M. Kubicki, H. Bassyouni, P. W. Codding
Jul 12, 2000
Citations
0
Influential Citations
18
Citations
Journal
Journal of Molecular Structure
Abstract
Abstract The crystal structures of three anticonvulsant enaminones: methyl 4-[(p-chlorophenyl)amino]-6-methyl-2-oxo-3-cyclohexen-1-carboxylate (1), methyl 4-[(p–ethylphenyl)amino]-6-methyl-2-oxo-3-cyclohexen-1-carboxylate (2), and methyl 4-[(4′-chloro-2′-pyridinyl)amino]-6-methyl-2-oxo-3-cyclohexen-1-carboxylate (3) have been determined. The cyclohexene rings adopt sofa conformations, with the methyl substituent at the out-of-plane carbon atom in equatorial position. The dihedral angle between the mean planes of cyclohexene and aromatic ring is significantly smaller for pyridinyl derivative as compared with phenyl ones; for the former an intramolecular C–H⋯N(pyridinyl) hydrogen bond closes nearly planar six-membered ring. For all compounds, the intermolecular N–H⋯OC hydrogen bonds form infinite chains of molecules. Both the graph-set notation and resonance-assisted hydrogen bond approach have been used for description of hydrogen bond networks. For 1 and 2, there is a significant disorder of the carbomethoxy groups, caused by a rotation of 180° around the C–C(OOC) single bond.