SYNTHESIS, CHARACTERIZATION, AND HIRSHFELD SURFACE ANALYSIS OF TWO SCHIFF BASES: (E)-3-(((4-IODOPHENYL)IMINO)METHYL)BENZENE-1,2-DIOL AND (E)-3-(((3-BROMO-4-METHYLPHENYL)IMINO)METHYL)BENZENE-1,2-DIOL

The title compounds, (E)-3-(((4-iodophenyl)imino)methyl)benzene-1,2-diol compound (1) and (E)-3-(((3-bromo-4-methylphenyl)imino)methyl)benzene-1,2-diol (2) were synthesized and comprehensively characterized through spectroscopic and crystallographic techniques, including single-crystal X-ray diffraction, IR, UV–Vis, 1H NMR, and 13C NMR analyses. Both compounds adopt an E configuration with respect to the C=N double bond and crystallize in the triclinic crystal system, space group P. Their crystal packings are primarily stabilized by O−H···O hydrogen bonds, complemented by C−H···π interactions, which extend the packing into a three-dimensional supramolecular framework. Hirshfeld surface analysis was employed to identify regions of potential hydrogen-bond formation and to quantify the relative contribution of different intermolecular contacts. The results reveal that C···H interactions dominate the surface contributions, underscoring their importance in the overall packing stability and molecular arrangement.