Abstract
The title compound, (I), has been solved by direct methods and refined to a final R value of 0.038 for 1835 independent reflections. In the structure, the planar [r.m.s deviation = 0.014 Å] chromen-2-one ring and the 7-propionate side chain are inclined to one another at an acute angle of 65.34(9)°. The molecules form R<sub>4</sub><sup>4</sup> (30) tetrameric units via C—H···O interactions which extend into layers approximately parallel to the <i>ab</i> plane. Furthermore, the crystal structure is supported by π–π stacking interactions between neighbouring benzene and pyrone or coumarin rings [centroid–centroid distances in the range 3.6097(8)–3.6475(9)Å], as well as C–H···π interactions [H···centroid distances in the range 2.95–3.00Å]. The molecular geometry of (I) was also optimized using density functional theory (DFT/RB3LYP), RMP2 and RHF methods with the 6-311<sup>++</sup>G(<i>d</i>, <i>p</i>) basis set in ground state. The theoretical data resulting from these quantum chemical calculations are in good agreement with the observed structure, although the observed C—O—C—C torsion angle between the coumarin ring system and the 7-propionate side chain (121.49 (16)°) is somewhat lower than the DFT/RB3LYP calculated value (132.32°) and larger than the RMP2 (114.65°) and the RHF (69.19°) values. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions.
Highlights
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
As expected in organic compounds, the H...H contacts are important with a 35.3% contribution to Hirshfeld surface; these appear in the central region of the fingerprint plots (FP) with a central blue tip spike at de = di = 1.30 Å Figure 8c whereas the C...H/H...C plot (15.9%) reveals information on the intermolecular hydrogen bonds Figure 8d
To predict reactive sites for electrophilic and nucleophilic attack for the title molecule, Molecular Electrostatic Potential (MEP) was computed at the density functional theory (DFT)/RB3LYP, RMP2 and restricted Hartree-Fock (RHF) optimized geometries using the 6-311++G(d,p) basis set
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 [1], anti-oxidant [2] and anti-inflammatory agents [3]
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