Bis(2-imino-methyl-5-methoxy-phenolato)nickel(II).

The title compound, [Ni(C(8)H(8)NO(2))(2)], is a centrosymmetric mononuclear nickel(II) complex. The Ni(II) ion, lying on an inversion centre, is four-coordinated in a square-planar geometry by two phenolate O and two imine N atoms from two symmetry-related 2-imino-methyl-5-methoxy-phenolate ligands. In the crystal, mol-ecules are linked into corrugated layers parallel to (100) by N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Angulo et al. (2001 ▶); Dey et al. (2004 ▶); Edison et al. (2004 ▶); Ramadevi et al. (2005 ▶); Suh et al. (1996 ▶); Tang (2009 ▶); Kamenar et al. (1990 ▶); Costes et al. (1994 ▶).

Experimental

Crystal data

[Ni(C8H8NO2)2]

M = 359.02

Orthorhombic,

a = 7.5704 (16) Å

b = 11.331 (2) Å

c = 17.227 (4) Å

V = 1477.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.34 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.795, T max = 0.805

7939 measured reflections

1620 independent reflections

1122 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.083

S = 1.01

1620 reflections

110 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039233/ci2923sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039233/ci2923Isup2.hkl

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

[Ni(C8H8NO2)2]	F(000) = 744
Mr = 359.02	Dx = 1.614 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1894 reflections
a = 7.5704 (16) Å	θ = 2.3–26.2°
b = 11.331 (2) Å	µ = 1.34 mm−1
c = 17.227 (4) Å	T = 298 K
V = 1477.7 (5) Å3	Block, red
Z = 4	0.18 × 0.17 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	1620 independent reflections
Radiation source: fine-focus sealed tube	1122 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→6
Tmin = 0.795, Tmax = 0.805	k = −11→14
7939 measured reflections	l = −21→22

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.384P] where P = (Fo2 + 2Fc2)/3
1620 reflections	(Δ/σ)max = 0.001
110 parameters	Δρmax = 0.28 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ni1	1.0000	0.0000	0.5000	0.03483 (14)
O1	0.98642 (18)	0.00398 (11)	0.39332 (9)	0.0407 (4)
O2	0.8757 (2)	0.14990 (13)	0.13928 (8)	0.0486 (4)
N1	0.9039 (3)	0.14925 (16)	0.51213 (9)	0.0422 (4)
C1	0.8581 (3)	0.19740 (17)	0.37798 (11)	0.0366 (5)
C2	0.9275 (3)	0.08998 (17)	0.34895 (11)	0.0352 (4)
C3	0.9336 (3)	0.07278 (17)	0.26800 (11)	0.0369 (5)
H3	0.9783	0.0026	0.2480	0.044*
C4	0.8738 (3)	0.15895 (18)	0.21830 (11)	0.0380 (5)
C5	0.8038 (3)	0.26481 (18)	0.24643 (12)	0.0457 (5)
H5	0.7634	0.3224	0.2123	0.055*
C6	0.7956 (3)	0.28230 (19)	0.32452 (12)	0.0426 (5)
H6	0.7473	0.3522	0.3433	0.051*
C7	0.8489 (3)	0.22017 (18)	0.45884 (12)	0.0423 (5)
H7	0.7997	0.2915	0.4746	0.051*
C8	0.9403 (4)	0.0435 (2)	0.10637 (13)	0.0547 (6)
H8A	1.0625	0.0338	0.1198	0.082*
H8B	0.9286	0.0467	0.0509	0.082*
H8C	0.8736	−0.0220	0.1261	0.082*
H1	0.897 (3)	0.176 (2)	0.5612 (8)	0.080*

	U11	U22	U33	U12	U13	U23
Ni1	0.0469 (2)	0.0262 (2)	0.0314 (2)	0.00123 (15)	−0.00135 (15)	−0.00138 (14)
O1	0.0622 (10)	0.0268 (8)	0.0330 (7)	0.0072 (6)	−0.0022 (6)	0.0002 (5)
O2	0.0658 (10)	0.0432 (9)	0.0367 (8)	0.0046 (7)	−0.0027 (7)	0.0072 (7)
N1	0.0578 (12)	0.0320 (10)	0.0367 (10)	0.0037 (9)	−0.0006 (8)	−0.0044 (7)
C1	0.0413 (11)	0.0290 (10)	0.0395 (11)	−0.0004 (8)	−0.0032 (8)	−0.0019 (9)
C2	0.0384 (11)	0.0289 (11)	0.0382 (11)	−0.0038 (9)	−0.0029 (8)	0.0015 (8)
C3	0.0442 (11)	0.0284 (10)	0.0381 (11)	0.0001 (9)	0.0005 (9)	−0.0001 (8)
C4	0.0402 (12)	0.0361 (11)	0.0378 (11)	−0.0045 (9)	−0.0036 (8)	0.0045 (9)
C5	0.0532 (12)	0.0351 (12)	0.0488 (13)	0.0023 (10)	−0.0072 (10)	0.0107 (10)
C6	0.0499 (13)	0.0279 (11)	0.0500 (13)	0.0058 (9)	−0.0032 (10)	0.0007 (10)
C7	0.0516 (14)	0.0281 (11)	0.0472 (13)	0.0038 (10)	−0.0018 (10)	−0.0050 (9)
C8	0.0743 (16)	0.0515 (14)	0.0382 (12)	0.0055 (13)	−0.0010 (11)	0.0029 (11)

Ni1—O1i	1.8411 (16)	C2—C3	1.409 (3)
Ni1—O1	1.8411 (16)	C3—C4	1.375 (3)
Ni1—N1i	1.8529 (18)	C3—H3	0.93
Ni1—N1	1.8529 (18)	C4—C5	1.398 (3)
O1—C2	1.316 (2)	C5—C6	1.361 (3)
O2—C4	1.365 (2)	C5—H5	0.93
O2—C8	1.419 (3)	C6—H6	0.93
N1—C7	1.289 (3)	C7—H7	0.93
N1—H1	0.901 (10)	C8—H8A	0.96
C1—C6	1.413 (3)	C8—H8B	0.96
C1—C2	1.417 (3)	C8—H8C	0.96
C1—C7	1.418 (3)
O1i—Ni1—O1	180	C2—C3—H3	119.8
O1i—Ni1—N1i	93.92 (6)	O2—C4—C3	124.35 (19)
O1—Ni1—N1i	86.08 (6)	O2—C4—C5	114.44 (18)
O1i—Ni1—N1	86.08 (6)	C3—C4—C5	121.21 (19)
O1—Ni1—N1	93.92 (6)	C6—C5—C4	119.00 (19)
N1i—Ni1—N1	180	C6—C5—H5	120.5
C2—O1—Ni1	128.08 (13)	C4—C5—H5	120.5
C4—O2—C8	117.75 (16)	C5—C6—C1	121.97 (19)
C7—N1—Ni1	127.97 (15)	C5—C6—H6	119.0
C7—N1—H1	116.0 (17)	C1—C6—H6	119.0
Ni1—N1—H1	116.0 (17)	N1—C7—C1	124.78 (19)
C6—C1—C2	118.63 (18)	N1—C7—H7	117.6
C6—C1—C7	119.98 (18)	C1—C7—H7	117.6
C2—C1—C7	121.40 (18)	O2—C8—H8A	109.5
O1—C2—C3	117.48 (18)	O2—C8—H8B	109.5
O1—C2—C1	123.82 (17)	H8A—C8—H8B	109.5
C3—C2—C1	118.69 (18)	O2—C8—H8C	109.5
C4—C3—C2	120.50 (19)	H8A—C8—H8C	109.5
C4—C3—H3	119.8	H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ii	0.90 (1)	2.39 (2)	3.166 (2)	144 (2)

Ni1—O1	1.8411 (16)
Ni1—N1	1.8529 (18)

O1i—Ni1—O1	180
O1—Ni1—N1i	86.08 (6)
O1—Ni1—N1	93.92 (6)
N1i—Ni1—N1	180

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ii	0.90 (1)	2.391 (18)	3.166 (2)	144 (2)

Symmetry code: (ii) .