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Volume 69 
Part 4 
Pages o598-o599  
April 2013  

Received 18 March 2013
Accepted 21 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.075
wR = 0.195
Data-to-parameter ratio = 19.3
Details
Open access

3,9-Dimethyl-2,3-dihydrospiro[carbazole-1,2'-[1,3]dithiolan]-4(9H)-one

aCelal Bayar University, Faculty of Arts and Sciences, Department of Chemistry, 45030 Muradiye, Manisa, Turkey,bDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey,cDokuz Eylül University, Faculty of Arts and Sciences, Department of Chemistry, Tinaztepe, 35160 Buca, Izmir, Turkey, and dHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

The title compound, C16H17NOS2, consists of a carbazole skeleton with methyl and dithiolane groups as substituents. In the indole ring system, the benzene and pyrrole rings are nearly coplanar, forming a dihedral angle of 1.02 (11)°. The cyclohexenone ring has a twisted conformation, while the dithiolane ring adopts an envelope conformation with one of the CH2 C atoms at the flap. In the crystal, weak C-H...O hydrogen bonds link the molecules into supramolecular chains nearly parallel to the c axis. These hydrogen bonds together with weak C-H...[pi] interactions link the molecules into a three-dimensional supramolecular network.

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, ch. 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.], 2009[Hökelek, T., Dal, H., Tercan, B., Göçmentürk, M. & Ergün, Y. (2009). Acta Cryst. E65, o1702-o1703.]); 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.]); Çaylak et al. (2007[Çaylak, N., Hökelek, T., Uludag, N. & Patir, S. (2007). Acta Cryst. E63, o3913-o3914.]); Uludag et al. (2009[Uludag, N., Öztürk, A., Hökelek, T. & Erdogan, Ü. I. (2009). Acta Cryst. E65, o595-o596.]). For the isolation of carbazole alkaloids such as 3-methylcarbazole and its several oxidized derivatives from taxonomically related higher plants, see: Chakraborty (1993[Chakraborty, D. P. (1993). The Alkaloids, edited by G. A. Cordell, Vol. 44, pp. 257-364. New York: Academic Press.]); Bhattacharyya & Chakraborty (1987[Bhattacharyya, P. & Chakraborty, D. P. (1987). Progress in the Chemistry of Organic Natural Products, edited by W. Hertz, H. Grisebach, G. W. Kirby & C. Tamm, Vol. 52, pp. 159-209. Wien, New York: Springer-Verlag.]). For the use of 4-oxo-tetrahydrocarbazole in the synthesis of antiemetic drugs, central nervous system active drugs and NPY-1 antagonists, see: Littell & Allen (1973[Littell, R. & Allen, G. R. (1973). US Patent No. 3 740 404.]); Ping & Guoping (1997[Ping, H. & Guoping, F. (1997). Assignee: Shanghai Hualian Pharmaceutical Co., People's Republic of China, Patent No. CN 1145902.]); Fabio et al. (2006[Fabio, R. D., Giovannini, R., Bertani, B., Borriello, M., Bozzoli, A., Donati, D., Falchi, A., Ghirlanda, D., Leslie, C. P., Pecunioso, A., Rumboldt, G. & Spada, S. (2006). Bioorg. Med. Chem. Lett. 16, 1749-1752.]); Kumar et al. (2008[Kumar, A., Singh, D., Jadhav, A., Pandya, N. D., Panmand, S. D. & Thakur, R. G. (2008). US Patent Appl. No. US 2008/0009635 A1.]). For the use of 4-oxo-tetrahydrocarbazole derivatives in the synthesis of indole alkaloids, see: Magnus et al. (1992[Magnus, P., Sear, N. L., Kim, C. S. & Vicker, N. (1992). J. Org. Chem. 57, 70-78.]); Ergün et al. (2000[Ergün, Y., Bayraktar, N., Patir, S. & Okay, G. (2000). J. Heterocycl. Chem. 37, 11-14.], 2002[Ergün, Y., Patir, S. & Okay, G. (2002). J. Heterocycl. Chem. 39, 315-317.]). For the synthesis of tetrahydrocarbazolone-based antitumor active compounds and inhibitors of HIV integrase from 4-oxo-tetrahydrocarbazoles, see: Li & Vince (2006[Li, X. & Vince, R. (2006). Bioorg. Med. Chem. 14, 2942-2955.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17NOS2

  • Mr = 303.43

  • Orthorhombic, P b c a

  • a = 16.8163 (3) Å

  • b = 9.8407 (2) Å

  • c = 17.2913 (4) Å

  • V = 2861.44 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.37 mm-1

  • T = 100 K

  • 0.47 × 0.32 × 0.29 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 = 0.847, Tmax = 0.901

  • 13394 measured reflections

  • 3540 independent reflections

  • 2912 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.075

  • wR(F2) = 0.195

  • S = 1.05

  • 3540 reflections

  • 183 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.73 e Å-3

  • [Delta][rho]min = -1.08 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the benzene ring.

D-H...A D-H H...A D...A D-H...A
C13-H13A...O1i 0.99 2.60 3.483 (5) 149
C2-H2A...Cg3ii 0.99 2.89 3.813 (4) 155
Symmetry codes: (i) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z].

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: XU5690 ).


Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskisehir, Turkey, for the use of the X-ray diffractometer.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bhattacharyya, P. & Chakraborty, D. P. (1987). Progress in the Chemistry of Organic Natural Products, edited by W. Hertz, H. Grisebach, G. W. Kirby & C. Tamm, Vol. 52, pp. 159-209. Wien, New York: Springer-Verlag.
Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA.
Çaylak, N., Hökelek, T., Uludag, N. & Patir, S. (2007). Acta Cryst. E63, o3913-o3914.  [CSD] [CrossRef] [details]
Chakraborty, D. P. (1993). The Alkaloids, edited by G. A. Cordell, Vol. 44, pp. 257-364. New York: Academic Press.
Ergün, Y., Bayraktar, N., Patir, S. & Okay, G. (2000). J. Heterocycl. Chem. 37, 11-14.
Ergün, Y., Patir, S. & Okay, G. (2002). J. Heterocycl. Chem. 39, 315-317.
Fabio, R. D., Giovannini, R., Bertani, B., Borriello, M., Bozzoli, A., Donati, D., Falchi, A., Ghirlanda, D., Leslie, C. P., Pecunioso, A., Rumboldt, G. & Spada, S. (2006). Bioorg. Med. Chem. Lett. 16, 1749-1752.  [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hökelek, T., Dal, H., Tercan, B., Göçmentürk, M. & Ergün, Y. (2009). Acta Cryst. E65, o1702-o1703.  [CSD] [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]
Kumar, A., Singh, D., Jadhav, A., Pandya, N. D., Panmand, S. D. & Thakur, R. G. (2008). US Patent Appl. No. US 2008/0009635 A1.
Li, X. & Vince, R. (2006). Bioorg. Med. Chem. 14, 2942-2955.  [CrossRef] [PubMed] [ChemPort]
Littell, R. & Allen, G. R. (1973). US Patent No. 3 740 404.
Magnus, P., Sear, N. L., Kim, C. S. & Vicker, N. (1992). J. Org. Chem. 57, 70-78.  [CrossRef] [ChemPort]
Patir, S., Okay, G., Gülce, A., Salih, B. & Hökelek, T. (1997). J. Heterocycl. Chem. 34, 1239-1242.  [ChemPort]
Ping, H. & Guoping, F. (1997). Assignee: Shanghai Hualian Pharmaceutical Co., People's Republic of China, Patent No. CN 1145902.
Saxton, J. E. (1983). Editor. Heterocyclic Compounds, Vol. 25, The Monoterpenoid Indole Alkaloids, ch. 8 and 11. New York: Wiley.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Uludag, N., Öztürk, A., Hökelek, T. & Erdogan, Ü. I. (2009). Acta Cryst. E65, o595-o596.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o598-o599   [ doi:10.1107/S1600536813007873 ]

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