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

• Main Authors: Hyunjin Park, Myong Yong Choi, Cheol Joo Moon, Tae Ho Kim
• Format: Article
• Language: English
• Published: International Union of Crystallography 2017-09-01
• Series: Acta Crystallographica Section E: Crystallographic Communications
• Subjects: crystal structure; theoretical calculations; quinolinic acid imide; hydrogen bonding
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S2056989017012142

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)°. In the crystal, each molecule forms two C—H...O hydrogen bonds and one weak C—O...π [O...ring centroid = 3.255 (2) Å] interaction with neighbouring molecules to generate a ladder structure along the b-axis direction. The ladders are linked by weak C—O...π [O...ring centroid = 3.330 (2) Å] 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).