#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226961.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_2226961
loop_
_publ_author_name
'Shi, Guang'
'Ma, Li'
'Deng, Hong'
_publ_section_title
;
 2-[1-(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)-1H-benzimidazol-2-yl]benzoic
 acid methanol solvate
;
_journal_coeditor_code           JH2172
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2034
_journal_paper_doi               10.1107/S1600536810026851
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C22 H14 N2 O4, C H4 O'
_chemical_formula_moiety         'C22 H14 N2 O4, C H4 O'
_chemical_formula_sum            'C23 H18 N2 O5'
_chemical_formula_weight         402.39
_chemical_name_systematic
;
2-[1-(3-Oxo-1,3-dihydro-2-benzofuran-1-yl)-1H-benzimidazol-
2-yl]benzoic acid methanol solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 103.985(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7946(8)
_cell_length_b                   9.7815(7)
_cell_length_c                   15.3083(9)
_cell_measurement_reflns_used    4300
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.20
_cell_measurement_theta_min      2.49
_cell_volume                     2004.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       '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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16115
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9812
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0793P)²+0.7223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1791
_reflns_number_gt                2220
_reflns_number_total             3618
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2172.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226961
_cod_database_fobs_code          2226961
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C C1 0.2698(3) 0.7568(4) 0.3140(2) 0.0646(8) Uani d . 1 . .
C C2 0.2114(2) 0.7749(3) 0.2192(2) 0.0574(8) Uani d . 1 . .
C C3 0.1577(3) 0.8940(3) 0.1918(2) 0.0735(9) Uani d . 1 . .
H H3 0.1539 0.9603 0.2344 0.088 Uiso calc R 1 . .
C C4 0.1102(3) 0.9157(4) 0.1035(3) 0.0837(11) Uani d . 1 . .
H H4 0.0743 0.9960 0.0869 0.100 Uiso calc R 1 . .
C C5 0.1153(3) 0.8195(4) 0.0393(2) 0.0802(10) Uani d . 1 . .
H H5 0.0842 0.8355 -0.0208 0.096 Uiso calc R 1 . .
C C6 0.1665(2) 0.6995(3) 0.0642(2) 0.0675(9) Uani d . 1 . .
H H6 0.1692 0.6343 0.0207 0.081 Uiso calc R 1 . .
C C7 0.2148(2) 0.6743(3) 0.15465(19) 0.0534(7) Uani d . 1 . .
C C8 0.2695(2) 0.5440(3) 0.17289(17) 0.0514(7) Uani d . 1 . .
C C9 0.3092(2) 0.3309(3) 0.21960(18) 0.0504(7) Uani d . 1 . .
C C10 0.3180(2) 0.1996(3) 0.2542(2) 0.0619(8) Uani d . 1 . .
H H10 0.2747 0.1664 0.2872 0.074 Uiso calc R 1 . .
C C11 0.3938(2) 0.1202(4) 0.2373(2) 0.0748(10) Uani d . 1 . .
H H11 0.4015 0.0313 0.2593 0.090 Uiso calc R 1 . .
C C12 0.4587(3) 0.1686(4) 0.1886(3) 0.0774(10) Uani d . 1 . .
H H12 0.5088 0.1113 0.1786 0.093 Uiso calc R 1 . .
C C13 0.4514(2) 0.2990(4) 0.1547(2) 0.0700(9) Uani d . 1 . .
H H13 0.4955 0.3313 0.1221 0.084 Uiso calc R 1 . .
C C14 0.3749(2) 0.3812(3) 0.17105(19) 0.0550(7) Uani d . 1 . .
C C15 0.2117(3) 0.3034(4) 0.4943(2) 0.0780(10) Uani d . 1 . .
H H15 0.2504 0.3200 0.5520 0.094 Uiso calc R 1 . .
C C16 0.1467(3) 0.1954(4) 0.4806(2) 0.0805(11) Uani d . 1 . .
H H16 0.1423 0.1408 0.5293 0.097 Uiso calc R 1 . .
C C17 0.0878(3) 0.1656(4) 0.3965(2) 0.0698(9) Uani d . 1 . .
H H17 0.0444 0.0913 0.3868 0.084 Uiso calc R 1 . .
C C18 0.0965(2) 0.2521(3) 0.32720(18) 0.0519(7) Uani d . 1 . .
C C19 0.1618(2) 0.3603(3) 0.34079(17) 0.0499(7) Uani d . 1 . .
C C20 0.2215(2) 0.3885(3) 0.42476(19) 0.0666(9) Uani d . 1 . .
H H20 0.2662 0.4613 0.4343 0.080 Uiso calc R 1 . .
C C21 0.1534(2) 0.4328(3) 0.25260(17) 0.0498(7) Uani d . 1 . .
H H21 0.1296 0.5263 0.2572 0.060 Uiso calc R 1 . .
C C22 0.0433(2) 0.2488(3) 0.2319(2) 0.0546(7) Uani d . 1 . .
C C24 0.4396(5) 0.6942(6) 0.5552(4) 0.149(2) Uani d . 1 . .
H H24A 0.5088 0.7002 0.5865 0.223 Uiso calc R 1 . .
H H24B 0.4319 0.6279 0.5078 0.223 Uiso calc R 1 . .
H H24C 0.4008 0.6671 0.5966 0.223 Uiso calc R 1 . .
N N1 0.34805(17) 0.5147(3) 0.14283(15) 0.0571(7) Uani d . 1 . .
N N2 0.24148(16) 0.4369(2) 0.22025(14) 0.0483(6) Uani d . 1 . .
O O1 0.3086(2) 0.6524(3) 0.34359(16) 0.0873(8) Uani d . 1 . .
O O2 0.2764(2) 0.8683(3) 0.36180(18) 0.1010(9) Uani d . 1 . .
H H2 0.3091 0.8530 0.4131 0.151 Uiso calc R 1 . .
O O3 -0.01827(18) 0.1711(3) 0.19162(15) 0.0789(7) Uani d . 1 . .
O O4 0.07646(14) 0.3553(2) 0.18969(12) 0.0556(5) Uani d . 1 . .
O O5 0.4054(2) 0.8271(3) 0.51697(18) 0.1090(10) Uani d . 1 . .
H H5A 0.3930 0.8763 0.5563 0.163 Uiso calc R 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 O2 . . 122.6(3) ?
O1 C1 C2 . . 124.1(3) ?
O2 C1 C2 . . 113.3(3) ?
C3 C2 C7 . . 118.7(3) ?
C3 C2 C1 . . 121.1(3) ?
C7 C2 C1 . . 120.0(3) ?
C4 C3 C2 . . 121.4(3) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 120.3(3) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C6 C5 C4 . . 119.8(3) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C7 . . 120.9(3) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C2 C7 C6 . . 118.8(3) ?
C2 C7 C8 . . 125.1(3) ?
C6 C7 C8 . . 116.0(3) ?
N1 C8 N2 . . 112.3(2) ?
N1 C8 C7 . . 123.6(2) ?
N2 C8 C7 . . 124.1(2) ?
C10 C9 C14 . . 121.6(3) ?
C10 C9 N2 . . 133.1(3) ?
C14 C9 N2 . . 105.3(2) ?
C11 C10 C9 . . 116.9(3) ?
C11 C10 H10 . . 121.5 ?
C9 C10 H10 . . 121.5 ?
C10 C11 C12 . . 122.0(3) ?
C10 C11 H11 . . 119.0 ?
C12 C11 H11 . . 119.0 ?
C13 C12 C11 . . 121.7(3) ?
C13 C12 H12 . . 119.2 ?
C11 C12 H12 . . 119.2 ?
C12 C13 C14 . . 117.2(3) ?
C12 C13 H13 . . 121.4 ?
C14 C13 H13 . . 121.4 ?
C9 C14 C13 . . 120.7(3) ?
C9 C14 N1 . . 109.7(2) ?
C13 C14 N1 . . 129.6(3) ?
C16 C15 C20 . . 122.0(3) ?
C16 C15 H15 . . 119.0 ?
C20 C15 H15 . . 119.0 ?
C15 C16 C17 . . 121.5(3) ?
C15 C16 H16 . . 119.2 ?
C17 C16 H16 . . 119.2 ?
C16 C17 C18 . . 116.4(3) ?
C16 C17 H17 . . 121.8 ?
C18 C17 H17 . . 121.8 ?
C19 C18 C17 . . 122.1(3) ?
C19 C18 C22 . . 108.7(2) ?
C17 C18 C22 . . 129.3(3) ?
C18 C19 C20 . . 121.2(3) ?
C18 C19 C21 . . 108.8(2) ?
C20 C19 C21 . . 130.0(3) ?
C19 C20 C15 . . 116.7(3) ?
C19 C20 H20 . . 121.6 ?
C15 C20 H20 . . 121.6 ?
N2 C21 O4 . . 109.3(2) ?
N2 C21 C19 . . 116.1(2) ?
O4 C21 C19 . . 103.4(2) ?
N2 C21 H21 . . 109.2 ?
O4 C21 H21 . . 109.2 ?
C19 C21 H21 . . 109.2 ?
O3 C22 O4 . . 121.4(3) ?
O3 C22 C18 . . 130.6(3) ?
O4 C22 C18 . . 108.0(2) ?
O5 C24 H24A . . 109.5 ?
O5 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
O5 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C8 N1 C14 . . 106.0(2) ?
C8 N2 C9 . . 106.6(2) ?
C8 N2 C21 . . 125.2(2) ?
C9 N2 C21 . . 127.7(2) ?
C1 O2 H2 . . 109.5 ?
C22 O4 C21 . . 111.0(2) ?
C24 O5 H5A . . 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
C1 O1 . 1.190(4) ?
C1 O2 . 1.305(4) ?
C1 C2 . 1.489(4) ?
C2 C3 . 1.390(4) ?
C2 C7 . 1.404(4) ?
C3 C4 . 1.369(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.376(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.405(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.473(4) ?
C8 N1 . 1.307(3) ?
C8 N2 . 1.381(3) ?
C9 C10 . 1.384(4) ?
C9 C14 . 1.393(4) ?
C9 N2 . 1.397(3) ?
C10 C11 . 1.376(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.372(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.397(4) ?
C13 H13 . 0.9300 ?
C14 N1 . 1.397(4) ?
C15 C16 . 1.368(5) ?
C15 C20 . 1.383(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.378(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.385(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.372(4) ?
C18 C22 . 1.467(4) ?
C19 C20 . 1.377(4) ?
C19 C21 . 1.505(4) ?
C20 H20 . 0.9300 ?
C21 N2 . 1.419(3) ?
C21 O4 . 1.461(3) ?
C21 H21 . 0.9800 ?
C22 O3 . 1.194(3) ?
C22 O4 . 1.362(3) ?
C24 O5 . 1.456(6) ?
C24 H24A . 0.9600 ?
C24 H24B . 0.9600 ?
C24 H24C . 0.9600 ?
O2 H2 . 0.8200 ?
O5 H5A . 0.8200 ?
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
O2 H2 O5 . 0.82 1.83 2.632(4) 167.4
O5 H5A N1 4_576 0.82 1.92 2.733(3) 173.2
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079356
