Intramolecular Hypervalent C=OS interactions in a series of 1,3-benzothiazole derivatives.

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 (17) 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 (COS, SS), hydrogen bonds YHX (Y = O, N, C; X = O, N, Cl, ?) and van der Waals contacts (Cl?, S?, HH) that are found to be the driving forces for the supramolecular arrangements present in the crystal structures.