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Volume 69 
Part 4 
Page o585  
April 2013  

Received 8 March 2013
Accepted 19 March 2013
Online 23 March 2013

Key indicators
Single-crystal X-ray study
T = 153 K
Mean [sigma](C-C) = 0.004 Å
R = 0.039
wR = 0.091
Data-to-parameter ratio = 24.2
Details
Open access

7-Iodo-3,3-diphenyloctahydrobenzofuran

aSchool of Chemical Engineering and Environment, Beijing Institue of Technology, Beijing 100081, People's Republic of China
Correspondence e-mail: fuxue.chen@bit.edu.cn

The title compound, C20H21IO, was synthesized by cyclohaloetherification of 2-(cyclohex-2-enyl)-2,2-diphenylethanol in CH2Cl2, and crystallized with two independent molecules in the asymmetric unit. The six-membered cyclohexane ring adopts a chair conformation, while the five-membered ring adopts an envelope conformation with the fused C atom opposite the O atom as the flap in each case [displacements of the flap atoms = 0.6813 (3) and 0.6679 (3) Å]. In the crystal, molecules are linked via pairs of C-H...[pi] interactions, forming inversion dimers.

Related literature

For the title compound as a core structure of many drugs and natural products, see: Huang & Chen (2007[Huang, J. & Chen, F. (2007). Helv. Chim. Acta, 90, 1366-1372.]); Trost et al. (2003[Trost, B. M., Shen, H. C. & Surivet, J. (2003). Angew. Chem. Int. Ed. 42, 3943-3947.]). For the synthesis of 2-(cyclohex-2-enyl)-2,2-diphenylethanol, see: Brooner & Widenhoefer (2011[Brooner, R. E. M. & Widenhoefer, R. A. (2011). Chem. Eur. J. 17, 6170-6178.]).

[Scheme 1]

Experimental

Crystal data
  • C20H21IO

  • Mr = 404.27

  • Triclinic, [P \overline 1]

  • a = 11.4082 (18) Å

  • b = 12.523 (2) Å

  • c = 14.007 (3) Å

  • [alpha] = 73.306 (8)°

  • [beta] = 71.646 (8)°

  • [gamma] = 64.945 (7)°

  • V = 1692.8 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.89 mm-1

  • T = 153 K

  • 0.33 × 0.27 × 0.10 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.572, Tmax = 0.833

  • 19455 measured reflections

  • 9610 independent reflections

  • 7599 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.091

  • S = 1.00

  • 9610 reflections

  • 397 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.05 e Å-3

  • [Delta][rho]min = -0.75 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9-C14 and C15'-C20' rings, respectively.

D-H...A D-H H...A D...A D-H...A
C2-H2...Cg1i 1.00 2.53 3.519 (3) 171
C2'-H2'...Cg2ii 1.00 2.54 3.533 (3) 171
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+2, -z.

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5298 ).


Acknowledgements

Financial support from Beijing Institute of Technology is acknowledged.

References

Brooner, R. E. M. & Widenhoefer, R. A. (2011). Chem. Eur. J. 17, 6170-6178.  [PubMed]
Huang, J. & Chen, F. (2007). Helv. Chim. Acta, 90, 1366-1372.  [CrossRef] [ChemPort]
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Trost, B. M., Shen, H. C. & Surivet, J. (2003). Angew. Chem. Int. Ed. 42, 3943-3947.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o585  [ doi:10.1107/S1600536813007563 ]

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