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In the present work a novel cocrystal adduct of N –phthaloyl–β–alanine and 2,2–bipyridyl as compound 1 with molecular formula C 16 H 13 N 3 O 4 was synthesized by slow evaporation process of the ethanoic solution containing these two moieties. In followings, the crystal structure and photophysical properties of 1 was characterized by single X-ray crystal analysis, FTIR, and UV–Vis spectra. The thermal behavior was analyzed by the Thermogravimetric/Differential Thermal Analyzer (TG-DTA). The cocrystal belong to monoclinic crystallographic system with space group P 21/ n , Z = 4. DPPH radical scavenging activity of the title cocrystal is slightly higher than coformer with lower IC 50 value. Finally, using DFT calculations executed at hybrid B3LYP/6–311+G ( d , p ) level of theory the geometric and electronic structures of the crystalline network of C 16 H 13 N 3 O 4 ( 1 ), studied. Inter-molecular conventional O H⋯N as well as the non-conventional C H⋯O hydrogen bonds (HBs) and C H···π and C O···π stacking interactions gathered the monomeric structures of 1 ( 1-mon ) to create the 3D architecture of the network ( 1-net ). The dispersion corrected density functional theory (DFT-D) calculations indicate that O H⋯N and C H⋯O HBs, govern the 1-net formation. The calculated UV–Vis spectrum in vacuo has agreement with the experimental one that shows five major bands in the range of 170–271 nm that could assigned to transitions between 2,2-bipyridyl and N -phthaloyl-β-alanine parts of 1 with n → π ∗ and π → π* ligand-ligand-charge transfer (LLCT) character. The calculated electronic spectra in solvents (water, acetonitrile, methanol, and n–heptane) comparing with the vacuo one show broad bands with blue shifts. [ABSTRACT FROM AUTHOR]

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, C 10 H 10 NO 3 Cl ( 1 ), constructed via hydrogen bonds (HBs) and stacking non–covalent interactions. Compound 1 was synthesized and characterized by FTIR, 1 H, and 13 C 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. [ABSTRACT FROM AUTHOR]