{2-[(3,5-Dichloro-2-oxidobenzyl­idene)amino-κ2 N,O]-3-methyl­penta­noato-κO}(N,N′-dimethyl­formamide-κO)copper(II)

Jin Hong Xia; Zheng Liu; Yuan Wang; Xiao Zhen Feng

doi:10.1107/S160053680800932X

. 2008 Apr 16;64(Pt 5):m660–m661. doi: 10.1107/S160053680800932X

{2-[(3,5-Dichloro-2-oxidobenzylidene)amino-κ² N,O]-3-methylpentanoato-κO}(N,N′-dimethylformamide-κO)copper(II)

Jin Hong Xia ^a, Zheng Liu ^b, Yuan Wang ^b, Xiao Zhen Feng ^b,^*

PMCID: PMC2961092 PMID: 21202205

Abstract

In the title compound, [Cu(C₁₃H₁₃Cl₂NO₃)(C₃H₇NO)], the Cu^II atom is coordinated in a slightly distorted square-planar geometry by two O atoms and one N atom from the tridentate chiral ligand 2-[(3,5-dichloro-2-oxidobenzylidene)amino]-3-methylpentanoate and by one O atom from dimethylformamide. In the crystal structure, the Cu atom forms contacts with Cl and O atoms of two units (Cu⋯Cl and Cu⋯O = 3.401 and 2.947 Å, respectively), thereby forming an approximately octahedral arrangement. A three-dimensional network is constructed through Cl⋯Cu, O⋯Cu, Cl⋯Cl contacts and C—H⋯O hydrogen bonds.

Related literature

For Schiff base complexes containing amino acids, see: Garcia-Raso et al. (1996 ▶); Dawes et al. (1982 ▶); Laurent et al. (1982 ▶); Zhang et al. (2006 ▶). For related literature, see: Cohen et al. (1964 ▶); Garcia-Orozco et al. (2002 ▶); Hu & Englert (2006 ▶); Royles & Sherrington (2000 ▶); Subramanian et al. (2000 ▶); Zaman et al. (2004 ▶); Zordan et al. (2005 ▶).

Experimental

Crystal data

[Cu(C₁₃H₁₃Cl₂NO₃)(C₃H₇NO)]
M _r = 438.78
Orthorhombic,
a = 11.671 (2) Å
b = 27.465 (3) Å
c = 5.8890 (18) Å
V = 1887.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.46 mm⁻¹
T = 298 (2) K
0.43 × 0.15 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.572, T _max = 0.833
9274 measured reflections
3260 independent reflections
2288 reflections with I > 2σ(I)
R _int = 0.086

Refinement

R[F ² > 2σ(F ²)] = 0.095
wR(F ²) = 0.242
S = 1.05
3260 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −1.08 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1915 Friedel pairs
Flack parameter: 0.11 (6)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800932X/gw2039sup1.cif

e-64-0m660-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800932X/gw2039Isup2.hkl

e-64-0m660-Isup2.hkl^{(160KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Cu1—O3	1.872 (9)
Cu1—O1	1.905 (9)
Cu1—O4	1.920 (9)
Cu1—N1	1.925 (10)

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O3—Cu1—O1	169.2 (4)
O3—Cu1—O4	92.5 (4)
O1—Cu1—O4	90.5 (3)
O3—Cu1—N1	94.2 (4)
O1—Cu1—N1	82.7 (4)
O4—Cu1—N1	173.1 (4)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15B⋯O2ⁱ	0.96	2.31	3.19 (2)	150

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge financial support by the Key Laboratory of Non-ferrous Metal Materials and New Processing Technology, Ministry of Education, China.

supplementary crystallographic information

Comment

Schiff bases is a kind of very important compounds in coordination chemistry. And Schiff base complexes have been increasing interest because of their antivial,anticancer and antibacterial activities.Just as the title compound, it's amino acid salicylicaldehyde of halogen substituent Schiff base. Meanwhile,we find some unusual bonds which look like hydrogen bond in this halogenated compound.

In (I),the Cu^II atom is coordinated by two O atoms, one N atom, which come from one tridentate ligand 2-[(3,5-dichloro-2-oxidobenzylidene)amino]-3-methylpentanoate and one O atom from N,N-Dimethyl-formamide, forming a slightly distorted planar square geometry (Fig. 1). In the unit one-dimensional chains, the distorted planar square with Cl and O which above or below of it form an approximately "octahedral". The weak interaction length of Cl–Cu and O–Cu is 3.401 Å. and 2.947 Å. These can be seen the reasults of Jahn-Teller effect. (Garcia-Orozco et al., 2002) People have interest in packing arrangements of halogenated compounds date back to what Schmidt called the 'chloro effect', where the presence of chloro substituents on aromatic compounds frequently arise from stacking arrangements with a short (ca 4 Å) crystallographic axis (Cohen et al., 1964; Zaman et al., 2004; Zordan et al., 2005). The title compound contains the dichloride ligand 2-[(3,5-dichloro-2-oxidobenzylidene)amino]-3-methylpentanoate, with two Cl atoms accessible at the periphery of the ligand. The three-dimensional network of (I) through short Cl–Cu, Cl–Cl, O–Cu contacts and C–H···O hydrogen bonds.(Fig.3). The weak interaction length of Cl–Cl is 3.349 Å. The final position parameters of the nonhydrogen atoms are given in Table 1. The selected bond lengths and bond angles are listed in Table 2.

Experimental

The title compound was produced from aqueous solution of copper chloride and A ethanol solution of (E)-2-(3,5-dichloro-2-hydroxybenzylideneamino)-3 -methylpentanoic acid with vapour volatilization of N,N-Dimethyl-formamide at room temperature.