data_2008880
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1535
_journal_page_last  1536
_publ_section_title
;
Bis(hydrazinium) 4-hydroxy-1-oxo-2H-phthalazine-6,7-dicarboxylate
;
loop_
_publ_author_name
  'Benniston, Andrew C.'
  'Yufit, D. S.'
  'Howard, Judith A. K.'
_chemical_formula_moiety  '2N2 H5 1+, C10 H4 N2 O6 2-'
_chemical_formula_sum  'C10 H14 N6 O6'
_chemical_formula_iupac  '2N2 H5 1+, C10 H4 N2 O6 2-'
_chemical_formula_weight  314.27
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  25.300(5)
_cell_length_b  7.366(2)
_cell_length_c  14.609(3)
_cell_angle_alpha  90.00
_cell_angle_beta  113.62(3)
_cell_angle_gamma  90.00
_cell_volume  2494.4(9)
_cell_formula_units_Z  8
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.674
_diffrn_ambient_temperature  100(2)
loop_
_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
_atom_site_type_symbol
  O1 -0.00189(5) 0.5182(2) 0.12520(10)
  0.0230(3) Uani d . 1 . . O
  O2 -0.05768(5) 1.2197(2) 0.03852(8) 0.0153(3) Uani d . 1 . . O
  O3 0.17570(5) 1.2165(2) 0.41534(8) 0.0158(3) Uani d . 1 . . O
  O4 0.16636(5) 1.3441(2) 0.27091(8) 0.0202(3) Uani d . 1 . . O
  O5 0.22221(5) 0.8840(2) 0.33606(8) 0.0158(3) Uani d . 1 . . O
  O6 0.18374(5) 0.7343(2) 0.42841(8) 0.0163(3) Uani d . 1 . . O
  N2 -0.06634(6) 0.7360(2) 0.03480(10)
  0.0131(3) Uani d . 1 . . N
  N3 -0.07722(6) 0.9196(2) 0.01880(10)
  0.0125(3) Uani d . 1 . . N
  C1 -0.01663(7) 0.6922(2) 0.10370(10)
  0.0132(3) Uani d . 1 . . C
  C4 -0.04189(6) 1.0598(2) 0.06450(10)
  0.0119(3) Uani d . 1 . . C
  C5 0.05651(7) 1.1380(2) 0.19340(10)
  0.0120(3) Uani d . 1 . . C
  C6 0.10950(6) 1.0835(2) 0.26440(10)
  0.0108(3) Uani d . 1 . . C
  C7 0.12111(6) 0.8976(2) 0.28580(10)
  0.0107(3) Uani d . 1 . . C
  C8 0.07984(7) 0.7683(2) 0.23590(10)
  0.0122(3) Uani d . 1 . . C
  C9 0.02650(6) 0.8227(2) 0.16220(10)
  0.0115(3) Uani d . 1 . . C
  C10 0.01443(6) 1.0079(2) 0.14180(10)
  0.0111(3) Uani d . 1 . . C
  C11 0.15408(6) 1.2256(2) 0.32110(10)
  0.0120(3) Uani d . 1 . . C
  C12 0.18035(7) 0.8343(2) 0.35720(10)
  0.0116(3) Uani d . 1 . . C
  N1S -0.19450(6) 0.9460(2) -0.13580(10)
  0.0155(3) Uani d . 1 . . N
  N2S -0.23278(6) 1.0031(2) -0.08900(10)
  0.0148(3) Uani d . 1 . . N
  N3S 0.16132(6) 0.3690(2) 0.62170(10)
  0.0175(3) Uani d . 1 . . N
  N4S 0.16930(6) 0.4841(2) 0.54740(10)
  0.0144(3) Uani d . 1 . . N
  H1O -0.0250(10)
  0.444(4) 0.090(2) 0.051(8) Uiso d . 1 . . H
  H3N -0.1100(10)
  0.944(3) -0.024(2) 0.025(6) Uiso d . 1 . . H
  H5 0.0487(9) 1.261(3) 0.1800(10)
  0.021(5) Uiso d . 1 . . H
  H8 0.0874(8) 0.643(3) 0.2500(10)
  0.017(5) Uiso d . 1 . . H
  H11S -0.1990(10)
  1.028(3) -0.183(2) 0.036(6) Uiso d . 1 . . H
  H12S -0.2110(10)
  0.848(3) -0.169(2) 0.030(6) Uiso d . 1 . . H
  H21S -0.2670(10)
  1.063(3) -0.137(2) 0.034(6) Uiso d . 1 . . H
  H22S -0.2450(10)
  0.898(3) -0.060(2) 0.043(7) Uiso d . 1 . . H
  H23S -0.2125(9) 1.090(3) -0.035(2) 0.030(6) Uiso d . 1 . . H
  H31S 0.1255(9) 0.314(3) 0.5880(10)
  0.020(5) Uiso d . 1 . . H
  H32S 0.1590(10)
  0.448(3) 0.670(2) 0.031(6) Uiso d . 1 . . H
  H41S 0.1697(9) 0.403(3) 0.496(2) 0.028(6) Uiso d . 1 . . H
  H42S 0.1400(10)
  0.575(3) 0.522(2) 0.032(6) Uiso d . 1 . . H
  H43S 0.2070(10)
  0.540(3) 0.580(2) 0.030(6) Uiso d . 1 . . H
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
  O1 0.0166(6) 0.0093(6) 0.0287(7) -0.0006(5) -0.0060(5) -0.0021(5)
  O2 0.0129(5) 0.0114(6) 0.0161(6) 0.0001(4) 0.0000(4) 0.0016(4)
  O3 0.0175(6) 0.0153(6) 0.0115(5) -0.0015(5) 0.0024(5) -0.0013(4)
  O4 0.0197(6) 0.0194(6) 0.0165(6) -0.0069(5) 0.0020(5) 0.0032(5)
  O5 0.0117(5) 0.0190(6) 0.0151(6) -0.0004(5) 0.0036(4) 0.0011(5)
  O6 0.0142(5) 0.0170(6) 0.0146(6) 0.0009(5) 0.0025(4) 0.0042(5)
  N2 0.0123(6) 0.0107(6) 0.0142(6) 0.0006(5) 0.0030(5) 0.0000(5)
  N3 0.0099(6) 0.0103(6) 0.0134(6) 0.0010(5) 0.0005(5) 0.0010(5)
  C1 0.0119(7) 0.0116(8) 0.0141(7) -0.0009(6) 0.0031(6) -0.0010(6)
  C4 0.0100(7) 0.0150(8) 0.0100(7) 0.0004(6) 0.0032(6) 0.0002(6)
  C5 0.0127(7) 0.0107(8) 0.0119(7) 0.0000(6) 0.0041(6) 0.0005(6)
  C6 0.0118(7) 0.0119(7) 0.0088(7) -0.0016(6) 0.0044(6) -0.0008(6)
  C7 0.0099(7) 0.0129(8) 0.0091(7) 0.0009(6) 0.0034(6) -0.0001(6)
  C8 0.0120(7) 0.0113(8) 0.0122(7) 0.0008(6) 0.0037(6) 0.0003(6)
  C9 0.0111(7) 0.0115(7) 0.0120(7) 0.0002(6) 0.0046(6) 0.0000(6)
  C10 0.0104(6) 0.0128(8) 0.0095(7) 0.0013(6) 0.0032(6) -0.0001(6)
  C11 0.0086(7) 0.0119(7) 0.0135(7) 0.0004(6) 0.0021(6) -0.0010(6)
  C12 0.0106(7) 0.0107(7) 0.0109(7) 0.0000(6) 0.0017(6) -0.0031(6)
  N1S 0.0146(6) 0.0167(7) 0.0148(7) -0.0003(6) 0.0056(6) 0.0004(6)
  N2S 0.0127(6) 0.0155(7) 0.0144(7) 0.0010(6) 0.0035(5) -0.0010(6)
  N3S 0.0202(7) 0.0169(7) 0.0144(7) -0.0056(6) 0.0057(6) 0.0008(6)
  N4S 0.0140(6) 0.0136(7) 0.0135(7) -0.0003(6) 0.0034(5) 0.0015(6)
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
  O1 C1 . 1.336(2) ?
  O2 C4 . 1.253(2) ?
  O3 C11 . 1.264(2) ?
  O4 C11 . 1.256(2) ?
  O5 C12 . 1.270(2) ?
  O6 C12 . 1.249(2) ?
  N2 C1 . 1.298(2) ?
  N2 N3 . 1.381(2) ?
  N3 C4 . 1.354(2) ?
  C1 C9 . 1.449(2) ?
  C4 C10 . 1.470(2) ?
  C5 C6 . 1.386(2) ?
  C5 C10 . 1.406(2) ?
  C6 C7 . 1.409(2) ?
  C6 C11 . 1.518(2) ?
  C7 C8 . 1.385(2) ?
  C7 C12 . 1.516(2) ?
  C8 C9 . 1.406(2) ?
  C9 C10 . 1.404(2) ?
  N1S N2S . 1.454(2) ?
  N3S N4S . 1.454(2) ?