Synthesis, crystal structure, Hirshfeld surface analysis, spectral characterizations and quantum computational assessments of 1‑hydroxy-3-methyl-11H-pyrido[2,1-b] quinazolin-11-one

Abstract

In this manuscript, a newly synthesized 1‑hydroxy-3-methyl-11H-pyrido[2,1-b] quinazolin-11-one molecule was analyzed in details for structural clarification by X-Ray crystallographic and FT-IR spectral data along with theoretical quantum chemical computations. The theoretical computations were performed by DFT/B3LYP method and 6–311++G(d,p) basis set in gas phase, and Potential Energy Distribution (PED) analysis of the DFT/B3LYP calculated IR spectrum of the compound was carried out by VEDA4 program. Hirshfeld surface analysis of the compound was performed to determine the most important contributions for the crystal packing. The 1H- and 13C- NMR chemical shift analyses were theoretically and experimentally studied for the compound. The existence of the n(O)→σ*(OH) hyperconjugative interaction resulted from the intra-molecular OH···O hydrogen bonding in the title compound were analyzed with NBO (Natural Bond Orbital) study. Additionally, the highest occupied molecular orbital (HOMO) - the lowest unoccupied molecular orbital (LUMO), the molecular electrostatic potential (MEP) and the non-linear optic values for the compound were found. Finally, the molecular docking study between the compound and macromolecule PDB:1EVE was done, and from the binding affinity value and the presence of inter-molecular interactions it was concluded that the title ligand compound may serve as a smart drug with nootropic property.