#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/60/2226082.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_2226082
loop_
_publ_author_name
'Dong, Gui-Ying'
'Liu, Xin-Hua'
'Liu, Tong-Fei'
'Khan, Islam Ullah'
_publ_section_title
;
 3,3'-(p-Phenylenedimethylene)di-1H-imidazol-1-ium
 bis(4-nitrobenzoate)--4-nitrobenzoic acid (1/2)
;
_journal_coeditor_code           CI5093
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1485
_journal_paper_doi               10.1107/S160053681001929X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H16 N4 2+, 2C7 H4 N O4-, 2C7 H5 N O4'
_chemical_formula_moiety
'C14 H16 N4 2+, 2(C7 H4 N O4 -), 2(C7 H5 N O4)'
_chemical_formula_sum            'C42 H34 N8 O16'
_chemical_formula_weight         906.77
_chemical_name_systematic
;
3,3'-(p-Phenylenedimethylene)di-1H-imidazol-1-ium
bis(4-nitrobenzoate)--4-nitrobenzoic acid (1/2)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                112.94(3)
_cell_angle_beta                 102.49(3)
_cell_angle_gamma                101.94(3)
_cell_formula_units_Z            1
_cell_length_a                   7.2659(15)
_cell_length_b                   12.689(3)
_cell_length_c                   13.028(3)
_cell_measurement_reflns_used    3889
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.68
_cell_measurement_theta_min      4.57
_cell_volume                     1021.8(6)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_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      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0656
_diffrn_reflns_av_sigmaI/netI    0.0870
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8835
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             470
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0814
_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)+(0.0648P)²+0.2399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1909
_reflns_number_gt                2019
_reflns_number_total             3590
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5093.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C42 H34 N8 O16 '
_cod_database_code               2226082
_cod_database_fobs_code          2226082
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O7 0.1748(5) 0.3773(3) 0.6201(3) 0.0628(9) Uani d . 1 . .
O O8 0.2413(5) 0.4626(3) 0.5069(3) 0.0636(9) Uani d . 1 . .
N N4 0.2722(5) 0.3310(3) 0.2960(3) 0.0468(9) Uani d . 1 . .
H H4A 0.2596 0.3328 0.3607 0.056 Uiso calc R 1 . .
N N3 0.3203(4) 0.3884(3) 0.1672(3) 0.0341(8) Uani d . 1 . .
C C11 0.2099(5) 0.5846(3) 0.6892(3) 0.0346(10) Uani d . 1 . .
C C12 0.1960(6) 0.5971(4) 0.7973(3) 0.0378(10) Uani d . 1 . .
H H12 0.1787 0.5305 0.8124 0.045 Uiso calc R 1 . .
C C20 0.0546(6) 0.4031(4) -0.0614(3) 0.0417(11) Uani d . 1 . .
H H20 0.0910 0.3371 -0.1031 0.050 Uiso calc R 1 . .
C C10 0.2349(6) 0.6835(4) 0.6673(4) 0.0454(11) Uani d . 1 . .
H H10 0.2447 0.6753 0.5947 0.054 Uiso calc R 1 . .
C C21 -0.1173(6) 0.4176(4) -0.1146(4) 0.0417(11) Uani d . 1 . .
H H21 -0.1952 0.3621 -0.1918 0.050 Uiso calc R 1 . .
C C13 0.2074(6) 0.7074(4) 0.8830(4) 0.0426(11) Uani d . 1 . .
H H13 0.1981 0.7160 0.9558 0.051 Uiso calc R 1 . .
C C17 0.2842(6) 0.2657(4) 0.1182(4) 0.0397(10) Uani d . 1 . .
H H17 0.2808 0.2161 0.0427 0.048 Uiso calc R 1 . .
C C8 0.2328(6) 0.8040(4) 0.8581(4) 0.0423(11) Uani d . 1 . .
C C14 0.2070(6) 0.4663(4) 0.5962(4) 0.0417(11) Uani d . 1 . .
C C19 0.1743(6) 0.4850(4) 0.0531(3) 0.0359(10) Uani d . 1 . .
C C9 0.2457(6) 0.7939(4) 0.7505(4) 0.0510(12) Uani d . 1 . .
H H9 0.2612 0.8603 0.7351 0.061 Uiso calc R 1 . .
N N2 0.2409(6) 0.9230(4) 0.9474(4) 0.0642(12) Uani d . 1 . .
C C15 0.3111(6) 0.4252(4) 0.2754(4) 0.0405(10) Uani d . 1 . .
H H15 0.3291 0.5044 0.3279 0.049 Uiso calc R 1 . .
O O6 0.2194(6) 0.9302(3) 1.0400(3) 0.0946(14) Uani d . 1 . .
C C16 0.2548(6) 0.2308(4) 0.1995(4) 0.0445(11) Uani d . 1 . .
H H16 0.2277 0.1525 0.1913 0.053 Uiso calc R 1 . .
O O5 0.2639(7) 1.0065(3) 0.9231(4) 0.1088(16) Uani d . 1 . .
C C18 0.3622(6) 0.4672(4) 0.1113(4) 0.0472(11) Uani d . 1 . .
H H18A 0.4226 0.4318 0.0525 0.057 Uiso calc R 1 . .
H H18B 0.4567 0.5452 0.1706 0.057 Uiso calc R 1 . .
C C4 0.4933(6) 0.8837(3) 0.5529(3) 0.0360(10) Uani d . 1 . .
O O3 0.4409(5) 0.7026(3) 0.3853(3) 0.0731(11) Uani d . 1 . .
O O2 0.4178(6) 1.2399(3) 0.8522(3) 0.0791(11) Uani d . 1 . .
O O4 0.7429(5) 0.7925(3) 0.5183(3) 0.0700(10) Uani d . 1 . .
C C1 0.3648(7) 1.0618(4) 0.6869(4) 0.0423(11) Uani d . 1 . .
N N1 0.2961(7) 1.1562(4) 0.7606(4) 0.0616(11) Uani d . 1 . .
C C5 0.6275(6) 0.9830(3) 0.6549(3) 0.0417(11) Uani d . 1 . .
H H5 0.7610 0.9887 0.6779 0.050 Uiso calc R 1 . .
C C3 0.2940(6) 0.8758(4) 0.5190(3) 0.0432(11) Uani d . 1 . .
H H3 0.2041 0.8099 0.4503 0.052 Uiso calc R 1 . .
C C2 0.2281(7) 0.9650(4) 0.5863(4) 0.0473(11) Uani d . 1 . .
H H2 0.0947 0.9596 0.5642 0.057 Uiso calc R 1 . .
C C6 0.5638(7) 1.0733(4) 0.7224(4) 0.0451(11) Uani d . 1 . .
H H6 0.6533 1.1403 0.7903 0.054 Uiso calc R 1 . .
C C7 0.5608(8) 0.7845(4) 0.4785(4) 0.0470(11) Uani d . 1 . .
O O1 0.1202(7) 1.1467(4) 0.7276(4) 0.1083(15) Uani d . 1 . .
H H2A 0.2107 0.3206 0.5773 0.162 Uiso d 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
C14 O7 H2A . . 111.6 ?
C15 N4 C16 . . 109.4(3) ?
C15 N4 H4A . . 125.3 ?
C16 N4 H4A . . 125.3 ?
C15 N3 C17 . . 108.0(3) ?
C15 N3 C18 . . 125.0(3) ?
C17 N3 C18 . . 127.0(3) ?
C10 C11 C12 . . 119.4(4) ?
C10 C11 C14 . . 119.0(4) ?
C12 C11 C14 . . 121.6(4) ?
C13 C12 C11 . . 120.7(4) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C21 C20 C19 . . 121.1(4) ?
C21 C20 H20 . . 119.4 ?
C19 C20 H20 . . 119.4 ?
C9 C10 C11 . . 121.2(4) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C20 C21 C19 . 2_565 120.0(4) ?
C20 C21 H21 . . 120.0 ?
C19 C21 H21 2_565 . 120.0 ?
C8 C13 C12 . . 118.3(4) ?
C8 C13 H13 . . 120.8 ?
C12 C13 H13 . . 120.8 ?
C16 C17 N3 . . 107.1(4) ?
C16 C17 H17 . . 126.4 ?
N3 C17 H17 . . 126.4 ?
C13 C8 C9 . . 122.2(4) ?
C13 C8 N2 . . 119.5(4) ?
C9 C8 N2 . . 118.2(4) ?
O8 C14 O7 . . 124.9(4) ?
O8 C14 C11 . . 119.4(4) ?
O7 C14 C11 . . 115.7(4) ?
C20 C19 C21 . 2_565 118.8(4) ?
C20 C19 C18 . . 120.6(4) ?
C21 C19 C18 2_565 . 120.5(4) ?
C10 C9 C8 . . 118.2(4) ?
C10 C9 H9 . . 120.9 ?
C8 C9 H9 . . 120.9 ?
O5 N2 O6 . . 123.9(4) ?
O5 N2 C8 . . 118.0(5) ?
O6 N2 C8 . . 118.1(5) ?
N4 C15 N3 . . 108.4(4) ?
N4 C15 H15 . . 125.8 ?
N3 C15 H15 . . 125.8 ?
C17 C16 N4 . . 107.0(4) ?
C17 C16 H16 . . 126.5 ?
N4 C16 H16 . . 126.5 ?
N3 C18 C19 . . 111.7(3) ?
N3 C18 H18A . . 109.3 ?
C19 C18 H18A . . 109.3 ?
N3 C18 H18B . . 109.3 ?
C19 C18 H18B . . 109.3 ?
H18A C18 H18B . . 107.9 ?
C5 C4 C3 . . 119.5(4) ?
C5 C4 C7 . . 121.0(4) ?
C3 C4 C7 . . 119.6(4) ?
C2 C1 C6 . . 122.6(4) ?
C2 C1 N1 . . 118.9(4) ?
C6 C1 N1 . . 118.5(4) ?
O1 N1 O2 . . 123.3(4) ?
O1 N1 C1 . . 118.3(4) ?
O2 N1 C1 . . 118.4(5) ?
C6 C5 C4 . . 120.4(4) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C2 C3 C4 . . 120.7(4) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C1 C2 C3 . . 118.4(4) ?
C1 C2 H2 . . 120.8 ?
C3 C2 H2 . . 120.8 ?
C1 C6 C5 . . 118.5(4) ?
C1 C6 H6 . . 120.7 ?
C5 C6 H6 . . 120.7 ?
O3 C7 O4 . . 124.3(4) ?
O3 C7 C4 . . 119.0(5) ?
O4 C7 C4 . . 116.7(4) ?
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
O7 C14 . 1.274(5) ?
O7 H2A . 0.85 ?
O8 C14 . 1.227(5) ?
N4 C15 . 1.313(5) ?
N4 C16 . 1.354(5) ?
N4 H4A . 0.86 ?
N3 C15 . 1.324(5) ?
N3 C17 . 1.373(5) ?
N3 C18 . 1.469(5) ?
C11 C10 . 1.378(5) ?
C11 C12 . 1.383(5) ?
C11 C14 . 1.510(5) ?
C12 C13 . 1.380(5) ?
C12 H12 . 0.93 ?
C20 C21 . 1.376(5) ?
C20 C19 . 1.385(5) ?
C20 H20 . 0.93 ?
C10 C9 . 1.370(6) ?
C10 H10 . 0.93 ?
C21 C19 2_565 1.387(5) ?
C21 H21 . 0.93 ?
C13 C8 . 1.373(5) ?
C13 H13 . 0.93 ?
C17 C16 . 1.336(5) ?
C17 H17 . 0.93 ?
C8 C9 . 1.382(6) ?
C8 N2 . 1.484(5) ?
C19 C21 2_565 1.387(5) ?
C19 C18 . 1.519(5) ?
C9 H9 . 0.93 ?
N2 O5 . 1.210(5) ?
N2 O6 . 1.220(5) ?
C15 H15 . 0.93 ?
C16 H16 . 0.93 ?
C18 H18A . 0.97 ?
C18 H18B . 0.97 ?
C4 C5 . 1.389(5) ?
C4 C3 . 1.389(5) ?
C4 C7 . 1.509(6) ?
O3 C7 . 1.224(5) ?
O2 N1 . 1.225(5) ?
O4 C7 . 1.279(5) ?
C1 C2 . 1.374(6) ?
C1 C6 . 1.377(6) ?
C1 N1 . 1.472(5) ?
N1 O1 . 1.221(5) ?
C5 C6 . 1.382(5) ?
C5 H5 . 0.93 ?
C3 C2 . 1.382(5) ?
C3 H3 . 0.93 ?
C2 H2 . 0.93 ?
C6 H6 . 0.93 ?
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
O7 H2A O3 2_666 0.85 2.57 3.167(5) 128
O7 H2A O4 2_666 0.85 1.65 2.494(5) 173
N4 H4A O8 1_555 0.86 2.03 2.690(5) 133
C15 H15 O3 . 0.93 2.23 3.073(7) 150
C17 H17 O5 1_544 0.93 2.46 3.228(7) 140
C21 H21 O3 2_565 0.93 2.46 3.321(6) 154
