Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029302/ci6650sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029302/ci6650Isup2.hkl
Contains datablock I

CCDC reference: 287515

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](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 CH2Cl2 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%.

Refinement top

H atoms were placed in calculated positions, with C—H = 0.93 or 0.97 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(parent atom).

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
[Figure 1] 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
Mr = 396.33Dx = 1.302 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 2325 reflections
a = 6.2777 (16) Åθ = 2.5–24.8°
b = 34.562 (9) ŵ = 0.75 mm1
c = 9.321 (2) ÅT = 294 K
β = 90.443 (4)°Block, red
V = 2022.3 (9) Å30.26 × 0.24 × 0.22 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3703 independent reflections
Radiation source: fine-focus sealed tube3102 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ϕ and ω scansθmax = 26.4°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.736, Tmax = 0.847k = 4220
5671 measured reflectionsl = 1011
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0341P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3703 reflectionsΔρmax = 0.20 e Å3
244 parametersΔρmin = 0.24 e Å3
2 restraintsAbsolute structure: Flack (1983), 1633 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (2)
Crystal data top
[Fe(C5H5)(C21H23)]V = 2022.3 (9) Å3
Mr = 396.33Z = 4
Monoclinic, CcMo Kα radiation
a = 6.2777 (16) ŵ = 0.75 mm1
b = 34.562 (9) ÅT = 294 K
c = 9.321 (2) Å0.26 × 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)
Tmin = 0.736, Tmax = 0.847Rint = 0.022
5671 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.080Δρmax = 0.20 e Å3
S = 1.00Δρmin = 0.24 e Å3
3703 reflectionsAbsolute structure: Flack (1983), 1633 Friedel pairs
244 parametersAbsolute 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
xyzUiso*/Ueq
Fe10.30239 (6)0.198045 (10)0.14011 (5)0.04286 (12)
C10.3981 (6)0.24047 (11)0.0024 (4)0.0673 (11)
H10.53820.24510.02460.081*
C20.2896 (13)0.25654 (9)0.1229 (6)0.0905 (15)
H20.34670.27390.18920.109*
C30.0823 (9)0.24157 (13)0.1236 (4)0.0812 (14)
H30.02200.24720.19080.097*
C40.0593 (6)0.21719 (11)0.0079 (4)0.0616 (10)
H40.06310.20350.01660.074*
C50.2510 (6)0.21657 (9)0.0664 (3)0.0507 (8)
H50.27680.20240.14920.061*
C60.2199 (5)0.14681 (8)0.2352 (3)0.0474 (8)
H60.09000.13420.22340.057*
C70.2660 (8)0.17519 (10)0.3394 (3)0.0658 (11)
H70.17280.18430.40880.079*
C80.4779 (8)0.18739 (10)0.3202 (4)0.0681 (12)
H80.54910.20600.37460.082*
C90.5637 (5)0.16643 (9)0.2034 (3)0.0472 (8)
H90.70060.16920.16740.057*
C100.4063 (4)0.14051 (8)0.1502 (3)0.0343 (6)
C110.4299 (4)0.10716 (8)0.0448 (3)0.0334 (6)
C120.2317 (4)0.10633 (10)0.0583 (3)0.0469 (7)
H12A0.12050.09170.01120.056*
H12B0.18040.13270.06830.056*
C130.2581 (6)0.08951 (11)0.2111 (4)0.0633 (10)
H13A0.35190.06720.20590.076*
H13B0.12040.08060.24550.076*
C140.3481 (7)0.11832 (13)0.3194 (3)0.0749 (11)
H14A0.31960.10870.41540.090*
H14B0.27280.14270.30940.090*
C150.5845 (6)0.12597 (13)0.3046 (3)0.0677 (10)
H15A0.62410.14530.37490.081*
H15B0.66020.10240.32800.081*
C160.6604 (5)0.13974 (9)0.1569 (3)0.0469 (8)
H16A0.57770.16230.13000.056*
H16B0.80800.14780.16390.056*
C170.6427 (4)0.10939 (9)0.0369 (3)0.0397 (7)
H17A0.75520.11440.03260.048*
H17B0.67000.08420.07850.048*
C180.4287 (4)0.06904 (8)0.1378 (3)0.0417 (7)
H180.30460.07000.20080.050*
C190.4168 (6)0.03164 (9)0.0519 (4)0.0631 (10)
H190.31090.02600.01520.076*
C200.5757 (8)0.00824 (10)0.0848 (5)0.0759 (12)
H200.59700.01600.04420.091*
C210.7120 (6)0.02548 (10)0.1927 (4)0.0579 (9)
C220.8991 (8)0.01294 (13)0.2608 (5)0.0831 (14)
H220.96110.01050.23500.100*
C230.9900 (7)0.03530 (15)0.3654 (6)0.0859 (15)
H231.11400.02690.41090.103*
C240.9013 (6)0.07012 (12)0.4048 (4)0.0678 (11)
H240.96610.08480.47660.081*
C250.7171 (5)0.08370 (9)0.3392 (3)0.0487 (8)
H250.65680.10700.36760.058*
C260.6238 (5)0.06181 (8)0.2300 (3)0.0414 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0645 (3)0.02994 (18)0.03414 (18)0.0058 (2)0.00076 (15)0.0037 (2)
C10.073 (2)0.058 (2)0.072 (3)0.014 (2)0.009 (2)0.033 (2)
C20.182 (5)0.0211 (14)0.067 (3)0.001 (3)0.054 (3)0.001 (2)
C30.120 (4)0.068 (3)0.056 (2)0.051 (3)0.011 (2)0.011 (2)
C40.062 (2)0.058 (2)0.064 (2)0.0163 (18)0.0002 (18)0.024 (2)
C50.071 (2)0.0425 (18)0.0389 (17)0.0110 (17)0.0020 (16)0.0105 (15)
C60.060 (2)0.0364 (16)0.0457 (19)0.0088 (15)0.0160 (15)0.0117 (15)
C70.124 (4)0.0403 (19)0.0338 (17)0.020 (2)0.0205 (19)0.0097 (15)
C80.125 (4)0.0379 (18)0.0406 (19)0.003 (2)0.031 (2)0.0034 (16)
C90.0560 (19)0.0381 (17)0.0473 (18)0.0044 (14)0.0157 (15)0.0023 (14)
C100.0385 (15)0.0311 (14)0.0332 (14)0.0032 (12)0.0002 (12)0.0047 (12)
C110.0261 (13)0.0357 (15)0.0384 (14)0.0002 (11)0.0025 (11)0.0054 (12)
C120.0302 (16)0.0528 (19)0.0576 (18)0.0020 (13)0.0075 (14)0.0096 (16)
C130.059 (2)0.071 (2)0.060 (2)0.0058 (19)0.0210 (17)0.018 (2)
C140.087 (3)0.094 (3)0.043 (2)0.005 (2)0.0226 (19)0.011 (2)
C150.075 (3)0.093 (3)0.0353 (17)0.005 (2)0.0006 (16)0.0053 (19)
C160.0375 (17)0.060 (2)0.0434 (17)0.0006 (15)0.0043 (13)0.0001 (15)
C170.0306 (15)0.0496 (17)0.0390 (14)0.0045 (13)0.0002 (12)0.0033 (13)
C180.0362 (16)0.0347 (15)0.0542 (18)0.0023 (13)0.0092 (13)0.0034 (14)
C190.081 (3)0.0341 (17)0.075 (2)0.0124 (18)0.002 (2)0.0058 (18)
C200.117 (4)0.0321 (18)0.079 (3)0.010 (2)0.022 (3)0.0045 (19)
C210.067 (2)0.0415 (18)0.066 (2)0.0174 (17)0.0225 (18)0.0122 (17)
C220.086 (3)0.074 (3)0.089 (3)0.044 (3)0.030 (3)0.033 (3)
C230.054 (2)0.107 (4)0.097 (3)0.024 (3)0.009 (2)0.060 (3)
C240.059 (2)0.084 (3)0.060 (2)0.001 (2)0.0079 (18)0.037 (2)
C250.054 (2)0.0464 (18)0.0457 (17)0.0008 (15)0.0001 (15)0.0164 (15)
C260.0423 (17)0.0347 (15)0.0472 (17)0.0040 (13)0.0100 (13)0.0111 (13)
Geometric parameters (Å, º) top
Fe1—C12.042 (3)C12—H12A0.97
Fe1—C22.029 (3)C12—H12B0.97
Fe1—C32.048 (4)C13—C141.530 (5)
Fe1—C42.063 (3)C13—H13A0.97
Fe1—C52.051 (3)C13—H13B0.97
Fe1—C62.048 (3)C14—C151.513 (5)
Fe1—C72.033 (3)C14—H14A0.97
Fe1—C82.034 (3)C14—H14B0.97
Fe1—C92.053 (3)C15—C161.529 (4)
Fe1—C102.095 (3)C15—H15A0.97
C1—C51.391 (5)C15—H15B0.97
C1—C21.431 (7)C16—C171.538 (4)
C1—H10.93C16—H16A0.97
C2—C31.400 (8)C16—H16B0.97
C2—H20.93C17—H17A0.97
C3—C41.375 (6)C17—H17B0.97
C3—H30.93C18—C261.512 (4)
C4—C51.393 (5)C18—C191.522 (4)
C4—H40.93C18—H180.98
C5—H50.93C19—C201.319 (6)
C6—C71.409 (5)C19—H190.93
C6—C101.435 (4)C20—C211.444 (6)
C6—H60.93C20—H200.93
C7—C81.408 (6)C21—C221.400 (5)
C7—H70.93C21—C261.417 (4)
C8—C91.417 (5)C22—C231.366 (6)
C8—H80.93C22—H220.93
C9—C101.420 (4)C23—C241.377 (6)
C9—H90.93C23—H230.93
C10—C111.523 (4)C24—C251.386 (4)
C11—C171.544 (4)C24—H240.93
C11—C121.567 (4)C25—C261.394 (4)
C11—C181.577 (4)C25—H250.93
C12—C131.548 (4)
C2—Fe1—C7117.03 (19)C9—C8—Fe170.44 (17)
C2—Fe1—C8105.44 (17)C7—C8—H8126.0
C7—Fe1—C840.51 (17)C9—C8—H8126.0
C2—Fe1—C141.1 (2)Fe1—C8—H8125.5
C7—Fe1—C1152.75 (16)C8—C9—C10108.9 (3)
C8—Fe1—C1119.25 (16)C8—C9—Fe169.0 (2)
C2—Fe1—C340.2 (2)C10—C9—Fe171.56 (16)
C7—Fe1—C3105.88 (16)C8—C9—H9125.6
C8—Fe1—C3123.77 (17)C10—C9—H9125.6
C1—Fe1—C368.09 (18)Fe1—C9—H9125.5
C2—Fe1—C6152.3 (2)C9—C10—C6106.2 (3)
C7—Fe1—C640.37 (13)C9—C10—C11129.2 (3)
C8—Fe1—C667.88 (15)C6—C10—C11123.7 (3)
C1—Fe1—C6165.74 (15)C9—C10—Fe168.42 (16)
C3—Fe1—C6119.67 (18)C6—C10—Fe168.01 (16)
C2—Fe1—C566.99 (17)C11—C10—Fe1136.15 (19)
C7—Fe1—C5163.85 (17)C10—C11—C17111.7 (2)
C8—Fe1—C5155.61 (17)C10—C11—C12109.2 (2)
C1—Fe1—C539.73 (13)C17—C11—C12112.6 (2)
C3—Fe1—C566.36 (15)C10—C11—C18106.0 (2)
C6—Fe1—C5129.60 (14)C17—C11—C18108.7 (2)
C2—Fe1—C9125.7 (2)C12—C11—C18108.3 (2)
C7—Fe1—C968.04 (15)C13—C12—C11118.7 (3)
C8—Fe1—C940.58 (15)C13—C12—H12A107.6
C1—Fe1—C9108.93 (15)C11—C12—H12A107.6
C3—Fe1—C9161.72 (17)C13—C12—H12B107.6
C6—Fe1—C967.65 (13)C11—C12—H12B107.6
C5—Fe1—C9123.70 (14)H12A—C12—H12B107.1
C2—Fe1—C466.7 (2)C14—C13—C12113.9 (3)
C7—Fe1—C4125.64 (16)C14—C13—H13A108.8
C8—Fe1—C4160.80 (16)C12—C13—H13A108.8
C1—Fe1—C467.29 (15)C14—C13—H13B108.8
C3—Fe1—C439.09 (16)C12—C13—H13B108.8
C6—Fe1—C4110.34 (14)H13A—C13—H13B107.7
C5—Fe1—C439.58 (14)C15—C14—C13114.9 (3)
C9—Fe1—C4158.07 (14)C15—C14—H14A108.6
C2—Fe1—C10164.0 (3)C13—C14—H14A108.6
C7—Fe1—C1068.11 (12)C15—C14—H14B108.6
C8—Fe1—C1067.94 (12)C13—C14—H14B108.6
C1—Fe1—C10128.09 (15)H14A—C14—H14B107.5
C3—Fe1—C10155.59 (18)C14—C15—C16115.8 (3)
C6—Fe1—C1040.50 (12)C14—C15—H15A108.3
C5—Fe1—C10112.66 (12)C16—C15—H15A108.3
C9—Fe1—C1040.02 (11)C14—C15—H15B108.3
C4—Fe1—C10124.06 (14)C16—C15—H15B108.3
C5—C1—C2105.9 (4)H15A—C15—H15B107.4
C5—C1—Fe170.48 (19)C15—C16—C17114.8 (3)
C2—C1—Fe168.9 (2)C15—C16—H16A108.6
C5—C1—H1127.1C17—C16—H16A108.6
C2—C1—H1127.1C15—C16—H16B108.6
Fe1—C1—H1125.1C17—C16—H16B108.6
C3—C2—C1107.9 (3)H16A—C16—H16B107.6
C3—C2—Fe170.6 (2)C16—C17—C11117.4 (2)
C1—C2—Fe169.9 (2)C16—C17—H17A108.0
C3—C2—H2126.0C11—C17—H17A108.0
C1—C2—H2126.0C16—C17—H17B108.0
Fe1—C2—H2125.0C11—C17—H17B108.0
C4—C3—C2108.3 (4)H17A—C17—H17B107.2
C4—C3—Fe171.1 (2)C26—C18—C19101.2 (3)
C2—C3—Fe169.2 (2)C26—C18—C11116.3 (2)
C4—C3—H3125.8C19—C18—C11114.9 (2)
C2—C3—H3125.8C26—C18—H18108.0
Fe1—C3—H3125.5C19—C18—H18108.0
C3—C4—C5108.2 (4)C11—C18—H18108.0
C3—C4—Fe169.9 (2)C20—C19—C18111.4 (3)
C5—C4—Fe169.76 (19)C20—C19—H19124.3
C3—C4—H4125.9C18—C19—H19124.3
C5—C4—H4125.9C19—C20—C21110.6 (3)
Fe1—C4—H4126.1C19—C20—H20124.7
C1—C5—C4109.6 (3)C21—C20—H20124.7
C1—C5—Fe169.79 (18)C22—C21—C26119.4 (4)
C4—C5—Fe170.66 (19)C22—C21—C20132.7 (4)
C1—C5—H5125.2C26—C21—C20107.8 (3)
C4—C5—H5125.2C23—C22—C21119.5 (4)
Fe1—C5—H5125.9C23—C22—H22120.2
C7—C6—C10108.8 (3)C21—C22—H22120.2
C7—C6—Fe169.24 (18)C22—C23—C24121.1 (4)
C10—C6—Fe171.49 (17)C22—C23—H23119.4
C7—C6—H6125.6C24—C23—H23119.4
C10—C6—H6125.6C23—C24—C25121.1 (4)
Fe1—C6—H6125.3C23—C24—H24119.4
C8—C7—C6108.0 (3)C25—C24—H24119.4
C8—C7—Fe169.78 (19)C24—C25—C26118.9 (3)
C6—C7—Fe170.39 (17)C24—C25—H25120.6
C8—C7—H7126.0C26—C25—H25120.6
C6—C7—H7126.0C25—C26—C21119.8 (3)
Fe1—C7—H7125.4C25—C26—C18131.3 (3)
C7—C8—C9108.0 (3)C21—C26—C18108.9 (3)
C7—C8—Fe169.7 (2)
C2—Fe1—C1—C5116.6 (4)C3—Fe1—C7—C6117.4 (3)
C7—Fe1—C1—C5161.1 (3)C5—Fe1—C7—C658.5 (6)
C8—Fe1—C1—C5163.6 (2)C9—Fe1—C7—C680.9 (2)
C3—Fe1—C1—C578.9 (3)C4—Fe1—C7—C679.5 (3)
C6—Fe1—C1—C546.8 (7)C10—Fe1—C7—C637.6 (2)
C9—Fe1—C1—C5120.3 (2)C6—C7—C8—C90.0 (4)
C4—Fe1—C1—C536.5 (2)Fe1—C7—C8—C960.3 (2)
C10—Fe1—C1—C579.8 (2)C6—C7—C8—Fe160.2 (2)
C7—Fe1—C1—C244.5 (5)C2—Fe1—C8—C7113.7 (3)
C8—Fe1—C1—C279.8 (3)C1—Fe1—C8—C7155.9 (2)
C3—Fe1—C1—C237.7 (3)C3—Fe1—C8—C774.0 (3)
C6—Fe1—C1—C2163.4 (6)C6—Fe1—C8—C737.79 (19)
C5—Fe1—C1—C2116.6 (4)C5—Fe1—C8—C7178.1 (3)
C9—Fe1—C1—C2123.1 (3)C9—Fe1—C8—C7118.8 (3)
C4—Fe1—C1—C280.1 (3)C4—Fe1—C8—C750.7 (6)
C10—Fe1—C1—C2163.6 (3)C10—Fe1—C8—C781.7 (2)
C5—C1—C2—C30.5 (4)C2—Fe1—C8—C9127.5 (3)
Fe1—C1—C2—C360.7 (2)C7—Fe1—C8—C9118.8 (3)
C5—C1—C2—Fe161.2 (2)C1—Fe1—C8—C985.3 (2)
C7—Fe1—C2—C382.6 (3)C3—Fe1—C8—C9167.2 (2)
C8—Fe1—C2—C3124.5 (3)C6—Fe1—C8—C981.0 (2)
C1—Fe1—C2—C3118.5 (3)C5—Fe1—C8—C959.4 (4)
C6—Fe1—C2—C352.8 (4)C4—Fe1—C8—C9169.5 (4)
C5—Fe1—C2—C380.1 (3)C10—Fe1—C8—C937.13 (19)
C9—Fe1—C2—C3164.0 (2)C7—C8—C9—C100.9 (4)
C4—Fe1—C2—C336.9 (2)Fe1—C8—C9—C1060.7 (2)
C10—Fe1—C2—C3172.2 (5)C7—C8—C9—Fe159.8 (2)
C7—Fe1—C2—C1158.9 (2)C2—Fe1—C9—C870.4 (3)
C8—Fe1—C2—C1117.0 (3)C7—Fe1—C9—C837.9 (2)
C3—Fe1—C2—C1118.5 (3)C1—Fe1—C9—C8113.2 (3)
C6—Fe1—C2—C1171.3 (3)C3—Fe1—C9—C835.9 (6)
C5—Fe1—C2—C138.4 (2)C6—Fe1—C9—C881.6 (2)
C9—Fe1—C2—C177.5 (3)C5—Fe1—C9—C8154.7 (2)
C4—Fe1—C2—C181.6 (2)C4—Fe1—C9—C8170.8 (4)
C10—Fe1—C2—C153.8 (7)C10—Fe1—C9—C8119.5 (3)
C1—C2—C3—C40.3 (4)C2—Fe1—C9—C10170.1 (3)
Fe1—C2—C3—C460.6 (3)C7—Fe1—C9—C1081.7 (2)
C1—C2—C3—Fe160.2 (2)C8—Fe1—C9—C10119.5 (3)
C2—Fe1—C3—C4119.1 (4)C1—Fe1—C9—C10127.3 (2)
C7—Fe1—C3—C4127.6 (3)C3—Fe1—C9—C10155.4 (5)
C8—Fe1—C3—C4168.1 (2)C6—Fe1—C9—C1037.91 (18)
C1—Fe1—C3—C480.5 (3)C5—Fe1—C9—C1085.7 (2)
C6—Fe1—C3—C486.2 (3)C4—Fe1—C9—C1051.2 (4)
C5—Fe1—C3—C437.3 (2)C8—C9—C10—C61.4 (3)
C9—Fe1—C3—C4164.6 (4)Fe1—C9—C10—C657.7 (2)
C10—Fe1—C3—C455.8 (4)C8—C9—C10—C11168.2 (3)
C7—Fe1—C3—C2113.3 (3)Fe1—C9—C10—C11132.7 (3)
C8—Fe1—C3—C272.8 (3)C8—C9—C10—Fe159.1 (2)
C1—Fe1—C3—C238.6 (3)C7—C6—C10—C91.5 (3)
C6—Fe1—C3—C2154.7 (3)Fe1—C6—C10—C957.9 (2)
C5—Fe1—C3—C281.8 (3)C7—C6—C10—C11168.9 (2)
C9—Fe1—C3—C245.5 (6)Fe1—C6—C10—C11131.7 (3)
C4—Fe1—C3—C2119.1 (4)C7—C6—C10—Fe159.4 (2)
C10—Fe1—C3—C2174.8 (4)C2—Fe1—C10—C930.6 (7)
C2—C3—C4—C50.0 (4)C7—Fe1—C10—C981.5 (2)
Fe1—C3—C4—C559.4 (2)C8—Fe1—C10—C937.6 (2)
C2—C3—C4—Fe159.4 (3)C1—Fe1—C10—C973.0 (2)
C2—Fe1—C4—C337.9 (3)C3—Fe1—C10—C9161.6 (3)
C7—Fe1—C4—C369.6 (3)C6—Fe1—C10—C9118.9 (3)
C8—Fe1—C4—C331.4 (6)C5—Fe1—C10—C9116.0 (2)
C1—Fe1—C4—C382.7 (3)C4—Fe1—C10—C9159.4 (2)
C6—Fe1—C4—C3112.4 (3)C2—Fe1—C10—C6149.5 (6)
C5—Fe1—C4—C3119.4 (4)C7—Fe1—C10—C637.5 (2)
C9—Fe1—C4—C3167.1 (4)C8—Fe1—C10—C681.3 (2)
C10—Fe1—C4—C3155.6 (3)C1—Fe1—C10—C6168.1 (2)
C2—Fe1—C4—C581.5 (3)C3—Fe1—C10—C642.6 (4)
C7—Fe1—C4—C5171.0 (2)C5—Fe1—C10—C6125.1 (2)
C8—Fe1—C4—C5150.8 (4)C9—Fe1—C10—C6118.9 (3)
C1—Fe1—C4—C536.7 (2)C4—Fe1—C10—C681.6 (2)
C3—Fe1—C4—C5119.4 (4)C2—Fe1—C10—C1194.1 (7)
C6—Fe1—C4—C5128.2 (2)C7—Fe1—C10—C11153.8 (3)
C9—Fe1—C4—C547.7 (5)C8—Fe1—C10—C11162.3 (3)
C10—Fe1—C4—C585.0 (2)C1—Fe1—C10—C1151.7 (3)
C2—C1—C5—C40.5 (4)C3—Fe1—C10—C1173.7 (5)
Fe1—C1—C5—C459.6 (2)C6—Fe1—C10—C11116.4 (3)
C2—C1—C5—Fe160.2 (2)C5—Fe1—C10—C118.7 (3)
C3—C4—C5—C10.3 (4)C9—Fe1—C10—C11124.7 (3)
Fe1—C4—C5—C159.1 (2)C4—Fe1—C10—C1134.7 (3)
C3—C4—C5—Fe159.5 (2)C9—C10—C11—C1715.3 (4)
C2—Fe1—C5—C139.7 (3)C6—C10—C11—C17176.7 (3)
C7—Fe1—C5—C1147.7 (5)Fe1—C10—C11—C1784.2 (3)
C8—Fe1—C5—C136.6 (4)C9—C10—C11—C12140.5 (3)
C3—Fe1—C5—C183.6 (3)C6—C10—C11—C1251.5 (4)
C6—Fe1—C5—C1166.5 (2)Fe1—C10—C11—C1241.1 (4)
C9—Fe1—C5—C178.9 (3)C9—C10—C11—C18103.0 (3)
C4—Fe1—C5—C1120.5 (3)C6—C10—C11—C1865.0 (3)
C10—Fe1—C5—C1122.9 (2)Fe1—C10—C11—C18157.6 (2)
C2—Fe1—C5—C480.8 (3)C10—C11—C12—C13152.1 (3)
C7—Fe1—C5—C427.2 (6)C17—C11—C12—C1327.4 (4)
C8—Fe1—C5—C4157.1 (3)C18—C11—C12—C1392.9 (3)
C1—Fe1—C5—C4120.5 (3)C11—C12—C13—C1483.0 (4)
C3—Fe1—C5—C436.8 (3)C12—C13—C14—C1575.5 (4)
C6—Fe1—C5—C473.0 (3)C13—C14—C15—C1655.7 (5)
C9—Fe1—C5—C4160.6 (2)C14—C15—C16—C1767.7 (4)
C10—Fe1—C5—C4116.6 (2)C15—C16—C17—C1187.9 (3)
C2—Fe1—C6—C743.1 (5)C10—C11—C17—C1675.4 (3)
C8—Fe1—C6—C737.9 (2)C12—C11—C17—C1647.9 (3)
C1—Fe1—C6—C7160.7 (6)C18—C11—C17—C16168.0 (2)
C3—Fe1—C6—C779.4 (3)C10—C11—C18—C2670.9 (3)
C5—Fe1—C6—C7162.1 (2)C17—C11—C18—C2649.3 (3)
C9—Fe1—C6—C781.9 (2)C12—C11—C18—C26172.0 (2)
C4—Fe1—C6—C7121.6 (2)C10—C11—C18—C19171.1 (3)
C10—Fe1—C6—C7119.4 (3)C17—C11—C18—C1968.7 (3)
C2—Fe1—C6—C10162.5 (4)C12—C11—C18—C1954.0 (3)
C7—Fe1—C6—C10119.4 (3)C26—C18—C19—C201.6 (4)
C8—Fe1—C6—C1081.5 (2)C11—C18—C19—C20124.6 (3)
C1—Fe1—C6—C1041.4 (7)C18—C19—C20—C210.0 (5)
C3—Fe1—C6—C10161.2 (2)C19—C20—C21—C22179.0 (4)
C5—Fe1—C6—C1078.5 (2)C19—C20—C21—C261.7 (5)
C9—Fe1—C6—C1037.47 (18)C26—C21—C22—C232.1 (6)
C4—Fe1—C6—C10119.1 (2)C20—C21—C22—C23177.2 (4)
C10—C6—C7—C80.9 (4)C21—C22—C23—C240.3 (6)
Fe1—C6—C7—C859.9 (2)C22—C23—C24—C250.2 (6)
C10—C6—C7—Fe160.8 (2)C23—C24—C25—C261.1 (5)
C2—Fe1—C7—C882.1 (3)C24—C25—C26—C213.0 (4)
C1—Fe1—C7—C851.0 (4)C24—C25—C26—C18178.8 (3)
C3—Fe1—C7—C8123.8 (3)C22—C21—C26—C253.5 (5)
C6—Fe1—C7—C8118.8 (3)C20—C21—C26—C25176.0 (3)
C5—Fe1—C7—C8177.3 (4)C22—C21—C26—C18177.9 (3)
C9—Fe1—C7—C837.9 (2)C20—C21—C26—C182.7 (4)
C4—Fe1—C7—C8161.7 (2)C19—C18—C26—C25175.9 (3)
C10—Fe1—C7—C881.2 (2)C11—C18—C26—C2558.9 (4)
C2—Fe1—C7—C6159.1 (3)C19—C18—C26—C212.5 (3)
C8—Fe1—C7—C6118.8 (3)C11—C18—C26—C21122.7 (3)
C1—Fe1—C7—C6169.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg1i0.932.763.689 (4)173
C17—H17B···Cg30.972.672.987 (3)100
C20—H20···Cg4ii0.932.873.618 (5)138
C25—H25···Cg20.932.803.540 (4)137
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x, y, z1/2.

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C21H23)]
Mr396.33
Crystal system, space groupMonoclinic, Cc
Temperature (K)294
a, b, c (Å)6.2777 (16), 34.562 (9), 9.321 (2)
β (°) 90.443 (4)
V3)2022.3 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.75
Crystal size (mm)0.26 × 0.24 × 0.22
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.736, 0.847
No. of measured, independent and
observed [I > 2σ(I)] reflections
5671, 3703, 3102
Rint0.022
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.080, 1.00
No. of reflections3703
No. of parameters244
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.24
Absolute structureFlack (1983), 1633 Friedel pairs
Absolute structure parameter0.01 (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—C12.042 (3)Fe1—C62.048 (3)
Fe1—C22.029 (3)Fe1—C72.033 (3)
Fe1—C32.048 (4)Fe1—C82.034 (3)
Fe1—C42.063 (3)Fe1—C92.053 (3)
Fe1—C52.051 (3)Fe1—C102.095 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg1i0.932.763.689 (4)173
C17—H17B···Cg30.972.672.987 (3)100
C20—H20···Cg4ii0.932.873.618 (5)138
C25—H25···Cg20.932.803.540 (4)137
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x, y, z1/2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds