#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/73/2217399.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_2217399
loop_
_publ_author_name
'Wojciech Starosta'
'Janusz Leciejewicz'
_publ_section_title
;
 Hydrazinediium bis(6-carboxypyridazine-3-carboxylate) dihydrate
;
_journal_coeditor_code           AT2534
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o461
_journal_page_last               o461
_journal_paper_doi               10.1107/S1600536808001037
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'N2 H6 2+ , 2C6 H3 N2 O4 - , 2H2 O'
_chemical_formula_moiety         'H6 N2 2+ , 2C6 H3 N2 O4 - , 2H2 O'
_chemical_formula_sum            'C12 H16 N6 O10'
_chemical_formula_weight         404.31
_chemical_name_systematic
;
Hydrazinediium bis(6-carboxypyridazine-3-carboxylate) dihydrate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.08(3)
_cell_angle_beta                 93.92(3)
_cell_angle_gamma                107.44(3)
_cell_formula_units_Z            1
_cell_length_a                   5.1727(10)
_cell_length_b                   6.6257(13)
_cell_length_c                   12.271(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      6
_cell_volume                     388.45(17)
_computing_cell_refinement       'KM-4 Software (Kuma, 1996)'
_computing_data_collection       'KM-4 Software (Kuma, 1996)'
_computing_data_reduction        'DATAPROC (Kuma, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Kuma KM-4 four-circle'
_diffrn_measurement_method       'profile data from ω/2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2512
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        3.72
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  3.072
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_F_000             210
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.092P)²] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1328
_reflns_number_gt                1431
_reflns_number_total             2279
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2534.cif
_cod_data_source_block           I
_cod_original_cell_volume        388.47(17)
_cod_database_code               2217399
_cod_database_fobs_code          2217399
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_occupancy
O O2 0.0745(3) 1.1260(2) 0.19096(9) 0.0301(3) Uani d 1
O O3 0.6795(3) 0.37197(19) 0.35261(9) 0.0292(3) Uani d 1
O O4 0.7130(3) 0.4033(2) 0.17502(10) 0.0319(3) Uani d 1
O O1 -0.0377(3) 1.1253(2) 0.36330(10) 0.0315(3) Uani d 1
N N2 0.3236(3) 0.8346(2) 0.19854(10) 0.0248(3) Uani d 1
N N1 0.4514(3) 0.6882(2) 0.19574(10) 0.0261(3) Uani d 1
C C6 0.4853(3) 0.6120(2) 0.28600(11) 0.0198(3) Uani d 1
C C3 0.2223(3) 0.9032(2) 0.29085(11) 0.0191(3) Uani d 1
C C7 0.0773(3) 1.0655(2) 0.27720(12) 0.0212(3) Uani d 1
C C4 0.2473(3) 0.8274(2) 0.38706(12) 0.0238(3) Uani d 1
C C8 0.6396(3) 0.4472(2) 0.26852(12) 0.0215(3) Uani d 1
C C5 0.3863(4) 0.6784(3) 0.38484(12) 0.0250(3) Uani d 1
O O6 0.1862(3) 0.3212(2) 0.98874(10) 0.0295(3) Uani d 1
N N3 0.3528(3) 0.9661(2) 0.99354(11) 0.0233(3) Uani d 1
H H5 0.169(4) 0.871(3) 0.4510(18) 0.031(5) Uiso d 1
H H6 0.411(4) 0.628(3) 0.4471(19) 0.037(6) Uiso d 1
H H62 0.268(6) 0.416(5) 1.044(2) 0.059(8) Uiso d 1
H H51 0.288(5) 0.840(4) 0.9317(19) 0.038(6) Uiso d 1
H H61 0.223(5) 0.395(4) 0.927(2) 0.045(6) Uiso d 1
H H53 0.307(5) 0.924(3) 1.0576(18) 0.035(5) Uiso d 1
H H52 0.288(5) 1.098(4) 0.9885(18) 0.036(5) Uiso d 1
H H1 -0.136(8) 1.234(6) 0.350(3) 0.117(14) Uiso d 1
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
O2 0.0426(8) 0.0379(6) 0.0231(5) 0.0268(6) 0.0091(5) 0.0143(4)
O3 0.0400(7) 0.0348(6) 0.0259(5) 0.0261(5) 0.0095(5) 0.0130(4)
O4 0.0465(8) 0.0369(6) 0.0248(5) 0.0295(6) 0.0119(5) 0.0082(4)
O1 0.0459(8) 0.0394(7) 0.0263(5) 0.0315(6) 0.0165(5) 0.0148(5)
N2 0.0362(8) 0.0282(6) 0.0197(5) 0.0208(6) 0.0089(5) 0.0098(5)
N1 0.0382(8) 0.0294(7) 0.0215(6) 0.0231(6) 0.0105(5) 0.0092(5)
C6 0.0237(7) 0.0200(6) 0.0200(6) 0.0123(5) 0.0051(5) 0.0055(5)
C3 0.0225(7) 0.0199(6) 0.0184(6) 0.0109(5) 0.0044(5) 0.0056(5)
C7 0.0238(7) 0.0222(7) 0.0210(6) 0.0119(6) 0.0037(5) 0.0053(5)
C4 0.0339(8) 0.0279(7) 0.0179(6) 0.0194(6) 0.0084(6) 0.0077(5)
C8 0.0249(8) 0.0202(6) 0.0231(6) 0.0124(6) 0.0036(5) 0.0058(5)
C5 0.0373(9) 0.0284(7) 0.0190(6) 0.0206(7) 0.0081(6) 0.0102(5)
O6 0.0375(7) 0.0290(6) 0.0237(6) 0.0128(5) 0.0049(5) 0.0070(4)
N3 0.0225(7) 0.0293(7) 0.0220(6) 0.0121(5) 0.0057(5) 0.0084(5)
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
C7 O1 H1 . 111(2)
N1 N2 C3 . 120.23(12)
N2 N1 C6 . 120.34(12)
N1 C6 C5 . 122.08(13)
N1 C6 C8 . 113.36(12)
C5 C6 C8 . 124.56(12)
N2 C3 C4 . 122.16(13)
N2 C3 C7 . 112.66(12)
C4 C3 C7 . 125.17(13)
O2 C7 O1 . 126.02(13)
O2 C7 C3 . 119.91(13)
O1 C7 C3 . 114.07(12)
C5 C4 C3 . 117.50(13)
C5 C4 H5 . 120.3(13)
C3 C4 H5 . 122.1(13)
O4 C8 O3 . 127.45(13)
O4 C8 C6 . 116.92(12)
O3 C8 C6 . 115.63(12)
C4 C5 C6 . 117.66(13)
C4 C5 H6 . 119.8(14)
C6 C5 H6 . 122.5(14)
H62 O6 H61 . 103(2)
N3 N3 H51 2_677 106.7(14)
N3 N3 H53 2_677 105.3(14)
H51 N3 H53 . 108(2)
N3 N3 H52 2_677 109.5(13)
H51 N3 H52 . 117.5(18)
H53 N3 H52 . 109.0(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O2 C7 . 1.2082(18)
O3 C8 . 1.2666(17)
O4 C8 . 1.2376(18)
O1 C7 . 1.2956(18)
O1 H1 . 1.03(4)
N2 N1 . 1.3241(17)
N2 C3 . 1.3313(18)
N1 C6 . 1.3317(17)
C6 C5 . 1.387(2)
C6 C8 . 1.5236(18)
C3 C4 . 1.3889(19)
C3 C7 . 1.5128(18)
C4 C5 . 1.382(2)
C4 H5 . 0.94(2)
C5 H6 . 0.91(2)
O6 H62 . 0.81(3)
O6 H61 . 0.98(3)
N3 N3 2_677 1.440(3)
N3 H51 . 0.96(2)
N3 H53 . 0.91(2)
N3 H52 . 1.04(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
O6 H62 N1 1_556 0.81(3) 2.23(3) 3.031(2) 174(3)
N3 H51 O4 2_666 0.96(2) 1.85(2) 2.770(2) 160(2)
O6 H61 O4 2_666 0.98(3) 1.99(3) 2.9581(18) 168(2)
O6 H61 N1 2_666 0.98(3) 2.45(2) 3.039(2) 118.5(18)
N3 H53 N2 1_556 0.91(2) 1.95(2) 2.8287(18) 163(2)
N3 H53 O2 1_556 0.91(2) 2.50(2) 3.0627(19) 120.7(17)
N3 H52 O6 1_565 1.04(2) 1.71(2) 2.7473(18) 176.6(19)
O1 H1 O3 1_465 1.03(4) 1.51(4) 2.5152(16) 165(3)
