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Volume 69 
Part 5 
Page o771  
May 2013  

Received 10 April 2013
Accepted 16 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.007 Å
R = 0.072
wR = 0.156
Data-to-parameter ratio = 28.3
Details
Open access

9H-Carbazole-9-carbothioic dithioperoxyanhydride

aDepartment of Chemistry, Namik Kemal University, 59030 Degirmenalti, Tekirdag, Turkey,bDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey,cDepartment of Physics, Dicle University, 21280 Sur, Diyarbakir, Turkey, and dDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The whole molecule of the title compound, C26H16N2S4, is generated by twofold rotational symmetry. The carbazole skeleton is nearly planar [maximum deviation = 0.054 (5) Å]. In the crystal, aromatic [pi]-[pi] stacking is observed between parallel carbazole ring systems of adjacent molecules, the shortest centroid-centroid distances between pyrrole and benzene rings being 3.948 (3) and 3.751 (3) Å.

Related literature

For tetrahydrocarbazole systems present in the framework of a number of indole-type alkaloids of biological interest, see: Saxton (1983[Saxton, J. E. (1983). Editor. Heterocyclic Compounds Vol. 25, The Monoterpenoid Indole Alkaloids, chs. 8 and 11. New York: Wiley.]). For related structures, see: Hökelek et al. (1994[Hökelek, T., Patir, S., Gülce, A. & Okay, G. (1994). Acta Cryst. C50, 450-453.], 1998[Hökelek, T., Gündüz, H., Patir, S. & Uludaug, N. (1998). Acta Cryst. C54, 1297-1299.], 1999[Hökelek, T., Patir, S. & Uludaug, N. (1999). Acta Cryst. C55, 114-116.]); Patir et al. (1997[Patir, S., Okay, G., Gülce, A., Salih, B. & Hökelek, T. (1997). J. Heterocycl. Chem. 34, 1239-1242.]); Hökelek & Patir (1999[Hökelek, T. & Patir, S. (1999). Acta Cryst. C55, 675-677.]). For hole-transporting mobility of charge carriers, see: Cloutet et al. (1999[Cloutet, E., Yammine, P., Ades, D. & Siove, A. (1999). Synth. Met. 102, 1302-1303.]). For photoluminescence efficiencies, see: Zhenhong et al. (2006[Zhenhong, W., Jingkun, X., Guangming, N., Yukou, D. & Shouzhi, P. (2006). J. Electroanal. Chem. 589, 112-119.]). For electroluminescent applications, see: Tirapattur et al. (2003[Tirapattur, S., Belletete, M., Drolet, N., Leclerc, M. & Durocher, G. (2003). Chem. Phys. Lett. 370, 799-804.]). For photoactive devices, see: Taoudi et al. (2001[Taoudi, H., Bernede, J. C., Del Valle, M. A., Bonnet, A. & Morsli, M. (2001). J. Mater. Sci. 36, 631-634.]). For sensors and rechargable batteries, see: Saraswathi et al. (1999[Saraswathi, R., Gerard, M. & Malhotra, B. D. (1999). J. Appl. Polym. Sci. 74, 145-150.]). For electrochromic displays, see: Sarac et al. (2000[Sarac, A. S., Yavuz, O. & Sezer, E. (2000). Polymer, 41, 839-847.]).

[Scheme 1]

Experimental

Crystal data
  • C26H16N2S4

  • Mr = 484.69

  • Orthorhombic, P 221 21

  • a = 3.9207 (2) Å

  • b = 14.9355 (4) Å

  • c = 18.1494 (5) Å

  • V = 1062.79 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.47 mm-1

  • T = 294 K

  • 0.35 × 0.15 × 0.10 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.920, Tmax = 0.954

  • 5384 measured reflections

  • 4100 independent reflections

  • 2471 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.072

  • wR(F2) = 0.156

  • S = 1.41

  • 4100 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1548 Friedel pairs

  • Flack parameter: 0.04 (18)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2587 ).


Acknowledgements

The authors are indebted to Dicle University Scientific and Technological Applied and Research Center, Diyarbakir, Turkey, for use of the X-ray diffractometer.

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cloutet, E., Yammine, P., Ades, D. & Siove, A. (1999). Synth. Met. 102, 1302-1303.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hökelek, T., Gündüz, H., Patir, S. & Uludaug, N. (1998). Acta Cryst. C54, 1297-1299.  [CSD] [CrossRef] [details]
Hökelek, T. & Patir, S. (1999). Acta Cryst. C55, 675-677.  [CSD] [CrossRef] [details]
Hökelek, T., Patir, S., Gülce, A. & Okay, G. (1994). Acta Cryst. C50, 450-453.  [CrossRef] [details]
Hökelek, T., Patir, S. & Uludaug, N. (1999). Acta Cryst. C55, 114-116.  [CSD] [CrossRef] [details]
Patir, S., Okay, G., Gülce, A., Salih, B. & Hökelek, T. (1997). J. Heterocycl. Chem. 34, 1239-1242.  [ChemPort]
Sarac, A. S., Yavuz, O. & Sezer, E. (2000). Polymer, 41, 839-847.  [ChemPort]
Saraswathi, R., Gerard, M. & Malhotra, B. D. (1999). J. Appl. Polym. Sci. 74, 145-150.  [CrossRef] [ChemPort]
Saxton, J. E. (1983). Editor. Heterocyclic Compounds Vol. 25, The Monoterpenoid Indole Alkaloids, chs. 8 and 11. New York: Wiley.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Taoudi, H., Bernede, J. C., Del Valle, M. A., Bonnet, A. & Morsli, M. (2001). J. Mater. Sci. 36, 631-634.  [ISI] [CrossRef] [ChemPort]
Tirapattur, S., Belletete, M., Drolet, N., Leclerc, M. & Durocher, G. (2003). Chem. Phys. Lett. 370, 799-804.  [ISI] [CrossRef] [ChemPort]
Zhenhong, W., Jingkun, X., Guangming, N., Yukou, D. & Shouzhi, P. (2006). J. Electroanal. Chem. 589, 112-119.


Acta Cryst (2013). E69, o771  [ doi:10.1107/S1600536813010349 ]

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