Crystal structure and Hirshfeld surface analysis of (E)-2-(2,4,6-trimethylbenzylidene)-3,4-dihydronaphthalen-1(2H)-one

Abstract

A novel chalcone, C20H20O, derived from benzylidenetetralone, was synthesized via Claissen-Schmidt condensation between tetralone and 2,4,6-trimethyl-benzaldehyde. In the crystal, molecules are linked by C-H center dot center dot center dot O hydrogen bonds, producing R-2(2)(20) and R-2(4)(12) ring motifs. In addition, weak C-H center dot center dot center dot pi and pi-stacking interactions are observed. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most important contributions for the crystal packing are from H center dot center dot center dot H (66.0%), H center dot center dot center dot C/C center dot center dot center dot H (22.3%), H center dot center dot center dot O/O center dot center dot center dot H (9.3%), and C center dot center dot center dot C (2.4%) interactions. Shape-index plots show pi-pi stacking interactions and the curvedness plots show flat surface patches characteristic of planar stacking.