title: Two isomers of 2,4-dibenzyl-8-azabicyclo[3.2.1]octan-3-ol.
abstract: The crystal structures of the title compounds, 2 alpha,4 alpha-dibenzyl-3 alpha-tropanol (2 alpha,4 alpha-dibenzyl-8-methyl-8-azabicyclo[3.2.1]octan-3 alpha-ol), C(22)H(27)NO, (I), and 2 alpha,4 alpha-dibenzyl-3 beta-tropanol (2 alpha,4 alpha-dibenzyl-8-methyl-8-azabicyclo[3.2.1]octan-3 beta-ol), C(22)H(27)NO, (II), show that both compounds have a piperidine ring in a chair conformation and a pyrrolidine ring in an envelope conformation. Isomer (I) is asymmetric, the benzyl groups having different orientations, whereas isomer (II) is mirror symmetric, and the N and O atoms, the C atom attached to the hydroxy group, and the methyl C atom attached to the N atom lie on the mirror plane. In the crystal structures of both (I) and (II), the molecules are linked together by intermolecular O-H...N hydrogen bonds to form chains that run parallel to the a direction in (I) and parallel to b in (II).
authors.affiliation: Department of Pharmaceutical Sciences, College of Pharmacy, University of Kentucky, Lexington, KY 40536, USA.
authors.forename: Guangrong
authors.initials: G
authors.lastname: Zheng
authors.forename: Sean
authors.initials: S
authors.lastname: Parkin
authors.forename: Linda P
authors.initials: LP
authors.lastname: Dwoskin
authors.forename: Peter A
authors.initials: PA
authors.lastname: Crooks
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D006574:Heterocyclic Compounds, 2-Ring / Q000737:chemistry*; D007536:Isomerism
chemical_list: C487752:2,4-dibenzyl-8-azabicyclo(3.2.1)octan-3-ol; D001372:Aza Compounds; D006574:Heterocyclic Compounds, 2-Ring