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The new cocrystal adducts of N-phthaloyl-β-alanine and benzimidazole (1:2) with molecular formula C 18 H 15 N 3 O 4 (1) was synthesized by slow evaporation process of the aqueous solution containing the two said moieties. The confirmation of proposed formula can be established through crystal structure as well as FTIR analysis. The crystal structure was confirmed by single X–ray crystal analysis. The experimental and theoretical studies of photophysical properties like Fourier Transform Infrared (FTIR) and ultraviolet–visible spectroscopy (UV–Vis) have been done. The cocrystal belong to monoclinic crystallographic system with space group P21/c, Z = 4. DPPH radical scavenging activity of the title cocrystal is slightly lower than coformer with lower IC 50 value, respectively. One dimensional infinite chain in direction of [010] parallel to b direction. Optimized crystalline network structure of 1 shows that conventional N−H⋯O, and O H⋯N, and the non−conventional C H⋯O hydrogen bonds (HBs) gathered the monomeric components of 1 (1−mon). The reliable calculations of the dispersion corrected density functional theory (DFT−D) display that N−H⋯O and O−H⋯N HBs more share in the stabilization of the network structure. The theoretical study of UV–Vis spectra in solvents (water, acetonitrile, methanol, and n–heptanes) confirms the experimental results as seven main bands in 180–270 nm range. They could attribute to intra-ligand charge transfer (ILCT) as benzimidazole → benzimidazole and N-phthaloyl-β-alanine → N-phthaloyl-β-alanine with π → π* character. Image 103013 • Synthesis a novel cocrystal adducts of N-phthaloyl-β-alanine and benzimidazole (1:2). • Structural characterization by single X–ray crystal, FTIR, and UV–Vis. • Having higher DPPH radical scavenging activity than coformers with lower IC 50 value. • Theoretical study of the constructive non–covalent interactions by DFT–D calculations. • The network stabilized by N−H⋯O, O−H⋯N, and C−H⋯O contacts. [ABSTRACT FROM AUTHOR]

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]