Chlorido(4-methylpyridin-2-amine-κN 1)(2-{[(4-methylpyridin-2-yl)imino-κN]methyl}phenolato-κO)copper(II)

In the title complex, [Cu(C13H11N2O)Cl(C6H8N2)], the CuII atom adopts a distorted tetrahedral geometry being coordinated by the phenolic O atom and the azomethine N atom of the Schiff base ligand N-salicylidene 2-aminopyridine, and by the 2-aminopyridine N atom and a Cl atom. The pyridyl N atom of the Schiff base and the imino N atom of the 4-methyl-pyridine-2-ylimino ligand are not involved in the coordination. There is an intramolecular N—H⋯N hydrogen bond involving the pyridine N atom and the amino group of the 2-aminopyridine ligand. In the crystal, molecules are linked via N—H⋯Cl hydrogen bonds, forming chains propagating along [001].

In the title complex, [Cu(C 13 H 11 N 2 O)Cl(C 6 H 8 N 2 )], the Cu II atom adopts a distorted tetrahedral geometry being coordinated by the phenolic O atom and the azomethine N atom of the Schiff base ligand N-salicylidene 2-aminopyridine, and by the 2-aminopyridine N atom and a Cl atom. The pyridyl N atom of the Schiff base and the imino N atom of the 4-methylpyridine-2-ylimino ligand are not involved in the coordination. There is an intramolecular N-HÁ Á ÁN hydrogen bond involving the pyridine N atom and the amino group of the 2aminopyridine ligand. In the crystal, molecules are linked via N-HÁ Á ÁCl hydrogen bonds, forming chains propagating along [001].

Experimental
Crystal data [Cu(C 13 Table 1 Hydrogen-bond geometry (Å , ). BB thanks the Department of Science and Technolgy, New Delhi, India, for financial support and for providing the singlecrystal X-ray diffractometer facility at the Department of Chemistry, Pondicherry University, under the DST-FIST program.
the complex Bis{2-[(2-pyridyl)iminomethyl]-phenolato}copper(II), has been prepared by (Miao et al., 2009), who reported that to a green solution of salicylaldehyde (0.19 mmol) and Cu(OAc) 2 .H 2 O (0.05 mmol) in ethanol they added slowly an enthanolic solution of 2-aminopyridine (0.22 mmol). The resulting mixture was allowed to stand and brown crystalline needles were obtained after 1 day. The same compound was prepared by an electrochemical method (Castineiras et al., 1989) and by a solution method (Parashar et al., 1988). We have used same procedure as (Miao et al., 2009), but using a 1:1:1 molar ratio that produced the yellow crystals of the title compound, whose crystal structure we report on herein.
In the title complex, Fig. 1, the copper atom has a slightly distorted tetahedral geometry. It coordinates to the phenolic atom O1 and the azomethine atom N4 of the Schiff base liagnd N-salicylidene 2-aminopyridine, and to the 2-aminopyridine atom N1 and a chlorine atom, Cl1. The Cu-O1 and Cu-N4 bond lengths are similar to those reported in related structures (Miao et al., 2009;Castineiras et al., 1989). The structure of the molecule is stablized by an intramolecular N-H..Cl hydrogen bond (Table 1).
In the crystal, the intermolecular N-H···Cl hydrogen bond ( Fig. 2 and Table 1) plays an important role in linking the molecules to form chains propagating along the c axis, as shown in Fig. 3.

Refinement
The NH 2 H-atoms were located in a difference Fourier map and refined with distances restraints: N-H = 0.86 (2) Å. The C-bound H atoms were positioned geometrically and refined using a riding model: C-H = 0.93 and 0.96 Å, for CH and CH 3 H atoms, respectively; U iso = k × U eq (N,C), where k = 1.5 for CH 3 H atoms, and = 1.2 for other H atoms.  The molecular structure of title compound, showing the atom numbering. The displacement ellipsoids are drawn at the 50% probability level. The intramolecular N-H···Cl bond is shown as a dashed line (see Table 1 for details).

Special details
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.