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

Zhang, C.-X.; Zhang, Y.-P.; Xia, A.-B.

doi:10.1107/S1600536813001426

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 (C-C) = 0.010 Å
R = 0.056
wR = 0.175
Data-to-parameter ratio = 17.2
Details

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

Chi-Xiao Zhang,^a Yan-Peng Zhang ^a and Ai-Bao Xia ^a ^*

^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-HO interactions, forming chains along the a-axis direction.

Related literature

For related compounds, see: Hayashi et al. (2005); Li et al. (2009); Xia et al. (2009); Wu et al. (2011). For asymmetric Michael addition reactions, see: Luo et al. (2007). For enantioselective organocatalytic Michael additions, see: Peelen et al. (2005); Ma et al. (2008).

Experimental

Crystal data

C₁₆H₂₀BrNO₃
M_r = 354.24
Monoclinic, P 2₁
a = 5.6434 (4) Å
b = 9.2179 (6) Å
c = 16.5472 (9) Å
= 101.782 (3)°
V = 842.65 (9) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.279, T_max = 0.644
7234 measured reflections
3277 independent reflections
1619 reflections with I > 2(I)
R_int = 0.071

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.175
S = 1.00
3277 reflections
191 parameters
1 restraint
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.29 e Å^-3
Absolute structure: Flack (1983), 1259 Friedel pairs
Flack parameter: 0.03 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O3ⁱ	0.93	2.56	3.478 (9)	169
C16-H16BO3ⁱ	0.97	2.58	3.500 (8)	158
Symmetry code: (i) x+1, y, z.

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

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

organic compounds