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Volume 69 
Part 12 
Pages o1797-o1798  
December 2013  

Received 4 November 2013
Accepted 12 November 2013
Online 20 November 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.116
Data-to-parameter ratio = 14.6
Details
Open access

2-{4-Methyl-N-[(2,3,4,9-tetra­hydro-1H-carbazol-3-yl)meth­yl]benzene­sulfon­amido}­ethyl 4-methyl­benzene­sulfonate

aDokuz Eylül University, Faculty of 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, C29H32N2O5S2, the indole ring system is nearly planar, with a maximum deviation of 0.013 (2) Å, and the cyclo­hexenone ring has an envelope conformation with the methine C atom as the flap. The two methyl­benzene rings are approximately perpendicular to each other, making a dihedral angle of 89.09 (8)°. In the crystal, N-H...O hydrogen bonds link the mol­ecules into a chain running along the a-axis direction, and weak C-H...O hydrogen bonds and 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 related structures, see: Hökelek et al. (2009[Hökelek, T., Dal, H., Tercan, B., Göçmentürk, M. & Ergün, Y. (2009). Acta Cryst. E65, o1702-o1703.]); 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.]); Gündogdu et al. (2011[Gündogdu, C., Göçmentürk, M., Ergün, Y., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, o1470-o1471.]). For the use of tetra­hydro­carbazolone in the synthesis of central-nervous-system-active drugs, see: Romeo et al. (2006[Romeo, G., Materia, L., Pittalá, V., Modica, M., Salerno, L., Siracusa, M., Russo, F. & Minneman, K. P. (2006). Bioorg. Med. Chem. 14, 5211-5219.]). For the syntheses of tetra­hydro­carbazolone-based anti­tumor-active compounds from tetra­hydro­carbazoles, see: Chen et al. (2009[Chen, J., Lou, J., Liu, T., Wu, R., Dong, X., He, Q., Yang, B. & Hu, Y. (2009). Arch. Pharm. 342, 165-172.]). For the syntheses of amino­tetra­hydro­carbazoles as central nervous system agents, see: Mooradian et al. (1977[Mooradian, A., Dupont, P. E., Hlavac, A. G., Aceto, M. D. & Pearl, J. (1977). J. Med. Chem. 20, 487-492.]). 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
  • C29H32N2O5S2

  • Mr = 552.69

  • Monoclinic, P 21 /c

  • a = 10.5719 (5) Å

  • b = 10.8783 (6) Å

  • c = 23.8868 (11) Å

  • [beta] = 93.507 (2)°

  • V = 2741.9 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.11 mm-1

  • T = 150 K

  • 0.21 × 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 = 0.701, Tmax = 0.761

  • 168526 measured reflections

  • 5101 independent reflections

  • 4955 reflections with I > 2[sigma](I)

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.05

  • 5101 reflections

  • 349 parameters

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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg5 are the centroids of the C4A/C5A/C8A/N9/C9A and C20-C25 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N9-H9...O5i 0.84 (2) 2.18 (2) 2.9561 (19) 154.1 (18)
C21-H21...O4ii 0.95 2.38 3.230 (2) 148
C8-H8...Cg5iii 0.95 2.81 3.5127 (18) 131
C10-H10B...Cg2iv 0.99 2.58 3.5538 (18) 168
Symmetry codes: (i) x-1, y, z; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: XU5750 ).


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.
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] [IUCr Journals]
Chen, J., Lou, J., Liu, T., Wu, R., Dong, X., He, Q., Yang, B. & Hu, Y. (2009). Arch. Pharm. 342, 165-172.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gündogdu, C., Göçmentürk, M., Ergün, Y., Tercan, B. & Hökelek, T. (2011). Acta Cryst. E67, o1470-o1471.  [CSD] [CrossRef] [IUCr Journals]
Hökelek, T., Dal, H., Tercan, B., Göçmentürk, M. & Ergün, Y. (2009). Acta Cryst. E65, o1702-o1703.  [CSD] [CrossRef] [IUCr Journals]
Mooradian, A., Dupont, P. E., Hlavac, A. G., Aceto, M. D. & Pearl, J. (1977). J. Med. Chem. 20, 487-492.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Romeo, G., Materia, L., Pittalá, V., Modica, M., Salerno, L., Siracusa, M., Russo, F. & Minneman, K. P. (2006). Bioorg. Med. Chem. 14, 5211-5219.  [CrossRef] [PubMed] [ChemPort]
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]
Uludag, N., Öztürk, A., Hökelek, T. & Erdogan, Ü. I. (2009). Acta Cryst. E65, o595-o596.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1797-o1798   [ doi:10.1107/S1600536813031097 ]

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