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Hydrogen bonds and C-H...Pi interactions in N-aryl-quinoline-2, 4-diones

The molecular and crystal structures of N-aryl-1, 2, 3, 4-tetrahydro-3, 3-dimethyl-2, 4-quinolinediones, bearing methoxy (1), methyl (2) and chloro (3) substituents in 2'-position of the phenyl ring, have been determined by X-ray crystal structure analysis. Because of restricted rotation about the C(sp2)-N(sp2) bond the ground state of these molecules is non-planar, which gives rise to chirality. The hydrogen bond of C-H...O type joins the molecules of 1 into dimers. The supramolecular structure also contains two C-H...Pi interactions linking the hydrogen-bonded dimers into sheets. In 2, one C-H...Pi interaction generates infinite chains, while two C-H...O hydrogen bonds and three C-H...Pi interactions form three-dimensional framework in the crystal structure of 3.

N-aryl-quinoline-2; 4-diones; atropisomerism; X-ray crystal structure analysis; hydrogen bonds; C-H...Pi interactions

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