1,1′-Bis[bis­(4-tert-butyl­phen­yl)meth­yl]ferrocene

Bauer, H.; Sun, Y.; Sitzmann, H.

doi:10.1107/S1600536812041360

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1450

doi:10.1107/S1600536812041360

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1,1′-Bis[bis(4-tert-butylphenyl)methyl]ferrocene

Heiko Bauer,^a Yu Sun ^a and Helmut Sitzmann ^a ^*

^aDepartment of Chemistry, Technical University of Kaiserslautern, 67663 Kaiserslautern, Germany
^*Correspondence e-mail: sitzmann@chemie.uni-kl.de

(Received 21 September 2012; accepted 2 October 2012; online 3 November 2012)

The molecule of the title compound, [Fe(C₂₆H₃₁)₂], is located on an inversion center. The two cyclopentadienyl rings exhibit a staggered conformation, which results from the bulky bis(4-tert-butylphenyl)methyl substituents situated on opposite sides of the molecule.

Related literature

For reports of the Gomberg radical, see: Gomberg (1900 , 1901 , 1902 ). For solution behavior of the triphenylmethyl radical, see: Lankamp et al. (1968 ); McBride (1974 ). For paramagnetic cyclopentadienyliron complexes, see: Sitzmann et al. (1996 ); Sitzmann (2001 ); Weismann et al. (2011 ). For cyclopentadienyl radicals, see: Sitzmann et al. (1998 , 2000 ).

Experimental

Crystal data

[Fe(C₂₆H₃₁)₂]
M_r = 742.87
Monoclinic, P 2₁ /n
a = 6.0893 (2) Å
b = 30.7616 (8) Å
c = 11.0983 (3) Å
β = 98.982 (3)°
V = 2053.40 (10) Å³
Z = 2
Cu Kα radiation
μ = 3.19 mm⁻¹
T = 150 K
0.18 × 0.13 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) $[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ T_min = 0.889, T_max = 1.000
12754 measured reflections
3267 independent reflections
2784 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.071
S = 1.01
3267 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812041360/mw2088sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041360/mw2088Isup2.hkl

checkCIF report

Comment top

Our interest in paramagnetic cyclopentadienyliron complexes (Sitzmann et al., 1996; Sitzmann, 2001; Weismann et al., 2011) and cyclopentadienyl radicals (Sitzmann et al., 1998; Sitzmann et al., 2000) stimulated experiments aimed at the generation of ferrocenyl derivatives of the Gomberg radical (Gomberg, 1900; Gomberg, 1901; Gomberg, 1902). The triphenylmethyl radical exists in solution in an equilibrium with its unsymmetrical dimer, where one para phenyl carbon atom forms a bond to the central methyl carbon of the second molecule (Lankamp et al., 1968; McBride, 1974). In order to prepare starting compounds for the synthesis of ferrocenyl diaryl radicals, diphenylfulvene was equipped with tert-butyl substituents in the para position to prevent such side reactions. Treatment with lithium aluminium hydride and metalation with n-butyllithium, followed by complexation with iron(II) chloride, gave the corresponding ferrocene with two bis(4-tert-butylphenyl)methyl substituents.

The iron center is bound to the cyclopentadienyl ring in the typical η⁵ manner. The distance between the two cyclopentadienyl ring planes is 3.315 Å, implying a Cp_cent—Fe distance of 1.658 Å. The two Cp rings are arranged in a staggered conformation which results from the large di(4-tert-butylphenyl)methyl substituents arranging on opposite sides of the molecule.

Related literature top

For reports of the Gomberg radical, see: Gomberg (1900, 1901, 1902). For solution behavior of the triphenylmethyl radical, see: Lankamp et al. (1968); McBride (1974). For paramagnetic cyclopentadienyiron complexes, see: Sitzmann et al. (1996); Sitzmann (2001); Weismann et al. (2011). For cyclopentadienyl radicals, see: Sitzmann et al. (1998, 2000).

Experimental top

Synthesis of 5-(di(4-tert-butylphenyl)methyl)-1,3-cyclopentadien: To a stirred solution of 1,1'-bis-(4-tert-butylphenyl)-(2,4-cyclopentadien-ylidenemethylene) (2.04 g, 6.0 mmol) in THF (60 mL) was added lithium aluminium hydride (300 mg, 8.0 mmol). The reaction mixture was heated at 65 °C for 15 h until the orange suspension became colourless. The colourless suspension was slowly poured onto a mixture of diluted sulfuric acid (10%) and ice. After separation, the aqueous layer was extracted with toluene (3 x 100 mL) and the combined organic layers were washed with water (100 mL), dried over MgSO₄ and taken to dryness in vacuo. This yielded a light yellow solid (1.88 g, 5.46 mmol, 91%).

Synthesis of (di(4-tert-butylphenyl))methyl-cyclopentadienyl lithium: To a stirred solution of 5-(di(4-tert-butylphenyl)methyl)-1,3-cyclopentadien (2.07 g, 6.0 mmol) in diethyl ether (100 mL) at 0 °C a solution (1.9 mol/l) of n-butyl lithium (4.0 mL, 6.4 mmol) in hexane was added dropwise. After stirring for ten minutes at 0 °C, the mixture was allowed to stir for 30 minutes at room temperature until the yellow solution turned to an orange suspension. The solvent was removed in vacuo and the residue was suspended in pentane (50 mL), filtered and washed with pentane (3 x 50 mL), yielding a colourless powder (1.77 g, 5.05 mmol, 84%).

Synthesis of 1,1'-bis[(di(4-tert-butylphenyl)methyl)cyclopentadienyl]iron: A mixture of (di(4-tert-butylphenyl))methyl-cyclopentadienyl lithium (1.77 g, 5.05 mmol) and anhydrous iron(II) chloride (659.1 mg, 5.20 mmol) in THF (250 mL) was stirred for 18 h at room temperature. The darkened solution was evaporated and the resulting residue extracted with pentane (5 x 100 mL). The yellow solution was taken to dryness and the yellow powder recrystallized from pentane. The product could be crystallized at low temperature yielding plate-like yellow crystals (1.16 g, 1.56 mmol, 62%).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2010); cell refinement: CrysAlis CCD (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. : View of the title compound showing thermal ellipsoids at 50% probability.
	Fig. 2. : View of the packing of the title compound.

1,1'-Bis[bis(4-tert-butylphenyl)methyl]ferrocene top

Crystal data top

[Fe(C₂₆H₃₁)₂]	F(000) = 800
M_r = 742.87	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 6229 reflections
a = 6.0893 (2) Å	θ = 2.9–62.6°
b = 30.7616 (8) Å	µ = 3.19 mm⁻¹
c = 11.0983 (3) Å	T = 150 K
β = 98.982 (3)°	Plate, yellow
V = 2053.40 (10) Å³	0.18 × 0.13 × 0.09 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	3267 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2784 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 16.1399 pixels mm^-1	θ_max = 62.7°, θ_min = 2.9°
ω scans	h = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −31→35
T_min = 0.889, T_max = 1.000	l = −12→12
12754 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0434P)²] where P = (F_o² + 2F_c²)/3
3267 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Fe(C₂₆H₃₁)₂]	V = 2053.40 (10) Å³
M_r = 742.87	Z = 2
Monoclinic, P2₁/n	Cu Kα radiation
a = 6.0893 (2) Å	µ = 3.19 mm⁻¹
b = 30.7616 (8) Å	T = 150 K
c = 11.0983 (3) Å	0.18 × 0.13 × 0.09 mm
β = 98.982 (3)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	3267 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2784 reflections with I > 2σ(I)
T_min = 0.889, T_max = 1.000	R_int = 0.028
12754 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
3267 reflections	Δρ_min = −0.29 e Å⁻³
247 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. All hydrogen atoms were placed in calculated positions (C–H 0.96, 0.98 or 1.00 Å) and refined by using a riding model.

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

	x	y	z	U_iso*/U_eq
C1	0.3111 (2)	0.44424 (5)	0.46953 (13)	0.0208 (3)
C2	0.5266 (3)	0.43796 (5)	0.43750 (13)	0.0236 (3)
H2	0.6324	0.4169	0.4717	0.028*
C3	0.5560 (3)	0.46865 (5)	0.34559 (14)	0.0269 (4)
H3	0.6848	0.4716	0.3078	0.032*
C4	0.3609 (3)	0.49414 (5)	0.31997 (13)	0.0265 (4)
H4	0.3355	0.5171	0.2624	0.032*
C5	0.2100 (3)	0.47904 (5)	0.39611 (13)	0.0228 (3)
H5	0.0653	0.4903	0.3978	0.027*
C6	0.1928 (2)	0.41733 (5)	0.55424 (13)	0.0207 (3)
H6	0.0580	0.4342	0.5671	0.025*
C7	0.1099 (2)	0.37397 (5)	0.49700 (13)	0.0213 (3)
C8	−0.0287 (3)	0.34847 (5)	0.55661 (14)	0.0266 (4)
H8	−0.0632	0.3579	0.6330	0.032*
C9	−0.1173 (3)	0.30991 (5)	0.50777 (15)	0.0289 (4)
H9	−0.2132	0.2937	0.5506	0.035*
C10	−0.0690 (2)	0.29413 (5)	0.39658 (14)	0.0235 (3)
C11	0.0726 (3)	0.31913 (5)	0.33893 (14)	0.0274 (4)
H11	0.1119	0.3092	0.2641	0.033*
C12	0.1593 (3)	0.35845 (5)	0.38752 (14)	0.0268 (4)
H12	0.2542	0.3749	0.3446	0.032*
C13	−0.1713 (3)	0.25134 (5)	0.34417 (15)	0.0291 (4)
C14	−0.1032 (3)	0.21442 (6)	0.43535 (18)	0.0439 (5)
H14A	0.0593	0.2127	0.4530	0.066*
H14B	−0.1631	0.1868	0.4002	0.066*
H14C	−0.1624	0.2202	0.5110	0.066*
C15	−0.4254 (3)	0.25543 (6)	0.32226 (19)	0.0446 (5)
H15A	−0.4774	0.2618	0.3996	0.067*
H15B	−0.4914	0.2281	0.2888	0.067*
H15C	−0.4699	0.2791	0.2644	0.067*
C16	−0.0956 (3)	0.23944 (6)	0.22250 (16)	0.0382 (4)
H16A	−0.1366	0.2628	0.1633	0.057*
H16B	−0.1679	0.2124	0.1912	0.057*
H16C	0.0661	0.2355	0.2354	0.057*
C17	0.3308 (2)	0.41091 (5)	0.67958 (13)	0.0211 (3)
C18	0.2846 (3)	0.43382 (5)	0.78101 (14)	0.0240 (3)
H18	0.1578	0.4522	0.7734	0.029*
C19	0.4209 (3)	0.43015 (5)	0.89289 (13)	0.0245 (4)
H19	0.3853	0.4462	0.9604	0.029*
C20	0.6087 (3)	0.40365 (5)	0.90922 (13)	0.0226 (3)
C21	0.6488 (3)	0.37976 (5)	0.80823 (13)	0.0244 (3)
H21	0.7732	0.3608	0.8162	0.029*
C22	0.5115 (3)	0.38301 (5)	0.69618 (14)	0.0240 (3)
H22	0.5421	0.3658	0.6297	0.029*
C23	0.7610 (3)	0.40157 (5)	1.03284 (14)	0.0260 (4)
C24	0.8546 (3)	0.44714 (6)	1.06587 (15)	0.0358 (4)
H24A	0.9356	0.4575	1.0017	0.054*
H24B	0.9560	0.4459	1.1436	0.054*
H24C	0.7321	0.4671	1.0733	0.054*
C25	0.6265 (3)	0.38601 (6)	1.13129 (14)	0.0320 (4)
H25A	0.5061	0.4066	1.1373	0.048*
H25B	0.7245	0.3842	1.2101	0.048*
H25C	0.5635	0.3573	1.1091	0.048*
C26	0.9574 (3)	0.37061 (6)	1.03084 (15)	0.0335 (4)
H26A	0.9017	0.3410	1.0130	0.050*
H26B	1.0530	0.3711	1.1105	0.050*
H26C	1.0432	0.3799	0.9677	0.050*
Fe1	0.5000	0.5000	0.5000	0.01935 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0256 (8)	0.0166 (8)	0.0194 (8)	−0.0032 (6)	0.0008 (6)	−0.0040 (6)
C2	0.0272 (9)	0.0183 (8)	0.0250 (8)	−0.0019 (7)	0.0036 (6)	−0.0059 (6)
C3	0.0333 (9)	0.0273 (9)	0.0213 (8)	−0.0084 (7)	0.0079 (7)	−0.0092 (7)
C4	0.0352 (9)	0.0256 (9)	0.0169 (8)	−0.0089 (7)	−0.0016 (6)	0.0000 (6)
C5	0.0235 (8)	0.0213 (8)	0.0215 (8)	−0.0021 (6)	−0.0028 (6)	−0.0027 (6)
C6	0.0225 (8)	0.0182 (8)	0.0214 (8)	0.0021 (6)	0.0031 (6)	0.0005 (6)
C7	0.0212 (8)	0.0201 (8)	0.0215 (8)	0.0025 (6)	−0.0002 (6)	0.0018 (6)
C8	0.0308 (9)	0.0257 (9)	0.0245 (9)	−0.0020 (7)	0.0082 (7)	−0.0023 (7)
C9	0.0291 (9)	0.0254 (9)	0.0332 (9)	−0.0050 (7)	0.0079 (7)	0.0009 (7)
C10	0.0227 (8)	0.0192 (8)	0.0270 (8)	0.0026 (7)	−0.0014 (6)	0.0005 (6)
C11	0.0334 (9)	0.0253 (9)	0.0235 (8)	−0.0021 (7)	0.0044 (7)	−0.0035 (7)
C12	0.0334 (9)	0.0239 (9)	0.0235 (8)	−0.0062 (7)	0.0056 (7)	0.0000 (7)
C13	0.0302 (9)	0.0210 (8)	0.0347 (9)	−0.0017 (7)	0.0007 (7)	−0.0029 (7)
C14	0.0592 (13)	0.0221 (9)	0.0485 (12)	−0.0034 (9)	0.0023 (10)	0.0008 (8)
C15	0.0308 (11)	0.0397 (11)	0.0609 (13)	−0.0070 (9)	−0.0006 (9)	−0.0137 (9)
C16	0.0429 (11)	0.0280 (10)	0.0424 (11)	−0.0061 (8)	0.0023 (8)	−0.0117 (8)
C17	0.0246 (8)	0.0182 (8)	0.0209 (8)	−0.0047 (6)	0.0044 (6)	0.0000 (6)
C18	0.0271 (9)	0.0206 (8)	0.0253 (8)	0.0008 (7)	0.0073 (7)	−0.0002 (6)
C19	0.0327 (9)	0.0218 (8)	0.0198 (8)	−0.0009 (7)	0.0066 (7)	−0.0024 (6)
C20	0.0281 (9)	0.0196 (8)	0.0207 (8)	−0.0035 (7)	0.0058 (6)	0.0015 (6)
C21	0.0269 (9)	0.0221 (8)	0.0237 (8)	0.0029 (7)	0.0028 (6)	0.0005 (6)
C22	0.0315 (9)	0.0197 (8)	0.0210 (8)	0.0011 (7)	0.0048 (6)	−0.0024 (6)
C23	0.0298 (9)	0.0276 (9)	0.0199 (8)	−0.0025 (7)	0.0018 (6)	−0.0003 (7)
C24	0.0411 (11)	0.0337 (10)	0.0308 (9)	−0.0081 (8)	−0.0006 (8)	−0.0033 (8)
C25	0.0383 (10)	0.0363 (10)	0.0212 (8)	−0.0017 (8)	0.0038 (7)	0.0010 (7)
C26	0.0343 (10)	0.0394 (10)	0.0254 (9)	0.0020 (8)	−0.0001 (7)	0.0023 (8)
Fe1	0.02376 (19)	0.01684 (18)	0.01674 (17)	−0.00199 (15)	0.00099 (12)	−0.00149 (14)

Geometric parameters (Å, º) top

C1—C2	1.425 (2)	C15—H15A	0.9800
C1—C5	1.425 (2)	C15—H15B	0.9800
C1—C6	1.516 (2)	C15—H15C	0.9800
C1—Fe1	2.0634 (14)	C16—H16A	0.9800
C2—C3	1.421 (2)	C16—H16B	0.9800
C2—Fe1	2.0455 (15)	C16—H16C	0.9800
C2—H2	0.9500	C17—C22	1.385 (2)
C3—C4	1.415 (2)	C17—C18	1.394 (2)
C3—Fe1	2.0409 (15)	C18—C19	1.386 (2)
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.420 (2)	C19—C20	1.393 (2)
C4—Fe1	2.0527 (15)	C19—H19	0.9500
C4—H4	0.9500	C20—C21	1.393 (2)
C5—Fe1	2.0560 (14)	C20—C23	1.533 (2)
C5—H5	0.9500	C21—C22	1.390 (2)
C6—C17	1.522 (2)	C21—H21	0.9500
C6—C7	1.529 (2)	C22—H22	0.9500
C6—H6	1.0000	C23—C26	1.532 (2)
C7—C12	1.382 (2)	C23—C24	1.536 (2)
C7—C8	1.393 (2)	C23—C25	1.541 (2)
C8—C9	1.379 (2)	C24—H24A	0.9800
C8—H8	0.9500	C24—H24B	0.9800
C9—C10	1.399 (2)	C24—H24C	0.9800
C9—H9	0.9500	C25—H25A	0.9800
C10—C11	1.385 (2)	C25—H25B	0.9800
C10—C13	1.531 (2)	C25—H25C	0.9800
C11—C12	1.394 (2)	C26—H26A	0.9800
C11—H11	0.9500	C26—H26B	0.9800
C12—H12	0.9500	C26—H26C	0.9800
C13—C15	1.534 (2)	Fe1—C3ⁱ	2.0409 (15)
C13—C14	1.535 (2)	Fe1—C2ⁱ	2.0455 (15)
C13—C16	1.538 (2)	Fe1—C4ⁱ	2.0527 (15)
C14—H14A	0.9800	Fe1—C5ⁱ	2.0560 (15)
C14—H14B	0.9800	Fe1—C1ⁱ	2.0634 (15)
C14—H14C	0.9800

C2—C1—C5	106.94 (13)	C17—C18—H18	119.5
C2—C1—C6	128.72 (13)	C18—C19—C20	121.92 (14)
C5—C1—C6	124.05 (14)	C18—C19—H19	119.0
C2—C1—Fe1	69.04 (8)	C20—C19—H19	119.0
C5—C1—Fe1	69.48 (8)	C19—C20—C21	116.58 (14)
C6—C1—Fe1	131.21 (10)	C19—C20—C23	120.70 (13)
C3—C2—C1	108.24 (14)	C21—C20—C23	122.72 (14)
C3—C2—Fe1	69.47 (9)	C22—C21—C20	121.70 (15)
C1—C2—Fe1	70.38 (8)	C22—C21—H21	119.2
C3—C2—H2	125.9	C20—C21—H21	119.2
C1—C2—H2	125.9	C17—C22—C21	121.21 (14)
Fe1—C2—H2	125.8	C17—C22—H22	119.4
C4—C3—C2	108.45 (14)	C21—C22—H22	119.4
C4—C3—Fe1	70.23 (8)	C26—C23—C20	112.19 (13)
C2—C3—Fe1	69.82 (8)	C26—C23—C24	108.03 (14)
C4—C3—H3	125.8	C20—C23—C24	109.01 (13)
C2—C3—H3	125.8	C26—C23—C25	108.64 (13)
Fe1—C3—H3	125.8	C20—C23—C25	109.48 (13)
C3—C4—C5	107.45 (14)	C24—C23—C25	109.45 (13)
C3—C4—Fe1	69.33 (8)	C23—C24—H24A	109.5
C5—C4—Fe1	69.91 (8)	C23—C24—H24B	109.5
C3—C4—H4	126.3	H24A—C24—H24B	109.5
C5—C4—H4	126.3	C23—C24—H24C	109.5
Fe1—C4—H4	126.1	H24A—C24—H24C	109.5
C4—C5—C1	108.92 (14)	H24B—C24—H24C	109.5
C4—C5—Fe1	69.66 (8)	C23—C25—H25A	109.5
C1—C5—Fe1	70.03 (8)	C23—C25—H25B	109.5
C4—C5—H5	125.5	H25A—C25—H25B	109.5
C1—C5—H5	125.5	C23—C25—H25C	109.5
Fe1—C5—H5	126.3	H25A—C25—H25C	109.5
C1—C6—C17	112.94 (12)	H25B—C25—H25C	109.5
C1—C6—C7	112.14 (12)	C23—C26—H26A	109.5
C17—C6—C7	111.48 (12)	C23—C26—H26B	109.5
C1—C6—H6	106.6	H26A—C26—H26B	109.5
C17—C6—H6	106.6	C23—C26—H26C	109.5
C7—C6—H6	106.6	H26A—C26—H26C	109.5
C12—C7—C8	117.03 (14)	H26B—C26—H26C	109.5
C12—C7—C6	124.30 (14)	C3ⁱ—Fe1—C3	180.00 (8)
C8—C7—C6	118.65 (13)	C3ⁱ—Fe1—C2ⁱ	40.71 (6)
C9—C8—C7	121.78 (15)	C3—Fe1—C2ⁱ	139.29 (6)
C9—C8—H8	119.1	C3ⁱ—Fe1—C2	139.29 (6)
C7—C8—H8	119.1	C3—Fe1—C2	40.71 (6)
C8—C9—C10	121.49 (15)	C2ⁱ—Fe1—C2	180.00 (3)
C8—C9—H9	119.3	C3ⁱ—Fe1—C4ⁱ	40.43 (6)
C10—C9—H9	119.3	C3—Fe1—C4ⁱ	139.57 (6)
C11—C10—C9	116.52 (14)	C2ⁱ—Fe1—C4ⁱ	68.31 (6)
C11—C10—C13	123.20 (14)	C2—Fe1—C4ⁱ	111.69 (6)
C9—C10—C13	120.29 (14)	C3ⁱ—Fe1—C4	139.57 (6)
C10—C11—C12	121.92 (15)	C3—Fe1—C4	40.43 (6)
C10—C11—H11	119.0	C2ⁱ—Fe1—C4	111.69 (6)
C12—C11—H11	119.0	C2—Fe1—C4	68.31 (6)
C7—C12—C11	121.24 (15)	C4ⁱ—Fe1—C4	180.000 (1)
C7—C12—H12	119.4	C3ⁱ—Fe1—C5ⁱ	67.80 (6)
C11—C12—H12	119.4	C3—Fe1—C5ⁱ	112.20 (6)
C10—C13—C15	109.28 (14)	C2ⁱ—Fe1—C5ⁱ	67.90 (6)
C10—C13—C14	109.49 (13)	C2—Fe1—C5ⁱ	112.10 (6)
C15—C13—C14	109.10 (15)	C4ⁱ—Fe1—C5ⁱ	40.43 (6)
C10—C13—C16	112.22 (14)	C4—Fe1—C5ⁱ	139.57 (6)
C15—C13—C16	108.29 (14)	C3ⁱ—Fe1—C5	112.20 (6)
C14—C13—C16	108.40 (14)	C3—Fe1—C5	67.80 (6)
C13—C14—H14A	109.5	C2ⁱ—Fe1—C5	112.10 (6)
C13—C14—H14B	109.5	C2—Fe1—C5	67.90 (6)
H14A—C14—H14B	109.5	C4ⁱ—Fe1—C5	139.57 (6)
C13—C14—H14C	109.5	C4—Fe1—C5	40.43 (6)
H14A—C14—H14C	109.5	C5ⁱ—Fe1—C5	180.00 (8)
H14B—C14—H14C	109.5	C3ⁱ—Fe1—C1ⁱ	68.37 (6)
C13—C15—H15A	109.5	C3—Fe1—C1ⁱ	111.63 (6)
C13—C15—H15B	109.5	C2ⁱ—Fe1—C1ⁱ	40.58 (6)
H15A—C15—H15B	109.5	C2—Fe1—C1ⁱ	139.42 (6)
C13—C15—H15C	109.5	C4ⁱ—Fe1—C1ⁱ	68.45 (6)
H15A—C15—H15C	109.5	C4—Fe1—C1ⁱ	111.55 (6)
H15B—C15—H15C	109.5	C5ⁱ—Fe1—C1ⁱ	40.49 (6)
C13—C16—H16A	109.5	C5—Fe1—C1ⁱ	139.51 (6)
C13—C16—H16B	109.5	C3ⁱ—Fe1—C1	111.63 (6)
H16A—C16—H16B	109.5	C3—Fe1—C1	68.37 (6)
C13—C16—H16C	109.5	C2ⁱ—Fe1—C1	139.42 (6)
H16A—C16—H16C	109.5	C2—Fe1—C1	40.58 (6)
H16B—C16—H16C	109.5	C4ⁱ—Fe1—C1	111.55 (6)
C22—C17—C18	117.55 (14)	C4—Fe1—C1	68.45 (6)
C22—C17—C6	121.06 (13)	C5ⁱ—Fe1—C1	139.51 (6)
C18—C17—C6	121.36 (14)	C5—Fe1—C1	40.49 (6)
C19—C18—C17	120.93 (15)	C1ⁱ—Fe1—C1	180.0
C19—C18—H18	119.5

C5—C1—C2—C3	0.02 (16)	C2—C3—Fe1—C5ⁱ	98.56 (10)
C6—C1—C2—C3	173.97 (14)	C4—C3—Fe1—C5	37.93 (9)
Fe1—C1—C2—C3	−59.37 (10)	C2—C3—Fe1—C5	−81.44 (10)
C5—C1—C2—Fe1	59.39 (10)	C4—C3—Fe1—C1ⁱ	−98.28 (9)
C6—C1—C2—Fe1	−126.66 (15)	C2—C3—Fe1—C1ⁱ	142.36 (9)
C1—C2—C3—C4	0.11 (16)	C4—C3—Fe1—C1	81.72 (9)
Fe1—C2—C3—C4	−59.84 (10)	C2—C3—Fe1—C1	−37.64 (9)
C1—C2—C3—Fe1	59.94 (10)	C3—C2—Fe1—C3ⁱ	180.000 (1)
C2—C3—C4—C5	−0.19 (17)	C1—C2—Fe1—C3ⁱ	60.78 (13)
Fe1—C3—C4—C5	−59.77 (10)	C1—C2—Fe1—C3	−119.22 (13)
C2—C3—C4—Fe1	59.58 (10)	C3—C2—Fe1—C4ⁱ	−142.53 (9)
C3—C4—C5—C1	0.20 (17)	C1—C2—Fe1—C4ⁱ	98.24 (9)
Fe1—C4—C5—C1	−59.20 (10)	C3—C2—Fe1—C4	37.47 (9)
C3—C4—C5—Fe1	59.40 (10)	C1—C2—Fe1—C4	−81.76 (9)
C2—C1—C5—C4	−0.14 (16)	C3—C2—Fe1—C5ⁱ	−98.81 (10)
C6—C1—C5—C4	−174.44 (13)	C1—C2—Fe1—C5ⁱ	141.97 (9)
Fe1—C1—C5—C4	58.98 (10)	C3—C2—Fe1—C5	81.19 (10)
C2—C1—C5—Fe1	−59.11 (10)	C1—C2—Fe1—C5	−38.03 (9)
C6—C1—C5—Fe1	126.59 (14)	C3—C2—Fe1—C1ⁱ	−60.78 (13)
C2—C1—C6—C17	53.1 (2)	C1—C2—Fe1—C1ⁱ	180.0
C5—C1—C6—C17	−133.93 (14)	C3—C2—Fe1—C1	119.22 (13)
Fe1—C1—C6—C17	−42.25 (19)	C3—C4—Fe1—C3ⁱ	180.000 (1)
C2—C1—C6—C7	−73.92 (18)	C5—C4—Fe1—C3ⁱ	−61.36 (13)
C5—C1—C6—C7	99.09 (17)	C5—C4—Fe1—C3	118.64 (13)
Fe1—C1—C6—C7	−169.23 (11)	C3—C4—Fe1—C2ⁱ	142.29 (9)
C1—C6—C7—C12	7.5 (2)	C5—C4—Fe1—C2ⁱ	−99.07 (10)
C17—C6—C7—C12	−120.27 (16)	C3—C4—Fe1—C2	−37.71 (9)
C1—C6—C7—C8	−171.08 (13)	C5—C4—Fe1—C2	80.93 (10)
C17—C6—C7—C8	61.17 (18)	C3—C4—Fe1—C5ⁱ	61.36 (13)
C12—C7—C8—C9	−1.4 (2)	C5—C4—Fe1—C5ⁱ	180.0
C6—C7—C8—C9	177.24 (14)	C3—C4—Fe1—C5	−118.64 (13)
C7—C8—C9—C10	1.1 (3)	C3—C4—Fe1—C1ⁱ	98.48 (10)
C8—C9—C10—C11	0.3 (2)	C5—C4—Fe1—C1ⁱ	−142.88 (9)
C8—C9—C10—C13	−179.54 (15)	C3—C4—Fe1—C1	−81.52 (10)
C9—C10—C11—C12	−1.3 (2)	C5—C4—Fe1—C1	37.12 (9)
C13—C10—C11—C12	178.54 (15)	C4—C5—Fe1—C3ⁱ	142.07 (9)
C8—C7—C12—C11	0.4 (2)	C1—C5—Fe1—C3ⁱ	−97.77 (10)
C6—C7—C12—C11	−178.15 (14)	C4—C5—Fe1—C3	−37.93 (9)
C10—C11—C12—C7	1.0 (3)	C1—C5—Fe1—C3	82.23 (10)
C11—C10—C13—C15	−119.29 (17)	C4—C5—Fe1—C2ⁱ	97.95 (10)
C9—C10—C13—C15	60.6 (2)	C1—C5—Fe1—C2ⁱ	−141.88 (9)
C11—C10—C13—C14	121.27 (17)	C4—C5—Fe1—C2	−82.05 (10)
C9—C10—C13—C14	−58.9 (2)	C1—C5—Fe1—C2	38.12 (9)
C11—C10—C13—C16	0.8 (2)	C4—C5—Fe1—C4ⁱ	180.0
C9—C10—C13—C16	−179.29 (14)	C1—C5—Fe1—C4ⁱ	−59.83 (13)
C1—C6—C17—C22	−73.47 (18)	C1—C5—Fe1—C4	120.17 (13)
C7—C6—C17—C22	53.85 (19)	C4—C5—Fe1—C1ⁱ	59.83 (13)
C1—C6—C17—C18	104.54 (16)	C1—C5—Fe1—C1ⁱ	180.0
C7—C6—C17—C18	−128.14 (15)	C4—C5—Fe1—C1	−120.17 (13)
C22—C17—C18—C19	2.8 (2)	C2—C1—Fe1—C3ⁱ	−142.24 (9)
C6—C17—C18—C19	−175.22 (14)	C5—C1—Fe1—C3ⁱ	99.29 (10)
C17—C18—C19—C20	−0.1 (2)	C6—C1—Fe1—C3ⁱ	−18.54 (16)
C18—C19—C20—C21	−2.1 (2)	C2—C1—Fe1—C3	37.76 (9)
C18—C19—C20—C23	177.73 (14)	C5—C1—Fe1—C3	−80.71 (10)
C19—C20—C21—C22	1.5 (2)	C6—C1—Fe1—C3	161.46 (16)
C23—C20—C21—C22	−178.33 (14)	C2—C1—Fe1—C2ⁱ	180.0
C18—C17—C22—C21	−3.5 (2)	C5—C1—Fe1—C2ⁱ	61.54 (12)
C6—C17—C22—C21	174.62 (14)	C6—C1—Fe1—C2ⁱ	−56.30 (17)
C20—C21—C22—C17	1.3 (2)	C5—C1—Fe1—C2	−118.46 (12)
C19—C20—C23—C26	−179.90 (14)	C6—C1—Fe1—C2	123.70 (17)
C21—C20—C23—C26	−0.1 (2)	C2—C1—Fe1—C4ⁱ	−98.61 (9)
C19—C20—C23—C24	−60.29 (19)	C5—C1—Fe1—C4ⁱ	142.93 (9)
C21—C20—C23—C24	119.54 (16)	C6—C1—Fe1—C4ⁱ	25.09 (16)
C19—C20—C23—C25	59.40 (19)	C2—C1—Fe1—C4	81.39 (9)
C21—C20—C23—C25	−120.76 (16)	C5—C1—Fe1—C4	−37.07 (9)
C4—C3—Fe1—C2ⁱ	−60.63 (13)	C6—C1—Fe1—C4	−154.91 (16)
C2—C3—Fe1—C2ⁱ	180.000 (1)	C2—C1—Fe1—C5ⁱ	−61.54 (12)
C4—C3—Fe1—C2	119.37 (13)	C5—C1—Fe1—C5ⁱ	180.0
C4—C3—Fe1—C4ⁱ	180.000 (1)	C6—C1—Fe1—C5ⁱ	62.17 (18)
C2—C3—Fe1—C4ⁱ	60.63 (13)	C2—C1—Fe1—C5	118.46 (12)
C2—C3—Fe1—C4	−119.37 (13)	C6—C1—Fe1—C5	−117.83 (18)
C4—C3—Fe1—C5ⁱ	−142.07 (9)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Fe(C₂₆H₃₁)₂]
M_r	742.87
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	6.0893 (2), 30.7616 (8), 11.0983 (3)
β (°)	98.982 (3)
V (Å³)	2053.40 (10)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	3.19
Crystal size (mm)	0.18 × 0.13 × 0.09

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.889, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12754, 3267, 2784
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.576

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.071, 1.01
No. of reflections	3267
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.29

Computer programs: CrysAlis CCD (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Gomberg, M. (1900). J. Am. Chem. Soc. 22, 757–771. CrossRef Google Scholar
Gomberg, M. (1901). J. Am. Chem. Soc. 23, 496–502. CrossRef Google Scholar
Gomberg, M. (1902). J. Am. Chem. Soc. 24, 597–628. CrossRef Google Scholar
Lankamp, H., Nauta, W. T. & MacLean, C. (1968). Tetrahedron Lett. 9, 249–254. CrossRef Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
McBride, J. M. (1974). Tetrahedron, 30, 2009–2022. CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2010). CrysAlis PRO, CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sitzmann, H. (2001). Coord, Chem. Rev. 214, 287–327. Google Scholar
Sitzmann, H., Dezember, T., Kaim, W., Baumann, F., Stalke, D., Kärcher, J., Dormann, E., Winter, H., Wachter, C. & Kelemen, M. (1996). Angew. Chem. Int. Ed. Engl. 35, 2872–2875. CSD CrossRef CAS Web of Science Google Scholar
Sitzmann, H., Dezember, T. & Ruck, M. (1998). Angew. Chem. Int. Ed. Engl. 37, 3114–3116. CrossRef CAS Google Scholar
Sitzmann, H., Dezember, T., Schmitt, O., Weber, F., Wolmershäuser, G. & Ruck, M. (2000). Z. Anorg. Allg. Chem. 625, 2241–2244. CrossRef Google Scholar
Weismann, D., Sun, Y., Lan, Y., Wolmershäuser, G., Powell, A. K. & Sitzmann, H. (2011). Chem. Eur. J. 17, 4700–4704. Web of Science CSD CrossRef CAS PubMed Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar