Exoconformers ofN-(pyridin-2-yl)- andN-(pyridin-3-yl)norbornene-5,6-dicarboximide crystals

Abstract

Two isomeric pyridine-substituted norbornenedicarboximide derivatives, namelyN-(pyridin-2-yl)-exo-norbornene-5,6-dicarboximide, (I), andN-(pyridin-3-yl)-exo-norbornene-5,6-dicarboximide, (II), both C14H12N2O4, have been crystallized and their structures unequivocally determined by single-crystal X-ray diffraction. The molecules consist of norbornene moieties fused to a dicarboximide ring substituted at the N atom by either pyridin-2-yl or pyridin-3-yl in ananticonfiguration with respect to the double bond, thus affordingexoisomers. In both compounds, the asymmetric unit consists of two independent molecules (Z′ = 2). In compound (I), the pyridine rings of the two independent molecules adopt different conformations,i.e. synandanti, with respect to the methylene bridge. The intermolecular contacts of (I) are dominated by C—H...O interactions. In contrast, in compound (II), the pyridine rings of both molecules have ananticonformation and the two independent molecules are linked by carbonyl–carbonyl interactions, as well as by C—H...O and C—H...N contacts.