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

In the title compound, [Co(C(8)H(8)NO(3))(2)], the Co(II) atom lies on a centre of inversion and is coordinated in a slightly distorted square-planar geometry by two N and two O atoms from the 2-hydroxy-imino-methyl-6-methoxy-phenolate ligands. Intra-molecular O-H⋯O hydrogen bonds are formed and the complexes form stacks along the b axis, with an inter-planar separation of 3.332 (1) Å between complexes. Pairs of C-H⋯O contacts are formed between complexes in neighbouring stacks.

Related literature

For recent related literature concerning Schiff-base compounds, see: Gupta & Sutar (2008 ▶); Sreenivasulu et al. (2005 ▶); Zhang et al. (2008 ▶); Raptopoulou et al. (2006 ▶); Milios et al. (2006 ▶); Yang et al. (2007 ▶).

Experimental

Crystal data

[Co(C8H8NO3)2]

M = 391.24

Monoclinic,

a = 8.4254 (19) Å

b = 4.9111 (11) Å

c = 18.951 (4) Å

β = 95.375 (3)°

V = 780.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 1.14 mm−1

T = 293 (2) K

0.22 × 0.18 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

4577 measured reflections

1433 independent reflections

1216 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.065

S = 1.04

1433 reflections

117 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039512/bi2324sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039512/bi2324Isup2.hkl

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

[Co(C8H8NO3)2]	F000 = 402
Mr = 391.24	Dx = 1.664 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4577 reflections
a = 8.4254 (19) Å	θ = 2.6–25.5º
b = 4.9111 (11) Å	µ = 1.14 mm−1
c = 18.951 (4) Å	T = 293 (2) K
β = 95.375 (3)º	Block, red
V = 780.7 (3) Å3	0.22 × 0.18 × 0.14 mm
Z = 2

Bruker SMART CCD diffractometer	1216 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Monochromator: graphite	θmax = 25.5º
T = 293(2) K	θmin = 2.6º
φ and ω scans	h = −10→10
Absorption correction: none	k = −5→5
4577 measured reflections	l = −22→22
1433 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0303P)2 + 0.2885P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1433 reflections	Δρmax = 0.23 e Å−3
117 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Co1	0.0000	0.5000	0.0000	0.03262 (15)
C1	0.1093 (2)	0.0793 (4)	0.09770 (10)	0.0353 (4)
C2	0.0701 (2)	−0.1107 (4)	0.14960 (10)	0.0377 (5)
C3	0.1851 (3)	−0.2781 (4)	0.18262 (11)	0.0448 (5)
H3	0.1581	−0.4028	0.2164	0.054*
C4	0.3423 (3)	−0.2610 (4)	0.16538 (11)	0.0477 (6)
H4	0.4196	−0.3744	0.1880	0.057*
C5	0.3837 (3)	−0.0794 (4)	0.11564 (11)	0.0429 (5)
H5	0.4889	−0.0696	0.1048	0.052*
C6	0.2676 (2)	0.0939 (4)	0.08055 (10)	0.0361 (4)
C7	0.3153 (2)	0.2796 (4)	0.02809 (10)	0.0386 (5)
H7	0.4217	0.2799	0.0187	0.046*
C8	−0.1391 (3)	−0.3153 (5)	0.20761 (12)	0.0535 (6)
H8A	−0.1090	−0.4897	0.1902	0.080*
H8B	−0.2529	−0.3074	0.2077	0.080*
H8C	−0.0903	−0.2898	0.2550	0.080*
N1	0.21926 (19)	0.4465 (3)	−0.00691 (8)	0.0363 (4)
O1	−0.00708 (15)	0.2354 (3)	0.06754 (7)	0.0387 (3)
O2	0.29495 (16)	0.6086 (3)	−0.05443 (8)	0.0487 (4)
H2	0.2301	0.7143	−0.0744	0.073*
O3	−0.08737 (17)	−0.1063 (3)	0.16291 (8)	0.0494 (4)

	U11	U22	U33	U12	U13	U23
Co1	0.0291 (2)	0.0337 (2)	0.0348 (2)	−0.00160 (15)	0.00146 (15)	0.00203 (16)
C1	0.0385 (11)	0.0311 (10)	0.0354 (11)	0.0001 (8)	−0.0005 (9)	−0.0038 (8)
C2	0.0415 (11)	0.0352 (10)	0.0362 (11)	−0.0016 (9)	0.0025 (9)	−0.0015 (9)
C3	0.0566 (14)	0.0375 (11)	0.0392 (11)	−0.0009 (10)	−0.0007 (10)	0.0040 (9)
C4	0.0503 (13)	0.0425 (12)	0.0478 (13)	0.0103 (10)	−0.0080 (10)	−0.0001 (10)
C5	0.0384 (11)	0.0455 (12)	0.0436 (12)	0.0057 (9)	−0.0030 (9)	−0.0045 (10)
C6	0.0360 (10)	0.0350 (10)	0.0364 (11)	−0.0010 (8)	−0.0017 (8)	−0.0043 (8)
C7	0.0286 (10)	0.0438 (11)	0.0429 (11)	0.0001 (9)	0.0016 (8)	−0.0041 (9)
C8	0.0591 (14)	0.0510 (14)	0.0524 (13)	−0.0079 (11)	0.0160 (11)	0.0078 (11)
N1	0.0327 (9)	0.0410 (10)	0.0352 (9)	−0.0053 (7)	0.0040 (7)	0.0019 (7)
O1	0.0332 (7)	0.0397 (8)	0.0434 (8)	0.0005 (6)	0.0044 (6)	0.0083 (6)
O2	0.0346 (8)	0.0598 (10)	0.0523 (9)	−0.0032 (7)	0.0070 (7)	0.0185 (8)
O3	0.0452 (9)	0.0493 (8)	0.0547 (9)	−0.0010 (7)	0.0105 (7)	0.0153 (8)

Co1—O1	1.8290 (13)	C4—H4	0.930
Co1—O1i	1.8290 (13)	C5—C6	1.414 (3)
Co1—N1	1.8826 (17)	C5—H5	0.930
Co1—N1i	1.8826 (17)	C6—C7	1.434 (3)
C1—O1	1.331 (2)	C7—N1	1.290 (2)
C1—C6	1.404 (3)	C7—H7	0.930
C1—C2	1.417 (3)	C8—O3	1.425 (2)
C2—O3	1.374 (2)	C8—H8A	0.960
C2—C3	1.376 (3)	C8—H8B	0.960
C3—C4	1.396 (3)	C8—H8C	0.960
C3—H3	0.930	N1—O2	1.400 (2)
C4—C5	1.367 (3)	O2—H2	0.820
O1—Co1—O1i	180.00 (8)	C6—C5—H5	119.8
O1—Co1—N1	92.64 (6)	C1—C6—C5	119.37 (19)
O1i—Co1—N1	87.36 (6)	C1—C6—C7	121.78 (18)
O1—Co1—N1i	87.36 (6)	C5—C6—C7	118.86 (18)
O1i—Co1—N1i	92.64 (6)	N1—C7—C6	123.89 (18)
N1—Co1—N1i	180.00 (13)	N1—C7—H7	118.1
O1—C1—C6	123.29 (18)	C6—C7—H7	118.1
O1—C1—C2	117.87 (18)	O3—C8—H8A	109.5
C6—C1—C2	118.84 (17)	O3—C8—H8B	109.5
O3—C2—C3	125.24 (19)	H8A—C8—H8B	109.5
O3—C2—C1	114.13 (17)	O3—C8—H8C	109.5
C3—C2—C1	120.62 (19)	H8A—C8—H8C	109.5
C2—C3—C4	120.0 (2)	H8B—C8—H8C	109.5
C2—C3—H3	120.0	C7—N1—O2	112.97 (16)
C4—C3—H3	120.0	C7—N1—Co1	128.68 (14)
C5—C4—C3	120.65 (19)	O2—N1—Co1	118.33 (12)
C5—C4—H4	119.7	C1—O1—Co1	129.71 (13)
C3—C4—H4	119.7	N1—O2—H2	109.5
C4—C5—C6	120.5 (2)	C2—O3—C8	116.90 (17)
C4—C5—H5	119.8

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.91	2.5336 (19)	132
C7—H7···O2ii	0.93	2.48	3.321 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.91	2.5336 (19)	132
C7—H7⋯O2ii	0.93	2.48	3.321 (2)	150

Symmetry codes: (i) ; (ii) .