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.
Highlights
Acta Crystallographica Section E moieties containing nitrogen, sulfur, oxygen and selenium, see: Nowak et al (2002); Pluta et al (2000)
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
H atoms treated by a mixture of independent and constrained refinement max = 0.42 e Å3
Summary
Suwińska,b,c Krystian Plutaa* and Beata MorakMłodawskaa a Department of Organic Chemistry, The Medical University of Silesia, ul. 4, PL–41 200 Sosnowiec, Poland, bInstitute of Physical Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, PL–01 224 Warsaw, Poland, and cFaculty of Biology and Environmental Sciences, Cardinal Stefan Wyszynski University, ul
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