#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/66/2236619.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_2236619
loop_
_publ_author_name
'Kuai, Hai-Wei'
_publ_section_title
;
 A monoclinic polymorph of
 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid
;
_journal_coeditor_code           SJ5265
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3068
_journal_paper_doi               10.1107/S1600536812041025
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H12 N2 O4'
_chemical_formula_moiety         'C16 H12 N2 O4'
_chemical_formula_sum            'C16 H12 N2 O4'
_chemical_formula_weight         296.28
_chemical_name_systematic
;
5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid
;
_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                 111.53(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.401(5)
_cell_length_b                   16.589(5)
_cell_length_c                   11.762(4)
_cell_measurement_reflns_used    479
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.53
_cell_measurement_theta_min      2.23
_cell_volume                     1343.3(11)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2000) and Mercury (Macrae et al.,
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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEXII CCD'
_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  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0838
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6722
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.23
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.215
_refine_ls_extinction_coef       0.0052(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0559
_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)+(0.0659P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1523
_reflns_number_gt                1239
_reflns_number_total             2358
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5265.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               2236619
_cod_database_fobs_code          2236619
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_symmetry_multiplicity
C C1 0.4929(4) 0.81173(19) 0.6457(3) 0.0337(8) Uani d . 1 1
C C2 0.3157(4) 0.81097(19) 0.5499(3) 0.0359(8) Uani d . 1 1
H H1 0.2128 0.7828 0.5586 0.043 Uiso calc R 1 1
C C3 0.2869(4) 0.85118(19) 0.4407(3) 0.0334(8) Uani d . 1 1
C C4 0.4398(4) 0.89389(18) 0.4285(3) 0.0322(8) Uani d . 1 1
H H2 0.4224 0.9211 0.3561 0.039 Uiso calc R 1 1
C C5 0.6190(4) 0.89614(19) 0.5242(3) 0.0335(8) Uani d . 1 1
C C6 0.6444(4) 0.85508(19) 0.6319(3) 0.0369(8) Uani d . 1 1
H H3 0.7645 0.8566 0.6957 0.044 Uiso calc R 1 1
C C11 0.5228(4) 0.7621(2) 0.7587(2) 0.0393(9) Uani d . 1 1
H H7 0.4032 0.7336 0.7480 0.047 Uiso calc R 1 1
H H6 0.6222 0.7220 0.7666 0.047 Uiso calc R 1 1
C C12 0.7566(4) 0.8106(2) 0.9604(3) 0.0419(9) Uani d . 1 1
H H8 0.8643 0.7849 0.9542 0.050 Uiso calc R 1 1
C C13 0.5734(5) 0.87902(19) 1.0306(3) 0.0391(9) Uani d . 1 1
C C14 0.4574(4) 0.85280(19) 0.9137(3) 0.0359(8) Uani d . 1 1
C C15 0.2615(5) 0.8708(2) 0.8615(3) 0.0526(10) Uani d . 1 1
H H9 0.1855 0.8535 0.7833 0.063 Uiso calc R 1 1
C C16 0.1854(6) 0.9155(2) 0.9315(4) 0.0641(11) Uani d . 1 1
H H10 0.0545 0.9293 0.8993 0.077 Uiso calc R 1 1
C C17 0.2977(6) 0.9410(2) 1.0494(4) 0.0616(11) Uani d . 1 1
H H11 0.2394 0.9698 1.0945 0.074 Uiso calc R 1 1
C C18 0.4931(5) 0.9243(2) 1.1002(3) 0.0529(10) Uani d . 1 1
H H12 0.5688 0.9424 1.1780 0.063 Uiso calc R 1 1
C C31 0.0929(5) 0.8454(2) 0.3395(3) 0.0421(9) Uani d . 1 1
C C51 0.7854(5) 0.9411(2) 0.5135(3) 0.0393(8) Uani d . 1 1
N N1 0.7629(4) 0.85258(17) 1.0568(2) 0.0451(8) Uani d . 1 1
N N2 0.5798(3) 0.80875(16) 0.8720(2) 0.0363(7) Uani d . 1 1
O O1 0.0865(3) 0.87513(17) 0.23681(19) 0.0661(8) Uani d . 1 1
H H4 -0.0285 0.8693 0.1880 0.079 Uiso d R 1 1
O O2 -0.0442(3) 0.81489(18) 0.3545(2) 0.0756(9) Uani d . 1 1
O O3 0.7501(3) 0.97884(14) 0.41101(19) 0.0493(7) Uani d . 1 1
H H5 0.8528 1.0018 0.4151 0.059 Uiso d R 1 1
O O4 0.9450(3) 0.94199(15) 0.5985(2) 0.0584(8) Uani d . 1 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
C2 C1 C6 118.4(3)
C2 C1 C11 120.1(3)
C6 C1 C11 121.4(3)
C1 C2 C3 121.7(3)
C1 C2 H1 119.1
C3 C2 H1 119.1
C4 C3 C2 119.1(3)
C4 C3 C31 122.2(3)
C2 C3 C31 118.8(3)
C3 C4 C5 120.2(3)
C3 C4 H2 119.9
C5 C4 H2 119.9
C6 C5 C4 119.6(3)
C6 C5 C51 119.1(3)
C4 C5 C51 121.3(3)
C5 C6 C1 121.0(3)
C5 C6 H3 119.5
C1 C6 H3 119.5
N2 C11 C1 114.4(3)
N2 C11 H7 108.7
C1 C11 H7 108.7
N2 C11 H6 108.7
C1 C11 H6 108.7
H7 C11 H6 107.6
N1 C12 N2 113.4(3)
N1 C12 H8 123.3
N2 C12 H8 123.3
N1 C13 C18 130.7(3)
N1 C13 C14 109.0(3)
C18 C13 C14 120.4(3)
C15 C14 N2 132.1(3)
C15 C14 C13 122.3(3)
N2 C14 C13 105.5(3)
C16 C15 C14 116.3(3)
C16 C15 H9 121.8
C14 C15 H9 121.8
C15 C16 C17 122.3(4)
C15 C16 H10 118.9
C17 C16 H10 118.9
C18 C17 C16 121.2(4)
C18 C17 H11 119.4
C16 C17 H11 119.4
C17 C18 C13 117.4(3)
C17 C18 H12 121.3
C13 C18 H12 121.3
O2 C31 O1 123.7(3)
O2 C31 C3 121.7(3)
O1 C31 C3 114.6(3)
O4 C51 O3 123.6(3)
O4 C51 C5 120.9(3)
O3 C51 C5 115.6(3)
C12 N1 C13 105.2(3)
C12 N2 C14 107.0(3)
C12 N2 C11 126.3(3)
C14 N2 C11 126.4(3)
C31 O1 H4 106.1
C51 O3 H5 107.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.380(4)
C1 C6 1.390(4)
C1 C11 1.510(4)
C2 C3 1.393(4)
C2 H1 0.9300
C3 C4 1.386(4)
C3 C31 1.494(4)
C4 C5 1.390(4)
C4 H2 0.9300
C5 C6 1.389(4)
C5 C51 1.484(4)
C6 H3 0.9300
C11 N2 1.463(4)
C11 H7 0.9700
C11 H6 0.9700
C12 N1 1.317(4)
C12 N2 1.340(4)
C12 H8 0.9300
C13 N1 1.392(4)
C13 C18 1.394(4)
C13 C14 1.397(4)
C14 C15 1.384(4)
C14 N2 1.386(4)
C15 C16 1.374(5)
C15 H9 0.9300
C16 C17 1.395(5)
C16 H10 0.9300
C17 C18 1.375(5)
C17 H11 0.9300
C18 H12 0.9300
C31 O2 1.203(4)
C31 O1 1.289(4)
C51 O4 1.236(3)
C51 O3 1.297(3)
O1 H4 0.8397
O3 H5 0.8356
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
O3 H5 O4 3_776 0.84 1.82 2.649(3) 171.4
O1 H4 N1 1_454 0.84 1.76 2.576(4) 164.1
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
C6 C1 C2 C3 1.0(5)
C11 C1 C2 C3 -175.2(3)
C1 C2 C3 C4 -0.8(5)
C1 C2 C3 C31 178.0(3)
C2 C3 C4 C5 0.1(5)
C31 C3 C4 C5 -178.6(3)
C3 C4 C5 C6 0.3(4)
C3 C4 C5 C51 179.7(3)
C4 C5 C6 C1 -0.1(5)
C51 C5 C6 C1 -179.6(3)
C2 C1 C6 C5 -0.5(5)
C11 C1 C6 C5 175.6(3)
C2 C1 C11 N2 -121.4(3)
C6 C1 C11 N2 62.6(4)
N1 C13 C14 C15 -179.2(3)
C18 C13 C14 C15 0.7(5)
N1 C13 C14 N2 1.4(3)
C18 C13 C14 N2 -178.7(3)
N2 C14 C15 C16 178.6(3)
C13 C14 C15 C16 -0.6(5)
C14 C15 C16 C17 -0.7(5)
C15 C16 C17 C18 1.9(6)
C16 C17 C18 C13 -1.7(5)
N1 C13 C18 C17 -179.7(3)
C14 C13 C18 C17 0.4(5)
C4 C3 C31 O2 -172.8(3)
C2 C3 C31 O2 8.5(5)
C4 C3 C31 O1 7.6(5)
C2 C3 C31 O1 -171.1(3)
C6 C5 C51 O4 0.3(5)
C4 C5 C51 O4 -179.2(3)
C6 C5 C51 O3 -179.1(3)
C4 C5 C51 O3 1.5(4)
N2 C12 N1 C13 1.3(4)
C18 C13 N1 C12 178.4(3)
C14 C13 N1 C12 -1.7(4)
N1 C12 N2 C14 -0.5(4)
N1 C12 N2 C11 -174.7(3)
C15 C14 N2 C12 -179.9(3)
C13 C14 N2 C12 -0.6(3)
C15 C14 N2 C11 -5.7(5)
C13 C14 N2 C11 173.6(3)
C1 C11 N2 C12 -106.8(3)
C1 C11 N2 C14 80.2(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657272
