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Volume 68 
Part 12 
Page m1450  
December 2012  

Received 21 September 2012
Accepted 2 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.027
wR = 0.071
Data-to-parameter ratio = 13.2
Details
Open access

1,1'-Bis[bis(4-tert-butylphenyl)methyl]ferrocene

aDepartment of Chemistry, Technical University of Kaiserslautern, 67663 Kaiserslautern, Germany
Correspondence e-mail: sitzmann@chemie.uni-kl.de

The molecule of the title compound, [Fe(C26H31)2], is located on an inversion center. The two cyclopentadienyl rings exhibit a staggered conformation, which results from the bulky bis(4-tert-butylphenyl)methyl substituents situated on opposite sides of the molecule.

Related literature

For reports of the Gomberg radical, see: Gomberg (1900[Gomberg, M. (1900). J. Am. Chem. Soc. 22, 757-771.], 1901[Gomberg, M. (1901). J. Am. Chem. Soc. 23, 496-502.], 1902[Gomberg, M. (1902). J. Am. Chem. Soc. 24, 597-628.]). For solution behavior of the triphenylmethyl radical, see: Lankamp et al. (1968[Lankamp, H., Nauta, W. T. & MacLean, C. (1968). Tetrahedron Lett. 9, 249-254.]); McBride (1974[McBride, J. M. (1974). Tetrahedron, 30, 2009-2022.]). For paramagnetic cyclopentadienyliron complexes, see: Sitzmann et al. (1996[Sitzmann, H., Dezember, T., Kaim, W., Baumann, F., Stalke, D., Kärcher, J., Dormann, E., Winter, H., Wachter, C. & Kelemen, M. (1996). Angew. Chem. Int. Ed. Engl. 35, 2872-2875.]); Sitzmann (2001[Sitzmann, H. (2001). Coord, Chem. Rev. 214, 287-327.]); Weismann et al. (2011[Weismann, D., Sun, Y., Lan, Y., Wolmershäuser, G., Powell, A. K. & Sitzmann, H. (2011). Chem. Eur. J. 17, 4700-4704.]). For cyclopentadienyl radicals, see: Sitzmann et al. (1998[Sitzmann, H., Dezember, T. & Ruck, M. (1998). Angew. Chem. Int. Ed. Engl. 37, 3114-3116.], 2000[Sitzmann, H., Dezember, T., Schmitt, O., Weber, F., Wolmershäuser, G. & Ruck, M. (2000). Z. Anorg. Allg. Chem. 625, 2241-2244.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C26H31)2]

  • Mr = 742.87

  • Monoclinic, P 21 /n

  • a = 6.0893 (2) Å

  • b = 30.7616 (8) Å

  • c = 11.0983 (3) Å

  • [beta] = 98.982 (3)°

  • V = 2053.40 (10) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 3.19 mm-1

  • T = 150 K

  • 0.18 × 0.13 × 0.09 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.] Tmin = 0.889, Tmax = 1.000

  • 12754 measured reflections

  • 3267 independent reflections

  • 2784 reflections with I > 2[sigma](I)

  • Rint = 0.028

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

  • wR(F2) = 0.071

  • S = 1.01

  • 3267 reflections

  • 247 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Data collection: CrysAlis CCD (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2088 ).


References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Gomberg, M. (1900). J. Am. Chem. Soc. 22, 757-771.  [CrossRef]
Gomberg, M. (1901). J. Am. Chem. Soc. 23, 496-502.  [CrossRef]
Gomberg, M. (1902). J. Am. Chem. Soc. 24, 597-628.  [CrossRef]
Lankamp, H., Nauta, W. T. & MacLean, C. (1968). Tetrahedron Lett. 9, 249-254.  [CrossRef]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
McBride, J. M. (1974). Tetrahedron, 30, 2009-2022.  [CrossRef] [ChemPort] [ISI]
Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sitzmann, H. (2001). Coord, Chem. Rev. 214, 287-327.
Sitzmann, H., Dezember, T., Kaim, W., Baumann, F., Stalke, D., Kärcher, J., Dormann, E., Winter, H., Wachter, C. & Kelemen, M. (1996). Angew. Chem. Int. Ed. Engl. 35, 2872-2875.  [CrossRef] [ChemPort] [ISI]
Sitzmann, H., Dezember, T. & Ruck, M. (1998). Angew. Chem. Int. Ed. Engl. 37, 3114-3116.  [CrossRef] [ChemPort]
Sitzmann, H., Dezember, T., Schmitt, O., Weber, F., Wolmershäuser, G. & Ruck, M. (2000). Z. Anorg. Allg. Chem. 625, 2241-2244.  [CrossRef]
Weismann, D., Sun, Y., Lan, Y., Wolmershäuser, G., Powell, A. K. & Sitzmann, H. (2011). Chem. Eur. J. 17, 4700-4704.  [CSD] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, m1450  [ doi:10.1107/S1600536812041360 ]

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