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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): m318.
Published online 2009 February 25. doi:  10.1107/S1600536809005996
PMCID: PMC2968630

Bis(2-hydroxy­imino­methyl-6-methoxy­phenolato-κ2 O 1,N)nickel(II)

Abstract

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

For the structure of o-vanillin oxime, see: Xu et al. (2004 [triangle]). For the structure of bis­(salicylaldoximato)nickel, see: Srivastava et al. (1967 [triangle]). 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 [triangle]); Lalia-Kantouri et al. (1999 [triangle]); Ma et al. (2007a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m318-scheme1.jpg

Experimental

Crystal data

  • [Ni(C8H8NO3)2]
  • M r = 391.02
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m318-efi1.jpg
  • a = 8.3464 (8) Å
  • b = 4.8596 (4) Å
  • c = 18.735 (2) Å
  • β = 95.376 (2)°
  • V = 756.5 (1) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.32 mm−1
  • T = 173 K
  • 0.48 × 0.16 × 0.15 mm

Data collection

  • Bruker APEX2 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.570, T max = 0.826
  • 3461 measured reflections
  • 1405 independent reflections
  • 1178 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.105
  • S = 1.13
  • 1405 reflections
  • 117 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.67 e Å−3

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005996/sj2577sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005996/sj2577Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

[Ni(C8H8NO3)2]F(000) = 404
Mr = 391.02Dx = 1.717 Mg m3
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 mm1
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

Bruker APEX2 diffractometer1405 independent reflections
Radiation source: fine-focus sealed tube1178 reflections with I > 2σ(I)
graphiteRint = 0.021
[var phi] 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

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 = 1.13w = 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 Å3
0 restraintsΔρmin = −0.66 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2577).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hultgren, V. M., Beddoes, R. V., Collison, D., Helliwell, M., Atkinson, I. M., Garner, C. D., Lindoy, L. F. & Tasker, P. A. (2001). Chem. Commun. pp. 573–574.
  • Lalia-Kantouri, M., Hatzidimitriou, A. & Uddin, M. (1999). Polyhedron, 26, 3441–3450.
  • Ma, Y., Zhang, W., Ou-Yang, Y., Yoshimura, K., Liao, D. Z., Jiang, Z.-H. & Yan, S.-P. (2007a). J. Mol. Struct.833, 98–101.
  • Ma, Y., Zhang, W., Xu, G.-F., Yoshimura, K. & Liao, D.-Z. (2007b). Z. Anorg. Allg. Chem.633, 657–660.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
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  • Westrip, S. P. (2009). publCIF In preparation.
  • Xu, T., Li, L.-Z. & Ji, H.-W. (2004). Hecheng Huaxue, 12, 22–24.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography