An oxy­gen-bridged bis­(sila­[1]­ferrocenophane), [Fe(η-C5H4)2Si(Me)]2O

Berenbaum, A.; Lough, A.J.; Manners, I.

doi:10.1107/S1600536802016690

An oxygen-bridged bis(sila[1]ferrocenophane), [Fe(η-C₅H₄)₂Si(Me)]₂O

A. Berenbaum, A. J. Lough and I. Manners

In the title compound, [Fe(C₅H₄)₂(CH₃Si)]₂O, the cyclopentadienyl rings in both ferrocenophane moieties are tilted towards the bridging Si atoms, with tilt angles of 19.7 (2) and 20.7 (2)°; the central Si—O—Si angle is 143.25 (12)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016690/ob6177sup1.cif Contains datablocks k99163, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016690/ob6177Isup2.hkl Contains datablock I

CCDC reference: 198308

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.029
wR factor = 0.069
Data-to-parameter ratio = 17.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.46
         From the CIF: _reflns_number_total               4381
         Count of symmetry unique reflns         2514
         Completeness (_total/calc)            174.26%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1867
         Fraction of Friedel pairs measured     0.743
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

Comment top

The title compound was isolated in trace amounts as an impurity from aged samples of the silicon-bridged [1]ferrocenophane, (II), (Zechel et al., 1996) which possesses a hydrolytically sensitive Si—Cl moiety. The bis(sila[1]ferrocenophane), (I), is of potential utility as a crosslinking agent in the polymerization of other sila[1]ferrocenophanes (MacLachlan et al., 1996, 2000; Kulbaba et al., 2001; Kulbaba & Manners, 2001); however, attempts to produce it on a large scale have been unsuccessful to date.

In (I), the cyclopentadienyl (Cp) rings of both of the ferrocenophane groups are tilted towards the bridging Si atoms. The angle between the least-squares planes of the Cp rings bonded to Fe1 is 19.7 (2)°, and the angle between the Cp rings bonded to Fe2 is 20.7 (2)°. The tilt of the Cp rings is also reflected in the variation of the Fe—C distances in each of the ferrocene groups. The Fe—C distances in the ferrocene group containing Fe1 range from 2.010 (2) to 2.082 (3) Å and in the ferrocene group containing Fe2, the Fe—C distances range from 2.009 (3) to 2.087 (3) Å. The shortest Fe—C distances are for the C atoms which are also bonded to the bridging Si atoms, namely C1, C6, C11 and C16 (see Table 1). The overall conformation of the molecule is twisted such that the ferrocene groups are rotated about the Si—O bonds so that the they are approximately perpendicular to each other (sse Fig. 1). The degree of rotation can be described by a torsion angle calculated using the non-bonded atoms Fe1—Si1—Si2—Fe2, which gives a value of 75.07 (5)°. The Si1—O1—Si2 angle is 143.25 (12)°.

Experimental top

Crystals of (I) were obtained at 243 K in trace amounts from the hexanes-soluble fraction of a reaction mixture which initially contained (II). No other hexanes-soluble products were formed in this reaction, and an investigation of the sample of (II) utilized in the synthesis revealed the presence of trace (< 5%) amounts of (I). For 1: ¹H NMR (400 MHz, C₆D₆, 298 K): δ = 4.46–4.44 (m, 4 H, Cp), 4.42–4.39 (m, 8 H, Cp), 3.87–3.86 (m, 4 H, Cp), 0.58 (s, 6 H, Me); ¹³C{¹H} NMR (100.4 MHz, C₆D₆, 298 K): δ = 78.4, 77.8, 75.9, 74.5 (Cp), 38.7 (ipso-Cp), −0.6 (Me); ²⁹Si{¹H} NMR (79.3 MHz, C₆D₆, 298 K): δ = −13.4.

Computing details top

Data collection: COLLECT (Nonius 1997-2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1999); program(s) used to refine structure: SHELXT; molecular graphics: SHELXT; software used to prepare material for publication: SHELXT.

Figures top

Fig. 1. View of molecule (I), with displacement ellipsoids drawn at the 50% probability level.

(I) top

Crystal data top

[Fe(C₅H₄)₂(CH₃Si)]₂O	F(000) = 968
M_r = 470.28	D_x = 1.631 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 19591 reflections
a = 7.5203 (1) Å	θ = 2.9–27.5°
b = 11.4213 (3) Å	µ = 1.65 mm⁻¹
c = 22.2986 (6) Å	T = 100 K
V = 1915.26 (8) Å³	Plate, orange
Z = 4	0.35 × 0.32 × 0.10 mm

Data collection top

Nonius Kappa-CCD diffractometer	4381 independent reflections
Radiation source: fine-focus sealed tube	3810 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ scans and ω scans with κ offsets	h = −9→9
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	k = −14→14
T_min = 0.596, T_max = 0.853	l = −28→28
19591 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.0359P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
4381 reflections	Δρ_max = 0.31 e Å⁻³
246 parameters	Δρ_min = −0.48 e Å⁻³
0 restraints	Absolute structure: (Flack, 1983), 1871 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.009 (13)

Crystal data top

[Fe(C₅H₄)₂(CH₃Si)]₂O	V = 1915.26 (8) Å³
M_r = 470.28	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5203 (1) Å	µ = 1.65 mm⁻¹
b = 11.4213 (3) Å	T = 100 K
c = 22.2986 (6) Å	0.35 × 0.32 × 0.10 mm

Data collection top

Nonius Kappa-CCD diffractometer	4381 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	3810 reflections with I > 2σ(I)
T_min = 0.596, T_max = 0.853	R_int = 0.075
19591 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.069	Δρ_max = 0.31 e Å⁻³
S = 1.00	Δρ_min = −0.48 e Å⁻³
4381 reflections	Absolute structure: (Flack, 1983), 1871 Friedel pairs
246 parameters	Absolute structure parameter: −0.009 (13)
0 restraints

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	0.48696 (5)	0.40794 (3)	0.070092 (16)	0.01818 (9)
Fe2	0.91547 (5)	0.44410 (3)	0.332136 (17)	0.01771 (9)
Si1	0.73986 (9)	0.55859 (7)	0.10626 (3)	0.01936 (16)
Si2	0.77709 (10)	0.57814 (6)	0.24443 (3)	0.01971 (16)
O1	0.8254 (2)	0.55946 (16)	0.17346 (8)	0.0220 (4)
C1	0.4897 (4)	0.5665 (2)	0.10918 (11)	0.0211 (5)
C2	0.3935 (4)	0.4853 (2)	0.14549 (13)	0.0240 (6)
H2A	0.4265	0.4623	0.1873	0.029*
C3	0.2454 (3)	0.4395 (3)	0.11270 (13)	0.0251 (6)
H3A	0.1593	0.3790	0.1271	0.030*
C4	0.2476 (4)	0.4922 (2)	0.05511 (13)	0.0266 (7)
H4A	0.1628	0.4747	0.0217	0.032*
C5	0.3937 (4)	0.5711 (2)	0.05198 (13)	0.0233 (6)
H5A	0.4267	0.6202	0.0165	0.028*
C6	0.7550 (3)	0.4089 (2)	0.07139 (12)	0.0211 (5)
C7	0.6860 (4)	0.3082 (2)	0.10450 (12)	0.0212 (6)
H7A	0.7060	0.2923	0.1481	0.025*
C8	0.5825 (4)	0.2377 (2)	0.06505 (13)	0.0238 (6)
H8A	0.5154	0.1655	0.0765	0.029*
C9	0.5844 (4)	0.2900 (2)	0.00733 (12)	0.0223 (6)
H9A	0.5193	0.2609	−0.0288	0.027*
C10	0.6909 (3)	0.3940 (2)	0.01038 (12)	0.0219 (6)
H10A	0.7142	0.4487	−0.0237	0.026*
C11	0.9868 (4)	0.5920 (2)	0.28970 (12)	0.0213 (5)
C12	0.9703 (4)	0.6127 (2)	0.35374 (12)	0.0241 (6)
H12A	0.8856	0.6687	0.3730	0.029*
C13	1.0925 (3)	0.5392 (2)	0.38468 (13)	0.0243 (6)
H13A	1.1057	0.5331	0.4292	0.029*
C14	1.1873 (4)	0.4722 (3)	0.34135 (13)	0.0274 (7)
H14A	1.2790	0.4111	0.3500	0.033*
C15	1.1240 (3)	0.5050 (3)	0.28363 (13)	0.0261 (6)
H15A	1.1663	0.4713	0.2448	0.031*
C16	0.6991 (3)	0.4375 (2)	0.27854 (12)	0.0205 (5)
C17	0.6473 (3)	0.4380 (2)	0.34176 (12)	0.0220 (6)
H17A	0.5732	0.4996	0.3615	0.026*
C18	0.7214 (4)	0.3389 (2)	0.37108 (14)	0.0260 (6)
H18A	0.7108	0.3204	0.4148	0.031*
C19	0.8180 (4)	0.2732 (2)	0.32837 (13)	0.0242 (6)
H19A	0.8875	0.2003	0.3366	0.029*
C20	0.8060 (4)	0.3321 (2)	0.27218 (13)	0.0223 (6)
H20A	0.8638	0.3056	0.2342	0.027*
C21	0.8374 (4)	0.6748 (2)	0.05862 (13)	0.0263 (6)
H21A	0.8372	0.7491	0.0806	0.040*
H21B	0.7668	0.6830	0.0219	0.040*
H21C	0.9598	0.6537	0.0481	0.040*
C22	0.6212 (4)	0.7006 (3)	0.25725 (14)	0.0319 (7)
H22A	0.6698	0.7722	0.2395	0.048*
H22B	0.6048	0.7120	0.3004	0.048*
H22C	0.5064	0.6824	0.2386	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01805 (18)	0.01509 (18)	0.02140 (19)	0.00138 (14)	−0.00007 (16)	−0.00107 (15)
Fe2	0.01664 (17)	0.01568 (18)	0.02082 (19)	−0.00169 (14)	−0.00093 (15)	0.00026 (15)
Si1	0.0212 (3)	0.0165 (4)	0.0204 (4)	−0.0003 (3)	−0.0010 (3)	−0.0006 (3)
Si2	0.0224 (3)	0.0157 (4)	0.0210 (4)	0.0002 (3)	−0.0010 (3)	0.0005 (3)
O1	0.0224 (8)	0.0234 (10)	0.0203 (9)	−0.0014 (8)	−0.0021 (8)	−0.0009 (9)
C1	0.0250 (12)	0.0140 (12)	0.0245 (13)	0.0055 (11)	−0.0007 (12)	−0.0049 (11)
C2	0.0210 (13)	0.0242 (14)	0.0268 (15)	0.0014 (11)	0.0028 (12)	−0.0071 (11)
C3	0.0189 (12)	0.0263 (15)	0.0302 (15)	−0.0008 (11)	0.0030 (11)	−0.0049 (12)
C4	0.0223 (14)	0.0244 (14)	0.0332 (18)	0.0068 (11)	−0.0054 (12)	−0.0074 (12)
C5	0.0264 (14)	0.0146 (13)	0.0288 (14)	0.0068 (11)	−0.0051 (11)	−0.0002 (11)
C6	0.0194 (12)	0.0214 (13)	0.0224 (13)	0.0044 (10)	0.0023 (11)	−0.0034 (12)
C7	0.0249 (14)	0.0175 (13)	0.0211 (14)	0.0035 (11)	−0.0036 (12)	−0.0020 (11)
C8	0.0276 (14)	0.0136 (12)	0.0303 (15)	0.0017 (11)	−0.0005 (13)	−0.0011 (12)
C9	0.0218 (13)	0.0200 (13)	0.0250 (14)	0.0028 (11)	−0.0014 (12)	−0.0053 (11)
C10	0.0212 (13)	0.0199 (14)	0.0245 (14)	0.0027 (11)	0.0016 (11)	−0.0028 (12)
C11	0.0258 (13)	0.0175 (12)	0.0208 (13)	−0.0066 (12)	−0.0002 (11)	0.0017 (11)
C12	0.0263 (14)	0.0182 (14)	0.0279 (15)	−0.0086 (11)	−0.0040 (11)	−0.0018 (11)
C13	0.0236 (13)	0.0254 (15)	0.0239 (14)	−0.0083 (12)	−0.0035 (12)	0.0017 (12)
C14	0.0144 (12)	0.0377 (17)	0.0302 (17)	−0.0023 (11)	−0.0004 (12)	0.0038 (13)
C15	0.0209 (14)	0.0347 (16)	0.0227 (15)	−0.0069 (12)	0.0039 (12)	−0.0022 (12)
C16	0.0160 (11)	0.0196 (14)	0.0259 (14)	−0.0023 (10)	−0.0021 (10)	−0.0014 (12)
C17	0.0152 (11)	0.0216 (14)	0.0291 (15)	−0.0034 (10)	0.0047 (10)	−0.0008 (12)
C18	0.0258 (15)	0.0242 (15)	0.0282 (16)	−0.0090 (11)	−0.0009 (12)	0.0038 (12)
C19	0.0264 (14)	0.0156 (13)	0.0306 (15)	−0.0033 (10)	−0.0060 (13)	0.0031 (12)
C20	0.0237 (13)	0.0177 (13)	0.0256 (15)	−0.0010 (11)	−0.0021 (12)	−0.0010 (11)
C21	0.0315 (15)	0.0230 (14)	0.0246 (16)	−0.0024 (12)	0.0029 (12)	0.0004 (12)
C22	0.0442 (19)	0.0212 (15)	0.0304 (17)	0.0072 (13)	−0.0059 (14)	−0.0027 (12)

Geometric parameters (Å, º) top

Fe1—C1	2.010 (2)	C4—C5	1.423 (4)
Fe1—C6	2.016 (2)	C4—H4A	1.0000
Fe1—C2	2.025 (3)	C5—H5A	1.0000
Fe1—C7	2.032 (3)	C6—C10	1.454 (4)
Fe1—C5	2.032 (3)	C6—C7	1.462 (4)
Fe1—C10	2.037 (3)	C7—C8	1.424 (4)
Fe1—C4	2.068 (3)	C7—H7A	1.0000
Fe1—C9	2.076 (3)	C8—C9	1.419 (4)
Fe1—C8	2.076 (3)	C8—H8A	1.0000
Fe1—C3	2.082 (3)	C9—C10	1.434 (4)
Fe1—Si1	2.6885 (8)	C9—H9A	1.0000
Fe2—C11	2.009 (3)	C10—H10A	1.0000
Fe2—C16	2.020 (3)	C11—C15	1.439 (4)
Fe2—C20	2.025 (3)	C11—C12	1.453 (4)
Fe2—C12	2.027 (3)	C12—C13	1.423 (4)
Fe2—C15	2.028 (3)	C12—H12A	1.0000
Fe2—C17	2.030 (2)	C13—C14	1.424 (4)
Fe2—C14	2.079 (3)	C13—H13A	1.0000
Fe2—C13	2.080 (3)	C14—C15	1.422 (4)
Fe2—C18	2.080 (3)	C14—H14A	1.0000
Fe2—C19	2.087 (3)	C15—H15A	1.0000
Fe2—Si2	2.6929 (8)	C16—C20	1.454 (4)
Si1—O1	1.6308 (18)	C16—C17	1.463 (4)
Si1—C21	1.851 (3)	C17—C18	1.421 (4)
Si1—C6	1.882 (3)	C17—H17A	1.0000
Si1—C1	1.885 (3)	C18—C19	1.413 (4)
Si2—O1	1.6377 (19)	C18—H18A	1.0000
Si2—C22	1.847 (3)	C19—C20	1.425 (4)
Si2—C16	1.871 (3)	C19—H19A	1.0000
Si2—C11	1.879 (3)	C20—H20A	1.0000
C1—C2	1.429 (4)	C21—H21A	0.9800
C1—C5	1.466 (4)	C21—H21B	0.9800
C2—C3	1.431 (4)	C21—H21C	0.9800
C2—H2A	1.0000	C22—H22A	0.9800
C3—C4	1.418 (4)	C22—H22B	0.9800
C3—H3A	1.0000	C22—H22C	0.9800

C1—Fe1—C6	88.78 (11)	C4—C3—H3A	126.3
C1—Fe1—C2	41.46 (11)	C2—C3—H3A	126.3
C6—Fe1—C2	109.43 (11)	Fe1—C3—H3A	126.3
C1—Fe1—C7	109.52 (11)	C3—C4—C5	108.8 (2)
C6—Fe1—C7	42.35 (10)	C3—C4—Fe1	70.52 (15)
C2—Fe1—C7	100.76 (11)	C5—C4—Fe1	68.31 (15)
C1—Fe1—C5	42.54 (10)	C3—C4—H4A	125.6
C6—Fe1—C5	110.06 (11)	C5—C4—H4A	125.6
C2—Fe1—C5	69.22 (11)	Fe1—C4—H4A	125.6
C7—Fe1—C5	147.55 (11)	C4—C5—C1	108.4 (2)
C1—Fe1—C10	110.26 (11)	C4—C5—Fe1	71.09 (15)
C6—Fe1—C10	42.03 (10)	C1—C5—Fe1	67.95 (14)
C2—Fe1—C10	146.94 (11)	C4—C5—H5A	125.8
C7—Fe1—C10	69.41 (11)	C1—C5—H5A	125.8
C5—Fe1—C10	101.64 (11)	Fe1—C5—H5A	125.8
C1—Fe1—C4	70.10 (11)	C10—C6—C7	105.2 (2)
C6—Fe1—C4	150.46 (11)	C10—C6—Si1	118.24 (19)
C2—Fe1—C4	68.23 (11)	C7—C6—Si1	119.00 (19)
C7—Fe1—C4	164.39 (12)	C10—C6—Fe1	69.75 (14)
C5—Fe1—C4	40.60 (11)	C7—C6—Fe1	69.38 (14)
C10—Fe1—C4	125.88 (11)	Si1—C6—Fe1	87.14 (10)
C1—Fe1—C9	150.85 (11)	C8—C7—C6	109.1 (2)
C6—Fe1—C9	70.15 (11)	C8—C7—Fe1	71.41 (15)
C2—Fe1—C9	164.83 (11)	C6—C7—Fe1	68.27 (14)
C7—Fe1—C9	68.32 (11)	C8—C7—H7A	125.4
C5—Fe1—C9	125.66 (11)	C6—C7—H7A	125.4
C10—Fe1—C9	40.79 (11)	Fe1—C7—H7A	125.4
C4—Fe1—C9	120.01 (11)	C9—C8—C7	108.5 (2)
C1—Fe1—C8	149.76 (11)	C9—C8—Fe1	70.01 (15)
C6—Fe1—C8	70.12 (11)	C7—C8—Fe1	68.04 (14)
C2—Fe1—C8	124.99 (12)	C9—C8—H8A	125.7
C7—Fe1—C8	40.55 (11)	C7—C8—H8A	125.7
C5—Fe1—C8	165.43 (12)	Fe1—C8—H8A	125.7
C10—Fe1—C8	68.33 (11)	C8—C9—C10	108.1 (2)
C4—Fe1—C8	136.73 (11)	C8—C9—Fe1	70.02 (15)
C9—Fe1—C8	39.98 (10)	C10—C9—Fe1	68.15 (15)
C1—Fe1—C3	69.81 (11)	C8—C9—H9A	125.9
C6—Fe1—C3	149.89 (11)	C10—C9—H9A	125.9
C2—Fe1—C3	40.76 (10)	Fe1—C9—H9A	125.9
C7—Fe1—C3	124.60 (11)	C9—C10—C6	109.1 (2)
C5—Fe1—C3	68.31 (12)	C9—C10—Fe1	71.06 (15)
C10—Fe1—C3	165.66 (11)	C6—C10—Fe1	68.22 (14)
C4—Fe1—C3	39.96 (11)	C9—C10—H10A	125.4
C9—Fe1—C3	136.73 (11)	C6—C10—H10A	125.4
C8—Fe1—C3	119.28 (12)	Fe1—C10—H10A	125.4
C11—Fe2—C16	88.15 (11)	C15—C11—C12	105.4 (2)
C11—Fe2—C20	109.18 (11)	C15—C11—Si2	119.56 (19)
C16—Fe2—C20	42.13 (11)	C12—C11—Si2	118.0 (2)
C11—Fe2—C12	42.19 (11)	C15—C11—Fe2	69.83 (15)
C16—Fe2—C12	109.86 (11)	C12—C11—Fe2	69.56 (14)
C20—Fe2—C12	147.08 (11)	Si2—C11—Fe2	87.59 (11)
C11—Fe2—C15	41.75 (11)	C13—C12—C11	109.0 (2)
C16—Fe2—C15	108.67 (11)	C13—C12—Fe2	71.73 (15)
C20—Fe2—C15	100.32 (12)	C11—C12—Fe2	68.25 (15)
C12—Fe2—C15	69.12 (12)	C13—C12—H12A	125.5
C11—Fe2—C17	110.12 (12)	C11—C12—H12A	125.5
C16—Fe2—C17	42.35 (10)	Fe2—C12—H12A	125.5
C20—Fe2—C17	69.14 (11)	C12—C13—C14	108.1 (2)
C12—Fe2—C17	102.09 (12)	C12—C13—Fe2	67.75 (15)
C15—Fe2—C17	146.79 (11)	C14—C13—Fe2	69.98 (15)
C11—Fe2—C14	69.77 (11)	C12—C13—H13A	125.9
C16—Fe2—C14	148.86 (11)	C14—C13—H13A	125.9
C20—Fe2—C14	124.23 (12)	Fe2—C13—H13A	125.9
C12—Fe2—C14	68.28 (12)	C15—C14—C13	107.8 (3)
C15—Fe2—C14	40.49 (11)	C15—C14—Fe2	67.82 (15)
C17—Fe2—C14	166.36 (11)	C13—C14—Fe2	69.99 (15)
C11—Fe2—C13	69.84 (11)	C15—C14—H14A	126.1
C16—Fe2—C13	150.27 (11)	C13—C14—H14A	126.1
C20—Fe2—C13	164.17 (11)	Fe2—C14—H14A	126.1
C12—Fe2—C13	40.52 (11)	C14—C15—C11	109.7 (2)
C15—Fe2—C13	68.05 (11)	C14—C15—Fe2	71.69 (16)
C17—Fe2—C13	126.48 (11)	C11—C15—Fe2	68.42 (14)
C14—Fe2—C13	40.04 (11)	C14—C15—H15A	125.2
C11—Fe2—C18	150.40 (12)	C11—C15—H15A	125.2
C16—Fe2—C18	70.15 (11)	Fe2—C15—H15A	125.2
C20—Fe2—C18	68.02 (12)	C20—C16—C17	104.2 (2)
C12—Fe2—C18	126.29 (11)	C20—C16—Si2	119.84 (19)
C15—Fe2—C18	164.42 (12)	C17—C16—Si2	118.2 (2)
C17—Fe2—C18	40.43 (11)	C20—C16—Fe2	69.11 (15)
C14—Fe2—C18	137.53 (12)	C17—C16—Fe2	69.17 (14)
C13—Fe2—C18	121.03 (11)	Si2—C16—Fe2	87.48 (10)
C11—Fe2—C19	149.46 (11)	C18—C17—C16	109.6 (2)
C16—Fe2—C19	70.02 (11)	C18—C17—Fe2	71.69 (15)
C20—Fe2—C19	40.52 (11)	C16—C17—Fe2	68.48 (13)
C12—Fe2—C19	165.80 (11)	C18—C17—H17A	125.2
C15—Fe2—C19	124.84 (12)	C16—C17—H17A	125.2
C17—Fe2—C19	67.84 (11)	Fe2—C17—H17A	125.2
C14—Fe2—C19	119.60 (12)	C19—C18—C17	108.3 (2)
C13—Fe2—C19	137.40 (11)	C19—C18—Fe2	70.43 (16)
C18—Fe2—C19	39.65 (11)	C17—C18—Fe2	67.88 (14)
O1—Si1—C21	111.50 (12)	C19—C18—H18A	125.8
O1—Si1—C6	111.18 (11)	C17—C18—H18A	125.8
C21—Si1—C6	112.97 (13)	Fe2—C18—H18A	125.8
O1—Si1—C1	111.21 (11)	C18—C19—C20	108.0 (2)
C21—Si1—C1	112.39 (13)	C18—C19—Fe2	69.92 (15)
C6—Si1—C1	96.82 (11)	C20—C19—Fe2	67.41 (15)
O1—Si2—C22	112.89 (12)	C18—C19—H19A	126.0
O1—Si2—C16	110.51 (11)	C20—C19—H19A	126.0
C22—Si2—C16	112.84 (13)	Fe2—C19—H19A	126.0
O1—Si2—C11	110.11 (11)	C19—C20—C16	109.9 (2)
C22—Si2—C11	112.69 (13)	C19—C20—Fe2	72.06 (16)
C16—Si2—C11	96.72 (11)	C16—C20—Fe2	68.76 (15)
Si1—O1—Si2	143.25 (12)	C19—C20—H20A	125.1
C2—C1—C5	105.5 (2)	C16—C20—H20A	125.1
C2—C1—Si1	119.59 (19)	Fe2—C20—H20A	125.1
C5—C1—Si1	117.58 (19)	Si1—C21—H21A	109.5
C2—C1—Fe1	69.82 (15)	Si1—C21—H21B	109.5
C5—C1—Fe1	69.51 (14)	H21A—C21—H21B	109.5
Si1—C1—Fe1	87.24 (11)	Si1—C21—H21C	109.5
C1—C2—C3	110.0 (2)	H21A—C21—H21C	109.5
C1—C2—Fe1	68.72 (15)	H21B—C21—H21C	109.5
C3—C2—Fe1	71.74 (15)	Si2—C22—H22A	109.5
C1—C2—H2A	125.0	Si2—C22—H22B	109.5
C3—C2—H2A	125.0	H22A—C22—H22B	109.5
Fe1—C2—H2A	125.0	Si2—C22—H22C	109.5
C4—C3—C2	107.4 (2)	H22A—C22—H22C	109.5
C4—C3—Fe1	69.52 (15)	H22B—C22—H22C	109.5
C2—C3—Fe1	67.50 (15)

Fe1—Si1—Si2—Fe2	75.07 (5)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₄)₂(CH₃Si)]₂O
M_r	470.28
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.5203 (1), 11.4213 (3), 22.2986 (6)
V (Å³)	1915.26 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.65
Crystal size (mm)	0.35 × 0.32 × 0.10

Data collection
Diffractometer	Nonius Kappa-CCD diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)
T_min, T_max	0.596, 0.853
No. of measured, independent and observed [I > 2σ(I)] reflections	19591, 4381, 3810
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.00
No. of reflections	4381
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.48
Absolute structure	(Flack, 1983), 1871 Friedel pairs
Absolute structure parameter	−0.009 (13)

Computer programs: COLLECT (Nonius 1997-2001), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1999), SHELXT.

Selected geometric parameters (Å, º) top

Fe1—C1	2.010 (2)	Fe2—C15	2.028 (3)
Fe1—C6	2.016 (2)	Fe2—C17	2.030 (2)
Fe1—C2	2.025 (3)	Fe2—C14	2.079 (3)
Fe1—C7	2.032 (3)	Fe2—C13	2.080 (3)
Fe1—C5	2.032 (3)	Fe2—C18	2.080 (3)
Fe1—C10	2.037 (3)	Fe2—C19	2.087 (3)
Fe1—C4	2.068 (3)	Si1—O1	1.6308 (18)
Fe1—C9	2.076 (3)	Si1—C21	1.851 (3)
Fe1—C8	2.076 (3)	Si1—C6	1.882 (3)
Fe1—C3	2.082 (3)	Si1—C1	1.885 (3)
Fe2—C11	2.009 (3)	Si2—O1	1.6377 (19)
Fe2—C16	2.020 (3)	Si2—C22	1.847 (3)
Fe2—C20	2.025 (3)	Si2—C16	1.871 (3)
Fe2—C12	2.027 (3)	Si2—C11	1.879 (3)

O1—Si1—C6	111.18 (11)	O1—Si2—C11	110.11 (11)
O1—Si1—C1	111.21 (11)	C16—Si2—C11	96.72 (11)
C6—Si1—C1	96.82 (11)	Si1—O1—Si2	143.25 (12)
O1—Si2—C16	110.51 (11)

Fe1—Si1—Si2—Fe2	75.07 (5)

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An oxy­gen-bridged bis­(sila­[1]­ferrocenophane), [Fe(η-C5H4)2Si(Me)]2O

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An oxygen-bridged bis(sila[1]ferrocenophane), [Fe(η-C₅H₄)₂Si(Me)]₂O