Bis[2,4-dibromo-6-(ethyl-imino-methyl)phenolato-κN,O]cobalt(II).

In the title compound, [Co(C(9)H(8)Br(2)NO)(2)], the Co(II) atom, located on a twofold axis, is in a pseudo-tetra-hedral environment, with two bidentate 2,4-dibromo-6-(ethyl-imino-meth-yl)phenolate Schiff base ligands acting as chelates through their phenolate O and azomethine N atoms. C-H⋯O hydrogen bonds link the complex mol-ecules to form a chain parallel to the b axis.

Related literature

For related Lewis base adducts, see: Akitsu et al. (2005 ▶); Bahron et al. (1994 ▶); Bermejo et al. (1996 ▶); Elerman et al. (1996 ▶); Groombridge et al. (1992 ▶); Li et al. (2008 ▶); Maneiro et al. (2001 ▶); Qiu et al. (2007 ▶). For a related structure, see: Jiang et al. (2008 ▶). For standard bond-distance values, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Co(C9H8Br2NO)2]

M = 670.90

Monoclinic,

a = 22.116 (3) Å

b = 4.8645 (5) Å

c = 19.652 (2) Å

β = 100.038 (3)°

V = 2081.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 8.52 mm−1

T = 298 K

0.30 × 0.21 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.089, T max = 0.392

6537 measured reflections

2028 independent reflections

1607 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.161

S = 1.00

2028 reflections

124 parameters

H-atom parameters constrained

Δρmax = 1.39 e Å−3

Δρmin = −1.08 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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶).; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032174/dn2591sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032174/dn2591Isup2.hkl

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

[Co(C9H8Br2NO)2]	F(000) = 1284
Mr = 670.90	Dx = 2.140 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2472 reflections
a = 22.116 (3) Å	θ = 2.6–27.2°
b = 4.8645 (5) Å	µ = 8.52 mm−1
c = 19.652 (2) Å	T = 298 K
β = 100.038 (3)°	Block, red
V = 2081.9 (4) Å3	0.30 × 0.21 × 0.11 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2028 independent reflections
Radiation source: fine-focus sealed tube	1607 reflections with I > 2σ(I)
graphite	Rint = 0.099
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −26→26
Tmin = 0.089, Tmax = 0.392	k = −6→5
6537 measured reflections	l = −24→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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0865P)2] where P = (Fo2 + 2Fc2)/3
2028 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 1.39 e Å−3
0 restraints	Δρmin = −1.08 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.5000	0.9495 (3)	0.2500	0.0396 (3)
N1	0.44643 (19)	0.7331 (11)	0.3012 (2)	0.0394 (11)
O1	0.43303 (17)	1.1213 (9)	0.1898 (2)	0.0423 (10)
Br1	0.36561 (3)	1.36837 (14)	0.05745 (3)	0.0477 (3)
Br2	0.18010 (3)	0.63810 (17)	0.10502 (4)	0.0595 (3)
C1	0.3544 (2)	0.8138 (12)	0.2155 (3)	0.0354 (12)
C2	0.3778 (2)	1.0161 (13)	0.1750 (3)	0.0343 (12)
C3	0.3371 (3)	1.1041 (12)	0.1146 (3)	0.0354 (13)
C4	0.2796 (2)	0.9972 (13)	0.0949 (3)	0.0398 (13)
H4	0.2549	1.0568	0.0544	0.048*
C5	0.2587 (2)	0.8016 (14)	0.1352 (3)	0.0405 (14)
C6	0.2942 (3)	0.7099 (14)	0.1949 (3)	0.0438 (14)
H6	0.2789	0.5792	0.2219	0.053*
C7	0.3891 (3)	0.6970 (13)	0.2770 (3)	0.0406 (13)
H7	0.3677	0.5820	0.3023	0.049*
C8	0.4728 (3)	0.5890 (14)	0.3657 (3)	0.0508 (16)
H8A	0.5098	0.4929	0.3593	0.061*
H8B	0.4437	0.4538	0.3767	0.061*
C9	0.4878 (4)	0.7869 (17)	0.4243 (3)	0.064 (2)
H9A	0.5131	0.9319	0.4116	0.096*
H9B	0.5094	0.6928	0.4642	0.096*
H9C	0.4505	0.8634	0.4349	0.096*

	U11	U22	U33	U12	U13	U23
Co1	0.0224 (5)	0.0503 (8)	0.0437 (6)	0.000	−0.0009 (4)	0.000
N1	0.026 (2)	0.043 (3)	0.048 (3)	0.006 (2)	0.0011 (19)	0.001 (2)
O1	0.0245 (19)	0.047 (3)	0.051 (2)	−0.0072 (16)	−0.0047 (17)	0.0032 (19)
Br1	0.0393 (4)	0.0488 (5)	0.0511 (4)	−0.0047 (2)	−0.0036 (3)	0.0089 (3)
Br2	0.0276 (4)	0.0697 (6)	0.0769 (5)	−0.0128 (3)	−0.0030 (3)	−0.0035 (4)
C1	0.022 (2)	0.040 (3)	0.043 (3)	0.002 (2)	0.000 (2)	−0.006 (2)
C2	0.026 (2)	0.032 (3)	0.042 (3)	0.003 (2)	−0.004 (2)	−0.006 (2)
C3	0.029 (3)	0.041 (4)	0.035 (3)	0.002 (2)	0.003 (2)	−0.002 (2)
C4	0.031 (3)	0.043 (4)	0.043 (3)	0.003 (2)	−0.003 (2)	−0.005 (3)
C5	0.022 (2)	0.051 (4)	0.046 (3)	0.000 (2)	−0.001 (2)	−0.008 (3)
C6	0.029 (3)	0.044 (4)	0.059 (4)	−0.003 (3)	0.010 (3)	−0.002 (3)
C7	0.032 (3)	0.041 (4)	0.048 (3)	−0.002 (2)	0.007 (2)	0.003 (3)
C8	0.039 (3)	0.049 (4)	0.058 (4)	0.006 (3)	−0.007 (3)	0.010 (3)
C9	0.071 (5)	0.077 (6)	0.044 (4)	0.016 (4)	0.009 (3)	0.009 (4)

Co1—O1i	1.918 (4)	C3—C4	1.366 (8)
Co1—O1	1.918 (4)	C4—C5	1.370 (9)
Co1—N1i	1.985 (5)	C4—H4	0.9300
Co1—N1	1.985 (5)	C5—C6	1.367 (9)
N1—C7	1.287 (7)	C6—H6	0.9300
N1—C8	1.477 (8)	C7—H7	0.9300
O1—C2	1.310 (6)	C8—C9	1.493 (10)
Br1—C3	1.886 (6)	C8—H8A	0.9700
Br2—C5	1.909 (5)	C8—H8B	0.9700
C1—C6	1.414 (8)	C9—H9A	0.9600
C1—C2	1.419 (8)	C9—H9B	0.9600
C1—C7	1.432 (8)	C9—H9C	0.9600
C2—C3	1.424 (8)
O1i—Co1—O1	128.3 (3)	C6—C5—C4	121.4 (5)
O1i—Co1—N1i	94.52 (17)	C6—C5—Br2	119.2 (5)
O1—Co1—N1i	112.53 (19)	C4—C5—Br2	119.4 (4)
O1i—Co1—N1	112.53 (19)	C5—C6—C1	120.0 (6)
O1—Co1—N1	94.52 (17)	C5—C6—H6	120.0
N1i—Co1—N1	116.0 (3)	C1—C6—H6	120.0
C7—N1—C8	118.0 (5)	N1—C7—C1	127.3 (6)
C7—N1—Co1	121.5 (4)	N1—C7—H7	116.3
C8—N1—Co1	120.4 (4)	C1—C7—H7	116.3
C2—O1—Co1	123.9 (4)	N1—C8—C9	110.9 (6)
C6—C1—C2	120.3 (5)	N1—C8—H8A	109.5
C6—C1—C7	116.0 (6)	C9—C8—H8A	109.5
C2—C1—C7	123.7 (5)	N1—C8—H8B	109.5
O1—C2—C1	124.3 (5)	C9—C8—H8B	109.5
O1—C2—C3	119.8 (5)	H8A—C8—H8B	108.0
C1—C2—C3	115.9 (5)	C8—C9—H9A	109.5
C4—C3—C2	122.9 (6)	C8—C9—H9B	109.5
C4—C3—Br1	118.8 (4)	H9A—C9—H9B	109.5
C2—C3—Br1	118.3 (4)	C8—C9—H9C	109.5
C3—C4—C5	119.5 (5)	H9A—C9—H9C	109.5
C3—C4—H4	120.2	H9B—C9—H9C	109.5
C5—C4—H4	120.2

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1ii	0.97	2.49	3.389 (8)	154.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.97	2.49	3.389 (8)	154

Symmetry code: (i) .