Acta Cryst. (2009). E65, m1278 [ doi:10.1107/S1600536809039129 ]
The title mononuclear nickel(II) complex, [Ni(C18H18N2O4)(H2O)], possesses crystallographic mirror symmetry. The Ni atom is five-coordinated in a square-pyramidal geometry, with two imine N and two phenolate O atoms of the Schiff base ligand in the square plane, and the water O atom in the axial position. In the crystal, the molecules are linked via intermolecular O-H
O hydrogen bonds, forming chains along the a axis.
4-Methoxy-2-hydroxybenzaldehyde (0.2 mmol, 30.5 mg), ethane-1,2-diamine (0.1 mmol, 6.0 mg) and nickel(II) nitrate hexahydrate (0.1 mmol, 29.1 mg) were mixed in a methanol solution (20 ml). The mixture was stirred at room temperature for 30 min to give a green solution. The solution was allowed to stand in air for 5 days, yielding green block-shaped crystals of the title complex.
Water H atoms were located from a difference Fourier map and refined isotropically, with O—H distance restrained to 0.85 (1) Å. Other H atoms were constrained to ideal geometries, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./sj2661fig1thm.gif)
| Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./sj2661fig2thm.gif)
| Fig. 2. Packing of the title complex, viewed along the c axis. Intermolecular O—H···O hydrogen bonds are shown as dashed lines. |
| [Ni(C18H18N2O4)(H2O)] | F(000) = 840 |
| Mr = 403.07 | Dx = 1.510 Mg m−3 |
| Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2n | Cell parameters from 4326 reflections |
| a = 8.7698 (3) Å | θ = 2.3–29.2° |
| b = 27.0608 (9) Å | µ = 1.13 mm−1 |
| c = 7.4731 (2) Å | T = 298 K |
| V = 1773.5 (1) Å3 | Block, green |
| Z = 4 | 0.18 × 0.17 × 0.17 mm |
| Bruker SMART CCD area detector diffractometer | 1978 independent reflections |
| Radiation source: fine-focus sealed tube | 1762 reflections with I > 2σ(I) |
| graphite | Rint = 0.023 |
| ω scans | θmax = 27.0°, θmin = 2.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→11 |
| Tmin = 0.823, Tmax = 0.832 | k = −34→32 |
| 9937 measured reflections | l = −9→8 |
| 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0327P)2 + 1.6368P] where P = (Fo2 + 2Fc2)/3 |
| 1978 reflections | (Δ/σ)max = 0.001 |
| 125 parameters | Δρmax = 0.39 e Å−3 |
| 1 restraint | Δρmin = −0.46 e Å−3 |
| [Ni(C18H18N2O4)(H2O)] | V = 1773.5 (1) Å3 |
| Mr = 403.07 | Z = 4 |
| Orthorhombic, Pnma | Mo Kα radiation |
| a = 8.7698 (3) Å | µ = 1.13 mm−1 |
| b = 27.0608 (9) Å | T = 298 K |
| c = 7.4731 (2) Å | 0.18 × 0.17 × 0.17 mm |
| Bruker SMART CCD area detector diffractometer | 1978 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1762 reflections with I > 2σ(I) |
| Tmin = 0.823, Tmax = 0.832 | Rint = 0.023 |
| 9937 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.085 | Δρmax = 0.39 e Å−3 |
| S = 1.04 | Δρmin = −0.46 e Å−3 |
| 1978 reflections | Absolute structure: ? |
| 125 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
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 | 0.04557 (4) | 0.2500 | 1.04045 (5) | 0.03460 (13) | |
| N1 | 0.1893 (2) | 0.29806 (9) | 0.9426 (3) | 0.0540 (5) | |
| O1 | −0.10331 (18) | 0.30124 (6) | 1.0871 (2) | 0.0459 (4) | |
| O2 | −0.3611 (2) | 0.45495 (6) | 1.0277 (2) | 0.0558 (5) | |
| O3 | 0.1380 (3) | 0.2500 | 1.3276 (3) | 0.0467 (5) | |
| C1 | 0.0251 (3) | 0.36946 (9) | 0.9443 (3) | 0.0425 (5) | |
| C2 | −0.1014 (3) | 0.34714 (8) | 1.0324 (3) | 0.0379 (5) | |
| C3 | −0.2323 (3) | 0.37628 (8) | 1.0615 (3) | 0.0412 (5) | |
| H3A | −0.3160 | 0.3625 | 1.1197 | 0.049* | |
| C4 | −0.2387 (3) | 0.42474 (9) | 1.0054 (3) | 0.0440 (5) | |
| C5 | −0.1154 (3) | 0.44666 (9) | 0.9178 (3) | 0.0535 (6) | |
| H5 | −0.1204 | 0.4793 | 0.8791 | 0.064* | |
| C6 | 0.0129 (3) | 0.41896 (9) | 0.8904 (3) | 0.0519 (6) | |
| H6 | 0.0958 | 0.4336 | 0.8336 | 0.062* | |
| C7 | 0.1637 (3) | 0.34352 (10) | 0.9075 (3) | 0.0501 (6) | |
| H7 | 0.2418 | 0.3613 | 0.8532 | 0.060* | |
| C8 | 0.3344 (3) | 0.27498 (13) | 0.8944 (7) | 0.1204 (18) | |
| H8A | 0.3633 | 0.2863 | 0.7760 | 0.144* | |
| H8B | 0.4119 | 0.2863 | 0.9774 | 0.144* | |
| C9 | −0.4961 (3) | 0.43441 (10) | 1.1044 (4) | 0.0623 (7) | |
| H9A | −0.5306 | 0.4073 | 1.0321 | 0.093* | |
| H9B | −0.5740 | 0.4593 | 1.1096 | 0.093* | |
| H9C | −0.4743 | 0.4228 | 1.2231 | 0.093* | |
| H3 | 0.194 (3) | 0.2744 (7) | 1.355 (4) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.02532 (19) | 0.0415 (2) | 0.0369 (2) | 0.000 | 0.00467 (15) | 0.000 |
| N1 | 0.0328 (10) | 0.0682 (14) | 0.0611 (13) | −0.0012 (9) | 0.0092 (9) | 0.0186 (11) |
| O1 | 0.0374 (8) | 0.0394 (8) | 0.0610 (10) | −0.0007 (7) | 0.0115 (7) | 0.0110 (7) |
| O2 | 0.0664 (11) | 0.0380 (9) | 0.0631 (11) | 0.0067 (8) | 0.0063 (9) | 0.0083 (8) |
| O3 | 0.0341 (12) | 0.0514 (14) | 0.0545 (14) | 0.000 | −0.0101 (11) | 0.000 |
| C1 | 0.0450 (12) | 0.0462 (12) | 0.0363 (11) | −0.0125 (10) | 0.0011 (9) | 0.0016 (10) |
| C2 | 0.0390 (11) | 0.0389 (11) | 0.0360 (10) | −0.0064 (9) | −0.0016 (9) | 0.0025 (9) |
| C3 | 0.0421 (12) | 0.0373 (11) | 0.0443 (12) | −0.0050 (9) | 0.0034 (10) | 0.0022 (9) |
| C4 | 0.0555 (14) | 0.0387 (12) | 0.0378 (11) | −0.0029 (10) | −0.0022 (10) | 0.0006 (9) |
| C5 | 0.0708 (17) | 0.0381 (12) | 0.0518 (14) | −0.0100 (12) | 0.0048 (13) | 0.0077 (11) |
| C6 | 0.0578 (15) | 0.0502 (14) | 0.0478 (13) | −0.0181 (12) | 0.0072 (12) | 0.0067 (11) |
| C7 | 0.0397 (12) | 0.0629 (16) | 0.0478 (13) | −0.0120 (11) | 0.0051 (10) | 0.0133 (12) |
| C8 | 0.0448 (16) | 0.104 (3) | 0.212 (5) | 0.0225 (16) | 0.056 (2) | 0.079 (3) |
| C9 | 0.0617 (16) | 0.0539 (15) | 0.0713 (18) | 0.0134 (13) | 0.0116 (15) | 0.0120 (14) |
| Ni1—O1i | 1.9363 (16) | C2—C3 | 1.410 (3) |
| Ni1—O1 | 1.9363 (16) | C3—C4 | 1.378 (3) |
| Ni1—N1i | 1.953 (2) | C3—H3A | 0.9300 |
| Ni1—N1 | 1.953 (2) | C4—C5 | 1.396 (3) |
| Ni1—O3 | 2.294 (2) | C5—C6 | 1.367 (4) |
| N1—C7 | 1.278 (3) | C5—H5 | 0.9300 |
| N1—C8 | 1.463 (3) | C6—H6 | 0.9300 |
| O1—C2 | 1.308 (3) | C7—H7 | 0.9300 |
| O2—C4 | 1.359 (3) | C8—C8i | 1.352 (7) |
| O2—C9 | 1.428 (3) | C8—H8A | 0.9700 |
| O3—H3 | 0.847 (10) | C8—H8B | 0.9700 |
| C1—C6 | 1.403 (3) | C9—H9A | 0.9600 |
| C1—C2 | 1.424 (3) | C9—H9B | 0.9600 |
| C1—C7 | 1.430 (3) | C9—H9C | 0.9600 |
| O1i—Ni1—O1 | 91.47 (9) | O2—C4—C3 | 124.6 (2) |
| O1i—Ni1—N1i | 91.48 (8) | O2—C4—C5 | 114.4 (2) |
| O1—Ni1—N1i | 168.38 (9) | C3—C4—C5 | 121.0 (2) |
| O1i—Ni1—N1 | 168.38 (9) | C6—C5—C4 | 118.3 (2) |
| O1—Ni1—N1 | 91.48 (8) | C6—C5—H5 | 120.8 |
| N1i—Ni1—N1 | 83.49 (13) | C4—C5—H5 | 120.8 |
| O1i—Ni1—O3 | 94.00 (7) | C5—C6—C1 | 122.9 (2) |
| O1—Ni1—O3 | 94.00 (7) | C5—C6—H6 | 118.6 |
| N1i—Ni1—O3 | 97.00 (8) | C1—C6—H6 | 118.6 |
| N1—Ni1—O3 | 97.00 (8) | N1—C7—C1 | 125.6 (2) |
| C7—N1—C8 | 120.9 (2) | N1—C7—H7 | 117.2 |
| C7—N1—Ni1 | 127.17 (17) | C1—C7—H7 | 117.2 |
| C8—N1—Ni1 | 111.69 (19) | C8i—C8—N1 | 115.27 (16) |
| C2—O1—Ni1 | 127.95 (14) | C8i—C8—H8A | 108.5 |
| C4—O2—C9 | 118.01 (19) | N1—C8—H8A | 108.5 |
| Ni1—O3—H3 | 115 (2) | C8i—C8—H8B | 108.5 |
| C6—C1—C2 | 118.6 (2) | N1—C8—H8B | 108.5 |
| C6—C1—C7 | 118.6 (2) | H8A—C8—H8B | 107.5 |
| C2—C1—C7 | 122.8 (2) | O2—C9—H9A | 109.5 |
| O1—C2—C3 | 118.17 (19) | O2—C9—H9B | 109.5 |
| O1—C2—C1 | 123.9 (2) | H9A—C9—H9B | 109.5 |
| C3—C2—C1 | 117.9 (2) | O2—C9—H9C | 109.5 |
| C4—C3—C2 | 121.2 (2) | H9A—C9—H9C | 109.5 |
| C4—C3—H3A | 119.4 | H9B—C9—H9C | 109.5 |
| C2—C3—H3A | 119.4 |
| Symmetry codes: (i) x, −y+1/2, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O1ii | 0.85 (1) | 1.97 (2) | 2.734 (2) | 150 (3) |
| Symmetry codes: (ii) x+1/2, y, −z+5/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O1i | 0.85 (1) | 1.97 (2) | 2.734 (2) | 150 (3) |
| Symmetry codes: (i) x+1/2, y, −z+5/2. |
Financial support from the Jiaying University research fund is gratefully acknowledged.
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Nickel(II) complexes play an important role in both bioinorganic chemistry and coordination chemistry (Suh et al., 1996; Dey et al., 2004; Angulo et al., 2001; Ramadevi et al., 2005; Edison et al., 2004). Recently, the author has reported a nickel(II) complex with a related Schiff base ligand (Tang, 2009). As a continuation of this work, the title mononuclear nickel(II) complex, Fig. 1, is reported here.
The molecule of the title complex possesses crystallographic mirror symmetry. The Ni atom in the complex is five-coordinated by two imine N and two phenolate O atoms of the Schiff base ligand, and by one water O atom, forming a square-pyramidal geometry.
In the crystal structure, the molecules are linked through intermolecular O—H···O hydrogen bonds (Table 1), forming chains along the a axis, as shown in Fig. 2.