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Volume 69 
Part 2 
Page o263  
February 2013  

Received 27 December 2012
Accepted 15 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.010 Å
R = 0.056
wR = 0.175
Data-to-parameter ratio = 17.2
Details
Open access

(2S,4R)-2-[(1R)-1-(4-Bromophenyl)-2-nitroethyl]-4-ethylcyclohexanone

aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: xiaaibao@zjut.edu.cn

The crystal structure of the title compound, C16H20BrNO3, contains three chiral centers in the configuration 1R,2S,6R. The cyclohexane ring is in a chair conformation. In the crystal, molecules are linked by weak C-H...O interactions, forming chains along the a-axis direction.

Related literature

For related compounds, see: Hayashi et al. (2005[Hayashi, Y., Gotog, H., Hayashi, T. & Shoji, M. (2005). Angew. Chem. Int. Ed. 44, 4212-4215.]); Li et al. (2009[Li, Z., Guo, Y., Li, B. & Luo, S. (2009). Acta Cryst. E65, o2023.]); Xia et al. (2009[Xia, A.-B., Tang, J., Jiang, J.-R., Wang, Y.-F. & Luo, S.-P. (2009). Acta Cryst. E65, o2091.]); Wu et al. (2011[Wu, C., Zhao, L. & Xia, A.-B. (2011). Acta Cryst. E67, o1939.]). For asymmetric Michael addition reactions, see: Luo et al. (2007[Luo, S., Zhang, L., Mi, X., Qiao, Y. & Cheng, J.-P. (2007). J. Org. Chem. 72, 9350-9352.]). For enantioselective organocatalytic Michael additions, see: Peelen et al. (2005[Peelen, T. J., Chi, Y. & Gellman, S. H. (2005). J. Am. Chem. Soc. 127, 11598-11599.]); Ma et al. (2008[Ma, A., Zhu, S. & Ma, D. (2008). Tetrahedron Lett. 49, 3075-3077.]).

[Scheme 1]

Experimental

Crystal data
  • C16H20BrNO3

  • Mr = 354.24

  • Monoclinic, P 21

  • a = 5.6434 (4) Å

  • b = 9.2179 (6) Å

  • c = 16.5472 (9) Å

  • [beta] = 101.782 (3)°

  • V = 842.65 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.45 mm-1

  • T = 296 K

  • 0.52 × 0.31 × 0.18 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 = 0.279, Tmax = 0.644

  • 7234 measured reflections

  • 3277 independent reflections

  • 1619 reflections with I > 2[sigma](I)

  • Rint = 0.071

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.175

  • S = 1.00

  • 3277 reflections

  • 191 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1259 Friedel pairs

  • Flack parameter: 0.03 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O3i 0.93 2.56 3.478 (9) 169
C16-H16B...O3i 0.97 2.58 3.500 (8) 158
Symmetry code: (i) x+1, y, z.

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, 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.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2194 ).


Acknowledgements

The authors thank Professor Jian-Ming Gu of Zhejiang University for his help.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hayashi, Y., Gotog, H., Hayashi, T. & Shoji, M. (2005). Angew. Chem. Int. Ed. 44, 4212-4215.  [ISI] [CrossRef] [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Li, Z., Guo, Y., Li, B. & Luo, S. (2009). Acta Cryst. E65, o2023.  [CSD] [CrossRef] [details]
Luo, S., Zhang, L., Mi, X., Qiao, Y. & Cheng, J.-P. (2007). J. Org. Chem. 72, 9350-9352.  [CSD] [CrossRef] [PubMed] [ChemPort]
Ma, A., Zhu, S. & Ma, D. (2008). Tetrahedron Lett. 49, 3075-3077.  [ISI] [CrossRef] [ChemPort]
Peelen, T. J., Chi, Y. & Gellman, S. H. (2005). J. Am. Chem. Soc. 127, 11598-11599.  [ISI] [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]
Wu, C., Zhao, L. & Xia, A.-B. (2011). Acta Cryst. E67, o1939.  [CrossRef] [details]
Xia, A.-B., Tang, J., Jiang, J.-R., Wang, Y.-F. & Luo, S.-P. (2009). Acta Cryst. E65, o2091.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o263  [ doi:10.1107/S1600536813001426 ]

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