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Volume 69 
Part 1 
Page m16  
January 2013  

Received 13 November 2012
Accepted 22 November 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.100
Data-to-parameter ratio = 19.1
Details
Open access

rac-(S,S)-Bis(1-ferrocenylbut-3-enyl) ether

aCollege of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou, Jiangsu 215123, People's Republic of China
Correspondence e-mail: wangjianjun1030@sohu.com

The title complex, [Fe2(C5H5)2(C18H20O)], formed by dehydration of 1-ferrocenylbut-3-en-1-ol, crystallizes as a racemic compound. The central C-O-C fragment, in which the C atoms are the chiral centers, is characterized by an angle of 116.26 (10)° at the O atom. One ferrocene group shows a staggered conformation whereas the other shows an eclipsed conformation.

Related literature

For general information on ferrocenyl ethers, see: Ferguson et al. (1996[Ferguson, G., Trotter, J., Glidewell, C. & Zakaria, C. M. (1996). Acta Cryst. C52, 775-777.]); Matkovic-Calogovic et al. (1993[Matkovic-Calogovic, D., Rapic, V. & Kovac, S. (1993). Acta Cryst. C49, 226-228.]); Gasser et al. (2007[Gasser, G., Fischmann, A. J., Forsyth, C. M. & Spiccia, L. (2007). J. Organomet. Chem. 692, 3835-3840.]). For applications of dinuclear ferrocenyl derivatives, see: Gao et al. (2011[Gao, Y., Li, H.-D., Ke, C.-F., Xie, L.-L., Wei, B. & Yuan, Y.-F. (2011). Appl. Organomet. Chem. 25, 407-411.]); Locke et al. (2001[Locke, A. J., Jones, C. & Richards, C. J. (2001). J. Organomet. Chem. 637-639, 669-676.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe2(C5H5)2(C18H20O)]

  • Mr = 494.22

  • Triclinic, [P \overline 1]

  • a = 9.7865 (15) Å

  • b = 9.8274 (15) Å

  • c = 12.1816 (19) Å

  • [alpha] = 99.405 (2)°

  • [beta] = 94.976 (2)°

  • [gamma] = 101.657 (2)°

  • V = 1123.3 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.31 mm-1

  • T = 150 K

  • 0.50 × 0.25 × 0.25 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.561, Tmax = 0.736

  • 7657 measured reflections

  • 5352 independent reflections

  • 4759 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.027

  • wR(F2) = 0.100

  • S = 0.81

  • 5352 reflections

  • 280 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: BH2465 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20874068), the Natural Science Foundation of Jiangsu Province (No. BK2009584) and the Undergraduate Innovating Experimentation Project of Soochow University (No. 5731510110).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Ferguson, G., Trotter, J., Glidewell, C. & Zakaria, C. M. (1996). Acta Cryst. C52, 775-777.  [CSD] [CrossRef] [details]
Gao, Y., Li, H.-D., Ke, C.-F., Xie, L.-L., Wei, B. & Yuan, Y.-F. (2011). Appl. Organomet. Chem. 25, 407-411.  [ISI] [CSD] [CrossRef] [ChemPort]
Gasser, G., Fischmann, A. J., Forsyth, C. M. & Spiccia, L. (2007). J. Organomet. Chem. 692, 3835-3840.  [CSD] [CrossRef] [ChemPort]
Locke, A. J., Jones, C. & Richards, C. J. (2001). J. Organomet. Chem. 637-639, 669-676.  [CrossRef] [ChemPort]
Matkovic-Calogovic, D., Rapic, V. & Kovac, S. (1993). Acta Cryst. C49, 226-228.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, m16  [ doi:10.1107/S1600536812048064 ]

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