##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-09-27
_journal_date_accepted     2007-11-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o300
_journal_page_last     o300
_journal_paper_category     QO
_journal_coeditor_code     XU2332
_publ_contact_author_name     'Karadayi, Nevzat'
_publ_contact_author_address
;
Samsun Vocational School
Ondokuz Mayis University
TR-55139 Samsun
Turkey
;
_publ_contact_author_email     nevzatk@omu.edu.tr
_publ_section_title
;
Bis(2,6-diaminopyridinium)--adipate--adipic acid--water (2/1/1/2)
;
loop_
    _publ_author_name
    _publ_author_address
    'Karadayı, Nevzat'
;
Samsun Vocational School
Ondokuz Mayıs University
TR-55139 Samsun
Turkey
;
data_I
_chemical_name_systematic
;
Bis(2,6-diaminopyridinium)--adipate--adipic acid--water (2/1/1/2)
;
_chemical_name_common     ?
_chemical_formula_moiety     '2C5 H8 N3 + , C6 H8 O4 2- , C6 H10 O4 , 2H2 O'
_chemical_formula_sum     'C22 H38 N6 O10'
_chemical_formula_iupac     '2C5 H8 N3 + , C6 H8 O4 2- , C6 H10 O4 , 2H2 O'
_chemical_formula_weight     546.58
_chemical_melting_point        .428E-305
_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     5.0645(7)
_cell_length_b     7.6261(11)
_cell_length_c     17.702(3)
_cell_angle_alpha     87.861(11)
_cell_angle_beta     85.169(11)
_cell_angle_gamma     73.323(11)
_cell_volume     652.55(18)
_cell_formula_units_Z     1
_cell_measurement_reflns_used     8371
_cell_measurement_theta_min     2.31
_cell_measurement_theta_max     27.93
_cell_measurement_temperature     296(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.60
_exptl_crystal_size_mid     0.48
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.391
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     292
_exptl_absorpt_coefficient_mu     0.110
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED32; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.9491
_exptl_absorpt_correction_T_max     0.9925
_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     'plane graphite'
_diffrn_measurement_device_type     'Stoe IPDS 2'
_diffrn_measurement_device     '2-circle goniometer'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7575
_diffrn_reflns_av_R_equivalents     0.0434
_diffrn_reflns_av_sigmaI/netI     0.0363
_diffrn_reflns_theta_min     2.31
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     22
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_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     2996
_reflns_number_gt     2261
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0564
_refine_ls_R_factor_gt     0.0413
_refine_ls_wR_factor_gt     0.1086
_refine_ls_wR_factor_ref     0.1177
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     2996
_refine_ls_number_parameters     192
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.0653P)²+0.039P] 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     0.212
_refine_diff_density_min     -0.184
_refine_ls_extinction_method     'SHELXL (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.038(10)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Farrugia, 1997) and PLUTON (Spek, 1997)
;
_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
    O O3 1.2490(2) 0.92346(16) 0.72447(6) 0.0543(3) Uani d D 1 . .
    O O4 1.5316(2) 0.79673(16) 0.62672(5) 0.0512(3) Uani d . 1 . .
    C C6 1.3110(3) 0.89651(18) 0.65252(7) 0.0374(3) Uani d . 1 . .
    N N3 1.1687(3) 0.4528(2) 0.91704(7) 0.0546(4) Uani d . 1 . .
    H H3A 1.0050 0.5265 0.9243 0.066 Uiso calc R 1 . .
    H H3B 1.2601 0.4051 0.9552 0.066 Uiso calc R 1 . .
    C C2 1.5414(3) 0.2937(2) 0.82983(8) 0.0460(3) Uani d . 1 . .
    H H2 1.6516 0.2374 0.8683 0.055 Uiso calc R 1 . .
    C C7 1.0880(3) 1.00201(19) 0.60401(7) 0.0418(3) Uani d . 1 . .
    H H7A 1.0818 1.1303 0.6047 0.050 Uiso calc R 1 . .
    H H7B 0.9120 0.9916 0.6267 0.050 Uiso calc R 1 . .
    C C1 1.2800(3) 0.41269(18) 0.84710(7) 0.0378(3) Uani d . 1 . .
    C C11 0.1384(3) 0.92888(18) 0.99095(7) 0.0382(3) Uani d . 1 . .
    H H11A 0.1273 0.8107 1.0108 0.046 Uiso calc R 1 . .
    H H11B 0.2798 0.9613 1.0164 0.046 Uiso calc R 1 . .
    O O2 0.6439(2) 0.69564(16) 0.93768(6) 0.0543(3) Uani d . 1 . .
    C C3 1.6345(3) 0.2603(2) 0.75544(9) 0.0501(4) Uani d . 1 . .
    H H3 1.8095 0.1809 0.7438 0.060 Uiso calc R 1 . .
    C C8 1.1183(3) 0.94351(18) 0.52225(7) 0.0388(3) Uani d . 1 . .
    H H8A 1.1244 0.8154 0.5207 0.047 Uiso calc R 1 . .
    H H8B 1.2916 0.9562 0.4985 0.047 Uiso calc R 1 . .
    C C9 0.5041(3) 0.77673(18) 0.88646(7) 0.0364(3) Uani d . 1 . .
    C C10 0.2239(3) 0.91266(19) 0.90622(7) 0.0388(3) Uani d . 1 . .
    H H10A 0.0849 0.8764 0.8812 0.047 Uiso calc R 1 . .
    H H10B 0.2273 1.0322 0.8862 0.047 Uiso calc R 1 . .
    N N1 1.1255(2) 0.49227(15) 0.78902(6) 0.0370(3) Uani d . 1 . .
    H H1 0.9640 0.5662 0.7997 0.044 Uiso calc R 1 . .
    C C4 1.4745(3) 0.3419(2) 0.69719(8) 0.0498(4) Uani d . 1 . .
    H H4 1.5402 0.3177 0.6469 0.060 Uiso calc R 1 . .
    O O1 0.58652(19) 0.75241(14) 0.81637(5) 0.0438(3) Uani d . 1 . .
    C C5 1.2154(3) 0.45998(19) 0.71505(7) 0.0396(3) Uani d . 1 . .
    N N2 1.0457(3) 0.5462(2) 0.66285(7) 0.0553(4) Uani d . 1 . .
    H H2A 0.8862 0.6189 0.6767 0.066 Uiso calc R 1 . .
    H H2B 1.0960 0.5289 0.6154 0.066 Uiso calc R 1 . .
    O O5 1.2848(3) 0.4164(2) 0.50152(7) 0.0631(4) Uani d DU 1 . .
    H H4A 1.373(4) 0.865(3) 0.7510(13) 0.094(8) Uiso d D 1 . .
    H H5A 1.335(4) 0.338(3) 0.4684(11) 0.076(6) Uiso d D 1 . .
    H H5B 1.114(4) 0.448(7) 0.506(3) 0.089(15) Uiso d PDU 0.50(4) A 1
    H H5C 1.416(7) 0.457(6) 0.507(3) 0.083(15) Uiso d PDU 0.50(4) . .
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 0.0458(6) 0.0706(7) 0.0278(5) 0.0149(5) -0.0071(4) -0.0044(5)
    O4 0.0367(5) 0.0684(7) 0.0338(5) 0.0096(4) -0.0053(4) -0.0049(4)
    C6 0.0346(6) 0.0427(7) 0.0292(6) -0.0012(5) -0.0052(5) -0.0017(5)
    N3 0.0456(7) 0.0723(8) 0.0295(6) 0.0086(6) -0.0002(5) 0.0004(5)
    C2 0.0378(7) 0.0526(8) 0.0361(7) 0.0061(6) -0.0075(5) 0.0038(6)
    C7 0.0372(7) 0.0470(7) 0.0322(6) 0.0043(5) -0.0076(5) -0.0020(5)
    C1 0.0358(6) 0.0415(7) 0.0310(6) -0.0029(5) -0.0029(5) 0.0011(5)
    C11 0.0341(6) 0.0455(7) 0.0288(6) -0.0018(5) -0.0010(5) -0.0020(5)
    O2 0.0410(5) 0.0729(7) 0.0315(5) 0.0124(5) -0.0062(4) 0.0011(5)
    C3 0.0370(7) 0.0570(8) 0.0419(7) 0.0092(6) -0.0005(6) -0.0042(6)
    C8 0.0343(6) 0.0441(7) 0.0309(6) 0.0016(5) -0.0079(5) 0.0001(5)
    C9 0.0322(6) 0.0426(6) 0.0292(6) -0.0021(5) -0.0027(5) -0.0017(5)
    C10 0.0335(6) 0.0443(7) 0.0311(6) 0.0006(5) -0.0013(5) -0.0006(5)
    N1 0.0298(5) 0.0424(6) 0.0312(5) 0.0016(4) -0.0012(4) -0.0001(4)
    C4 0.0418(7) 0.0618(9) 0.0324(7) 0.0056(6) 0.0021(6) -0.0043(6)
    O1 0.0373(5) 0.0547(6) 0.0274(5) 0.0052(4) 0.0000(4) -0.0023(4)
    C5 0.0366(6) 0.0456(7) 0.0311(6) -0.0032(5) -0.0031(5) 0.0016(5)
    N2 0.0421(7) 0.0760(9) 0.0331(6) 0.0073(6) -0.0075(5) 0.0038(6)
    O5 0.0483(7) 0.0801(9) 0.0503(7) 0.0009(6) -0.0029(6) -0.0218(6)
_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 C6 . 1.2955(15) ?
    O3 H4A . 0.829(17) ?
    O4 C6 . 1.2196(16) ?
    C6 C7 . 1.5001(18) ?
    N3 C1 . 1.3252(17) ?
    N3 H3A . 0.8600 ?
    N3 H3B . 0.8600 ?
    C2 C3 . 1.369(2) ?
    C2 C1 . 1.3901(18) ?
    C2 H2 . 0.9300 ?
    C7 C8 . 1.5129(17) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C1 N1 . 1.3617(17) ?
    C11 C11 2_577 1.524(2) ?
    C11 C10 . 1.5253(17) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    O2 C9 . 1.2332(16) ?
    C3 C4 . 1.382(2) ?
    C3 H3 . 0.9300 ?
    C8 C8 2_776 1.521(2) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 O1 . 1.2781(15) ?
    C9 C10 . 1.5199(16) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    N1 C5 . 1.3572(16) ?
    N1 H1 . 0.8600 ?
    C4 C5 . 1.3806(18) ?
    C4 H4 . 0.9300 ?
    C5 N2 . 1.3375(17) ?
    N2 H2A . 0.8600 ?
    N2 H2B . 0.8600 ?
    O5 H5A . 0.824(16) ?
    O5 H5B . 0.824(19) ?
    O5 H5C . 0.823(19) ?
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
    C6 O3 H4A . . 113.2(17) ?
    O4 C6 O3 . . 123.06(12) ?
    O4 C6 C7 . . 123.27(11) ?
    O3 C6 C7 . . 113.66(11) ?
    C1 N3 H3A . . 120.0 ?
    C1 N3 H3B . . 120.0 ?
    H3A N3 H3B . . 120.0 ?
    C3 C2 C1 . . 119.16(13) ?
    C3 C2 H2 . . 120.4 ?
    C1 C2 H2 . . 120.4 ?
    C6 C7 C8 . . 115.81(10) ?
    C6 C7 H7A . . 108.3 ?
    C8 C7 H7A . . 108.3 ?
    C6 C7 H7B . . 108.3 ?
    C8 C7 H7B . . 108.3 ?
    H7A C7 H7B . . 107.4 ?
    N3 C1 N1 . . 117.35(12) ?
    N3 C1 C2 . . 124.09(13) ?
    N1 C1 C2 . . 118.55(12) ?
    C11 C11 C10 2_577 . 113.06(13) ?
    C11 C11 H11A 2_577 . 109.0 ?
    C10 C11 H11A . . 109.0 ?
    C11 C11 H11B 2_577 . 109.0 ?
    C10 C11 H11B . . 109.0 ?
    H11A C11 H11B . . 107.8 ?
    C2 C3 C4 . . 121.51(13) ?
    C2 C3 H3 . . 119.2 ?
    C4 C3 H3 . . 119.2 ?
    C7 C8 C8 . 2_776 112.10(13) ?
    C7 C8 H8A . . 109.2 ?
    C8 C8 H8A 2_776 . 109.2 ?
    C7 C8 H8B . . 109.2 ?
    C8 C8 H8B 2_776 . 109.2 ?
    H8A C8 H8B . . 107.9 ?
    O2 C9 O1 . . 122.48(11) ?
    O2 C9 C10 . . 119.63(11) ?
    O1 C9 C10 . . 117.89(11) ?
    C9 C10 C11 . . 114.35(11) ?
    C9 C10 H10A . . 108.7 ?
    C11 C10 H10A . . 108.7 ?
    C9 C10 H10B . . 108.7 ?
    C11 C10 H10B . . 108.7 ?
    H10A C10 H10B . . 107.6 ?
    C5 N1 C1 . . 122.82(11) ?
    C5 N1 H1 . . 118.6 ?
    C1 N1 H1 . . 118.6 ?
    C5 C4 C3 . . 118.80(13) ?
    C5 C4 H4 . . 120.6 ?
    C3 C4 H4 . . 120.6 ?
    N2 C5 N1 . . 117.53(12) ?
    N2 C5 C4 . . 123.31(12) ?
    N1 C5 C4 . . 119.16(12) ?
    C5 N2 H2A . . 120.0 ?
    C5 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    H5A O5 H5B . . 108(4) ?
    H5A O5 H5C . . 107(4) ?
    H5B O5 H5C . . 140(5) ?
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
    O4 C6 C7 C8 . . . . 14.8(2) ?
    O3 C6 C7 C8 . . . . -166.16(13) ?
    C3 C2 C1 N3 . . . . 179.15(16) ?
    C3 C2 C1 N1 . . . . -0.1(2) ?
    C1 C2 C3 C4 . . . . -0.1(3) ?
    C6 C7 C8 C8 . . . 2_776 179.37(15) ?
    O2 C9 C10 C11 . . . . -2.29(19) ?
    O1 C9 C10 C11 . . . . 178.28(12) ?
    C11 C11 C10 C9 2_577 . . . 177.91(14) ?
    N3 C1 N1 C5 . . . . -179.08(13) ?
    C2 C1 N1 C5 . . . . 0.2(2) ?
    C2 C3 C4 C5 . . . . 0.2(3) ?
    C1 N1 C5 N2 . . . . -179.90(13) ?
    C1 N1 C5 C4 . . . . -0.1(2) ?
    C3 C4 C5 N2 . . . . 179.70(16) ?
    C3 C4 C5 N1 . . . . -0.1(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 H1 O1 . 0.86 2.03 2.8917(14) 175
    N2 H2A O4 1_455 0.86 2.15 2.8589(16) 139
    N2 H2B O5 . 0.86 2.25 3.0892(18) 166
    N3 H3A O2 . 0.86 1.91 2.7729(16) 178
    N3 H3B O2 2_767 0.86 2.06 2.8936(17) 162
    O3 H4A O1 1_655 0.829(17) 1.688(17) 2.5099(15) 171(3)
    O5 H5A O4 2_866 0.824(16) 1.972(17) 2.7773(15) 165(2)
    O5 H5B O5 2_766 0.824(19) 2.00(2) 2.804(3) 164(5)
    O5 H5C O5 2_866 0.823(19) 2.01(2) 2.819(3) 168(5)
