Research Article: (7aS)-(–)-Dimeth­yl(1-oxido-3-oxo-5,6,7,7a-tetra­hydro-3H-pyrrolizin-2-yl)sulfonium

Date Published: March 01, 2012

Publisher: International Union of Crystallography

Author(s): Leonardo Gutiérrez-Lazcano, Joel L. Terán, Jorge R. Juárez, Marcos Flores-Alamo, Angel Mendoza.


In the zwitterionic title compound, C9H13NO2S, the pyrrolidine heterocycle adopts an envelope conformation (with the C atom in the 7-position as the flap). The negative charge is delocalized over the two carbonyl groups and the C atom connecting them. The positive charge is located on the S atom. Two inter­molecular C—H⋯O inter­actions are observed. The molecular geometry at the S atom is trigonal pyramidal.

Partial Text

For background to the synthesis of chiral non-racemic zwitterionic compounds, see: Zang et al. (2008 ▶); Kappe et al. (1983 ▶); Palillero et al. (2009 ▶). For the biological activity of related structures, see: Basco et al. (1994 ▶); Koruznjak et al. (2003 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).