{4,4′,6,6′-Tetra­chloro-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methanylyl­idene)]}copper(II)

Hadi Kargar; Reza Kia; Saeideh Abbasian; Muhammad Nawaz Tahir

doi:10.1107/S160053681200195X

. 2012 Jan 21;68(Pt 2):m182. doi: 10.1107/S160053681200195X

{4,4′,6,6′-Tetrachloro-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]}copper(II)

Hadi Kargar ^a,^*, Reza Kia ^b,^c, Saeideh Abbasian ^a, Muhammad Nawaz Tahir ^d,^*

PMCID: PMC3274908 PMID: 22346855

Abstract

In the title Schiff base complex, [Cu(C₁₉H₁₆Cl₄N₂O₂)], the geometry around the Cu^II atom is distorted square-planar defined by the N₂O₂ donor atoms of the coordinated ligand. The dihedral angle between the substituted benzene rings is 29.95 (16)°. In the crystal, molecules are linked along the b axis, forming individual dimers through C—H⋯O interactions. The crystal structure is further stabilized by intermolecular π–π interactions [centroid–centroid distance = 3.6131 (17) Å].

Related literature

For standard values of bond lengths, see: Allen et al. (1987 ▶). For applications of Schiff bases in coordination chemistry, see, for example: Granovski et al. (1993 ▶); Blower (1998 ▶). For related structures see, for example: Ghaemi et al. (2011 ▶); Kargar et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

[Cu(C₁₉H₁₆Cl₄N₂O₂)]
M _r = 509.68
Monoclinic,
a = 12.4002 (10) Å
b = 8.4570 (7) Å
c = 20.0316 (19) Å
β = 97.278 (4)°
V = 2083.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.58 mm⁻¹
T = 291 K
0.25 × 0.18 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.694, T _max = 0.871
18291 measured reflections
4988 independent reflections
2882 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.105
S = 1.00
4988 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681200195X/hp2025sup1.cif

e-68-0m182-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200195X/hp2025Isup2.hkl

e-68-0m182-Isup2.hkl^{(244.3KB, 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
C8—H8A⋯O1ⁱ	0.97	2.56	3.331 (4)	136

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Symmetry code: (i) Inline graphic .

Acknowledgments

HK and SA thank PNU for financial support. MNT thanks GC University of Sargodha, Pakistan for the research facilities.

supplementary crystallographic information

Comment

Schiff base complexes are one of the most important stereochemical models in transition metal coordination chemistry, with the ease of preparation and structural variations (Granovski et al., 1993; Blower et al., (1998). In continuation of our work on the crystal structure of Schiff base metal complexes (Kargar et al., 2012; Kargar et al., 2011; Ghaemi, et al., (2011), we determined the X-ray structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a Schiff base complex. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable to the related structure (Kargar et al., 2012; Kargar et al., 2011; Ghaemi, et al., (2011).

The geometry around Cu^II is a distorted square-planar which is supported by the N₂O₂ donor atoms of the coordinated Schiff base ligand. The dihedral angle between the substituted benzene rings is 29.95 (16)°. In the crystal structure the molecules are linked together along the b-axis, forming individual dimers through the intermolecular C—H···O interactions (Table 1, Fig. 2). The crystal structure is further stabilized by the intermolecular π-π interaction [Cg1···Cg1ⁱⁱ = 3.6131 (17)Å; (ii) 1 - X, 1- Y,-Z; Cg1 is the centroid of Cu(1)/O(2)/C(19)/C(14)/C(13)/N(2) ring].

Experimental

The title compound was synthesized by adding 3,5-dichloro-salicylaldehyde-2,2-dimethyl-1, 3-propanediamine (2 mmol) to a solution of CuCl₂. 4H₂O (2.1 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered. Dark-green single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.