metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(2E,6E)-2,6-Bis(ferrocenyl­methyl­­idene)cyclo­hexa­none di­chloro­methane monosolvate

aCollege of Life Science and Chemistry, Tianshui Normal University, Tianshui 741001, People's Republic of China, bCollege of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China, and cCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China
*Correspondence e-mail: longsjtsu@yahoo.com.cn

(Received 18 May 2012; accepted 6 July 2012; online 14 July 2012)

In the title compound, [Fe2(C5H5)2(C18H16O)]·CH2Cl2, the C=C bonds both adopt E conformations. In one ferrocenyl group, the five-membered rings are in a near-eclipsed conformation, whereas in the other they are mutually rotated by ca 21.5°. The central cyclo­hexa­none ring adopts a sofa conformation. In the crystal, the dichloro­methane solvent moleucle forms C—H⋯O hydrogen bonds to the organometallic mol­ecules to generate [010] chains of alternating solvent and organometallic species.

Related literature

For our ongoing research in this area, see: Long et al. (2008[Long, S.-J., Liu, X.-L. & Liu, Y.-H. (2008). Acta Cryst. E64, m1164.]); Liu & Guo (2010[Liu, Y.-H. & Guo, R. (2010). Acta Cryst. E66, m479.]); Liu et al. (2008[Liu, Y.-H., Ye, J., Liu, X.-L., Liu, W.-L. & Shi, Y.-C. (2008). Acta Cryst. E64, m1241.]). For synthesis, see: Bai et al. (2004[Bai, Y.-J., Lu, J., Wang, Z.-J., Su, Y.-C. & Shi, Z.-Z. (2004). Chin. J. Org. Chem. 24, 396-398.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe2(C5H5)2(C18H16O)]·CH2Cl2

  • Mr = 575.11

  • Monoclinic, P 21

  • a = 9.417 (4) Å

  • b = 9.330 (4) Å

  • c = 14.449 (6) Å

  • β = 100.127 (5)°

  • V = 1249.7 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.40 mm−1

  • T = 296 K

  • 0.42 × 0.16 × 0.14 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.592, Tmax = 0.829

  • 6984 measured reflections

  • 4224 independent reflections

  • 2923 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.127

  • S = 1.00

  • 4224 reflections

  • 307 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.49 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 1883 Friedel pairs

  • Flack parameter: 0.60 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1S—H1S1⋯O1 0.97 2.46 3.210 (9) 133
C1S—H1S2⋯O1i 0.97 2.25 3.098 (9) 145
Symmetry code: (i) [-x+2, y-{\script{1\over 2}}, -z+1].

Table 2
Dihedral angles (°) for selected planes

  Atoms defining plane 1-Plane Cps1-Plane Cp1-Plane Cp2-Plane
1-Plane O1/C12/C16/C17        
Cps1-Plane C19–C23 11.2 (4)      
Cp1-Plane C24–C28 10.5 (6) 1.2 (6)    
Cp2-Plane C1–C5 19.4 (5) 9.3 (5) 9.4 (6)  
Cps2-Plane C6–C10 20.3 (4) 10.0 (5) 10.1 (6) 1.1 (5)

Data collection: SMART (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

As part of our ongoing studies of ferrocenyl derivatives (Long et al., 2008; Liu et al., 2008; Liu & Guo, 2010) we now report the structure of the title compound.

The molecule of the title compound (I) exists as the most stable configuration of (E,E)-isomer (Fig.1). In the two ferrocenyl moieties Fe1 atom is further to the plane of Cps1 (the substituted cyclopentadienyl ring) (Table 1) and nearer to the plane of Cp1 (the unsubstituted cyclopentadienyl ring) but Fe2 atom is nearer to the plane of Cps2 and further to the plane of Cp2, just in reverse manner, with distances of Fe1 to Cg1 and Cgs1 (Cg and Cgs are respectively the centers of Cp and Cps in the every ferroceneyl group) 1.649 (5) Å and 1.641 (4) Å, respectively, and these of Fe2 to Cgs2 and Cg2 1.635 (4) Å and 1.651 (4) Å, respectively. The two planes of Cp and Cps in the every ferrocenyl group are almost parallel because the dihedral angles of Cp1 to Cps1 and Cp2 to Cps2 are 1.1 (5)° and 1.2 (6)° (Table 2), respectively.

The angles of Cgs1—Fe1—Cg1 and Cgs2—Fe2—Cg2 are 177.9 (2) and 179.1 (2)°, respectively. The correlative carbon atoms in Cp1 and Cps1 of ferrocenyl moiety containing Fe1 atom are in an eclipsed conformation but these of containing Fe2 in a slightly cross one because the five pseudo-torsion angles is in the ranges of 4.9 (2)–6.7 (3)° and 22.0 (2)–21.1 (3). All the ferrocenyl data lie in the normal range and just like our previous reported data (Long et al., 2008; Liu et al., 2008; Liu & Guo, 2010).

The conjugated bridge atoms of C11, C12, O1, C16, C17 and C18 are almost co-plane with the plane-1 (determined by perfect co-plane atoms of C12, O1, C16 and C17). The central cyclohexanone ring adopts an safa conformation beause C15 are also co-plane with the plane-1 but C13 and C14 deprivete – 0.101 (8) and 0.669 (8)(8) Å from the plane, respectively.

In the crystal, the molecules are linked by two C—H···O hydrogen-bonds.

Related literature top

For our ongoing research in this area, see: Long et al. (2008); Liu & Guo (2010); Liu et al. (2008). For synthesis, see: Bai et al. (2004). [Please check added text]

Experimental top

Under the protection of argon gas a total of powder potassium hydroxide (1.68 g, 0.03 mol), ferrocenecarboxaldehyde (4.28 g, 0.02 mol) and cyclohexanone (0.98 g, 0.01 mol) were dissolved in 50 ml ethanol and the mixture solution was reacted in a microwave (700 W, generating 2450 MHz frequency) refluxing system for 3 min. Then the red mixture solid was poured into 40 ml water, filtered off, washed with water and and a water/ethanol (1:1) mixture three times. After drying and recrystallization from 95% ethanol, the title compound (4.20 g) was obtained, yield 85.5% and m.p. 436.5–437.8 K (lit. 435.5–436.5; Bai et al., 2004). Orange needles were obtained by slow evaporation of a solution of the solid in dichloromethane/ether (9:1 volume ratio) at room temperature over a period of 8 d.

Refinement top

After their location in a difference map, all H atoms were fixed geometrically at ideal positions and allowed to ride on the parent C atoms, with C—H distances of 0.93 Å (aryl) and 0.97 Å (CH2), and with Uiso(H) values of 1.2Ueq(C).

Structure description top

In the molecule beside of the ferrocenyl acoms, the deviations of the rest non-hydrogen atoms of C11, C12, C13, C14, C15, C16, O1, C17 and C18 to the plane-1 (determined by C12, C16, C17 and O1 atoms and the least square plane equation of them are -4.94 (3) x + 7.703 (17) y + 4.29 (5) z = 3.32 (4)) are 0.080 (6), 0.000 (6), -0.101 (8), 0.669 (8), 0.089 (8), 0.000 (7), 0.001 (5), -0.001 (7) and -0.057 (7) Å, respectively.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound, showing the two C—H···O intermolecular hydrogen-bonds linking the molecules into [010] chains. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.
(2E,6E)-2,6-Bis(ferrocenylmethylidene)cyclohexanone dichloromethane monosolvate top
Crystal data top
[Fe2(C5H5)2(C18H16O)]·CH2Cl2F(000) = 592
Mr = 575.11Dx = 1.528 Mg m3
Monoclinic, P21Melting point < 436 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 9.417 (4) ÅCell parameters from 1462 reflections
b = 9.330 (4) Åθ = 2.6–22.3°
c = 14.449 (6) ŵ = 1.40 mm1
β = 100.127 (5)°T = 296 K
V = 1249.7 (8) Å3Needle, orange
Z = 20.42 × 0.16 × 0.14 mm
Data collection top
Bruker SMART CCD
diffractometer
4224 independent reflections
Radiation source: fine-focus sealed tube2923 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
h = 1110
Tmin = 0.592, Tmax = 0.829k = 1110
6984 measured reflectionsl = 1715
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)] = 0.052H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0556P)2 + 0.3275P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4224 reflectionsΔρmax = 0.40 e Å3
307 parametersΔρmin = 0.49 e Å3
1 restraintAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.60 (4)
Crystal data top
[Fe2(C5H5)2(C18H16O)]·CH2Cl2V = 1249.7 (8) Å3
Mr = 575.11Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.417 (4) ŵ = 1.40 mm1
b = 9.330 (4) ÅT = 296 K
c = 14.449 (6) Å0.42 × 0.16 × 0.14 mm
β = 100.127 (5)°
Data collection top
Bruker SMART CCD
diffractometer
4224 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
2923 reflections with I > 2σ(I)
Tmin = 0.592, Tmax = 0.829Rint = 0.036
6984 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.40 e Å3
S = 1.00Δρmin = 0.49 e Å3
4224 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs?
307 parametersAbsolute structure parameter: 0.60 (4)
1 restraint
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C70.9697 (9)0.5905 (10)0.9230 (5)0.067 (2)
H71.03200.62770.97450.080*
C270.6739 (10)0.3833 (11)0.1317 (8)0.090 (3)
H270.74510.45190.13010.109*
Cl1S0.8503 (2)0.2625 (3)0.47016 (17)0.0799 (7)
Fe10.47321 (9)0.42146 (10)0.15974 (6)0.0430 (3)
Fe21.01841 (9)0.43903 (11)0.83256 (5)0.0446 (3)
C170.6810 (7)0.5830 (8)0.5096 (4)0.0423 (16)
C200.3276 (7)0.4630 (9)0.2457 (4)0.051 (2)
H200.29840.40050.28890.061*
C210.2612 (8)0.4782 (8)0.1490 (5)0.053 (2)
H210.18190.42700.11840.064*
C180.5523 (7)0.5822 (7)0.3498 (4)0.0444 (16)
H180.63330.63370.34090.053*
C220.3371 (8)0.5839 (8)0.1088 (5)0.053 (2)
H220.31660.61490.04670.064*
C110.8029 (6)0.5823 (7)0.6702 (4)0.0436 (16)
H110.86590.64110.64480.052*
C100.8438 (7)0.5580 (8)0.7710 (5)0.0471 (18)
C190.4470 (7)0.5608 (8)0.2646 (4)0.0437 (18)
C230.4501 (8)0.6353 (9)0.1785 (5)0.049 (2)
H230.51590.70610.16970.058*
C150.4325 (6)0.4580 (9)0.4690 (4)0.057 (2)
H15A0.34140.49100.43320.068*
H15B0.44280.35740.45470.068*
C41.0743 (10)0.2315 (10)0.8150 (6)0.070 (2)
H41.01690.15170.81960.084*
C31.1693 (10)0.2949 (11)0.8887 (6)0.070 (3)
H31.18530.26570.95120.084*
C140.4291 (6)0.4738 (9)0.5720 (4)0.055 (2)
H14A0.35560.41130.58920.066*
H14B0.40470.57180.58530.066*
O10.7765 (5)0.6576 (5)0.4860 (3)0.0511 (12)
C280.6514 (11)0.3016 (13)0.2092 (6)0.082 (3)
H280.70670.30600.26920.099*
C21.2355 (7)0.4091 (12)0.8521 (6)0.072 (2)
H21.30560.46860.88550.086*
C51.0807 (10)0.3089 (11)0.7337 (6)0.072 (3)
H51.02810.29000.67420.087*
C250.4841 (10)0.2364 (11)0.0889 (8)0.086 (3)
H250.40660.18880.05320.103*
C11.1794 (9)0.4193 (13)0.7568 (5)0.074 (2)
H11.20360.48810.71570.089*
C60.9474 (8)0.6446 (9)0.8295 (5)0.054 (2)
H60.99350.72410.80960.065*
C130.5755 (6)0.4355 (9)0.6298 (4)0.0481 (15)
H13A0.57100.44220.69620.058*
H13B0.59980.33750.61650.058*
C160.5541 (7)0.5414 (7)0.4386 (4)0.0419 (15)
C240.5346 (12)0.2143 (11)0.1820 (8)0.086 (3)
H240.49620.15070.22070.103*
C120.6901 (6)0.5347 (7)0.6072 (4)0.0417 (15)
C260.5655 (14)0.3394 (13)0.0564 (6)0.091 (4)
H260.55210.37470.00470.109*
Cl2S1.0017 (2)0.4477 (3)0.35867 (14)0.0868 (7)
C1S0.9880 (7)0.3919 (8)0.4715 (5)0.059 (2)
H1S10.96760.47410.50820.071*
H1S21.07950.35150.50160.071*
C90.8017 (7)0.4478 (11)0.8289 (4)0.061 (2)
H90.73610.37470.80960.074*
C80.8797 (8)0.4705 (10)0.9230 (5)0.067 (3)
H80.87170.41460.97520.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C70.057 (5)0.087 (7)0.052 (5)0.026 (5)0.002 (4)0.020 (5)
C270.054 (5)0.091 (8)0.134 (9)0.013 (5)0.038 (6)0.041 (7)
Cl1S0.0637 (14)0.0742 (16)0.1001 (16)0.0055 (12)0.0095 (12)0.0086 (13)
Fe10.0381 (5)0.0520 (7)0.0385 (5)0.0012 (6)0.0057 (4)0.0013 (6)
Fe20.0410 (5)0.0547 (7)0.0374 (5)0.0005 (6)0.0053 (4)0.0011 (6)
C170.043 (4)0.035 (4)0.046 (4)0.000 (3)0.003 (3)0.005 (3)
C200.044 (4)0.062 (6)0.047 (4)0.005 (4)0.012 (3)0.007 (4)
C210.042 (4)0.067 (6)0.048 (4)0.000 (4)0.003 (3)0.009 (4)
C180.038 (4)0.050 (4)0.044 (4)0.000 (3)0.004 (3)0.002 (3)
C220.056 (5)0.059 (5)0.043 (4)0.013 (4)0.007 (3)0.006 (4)
C110.036 (4)0.043 (4)0.052 (4)0.002 (3)0.009 (3)0.007 (3)
C100.043 (4)0.049 (5)0.048 (4)0.004 (3)0.004 (3)0.002 (3)
C190.038 (4)0.055 (5)0.039 (4)0.002 (3)0.010 (3)0.003 (3)
C230.044 (4)0.051 (5)0.052 (4)0.001 (4)0.010 (3)0.003 (4)
C150.033 (3)0.088 (6)0.048 (3)0.014 (4)0.003 (3)0.003 (4)
C40.079 (6)0.048 (6)0.086 (6)0.003 (5)0.024 (5)0.005 (5)
C30.074 (6)0.086 (7)0.051 (5)0.032 (6)0.011 (4)0.003 (5)
C140.028 (3)0.096 (6)0.043 (3)0.009 (3)0.008 (3)0.003 (4)
O10.041 (3)0.062 (3)0.050 (3)0.015 (2)0.005 (2)0.006 (2)
C280.066 (6)0.125 (9)0.048 (5)0.046 (6)0.009 (4)0.004 (6)
C20.036 (4)0.093 (7)0.087 (6)0.000 (5)0.012 (4)0.021 (6)
C50.088 (7)0.076 (7)0.051 (5)0.017 (6)0.005 (4)0.021 (5)
C250.060 (6)0.071 (7)0.120 (9)0.011 (5)0.002 (6)0.043 (7)
C10.084 (6)0.075 (6)0.074 (5)0.000 (7)0.044 (4)0.000 (6)
C60.050 (5)0.052 (5)0.059 (5)0.008 (4)0.002 (4)0.008 (4)
C130.040 (3)0.059 (4)0.045 (3)0.003 (4)0.007 (3)0.007 (4)
C160.037 (4)0.051 (4)0.038 (4)0.005 (3)0.008 (3)0.007 (3)
C240.077 (7)0.068 (7)0.113 (9)0.015 (6)0.018 (7)0.017 (6)
C120.035 (4)0.039 (4)0.051 (4)0.000 (3)0.006 (3)0.002 (3)
C260.124 (9)0.104 (9)0.051 (5)0.056 (7)0.031 (6)0.011 (6)
Cl2S0.0900 (15)0.0893 (18)0.0846 (13)0.0011 (16)0.0246 (11)0.0082 (15)
C1S0.040 (4)0.059 (5)0.073 (5)0.006 (4)0.002 (3)0.003 (4)
C90.043 (4)0.088 (6)0.052 (4)0.011 (5)0.004 (3)0.010 (5)
C80.049 (4)0.100 (8)0.056 (4)0.022 (5)0.019 (3)0.010 (5)
Geometric parameters (Å, º) top
C7—C81.405 (11)C11—C101.458 (8)
C7—C61.424 (10)C11—H110.9300
C7—Fe22.032 (8)C10—C61.424 (9)
C7—H70.9300C10—C91.425 (11)
C27—C281.401 (14)C19—C231.429 (9)
C27—C261.415 (13)C23—H230.9300
C27—Fe12.033 (8)C15—C141.502 (8)
C27—H270.9300C15—C161.512 (8)
Cl1S—C1S1.770 (7)C15—H15A0.9700
Fe1—C262.007 (8)C15—H15B0.9700
Fe1—C252.019 (9)C4—C51.390 (11)
Fe1—C242.027 (10)C4—C31.395 (11)
Fe1—C232.030 (8)C4—H40.9300
Fe1—C222.037 (7)C3—C21.386 (13)
Fe1—C282.039 (8)C3—H30.9300
Fe1—C202.043 (6)C14—C131.524 (8)
Fe1—C192.044 (7)C14—H14A0.9700
Fe1—C212.045 (7)C14—H14B0.9700
Fe2—C32.020 (8)C28—C241.370 (14)
Fe2—C82.025 (7)C28—H280.9300
Fe2—C12.028 (7)C2—C11.388 (10)
Fe2—C62.029 (8)C2—H20.9300
Fe2—C92.034 (6)C5—C11.388 (13)
Fe2—C22.034 (7)C5—H50.9300
Fe2—C42.034 (9)C25—C241.362 (13)
Fe2—C52.038 (8)C25—C261.363 (13)
Fe2—C102.053 (7)C25—H250.9300
C17—O11.232 (8)C1—H10.9300
C17—C121.468 (8)C6—H60.9300
C17—C161.484 (8)C13—C121.500 (9)
C20—C211.434 (9)C13—H13A0.9700
C20—C191.436 (9)C13—H13B0.9700
C20—H200.9300C24—H240.9300
C21—C221.402 (10)C26—H260.9300
C21—H210.9300Cl2S—C1S1.738 (7)
C18—C161.335 (8)C1S—H1S10.9700
C18—C191.453 (8)C1S—H1S20.9700
C18—H180.9300C9—C81.443 (9)
C22—C231.414 (9)C9—H90.9300
C22—H220.9300C8—H80.9300
C11—C121.346 (8)
C8—C7—C6107.1 (7)Fe1—C22—H22126.3
C8—C7—Fe269.5 (5)C12—C11—C10131.5 (6)
C6—C7—Fe269.4 (4)C12—C11—H11114.2
C8—C7—H7126.4C10—C11—H11114.2
C6—C7—H7126.4C6—C10—C9107.1 (6)
Fe2—C7—H7126.3C6—C10—C11122.5 (6)
C28—C27—C26105.5 (9)C9—C10—C11130.3 (7)
C28—C27—Fe170.1 (5)C6—C10—Fe268.7 (4)
C26—C27—Fe168.5 (5)C9—C10—Fe268.9 (4)
C28—C27—H27127.3C11—C10—Fe2124.6 (5)
C26—C27—H27127.3C23—C19—C20106.2 (6)
Fe1—C27—H27125.7C23—C19—C18123.8 (7)
C26—Fe1—C2539.6 (4)C20—C19—C18130.0 (6)
C26—Fe1—C2466.8 (4)C23—C19—Fe168.9 (4)
C25—Fe1—C2439.3 (4)C20—C19—Fe169.4 (4)
C26—Fe1—C23123.0 (4)C18—C19—Fe1124.2 (5)
C25—Fe1—C23157.6 (4)C22—C23—C19109.1 (7)
C24—Fe1—C23161.8 (4)C22—C23—Fe169.9 (4)
C26—Fe1—C2741.0 (4)C19—C23—Fe170.0 (4)
C25—Fe1—C2767.5 (4)C22—C23—H23125.5
C24—Fe1—C2767.4 (4)C19—C23—H23125.5
C23—Fe1—C27108.9 (4)Fe1—C23—H23126.2
C26—Fe1—C22110.0 (3)C14—C15—C16112.7 (6)
C25—Fe1—C22122.5 (4)C14—C15—H15A109.0
C24—Fe1—C22155.6 (4)C16—C15—H15A109.0
C23—Fe1—C2240.7 (3)C14—C15—H15B109.0
C27—Fe1—C22127.3 (4)C16—C15—H15B109.0
C26—Fe1—C2867.3 (4)H15A—C15—H15B107.8
C25—Fe1—C2866.2 (4)C5—C4—C3107.9 (9)
C24—Fe1—C2839.4 (4)C5—C4—Fe270.2 (5)
C23—Fe1—C28126.4 (4)C3—C4—Fe269.3 (5)
C27—Fe1—C2840.3 (4)C5—C4—H4126.0
C22—Fe1—C28164.1 (4)C3—C4—H4126.0
C26—Fe1—C20161.8 (5)Fe2—C4—H4126.0
C25—Fe1—C20124.8 (4)C2—C3—C4107.8 (8)
C24—Fe1—C20106.7 (4)C2—C3—Fe270.5 (5)
C23—Fe1—C2068.5 (3)C4—C3—Fe270.4 (5)
C27—Fe1—C20154.3 (4)C2—C3—H3126.1
C22—Fe1—C2068.4 (3)C4—C3—H3126.1
C28—Fe1—C20119.3 (3)Fe2—C3—H3124.6
C26—Fe1—C19156.7 (5)C15—C14—C13110.2 (5)
C25—Fe1—C19160.6 (4)C15—C14—H14A109.6
C24—Fe1—C19123.9 (4)C13—C14—H14A109.6
C23—Fe1—C1941.1 (3)C15—C14—H14B109.6
C27—Fe1—C19119.8 (3)C13—C14—H14B109.6
C22—Fe1—C1969.2 (3)H14A—C14—H14B108.1
C28—Fe1—C19106.7 (3)C24—C28—C27108.7 (8)
C20—Fe1—C1941.2 (3)C24—C28—Fe169.8 (5)
C26—Fe1—C21126.0 (4)C27—C28—Fe169.6 (5)
C25—Fe1—C21108.6 (3)C24—C28—H28125.6
C24—Fe1—C21120.4 (4)C27—C28—H28125.6
C23—Fe1—C2168.3 (3)Fe1—C28—H28126.4
C27—Fe1—C21163.7 (4)C3—C2—C1108.2 (9)
C22—Fe1—C2140.2 (3)C3—C2—Fe269.5 (5)
C28—Fe1—C21154.3 (4)C1—C2—Fe269.8 (4)
C20—Fe1—C2141.1 (2)C3—C2—H2125.9
C19—Fe1—C2169.4 (3)C1—C2—H2125.9
C3—Fe2—C8109.0 (3)Fe2—C2—H2126.4
C3—Fe2—C167.5 (4)C1—C5—C4107.9 (8)
C8—Fe2—C1171.7 (4)C1—C5—Fe269.6 (5)
C3—Fe2—C6147.6 (4)C4—C5—Fe269.9 (5)
C8—Fe2—C668.3 (3)C1—C5—H5126.0
C1—Fe2—C6110.4 (4)C4—C5—H5126.0
C3—Fe2—C7115.3 (3)Fe2—C5—H5126.0
C8—Fe2—C740.5 (3)C24—C25—C26109.1 (10)
C1—Fe2—C7133.3 (4)C24—C25—Fe170.6 (6)
C6—Fe2—C741.0 (3)C26—C25—Fe169.7 (5)
C3—Fe2—C9132.0 (4)C24—C25—H25125.4
C8—Fe2—C941.6 (3)C26—C25—H25125.4
C1—Fe2—C9146.2 (3)Fe1—C25—H25125.8
C6—Fe2—C968.7 (4)C2—C1—C5108.1 (9)
C7—Fe2—C969.5 (3)C2—C1—Fe270.2 (4)
C3—Fe2—C240.0 (4)C5—C1—Fe270.4 (5)
C8—Fe2—C2132.6 (3)C2—C1—H1126.0
C1—Fe2—C240.0 (3)C5—C1—H1126.0
C6—Fe2—C2116.9 (4)Fe2—C1—H1125.0
C7—Fe2—C2110.0 (4)C7—C6—C10109.5 (7)
C9—Fe2—C2171.5 (4)C7—C6—Fe269.6 (4)
C3—Fe2—C440.3 (3)C10—C6—Fe270.5 (4)
C8—Fe2—C4115.4 (4)C7—C6—H6125.3
C1—Fe2—C467.2 (4)C10—C6—H6125.3
C6—Fe2—C4171.3 (3)Fe2—C6—H6126.2
C7—Fe2—C4146.6 (4)C12—C13—C14110.6 (6)
C9—Fe2—C4108.4 (4)C12—C13—H13A109.5
C2—Fe2—C467.1 (4)C14—C13—H13A109.5
C3—Fe2—C567.4 (3)C12—C13—H13B109.5
C8—Fe2—C5146.8 (4)C14—C13—H13B109.5
C1—Fe2—C539.9 (4)H13A—C13—H13B108.1
C6—Fe2—C5133.0 (3)C18—C16—C17117.6 (6)
C7—Fe2—C5172.2 (4)C18—C16—C15122.9 (6)
C9—Fe2—C5114.6 (4)C17—C16—C15119.5 (5)
C2—Fe2—C567.0 (3)C25—C24—C28108.4 (9)
C4—Fe2—C539.9 (3)C25—C24—Fe170.0 (6)
C3—Fe2—C10170.9 (4)C28—C24—Fe170.8 (6)
C8—Fe2—C1069.1 (3)C25—C24—H24125.8
C1—Fe2—C10115.7 (3)C28—C24—H24125.8
C6—Fe2—C1040.8 (3)Fe1—C24—H24125.0
C7—Fe2—C1069.4 (3)C11—C12—C17117.0 (6)
C9—Fe2—C1040.8 (3)C11—C12—C13124.6 (6)
C2—Fe2—C10147.5 (4)C17—C12—C13118.4 (6)
C4—Fe2—C10131.8 (3)C25—C26—C27108.2 (9)
C5—Fe2—C10109.0 (3)C25—C26—Fe170.7 (5)
O1—C17—C12121.2 (6)C27—C26—Fe170.5 (5)
O1—C17—C16119.6 (6)C25—C26—H26125.9
C12—C17—C16119.2 (6)C27—C26—H26125.9
C21—C20—C19108.3 (6)Fe1—C26—H26124.5
C21—C20—Fe169.5 (4)Cl2S—C1S—Cl1S111.7 (4)
C19—C20—Fe169.5 (4)Cl2S—C1S—H1S1109.3
C21—C20—H20125.8Cl1S—C1S—H1S1109.3
C19—C20—H20125.8Cl2S—C1S—H1S2109.3
Fe1—C20—H20126.8Cl1S—C1S—H1S2109.3
C22—C21—C20107.9 (7)H1S1—C1S—H1S2108.0
C22—C21—Fe169.6 (4)C10—C9—C8107.4 (8)
C20—C21—Fe169.4 (4)C10—C9—Fe270.3 (4)
C22—C21—H21126.1C8—C9—Fe268.9 (4)
C20—C21—H21126.1C10—C9—H9126.3
Fe1—C21—H21126.5C8—C9—H9126.3
C16—C18—C19131.9 (6)Fe2—C9—H9126.1
C16—C18—H18114.1C7—C8—C9108.9 (7)
C19—C18—H18114.1C7—C8—Fe270.0 (4)
C21—C22—C23108.5 (6)C9—C8—Fe269.5 (4)
C21—C22—Fe170.2 (4)C7—C8—H8125.5
C23—C22—Fe169.4 (4)C9—C8—H8125.5
C21—C22—H22125.7Fe2—C8—H8126.5
C23—C22—H22125.7
C28—C27—Fe1—C26116.6 (9)C20—Fe1—C28—C2480.5 (6)
C28—C27—Fe1—C2579.3 (7)C19—Fe1—C28—C24123.4 (6)
C26—C27—Fe1—C2537.3 (6)C21—Fe1—C28—C2446.2 (10)
C28—C27—Fe1—C2436.5 (6)C26—Fe1—C28—C2739.5 (6)
C26—C27—Fe1—C2480.1 (7)C25—Fe1—C28—C2782.7 (6)
C28—C27—Fe1—C23124.4 (6)C24—Fe1—C28—C27120.0 (8)
C26—C27—Fe1—C23119.0 (7)C23—Fe1—C28—C2775.7 (6)
C28—C27—Fe1—C22166.2 (6)C22—Fe1—C28—C2744.0 (13)
C26—C27—Fe1—C2277.2 (7)C20—Fe1—C28—C27159.5 (6)
C26—C27—Fe1—C28116.6 (9)C19—Fe1—C28—C27116.6 (6)
C28—C27—Fe1—C2045.0 (11)C21—Fe1—C28—C27166.3 (7)
C26—C27—Fe1—C20161.6 (8)C4—C3—C2—C11.6 (10)
C28—C27—Fe1—C1980.7 (7)Fe2—C3—C2—C159.2 (7)
C26—C27—Fe1—C19162.7 (6)C4—C3—C2—Fe260.9 (6)
C28—C27—Fe1—C21158.5 (11)C8—Fe2—C2—C365.8 (8)
C26—C27—Fe1—C2141.9 (15)C1—Fe2—C2—C3119.6 (10)
C8—C7—Fe2—C390.0 (5)C6—Fe2—C2—C3150.2 (5)
C6—C7—Fe2—C3151.5 (5)C7—Fe2—C2—C3105.9 (6)
C6—C7—Fe2—C8118.5 (6)C9—Fe2—C2—C321 (3)
C8—C7—Fe2—C1172.1 (5)C4—Fe2—C2—C338.3 (5)
C6—C7—Fe2—C169.4 (6)C5—Fe2—C2—C381.8 (6)
C8—C7—Fe2—C6118.5 (6)C10—Fe2—C2—C3171.3 (6)
C8—C7—Fe2—C937.8 (4)C3—Fe2—C2—C1119.6 (10)
C6—C7—Fe2—C980.7 (5)C8—Fe2—C2—C1174.6 (7)
C8—C7—Fe2—C2133.2 (5)C6—Fe2—C2—C190.2 (7)
C6—C7—Fe2—C2108.4 (5)C7—Fe2—C2—C1134.5 (7)
C8—C7—Fe2—C454.8 (8)C9—Fe2—C2—C1141 (2)
C6—C7—Fe2—C4173.2 (6)C4—Fe2—C2—C181.3 (7)
C8—C7—Fe2—C5161 (2)C5—Fe2—C2—C137.8 (7)
C6—C7—Fe2—C543 (3)C10—Fe2—C2—C151.7 (10)
C8—C7—Fe2—C1081.5 (5)C3—C4—C5—C10.2 (10)
C6—C7—Fe2—C1037.0 (4)Fe2—C4—C5—C159.4 (6)
C26—Fe1—C20—C2151.3 (13)C3—C4—C5—Fe259.3 (6)
C25—Fe1—C20—C2178.2 (6)C3—Fe2—C5—C181.4 (6)
C24—Fe1—C20—C21117.4 (6)C8—Fe2—C5—C1171.9 (6)
C23—Fe1—C20—C2181.2 (5)C6—Fe2—C5—C168.2 (7)
C27—Fe1—C20—C21170.2 (8)C7—Fe2—C5—C131 (3)
C22—Fe1—C20—C2137.2 (5)C9—Fe2—C5—C1151.3 (5)
C28—Fe1—C20—C21158.2 (6)C2—Fe2—C5—C137.8 (6)
C19—Fe1—C20—C21119.9 (7)C4—Fe2—C5—C1119.1 (8)
C26—Fe1—C20—C19171.2 (10)C10—Fe2—C5—C1107.6 (6)
C25—Fe1—C20—C19161.9 (5)C3—Fe2—C5—C437.7 (6)
C24—Fe1—C20—C19122.7 (5)C8—Fe2—C5—C452.8 (9)
C23—Fe1—C20—C1938.7 (4)C1—Fe2—C5—C4119.1 (8)
C27—Fe1—C20—C1950.3 (10)C6—Fe2—C5—C4172.7 (6)
C22—Fe1—C20—C1982.6 (5)C7—Fe2—C5—C4150 (2)
C28—Fe1—C20—C1981.9 (6)C9—Fe2—C5—C489.6 (6)
C21—Fe1—C20—C19119.9 (7)C2—Fe2—C5—C481.3 (6)
C19—C20—C21—C220.4 (8)C10—Fe2—C5—C4133.3 (6)
Fe1—C20—C21—C2259.2 (5)C26—Fe1—C25—C24120.0 (9)
C19—C20—C21—Fe158.8 (5)C23—Fe1—C25—C24166.5 (8)
C26—Fe1—C21—C2278.3 (6)C27—Fe1—C25—C2481.3 (7)
C25—Fe1—C21—C22118.7 (5)C22—Fe1—C25—C24157.7 (6)
C24—Fe1—C21—C22160.3 (5)C28—Fe1—C25—C2437.4 (6)
C23—Fe1—C21—C2237.6 (4)C20—Fe1—C25—C2472.8 (7)
C27—Fe1—C21—C2245.5 (14)C19—Fe1—C25—C2434.9 (13)
C28—Fe1—C21—C22167.6 (8)C21—Fe1—C25—C24115.6 (6)
C20—Fe1—C21—C22119.3 (7)C24—Fe1—C25—C26120.0 (9)
C19—Fe1—C21—C2281.7 (5)C23—Fe1—C25—C2646.5 (11)
C26—Fe1—C21—C20162.4 (6)C27—Fe1—C25—C2638.7 (6)
C25—Fe1—C21—C20122.0 (6)C22—Fe1—C25—C2682.3 (7)
C24—Fe1—C21—C2080.4 (6)C28—Fe1—C25—C2682.6 (7)
C23—Fe1—C21—C2081.7 (5)C20—Fe1—C25—C26167.2 (6)
C27—Fe1—C21—C20164.8 (11)C19—Fe1—C25—C26154.9 (9)
C22—Fe1—C21—C20119.3 (7)C21—Fe1—C25—C26124.4 (6)
C28—Fe1—C21—C2048.3 (10)C3—C2—C1—C51.5 (11)
C19—Fe1—C21—C2037.6 (5)Fe2—C2—C1—C560.6 (6)
C20—C21—C22—C230.1 (8)C3—C2—C1—Fe259.0 (6)
Fe1—C21—C22—C2359.0 (5)C4—C5—C1—C20.8 (11)
C20—C21—C22—Fe159.0 (5)Fe2—C5—C1—C260.4 (6)
C26—Fe1—C22—C21122.5 (6)C4—C5—C1—Fe259.6 (6)
C25—Fe1—C22—C2180.3 (6)C3—Fe2—C1—C237.2 (7)
C24—Fe1—C22—C2144.8 (10)C8—Fe2—C1—C229 (3)
C23—Fe1—C22—C21119.7 (6)C6—Fe2—C1—C2107.9 (7)
C27—Fe1—C22—C21165.4 (5)C7—Fe2—C1—C267.0 (9)
C28—Fe1—C22—C21160.2 (10)C9—Fe2—C1—C2170.3 (8)
C20—Fe1—C22—C2138.1 (4)C4—Fe2—C1—C281.0 (7)
C19—Fe1—C22—C2182.3 (4)C5—Fe2—C1—C2118.5 (10)
C26—Fe1—C22—C23117.8 (6)C10—Fe2—C1—C2152.1 (7)
C25—Fe1—C22—C23160.0 (5)C3—Fe2—C1—C581.3 (6)
C24—Fe1—C22—C23164.5 (8)C8—Fe2—C1—C5147 (3)
C27—Fe1—C22—C2374.8 (6)C6—Fe2—C1—C5133.6 (5)
C28—Fe1—C22—C2340.5 (12)C7—Fe2—C1—C5174.5 (5)
C20—Fe1—C22—C2381.7 (4)C9—Fe2—C1—C551.7 (10)
C19—Fe1—C22—C2337.4 (4)C2—Fe2—C1—C5118.5 (10)
C21—Fe1—C22—C23119.7 (6)C4—Fe2—C1—C537.5 (6)
C12—C11—C10—C6164.4 (7)C10—Fe2—C1—C589.4 (6)
C12—C11—C10—C919.8 (12)C8—C7—C6—C100.1 (8)
C12—C11—C10—Fe2110.4 (7)Fe2—C7—C6—C1059.4 (5)
C3—Fe2—C10—C6159.9 (17)C8—C7—C6—Fe259.5 (5)
C8—Fe2—C10—C680.6 (5)C9—C10—C6—C70.5 (8)
C1—Fe2—C10—C692.0 (5)C11—C10—C6—C7177.1 (6)
C7—Fe2—C10—C637.1 (4)Fe2—C10—C6—C758.8 (5)
C9—Fe2—C10—C6119.3 (6)C9—C10—C6—Fe258.4 (5)
C2—Fe2—C10—C658.0 (7)C11—C10—C6—Fe2118.3 (6)
C4—Fe2—C10—C6173.5 (5)C3—Fe2—C6—C753.6 (8)
C5—Fe2—C10—C6134.8 (5)C8—Fe2—C6—C737.9 (4)
C3—Fe2—C10—C941 (2)C1—Fe2—C6—C7133.4 (5)
C8—Fe2—C10—C938.6 (5)C9—Fe2—C6—C782.9 (5)
C1—Fe2—C10—C9148.7 (5)C2—Fe2—C6—C790.1 (5)
C6—Fe2—C10—C9119.3 (6)C4—Fe2—C6—C7155 (2)
C7—Fe2—C10—C982.1 (5)C5—Fe2—C6—C7172.8 (5)
C2—Fe2—C10—C9177.2 (6)C10—Fe2—C6—C7120.6 (6)
C4—Fe2—C10—C967.2 (6)C3—Fe2—C6—C10174.2 (5)
C5—Fe2—C10—C9106.0 (5)C8—Fe2—C6—C1082.7 (5)
C3—Fe2—C10—C1184.5 (19)C1—Fe2—C6—C10106.1 (5)
C8—Fe2—C10—C11163.8 (7)C7—Fe2—C6—C10120.6 (6)
C1—Fe2—C10—C1123.6 (8)C9—Fe2—C6—C1037.7 (4)
C6—Fe2—C10—C11115.6 (8)C2—Fe2—C6—C10149.3 (4)
C7—Fe2—C10—C11152.7 (7)C4—Fe2—C6—C1034 (3)
C9—Fe2—C10—C11125.2 (8)C5—Fe2—C6—C1066.6 (6)
C2—Fe2—C10—C1157.6 (9)C15—C14—C13—C1261.5 (8)
C4—Fe2—C10—C1157.9 (8)C19—C18—C16—C17179.7 (7)
C5—Fe2—C10—C1119.2 (7)C19—C18—C16—C150.7 (11)
C21—C20—C19—C230.6 (8)O1—C17—C16—C183.0 (10)
Fe1—C20—C19—C2359.4 (5)C12—C17—C16—C18177.3 (6)
C21—C20—C19—C18176.8 (7)O1—C17—C16—C15176.0 (7)
Fe1—C20—C19—C18118.0 (7)C12—C17—C16—C153.7 (9)
C21—C20—C19—Fe158.8 (5)C14—C15—C16—C18157.5 (6)
C16—C18—C19—C23167.6 (7)C14—C15—C16—C1721.4 (9)
C16—C18—C19—C2015.4 (13)C26—C25—C24—C281.3 (12)
C16—C18—C19—Fe1106.3 (8)Fe1—C25—C24—C2860.6 (7)
C26—Fe1—C19—C2355.4 (10)C26—C25—C24—Fe159.3 (7)
C25—Fe1—C19—C23167.8 (9)C27—C28—C24—C251.2 (12)
C24—Fe1—C19—C23166.3 (5)Fe1—C28—C24—C2560.2 (7)
C27—Fe1—C19—C2384.9 (6)C27—C28—C24—Fe159.0 (7)
C22—Fe1—C19—C2337.1 (4)C26—Fe1—C24—C2536.9 (6)
C28—Fe1—C19—C23126.7 (6)C23—Fe1—C24—C25163.3 (10)
C20—Fe1—C19—C23117.7 (6)C27—Fe1—C24—C2581.6 (6)
C21—Fe1—C19—C2380.2 (4)C22—Fe1—C24—C2550.6 (11)
C26—Fe1—C19—C20173.0 (8)C28—Fe1—C24—C25118.9 (8)
C25—Fe1—C19—C2050.1 (11)C20—Fe1—C24—C25125.0 (6)
C24—Fe1—C19—C2076.0 (5)C19—Fe1—C24—C25166.8 (6)
C23—Fe1—C19—C20117.7 (6)C21—Fe1—C24—C2582.4 (7)
C27—Fe1—C19—C20157.4 (5)C26—Fe1—C24—C2882.0 (6)
C22—Fe1—C19—C2080.6 (4)C25—Fe1—C24—C28118.9 (8)
C28—Fe1—C19—C20115.7 (5)C23—Fe1—C24—C2844.4 (14)
C21—Fe1—C19—C2037.5 (4)C27—Fe1—C24—C2837.3 (5)
C26—Fe1—C19—C1861.9 (11)C22—Fe1—C24—C28169.5 (6)
C25—Fe1—C19—C1874.9 (12)C20—Fe1—C24—C28116.1 (6)
C24—Fe1—C19—C1849.0 (8)C19—Fe1—C24—C2874.3 (6)
C23—Fe1—C19—C18117.3 (8)C21—Fe1—C24—C28158.7 (5)
C27—Fe1—C19—C1832.4 (8)C10—C11—C12—C17179.1 (7)
C22—Fe1—C19—C18154.4 (7)C10—C11—C12—C131.6 (11)
C28—Fe1—C19—C189.4 (7)O1—C17—C12—C113.6 (10)
C20—Fe1—C19—C18125.0 (8)C16—C17—C12—C11176.1 (6)
C21—Fe1—C19—C18162.5 (7)O1—C17—C12—C13175.7 (7)
C21—C22—C23—C190.3 (8)C16—C17—C12—C134.5 (9)
Fe1—C22—C23—C1959.2 (5)C14—C13—C12—C11144.0 (6)
C21—C22—C23—Fe159.5 (5)C14—C13—C12—C1736.7 (8)
C20—C19—C23—C220.5 (8)C24—C25—C26—C270.9 (11)
C18—C19—C23—C22177.0 (6)Fe1—C25—C26—C2760.8 (6)
Fe1—C19—C23—C2259.1 (5)C24—C25—C26—Fe159.9 (7)
C20—C19—C23—Fe159.7 (5)C28—C27—C26—C250.2 (10)
C18—C19—C23—Fe1117.9 (7)Fe1—C27—C26—C2560.9 (6)
C26—Fe1—C23—C2282.5 (6)C28—C27—C26—Fe160.7 (6)
C25—Fe1—C23—C2249.1 (10)C24—Fe1—C26—C2536.7 (6)
C24—Fe1—C23—C22159.3 (11)C23—Fe1—C26—C25160.7 (6)
C27—Fe1—C23—C22125.8 (5)C27—Fe1—C26—C25118.4 (9)
C28—Fe1—C23—C22167.2 (5)C22—Fe1—C26—C25117.2 (6)
C20—Fe1—C23—C2281.5 (4)C28—Fe1—C26—C2579.6 (7)
C19—Fe1—C23—C22120.3 (6)C20—Fe1—C26—C2535.7 (14)
C21—Fe1—C23—C2237.1 (4)C19—Fe1—C26—C25159.1 (8)
C26—Fe1—C23—C19157.2 (5)C21—Fe1—C26—C2575.0 (7)
C25—Fe1—C23—C19169.4 (8)C25—Fe1—C26—C27118.4 (9)
C24—Fe1—C23—C1939.0 (13)C24—Fe1—C26—C2781.7 (6)
C27—Fe1—C23—C19114.0 (5)C23—Fe1—C26—C2780.9 (7)
C22—Fe1—C23—C19120.3 (6)C22—Fe1—C26—C27124.4 (6)
C28—Fe1—C23—C1972.5 (6)C28—Fe1—C26—C2738.8 (6)
C20—Fe1—C23—C1938.8 (4)C20—Fe1—C26—C27154.1 (10)
C21—Fe1—C23—C1983.2 (4)C19—Fe1—C26—C2740.7 (12)
C3—Fe2—C4—C5119.1 (8)C21—Fe1—C26—C27166.6 (6)
C8—Fe2—C4—C5151.1 (6)C6—C10—C9—C80.9 (8)
C1—Fe2—C4—C537.5 (5)C11—C10—C9—C8177.1 (7)
C6—Fe2—C4—C538 (3)Fe2—C10—C9—C859.1 (5)
C7—Fe2—C4—C5172.9 (6)C6—C10—C9—Fe258.2 (5)
C9—Fe2—C4—C5106.7 (6)C11—C10—C9—Fe2118.0 (7)
C2—Fe2—C4—C581.0 (6)C3—Fe2—C9—C10172.0 (5)
C10—Fe2—C4—C567.2 (7)C8—Fe2—C9—C10118.6 (8)
C8—Fe2—C4—C389.8 (6)C1—Fe2—C9—C1057.3 (10)
C1—Fe2—C4—C381.6 (6)C6—Fe2—C9—C1037.8 (4)
C6—Fe2—C4—C3157 (2)C7—Fe2—C9—C1081.8 (5)
C7—Fe2—C4—C353.9 (9)C2—Fe2—C9—C10170 (2)
C9—Fe2—C4—C3134.3 (5)C4—Fe2—C9—C10133.5 (5)
C2—Fe2—C4—C338.0 (5)C5—Fe2—C9—C1091.0 (6)
C5—Fe2—C4—C3119.1 (8)C3—Fe2—C9—C869.3 (7)
C10—Fe2—C4—C3173.7 (5)C1—Fe2—C9—C8176.0 (8)
C5—C4—C3—C21.1 (10)C6—Fe2—C9—C880.9 (6)
Fe2—C4—C3—C260.9 (6)C7—Fe2—C9—C836.8 (5)
C5—C4—C3—Fe259.9 (6)C2—Fe2—C9—C851 (3)
C8—Fe2—C3—C2134.8 (5)C4—Fe2—C9—C8107.8 (6)
C1—Fe2—C3—C237.2 (6)C5—Fe2—C9—C8150.4 (6)
C6—Fe2—C3—C255.6 (8)C10—Fe2—C9—C8118.6 (8)
C7—Fe2—C3—C291.4 (6)C6—C7—C8—C90.6 (9)
C9—Fe2—C3—C2175.9 (5)Fe2—C7—C8—C958.8 (5)
C4—Fe2—C3—C2118.0 (7)C6—C7—C8—Fe259.4 (5)
C5—Fe2—C3—C280.6 (6)C10—C9—C8—C70.9 (9)
C10—Fe2—C3—C2149.1 (17)Fe2—C9—C8—C759.1 (5)
C8—Fe2—C3—C4107.2 (6)C10—C9—C8—Fe260.0 (5)
C1—Fe2—C3—C480.8 (6)C3—Fe2—C8—C7107.1 (5)
C6—Fe2—C3—C4173.7 (6)C1—Fe2—C8—C744 (3)
C7—Fe2—C3—C4150.6 (5)C6—Fe2—C8—C738.4 (4)
C9—Fe2—C3—C466.1 (6)C9—Fe2—C8—C7120.3 (7)
C2—Fe2—C3—C4118.0 (7)C2—Fe2—C8—C768.8 (7)
C5—Fe2—C3—C437.4 (5)C4—Fe2—C8—C7150.2 (5)
C10—Fe2—C3—C431 (2)C5—Fe2—C8—C7175.4 (6)
C16—C15—C14—C1353.7 (9)C10—Fe2—C8—C782.4 (5)
C26—C27—C28—C240.6 (11)C3—Fe2—C8—C9132.7 (6)
Fe1—C27—C28—C2459.1 (7)C1—Fe2—C8—C9164 (3)
C26—C27—C28—Fe159.7 (6)C6—Fe2—C8—C981.9 (6)
C26—Fe1—C28—C2480.5 (7)C7—Fe2—C8—C9120.3 (7)
C25—Fe1—C28—C2437.3 (6)C2—Fe2—C8—C9171.0 (7)
C23—Fe1—C28—C24164.3 (5)C4—Fe2—C8—C989.5 (6)
C27—Fe1—C28—C24120.0 (8)C5—Fe2—C8—C955.1 (9)
C22—Fe1—C28—C24164.0 (10)C10—Fe2—C8—C937.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1S—H1S1···O10.972.463.210 (9)133
C1S—H1S2···O1i0.972.253.098 (9)145
Symmetry code: (i) x+2, y1/2, z+1.

Experimental details

Crystal data
Chemical formula[Fe2(C5H5)2(C18H16O)]·CH2Cl2
Mr575.11
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)9.417 (4), 9.330 (4), 14.449 (6)
β (°) 100.127 (5)
V3)1249.7 (8)
Z2
Radiation typeMo Kα
µ (mm1)1.40
Crystal size (mm)0.42 × 0.16 × 0.14
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008a)
Tmin, Tmax0.592, 0.829
No. of measured, independent and
observed [I > 2σ(I)] reflections
6984, 4224, 2923
Rint0.036
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.127, 1.00
No. of reflections4224
No. of parameters307
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.49
Absolute structureFlack (1983), with how many Friedel pairs?
Absolute structure parameter0.60 (4)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1S—H1S1···O10.972.463.210 (9)133
C1S—H1S2···O1i0.972.253.098 (9)145
Symmetry code: (i) x+2, y1/2, z+1.
Dihedral angles (°) for selected planes top
Atoms defining plane1-PlaneCps1-PlaneCp1-PlaneCp2-Plane
1-PlaneO1/C12/C16/C17
Cps1-PlaneC19–C2311.2 (4)
Cp1-PlaneC24–C2810.5 (6)1.2 (6)
Cp2-PlaneC1–C519.4 (5)9.3 (5)9.4 (6)
Cps2-PlaneC6–C1020.3 (4)10.0 (5)10.1 (6)1.1 (5)
 

Acknowledgements

The authors thank the Natural Science Foundation of China (grant No. 20873101) and Tianshui Normal University (grant No. TSB0715) for financial support of this work.

References

First citationBai, Y.-J., Lu, J., Wang, Z.-J., Su, Y.-C. & Shi, Z.-Z. (2004). Chin. J. Org. Chem. 24, 396–398.  CAS Google Scholar
First citationBruker (2007). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationLiu, Y.-H. & Guo, R. (2010). Acta Cryst. E66, m479.  Web of Science CrossRef IUCr Journals Google Scholar
First citationLiu, Y.-H., Ye, J., Liu, X.-L., Liu, W.-L. & Shi, Y.-C. (2008). Acta Cryst. E64, m1241.  Web of Science CrossRef IUCr Journals Google Scholar
First citationLong, S.-J., Liu, X.-L. & Liu, Y.-H. (2008). Acta Cryst. E64, m1164.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008b). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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