Intramolecular hypervalent CO⋯S interactions in a series of 1,3-benzothiazole derivatives

Abstract

Seven compounds derived from 2-(4-chlorophenoxy)-2-methylpropionic acid and 2-aminobenzothiazole, 2-amino-6-methylbenzothiazole, 2-amino-6-methoxybenzothiazole, 2-amino-6-ethoxybenzothiazole, 2-amino-6-chlorobenzothiazole, 2-amino-6-nitrobenzothiazole, and 2-amino-6-(methylsulfonyl) benzothiazole have been prepared and structurally characterized. This set of 1,3-benzothiazole derivatives (1–7) has been studied by means of elemental analysis, mass spectrometry, IR, NMR (¹H, ¹³C) spectroscopy, and single-crystal X-ray diffraction analysis. This work focuses on the description of the hypervalent contacts (CO⋯S, S⋯S), hydrogen bonds Y–H⋯X (Y = O, N, C; X = O, N, Cl, π) and van der Waals contacts (Cl⋯π, S⋯π, H⋯H) that are found to be the driving forces for the supramolecular arrangements present in the crystal structures.