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Volume 70 
Part 1 
Pages o78-o79  
January 2014  

Received 9 December 2013
Accepted 17 December 2013
Online 21 December 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.031
wR = 0.090
Data-to-parameter ratio = 14.4
Details
Open access

2-{N-[(2,3,4,9-Tetra­hydro-1H-carbazol-3-yl)meth­yl]methyl­sulfonamido}­ethyl methane­sulfonate

aDokuz Eylül University, Faculty of Arts and Sciences, Department of Chemistry, Tinaztepe, 35160 Buca, Izmir, Turkey,bUniversité de Montréal, Département de Chimie, H3C 3J7, Montréal, Québec, Canada,cDepartment of Physics, Sakarya University, 54187 Esentepe, Sakarya, Turkey, and dHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey
Correspondence e-mail: merzifon@hacettepe.edu.tr

In the title compound, C17H24N2O5S2, the indole ring system is nearly planar [maximum deviation = 0.032 (1) Å] and the cyclo­hexene ring has a half-chair conformation. In the crystal, N-H...O hydrogen bonds link the mol­ecules into a chain running along the b-axis direction. Weak C-H...O hydrogen bonds and weak C-H...[pi] inter­actions are observed between the chains.

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 the anti­tumor activity of tetra­hydro­carbazoles containing an amine unit, see: Chen et al. (2009[Chen, J., Lou, J., Liu, T., Wu, R., Dong, X., He, Q., Yang, B. & Hu, Y. (2009). Arch. Pharm. Chem. 342, 165-167.]). For the most potent drugs, such as ellipcitine and olivacine, for the treatment of a variety of cancers, see: Pelletier (1970[Pelletier, S. W. (1970). Chemistry of Alkaloids, pp. 1-9. New York: Nostrand Reinhold Company.]). For the use of tetra­hydro­carbazoles in the synthesis of pyridocarbazoles, see: Knölker & Reddy (2002[Knölker, H. J. & Reddy, K. R. (2002). Chem. Rev. 102, 4303-4427.]). For related structures, see: Patir et al. (1997[Patir, S., Okay, G., Gülce, A., Salih, B. & Hökelek, T. (1997). J. Heterocycl. Chem., 34, 1239-1242.]); Gündogdu et al. (2011[Gündogdu, C., Göçmentürk, M., Ergün, Y., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, o1470-o1471.]); Göçmen­türk et al. (2013[Göçmentürk, M., Ergün, Y., Mougang-Soume, B., Çaylak Delibas, N. & Hökelek, T. (2013). Acta Cryst. E69, o1797-o1798.]).

[Scheme 1]

Experimental

Crystal data
  • C17H24N2O5S2

  • Mr = 400.50

  • Monoclinic, P 21 /c

  • a = 5.4399 (2) Å

  • b = 18.0322 (6) Å

  • c = 19.0103 (6) Å

  • [beta] = 98.973 (2)°

  • V = 1841.96 (11) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.90 mm-1

  • T = 150 K

  • 0.18 × 0.16 × 0.13 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 = 0.623, Tmax = 0.686

  • 47392 measured reflections

  • 3472 independent reflections

  • 3357 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.090

  • S = 1.05

  • 3472 reflections

  • 241 parameters

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

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4a/C5a/C8a/N9/C9a ring.

D-H...A D-H H...A D...A D-H...A
N9-H9...O2i 0.83 (2) 2.17 (2) 2.9804 (16) 166 (2)
C11-H11C...O4ii 0.98 2.45 3.171 (2) 130
C13-H13A...O5iii 0.99 2.46 3.4148 (19) 161
C14-H14B...O5iv 0.98 2.42 3.317 (2) 152
C11-H11A...Cg2ii 0.98 2.95 3.6705 (19) 131
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y, -z; (iv) -x, -y, -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: XU5758 ).


References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, J., Lou, J., Liu, T., Wu, R., Dong, X., He, Q., Yang, B. & Hu, Y. (2009). Arch. Pharm. Chem. 342, 165-167.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Göçmentürk, M., Ergün, Y., Mougang-Soume, B., Çaylak Delibas, N. & Hökelek, T. (2013). Acta Cryst. E69, o1797-o1798.  [CSD] [CrossRef] [IUCr Journals]
Gündogdu, C., Göçmentürk, M., Ergün, Y., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, o1470-o1471.  [CSD] [CrossRef] [IUCr Journals]
Knölker, H. J. & Reddy, K. R. (2002). Chem. Rev. 102, 4303-4427.  [Web of Science] [PubMed]
Patir, S., Okay, G., Gülce, A., Salih, B. & Hökelek, T. (1997). J. Heterocycl. Chem., 34, 1239-1242.
Pelletier, S. W. (1970). Chemistry of Alkaloids, pp. 1-9. New York: Nostrand Reinhold Company.
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] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o78-o79   [ doi:10.1107/S1600536813034016 ]

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