##############################################################################
###                                                                        ###
###        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
;
Bis(2-amino-3-nitropyridinium) dihydrogendiphosphate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C5 H6 N3 O2 +), H2 O7 P2 2-'
_chemical_formula_sum     'C10 H14 N6 O11 P2'
_chemical_formula_iupac     '2C5 H6 N3 O2 +, H2 O7 P2 2-'
_chemical_formula_weight     456.21
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P c a 21'
_symmetry_space_group_name_Hall     'P 2c -2ac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    '-x+1/2, y, z+1/2'
    'x+1/2, -y, z'
_cell_length_a     34.250(5)
_cell_length_b     5.763(2)
_cell_length_c     8.991(3)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1774.8(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     12
_cell_measurement_temperature     298
_exptl_crystal_description     prism
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.29
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.19
_exptl_crystal_density_diffrn     1.707
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     936
_exptl_absorpt_coefficient_mu     0.320
_exptl_absorpt_correction_type     none
_diffrn_ambient_temperature     298
_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     'Enraf--Nonius CAD-4'
_diffrn_measurement_device     'κ-geometry diffractometer'
_diffrn_measurement_method     'non-profiled ω'
_diffrn_reflns_number     2726
_diffrn_reflns_av_R_equivalents     0.0077
_diffrn_reflns_av_sigmaI/netI     0.0194
_diffrn_reflns_theta_min     3.29
_diffrn_reflns_theta_max     29.97
_diffrn_reflns_theta_full     29.97
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -48
_diffrn_reflns_limit_h_max     0
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     2
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     3
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    3 -2 3
    3 2 -3
_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     2724
_reflns_number_gt     2279
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0543
_refine_ls_R_factor_gt     0.0331
_refine_ls_wR_factor_gt     0.0785
_refine_ls_wR_factor_ref     0.0906
_refine_ls_goodness_of_fit_ref     1.092
_refine_ls_restrained_S_all     1.092
_refine_ls_number_reflns     2724
_refine_ls_number_parameters     265
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0391P)²+0.7964P] 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     0.526
_refine_diff_density_min     -0.277
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0192(12)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983)'
_refine_ls_abs_structure_Flack     -0.15(11)
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'
    'P' 'P' 0.1023 0.0942
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_cell_refinement     'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
   'ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    P P1 0.05181(2) 0.76331(12) 0.64677(9) 0.02939(15) Uani d . 1 . .
    P P2 0.06740(2) 0.49228(13) 0.38188(9) 0.02940(15) Uani d . 1 . .
    O O1 0.02869(6) 0.6068(4) 0.7473(3) 0.0388(5) Uani d . 1 . .
    O O2 0.03160(6) 1.0043(4) 0.6468(3) 0.0380(5) Uani d . 1 . .
    H H2 0.0432 1.0916 0.5898 0.057 Uiso calc R 1 . .
    O O3 0.09419(6) 0.7686(4) 0.6795(3) 0.0406(5) Uani d . 1 . .
    O O4 0.04503(6) 0.6839(4) 0.4767(2) 0.0349(4) Uani d . 1 . .
    O O5 0.06725(7) 0.2687(4) 0.4645(3) 0.0442(6) Uani d . 1 . .
    O O6 0.10798(6) 0.5779(4) 0.3433(3) 0.0381(5) Uani d . 1 . .
    O O7 0.04355(6) 0.4892(4) 0.2361(2) 0.0367(5) Uani d . 1 . .
    H H7 0.0207 0.4592 0.2548 0.055 Uiso calc R 1 . .
    O O8 0.17007(11) 0.0987(8) 1.2413(5) 0.0996(14) Uani d . 1 . .
    O O9 0.17848(8) 0.4036(7) 1.1115(4) 0.0796(12) Uani d . 1 . .
    O O10 0.17870(9) -0.0306(6) 0.8224(4) 0.0689(9) Uani d . 1 . .
    O O11 0.23687(9) 0.0861(7) 0.8703(5) 0.0899(12) Uani d . 1 . .
    N N1 0.07030(7) 0.3161(5) 0.9226(3) 0.0334(5) Uani d . 1 . .
    H H1 0.0606 0.4078 0.8567 0.040 Uiso calc R 1 . .
    N N2 0.12502(8) 0.5449(5) 0.9194(3) 0.0445(7) Uani d . 1 . .
    H H2A 0.1139 0.6299 0.8532 0.053 Uiso calc R 1 . .
    H H2B 0.1481 0.5788 0.9499 0.053 Uiso calc R 1 . .
    N N3 0.15874(9) 0.2373(7) 1.1479(5) 0.0578(9) Uani d . 1 . .
    N N4 0.16725(8) 0.4967(5) 0.5130(4) 0.0396(6) Uani d . 1 . .
    H H4 0.1465 0.5191 0.4608 0.048 Uiso calc R 1 . .
    N N5 0.13779(8) 0.1725(6) 0.6059(4) 0.0522(8) Uani d . 1 . .
    H H5A 0.1184 0.1998 0.5479 0.063 Uiso calc R 1 . .
    H H5B 0.1374 0.0536 0.6637 0.063 Uiso calc R 1 . .
    N N6 0.20652(10) 0.1031(6) 0.8028(4) 0.0548(8) Uani d . 1 . .
    C C1 0.04851(9) 0.1383(5) 0.9672(4) 0.0374(6) Uani d . 1 . .
    H H1A 0.0236 0.1196 0.9281 0.045 Uiso calc R 1 . .
    C C2 0.06201(11) -0.0169(6) 1.0689(4) 0.0450(8) Uani d . 1 . .
    H H2C 0.0469 -0.1431 1.0978 0.054 Uiso calc R 1 . .
    C C3 0.09860(10) 0.0180(6) 1.1278(4) 0.0453(8) Uani d . 1 . .
    H H3 0.1084 -0.0843 1.1986 0.054 Uiso calc R 1 . .
    C C4 0.12081(9) 0.2041(6) 1.0822(4) 0.0404(7) Uani d . 1 . .
    C C5 0.10672(8) 0.3631(5) 0.9740(4) 0.0350(6) Uani d . 1 . .
    C C6 0.19675(10) 0.6453(6) 0.4979(5) 0.0470(8) Uani d . 1 . .
    H H6 0.1943 0.7678 0.4312 0.056 Uiso calc R 1 . .
    C C7 0.23056(10) 0.6223(7) 0.5778(5) 0.0550(10) Uani d . 1 . .
    H H7C 0.2512 0.7255 0.5652 0.066 Uiso calc R 1 . .
    C C8 0.23302(9) 0.4406(7) 0.6779(4) 0.0511(9) Uani d . 1 . .
    H H8 0.2554 0.4221 0.7352 0.061 Uiso calc R 1 . .
    C C9 0.20255(9) 0.2872(6) 0.6933(4) 0.0417(7) Uani d . 1 . .
    C C10 0.16813(9) 0.3125(6) 0.6061(4) 0.0389(7) Uani d . 1 . .
_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
    P1 O3 . 1.481(2) ?
    P1 O1 . 1.503(2) ?
    P1 O2 . 1.552(2) ?
    P1 O4 . 1.613(2) ?
    P2 O5 . 1.487(2) ?
    P2 O6 . 1.515(2) ?
    P2 O7 . 1.545(2) ?
    P2 O4 . 1.592(2) ?
    O2 H2 . 0.8200 ?
    O7 H7 . 0.8200 ?
    O8 N3 . 1.222(5) ?
    O9 N3 . 1.217(5) ?
    O10 N6 . 1.238(4) ?
    O11 N6 . 1.208(4) ?
    N1 C1 . 1.330(4) ?
    N1 C5 . 1.358(4) ?
    N1 H1 . 0.8600 ?
    N2 C5 . 1.316(4) ?
    N2 H2A . 0.8600 ?
    N2 H2B . 0.8600 ?
    N3 C4 . 1.440(4) ?
    N4 C6 . 1.331(4) ?
    N4 C10 . 1.353(4) ?
    N4 H4 . 0.8600 ?
    N5 C10 . 1.316(4) ?
    N5 H5A . 0.8600 ?
    N5 H5B . 0.8600 ?
    N6 C9 . 1.454(5) ?
    C1 C2 . 1.360(5) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.375(5) ?
    C2 H2C . 0.9300 ?
    C3 C4 . 1.377(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.420(4) ?
    C6 C7 . 1.369(5) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.383(5) ?
    C7 H7C . 0.9300 ?
    C8 C9 . 1.375(5) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.423(5) ?
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
    O3 P1 O1 . . 114.15(13) ?
    O3 P1 O2 . . 114.74(13) ?
    O1 P1 O2 . . 107.60(13) ?
    O3 P1 O4 . . 109.59(13) ?
    O1 P1 O4 . . 108.93(14) ?
    O2 P1 O4 . . 100.93(13) ?
    O5 P2 O6 . . 113.55(13) ?
    O5 P2 O7 . . 114.34(15) ?
    O6 P2 O7 . . 107.14(13) ?
    O5 P2 O4 . . 109.41(14) ?
    O6 P2 O4 . . 109.76(13) ?
    O7 P2 O4 . . 101.99(12) ?
    P1 O2 H2 . . 109.5 ?
    P2 O4 P1 . . 129.43(14) ?
    P2 O7 H7 . . 109.5 ?
    C1 N1 C5 . . 124.5(3) ?
    C1 N1 H1 . . 117.7 ?
    C5 N1 H1 . . 117.7 ?
    C5 N2 H2A . . 120.0 ?
    C5 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    O9 N3 O8 . . 121.5(4) ?
    O9 N3 C4 . . 119.7(3) ?
    O8 N3 C4 . . 118.8(4) ?
    C6 N4 C10 . . 123.4(3) ?
    C6 N4 H4 . . 118.3 ?
    C10 N4 H4 . . 118.3 ?
    C10 N5 H5A . . 120.0 ?
    C10 N5 H5B . . 120.0 ?
    H5A N5 H5B . . 120.0 ?
    O11 N6 O10 . . 122.7(4) ?
    O11 N6 C9 . . 118.7(3) ?
    O10 N6 C9 . . 118.6(3) ?
    N1 C1 C2 . . 121.2(3) ?
    N1 C1 H1A . . 119.4 ?
    C2 C1 H1A . . 119.4 ?
    C1 C2 C3 . . 118.2(3) ?
    C1 C2 H2C . . 120.9 ?
    C3 C2 H2C . . 120.9 ?
    C2 C3 C4 . . 120.2(3) ?
    C2 C3 H3 . . 119.9 ?
    C4 C3 H3 . . 119.9 ?
    C3 C4 C5 . . 121.2(3) ?
    C3 C4 N3 . . 118.7(3) ?
    C5 C4 N3 . . 120.1(3) ?
    N2 C5 N1 . . 118.0(3) ?
    N2 C5 C4 . . 127.4(3) ?
    N1 C5 C4 . . 114.6(3) ?
    N4 C6 C7 . . 121.7(4) ?
    N4 C6 H6 . . 119.1 ?
    C7 C6 H6 . . 119.1 ?
    C6 C7 C8 . . 117.8(3) ?
    C6 C7 H7C . . 121.1 ?
    C8 C7 H7C . . 121.1 ?
    C9 C8 C7 . . 120.4(3) ?
    C9 C8 H8 . . 119.8 ?
    C7 C8 H8 . . 119.8 ?
    C8 C9 C10 . . 120.5(3) ?
    C8 C9 N6 . . 117.8(3) ?
    C10 C9 N6 . . 121.7(3) ?
    N5 C10 N4 . . 117.6(3) ?
    N5 C10 C9 . . 126.3(3) ?
    N4 C10 C9 . . 116.1(3) ?
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    O5 P2 O4 P1 . . . . 53.0(2) ?
    O6 P2 O4 P1 . . . . -72.2(2) ?
    O7 P2 O4 P1 . . . . 174.45(18) ?
    O3 P1 O4 P2 . . . . 39.2(2) ?
    O1 P1 O4 P2 . . . . -86.3(2) ?
    O2 P1 O4 P2 . . . . 160.61(18) ?
    C5 N1 C1 C2 . . . . -1.3(5) ?
    N1 C1 C2 C3 . . . . 1.6(5) ?
    C1 C2 C3 C4 . . . . -0.9(5) ?
    C2 C3 C4 C5 . . . . -0.1(5) ?
    C2 C3 C4 N3 . . . . 179.0(4) ?
    O9 N3 C4 C3 . . . . -178.4(4) ?
    O8 N3 C4 C3 . . . . 0.5(6) ?
    O9 N3 C4 C5 . . . . 0.7(6) ?
    O8 N3 C4 C5 . . . . 179.6(4) ?
    C1 N1 C5 N2 . . . . 179.7(3) ?
    C1 N1 C5 C4 . . . . 0.2(4) ?
    C3 C4 C5 N2 . . . . -179.0(3) ?
    N3 C4 C5 N2 . . . . 1.9(6) ?
    C3 C4 C5 N1 . . . . 0.4(5) ?
    N3 C4 C5 N1 . . . . -178.7(3) ?
    C10 N4 C6 C7 . . . . -0.5(6) ?
    N4 C6 C7 C8 . . . . -1.1(6) ?
    C6 C7 C8 C9 . . . . 1.2(6) ?
    C7 C8 C9 C10 . . . . 0.2(6) ?
    C7 C8 C9 N6 . . . . -178.6(4) ?
    O11 N6 C9 C8 . . . . -3.4(6) ?
    O10 N6 C9 C8 . . . . 177.0(4) ?
    O11 N6 C9 C10 . . . . 177.8(4) ?
    O10 N6 C9 C10 . . . . -1.8(5) ?
    C6 N4 C10 N5 . . . . -176.9(4) ?
    C6 N4 C10 C9 . . . . 1.9(5) ?
    C8 C9 C10 N5 . . . . 177.0(4) ?
    N6 C9 C10 N5 . . . . -4.2(6) ?
    C8 C9 C10 N4 . . . . -1.7(5) ?
    N6 C9 C10 N4 . . . . 177.1(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
    O2 H2 O5 1_565 0.82 1.73 2.549(3) 177.9
    O7 H7 O1 2_564 0.82 1.73 2.537(3) 165.9
    N1 H1 O1 . 0.86 1.87 2.706(3) 165.1
    N2 H2A O3 . 0.86 1.88 2.726(4) 167.5
    N2 H2B O9 . 0.86 2.05 2.645(4) 125.5
    N4 H4 O6 . 0.86 1.72 2.582(4) 174.2
    N5 H5A O5 . 0.86 1.95 2.786(4) 165.4
    N5 H5B O10 . 0.86 2.07 2.669(5) 126.4
    N5 H5B O3 1_545 0.86 2.22 2.843(4) 129.8
    C2 H2C O7 1_546 0.93 2.46 3.280(4) 147.3
    C3 H3 O6 1_546 0.93 2.34 3.208(4) 154.9
    C8 H8 O9 3_554 0.93 2.52 3.097(4) 120.1
data_global
_journal_date_recd_electronic     2010-01-05
_journal_date_accepted     2010-01-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      2
_journal_page_first     o358
_journal_page_last     o358
_journal_paper_category     QO
_journal_coeditor_code     DN2529
_publ_contact_author_name     'Dr. Toumi Akriche Samah'
_publ_contact_author_address
;
Laboratoire de Chimie des Matériaux
Faculté des Sciences de Bizerte
7021 Zarzouna Bizerte
Tunisie.
;
_publ_contact_author_email     'toumiakriche@yahoo.fr'
_publ_contact_author_fax     '216 72 590 566'
_publ_contact_author_phone     '216 72 591 906'
_publ_section_title
;
Bis(2-amino-3-nitropyridinium) dihydrogendiphosphate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Toumi Akriche, Samah' .
;
Laboratoire de Chimie des Matériaux
Faculté des Sciences de Bizerte
7021 Zarzouna Bizerte
Tunisia
;
    'Rzaigui, Mohamed' .
;
Laboratoire de Chimie des Matériaux
Faculté des Sciences de Bizerte
7021 Zarzouna Bizerte
Tunisia
;
    'Elothman, Zeid  Abdellah  ' .
;
Chemistry Department,
Faculty of Science, King Saud University,
PO Box 2455, Riyadh 11451,
Saudi Arabia
;
    'Mahfouz, Refaat Mohamed' .
;
Chemistry Department,
Faculty of Science, King Saud University,
PO Box 2455, Riyadh 11451,
Saudi Arabia
;
