title: Crystalline structure of N-(S)-2-heptyl (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanecarboxamide that differs from its preferred conformation in the solvent used for crystallization.
abstract: The crystalline structure of N-(S)-2-heptyl (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexamide (1), which was crystallized from methanol, was determined by an X-ray analysis and had a different conformation from its preferred one in CD3OD by a 1H-NMR analysis. Inter- and intra-molecular CH-pi interaction in a crystal plays a very important role in crystal packing. The preferred conformation of the amide derivative in a solution allows us to exploit (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexanecarbonyl chloride as a conversion reagent to determine the absolute configuration of chiral amines by 1H-NMR.
authors.affiliation: Graduate School of Life Sciences, Tohoku University, Aobaku, Sendai, Japan. akasaka@biochem.tohoku.ac.jp
authors.forename: Kazuaki
authors.initials: K
authors.lastname: Akasaka
authors.forename: Takashi
authors.initials: T
authors.lastname: Ohtaki
authors.forename: Chizuko
authors.initials: C
authors.lastname: Kabuto
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kitahara
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Ohrui
mesh_terms: D000577:Amides / Q000737:chemistry*; D000873:Anthracenes / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D012996:Solutions; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000873:Anthracenes; D007202:Indicators and Reagents; C507158:N-(S)-2-heptyl (1R,2R)-2-(2,3-anthracenedicarboximido)cyclohexamide; D012996:Solutions