Diferrocen­yl(meth­yl)phenyl­silane

Yu-Peng Liu; Zong-Qi Li; Yong-Xia Tan; Zhi-Jie Zhang

doi:10.1107/S1600536811014917

. 2011 Apr 29;67(Pt 5):m635. doi: 10.1107/S1600536811014917

Diferrocenyl(methyl)phenylsilane

Yu-Peng Liu ^a, Zong-Qi Li ^a, Yong-Xia Tan ^a, Zhi-Jie Zhang ^a,^*

PMCID: PMC3089330 PMID: 21754343

Abstract

In the title molecule, [Fe₂(C₅H₅)₂(C₁₇H₁₆Si)], the cyclopentadienyl rings linked to the same Fe atom are approximately eclipsed and the interplanar angles are 1.8 (2) and 3.4 (2)°. The Fe atom is slightly closer to the substituted cyclopentadienyl ring.

Related literature

For general background, see: Togni & Hayashi (1994 ▶).

Experimental

Crystal data

[Fe₂(C₅H₅)₂(C₁₇H₁₆Si)]
M _r = 490.27
Triclinic,
a = 7.3840 (15) Å
b = 11.749 (2) Å
c = 13.107 (3) Å
α = 84.18 (3)°
β = 76.18 (3)°
γ = 79.04 (3)°
V = 1082.2 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.41 mm⁻¹
T = 173 K
0.30 × 0.28 × 0.07 mm

Data collection

Rigaku MM007HF + CCD (Saturn724+) diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T _min = 0.368, T _max = 1.000
14130 measured reflections
4942 independent reflections
4477 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.134
S = 1.13
4942 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014917/qm2006sup1.cif

e-67-0m635-sup1.cif^{(51.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014917/qm2006Isup2.hkl

e-67-0m635-Isup2.hkl^{(242KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Science Foundation of China (NSFC, grant No. 50803070).

supplementary crystallographic information

Comment

Ferrocene compounds are of great interest in the field of material chemistry (Togni & Hayashi, 1994). In this paper we reported the synthesis and crystal structure of the title compound. The molecular structure of the compound consists of a methylphenylsilyl unit and two ferrocene units. In the ferrocene unit, the cyclopentaienyl rings linked to the same Fe atom are approximately eclipsed and the interplanar angles are 1.76 (24) and 3.35 (21)°, respectively. The Fe atom is slightly closer to the substituted cyclopentadienyl ring. The distances of the Fe1 atom from the centroids of the unsubstituted and substituted cyclopentadienyl (Cp) rings is 1.648 (1) and 1.645 (1) Å, respectively. The distances of the Fe2 atom from the centroids of the unsubstituted and substituted Cp rings is 1.653 (2) and 1.650 (2) Å, respectively.

Experimental

Ferrocene (2.00 g, 26.88 mmol) was dissolved in 12 ml of anhydrous tetrahydrofuran (THF). In the course of 15 min a solution of 10.8 mmol t-BuLi (7.16 ml of a 1.5 M n-Pentance solution) was added dropwise at 0°C. n-Hexane (16 ml) was then added, and the solution was kept at -78°C for 15 min, before the orange precipitate was filtered off. The precipitate was washed with small portions of n-hexane. The FcLi was dissolved in THF (15 ml) and added to a solution of dichloromethylphenylsilane (0.8 g, 4.69 mmol) in n-hexane (20 ml) at 0°C, and then stirred overnight at room temperature. The precipitate was filtered and the solvent was evaporated under vacuum. the orange residue was purified by recrystallization from n-hexane to give 4.04 g of orange product in 88% yield.