{4-Chloro-2-[(2-hy-droxy-eth-yl)imino-meth-yl]phenolato}{4-chloro-2-[(2-oxido-eth-yl)imino-meth-yl]phenolato}cobalt(III).

In the title mononuclear cobalt(III) compound, [Co(C(9)H(8)ClNO(2))(C(9)H(9)ClNO(2))], the Co(II) atom is six-coordinated by two imine N atoms, two phenolate O atoms, and one hy-droxy and one oxide O atom from two Schiff base ligands, forming an octa-hedral geometry. In the crystal structure, adjacent mol-ecules are linked through inter-molecular O-H⋯O hydrogen bonds. The 2-oxidoethyl group is disordered over two positions in a 0.638 (3):0.362 (3) ratio.

Related literature

For general background to Schiff base cobalt(III) complexes, see: Zhang et al. (2010 ▶); Rodriguez et al. (2010 ▶); Khalaji et al. (2010 ▶); Luo & Luo (2010 ▶). For related cobalt complexes with octa­hedral coordination, see: De et al. (2001 ▶); Sun (2005 ▶); Zhu et al. (2003 ▶); Yuan (2006 ▶).

Experimental

Crystal data

[Co(C9H8ClNO2)(C9H9ClNO2)]

M = 455.17

Hexagonal,

a = 18.675 (2) Å

c = 27.595 (3) Å

V = 8334.6 (16) Å3

Z = 18

Mo Kα radiation

μ = 1.24 mm−1

T = 298 K

0.32 × 0.30 × 0.27 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.692, T max = 0.730

13818 measured reflections

4045 independent reflections

2390 reflections with I > 2σ(I)

R int = 0.126

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.00

4045 reflections

257 parameters

9 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.44 e Å−3

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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033088/hg2699sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033088/hg2699Isup2.hkl

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

[Co(C9H8ClNO2)(C9H9ClNO2)]	Dx = 1.632 Mg m−3
Mr = 455.17	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3	Cell parameters from 2130 reflections
Hall symbol: -R 3	θ = 2.5–24.5°
a = 18.675 (2) Å	µ = 1.24 mm−1
c = 27.595 (3) Å	T = 298 K
V = 8334.6 (16) Å3	Block, red
Z = 18	0.32 × 0.30 × 0.27 mm
F(000) = 4176

Bruker APEXII CCD area-detector diffractometer	4045 independent reflections
Radiation source: fine-focus sealed tube	2390 reflections with I > 2σ(I)
graphite	Rint = 0.126
ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→22
Tmin = 0.692, Tmax = 0.730	k = −23→23
13818 measured reflections	l = −35→23

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0437P)2] where P = (Fo2 + 2Fc2)/3
4045 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.40 e Å−3
9 restraints	Δρmin = −0.44 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	Occ. (<1)
Co1	0.55643 (3)	0.59070 (3)	0.127819 (16)	0.04116 (18)
Cl1	0.98997 (7)	0.87669 (9)	0.09447 (5)	0.0861 (4)
Cl2	0.41025 (9)	0.19824 (7)	0.01276 (5)	0.0928 (5)
N1	0.63370 (19)	0.63087 (18)	0.17903 (10)	0.0430 (7)
N2	0.47432 (18)	0.5496 (2)	0.07872 (10)	0.0453 (8)
O1	0.63160 (15)	0.65983 (16)	0.08074 (9)	0.0539 (7)
O2	0.47877 (16)	0.51745 (17)	0.17488 (9)	0.0503 (7)
O3	0.58854 (15)	0.51130 (16)	0.11779 (8)	0.0514 (7)
C1	0.7546 (2)	0.7142 (2)	0.12998 (13)	0.0433 (9)
C2	0.7114 (2)	0.7059 (2)	0.08620 (13)	0.0455 (9)
C3	0.7592 (2)	0.7521 (3)	0.04638 (14)	0.0538 (10)
H3	0.7327	0.7476	0.0171	0.065*
C4	0.8429 (2)	0.8033 (2)	0.04895 (15)	0.0536 (10)
H4	0.8723	0.8338	0.0220	0.064*
C5	0.8833 (2)	0.8092 (2)	0.09172 (16)	0.0540 (11)
C6	0.8408 (2)	0.7664 (2)	0.13157 (14)	0.0505 (10)
H6	0.8691	0.7716	0.1603	0.061*
C7	0.7118 (2)	0.6768 (2)	0.17474 (13)	0.0436 (9)
H7	0.7437	0.6871	0.2025	0.052*
C8	0.5941 (3)	0.5974 (2)	0.22574 (12)	0.0543 (10)
H8A	0.5756	0.6328	0.2402	0.065*
H8B	0.6326	0.5939	0.2478	0.065*
C9	0.5219 (3)	0.5132 (3)	0.21629 (14)	0.0587 (11)
H9A	0.5410	0.4742	0.2106	0.070*
H9B	0.4854	0.4945	0.2442	0.070*
C10	0.4806 (2)	0.4271 (2)	0.06097 (12)	0.0459 (9)
C11	0.5442 (2)	0.4424 (2)	0.09464 (13)	0.0446 (9)
C12	0.5605 (3)	0.3772 (3)	0.10272 (14)	0.0549 (11)
H12	0.5999	0.3841	0.1257	0.066*
C13	0.5200 (3)	0.3042 (3)	0.07785 (15)	0.0608 (11)
H13	0.5324	0.2626	0.0838	0.073*
C14	0.4608 (3)	0.2926 (2)	0.04396 (14)	0.0575 (11)
C15	0.4415 (2)	0.3523 (2)	0.03509 (13)	0.0518 (10)
H15	0.4022	0.3438	0.0117	0.062*
C16	0.4515 (2)	0.4846 (2)	0.05371 (13)	0.0458 (9)
H16	0.4134	0.4735	0.0290	0.055*
O4	0.52234 (16)	0.67011 (15)	0.14056 (9)	0.0524 (7)	0.638 (18)
C17	0.4410 (3)	0.6051 (3)	0.07147 (16)	0.0722 (14)	0.638 (18)
H17A	0.3836	0.5734	0.0615	0.087*	0.638 (18)
H17B	0.4717	0.6446	0.0460	0.087*	0.638 (18)
C18	0.4473 (6)	0.6495 (6)	0.1169 (4)	0.061 (3)	0.638 (18)
H18A	0.4455	0.6994	0.1098	0.073*	0.638 (18)
H18B	0.4010	0.6148	0.1378	0.073*	0.638 (18)
O4'	0.52234 (16)	0.67011 (15)	0.14056 (9)	0.0524 (7)	0.362 (18)
C17'	0.4410 (3)	0.6051 (3)	0.07147 (16)	0.0722 (14)	0.362 (18)
H17C	0.4407	0.6163	0.0372	0.087*	0.362 (18)
H17D	0.3844	0.5787	0.0831	0.087*	0.362 (18)
C18'	0.4876 (12)	0.6776 (8)	0.0957 (6)	0.062 (5)	0.362 (18)
H18C	0.4536	0.7022	0.1024	0.074*	0.362 (18)
H18D	0.5324	0.7153	0.0747	0.074*	0.362 (18)
H2	0.4293 (12)	0.507 (3)	0.1794 (16)	0.080*

	U11	U22	U33	U12	U13	U23
Co1	0.0373 (3)	0.0420 (3)	0.0389 (3)	0.0159 (3)	−0.0011 (2)	−0.0015 (2)
Cl1	0.0381 (7)	0.0883 (10)	0.1121 (10)	0.0166 (6)	0.0011 (6)	0.0099 (8)
Cl2	0.1280 (12)	0.0464 (7)	0.0801 (8)	0.0257 (7)	−0.0243 (8)	−0.0136 (6)
N1	0.046 (2)	0.0418 (18)	0.0354 (16)	0.0175 (16)	−0.0015 (14)	−0.0045 (13)
N2	0.0376 (18)	0.055 (2)	0.0399 (17)	0.0202 (16)	−0.0004 (13)	−0.0005 (15)
O1	0.0357 (16)	0.0643 (18)	0.0447 (14)	0.0121 (14)	−0.0010 (11)	0.0086 (13)
O2	0.0366 (15)	0.0582 (17)	0.0497 (15)	0.0188 (14)	0.0006 (12)	0.0096 (12)
O3	0.0427 (16)	0.0563 (18)	0.0551 (15)	0.0246 (14)	−0.0131 (12)	−0.0166 (13)
C1	0.043 (2)	0.040 (2)	0.046 (2)	0.0194 (19)	−0.0029 (17)	−0.0037 (16)
C2	0.039 (2)	0.048 (2)	0.048 (2)	0.021 (2)	0.0018 (17)	−0.0018 (17)
C3	0.047 (3)	0.062 (3)	0.049 (2)	0.025 (2)	0.0038 (18)	0.0041 (19)
C4	0.040 (2)	0.054 (3)	0.062 (3)	0.019 (2)	0.0103 (19)	0.009 (2)
C5	0.033 (2)	0.047 (2)	0.077 (3)	0.017 (2)	0.004 (2)	0.000 (2)
C6	0.044 (2)	0.055 (3)	0.058 (2)	0.029 (2)	−0.0064 (19)	−0.009 (2)
C7	0.047 (3)	0.043 (2)	0.042 (2)	0.024 (2)	−0.0092 (17)	−0.0067 (16)
C8	0.062 (3)	0.052 (3)	0.035 (2)	0.018 (2)	0.0011 (18)	−0.0012 (17)
C9	0.055 (3)	0.065 (3)	0.048 (2)	0.024 (2)	−0.0023 (19)	0.011 (2)
C10	0.045 (2)	0.047 (2)	0.036 (2)	0.016 (2)	0.0040 (17)	0.0027 (17)
C11	0.039 (2)	0.048 (2)	0.041 (2)	0.0180 (19)	0.0028 (16)	−0.0037 (17)
C12	0.056 (3)	0.061 (3)	0.050 (2)	0.032 (2)	−0.0057 (19)	−0.005 (2)
C13	0.075 (3)	0.055 (3)	0.057 (3)	0.036 (3)	0.003 (2)	0.002 (2)
C14	0.072 (3)	0.044 (2)	0.045 (2)	0.020 (2)	0.004 (2)	0.0004 (18)
C15	0.051 (3)	0.045 (2)	0.043 (2)	0.012 (2)	−0.0058 (17)	−0.0031 (18)
C16	0.034 (2)	0.052 (3)	0.0365 (19)	0.0104 (19)	0.0005 (15)	0.0010 (18)
O4	0.0542 (17)	0.0457 (17)	0.0576 (16)	0.0252 (14)	−0.0065 (13)	−0.0045 (12)
C17	0.080 (3)	0.102 (4)	0.065 (3)	0.067 (3)	−0.009 (2)	−0.008 (3)
C18	0.047 (5)	0.064 (6)	0.080 (6)	0.034 (5)	−0.002 (4)	0.003 (4)
O4'	0.0542 (17)	0.0457 (17)	0.0576 (16)	0.0252 (14)	−0.0065 (13)	−0.0045 (12)
C17'	0.080 (3)	0.102 (4)	0.065 (3)	0.067 (3)	−0.009 (2)	−0.008 (3)
C18'	0.063 (9)	0.051 (7)	0.073 (8)	0.030 (6)	−0.006 (6)	−0.001 (6)

Co1—O1	1.874 (2)	C7—H7	0.9300
Co1—O3	1.877 (3)	C8—C9	1.496 (5)
Co1—N1	1.887 (3)	C8—H8A	0.9700
Co1—N2	1.897 (3)	C8—H8B	0.9700
Co1—O4	1.916 (3)	C9—H9A	0.9700
Co1—O2	1.918 (3)	C9—H9B	0.9700
Cl1—C5	1.747 (4)	C10—C15	1.405 (5)
Cl2—C14	1.753 (4)	C10—C11	1.420 (5)
N1—C7	1.275 (4)	C10—C16	1.440 (5)
N1—C8	1.462 (4)	C11—C12	1.413 (5)
N2—C16	1.270 (4)	C12—C13	1.367 (5)
N2—C17	1.465 (5)	C12—H12	0.9300
O1—C2	1.305 (4)	C13—C14	1.380 (6)
O2—C9	1.423 (4)	C13—H13	0.9300
O2—H2	0.855 (10)	C14—C15	1.356 (6)
O3—C11	1.298 (4)	C15—H15	0.9300
C1—C6	1.404 (5)	C16—H16	0.9300
C1—C2	1.418 (5)	O4—C18	1.414 (7)
C1—C7	1.447 (5)	C17—C18	1.474 (8)
C2—C3	1.406 (5)	C17—H17A	0.9700
C3—C4	1.368 (5)	C17—H17B	0.9700
C3—H3	0.9300	C18—H18A	0.9700
C4—C5	1.375 (5)	C18—H18B	0.9700
C4—H4	0.9300	C18'—H18C	0.9700
C5—C6	1.359 (5)	C18'—H18D	0.9700
C6—H6	0.9300
O1—Co1—O3	90.97 (12)	N1—C8—C9	107.0 (3)
O1—Co1—N1	94.87 (12)	N1—C8—H8A	110.3
O3—Co1—N1	86.66 (12)	C9—C8—H8A	110.3
O1—Co1—N2	87.65 (12)	N1—C8—H8B	110.3
O3—Co1—N2	95.06 (12)	C9—C8—H8B	110.3
N1—Co1—N2	176.94 (12)	H8A—C8—H8B	108.6
O1—Co1—O4	91.05 (11)	O2—C9—C8	108.6 (3)
O3—Co1—O4	177.77 (11)	O2—C9—H9A	110.0
N1—Co1—O4	92.22 (12)	C8—C9—H9A	110.0
N2—Co1—O4	85.98 (12)	O2—C9—H9B	110.0
O1—Co1—O2	178.46 (12)	C8—C9—H9B	110.0
O3—Co1—O2	87.87 (12)	H9A—C9—H9B	108.4
N1—Co1—O2	86.08 (12)	C15—C10—C11	119.9 (4)
N2—Co1—O2	91.44 (12)	C15—C10—C16	118.0 (4)
O4—Co1—O2	90.13 (12)	C11—C10—C16	122.0 (3)
C7—N1—C8	122.3 (3)	O3—C11—C12	118.1 (3)
C7—N1—Co1	126.0 (2)	O3—C11—C10	125.2 (4)
C8—N1—Co1	111.5 (2)	C12—C11—C10	116.7 (3)
C16—N2—C17	122.9 (3)	C13—C12—C11	122.0 (4)
C16—N2—Co1	126.3 (3)	C13—C12—H12	119.0
C17—N2—Co1	110.8 (3)	C11—C12—H12	119.0
C2—O1—Co1	126.1 (2)	C12—C13—C14	119.9 (4)
C9—O2—Co1	109.7 (2)	C12—C13—H13	120.1
C9—O2—H2	117 (3)	C14—C13—H13	120.1
Co1—O2—H2	127 (3)	C15—C14—C13	120.9 (4)
C11—O3—Co1	123.9 (2)	C15—C14—Cl2	120.5 (3)
C6—C1—C2	119.6 (3)	C13—C14—Cl2	118.6 (4)
C6—C1—C7	118.2 (3)	C14—C15—C10	120.5 (4)
C2—C1—C7	121.8 (3)	C14—C15—H15	119.8
O1—C2—C3	118.6 (3)	C10—C15—H15	119.8
O1—C2—C1	124.8 (3)	N2—C16—C10	124.5 (3)
C3—C2—C1	116.6 (3)	N2—C16—H16	117.8
C4—C3—C2	122.7 (4)	C10—C16—H16	117.8
C4—C3—H3	118.6	C18—O4—Co1	111.8 (3)
C2—C3—H3	118.6	N2—C17—C18	109.8 (4)
C3—C4—C5	119.4 (4)	N2—C17—H17A	109.7
C3—C4—H4	120.3	C18—C17—H17A	109.7
C5—C4—H4	120.3	N2—C17—H17B	109.7
C6—C5—C4	120.8 (4)	C18—C17—H17B	109.7
C6—C5—Cl1	120.6 (3)	H17A—C17—H17B	108.2
C4—C5—Cl1	118.5 (3)	O4—C18—C17	109.6 (5)
C5—C6—C1	120.9 (4)	O4—C18—H18A	109.7
C5—C6—H6	119.6	C17—C18—H18A	109.7
C1—C6—H6	119.6	O4—C18—H18B	109.7
N1—C7—C1	125.1 (3)	C17—C18—H18B	109.7
N1—C7—H7	117.5	H18A—C18—H18B	108.2
C1—C7—H7	117.5	H18C—C18'—H18D	107.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4i	0.86 (1)	1.59 (1)	2.436 (4)	173 (5)

Table 1

Selected bond lengths (Å)

Co1—O1	1.874 (2)
Co1—O3	1.877 (3)
Co1—N1	1.887 (3)
Co1—N2	1.897 (3)
Co1—O4	1.916 (3)
Co1—O2	1.918 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4i	0.86 (1)	1.59 (1)	2.436 (4)	173 (5)

Symmetry code: (i) .