Bis{2,4-dibromo-6-[(2-phenyl­eth­yl)imino­meth­yl]phenolato-κ2 N,O}cobalt(II)

Yanli Yin; Jinrong Wang; Yongliang Zhao; Liang Huang

doi:10.1107/S160053681104459X

. 2011 Oct 29;67(Pt 11):m1642. doi: 10.1107/S160053681104459X

Bis{2,4-dibromo-6-[(2-phenylethyl)iminomethyl]phenolato-κ² N,O}cobalt(II)

Yanli Yin ^a,^*, Jinrong Wang ^a, Yongliang Zhao ^a, Liang Huang ^a

PMCID: PMC3247558 PMID: 22219863

Abstract

In the title complex, [Co(C₁₅H₁₂Br₂NO)₂], the Co^II atom is four-coordinated by two N,O-bidentate chelate Schiff base ligands, displaying a flattened tetrahedral coordination environment. The Co^II atom occupies a special position on a twofold rotation axis. In the crystal, molecules are linked via weak C—H⋯Br interactions.

Related literature

For background to vitamin B12, see: Randaccio et al. (2010 ▶). For the antitumour activity of Schiff base–metal complexes, see: Ren et al. (2002 ▶) and for their anti-microbial activity, see: Panneerselvam et al. (2005 ▶). For related structures, see: Chen et al. (2010 ▶); Li et al. (2010 ▶); Jiang et al. (2008 ▶); For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Co(C₁₅H₁₂Br₂NO)₂]
M _r = 823.08
Monoclinic,
a = 22.5087 (16) Å
b = 4.8717 (4) Å
c = 28.864 (2) Å
β = 111.505 (1)°
V = 2944.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 6.04 mm⁻¹
T = 291 K
0.24 × 0.23 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.325, T _max = 0.350
14453 measured reflections
2876 independent reflections
2478 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.108
S = 1.01
2876 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104459X/br2176sup1.cif

e-67-m1642-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104459X/br2176Isup2.hkl

e-67-m1642-Isup2.hkl^{(141.3KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Co1—O1	1.916 (2)
Co1—N1	1.986 (3)

Open in a new tab

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Br2ⁱ	0.93	3.01	3.940 (3)	173
C8—H8B⋯Br1ⁱⁱ	0.97	2.93	3.814 (3)	151
C9—H9B⋯Br2ⁱⁱⁱ	0.97	2.94	3.854 (3)	157

Open in a new tab

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

Acknowledgments

This work was supported by the school scientific research fund of Henan University of Technology.

supplementary crystallographic information

Comment

Cobalt is an important life-required element. For example, vitamin B12, also called cobalamin, is a water soluble vitamin with a key role in the normal functioning of the brain and nervous system, and for the formation of blood (Randaccio et al., 2010). In addition, the Schiff base metal complexes generally possess antitumour activities (Ren et al., 2002) and antimicrobial activities (Panneerselvam et al., 2005). By taking the biological importance of element cobalt into account, we synthesized the title complex with the bidentate N,O-donor Schiff base ligands (Scheme I).

In the title compound, the Co^II atom occupies a special position on a twofold rotation axis to form a distorted tetrahedral coordination sphere. Cobalt(II) atom is four-coordinated by two imino N atoms and two phenolic O atoms from two bidentate Schiff-base ligands derived from the condensation of 3,5-dibromosalicylaldehyde and 2-phenylethylamine (Fig. 1). All bond lengths are within normal ranges (Allen et al., 1987). The C7═N1 bond length of 1.284 (4) Å is within the range of 1.256 (14)–1.310 (15) Å observed in the analogous tetrahedral Co(II) species (Chen et al., 2010; Li et al., 2010). The Co–O and Co–N bond distances of 1.916 (2) and 1.986 (3) Å are also similar to those of 1.935 (2) and 2.006 (3) Å previously reported in the related cobalt(II) complex of a Schiff base ligand derived from the condensation of 3,5-dibromosalicylaldehyde and benzylamine (Jiang et al., 2008).

In the crystal structure, the molecules are linked via weak C–H···Br interactions (Fig.2).

Experimental

3,5-Dibromosalicylaldehyde (560 mg, 2 mmol) and 2-phenylethylamine (242 mg, 2 mmol) were dissolved in a methanol solution (25 mL).The mixture was stirred at room temperature for 1 h to give an orange solution, which was added to a methanol solution (15 mL) of Co(NO₃)₂.6H₂O (280 mg, 1 mmol). The mixture was stirred for another 25 min at room temperature to give a red solution and then filtered. The filtrate was kept in air for 7 days, forming red blocky crystals. The crystals were isolated and dried in a vacuum desiccator containing anhydrous CaCl₂, in about 64% yield. Anal. Calcd for C₃₀H₂₄Br₄CoN₂O₂: C, 43.78; H, 2.94; N, 3.40. Found: C, 43.66; H, 2.99; N, 3.31%. IR (KBr, cm^-1): 3423, 2909, 2361, 1614, 1502, 1433, 1410, 1310, 1210, 1152, 865, 749, 703, 486, 437.