7-Phenyl-1-oxa-4-thiaspiro[4.5]decan-7-ol stereoisomers

Abstract

The stereoisomers of 7-phenyl-1-oxa-4-thiaspiro[4.5]decan-7-ol, C₁₄H₁₈O₂S, have the same stereochemistry at the C atom bearing an OH group, i.e. axial OH and equatorial phenyl groups. However, the acetal S and O atoms are axial and equatorial, respectively, in one isomer and reversed in the second. Furthermore, the crystals of one isomer are composed of hydrogen-bonded molecules involving the hydroxyl H atom and the O atom of the five-membered heterocyclic ring, with an O...O distance of 2.962 (3) Å, forming a polymeric chain along the b axis. The asymmetric unit of the other isomer is composed of two molecules, wherein hydroxyl H atoms and the O atoms of the five-membered heterocyclic rings display intramolecular O-H...O hydrogen bonds with O...O separations of 2.820 (2) and 2.834 (2) Å.