(E, E)-3-Methyl-2,5-bis-(4-methyl-benzyl-idene)cyclo-penta-none: synthesis, characterization, Hirshfeld surface analysis and anti-bacterial activity

Acta Crystallogr E Crystallogr Commun. 2019 Mar 26;75(Pt 4):506-511. doi: 10.1107/S2056989019003827. eCollection 2019 Apr 1.

Abstract

The title compound, (E,E)-3-methyl-2,5-bis-(4-methyl-benzyl-idene)cyclo-penta-none (MBMCP), C22H22O, was obtained by Claisen-Schmidt condensation of 4-methyl-benzaldehyde with 3-methyl-cyclo-penta-none in good yield. The structure of MBMCP was studied using UV, FT-IR and Raman spectroscopy, single-crystal X-ray diffraction (XRD) measurements, and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy. The mol-ecular structure of MBMCP is fully extended in the E,E configuration. C-H⋯π stacking inter-actions play a significant role in the stabilization of the mol-ecular packing. Hirshfeld surface analysis was used to qu-antify the non-covalent inter-actions in the crystal lattice. Microbiological studies were performed to investigate the anti-microbial activity of this new product.

Keywords: Claisen–Schmidt reaction; crossed-aldol condensation; crystal structure; spectroscopic studies.

Grants and funding

This work was funded by Ministère de l’Enseignement Supérieur et de la Recherche Scientifique grant .