##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-12-06
_journal_date_accepted     2010-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      2
_journal_page_first     o263
_journal_page_last     o263
_journal_paper_category     QO
_journal_coeditor_code     DS2078
_publ_contact_author_name     'Ren, Chun-Xia; Shang, Shao-Ming'
_publ_contact_author_address
;
      School of Chemical and Material Engineering
      Jiangnan University
      1800 Lihu Road
      Wuxi
      Jiangsu Province 214122
      People's Republic of China
;
_publ_contact_author_email     'chunxiaren@yahoo.com.cn, smshang@126.com'
_publ_contact_author_phone     '0086-13382888962'
_publ_section_title
;
2,2'-(<i>p</i>-Phenylene)bis(4,5-dihydro-1<i>H</i>-imidazol-3-ium)
bis(3-nitrobenzoate)
;
loop_
    _publ_author_name
    _publ_author_address
    'Xiu-Mei Song'
;
School of Chemical and Material Engineering
Jiangnan University
1800 Lihu Road
Wuxi
Jiangsu Province 214122
People's Republic of China
;
    'Jun-Jun Li'
;
College of Pharmacy
GuangDong Pharmaceutical University
Guangzhou
Guangdong Province 510006
People's Republic of China
;
    'Xin-Hua Liu'
;
School of Chemical and Material Engineering
Jiangnan University
1800 Lihu Road
Wuxi
Jiangsu Province 214122
People's Republic of China
;
    'Chun-Xia Ren'
;
School of Chemical and Material Engineering
Jiangnan University
1800 Lihu Road
Wuxi
Jiangsu Province 214122
People's Republic of China
;
    'Shao-Ming Shang'
;
School of Chemical and Material Engineering
Jiangnan University
1800 Lihu Road
Wuxi
Jiangsu Province 214122
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2,2'-(<i>p</i>-Phenylene)bis(4,5-dihydro-1<i>H</i>-imidazol-3-ium)
bis(3-nitrobenzoate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H16 N4 2+, 2(C7 H4 N O4 -)'
_chemical_formula_sum     'C26 H24 N6 O8'
_chemical_formula_iupac     'C12 H16 N4 2+, 2C7 H4 N O4 -'
_chemical_formula_weight     548.51
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.9882(12)
_cell_length_b     7.4165(12)
_cell_length_c     13.233(2)
_cell_angle_alpha     81.343(3)
_cell_angle_beta     82.443(3)
_cell_angle_gamma     62.699(2)
_cell_volume     600.96(17)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     ?
_cell_measurement_theta_max     ?
_cell_measurement_temperature     273(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.67
_exptl_crystal_size_mid     0.55
_exptl_crystal_size_min     0.42
_exptl_crystal_density_diffrn     1.516
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     286
_exptl_absorpt_coefficient_mu     0.115
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1998)'
_exptl_absorpt_correction_T_min     0.9269
_exptl_absorpt_correction_T_max     0.9533
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     '\f and \w'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3714
_diffrn_reflns_av_R_equivalents     0.0161
_diffrn_reflns_av_sigmaI/netI     0.0345
_diffrn_reflns_theta_min     1.56
_diffrn_reflns_theta_max     27.01
_diffrn_reflns_theta_full     27.01
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full     0.982
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2575
_reflns_number_gt     1676
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0839
_refine_ls_R_factor_gt     0.0534
_refine_ls_wR_factor_gt     0.1291
_refine_ls_wR_factor_ref     0.1510
_refine_ls_goodness_of_fit_ref     1.067
_refine_ls_restrained_S_all     1.067
_refine_ls_number_reflns     2575
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.1694P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.197
_refine_diff_density_min     -0.284
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     '<i>SMART</i> (Bruker, 1998)'
_computing_cell_refinement     '<i>SAINT-Plus</i> (Bruker, 1998)'
_computing_data_reduction     '<i>SAINT-Plus</i> (Bruker, 1998)'
_computing_structure_solution     '<i>SHELXS97</i> (Sheldrick, 2008)'
_computing_structure_refinement     '<i>SHELXL97</i> (Sheldrick, 2008)'
_computing_molecular_graphics     '<i>SHELXTL</i> (Sheldrick, 2008)'
_computing_publication_material     '<i>SHELXTL</i> (Sheldrick, 2008)'
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 0.7607(4) 0.1903(4) 0.18562(17) 0.0483(6) Uani d . 1 . .
    H H1A 0.7398 0.2592 0.2458 0.058 Uiso calc R 1 . .
    H H1B 0.6839 0.1075 0.1981 0.058 Uiso calc R 1 . .
    C C2 0.6871(4) 0.3430(3) 0.09029(18) 0.0492(6) Uani d . 1 . .
    H H2A 0.5961 0.3147 0.0521 0.059 Uiso calc R 1 . .
    H H2B 0.6093 0.4820 0.1083 0.059 Uiso calc R 1 . .
    C C3 1.0544(3) 0.1481(3) 0.07401(15) 0.0383(5) Uani d . 1 . .
    C C4 1.2831(3) 0.0707(3) 0.03509(15) 0.0373(5) Uani d . 1 . .
    C C5 1.3404(3) 0.1420(3) -0.06192(15) 0.0414(5) Uani d . 1 . .
    H H5 1.2337 0.2373 -0.1034 0.050 Uiso calc R 1 . .
    C C6 1.5554(4) 0.0716(3) -0.09660(15) 0.0416(5) Uani d . 1 . .
    H H6 1.5925 0.1195 -0.1615 0.050 Uiso calc R 1 . .
    C C7 0.1900(4) 0.5421(5) 0.2448(2) 0.0620(8) Uani d . 1 . .
    C C8 0.2163(3) 0.3932(3) 0.33993(16) 0.0437(5) Uani d . 1 . .
    C C9 0.1925(4) 0.2191(4) 0.33805(19) 0.0529(6) Uani d . 1 . .
    H H9 0.1691 0.1887 0.2765 0.064 Uiso calc R 1 . .
    C C10 0.2027(4) 0.0885(4) 0.4264(2) 0.0639(7) Uani d . 1 . .
    H H10 0.1849 -0.0275 0.4239 0.077 Uiso calc R 1 . .
    C C11 0.2391(4) 0.1307(4) 0.5170(2) 0.0620(7) Uani d . 1 . .
    H H11 0.2445 0.0452 0.5769 0.074 Uiso calc R 1 . .
    C C12 0.2671(3) 0.3009(4) 0.51797(16) 0.0507(6) Uani d U 1 . .
    C C13 0.2561(3) 0.4345(3) 0.43168(17) 0.0462(5) Uani d . 1 . .
    H H13 0.2750 0.5497 0.4350 0.055 Uiso calc R 1 . .
    N N1 0.8925(3) 0.3081(3) 0.03187(14) 0.0482(5) Uani d . 1 . .
    H H1 0.9055 0.3822 -0.0226 0.058 Uiso calc R 1 . .
    N N2 0.9901(3) 0.0671(3) 0.15833(13) 0.0438(5) Uani d . 1 . .
    H H2 1.0721 -0.0439 0.1930 0.053 Uiso calc R 1 . .
    N N3 0.3060(4) 0.3471(5) 0.61616(18) 0.0776(8) Uani d U 1 . .
    O O1 0.1555(3) 0.4959(3) 0.16467(14) 0.0884(7) Uani d . 1 . .
    O O2 0.2025(3) 0.7013(3) 0.25649(18) 0.0916(8) Uani d . 1 . .
    O O3 0.3241(4) 0.5037(6) 0.6153(2) 0.1100(10) Uani d . 1 . .
    O O4 0.3135(4) 0.2288(5) 0.69216(16) 0.1205(11) Uani d . 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    C1 0.0495(13) 0.0543(13) 0.0410(12) -0.0242(11) -0.0023(10) -0.0025(10)
    C2 0.0456(13) 0.0468(12) 0.0473(13) -0.0152(10) -0.0034(10) -0.0009(10)
    C3 0.0477(12) 0.0387(10) 0.0286(10) -0.0187(9) -0.0089(9) -0.0010(8)
    C4 0.0446(12) 0.0356(10) 0.0298(10) -0.0160(9) -0.0068(8) -0.0011(8)
    C5 0.0472(12) 0.0380(11) 0.0323(11) -0.0142(9) -0.0099(9) 0.0053(8)
    C6 0.0516(13) 0.0424(11) 0.0273(10) -0.0197(10) -0.0045(9) 0.0040(8)
    C7 0.0410(13) 0.0717(18) 0.0494(16) -0.0137(12) -0.0021(11) 0.0233(13)
    C8 0.0359(11) 0.0477(12) 0.0367(12) -0.0129(9) -0.0031(9) 0.0074(9)
    C9 0.0513(14) 0.0599(15) 0.0463(14) -0.0226(11) -0.0085(11) -0.0052(11)
    C10 0.0610(16) 0.0510(14) 0.080(2) -0.0292(13) -0.0097(14) 0.0104(13)
    C11 0.0513(15) 0.0686(17) 0.0530(16) -0.0235(13) -0.0059(12) 0.0225(13)
    C12 0.0350(12) 0.0701(16) 0.0336(12) -0.0131(11) -0.0033(9) -0.0013(11)
    C13 0.0362(11) 0.0487(12) 0.0484(13) -0.0153(10) -0.0014(9) -0.0037(10)
    N1 0.0481(11) 0.0478(10) 0.0372(10) -0.0146(9) -0.0047(8) 0.0072(8)
    N2 0.0464(10) 0.0434(10) 0.0365(10) -0.0181(8) -0.0060(8) 0.0062(8)
    N3 0.0438(13) 0.124(2) 0.0481(14) -0.0212(14) -0.0029(10) -0.0174(15)
    O1 0.0837(14) 0.1023(16) 0.0365(10) -0.0115(12) -0.0080(9) 0.0177(10)
    O2 0.0766(14) 0.0759(14) 0.1167(19) -0.0418(12) -0.0346(12) 0.0561(13)
    O3 0.0816(17) 0.173(3) 0.0934(19) -0.0593(18) 0.0042(13) -0.0671(19)
    O4 0.0984(18) 0.183(3) 0.0363(12) -0.0305(18) -0.0134(11) 0.0122(15)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 N2 . 1.462(3) ?
    C1 C2 . 1.531(3) ?
    C1 H1A . 0.9700 ?
    C1 H1B . 0.9700 ?
    C2 N1 . 1.468(3) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N2 . 1.312(3) ?
    C3 N1 . 1.317(3) ?
    C3 C4 . 1.476(3) ?
    C4 C6 2_855 1.393(3) ?
    C4 C5 . 1.394(3) ?
    C5 C6 . 1.383(3) ?
    C5 H5 . 0.9300 ?
    C6 C4 2_855 1.393(3) ?
    C6 H6 . 0.9300 ?
    C7 O1 . 1.246(4) ?
    C7 O2 . 1.257(4) ?
    C7 C8 . 1.514(3) ?
    C8 C9 . 1.380(3) ?
    C8 C13 . 1.387(3) ?
    C9 C10 . 1.388(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.367(4) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.366(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.380(3) ?
    C12 N3 . 1.481(3) ?
    C13 H13 . 0.9300 ?
    N1 H1 . 0.8600 ?
    N2 H2 . 0.8600 ?
    N3 O4 . 1.221(3) ?
    N3 O3 . 1.222(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
    N2 C1 C2 . . 102.53(17) ?
    N2 C1 H1A . . 111.3 ?
    C2 C1 H1A . . 111.3 ?
    N2 C1 H1B . . 111.3 ?
    C2 C1 H1B . . 111.3 ?
    H1A C1 H1B . . 109.2 ?
    N1 C2 C1 . . 102.37(17) ?
    N1 C2 H2A . . 111.3 ?
    C1 C2 H2A . . 111.3 ?
    N1 C2 H2B . . 111.3 ?
    C1 C2 H2B . . 111.3 ?
    H2A C2 H2B . . 109.2 ?
    N2 C3 N1 . . 111.85(19) ?
    N2 C3 C4 . . 122.98(18) ?
    N1 C3 C4 . . 125.13(18) ?
    C6 C4 C5 2_855 . 119.30(19) ?
    C6 C4 C3 2_855 . 119.93(18) ?
    C5 C4 C3 . . 120.75(18) ?
    C6 C5 C4 . . 120.20(19) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C5 C6 C4 . 2_855 120.50(19) ?
    C5 C6 H6 . . 119.7 ?
    C4 C6 H6 2_855 . 119.7 ?
    O1 C7 O2 . . 127.2(2) ?
    O1 C7 C8 . . 117.2(3) ?
    O2 C7 C8 . . 115.6(3) ?
    C9 C8 C13 . . 118.9(2) ?
    C9 C8 C7 . . 120.8(2) ?
    C13 C8 C7 . . 120.2(2) ?
    C8 C9 C10 . . 121.2(2) ?
    C8 C9 H9 . . 119.4 ?
    C10 C9 H9 . . 119.4 ?
    C11 C10 C9 . . 119.9(2) ?
    C11 C10 H10 . . 120.1 ?
    C9 C10 H10 . . 120.1 ?
    C12 C11 C10 . . 118.7(2) ?
    C12 C11 H11 . . 120.7 ?
    C10 C11 H11 . . 120.7 ?
    C11 C12 C13 . . 122.8(2) ?
    C11 C12 N3 . . 118.7(2) ?
    C13 C12 N3 . . 118.4(3) ?
    C12 C13 C8 . . 118.5(2) ?
    C12 C13 H13 . . 120.7 ?
    C8 C13 H13 . . 120.7 ?
    C3 N1 C2 . . 110.95(18) ?
    C3 N1 H1 . . 124.5 ?
    C2 N1 H1 . . 124.5 ?
    C3 N2 C1 . . 111.14(17) ?
    C3 N2 H2 . . 124.4 ?
    C1 N2 H2 . . 124.4 ?
    O4 N3 O3 . . 124.9(3) ?
    O4 N3 C12 . . 117.8(3) ?
    O3 N3 C12 . . 117.3(3) ?
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
    C6 H6 O2 2_765 0.93 2.48 3.283(3) 144
    N1 H1 O1 2_665 0.86 1.97 2.763(3) 153
    N2 H2 O2 1_645 0.86 1.80 2.646(3) 166

