Redetermination of the structure of diferrocenyl ketone at low temperature

The structure of diferrocenyl ketone, [Fe₂(C₅H₅)₂(C₁₁H₈O)], was redetermined as part of our investigations of carbon-iron hyperconjugation. The title ketone lies on a twofold axis of symmetry. Lengthening of the carbonyl C=O bond [1.237 (3) Å compared with that expected for simple ketones, 1.210 Å] and slight slippage of the Fe atom towards the carbonyl carbon are consistent with the presence of strong hyperconjugation of the carbonyl group with the adjacent Fe-C bond. The structure was determined at 130 K.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.094
• Data-to-parameter ratio = 12.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.829
          Tmax scaled      0.829 Tmin scaled      0.713

---

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(1)

Crystal data

[Fe2(C5H5)2(C11H8O)]	F(000) = 408
Mr = 398.05	Dx = 1.705 Mg m^−3
Monoclinic, P2/c	Melting point: 211.5 K
Hall symbol: -P 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 10.4058 (11) Å	Cell parameters from 2038 reflections
b = 6.1448 (7) Å	θ = 3.3–28.8°
c = 12.9773 (14) Å	µ = 1.87 mm^−1
β = 110.835 (2)°	T = 130 K
V = 775.53 (15) Å^3	Rod, red
Z = 2	0.35 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1368 independent reflections
Radiation source: fine-focus sealed tube	1228 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Blessing, 1995; Sheldrick, 2001)	h = −12→12
Tmin = 0.86, Tmax = 1.0	k = −7→4
3879 measured reflections	l = −14→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0614P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
1368 reflections	Δρmax = 0.80 e Å^−3
111 parameters	Δρmin = −0.46 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.007 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6301 (2)	0.1018 (3)	0.26450 (16)	0.0192 (5)
C2	0.6544 (2)	0.3244 (4)	0.24073 (17)	0.0213 (5)
H2	0.5863	0.4330	0.2109	0.026*
C3	0.7976 (2)	0.3511 (4)	0.26977 (17)	0.0227 (5)
H3	0.8425	0.4815	0.2623	0.027*
C4	0.8639 (2)	0.1499 (4)	0.31219 (17)	0.0235 (5)
H4	0.9601	0.1235	0.3386	0.028*
C5	0.7603 (2)	−0.0035 (3)	0.30789 (16)	0.0225 (5)
H5	0.7752	−0.1515	0.3302	0.027*
C6	0.6438 (3)	0.2692 (3)	0.5090 (2)	0.0311 (7)
H6	0.5527	0.2186	0.4942	0.037*
C7	0.7657 (2)	0.1468 (4)	0.55660 (17)	0.0287 (5)
H7	0.7707	−0.0009	0.5793	0.034*
C8	0.8795 (3)	0.2827 (4)	0.5647 (2)	0.0286 (6)
H8	0.9737	0.2421	0.5933	0.034*
C9	0.8268 (2)	0.4899 (3)	0.52219 (17)	0.0275 (5)
H9	0.8797	0.6131	0.5178	0.033*
C10	0.6820 (2)	0.4814 (4)	0.48745 (18)	0.0304 (5)
H10	0.6206	0.5977	0.4552	0.036*
C11	0.5000	−0.0124 (4)	0.2500	0.0220 (6)
O1	0.5000	−0.2137 (3)	0.2500	0.0372 (7)
Fe1	0.75090 (3)	0.25631 (4)	0.40398 (2)	0.0176 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0249 (11)	0.0146 (10)	0.0168 (10)	−0.0005 (8)	0.0058 (8)	−0.0030 (8)
C2	0.0285 (12)	0.0171 (10)	0.0176 (11)	0.0011 (10)	0.0071 (9)	0.0004 (9)
C3	0.0290 (12)	0.0216 (11)	0.0208 (11)	−0.0037 (10)	0.0127 (9)	−0.0023 (10)
C4	0.0214 (11)	0.0269 (12)	0.0246 (12)	0.0017 (10)	0.0111 (9)	−0.0056 (10)
C5	0.0259 (11)	0.0181 (10)	0.0235 (11)	0.0046 (8)	0.0087 (9)	−0.0022 (9)
C6	0.0303 (15)	0.0443 (16)	0.0230 (14)	−0.0016 (10)	0.0148 (12)	−0.0049 (9)
C7	0.0371 (13)	0.0295 (13)	0.0201 (12)	0.0008 (10)	0.0109 (10)	0.0026 (10)
C8	0.0264 (13)	0.0370 (13)	0.0193 (13)	0.0024 (10)	0.0043 (11)	−0.0018 (10)
C9	0.0347 (12)	0.0260 (11)	0.0207 (11)	−0.0024 (9)	0.0086 (9)	−0.0081 (9)
C10	0.0370 (13)	0.0331 (13)	0.0231 (12)	0.0098 (10)	0.0132 (10)	−0.0054 (10)
C11	0.0247 (15)	0.0167 (14)	0.0216 (15)	0.000	0.0044 (12)	0.000
O1	0.0279 (13)	0.0117 (10)	0.065 (2)	0.000	0.0081 (13)	0.000
Fe1	0.0184 (3)	0.0162 (3)	0.0180 (3)	0.00138 (10)	0.00631 (19)	−0.00086 (10)

Geometric parameters (Å, º)

C1—C5	1.424 (3)	C6—C10	1.420 (3)
C1—C2	1.444 (3)	C6—Fe1	2.046 (3)
C1—C11	1.477 (2)	C6—H6	0.9500
C1—Fe1	2.0344 (19)	C7—C8	1.422 (3)
C2—C3	1.411 (3)	C7—Fe1	2.045 (2)
C2—Fe1	2.039 (2)	C7—H7	0.9500
C2—H2	0.9500	C8—C9	1.418 (3)
C3—C4	1.427 (3)	C8—Fe1	2.045 (3)
C3—Fe1	2.052 (2)	C8—H8	0.9500
C3—H3	0.9500	C9—C10	1.412 (3)
C4—C5	1.418 (3)	C9—Fe1	2.043 (2)
C4—Fe1	2.056 (2)	C9—H9	0.9500
C4—H4	0.9500	C10—Fe1	2.038 (2)
C5—Fe1	2.0495 (19)	C10—H10	0.9500
C5—H5	0.9500	C11—O1	1.237 (3)
C6—C7	1.413 (3)	C11—C1^i	1.477 (2)
C5—C1—C2	107.53 (18)	C9—C10—C6	108.2 (2)
C5—C1—C11	122.32 (17)	C9—C10—Fe1	69.96 (12)
C2—C1—C11	130.15 (18)	C6—C10—Fe1	69.96 (14)
C5—C1—Fe1	70.17 (11)	C9—C10—H10	125.9
C2—C1—Fe1	69.42 (11)	C6—C10—H10	125.9
C11—C1—Fe1	125.69 (12)	Fe1—C10—H10	125.8
C3—C2—C1	107.54 (19)	O1—C11—C1	118.37 (12)
C3—C2—Fe1	70.32 (12)	O1—C11—C1^i	118.37 (12)
C1—C2—Fe1	69.06 (11)	C1—C11—C1^i	123.3 (2)
C3—C2—H2	126.2	C1—Fe1—C10	124.53 (9)
C1—C2—H2	126.2	C1—Fe1—C2	41.52 (8)
Fe1—C2—H2	126.0	C10—Fe1—C2	106.06 (9)
C2—C3—C4	108.8 (2)	C1—Fe1—C9	161.31 (9)
C2—C3—Fe1	69.34 (12)	C10—Fe1—C9	40.47 (9)
C4—C3—Fe1	69.80 (11)	C2—Fe1—C9	123.50 (9)
C2—C3—H3	125.6	C1—Fe1—C8	156.57 (9)
C4—C3—H3	125.6	C10—Fe1—C8	68.31 (10)
Fe1—C3—H3	126.8	C2—Fe1—C8	160.94 (10)
C5—C4—C3	107.71 (19)	C9—Fe1—C8	40.58 (8)
C5—C4—Fe1	69.56 (11)	C1—Fe1—C6	107.48 (10)
C3—C4—Fe1	69.54 (11)	C10—Fe1—C6	40.68 (8)
C5—C4—H4	126.1	C2—Fe1—C6	120.03 (10)
C3—C4—H4	126.1	C9—Fe1—C6	68.23 (9)
Fe1—C4—H4	126.3	C8—Fe1—C6	68.37 (12)
C4—C5—C1	108.43 (18)	C1—Fe1—C7	121.20 (9)
C4—C5—Fe1	70.02 (11)	C10—Fe1—C7	68.16 (9)
C1—C5—Fe1	69.03 (11)	C2—Fe1—C7	155.95 (10)
C4—C5—H5	125.8	C9—Fe1—C7	68.16 (9)
C1—C5—H5	125.8	C8—Fe1—C7	40.70 (10)
Fe1—C5—H5	126.7	C6—Fe1—C7	40.42 (10)
C7—C6—C10	107.7 (2)	C1—Fe1—C5	40.81 (8)
C7—C6—Fe1	69.75 (14)	C10—Fe1—C5	162.56 (9)
C10—C6—Fe1	69.36 (14)	C2—Fe1—C5	68.90 (9)
C7—C6—H6	126.1	C9—Fe1—C5	156.17 (9)
C10—C6—H6	126.1	C8—Fe1—C5	121.80 (9)
Fe1—C6—H6	126.3	C6—Fe1—C5	126.20 (9)
C6—C7—C8	108.3 (2)	C7—Fe1—C5	109.24 (9)
C6—C7—Fe1	69.83 (14)	C1—Fe1—C3	68.60 (8)
C8—C7—Fe1	69.63 (14)	C10—Fe1—C3	119.53 (9)
C6—C7—H7	125.9	C2—Fe1—C3	40.34 (8)
C8—C7—H7	125.9	C9—Fe1—C3	107.04 (9)
Fe1—C7—H7	126.3	C8—Fe1—C3	125.21 (10)
C9—C8—C7	107.6 (2)	C6—Fe1—C3	154.68 (10)
C9—C8—Fe1	69.65 (13)	C7—Fe1—C3	163.03 (9)
C7—C8—Fe1	69.67 (13)	C5—Fe1—C3	68.15 (8)
C9—C8—H8	126.2	C1—Fe1—C4	68.63 (8)
C7—C8—H8	126.2	C10—Fe1—C4	154.94 (9)
Fe1—C8—H8	126.0	C2—Fe1—C4	68.59 (9)
C10—C9—C8	108.2 (2)	C9—Fe1—C4	120.71 (9)
C10—C9—Fe1	69.57 (12)	C8—Fe1—C4	108.34 (10)
C8—C9—Fe1	69.76 (13)	C6—Fe1—C4	163.28 (9)
C10—C9—H9	125.9	C7—Fe1—C4	126.52 (9)
C8—C9—H9	125.9	C5—Fe1—C4	40.43 (8)
Fe1—C9—H9	126.3	C3—Fe1—C4	40.66 (9)
C5—C1—C2—C3	0.0 (2)	C10—C9—Fe1—C7	−81.50 (14)
C11—C1—C2—C3	179.96 (17)	C8—C9—Fe1—C7	38.03 (15)
Fe1—C1—C2—C3	60.06 (15)	C10—C9—Fe1—C5	−169.87 (18)
C5—C1—C2—Fe1	−60.09 (14)	C8—C9—Fe1—C5	−50.3 (3)
C11—C1—C2—Fe1	119.90 (19)	C10—C9—Fe1—C3	115.78 (13)
C1—C2—C3—C4	−0.5 (2)	C8—C9—Fe1—C3	−124.69 (16)
Fe1—C2—C3—C4	58.80 (14)	C10—C9—Fe1—C4	157.99 (13)
C1—C2—C3—Fe1	−59.27 (14)	C8—C9—Fe1—C4	−82.48 (17)
C2—C3—C4—C5	0.8 (2)	C9—C8—Fe1—C1	−165.5 (2)
Fe1—C3—C4—C5	59.30 (14)	C7—C8—Fe1—C1	−46.8 (3)
C2—C3—C4—Fe1	−58.52 (15)	C9—C8—Fe1—C10	−37.43 (14)
C3—C4—C5—C1	−0.8 (2)	C7—C8—Fe1—C10	81.29 (15)
Fe1—C4—C5—C1	58.49 (14)	C9—C8—Fe1—C2	38.7 (4)
C3—C4—C5—Fe1	−59.29 (14)	C7—C8—Fe1—C2	157.4 (2)
C2—C1—C5—C4	0.5 (2)	C7—C8—Fe1—C9	118.7 (2)
C11—C1—C5—C4	−179.48 (16)	C9—C8—Fe1—C6	−81.36 (15)
Fe1—C1—C5—C4	−59.10 (14)	C7—C8—Fe1—C6	37.36 (13)
C2—C1—C5—Fe1	59.61 (13)	C9—C8—Fe1—C7	−118.7 (2)
C11—C1—C5—Fe1	−120.38 (17)	C9—C8—Fe1—C5	158.53 (13)
C10—C6—C7—C8	0.0 (3)	C7—C8—Fe1—C5	−82.75 (16)
Fe1—C6—C7—C8	59.21 (17)	C9—C8—Fe1—C3	74.19 (17)
C10—C6—C7—Fe1	−59.17 (17)	C7—C8—Fe1—C3	−167.09 (13)
C6—C7—C8—C9	0.3 (3)	C9—C8—Fe1—C4	116.10 (15)
Fe1—C7—C8—C9	59.59 (17)	C7—C8—Fe1—C4	−125.18 (14)
C6—C7—C8—Fe1	−59.33 (16)	C7—C6—Fe1—C1	117.89 (14)
C7—C8—C9—C10	−0.5 (3)	C10—C6—Fe1—C1	−123.04 (15)
Fe1—C8—C9—C10	59.14 (15)	C7—C6—Fe1—C10	−119.1 (2)
C7—C8—C9—Fe1	−59.60 (16)	C7—C6—Fe1—C2	161.45 (13)
C8—C9—C10—C6	0.5 (3)	C10—C6—Fe1—C2	−79.48 (17)
Fe1—C9—C10—C6	59.74 (16)	C7—C6—Fe1—C9	−81.44 (15)
C8—C9—C10—Fe1	−59.26 (16)	C10—C6—Fe1—C9	37.62 (14)
C7—C6—C10—C9	−0.3 (3)	C7—C6—Fe1—C8	−37.61 (13)
Fe1—C6—C10—C9	−59.74 (15)	C10—C6—Fe1—C8	81.46 (16)
C7—C6—C10—Fe1	59.42 (17)	C10—C6—Fe1—C7	119.1 (2)
C5—C1—C11—O1	−17.7 (2)	C7—C6—Fe1—C5	76.73 (17)
C2—C1—C11—O1	162.34 (17)	C10—C6—Fe1—C5	−164.20 (13)
Fe1—C1—C11—O1	−105.38 (13)	C7—C6—Fe1—C3	−165.34 (19)
C5—C1—C11—C1^i	162.3 (2)	C10—C6—Fe1—C3	−46.3 (3)
C2—C1—C11—C1^i	−17.66 (17)	C7—C6—Fe1—C4	44.1 (4)
Fe1—C1—C11—C1^i	74.62 (13)	C10—C6—Fe1—C4	163.2 (3)
C5—C1—Fe1—C10	−167.19 (12)	C6—C7—Fe1—C1	−80.25 (15)
C2—C1—Fe1—C10	74.29 (15)	C8—C7—Fe1—C1	160.21 (13)
C11—C1—Fe1—C10	−51.0 (2)	C6—C7—Fe1—C10	37.86 (13)
C5—C1—Fe1—C2	118.52 (18)	C8—C7—Fe1—C10	−81.68 (15)
C11—C1—Fe1—C2	−125.3 (2)	C6—C7—Fe1—C2	−42.5 (3)
C5—C1—Fe1—C9	160.8 (2)	C8—C7—Fe1—C2	−162.1 (2)
C2—C1—Fe1—C9	42.2 (3)	C6—C7—Fe1—C9	81.62 (15)
C11—C1—Fe1—C9	−83.1 (3)	C8—C7—Fe1—C9	−37.92 (13)
C5—C1—Fe1—C8	−49.8 (3)	C6—C7—Fe1—C8	119.5 (2)
C2—C1—Fe1—C8	−168.4 (2)	C8—C7—Fe1—C6	−119.5 (2)
C11—C1—Fe1—C8	66.3 (3)	C6—C7—Fe1—C5	−123.71 (14)
C5—C1—Fe1—C6	−125.64 (13)	C8—C7—Fe1—C5	116.75 (14)
C2—C1—Fe1—C6	115.84 (13)	C6—C7—Fe1—C3	158.2 (3)
C11—C1—Fe1—C6	−9.5 (2)	C8—C7—Fe1—C3	38.7 (4)
C5—C1—Fe1—C7	−83.57 (14)	C6—C7—Fe1—C4	−165.57 (12)
C2—C1—Fe1—C7	157.90 (13)	C8—C7—Fe1—C4	74.89 (16)
C11—C1—Fe1—C7	32.6 (2)	C4—C5—Fe1—C1	119.98 (17)
C2—C1—Fe1—C5	−118.52 (18)	C4—C5—Fe1—C10	157.5 (3)
C11—C1—Fe1—C5	116.1 (2)	C1—C5—Fe1—C10	37.6 (3)
C5—C1—Fe1—C3	80.92 (13)	C4—C5—Fe1—C2	81.35 (13)
C2—C1—Fe1—C3	−37.60 (12)	C1—C5—Fe1—C2	−38.63 (12)
C11—C1—Fe1—C3	−162.9 (2)	C4—C5—Fe1—C9	−44.9 (3)
C5—C1—Fe1—C4	37.10 (12)	C1—C5—Fe1—C9	−164.84 (19)
C2—C1—Fe1—C4	−81.42 (14)	C4—C5—Fe1—C8	−80.97 (15)
C11—C1—Fe1—C4	153.25 (19)	C1—C5—Fe1—C8	159.05 (13)
C9—C10—Fe1—C1	−164.81 (12)	C4—C5—Fe1—C6	−166.16 (13)
C6—C10—Fe1—C1	76.05 (18)	C1—C5—Fe1—C6	73.86 (16)
C9—C10—Fe1—C2	−123.20 (13)	C4—C5—Fe1—C7	−124.22 (13)
C6—C10—Fe1—C2	117.66 (16)	C1—C5—Fe1—C7	115.81 (13)
C6—C10—Fe1—C9	−119.1 (2)	C4—C5—Fe1—C3	37.86 (14)
C9—C10—Fe1—C8	37.53 (14)	C1—C5—Fe1—C3	−82.12 (13)
C6—C10—Fe1—C8	−81.61 (17)	C1—C5—Fe1—C4	−119.98 (17)
C9—C10—Fe1—C6	119.1 (2)	C2—C3—Fe1—C1	38.66 (13)
C9—C10—Fe1—C7	81.51 (14)	C4—C3—Fe1—C1	−81.70 (14)
C6—C10—Fe1—C7	−37.63 (15)	C2—C3—Fe1—C10	−79.87 (15)
C9—C10—Fe1—C5	166.3 (2)	C4—C3—Fe1—C10	159.77 (13)
C6—C10—Fe1—C5	47.1 (3)	C4—C3—Fe1—C2	−120.36 (19)
C9—C10—Fe1—C3	−81.66 (15)	C2—C3—Fe1—C9	−122.07 (13)
C6—C10—Fe1—C3	159.20 (16)	C4—C3—Fe1—C9	117.57 (14)
C9—C10—Fe1—C4	−49.5 (3)	C2—C3—Fe1—C8	−162.96 (13)
C6—C10—Fe1—C4	−168.67 (18)	C4—C3—Fe1—C8	76.68 (16)
C3—C2—Fe1—C1	−118.65 (18)	C2—C3—Fe1—C6	−47.1 (3)
C3—C2—Fe1—C10	116.96 (13)	C4—C3—Fe1—C6	−167.46 (19)
C1—C2—Fe1—C10	−124.39 (13)	C2—C3—Fe1—C7	167.1 (3)
C3—C2—Fe1—C9	76.32 (15)	C4—C3—Fe1—C7	46.7 (4)
C1—C2—Fe1—C9	−165.03 (12)	C2—C3—Fe1—C5	82.71 (13)
C3—C2—Fe1—C8	47.1 (3)	C4—C3—Fe1—C5	−37.65 (13)
C1—C2—Fe1—C8	165.8 (3)	C2—C3—Fe1—C4	120.36 (19)
C3—C2—Fe1—C6	158.79 (13)	C5—C4—Fe1—C1	−37.44 (12)
C1—C2—Fe1—C6	−82.56 (14)	C3—C4—Fe1—C1	81.61 (14)
C3—C2—Fe1—C7	−170.80 (19)	C5—C4—Fe1—C10	−164.31 (19)
C1—C2—Fe1—C7	−52.1 (3)	C3—C4—Fe1—C10	−45.3 (3)
C3—C2—Fe1—C5	−80.67 (13)	C5—C4—Fe1—C2	−82.18 (13)
C1—C2—Fe1—C5	37.98 (12)	C3—C4—Fe1—C2	36.87 (13)
C1—C2—Fe1—C3	118.65 (18)	C5—C4—Fe1—C9	160.64 (12)
C3—C2—Fe1—C4	−37.15 (13)	C3—C4—Fe1—C9	−80.31 (15)
C1—C2—Fe1—C4	81.50 (13)	C5—C4—Fe1—C8	117.84 (13)
C10—C9—Fe1—C1	42.4 (3)	C3—C4—Fe1—C8	−123.11 (14)
C8—C9—Fe1—C1	161.9 (3)	C5—C4—Fe1—C6	42.1 (4)
C8—C9—Fe1—C10	119.5 (2)	C3—C4—Fe1—C6	161.2 (3)
C10—C9—Fe1—C2	74.65 (15)	C5—C4—Fe1—C7	76.29 (15)
C8—C9—Fe1—C2	−165.83 (14)	C3—C4—Fe1—C7	−164.66 (13)
C10—C9—Fe1—C8	−119.5 (2)	C3—C4—Fe1—C5	119.05 (19)
C10—C9—Fe1—C6	−37.81 (14)	C5—C4—Fe1—C3	−119.05 (19)
C8—C9—Fe1—C6	81.72 (17)

Symmetry code: (i) −x+1, y, −z+1/2.