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Volume 64 
Part 7 
Page o1304  
July 2008  

Received 10 April 2008
Accepted 16 June 2008
Online 19 June 2008

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Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.004 Å
R = 0.024
wR = 0.042
Data-to-parameter ratio = 17.6
Details
Open access

3,9-Dibromo-5,7-dihydrodibenzo[c,e]oxepine

Hai-Quan Zhang,a* Bao-Li,b Guang-Di Yangb and Yu-Guang Mab

aState Key Laboratory of Metastable Materials Science and Technology, Yanshan University, Qinhuangdao 066004, People's Republic of China, and bState Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, People's Republic of China
Correspondence e-mail: hqzhang@ysu.edu.cn

The title compound, C14H10Br2O, is a biphenyl derivative containing a -CH2-O-CH2- bridge in the 2,2'-position. The compound displays a twisted conformation with the two benzene rings making a dihedral angle of 45.02 (5)°, while the central seven-membered ring is in a boat conformation. The molecule lies on a crystallographic twofold axis of symmetry passing through the O atom and bisecting the 1,1' C-C bond.

Related literature

For a previous synthesis of related biphenyl molecules, see: Mislow & Glass (1961[Mislow, K. & Glass, M. (1961). J. Am. Chem. Soc. 83, 2780-2781.]).

[Scheme 1]

Experimental

Crystal data

  • C14H10Br2O

  • Mr = 354.04

  • Orthorhombic, P b c n

  • a = 16.5965 (3) Å

  • b = 10.2476 (6) Å

  • c = 7.2626 (14) Å

  • V = 1235.2 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 6.54 mm-1

  • T = 291 (2) K

  • 0.14 × 0.14 × 0.12 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.457, Tmax = 0.498 (expected range = 0.419-0.456)

  • 2468 measured reflections

  • 1371 independent reflections

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

  • Rint = 0.014
Refinement

  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.042

  • S = 1.05

  • 1371 reflections

  • 78 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.46 e Å-3

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., 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: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2098 ).

Acknowledgements

The authors acknowledge financial support from the National Science Foundation of China (20125421, 90101026, 50303007 and 60207003) and the Ministry of Science and Technology of China (2002CB6134003 and 2003CB3147032).

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Mislow, K. & Glass, M. (1961). J. Am. Chem. Soc. 83, 2780-2781.  [CrossRef] [ChemPort]
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2008). E64, o1304  [ doi:10.1107/S1600536808018175 ]

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