Crystal structure of 2-oxo-2 H -chromen-7-yl 4-fluorobenzoate

Abstract

In the title compound, C16 H9 FO4, (I), the benzene ring is oriented at an acute angle of 59.03 (15)°relative to the coumarin plane (r.m.s deviation = 0.009 Å). This conformation of (I) is stabilized by an intramolecular C - H...O hydrogen bond, which closes a five-membering ring. In the crystal, molecules of (I) form infinite zigzag chains along the b-axis direction, linked by C - H...O hydrogen bonds. Furthermore, the crystal structure is supported by π-π stacking interactions between neighbouring pyrone and benzene or coumarin rings [centroid-centroid distances in the range 3.5758 (18)-3.6115 (16) Å], as well as C=O...π interactions [O...centroid distances in the range 3.266 (3)-3.567 (3) Å]. The theoretical data for (I) obtained from quantum chemical calculations are in good agreement with the observed structure, although the calculated C - O - C - C torsion angle between the coumarin fragment and the benzene ring (73.7°) is somewhat larger than the experimental value [63.4 (4)°]. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions.