Crystal structure of N-[2-(cyclohexylsulfanyl)ethyl]quinolinic acid imide

Abstract

The title compound, C15H18N2O2S {systematic name: 6-[2-(cyclohexylsulfanyl)ethyl]-5H-pyrrolo[3,4-b] pyridine-5,7(6H)-dione}, was obtained from the reaction of pyridine-2,3-dicarboxylic anhydride (synonym: quinolinic anhydride) with 2-(cyclohexylsulfanyl) ethylamine. The dihedral angle between the mean plane of the cyclohexyl ring and the quinolinic acid imide ring is 25.43 (11)degrees. In the crystal, each molecule forms two C-H center dot center dot center dot O hydrogen bonds and one weak C-O center dot center dot center dot pi[O center dot center dot center dot ring centroid = 3.255 (2) angstrom] interaction with neighbouring molecules to generate a ladder structure along the b-axis direction. The ladders are linked by weak C-O center dot center dot center dot pi[O center dot center dot center dot ring centroid = 3.330 (2) angstrom] interactions, resulting in sheets extending parallel to the ab plane. The molecular structure is broadly consistent with theoretical calculations performed by density functional theory (DFT).