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Crystal and Molecular Structures of Atropisomeric N-aryl-1, 2, 3, 4-tetrahydro-3, 3-dimethyl-2, 4-quinolinediones

The 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. The heterocyclic ring in 1-3 adopts an envelope conformation, with the smallest ring puckering in the ortho-chloro derivative 3. The N-aryl ring is almost perpendicular with respect to the quinoline-2, 4-dione ring. The corresponding dihedral angle values are 83.2(1), 80.0(9) and 83.4(2)º in 1, 2 and 3, respectively. The hydrogen bond of C H• • • O type joins the molecules of the ortho-methoxy derivative 1 into dimers. The supramolecular structure also contains two C H• • •  interactions that link the hydrogen-bonded dimers into sheets. In ortho-methyl derivative 2, one C H• • •  interaction generates infinite chains, while two C H• • • O hydrogen bonds and three C H• • •  interactions in the ortho-chloro derivative 3 form three-dimensional framework.

crystal and molecular structures; quinolinediones

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