Dichlorido(2-{[2-(piperazin-4-ium-1-yl)eth­yl]imino­meth­yl}phenolate)cadmium(II)

Muhammad Saleh Salga; Hamid Khaledi; Hapipah Mohd Ali

doi:10.1107/S1600536810032563

. 2010 Aug 18;66(Pt 9):m1131. doi: 10.1107/S1600536810032563

Dichlorido(2-{[2-(piperazin-4-ium-1-yl)ethyl]iminomethyl}phenolate)cadmium(II)

Muhammad Saleh Salga ^a, Hamid Khaledi ^a,^*, Hapipah Mohd Ali ^a

PMCID: PMC3007917 PMID: 21588532

Abstract

In the title compound, [CdCl₂(C₁₃H₁₉N₃O)], the Cd^II ion is pentacoordinated with the N,N,O-tridentate Schiff base 2-{[2-(piperazin-4-ium-1-yl)ethyl]iminomethyl}phenolate ligand and two Cl atoms in a highly distorted square-pyramidal geometry; the piperazine ring adopts a chair conformation. In the crystal structure, adjacent molecules are linked together via N—H⋯O and N—H⋯Cl hydrogen bonds, forming infinite layers parallel to the ab plane. The layers are further connected through C—H⋯Cl interactions into a three-dimensional network.

Related literature

For related structures, see: Mukhopadhyay et al. (2003 ▶); Xu et al. (2008 ▶).

Experimental

Crystal data

[CdCl₂(C₁₃H₁₉N₃O)]
M _r = 416.61
Orthorhombic,
a = 14.7512 (16) Å
b = 13.1406 (15) Å
c = 16.6188 (19) Å
V = 3221.4 (6) Å³
Z = 8
Mo Kα radiation
μ = 1.69 mm⁻¹
T = 100 K
0.45 × 0.39 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.518, T _max = 0.751
38841 measured reflections
3700 independent reflections
3409 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.017
wR(F ²) = 0.045
S = 1.06
3700 reflections
187 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032563/pv2318sup1.cif

e-66-m1131-sup1.cif^{(18KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032563/pv2318Isup2.hkl

e-66-m1131-Isup2.hkl^{(181.5KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯Cl1ⁱ	0.89 (2)	2.53 (2)	3.3108 (14)	146 (2)
N3—H3A⋯Cl2ⁱⁱ	0.89 (2)	2.78 (2)	3.2689 (14)	116 (2)
N3—H3B⋯O1ⁱⁱ	0.89 (2)	1.80 (2)	2.6743 (17)	167 (2)
C11—H11B⋯Cl2	0.99	2.70	3.6372 (16)	157
C13—H13B⋯Cl1	0.99	2.78	3.4302 (16)	124
C4—H4⋯Cl1ⁱⁱⁱ	0.95	2.80	3.7165 (17)	161
C13—H13A⋯Cl1ⁱ	0.99	2.82	3.5851 (16)	134

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

Acknowledgments

The authors thank the University of Malaya for funding this study (FRGS grant No. FP009/2008 C).

supplementary crystallographic information

Comment

The title compound is a cadmium (II) complex of the Schiff base ligand, 1-(2-salicylaldiminoethyl)piperazine. The piperazinyl arm of the ligand can, in principle, have both boat and chair conformations that makes the molecule to display ambidentate coordination behavior. The ligand has been shown to act as a tetradentate or tridentate chelate with nickel(II) ions, depending on the piperazine ring conformation (Mukhopadhyay et al., 2003). In the title complex, the piperazine ring adopts the chair conformation and the ligand is bound to the metal ion in a NNO-tridentate fashion. The cadmium(II) atom is penta-coordinated by the Schiff base ligand and two chloride atoms in a highly distorted square planar geometry (index τ = 0.38). The piperzaine nitrogen atom, N3, which stays away from coordination, is protonated, implying the zwitterionic nature of the complex. In the crystal structure, intermolecular N—H···O, N—H···Cl and C—H···Cl hydrogen bonds connect the adjacent molecules into infinite three-dimensional network (Fig. 2). Morever, intramolecular C—H···Cl hydrogen bondings are observed. The crystal structure contains void spaces with the size of 199 Å^-3(6.2% of the cell volume) within which there is no evidence for included solvent.

Experimental

The Schiff base ligand was prepared following the procedure reported previously (Mukhopadhyay et al., 2003). The cadmium (II) complex was synthesized by treatment of the ligand (0.233 g, 1 mmol) with cadmium (II) chloride (0.183 g, 1 mmol) in ethanol (20 ml). The mixture was stirred at room temperature for 10 min and then set aside for a few days whereupon the yellow crystals of the title compound were obtained.