Crystal, spectral characterization, molecular docking, Hirshfeld computational studies and 3D-energy framework analysis of a novel puckered compound (C14H15Cl O): 2-Chloro-3-phenyl-5,5-dimethylcyclohex-2-en-1-one

• Published in: Journal of molecular structure 2020-06, Vol.1210, p.127979, Article 127979
• Main Authors: Sreenatha, N.R., Jeevan Chakravarthy, A.S., Suchithra, B., Lakshminarayana, B.N., Hariprasad, S., Ganesha, D.P.
• Format: Article
• Language: English
• Subjects: 3D-interaction energies; Hirshfeld surfaces; Molecular docking; Puckering parameters; XRD & spectral analysis
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2020.127979

A novel compound, 2-chloro-3-phenyl-5,5-dimethylcyclohex-2-en-1-one, was synthesized and characterized by FT-IR, GC-Mass spectroscopy and NMR techniques. The single crystal XRD data of the compound, obtained by slow evaporation technique, revealed that the compound crystallized in a monoclinic lattice system, with the space group P21/n. Its asymmetric unit comprises of two molecules A and B, both adopting a non-planar structure. The Cg1A and Cg1B rings are puckered and adopt nearly envelope E1 and E1 conformations in A and B, respectively. The anionic and cationic entities in the crystal are interconnected by very weak intermolecular C–H⋯O interactions. The three dimensional Hirshfeld surfaces and associated two dimensional fingerprint plots have been performed to gain insight into these interactions. The interaction energies play a major role in the supramolecular architecture of molecular units in a crystal. These were calculated and analyzed using the energy density wave function of B3LYP/6-31G(d,p), which revealed the domination of dispersion energies over classical electrostatic energy frameworks. In addition, molecular docking studies were performed over several proteins out of which good binding results were observed for secreted aspartic protease from Candida albicans and nicotinic acetyl choline receptor. [Display omitted] •The novel compound was synthesized and characterized by FT-IR, GC-Mass, H1 and C13 NMR.•The single crystal XRD of 2-chloro-3-phenyl-5,5-dimethylcyclohex-2-en-1-one was studied and analyzed.•Molecular docking studies of the molecule was performed on different proteins, to screen its properties.•Analysis of intermolecular interactions by Hirshfeld surfaces and its related 2D fingerprint plots are reported.•Interaction energies between the molecular pairs was studied and analyzed.