 C3 . 109.62(12)
C7 C2 C3 . 120.19(14)
N1 C3 C4 . 131.74(14)
N1 C3 C2 . 105.52(12)
C4 C3 C2 . 122.74(14)
C5 C4 C3 . 116.22(16)
C5 C4 H4 . 121.9
C3 C4 H4 . 121.9
C4 C5 C6 . 121.83(16)
C4 C5 H5 . 119.1
C6 C5 H5 . 119.1
C7 C6 C5 . 121.91(15)
C7 C6 H6 . 119.0
C5 C6 H6 . 119.0
C6 C7 C2 . 117.10(16)
C6 C7 H7 . 121.4
C2 C7 H7 . 121.4
N1 C8 C11 . 112.97(11)
N1 C8 H8A . 109.0
C11 C8 H8A . 109.0
N1 C8 H8B . 109.0
C11 C8 H8B . 109.0
H8A C8 H8B . 107.8
C16 C11 C12 . 118.72(13)
C16 C11 C8 . 122.58(12)
C12 C11 C8 . 118.69(12)
O1 C12 C13 . 122.49(12)
O1 C12 C11 . 117.60(12)
C13 C12 C11 . 119.91(13)
C14 C13 C12 . 120.37(13)
C14 C13 H13 . 119.8
C12 C13 H13 . 119.8
C15 C14 C13 . 120.17(13)
C15 C14 H14 . 119.9
C13 C14 H14 . 119.9
C14 C15 C16 . 119.39(13)
C14 C15 H15 . 120.3
C16 C15 H15 . 120.3
C15 C16 C11 . 121.41(13)
C15 C16 H16 . 119.3
C11 C16 H16 . 119.3
C22 C21 C23 2_676 119.45(16)
C22 C21 H21 2_676 120.3
C23 C21 H21 . 120.3
C21 C22 C23 2_676 120.50(16)
C21 C22 H22 2_676 119.8
C23 C22 H22 . 119.8
C22 C23 C21 . 120.05(17)
C22 C23 H23 . 120.0
C21 C23 H23 . 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C12 . 1.3602(17)
O1 H1 . 0.98(2)
N1 C1 . 1.3531(18)
N1 C3 . 1.3807(19)
N1 C8 . 1.4570(17)
N2 C1 . 1.3101(19)
N2 C2 . 1.390(2)
C1 H1A . 0.9500
C2 C7 . 1.395(2)
C2 C3 . 1.398(2)
C3 C4 . 1.390(2)
C4 C5 . 1.374(3)
C4 H4 . 0.9500
C5 C6 . 1.398(3)
C5 H5 . 0.9500
C6 C7 . 1.379(3)
C6 H6 . 0.9500
C7 H7 . 0.9500
C8 C11 . 1.5114(19)
C8 H8A . 0.9900
C8 H8B . 0.9900
C11 C16 . 1.390(2)
C11 C12 . 1.3999(19)
C12 C13 . 1.391(2)
C13 C14 . 1.386(2)
C13 H13 . 0.9500
C14 C15 . 1.385(2)
C14 H14 . 0.9500
C15 C16 . 1.387(2)
C15 H15 . 0.9500
C16 H16 . 0.9500
C21 C22 2_676 1.370(3)
C21 C23 . 1.383(3)
C21 H21 . 0.9500
C22 C21 2_676 1.370(3)
C22 C23 . 1.375(3)
C22 H22 . 0.9500
C23 H23 . 0.9500
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 1_455 0.98(2) 1.74(2) 2.7200(16) 174(2)
C22 H22 Cg1 . 0.95 3.25 3.868 124
C22 H22 Cg2 . 0.95 3.10 3.844 137
C15 H15 Cg3 . 0.95 3.06 3.761 132
C16 H16 Cg3 . 0.95 3.30 3.883 122
C1 H1A Cg4 2_675 0.95 2.65 3.467 145
C5 H5 Cg4 2_666 0.95 3.17 3.922 138
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_site_symmetry_1
_geom_torsion
C2 N2 C1 N1 . -0.25(16)
C3 N1 C1 N2 . 0.43(16)
C8 N1 C1 N2 . -179.40(12)
C1 N2 C2 C7 . -179.68(15)
C1 N2 C2 C3 . -0.02(15)
C1 N1 C3 C4 . 179.49(15)
C8 N1 C3 C4 . -0.7(2)
C1 N1 C3 C2 . -0.40(14)
C8 N1 C3 C2 . 179.42(12)
N2 C2 C3 N1 . 0.27(15)
C7 C2 C3 N1 . 179.96(12)
N2 C2 C3 C4 . -179.63(12)
C7 C2 C3 C4 . 0.1(2)
N1 C3 C4 C5 . -179.58(14)
C2 C3 C4 C5 . 0.3(2)
C3 C4 C5 C6 . -0.6(2)
C4 C5 C6 C7 . 0.6(3)
C5 C6 C7 C2 . -0.2(2)
N2 C2 C7 C6 . 179.51(14)
C3 C2 C7 C6 . -0.1(2)
C1 N1 C8 C11 . -110.59(16)
C3 N1 C8 C11 . 69.62(17)
N1 C8 C11 C16 . 15.8(2)
N1 C8 C11 C12 . -163.13(12)
C16 C11 C12 O1 . -179.84(12)
C8 C11 C12 O1 . -0.84(19)
C16 C11 C12 C13 . 0.2(2)
C8 C11 C12 C13 . 179.21(13)
O1 C12 C13 C14 . 178.38(13)
C11 C12 C13 C14 . -1.7(2)
C12 C13 C14 C15 . 1.7(2)
C13 C14 C15 C16 . -0.3(2)
C14 C15 C16 C11 . -1.2(2)
C12 C11 C16 C15 . 1.2(2)
C8 C11 C16 C15 . -177.73(13)
C21 C22 C23 C21 2_676 -0.3(3)
C22 C21 C23 C22 2_676 0.3(3)
