Supramolecular structure of S-(+)-marmesin—a linear dihydrofuranocoumarin

Abstract

The title compound, C₁₄H₁₄O₄, a linear dihydrofuranocoumarin, was isolated from the bark ofAegle marmelos, a plant widely used in Ayurvedic system of medicine for the treatment of various ailments. The crystal structure was determined from X-ray diffraction data using direct methods. The compound crystallizes into monoclinic space group P2₁ with unit cell parameters:a] = 5.721(1) Å, b= 13.810(1) Å, c= 7.864(2) Å, β = 100.39(1)°, Z = 2. The structure was refined by full-matrix least-squares to a finalR value of 0.0523 for 1184 observed reflections. The benzopyran moiety is perfectly planar. The dihedral angle between the pyrone and benzene rings is 0.3(1)°. The furan ring has a 2α-envelope conformation. The molecules are linked by O-H…O hydrogen bonds into chains and these chains are linked into sheets by C-H…O hydrogen bonds. Further, the π-π stacking and C-H…π (arene) interactions link all of the sheets into a supramolecular structure.