Bis(2-hydroxy­imino­methyl-6-methoxy­phenolato-κ2O1,N)nickel(II)

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

doi:10.1107/S1600536809005996

metal-organic compounds

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doi:10.1107/S1600536809005996

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Bis(2-hydroxyiminomethyl-6-methoxyphenolato-κ²O¹,N)nickel(II)

Bing-Wen Li,^a Ming-Hua Zeng ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Guangxi Normal University, Guilin 541000, Guangxi, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 18 February 2009; accepted 19 February 2009; online 25 February 2009)

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, P 2₁ /n
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[F² > 2σ(F²)] = 0.036
wR(F²) = 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

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) -x+1, -y+1, -z+1.

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 ).

Supporting information

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

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

checkCIF report

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.

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

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
M_r = 391.02	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0656P)² + 0.2378P] where P = (F_o² + 2F_c²)/3
1405 reflections	(Δ/σ)_max = 0.001
117 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Ni(C₈H₈NO₃)₂]	V = 756.5 (1) Å³
M_r = 391.02	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.3464 (8) Å	µ = 1.32 mm⁻¹
b = 4.8596 (4) Å	T = 173 K
c = 18.735 (2) Å	0.48 × 0.16 × 0.15 mm
β = 95.376 (2)°

Data collection top

Bruker APEX2 diffractometer	1405 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1178 reflections with I > 2σ(I)
T_min = 0.570, T_max = 0.826	R_int = 0.021
3461 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.13	Δρ_max = 0.37 e Å⁻³
1405 reflections	Δρ_min = −0.67 e Å⁻³
117 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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 code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ni(C₈H₈NO₃)₂]
M_r	391.02
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	8.3464 (8), 4.8596 (4), 18.735 (2)
β (°)	95.376 (2)
V (Å³)	756.5 (1)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.48 × 0.16 × 0.15

Data collection
Diffractometer	Bruker APEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.570, 0.826
No. of measured, independent and observed [I > 2σ(I)] reflections	3461, 1405, 1178
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.105, 1.13
No. of reflections	1405
No. of parameters	117
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.67

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Ni1—O1

1.827 (2)

Ni1—N1

1.866 (2)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

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

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m318

doi:10.1107/S1600536809005996

Open

access