LAUSR

Abstract The presented work studies the geometric and electronic structures of the crystalline network of a novel amide based carboxylic acid derivative, N–[(4–chlorophenyl)]–4–oxo–4–[oxy] butane amide, C10H10NO3Cl (1), constructed via hydrogen bonds (HBs) and stacking non–covalent interactions. Compound 1 was synthesized and characterized by FTIR, 1H, and 13C NMR, and UV–Vis spectra, X–ray structural, DTA–TG, and EI–MS, analyses. DFT calculations about molecular and related network of 1 were performed at hybrid B3LYP/6–311+G (d, p) level of theory to support the experimental data. The neutral monomeric structures join together via inter−molecular conventional O/N H⋯O and non−conventional C H⋯O HBs and O H···π and C O···π stacking interactions to create 2−D architecture of the network. The results of dispersion corrected density functional theory (DFT−D) calculations within the binding energy of the constructive non−covalent interactions demonstrate that HBs, especially conventional O H⋯O and N H⋯O, govern the network formation. The calculated electronic spectrum show six major bands in the range of 180–270 nm which confirm the experimental one within an intense band around 250 nm. These charge transfer bands result from shift of lone pair electron density of phenyl to chlorine or hydroxyl or phenyl functional groups that possess π → π* and π → n characters.