Crystal structure determination, hirshfeld surface analysis and quantum computational studies of (3E,5E)-1-ethyl-3,5-bis (naphthalen-1-yl-methylidene) piperidin-4-one: A novel RORc inhibitor

Abstract

The title compound (3E,5E)-1-ethyl-3,5-bis (naphthalen-1-yl-methylidene) piperidin-4-one (C29H25NO), belongs to a class of polysubstituted piperidones with the olefinic double bonds being in an E configuration. It crystallizes in the monoclinic space group with one molecule in the asymmetric unit. The crystal packing in the α, β-unsaturated ketone is a consequence of dominant intra and intermolecular C—H···O interactions. The crystal structure is further stabilized by four C—H···π interactions. Hirshfeld surface analysis was carried out to quantify the interactions and an interaction energy analysis was done to study the interactions between pairs of molecules. The optimized structure calculated was calculated using density functional theory at the B3LYP/ 6–31G(d,p) level and was compared with the experimentally determined solid state structure. Molecular docking studies was carried out in silico to investigate the biological activity of the title compound with the human RORc protein (PDB ID: 4WLB).