The synthesis and structure of two novel N-(benzothiazol-2-yl)benzamides

Two novel benzothiazoles 2-chloro-N-(benzothiazol-2-yl)benzamide (1) and 2-chloro-N-(6-cyanobenzothiazol-2-yl)benzamide (2) were obtained in multistep synthesis. They were characterised by means of IR, H-1- and C-13-NMR spectroscopy and also by single-crystal X-ray diffraction. The compound 1 crystallises with triclinic space group P (1) over bar, a = 9.5923(8) angstrom, b = 9.8583(8) angstrom, c = 13.8962(10) angstrom, alpha = 89.162(6)degrees, beta = 77.741(7)degrees, gamma = 80.064(7)degrees, V = 1264.5(2) angstrom(3), Z = 4 and compound 2 crystallises as methanol solvate with monoclinic space group P 2(1)/n, a = 7.5093(9) angstrom, b = 13.0211(14) angstrom, c = 16.032(2) angstrom, beta = 92.717(10)degrees, V = 1565.9(3) angstrom(3), Z = 4. Both crystal structures consist of discrete dimers connected into a three-dimensional network by intermolecular C-H center dot center dot center dot O and C-H center dot center dot center dot X (X = Cl or S) hydrogen bonds and by face-to-face pi-pi stacking interactions.