Quinolin-3-amine

In the crystal structur of the achiral title compound, C9H8N2, N—H⋯N hydrogen bonds connect the molecules into zigzag chains in [100]. Weak intermolecular N–H⋯π interactions further consolidate the crystal packing.

In the crystal structur of the achiral title compound, C 9 H 8 N 2 , N-HÁ Á ÁN hydrogen bonds connect the molecules into zigzag chains in [100]. Weak intermolecular N-HÁ Á Á interactions further consolidate the crystal packing.

Related literature
For novel applications of quinolin-3-amine and its derivatives, see: Rohmer et al. (2010); Kaneshiro et al. (2011). For the crystal structure of a rhodium coordination compound featuring the title compound as a ligand, see: Garralda et al. (1999). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009). AMI is thankful to the Director of the National Institute of Technology for providing research facilities and also thanks the Board for Research in Nuclear Sciences, the Department of Atomic Energy and the Government of India for a Young Scientist award. mass-spectrometry of oligosaccharides (Rohmer et al., 2010) and glycans (Kaneshiro et al., 2011). Herewith we present the crystal structure of 3-aminoquinoline, (I).
In (I) (Fig. 1), the molecule bears an amino group in meta position to the intracyclic nitrogen atom. Intracyclic angles in the six-membered ring containing the nitrogen atom cover a range of 117.42 (12)-125.27 (11) ° with the smallest angle found on the carbon atom bearing the amino group and the biggest angle present on the hydrogen-bearing carbon atom in ortho position to the intracyclic nitrogen atom. The molecule is essentially planar (r.m.s. deviation of of all fitted nonhydrogen atoms = 0.0091 Å). The least-squares planes defined by the non-hydrogen atoms of the heterocycle on the one hand and the atoms of the amino group on the other hand intersect at an angle of 11.97(2.58) °.
In the crystal, N-H···N hydrogen bonds (Table 1) are observed between the amino group and the intracyclic nitrogen atom that connect the molecules to zigzag chains along the crystallographic a axis (Fig. 2). In terms of graph-set analysis (Etter et al., 1990;Bernstein et al., 1995), the descriptor for these contacts is C 1 1 (5) on the unary level. In addition, a N-H···π interaction (Table 1) involving the non-heterocyclic moiety of the quinoline core as acceptor contribute to the crystal packing stability.
The batch was hydrogenated at a pressure of 10 bar for 12 h. Subsequently, the reaction mixture was filtered and concentrated under reduced pressure to afford the title compound as a pale yellow solid. The solid was dissolved in absolute ethanol and allowed to stand and evaporate at room temperature overnight. The crystalline solid that developed was filtered and dried under high vacuum (yield: 0.8 g, 97.5%).

Refinement
C-bound H atoms were placed in calculated positions (C-H 0.95 Å) and were included in the refinement in the riding model approximation, with U iso (H) set to 1.2U eq (C). Both amino H atoms were located on a difference Fourier map and refined freely. In the absence of strong anomalous scatterers, 737 Friedel pairs were merged before the final refinement.