N-[4-(9-Chloroquino[3,2-b]benzo[1,4]thiazin-6-yl)butyl]acetamidePart CXXXIII in the series of Azinyl sulfides.

Abstract

In the title molecule, C21H20ClN3OS, the tetracyclic system is close to planar [r.m.s. deviation = 0.110 (4) Å]. The dihedral angle between the quinoline ring system and the benzene ring is 178.3 (1)° and the angle between two (S—C=C—N) halves of the thiazine ring is 173.4 (1)°. In the crystal, molecules are arranged via π–π interactions [centroid–centroid distances = 3.603 (2)–3.739 (2) Å] into slipped stacks extending along [010]. Intermolecular N—H...O hydrogen bonds link the amide groups of neighbouring molecules along the stack, generating a C(4) motif. The title compound shows promising antiproliferative and anticancer activity.