Bis[2-(5-methyl­sulfanyl-1,3,4-oxadiazol-2-yl-κN 3)phenolato-κO 1]copper(II)

Souheila Ouilia; Chahrazed Beghidja; Adel Beghidja; François Michaud

doi:10.1107/S1600536812026815

. 2012 Jun 20;68(Pt 7):m943. doi: 10.1107/S1600536812026815

Bis[2-(5-methylsulfanyl-1,3,4-oxadiazol-2-yl-κN ³)phenolato-κO ¹]copper(II)

Souheila Ouilia ^a, Chahrazed Beghidja ^a, Adel Beghidja ^a,^*, François Michaud ^b

PMCID: PMC3393202 PMID: 22807770

Abstract

In the title complex, [Cu(C₉H₇N₂O₂S)₂], the Cu^II ion, located on an inversion center, adopts an N₂O₂ square-planar coordination. The 2-(5-methylsulfanyl-1,3,4-oxadiazol-2-yl)phenolate ligand is chelated to the central Cu^II ion in an N,O-bidentate manner.

Related literature

For general background to derivatives of dithiocarbazate ligands and their metal complexes, see: Beghidja et al. (2005 ▶; 2006 ▶); Bouchameni et al. (2011 ▶); Beghidja, Bouslimani & Welter (2007 ▶); Beghidja, Rogez & Welter (2007 ▶). For similar structures, see: Kala et al. (2007 ▶); Liu et al. (2008 ▶); Zhang et al. (2001 ▶). For the preparation of the ligand, see: Dolman et al. (2006 ▶); Young & Wood (1955 ▶).

Experimental

Crystal data

[Cu(C₉H₇N₂O₂S)₂]
M _r = 478.02
Monoclinic,
a = 12.5695 (7) Å
b = 4.4216 (3) Å
c = 17.3861 (9) Å
β = 106.005 (6)°
V = 928.81 (9) Å³
Z = 2
Mo Kα radiation
μ = 1.44 mm⁻¹
T = 170 K
0.18 × 0.12 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.926, T _max = 1.000
6693 measured reflections
1906 independent reflections
1250 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.066
S = 0.99
1906 reflections
133 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ATOMS (Dowty, 1995 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026815/hp2039sup1.cif

e-68-0m943-sup1.cif^{(23.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026815/hp2039Isup2.hkl

e-68-0m943-Isup2.hkl^{(91.9KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Cu1—O2	1.896 (2)
Cu1—N1	1.9746 (19)

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Acknowledgments

The authors thank the Algerian MESRS for financial support (PNR project).

supplementary crystallographic information

Comment

The molecular structure of the complex (1) shows that the Cu^II ion is located on an inversion center and chelated by two bidentate anions HL^- (Fig. 1). This ligand has been obtained from the in situ cyclization of 2-hydroxy [bis(methylsulfanyl)methylene]hydrazide HL⁽¹⁾ described previously by (Young et al.,1955; Dolman et al., 2006). The title mononuclear complex, [Cu (C₉H₇O₂N₂S)₂] (1) has a square-plane geometry formed by the N₂O₂ donor atoms (N1, O2). Several mononuclear compounds with similar structures have been reported previously (Kala et al., 2007; Liu et al., 2008). The whole molecule is planar with a small deviation at C8 from the mean plane. The distances in the coordination planes around the Cu^II ion [Cu₁—N₁= 1.975 (19) Å and Cu₁—O₂= 1.896 (2) Å] are in agreement with other square-planar complexes, such as [Cu(C₁₅H₂₂O)2] [Cu—O = 1.88 (3) Å and Cu—N = 2.00 (3) Å; (Zhang et al., 2001)]. From a supramolecular point of view, this structure can be described as a zigzag chain within which the molecular complexes are connected to each other via the weak hydrogen bonding C—H···O. In the crystal the layers are held together by normal van der Waals interactions (Fig. 2).

Experimental

The ligand HL⁽¹⁾ (0.128 g, 0.05 mmol) was dissolved in minimum of DMF. The solution of CuCl₂.2H₂O (0.0085 g, 0.05 mmol) in DMF was added to the first when the ligand was dissolved completely. Green crystals of the complex 1 were isolated from the solution after two weeks.