Bis(2-hydroxy-imino-methyl-6-methoxy-phenolato-κO,N)nickel(II).

The Ni atom in the title compound, [Ni(C(8)H(8)NO(3))(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 ▶). 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. (2007 ▶).

Experimental

Crystal data

[Ni(C8H8NO3)2]

M = 391.02

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 ▶).

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

[Ni(C8H8NO3)2]	F(000) = 404
Mr = 391.02	Dx = 1.717 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1702 reflections
a = 8.3464 (8) Å	θ = 2.6–26.0°
b = 4.8596 (4) Å	µ = 1.32 mm−1
c = 18.735 (2) Å	T = 173 K
β = 95.376 (2)°	Prism, green
V = 756.5 (1) Å3	0.48 × 0.16 × 0.15 mm
Z = 2

Bruker APEX2 diffractometer	1405 independent reflections
Radiation source: fine-focus sealed tube	1178 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
Tmin = 0.570, Tmax = 0.826	k = −5→4
3461 measured reflections	l = −14→23

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-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 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

	x	y	z	Uiso*/Ueq
Ni1	0.5000	0.5000	0.5000	0.0169 (2)
O1	0.5102 (2)	0.2294 (4)	0.43290 (9)	0.0214 (4)
O2	0.5912 (2)	−0.1173 (5)	0.33768 (9)	0.0262 (5)
O3	0.2047 (2)	0.6111 (5)	0.55486 (10)	0.0257 (5)
H3	0.2703	0.7276	0.5735	0.039*
N1	0.2806 (3)	0.4473 (5)	0.50729 (11)	0.0192 (5)
C1	0.3919 (3)	0.0737 (6)	0.40274 (13)	0.0210 (6)
C2	0.4326 (3)	−0.1201 (6)	0.35041 (12)	0.0207 (6)
C3	0.3162 (3)	−0.2898 (6)	0.31716 (13)	0.0247 (6)
H3A	0.3443	−0.4196	0.2825	0.030*
C4	0.1567 (3)	−0.2720 (6)	0.33415 (13)	0.0249 (6)
H4	0.0773	−0.3896	0.3109	0.030*
C5	0.1144 (3)	−0.0863 (6)	0.38401 (13)	0.0227 (6)
H5	0.0057	−0.0748	0.3949	0.027*
C6	0.2328 (3)	0.0897 (6)	0.41955 (13)	0.0201 (6)
C7	0.1836 (3)	0.2781 (6)	0.47199 (12)	0.0212 (6)
H7	0.0737	0.2788	0.4814	0.025*
C8	0.6428 (4)	−0.3281 (6)	0.29197 (14)	0.0280 (7)
H8A	0.7599	−0.3188	0.2912	0.042*
H8B	0.5910	−0.3019	0.2433	0.042*
H8C	0.6128	−0.5084	0.3100	0.042*

	U11	U22	U33	U12	U13	U23
Ni1	0.0126 (3)	0.0189 (3)	0.0194 (3)	0.00116 (19)	0.00209 (17)	−0.00161 (17)
O1	0.0155 (10)	0.0228 (11)	0.0263 (8)	−0.0005 (8)	0.0032 (7)	−0.0067 (7)
O2	0.0226 (11)	0.0263 (12)	0.0304 (10)	0.0010 (9)	0.0063 (8)	−0.0080 (9)
O3	0.0148 (10)	0.0342 (13)	0.0288 (9)	0.0006 (9)	0.0055 (7)	−0.0106 (9)
N1	0.0151 (12)	0.0226 (14)	0.0201 (10)	0.0038 (9)	0.0021 (8)	−0.0004 (8)
C1	0.0201 (14)	0.0205 (15)	0.0220 (12)	−0.0015 (11)	−0.0004 (10)	0.0023 (10)
C2	0.0205 (14)	0.0220 (15)	0.0197 (11)	0.0016 (12)	0.0021 (9)	0.0038 (10)
C3	0.0293 (16)	0.0220 (16)	0.0225 (11)	0.0004 (12)	0.0016 (10)	−0.0021 (11)
C4	0.0235 (15)	0.0253 (17)	0.0248 (12)	−0.0053 (12)	−0.0039 (10)	0.0023 (11)
C5	0.0186 (14)	0.0259 (16)	0.0235 (12)	−0.0039 (12)	0.0011 (10)	0.0040 (11)
C6	0.0190 (14)	0.0199 (14)	0.0210 (11)	−0.0014 (11)	−0.0001 (10)	0.0024 (10)
C7	0.0140 (13)	0.0253 (15)	0.0242 (12)	0.0014 (11)	0.0006 (9)	0.0019 (11)
C8	0.0287 (16)	0.0283 (18)	0.0278 (13)	0.0033 (12)	0.0065 (11)	−0.0041 (11)

Ni1—O1	1.827 (2)	C2—C3	1.378 (4)
Ni1—O1i	1.827 (2)	C3—C4	1.400 (4)
Ni1—N1	1.866 (2)	C3—H3A	0.9500
Ni1—N1i	1.866 (2)	C4—C5	1.369 (4)
O1—C1	1.328 (3)	C4—H4	0.9500
O2—C2	1.367 (3)	C5—C6	1.424 (4)
O2—C8	1.427 (3)	C5—H5	0.9500
O3—N1	1.391 (3)	C6—C7	1.431 (4)
O3—H3	0.8400	C7—H7	0.9500
N1—C7	1.292 (3)	C8—H8A	0.9800
C1—C6	1.395 (4)	C8—H8B	0.9800
C1—C2	1.423 (4)	C8—H8C	0.9800
O1—Ni1—O1i	180.00 (7)	C4—C3—H3A	119.8
O1—Ni1—N1	93.50 (9)	C5—C4—C3	120.5 (3)
O1i—Ni1—N1	86.50 (9)	C5—C4—H4	119.7
O1—Ni1—N1i	86.50 (9)	C3—C4—H4	119.7
O1i—Ni1—N1i	93.50 (9)	C4—C5—C6	120.2 (3)
N1—Ni1—N1i	180.00 (12)	C4—C5—H5	119.9
C1—O1—Ni1	128.47 (17)	C6—C5—H5	119.9
C2—O2—C8	116.7 (2)	C1—C6—C5	119.7 (3)
N1—O3—H3	109.5	C1—C6—C7	122.1 (3)
C7—N1—O3	113.0 (2)	C5—C6—C7	118.3 (2)
C7—N1—Ni1	128.46 (19)	N1—C7—C6	123.5 (2)
O3—N1—Ni1	118.51 (16)	N1—C7—H7	118.2
O1—C1—C6	123.9 (2)	C6—C7—H7	118.2
O1—C1—C2	117.0 (2)	O2—C8—H8A	109.5
C6—C1—C2	119.1 (3)	O2—C8—H8B	109.5
O2—C2—C3	125.5 (2)	H8A—C8—H8B	109.5
O2—C2—C1	114.3 (2)	O2—C8—H8C	109.5
C3—C2—C1	120.2 (2)	H8A—C8—H8C	109.5
C2—C3—C4	120.4 (3)	H8B—C8—H8C	109.5
C2—C3—H3A	119.8
N1—Ni1—O1—C1	2.2 (2)	O2—C2—C3—C4	−179.3 (2)
N1i—Ni1—O1—C1	−177.8 (2)	C1—C2—C3—C4	0.4 (4)
O1—Ni1—N1—C7	−2.1 (2)	C2—C3—C4—C5	−0.1 (4)
O1i—Ni1—N1—C7	177.9 (2)	C3—C4—C5—C6	−0.4 (4)
O1—Ni1—N1—O3	179.66 (18)	O1—C1—C6—C5	179.9 (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—C2	178.79 (17)	C2—C1—C6—C7	179.5 (2)
C8—O2—C2—C3	−7.2 (4)	C4—C5—C6—C1	0.6 (4)
C8—O2—C2—C1	173.0 (2)	C4—C5—C6—C7	−179.2 (2)
O1—C1—C2—O2	−0.6 (3)	O3—N1—C7—C6	179.5 (2)
C6—C1—C2—O2	179.6 (2)	Ni1—N1—C7—C6	1.3 (4)
O1—C1—C2—C3	179.6 (2)	C1—C6—C7—N1	0.4 (4)
C6—C1—C2—C3	−0.2 (4)	C5—C6—C7—N1	−179.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.84	1.86	2.492 (3)	131

Table 1

Selected bond lengths (Å)

Ni1—O1	1.827 (2)
Ni1—N1	1.866 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1i	0.84	1.86	2.492 (3)	131

Symmetry code: (i) .