Crystal structure of (–)-(R,E)-3-(1,3-benzodioxol-5-yl)-5-[(4S,5R)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-N,N-dimethylpent-4-enamide

Abstract

In the title compound, C20H27NO6, the amide moiety is essentially planar, with a maximum deviation of 0.073 (3) Å, and one of the N-methyl groups shows rotational disorder. The five-membered 1,3-dioxolane ring adopts an envelope form, with the C atom bonded to the olefin side chain as the flap, which deviates from the mean plane through the other four atoms by 0.564 (7) Å. The 1,3-dioxole ring fused to the benzene ring adopts a flattened envelope form, with the C atom between the two O atoms as the flap, which deviates from the mean plane through the other four atoms by 0.215 (7) Å. The C—C=C—C olefin moiety is essentially planar and makes a dihedral angle of 87.1 (3)° with the benzene ring. An intramolecular O—H...O hydrogen bond supports the molecular conformation, enclosing an S(11) graph-set motif. In the crystal, intermolecular C—H...O hydrogen bonding links the molecules into a tape running along the b axis. Furthermore, other weak C—H...O hydrogen bonds and a C—H...π interaction connect the tapes into a sheet structure parallel to (100).