Molecular Structure and Supramolecular Architecture of ( E )-2-Bromo-6-[(2,4,6-Tribromophenylimino)methyl]-4-Chloropheno
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Molecular Structure and Supramolecular Architecture of (E)-2-Bromo-6-[(2,4,6-Tribromophenylimino)methyl]-4-Chlorophenol Ç. Albayrak Kaştaşa,*, G. Kaştaşb, B. Koşar Kırcac, and C. C. Ersanlıd a
b
Department of Chemistry, Faculty of Arts and Sciences, Sinop University, Sinop, Turkey Department of Aircraft Maintenance, Faculty of Aeronautics and Astronautics, Samsun University, Samsun, Turkey c Department of Science Education, Faculty of Education, Sinop University, Sinop, Turkey d Department of Physics, Faculty of Arts and Sciences, Sinop University, Sinop, Turkey *e-mail: [email protected] Received April 22, 2019; revised October 4, 2019; accepted October 7, 2019
Abstract—In this study, the molecular structure and supramolecular architecture of a new compound have been studied in depth using single crystal X-ray diffraction (XRD) technique. Crystallographic results show that the compound exists in phenol-imine form that is twisted with the dihedral angle of 51.77° between the aromatic rings of the molecule. Various types of non-covalent interactions (C⋅⋅⋅O, C–H⋅⋅⋅O, Br⋅⋅⋅Br, C–H⋅⋅⋅Cl, π⋅⋅⋅π, O⋅⋅⋅Br, and Br⋅⋅⋅π) take part effectively in the construction of 3D network in the compound. The C⋅⋅⋅O and C–H⋅⋅⋅O interactions have the role of forming the 1D structure along the direction [010] with the support of π⋅⋅⋅π and π⋅⋅⋅Br interactions. The 2D structure of the compound is reached by the inter-connection of 1D chains in the (101) plane through the C–H⋅⋅⋅Cl interactions. The 3D supramolecular structure of the compound is completed by the non-covalent Br⋅⋅⋅Br and Br⋅⋅⋅O interactions responsible for the connection of 2D sheets. DOI: 10.1134/S1063774520070093
INTRODUCTION Salicylidenanilines continue to be the intense research subject in scientific and industrial fields due to a number of useful properties (antimicrobial, antifungal, antitumor and cytotoxic activites, catalysts, DNA cleavage, optical switch, ophthalmic glasses, dyes, polymers and so on.) that are known to be associated with their interesting molecular geometries [1– 8] as well as their crystal packings as in the photochromic and thermochromic phenomena [9, 10]. From the perspective of molecular geometry, these compounds have two tautomeric forms in both solid state and solvent media as phenol-imine and keto-amine forms [11–13]. Previous studies reveal that there are two other possible molecular geometries of these compounds named Zwitter ionic and resonance hybrid structures [14, 15]. In this study, a new salicylidenaniline derivative, (E)-2-bromo-6-[(2,4,6-tribromophenylimino)methyl]4-chlorophenol, has been synthesized. The molecular structure and supramolecular architecture of the compound have been investigated in detail by using X-ray diffraction technique (XRD).
EXPERIMENTAL METHODS Synthesis The solution of 3-bromo-5-chloro-2-hydroxybenzaldehyde (0.15 g; 0.64 mmol) and ethanol (20 mL) was added to solution of 2,4,6-tribromoaniline (0.165 g; 0.64 mmol) and ethanol (20 mL). After the mixture was refluxed by stirrin
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