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Volume 68 
Part 1 
Page o110  
January 2012  

Received 18 November 2011
Accepted 1 December 2011
Online 14 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.033
wR = 0.104
Data-to-parameter ratio = 17.0
Details
Open access

(S)-3-Acetyl-3-[(R)-1-(4-bromophenyl)-2-nitroethyl]oxolan-2-one

aCatalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China, and bHangzhou Minsheng Pharmaceutical Group Co. Ltd, Hangzhou, People's Republic of China
Correspondence e-mail: chrc@zjut.edu.cn

The title compound, C14H14BrNO5, has two chiral C atoms. The quaternary C atom in the oxolanone ring has an S configuration, while the adjacent tertiary C atom has an R configuration. The oxolanone ring adopts an envelope conformation, with the flap C atom lying 0.298 (3) Å from the mean plane of the remaining four atoms. In the crystal, molecules are connected into chains along [010] via weak C-H...O hydrogen bonds.

Related literature

For general background, see: Li et al. (2009[Li, N., Xi, G. H., Wu, Q. H., Liu, W. H., Ma, J. J. & Wang, C. (2009). Chin. J. Org. Chem. 29, 1018-1038.]), Malerich et al. (2008[Malerich, J. P., Hagihara, K. & Rawal, V. H. (2008). J. Am. Chem. Soc. 130, 14416-14417.]); For related structures, see: Li et al. (2005[Li, H. M., Wang, Y., Tang, L., Wu, F. H., Liu, X. F., Guo, C. Y., Foxman, B. M. & Deng, L. (2005). Angew. Chem. Int. Ed. 44, 105-108.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14BrNO5

  • Mr = 356.17

  • Monoclinic, P 21

  • a = 9.6237 (7) Å

  • b = 6.6547 (4) Å

  • c = 12.0503 (8) Å

  • [beta] = 105.794 (2)°

  • V = 742.60 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.79 mm-1

  • T = 296 K

  • 0.43 × 0.27 × 0.22 mm

Data collection
  • Rigaku R-AXIS RAPID/ZJUG diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.301, Tmax = 0.542

  • 7336 measured reflections

  • 3272 independent reflections

  • 1893 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.104

  • S = 1.00

  • 3272 reflections

  • 192 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1327 Friedel pairs

  • Flack parameter: 0.014 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O5i 0.93 2.58 3.306 (2) 135
C10-H10...O3ii 0.93 2.63 3.514 (2) 158
Symmetry codes: (i) x, y-1, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: PROCESS-AUTO (Rigaku, 2006[Rigaku (2006). PROCESS_AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.]); 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, 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: PK2367 ).


Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (No. Y4110373) and the Foundation of Zhejiang Education Committee (No. Y201018458). We are also grateful for the help of Professor Jian-Ming Gu of Zhejiang University.

References

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]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Li, H. M., Wang, Y., Tang, L., Wu, F. H., Liu, X. F., Guo, C. Y., Foxman, B. M. & Deng, L. (2005). Angew. Chem. Int. Ed. 44, 105-108.  [ISI] [CSD] [CrossRef] [ChemPort]
Li, N., Xi, G. H., Wu, Q. H., Liu, W. H., Ma, J. J. & Wang, C. (2009). Chin. J. Org. Chem. 29, 1018-1038.  [ChemPort]
Malerich, J. P., Hagihara, K. & Rawal, V. H. (2008). J. Am. Chem. Soc. 130, 14416-14417.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Rigaku (2006). PROCESS_AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o110  [ doi:10.1107/S1600536811051725 ]

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