[(E)-N′-(5-Chloro-2-oxidobenzyl­idene-κO)-3,4,5-trimeth­oxy­benzohydrazidato-κ2 N′,O](pyridine-κN)copper(II)

Yu-Min Wang; Xiao-Hui Lin; Zhen Chen; Hong-Li Jiang; Chang-Jun Zhang

doi:10.1107/S1600536811009901

. 2011 Apr 7;67(Pt 5):m526. doi: 10.1107/S1600536811009901

[(E)-N′-(5-Chloro-2-oxidobenzylidene-κO)-3,4,5-trimethoxybenzohydrazidato-κ² N′,O](pyridine-κN)copper(II)

Yu-Min Wang ^a,^*, Xiao-Hui Lin ^a, Zhen Chen ^a, Hong-Li Jiang ^a, Chang-Jun Zhang ^a

PMCID: PMC3089131 PMID: 21754268

Abstract

In the title compound, [Cu(C₁₇H₁₅ClN₂O₅)(C₅H₅N)], the Cu^II atom is coordinated by one N atom and two O atoms from an anionic salicylaldehyde benzoylhydrazone ligand and one pyridine N atom in a distorted square-planar geometry. The bonds displays the usual elongation with mean Cu—O and Cu—N bond lengths of 1.926 and 1.976 Å, respectively. The pyridine ring makes dihedral angles of 26.12 (13) and 11.08 (12)°, respectively, with the trimethoxyphenyl and phenolate rings, which make a dihedral angle of 16.05 (12)° with one another.

Related literature

For the biolgical activity of salicylaldehyde derivatives, see: Chan et al. (1995 ▶); Ranford et al. (1998 ▶); Monfared et al. (2009 ▶). For related structures, see: Lee et al. (2003 ▶).

Experimental

Crystal data

[Cu(C₁₇H₁₅ClN₂O₅)(C₅H₅N)]
M _r = 505.40
Monoclinic,
a = 14.274 (4) Å
b = 7.5763 (18) Å
c = 20.753 (5) Å
β = 99.108 (4)°
V = 2216.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.15 mm⁻¹
T = 298 K
0.19 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.812, T _max = 0.875
11265 measured reflections
3908 independent reflections
3184 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.086
S = 1.04
3908 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 I, global. DOI: 10.1107/S1600536811009901/jh2271sup1.cif

e-67-0m526-sup1.cif^{(22.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009901/jh2271Isup2.hkl

e-67-0m526-Isup2.hkl^{(191.6KB, hkl)}

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

supplementary crystallographic information

Comment

Transition metal complexes with potential biological activity are the focus of extensive investigation. Salicylaldehyde benzoylhydrazone possess mild bacteriostatic activity and inhibits DNA synthesis and cell growth (Chan et al.; 1995). Salicylaldehyde acetylhydrazone displays radioprotective properties (Ranford et al.; 1998). Because of the biological interest in this type of chelate system, several structural studies have been carried out on copper with their analogues (Lee et al.; 2003). The copper(II) complex was shown to be significantly more potent than the metal-free chelate, leading to the suggestion that the metal complex was the biologically active species (Monfared et al.; 2009). We report here the crystal structure of the title compound, (I) (Fig. 1). It can be seen that the coordination environment of the copper atom consists of two oxygen atoms and one nitrogen atom from the salicylaldehyde benzoylhydrazone, and one nitrogen atom from the pyridine groups, making up a distorted square-planar environment. The bond length displays the usual elongation: Cu—O = 1.9256 (average) and Cu—N = 1.9755 (average). The pyridine ring makes dihedral angles of 26.12° and 11.08°, respectively, with the C9—C14 and C1—C6 phenyl rings. The C1—C6 benzene ring system makes a dihedral angle of 16.05° with the other C9—C14 benzene ring.

Experimental

Mixture of 20 ml aqueous solution of copper (II) acetate (0.2 mmol) with 2 ml of pyridine was stirred with 20 ml e thanolic solution of (E)-N'-(5-chloro-2-hydroxybenzylidene) -3,4,5-trimethoxybenzohydrazide for 1 h. The resulted solution was leaved in dark place for evaporation. After 1 week of stating blue needle-like shape crystals were grown.