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###                                                                        ###
###        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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis(guanidinium)
bis(4-hydroxypyridine-2,6-dicarboxylato-κ³O²,N,O⁶)nickelate(II)
dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     '2(C H6 N3 +), C14 H6 N2 Ni O10 2-, 2(H2 O)'
_chemical_formula_sum     'C16 H22 N8 Ni O12'
_chemical_formula_iupac     '(C H6 N3)2 [Ni (C7 H3 N O5)2], 2H2 O'
_chemical_formula_weight     577.13
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.9253(6)
_cell_length_b     9.9060(6)
_cell_length_c     13.2186(9)
_cell_angle_alpha     101.415(3)
_cell_angle_beta     103.099(3)
_cell_angle_gamma     91.938(3)
_cell_volume     1111.99(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9699
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     36.26
_cell_measurement_temperature     150(2)
_exptl_crystal_description     block
_exptl_crystal_colour     green
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.32
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.724
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     596
_exptl_absorpt_coefficient_mu     0.956
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1998)'
_exptl_absorpt_correction_T_min     0.6465
_exptl_absorpt_correction_T_max     0.8699
_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     graphite
_diffrn_measurement_device_type     'Bruker SMART 1000'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     8.3
_diffrn_reflns_number     46516
_diffrn_reflns_av_R_equivalents     0.0194
_diffrn_reflns_av_sigmaI/netI     0.0151
_diffrn_reflns_theta_min     1.62
_diffrn_reflns_theta_max     36.35
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.972
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_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.
;
_reflns_number_total     10497
_reflns_number_gt     9650
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0289
_refine_ls_R_factor_gt     0.0258
_refine_ls_wR_factor_gt     0.0737
_refine_ls_wR_factor_ref     0.0758
_refine_ls_goodness_of_fit_ref     1.056
_refine_ls_restrained_S_all     1.056
_refine_ls_number_reflns     10497
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0430P)²+0.2702P] 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     0.002
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.560
_refine_diff_density_min     -0.612
_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'
    'Ni' 'Ni' 0.3393 1.1124
                         '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, 1998)'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
;
SHELXTL (Bruker, 2005) and
Mercury (Version 1.4.2; Macrae et al.,  2006)
;
_computing_publication_material     'SHELXL97 (Sheldrick, 1997)'
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
    Ni Ni1 0.173117(11) 0.423258(10) 0.259400(7) 0.01287(3) Uani d . 1 . .
    O O1 -0.00784(7) 0.27245(6) 0.24384(5) 0.01774(10) Uani d . 1 . .
    O O2 -0.16765(9) 0.11004(7) 0.12138(5) 0.02439(13) Uani d . 1 . .
    O O3 -0.02586(9) 0.20971(7) -0.21698(5) 0.02167(12) Uani d . 1 . .
    H H3C -0.0206 0.2745 -0.2554 0.026 Uiso d R 1 . .
    O O4 0.35691(8) 0.60277(7) 0.04763(5) 0.02381(12) Uani d . 1 . .
    O O5 0.31707(7) 0.56247(6) 0.20082(5) 0.01687(10) Uani d . 1 . .
    O O6 0.05225(7) 0.59263(6) 0.32052(4) 0.01635(10) Uani d . 1 . .
    O O7 0.02582(8) 0.72029(7) 0.47531(5) 0.02065(11) Uani d . 1 . .
    O O8 0.37838(8) 0.46857(7) 0.73456(5) 0.02054(11) Uani d . 1 . .
    H H8 0.4719 0.4367 0.7525 0.025 Uiso d R 1 . .
    O O9 0.51375(8) 0.19318(7) 0.39007(5) 0.02143(11) Uani d . 1 . .
    O O10 0.34554(7) 0.27853(6) 0.26981(5) 0.01768(10) Uani d . 1 . .
    O O11 0.32536(8) -0.04310(7) 0.73709(5) 0.02032(11) Uani d . 1 . .
    H H11A 0.3814 -0.1076 0.7089 0.024 Uiso d R 1 . .
    H H11B 0.2653 -0.0814 0.7719 0.024 Uiso d R 1 . .
    O O12 0.37899(13) 0.87354(12) 0.25296(8) 0.0491(3) Uani d . 1 . .
    H H12B 0.4704 0.9157 0.2539 0.059 Uiso d R 1 . .
    H H12A 0.3664 0.7820 0.2257 0.059 Uiso d R 1 . .
    N N1 0.09970(7) 0.36856(6) 0.10372(5) 0.01309(10) Uani d . 1 . .
    N N2 0.25270(7) 0.44832(6) 0.41390(5) 0.01274(10) Uani d . 1 . .
    N N3 0.50285(9) 0.28895(8) 0.10335(6) 0.02072(13) Uani d . 1 . .
    H H3A 0.5659 0.3475 0.0847 0.025 Uiso d R 1 . .
    H H3B 0.4860 0.3064 0.1691 0.025 Uiso d R 1 . .
    N N4 0.43549(11) 0.16824(9) -0.06920(7) 0.02808(17) Uani d . 1 . .
    H H4A 0.5014 0.2288 -0.0833 0.034 Uiso d R 1 . .
    H H4B 0.3907 0.0927 -0.1182 0.034 Uiso d R 1 . .
    N N5 0.32885(10) 0.09767(8) 0.05716(6) 0.02313(14) Uani d . 1 . .
    H H5A 0.3226 0.1189 0.1254 0.028 Uiso d R 1 . .
    H H5B 0.2719 0.0285 0.0071 0.028 Uiso d R 1 . .
    N N6 0.12908(10) 0.08178(8) 0.38427(6) 0.02258(13) Uani d . 1 . .
    H H6A 0.0636 0.1481 0.3920 0.027 Uiso d R 1 . .
    H H6B 0.1274 0.0351 0.3182 0.027 Uiso d R 1 . .
    N N7 0.29526(10) -0.06930(9) 0.45012(7) 0.02577(15) Uani d . 1 . .
    H H7A 0.3483 -0.1044 0.5041 0.031 Uiso d R 1 . .
    H H7B 0.3174 -0.0873 0.3859 0.031 Uiso d R 1 . .
    N N8 0.18342(10) 0.08088(8) 0.56283(6) 0.02222(13) Uani d . 1 . .
    H H8A 0.1141 0.1442 0.5680 0.027 Uiso d R 1 . .
    H H8B 0.2214 0.0388 0.6166 0.027 Uiso d R 1 . .
    C C1 -0.06666(9) 0.20926(8) 0.14912(6) 0.01563(12) Uani d . 1 . .
    C C2 -0.00601(8) 0.26094(7) 0.06391(6) 0.01391(11) Uani d . 1 . .
    C C3 -0.04990(9) 0.20506(8) -0.04397(6) 0.01656(12) Uani d . 1 . .
    H H3 -0.1226 0.1295 -0.0705 0.020 Uiso calc R 1 . .
    C C4 0.01756(9) 0.26469(8) -0.11267(6) 0.01546(12) Uani d . 1 . .
    C C5 0.12882(9) 0.37751(8) -0.06979(6) 0.01465(11) Uani d . 1 . .
    H H5 0.1754 0.4190 -0.1134 0.018 Uiso calc R 1 . .
    C C6 0.16685(8) 0.42490(7) 0.03947(5) 0.01292(11) Uani d . 1 . .
    C C7 0.28988(9) 0.53963(8) 0.09859(6) 0.01487(11) Uani d . 1 . .
    C C8 0.08025(9) 0.62575(7) 0.42266(6) 0.01421(11) Uani d . 1 . .
    C C9 0.19209(8) 0.53834(7) 0.47982(5) 0.01287(11) Uani d . 1 . .
    C C10 0.23152(9) 0.54827(8) 0.58878(6) 0.01447(11) Uani d . 1 . .
    H H10 0.1879 0.6108 0.6338 0.017 Uiso calc R 1 . .
    C C11 0.33960(9) 0.46069(8) 0.62872(6) 0.01443(11) Uani d . 1 . .
    C C12 0.40380(9) 0.36772(8) 0.55896(6) 0.01472(11) Uani d . 1 . .
    H H12 0.4767 0.3100 0.5843 0.018 Uiso calc R 1 . .
    C C13 0.35558(8) 0.36443(7) 0.45134(6) 0.01300(11) Uani d . 1 . .
    C C14 0.41057(9) 0.26960(7) 0.36476(6) 0.01460(11) Uani d . 1 . .
    C C15 0.42237(9) 0.18398(8) 0.03028(6) 0.01729(12) Uani d . 1 . .
    C C16 0.20223(9) 0.02991(8) 0.46651(7) 0.01741(12) Uani d . 1 . .
_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
    Ni1 N2 . 1.9665(6) y
    Ni1 N1 . 1.9700(6) y
    Ni1 O1 . 2.1088(6) y
    Ni1 O10 . 2.1387(6) y
    Ni1 O6 . 2.1477(6) y
    Ni1 O5 . 2.2149(6) y
    O1 C1 . 1.2668(9) ?
    O2 C1 . 1.2492(10) ?
    O3 C4 . 1.3394(9) ?
    O3 H3C . 0.9000 ?
    O4 C7 . 1.2357(9) ?
    O5 C7 . 1.2895(9) ?
    O6 C8 . 1.2880(9) ?
    O7 C8 . 1.2343(10) ?
    O8 C11 . 1.3485(9) ?
    O8 H8 . 0.9000 ?
    O9 C14 . 1.2413(9) ?
    O10 C14 . 1.2796(9) ?
    O11 H11A . 0.9000 ?
    O11 H11B . 0.9001 ?
    O12 H12B . 0.9000 ?
    O12 H12A . 0.9000 ?
    N1 C6 . 1.3371(9) ?
    N1 C2 . 1.3374(9) ?
    N2 C9 . 1.3363(9) ?
    N2 C13 . 1.3368(9) ?
    N3 C15 . 1.3296(10) ?
    N3 H3A . 0.9001 ?
    N3 H3B . 0.9001 ?
    N4 C15 . 1.3256(11) ?
    N4 H4A . 0.9000 ?
    N4 H4B . 0.9000 ?
    N5 C15 . 1.3267(11) ?
    N5 H5A . 0.9002 ?
    N5 H5B . 0.9000 ?
    N6 C16 . 1.3394(10) ?
    N6 H6A . 0.9000 ?
    N6 H6B . 0.9001 ?
    N7 C16 . 1.3247(11) ?
    N7 H7A . 0.9000 ?
    N7 H7B . 0.8999 ?
    N8 C16 . 1.3238(11) ?
    N8 H8A . 0.9000 ?
    N8 H8B . 0.9002 ?
    C1 C2 . 1.5198(10) ?
    C2 C3 . 1.3832(10) ?
    C3 C4 . 1.4044(11) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.4055(11) ?
    C5 C6 . 1.3857(10) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.5111(10) ?
    C8 C9 . 1.5141(10) ?
    C9 C10 . 1.3856(10) ?
    C10 C11 . 1.4032(11) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.4021(11) ?
    C12 C13 . 1.3833(10) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.5143(10) ?
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
    N2 Ni1 N1 . . 171.30(3) y
    O1 Ni1 O5 . . 154.97(2) y
    O10 Ni1 O6 . . 154.87(2) y
    N2 Ni1 O1 . . 96.84(2) ?
    N1 Ni1 O1 . . 78.70(2) ?
    N2 Ni1 O10 . . 77.95(2) ?
    N1 Ni1 O10 . . 94.76(2) ?
    O1 Ni1 O10 . . 93.41(3) y
    N2 Ni1 O6 . . 77.41(2) ?
    N1 Ni1 O6 . . 110.20(2) ?
    O1 Ni1 O6 . . 94.31(2) ?
    N2 Ni1 O5 . . 108.19(2) ?
    N1 Ni1 O5 . . 76.46(2) ?
    O10 Ni1 O5 . . 91.73(2) ?
    O6 Ni1 O5 . . 91.30(2) y
    C1 O1 Ni1 . . 114.35(5) ?
    C4 O3 H3C . . 111.0 ?
    C7 O5 Ni1 . . 113.28(5) ?
    C8 O6 Ni1 . . 114.63(5) ?
    C11 O8 H8 . . 109.2 ?
    C14 O10 Ni1 . . 114.35(5) ?
    H11A O11 H11B . . 109.4 ?
    H12B O12 H12A . . 115.5 ?
    C6 N1 C2 . . 120.41(6) ?
    C6 N1 Ni1 . . 121.23(5) ?
    C2 N1 Ni1 . . 117.81(5) ?
    C9 N2 C13 . . 120.78(6) ?
    C9 N2 Ni1 . . 119.82(5) ?
    C13 N2 Ni1 . . 119.03(5) ?
    C15 N3 H3A . . 119.6 ?
    C15 N3 H3B . . 119.6 ?
    H3A N3 H3B . . 120.4 ?
    C15 N4 H4A . . 117.6 ?
    C15 N4 H4B . . 120.5 ?
    H4A N4 H4B . . 121.3 ?
    C15 N5 H5A . . 115.0 ?
    C15 N5 H5B . . 119.8 ?
    H5A N5 H5B . . 125.0 ?
    C16 N6 H6A . . 121.8 ?
    C16 N6 H6B . . 118.1 ?
    H6A N6 H6B . . 118.4 ?
    C16 N7 H7A . . 121.3 ?
    C16 N7 H7B . . 116.5 ?
    H7A N7 H7B . . 121.1 ?
    C16 N8 H8A . . 116.9 ?
    C16 N8 H8B . . 119.8 ?
    H8A N8 H8B . . 121.8 ?
    O2 C1 O1 . . 125.67(7) ?
    O2 C1 C2 . . 118.69(7) ?
    O1 C1 C2 . . 115.64(6) ?
    N1 C2 C3 . . 121.56(7) ?
    N1 C2 C1 . . 112.83(6) ?
    C3 C2 C1 . . 125.60(7) ?
    C2 C3 C4 . . 118.69(7) ?
    C2 C3 H3 . . 120.7 ?
    C4 C3 H3 . . 120.7 ?
    O3 C4 C3 . . 118.15(7) ?
    O3 C4 C5 . . 122.66(7) ?
    C3 C4 C5 . . 119.18(7) ?
    C6 C5 C4 . . 117.89(6) ?
    C6 C5 H5 . . 121.1 ?
    C4 C5 H5 . . 121.1 ?
    N1 C6 C5 . . 122.25(7) ?
    N1 C6 C7 . . 113.16(6) ?
    C5 C6 C7 . . 124.55(6) ?
    O4 C7 O5 . . 125.12(7) ?
    O4 C7 C6 . . 119.22(7) ?
    O5 C7 C6 . . 115.66(6) ?
    O7 C8 O6 . . 126.10(7) ?
    O7 C8 C9 . . 119.17(7) ?
    O6 C8 C9 . . 114.73(6) ?
    N2 C9 C10 . . 121.93(7) ?
    N2 C9 C8 . . 112.93(6) ?
    C10 C9 C8 . . 125.14(7) ?
    C9 C10 C11 . . 117.64(7) ?
    C9 C10 H10 . . 121.2 ?
    C11 C10 H10 . . 121.2 ?
    O8 C11 C12 . . 121.73(7) ?
    O8 C11 C10 . . 118.30(7) ?
    C12 C11 C10 . . 119.96(6) ?
    C13 C12 C11 . . 118.05(7) ?
    C13 C12 H12 . . 121.0 ?
    C11 C12 H12 . . 121.0 ?
    N2 C13 C12 . . 121.62(7) ?
    N2 C13 C14 . . 113.12(6) ?
    C12 C13 C14 . . 125.25(7) ?
    O9 C14 O10 . . 125.71(7) ?
    O9 C14 C13 . . 119.11(7) ?
    O10 C14 C13 . . 115.17(6) ?
    N4 C15 N5 . . 120.87(8) ?
    N4 C15 N3 . . 119.19(8) ?
    N5 C15 N3 . . 119.93(8) ?
    N8 C16 N7 . . 121.25(8) ?
    N8 C16 N6 . . 119.57(8) ?
    N7 C16 N6 . . 119.16(8) ?
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
    N2 Ni1 O1 C1 . . . . -165.80(6) ?
    N1 Ni1 O1 C1 . . . . 6.63(6) ?
    O10 Ni1 O1 C1 . . . . -87.54(6) ?
    O6 Ni1 O1 C1 . . . . 116.39(6) ?
    O5 Ni1 O1 C1 . . . . 13.95(10) ?
    N2 Ni1 O5 C7 . . . . 170.16(5) ?
    N1 Ni1 O5 C7 . . . . -2.20(5) ?
    O1 Ni1 O5 C7 . . . . -9.58(9) ?
    O10 Ni1 O5 C7 . . . . 92.27(5) y
    O6 Ni1 O5 C7 . . . . -112.67(5) ?
    N2 Ni1 O6 C8 . . . . -2.86(5) ?
    N1 Ni1 O6 C8 . . . . 172.73(5) ?
    O1 Ni1 O6 C8 . . . . 93.20(5) y
    O10 Ni1 O6 C8 . . . . -14.34(9) ?
    O5 Ni1 O6 C8 . . . . -111.22(5) ?
    N2 Ni1 O10 C14 . . . . 3.50(5) ?
    N1 Ni1 O10 C14 . . . . -171.70(6) ?
    O1 Ni1 O10 C14 . . . . -92.77(6) ?
    O6 Ni1 O10 C14 . . . . 14.95(9) ?
    O5 Ni1 O10 C14 . . . . 111.74(6) ?
    N2 Ni1 N1 C6 . . . . -119.19(16) ?
    O1 Ni1 N1 C6 . . . . -179.02(6) ?
    O10 Ni1 N1 C6 . . . . -86.48(6) ?
    O6 Ni1 N1 C6 . . . . 90.51(6) ?
    O5 Ni1 N1 C6 . . . . 4.16(6) ?
    N2 Ni1 N1 C2 . . . . 52.35(19) ?
    O1 Ni1 N1 C2 . . . . -7.48(6) ?
    O10 Ni1 N1 C2 . . . . 85.06(6) ?
    O6 Ni1 N1 C2 . . . . -97.95(6) ?
    O5 Ni1 N1 C2 . . . . 175.70(6) ?
    N1 Ni1 N2 C9 . . . . -145.37(15) ?
    O1 Ni1 N2 C9 . . . . -86.74(6) ?
    O10 Ni1 N2 C9 . . . . -178.78(6) ?
    O6 Ni1 N2 C9 . . . . 6.18(5) ?
    O5 Ni1 N2 C9 . . . . 93.38(6) ?
    N1 Ni1 N2 C13 . . . . 27.7(2) ?
    O1 Ni1 N2 C13 . . . . 86.32(6) ?
    O10 Ni1 N2 C13 . . . . -5.72(5) ?
    O6 Ni1 N2 C13 . . . . 179.23(6) ?
    O5 Ni1 N2 C13 . . . . -93.57(6) ?
    Ni1 O1 C1 O2 . . . . 174.96(7) ?
    Ni1 O1 C1 C2 . . . . -4.79(9) ?
    C6 N1 C2 C3 . . . . -0.36(11) ?
    Ni1 N1 C2 C3 . . . . -171.97(6) ?
    C6 N1 C2 C1 . . . . 178.76(6) ?
    Ni1 N1 C2 C1 . . . . 7.15(8) ?
    O2 C1 C2 N1 . . . . 179.06(7) ?
    O1 C1 C2 N1 . . . . -1.17(10) ?
    O2 C1 C2 C3 . . . . -1.87(12) ?
    O1 C1 C2 C3 . . . . 177.90(8) ?
    N1 C2 C3 C4 . . . . -0.79(12) ?
    C1 C2 C3 C4 . . . . -179.78(7) ?
    C2 C3 C4 O3 . . . . -179.99(7) ?
    C2 C3 C4 C5 . . . . 0.95(12) ?
    O3 C4 C5 C6 . . . . -179.04(7) ?
    C3 C4 C5 C6 . . . . -0.02(11) ?
    C2 N1 C6 C5 . . . . 1.36(11) ?
    Ni1 N1 C6 C5 . . . . 172.68(5) ?
    C2 N1 C6 C7 . . . . -176.55(6) ?
    Ni1 N1 C6 C7 . . . . -5.23(8) ?
    C4 C5 C6 N1 . . . . -1.14(11) ?
    C4 C5 C6 C7 . . . . 176.52(7) ?
    Ni1 O5 C7 O4 . . . . -179.06(7) ?
    Ni1 O5 C7 C6 . . . . 0.27(8) ?
    N1 C6 C7 O4 . . . . -177.72(7) ?
    C5 C6 C7 O4 . . . . 4.43(12) ?
    N1 C6 C7 O5 . . . . 2.91(10) ?
    C5 C6 C7 O5 . . . . -174.94(7) ?
    Ni1 O6 C8 O7 . . . . 179.06(7) ?
    Ni1 O6 C8 C9 . . . . -0.37(8) ?
    C13 N2 C9 C10 . . . . -0.51(11) ?
    Ni1 N2 C9 C10 . . . . 172.42(5) ?
    C13 N2 C9 C8 . . . . 178.98(6) ?
    Ni1 N2 C9 C8 . . . . -8.09(8) ?
    O7 C8 C9 N2 . . . . -174.29(7) ?
    O6 C8 C9 N2 . . . . 5.18(9) ?
    O7 C8 C9 C10 . . . . 5.17(11) ?
    O6 C8 C9 C10 . . . . -175.36(7) ?
    N2 C9 C10 C11 . . . . 0.58(11) ?
    C8 C9 C10 C11 . . . . -178.84(7) ?
    C9 C10 C11 O8 . . . . -179.59(7) ?
    C9 C10 C11 C12 . . . . 0.16(11) ?
    O8 C11 C12 C13 . . . . 178.81(7) ?
    C10 C11 C12 C13 . . . . -0.94(11) ?
    C9 N2 C13 C12 . . . . -0.33(11) ?
    Ni1 N2 C13 C12 . . . . -173.32(5) ?
    C9 N2 C13 C14 . . . . 179.79(6) ?
    Ni1 N2 C13 C14 . . . . 6.80(8) ?
    C11 C12 C13 N2 . . . . 1.04(11) ?
    C11 C12 C13 C14 . . . . -179.09(7) ?
    Ni1 O10 C14 O9 . . . . -179.76(7) ?
    Ni1 O10 C14 C13 . . . . -1.05(8) ?
    N2 C13 C14 O9 . . . . 175.34(7) ?
    C12 C13 C14 O9 . . . . -4.54(11) ?
    N2 C13 C14 O10 . . . . -3.46(9) ?
    C12 C13 C14 O10 . . . . 176.66(7) ?
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
    O3 H3C O6 2_565 0.90 1.71 2.5901(8) 165.9
    O8 H8 O5 2_666 0.90 1.84 2.7057(9) 159.7
    O11 H11A O9 2_656 0.90 1.86 2.7106(9) 156.0
    O11 H11B O2 2_556 0.90 1.88 2.7464(9) 161.3
    O12 H12B O11 2_666 0.90 2.15 3.0425(12) 171.9
    O12 H12A O5 . 0.90 2.15 3.0244(13) 164.0
    O12 H12A O4 . 0.90 2.64 3.3823(12) 141.0
    N3 H3A O4 2_665 0.90 2.15 2.9307(10) 143.9
    N3 H3B O10 . 0.90 2.07 2.8817(10) 149.0
    N4 H4A O4 2_665 0.90 1.97 2.8072(11) 154.0
    N4 H4B O11 1_554 0.90 2.06 2.9161(10) 159.3
    N5 H5A O10 . 0.90 2.19 2.9887(10) 147.7
    N5 H5B O2 2 0.90 1.98 2.8656(10) 169.0
    N6 H6A O7 2_566 0.90 2.28 3.0178(11) 138.6
    N6 H6A O1 . 0.90 2.49 3.0038(9) 116.7
    N6 H6B O3 2 0.90 2.55 3.2320(11) 132.8
    N7 H7A O9 2_656 0.90 2.01 2.8999(10) 171.6
    N7 H7B O12 1_545 0.90 1.93 2.8282(13) 176.2
    N8 H8A O7 2_566 0.90 1.94 2.7993(10) 157.9
    N8 H8B O11 . 0.90 1.99 2.8847(10) 174.2
    N5 H5A Cg1(N1/C2--C6) 1_555 0.90 3.47 3.362(7) 75.3
data_global
_journal_date_recd_electronic     2007-11-05
_journal_date_accepted     2007-12-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     m144
_journal_page_last     m145
_journal_paper_category     QM
_journal_coeditor_code     OM2189
_publ_contact_author_name     'Hossein Aghabozorg'
_publ_contact_author_address
;
Faculty of Chemistry, Teacher Training University, Tehran, Iran
;
_publ_contact_author_email     haghabozorg@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
Bis(guanidinium)
bis(4-hydroxypyridine-2,6-dicarboxylato-κ³O²,N,\
O⁶)nickelate(II) dihydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Aghabozorg, Hossein' .
;
Faculty of Chemistry, Teacher Training University, Tehran, Iran
;
    'Motyeian, Elham' .
;
Faculty of Chemistry, Teacher Training University, Tehran, Iran
;
    'Attar Gharamaleki, Jafar' .
;
Faculty of Chemistry, Teacher Training University, Tehran, Iran
;
    'Soleimannejad, Janet' .
;
Faculty of Science, Department of Chemistry, Ilam University, Iran
;
    'Ghadermazi, Mohammad' .
;
Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj,
Iran
;
    'Elizabeth Spey Sharon' .
;Department of Chemistry, Sheffield University, Sheffield S3 7HF, England
;
