Structure analysis of a reversible monoamine oxidase A inhibitor: 3-{4-[(R)-3-hydroxybutoxy]phenyl}-(R)-5-methoxymethyl-1,3-oxazolidin-2-one

Abstract

The structure of a new reversible type-A MAO inhibitor and analogue of befloxatone is reported. Within experimental deviations, the oxazolidinone moiety of the title compound is planar and quasi coplanar with the adjacent phenyl ring [12.2 (5) o ]. The sum of the angles at the N atom is 359.8 o , indicating sp 2 hybridization of this atom. This is consistent with electron delocalization between the N atom and the carbonyl group [N-(C=O) 1.365 (4) A] in the oxazolidinone ring. The lateral butoxy chain is all trans. As a result, the molecule is very flat with only the (R)-5-methoxymethyl chain and the terminal hydroxyl group out of the plane. The hydroxyl group is involved in the hydrogen bonding responsible for crystal cohesion