title: Crystal and molecular structures of new enantiopure quinuclidines.
abstract: X-ray crystal structure analysis was performed on single crystals of two diastereomeric enantiopure quinuclidines, (3R,8R)-3-vinyl-8-hydroxymethyl-quinuclidine (quincoridine, QCD) and (3R,8S)-3-vinyl-8-hydroxymethyl-quinuclidine (quincorine, QCI) as their salts with tartaric and p-toluenesulphonate anions, respectively. The molecules of these quinuclidine derivatives are considered here as fragments of the Cinchona alkaloids, quinidine and quinine. A comparison of the conformational features of QCD, QCI, and Cinchona alkaloids in the crystalline state shows that the molecular geometry of the title compounds is similar to that of threo-alkaloids (e.g., R,R isomer of epicinchonine) rather than to quinidine and quinine. The packing of the molecules in both structures is dominated by intermolecular hydrogen bonds.
authors.affiliation: Faculty of Chemistry, Jagiellonian University, ul. Ingardena 3, 30-060 Kraków, Poland. ikania@chemia.uj.edu.pl
authors.forename: Iwona
authors.initials: I
authors.lastname: Kania
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Stadnicka
authors.forename: Barbara J
authors.initials: BJ
authors.lastname: Oleksyn