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Volume 69 
Part 6 
Page o979  
June 2013  

Received 19 April 2013
Accepted 20 May 2013
Online 31 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.102
Data-to-parameter ratio = 25.2
Details
Open access

5-Benzyloxy-3-methyl-1-tosyl-1H-indole

aDepartamento de Química Orgânica, Instituto de Química, Universidade Federal do Rio Grande do Sul, Porto Alegre/RS, 91501-970, Brazil,bDepartment of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556, USA, and cBruker ACS Inc., 5465 East Cheryl Parkway, Madison, WI 53711, USA
Correspondence e-mail: gustavo.silveira@iq.ufrgs.br

The title compound, C23H21NO3S, represents one of the few examples of a 5-substituted indole with a toluenesulfonyl group bonded to the N atom. The benzyl group adopts a synclinal geometry with respect to the indole ring [dihedral angle = 59.95 (4)°], while the tolyl ring is oriented close to perpendicular to the indole ring, making a dihedral angle of 81.85 (3)°. The indole N atom exhibits a slight pyramidalization.

Related literature

For background to physostigmine and related marine natural products, see: Marino et al. (1989[Marino, J. P., Kim, M.-W. & Lawrence, R. (1989). J. Org. Chem. 54, 1782-1784.], 1992[Marino, J. P., Bogdan, S. & Kimura, K. (1992). J. Am. Chem. Soc. 114, 5566-5572.]). For recent, related structural and synthetic studies, see: Pozza Silveira et al. (2012[Pozza Silveira, G., Bonfante de Carvallho, C. & Oliver, A. (2012). Acta Cryst. E68, o2048.]); Silveira & Marino (2013[Silveira, G. P. & Marino, J. P. (2013). J. Org. Chem. 78, 3379-3383.]). For related compounds, see: Xiong et al. (2001[Xiong, W.-N., Yang, C.-G. & Jiang, B. (2001). Bioorg. Med. Chem. 9, 1773-1780.]); Witulski et al. (2000[Witulski, B., Bushcmann, N. & Bergsträsser, U. (2000). Tetrahedron, 56, 8473-8480.]). For reference structural data see: Allen et al. (1995[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1995). International Tables for Crystallography, Vol. C, edited by A. J. C. Wilson, pp. 685-706. Dordrecht: Kluwer.]).

[Scheme 1]

Experimental

Crystal data
  • C23H21NO3S

  • Mr = 391.47

  • Monoclinic, P 21 /n

  • a = 8.317 (3) Å

  • b = 15.601 (6) Å

  • c = 14.752 (5) Å

  • [beta] = 90.884 (11)°

  • V = 1914.1 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 100 K

  • 0.39 × 0.33 × 0.15 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.636, Tmax = 0.746

  • 30660 measured reflections

  • 6415 independent reflections

  • 5550 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.102

  • S = 1.04

  • 6415 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.59 e Å-3

  • [Delta][rho]min = -0.42 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS 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: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: KJ2226 ).


Acknowledgements

We thank the University of Notre Dame for its generous support of this program.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1995). International Tables for Crystallography, Vol. C, edited by A. J. C. Wilson, pp. 685-706. Dordrecht: Kluwer.
Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Marino, J. P., Bogdan, S. & Kimura, K. (1992). J. Am. Chem. Soc. 114, 5566-5572.  [CrossRef] [ChemPort]
Marino, J. P., Kim, M.-W. & Lawrence, R. (1989). J. Org. Chem. 54, 1782-1784.  [CrossRef] [ChemPort]
Pozza Silveira, G., Bonfante de Carvallho, C. & Oliver, A. (2012). Acta Cryst. E68, o2048.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Silveira, G. P. & Marino, J. P. (2013). J. Org. Chem. 78, 3379-3383.  [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Witulski, B., Bushcmann, N. & Bergsträsser, U. (2000). Tetrahedron, 56, 8473-8480.  [CrossRef] [ChemPort]
Xiong, W.-N., Yang, C.-G. & Jiang, B. (2001). Bioorg. Med. Chem. 9, 1773-1780.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o979  [ doi:10.1107/S1600536813014001 ]

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