Acta Cryst. (2007). E63, m2415 [ doi:10.1107/S1600536807041268 ]
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2N1,O2)nickel(II) dihydrateIn the title compound, [Ni(C5H3N2O2)2]·2H2O, the NiII cation is four-coordinated by two N and two O atoms belonging to two pyrazine-2-carboxylate ligands. The NiII atom occupies a special position at a centre of symmetry. Hydrogen bonds between water molecules, and between water molecules and carboxylate O atoms, stabilize the crystal structure.
The 8 ml etanol solution of nickel acetate (0.5 mmol), pyrazine-2-carboxylic acid (1.0 mmol) in a 25 ml Teflon-lined stainless steel autoclave was kept at 423 K for three days. Green crystals were obtained after cooling to room temperature with a yield of 35%. Anal. Calc. for C10H10N4Ni: C 35.19, H 2.93, N 16.42%; Found: C 35.11, H 2.97, N 16.38%.
The H atoms of the water molecule were located from difference density maps and were refined with distance restraints of d(H–H) = 1.38 (2)Å and d(O–H) = 0.82 (2) Å. All other H atoms were placed in calculated positions with a C—H bond distance of 0.93 Å and Uiso(H) = 1.2Ueq of the respective carrier atom.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
![[Figure 1]](./kp2122fig1thm.gif)
| Fig. 1. The molecular structure of (I) with the 30% probability displacement ellipsoids. Symmetry operator i: 1 x, y, z + 1. |
![[Figure 2]](./kp2122fig2thm.gif)
| Fig. 2. The packing diagram of the title compound along the direction [010]. |
| [Ni(C5H3N2O2)2]·2H2O | Z = 1 |
| Mr = 340.93 | F000 = 174 |
| Triclinic, P1 | Dx = 1.632 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 5.5576 (6) Å | Cell parameters from 1208 reflections |
| b = 7.3252 (9) Å | θ = 2.3–25.0º |
| c = 9.3021 (11) Å | µ = 1.43 mm−1 |
| α = 75.065 (2)º | T = 293 (2) K |
| β = 84.298 (2)º | Cube, green |
| γ = 71.503 (2)º | 0.10 × 0.10 × 0.10 mm |
| V = 346.93 (7) Å3 |
| Bruker APEX II CCD area-detector diffractometer | 1208 independent reflections |
| Radiation source: fine-focus sealed tube | 1111 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.050 |
| T = 293(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 2.3º |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −6→5 |
| Tmin = 0.870, Tmax = 0.870 | k = −8→8 |
| 1705 measured reflections | l = −8→11 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max < 0.001 |
| 1208 reflections | Δρmax = 0.54 e Å−3 |
| 103 parameters | Δρmin = −0.51 e Å−3 |
| 3 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Ni(C5H3N2O2)2]·2H2O | γ = 71.503 (2)º |
| Mr = 340.93 | V = 346.93 (7) Å3 |
| Triclinic, P1 | Z = 1 |
| a = 5.5576 (6) Å | Mo Kα |
| b = 7.3252 (9) Å | µ = 1.43 mm−1 |
| c = 9.3021 (11) Å | T = 293 (2) K |
| α = 75.065 (2)º | 0.10 × 0.10 × 0.10 mm |
| β = 84.298 (2)º |
| Bruker APEX II CCD area-detector diffractometer | 1208 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1111 reflections with I > 2σ(I) |
| Tmin = 0.870, Tmax = 0.870 | Rint = 0.050 |
| 1705 measured reflections |
| R[F2 > 2σ(F2)] = 0.039 | 3 restraints |
| wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.00 | Δρmax = 0.54 e Å−3 |
| 1208 reflections | Δρmin = −0.51 e Å−3 |
| 103 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 | ||
| Ni1 | 1.0000 | 0.0000 | 1.0000 | 0.0297 (2) | |
| C1 | 0.4654 (6) | 0.1781 (4) | 1.0641 (4) | 0.0332 (7) | |
| C2 | 0.5285 (6) | 0.3005 (4) | 0.9152 (4) | 0.0317 (7) | |
| C3 | 0.3444 (6) | 0.4682 (5) | 0.8416 (4) | 0.0385 (8) | |
| H3 | 0.1797 | 0.5093 | 0.8789 | 0.046* | |
| C4 | 0.6886 (8) | 0.4949 (5) | 0.6507 (4) | 0.0481 (9) | |
| H4 | 0.7394 | 0.5640 | 0.5604 | 0.058* | |
| C5 | 0.8593 (7) | 0.3250 (5) | 0.7289 (4) | 0.0412 (8) | |
| H5 | 1.0228 | 0.2770 | 0.6919 | 0.049* | |
| N1 | 0.7810 (5) | 0.2302 (4) | 0.8615 (3) | 0.0326 (6) | |
| N2 | 0.4262 (7) | 0.5699 (5) | 0.7071 (4) | 0.0652 (10) | |
| O1 | 0.6702 (4) | 0.0410 (3) | 1.1256 (2) | 0.0378 (5) | |
| O2 | 0.2286 (4) | 0.2137 (3) | 1.1166 (3) | 0.0455 (6) | |
| O1W | 0.2352 (8) | 0.0433 (7) | 0.4397 (4) | 0.1007 (13) | |
| H1W | 0.212 (13) | 0.087 (10) | 0.347 (3) | 0.151* | |
| H2W | 0.369 (8) | −0.051 (8) | 0.455 (7) | 0.151* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0229 (3) | 0.0247 (3) | 0.0327 (3) | −0.0004 (2) | 0.0048 (2) | −0.0021 (2) |
| C1 | 0.0315 (17) | 0.0276 (15) | 0.0401 (18) | −0.0068 (13) | 0.0029 (13) | −0.0115 (13) |
| C2 | 0.0307 (16) | 0.0260 (15) | 0.0393 (18) | −0.0074 (13) | 0.0009 (13) | −0.0114 (13) |
| C3 | 0.0374 (18) | 0.0293 (16) | 0.0450 (19) | −0.0040 (14) | −0.0017 (14) | −0.0100 (14) |
| C4 | 0.061 (2) | 0.0363 (18) | 0.041 (2) | −0.0155 (17) | −0.0010 (17) | 0.0021 (15) |
| C5 | 0.0383 (18) | 0.0409 (18) | 0.0406 (19) | −0.0125 (15) | 0.0048 (15) | −0.0046 (15) |
| N1 | 0.0315 (14) | 0.0272 (13) | 0.0365 (15) | −0.0072 (11) | 0.0026 (11) | −0.0065 (11) |
| N2 | 0.074 (3) | 0.0471 (19) | 0.067 (2) | −0.0094 (17) | −0.0119 (19) | −0.0083 (17) |
| O1 | 0.0340 (12) | 0.0307 (11) | 0.0390 (13) | −0.0014 (9) | 0.0043 (10) | −0.0043 (10) |
| O2 | 0.0343 (13) | 0.0406 (13) | 0.0530 (15) | −0.0033 (10) | 0.0137 (11) | −0.0121 (11) |
| O1W | 0.106 (3) | 0.127 (4) | 0.059 (2) | −0.051 (3) | −0.002 (2) | 0.014 (2) |
| Ni1—N1 | 1.968 (3) | C3—N2 | 1.395 (5) |
| Ni1—N1i | 1.968 (3) | C3—H3 | 0.9300 |
| Ni1—O1i | 2.054 (2) | C4—C5 | 1.378 (5) |
| Ni1—O1 | 2.054 (2) | C4—N2 | 1.481 (5) |
| C1—O1 | 1.319 (4) | C4—H4 | 0.9300 |
| C1—O2 | 1.326 (4) | C5—N1 | 1.355 (4) |
| C1—C2 | 1.519 (4) | C5—H5 | 0.9300 |
| C2—C3 | 1.390 (5) | O1W—H1W | 0.84 (2) |
| C2—N1 | 1.421 (4) | O1W—H2W | 0.83 (5) |
| N1—Ni1—N1i | 180.00 (14) | N2—C3—H3 | 122.6 |
| N1—Ni1—O1i | 99.06 (9) | C5—C4—N2 | 121.5 (3) |
| N1i—Ni1—O1i | 80.94 (9) | C5—C4—H4 | 119.3 |
| N1—Ni1—O1 | 80.94 (9) | N2—C4—H4 | 119.3 |
| N1i—Ni1—O1 | 99.06 (9) | N1—C5—C4 | 117.8 (3) |
| O1i—Ni1—O1 | 180.0 | N1—C5—H5 | 121.1 |
| O1—C1—O2 | 127.9 (3) | C4—C5—H5 | 121.1 |
| O1—C1—C2 | 111.3 (2) | C5—N1—C2 | 120.9 (3) |
| O2—C1—C2 | 120.8 (3) | C5—N1—Ni1 | 124.8 (2) |
| C3—C2—N1 | 124.7 (3) | C2—N1—Ni1 | 114.3 (2) |
| C3—C2—C1 | 120.0 (3) | C3—N2—C4 | 120.5 (3) |
| N1—C2—C1 | 115.3 (3) | C1—O1—Ni1 | 117.65 (19) |
| C2—C3—N2 | 114.7 (3) | H1W—O1W—H2W | 110 (3) |
| C2—C3—H3 | 122.6 |
| Symmetry codes: (i) −x+2, −y, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1W—H2W···O1Wii | 0.83 (5) | 2.52 (6) | 3.071 (9) | 125 (6) |
| O1W—H1W···O2iii | 0.84 (2) | 2.11 (3) | 2.941 (4) | 167 (7) |
| Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x, y, z−1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1W—H2W···O1Wi | 0.83 (5) | 2.52 (6) | 3.071 (9) | 125 (6) |
| O1W—H1W···O2ii | 0.84 (2) | 2.11 (3) | 2.941 (4) | 167 (7) |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y, z−1. |
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In recent years carboxylic acids have been widely used as polydentate ligands, which can coordinate to transition or rare earth ions yielding complexes with interesting properties that are useful in materials science (Church & Halvorson, 1959; Chung et al., 1971) and in biological systems (Okabe & Oya, 2000; Serre et al., 2005; Pocker & Fong, 1980; Scapin et al., 1997). Herein, we report the synthesis and X-ray crystal structure analysis of the title compound bis(pyrazine-2-carboxylato)nickel(II) hydrate (Fig. 1). The nickel cation is tetra-coordinated by two O an d two N atoms belonging to two pyrazine-2-carboxylate. Hydrogen bonds between symmetry operated water molecules, and water molecule and carboxylate oxygen atom stablize the crystal structure (Table 1 and Fig. 2).