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Volume 69 
Part 8 
Page o1270  
August 2013  

Received 18 June 2013
Accepted 11 July 2013
Online 17 July 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.007 Å
R = 0.051
wR = 0.108
Data-to-parameter ratio = 15.0
Details
Open access

(2S,3S)-3-(3-Bromophenyl)-6,6-dimethyl-2-nitro-2,3,6,7-tetrahydrobenzofuran-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, C16H16BrNO4, has two adjacent chiral C atoms and both have an S configuration. The fused cyclohex-2-enone and dihydrofuran rings both adopt envelope conformations, with the quaternary C atom and the nitro-substituted C atoms as the respective flap. The flap atoms lie 0.607 (3) and -0.253 (2) Å, respectively, from the mean plane of the remaining ring atoms on opposite sides. The dihedral angle between the mean plane of the four coplanar atoms of the dihydrofuran ring and the phenyl ring is 86.16 (3)°. In the crystal, molecules are linked by weak C-H...O interactions, forming a ladder motif parallel to the b axis.

Related literature

For the occurrence of dihydrofurans in nature and their synthetic applications, see: Fraga (1992[Fraga, B. M. (1992). Nat. Prod. Rep. 9, 217-241.]); Lipshutz (1986[Lipshutz, B. H. (1986). Chem. Rev. 86, 795-819.]). For synthetic procedures, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16BrNO4

  • Mr = 366.21

  • Orthorhombic, P 21 21 21

  • a = 6.6799 (7) Å

  • b = 7.3713 (9) Å

  • c = 32.9075 (14) Å

  • V = 1620.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.55 mm-1

  • T = 296 K

  • 0.38 × 0.36 × 0.31 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.384, Tmax = 0.455

  • 13344 measured reflections

  • 2997 independent reflections

  • 1857 reflections with I > 2[sigma](I)

  • Rint = 0.066

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.108

  • S = 1.00

  • 2997 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.51 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1221 Friedel pairs

  • Absolute structure parameter: 0.003 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...O1i 0.98 2.29 3.165 (6) 148
C5-H5A...O2ii 0.97 2.66 3.351 (6) 129
C14-H14...O1iii 0.93 2.65 3.559 (7) 167
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: FY2101 ).


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]
Fraga, B. M. (1992). Nat. Prod. Rep. 9, 217-241.  [CrossRef] [PubMed] [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Lipshutz, B. H. (1986). Chem. Rev. 86, 795-819.  [CrossRef] [ChemPort] [Web of Science]
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, o1270  [ doi:10.1107/S160053681301920X ]

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