(E)-4-{2-[(2-Hydroxynaphthalen-1-yl)methylidene]hydrazinecarbonyl}pyridinium nitrate

The title compound, C17H14N3O2 +·NO3 −, is an aroylhydrazone-based material consisting of a 4-(hydrazinecarbonyl)pyridinium cation and a nitrate anion. In the cation, the dihedral angle between the benzene ring and the naphthalene ring system is 2.20 (7)°. In the cation, the configuration about the C=N bond is E. There is an intramolecular O—H⋯N hydrogen bond in the cation, and the supramolecular structure is stabilized by intermolecular N—H⋯O hydrogen bonds and weak C—H⋯O contacts between the cation and the nitrate anion.

The title compound, C 17 H 14 N 3 O 2 + ÁNO 3 À , is an aroylhydrazone-based material consisting of a 4-(hydrazinecarbonyl)pyridinium cation and a nitrate anion. In the cation, the dihedral angle between the benzene ring and the naphthalene ring system is 2.20 (7) . In the cation, the configuration about the C N bond is E. There is an intramolecular O-HÁ Á ÁN hydrogen bond in the cation, and the supramolecular structure is stabilized by intermolecular N-HÁ Á ÁO hydrogen bonds and weak C-HÁ Á ÁO contacts between the cation and the nitrate anion.

D-HÁ
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).  As part of our studies on the synthesis and characterization of hydrazone derivatives, we report here the crystal structure of (E)-4-(2-((2-hydroxynaphthalen-1-yl)methylene)hydrazinecarbonyl)pyridinium nitrate. The asymmetric unit of C 17 H 14 N 4 O 5 , consists of a (E)-4-(2-((2-hydroxynaphthalen-1-yl)methylene)hydrazinecarbonyl)pyridinium cation and a nitrate anion (Fig. 1). The dihedral angle between the mean planes of the benzene and naphthalene rings is 2.20 (7)°. The cation displays a trans configuration with respect to the C=N and N-N bonds. It is to note that the overall structure of the cation is very similar to that found for free ligand Richardson & Bernhardt (1999). The packing diagram of the title compound is shown in Fig. 2. There is a strong intramolecular O-H···N hydrogen bond in which the N of the azomethine group (-C=N-) acts as hydrogen acceptor for the hydrogen O-H group attached to the naphthalene ring. Two intermolecular N-H···O hydrogen bonds are formed between cation and anion where NO 3 acts as hydrogen bonds acceptor (Fig. 3). The supramolecular structure is further stabilised by C-H···O interactions.

Experimental
All reagents were commercially available and used as received. A methanol (10 ml) solution of 2-hydroxy-1-naphthaldehyde (1.63 mmol) was dropwise added to a methanol solution (10 ml) of 4-pyridine carboxylic acid hydrazide (1.63 mmol), and the mixture was refluxed for 3 hrs. Then the solution was evaporated on a steam bath to 5 ml and cooled to room temperature.
The resultant yellow precipitate was separated and filtered off, washed with 5 ml of cooled methanol and then dried in air.
1 mmol of this solid was placed in one arm of a branched tube with 2 mmol of Mn(NO 3 ) 2 .4H 2 O. Methanol was carefully added to fill the arms, the tube was sealed and the arm containing the reagents was immersed in an oil bath at 60 °C while the other arm was kept at ambient temperature. After 4 days, crystals were deposited in the cooler arm, which were filtered Figures Fig. 1. The molecular structure of the title compound with labelling scheme and anisotropic displacement ellipsoids (drawn at 30% probability level for non-H atoms).