[Journal logo]

Volume 69 
Part 6 
Pages o972-o973  
June 2013  

Received 18 March 2013
Accepted 20 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.093
Data-to-parameter ratio = 22.5
Details
Open access

6-[3-(p-Tolylsulfonylamino)propyl]diquinothiazine1

aDepartment of Organic Chemistry, The Medical University of Silesia, ul. Jagiellonska 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. Wóycickiego 1/3, PL-01 938, Warszawa, Poland
Correspondence e-mail: pluta@sum.edu.pl

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.

Related literature

For the structures of heteropentacenes, see: Anthony (2006[Anthony, J. E. (2006). Chem. Rev. 106, 5028-5048.]); Isaia et al. (2009[Isaia, F., Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Ennas, G., Garau, A., Lippolis, V., Mancini, A. & Verani, G. (2009). Eur. J. Inorg. Chem. pp. 3667-3672.]); Yoshida et al. (1994[Yoshida, S., Kozawa, K., Sato, N. & Uchida, T. (1994). Bull. Chem. Soc. Jpn, 67, 2017-2023.]). For recent literature on the biological activity of phenothiazines, see: Aaron et al. (2009[Aaron, J. J., Gaye Seye, M. D., Trajkovska, S. & Motohashi, N. (2009). Top. Heterocycl. Chem. 16, 153-231.]); Pluta et al. (2011[Pluta, K., Morak-Mlodawska, B. & Jelen, M. (2011). Eur. J. Med. Chem. 46, 3179-3189.]). For the synthesis and biological activity of 6-substituted diquinothiazines, see: Nowak et al. (2007[Nowak, M., Pluta, K., Suwinska, K. & Straver, L. (2007). J. Heterocycl. Chem. 44, 543-550.]); Jelen & Pluta (2009[Jelen, M. & Pluta, K. (2009). Heterocycles, 78, 2325-2336.]); Pluta et al. (2010[Pluta, K., Jelen, M., Morak-Mlodawska, B., Zimecki, M., Artym, J. & Kocieba, M. (2010). Pharmacol. Rep. 62, 319-332.]). For crystal structures of phenothiazines, see: Chu (1988[Chu, S. S. C. (1988). Phenothiazines and 1,4-Benzothiazines - Chemical and Biological Aspects, edited by R. R. Gupta, pp. 475-526. Amsterdam: Elsevier.]). For information on azaphenothiazines, their nomenclature and synthesis, see: Pluta et al. (2009[Pluta, K., Morak-Mlodawska, B. & Jelen, M. (2009). J. Heterocycl. Chem. 46, 355-391.]). For heteropentacenes with quinoline moieties containing nitrogen, sulfur, oxygen and selenium, see: Nowak et al. (2002[Nowak, M., Pluta, K. & Suwinska, K. (2002). New J. Chem. 26, 1216-1220.]); Pluta et al. (2000[Pluta, K., Nowak, M. & Suwinska, K. (2000). J. Chem. Crystallogr. 30, 479-482.]).

[Scheme 1]

Experimental

Crystal data
  • C28H24N4O2S2

  • Mr = 512.63

  • Triclinic, [P \overline 1]

  • a = 9.3986 (3) Å

  • b = 10.3793 (3) Å

  • c = 12.6207 (3) Å

  • [alpha] = 80.735 (2)°

  • [beta] = 81.959 (2)°

  • [gamma] = 77.999 (2)°

  • V = 1181.30 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 100 K

  • 0.39 × 0.34 × 0.23 mm

Data collection
  • Agilent SuperNova Dual (Cu at zero, Eos) diffractometer

  • Absorption correction: analytical [CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) and Clark & Reid (1995[Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.])] Tmin = 0.937, Tmax = 0.965

  • 24091 measured reflections

  • 7396 independent reflections

  • 6770 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.093

  • S = 1.04

  • 7396 reflections

  • 329 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N18-H18...N5 0.876 (14) 2.243 (15) 2.9973 (12) 144.1 (12)
C15-H15A...O20i 0.99 2.33 3.1641 (12) 141
C11-H11...O21ii 0.95 2.55 3.3933 (13) 149
C15-H15B...S13iii 0.99 2.86 3.6912 (11) 142
C17-H17B...O21iv 0.99 2.47 3.3013 (13) 141
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y, z-1; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2566 ).


Acknowledgements

The work was supported by the Medical University of Silesia (grant KNW-1-006/P/2/0).

References

Aaron, J. J., Gaye Seye, M. D., Trajkovska, S. & Motohashi, N. (2009). Top. Heterocycl. Chem. 16, 153-231.  [CrossRef] [ChemPort]
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Anthony, J. E. (2006). Chem. Rev. 106, 5028-5048.  [ISI] [CrossRef] [PubMed] [ChemPort]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Chu, S. S. C. (1988). Phenothiazines and 1,4-Benzothiazines - Chemical and Biological Aspects, edited by R. R. Gupta, pp. 475-526. Amsterdam: Elsevier.
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897.  [CrossRef] [details]
Isaia, F., Aragoni, M. C., Arca, M., Demartin, F., Devillanova, F. A., Ennas, G., Garau, A., Lippolis, V., Mancini, A. & Verani, G. (2009). Eur. J. Inorg. Chem. pp. 3667-3672.  [ISI] [CSD] [CrossRef]
Jelen, M. & Pluta, K. (2009). Heterocycles, 78, 2325-2336.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Nowak, M., Pluta, K. & Suwinska, K. (2002). New J. Chem. 26, 1216-1220.  [ISI] [CSD] [CrossRef] [ChemPort]
Nowak, M., Pluta, K., Suwinska, K. & Straver, L. (2007). J. Heterocycl. Chem. 44, 543-550.  [CrossRef] [ChemPort]
Pluta, K., Jelen, M., Morak-Mlodawska, B., Zimecki, M., Artym, J. & Kocieba, M. (2010). Pharmacol. Rep. 62, 319-332.  [ChemPort] [PubMed]
Pluta, K., Morak-Mlodawska, B. & Jelen, M. (2009). J. Heterocycl. Chem. 46, 355-391.  [CrossRef] [ChemPort]
Pluta, K., Morak-Mlodawska, B. & Jelen, M. (2011). Eur. J. Med. Chem. 46, 3179-3189.  [ISI] [CrossRef] [ChemPort] [PubMed]
Pluta, K., Nowak, M. & Suwinska, K. (2000). J. Chem. Crystallogr. 30, 479-482.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Yoshida, S., Kozawa, K., Sato, N. & Uchida, T. (1994). Bull. Chem. Soc. Jpn, 67, 2017-2023.  [CrossRef] [ChemPort] [ISI]


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

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.