Tris(2-{[2-(4-meth­oxy­phen­yl)eth­yl]imino­meth­yl}phenolato-κ2 N,O 1)cobalt(III)

Ali Ourari; Yasmina Ouennoughi; Sofiane Bouacida

doi:10.1107/S1600536812023033

. 2012 May 26;68(Pt 6):m803–m804. doi: 10.1107/S1600536812023033

Tris(2-{[2-(4-methoxyphenyl)ethyl]iminomethyl}phenolato-κ² N,O ¹)cobalt(III)

Ali Ourari ^a, Yasmina Ouennoughi ^a, Sofiane Bouacida ^b,^*

PMCID: PMC3379129 PMID: 22719350

Abstract

In the title compound, [Co(C₁₆H₁₆NO₂)₃], the Co^III atom is six-coordinated in an irregular octahedral geometry by three N,O-chelating 2-{[2-(4-methoxyphenyl)ethyl]iminomethyl}phenolate groups. One of the three methoxy group is disordered over two sets of sites with an occupancy ratio of 0.768 (5):0.232 (5). The crystal packing can be described by alternating zigzag layers of organic ligands and CoN₃O₃ octahedra along the c axis. There are no classical hydrogen bonds in the structure, but C—H⋯π interactions occur.

Related literature

For the synthesis and applications of similar compounds and derivates see: Ourari et al. (2008 ▶, 2011 ▶); Van Praag (1981 ▶); Yu et al. (2003 ▶). graphic file with name e-68-0m803-scheme1.jpg

Experimental

Crystal data

[Co(C₁₆H₁₆NO₂)₃]
M _r = 821.82
Orthorhombic,
a = 15.9798 (5) Å
b = 19.2968 (6) Å
c = 27.4387 (9) Å
V = 8461.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 150 K
0.51 × 0.15 × 0.09 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.789, T _max = 0.960
39521 measured reflections
9652 independent reflections
6226 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.056
wR(F ²) = 0.125
S = 1.01
9652 reflections
531 parameters
H-atom parameters constrained
Δρ_max = 1.10 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and CRYSCAL (T. Roisnel, local program).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023033/bq2360sup1.cif

e-68-0m803-sup1.cif^{(49.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023033/bq2360Isup2.hkl

e-68-0m803-Isup2.hkl^{(462.8KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Co1—O1	1.9054 (16)
Co1—N9	1.952 (2)
Co1—O21	1.8791 (17)
Co1—N29	1.9512 (19)
Co1—O41	1.8955 (18)
Co1—N49	1.944 (2)

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Table 2. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C52–C57 and C42–C47 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1ⁱ	0.95	2.56	3.475 (3)	162
C30—H30B⋯Cg2ⁱⁱ	0.99	2.91	3.838 (3)	157

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank the Algerian Ministère de l’Enseignement Supérieur et de la recherche scientifique for financial support and Professor L. Ouahab (Laboratoire des Sciences Chimiques, Rennes1 France) for helpful discussions.

supplementary crystallographic information

Comment

The O-methyltyramine (4-Mthoxyphenyl)ethlamine is an important pharmaceutical product which is metabolized by monoamineoxidases. This compound may be considered a precursor for neurotransmitter in the central nervous system (Van Praag, 1981) and neurohormone in the blood circulation. This amine reacted, in ethanolic solution, with salicylaldehyde to give N-Salicylidene(4-methoxyphenylethylamine) as bidentate Schiff base ligand (HL). This ligand, dissolved in absolute ethanol with a cobalt salt leads to the formation of its corresponding cobalt complex (Co(III)-3L). The electrocatalytic performaces of this cobalt complex towards the oxidation saturated hydrocarbons or epoxidation of olefins via cytochrome P450 model (Yu et al., 2003) by using molecular oxygen is now under progress in our laboratory (Ourari et al., 2008; Ourari et al., 2011). Thus, we report here the synthesis of title compound and its crystal structure. The molecular geometry of (I), and the atomic numbering used, is illustrated in Fig. 1. The Co atom is six coordinated in a irregular octahedral geometry by three (Salicylidene-(4-Methoxyphenyl)ethylamine)groups, while each one is in bidentate chelating coordination with N and O atoms. The bond lengths for co-ordination cobalt sphere is ranging from 1.8791 (17) to 1.9054 (16) Å for Co—O distances and from 1.944 (2) to 1.952 (2) Å for Co—N distances (Table 1). The crystal packing in the title structure can be described by alterning layers in zigzag of organic ligand and CoN₃O₃ octahedral along the c axis (Fig. 2). C—H···π interactions consolidate the stabilization (Table 2).

Experimental

151 mg (1 mmol) of (4-methoxyphenyl)ethylamine were dissolved in 8 ml of absolute ethanol and placed in three necked flask surmounted by a condenser. Then, an ethanolic solution of 122 mg (1 mmol) of salicylaldehyde (5 ml) was added drop wise to the previous solution. After addition of the first drops under stirring, the solution turns to the yellow color and then is heated to reflux for 2 h. 238 mg of cobalt chloride hexahydrated (CoCl₂,6H₂O) were also dissolved in 8 ml of absolute ethanol and added to the ligand solution. This mixture was refluxed again under stirring for 2 other hours to give finally a solid which is recovered by filtration, washed several times with small portions of distilled water. The solid (crystals) was dried in vaccuo in presence of CaCl₂ to yield 168 mg (61%).