1-Ferrocenyl-1-(1-inden­yl)cyclo­hexa­ne

Lin, J.; Xu, S.-S.; Song, H.-B.

doi:10.1107/S1600536805028308

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1-Ferrocenyl-1-(1-indenyl)cyclohexane

J. Lin, S.-S. Xu and H.-B. Song

In the title compound, [Fe(C₅H₅)(C₂₀H₂₃)], the two five-membered cyclopentadienyl rings are nearly parallel, with a dihedral angle of only 3.8 (1)°. The dihedral angle between the indenyl plane and the substituted cyclopentadienyl ring is 58.1 (2)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028308/cf6450sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028308/cf6450Isup2.hkl Contains datablock I

CCDC reference: 287496

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.044
wR factor = 0.121
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C10

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.86 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Fe1

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

A number of ferrocene derivatives substituted with an indenyl group have been structurally characterized, including 2-ferrocenyl-2-(3-indenyl)propane (Gaede, 2000), 1-(ferrocenyl)indene and 2-(ferrocenyl)indene (Plenio, 1992). As a further contribution, we report here the synthesis and crystal structure of 1-ferrocenyl-1-(1-indenyl)cyclohexane, (I).

A view of (I) is shown in Fig. 1 and selected bond lengths and angles are listed in Table 1. The dihedral angle between the indenyl plane and the substituted cyclopentadienyl ring is 58.1 (2)°. The Fe atom is η₅-coordinated by both cyclopentadienyl rings, with distances ranging from 2.015 (4) (to C10) to 2.074 (3) Å (to C1). The two five-membered cyclopentadienyl rings are nearly parallel, forming a dihedral angle of only 3.8 (1)°. The cyclohexane ring has a normal chair conformation.

Experimental top

A solution of indene (1.39 ml, 12 mmol) in tetrahydrofuran (THF, 100 ml) was reacted with n-butyllithium (12 mmol) at 273 K for 2 h and then stirred at room temperature for 4 h. A solution of 6,6-pentamethylenefulvene (1.75 g, 12 mmol) in THF (20 ml) was added dropwise at 273 K with stirring. When the addition was complete, the solution was warmed to room temperature and stirring was continued overnight. Cyclopentadienyllithium (12 mmol) in THF (20 ml) was added to this reaction mixture, followed by FeCl₂·1.44THF (2.78 g, 12 mmol), and the mixture was then stirred overnight. The solvent was removed under vacuum. The residue was chromatographed through a short column of Al₂O₃ with CH₂Cl₂, yielding an orange solid, which was collected and purified by chromatography on alumina to give orange crystals (yield 1.24 g, 27.07%). Calculated for C₂₆H₂₈Fe: C 78.54, H 6.85%; found: C 78.65, H 6.61%.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omited for clarity.

1-Ferrocenyl-1-(1-indenyl)cyclohexane top

Crystal data top

[Fe(C₅H₅)(C₂₀H₂₁)]	F(000) = 808
M_r = 382.31	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.232 (2) Å	Cell parameters from 2652 reflections
b = 11.6546 (18) Å	θ = 2.3–24.3°
c = 12.293 (2) Å	µ = 0.80 mm⁻¹
β = 92.881 (3)°	T = 294 K
V = 1893.4 (5) Å³	Block, red
Z = 4	0.26 × 0.24 × 0.18 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3887 independent reflections
Radiation source: fine-focus sealed tube	2407 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 26.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.793, T_max = 0.866	k = −14→6
10458 measured reflections	l = −15→15

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0562P)² + 0.5012P] where P = (F_o² + 2F_c²)/3
3887 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₂₀H₂₁)]	V = 1893.4 (5) Å³
M_r = 382.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.232 (2) Å	µ = 0.80 mm⁻¹
b = 11.6546 (18) Å	T = 294 K
c = 12.293 (2) Å	0.26 × 0.24 × 0.18 mm
β = 92.881 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3887 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2407 reflections with I > 2σ(I)
T_min = 0.793, T_max = 0.866	R_int = 0.038
10458 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	Δρ_max = 0.41 e Å⁻³
3887 reflections	Δρ_min = −0.30 e Å⁻³
235 parameters

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	0.28071 (3)	−0.07033 (4)	0.58622 (3)	0.04852 (17)
C1	0.2795 (2)	0.0327 (2)	0.7237 (2)	0.0409 (7)
C2	0.2929 (2)	−0.0853 (2)	0.7522 (2)	0.0466 (7)
H2	0.2507	−0.1278	0.7950	0.056*
C3	0.3805 (3)	−0.1266 (3)	0.7051 (2)	0.0602 (9)
H3	0.4062	−0.2007	0.7116	0.072*
C4	0.4227 (3)	−0.0356 (3)	0.6460 (3)	0.0633 (9)
H4	0.4810	−0.0394	0.6069	0.076*
C5	0.3608 (2)	0.0616 (3)	0.6569 (3)	0.0522 (8)
H5	0.3713	0.1330	0.6257	0.063*
C6	0.1719 (4)	−0.1759 (5)	0.5225 (3)	0.0965 (16)
H6	0.1321	−0.2246	0.5622	0.116*
C7	0.2592 (5)	−0.2030 (4)	0.4800 (4)	0.0955 (15)
H7	0.2903	−0.2744	0.4859	0.115*
C8	0.2951 (4)	−0.1150 (5)	0.4287 (3)	0.0968 (14)
H8	0.3556	−0.1153	0.3934	0.116*
C9	0.2331 (5)	−0.0240 (4)	0.4333 (3)	0.0974 (17)
H9	0.2426	0.0473	0.4015	0.117*
C10	0.1498 (4)	−0.0569 (6)	0.4961 (4)	0.117 (2)
H10	0.0949	−0.0128	0.5153	0.140*
C11	0.2002 (2)	0.1131 (2)	0.7658 (2)	0.0411 (7)
C12	0.1038 (2)	0.0461 (2)	0.7892 (3)	0.0488 (7)
H12A	0.0817	0.0038	0.7243	0.059*
H12B	0.1196	−0.0093	0.8465	0.059*
C13	0.0170 (2)	0.1222 (3)	0.8235 (3)	0.0627 (9)
H13A	−0.0423	0.0753	0.8342	0.075*
H13B	0.0360	0.1595	0.8920	0.075*
C14	−0.0084 (3)	0.2126 (3)	0.7372 (3)	0.0734 (10)
H14A	−0.0356	0.1754	0.6715	0.088*
H14B	−0.0601	0.2635	0.7630	0.088*
C15	0.0836 (3)	0.2823 (3)	0.7107 (3)	0.0675 (10)
H15A	0.1045	0.3287	0.7734	0.081*
H15B	0.0659	0.3337	0.6507	0.081*
C16	0.1712 (2)	0.2064 (3)	0.6801 (3)	0.0561 (8)
H16A	0.2298	0.2544	0.6698	0.067*
H16B	0.1534	0.1692	0.6112	0.067*
C17	0.2476 (2)	0.1731 (2)	0.8710 (2)	0.0439 (7)
H17	0.1982	0.2292	0.8948	0.053*
C18	0.3447 (3)	0.2372 (3)	0.8537 (3)	0.0558 (8)
H18	0.3527	0.2910	0.7990	0.067*
C19	0.4169 (3)	0.2070 (3)	0.9260 (3)	0.0618 (9)
H19	0.4823	0.2365	0.9293	0.074*
C20	0.3799 (2)	0.1215 (3)	0.9995 (2)	0.0486 (7)
C21	0.2782 (2)	0.0996 (2)	0.9682 (2)	0.0410 (7)
C22	0.2237 (2)	0.0261 (3)	1.0322 (2)	0.0492 (7)
H22	0.1558	0.0114	1.0144	0.059*
C23	0.2710 (3)	−0.0250 (3)	1.1223 (3)	0.0612 (9)
H23	0.2343	−0.0738	1.1654	0.073*
C24	0.3716 (3)	−0.0050 (3)	1.1496 (3)	0.0663 (9)
H24	0.4026	−0.0418	1.2096	0.080*
C25	0.4264 (3)	0.0689 (3)	1.0889 (3)	0.0635 (9)
H25	0.4941	0.0834	1.1079	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0677 (3)	0.0461 (3)	0.0316 (2)	−0.0057 (2)	0.00016 (19)	−0.00341 (19)
C1	0.0480 (17)	0.0434 (16)	0.0310 (14)	−0.0034 (13)	−0.0016 (12)	−0.0037 (12)
C2	0.0625 (19)	0.0469 (18)	0.0299 (14)	0.0066 (15)	−0.0033 (13)	0.0001 (12)
C3	0.072 (2)	0.063 (2)	0.0454 (18)	0.0206 (19)	−0.0049 (16)	−0.0080 (16)
C4	0.054 (2)	0.079 (2)	0.058 (2)	0.0048 (18)	0.0067 (16)	−0.0196 (19)
C5	0.0559 (18)	0.0524 (19)	0.0486 (17)	−0.0088 (16)	0.0053 (14)	−0.0078 (15)
C6	0.109 (4)	0.133 (5)	0.046 (2)	−0.070 (4)	−0.007 (2)	−0.005 (3)
C7	0.165 (5)	0.064 (3)	0.056 (3)	−0.019 (3)	−0.015 (3)	−0.017 (2)
C8	0.143 (4)	0.114 (4)	0.034 (2)	−0.013 (4)	0.009 (2)	−0.011 (2)
C9	0.175 (5)	0.058 (3)	0.053 (3)	−0.010 (3)	−0.046 (3)	0.011 (2)
C10	0.086 (3)	0.177 (6)	0.082 (3)	0.055 (4)	−0.049 (3)	−0.078 (4)
C11	0.0463 (17)	0.0375 (15)	0.0394 (15)	−0.0022 (13)	0.0023 (12)	0.0022 (12)
C12	0.0498 (18)	0.0478 (18)	0.0483 (17)	−0.0039 (14)	−0.0018 (14)	−0.0021 (14)
C13	0.050 (2)	0.068 (2)	0.070 (2)	0.0006 (17)	0.0088 (17)	−0.0031 (19)
C14	0.060 (2)	0.083 (3)	0.076 (3)	0.020 (2)	−0.0076 (19)	−0.004 (2)
C15	0.078 (2)	0.057 (2)	0.066 (2)	0.0170 (19)	−0.0061 (18)	0.0117 (17)
C16	0.067 (2)	0.0505 (19)	0.0508 (19)	0.0050 (16)	0.0006 (15)	0.0101 (15)
C17	0.0534 (17)	0.0347 (15)	0.0441 (16)	−0.0012 (13)	0.0083 (13)	−0.0051 (13)
C18	0.074 (2)	0.0440 (18)	0.0507 (19)	−0.0193 (16)	0.0117 (17)	−0.0039 (15)
C19	0.060 (2)	0.070 (2)	0.056 (2)	−0.0285 (18)	0.0105 (17)	−0.0130 (17)
C20	0.0487 (18)	0.0555 (18)	0.0418 (16)	−0.0060 (15)	0.0057 (13)	−0.0127 (14)
C21	0.0466 (17)	0.0421 (16)	0.0347 (15)	−0.0020 (13)	0.0038 (12)	−0.0103 (12)
C22	0.0506 (18)	0.0558 (18)	0.0416 (17)	−0.0091 (15)	0.0071 (14)	−0.0028 (14)
C23	0.078 (2)	0.064 (2)	0.0419 (18)	−0.0104 (18)	0.0081 (17)	0.0022 (16)
C24	0.080 (3)	0.077 (2)	0.0411 (18)	0.006 (2)	−0.0068 (18)	−0.0013 (18)
C25	0.0541 (19)	0.088 (3)	0.0473 (19)	0.0022 (19)	−0.0050 (16)	−0.0113 (19)

Geometric parameters (Å, º) top

Fe1—C1	2.074 (3)	C11—C17	1.573 (4)
Fe1—C2	2.046 (3)	C12—C13	1.528 (4)
Fe1—C3	2.028 (3)	C12—H12A	0.970
Fe1—C4	2.023 (3)	C12—H12B	0.970
Fe1—C5	2.037 (3)	C13—C14	1.521 (5)
Fe1—C6	2.021 (4)	C13—H13A	0.970
Fe1—C7	2.035 (4)	C13—H13B	0.970
Fe1—C8	2.024 (4)	C14—C15	1.512 (5)
Fe1—C9	2.026 (4)	C14—H14A	0.970
Fe1—C10	2.015 (4)	C14—H14B	0.970
C1—C5	1.426 (4)	C15—C16	1.520 (4)
C1—C2	1.428 (4)	C15—H15A	0.970
C1—C11	1.517 (4)	C15—H15B	0.970
C2—C3	1.406 (4)	C16—H16A	0.970
C2—H2	0.930	C16—H16B	0.970
C3—C4	1.416 (5)	C17—C21	1.509 (4)
C3—H3	0.930	C17—C18	1.510 (4)
C4—C5	1.408 (4)	C17—H17	0.980
C4—H4	0.930	C18—C19	1.319 (4)
C5—H5	0.930	C18—H18	0.930
C6—C7	1.329 (6)	C19—C20	1.447 (4)
C6—C10	1.450 (7)	C19—H19	0.930
C6—H6	0.930	C20—C25	1.377 (4)
C7—C8	1.305 (6)	C20—C21	1.404 (4)
C7—H7	0.930	C21—C22	1.388 (4)
C8—C9	1.344 (7)	C22—C23	1.380 (4)
C8—H8	0.930	C22—H22	0.930
C9—C10	1.429 (7)	C23—C24	1.377 (5)
C9—H9	0.930	C23—H23	0.930
C10—H10	0.930	C24—C25	1.371 (5)
C11—C12	1.536 (4)	C24—H24	0.930
C11—C16	1.548 (4)	C25—H25	0.930

C10—Fe1—C6	42.1 (2)	Fe1—C7—H7	125.7
C10—Fe1—C4	160.2 (3)	C7—C8—C9	111.2 (5)
C6—Fe1—C4	153.2 (2)	C7—C8—Fe1	71.7 (2)
C10—Fe1—C8	67.2 (2)	C9—C8—Fe1	70.7 (2)
C6—Fe1—C8	64.65 (19)	C7—C8—H8	124.4
C4—Fe1—C8	105.62 (18)	C9—C8—H8	124.4
C10—Fe1—C9	41.4 (2)	Fe1—C8—H8	124.8
C6—Fe1—C9	67.68 (18)	C8—C9—C10	107.5 (4)
C4—Fe1—C9	121.6 (2)	C8—C9—Fe1	70.5 (2)
C8—Fe1—C9	38.76 (19)	C10—C9—Fe1	68.9 (2)
C10—Fe1—C3	158.7 (3)	C8—C9—H9	126.3
C6—Fe1—C3	120.5 (2)	C10—C9—H9	126.3
C4—Fe1—C3	40.90 (14)	Fe1—C9—H9	125.9
C8—Fe1—C3	121.16 (19)	C9—C10—C6	103.0 (4)
C9—Fe1—C3	156.3 (2)	C9—C10—Fe1	69.7 (2)
C10—Fe1—C7	67.50 (19)	C6—C10—Fe1	69.2 (2)
C6—Fe1—C7	38.27 (19)	C9—C10—H10	128.5
C4—Fe1—C7	118.9 (2)	C6—C10—H10	128.5
C8—Fe1—C7	37.52 (17)	Fe1—C10—H10	124.4
C9—Fe1—C7	65.15 (18)	C1—C11—C12	110.2 (2)
C3—Fe1—C7	106.38 (17)	C1—C11—C16	110.7 (2)
C10—Fe1—C5	126.2 (2)	C12—C11—C16	107.7 (2)
C6—Fe1—C5	165.9 (2)	C1—C11—C17	107.5 (2)
C4—Fe1—C5	40.56 (12)	C12—C11—C17	111.9 (2)
C8—Fe1—C5	122.05 (18)	C16—C11—C17	108.8 (2)
C9—Fe1—C5	109.02 (16)	C13—C12—C11	113.5 (2)
C3—Fe1—C5	68.32 (14)	C13—C12—H12A	108.9
C7—Fe1—C5	154.2 (2)	C11—C12—H12A	108.9
C10—Fe1—C2	125.3 (2)	C13—C12—H12B	108.9
C6—Fe1—C2	110.72 (15)	C11—C12—H12B	108.9
C4—Fe1—C2	68.24 (13)	H12A—C12—H12B	107.7
C8—Fe1—C2	157.83 (19)	C14—C13—C12	110.7 (3)
C9—Fe1—C2	162.4 (2)	C14—C13—H13A	109.5
C3—Fe1—C2	40.38 (12)	C12—C13—H13A	109.5
C7—Fe1—C2	125.25 (16)	C14—C13—H13B	109.5
C5—Fe1—C2	67.99 (12)	C12—C13—H13B	109.5
C10—Fe1—C1	111.20 (15)	H13A—C13—H13B	108.1
C6—Fe1—C1	129.33 (19)	C15—C14—C13	111.7 (3)
C4—Fe1—C1	68.47 (12)	C15—C14—H14A	109.3
C8—Fe1—C1	159.04 (19)	C13—C14—H14A	109.3
C9—Fe1—C1	125.96 (18)	C15—C14—H14B	109.3
C3—Fe1—C1	68.37 (12)	C13—C14—H14B	109.3
C7—Fe1—C1	163.05 (18)	H14A—C14—H14B	107.9
C5—Fe1—C1	40.58 (11)	C14—C15—C16	111.9 (3)
C2—Fe1—C1	40.53 (11)	C14—C15—H15A	109.2
C5—C1—C2	106.3 (3)	C16—C15—H15A	109.2
C5—C1—C11	127.3 (3)	C14—C15—H15B	109.2
C2—C1—C11	126.2 (3)	C16—C15—H15B	109.2
C5—C1—Fe1	68.32 (16)	H15A—C15—H15B	107.9
C2—C1—Fe1	68.69 (15)	C15—C16—C11	114.0 (3)
C11—C1—Fe1	131.98 (19)	C15—C16—H16A	108.8
C3—C2—C1	108.9 (3)	C11—C16—H16A	108.8
C3—C2—Fe1	69.12 (17)	C15—C16—H16B	108.8
C1—C2—Fe1	70.78 (15)	C11—C16—H16B	108.8
C3—C2—H2	125.6	H16A—C16—H16B	107.7
C1—C2—H2	125.6	C21—C17—C18	101.3 (2)
Fe1—C2—H2	126.1	C21—C17—C11	118.6 (2)
C2—C3—C4	108.0 (3)	C18—C17—C11	114.3 (2)
C2—C3—Fe1	70.50 (17)	C21—C17—H17	107.3
C4—C3—Fe1	69.37 (19)	C18—C17—H17	107.3
C2—C3—H3	126.0	C11—C17—H17	107.3
C4—C3—H3	126.0	C19—C18—C17	111.4 (3)
Fe1—C3—H3	125.7	C19—C18—H18	124.3
C5—C4—C3	107.9 (3)	C17—C18—H18	124.3
C5—C4—Fe1	70.25 (18)	C18—C19—C20	110.4 (3)
C3—C4—Fe1	69.74 (19)	C18—C19—H19	124.8
C5—C4—H4	126.0	C20—C19—H19	124.8
C3—C4—H4	126.0	C25—C20—C21	121.4 (3)
Fe1—C4—H4	125.6	C25—C20—C19	130.8 (3)
C4—C5—C1	108.9 (3)	C21—C20—C19	107.7 (3)
C4—C5—Fe1	69.19 (18)	C22—C21—C20	118.4 (3)
C1—C5—Fe1	71.10 (16)	C22—C21—C17	132.3 (3)
C4—C5—H5	125.5	C20—C21—C17	109.2 (2)
C1—C5—H5	125.5	C23—C22—C21	119.6 (3)
Fe1—C5—H5	125.7	C23—C22—H22	120.2
C7—C6—C10	108.0 (4)	C21—C22—H22	120.2
C7—C6—Fe1	71.4 (2)	C24—C23—C22	121.1 (3)
C10—C6—Fe1	68.7 (2)	C24—C23—H23	119.4
C7—C6—H6	126.0	C22—C23—H23	119.4
C10—C6—H6	126.0	C25—C24—C23	120.3 (3)
Fe1—C6—H6	125.4	C25—C24—H24	119.8
C8—C7—C6	110.3 (5)	C23—C24—H24	119.8
C8—C7—Fe1	70.8 (2)	C24—C25—C20	119.2 (3)
C6—C7—Fe1	70.3 (3)	C24—C25—H25	120.4
C8—C7—H7	124.8	C20—C25—H25	120.4
C6—C7—H7	124.8

C10—Fe1—C1—C5	−121.4 (3)	C10—C6—C7—C8	−0.4 (5)
C6—Fe1—C1—C5	−166.1 (3)	Fe1—C6—C7—C8	−59.6 (3)
C4—Fe1—C1—C5	37.36 (19)	C10—C6—C7—Fe1	59.2 (3)
C8—Fe1—C1—C5	−39.9 (5)	C10—Fe1—C7—C8	81.5 (4)
C9—Fe1—C1—C5	−76.8 (3)	C6—Fe1—C7—C8	121.0 (5)
C3—Fe1—C1—C5	81.5 (2)	C4—Fe1—C7—C8	−77.7 (4)
C7—Fe1—C1—C5	156.4 (6)	C9—Fe1—C7—C8	36.1 (3)
C2—Fe1—C1—C5	118.6 (3)	C3—Fe1—C7—C8	−120.2 (4)
C10—Fe1—C1—C2	120.0 (3)	C5—Fe1—C7—C8	−46.2 (6)
C6—Fe1—C1—C2	75.3 (3)	C2—Fe1—C7—C8	−160.3 (3)
C4—Fe1—C1—C2	−81.3 (2)	C1—Fe1—C7—C8	170.5 (5)
C8—Fe1—C1—C2	−158.5 (5)	C10—Fe1—C7—C6	−39.6 (3)
C9—Fe1—C1—C2	164.6 (3)	C4—Fe1—C7—C6	161.3 (3)
C3—Fe1—C1—C2	−37.13 (19)	C8—Fe1—C7—C6	−121.0 (5)
C7—Fe1—C1—C2	37.8 (6)	C9—Fe1—C7—C6	−84.9 (3)
C5—Fe1—C1—C2	−118.6 (3)	C3—Fe1—C7—C6	118.8 (3)
C10—Fe1—C1—C11	−0.2 (4)	C5—Fe1—C7—C6	−167.3 (3)
C6—Fe1—C1—C11	−44.9 (4)	C2—Fe1—C7—C6	78.7 (3)
C4—Fe1—C1—C11	158.6 (3)	C1—Fe1—C7—C6	49.5 (7)
C8—Fe1—C1—C11	81.4 (6)	C6—C7—C8—C9	−0.5 (5)
C9—Fe1—C1—C11	44.4 (4)	Fe1—C7—C8—C9	−59.9 (3)
C3—Fe1—C1—C11	−157.3 (3)	C6—C7—C8—Fe1	59.4 (3)
C7—Fe1—C1—C11	−82.4 (7)	C10—Fe1—C8—C7	−82.2 (4)
C5—Fe1—C1—C11	121.2 (3)	C6—Fe1—C8—C7	−36.0 (3)
C2—Fe1—C1—C11	−120.1 (3)	C4—Fe1—C8—C7	117.3 (4)
C5—C1—C2—C3	0.6 (3)	C9—Fe1—C8—C7	−121.3 (5)
C11—C1—C2—C3	−174.0 (3)	C3—Fe1—C8—C7	75.7 (4)
Fe1—C1—C2—C3	58.8 (2)	C5—Fe1—C8—C7	158.2 (3)
C5—C1—C2—Fe1	−58.19 (19)	C2—Fe1—C8—C7	46.8 (6)
C11—C1—C2—Fe1	127.2 (3)	C1—Fe1—C8—C7	−172.3 (4)
C10—Fe1—C2—C3	158.4 (3)	C10—Fe1—C8—C9	39.1 (3)
C6—Fe1—C2—C3	113.1 (3)	C6—Fe1—C8—C9	85.4 (3)
C4—Fe1—C2—C3	−38.1 (2)	C4—Fe1—C8—C9	−121.4 (3)
C8—Fe1—C2—C3	39.7 (5)	C3—Fe1—C8—C9	−162.9 (3)
C9—Fe1—C2—C3	−165.5 (5)	C7—Fe1—C8—C9	121.3 (5)
C7—Fe1—C2—C3	72.6 (3)	C5—Fe1—C8—C9	−80.5 (4)
C5—Fe1—C2—C3	−82.0 (2)	C2—Fe1—C8—C9	168.1 (4)
C1—Fe1—C2—C3	−120.0 (3)	C1—Fe1—C8—C9	−51.0 (6)
C10—Fe1—C2—C1	−81.6 (3)	C7—C8—C9—C10	1.2 (5)
C6—Fe1—C2—C1	−126.9 (3)	Fe1—C8—C9—C10	−59.2 (3)
C4—Fe1—C2—C1	81.88 (19)	C7—C8—C9—Fe1	60.5 (3)
C8—Fe1—C2—C1	159.7 (4)	C10—Fe1—C9—C8	−118.5 (4)
C9—Fe1—C2—C1	−45.6 (6)	C6—Fe1—C9—C8	−76.8 (3)
C3—Fe1—C2—C1	120.0 (3)	C4—Fe1—C9—C8	74.9 (3)
C7—Fe1—C2—C1	−167.4 (3)	C3—Fe1—C9—C8	38.6 (6)
C5—Fe1—C2—C1	38.01 (17)	C7—Fe1—C9—C8	−35.0 (3)
C1—C2—C3—C4	−0.3 (3)	C5—Fe1—C9—C8	117.9 (3)
Fe1—C2—C3—C4	59.5 (2)	C2—Fe1—C9—C8	−165.1 (4)
C1—C2—C3—Fe1	−59.8 (2)	C1—Fe1—C9—C8	159.9 (3)
C10—Fe1—C3—C2	−55.8 (5)	C6—Fe1—C9—C10	41.7 (3)
C6—Fe1—C3—C2	−86.6 (3)	C4—Fe1—C9—C10	−166.6 (3)
C4—Fe1—C3—C2	118.9 (3)	C8—Fe1—C9—C10	118.5 (4)
C8—Fe1—C3—C2	−163.6 (2)	C3—Fe1—C9—C10	157.2 (4)
C9—Fe1—C3—C2	169.2 (4)	C7—Fe1—C9—C10	83.5 (3)
C7—Fe1—C3—C2	−125.7 (2)	C5—Fe1—C9—C10	−123.6 (3)
C5—Fe1—C3—C2	81.1 (2)	C2—Fe1—C9—C10	−46.6 (6)
C1—Fe1—C3—C2	37.27 (18)	C1—Fe1—C9—C10	−81.6 (3)
C10—Fe1—C3—C4	−174.7 (4)	C8—C9—C10—C6	−1.4 (4)
C6—Fe1—C3—C4	154.5 (3)	Fe1—C9—C10—C6	−61.7 (2)
C8—Fe1—C3—C4	77.4 (3)	C8—C9—C10—Fe1	60.3 (3)
C9—Fe1—C3—C4	50.3 (5)	C7—C6—C10—C9	1.1 (4)
C7—Fe1—C3—C4	115.4 (3)	Fe1—C6—C10—C9	62.0 (3)
C5—Fe1—C3—C4	−37.84 (18)	C7—C6—C10—Fe1	−60.9 (3)
C2—Fe1—C3—C4	−118.9 (3)	C6—Fe1—C10—C9	−113.4 (4)
C1—Fe1—C3—C4	−81.6 (2)	C4—Fe1—C10—C9	35.7 (6)
C2—C3—C4—C5	−0.1 (4)	C8—Fe1—C10—C9	−36.6 (3)
Fe1—C3—C4—C5	60.1 (2)	C3—Fe1—C10—C9	−154.6 (4)
C2—C3—C4—Fe1	−60.2 (2)	C7—Fe1—C10—C9	−77.4 (3)
C10—Fe1—C4—C5	55.6 (5)	C5—Fe1—C10—C9	77.3 (3)
C6—Fe1—C4—C5	−174.3 (3)	C2—Fe1—C10—C9	164.4 (3)
C8—Fe1—C4—C5	121.4 (3)	C1—Fe1—C10—C9	120.8 (3)
C9—Fe1—C4—C5	82.5 (3)	C4—Fe1—C10—C6	149.1 (5)
C3—Fe1—C4—C5	−118.8 (3)	C8—Fe1—C10—C6	76.8 (3)
C7—Fe1—C4—C5	159.5 (2)	C9—Fe1—C10—C6	113.4 (4)
C2—Fe1—C4—C5	−81.1 (2)	C3—Fe1—C10—C6	−41.1 (6)
C1—Fe1—C4—C5	−37.38 (18)	C7—Fe1—C10—C6	36.0 (3)
C10—Fe1—C4—C3	174.3 (4)	C5—Fe1—C10—C6	−169.2 (3)
C6—Fe1—C4—C3	−55.5 (4)	C2—Fe1—C10—C6	−82.2 (3)
C8—Fe1—C4—C3	−119.9 (2)	C1—Fe1—C10—C6	−125.8 (3)
C9—Fe1—C4—C3	−158.7 (2)	C5—C1—C11—C12	155.0 (3)
C7—Fe1—C4—C3	−81.7 (2)	C2—C1—C11—C12	−31.5 (4)
C5—Fe1—C4—C3	118.8 (3)	Fe1—C1—C11—C12	61.5 (3)
C2—Fe1—C4—C3	37.63 (18)	C5—C1—C11—C16	35.9 (4)
C1—Fe1—C4—C3	81.39 (19)	C2—C1—C11—C16	−150.6 (3)
C3—C4—C5—C1	0.4 (4)	Fe1—C1—C11—C16	−57.6 (3)
Fe1—C4—C5—C1	60.2 (2)	C5—C1—C11—C17	−82.8 (3)
C3—C4—C5—Fe1	−59.8 (2)	C2—C1—C11—C17	90.7 (3)
C2—C1—C5—C4	−0.6 (3)	Fe1—C1—C11—C17	−176.3 (2)
C11—C1—C5—C4	173.9 (3)	C1—C11—C12—C13	−175.5 (2)
Fe1—C1—C5—C4	−59.1 (2)	C16—C11—C12—C13	−54.6 (3)
C2—C1—C5—Fe1	58.42 (19)	C17—C11—C12—C13	64.9 (3)
C11—C1—C5—Fe1	−127.0 (3)	C11—C12—C13—C14	57.0 (4)
C10—Fe1—C5—C4	−159.8 (3)	C12—C13—C14—C15	−54.6 (4)
C6—Fe1—C5—C4	169.3 (6)	C13—C14—C15—C16	53.4 (4)
C8—Fe1—C5—C4	−75.9 (3)	C14—C15—C16—C11	−53.8 (4)
C9—Fe1—C5—C4	−116.7 (3)	C1—C11—C16—C15	173.5 (3)
C3—Fe1—C5—C4	38.1 (2)	C12—C11—C16—C15	52.9 (3)
C7—Fe1—C5—C4	−44.7 (4)	C17—C11—C16—C15	−68.6 (3)
C2—Fe1—C5—C4	81.8 (2)	C1—C11—C17—C21	−62.5 (3)
C1—Fe1—C5—C4	119.8 (3)	C12—C11—C17—C21	58.7 (3)
C10—Fe1—C5—C1	80.5 (3)	C16—C11—C17—C21	177.6 (2)
C6—Fe1—C5—C1	49.6 (7)	C1—C11—C17—C18	56.9 (3)
C4—Fe1—C5—C1	−119.8 (3)	C12—C11—C17—C18	178.1 (2)
C8—Fe1—C5—C1	164.3 (2)	C16—C11—C17—C18	−63.0 (3)
C9—Fe1—C5—C1	123.5 (3)	C21—C17—C18—C19	0.0 (3)
C3—Fe1—C5—C1	−81.62 (19)	C11—C17—C18—C19	−128.7 (3)
C7—Fe1—C5—C1	−164.4 (3)	C17—C18—C19—C20	0.0 (4)
C2—Fe1—C5—C1	−37.97 (17)	C18—C19—C20—C25	−177.3 (3)
C10—Fe1—C6—C7	118.7 (4)	C18—C19—C20—C21	0.0 (4)
C4—Fe1—C6—C7	−38.6 (5)	C25—C20—C21—C22	2.3 (4)
C8—Fe1—C6—C7	35.3 (3)	C19—C20—C21—C22	−175.2 (3)
C9—Fe1—C6—C7	77.7 (3)	C25—C20—C21—C17	177.6 (3)
C3—Fe1—C6—C7	−77.4 (3)	C19—C20—C21—C17	0.0 (3)
C5—Fe1—C6—C7	156.8 (6)	C18—C17—C21—C22	174.3 (3)
C2—Fe1—C6—C7	−121.1 (3)	C11—C17—C21—C22	−59.8 (4)
C1—Fe1—C6—C7	−163.3 (2)	C18—C17—C21—C20	0.0 (3)
C4—Fe1—C6—C10	−157.3 (4)	C11—C17—C21—C20	125.9 (3)
C8—Fe1—C6—C10	−83.4 (3)	C20—C21—C22—C23	−1.5 (4)
C9—Fe1—C6—C10	−41.0 (3)	C17—C21—C22—C23	−175.5 (3)
C3—Fe1—C6—C10	163.9 (3)	C21—C22—C23—C24	−0.4 (5)
C7—Fe1—C6—C10	−118.7 (4)	C22—C23—C24—C25	1.7 (5)
C5—Fe1—C6—C10	38.1 (8)	C23—C24—C25—C20	−0.9 (5)
C2—Fe1—C6—C10	120.2 (3)	C21—C20—C25—C24	−1.1 (5)
C1—Fe1—C6—C10	77.9 (3)	C19—C20—C25—C24	175.8 (3)

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₂₀H₂₁)]
M_r	382.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	13.232 (2), 11.6546 (18), 12.293 (2)
β (°)	92.881 (3)
V (Å³)	1893.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.26 × 0.24 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.793, 0.866
No. of measured, independent and observed [I > 2σ(I)] reflections	10458, 3887, 2407
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.121, 1.01
No. of reflections	3887
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Selected bond lengths (Å) top

Fe1—C1	2.074 (3)	Fe1—C6	2.021 (4)
Fe1—C2	2.046 (3)	Fe1—C7	2.035 (4)
Fe1—C3	2.028 (3)	Fe1—C8	2.024 (4)
Fe1—C4	2.023 (3)	Fe1—C9	2.026 (4)
Fe1—C5	2.037 (3)	Fe1—C10	2.015 (4)

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