Structural, Hirshfeld, spectroscopic, quantum chemical and molecular docking studies of N'-(4-(4-Chlorophenyl)-1,3-dicyano-5,6,7,8,9,10-hexahydrobenzo[8]annulen 2-yl) N,N-dimethylformimidamide as CCR2 inhibitors

Abstract

In the present study, a novel N'-(4-(4-Chlorophenyl)-1,3-dicyano-5,6,7,8,9,10-hexahydrobenzo[8]annulen2-yl)- N,N-dimethylformimidamide (CBAD) crystal was grown by the slow evaporation method. The single crystal X-ray diffraction analysis and density functional theory (DFT) calculations were carried out for the CBAD crystal. The CBAD crystallizes in the Triclinic space group P-1 with a = 10.1233 (9) Å, b = 10.7577 (10) Å, c = 10.8471 (10) Å. Hirshfeld surface and finger print plots were analysed using Crystal Explorer to confirm the existence of intermolecular, intramolecular and other weak interactions. The optimized molecular structure and vibrational wavenumbers were calculated using density functional theory (DFT/B3LYP) method with the 6–31 G (d,p) basis set using Gaussian 09 software. The optimized geometrical parameters, structures and vibrational wavenumbers were compared with the experimental results. Natural Bond Orbital analysis (NBO) was carried out to evaluate the intramolecular stabilization interactions of the crystal. The highest occupied molecular orbital (HOMO) energy, the lowest unoccupied molecular orbital (LUMO) energy and their energy gap (ΔE) of the CBAD crystal were calculated. In addition, the molecular docking analysis was carried out to explore the inhibitory nature of the crystal against CCR2, NMDA and SHP2 receptors. Docking results suggest that su the CBAD crystal could be a novel inhibitor candidate of CCR2 receptor which causes psoriasis.