CRYSTAL STRUCTURE, HIRSHFELD SURFACE ANALYSIS AND ENERGY FRAMEWORK CALCULATION OF A CHIRAL ISOBENZOFURANONE 3-[2(4-METHYLPHENYL)-2-OXOETHYL]ISOBENZOFURAN-1(3H)-ONE

The title molecule, 3-[2(4-methylphenyl)-2-oxoethyl]isobenzofuran-1(3H)-one, was prepared via ZrOCl28H2O catalyzed condensation reactions between phthalaldehydic acid and 4-methylacetophenone. The X-ray crystallographic method was used to determine the crystal structure and features of the molecular structure of compound 1. The compound crystallizes in the centrosymmetric space group, where the C3 atom of the isobenzofuranone is an asymmetric carbon and the refined molecule of compound has an R configuration. The crystal packing shows two dimers that generate R_2^2(10) and R_2^2(16) ring motifs. Hirshfeld surface was used to explore the intermolecular interactions in the crystal structure and analysed dnorm, shape index, curvedness, electrostatic potential. 2D fingerprint plots were carried out to discuss the role of the intramolecular and intermolecular contacts in crystal lattice. This analysis revealed that supramolecular structure of compound is stabilized mainly by H···H, C···H/H···C and O···H/H···O interactions with the largest portion of total Hirshfeld surface belongs to non-classical H···H contacts. However, the C···H interaction between the H atoms and the π-system of isobenzofuranone and phenyl rings show very high values whereas that π···π interactions there are no significant within the crystals. The analysis of the energy framework was performed to explore the energies of intermolecular interaction between neighboring molecules, providing a potentially useful tool for a full understanding of the intermolecular interactions in isobenzofuranone derivatives.