(IUCr) 1,4-Diferrocenylbutane-1,4-dione

Volume 64
Part 3
Pages m444-m445
March 2008

Received 14 January 2008
Accepted 29 January 2008
Online 6 February 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R = 0.036
wR = 0.076
Data-to-parameter ratio = 14.2
Details

1,4-Diferrocenylbutane-1,4-dione

Mustafa Tombul,^a ^* Adnan Bulut,^a ⁺ Kutalmis Güven ^b and Orhan Büyükgüngör ^c

^aDepartment of Chemistry, Faculty of Arts and Science, University of Kirikkale, Campus, Yahsihan, 71450 Kirikkale, Turkey,^bDepartment of Physics, Faculty of Arts and Science, University of Kirikkale, Campus, Yahsihan, 71450 Kirikkale, Turkey, and ^cDepartment of Physics, Faculty of Arts and Science, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: mustafatombul38@gmail.com

In the crystal structure of the title compound, [Fe₂(C₅H₅)₂(C₁₄H₁₂O₂)], each carbonyl group is coplanar with the adjacent cyclopentadienyl ring, thus maximizing the [pi] -orbital overlap and electronic interactions between the groups. In the crystal structure, there are inter- and intramolecular C-HO contacts.

Related literature

For related literature, see: Brown et al. (2005); Chidsey et al. (1990); Creager & Rowe (1997); Gemici (2005); Hickman et al. (1991); Kealy & Pauson (1951); Miller et al. (1988); Navarro et al. (2005); Nicolosi et al. (1994); Okochi et al. (2005); Pugh et al. (2006); Sawamura & Ito (1992); Togni & Hayashi (1995).

Experimental

Crystal data

[Fe₂(C₅H₅)₂(C₁₄H₁₂O₂)]
M_r = 454.12
Orthorhombic, P c a 2₁
a = 10.4175 (7) Å
b = 18.5954 (10) Å
c = 9.9690 (6) Å
V = 1931.2 (2) Å³
Z = 4
Mo K radiation
= 1.52 mm^-1
T = 298 (2) K
0.45 × 0.33 × 0.08 mm

Data collection

Stoe IPDS2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.525, T_max = 0.899
11622 measured reflections
3612 independent reflections
2941 reflections with I > 2(I)
R_int = 0.0383

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.075
S = 1.01
3612 reflections
254 parameters
1 restraint
H-atom parameters not refined
_max = 0.36 e Å^-3
_min = -0.22 e Å^-3
Absolute structure: Flack (1983), 1418 Freidel pairs
Flack parameter: 0.01 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12BO1ⁱ	0.97	2.51	3.448 (5)	164
C13-H13BO2ⁱ	0.97	2.55	3.400 (6)	147
C23-H23O1	0.93	2.60	3.499 (5)	164
C10-H10O2	0.93	2.58	3.457 (6)	157
Symmetry code: (i) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2537 ).

Acknowledgements

The authors gratefully acknowledge the Faculty of Arts and Science, Kirikkale University, for financial support and the Faculty of Arts and Science, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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Chidsey, C. E. D., Bertozzi, C. R., Putvinski, T. M. & Mujsce, A. M. (1990). J. Am. Chem. Soc. 112, 4301-4306.
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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gemici, S. (2005). MSc Thesis The synthesis of dicarbonyl unsaturated ferrocene derivatives, Graduate School of Natural and Applied Sciences, Kirikkale University, Turkey.
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Pugh, C. A., Lufaso, M. W., Zeller, M., Wagner, T. R. & Curtin, L. S. (2006). J. Organomet. Chem. 691, 680-686.
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Togni, A. & Hayashi, T. (1995). Editors. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science. Weinheim: VCH.
Westrip, S. P. (2008). publCIF. In preparation.

metal-organic compounds