Single stranded helical chains of C–H⋯π interactions further connected by halogen–halogen interactions of type I to construct supramolecular structure of (E)-5-(diethylamino)-2-[(4-iodophenylimino)methyl]phenol compound

In this study, (E)-5-(diethylamino)-2-[(4-iodophenylimino)methyl]phenol compound was investigated from the point of stacking interactions assembling the supramolecular network, conformational isomerism and tautomerism. For this purpose, X-ray diffraction, FT-IR and UV/Vis spectroscopic techniques were used, giving the following structural and spectroscopic properties of the compound: The title compound has two conformers (anti and eclipsed) in the crystal structure resulting from rotation about C–N single bond of ethyl group. Both conformers prefer enol form in the solid state, adopting E configuration about the CN double bond. The supramolecular architecture of the compound is constructed by two non-covalent interactions as C–H⋯π and halogen–halogen interactions. The repetition of C–H⋯π interactions is resulted in a single-stranded helical structure. The helical structures are further connected by C–I⋯I–C interactions of Type I to construct the two dimensional supramolecular network defined as (6,3)-net in Wells nomenclature. The title compound adopts both enol and keto forms in EtOH (a polar and protic solvent) while enol form is preferred in the solid state.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Supramolecular structure was studied. ► Isomerism and tautomerism were investigated. ► Investigation of tautomerism was performed depending on solute–solvent interactions.