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

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.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.105
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
            Value of measurement temperature given =   173.000
            Value of melting point given =     0.000
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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).

S1. 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.

S2. 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.

Computing details

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

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)

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) Å^3	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 monochromator	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 F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.13	w = 1/[σ^2(Fo^2) + (0.0656P)^2 + 0.2378P] where P = (Fo^2 + 2Fc^2)/3
1405 reflections	(Δ/σ)max = 0.001
117 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.67 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)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Ni1—O1	1.827 (2)	C2—C3	1.378 (4)
Ni1—O1^i	1.827 (2)	C3—C4	1.400 (4)
Ni1—N1	1.866 (2)	C3—H3A	0.9500
Ni1—N1^i	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—O1^i	180.00 (7)	C4—C3—H3A	119.8
O1—Ni1—N1	93.50 (9)	C5—C4—C3	120.5 (3)
O1^i—Ni1—N1	86.50 (9)	C5—C4—H4	119.7
O1—Ni1—N1^i	86.50 (9)	C3—C4—H4	119.7
O1^i—Ni1—N1^i	93.50 (9)	C4—C5—C6	120.2 (3)
N1—Ni1—N1^i	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)
N1^i—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)
O1^i—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)
O1^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^i	0.84	1.86	2.492 (3)	131

Symmetry code: (i) −x+1, −y+1, −z+1.