##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-04-29
_journal_date_accepted     2009-05-14
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      6
_journal_page_first     o1335
_journal_page_last     o1335
_journal_paper_category     QO
_journal_coeditor_code     SI2172
_publ_contact_author_name     'Prof. Xie, Ya-Bo'
_publ_contact_author_address
;
College of Environmental and Energy Engineering
Beijing University of Technology
Beijing 100124
People's Republic of China
;
_publ_contact_author_email     'xieyabo@bjut.edu.cn'
_publ_contact_author_fax     '86-10-67391983'
_publ_contact_author_phone     '86-10-67392130'
_publ_section_title
;
Bis(5,6-dicarboxybenzimidazolium) sulfate monohydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Cui, Yue'
;
College of Environmental and Energy Engineering
Beijing University of Technology
Beijing 100124
People's Republic of China
;
    'Gao, Qian'
;
College of Environmental and Energy Engineering
Beijing University of Technology
Beijing 100124
People's Republic of China
;
    'Zhang, Chao-Yan'
;
College of Environmental and Energy Engineering
Beijing University of Technology
Beijing 100124
People's Republic of China
;
    'Xie, Ya-Bo'
;
College of Environmental and Energy Engineering
Beijing University of Technology
Beijing 100124
People's Republic of China
;
data_I
_chemical_name_systematic
;
Bis(5,6-dicarboxybenzimidazolium) sulfate monohydrate
;
_chemical_formula_moiety     '2(C9 H7 N2 O4 +), O4 S 2-, H2 O'
_chemical_formula_sum     'C18 H16 N4 O13 S'
_chemical_formula_iupac     '2C9 H7 N2 O4 +, S1 O4 2-, H2 O'
_chemical_formula_weight     528.41
_chemical_melting_point     ?
_symmetry_cell_setting     'Orthorhombic'
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x, y, -z+1/2'
    '-x, -y, -z'
    'x-1/2, y-1/2, -z-1/2'
    '-x-1/2, y-1/2, z'
    'x, -y, z-1/2'
_cell_length_a     14.691(3)
_cell_length_b     7.7968(17)
_cell_length_c     17.983(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2059.8(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2413
_cell_measurement_theta_min     2.27
_cell_measurement_theta_max     25.00
_cell_measurement_temperature     296(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.12
_exptl_crystal_size_mid     0.11
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.704
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1088
_exptl_absorpt_coefficient_mu     0.243
_exptl_absorpt_correction_type     'Multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 1998)'
_exptl_absorpt_correction_T_min     0.971
_exptl_absorpt_correction_T_max     0.976
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(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 CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11525
_diffrn_reflns_av_R_equivalents     0.0603
_diffrn_reflns_av_sigmaI/netI     0.0406
_diffrn_reflns_theta_min     2.27
_diffrn_reflns_theta_max     27.80
_diffrn_reflns_theta_full     27.80
_diffrn_measured_fraction_theta_max     0.988
_diffrn_measured_fraction_theta_full     0.988
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2413
_reflns_number_gt     1994
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0583
_refine_ls_R_factor_gt     0.0483
_refine_ls_wR_factor_gt     0.1268
_refine_ls_wR_factor_ref     0.1377
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.004
_refine_ls_number_reflns     2413
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0847P)²+0.8915P] where P=(Fo²+2Fc²)/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     0.461
_refine_diff_density_min     -0.397
_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'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (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
    O O1 0.35417(10) 0.1890(2) 0.09502(8) 0.0418(4) Uani d . 1 . .
    H H28 0.3685 0.1903 0.1408 0.050 Uiso d R 1 . .
    O O2 0.22201(11) 0.2483(3) 0.15019(8) 0.0553(5) Uani d . 1 . .
    O O3 0.00994(12) 0.3035(2) 0.08983(10) 0.0586(5) Uani d . 1 . .
    O O4 0.08286(11) 0.05673(19) 0.07644(9) 0.0474(4) Uani d . 1 . .
    H H21 0.0465 0.0172 0.1089 0.057 Uiso d R 1 . .
    N N1 0.29633(11) 0.4817(2) -0.16017(8) 0.0344(4) Uani d . 1 . .
    H H25 0.3535 0.4982 -0.1718 0.041 Uiso d R 1 . .
    N N2 0.15053(11) 0.5073(2) -0.17520(9) 0.0358(4) Uani d . 1 . .
    H H22 0.0969 0.5355 -0.1962 0.043 Uiso d R 1 . .
    C C1 0.26786(14) 0.2354(2) 0.09487(10) 0.0339(4) Uani d . 1 . .
    C C2 0.23266(12) 0.2806(2) 0.01950(9) 0.0280(4) Uani d . 1 . .
    C C3 0.29283(11) 0.3365(2) -0.03408(10) 0.0293(4) Uani d . 1 . .
    H H3A 0.3554 0.3271 -0.0276 0.035 Uiso calc R 1 . .
    C C4 0.25595(12) 0.4077(2) -0.09819(9) 0.0282(4) Uani d . 1 . .
    C C5 0.23151(14) 0.5390(3) -0.20452(11) 0.0381(4) Uani d . 1 . .
    H H5A 0.2413 0.5936 -0.2498 0.046 Uiso calc R 1 . .
    C C6 0.16218(12) 0.4236(2) -0.10814(10) 0.0295(4) Uani d . 1 . .
    C C7 0.10081(12) 0.3636(2) -0.05544(10) 0.0316(4) Uani d . 1 . .
    H H7A 0.0383 0.3721 -0.0626 0.038 Uiso calc R 1 . .
    C C8 0.13689(12) 0.2909(2) 0.00784(10) 0.0301(4) Uani d . 1 . .
    C C9 0.07088(12) 0.2201(3) 0.06351(11) 0.0345(4) Uani d . 1 . .
    S S1 0.0000 -0.14201(8) 0.2500 0.0295(2) Uani d S 1 . .
    O O9 0.07896(13) -0.2429(2) 0.22937(9) 0.0630(6) Uani d . 1 . .
    O O11 -0.02520(10) -0.0310(2) 0.18688(9) 0.0533(5) Uani d . 1 . .
    O O1W 0.0000 0.3439(3) 0.2500 0.0540(6) Uani d S 1 . .
    H H1WA -0.024(5) 0.266(8) 0.286(3) 0.20(3) Uiso 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
    O1 0.0398(8) 0.0540(9) 0.0318(7) 0.0075(6) -0.0091(6) 0.0022(6)
    O2 0.0509(9) 0.0893(13) 0.0258(7) 0.0019(9) 0.0010(6) -0.0032(7)
    O3 0.0511(10) 0.0602(10) 0.0645(11) 0.0225(8) 0.0302(8) 0.0198(9)
    O4 0.0501(9) 0.0412(8) 0.0510(9) 0.0022(7) 0.0229(7) 0.0079(7)
    N1 0.0301(8) 0.0445(9) 0.0285(8) -0.0057(7) 0.0029(6) 0.0030(6)
    N2 0.0331(8) 0.0436(9) 0.0306(8) -0.0038(7) -0.0061(6) 0.0050(7)
    C1 0.0392(10) 0.0365(10) 0.0260(9) -0.0010(8) -0.0034(7) -0.0017(7)
    C2 0.0283(8) 0.0305(9) 0.0253(8) 0.0027(7) -0.0014(6) -0.0028(6)
    C3 0.0239(8) 0.0355(10) 0.0284(8) -0.0007(7) -0.0010(6) -0.0025(7)
    C4 0.0264(8) 0.0330(9) 0.0252(8) -0.0035(7) 0.0010(6) -0.0035(7)
    C5 0.0404(10) 0.0445(11) 0.0295(9) -0.0061(9) -0.0012(8) 0.0035(8)
    C6 0.0281(8) 0.0328(9) 0.0275(8) -0.0020(7) -0.0039(6) -0.0003(7)
    C7 0.0222(8) 0.0381(10) 0.0345(9) -0.0011(7) 0.0002(7) 0.0012(7)
    C8 0.0292(8) 0.0321(9) 0.0291(9) 0.0009(7) 0.0040(7) -0.0014(7)
    C9 0.0287(9) 0.0426(11) 0.0323(9) 0.0032(7) 0.0055(7) 0.0038(8)
    S1 0.0309(3) 0.0334(4) 0.0243(3) 0.000 0.0043(2) 0.000
    O9 0.0814(13) 0.0702(12) 0.0374(8) 0.0449(10) 0.0205(8) 0.0090(8)
    O11 0.0300(7) 0.0781(11) 0.0517(9) 0.0056(8) 0.0054(6) 0.0308(8)
    O1W 0.0597(16) 0.0487(14) 0.0538(15) 0.000 -0.0195(11) 0.000
_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
    O1 C1 . 1.319(2) ?
    O1 H28 . 0.8499 ?
    O2 C1 . 1.205(2) ?
    O3 C9 . 1.204(2) ?
    O4 C9 . 1.306(3) ?
    O4 H21 . 0.8496 ?
    N1 C5 . 1.320(3) ?
    N1 C4 . 1.388(2) ?
    N1 H25 . 0.8747 ?
    N2 C5 . 1.325(3) ?
    N2 C6 . 1.382(2) ?
    N2 H22 . 0.9011 ?
    C1 C2 . 1.493(2) ?
    C2 C3 . 1.379(2) ?
    C2 C8 . 1.425(2) ?
    C3 C4 . 1.389(3) ?
    C3 H3A . 0.9300 ?
    C4 C6 . 1.395(3) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.389(3) ?
    C7 C8 . 1.377(3) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.499(2) ?
    S1 O9 4 1.4498(16) ?
    S1 O9 . 1.4498(16) ?
    S1 O11 4 1.4745(15) ?
    S1 O11 . 1.4745(15) ?
    O1W H1WA . 0.95(6) ?
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
    C1 O1 H28 . . 103.7 ?
    C9 O4 H21 . . 113.0 ?
    C5 N1 C4 . . 108.51(16) ?
    C5 N1 H25 . . 119.9 ?
    C4 N1 H25 . . 131.5 ?
    C5 N2 C6 . . 108.92(16) ?
    C5 N2 H22 . . 124.9 ?
    C6 N2 H22 . . 126.1 ?
    O2 C1 O1 . . 123.95(17) ?
    O2 C1 C2 . . 122.41(18) ?
    O1 C1 C2 . . 113.55(16) ?
    C3 C2 C8 . . 120.82(16) ?
    C3 C2 C1 . . 119.15(16) ?
    C8 C2 C1 . . 119.28(16) ?
    C2 C3 C4 . . 117.14(16) ?
    C2 C3 H3A . . 121.4 ?
    C4 C3 H3A . . 121.4 ?
    N1 C4 C3 . . 131.72(17) ?
    N1 C4 C6 . . 106.39(15) ?
    C3 C4 C6 . . 121.81(16) ?
    N1 C5 N2 . . 110.14(17) ?
    N1 C5 H5A . . 124.9 ?
    N2 C5 H5A . . 124.9 ?
    N2 C6 C7 . . 132.38(17) ?
    N2 C6 C4 . . 106.03(15) ?
    C7 C6 C4 . . 121.58(17) ?
    C8 C7 C6 . . 116.90(17) ?
    C8 C7 H7A . . 121.6 ?
    C6 C7 H7A . . 121.6 ?
    C7 C8 C2 . . 121.67(16) ?
    C7 C8 C9 . . 117.03(16) ?
    C2 C8 C9 . . 121.30(16) ?
    O3 C9 O4 . . 123.86(18) ?
    O3 C9 C8 . . 122.97(18) ?
    O4 C9 C8 . . 113.02(16) ?
    O9 S1 O9 4 . 114.29(17) ?
    O9 S1 O11 4 4 108.80(9) ?
    O9 S1 O11 . 4 108.33(10) ?
    O9 S1 O11 4 . 108.33(10) ?
    O9 S1 O11 . . 108.80(9) ?
    O11 S1 O11 4 . 108.15(16) ?
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
    O1W H1WA O3 4 0.96(6) 2.26(5) 2.9012(11) 123.6
    O1W H1WA O11 4 0.96(6) 2.47(6) 3.1575(16) 128.4
    O4 H21 O11 . 0.85 1.79 2.6330(11) 169.4
    N2 H22 O1W 5_565 0.90 1.96 2.8365(10) 163.4
    N1 H25 O11 3 0.88 1.82 2.6931(12) 174.7
    O1 H28 O9 7_665 0.85 1.84 2.6616(11) 160.6
    C5 H5A O2 8_565 0.93 2.20 3.098(3) 162.4
