title: 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.
abstract: 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.
authors.affiliation: Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey. gkastas@omu.edu.tr
authors.forename: Gökhan
authors.initials: G
authors.lastname: Kaştaş
authors.forename: Ciğdem
authors.initials: C
authors.lastname: Albayrak
authors.forename: Mustafa
authors.initials: M
authors.lastname: Odabaşoğlu
authors.forename: René
authors.initials: R
authors.lastname: Frank
mesh_terms: D018360:Crystallography, X-Ray; D005021:Ethylamines / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: C575202:(E)-5-(diethylamino)-2-((4-iodophenylimino)methyl)phenol; D005021:Ethylamines; D006219:Halogens; D010636:Phenols; D012997:Solvents