Research Article: 2-{1-[2,8-Bis(trifluoro­meth­yl)quinolin-4-yl]-3,5,6,7,8,8a-hexa­hydro-1H-1,3-oxazolo[3,4-a]pyridin-3-yl}phenol

Date Published: July 01, 2011

Publisher: International Union of Crystallography

Author(s): Raoni S. B. Gonçalves, Carlos R. Kaiser, Marcus V. N. de Souza, James L. Wardell, Solange M. S. V. Wardell, Edward R. T. Tiekink.


In the title mefloquine–oxazolidine derivative, C24H20F6N2O2, the oxazoline ring adopts an envelope conformation (the flap atom is N) and the piperidine ring has a chair conformation. The oxazoline and benzene residues lie away from the C6 ring of the quinoline group and, to a first approximation, to one side of the plane through the ten atoms (r.m.s. deviation = 0.025 Å). An intra­molecular O—H⋯N(piperidine) hydrogen bond is present. The crystal packing features C—H⋯O, C—H⋯F and C—H⋯π(hy­droxy­benzene) inter­actions.

Partial Text

For background to the anti-mycobacterial activities of quinoline derivatives related to mefloquine, see: Gonçalves et al. (2010 ▶). For additional geometric analysis, see: Cremer & Pople (1975 ▶); Spek (2009 ▶).




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