Synthesis, characterization, crystal structure and theoretical simulation of novel ethyl 2-(7-hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)acetate

Abstract

Abstract Novel coumarin derivative, ethyl 2-(7-hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)acetate has been synthesized by Pechmann condensation reaction and the single crystals of the compound were obtained by slow evaporation technique using ethanol as crystallization solvent. The compound C28H28O10 was spectroscopically characterized using 1H NMR, 13C NMR and IR techniques. Finally single crystal X-ray diffraction studies revealed the molecular structure conformation of the coumarin derivative. The compound crystallized in the orthorhombic crystal system with P212121 space group. The crystal structure of C28H28O10 is stabilized by various intra and inter (O--H...O and C--H...O) intermolecular hydrogen bond interactions. The existence and nature of various intermolecular interactions are quantified by the 3-D molecular Hirshfeld surface and 2-D fingerprint plot analysis. Further, the DFT calculations were performed to optimize structural coordinates and the minima point on the potential energy surface is confirmed by the frequency calculation. The optimized structural parameters showed very good correlation with the single crystal XRD results. Frontier molecular orbitals (HOMO-LUMO), their energy gap and associated reactive parameters were determined to understand the properties of the molecule.