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Volume 69 
Part 8 
Page o1197  
August 2013  

Received 17 June 2013
Accepted 27 June 2013
Online 3 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.010 Å
R = 0.059
wR = 0.125
Data-to-parameter ratio = 14.0
Details
Open access

(2S,3R)-3-(2-Bromophenyl)-2-nitro-2,3,6,7-tetrahydro-1-benzofuran-4(5H)-one

aCatalytic Hydrogenation Research Center, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: chrc@zjut.edu.cn

The title compound, C14H12BrNO4, has two chiral C atoms. The C atom next to the O atom in the dihydrofuran ring has an S configuration, while the adjacent chiral C atom has an R configuration. The cyclohex-2-enone and dihydrofuran rings both adopt envelope conformations, with the flap atoms (middle CH2 in cyclohex-2-enone and NO2-substituted C in dihydrofuran) lying 0.612 (3) and 0.295 (2) Å, respectively, from the mean plane of the remaining atoms. The dihedral angle between the mean planes of the furan and benzene rings is 80.0 (3)°. In the crystal, the molecules are linked by C-H...O interactions, generating a three-dimensional network.

Related literature

For global background on functionalized 2,3-dihydrofurans, see: Fan et al. (2010[Fan, L. P., Li, P., Li, X. S., Xu, D. C., Ge, M. M., Zhu, W. D. & Xie, J. W. (2010). J. Org. Chem. 75, 8716-8719.]); Rueping et al. (2010[Rueping, M., Parra, A., Uria, U., Besselievre, F. & Merino, E. (2010). Org. Lett. 12, 5680-5683.]). The absolute configuration was assigned by the method of Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12BrNO4

  • Mr = 338.16

  • Orthorhombic, P 21 21 21

  • a = 7.2162 (8) Å

  • b = 7.3372 (8) Å

  • c = 25.9727 (13) Å

  • V = 1375.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 3.00 mm-1

  • T = 296 K

  • 0.54 × 0.31 × 0.23 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 = 0.334, Tmax = 0.505

  • 10897 measured reflections

  • 2548 independent reflections

  • 1456 reflections with I > 2[sigma](I)

  • Rint = 0.068

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.125

  • S = 1.00

  • 2548 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.57 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1041 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
C1-H1...O1i 0.98 2.51 3.486 (12) 171
C7-H7A...O3ii 0.97 2.66 3.403 (12) 134
C7-H7B...O3iii 0.97 2.52 3.480 (13) 172
Symmetry codes: (i) x+1, y, z; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iii) x, y+1, 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: PK2489 ).


Acknowledgements

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

References

Fan, L. P., Li, P., Li, X. S., Xu, D. C., Ge, M. M., Zhu, W. D. & Xie, J. W. (2010). J. Org. Chem. 75, 8716-8719.  [CSD] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (2006). PROCESS_AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku Americas, The Woodlands, Texas, USA.
Rueping, M., Parra, A., Uria, U., Besselievre, F. & Merino, E. (2010). Org. Lett. 12, 5680-5683.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1197  [ doi:10.1107/S1600536813017698 ]

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