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Acta Cryst. (2009). E65, m318    [ doi:10.1107/S1600536809005996 ]

Bis(2-hydroxyiminomethyl-6-methoxyphenolato-[kappa]2O1,N)nickel(II)

B.-W. Li, M.-H. Zeng and S. W. Ng

Abstract top

The Ni atom in the title compound, [Ni(C8H8NO3)2], lies on a center of inversion in a square-planar coordination enviroment. The hydroxyl group of one anion forms a short hydrogen bond to the metal-coordinated O atom of the other anion.

Related literature top

For the structure of o-vanillin oxime, see: Xu et al. (2004). For the structure of bis(salicylaldoximato)nickel, see: Srivastava et al. (1967). The title compound is expected to form complexes with nitrogen-donor ligands as bis(salicylaldoxinato)nickel forms such adducts; see, for example, Hultgren et al. (2001); Lalia-Kantouri et al. (1999); Ma et al. (2007a,b).

Experimental top

Nickel perchlorate hexahydrate (0.36 g, 1 mmol), 3-methoxysalicylaldoxime (0.17 g, 1 mmol) and DMF (8 ml) were placed in a 15 ml Teflon-lined autoclave. The autoclave was heated at 353 K for 3 days. The autoclave was cooled over a period of 8 h at a rate of 10 K per hour. Green crystals were collected by filtration, washed with methanol, and dried in air; yield 30% based on Ni.

Refinement top

Carbon-bound H atoms were placed at calculated positions (C–H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5 times Ueq(C).

The crystal was original measured in the triclinic setting; the raw data when processed for absorption effects in the correct monoclinic setting had somewhat fewer reflections.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ni(C8H8NO3)2. Displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius. The dashed lines denote hydrogen bonds.
Bis(2-hydroxyiminomethyl-6-methoxyphenolato- κ2O1,N)nickel(II) top
Crystal data top
[Ni(C8H8NO3)2]F(000) = 404
Mr = 391.02Dx = 1.717 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1702 reflections
a = 8.3464 (8) Åθ = 2.6–26.0°
b = 4.8596 (4) ŵ = 1.32 mm−1
c = 18.735 (2) ÅT = 173 K
β = 95.376 (2)°Prism, green
V = 756.5 (1) Å30.48 × 0.16 × 0.15 mm
Z = 2
Data collection top
Bruker APEX2
diffractometer		1405 independent reflections
Radiation source: fine-focus sealed tube1178 reflections with I > 2σ(I)
graphiteRint = 0.021
φ and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→10
Tmin = 0.570, Tmax = 0.826k = −5→4
3461 measured reflectionsl = −14→23
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.2378P]
where P = (Fo2 + 2Fc2)/3
1405 reflections(Δ/σ)max = 0.001
117 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.66 e Å−3
Crystal data top
[Ni(C8H8NO3)2]V = 756.5 (1) Å3
Mr = 391.02Z = 2
Monoclinic, P21/nMo Kα radiation
a = 8.3464 (8) ŵ = 1.32 mm−1
b = 4.8596 (4) ÅT = 173 K
c = 18.735 (2) Å0.48 × 0.16 × 0.15 mm
β = 95.376 (2)°
Data collection top
Bruker APEX2
diffractometer		1178 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.021
Tmin = 0.570, Tmax = 0.826θmax = 26.0°
3461 measured reflectionsStandard reflections: 0
1405 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.105Δρmax = 0.37 e Å−3
S = 1.13Δρmin = −0.66 e Å−3
1405 reflectionsAbsolute structure: ?
117 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.0169 (2)
O10.5102 (2)0.2294 (4)0.43290 (9)0.0214 (4)
O20.5912 (2)−0.1173 (5)0.33768 (9)0.0262 (5)
O30.2047 (2)0.6111 (5)0.55486 (10)0.0257 (5)
H30.27030.72760.57350.039*
N10.2806 (3)0.4473 (5)0.50729 (11)0.0192 (5)
C10.3919 (3)0.0737 (6)0.40274 (13)0.0210 (6)
C20.4326 (3)−0.1201 (6)0.35041 (12)0.0207 (6)
C30.3162 (3)−0.2898 (6)0.31716 (13)0.0247 (6)
H3A0.3443−0.41960.28250.030*
C40.1567 (3)−0.2720 (6)0.33415 (13)0.0249 (6)
H40.0773−0.38960.31090.030*
C50.1144 (3)−0.0863 (6)0.38401 (13)0.0227 (6)
H50.0057−0.07480.39490.027*
C60.2328 (3)0.0897 (6)0.41955 (13)0.0201 (6)
C70.1836 (3)0.2781 (6)0.47199 (12)0.0212 (6)
H70.07370.27880.48140.025*
C80.6428 (4)−0.3281 (6)0.29197 (14)0.0280 (7)
H8A0.7599−0.31880.29120.042*
H8B0.5910−0.30190.24330.042*
H8C0.6128−0.50840.31000.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0126 (3)0.0189 (3)0.0194 (3)0.00116 (19)0.00209 (17)−0.00161 (17)
O10.0155 (10)0.0228 (11)0.0263 (8)−0.0005 (8)0.0032 (7)−0.0067 (7)
O20.0226 (11)0.0263 (12)0.0304 (10)0.0010 (9)0.0063 (8)−0.0080 (9)
O30.0148 (10)0.0342 (13)0.0288 (9)0.0006 (9)0.0055 (7)−0.0106 (9)
N10.0151 (12)0.0226 (14)0.0201 (10)0.0038 (9)0.0021 (8)−0.0004 (8)
C10.0201 (14)0.0205 (15)0.0220 (12)−0.0015 (11)−0.0004 (10)0.0023 (10)
C20.0205 (14)0.0220 (15)0.0197 (11)0.0016 (12)0.0021 (9)0.0038 (10)
C30.0293 (16)0.0220 (16)0.0225 (11)0.0004 (12)0.0016 (10)−0.0021 (11)
C40.0235 (15)0.0253 (17)0.0248 (12)−0.0053 (12)−0.0039 (10)0.0023 (11)
C50.0186 (14)0.0259 (16)0.0235 (12)−0.0039 (12)0.0011 (10)0.0040 (11)
C60.0190 (14)0.0199 (14)0.0210 (11)−0.0014 (11)−0.0001 (10)0.0024 (10)
C70.0140 (13)0.0253 (15)0.0242 (12)0.0014 (11)0.0006 (9)0.0019 (11)
C80.0287 (16)0.0283 (18)0.0278 (13)0.0033 (12)0.0065 (11)−0.0041 (11)
Geometric parameters (Å, °) top
Ni1—O11.827 (2)C2—C31.378 (4)
Ni1—O1i1.827 (2)C3—C41.400 (4)
Ni1—N11.866 (2)C3—H3A0.9500
Ni1—N1i1.866 (2)C4—C51.369 (4)
O1—C11.328 (3)C4—H40.9500
O2—C21.367 (3)C5—C61.424 (4)
O2—C81.427 (3)C5—H50.9500
O3—N11.391 (3)C6—C71.431 (4)
O3—H30.8400C7—H70.9500
N1—C71.292 (3)C8—H8A0.9800
C1—C61.395 (4)C8—H8B0.9800
C1—C21.423 (4)C8—H8C0.9800
O1—Ni1—O1i180.00 (7)C4—C3—H3A119.8
O1—Ni1—N193.50 (9)C5—C4—C3120.5 (3)
O1i—Ni1—N186.50 (9)C5—C4—H4119.7
O1—Ni1—N1i86.50 (9)C3—C4—H4119.7
O1i—Ni1—N1i93.50 (9)C4—C5—C6120.2 (3)
N1—Ni1—N1i180.00 (12)C4—C5—H5119.9
C1—O1—Ni1128.47 (17)C6—C5—H5119.9
C2—O2—C8116.7 (2)C1—C6—C5119.7 (3)
N1—O3—H3109.5C1—C6—C7122.1 (3)
C7—N1—O3113.0 (2)C5—C6—C7118.3 (2)
C7—N1—Ni1128.46 (19)N1—C7—C6123.5 (2)
O3—N1—Ni1118.51 (16)N1—C7—H7118.2
O1—C1—C6123.9 (2)C6—C7—H7118.2
O1—C1—C2117.0 (2)O2—C8—H8A109.5
C6—C1—C2119.1 (3)O2—C8—H8B109.5
O2—C2—C3125.5 (2)H8A—C8—H8B109.5
O2—C2—C1114.3 (2)O2—C8—H8C109.5
C3—C2—C1120.2 (2)H8A—C8—H8C109.5
C2—C3—C4120.4 (3)H8B—C8—H8C109.5
C2—C3—H3A119.8
N1—Ni1—O1—C12.2 (2)O2—C2—C3—C4−179.3 (2)
N1i—Ni1—O1—C1−177.8 (2)C1—C2—C3—C40.4 (4)
O1—Ni1—N1—C7−2.1 (2)C2—C3—C4—C5−0.1 (4)
O1i—Ni1—N1—C7177.9 (2)C3—C4—C5—C6−0.4 (4)
O1—Ni1—N1—O3179.66 (18)O1—C1—C6—C5179.9 (2)
O1i—Ni1—N1—O3−0.34 (18)C2—C1—C6—C5−0.3 (4)
Ni1—O1—C1—C6−1.4 (4)O1—C1—C6—C7−0.3 (4)
Ni1—O1—C1—C2178.79 (17)C2—C1—C6—C7179.5 (2)
C8—O2—C2—C3−7.2 (4)C4—C5—C6—C10.6 (4)
C8—O2—C2—C1173.0 (2)C4—C5—C6—C7−179.2 (2)
O1—C1—C2—O2−0.6 (3)O3—N1—C7—C6179.5 (2)
C6—C1—C2—O2179.6 (2)Ni1—N1—C7—C61.3 (4)
O1—C1—C2—C3179.6 (2)C1—C6—C7—N10.4 (4)
C6—C1—C2—C3−0.2 (4)C5—C6—C7—N1−179.8 (3)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.841.862.492 (3)131
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å) top
Ni1—O11.827 (2)Ni1—N11.866 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.841.862.492 (3)131
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

We thank the Natural Science Foundation of Guangxi, Guangxi Normal University and the University of Malaya for support.

references
References top

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