Fig 1.
Synthesis of (1,3‐dioxo‐2,3‐dihydro‐1H‐isoindol‐2‐yl)methyl (substituted) benzoates 4(a-n).
Fig 2.
ORTEP diagram of compounds 4a to 4n (excluding 4d, 4h and 4m).
Compounds 4b, 4f, 4g, 4j, 4k and 4n are drawn at 50% ellipsoids for non-hydrogen atoms and the remaining compounds are drawn at 30% ellipsoids for non-hydrogen atoms.
Table 1.
Crystal data and parameters for structure refinement of 4a, 4b, 4c, 4e and 4f.
Table 2.
Crystal data and parameters for structure refinement of 4g, 4i, 4j, 4k, 4l and 4n.
Table 3.
Hydrogen bond geometries for the compounds 4a-4n (excluding 4d, 4h and 4m).
Table 4.
Dihedral angles and torsion angles formed between the phthalimide and benzene ring systems.
Fig 3.
Crystal structure of 4a, showing the sheet parallel to bc-plane, viewed along the b-axis.
Fig 4.
Crystal structure of 4b, showing the formation of sheet parallel to ab-plane.
Fig 5.
Crystal structure of 4c, showing the three-dimensional network, viewed along the b-axis.
Fig 6.
Crystal structure of 4e, showing the ring motifs which lead to the formation of sheet parallel to bc-plane.
Fig 7.
Overlay of all non-H atoms in compounds 4a, 4b, 4c and 4e, calculated using the phthalimide moiety.
Fig 8.
Crystal structure of 4f, showing the dimers which are further linked into sheet parallel to ab-plane.
Fig 9.
Crystal structure of 4g, showing the formation of dimers stacked along the a-axis.
Fig 10.
Overlay of all non-H atoms in compounds 4a, 4f and 4g, calculated using the phthalimide moiety.
Fig 11.
Overlay of all non-H atoms in compounds 4a, 4i, 4j and 4k, calculated using the phthalimide moiety.
Fig 12.
Crystal structure of 4j, showing the column formed along [–110] via intermolecular C—H···O hydrogen bonds.
Fig 13.
Crystal structure of 4k, showing the sheet formed parallel to ac-plane via intermolecular C—H···O hydrogen bonds.
Fig 14.
Overlay of all non-H atoms in compounds 4a, 4l and 4n, calculated using the phthalimide moiety.
Fig 15.
Crystal structure of 4l, showing the dimers which are further connected to form sheet parallel to ab-plane.
Fig 16.
Crystal structure of 4n, showing the ring motifs which are linked into chain along b-axis via intermolecular C—H···O hydrogen bonds.
Fig 17.
Overlay of all molecular structures, excluding H atoms and substituents at benzene rings where 4i and 4j are highlighted in blue and pink, respectively.
Fig 18.
IC50 (concentration required for 50% inhibition) values for DPPH radical scavenging activities of the compounds 4(a–n) in comparison with the standard antioxidant BHT.
Lower IC50 values indicate higher radical scavenging activity.
Fig 19.
Ferric and cupric ion reducing power abilities of the tested samples at 10 μg concentration measured at 700 nm.
Values are expressed as absorbance; high absorbance indicates high reducing power