Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 6 (June 2013)


organic compounds



gk2566 scheme

Acta Cryst. (2013). E69, o972-o973    [ doi:10.1107/S1600536813013950 ]

6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine

M. Jelen, A. Shkurenko, K. Suwinska, K. Pluta and B. Morak-Mlodawska

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 [pi]-[pi] 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.


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