#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/49/2214914.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_2214914
loop_
_publ_author_name
'Qing-Guang Zhan'
'Mao-Sheng Liu'
'Rong-Hua Zeng'
'Ding-Qiao Yang'
'Yue-Peng Cai'
_publ_section_title
;
 4-(1H-Benzo[d]imidazol-2-yl)phenol
;
_journal_coeditor_code           XU2292
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3470
_journal_page_last               o3470
_journal_paper_doi               10.1107/S1600536807033612
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H10 N2 O'
_chemical_formula_moiety         'C13 H10 N2 O'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23
_chemical_melting_point          508
_chemical_name_systematic
;
4-(1H-Benzo[d]imidazol-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                 90.556(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1679(3)
_cell_length_b                   15.1517(6)
_cell_length_c                   9.9079(4)
_cell_measurement_reflns_used    5172
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     1076.01(8)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.019
_diffrn_reflns_av_sigmaI/netI    0.016
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10089
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.4
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.037
_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)+(0.0496P)²+0.1927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.098
_refine_ls_wR_factor_ref         0.103
_reflns_number_gt                2092
_reflns_number_total             2464
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2292.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214914
_cod_database_fobs_code          2214914
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 0.12380(10) 0.35627(6) 0.15835(9) 0.0498(2) Uani d . 1
H H1A 0.0185 0.3760 0.1462 0.075 Uiso calc R 1
N N2 0.29490(13) 0.06719(6) 0.61996(10) 0.0455(2) Uani d . 1
N N1 -0.01358(12) 0.06759(6) 0.63364(10) 0.0406(2) Uani d D 1
C C1 0.24064(16) 0.00742(8) 0.71879(12) 0.0460(3) Uani d . 1
C C2 0.3466(2) -0.04686(10) 0.80335(16) 0.0646(4) Uani d . 1
H H2 0.4761 -0.0477 0.7984 0.078 Uiso calc R 1
C C3 0.2541(2) -0.09910(10) 0.89419(16) 0.0691(4) Uani d . 1
H H3 0.3225 -0.1360 0.9511 0.083 Uiso calc R 1
C C4 0.0615(2) -0.09817(9) 0.90314(14) 0.0614(4) Uani d . 1
H H4 0.0036 -0.1344 0.9659 0.074 Uiso calc R 1
C C5 -0.04601(19) -0.04497(9) 0.82150(13) 0.0522(3) Uani d . 1
H H5 -0.1754 -0.0442 0.8278 0.063 Uiso calc R 1
C C6 0.04717(15) 0.00766(7) 0.72905(11) 0.0412(3) Uani d . 1
C C7 0.13874(14) 0.10192(7) 0.57169(11) 0.0381(2) Uani d . 1
C C8 0.12968(14) 0.16878(7) 0.46561(10) 0.0381(2) Uani d . 1
C C9 0.29061(15) 0.19137(8) 0.39541(12) 0.0448(3) Uani d . 1
H H9 0.4029 0.1639 0.4175 0.054 Uiso calc R 1
C C10 0.28632(15) 0.25331(8) 0.29430(12) 0.0467(3) Uani d . 1
H H10 0.3953 0.2671 0.2487 0.056 Uiso calc R 1
C C11 0.12059(15) 0.29563(8) 0.25943(11) 0.0407(3) Uani d . 1
C C12 -0.04087(15) 0.27377(8) 0.32846(12) 0.0446(3) Uani d . 1
H H12 -0.1528 0.3016 0.3065 0.054 Uiso calc R 1
C C13 -0.03603(15) 0.21105(8) 0.42931(11) 0.0435(3) Uani d . 1
H H13 -0.1455 0.1967 0.4739 0.052 Uiso calc R 1
H H1 -0.1306(13) 0.0848(9) 0.6208(13) 0.052 Uiso d D 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
C11 O1 H1A 109.5
C7 N2 C1 105.79(9)
C7 N1 C6 108.16(9)
C7 N1 H1 125.8(9)
C6 N1 H1 125.8(9)
C6 C1 N2 109.58(10)
C6 C1 C2 119.69(12)
N2 C1 C2 130.72(12)
C3 C2 C1 118.03(13)
C3 C2 H2 121.0
C1 C2 H2 121.0
C2 C3 C4 121.61(13)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 121.50(14)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 117.02(13)
C4 C5 H5 121.5
C6 C5 H5 121.5
N1 C6 C5 132.78(11)
N1 C6 C1 105.07(10)
C5 C6 C1 122.15(11)
N2 C7 N1 111.40(10)
N2 C7 C8 124.60(10)
N1 C7 C8 124.00(9)
C13 C8 C9 117.74(11)
C13 C8 C7 122.42(10)
C9 C8 C7 119.83(10)
C10 C9 C8 121.24(10)
C10 C9 H9 119.4
C8 C9 H9 119.4
C9 C10 C11 120.63(10)
C9 C10 H10 119.7
C11 C10 H10 119.7
O1 C11 C12 122.93(10)
O1 C11 C10 118.30(10)
C12 C11 C10 118.76(11)
C13 C12 C11 120.36(10)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C8 121.27(10)
C12 C13 H13 119.4
C8 C13 H13 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.3595(14)
O1 H1A 0.8200
N2 C7 1.3221(14)
N2 C1 1.3920(15)
N1 C7 1.3610(14)
N1 C6 1.3784(15)
N1 H1 0.886(8)
C1 C6 1.3915(16)
C1 C2 1.3939(18)
C2 C3 1.374(2)
C2 H2 0.9300
C3 C4 1.384(2)
C3 H3 0.9300
C4 C5 1.3733(19)
C4 H4 0.9300
C5 C6 1.3902(17)
C5 H5 0.9300
C7 C8 1.4609(16)
C8 C13 1.3935(15)
C8 C9 1.3953(15)
C9 C10 1.3728(17)
C9 H9 0.9300
C10 C11 1.3906(15)
C10 H10 0.9300
C11 C12 1.3901(15)
C12 C13 1.3792(16)
C12 H12 0.9300
C13 H13 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 H1A N2 4_565 0.82 1.84 2.6515(12) 174
N1 H1 O1 4_566 0.886(8) 2.012(9) 2.8564(12) 158.8(12)
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 N2 C1 C6 -0.36(13)
C7 N2 C1 C2 -179.12(14)
C6 C1 C2 C3 0.4(2)
N2 C1 C2 C3 179.05(13)
C1 C2 C3 C4 -0.4(2)
C2 C3 C4 C5 0.0(2)
C3 C4 C5 C6 0.3(2)
C7 N1 C6 C5 178.88(12)
C7 N1 C6 C1 -0.89(12)
C4 C5 C6 N1 -179.96(12)
C4 C5 C6 C1 -0.23(18)
N2 C1 C6 N1 0.77(13)
C2 C1 C6 N1 179.70(12)
N2 C1 C6 C5 -179.02(10)
C2 C1 C6 C5 -0.10(18)
C1 N2 C7 N1 -0.22(12)
C1 N2 C7 C8 179.65(10)
C6 N1 C7 N2 0.72(12)
C6 N1 C7 C8 -179.15(9)
N2 C7 C8 C13 -172.12(11)
N1 C7 C8 C13 7.74(16)
N2 C7 C8 C9 8.78(16)
N1 C7 C8 C9 -171.36(10)
C13 C8 C9 C10 0.21(17)
C7 C8 C9 C10 179.36(11)
C8 C9 C10 C11 0.26(19)
C9 C10 C11 O1 -179.84(11)
C9 C10 C11 C12 -0.28(18)
O1 C11 C12 C13 179.35(11)
C10 C11 C12 C13 -0.18(18)
C11 C12 C13 C8 0.67(18)
C9 C8 C13 C12 -0.68(17)
C7 C8 C13 C12 -179.80(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11326757
2 PubChem 675624
