metal-organic compounds
1,1′-Bis(tert-butyldimethylsilyl)ferrocene
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
The 11H19Si)2], consists of one half of a ferrocene derivative. The FeII 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.
of the title compound, [Fe(CRelated 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
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Data collection: APEX2 (Bruker, 2005); cell 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
https://doi.org/10.1107/S1600536812049069/is5223sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812049069/is5223Isup2.hkl
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.
All hydrogen atoms were positioned geometrically with C—H = 0.95 or 0.98 Å and included in a riding model approximation with Uiso (H) = 1.2Ueq(C).
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
of the title compound comprises a half of a ferrocene drivative (Fig. 1). The FeII 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).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).
Data collection: APEX2 (Bruker, 2005); cell
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).[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 |
[Fe(C11H19Si)2] | V = 2282.6 (3) Å3 |
Mr = 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 |
Bruker APEXII CCD diffractometer | 2529 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2323 reflections with I > 2σ(I) |
Tmin = 0.861, Tmax = 0.927 | Rint = 0.037 |
17220 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.36 e Å−3 |
2529 reflections | Δρmin = −0.24 e Å−3 |
114 parameters |
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) |
Symmetry code: (i) −x+2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C11H19Si)2] |
Mr | 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) |
Tmin, Tmax | 0.861, 0.927 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17220, 2529, 2323 |
Rint | 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 |
Δρmax, Δρmin (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
Liu, J., Castro, R., Abboud, K. A. & Kaifer, A. E. (2000). J. Org. Chem. 65, 6973–6976. Web of Science CSD CrossRef PubMed CAS Google Scholar
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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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 FeII 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).