#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/73/2217366.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2217366
loop_
_publ_author_name
'Karadayı, Nevzat'
_publ_section_title
;
 Bis(2,6-diaminopyridinium)--adipate--adipic acid--water (2/1/1/2)
;
_journal_coeditor_code           XU2332
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o300
_journal_page_last               o300
_journal_paper_doi               10.1107/S1600536807055602
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac
'2C5 H8 N3 + , C6 H8 O4 2- , C6 H10 O4 , 2H2 O'
_chemical_formula_moiety
'2C5 H8 N3 + , C6 H8 O4 2- , C6 H10 O4 , 2H2 O'
_chemical_formula_sum            'C22 H38 N6 O10'
_chemical_formula_weight         546.58
_chemical_melting_point          .428E-305
_chemical_name_systematic
;
Bis(2,6-diaminopyridinium)--adipate--adipic acid--water (2/1/1/2)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                87.861(11)
_cell_angle_beta                 85.169(11)
_cell_angle_gamma                73.323(11)
_cell_formula_units_Z            1
_cell_length_a                   5.0645(7)
_cell_length_b                   7.6261(11)
_cell_length_c                   17.702(3)
_cell_measurement_reflns_used    8371
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.31
_cell_volume                     652.55(18)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics
;
ORTEPIII (Farrugia, 1997) and PLUTON (Spek, 1997)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7575
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.31
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9491
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.184
_refine_ls_extinction_coef       0.038(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0653P)²+0.039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1177
_reflns_number_gt                2261
_reflns_number_total             2996
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2332.cif
_cod_data_source_block           I
_cod_database_code               2217366
_cod_database_fobs_code          2217366
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
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_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)
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_4
_geom_torsion
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)
