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Two novel 2-(benzofuran-2-yl)-2-oxoethyl 3-(methyl/amino)benzoates  2 ( a–b ), were synthesized under mild conditions and characterized by spectroscopic analysis. The three-dimensional (3D) crystal structures of these compounds were further determined using single crystal X-ray diffraction technique and revealed that both compounds tend to twist away with respect to their attached carbonyl groups at the C(=O)–C–O–C(=O) connecting bridge, exhibiting a nearly perpendicular conformation with torsion angle in a range of 75–94°. In both compounds, each of the benzofuran and substituted phenyl rings are individually planar while almost perpendicular to each other. Their molecular conformation are comparable with related structures from the Cambridge Structural Database (CSD). Furthermore, the intermolecular interactions in these crystal structures were quantified and analyzed using Hirshfeld surfaces computational method. The quantitative data on the percentage contributions of overall interactions on the molecules 2a and 2b ( A  &amp;  B ) is calculated by the 2-D fingerprint plots from the HS analysis. These structures were evaluated for their antioxidant properties by diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, ferrous ion chelating (FIC) and hydrogen peroxide radical scavenging assays (H 2 O 2 ). Noteworthy, compound  2b  with an amino substituent attached to the phenyl ring exhibited an IC 50  value of 45.37 μg/mL in H 2 O 2  scavenging assay, which showed better scavenging effect than the standard drug, ascorbic acid (IC 50 =81.02 μg/mL).

Radical scavenging potency of 2-(benzofuran-2-yl)-2-oxoethyl 3-(methyl/amino)benzoate: synthesis, crystal structure and Hirshfeld surface analysis