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 ▶). 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

Crystal data

• [Ni(C₈H₈NO₃)₂]

• M _r = 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) ų

• 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

• Δρ_max = 0.37 e Å⁻³

• Δρ_min = −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 ▶).

Supplementary Material

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

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) .

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 U_eq(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 = 391.02	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

Data collection

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

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

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

	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*

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, °)

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)

Symmetry codes: (i) −x+1, −y+1, −z+1.

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 codes: (i) −x+1, −y+1, −z+1.