Crystal structure of a photobiologically active furanocoumarin fromArtemisia reticulata

Abstract

The title furanocoumarin, C14H12O4[systematic name: 9-hydroxy-2-(prop-1-en-2-yl)-2,3-dihydro-7H-furo[3,2-g]chromen-7-one], crystallizes with two independent molecules (AandB) in the asymmetric unit. The two molecules differ essentially in the orientation of the propenyl group with respect to the mean plane of the furanocoumarin moiety; the O—C(H)—C=C torsion angle is 122.2 (7)° in moleculeAand −10.8 (11)° in moleculeB. In the crystal, theAandBmolecules are linkedviaO—H...O hydrogen bonds, forming zigzag –A–B–A–B– chains propagating along [001]. The chains are reinforced by bifurcated C—H...(O,O) hydrogen bonds, forming ribbons which are linkedviaC—H...π and π–π interactions [intercentroid distance = 3.602 (2) Å], forming a three-dimensional structure.