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Acta Cryst. (2008). E64, m444-m445    [ doi:10.1107/S1600536808003218 ]

1,4-Diferrocenylbutane-1,4-dione

M. Tombul, A. Bulut, K. Güven and O. Büyükgüngör

Abstract top

In the crystal structure of the title compound, [Fe2(C5H5)2(C14H12O2)], each carbonyl group is coplanar with the adjacent cyclopentadienyl ring, thus maximizing the [pi]-orbital overlap and electronic interactions between the groups. In the crystal structure, there are inter- and intramolecular C-H...O contacts.

Comment top

Since its first discovery in 1951 (Kealy & Pauson, 1951), particular attention has been paid to ferrocene and its derivatives owing to their unique structural, spectroscopic and electrochemical properties. In recent years, a number of extensive studies has been conducted on ferrocene containing compounds and polymers, and particularly compounds exhibiting multiple ferrocene groups with the opportunity for producing mixed-valent states due to their potential use in chemical and biochemical sensors (Navarro et al., 2005; Brown et al., 2005; Okochi et al., 2005; Hickman et al., 1991), as redox active catalysts (Togni & Hayashi, 1995; Sawamura & Ito, 1992; Nicolosi et al., 1994), because of their application in molecular magnets (Miller et al., 1988), and for use in self-assembled monolayer chemistry (Chidsey et al., 1990; Creager & Rowe, 1997). Such monolayers containing covalently connected ferrocene groups have been reported to be prepared in mixed-valent, fully oxidized or fully reduced states (Pugh et al., 2006). Hence, in order to increase their potential for the aforementioned applications, the chemical properties of the monolayers can be controlled via application of the appropriate voltage. Due to the electron transfer of ferrocene being generally chemically and electrochemically reversible and occurring via an outer-sphere redox mechanism, ferrocene derivatives are not only perfect candidates to be incorporated into technological devices, but also ideal molecules for the study of interfacial electron and charge transfer. We report here the single-crystal structure of the title compound (I).

The molecular structure of (I), is shown in Fig. 1. Succinylferrocene crystallizes in the orthorhombic space group Pca21 with one molecule in the asymmetric unit. The ferrocene groups themselves are in the eclipsed conformation and the bond lengths and angles associated with the ferrocene groups are as expected. Two ferrocenyl groups are almost trans to each other. The average values of the C—Cg1—Cg2—C and C—Cg3—Cg4—C (Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1—C5, C6—C10, C15—C19 and C20—C24 rings, respectively) pseuodo-torsion angles are 5.50 (2)° and 7.13 (2)° respectively. The Fe1–Cg1, Fe1–Cg2, Fe2–Cg3 and Fe2–Cg4 distances are 1.635 (2) Å, 1.649 (2) Å, 1.645 (3)Å and 1.647 (2) Å, respectively, with Cg1–Fe1–Cg2 and Cg3–Fe2–Cg4 angles of 179.54 (10)° and 178.65 (11)°. Within the molecule, the carbonyl substituents are almost coplanar with the plane of the adjacent Cp rings (r.m.s. deviations = 0.0278 (2) Å and 0.0559 (2) Å; Cp versus. C=O dihedral angles: 7.42 (6)° and 13.74 (5)° respectively), therefore maximizing the π-orbital overlap and electronic interactions between the groups. In (I), the intermolecular bond lengths and angles are unexceptional; the central C—C distance, 1.492 (6) Å, is close to the value found in 1,6-diferrocenylhexane-1,6-dione, 1.506 (5) Å (Pugh et al., 2006). The space between the ferrocene units is nearly close packed and the ferrocene moieties are closer to each other in the solid state (7.903 (21) Å which is the distance between Fe1 and Fe2) than they would be on average in solution.

In the crystal structure, weak inter and intramolecular C—H···O hydrogen bonding interactions link molecules (Table 1, Fig. 2) and may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Brown et al. (2005); Chidsey et al. (1990); Creager & Rowe (1997); Gemici (2005); Hickman et al. (1991); Kealy & Pauson (1951); Miller et al. (1988); Navarro et al. (2005); Nicolosi et al. (1994); Okochi et al. (2005); Pugh et al. (2006); Sawamura & Ito (1992); Togni & Hayashi (1995).

Experimental top

The title compound (I) was prepared by employing Alkyl Lewis acid, EtAlCl2 (Gemici, 2005). To a CH2Cl2 solution (10 ml) containing ferrocene (1.27 g, 6.8 mmol), EtAlCl2 (6.8 ml; 1.0 M in hexane) was added dropwise at 273 K under nitrogen. The resulting mixture was stirred at 273 K for 1,5 h. The solution was then extracted with portions of CH2Cl2 (3 times; in total 75 ml), dried over Na2SO4 and evaporated to dryness. Final purification was achieved by flash chromatography on silica gel utilizing CHCl3 as the eluant. The product was obtained in 76% yield. 1H-NMR (400 MHz, CHCl3, δ, p.p.m.): 3.05 (broad m, 4H, COCH2CH2CO), 4.20 (s, 10H, 2xC5H5), 4.40 (broad s, 4H, C5H4), 4.76 (broad s, 4H, C5H4). X-ray quality single crystals of (I) were prepared via solvent evaporation from hexane/ethyl acetate solutions to give reddish platelets.

Refinement top

The H atoms were all located in a difference map, but they were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H = 0.93 and 0.97 Å) and Uiso(H) = 1.2 times Ueq of the parent atom, after which the positions were refined with riding constraints.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Showing the atom-labelling scheme of (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The packing diagram and the intermolecular C—H···O hydrogen bonding interactions of (I), viewed down the a axis. For clarity, H atoms not involved in hydrogen bonding have been omitted.
1,4-Diferrocenylbutane-1,4-dione top
Crystal data top
[Fe2(C5H5)2(C14H12O2)]F000 = 936
Mr = 454.12Dx = 1.562 Mg m−3
Orthorhombic, Pca21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 17802 reflections
a = 10.4175 (7) Åθ = 2.0–27.3º
b = 18.5954 (10) ŵ = 1.52 mm−1
c = 9.9690 (6) ÅT = 298 (2) K
V = 1931.2 (2) Å3Prismatic stick, red
Z = 40.45 × 0.33 × 0.08 mm
Data collection top
Stoe IPDS 2
diffractometer		3612 independent reflections
Monochromator: plane graphite2941 reflections with I > 2u(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.038
T = 298(2) Kθmax = 26.8º
ω scansθmin = 2.0º
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		h = −13→13
Tmin = 0.525, Tmax = 0.899k = −20→23
11622 measured reflectionsl = −12→12
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.036  w = 1/[σ2(Fo2) + (0.0398P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.075(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.37 e Å−3
3612 reflectionsΔρmin = −0.22 e Å−3
254 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 1418 Freidel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (2)
Secondary atom site location: difference Fourier map
Crystal data top
[Fe2(C5H5)2(C14H12O2)]V = 1931.2 (2) Å3
Mr = 454.12Z = 4
Orthorhombic, Pca21Mo Kα
a = 10.4175 (7) ŵ = 1.52 mm−1
b = 18.5954 (10) ÅT = 298 (2) K
c = 9.9690 (6) Å0.45 × 0.33 × 0.08 mm
Data collection top
Stoe IPDS 2
diffractometer		3612 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		2941 reflections with I > 2u(I)
Tmin = 0.525, Tmax = 0.899Rint = 0.038
11622 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters not refined
wR(F2) = 0.075Δρmax = 0.37 e Å−3
S = 1.01Δρmin = −0.22 e Å−3
3612 reflectionsAbsolute structure: Flack (1983), 1418 Freidel pairs
254 parametersFlack parameter: 0.01 (2)
1 restraint
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
C10.3828 (4)0.9008 (2)0.2532 (4)0.0488 (9)
C20.3776 (3)0.9545 (2)0.1526 (5)0.0557 (10)
H20.31450.95900.08710.067*
C30.4842 (4)1.0000 (2)0.1689 (5)0.0601 (13)
H30.50371.03980.11610.072*
C40.5553 (4)0.9756 (2)0.2773 (5)0.0642 (11)
H40.63020.99650.31000.077*
C50.4951 (4)0.9137 (2)0.3299 (5)0.0553 (10)
H50.52390.88630.40190.066*
C60.5458 (4)0.8510 (3)−0.0499 (5)0.0676 (12)
H60.48500.8567−0.11740.081*
C70.6536 (5)0.8933 (3)−0.0304 (6)0.0758 (14)
H70.67690.9327−0.08260.091*
C80.7222 (4)0.8674 (3)0.0808 (6)0.0798 (17)
H80.79800.88620.11550.096*
C90.6542 (4)0.8078 (3)0.1296 (7)0.0794 (14)
H90.67830.77960.20250.095*
C100.5444 (4)0.7974 (3)0.0512 (5)0.0696 (13)
H100.48220.76210.06310.083*
C110.2960 (4)0.8382 (2)0.2666 (4)0.0505 (9)
C120.3305 (4)0.7823 (2)0.3686 (4)0.0568 (10)
H12A0.41630.76510.34900.068*
H12B0.33320.80510.45610.068*
C130.2431 (5)0.7189 (2)0.3771 (4)0.0567 (9)
H13A0.15530.73590.37160.068*
H13B0.25400.69670.46440.068*
C140.2621 (4)0.6621 (2)0.2717 (4)0.0517 (9)
C150.1743 (4)0.5999 (2)0.2724 (4)0.0502 (9)
C160.1563 (4)0.5503 (2)0.1648 (4)0.0587 (12)
H160.20170.54960.08440.070*
C170.0573 (4)0.5024 (2)0.2023 (5)0.0656 (11)
H170.02620.46460.15060.079*
C180.0139 (4)0.5214 (2)0.3300 (5)0.0662 (12)
H18−0.05070.49830.37770.079*
C190.0845 (4)0.5817 (2)0.3745 (4)0.0571 (10)
H190.07420.60520.45610.069*
C20−0.1607 (5)0.6109 (3)0.0730 (5)0.0652 (13)
H20−0.19360.57290.02310.078*
C21−0.1998 (4)0.6299 (3)0.2023 (6)0.0654 (11)
H21−0.26280.60720.25320.078*
C22−0.1253 (4)0.6901 (3)0.2414 (6)0.0710 (15)
H22−0.13070.71400.32320.085*
C23−0.0425 (4)0.7074 (2)0.1362 (6)0.0691 (12)
H230.01670.74490.13550.083*
C24−0.0647 (4)0.6579 (3)0.0306 (5)0.0671 (12)
H24−0.02280.6569−0.05180.081*
O10.1985 (2)0.83401 (17)0.1994 (3)0.0669 (7)
O20.3494 (2)0.66641 (17)0.1891 (3)0.0680 (8)
Fe10.54062 (5)0.89622 (3)0.13663 (6)0.04646 (14)
Fe2−0.00932 (5)0.60553 (3)0.20155 (6)0.04697 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.052 (2)0.047 (2)0.047 (2)0.0039 (18)0.0009 (17)−0.002 (2)
C20.054 (2)0.058 (3)0.055 (3)0.0143 (17)0.0015 (18)0.004 (2)
C30.071 (2)0.049 (2)0.060 (4)0.0085 (18)0.0098 (19)0.003 (2)
C40.075 (3)0.053 (3)0.064 (3)−0.012 (2)−0.002 (2)−0.009 (2)
C50.070 (2)0.050 (2)0.046 (2)−0.0058 (19)−0.0101 (18)−0.0018 (19)
C60.068 (3)0.077 (3)0.057 (3)−0.001 (2)0.007 (2)−0.015 (3)
C70.070 (3)0.072 (3)0.085 (4)−0.004 (3)0.031 (3)−0.004 (3)
C80.044 (2)0.081 (4)0.114 (5)−0.001 (2)0.008 (2)−0.023 (3)
C90.072 (3)0.069 (3)0.097 (4)0.032 (2)−0.010 (3)−0.011 (4)
C100.071 (3)0.063 (3)0.074 (3)−0.005 (2)0.011 (2)−0.020 (3)
C110.055 (2)0.056 (2)0.0403 (19)0.0052 (18)0.0055 (18)−0.002 (2)
C120.074 (3)0.055 (3)0.042 (2)−0.007 (2)−0.0032 (17)0.000 (2)
C130.075 (2)0.059 (2)0.0362 (19)−0.007 (2)0.0026 (16)−0.001 (2)
C140.058 (2)0.055 (2)0.042 (2)0.0067 (18)−0.0024 (18)0.008 (2)
C150.061 (2)0.047 (2)0.043 (2)0.0057 (18)−0.0036 (18)0.006 (2)
C160.065 (2)0.053 (2)0.058 (4)0.0120 (17)0.0003 (17)−0.007 (2)
C170.084 (3)0.042 (2)0.071 (3)0.0021 (18)−0.015 (3)−0.003 (3)
C180.077 (3)0.057 (3)0.065 (3)−0.011 (2)−0.010 (2)0.019 (2)
C190.075 (3)0.052 (2)0.044 (2)−0.003 (2)−0.0067 (19)0.008 (2)
C200.077 (3)0.056 (3)0.063 (3)−0.007 (2)−0.020 (2)0.002 (3)
C210.050 (2)0.070 (3)0.076 (3)−0.0053 (18)0.000 (3)−0.001 (3)
C220.062 (2)0.060 (3)0.091 (4)0.017 (2)−0.015 (2)−0.019 (3)
C230.063 (2)0.045 (2)0.099 (3)−0.0026 (19)−0.030 (3)0.011 (3)
C240.062 (2)0.073 (3)0.066 (3)−0.008 (2)−0.009 (2)0.022 (3)
O10.0594 (15)0.080 (2)0.0610 (16)−0.0037 (13)−0.0077 (16)0.0057 (19)
O20.0693 (16)0.078 (2)0.0571 (18)0.0002 (14)0.0090 (15)−0.0070 (17)
Fe10.0457 (3)0.0446 (3)0.0491 (3)0.0020 (2)−0.0029 (3)−0.0021 (4)
Fe20.0525 (3)0.0418 (3)0.0466 (3)−0.0013 (2)−0.0022 (2)0.0020 (4)
Geometric parameters (Å, °) top
C1—C21.417 (6)C13—C141.503 (6)
C1—C51.418 (6)C13—H13A0.9700
C1—C111.480 (6)C13—H13B0.9700
C1—Fe12.015 (4)C14—O21.229 (4)
C2—C31.406 (6)C14—C151.475 (6)
C2—Fe12.022 (3)C15—C191.423 (6)
C2—H20.9300C15—C161.427 (6)
C3—C41.387 (6)C15—Fe22.042 (4)
C3—Fe12.044 (4)C16—C171.413 (6)
C3—H30.9300C16—Fe22.042 (4)
C4—C51.411 (6)C16—H160.9300
C4—Fe12.042 (4)C17—C181.396 (7)
C4—H40.9300C17—Fe22.039 (4)
C5—Fe12.011 (5)C17—H170.9300
C5—H50.9300C18—C191.412 (6)
C6—C71.386 (7)C18—Fe22.035 (4)
C6—C101.417 (7)C18—H180.9300
C6—Fe12.041 (5)C19—Fe22.032 (4)
C6—H60.9300C19—H190.9300
C7—C81.404 (8)C20—C241.394 (6)
C7—Fe12.040 (5)C20—C211.397 (7)
C7—H70.9300C20—Fe22.034 (5)
C8—C91.404 (7)C20—H200.9300
C8—Fe12.043 (4)C21—C221.417 (6)
C8—H80.9300C21—Fe22.035 (4)
C9—C101.399 (7)C21—H210.9300
C9—Fe12.027 (4)C22—C231.396 (7)
C9—H90.9300C22—Fe22.023 (4)
C10—Fe12.026 (5)C22—H220.9300
C10—H100.9300C23—C241.418 (7)
C11—O11.219 (5)C23—Fe22.033 (4)
C11—C121.499 (6)C23—H230.9300
C12—C131.492 (6)C24—Fe22.046 (4)
C12—H12A0.9700C24—H240.9300
C12—H12B0.9700
C2—C1—C5107.1 (4)C20—C21—C22107.1 (5)
C2—C1—C11126.5 (4)C20—C21—Fe269.9 (3)
C5—C1—C11126.0 (4)C22—C21—Fe269.1 (2)
C2—C1—Fe169.7 (2)C20—C21—H21126.5
C5—C1—Fe169.2 (2)C22—C21—H21126.5
C11—C1—Fe1121.2 (3)Fe2—C21—H21126.1
C3—C2—C1108.2 (4)C23—C22—C21108.3 (5)
C3—C2—Fe170.6 (2)C23—C22—Fe270.3 (2)
C1—C2—Fe169.2 (2)C21—C22—Fe270.0 (3)
C3—C2—H2125.9C23—C22—H22125.8
C1—C2—H2125.9C21—C22—H22125.8
Fe1—C2—H2125.9Fe2—C22—H22125.4
C4—C3—C2108.4 (4)C22—C23—C24107.9 (4)
C4—C3—Fe170.1 (2)C22—C23—Fe269.5 (3)
C2—C3—Fe168.9 (2)C24—C23—Fe270.1 (2)
C4—C3—H3125.8C22—C23—H23126.0
C2—C3—H3125.8C24—C23—H23126.0
Fe1—C3—H3126.7Fe2—C23—H23125.9
C3—C4—C5108.6 (4)C20—C24—C23107.4 (5)
C3—C4—Fe170.2 (3)C20—C24—Fe269.6 (3)
C5—C4—Fe168.4 (2)C23—C24—Fe269.2 (3)
C3—C4—H4125.7C20—C24—H24126.3
C5—C4—H4125.7C23—C24—H24126.3
Fe1—C4—H4127.2Fe2—C24—H24126.5
C4—C5—C1107.7 (4)C5—Fe1—C141.26 (16)
C4—C5—Fe170.8 (3)C5—Fe1—C268.88 (18)
C1—C5—Fe169.5 (2)C1—Fe1—C241.09 (17)
C4—C5—H5126.1C5—Fe1—C10123.65 (19)
C1—C5—H5126.1C1—Fe1—C10107.25 (18)
Fe1—C5—H5125.1C2—Fe1—C10122.41 (18)
C7—C6—C10108.0 (4)C5—Fe1—C9107.6 (2)
C7—C6—Fe170.1 (3)C1—Fe1—C9122.0 (2)
C10—C6—Fe169.0 (3)C2—Fe1—C9158.17 (19)
C7—C6—H6126.0C10—Fe1—C940.4 (2)
C10—C6—H6126.0C5—Fe1—C7157.3 (2)
Fe1—C6—H6126.5C1—Fe1—C7160.5 (2)
C6—C7—C8109.2 (5)C2—Fe1—C7124.3 (2)
C6—C7—Fe170.2 (3)C10—Fe1—C767.8 (2)
C8—C7—Fe170.0 (3)C9—Fe1—C767.3 (2)
C6—C7—H7125.4C5—Fe1—C6161.01 (18)
C8—C7—H7125.4C1—Fe1—C6124.33 (18)
Fe1—C7—H7125.9C2—Fe1—C6108.36 (19)
C9—C8—C7106.7 (5)C10—Fe1—C640.8 (2)
C9—C8—Fe169.2 (2)C9—Fe1—C667.6 (2)
C7—C8—Fe169.8 (3)C7—Fe1—C639.70 (19)
C9—C8—H8126.6C5—Fe1—C440.76 (17)
C7—C8—H8126.6C1—Fe1—C468.56 (17)
Fe1—C8—H8125.9C2—Fe1—C467.73 (19)
C10—C9—C8109.1 (5)C10—Fe1—C4160.6 (2)
C10—C9—Fe169.7 (2)C9—Fe1—C4124.5 (2)
C8—C9—Fe170.4 (3)C7—Fe1—C4122.4 (2)
C10—C9—H9125.4C6—Fe1—C4157.16 (19)
C8—C9—H9125.4C5—Fe1—C8121.4 (2)
Fe1—C9—H9126.0C1—Fe1—C8157.5 (2)
C9—C10—C6107.0 (4)C2—Fe1—C8160.0 (2)
C9—C10—Fe169.9 (3)C10—Fe1—C868.29 (19)
C6—C10—Fe170.2 (3)C9—Fe1—C840.3 (2)
C9—C10—H10126.5C7—Fe1—C840.2 (2)
C6—C10—H10126.5C6—Fe1—C867.6 (2)
Fe1—C10—H10125.0C4—Fe1—C8107.9 (2)
O1—C11—C1120.7 (4)C5—Fe1—C368.19 (18)
O1—C11—C12121.9 (4)C1—Fe1—C368.56 (17)
C1—C11—C12117.4 (3)C2—Fe1—C340.46 (16)
C13—C12—C11116.2 (4)C10—Fe1—C3158.24 (19)
C13—C12—H12A108.2C9—Fe1—C3160.00 (18)
C11—C12—H12A108.2C7—Fe1—C3108.6 (2)
C13—C12—H12B108.2C6—Fe1—C3122.7 (2)
C11—C12—H12B108.2C4—Fe1—C339.69 (18)
H12A—C12—H12B107.4C8—Fe1—C3123.8 (2)
C12—C13—C14115.8 (4)C22—Fe2—C19106.9 (2)
C12—C13—H13A108.3C22—Fe2—C2340.3 (2)
C14—C13—H13A108.3C19—Fe2—C23123.9 (2)
C12—C13—H13B108.3C22—Fe2—C2067.8 (2)
C14—C13—H13B108.3C19—Fe2—C20156.70 (19)
H13A—C13—H13B107.4C23—Fe2—C2067.71 (18)
O2—C14—C15120.9 (4)C22—Fe2—C2140.87 (18)
O2—C14—C13121.3 (4)C19—Fe2—C21121.0 (2)
C15—C14—C13117.8 (4)C23—Fe2—C2168.17 (19)
C19—C15—C16107.4 (4)C20—Fe2—C2140.2 (2)
C19—C15—C14126.7 (4)C22—Fe2—C18123.0 (2)
C16—C15—C14125.8 (4)C19—Fe2—C1840.62 (17)
C19—C15—Fe269.2 (2)C23—Fe2—C18159.7 (2)
C16—C15—Fe269.5 (2)C20—Fe2—C18121.74 (19)
C14—C15—Fe2122.6 (3)C21—Fe2—C18106.5 (2)
C17—C16—C15107.7 (4)C22—Fe2—C17159.0 (2)
C17—C16—Fe269.6 (2)C19—Fe2—C1768.14 (19)
C15—C16—Fe269.5 (2)C23—Fe2—C17159.3 (2)
C17—C16—H16126.2C20—Fe2—C17108.2 (2)
C15—C16—H16126.2C21—Fe2—C17122.74 (18)
Fe2—C16—H16126.2C18—Fe2—C1740.1 (2)
C18—C17—C16108.6 (4)C22—Fe2—C15122.14 (18)
C18—C17—Fe269.8 (3)C19—Fe2—C1540.91 (17)
C16—C17—Fe269.9 (2)C23—Fe2—C15108.56 (16)
C18—C17—H17125.7C20—Fe2—C15161.2 (2)
C16—C17—H17125.7C21—Fe2—C15157.4 (2)
Fe2—C17—H17126.2C18—Fe2—C1568.36 (17)
C17—C18—C19108.6 (4)C17—Fe2—C1568.37 (16)
C17—C18—Fe270.1 (3)C22—Fe2—C16158.68 (19)
C19—C18—Fe269.5 (2)C19—Fe2—C1668.64 (17)
C17—C18—H18125.7C23—Fe2—C16123.7 (2)
C19—C18—H18125.7C20—Fe2—C16124.5 (2)
Fe2—C18—H18126.3C21—Fe2—C16159.50 (19)
C18—C19—C15107.8 (4)C18—Fe2—C1668.02 (19)
C18—C19—Fe269.8 (2)C17—Fe2—C1640.52 (17)
C15—C19—Fe269.9 (2)C15—Fe2—C1640.91 (16)
C18—C19—H19126.1C22—Fe2—C2468.0 (2)
C15—C19—H19126.1C19—Fe2—C24161.24 (18)
Fe2—C19—H19125.7C23—Fe2—C2440.7 (2)
C24—C20—C21109.3 (5)C20—Fe2—C2439.96 (17)
C24—C20—Fe270.5 (3)C21—Fe2—C2467.8 (2)
C21—C20—Fe269.9 (2)C18—Fe2—C24157.4 (2)
C24—C20—H20125.3C17—Fe2—C24123.1 (2)
C21—C20—H20125.3C15—Fe2—C24125.22 (17)
Fe2—C20—H20125.8C16—Fe2—C24109.14 (19)
C5—C1—C2—C3−0.8 (5)C5—C4—Fe1—C10−42.4 (7)
C11—C1—C2—C3−174.5 (4)C3—C4—Fe1—C9163.2 (3)
Fe1—C1—C2—C3−60.1 (3)C5—C4—Fe1—C9−76.3 (3)
C5—C1—C2—Fe159.3 (3)C3—C4—Fe1—C780.0 (3)
C11—C1—C2—Fe1−114.4 (4)C5—C4—Fe1—C7−159.5 (3)
C1—C2—C3—C40.0 (5)C3—C4—Fe1—C647.1 (6)
Fe1—C2—C3—C4−59.2 (3)C5—C4—Fe1—C6167.6 (4)
C1—C2—C3—Fe159.2 (3)C3—C4—Fe1—C8121.8 (3)
C2—C3—C4—C50.7 (5)C5—C4—Fe1—C8−117.7 (3)
Fe1—C3—C4—C5−57.8 (3)C5—C4—Fe1—C3120.5 (4)
C2—C3—C4—Fe158.5 (3)C9—C8—Fe1—C580.0 (4)
C3—C4—C5—C1−1.2 (5)C7—C8—Fe1—C5−162.1 (3)
Fe1—C4—C5—C1−60.0 (3)C9—C8—Fe1—C145.6 (7)
C3—C4—C5—Fe158.9 (3)C7—C8—Fe1—C1163.5 (4)
C2—C1—C5—C41.2 (5)C9—C8—Fe1—C2−163.5 (6)
C11—C1—C5—C4174.9 (4)C7—C8—Fe1—C2−45.6 (8)
Fe1—C1—C5—C460.8 (3)C9—C8—Fe1—C10−37.1 (4)
C2—C1—C5—Fe1−59.7 (3)C7—C8—Fe1—C1080.8 (4)
C11—C1—C5—Fe1114.1 (4)C7—C8—Fe1—C9117.9 (5)
C10—C6—C7—C80.6 (5)C9—C8—Fe1—C7−117.9 (5)
Fe1—C6—C7—C859.4 (4)C9—C8—Fe1—C6−81.2 (4)
C10—C6—C7—Fe1−58.8 (3)C7—C8—Fe1—C636.7 (3)
C6—C7—C8—C90.1 (6)C9—C8—Fe1—C4122.6 (4)
Fe1—C7—C8—C959.6 (3)C7—C8—Fe1—C4−119.4 (3)
C6—C7—C8—Fe1−59.5 (3)C9—C8—Fe1—C3163.4 (3)
C7—C8—C9—C10−0.8 (6)C7—C8—Fe1—C3−78.7 (4)
Fe1—C8—C9—C1059.2 (3)C4—C3—Fe1—C537.3 (3)
C7—C8—C9—Fe1−60.0 (3)C2—C3—Fe1—C5−82.6 (3)
C8—C9—C10—C61.1 (6)C4—C3—Fe1—C181.8 (3)
Fe1—C9—C10—C660.7 (3)C2—C3—Fe1—C1−38.1 (3)
C8—C9—C10—Fe1−59.6 (3)C4—C3—Fe1—C2119.9 (4)
C7—C6—C10—C9−1.0 (5)C4—C3—Fe1—C10164.7 (5)
Fe1—C6—C10—C9−60.5 (3)C2—C3—Fe1—C1044.8 (6)
C7—C6—C10—Fe159.5 (3)C4—C3—Fe1—C9−44.1 (8)
C2—C1—C11—O1−10.7 (6)C2—C3—Fe1—C9−164.0 (6)
C5—C1—C11—O1176.7 (4)C4—C3—Fe1—C7−118.7 (3)
Fe1—C1—C11—O1−97.5 (4)C2—C3—Fe1—C7121.4 (3)
C2—C1—C11—C12171.3 (4)C4—C3—Fe1—C6−160.2 (3)
C5—C1—C11—C12−1.3 (6)C2—C3—Fe1—C679.8 (3)
Fe1—C1—C11—C1284.5 (4)C2—C3—Fe1—C4−119.9 (4)
O1—C11—C12—C133.7 (6)C4—C3—Fe1—C8−76.8 (3)
C1—C11—C12—C13−178.3 (4)C2—C3—Fe1—C8163.3 (3)
C11—C12—C13—C1479.5 (5)C23—C22—Fe2—C19122.9 (3)
C12—C13—C14—O24.0 (6)C21—C22—Fe2—C19−118.1 (3)
C12—C13—C14—C15−177.4 (4)C21—C22—Fe2—C23119.0 (5)
O2—C14—C15—C19168.3 (4)C23—C22—Fe2—C20−81.2 (3)
C13—C14—C15—C19−10.2 (6)C21—C22—Fe2—C2037.8 (3)
O2—C14—C15—C16−17.5 (6)C23—C22—Fe2—C21−119.0 (5)
C13—C14—C15—C16164.0 (4)C23—C22—Fe2—C18164.4 (3)
O2—C14—C15—Fe2−104.6 (4)C21—C22—Fe2—C18−76.6 (4)
C13—C14—C15—Fe276.9 (5)C23—C22—Fe2—C17−164.3 (5)
C19—C15—C16—C17−0.4 (5)C21—C22—Fe2—C17−45.2 (7)
C14—C15—C16—C17−175.5 (4)C23—C22—Fe2—C1580.8 (3)
Fe2—C15—C16—C17−59.4 (3)C21—C22—Fe2—C15−160.2 (3)
C19—C15—C16—Fe259.0 (3)C23—C22—Fe2—C1648.5 (7)
C14—C15—C16—Fe2−116.1 (4)C21—C22—Fe2—C16167.5 (5)
C15—C16—C17—C180.1 (5)C23—C22—Fe2—C24−37.9 (3)
Fe2—C16—C17—C18−59.3 (3)C21—C22—Fe2—C2481.1 (3)
C15—C16—C17—Fe259.4 (3)C18—C19—Fe2—C22121.4 (3)
C16—C17—C18—C190.3 (5)C15—C19—Fe2—C22−119.9 (3)
Fe2—C17—C18—C19−59.1 (3)C18—C19—Fe2—C23162.2 (3)
C16—C17—C18—Fe259.3 (3)C15—C19—Fe2—C23−79.1 (3)
C17—C18—C19—C15−0.5 (5)C18—C19—Fe2—C2048.4 (6)
Fe2—C18—C19—C15−59.9 (3)C15—C19—Fe2—C20167.1 (5)
C17—C18—C19—Fe259.4 (3)C18—C19—Fe2—C2179.0 (3)
C16—C15—C19—C180.5 (5)C15—C19—Fe2—C21−162.2 (3)
C14—C15—C19—C18175.6 (4)C15—C19—Fe2—C18118.7 (4)
Fe2—C15—C19—C1859.8 (3)C18—C19—Fe2—C17−37.0 (3)
C16—C15—C19—Fe2−59.3 (3)C15—C19—Fe2—C1781.7 (3)
C14—C15—C19—Fe2115.8 (4)C18—C19—Fe2—C15−118.7 (4)
C24—C20—C21—C22−0.3 (5)C18—C19—Fe2—C16−80.7 (3)
Fe2—C20—C21—C2259.3 (3)C15—C19—Fe2—C1638.0 (2)
C24—C20—C21—Fe2−59.7 (3)C18—C19—Fe2—C24−167.5 (6)
C20—C21—C22—C230.3 (5)C15—C19—Fe2—C24−48.8 (7)
Fe2—C21—C22—C2360.1 (3)C24—C23—Fe2—C22−119.0 (3)
C20—C21—C22—Fe2−59.8 (3)C22—C23—Fe2—C19−75.4 (3)
C21—C22—C23—C24−0.1 (5)C24—C23—Fe2—C19165.6 (3)
Fe2—C22—C23—C2459.8 (3)C22—C23—Fe2—C2081.5 (3)
C21—C22—C23—Fe2−60.0 (3)C24—C23—Fe2—C20−37.4 (3)
C21—C20—C24—C230.2 (5)C22—C23—Fe2—C2138.1 (3)
Fe2—C20—C24—C23−59.1 (3)C24—C23—Fe2—C21−80.9 (3)
C21—C20—C24—Fe259.3 (3)C22—C23—Fe2—C18−40.5 (6)
C22—C23—C24—C20−0.1 (5)C24—C23—Fe2—C18−159.5 (5)
Fe2—C23—C24—C2059.3 (3)C22—C23—Fe2—C17164.1 (4)
C22—C23—C24—Fe2−59.4 (3)C24—C23—Fe2—C1745.1 (6)
C4—C5—Fe1—C1−118.3 (4)C22—C23—Fe2—C15−118.1 (3)
C4—C5—Fe1—C2−80.0 (3)C24—C23—Fe2—C15122.9 (3)
C1—C5—Fe1—C238.3 (2)C22—C23—Fe2—C16−160.9 (3)
C4—C5—Fe1—C10164.4 (3)C24—C23—Fe2—C1680.1 (3)
C1—C5—Fe1—C10−77.4 (3)C22—C23—Fe2—C24119.0 (3)
C4—C5—Fe1—C9122.9 (3)C24—C20—Fe2—C2281.8 (3)
C1—C5—Fe1—C9−118.9 (3)C21—C20—Fe2—C22−38.5 (3)
C4—C5—Fe1—C749.9 (6)C24—C20—Fe2—C19162.9 (4)
C1—C5—Fe1—C7168.2 (5)C21—C20—Fe2—C1942.7 (6)
C4—C5—Fe1—C6−165.1 (5)C24—C20—Fe2—C2338.1 (3)
C1—C5—Fe1—C6−46.8 (7)C21—C20—Fe2—C23−82.1 (3)
C1—C5—Fe1—C4118.3 (4)C24—C20—Fe2—C21120.2 (4)
C4—C5—Fe1—C880.9 (3)C24—C20—Fe2—C18−162.2 (3)
C1—C5—Fe1—C8−160.8 (3)C21—C20—Fe2—C1877.6 (4)
C4—C5—Fe1—C3−36.4 (3)C24—C20—Fe2—C17−120.2 (3)
C1—C5—Fe1—C381.9 (3)C21—C20—Fe2—C17119.6 (3)
C2—C1—Fe1—C5118.4 (3)C24—C20—Fe2—C15−44.0 (7)
C11—C1—Fe1—C5−120.4 (4)C21—C20—Fe2—C15−164.3 (5)
C5—C1—Fe1—C2−118.4 (3)C24—C20—Fe2—C16−78.4 (4)
C11—C1—Fe1—C2121.2 (5)C21—C20—Fe2—C16161.4 (3)
C2—C1—Fe1—C10−119.9 (3)C21—C20—Fe2—C24−120.2 (4)
C5—C1—Fe1—C10121.7 (3)C20—C21—Fe2—C22118.3 (5)
C11—C1—Fe1—C101.4 (4)C20—C21—Fe2—C19−161.8 (3)
C2—C1—Fe1—C9−161.6 (3)C22—C21—Fe2—C1979.9 (4)
C5—C1—Fe1—C980.0 (3)C20—C21—Fe2—C2380.8 (3)
C11—C1—Fe1—C9−40.4 (4)C22—C21—Fe2—C23−37.5 (3)
C2—C1—Fe1—C7−47.9 (7)C22—C21—Fe2—C20−118.3 (5)
C5—C1—Fe1—C7−166.3 (5)C20—C21—Fe2—C18−119.9 (3)
C11—C1—Fe1—C773.3 (7)C22—C21—Fe2—C18121.7 (3)
C2—C1—Fe1—C6−78.3 (3)C20—C21—Fe2—C17−79.3 (4)
C5—C1—Fe1—C6163.3 (3)C22—C21—Fe2—C17162.4 (3)
C11—C1—Fe1—C642.9 (4)C20—C21—Fe2—C15166.8 (4)
C2—C1—Fe1—C480.3 (3)C22—C21—Fe2—C1548.5 (7)
C5—C1—Fe1—C4−38.2 (3)C20—C21—Fe2—C16−48.7 (8)
C11—C1—Fe1—C4−158.5 (4)C22—C21—Fe2—C16−167.0 (5)
C2—C1—Fe1—C8165.4 (5)C20—C21—Fe2—C2436.8 (3)
C5—C1—Fe1—C846.9 (6)C22—C21—Fe2—C24−81.5 (3)
C11—C1—Fe1—C8−73.4 (6)C17—C18—Fe2—C22163.2 (3)
C2—C1—Fe1—C337.5 (2)C19—C18—Fe2—C22−77.0 (3)
C5—C1—Fe1—C3−80.9 (3)C17—C18—Fe2—C19−119.8 (4)
C11—C1—Fe1—C3158.7 (4)C17—C18—Fe2—C23−166.8 (4)
C3—C2—Fe1—C580.7 (3)C19—C18—Fe2—C23−47.0 (6)
C1—C2—Fe1—C5−38.4 (2)C17—C18—Fe2—C2080.5 (3)
C3—C2—Fe1—C1119.2 (4)C19—C18—Fe2—C20−159.7 (3)
C3—C2—Fe1—C10−162.0 (3)C17—C18—Fe2—C21121.6 (3)
C1—C2—Fe1—C1078.8 (3)C19—C18—Fe2—C21−118.6 (3)
C3—C2—Fe1—C9165.3 (6)C19—C18—Fe2—C17119.8 (4)
C1—C2—Fe1—C946.1 (7)C17—C18—Fe2—C15−81.7 (3)
C3—C2—Fe1—C7−78.3 (3)C19—C18—Fe2—C1538.2 (3)
C1—C2—Fe1—C7162.6 (3)C17—C18—Fe2—C16−37.5 (3)
C3—C2—Fe1—C6−119.2 (3)C19—C18—Fe2—C1682.4 (3)
C1—C2—Fe1—C6121.6 (3)C17—C18—Fe2—C2449.7 (6)
C3—C2—Fe1—C436.7 (3)C19—C18—Fe2—C24169.5 (4)
C1—C2—Fe1—C4−82.4 (3)C18—C17—Fe2—C22−42.6 (6)
C3—C2—Fe1—C8−44.3 (7)C16—C17—Fe2—C22−162.4 (5)
C1—C2—Fe1—C8−163.5 (6)C18—C17—Fe2—C1937.5 (3)
C1—C2—Fe1—C3−119.2 (4)C16—C17—Fe2—C19−82.3 (3)
C9—C10—Fe1—C5−77.1 (4)C18—C17—Fe2—C23167.1 (4)
C6—C10—Fe1—C5165.3 (2)C16—C17—Fe2—C2347.3 (6)
C9—C10—Fe1—C1−119.5 (4)C18—C17—Fe2—C20−118.0 (3)
C6—C10—Fe1—C1123.0 (3)C16—C17—Fe2—C20122.3 (3)
C9—C10—Fe1—C2−161.9 (3)C18—C17—Fe2—C21−76.2 (3)
C6—C10—Fe1—C280.5 (3)C16—C17—Fe2—C21164.1 (3)
C6—C10—Fe1—C9