Date Published: April 01, 2012
Publisher: International Union of Crystallography
Author(s): Marcus V. N. de Souza, Marcelle de Lima Ferreira, Solange M. S. V. Wardell, Edward R. T. Tiekink, James L. Wardell.
In the nearly planar title compound (r.m.s. deviation for the 24 non-H atoms = 0.064 Å), C18H16ClN3O2, the conformation about the N=C bond is E. Supramolecular chains propagated by glide symmetry along  are found in the crystal packing. These are sustained by N—H⋯N hydrogen bonds with the quinoline N atom being the acceptor. The chains are connected into a three-dimensional architecture by π–π interactions involving all three aromatic rings [centroid–centroid distances = 3.5650 (9)–3.6264 (9) Å].
For the biological activity, including anti-tubercular and anti-tumour activity, of compounds containing the quinolinyl nucleus, see: de Souza et al. (2009 ▶); Candea et al. (2009 ▶); Montenegro et al. (2011 ▶, 2012 ▶). For related structures, see: Howie et al. (2010 ▶); de Souza et al. (2010 ▶); de Lima Ferreira et al. (2010 ▶). For the synthesis, see: Montenegro et al. (2012 ▶).