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

Bauer, H.; Sun, Y.; Sitzmann, H.

doi:10.1107/S1600536812041360

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 (C-C) = 0.002 Å
R = 0.027
wR = 0.071
Data-to-parameter ratio = 13.2
Details

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

Heiko Bauer,^a Yu Sun ^a and Helmut Sitzmann ^a ^*

^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, 1901, 1902). For solution behavior of the triphenylmethyl radical, see: Lankamp et al. (1968); McBride (1974). For paramagnetic cyclopentadienyliron complexes, see: Sitzmann et al. (1996); Sitzmann (2001); Weismann et al. (2011). For cyclopentadienyl radicals, see: Sitzmann et al. (1998, 2000).

Experimental

Crystal data

[Fe(C₂₆H₃₁)₂]
M_r = 742.87
Monoclinic, P 2₁ /n
a = 6.0893 (2) Å
b = 30.7616 (8) Å
c = 11.0983 (3) Å
= 98.982 (3)°
V = 2053.40 (10) Å³
Z = 2
Cu K radiation
= 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) $[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ T_min = 0.889, T_max = 1.000
12754 measured reflections
3267 independent reflections
2784 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.071
S = 1.01
3267 reflections
247 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
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Gomberg, M. (1901). J. Am. Chem. Soc. 23, 496-502.
Gomberg, M. (1902). J. Am. Chem. Soc. 24, 597-628.
Lankamp, H., Nauta, W. T. & MacLean, C. (1968). Tetrahedron Lett. 9, 249-254.
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McBride, J. M. (1974). Tetrahedron, 30, 2009-2022.
Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
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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, H., Dezember, T. & Ruck, M. (1998). Angew. Chem. Int. Ed. Engl. 37, 3114-3116.
Sitzmann, H., Dezember, T., Schmitt, O., Weber, F., Wolmershäuser, G. & Ruck, M. (2000). Z. Anorg. Allg. Chem. 625, 2241-2244.
Weismann, D., Sun, Y., Lan, Y., Wolmershäuser, G., Powell, A. K. & Sitzmann, H. (2011). Chem. Eur. J. 17, 4700-4704.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

metal-organic compounds