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Volume 64 
Part 8 
Page o1448  
August 2008  

Received 10 June 2008
Accepted 3 July 2008
Online 9 July 2008

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Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.008 Å
R = 0.052
wR = 0.140
Data-to-parameter ratio = 15.8
Details
Open access

(2R)-Ethyl 2-(5-bromo-2,3-dioxoindolin-1-yl)propanoate

Alexander V. Kurkin,a* Anna A. Bernovskaya,a Marina A. Yurovskayaa and Victor B. Rybakova

aDepartment of Chemistry, Moscow State University, 119991 Moscow, Russian Federation
Correspondence e-mail: kurkin@direction.chem.msu.ru

The title compound, C13H12BrNO4, was obtained from an optically active aniline derivative. The structure was characterized by 1H NMR, 13C NMR, MS and X-ray diffraction techniques. 86% of the atoms of the two independent molecules in the asymmetric unit show non-crystallographic inversion symmetry.

Related literature

For related structures, see: Akkurt et al. (2006[Akkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575-o1577.]); Miehe et al. (1991[Miehe, G., Susse, P., Kupcik, V., Egert, E., Nieger, M., Kunz, G., Gerke, R., Knieriem, B., Niemeyer, M. & Luttke, W. (1991). Angew. Chem. Int. Ed. Engl. 30, 964-967.]); Robeyns et al. (2007[Robeyns, K., Rohand, T., Bouhfid, R., Essassi, E. L. M. & Van Meervelt, L. (2007). Acta Cryst. E63, o1747-o1748.]). For general background, see: Sandmeyer (1919[Sandmeyer, T. (1919). Helv. Chim. Acta, 2, 234-242.]); Silva et al. (2001[Silva, J. F., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.]); Spek (2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

[Scheme 1]

Experimental

Crystal data

  • C13H12BrNO4

  • Mr = 326.14

  • Monoclinic, P 21

  • a = 9.7390 (13) Å

  • b = 14.355 (2) Å

  • c = 9.8361 (10) Å

  • [beta] = 95.779 (9)°

  • V = 1368.1 (3) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 4.20 mm-1

  • T = 293 (2) K

  • 0.20 × 0.20 × 0.20 mm
Data collection

  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.385, Tmax = 0.432

  • 6047 measured reflections

  • 5502 independent reflections

  • 3935 reflections with I > 2[sigma](I)

  • Rint = 0.020

  • 1 standard reflection frequency: 60 min intensity decay: 2%
Refinement

  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.140

  • S = 1.02

  • 5502 reflections

  • 348 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2566 Friedel pairs

  • Flack parameter: -0.06 (3)

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2723 ).

Acknowledgements

The authors are indebted to the Russian Foundation for Basic Research for covering the licence fee for use of the Cambridge Structural Database.

References

Akkurt, M., Türktekin, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1575-o1577.  [CSD] [CrossRef] [details]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Miehe, G., Susse, P., Kupcik, V., Egert, E., Nieger, M., Kunz, G., Gerke, R., Knieriem, B., Niemeyer, M. & Luttke, W. (1991). Angew. Chem. Int. Ed. Engl. 30, 964-967.  [CrossRef]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Robeyns, K., Rohand, T., Bouhfid, R., Essassi, E. L. M. & Van Meervelt, L. (2007). Acta Cryst. E63, o1747-o1748.  [CrossRef] [details]
Sandmeyer, T. (1919). Helv. Chim. Acta, 2, 234-242.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Silva, J. F., Garden, S. J. & Pinto, A. C. (2001). J. Braz. Chem. Soc. 12, 273-324.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2008). E64, o1448  [ doi:10.1107/S1600536808020588 ]

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