1,1'-Bis(tert-butyl-dimethyl-sil-yl)ferrocene.

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 cyclo-penta-dienyl ligands. No significant inter-molecular inter-actions 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 = 414.55

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.067

S = 1.05

2529 reflections

114 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812049069/is5223sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049069/is5223Isup2.hkl

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

[Fe(C11H19Si)2]	F(000) = 896
Mr = 414.55	Dx = 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

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

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(Fo2) + (0.0312P)2 + 1.1338P] where P = (Fo2 + 2Fc2)/3
2529 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)