2-Hydrazinylquinoline

In the title compound, C9H9N3, the 12 non-H atoms are essentially planar (r.m.s. deviation = 0.068 Å). The maximum deviation from planarity is reflected in the torsion angle between the β-N atom of the hydrazinyl residue and the quinolinyl N atom [N—N—C—N = −12.7 (3)°]; these atoms are syn. In the crystal, supramolecular layers in the bc plane are formed via N—H⋯N hydrogen bonds.

In the title compound, C 9 H 9 N 3 , the 12 non-H atoms are essentially planar (r.m.s. deviation = 0.068 Å ). The maximum deviation from planarity is reflected in the torsion angle between the -N atom of the hydrazinyl residue and the quinolinyl N atom [N-N-C-N = À12.7 (3) ]; these atoms are syn. In the crystal, supramolecular layers in the bc plane are formed via N-HÁ Á ÁN hydrogen bonds.

Related literature
For applications of coordination complexes of hydrazones as organic light emitting diodes and supramolecular magnetic clusters, see: Zhang et al. (2011);Petukhov et al. (2009). For background to the synthesis of hydrazones, see: Gupta et al. (2007); Anwar et al. (2011). For a related structure, see: Najib et al. (2012).

Comment
Hydrazones are versatile nitrogen donor ligands which have been used extensively for making coordination complexes for a variety of applications from organic light emitting diode (OLED) materials (Zhang et al., 2011) to supramolecular magnetic clusters (Petukhov et al., 2009). These ligands are made by condensation of a carbonyl compound with an organic hydrazine or hydrazide (Anwar et al., 2011). We have previously reported the solid-state structure of the zinc(II) complex of 3,5-dimethyl-1-(2′-quinolyl)pyrazole (Najib et al., 2012). The ligand in that complex was made by the condensation of acetylacetone with the title compound (Gupta et al., 2007). Herein, the crystal and molecular structure of the title compound is described.
In the crystal, molecules assemble into supramolecular layers in the bc plane via N-H···N hydrogen bonds, Fig. 2 and Table 1. The secondary amine-H hydrogen bonds to the primary amine-N2 atom. One of the primary amine-H atoms forms a hydrogen bond with the quinolinyl-N atom and the other forms a weak interaction with the secondary amine-N2 atom. The layers stack along the a axis with no specific interactions between them, Fig. 3.

Experimental
The title compound was prepared by modification of a literature procedure (Gupta et al., 2007). 2-Chloroquinoline (10.06 g) and hydrazine monohydrate (64-65% N 2 H 4 ) in water (10 ml) were refluxed for 2 h. The water was removed using a rotary evaporator to provide a scarlet residue which was triturated with water and filtered. This scarlet solid was recrystallized from CH 2 Cl 2 and hexane to provide 6.48 g (66.6%) of the title compound [M.p. = 417 K]. Spectroscopic data for the title compound are given in the archived CIF.

Refinement
C-bound H-atoms were placed in calculated positions [C-H = 0.95 Å, U iso (H) = 1.2U eq (C)] and were included in the refinement in the riding model approximation. The N-bound H-atoms were located in a difference Fourier map and refined freely.

Figure 2
A view of the supramolecular layer in the bc plane in the crystal of the title compound. The N-H···N hydrogen bonds are shown as blue dashed lines (see Table 1 for details).   Table 1 for details).