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###                                                                        ###
###        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.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Piperazine-1,4-diium bis(3,5-dicarboxybenzoate)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C4 H12 N2 2+, 2C9 H5 O6 -'
_chemical_formula_sum     'C22 H22 N2 O12'
_chemical_formula_iupac     'C4 H12 N2 2+, 2C9 H5 O6 -'
_chemical_formula_weight     506.42
_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     7.3029(15)
_cell_length_b     8.6758(17)
_cell_length_c     9.0422(18)
_cell_angle_alpha     87.04(3)
_cell_angle_beta     69.94(3)
_cell_angle_gamma     83.76(3)
_cell_volume     534.9(2)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     2886
_cell_measurement_theta_min     4.07
_cell_measurement_theta_max     23.68
_cell_measurement_temperature     295(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.21
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.572
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     264
_exptl_absorpt_coefficient_mu     0.130
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.968
_exptl_absorpt_correction_T_max     0.971
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(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 scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5586
_diffrn_reflns_av_R_equivalents     0.0475
_diffrn_reflns_av_sigmaI/netI     0.0694
_diffrn_reflns_theta_min     3.13
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_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 > 2sigma(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     2443
_reflns_number_gt     1563
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1206
_refine_ls_R_factor_gt     0.0686
_refine_ls_wR_factor_gt     0.1942
_refine_ls_wR_factor_ref     0.2185
_refine_ls_goodness_of_fit_ref     1.004
_refine_ls_restrained_S_all     1.004
_refine_ls_number_reflns     2443
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.1021P)²+0.7768P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.347
_refine_diff_density_min     -0.220
_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     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_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 O3 0.5054(4) -0.0789(3) -0.2891(3) 0.0327(7) Uani d . 1 . .
    O O4 0.3840(4) -0.2898(3) -0.1607(3) 0.0351(7) Uani d . 1 . .
    O O5 -0.2059(4) 0.0124(3) 0.4770(3) 0.0299(6) Uani d . 1 . .
    H H5 -0.2853 -0.0331 0.5479 0.045 Uiso calc R 1 . .
    O O6 -0.0820(4) -0.2283(3) 0.3989(3) 0.0401(8) Uani d . 1 . .
    C C6 0.0627(5) 0.1419(4) 0.2228(4) 0.0244(8) Uani d . 1 . .
    H H6 -0.0104 0.2046 0.3073 0.029 Uiso calc R 1 . .
    O O2 0.3069(5) 0.4294(3) -0.0579(3) 0.0507(9) Uani d . 1 . .
    H H2 0.3110 0.5232 -0.0547 0.076 Uiso calc R 1 . .
    C C2 0.2932(5) 0.1130(4) -0.0401(4) 0.0213(7) Uani d . 1 . .
    H H2A 0.3740 0.1567 -0.1322 0.026 Uiso calc R 1 . .
    C C3 0.2797(5) -0.0471(4) -0.0306(4) 0.0200(7) Uani d . 1 . .
    C C5 0.0477(5) -0.0166(4) 0.2327(4) 0.0220(7) Uani d . 1 . .
    C C1 0.1875(5) 0.2071(4) 0.0863(4) 0.0238(8) Uani d . 1 . .
    C C4 0.1576(5) -0.1116(4) 0.1067(4) 0.0231(8) Uani d . 1 . .
    H H4 0.1490 -0.2181 0.1146 0.028 Uiso calc R 1 . .
    C C8 0.3998(5) -0.1456(4) -0.1710(4) 0.0221(7) Uani d . 1 . .
    O O1 0.1355(6) 0.4589(3) 0.1961(4) 0.0588(10) Uani d . 1 . .
    C C9 -0.0858(5) -0.0890(4) 0.3773(4) 0.0243(8) Uani d . 1 . .
    C C7 0.2045(6) 0.3776(4) 0.0825(4) 0.0324(9) Uani d . 1 . .
    N N1 0.6111(5) 0.5988(3) 0.5510(3) 0.0294(7) Uani d . 1 . .
    H H1A 0.5332 0.6181 0.6509 0.035 Uiso calc R 1 . .
    H H1B 0.7184 0.6495 0.5311 0.035 Uiso calc R 1 . .
    C C11 0.5066(7) 0.6562(4) 0.4430(5) 0.0375(10) Uani d . 1 . .
    H H11A 0.5946 0.6439 0.3352 0.045 Uiso calc R 1 . .
    H H11B 0.4656 0.7659 0.4602 0.045 Uiso calc R 1 . .
    C C10 0.3299(6) 0.5704(4) 0.4671(5) 0.0385(10) Uani d . 1 . .
    H H10A 0.2357 0.5906 0.5716 0.046 Uiso calc R 1 . .
    H H10B 0.2682 0.6068 0.3907 0.046 Uiso calc R 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
    O3 0.0350(14) 0.0304(14) 0.0214(13) -0.0079(11) 0.0066(11) -0.0010(10)
    O4 0.0490(17) 0.0175(13) 0.0256(14) -0.0037(12) 0.0047(12) -0.0024(10)
    O5 0.0265(14) 0.0288(14) 0.0223(13) -0.0038(11) 0.0074(10) 0.0010(10)
    O6 0.0459(17) 0.0261(14) 0.0318(15) -0.0108(12) 0.0099(13) 0.0006(11)
    C6 0.0257(18) 0.0196(16) 0.0219(17) -0.0002(14) -0.0002(14) -0.0049(13)
    O2 0.085(2) 0.0214(14) 0.0282(15) -0.0164(15) 0.0054(15) 0.0018(11)
    C2 0.0253(18) 0.0196(16) 0.0157(15) -0.0037(14) -0.0025(13) 0.0021(13)
    C3 0.0183(16) 0.0200(16) 0.0189(16) -0.0021(13) -0.0027(13) -0.0005(12)
    C5 0.0229(17) 0.0230(17) 0.0162(16) -0.0035(14) -0.0015(13) 0.0003(13)
    C1 0.0280(18) 0.0199(17) 0.0224(17) -0.0043(14) -0.0064(14) 0.0000(13)
    C4 0.0268(18) 0.0203(16) 0.0207(17) -0.0048(14) -0.0052(14) -0.0014(13)
    C8 0.0220(17) 0.0220(17) 0.0198(16) -0.0035(14) -0.0034(14) -0.0008(13)
    O1 0.091(3) 0.0257(15) 0.0370(17) -0.0137(16) 0.0105(17) -0.0093(13)
    C9 0.0232(17) 0.0249(18) 0.0208(17) -0.0078(15) -0.0010(14) 0.0005(14)
    C7 0.041(2) 0.0224(18) 0.0285(19) -0.0098(17) -0.0025(17) 0.0000(15)
    N1 0.0306(17) 0.0261(16) 0.0255(16) -0.0069(13) 0.0001(13) -0.0063(13)
    C11 0.058(3) 0.0202(18) 0.033(2) -0.0037(18) -0.0124(19) -0.0006(15)
    C10 0.038(2) 0.033(2) 0.044(2) 0.0074(18) -0.0150(19) -0.0115(18)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    O3 C8 . 1.240(4) ?
    O4 C8 . 1.265(4) ?
    O5 C9 . 1.314(4) ?
    O5 H5 . 0.82 ?
    O6 C9 . 1.213(4) ?
    C6 C5 . 1.387(5) ?
    C6 C1 . 1.394(5) ?
    C6 H6 . 0.93 ?
    O2 C7 . 1.318(4) ?
    O2 H2 . 0.8200 ?
    C2 C1 . 1.387(5) ?
    C2 C3 . 1.399(4) ?
    C2 H2A . 0.93 ?
    C3 C4 . 1.388(5) ?
    C3 C8 . 1.516(5) ?
    C5 C4 . 1.396(5) ?
    C5 C9 . 1.493(4) ?
    C1 C7 . 1.496(5) ?
    C4 H4 . 0.93 ?
    O1 C7 . 1.204(5) ?
    N1 C11 . 1.471(5) ?
    N1 C10 2_666 1.485(5) ?
    N1 H1A . 0.90 ?
    N1 H1B . 0.90 ?
    C11 C10 . 1.505(6) ?
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C10 N1 2_666 1.485(5) ?
    C10 H10A . 0.97 ?
    C10 H10B . 0.97 ?
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
    C9 O5 H5 . . 109.5 ?
    C5 C6 C1 . . 120.0(3) ?
    C5 C6 H6 . . 120.0 ?
    C1 C6 H6 . . 120.0 ?
    C7 O2 H2 . . 109.5 ?
    C1 C2 C3 . . 120.7(3) ?
    C1 C2 H2A . . 119.6 ?
    C3 C2 H2A . . 119.6 ?
    C4 C3 C2 . . 119.4(3) ?
    C4 C3 C8 . . 121.7(3) ?
    C2 C3 C8 . . 118.9(3) ?
    C6 C5 C4 . . 120.3(3) ?
    C6 C5 C9 . . 121.0(3) ?
    C4 C5 C9 . . 118.7(3) ?
    C2 C1 C6 . . 119.6(3) ?
    C2 C1 C7 . . 122.1(3) ?
    C6 C1 C7 . . 118.3(3) ?
    C3 C4 C5 . . 119.9(3) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    O3 C8 O4 . . 124.4(3) ?
    O3 C8 C3 . . 117.7(3) ?
    O4 C8 C3 . . 117.9(3) ?
    O6 C9 O5 . . 124.0(3) ?
    O6 C9 C5 . . 122.5(3) ?
    O5 C9 C5 . . 113.5(3) ?
    O1 C7 O2 . . 123.3(3) ?
    O1 C7 C1 . . 123.8(3) ?
    O2 C7 C1 . . 112.9(3) ?
    C11 N1 C10 . 2_666 111.1(3) ?
    C11 N1 H1A . . 109.4 ?
    C10 N1 H1A 2_666 . 109.4 ?
    C11 N1 H1B . . 109.4 ?
    C10 N1 H1B 2_666 . 109.4 ?
    H1A N1 H1B . . 108.0 ?
    N1 C11 C10 . . 111.5(3) ?
    N1 C11 H11A . . 109.3 ?
    C10 C11 H11A . . 109.3 ?
    N1 C11 H11B . . 109.3 ?
    C10 C11 H11B . . 109.3 ?
    H11A C11 H11B . . 108.0 ?
    N1 C10 C11 2_666 . 110.1(3) ?
    N1 C10 H10A 2_666 . 109.6 ?
    C11 C10 H10A . . 109.6 ?
    N1 C10 H10B 2_666 . 109.6 ?
    C11 C10 H10B . . 109.6 ?
    H10A C10 H10B . . 108.2 ?
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
    N1 H1A O4 1_566 0.90 1.85 2.725(4) 165
    N1 H1B O6 1_665 0.90 1.92 2.751(4) 153
    O2 H2 O4 1_565 0.82 1.87 2.612(4) 149
    O5 H5 O3 1_456 0.82 1.79 2.584(4) 164
data_global
_journal_date_recd_electronic     2010-04-05
_journal_date_accepted     2010-04-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      5
_journal_page_first     o1097
_journal_page_last     o1097
_journal_paper_category     QO
_journal_coeditor_code     CI5078
_publ_contact_author_name     'Islam Ullah Khan'
_publ_contact_author_address
;
Materials Chemistry Laboratory,
Department of
Chemistry,
Government College University,
Lahore 54000,
Pakistan
;
_publ_contact_author_email     'iukhangcu@126.com'
_publ_contact_author_fax     '+90-352-4374933'
_publ_contact_author_phone     '+90-352-4374901 extra 33106'
_publ_section_title
;
Piperazine-1,4-diium bis(3,5-dicarboxybenzoate)
;
loop_
    _publ_author_name
    _publ_author_address
    'Gui-Ying Dong'
;
College of Chemical Engineering and Biotechnology
Hebei Polytechnic University
Tangshan 063009
People's Republic of China
;
    'Li-Hua Fan'
;
College of Chemical Engineering and Biotechnology
Hebei Polytechnic University
Tangshan 063009
People's Republic of China
;
    'Li-Xia Yang'
;
College of Chemical Engineering and Biotechnology
Hebei Polytechnic University
Tangshan 063009
People's Republic of China
;
    'Islam Ullah Khan'
;
Materials Chemistry Laboratory
Department of Chemistry
Government College University
Lahore 54000
Pakistan
;
