Abstract
In the title compound, C16H9FO4, (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 intra-molecular C-H⋯O hydrogen bond, which closes a five-membering ring. In the crystal, mol-ecules 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 inter-actions 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 inter-actions [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 qu-antify the supra-molecular inter-actions.
Highlights
C16H9FO4, (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 A )
The theoretical data for (I) obtained from quantum chemical calculations are in good agreement with the observed structure, 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)]
In view of their importance and as a continuation of our work on the crystal structure analysis of coumarin derivatives (Abou et al, 2013; Ouedraogo et al, 2018), we report the synthesis, crystal structure, geometry optimization and Hirshfeld surface analysis of the title coumarin derivative (I)
Summary
Coumarins and their derivatives constitute one of the major classes of naturally occurring compounds and interest in their chemistry continues unabated because of their usefulness as biologically active agents. They form the core of several molecules of pharmaceutical importance. Coumarin and its derivatives have been reported to serve as anti-bacterial (Basanagouda et al, 2009), anti-oxidant (Vukovicet al., 2010) and anti-inflammatory agents (Emmanuel-Giota et al, 2001). In view of their importance and as a continuation of our work on the crystal structure analysis of coumarin derivatives (Abou et al, 2013; Ouedraogo et al, 2018), we report the synthesis, crystal structure, geometry optimization and Hirshfeld surface analysis of the title coumarin derivative (I)
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