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Structures of 4-{3-(X-phenyl)perhydro-1,3-oxazolo[3,4-a]pyridin-1-yl}-2,8-bis(trifluoromethyl)quinolines (X = H, 2-O N, 3-O N and 4-O N), derived from mefloquine

Authors: Gonçalves, R.S.B.; Kaiser, C.R.; De Souza, M.V.N.; Wardell, J.L.; Wardell, S.M.S.V.; Howie, R.A.


Abstract

The crystal structures of four 4-{3-(X-phenyl)perhydro-1,3-oxazolo[3,4-a]pyridin-1-yl}-2,8-bis(trifluoro-methyl)quinolines, (2: X = H, 2-O2N, 3-O2N and 4-O2N) are reported. Differences in the conformations of the molecules are illustrated by the angles between the best planes through the various ring moieties. There are no strong intermolecular interactions, such as O—H···O, present in any of the four compounds. Instead, present in each of the four compounds are different combinations of some of C—H···F, C—H···O(nitro), C—H···π, C—F···π, N—O···π and π···π-stacking interactions, which result in very different supramolecular arrangements.
Keywords: Mefloquine derivatives; Hydrogen bonding; Intermolecular interactions; Single crystal structure analysis; X-ray diffraction Document Type: Research Article DOI: http://dx.doi.org/10.1524/zkri.2011.1426 Publication date: 9 de Agosto de 2011

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