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

Xie, H.-J.; Zhao, C.-Z.; Sun, J.; Chen, S.; Wang, J.-J.

doi:10.1107/S1600536812048064

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 (C-C) = 0.002 Å
R = 0.027
wR = 0.100
Data-to-parameter ratio = 19.1
Details

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

Hao-Jun Xie,^a Chun-Zheng Zhao,^a Jun Sun,^a Si Chen ^a and Jian-Jun Wang ^a ^*

^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); Matkovic-Calogovic et al. (1993); Gasser et al. (2007). For applications of dinuclear ferrocenyl derivatives, see: Gao et al. (2011); Locke et al. (2001).

Experimental

Crystal data

[Fe₂(C₅H₅)₂(C₁₈H₂₀O)]
M_r = 494.22
Triclinic, $[P \overline 1]$
a = 9.7865 (15) Å
b = 9.8274 (15) Å
c = 12.1816 (19) Å
= 99.405 (2)°
= 94.976 (2)°
= 101.657 (2)°
V = 1123.3 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.561, T_max = 0.736
7657 measured reflections
5352 independent reflections
4759 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.100
S = 0.81
5352 reflections
280 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.37 e Å^-3

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Gao, Y., Li, H.-D., Ke, C.-F., Xie, L.-L., Wei, B. & Yuan, Y.-F. (2011). Appl. Organomet. Chem. 25, 407-411.
Gasser, G., Fischmann, A. J., Forsyth, C. M. & Spiccia, L. (2007). J. Organomet. Chem. 692, 3835-3840.
Locke, A. J., Jones, C. & Richards, C. J. (2001). J. Organomet. Chem. 637-639, 669-676.
Matkovic-Calogovic, D., Rapic, V. & Kovac, S. (1993). Acta Cryst. C49, 226-228.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

metal-organic compounds