N′-[(E)-Furan-2-ylmethylidene]pyridine-3-carbohydrazide

The title compound, C11H9N3O2, exists in the E conformation with respect to the azomethane C=N bond, and has the keto form. There are two independent molecules in the asymmetric unit and each of these features a slight slanting of the pyridine and furan rings, which form a dihedral angle of 14.96 (10)° in one of the molecules and 5.53 (10)° in the other. The crystal structure is stabilized by N—H⋯O and N—H⋯N hydrogen bonds, weak C—H⋯O and C—H⋯N hydrogen bonds and C—H⋯π interactions and π–π interactions [shortest centroid–centroid distance = 3.7864 (15) Å].

The title compound, (I), crystallizes in triclinic space group P1.There are two independent molecules ( Fig. 1) in the asymmetric unit with almost the same bond length and bond angle, and therefore the detailed description can be limited to one of these molecules. The molecule adopts an E configuration with respect to C7═N3 bond and it exists in the keto form with C6═O1 bond length of 1.226 (2) Å which is very close to a formal C═O bond length [1.21 Å] (Allen et al., 1987). The dihedral angle between pyridine and furan rings is 14.96 (10)°. The O1 and N3 atoms are syn with respect to the C6-N2 bond having a torsion angle of -2.0 (3)°. The molecule is almost planar with maximum deviation of 0.265 (2) Å for atom C2; the other molecule has the maximum deviation of 0.212 (1) Å for the atom O3 from its least-squares plane.

Experimental
The title compound, (I), was prepared by adapting a reported procedure (Fun et al., 2008) by refluxing a mixture of a methanol solutions of furan-2-carboxaldehyde (0.960 g, 10 mmol) and pyridine-3-carbohydrazide (1.370 g, 10 mmol) for 3 h. The formed crystals were collected and recrystallized from a mixture of ethanol and dimethylformamide (1:1 v/v).
Light-green crystals were obtained.

Refinement
All C-bound H atoms were placed in calculated positions with C-H = 0.93 Å, and with U iso =1.2U eq (C). The N-bound H atoms were refined with N-H = 0.88±0.1 Å and free U iso .
supplementary materials sup-2 Figures Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.  (