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

Wang, Y.; Chen, R.; Li, Z.; Xu, D.

doi:10.1107/S1600536811051725

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 (C-C) = 0.007 Å
R = 0.033
wR = 0.104
Data-to-parameter ratio = 17.0
Details

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

Yifeng Wang,^a Ruxiang Chen,^a Zhaobo Li ^b and Danqian Xu ^a ^*

^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-HO hydrogen bonds.

Related literature

For general background, see: Li et al. (2009), Malerich et al. (2008); For related structures, see: Li et al. (2005).

Experimental

Crystal data

C₁₄H₁₄BrNO₅
M_r = 356.17
Monoclinic, P 2₁
a = 9.6237 (7) Å
b = 6.6547 (4) Å
c = 12.0503 (8) Å
= 105.794 (2)°
V = 742.60 (9) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.301, T_max = 0.542
7336 measured reflections
3272 independent reflections
1893 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.104
S = 1.00
3272 reflections
192 parameters
1 restraint
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.45 e Å^-3
Absolute structure: Flack (1983), 1327 Friedel pairs
Flack parameter: 0.014 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O5ⁱ	0.93	2.58	3.306 (2)	135
C10-H10O3ⁱⁱ	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); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
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.
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, J. P., Hagihara, K. & Rawal, V. H. (2008). J. Am. Chem. Soc. 130, 14416-14417.
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.

organic compounds