{4-Chloro-2-[(2-hy­droxy­eth­yl)imino­meth­yl]phenolato}{4-chloro-2-[(2-oxido­eth­yl)imino­meth­yl]phenolato}cobalt(III)

Liu, L.-J.

doi:10.1107/S1600536810033088

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1143

https://doi.org/10.1107/S1600536810033088

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{4-Chloro-2-[(2-hydroxyethyl)iminomethyl]phenolato}{4-chloro-2-[(2-oxidoethyl)iminomethyl]phenolato}cobalt(III)

Li-Jun Liu ^a ^*

^aExperimental Center, Linyi Normal University, Linyi Shandong 276005, People's Republic of China
^*Correspondence e-mail: xiaoerduoaa@hotmail.com

(Received 10 August 2010; accepted 17 August 2010; online 21 August 2010)

In the title mononuclear cobalt(III) compound, [Co(C₉H₈ClNO₂)(C₉H₉ClNO₂)], the Co^II atom is six-coordinated by two imine N atoms, two phenolate O atoms, and one hydroxy and one oxide O atom from two Schiff base ligands, forming an octahedral geometry. In the crystal structure, adjacent molecules are linked through intermolecular 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_r = 455.17
Hexagonal, $[R \overline 3]$
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.135
S = 1.00
4045 reflections
257 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.44 e Å⁻³

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) $[y-{\script{1\over 3}}, -x+y+{\script{1\over 3}}, -z+{\script{1\over 3}}]$ .

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033088/hg2699Isup2.hkl

checkCIF report

Comment top

Cobalt(III) complexes with Schiff bases have been widely investigated in coordination chemistry and biological chemistry (Zhang et al., 2010; Rodriguez et al., 2010; Khalaji et al., 2010; Luo & Luo, 2010). In the present paper, the title new cobalt(III) complex with the Schiff base ligand 4-chloro-2-[(2-hydroxyethylimino)methyl]phenol, is reported.

The Co^III atom in the title complex (Fig. 1) is six-coordinated by two imine N atoms, two phenolate O atoms, and two hydroxy O atoms from two Schiff base ligands, forming an octahedral geometry. The mainly difference in the two ligands is that one of the hydroxy groups is deprotonated. The bond lengths and angles (Table 1) related to the Co atom are comparable with those observed in similar cobalt complexes with octahedral geometry (De et al., 2001; Sun, 2005; Zhu et al., 2003; Yuan, 2006). In the crystal structure, the adjacent molecules are linked through intermolecular O—H···O hydrogen bonds (Table 2, Fig. 2).

Related literature top

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 top

5-Chlorosalicylaldehyde (0.1 mmol, 15.6 mg), 2-(2-aminoethylamino)ethanol (0.1 mmol, 10.4 mg), and cobalt acetate tetrahydrate (0.1 mmol, 24.9 mg) were mixed and stirred in methanol (20 ml) at reflux for 2 h, to give a red solution. The solution was cooled to room temperature, and red block-shaped single crystals were formed by slow evaporation of the solution in air. The characteristic IR absorption for the hydroxy group is at 3327 cm^-1.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title complex with 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title complex, viewed along the c axis. Hydrogen bonds are shown as dashed lines.

{4-Chloro-2-[(2-hydroxyethyl)iminomethyl]phenolato}{4-chloro-2-[(2- oxidoethyl)iminomethyl]phenolato}cobalt(III) top

Crystal data top

[Co(C₉H₈ClNO₂)(C₉H₉ClNO₂)]	D_x = 1.632 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0437P)²] where P = (F_o² + 2F_c²)/3
4045 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.40 e Å⁻³
9 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Co(C₉H₈ClNO₂)(C₉H₉ClNO₂)]	Z = 18
M_r = 455.17	Mo Kα radiation
Hexagonal, R3	µ = 1.24 mm⁻¹
a = 18.675 (2) Å	T = 298 K
c = 27.595 (3) Å	0.32 × 0.30 × 0.27 mm
V = 8334.6 (16) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4045 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2390 reflections with I > 2σ(I)
T_min = 0.692, T_max = 0.730	R_int = 0.126
13818 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	9 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.40 e Å⁻³
4045 reflections	Δρ_min = −0.44 e Å⁻³
257 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) y−1/3, −x+y+1/3, −z+1/3.

Experimental details

Crystal data
Chemical formula	[Co(C₉H₈ClNO₂)(C₉H₉ClNO₂)]
M_r	455.17
Crystal system, space group	Hexagonal, R3
Temperature (K)	298
a, c (Å)	18.675 (2), 27.595 (3)
V (Å³)	8334.6 (16)
Z	18
Radiation type	Mo Kα
µ (mm⁻¹)	1.24
Crystal size (mm)	0.32 × 0.30 × 0.27

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.692, 0.730
No. of measured, independent and observed [I > 2σ(I)] reflections	13818, 4045, 2390
R_int	0.126
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.135, 1.00
No. of reflections	4045
No. of parameters	257
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.44

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

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

O1—Co1—O3	90.97 (12)	N1—Co1—O4	92.22 (12)
O1—Co1—N1	94.87 (12)	N2—Co1—O4	85.98 (12)
O3—Co1—N1	86.66 (12)	O1—Co1—O2	178.46 (12)
O1—Co1—N2	87.65 (12)	O3—Co1—O2	87.87 (12)
O3—Co1—N2	95.06 (12)	N1—Co1—O2	86.08 (12)
N1—Co1—N2	176.94 (12)	N2—Co1—O2	91.44 (12)
O1—Co1—O4	91.05 (11)	O4—Co1—O2	90.13 (12)
O3—Co1—O4	177.77 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4ⁱ	0.855 (10)	1.586 (12)	2.436 (4)	173 (5)

Symmetry code: (i) y−1/3, −x+y+1/3, −z+1/3.

Acknowledgements

The author acknowledges the Linyi Normal University for supporting this work.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
De, R. L., Samanta, K., Maiti, K. & Keller, E. (2001). Inorg. Chim. Acta, 316, 113–116. Web of Science CSD CrossRef CAS Google Scholar
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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{4-Chloro-2-[(2-hy­dr­oxy­eth­yl)imino­meth­yl]phenolato}{4-chloro-2-[(2-oxido­eth­yl)imino­meth­yl]phenolato}cobalt(III)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{4-Chloro-2-[(2-hydroxyethyl)iminomethyl]phenolato}{4-chloro-2-[(2-oxidoethyl)iminomethyl]phenolato}cobalt(III)