#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/07/2210711.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_2210711
loop_
_publ_author_name
'Ding-Ben Chen'
'Ling Huang'
_publ_section_title
;
 1-(Carboxymethyl)-1,3-benzimidazol-3-ium-3-acetate
;
_journal_coeditor_code           LH2183
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4686
_journal_page_last               o4688
_journal_paper_doi               10.1107/S1600536806038335
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H10 N2 O4'
_chemical_formula_moiety         'C11 H10 N2 O4'
_chemical_formula_sum            'C11 H10 N2 O4'
_chemical_formula_weight         234.21
_chemical_melting_point          573.45(5)
_chemical_name_systematic
;
1-(Carboxymethyl)-1,3-benzimidazol-3-ium-3-acetate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 102.2830(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.9168(17)
_cell_length_b                   9.8014(11)
_cell_length_c                   14.3344(16)
_cell_measurement_reflns_used    2512
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.5
_cell_volume                     2047.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Siemens SMART CCD area-detector
;
_diffrn_measurement_method       'ω and φ'
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8976
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.50
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.196
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.051P)²+0.7851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                1991
_reflns_number_total             2512
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2183.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '573.4- 573.5' was changed to
'573.45(5)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '573.4- 573.5' was changed to
'573.45(5)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210711
_cod_database_fobs_code          2210711
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_occupancy
O O1 0.34245(7) 0.57941(10) 0.29096(7) 0.0434(3) Uani d 1
O O2 0.25165(7) 0.76108(10) 0.29187(7) 0.0428(3) Uani d 1
O O3 -0.15054(7) 1.04349(11) 0.00920(8) 0.0496(3) Uani d 1
O O4 -0.08041(7) 0.86736(10) -0.04436(7) 0.0481(3) Uani d 1
N N1 -0.00180(7) 0.77652(10) 0.12957(7) 0.0319(2) Uani d 1
N N2 0.11894(7) 0.64458(10) 0.14693(7) 0.0301(2) Uani d 1
C C1 0.08969(9) 0.77319(13) 0.14479(9) 0.0328(3) Uani d 1
H H1 0.1279(10) 0.8532(16) 0.1538(11) 0.039(4) Uiso d 1
H H3 -0.1754(11) 0.6490(16) 0.0872(12) 0.045(4) Uiso d 1
H H4 -0.1909(13) 0.4082(17) 0.0789(12) 0.054(5) Uiso d 1
H H5 -0.0628(13) 0.264(2) 0.1023(13) 0.063(5) Uiso d 1
H H6 0.0886(12) 0.3592(16) 0.1351(12) 0.048(4) Uiso d 1
H H8A 0.2144(11) 0.4993(18) 0.1674(12) 0.049(4) Uiso d 1
H H8B 0.2418(12) 0.6274(17) 0.1110(13) 0.053(5) Uiso d 1
H H10A -0.1074(12) 0.8852(16) 0.1542(12) 0.047(4) Uiso d 1
H H10B -0.0163(11) 0.9762(17) 0.1507(11) 0.044(4) Uiso d 1
H H11 -0.1184(16) 0.892(2) -0.1196(18) 0.098(8) Uiso d 1
C C2 -0.03439(8) 0.64281(13) 0.11931(8) 0.0306(3) Uani d 1
C C3 -0.12306(9) 0.59001(15) 0.09940(10) 0.0388(3) Uani d 1
C C4 -0.13054(10) 0.44945(17) 0.09524(11) 0.0447(3) Uani d 1
C C5 -0.05310(10) 0.36453(16) 0.10885(11) 0.0442(3) Uani d 1
C C6 0.03488(10) 0.41730(14) 0.12684(10) 0.0374(3) Uani d 1
C C7 0.04236(8) 0.55855(13) 0.13173(8) 0.0293(3) Uani d 1
C C8 0.21464(9) 0.59868(15) 0.16436(10) 0.0353(3) Uani d 1
C C9 0.27245(8) 0.65448(12) 0.25710(9) 0.0304(3) Uani d 1
C C10 -0.05789(10) 0.90007(14) 0.12270(10) 0.0377(3) Uani d 1
C C11 -0.10142(8) 0.94271(13) 0.02086(9) 0.0333(3) Uani 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
_geom_angle_publ_flag
C11 O4 H11 114.9(12) ?
C1 N1 C2 108.38(10) yes
C1 N1 C10 125.51(11) ?
C2 N1 C10 126.10(11) ?
C1 N2 C7 108.31(10) yes
C1 N2 C8 126.61(11) ?
C7 N2 C8 125.07(11) ?
N2 C1 N1 110.19(11) yes
N2 C1 H1 125.9(9) ?
N1 C1 H1 123.9(9) ?
C7 C2 C3 121.69(12) ?
C7 C2 N1 106.58(11) yes
C3 C2 N1 131.72(12) ?
C4 C3 C2 116.34(13) ?
C4 C3 H3 122.6(10) ?
C2 C3 H3 121.0(10) ?
C3 C4 C5 121.91(13) ?
C3 C4 H4 119.2(10) ?
C5 C4 H4 118.8(10) ?
C6 C5 C4 121.64(14) ?
C6 C5 H5 120.0(11) ?
C4 C5 H5 118.3(11) ?
C5 C6 C7 116.42(13) ?
C5 C6 H6 122.0(10) ?
C7 C6 H6 121.6(10) ?
C6 C7 C2 121.97(12) ?
C6 C7 N2 131.50(12) ?
C2 C7 N2 106.52(11) yes
N2 C8 C9 112.84(11) ?
N2 C8 H8A 107.5(10) ?
C9 C8 H8A 109.0(10) ?
N2 C8 H8B 109.1(10) ?
C9 C8 H8B 109.1(10) ?
H8A C8 H8B 109.2(14) ?
O2 C9 O1 126.16(12) ?
O2 C9 C8 121.03(11) ?
O1 C9 C8 112.80(11) ?
N1 C10 C11 114.35(11) ?
N1 C10 H10A 109.3(10) ?
C11 C10 H10A 106.2(10) ?
N1 C10 H10B 107.1(9) ?
C11 C10 H10B 106.4(9) ?
H10A C10 H10B 113.6(13) ?
O3 C11 O4 126.84(12) yes
O3 C11 C10 118.31(12) ?
O4 C11 C10 114.84(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 1.2853(15) yes
O2 C9 1.2256(15) yes
O3 C11 1.2200(15) yes
O4 C11 1.2816(16) yes
O4 H11 1.13(2) ?
N1 C1 1.3358(17) yes
N1 C2 1.3947(16) yes
N1 C10 1.4632(16) yes
N2 C1 1.3322(16) yes
N2 C7 1.3990(15) yes
N2 C8 1.4667(16) yes
C1 H1 0.962(16) ?
C2 C7 1.3920(16) yes
C2 C3 1.3922(18) ?
C3 C4 1.382(2) ?
C3 H3 0.958(16) ?
C4 C5 1.403(2) ?
C4 H4 0.969(18) ?
C5 C6 1.383(2) ?
C5 H5 0.997(19) ?
C6 C7 1.3895(18) ?
C6 H6 0.970(17) ?
C8 C9 1.5239(18) ?
C8 H8A 0.975(18) ?
C8 H8B 0.979(18) ?
C10 C11 1.5244(19) ?
C10 H10A 0.955(17) ?
C10 H10B 0.998(17) ?
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
_geom_hbond_publ_flag
O4 H11 O1 8_465 1.13(2) 1.32(2) 2.4521(13) 176(2) yes
O4 H11 O2 8_465 1.13(2) 2.56(2) 3.2968(14) 121.2(15) yes
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
C1 N1 C2 C7 1.58(14)
C10 N1 C2 C7 -179.73(11)
C1 N1 C2 C3 -177.52(13)
C10 N1 C2 C3 1.2(2)
C7 N2 C1 N1 0.34(14)
C8 N2 C1 N1 -178.32(11)
C2 N1 C1 N2 -1.20(15)
C10 N1 C1 N2 -179.90(11)
C5 C6 C7 C2 0.04(19)
C5 C6 C7 N2 -178.87(12)
C3 C2 C7 C6 -1.29(19)
N1 C2 C7 C6 179.50(12)
C3 C2 C7 N2 177.87(11)
N1 C2 C7 N2 -1.34(12)
C1 N2 C7 C6 179.69(14)
C8 N2 C7 C6 -1.6(2)
C1 N2 C7 C2 0.65(13)
C8 N2 C7 C2 179.34(11)
C1 N2 C8 C9 54.54(18)
C7 N2 C8 C9 -123.91(13)
O2 C9 C8 N2 -25.34(18)
O1 C9 C8 N2 155.44(11)
C7 C2 C3 C4 1.70(19)
N1 C2 C3 C4 -179.32(13)
C7 C6 C5 C4 0.7(2)
C1 N1 C10 C11 100.56(15)
C2 N1 C10 C11 -77.91(17)
O3 C11 C10 N1 178.75(12)
O4 C11 C10 N1 -2.24(18)
C2 C3 C4 C5 -1.0(2)
C6 C5 C4 C3 -0.2(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2556343
