Abstract
In the title compound, C20H18O4, the benzoate ring is oriented at an acute angle of 33.10 (12)° with respect to the planar (r.m.s deviation = 0.016 Å) coumarin ring system. An intra-molecular C-H⋯O hydrogen bond closes an S(6) ring motif. In the crystal, C-H⋯O contacts generate infinite C(6) chains along the b-axis direction. Also present are π-π stacking inter-actions between neighbouring pyrone and benzene rings [centroid-centroid distance = 3.7034 (18) Å] and C=O⋯π inter-actions [O⋯centroid = 3.760 (3) Å]. The data obtained from quantum chemical calculations performed on the title compound are in good agreement with the observed structure, although the calculated C-O-C-C torsion angle between the coumarin ring system and the benzoate ring (129.1°) is somewhat lower than the observed value [141.3 (3)°]. Hirshfeld surface analysis has been used to confirm and qu-antify the supra-molecular inter-actions.
Highlights
C20H18O4, the benzoate ring is oriented at an acute angle of 33.10 (12) with respect to the planar (r.m.s deviation = 0.016 A ) coumarin ring system
The data obtained from quantum chemical calculations performed on the title compound are in good agreement with the observed structure, the calculated C—O—C—C torsion angle between the coumarin ring system and the benzoate ring (129.1) is somewhat lower than the observed value [141.3 (3)]
In view of their importance and as a continuation of our work on the crystal structure analysis of coumarin derivatives (Abou et al, 2012, 2013), 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 (Vukovic et 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, 2012, 2013), we report the synthesis, crystal structure, geometry optimization and Hirshfeld surface analysis of the title coumarin derivative, (I)
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