1-Ferrocenyl-1-(1H-inden­yl)cyclo­hepta­ne

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

doi:10.1107/S1600536805029302

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1-Ferrocenyl-1-(1H-indenyl)cycloheptane

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

In the title compound, [Fe(C₅H₅)(C₂₁H₂₃)], the cyclopentadienyl (Cp) rings deviate slightly from an eclipsed geometry. The cycloheptane ring adopts a chair conformation. The unsubstituted and substituted Cp rings form dihedral angles of 55.62 (12) and 54.13 (10)°, respectively, with the indene ring system.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029302/ci6650sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029302/ci6650Isup2.hkl Contains datablock I

CCDC reference: 287515

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R factor = 0.036
wR factor = 0.080
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.90
PLAT213_ALERT_2_C Atom C2      has ADP max/min Ratio .............       3.10 prolat
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.69 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       6.78 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C3
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

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           26.39
           From the CIF: _reflns_number_total               3703
           Count of symmetry unique reflns         2080
           Completeness (_total/calc)            178.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1623
           Fraction of Friedel pairs measured     0.780
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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-substituted indenyl derivatives, e.g. 2-(3-indenyl)-2-(ferrocenyl)propane (Gaede, 2000), 1-(ferrocenyl)indene and 2-(ferrocenyl)indene (Plenio, 1992), have been structurally characterized due to their catalytic properties. We present here the synthesis and crystal structure of the title compound, (I).

A view of (I), with the atomic numbering scheme, is shown in Fig. 1; selected bond lengths and angles are given in Table 1. The Fe1—C bond lengths for the unsubstituted cyclopentadienyl (Cp) ring of (I) are in the range 2.029 (2)–2.063 (3) Å and those for substituted Cp ring are in the range 2.033 (3)–2.095 (3) Å. The Fe1···Cg1 and Fe1···Cg2 distances are 1.666 (2) and 1.661 (2) Å, respectively, and the Cg1—Fe1—Cg2 angle is 176.86 (8)°, where Cg1 and Cg2 are the centroids of the unsubstituted and substituted Cp rings, respectively. The Cp rings deviate slightly from an eclipsed geometry. The indene ring system is planar, with an r.m.s. deviation of 0.025 Å. The unsubstituted and substituted Cp rings form dihedral angles of 55.62 (12) and 54.13 (10)° with the indene plane. The cycloheptane ring adopts a chair conformation. The crystal packing is stabilized by weak C—H···π interactions (Table 1; Cg3 and Cg4 denote C18–C20/C26 and C21–C26 ring centroids).

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-hexamethylenefulvene (1.92 g, 12 mmol) in THF (20 ml) was added dropwise to above reaction system at 273 K with stirring. When the addition was completed, 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. FeCl₂·1.44THF (2.78 g, 12 mmol) was then added to the above mixture and the resulting mixture stirred overnight. The solvent was removed in a vacuum. The residue was run through a short column of Al₂O₃ with C_H2_Cl2 yielding compound (I), which was collected and purified by chromatography on alumina, to give crystals of (I) (1.23 g, yield 25.86%). Analysis calculated for C₂₆H₂₈Fe: C 78.79, H 7.12%; found: C 78.50, H 6.99%.

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-(1H-indenyl)cycloheptane top

Crystal data top

[Fe(C₅H₅)(C₂₁H₂₃)]	F(000) = 840
M_r = 396.33	D_x = 1.302 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2325 reflections
a = 6.2777 (16) Å	θ = 2.5–24.8°
b = 34.562 (9) Å	µ = 0.75 mm⁻¹
c = 9.321 (2) Å	T = 294 K
β = 90.443 (4)°	Block, red
V = 2022.3 (9) Å³	0.26 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3703 independent reflections
Radiation source: fine-focus sealed tube	3102 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.736, T_max = 0.847	k = −42→20
5671 measured reflections	l = −10→11

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0341P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3703 reflections	Δρ_max = 0.20 e Å⁻³
244 parameters	Δρ_min = −0.24 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1633 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Crystal data top

[Fe(C₅H₅)(C₂₁H₂₃)]	V = 2022.3 (9) Å³
M_r = 396.33	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 6.2777 (16) Å	µ = 0.75 mm⁻¹
b = 34.562 (9) Å	T = 294 K
c = 9.321 (2) Å	0.26 × 0.24 × 0.22 mm
β = 90.443 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3703 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3102 reflections with I > 2σ(I)
T_min = 0.736, T_max = 0.847	R_int = 0.022
5671 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.080	Δρ_max = 0.20 e Å⁻³
S = 1.00	Δρ_min = −0.24 e Å⁻³
3703 reflections	Absolute structure: Flack (1983), 1633 Friedel pairs
244 parameters	Absolute structure parameter: 0.01 (2)
2 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	0.30239 (6)	0.198045 (10)	0.14011 (5)	0.04286 (12)
C1	0.3981 (6)	0.24047 (11)	0.0024 (4)	0.0673 (11)
H1	0.5382	0.2451	−0.0246	0.081*
C2	0.2896 (13)	0.25654 (9)	0.1229 (6)	0.0905 (15)
H2	0.3467	0.2739	0.1892	0.109*
C3	0.0823 (9)	0.24157 (13)	0.1236 (4)	0.0812 (14)
H3	−0.0220	0.2472	0.1908	0.097*
C4	0.0593 (6)	0.21719 (11)	0.0079 (4)	0.0616 (10)
H4	−0.0631	0.2035	−0.0166	0.074*
C5	0.2510 (6)	0.21657 (9)	−0.0664 (3)	0.0507 (8)
H5	0.2768	0.2024	−0.1492	0.061*
C6	0.2199 (5)	0.14681 (8)	0.2352 (3)	0.0474 (8)
H6	0.0900	0.1342	0.2234	0.057*
C7	0.2660 (8)	0.17519 (10)	0.3394 (3)	0.0658 (11)
H7	0.1728	0.1843	0.4088	0.079*
C8	0.4779 (8)	0.18739 (10)	0.3202 (4)	0.0681 (12)
H8	0.5491	0.2060	0.3746	0.082*
C9	0.5637 (5)	0.16643 (9)	0.2034 (3)	0.0472 (8)
H9	0.7006	0.1692	0.1674	0.057*
C10	0.4063 (4)	0.14051 (8)	0.1502 (3)	0.0343 (6)
C11	0.4299 (4)	0.10716 (8)	0.0448 (3)	0.0334 (6)
C12	0.2317 (4)	0.10633 (10)	−0.0583 (3)	0.0469 (7)
H12A	0.1205	0.0917	−0.0112	0.056*
H12B	0.1804	0.1327	−0.0683	0.056*
C13	0.2581 (6)	0.08951 (11)	−0.2111 (4)	0.0633 (10)
H13A	0.3519	0.0672	−0.2059	0.076*
H13B	0.1204	0.0806	−0.2455	0.076*
C14	0.3481 (7)	0.11832 (13)	−0.3194 (3)	0.0749 (11)
H14A	0.3196	0.1087	−0.4154	0.090*
H14B	0.2728	0.1427	−0.3094	0.090*
C15	0.5845 (6)	0.12597 (13)	−0.3046 (3)	0.0677 (10)
H15A	0.6241	0.1453	−0.3749	0.081*
H15B	0.6602	0.1024	−0.3280	0.081*
C16	0.6604 (5)	0.13974 (9)	−0.1569 (3)	0.0469 (8)
H16A	0.5777	0.1623	−0.1300	0.056*
H16B	0.8080	0.1478	−0.1639	0.056*
C17	0.6427 (4)	0.10939 (9)	−0.0369 (3)	0.0397 (7)
H17A	0.7552	0.1144	0.0326	0.048*
H17B	0.6700	0.0842	−0.0785	0.048*
C18	0.4287 (4)	0.06904 (8)	0.1378 (3)	0.0417 (7)
H18	0.3046	0.0700	0.2008	0.050*
C19	0.4168 (6)	0.03164 (9)	0.0519 (4)	0.0631 (10)
H19	0.3109	0.0260	−0.0152	0.076*
C20	0.5757 (8)	0.00824 (10)	0.0848 (5)	0.0759 (12)
H20	0.5970	−0.0160	0.0442	0.091*
C21	0.7120 (6)	0.02548 (10)	0.1927 (4)	0.0579 (9)
C22	0.8991 (8)	0.01294 (13)	0.2608 (5)	0.0831 (14)
H22	0.9611	−0.0105	0.2350	0.100*
C23	0.9900 (7)	0.03530 (15)	0.3654 (6)	0.0859 (15)
H23	1.1140	0.0269	0.4109	0.103*
C24	0.9013 (6)	0.07012 (12)	0.4048 (4)	0.0678 (11)
H24	0.9661	0.0848	0.4766	0.081*
C25	0.7171 (5)	0.08370 (9)	0.3392 (3)	0.0487 (8)
H25	0.6568	0.1070	0.3676	0.058*
C26	0.6238 (5)	0.06181 (8)	0.2300 (3)	0.0414 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0645 (3)	0.02994 (18)	0.03414 (18)	0.0058 (2)	0.00076 (15)	0.0037 (2)
C1	0.073 (2)	0.058 (2)	0.072 (3)	−0.014 (2)	−0.009 (2)	0.033 (2)
C2	0.182 (5)	0.0211 (14)	0.067 (3)	−0.001 (3)	−0.054 (3)	0.001 (2)
C3	0.120 (4)	0.068 (3)	0.056 (2)	0.051 (3)	0.011 (2)	0.011 (2)
C4	0.062 (2)	0.058 (2)	0.064 (2)	0.0163 (18)	−0.0002 (18)	0.024 (2)
C5	0.071 (2)	0.0425 (18)	0.0389 (17)	0.0110 (17)	0.0020 (16)	0.0105 (15)
C6	0.060 (2)	0.0364 (16)	0.0457 (19)	0.0088 (15)	0.0160 (15)	0.0117 (15)
C7	0.124 (4)	0.0403 (19)	0.0338 (17)	0.020 (2)	0.0205 (19)	0.0097 (15)
C8	0.125 (4)	0.0379 (18)	0.0406 (19)	0.003 (2)	−0.031 (2)	−0.0034 (16)
C9	0.0560 (19)	0.0381 (17)	0.0473 (18)	−0.0044 (14)	−0.0157 (15)	0.0023 (14)
C10	0.0385 (15)	0.0311 (14)	0.0332 (14)	0.0032 (12)	−0.0002 (12)	0.0047 (12)
C11	0.0261 (13)	0.0357 (15)	0.0384 (14)	0.0002 (11)	−0.0025 (11)	−0.0054 (12)
C12	0.0302 (16)	0.0528 (19)	0.0576 (18)	−0.0020 (13)	−0.0075 (14)	−0.0096 (16)
C13	0.059 (2)	0.071 (2)	0.060 (2)	−0.0058 (19)	−0.0210 (17)	−0.018 (2)
C14	0.087 (3)	0.094 (3)	0.043 (2)	−0.005 (2)	−0.0226 (19)	−0.011 (2)
C15	0.075 (3)	0.093 (3)	0.0353 (17)	−0.005 (2)	0.0006 (16)	−0.0053 (19)
C16	0.0375 (17)	0.060 (2)	0.0434 (17)	−0.0006 (15)	0.0043 (13)	0.0001 (15)
C17	0.0306 (15)	0.0496 (17)	0.0390 (14)	0.0045 (13)	0.0002 (12)	−0.0033 (13)
C18	0.0362 (16)	0.0347 (15)	0.0542 (18)	−0.0023 (13)	0.0092 (13)	−0.0034 (14)
C19	0.081 (3)	0.0341 (17)	0.075 (2)	−0.0124 (18)	−0.002 (2)	−0.0058 (18)
C20	0.117 (4)	0.0321 (18)	0.079 (3)	0.010 (2)	0.022 (3)	−0.0045 (19)
C21	0.067 (2)	0.0415 (18)	0.066 (2)	0.0174 (17)	0.0225 (18)	0.0122 (17)
C22	0.086 (3)	0.074 (3)	0.089 (3)	0.044 (3)	0.030 (3)	0.033 (3)
C23	0.054 (2)	0.107 (4)	0.097 (3)	0.024 (3)	0.009 (2)	0.060 (3)
C24	0.059 (2)	0.084 (3)	0.060 (2)	−0.001 (2)	−0.0079 (18)	0.037 (2)
C25	0.054 (2)	0.0464 (18)	0.0457 (17)	0.0008 (15)	0.0001 (15)	0.0164 (15)
C26	0.0423 (17)	0.0347 (15)	0.0472 (17)	0.0040 (13)	0.0100 (13)	0.0111 (13)

Geometric parameters (Å, º) top

Fe1—C1	2.042 (3)	C12—H12A	0.97
Fe1—C2	2.029 (3)	C12—H12B	0.97
Fe1—C3	2.048 (4)	C13—C14	1.530 (5)
Fe1—C4	2.063 (3)	C13—H13A	0.97
Fe1—C5	2.051 (3)	C13—H13B	0.97
Fe1—C6	2.048 (3)	C14—C15	1.513 (5)
Fe1—C7	2.033 (3)	C14—H14A	0.97
Fe1—C8	2.034 (3)	C14—H14B	0.97
Fe1—C9	2.053 (3)	C15—C16	1.529 (4)
Fe1—C10	2.095 (3)	C15—H15A	0.97
C1—C5	1.391 (5)	C15—H15B	0.97
C1—C2	1.431 (7)	C16—C17	1.538 (4)
C1—H1	0.93	C16—H16A	0.97
C2—C3	1.400 (8)	C16—H16B	0.97
C2—H2	0.93	C17—H17A	0.97
C3—C4	1.375 (6)	C17—H17B	0.97
C3—H3	0.93	C18—C26	1.512 (4)
C4—C5	1.393 (5)	C18—C19	1.522 (4)
C4—H4	0.93	C18—H18	0.98
C5—H5	0.93	C19—C20	1.319 (6)
C6—C7	1.409 (5)	C19—H19	0.93
C6—C10	1.435 (4)	C20—C21	1.444 (6)
C6—H6	0.93	C20—H20	0.93
C7—C8	1.408 (6)	C21—C22	1.400 (5)
C7—H7	0.93	C21—C26	1.417 (4)
C8—C9	1.417 (5)	C22—C23	1.366 (6)
C8—H8	0.93	C22—H22	0.93
C9—C10	1.420 (4)	C23—C24	1.377 (6)
C9—H9	0.93	C23—H23	0.93
C10—C11	1.523 (4)	C24—C25	1.386 (4)
C11—C17	1.544 (4)	C24—H24	0.93
C11—C12	1.567 (4)	C25—C26	1.394 (4)
C11—C18	1.577 (4)	C25—H25	0.93
C12—C13	1.548 (4)

C2—Fe1—C7	117.03 (19)	C9—C8—Fe1	70.44 (17)
C2—Fe1—C8	105.44 (17)	C7—C8—H8	126.0
C7—Fe1—C8	40.51 (17)	C9—C8—H8	126.0
C2—Fe1—C1	41.1 (2)	Fe1—C8—H8	125.5
C7—Fe1—C1	152.75 (16)	C8—C9—C10	108.9 (3)
C8—Fe1—C1	119.25 (16)	C8—C9—Fe1	69.0 (2)
C2—Fe1—C3	40.2 (2)	C10—C9—Fe1	71.56 (16)
C7—Fe1—C3	105.88 (16)	C8—C9—H9	125.6
C8—Fe1—C3	123.77 (17)	C10—C9—H9	125.6
C1—Fe1—C3	68.09 (18)	Fe1—C9—H9	125.5
C2—Fe1—C6	152.3 (2)	C9—C10—C6	106.2 (3)
C7—Fe1—C6	40.37 (13)	C9—C10—C11	129.2 (3)
C8—Fe1—C6	67.88 (15)	C6—C10—C11	123.7 (3)
C1—Fe1—C6	165.74 (15)	C9—C10—Fe1	68.42 (16)
C3—Fe1—C6	119.67 (18)	C6—C10—Fe1	68.01 (16)
C2—Fe1—C5	66.99 (17)	C11—C10—Fe1	136.15 (19)
C7—Fe1—C5	163.85 (17)	C10—C11—C17	111.7 (2)
C8—Fe1—C5	155.61 (17)	C10—C11—C12	109.2 (2)
C1—Fe1—C5	39.73 (13)	C17—C11—C12	112.6 (2)
C3—Fe1—C5	66.36 (15)	C10—C11—C18	106.0 (2)
C6—Fe1—C5	129.60 (14)	C17—C11—C18	108.7 (2)
C2—Fe1—C9	125.7 (2)	C12—C11—C18	108.3 (2)
C7—Fe1—C9	68.04 (15)	C13—C12—C11	118.7 (3)
C8—Fe1—C9	40.58 (15)	C13—C12—H12A	107.6
C1—Fe1—C9	108.93 (15)	C11—C12—H12A	107.6
C3—Fe1—C9	161.72 (17)	C13—C12—H12B	107.6
C6—Fe1—C9	67.65 (13)	C11—C12—H12B	107.6
C5—Fe1—C9	123.70 (14)	H12A—C12—H12B	107.1
C2—Fe1—C4	66.7 (2)	C14—C13—C12	113.9 (3)
C7—Fe1—C4	125.64 (16)	C14—C13—H13A	108.8
C8—Fe1—C4	160.80 (16)	C12—C13—H13A	108.8
C1—Fe1—C4	67.29 (15)	C14—C13—H13B	108.8
C3—Fe1—C4	39.09 (16)	C12—C13—H13B	108.8
C6—Fe1—C4	110.34 (14)	H13A—C13—H13B	107.7
C5—Fe1—C4	39.58 (14)	C15—C14—C13	114.9 (3)
C9—Fe1—C4	158.07 (14)	C15—C14—H14A	108.6
C2—Fe1—C10	164.0 (3)	C13—C14—H14A	108.6
C7—Fe1—C10	68.11 (12)	C15—C14—H14B	108.6
C8—Fe1—C10	67.94 (12)	C13—C14—H14B	108.6
C1—Fe1—C10	128.09 (15)	H14A—C14—H14B	107.5
C3—Fe1—C10	155.59 (18)	C14—C15—C16	115.8 (3)
C6—Fe1—C10	40.50 (12)	C14—C15—H15A	108.3
C5—Fe1—C10	112.66 (12)	C16—C15—H15A	108.3
C9—Fe1—C10	40.02 (11)	C14—C15—H15B	108.3
C4—Fe1—C10	124.06 (14)	C16—C15—H15B	108.3
C5—C1—C2	105.9 (4)	H15A—C15—H15B	107.4
C5—C1—Fe1	70.48 (19)	C15—C16—C17	114.8 (3)
C2—C1—Fe1	68.9 (2)	C15—C16—H16A	108.6
C5—C1—H1	127.1	C17—C16—H16A	108.6
C2—C1—H1	127.1	C15—C16—H16B	108.6
Fe1—C1—H1	125.1	C17—C16—H16B	108.6
C3—C2—C1	107.9 (3)	H16A—C16—H16B	107.6
C3—C2—Fe1	70.6 (2)	C16—C17—C11	117.4 (2)
C1—C2—Fe1	69.9 (2)	C16—C17—H17A	108.0
C3—C2—H2	126.0	C11—C17—H17A	108.0
C1—C2—H2	126.0	C16—C17—H17B	108.0
Fe1—C2—H2	125.0	C11—C17—H17B	108.0
C4—C3—C2	108.3 (4)	H17A—C17—H17B	107.2
C4—C3—Fe1	71.1 (2)	C26—C18—C19	101.2 (3)
C2—C3—Fe1	69.2 (2)	C26—C18—C11	116.3 (2)
C4—C3—H3	125.8	C19—C18—C11	114.9 (2)
C2—C3—H3	125.8	C26—C18—H18	108.0
Fe1—C3—H3	125.5	C19—C18—H18	108.0
C3—C4—C5	108.2 (4)	C11—C18—H18	108.0
C3—C4—Fe1	69.9 (2)	C20—C19—C18	111.4 (3)
C5—C4—Fe1	69.76 (19)	C20—C19—H19	124.3
C3—C4—H4	125.9	C18—C19—H19	124.3
C5—C4—H4	125.9	C19—C20—C21	110.6 (3)
Fe1—C4—H4	126.1	C19—C20—H20	124.7
C1—C5—C4	109.6 (3)	C21—C20—H20	124.7
C1—C5—Fe1	69.79 (18)	C22—C21—C26	119.4 (4)
C4—C5—Fe1	70.66 (19)	C22—C21—C20	132.7 (4)
C1—C5—H5	125.2	C26—C21—C20	107.8 (3)
C4—C5—H5	125.2	C23—C22—C21	119.5 (4)
Fe1—C5—H5	125.9	C23—C22—H22	120.2
C7—C6—C10	108.8 (3)	C21—C22—H22	120.2
C7—C6—Fe1	69.24 (18)	C22—C23—C24	121.1 (4)
C10—C6—Fe1	71.49 (17)	C22—C23—H23	119.4
C7—C6—H6	125.6	C24—C23—H23	119.4
C10—C6—H6	125.6	C23—C24—C25	121.1 (4)
Fe1—C6—H6	125.3	C23—C24—H24	119.4
C8—C7—C6	108.0 (3)	C25—C24—H24	119.4
C8—C7—Fe1	69.78 (19)	C24—C25—C26	118.9 (3)
C6—C7—Fe1	70.39 (17)	C24—C25—H25	120.6
C8—C7—H7	126.0	C26—C25—H25	120.6
C6—C7—H7	126.0	C25—C26—C21	119.8 (3)
Fe1—C7—H7	125.4	C25—C26—C18	131.3 (3)
C7—C8—C9	108.0 (3)	C21—C26—C18	108.9 (3)
C7—C8—Fe1	69.7 (2)

C2—Fe1—C1—C5	−116.6 (4)	C3—Fe1—C7—C6	117.4 (3)
C7—Fe1—C1—C5	−161.1 (3)	C5—Fe1—C7—C6	58.5 (6)
C8—Fe1—C1—C5	163.6 (2)	C9—Fe1—C7—C6	−80.9 (2)
C3—Fe1—C1—C5	−78.9 (3)	C4—Fe1—C7—C6	79.5 (3)
C6—Fe1—C1—C5	46.8 (7)	C10—Fe1—C7—C6	−37.6 (2)
C9—Fe1—C1—C5	120.3 (2)	C6—C7—C8—C9	0.0 (4)
C4—Fe1—C1—C5	−36.5 (2)	Fe1—C7—C8—C9	−60.3 (2)
C10—Fe1—C1—C5	79.8 (2)	C6—C7—C8—Fe1	60.2 (2)
C7—Fe1—C1—C2	−44.5 (5)	C2—Fe1—C8—C7	113.7 (3)
C8—Fe1—C1—C2	−79.8 (3)	C1—Fe1—C8—C7	155.9 (2)
C3—Fe1—C1—C2	37.7 (3)	C3—Fe1—C8—C7	74.0 (3)
C6—Fe1—C1—C2	163.4 (6)	C6—Fe1—C8—C7	−37.79 (19)
C5—Fe1—C1—C2	116.6 (4)	C5—Fe1—C8—C7	−178.1 (3)
C9—Fe1—C1—C2	−123.1 (3)	C9—Fe1—C8—C7	−118.8 (3)
C4—Fe1—C1—C2	80.1 (3)	C4—Fe1—C8—C7	50.7 (6)
C10—Fe1—C1—C2	−163.6 (3)	C10—Fe1—C8—C7	−81.7 (2)
C5—C1—C2—C3	0.5 (4)	C2—Fe1—C8—C9	−127.5 (3)
Fe1—C1—C2—C3	−60.7 (2)	C7—Fe1—C8—C9	118.8 (3)
C5—C1—C2—Fe1	61.2 (2)	C1—Fe1—C8—C9	−85.3 (2)
C7—Fe1—C2—C3	−82.6 (3)	C3—Fe1—C8—C9	−167.2 (2)
C8—Fe1—C2—C3	−124.5 (3)	C6—Fe1—C8—C9	81.0 (2)
C1—Fe1—C2—C3	118.5 (3)	C5—Fe1—C8—C9	−59.4 (4)
C6—Fe1—C2—C3	−52.8 (4)	C4—Fe1—C8—C9	169.5 (4)
C5—Fe1—C2—C3	80.1 (3)	C10—Fe1—C8—C9	37.13 (19)
C9—Fe1—C2—C3	−164.0 (2)	C7—C8—C9—C10	−0.9 (4)
C4—Fe1—C2—C3	36.9 (2)	Fe1—C8—C9—C10	−60.7 (2)
C10—Fe1—C2—C3	172.2 (5)	C7—C8—C9—Fe1	59.8 (2)
C7—Fe1—C2—C1	158.9 (2)	C2—Fe1—C9—C8	70.4 (3)
C8—Fe1—C2—C1	117.0 (3)	C7—Fe1—C9—C8	−37.9 (2)
C3—Fe1—C2—C1	−118.5 (3)	C1—Fe1—C9—C8	113.2 (3)
C6—Fe1—C2—C1	−171.3 (3)	C3—Fe1—C9—C8	35.9 (6)
C5—Fe1—C2—C1	−38.4 (2)	C6—Fe1—C9—C8	−81.6 (2)
C9—Fe1—C2—C1	77.5 (3)	C5—Fe1—C9—C8	154.7 (2)
C4—Fe1—C2—C1	−81.6 (2)	C4—Fe1—C9—C8	−170.8 (4)
C10—Fe1—C2—C1	53.8 (7)	C10—Fe1—C9—C8	−119.5 (3)
C1—C2—C3—C4	−0.3 (4)	C2—Fe1—C9—C10	−170.1 (3)
Fe1—C2—C3—C4	−60.6 (3)	C7—Fe1—C9—C10	81.7 (2)
C1—C2—C3—Fe1	60.2 (2)	C8—Fe1—C9—C10	119.5 (3)
C2—Fe1—C3—C4	119.1 (4)	C1—Fe1—C9—C10	−127.3 (2)
C7—Fe1—C3—C4	−127.6 (3)	C3—Fe1—C9—C10	155.4 (5)
C8—Fe1—C3—C4	−168.1 (2)	C6—Fe1—C9—C10	37.91 (18)
C1—Fe1—C3—C4	80.5 (3)	C5—Fe1—C9—C10	−85.7 (2)
C6—Fe1—C3—C4	−86.2 (3)	C4—Fe1—C9—C10	−51.2 (4)
C5—Fe1—C3—C4	37.3 (2)	C8—C9—C10—C6	1.4 (3)
C9—Fe1—C3—C4	164.6 (4)	Fe1—C9—C10—C6	−57.7 (2)
C10—Fe1—C3—C4	−55.8 (4)	C8—C9—C10—C11	−168.2 (3)
C7—Fe1—C3—C2	113.3 (3)	Fe1—C9—C10—C11	132.7 (3)
C8—Fe1—C3—C2	72.8 (3)	C8—C9—C10—Fe1	59.1 (2)
C1—Fe1—C3—C2	−38.6 (3)	C7—C6—C10—C9	−1.5 (3)
C6—Fe1—C3—C2	154.7 (3)	Fe1—C6—C10—C9	57.9 (2)
C5—Fe1—C3—C2	−81.8 (3)	C7—C6—C10—C11	168.9 (2)
C9—Fe1—C3—C2	45.5 (6)	Fe1—C6—C10—C11	−131.7 (3)
C4—Fe1—C3—C2	−119.1 (4)	C7—C6—C10—Fe1	−59.4 (2)
C10—Fe1—C3—C2	−174.8 (4)	C2—Fe1—C10—C9	30.6 (7)
C2—C3—C4—C5	0.0 (4)	C7—Fe1—C10—C9	−81.5 (2)
Fe1—C3—C4—C5	−59.4 (2)	C8—Fe1—C10—C9	−37.6 (2)
C2—C3—C4—Fe1	59.4 (3)	C1—Fe1—C10—C9	73.0 (2)
C2—Fe1—C4—C3	−37.9 (3)	C3—Fe1—C10—C9	−161.6 (3)
C7—Fe1—C4—C3	69.6 (3)	C6—Fe1—C10—C9	−118.9 (3)
C8—Fe1—C4—C3	31.4 (6)	C5—Fe1—C10—C9	116.0 (2)
C1—Fe1—C4—C3	−82.7 (3)	C4—Fe1—C10—C9	159.4 (2)
C6—Fe1—C4—C3	112.4 (3)	C2—Fe1—C10—C6	149.5 (6)
C5—Fe1—C4—C3	−119.4 (4)	C7—Fe1—C10—C6	37.5 (2)
C9—Fe1—C4—C3	−167.1 (4)	C8—Fe1—C10—C6	81.3 (2)
C10—Fe1—C4—C3	155.6 (3)	C1—Fe1—C10—C6	−168.1 (2)
C2—Fe1—C4—C5	81.5 (3)	C3—Fe1—C10—C6	−42.6 (4)
C7—Fe1—C4—C5	−171.0 (2)	C5—Fe1—C10—C6	−125.1 (2)
C8—Fe1—C4—C5	150.8 (4)	C9—Fe1—C10—C6	118.9 (3)
C1—Fe1—C4—C5	36.7 (2)	C4—Fe1—C10—C6	−81.6 (2)
C3—Fe1—C4—C5	119.4 (4)	C2—Fe1—C10—C11	−94.1 (7)
C6—Fe1—C4—C5	−128.2 (2)	C7—Fe1—C10—C11	153.8 (3)
C9—Fe1—C4—C5	−47.7 (5)	C8—Fe1—C10—C11	−162.3 (3)
C10—Fe1—C4—C5	−85.0 (2)	C1—Fe1—C10—C11	−51.7 (3)
C2—C1—C5—C4	−0.5 (4)	C3—Fe1—C10—C11	73.7 (5)
Fe1—C1—C5—C4	59.6 (2)	C6—Fe1—C10—C11	116.4 (3)
C2—C1—C5—Fe1	−60.2 (2)	C5—Fe1—C10—C11	−8.7 (3)
C3—C4—C5—C1	0.3 (4)	C9—Fe1—C10—C11	−124.7 (3)
Fe1—C4—C5—C1	−59.1 (2)	C4—Fe1—C10—C11	34.7 (3)
C3—C4—C5—Fe1	59.5 (2)	C9—C10—C11—C17	−15.3 (4)
C2—Fe1—C5—C1	39.7 (3)	C6—C10—C11—C17	176.7 (3)
C7—Fe1—C5—C1	147.7 (5)	Fe1—C10—C11—C17	84.2 (3)
C8—Fe1—C5—C1	−36.6 (4)	C9—C10—C11—C12	−140.5 (3)
C3—Fe1—C5—C1	83.6 (3)	C6—C10—C11—C12	51.5 (4)
C6—Fe1—C5—C1	−166.5 (2)	Fe1—C10—C11—C12	−41.1 (4)
C9—Fe1—C5—C1	−78.9 (3)	C9—C10—C11—C18	103.0 (3)
C4—Fe1—C5—C1	120.5 (3)	C6—C10—C11—C18	−65.0 (3)
C10—Fe1—C5—C1	−122.9 (2)	Fe1—C10—C11—C18	−157.6 (2)
C2—Fe1—C5—C4	−80.8 (3)	C10—C11—C12—C13	152.1 (3)
C7—Fe1—C5—C4	27.2 (6)	C17—C11—C12—C13	27.4 (4)
C8—Fe1—C5—C4	−157.1 (3)	C18—C11—C12—C13	−92.9 (3)
C1—Fe1—C5—C4	−120.5 (3)	C11—C12—C13—C14	−83.0 (4)
C3—Fe1—C5—C4	−36.8 (3)	C12—C13—C14—C15	75.5 (4)
C6—Fe1—C5—C4	73.0 (3)	C13—C14—C15—C16	−55.7 (5)
C9—Fe1—C5—C4	160.6 (2)	C14—C15—C16—C17	67.7 (4)
C10—Fe1—C5—C4	116.6 (2)	C15—C16—C17—C11	−87.9 (3)
C2—Fe1—C6—C7	−43.1 (5)	C10—C11—C17—C16	−75.4 (3)
C8—Fe1—C6—C7	37.9 (2)	C12—C11—C17—C16	47.9 (3)
C1—Fe1—C6—C7	160.7 (6)	C18—C11—C17—C16	168.0 (2)
C3—Fe1—C6—C7	−79.4 (3)	C10—C11—C18—C26	−70.9 (3)
C5—Fe1—C6—C7	−162.1 (2)	C17—C11—C18—C26	49.3 (3)
C9—Fe1—C6—C7	81.9 (2)	C12—C11—C18—C26	172.0 (2)
C4—Fe1—C6—C7	−121.6 (2)	C10—C11—C18—C19	171.1 (3)
C10—Fe1—C6—C7	119.4 (3)	C17—C11—C18—C19	−68.7 (3)
C2—Fe1—C6—C10	−162.5 (4)	C12—C11—C18—C19	54.0 (3)
C7—Fe1—C6—C10	−119.4 (3)	C26—C18—C19—C20	−1.6 (4)
C8—Fe1—C6—C10	−81.5 (2)	C11—C18—C19—C20	124.6 (3)
C1—Fe1—C6—C10	41.4 (7)	C18—C19—C20—C21	0.0 (5)
C3—Fe1—C6—C10	161.2 (2)	C19—C20—C21—C22	−179.0 (4)
C5—Fe1—C6—C10	78.5 (2)	C19—C20—C21—C26	1.7 (5)
C9—Fe1—C6—C10	−37.47 (18)	C26—C21—C22—C23	2.1 (6)
C4—Fe1—C6—C10	119.1 (2)	C20—C21—C22—C23	−177.2 (4)
C10—C6—C7—C8	0.9 (4)	C21—C22—C23—C24	−0.3 (6)
Fe1—C6—C7—C8	−59.9 (2)	C22—C23—C24—C25	−0.2 (6)
C10—C6—C7—Fe1	60.8 (2)	C23—C24—C25—C26	−1.1 (5)
C2—Fe1—C7—C8	−82.1 (3)	C24—C25—C26—C21	3.0 (4)
C1—Fe1—C7—C8	−51.0 (4)	C24—C25—C26—C18	−178.8 (3)
C3—Fe1—C7—C8	−123.8 (3)	C22—C21—C26—C25	−3.5 (5)
C6—Fe1—C7—C8	118.8 (3)	C20—C21—C26—C25	176.0 (3)
C5—Fe1—C7—C8	177.3 (4)	C22—C21—C26—C18	177.9 (3)
C9—Fe1—C7—C8	37.9 (2)	C20—C21—C26—C18	−2.7 (4)
C4—Fe1—C7—C8	−161.7 (2)	C19—C18—C26—C25	−175.9 (3)
C10—Fe1—C7—C8	81.2 (2)	C11—C18—C26—C25	58.9 (4)
C2—Fe1—C7—C6	159.1 (3)	C19—C18—C26—C21	2.5 (3)
C8—Fe1—C7—C6	−118.8 (3)	C11—C18—C26—C21	−122.7 (3)
C1—Fe1—C7—C6	−169.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg1ⁱ	0.93	2.76	3.689 (4)	173
C17—H17B···Cg3	0.97	2.67	2.987 (3)	100
C20—H20···Cg4ⁱⁱ	0.93	2.87	3.618 (5)	138
C25—H25···Cg2	0.93	2.80	3.540 (4)	137

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, −y, z−1/2.

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₂₁H₂₃)]
M_r	396.33
Crystal system, space group	Monoclinic, Cc
Temperature (K)	294
a, b, c (Å)	6.2777 (16), 34.562 (9), 9.321 (2)
β (°)	90.443 (4)
V (Å³)	2022.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.26 × 0.24 × 0.22

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.736, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	5671, 3703, 3102
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.080, 1.00
No. of reflections	3703
No. of parameters	244
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24
Absolute structure	Flack (1983), 1633 Friedel pairs
Absolute structure parameter	0.01 (2)

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	2.042 (3)	Fe1—C6	2.048 (3)
Fe1—C2	2.029 (3)	Fe1—C7	2.033 (3)
Fe1—C3	2.048 (4)	Fe1—C8	2.034 (3)
Fe1—C4	2.063 (3)	Fe1—C9	2.053 (3)
Fe1—C5	2.051 (3)	Fe1—C10	2.095 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg1ⁱ	0.93	2.76	3.689 (4)	173
C17—H17B···Cg3	0.97	2.67	2.987 (3)	100
C20—H20···Cg4ⁱⁱ	0.93	2.87	3.618 (5)	138
C25—H25···Cg2	0.93	2.80	3.540 (4)	137

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x, −y, z−1/2.

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