Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038135/lh2467sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038135/lh2467Isup2.hkl |
CCDC reference: 660229
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.138
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT353_ALERT_3_B Long N-H Bond (0.87A) N3 - H32 ... 1.10 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H7 .. H122 .. 1.68 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H32 .. H112 .. 2.07 Ang. PLAT432_ALERT_2_B Short Inter X...Y Contact O3 .. C7 .. 2.90 Ang.
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.609 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.61 e/A PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT245_ALERT_2_C U(iso) H122 Smaller than U(eq) O12 by ... 0.01 AngSq PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04 PLAT323_ALERT_2_C Check Hybridisation of H121 in Solvent/Ion ? PLAT353_ALERT_3_C Long N-H Bond (0.87A) N3 - H31 ... 1.01 Ang. PLAT417_ALERT_2_C Short Inter D-H..H-D H1 .. H102 .. 2.10 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H122 .. N1 .. 2.79 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H122 .. O1 .. 2.79 Ang. PLAT482_ALERT_4_C Small D-H..A Angle Rep for O12 .. N1 .. 97.00 Deg. PLAT482_ALERT_4_C Small D-H..A Angle Rep for O12 .. O1 .. 95.00 Deg.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the crystal structures of metal cations and the title anion, see: Marioni et al. (1994); Gryz et al. (2005).
The title compound was obtained unintentionally in the course of attempts to obtain single crystals of a zinc complex with pyrazine-2,3,5,6-tetracarboxylic ligand. Pale-yellow single crystals of the title compound were separated from a mass of polycrystalline material, washed with cold water and dried in the air. Hydrazine was used to maintain the acidity of the initial solution.
All H atoms were located in a difference map and refined with isotropic displacement parameters.
The molecular structure of the title compound contains one doubly- protonated hydrazine cation having its geometrical centre on an inversion centre at 1/2,1/2,0, two symmetry related singly-deprotonated pyrazine- 2,3, 5,6-tetracarboxylate anions and three pairs of symmetry related solvent water molecules. Fig.1. shows the asymmetric unit with atom labelling scheme. Atoms forming the pyrazine ring are coplanar (r.m.s. 0.0032 Å). Carboxylate groups form the following angles with the plane of the pyrazine ring: 11.3 (2)° (C7/O1/O2), 58.5 (2)° (C8/O3/O4), 82.1 (2)° (C9/O5/O6) and 23.5 (2)° (C10/O7/O8). Bond lengths and bond angles within the pyrazine ring do not differ from those reported in other ionic metal complexes with the title ligand (Gryz et al., 2005; Marioni et al., 1994). In the crystal structure, an extended hydrogen bond network is constructed (Fig. 2) via protonated carboxylate O atoms of the anions acting as donors in strong bonds [2.480 (2)- 2.626 (2) Å] to solvent water and non-protonated carboxylate O atoms. Hydrazine N atoms also act as also donors in hydrogen bonds bonds to non-protonated carboxylate and solvent water O atoms, the latter donate their O atoms to weak bonds linking them to carboxylate O atoms.
For the crystal structures of metal cations and the title anion, see: Marioni et al. (1994); Gryz et al. (2005).
Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.
N2H62+·2C8H3N2O8−·6H2O | Z = 1 |
Mr = 652.41 | F(000) = 338 |
Triclinic, P1 | Dx = 1.754 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3871 (15) Å | Cell parameters from 25 reflections |
b = 9.3453 (19) Å | θ = 6–15° |
c = 9.4942 (19) Å | µ = 0.17 mm−1 |
α = 82.93 (3)° | T = 293 K |
β = 83.73 (3)° | Rectangular blocks, pale yellow |
γ = 72.24 (3)° | 0.30 × 0.12 × 0.07 mm |
V = 617.7 (2) Å3 |
Kuma KM-4 four-circle diffractometer | 2606 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.010 |
Graphite monochromator | θmax = 30.1°, θmin = 2.2° |
profile data from ω/–2θ scans | h = −9→10 |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2000) | k = 0→12 |
Tmin = 0.975, Tmax = 0.985 | l = −13→13 |
3809 measured reflections | 3 standard reflections every 200 reflections |
3606 independent reflections | intensity decay: 0.4% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0911P)2 + 0.1092P] where P = (Fo2 + 2Fc2)/3 |
3606 reflections | (Δ/σ)max < 0.001 |
247 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
N2H62+·2C8H3N2O8−·6H2O | γ = 72.24 (3)° |
Mr = 652.41 | V = 617.7 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 7.3871 (15) Å | Mo Kα radiation |
b = 9.3453 (19) Å | µ = 0.17 mm−1 |
c = 9.4942 (19) Å | T = 293 K |
α = 82.93 (3)° | 0.30 × 0.12 × 0.07 mm |
β = 83.73 (3)° |
Kuma KM-4 four-circle diffractometer | 2606 reflections with I > 2σ(I) |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2000) | Rint = 0.010 |
Tmin = 0.975, Tmax = 0.985 | 3 standard reflections every 200 reflections |
3809 measured reflections | intensity decay: 0.4% |
3606 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.138 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.61 e Å−3 |
3606 reflections | Δρmin = −0.36 e Å−3 |
247 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. 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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
N2 | 0.20465 (16) | 0.36376 (12) | 0.60373 (11) | 0.0189 (2) | |
N1 | 0.24160 (17) | 0.10473 (12) | 0.47527 (11) | 0.0202 (2) | |
C9 | 0.11430 (19) | 0.26486 (15) | 0.83419 (13) | 0.0205 (3) | |
C4 | 0.27719 (19) | 0.22494 (14) | 0.40009 (13) | 0.0182 (2) | |
C1 | 0.16787 (18) | 0.24388 (14) | 0.67820 (13) | 0.0178 (2) | |
C6 | 0.18665 (19) | 0.11358 (14) | 0.61342 (13) | 0.0187 (2) | |
C10 | 0.32009 (19) | 0.48649 (14) | 0.38932 (13) | 0.0200 (2) | |
C7 | 0.1434 (2) | −0.02063 (15) | 0.69872 (14) | 0.0222 (3) | |
C3 | 0.26019 (18) | 0.35528 (14) | 0.46594 (13) | 0.0178 (2) | |
C8 | 0.3337 (2) | 0.20828 (15) | 0.24250 (13) | 0.0200 (3) | |
O7 | 0.24607 (19) | 0.61045 (12) | 0.45014 (12) | 0.0327 (3) | |
O3 | 0.47317 (18) | 0.10377 (13) | 0.21073 (12) | 0.0337 (3) | |
O2 | 0.06495 (19) | −0.01124 (13) | 0.81724 (12) | 0.0334 (3) | |
O12 | 0.3699 (3) | 0.82052 (15) | 0.33870 (14) | 0.0375 (3) | |
O5 | 0.26197 (18) | 0.20910 (17) | 0.90837 (12) | 0.0382 (3) | |
O6 | −0.04224 (17) | 0.33557 (15) | 0.87695 (12) | 0.0347 (3) | |
O8 | 0.43073 (17) | 0.47009 (12) | 0.28463 (11) | 0.0289 (2) | |
O1 | 0.1973 (2) | −0.14131 (13) | 0.62962 (12) | 0.0353 (3) | |
O11 | 0.33128 (19) | 0.83427 (15) | 0.04456 (14) | 0.0350 (3) | |
O10 | 0.16102 (17) | 0.61037 (12) | 0.77595 (12) | 0.0260 (2) | |
H121 | 0.378 (3) | 0.833 (3) | 0.243 (3) | 0.036 (5)* | |
N3 | 0.39902 (19) | 0.53719 (17) | 0.00114 (14) | 0.0297 (3) | |
O4 | 0.22560 (17) | 0.30338 (13) | 0.15643 (10) | 0.0288 (2) | |
H31 | 0.342 (4) | 0.470 (3) | 0.071 (3) | 0.050 (6)* | |
H33 | 0.353 (3) | 0.547 (3) | −0.088 (2) | 0.037 (5)* | |
H101 | 0.049 (4) | 0.627 (3) | 0.802 (2) | 0.036 (6)* | |
H102 | 0.192 (4) | 0.558 (3) | 0.715 (3) | 0.055 (7)* | |
H112 | 0.216 (5) | 0.878 (4) | 0.040 (3) | 0.059 (8)* | |
H1 | 0.184 (5) | −0.214 (4) | 0.681 (4) | 0.077 (10)* | |
H122 | 0.277 (3) | 0.851 (3) | 0.336 (2) | 0.024 (6)* | |
H32 | 0.362 (4) | 0.651 (3) | 0.037 (3) | 0.062 (8)* | |
H5 | 0.248 (6) | 0.243 (4) | 1.005 (5) | 0.101 (12)* | |
H111 | 0.395 (4) | 0.873 (3) | −0.030 (3) | 0.056 (7)* | |
H7 | 0.294 (5) | 0.673 (5) | 0.404 (4) | 0.089 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N2 | 0.0276 (5) | 0.0150 (5) | 0.0157 (5) | −0.0084 (4) | 0.0005 (4) | −0.0036 (4) |
N1 | 0.0307 (6) | 0.0160 (5) | 0.0155 (5) | −0.0090 (4) | −0.0007 (4) | −0.0031 (4) |
C9 | 0.0289 (6) | 0.0180 (5) | 0.0155 (5) | −0.0089 (5) | 0.0024 (4) | −0.0030 (4) |
C4 | 0.0256 (6) | 0.0149 (5) | 0.0143 (5) | −0.0060 (4) | −0.0006 (4) | −0.0028 (4) |
C1 | 0.0228 (5) | 0.0167 (5) | 0.0144 (5) | −0.0063 (4) | −0.0003 (4) | −0.0035 (4) |
C6 | 0.0263 (6) | 0.0155 (5) | 0.0154 (5) | −0.0079 (4) | −0.0014 (4) | −0.0019 (4) |
C10 | 0.0275 (6) | 0.0174 (6) | 0.0171 (5) | −0.0090 (5) | −0.0028 (4) | −0.0021 (4) |
C7 | 0.0303 (6) | 0.0181 (6) | 0.0197 (6) | −0.0102 (5) | −0.0011 (5) | −0.0011 (4) |
C3 | 0.0246 (6) | 0.0147 (5) | 0.0150 (5) | −0.0068 (4) | −0.0012 (4) | −0.0026 (4) |
C8 | 0.0302 (6) | 0.0184 (6) | 0.0139 (5) | −0.0106 (5) | 0.0009 (4) | −0.0042 (4) |
O7 | 0.0537 (7) | 0.0179 (5) | 0.0287 (5) | −0.0169 (5) | 0.0115 (5) | −0.0076 (4) |
O3 | 0.0418 (6) | 0.0269 (5) | 0.0242 (5) | 0.0005 (5) | 0.0055 (4) | −0.0055 (4) |
O2 | 0.0485 (7) | 0.0267 (5) | 0.0239 (5) | −0.0142 (5) | 0.0098 (5) | −0.0008 (4) |
O12 | 0.0590 (10) | 0.0221 (5) | 0.0329 (6) | −0.0176 (6) | 0.0082 (6) | −0.0039 (4) |
O5 | 0.0341 (6) | 0.0552 (8) | 0.0193 (5) | 0.0003 (5) | −0.0050 (4) | −0.0132 (5) |
O6 | 0.0315 (6) | 0.0386 (6) | 0.0279 (5) | −0.0020 (5) | 0.0057 (4) | −0.0093 (4) |
O8 | 0.0380 (6) | 0.0266 (5) | 0.0230 (5) | −0.0135 (4) | 0.0068 (4) | −0.0036 (4) |
O1 | 0.0641 (8) | 0.0193 (5) | 0.0270 (5) | −0.0216 (5) | 0.0077 (5) | −0.0050 (4) |
O11 | 0.0343 (6) | 0.0357 (6) | 0.0341 (6) | −0.0114 (5) | 0.0001 (5) | 0.0003 (5) |
O10 | 0.0317 (5) | 0.0235 (5) | 0.0252 (5) | −0.0119 (4) | 0.0049 (4) | −0.0085 (4) |
N3 | 0.0286 (6) | 0.0354 (7) | 0.0229 (6) | −0.0072 (5) | −0.0004 (5) | −0.0018 (5) |
O4 | 0.0371 (6) | 0.0302 (5) | 0.0162 (4) | −0.0044 (4) | −0.0038 (4) | −0.0039 (4) |
N2—C3 | 1.3321 (16) | C8—O3 | 1.2234 (18) |
N2—C1 | 1.3333 (17) | C8—O4 | 1.2753 (18) |
N1—C6 | 1.3349 (16) | O7—H7 | 0.83 (4) |
N1—C4 | 1.3351 (17) | O12—H121 | 0.90 (2) |
C9—O6 | 1.1983 (18) | O12—H122 | 0.66 (2) |
C9—O5 | 1.2993 (18) | O5—H5 | 0.99 (4) |
C9—C1 | 1.5115 (17) | O1—H1 | 0.81 (4) |
C4—C3 | 1.4026 (17) | O11—H112 | 0.83 (3) |
C4—C8 | 1.5226 (17) | O11—H111 | 0.91 (3) |
C1—C6 | 1.3939 (17) | O10—H101 | 0.81 (3) |
C6—C7 | 1.5063 (18) | O10—H102 | 0.77 (3) |
C10—O8 | 1.2096 (17) | N3—N3i | 1.440 (3) |
C10—O7 | 1.2976 (17) | N3—H31 | 1.00 (3) |
C10—C3 | 1.5065 (18) | N3—H33 | 0.93 (2) |
C7—O2 | 1.2087 (17) | N3—H32 | 1.10 (3) |
C7—O1 | 1.3083 (17) | ||
C3—N2—C1 | 118.13 (11) | O1—C7—C6 | 112.71 (12) |
C6—N1—C4 | 118.09 (11) | N2—C3—C4 | 121.16 (12) |
O6—C9—O5 | 126.47 (13) | N2—C3—C10 | 116.41 (11) |
O6—C9—C1 | 122.20 (13) | C4—C3—C10 | 122.20 (11) |
O5—C9—C1 | 111.05 (12) | O3—C8—O4 | 126.48 (12) |
N1—C4—C3 | 120.52 (11) | O3—C8—C4 | 117.62 (12) |
N1—C4—C8 | 115.17 (11) | O4—C8—C4 | 115.86 (12) |
C3—C4—C8 | 124.31 (11) | C10—O7—H7 | 106 (3) |
N2—C1—C6 | 120.85 (11) | H121—O12—H122 | 87 (2) |
N2—C1—C9 | 113.15 (11) | C9—O5—H5 | 116 (2) |
C6—C1—C9 | 125.95 (11) | C7—O1—H1 | 111 (2) |
N1—C6—C1 | 121.25 (12) | H112—O11—H111 | 108 (3) |
N1—C6—C7 | 118.50 (11) | H101—O10—H102 | 112 (3) |
C1—C6—C7 | 120.25 (11) | N3i—N3—H31 | 103.8 (15) |
O8—C10—O7 | 126.14 (13) | N3i—N3—H33 | 111.9 (14) |
O8—C10—C3 | 120.78 (12) | H31—N3—H33 | 111 (2) |
O7—C10—C3 | 113.04 (12) | N3i—N3—H32 | 111.7 (15) |
O2—C7—O1 | 126.05 (13) | H31—N3—H32 | 111 (2) |
O2—C7—C6 | 121.23 (12) | H33—N3—H32 | 107 (2) |
Symmetry code: (i) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H121···O11 | 0.90 (2) | 1.95 (2) | 2.8212 (19) | 162 (2) |
N3—H31···O4 | 1.00 (3) | 2.04 (3) | 3.015 (2) | 162 (2) |
N3—H31···O8 | 1.00 (3) | 2.20 (3) | 2.7064 (18) | 109.4 (19) |
N3—H33···O10ii | 0.93 (2) | 1.93 (2) | 2.8031 (19) | 155 (2) |
N3—H33···O8i | 0.93 (2) | 2.30 (2) | 2.8627 (19) | 118.0 (17) |
O10—H101···O4iii | 0.81 (3) | 1.94 (3) | 2.7461 (18) | 171 (2) |
O10—H102···N2 | 0.77 (3) | 2.18 (3) | 2.9066 (17) | 156 (3) |
O10—H102···O7 | 0.77 (3) | 2.51 (3) | 3.0884 (17) | 132 (3) |
O11—H112···O2iii | 0.83 (3) | 2.43 (3) | 3.125 (2) | 141 (3) |
O11—H112···O2iv | 0.83 (3) | 2.46 (3) | 3.007 (2) | 124 (2) |
O1—H1···O10v | 0.81 (4) | 1.82 (4) | 2.6252 (17) | 173 (3) |
O12—H122···N1vi | 0.66 (2) | 2.79 (2) | 2.9458 (19) | 97 (2) |
O12—H122···O1vi | 0.66 (2) | 2.79 (2) | 2.929 (2) | 95 (2) |
N3—H32···O11 | 1.10 (3) | 1.67 (3) | 2.742 (2) | 164 (2) |
O5—H5···O4vii | 0.99 (4) | 1.58 (4) | 2.5736 (16) | 177 (4) |
O11—H111···O3i | 0.91 (3) | 1.90 (3) | 2.7744 (19) | 161 (3) |
O7—H7···O12 | 0.83 (4) | 1.67 (4) | 2.4865 (18) | 169 (4) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z−1; (iii) −x, −y+1, −z+1; (iv) x, y+1, z−1; (v) x, y−1, z; (vi) x, y+1, z; (vii) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | N2H62+·2C8H3N2O8−·6H2O |
Mr | 652.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.3871 (15), 9.3453 (19), 9.4942 (19) |
α, β, γ (°) | 82.93 (3), 83.73 (3), 72.24 (3) |
V (Å3) | 617.7 (2) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.17 |
Crystal size (mm) | 0.30 × 0.12 × 0.07 |
Data collection | |
Diffractometer | Kuma KM-4 four-circle |
Absorption correction | Analytical (CrysAlis RED; Oxford Diffraction, 2000) |
Tmin, Tmax | 0.975, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3809, 3606, 2606 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.138, 1.05 |
No. of reflections | 3606 |
No. of parameters | 247 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.61, −0.36 |
Computer programs: KM-4 Software (Kuma, 1996), KM-4 Software, DATAPROC (Kuma, 2001), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O12—H121···O11 | 0.90 (2) | 1.95 (2) | 2.8212 (19) | 162 (2) |
N3—H31···O4 | 1.00 (3) | 2.04 (3) | 3.015 (2) | 162 (2) |
N3—H31···O8 | 1.00 (3) | 2.20 (3) | 2.7064 (18) | 109.4 (19) |
N3—H33···O10i | 0.93 (2) | 1.93 (2) | 2.8031 (19) | 155 (2) |
N3—H33···O8ii | 0.93 (2) | 2.30 (2) | 2.8627 (19) | 118.0 (17) |
O10—H101···O4iii | 0.81 (3) | 1.94 (3) | 2.7461 (18) | 171 (2) |
O10—H102···N2 | 0.77 (3) | 2.18 (3) | 2.9066 (17) | 156 (3) |
O10—H102···O7 | 0.77 (3) | 2.51 (3) | 3.0884 (17) | 132 (3) |
O11—H112···O2iii | 0.83 (3) | 2.43 (3) | 3.125 (2) | 141 (3) |
O11—H112···O2iv | 0.83 (3) | 2.46 (3) | 3.007 (2) | 124 (2) |
O1—H1···O10v | 0.81 (4) | 1.82 (4) | 2.6252 (17) | 173 (3) |
O12—H122···N1vi | 0.66 (2) | 2.79 (2) | 2.9458 (19) | 97 (2) |
O12—H122···O1vi | 0.66 (2) | 2.79 (2) | 2.929 (2) | 95 (2) |
N3—H32···O11 | 1.10 (3) | 1.67 (3) | 2.742 (2) | 164 (2) |
O5—H5···O4vii | 0.99 (4) | 1.58 (4) | 2.5736 (16) | 177 (4) |
O11—H111···O3ii | 0.91 (3) | 1.90 (3) | 2.7744 (19) | 161 (3) |
O7—H7···O12 | 0.83 (4) | 1.67 (4) | 2.4865 (18) | 169 (4) |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z; (iii) −x, −y+1, −z+1; (iv) x, y+1, z−1; (v) x, y−1, z; (vi) x, y+1, z; (vii) x, y, z+1. |
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The molecular structure of the title compound contains one doubly- protonated hydrazine cation having its geometrical centre on an inversion centre at 1/2,1/2,0, two symmetry related singly-deprotonated pyrazine- 2,3, 5,6-tetracarboxylate anions and three pairs of symmetry related solvent water molecules. Fig.1. shows the asymmetric unit with atom labelling scheme. Atoms forming the pyrazine ring are coplanar (r.m.s. 0.0032 Å). Carboxylate groups form the following angles with the plane of the pyrazine ring: 11.3 (2)° (C7/O1/O2), 58.5 (2)° (C8/O3/O4), 82.1 (2)° (C9/O5/O6) and 23.5 (2)° (C10/O7/O8). Bond lengths and bond angles within the pyrazine ring do not differ from those reported in other ionic metal complexes with the title ligand (Gryz et al., 2005; Marioni et al., 1994). In the crystal structure, an extended hydrogen bond network is constructed (Fig. 2) via protonated carboxylate O atoms of the anions acting as donors in strong bonds [2.480 (2)- 2.626 (2) Å] to solvent water and non-protonated carboxylate O atoms. Hydrazine N atoms also act as also donors in hydrogen bonds bonds to non-protonated carboxylate and solvent water O atoms, the latter donate their O atoms to weak bonds linking them to carboxylate O atoms.