Crystal structure of bergapten: A photomutagenic and photobiologically active furanocoumarin

Abstract

The title compound, C12H8O4, is a furanocoumarin [systematic name: 4-methoxy-7H-furo[3,2-g]chromen-7-one], which was isolated from the Indian herb T. stictocarpum. The molecule is almost planar with an r.m.s. deviation of 0.024Å for the hetero atoms of the fused-ring system. In the crystal, molecules are linked by C - H···O hydrogen bonds, forming a three-dimensional framework. There are offset π-π interactions present involving the coumarin moieties stacking along the a-axis direction [shortest inter-centroid distance = 3.717(3)Å].