##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
;
_chemical_name_common     '(tetpy2H) (NO3)2'
_chemical_formula_moiety     'C12 H12 N4 O 2+, 2N O3 1-'
_chemical_formula_sum     'C12 H12 N6 O7'
_chemical_formula_iupac     'C12 H12 N4 O 2+, 2N O3 1-'
_chemical_formula_weight     352.28
_chemical_melting_point     unknown
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     7.9639(9)
_cell_length_b     14.017(2)
_cell_length_c     13.0563(15)
_cell_angle_alpha     90.00
_cell_angle_beta     95.995(2)
_cell_angle_gamma     90.00
_cell_volume     1449.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3001
_cell_measurement_theta_min     2.85
_cell_measurement_theta_max     27.55
_cell_measurement_temperature     150(2)
_exptl_crystal_description     'rectangular block'
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.614
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     0.135
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     150(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 SMART1000 CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10487
_diffrn_reflns_av_R_equivalents     0.040
_diffrn_reflns_av_sigmaI/netI     0.046
_diffrn_reflns_theta_min     2.14
_diffrn_reflns_theta_max     28.85
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.909
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     20
_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 > 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.
Pyridinium H atoms were located from /DF syntheses and refined with
the N-H distance restrained to be 0.88(1) A and with Uiso(H) =
1.5Ueq(N). Aromatic hydrogens, after location from /DF syntheses
were placed geometrically and refined with a riding model for which
the C-H distance was constrained to be 0.96 A and Uiso(H) =
1.2Ueq(C).
;
_reflns_number_total     3595
_reflns_number_gt     2275
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0756
_refine_ls_R_factor_gt     0.0423
_refine_ls_wR_factor_gt     0.1071
_refine_ls_wR_factor_ref     0.1159
_refine_ls_goodness_of_fit_ref     1.000
_refine_ls_restrained_S_all     1.000
_refine_ls_number_reflns     3449
_refine_ls_number_parameters     235
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0615P)²] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     'direct method'
_atom_sites_solution_secondary     'difference Fourer method'
_refine_ls_shift/su_max     <0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.316
_refine_diff_density_min     -0.200
_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, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)'
_computing_publication_material     'SHELXL97 and PLATON (Spek, 2001)'
loop_
    _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
    _atom_site_type_symbol
    O3R 0.96466(17) -0.07286(9) 0.76440(10) 0.0307(3) Uani d . 1 . . O
    O1R 1.02768(17) -0.07953(10) 0.60743(10) 0.0354(4) Uani d . 1 . . O
    O2R 1.14799(17) -0.17627(10) 0.72197(11) 0.0394(4) Uani d . 1 . . O
    N1R 1.04898(19) -0.10988(11) 0.69672(13) 0.0277(4) Uani d . 1 . . N
    O1N -0.14682(17) 0.86438(10) 0.26074(11) 0.0388(4) Uani d . 1 . . O
    N1N -0.24467(19) 0.89916(11) 0.32060(13) 0.0282(4) Uani d . 1 . . N
    O3N -0.23428(17) 0.86905(10) 0.41123(11) 0.0355(3) Uani d . 1 . . O
    O2N -0.34792(18) 0.96135(10) 0.29023(12) 0.0439(4) Uani d . 1 . . O
    N1 -0.02143(19) 0.70651(11) 0.38730(14) 0.0333(4) Uani d D 1 . . N
    H1 -0.079(2) 0.7550(11) 0.3583(15) 0.040 Uiso d D 1 . . H
    C6 0.0371(2) 0.71637(13) 0.48571(16) 0.0322(5) Uani d . 1 . . C
    H6 0.0103 0.7718 0.5227 0.039 Uiso calc R 1 . . H
    C5 0.1372(2) 0.64558(13) 0.53424(15) 0.0282(4) Uani d . 1 . . C
    H5 0.1808 0.6521 0.6044 0.034 Uiso calc R 1 . . H
    C4 0.1732(2) 0.56442(12) 0.47855(14) 0.0222(4) Uani d . 1 . . C
    C3 0.1057(2) 0.55751(13) 0.37634(14) 0.0269(4) Uani d . 1 . . C
    H3 0.1267 0.5024 0.3373 0.032 Uiso calc R 1 . . H
    C2 0.0095(2) 0.62969(14) 0.33207(16) 0.0335(5) Uani d . 1 . . C
    H2 -0.0355 0.6253 0.2619 0.040 Uiso calc R 1 . . H
    C7 0.2803(2) 0.48987(12) 0.53032(15) 0.0253(4) Uani d . 1 . . C
    H7 0.3254 0.4971 0.6002 0.030 Uiso calc R 1 . . H
    N8 0.31189(18) 0.41513(10) 0.47982(12) 0.0247(3) Uani d . 1 . . N
    N9 0.41337(18) 0.34818(11) 0.53276(12) 0.0245(3) Uani d D 1 . . N
    H9 0.451(2) 0.3590(14) 0.5970(8) 0.029 Uiso d D 1 . . H
    C10 0.4481(2) 0.26557(13) 0.48578(15) 0.0274(4) Uani d . 1 . . C
    O11 0.39318(19) 0.24550(10) 0.39825(11) 0.0424(4) Uani d . 1 . . O
    C12 0.5661(2) 0.19818(13) 0.54911(14) 0.0251(4) Uani d . 1 . . C
    C13 0.6137(2) 0.11657(13) 0.49977(15) 0.0297(4) Uani d . 1 . . C
    H13 0.5722 0.1050 0.4300 0.036 Uiso calc R 1 . . H
    C14 0.7217(2) 0.05217(13) 0.55246(15) 0.0313(5) Uani d . 1 . . C
    H14 0.7550 -0.0040 0.5192 0.038 Uiso calc R 1 . . H
    N15 0.77876(19) 0.06924(11) 0.65007(13) 0.0281(4) Uani d D 1 . . N
    H15 0.844(2) 0.0264(11) 0.6845(14) 0.034 Uiso d D 1 . . H
    C16 0.7354(2) 0.14668(13) 0.70104(15) 0.0298(4) Uani d . 1 . . C
    H16 0.7778 0.1559 0.7711 0.036 Uiso calc R 1 . . H
    C17 0.6291(2) 0.21258(13) 0.65112(15) 0.0294(4) Uani d . 1 . . C
    H17 0.5985 0.2682 0.6864 0.035 Uiso calc R 1 . . H
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
    O3R 0.0361(7) 0.0301(7) 0.0256(7) 0.0046(6) 0.0026(6) -0.0009(6)
    O1R 0.0419(8) 0.0371(8) 0.0266(8) 0.0087(6) 0.0004(6) 0.0032(6)
    O2R 0.0326(7) 0.0334(8) 0.0512(10) 0.0106(6) -0.0009(7) 0.0088(7)
    N1R 0.0257(8) 0.0230(8) 0.0334(10) 0.0015(6) -0.0017(7) 0.0002(7)
    O1N 0.0387(8) 0.0422(8) 0.0346(8) 0.0072(7) 0.0001(7) -0.0048(7)
    N1N 0.0268(8) 0.0209(8) 0.0348(10) 0.0008(6) -0.0067(7) 0.0009(7)
    O3N 0.0373(7) 0.0342(8) 0.0345(9) 0.0054(6) 0.0012(6) 0.0061(6)
    O2N 0.0415(8) 0.0318(8) 0.0551(10) 0.0136(6) -0.0110(7) 0.0060(7)
    N1 0.0264(8) 0.0214(8) 0.0491(11) 0.0042(7) -0.0097(8) 0.0046(8)
    C6 0.0276(9) 0.0218(10) 0.0472(13) 0.0007(8) 0.0041(9) -0.0074(9)
    C5 0.0277(9) 0.0301(10) 0.0262(10) -0.0031(8) 0.0003(8) -0.0027(8)
    C4 0.0189(8) 0.0199(8) 0.0279(10) -0.0006(7) 0.0027(7) 0.0035(7)
    C3 0.0284(9) 0.0245(9) 0.0272(10) 0.0014(7) 0.0004(8) -0.0033(8)
    C2 0.0354(10) 0.0318(11) 0.0310(12) -0.0005(8) -0.0077(9) 0.0009(8)
    C7 0.0243(9) 0.0240(9) 0.0268(10) 0.0005(7) -0.0002(8) 0.0031(8)
    N8 0.0225(7) 0.0217(8) 0.0299(9) 0.0027(6) 0.0020(6) 0.0052(7)
    N9 0.0250(7) 0.0234(8) 0.0240(9) 0.0055(6) -0.0031(6) 0.0028(7)
    C10 0.0303(10) 0.0263(10) 0.0253(11) 0.0020(8) 0.0005(8) 0.0029(8)
    O11 0.0597(10) 0.0366(8) 0.0282(8) 0.0143(7) -0.0082(7) -0.0001(6)
    C12 0.0244(9) 0.0228(9) 0.0279(10) 0.0015(7) 0.0024(8) 0.0062(8)
    C13 0.0347(10) 0.0310(10) 0.0229(10) 0.0011(8) 0.0010(8) 0.0002(8)
    C14 0.0359(10) 0.0256(10) 0.0331(12) 0.0054(8) 0.0076(9) -0.0041(8)
    N15 0.0255(8) 0.0241(8) 0.0335(9) 0.0056(6) -0.0019(7) 0.0037(7)
    C16 0.0318(9) 0.0296(10) 0.0267(11) -0.0013(8) -0.0025(8) -0.0027(8)
    C17 0.0305(9) 0.0229(9) 0.0342(11) 0.0037(8) 0.0004(8) -0.0042(8)
_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
    O3R N1R . 1.275(2) ?
    O1R N1R . 1.236(2) ?
    O2R N1R . 1.2418(19) ?
    O1N N1N . 1.258(2) ?
    N1N O2N . 1.2349(19) ?
    N1N O3N . 1.251(2) ?
    N1 C6 . 1.327(3) ?
    N1 C2 . 1.333(3) ?
    N1 H1 . 0.882(9) ?
    C6 C5 . 1.384(3) ?
    C6 H6 . 0.9500 ?
    C5 C4 . 1.396(3) ?
    C5 H5 . 0.9500 ?
    C4 C3 . 1.389(2) ?
    C4 C7 . 1.469(2) ?
    C3 C2 . 1.361(3) ?
    C3 H3 . 0.9500 ?
    C2 H2 . 0.9500 ?
    C7 N8 . 1.277(2) ?
    C7 H7 . 0.9500 ?
    N8 N9 . 1.376(2) ?
    N9 C10 . 1.353(2) ?
    N9 H9 . 0.874(9) ?
    C10 O11 . 1.213(2) ?
    C10 C12 . 1.515(2) ?
    C12 C13 . 1.385(3) ?
    C12 C17 . 1.388(3) ?
    C13 C14 . 1.380(3) ?
    C13 H13 . 0.9500 ?
    C14 N15 . 1.329(2) ?
    C14 H14 . 0.9500 ?
    N15 C16 . 1.337(2) ?
    N15 H15 . 0.887(9) ?
    C16 C17 . 1.371(3) ?
    C16 H16 . 0.9500 ?
    C17 H17 . 0.9500 ?
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
    O1R N1R O2R . . 121.94(17) ?
    O1R N1R O3R . . 118.91(14) ?
    O2R N1R O3R . . 119.14(16) ?
    O2N N1N O3N . . 121.19(17) ?
    O2N N1N O1N . . 120.59(17) ?
    O3N N1N O1N . . 118.22(15) ?
    C6 N1 C2 . . 122.80(16) ?
    C6 N1 H1 . . 116.7(14) ?
    C2 N1 H1 . . 120.5(14) ?
    N1 C6 C5 . . 119.70(18) ?
    N1 C6 H6 . . 120.2 ?
    C5 C6 H6 . . 120.2 ?
    C6 C5 C4 . . 119.05(18) ?
    C6 C5 H5 . . 120.5 ?
    C4 C5 H5 . . 120.5 ?
    C3 C4 C5 . . 118.52(16) ?
    C3 C4 C7 . . 122.71(17) ?
    C5 C4 C7 . . 118.77(17) ?
    C2 C3 C4 . . 120.02(18) ?
    C2 C3 H3 . . 120.0 ?
    C4 C3 H3 . . 120.0 ?
    N1 C2 C3 . . 119.89(18) ?
    N1 C2 H2 . . 120.1 ?
    C3 C2 H2 . . 120.1 ?
    N8 C7 C4 . . 118.85(17) ?
    N8 C7 H7 . . 120.6 ?
    C4 C7 H7 . . 120.6 ?
    C7 N8 N9 . . 115.92(15) ?
    C10 N9 N8 . . 119.55(15) ?
    C10 N9 H9 . . 121.2(13) ?
    N8 N9 H9 . . 119.2(13) ?
    O11 C10 N9 . . 123.70(17) ?
    O11 C10 C12 . . 120.76(17) ?
    N9 C10 C12 . . 115.52(16) ?
    C13 C12 C17 . . 118.52(16) ?
    C13 C12 C10 . . 116.44(16) ?
    C17 C12 C10 . . 125.04(17) ?
    C14 C13 C12 . . 119.67(18) ?
    C14 C13 H13 . . 120.2 ?
    C12 C13 H13 . . 120.2 ?
    N15 C14 C13 . . 119.55(17) ?
    N15 C14 H14 . . 120.2 ?
    C13 C14 H14 . . 120.2 ?
    C14 N15 C16 . . 122.88(16) ?
    C14 N15 H15 . . 119.2(13) ?
    C16 N15 H15 . . 117.8(13) ?
    N15 C16 C17 . . 119.28(18) ?
    N15 C16 H16 . . 120.4 ?
    C17 C16 H16 . . 120.4 ?
    C16 C17 C12 . . 120.10(17) ?
    C16 C17 H17 . . 120.0 ?
    C12 C17 H17 . . 120.0 ?
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
    C2 N1 C6 C5 . . . . 1.2(3) ?
    N1 C6 C5 C4 . . . . -0.7(3) ?
    C6 C5 C4 C3 . . . . -0.5(3) ?
    C6 C5 C4 C7 . . . . 179.62(17) ?
    C5 C4 C3 C2 . . . . 1.2(3) ?
    C7 C4 C3 C2 . . . . -178.89(17) ?
    C6 N1 C2 C3 . . . . -0.4(3) ?
    C4 C3 C2 N1 . . . . -0.8(3) ?
    C3 C4 C7 N8 . . . . -0.6(3) ?
    C5 C4 C7 N8 . . . . 179.26(17) ?
    C4 C7 N8 N9 . . . . 179.86(15) ?
    C7 N8 N9 C10 . . . . 177.81(17) ?
    N8 N9 C10 O11 . . . . -0.8(3) ?
    N8 N9 C10 C12 . . . . 177.82(15) ?
    O11 C10 C12 C13 . . . . 3.5(3) ?
    N9 C10 C12 C13 . . . . -175.19(17) ?
    O11 C10 C12 C17 . . . . -176.79(19) ?
    N9 C10 C12 C17 . . . . 4.5(3) ?
    C17 C12 C13 C14 . . . . -0.1(3) ?
    C10 C12 C13 C14 . . . . 179.64(18) ?
    C12 C13 C14 N15 . . . . 0.0(3) ?
    C13 C14 N15 C16 . . . . 0.5(3) ?
    C14 N15 C16 C17 . . . . -0.8(3) ?
    N15 C16 C17 C12 . . . . 0.7(3) ?
    C13 C12 C17 C16 . . . . -0.2(3) ?
    C10 C12 C17 C16 . . . . -179.97(18) ?
data_global
_journal_date_recd_electronic     2002-03-18
_journal_date_accepted     2002-04-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2002
_journal_volume     58
_journal_issue      5
_journal_page_first     o519
_journal_page_last     o522
_journal_paper_category     EO
_publ_contact_author_name     'Dr Claire Wilson'
_publ_contact_author_address
;
School of Chemistry
University of Nottingham
University Park
Nottingham NG7 2RD
England
;
_publ_contact_author_email     claire.wilson@nott.ac.uk
_publ_contact_author_fax     '01159513563'
_publ_contact_author_phone     '01159513511'
_publ_section_title
;
1-(4-Pyridinio)-2'-[4-pyridinio-(E)-methylidene]hydrazide dinitrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Marina Felloni'
;
School of Chemistry
University of Nottingham
University Park
Nottingham NG7 2RD
England
;
    'Peter Hubberstey'
;
School of Chemistry
University of Nottingham
University Park
Nottingham NG7 2RD
England
;
    'Martin Schröder'
;
School of Chemistry
University of Nottingham
University Park
Nottingham NG7 2RD
England
;
    'Claire Wilson'
;
School of Chemistry
University of Nottingham
University Park
Nottingham NG7 2RD
England
;
