1,1′-Bis(tert-butyl­dimethyl­sil­yl)ferrocene

Abri, A.; Soltani, B.; Ziegler, C.J.; Engle, J.T.; Kia, R.

doi:10.1107/S1600536812049069

metal-organic compounds

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Volume 69| Part 1| January 2013| Page m46

https://doi.org/10.1107/S1600536812049069

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1,1′-Bis(tert-butyldimethylsilyl)ferrocene

Abdolreza Abri,^a ^* Behzad Soltani,^a Christopher J. Ziegler,^b James T. Engle ^b and Reza Kia ^c

^aDepartment of Chemistry, Azarbaijan Shahid Madani University, Tabriz, Iran, ^bDepartment of Chemistry, University of Akron, Akron, OH, USA, and ^cDepartment of Chemistry, Science and Rsearch Branch, Islamic Azad University, Tehran, Iran
^*Correspondence e-mail: Ar.abri@azaruniv.edu

(Received 21 November 2012; accepted 29 November 2012; online 12 December 2012)

The asymmetric unit of the title compound, [Fe(C₁₁H₁₉Si)₂], consists of one half of a ferrocene derivative. The Fe^II atom lies on a twofold rotation axis, giving an eclipsed conformation for the cyclopentadienyl ligands. No significant intermolecular interactions are observed in the crystal structure.

Related literature

For background to ferrocene derivatives and their applications, see: Hudson et al. (2001 ); Liu et al. (2000 ). For a related structure, see: Ren et al. (2012 ).

Experimental

Crystal data

[Fe(C₁₁H₁₉Si)₂]
M_r = 414.55
Orthorhombic, P b c n
a = 7.1282 (6) Å
b = 12.1466 (10) Å
c = 26.363 (2) Å
V = 2282.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 100 K
0.20 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.861, T_max = 0.927
17220 measured reflections
2529 independent reflections
2323 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.067
S = 1.05
2529 reflections
114 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812049069/is5223sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049069/is5223Isup2.hkl

checkCIF report

Comment top

Ferrocene has attracted the interest of many scientists and research groups worldwide because of its applications in materials science (Hudson et al., 2001; Liu et al., 2000). Ferrocene as a starting material in synthetic organometallic systems and its derivatives in industrial applications have become a great area of interest for many researchers and industrial chemists.

The asymmetric unit of the title compound comprises a half of a ferrocene drivative (Fig. 1). The Fe^II atom lies on a twofold rotation axis, giving an eclipsed conformation for the cyclopentadienyl ligands. The bond lengths and angles are within the normal ranges and are comparable to the related structure (Ren et al., 2012).

Related literature top

For background to ferrocene derivatives and their applications, see: Hudson et al. (2001); Liu et al. (2000). For a related structure, see: Ren et al. (2012).

Experimental top

To a stirred solution of ferrocene (5.00 g, 26.88 mmol) in 100 ml of n-hexane, a solution containing 9.2 ml (60 mmol) tetramethylethylenediamine (tmeda) and 35 ml (56 mmol) of a 1.6 M of n-BuLi in 30 ml of n-hexane was added dropwise over 5 min, and mixture was stirred overnight. The orange precipitate of FcLi₂ was collected. A THF solution (20 ml) containing FcLi₂ (0.67 g, 3.5 mmol) was added dropwise to a THF solution (10 ml) of 1.67 ml t-butyldimethylchlorosilane (13.9 mmol) at -30 °C, and were kept for 30 min at -30 °C and then stirred over night at room temperature. The solvent THF was evaporated together with the excess of chlorosilane under vacuum, then, the orange residue dissolved in n-hexane (30 ml) and the solution filtered over Na₂SO₄. The solvent n-hexane was removed under vacuum and the product heated up for 1 h in order to sublime the impurities of ferrocene off. The remaining dark-orange oil or solid (0.69 g, 55% yield) was obtained. Single Crystals suitable for X-ray analysis were obtained by slow evaporation from a n-hexane solution at room temperature.

Structure description top

For background to ferrocene derivatives and their applications, see: Hudson et al. (2001); Liu et al. (2000). For a related structure, see: Ren et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering [symmetry code for suffix A: -x + 2, y, -z + 1/2]. The H atoms were omitted for clarity.

1,1'-Bis(tert-butyldimethylsilyl)ferrocene top

Crystal data top

[Fe(C₁₁H₁₉Si)₂]	F(000) = 896
M_r = 414.55	D_x = 1.206 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9976 reflections
a = 7.1282 (6) Å	θ = 2.3–27.2°
b = 12.1466 (10) Å	µ = 0.77 mm⁻¹
c = 26.363 (2) Å	T = 100 K
V = 2282.6 (3) Å³	Block, orange
Z = 4	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	2529 independent reflections
Radiation source: fine-focus sealed tube	2323 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 27.2°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.861, T_max = 0.927	k = −15→15
17220 measured reflections	l = −33→33

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0312P)² + 1.1338P] where P = (F_o² + 2F_c²)/3
2529 reflections	(Δ/σ)_max = 0.001
114 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Fe(C₁₁H₁₉Si)₂]	V = 2282.6 (3) Å³
M_r = 414.55	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 7.1282 (6) Å	µ = 0.77 mm⁻¹
b = 12.1466 (10) Å	T = 100 K
c = 26.363 (2) Å	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	2529 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2323 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.927	R_int = 0.037
17220 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.05	Δρ_max = 0.36 e Å⁻³
2529 reflections	Δρ_min = −0.24 e Å⁻³
114 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	1.0000	0.03916 (2)	0.2500	0.01182 (9)
Si1	0.96501 (5)	0.11765 (3)	0.122364 (13)	0.01274 (10)
C1	0.7486 (2)	−0.04225 (12)	0.24866 (5)	0.0212 (3)
H1	0.7161	−0.1051	0.2682	0.025*
C2	0.8338 (2)	−0.04320 (11)	0.19970 (5)	0.0181 (3)
H2	0.8674	−0.1072	0.1811	0.022*
C3	0.86070 (18)	0.06855 (10)	0.18305 (5)	0.0143 (3)
C4	0.78856 (18)	0.13706 (11)	0.22318 (5)	0.0167 (3)
H4	0.7866	0.2153	0.2230	0.020*
C5	0.72076 (18)	0.06891 (12)	0.26299 (5)	0.0197 (3)
H5	0.6663	0.0936	0.2938	0.024*
C6	1.14332 (19)	0.01654 (11)	0.09925 (5)	0.0198 (3)
H6A	1.2446	0.0103	0.1242	0.030*
H6B	1.1949	0.0419	0.0668	0.030*
H6C	1.0839	−0.0555	0.0946	0.030*
C7	1.0752 (2)	0.25562 (11)	0.13317 (5)	0.0203 (3)
H7A	1.1764	0.2486	0.1581	0.030*
H7B	0.9803	0.3071	0.1459	0.030*
H7C	1.1266	0.2833	0.1012	0.030*
C8	0.76825 (18)	0.13000 (10)	0.07396 (5)	0.0156 (3)
C9	0.6877 (2)	0.01524 (12)	0.06271 (5)	0.0231 (3)
H9A	0.5864	0.0216	0.0378	0.035*
H9B	0.6384	−0.0170	0.0941	0.035*
H9D	0.7870	−0.0321	0.0491	0.035*
C10	0.61107 (19)	0.20356 (12)	0.09496 (5)	0.0212 (3)
H10A	0.5103	0.2095	0.0698	0.032*
H10D	0.6613	0.2770	0.1022	0.032*
H10B	0.5613	0.1711	0.1262	0.032*
C11	0.8419 (2)	0.18068 (12)	0.02429 (5)	0.0233 (3)
H11D	0.7389	0.1864	−0.0002	0.035*
H11A	0.9409	0.1337	0.0103	0.035*
H11B	0.8927	0.2542	0.0311	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01172 (14)	0.01365 (14)	0.01008 (14)	0.000	−0.00130 (9)	0.000
Si1	0.01328 (17)	0.01321 (18)	0.01173 (17)	−0.00049 (13)	−0.00074 (13)	0.00000 (12)
C1	0.0187 (7)	0.0279 (8)	0.0170 (7)	−0.0100 (6)	−0.0031 (5)	0.0032 (5)
C2	0.0212 (7)	0.0189 (7)	0.0142 (6)	−0.0060 (5)	−0.0039 (5)	−0.0003 (5)
C3	0.0130 (6)	0.0168 (6)	0.0130 (6)	−0.0010 (5)	−0.0042 (5)	−0.0004 (5)
C4	0.0135 (6)	0.0221 (7)	0.0146 (6)	0.0036 (5)	−0.0030 (5)	−0.0009 (5)
C5	0.0107 (6)	0.0339 (8)	0.0145 (6)	0.0004 (6)	−0.0010 (5)	−0.0009 (5)
C6	0.0175 (6)	0.0218 (7)	0.0202 (7)	0.0021 (6)	0.0002 (5)	−0.0022 (5)
C7	0.0217 (7)	0.0179 (7)	0.0212 (7)	−0.0034 (6)	−0.0016 (6)	0.0004 (5)
C8	0.0171 (6)	0.0177 (6)	0.0121 (6)	0.0005 (5)	−0.0012 (5)	0.0011 (5)
C9	0.0236 (7)	0.0245 (7)	0.0213 (7)	−0.0034 (6)	−0.0079 (6)	−0.0021 (5)
C10	0.0185 (7)	0.0271 (7)	0.0179 (6)	0.0051 (6)	−0.0019 (5)	0.0022 (5)
C11	0.0244 (7)	0.0309 (8)	0.0146 (6)	0.0029 (6)	0.0009 (6)	0.0043 (5)

Geometric parameters (Å, º) top

Fe1—C2ⁱ	2.0401 (13)	C4—H4	0.9500
Fe1—C2	2.0402 (13)	C5—H5	0.9500
Fe1—C4	2.0460 (13)	C6—H6A	0.9800
Fe1—C4ⁱ	2.0460 (13)	C6—H6B	0.9800
Fe1—C1ⁱ	2.0473 (15)	C6—H6C	0.9800
Fe1—C1	2.0473 (15)	C7—H7A	0.9800
Fe1—C5ⁱ	2.0518 (13)	C7—H7B	0.9800
Fe1—C5	2.0518 (13)	C7—H7C	0.9800
Fe1—C3	2.0564 (12)	C8—C9	1.5363 (19)
Fe1—C3ⁱ	2.0565 (12)	C8—C10	1.5364 (18)
Si1—C3	1.8622 (13)	C8—C11	1.5391 (17)
Si1—C6	1.8696 (14)	C9—H9A	0.9800
Si1—C7	1.8726 (14)	C9—H9B	0.9800
Si1—C8	1.9022 (13)	C9—H9D	0.9800
C1—C5	1.416 (2)	C10—H10A	0.9800
C1—C2	1.4267 (19)	C10—H10D	0.9800
C1—H1	0.9500	C10—H10B	0.9800
C2—C3	1.4394 (17)	C11—H11D	0.9800
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.4409 (17)	C11—H11B	0.9800
C4—C5	1.4214 (19)

C2ⁱ—Fe1—C2	121.27 (8)	C3—C2—Fe1	70.04 (7)
C2ⁱ—Fe1—C4	159.61 (5)	C1—C2—H2	125.5
C2—Fe1—C4	68.45 (5)	C3—C2—H2	125.5
C2ⁱ—Fe1—C4ⁱ	68.45 (5)	Fe1—C2—H2	126.2
C2—Fe1—C4ⁱ	159.61 (5)	C2—C3—C4	105.85 (11)
C4—Fe1—C4ⁱ	108.92 (8)	C2—C3—Si1	128.11 (10)
C2ⁱ—Fe1—C1ⁱ	40.86 (5)	C4—C3—Si1	126.04 (10)
C2—Fe1—C1ⁱ	106.42 (6)	C2—C3—Fe1	68.82 (7)
C4—Fe1—C1ⁱ	158.69 (5)	C4—C3—Fe1	69.05 (7)
C4ⁱ—Fe1—C1ⁱ	68.27 (6)	Si1—C3—Fe1	126.88 (7)
C2ⁱ—Fe1—C1	106.42 (6)	C5—C4—C3	109.09 (12)
C2—Fe1—C1	40.86 (5)	C5—C4—Fe1	69.92 (7)
C4—Fe1—C1	68.27 (6)	C3—C4—Fe1	69.83 (7)
C4ⁱ—Fe1—C1	158.69 (5)	C5—C4—H4	125.5
C1ⁱ—Fe1—C1	122.24 (9)	C3—C4—H4	125.5
C2ⁱ—Fe1—C5ⁱ	68.38 (6)	Fe1—C4—H4	126.4
C2—Fe1—C5ⁱ	122.76 (6)	C1—C5—C4	108.11 (12)
C4—Fe1—C5ⁱ	123.69 (6)	C1—C5—Fe1	69.62 (8)
C4ⁱ—Fe1—C5ⁱ	40.59 (5)	C4—C5—Fe1	69.48 (7)
C1ⁱ—Fe1—C5ⁱ	40.42 (6)	C1—C5—H5	125.9
C1—Fe1—C5ⁱ	158.67 (6)	C4—C5—H5	125.9
C2ⁱ—Fe1—C5	122.76 (6)	Fe1—C5—H5	126.5
C2—Fe1—C5	68.38 (6)	Si1—C6—H6A	109.5
C4—Fe1—C5	40.59 (5)	Si1—C6—H6B	109.5
C4ⁱ—Fe1—C5	123.68 (6)	H6A—C6—H6B	109.5
C1ⁱ—Fe1—C5	158.67 (6)	Si1—C6—H6C	109.5
C1—Fe1—C5	40.42 (6)	H6A—C6—H6C	109.5
C5ⁱ—Fe1—C5	159.71 (9)	H6B—C6—H6C	109.5
C2ⁱ—Fe1—C3	157.42 (5)	Si1—C7—H7A	109.5
C2—Fe1—C3	41.14 (5)	Si1—C7—H7B	109.5
C4—Fe1—C3	41.13 (5)	H7A—C7—H7B	109.5
C4ⁱ—Fe1—C3	123.47 (5)	Si1—C7—H7C	109.5
C1ⁱ—Fe1—C3	121.43 (5)	H7A—C7—H7C	109.5
C1—Fe1—C3	69.29 (5)	H7B—C7—H7C	109.5
C5ⁱ—Fe1—C3	107.13 (5)	C9—C8—C10	108.95 (11)
C5—Fe1—C3	69.16 (5)	C9—C8—C11	109.03 (11)
C2ⁱ—Fe1—C3ⁱ	41.14 (5)	C10—C8—C11	108.82 (11)
C2—Fe1—C3ⁱ	157.42 (5)	C9—C8—Si1	109.48 (9)
C4—Fe1—C3ⁱ	123.46 (5)	C10—C8—Si1	109.98 (9)
C4ⁱ—Fe1—C3ⁱ	41.13 (5)	C11—C8—Si1	110.54 (9)
C1ⁱ—Fe1—C3ⁱ	69.29 (5)	C8—C9—H9A	109.5
C1—Fe1—C3ⁱ	121.42 (5)	C8—C9—H9B	109.5
C5ⁱ—Fe1—C3ⁱ	69.16 (5)	H9A—C9—H9B	109.5
C5—Fe1—C3ⁱ	107.13 (5)	C8—C9—H9D	109.5
C3—Fe1—C3ⁱ	160.00 (7)	H9A—C9—H9D	109.5
C3—Si1—C6	109.94 (6)	H9B—C9—H9D	109.5
C3—Si1—C7	108.87 (6)	C8—C10—H10A	109.5
C6—Si1—C7	110.63 (6)	C8—C10—H10D	109.5
C3—Si1—C8	107.89 (6)	H10A—C10—H10D	109.5
C6—Si1—C8	109.53 (6)	C8—C10—H10B	109.5
C7—Si1—C8	109.93 (6)	H10A—C10—H10B	109.5
C5—C1—C2	107.98 (12)	H10D—C10—H10B	109.5
C5—C1—Fe1	69.96 (8)	C8—C11—H11D	109.5
C2—C1—Fe1	69.30 (8)	C8—C11—H11A	109.5
C5—C1—H1	126.0	H11D—C11—H11A	109.5
C2—C1—H1	126.0	C8—C11—H11B	109.5
Fe1—C1—H1	126.3	H11D—C11—H11B	109.5
C1—C2—C3	108.96 (12)	H11A—C11—H11B	109.5
C1—C2—Fe1	69.84 (8)

C2ⁱ—Fe1—C1—C5	121.60 (8)	C5—Fe1—C3—C4	36.93 (8)
C2—Fe1—C1—C5	−119.28 (11)	C3ⁱ—Fe1—C3—C4	−45.93 (7)
C4—Fe1—C1—C5	−37.55 (8)	C2ⁱ—Fe1—C3—Si1	−76.71 (17)
C4ⁱ—Fe1—C1—C5	48.96 (18)	C2—Fe1—C3—Si1	−122.46 (12)
C1ⁱ—Fe1—C1—C5	163.33 (9)	C4—Fe1—C3—Si1	120.02 (12)
C5ⁱ—Fe1—C1—C5	−165.93 (10)	C4ⁱ—Fe1—C3—Si1	39.57 (11)
C3—Fe1—C1—C5	−81.80 (8)	C1ⁱ—Fe1—C3—Si1	−43.76 (11)
C3ⁱ—Fe1—C1—C5	79.33 (9)	C1—Fe1—C3—Si1	−159.69 (10)
C2ⁱ—Fe1—C1—C2	−119.12 (9)	C5ⁱ—Fe1—C3—Si1	−1.95 (10)
C4—Fe1—C1—C2	81.73 (8)	C5—Fe1—C3—Si1	156.94 (10)
C4ⁱ—Fe1—C1—C2	168.24 (14)	C3ⁱ—Fe1—C3—Si1	74.08 (7)
C1ⁱ—Fe1—C1—C2	−77.39 (8)	C2—C3—C4—C5	0.22 (14)
C5ⁱ—Fe1—C1—C2	−46.65 (18)	Si1—C3—C4—C5	179.86 (9)
C5—Fe1—C1—C2	119.28 (11)	Fe1—C3—C4—C5	−59.06 (9)
C3—Fe1—C1—C2	37.48 (8)	C2—C3—C4—Fe1	59.28 (9)
C3ⁱ—Fe1—C1—C2	−161.39 (8)	Si1—C3—C4—Fe1	−121.08 (10)
C5—C1—C2—C3	0.20 (16)	C2ⁱ—Fe1—C4—C5	−41.15 (19)
Fe1—C1—C2—C3	−59.29 (10)	C2—Fe1—C4—C5	81.50 (9)
C5—C1—C2—Fe1	59.49 (10)	C4ⁱ—Fe1—C4—C5	−120.06 (9)
C2ⁱ—Fe1—C2—C1	78.66 (8)	C1ⁱ—Fe1—C4—C5	161.35 (15)
C4—Fe1—C2—C1	−81.27 (9)	C1—Fe1—C4—C5	37.39 (8)
C4ⁱ—Fe1—C2—C1	−167.72 (15)	C5ⁱ—Fe1—C4—C5	−162.65 (8)
C1ⁱ—Fe1—C2—C1	120.62 (11)	C3—Fe1—C4—C5	120.35 (11)
C5ⁱ—Fe1—C2—C1	161.66 (9)	C3ⁱ—Fe1—C4—C5	−76.78 (10)
C5—Fe1—C2—C1	−37.47 (8)	C2ⁱ—Fe1—C4—C3	−161.50 (15)
C3—Fe1—C2—C1	−120.11 (12)	C2—Fe1—C4—C3	−38.85 (8)
C3ⁱ—Fe1—C2—C1	45.19 (18)	C4ⁱ—Fe1—C4—C3	119.58 (8)
C2ⁱ—Fe1—C2—C3	−161.23 (9)	C1ⁱ—Fe1—C4—C3	41.00 (19)
C4—Fe1—C2—C3	38.84 (8)	C1—Fe1—C4—C3	−82.96 (8)
C4ⁱ—Fe1—C2—C3	−47.61 (19)	C5ⁱ—Fe1—C4—C3	76.99 (9)
C1ⁱ—Fe1—C2—C3	−119.27 (8)	C5—Fe1—C4—C3	−120.35 (11)
C1—Fe1—C2—C3	120.11 (12)	C3ⁱ—Fe1—C4—C3	162.87 (7)
C5ⁱ—Fe1—C2—C3	−78.22 (10)	C2—C1—C5—C4	−0.06 (16)
C5—Fe1—C2—C3	82.65 (8)	Fe1—C1—C5—C4	59.01 (9)
C3ⁱ—Fe1—C2—C3	165.30 (9)	C2—C1—C5—Fe1	−59.08 (10)
C1—C2—C3—C4	−0.26 (15)	C3—C4—C5—C1	−0.10 (15)
Fe1—C2—C3—C4	−59.42 (8)	Fe1—C4—C5—C1	−59.10 (10)
C1—C2—C3—Si1	−179.89 (10)	C3—C4—C5—Fe1	59.00 (9)
Fe1—C2—C3—Si1	120.94 (11)	C2ⁱ—Fe1—C5—C1	−76.28 (9)
C1—C2—C3—Fe1	59.17 (10)	C2—Fe1—C5—C1	37.86 (8)
C6—Si1—C3—C2	−30.07 (14)	C4—Fe1—C5—C1	119.54 (11)
C7—Si1—C3—C2	−151.41 (12)	C4ⁱ—Fe1—C5—C1	−160.77 (7)
C8—Si1—C3—C2	89.33 (13)	C1ⁱ—Fe1—C5—C1	−41.8 (2)
C6—Si1—C3—C4	150.36 (11)	C5ⁱ—Fe1—C5—C1	165.22 (8)
C7—Si1—C3—C4	29.03 (13)	C3—Fe1—C5—C1	82.14 (8)
C8—Si1—C3—C4	−90.24 (12)	C3ⁱ—Fe1—C5—C1	−118.66 (8)
C6—Si1—C3—Fe1	60.76 (9)	C2ⁱ—Fe1—C5—C4	164.18 (8)
C7—Si1—C3—Fe1	−60.57 (10)	C2—Fe1—C5—C4	−81.67 (8)
C8—Si1—C3—Fe1	−179.84 (7)	C4ⁱ—Fe1—C5—C4	79.69 (11)
C2ⁱ—Fe1—C3—C2	45.8 (2)	C1ⁱ—Fe1—C5—C4	−161.38 (13)
C4—Fe1—C3—C2	−117.52 (11)	C1—Fe1—C5—C4	−119.54 (11)
C4ⁱ—Fe1—C3—C2	162.04 (8)	C5ⁱ—Fe1—C5—C4	45.68 (7)
C1ⁱ—Fe1—C3—C2	78.70 (10)	C3—Fe1—C5—C4	−37.39 (8)
C1—Fe1—C3—C2	−37.23 (8)	C3ⁱ—Fe1—C5—C4	121.81 (8)
C5ⁱ—Fe1—C3—C2	120.52 (9)	C3—Si1—C8—C9	−65.20 (10)
C5—Fe1—C3—C2	−80.59 (9)	C6—Si1—C8—C9	54.46 (11)
C3ⁱ—Fe1—C3—C2	−163.45 (8)	C7—Si1—C8—C9	176.22 (9)
C2ⁱ—Fe1—C3—C4	163.27 (13)	C3—Si1—C8—C10	54.48 (10)
C2—Fe1—C3—C4	117.52 (11)	C6—Si1—C8—C10	174.14 (9)
C4ⁱ—Fe1—C3—C4	−80.44 (11)	C7—Si1—C8—C10	−64.10 (11)
C1ⁱ—Fe1—C3—C4	−163.78 (8)	C3—Si1—C8—C11	174.68 (9)
C1—Fe1—C3—C4	80.29 (8)	C6—Si1—C8—C11	−65.67 (11)
C5ⁱ—Fe1—C3—C4	−121.96 (8)	C7—Si1—C8—C11	56.09 (11)

Symmetry code: (i) −x+2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₁₁H₁₉Si)₂]
M_r	414.55
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	7.1282 (6), 12.1466 (10), 26.363 (2)
V (Å³)	2282.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.861, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	17220, 2529, 2323
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.067, 1.05
No. of reflections	2529
No. of parameters	114
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

AA thanks Azarbaijan Shahid Madani University for financial support. CJZ and JTE thank University of Akron for the X-ray facility.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hudson, R. D. A. (2001). J. Organomet. Chem. 637, 47–50. Web of Science CrossRef Google Scholar
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Ren, X., Wang, L. & Li, Y. (2012). Acta Cryst. E68, m922. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar