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Volume 69 
Part 5 
Page o794  
May 2013  

Received 19 February 2013
Accepted 29 March 2013
Online 27 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.009 Å
R = 0.052
wR = 0.137
Data-to-parameter ratio = 14.7
Details
Open access

(4aR,9R,9aR)-7-Bromo-9-nitromethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-1-one

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 title compound, C14H14BrNO4, contains a tricyclic ring system including three contiguous stereocenters all of which exhibit an R configuration. The cyclohexanone ring adopts a chair conformation. The central oxane ring assumes a strained envelope conformation, with five of the ring atoms being nearly coplanar with the bromophenyl group and with the C atom adjacent to the O atom and fused with the cyclohexanone ring as the flap. In the crystal, molecules are linked into a three-dimensional network by C-H...O interactions.

Related literature

For related structures, see: Shi et al. (2004[Shi, G.-F., Lu, R.-H., Yang, Y.-S., Li, C.-L., Yang, A.-M. & Cai, L.-X. (2004). Acta Cryst. E60, o878-o880.]); Xia et al. (2009[Xia, A.-B., Tang, J., Jiang, J.-R., Wang, Y.-F. & Luo, S.-P. (2009). Acta Cryst. E65, o2091.]); Ndjakou Lenta et al. (2007[Ndjakou Lenta, B., Devkota, K. P., Neumann, B., Tsamo, E. & Sewald, N. (2007). Acta Cryst. E63, o1629-o1631.]). For background information on domino reactions, see Enders et al. (2007[Enders, D., Grondal, C. & Huttl, M. R. M. (2007). Angew. Chem. Int. Ed. 46, 1570-1581.]); Yu & Wang (2002[Yu, X. & Wang, W. (2002). Org. Biomol. Chem. 6, 2037-2046.]).

[Scheme 1]

Experimental

Crystal data
  • C14H14BrNO4

  • Mr = 340.17

  • Monoclinic, P 21

  • a = 10.3457 (7) Å

  • b = 5.4662 (5) Å

  • c = 13.2446 (12) Å

  • [beta] = 102.849 (2)°

  • V = 730.25 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.83 mm-1

  • T = 296 K

  • 0.53 × 0.47 × 0.14 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.224, Tmax = 0.673

  • 6335 measured reflections

  • 2655 independent reflections

  • 1537 reflections with I > 2[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.137

  • S = 1.00

  • 2655 reflections

  • 181 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1058 Friedel pairs

  • Flack parameter: 0.021 (17)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O1i 0.93 2.71 3.520 (9) 146
C8-H8B...O2ii 0.97 2.59 3.489 (6) 155
C8-H8A...O4iii 0.97 2.54 3.253 (4) 131
C10-H10...O2iv 0.98 2.53 3.300 (8) 135
C11-H11...O3v 0.98 2.59 3.547 (8) 165
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) [-x+1, y-{\script{1\over 2}}, -z]; (iii) [-x+1, y+{\script{1\over 2}}, -z]; (iv) x, y-1, z; (v) 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 Corporation, 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: FY2090 ).


Acknowledgements

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

References

Enders, D., Grondal, C. & Huttl, M. R. M. (2007). Angew. Chem. Int. Ed. 46, 1570-1581.  [ISI] [CrossRef] [ChemPort]
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]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Ndjakou Lenta, B., Devkota, K. P., Neumann, B., Tsamo, E. & Sewald, N. (2007). Acta Cryst. E63, o1629-o1631.  [CSD] [CrossRef] [details]
Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2007). CrystalStructure. Rigaku Americas Corporation, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Shi, G.-F., Lu, R.-H., Yang, Y.-S., Li, C.-L., Yang, A.-M. & Cai, L.-X. (2004). Acta Cryst. E60, o878-o880.  [CSD] [CrossRef] [ChemPort] [details]
Xia, A.-B., Tang, J., Jiang, J.-R., Wang, Y.-F. & Luo, S.-P. (2009). Acta Cryst. E65, o2091.  [CSD] [CrossRef] [details]
Yu, X. & Wang, W. (2002). Org. Biomol. Chem. 6, 2037-2046.  [CrossRef]


Acta Cryst (2013). E69, o794  [ doi:10.1107/S1600536813008659 ]

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