Crystal, molecular and electronic structure of (5S,11R,11aS)-11-hydroxy-5-methyl-1,2,3,4,5,6,11,11a-octahydropyrido[1,2-b]isoquinolin-5-ium iodide

Abstract

The title compound, C 14 H 20 INO, is a molecule with three stereogenic centres. It absolute confi guration was derived from the synthesis and confi rmed by structure determination (AD, Flack (Parsons') parameter: 0.031 (8)). The expected stereochemistry of atoms N1 was confi rmed to be S, C5 was confi rmed to S, C6 was confi rmed to R. The central N-heterocyclic ring is not planar and adopts a half-chair conformation. A calculation of least-squares planes showed that these rings are puckered in such a manner that the fi ve atoms: C5, C6, C7, C12 and C13 (the second ring: C1, C2, C3, C4, C5 and N1) are planar, while atom N1 is displaced from these plane with the out-of-plane displacement of -0.694 (4) and -0.670 (5) Å in the second ring, respectively. Dihedral angle between the planes of the central N-heterocyclic rings is 23.4 (2)°. Crystal structure is also stabilized by C-H···O hydrogen interactions.