#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/43/2234306.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_2234306
loop_
_publ_author_name
'Starosta, Wojciech'
'Leciejewicz, Janusz'
_publ_section_title
;
 Poly[hydrazin-1-ium
 [diaquabis(μ₄-pyridazine-3,6-dicarboxylato)trilithate] monohydrate]
;
_journal_coeditor_code           KP2395
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m496
_journal_page_last               m497
_journal_paper_doi               10.1107/S1600536812012743
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '(N2 H5) [Li3 (C6 H2 N2 O4)2 (H2 O1)2], H2 O'
_chemical_formula_moiety         'H5 N2 +, C12 H8 Li3 N4 O10 -, H2 O'
_chemical_formula_sum            'C12 H15 Li3 N6 O11'
_chemical_formula_weight         440.12
_chemical_name_systematic
;
Poly[hydrazin-1-ium
[diaquabis(μ₄-pyridazine-3,6-dicarboxylato)trilithate] monohydrate]
;
_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                97.62(3)
_cell_angle_beta                 90.62(3)
_cell_angle_gamma                95.77(3)
_cell_formula_units_Z            2
_cell_length_a                   5.2150(10)
_cell_length_b                   7.3356(15)
_cell_length_c                   24.001(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      6
_cell_volume                     905.2(3)
_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  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'Kuma KM-4 four-cricle'
_diffrn_measurement_method       'profile data from ω/2θ scans'
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5141
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         1.71
_diffrn_standards_decay_%        1.43
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  0.99238
_exptl_absorpt_correction_T_min  0.98210
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.056
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.477
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4676
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0574
_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)+(0.1704P)²+0.0007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.2426
_reflns_number_gt                2660
_reflns_number_total             4676
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kp2395.cif
_cod_data_source_block           I
_cod_database_code               2234306
_cod_database_fobs_code          2234306
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_symmetry_multiplicity
O O21 0.5659(4) 0.6958(3) -0.10200(9) 0.0309(5) Uani d . 1 1
O O12 0.1688(4) 0.6942(3) 0.56969(10) 0.0294(5) Uani d . 1 1
N N21 0.7101(4) 0.8483(3) 0.00022(10) 0.0205(5) Uani d . 1 1
O O11 0.5736(4) 0.7887(3) 0.60076(9) 0.0306(5) Uani d . 1 1
N N11 0.7993(5) 0.8737(3) 0.44798(10) 0.0227(5) Uani d . 1 1
O O23 0.6818(5) 0.9204(3) 0.19576(9) 0.0301(5) Uani d . 1 1
O O22 0.1624(4) 0.6266(3) -0.07499(10) 0.0307(5) Uani d . 1 1
N N12 0.7115(5) 0.8489(3) 0.49847(10) 0.0219(5) Uani d . 1 1
O O24 0.9860(5) 1.0790(3) 0.15156(9) 0.0335(5) Uani d . 1 1
C C23 0.6641(5) 0.8841(4) 0.09640(12) 0.0215(6) Uani d . 1 1
C C17 0.4028(5) 0.7428(4) 0.56305(12) 0.0218(5) Uani d . 1 1
N N22 0.7999(5) 0.9209(3) 0.05164(10) 0.0225(5) Uani d . 1 1
C C28 0.7876(6) 0.9699(4) 0.15267(13) 0.0255(6) Uani d . 1 1
C C18 0.7881(6) 0.8250(4) 0.34710(12) 0.0258(6) Uani d . 1 1
O O13 0.9742(5) 0.9479(3) 0.34981(10) 0.0368(6) Uani d . 1 1
C C16 0.6660(6) 0.7916(4) 0.40213(12) 0.0219(6) Uani d . 1 1
C C27 0.3945(5) 0.6834(4) -0.06642(12) 0.0225(6) Uani d . 1 1
C C14 0.3368(6) 0.6633(4) 0.45630(12) 0.0244(6) Uani d . 1 1
H H14 0.1787 0.5962 0.4605 0.029 Uiso calc R 1 1
C C24 0.4272(6) 0.7763(4) 0.09217(13) 0.0261(6) Uani d . 1 1
H H24 0.3370 0.7524 0.1241 0.031 Uiso calc R 1 1
C C26 0.4807(5) 0.7464(4) -0.00552(12) 0.0199(5) Uani d . 1 1
C C25 0.3319(5) 0.7071(4) 0.03952(13) 0.0259(6) Uani d . 1 1
H H25 0.1732 0.6362 0.0342 0.031 Uiso calc R 1 1
C C13 0.4859(5) 0.7499(4) 0.50274(12) 0.0198(5) Uani d . 1 1
C C15 0.4332(6) 0.6814(4) 0.40447(13) 0.0275(6) Uani d . 1 1
H H15 0.3468 0.6225 0.3719 0.033 Uiso calc R 1 1
Li Li1 1.0824(10) 1.0999(8) 0.4223(2) 0.0296(11) Uani d . 1 1
Li Li2 0.9101(9) 0.8297(8) -0.0796(2) 0.0283(11) Uani d . 1 1
Li Li3 0.7103(10) 0.6895(7) 0.2248(2) 0.0278(11) Uani d . 1 1
N N1 0.4289(6) 0.1897(5) 0.27436(13) 0.0376(7) Uani d D 1 1
N N2 0.1607(6) 0.1293(5) 0.26487(13) 0.0404(7) Uani d D 1 1
O O1 0.4489(5) 0.4788(4) 0.20777(11) 0.0344(6) Uani d . 1 1
H H11 0.449(10) 0.404(7) 0.230(2) 0.052 Uiso d . 1 1
H H12 0.449(9) 0.426(7) 0.170(2) 0.052 Uiso d . 1 1
O O3 0.9495(6) 0.4090(4) 0.32720(12) 0.0462(7) Uani d D 1 1
H H31 0.912(10) 0.399(8) 0.3605(11) 0.069 Uiso d D 1 1
H H32 0.852(9) 0.474(7) 0.3144(19) 0.069 Uiso d D 1 1
O O2 0.9871(5) 0.5947(4) 0.18013(13) 0.0465(7) Uani d D 1 1
O O14 0.6997(5) 0.7239(4) 0.30427(10) 0.0383(6) Uani d . 1 1
H H22 0.977(14) 0.524(8) 0.1501(17) 0.10(2) Uiso d D 1 1
H H21 1.112(9) 0.559(8) 0.195(3) 0.08(2) Uiso d D 1 1
H H1 0.451(11) 0.188(7) 0.3107(9) 0.064(16) Uiso d D 1 1
H H4 0.138(13) 0.029(6) 0.283(2) 0.081(18) Uiso d D 1 1
H H2 0.497(9) 0.104(5) 0.2505(18) 0.058(14) Uiso d D 1 1
H H5 0.066(12) 0.221(7) 0.280(3) 0.11(3) Uiso d D 1 1
H H3 0.124(12) 0.102(8) 0.2283(10) 0.082(19) Uiso d D 1 1
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'
Li Li -0.0003 0.0001 '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
C27 O21 Li2 . . 120.1(3)
C17 O12 Li1 . 2_676 117.5(2)
N22 N21 C26 . . 119.4(2)
N22 N21 Li2 . . 129.1(2)
C26 N21 Li2 . . 110.7(2)
C17 O11 Li1 . 2_776 117.2(2)
N12 N11 C16 . . 119.5(2)
N12 N11 Li1 . . 129.9(2)
C16 N11 Li1 . . 108.1(2)
C28 O23 Li3 . . 126.2(3)
C27 O22 Li2 . 1_455 116.2(2)
N11 N12 C13 . . 119.7(2)
N11 N12 Li1 . 2_776 128.2(2)
C13 N12 Li1 . 2_776 110.9(2)
C28 O24 Li2 . 2_775 119.8(2)
N22 C23 C24 . . 123.0(3)
N22 C23 C28 . . 114.7(2)
C24 C23 C28 . . 122.3(2)
O11 C17 O12 . . 126.9(3)
O11 C17 C13 . . 116.8(2)
O12 C17 C13 . . 116.3(3)
C23 N22 N21 . . 119.3(2)
C23 N22 Li2 . 2_775 107.7(2)
N21 N22 Li2 . 2_775 130.4(2)
O24 C28 O23 . . 126.5(3)
O24 C28 C23 . . 117.1(3)
O23 C28 C23 . . 116.5(3)
O14 C18 O13 . . 126.7(3)
O14 C18 C16 . . 116.8(3)
O13 C18 C16 . . 116.4(3)
C18 O13 Li1 . . 120.8(2)
N11 C16 C15 . . 122.9(3)
N11 C16 C18 . . 114.9(2)
C15 C16 C18 . . 122.2(3)
O22 C27 O21 . . 127.7(3)
O22 C27 C26 . . 116.6(3)
O21 C27 C26 . . 115.8(2)
C15 C14 C13 . . 117.0(3)
C15 C14 H14 . . 121.5
C13 C14 H14 . . 121.5
C25 C24 C23 . . 117.7(3)
C25 C24 H24 . . 121.2
C23 C24 H24 . . 121.2
N21 C26 C25 . . 123.3(3)
N21 C26 C27 . . 113.8(2)
C25 C26 C27 . . 122.9(2)
C24 C25 C26 . . 117.4(3)
C24 C25 H25 . . 121.3
C26 C25 H25 . . 121.3
N12 C13 C14 . . 123.2(2)
N12 C13 C17 . . 113.8(2)
C14 C13 C17 . . 122.9(2)
C14 C15 C16 . . 117.6(3)
C14 C15 H15 . . 121.2
C16 C15 H15 . . 121.2
O13 Li1 O11 . 2_776 98.3(3)
O13 Li1 O12 . 2_676 103.8(3)
O11 Li1 O12 2_776 2_676 108.2(3)
O13 Li1 N12 . 2_776 153.2(3)
O11 Li1 N12 2_776 2_776 79.1(2)
O12 Li1 N12 2_676 2_776 102.3(2)
O13 Li1 N11 . . 76.6(2)
O11 Li1 N11 2_776 . 155.5(3)
O12 Li1 N11 2_676 . 96.3(2)
N12 Li1 N11 2_776 . 94.7(2)
O21 Li2 O24 . 2_775 100.7(3)
O21 Li2 O22 . 1_655 106.4(3)
O24 Li2 O22 2_775 1_655 101.2(2)
O21 Li2 N21 . . 77.79(19)
O24 Li2 N21 2_775 . 153.1(3)
O22 Li2 N21 1_655 . 105.0(3)
O21 Li2 N22 . 2_775 156.5(3)
O24 Li2 N22 2_775 2_775 76.4(2)
O22 Li2 N22 1_655 2_775 97.0(2)
N21 Li2 N22 . 2_775 94.3(2)
O14 Li3 O23 . . 110.5(3)
O14 Li3 O2 . . 126.1(3)
O23 Li3 O2 . . 101.0(3)
O14 Li3 O1 . . 99.9(3)
O23 Li3 O1 . . 121.7(3)
O2 Li3 O1 . . 99.0(3)
N2 N1 H1 . . 103(4)
N2 N1 H2 . . 100(3)
H1 N1 H2 . . 118(5)
N1 N2 H4 . . 103(4)
N1 N2 H5 . . 109(5)
H4 N2 H5 . . 112(6)
N1 N2 H3 . . 111(4)
H4 N2 H3 . . 112(6)
H5 N2 H3 . . 109(6)
Li3 O1 H11 . . 114(4)
Li3 O1 H12 . . 113(3)
H11 O1 H12 . . 113(5)
H31 O3 H32 . . 109(3)
Li3 O2 H22 . . 129(5)
Li3 O2 H21 . . 121(5)
H22 O2 H21 . . 100(6)
C18 O14 Li3 . . 143.4(3)
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
O21 C27 . 1.248(4) ?
O12 C17 . 1.254(3) ?
O12 Li1 2_676 2.088(6) ?
N21 N22 . 1.337(3) ?
N21 C26 . 1.341(3) ?
O11 C17 . 1.252(4) ?
O11 Li1 2_776 2.010(6) ?
N11 N12 . 1.329(3) ?
N11 C16 . 1.334(4) ?
O23 C28 . 1.256(4) ?
O22 C27 . 1.246(4) ?
O22 Li2 1_455 2.097(6) ?
N12 C13 . 1.331(4) ?
N12 Li1 2_776 2.144(6) ?
O24 C28 . 1.245(4) ?
O24 Li2 2_775 1.995(6) ?
C23 N22 . 1.335(4) ?
C23 C24 . 1.393(4) ?
C23 C28 . 1.520(4) ?
C17 C13 . 1.521(4) ?
N22 Li2 2_775 2.276(6) ?
C18 O14 . 1.240(4) ?
C18 O13 . 1.251(4) ?
C18 C16 . 1.511(4) ?
C16 C15 . 1.396(4) ?
C27 C26 . 1.522(4) ?
C14 C15 . 1.364(4) ?
C14 C13 . 1.395(4) ?
C14 H14 . 0.9300 ?
C24 C25 . 1.367(4) ?
C24 H24 . 0.9300 ?
C26 C25 . 1.382(4) ?
C25 H25 . 0.9300 ?
C15 H15 . 0.9300 ?
Li1 N11 . 2.260(6) y
Li1 O13 . 1.982(6) y
Li1 O11 2_776 2.010(5) y
Li1 O12 2_676 2.088(6) y
Li1 N12 2_776 2.144(6) y
Li2 O21 . 1.990(6) y
Li2 N21 . 2.186(6) y
Li2 O24 2_775 1.995(6) y
Li2 O22 1_655 2.097(6) y
Li2 N22 2_775 2.276(6) y
Li3 O14 . 1.893(5) y
Li3 O2 . 1.938(6) y
Li3 O1 . 1.952(6) y
Li3 O23 . 1.934(6) y
N1 N2 . 1.430(4) ?
N1 H1 . 0.88(2) ?
N1 H2 . 0.897(19) ?
N2 H4 . 0.90(2) ?
N2 H5 . 0.92(2) ?
N2 H3 . 0.89(2) ?
O1 H11 . 0.82(5) ?
O1 H12 . 0.93(5) ?
O3 H31 . 0.835(19) ?
O3 H32 . 0.814(19) ?
O2 H22 . 0.83(2) ?
O2 H21 . 0.82(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
N2 H3 O24 1_445 0.89(2) 1.95(2) 2.824(4) 168(6)
N2 H5 O3 1_455 0.92(2) 1.82(3) 2.709(5) 162(7)
N1 H2 O23 1_545 0.897(19) 2.07(2) 2.965(4) 175(5)
N2 H4 O13 1_445 0.90(2) 1.96(5) 2.716(4) 140(6)
N1 H1 O11 2_666 0.88(2) 2.12(2) 2.981(4) 167(5)
O2 H21 O1 1_655 0.82(2) 1.94(3) 2.737(4) 163(7)
O2 H22 O22 2_665 0.83(2) 2.07(3) 2.868(4) 162(7)
O3 H31 O12 2_666 0.835(19) 1.93(2) 2.741(4) 164(5)
O3 H32 O14 . 0.814(19) 2.11(3) 2.875(4) 156(5)
O1 H12 O21 2_665 0.93(5) 1.76(5) 2.684(3) 174(4)
O1 H11 N1 . 0.82(5) 2.00(5) 2.814(4) 171(5)
