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Volume 65 
Part 9 
Page o2069  
September 2009  

Received 26 July 2009
Accepted 28 July 2009
Online 8 August 2009

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Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.153
Data-to-parameter ratio = 22.7
Details
Open access

Ethyl 2-acetoxymethyl-1-phenylsulfonyl-1H-indole-3-carboxylate

B. Gunasekaran,a Radhakrishnan Sureshbabu,b A. K. Mohanakrishnan,b G. Chakkaravarthic and V. Manivannand*

aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India,cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: manivan_1999@yahoo.com

In the title compound, C20H19NO6S, the phenyl ring of the phenylsulfonyl group makes a dihedral angle of 83.35 (5)° with the indole ring system. The molecular structure exhibits a number of short intramolecular C-H...O contacts.

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001[Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug Des. 16, 167-174.]); Quetin-Leclercq (1994[Quetin-Leclercq, J. (1994). J. Pharm. Belg. 49, 181-192.]); Mukhopadhyay et al. (1981[Mukhopadhyay, S., Handy, G. A., Funayama, S. & Cordell, G. A. (1981). J. Nat. Prod. 44, 696-700.]); Singh et al. (2000[Singh, U. P., Sarma, B. K., Mishra, P. K. & Ray, A. B. (2000). Fol. Microbiol. 45, 173-176.]). For related structures, see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.], 2008[Chakkaravarthi, G., Sureshbabu, R., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o732.]); Gunasekaran et al. (2009[Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o1856.]); For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C20H19NO6S

  • Mr = 401.42

  • Orthorhombic, P b c a

  • a = 18.9097 (6) Å

  • b = 7.9737 (2) Å

  • c = 24.7877 (7) Å

  • V = 3737.50 (18) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 295 K

  • 0.25 × 0.20 × 0.20 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.949, Tmax = 0.959

  • 28247 measured reflections

  • 5788 independent reflections

  • 3533 reflections with I > 2[sigma](I)

  • Rint = 0.031
Refinement

  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.153

  • S = 1.01

  • 5788 reflections

  • 255 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O5 0.93 2.57 3.446 (2) 157
C6-H6...O2 0.93 2.50 2.875 (3) 105
C8-H8...O2 0.93 2.42 2.993 (3) 120
C11-H11...O3 0.93 2.48 3.003 (3) 116
C18-H18A...O4 0.97 2.31 2.886 (3) 117
C18-H18B...O1 0.97 2.30 2.793 (3) 111

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2226 ).

Acknowledgements

BG thanks AMET University management, India, for their kind support.

References

Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug Des. 16, 167-174.  [PubMed] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698.  [CSD] [CrossRef] [details]
Chakkaravarthi, G., Sureshbabu, R., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o732.  [CSD] [CrossRef] [details]
Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o1856.  [CSD] [CrossRef] [details]
Mukhopadhyay, S., Handy, G. A., Funayama, S. & Cordell, G. A. (1981). J. Nat. Prod. 44, 696-700.  [CrossRef] [ChemPort] [PubMed] [ISI]
Quetin-Leclercq, J. (1994). J. Pharm. Belg. 49, 181-192.  [ChemPort] [PubMed]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, U. P., Sarma, B. K., Mishra, P. K. & Ray, A. B. (2000). Fol. Microbiol. 45, 173-176.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2009). E65, o2069  [ doi:10.1107/S1600536809029985 ]

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