(2-Oxido-1-naphthaldehyde benzoylhydrazonato-κ3 N,N′,O)pyridinecopper(II)

In the mononuclear title compound, [CuII(C18H12N2O2)(C5H5N)], the CuII ion is coordinated by two O atoms and one N atom from the dianionic tridentate L 2− ligand (H2 L is 2-hydroxy-1-naphthaldehyde benzoylhydrazide) and one N atom from a pyridine molecule in a CuN2O2 distorted square-planar coordination environment.

In the mononuclear title compound, [Cu II (C 18 H 12 N 2 O 2 )-(C 5 H 5 N)], the Cu II ion is coordinated by two O atoms and one N atom from the dianionic tridentate L 2À ligand (H 2 L is 2hydroxy-1-naphthaldehyde benzoylhydrazide) and one N atom from a pyridine molecule in a CuN 2 O 2 distorted square-planar coordination environment.

Experimental
Crystal data [Cu(C 18 Table 1 Selected geometric parameters (Å , ).  (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010). Table 1. The Cu II ion is coordinated by two O atoms and one N atom from the dianionic tridentate ligand L 2ligand (H 2 L is 2-hydroxy-1-naphthaldehyde benzoylhydrazide), and one N atom from a pyridine molecule. The Cu II ion adopts a CuN 2 O 2 distorted square-planar coordination environment. The Cu-O and Cu-N bond distances are similar to the corresponding bond distances observed in related compounds (Ali et al., 2004;Xu et al., 2006;Sun et al., 2011). There is no significant deviation of the metal centre from the N 2 O 2 equatorial plane. The maximum displacements from the least-squares plane through N1, N3, O1, and O2 (rms deviation = 0.0895 Å) are 0.096

Selected bond lengths and angles are given in
(1) and -0.094 (1) Å for atoms N1 and O2; Cu1 is -0.013 (1) Å below the mean plane. The coordinated pyridine molecule is almost coplanar with the previous N 2 O 2 plane, the dihedral angle between the mean planes is 7.2 (1)°.

Experimental
The 2-hydroxy-1-naphthaldehyde benzoylhydrazide ligand (H 2 L) was prepared in a similar manner to the reported procedures (Qiao et al., 2010). The title compound was synthesized by adding pyridine (0.2 mL) to a solution of H 2 L (0.1 mmol) and Cu(OAc) 2 (0.1 mmol) in methanol/dichloromethane (1:1, 20 mL), and the resulting mixture was stirred for about 6 h to afford a green solution. A week later, brown crystals of the title compound were isolated from the solution.

Refinement
All H atoms were placed in calculated positions and refined using a riding model [C-H = 0.95 Å and U iso (H) = 1.5U eq (C)].
supplementary materials sup-2 Figures Fig. 1. A view of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq