6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazinePart CXXXVII in the series of `Azinyl Sulfides'.

Abstract

In the title molecule {systematic name: N-[3-(diquino[3,2-b;2′,3′-e][1,4]thiazin-6-yl)propyl]-4-methylbenzenesulfonamide}, C28H24N4O2S2, the pentacyclic system is relatively planar [maximum deviation from the mean plane = 0.242 (1) Å]. The dihedral angle between two quinoline ring systems is 8.23 (2)° and that between the two halves of the 1,4-thiazine ring is 5.68 (3)°. The conformation adopted by the 3-(p-tolylsulfonylamino)propyl substituent allows for the formation of an intramolecular N—H...N hydrogen bond and places the benzene ring of this substituent above one of the quinoline fragments of the pentacyclic system. In the crystal, molecules are arranged via π–π stacking interactions into (0-11) layers [centroid–centroid distances = 3.981 (1)–4.320 (1) Å for the rings in the pentacyclic system and 3.645 (1) Å for the tolyl benzene rings]. In addition, molecules are involved in weak C—H...O, which connect the layers, and C—H...S hydrogen bonds. The title compound shows promising anticancer activity against renal cancer cell line UO-31.