Date Published: June 01, 2010
Publisher: International Union of Crystallography
Author(s): Maddela Prabhakar, J. S. N. Reddy, N. Ravi Kumar, S. Viswanadha Ganesh, K. Anand Solomon.
The title compound, C16H14O5, was prepared from the reaction of 3-carbethoxycoumarin with furan in the presence of AlCl3 as catalyst. In the crystal, intermolecular C—H⋯O hydrogen-bonding interactions between four molecules lead to a tetramer in the unit cell. The furan ring is antiperiplanar [C—C—C—O = 167.9 (13)°] and the ethoxycarbonyl group is (−)anticlinal [C—C—C—O = −128.6 (14)°] to the lactone ring.
For the medicinal and biological activity of coumarins and their derivatives, see: Borges et al. (2005 ▶); Kontogiorgis & Hadjipavlou-Litina (2005 ▶); Gursoy & Karali (2003 ▶); Prabhakar et al. (2010 ▶). For the assignment of conformations and the orientation of the substituents, see: Nardelli (1983 ▶, 1995 ▶); Klyne & Prelog (1960 ▶).