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The crystal structures of three isomeric 4-[3-(dichlorophenyl)-hexahydro[1,3]oxazolo[3,4-a]pyridin-1-yl]-2,8-bis(trifluoromethyl)quinolines, ( 5 : X 2  = 2,3-, 2,4- and 2,5-Cl 2 ) have been determined and have been compared to those of related compounds. The crystallographic asymmetric unit of each of ( 5 : X 2  = 2,4-Cl 2 ) and ( 5 : X 2  = 3,4-Cl 2 ) consists of a single molecule, while that of ( 5 : X 2  = 2,3-Cl 2 ) contains two independent molecules – Molecule A and Molecule B. Each of the three compounds crystallizes in the triclinic space group,  P 1̅. The supramoleular arrangements of the three compounds are generated from combinations of some of C–H⋯X (X = F, Cl, and O), C–X⋯π (X = H, F and Cl) and π⋯π interactions. The presence and significance of two centrosymmetric structural dimeric motives – cage-type dimers, formed (i) from the intermeshing of “F”-shaped monomers, and (ii) π(quinoline)⋯π(quinoline) interactions, reported to arise frequently in other 4-[3-aryl-hexahydro[1,3]oxazolo[3,4-a]pyridin-1-yl]-2,8-bis(trifluoromethyl)quinolone compounds, were investigated. Both ( 5 : X 2  = 2,4-Cl 2 ) and ( 5 : X 2  = 3,4-Cl 2 ) exhibit cage-type dimers. In the cases of molecule B of ( 5 : X 2  = 2,3-Cl 2 ) and ( 5 : X 2  = 3,4-Cl 2 ), the π(quinoline)⋯π(quinoline) interactions are strong, but are much weaker in molecule A of ( 5 : X 2  = 2,3-Cl 2 ) and ( 5 : X 2  = 2,4-Cl 2 ).

zeitschrift für kristallographie - crystalline materials

Crystal structures of three isomeric 4-[3-(dichlorophenyl)-hexahydro[1,3]oxazolo[3,4-a]pyridin-1-yl]-2,8-bis(trifluoromethyl)quinolines: importance of cage-type and π(quinoline)⋯π(quinoline) dimeric motifs