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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 10| October 2009| Page m1201
doi:10.1107/S1600536809035788

(R,R)-(N,N′-Diferrocenylcyclo­hexane-1,2-diyldi­imino)dibenzo­nitrile

Fang Chena*

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: fangc2009@yahoo.cn

(Received 27 July 2009; accepted 4 September 2009; online 12 September 2009)

In the title compound, [Fe2(C5H5)2(C34H34N4)], two ferrocenes are bridged by a cyclo­hexane-1,2-diamine unit. The cyclo­penta­dienyl rings of the two ferrocene units are almost parallel [dihedral angles of 0.7 (4) and 1.0 (4)° in the two units] and eclipsed, as is typically found for similar monosubstituted ferrocene derivatives. The dihedral angle formed by the two benzene rings is 20.2 (3)°. The Fe—C bond lengths to the two substituted Cp rings vary from 2.014 (4) to 2.070 (3) Å, and are in the normal range. In the crystal, mol­ecules are linked by C—H⋯N inter­actions, forming an infinite two-dimensional network.

Related literature

For the applications of ferrocene derivatives, see: Yang et al. (2002[Yang, J.-X., Tian, Y.-P., Liu, Q.-L., Xie, Y.-S., Fun, H.-K., Chantrapromma, S. & Razak, I. A. (2002). Acta Cryst. C58, m43-m44.]); Roberto et al. (2000[Roberto, D., Ugo, R., Bruni, S., Cariati, E., Cariati, F., Fantucci, P., Invernizzi, I., Quici, S., Ledoux, I. & Zyss, J. (2000). Organometallics, 19, 1775-1788.]); Long (1995[Long, N. J. (1995). Angew. Chem. Int. Ed. Engl. 34, 21-75.]). For related structures, see: Hess et al. (1999[Hess, A., Brosch, O., Weyhermuller, T. & Metzler-Nolte, N. (1999). J. Organomet. Chem. 589, 75-84.]); Base et al. (2002[Base, T., Cisarova, I. & Stepnicka, P. (2002). Inorg. Chem. Commun. 5, 46-50.]); For the synthetic strategy, see: Cho et al. (1999[Cho, D.-J., Jeon, S.-J., Kim, H.-S., Cho, C.-S., Shim, S.-C. & Kim, T.-J. (1999). Tetrahedron Asymmetry, 10, 3833-3848.]); Sutcliffe et al. (2002[Sutcliffe, O. B., Bryce, M. R. & Batsanov, A. S. (2002). J. Organomet. Chem. 656, 211-216.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe2(C5H5)2(C34H34N4)]

  • Mr = 740.53

  • Monoclinic, P 21

  • a = 10.302 (2) Å

  • b = 17.573 (4) Å

  • c = 10.746 (2) Å

  • β = 108.40 (3)°

  • V = 1846.0 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.82 mm−1

  • T = 298 K

  • 0.50 × 0.40 × 0.40 mm
Data collection

  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.606, Tmax = 0.720

  • 19480 measured reflections

  • 8770 independent reflections

  • 6719 reflections with I > 2σ(I)

  • Rint = 0.039
Refinement

  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.171

  • S = 1.08

  • 8770 reflections

  • 391 parameters

  • 1 restraint

  • All H-atom parameters refined

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.39 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4198 Friedel pairs

  • Flack parameter: 0.004 (21)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C21—H21A⋯N1i 0.97 2.59 3.486 (9) 154
C37—H37⋯N2ii 0.93 2.59 3.364 (11) 141
Symmetry codes: (i) x, y, z-1; (ii) [-x, y-{\script{1\over 2}}, -z+2].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035788/su2133sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035788/su2133Isup2.hkl

checkCIF report


Comment top

The chemistry of ferrocene has received much attention because of its applications in many fields, such as in catalysis (Yang et al., 2002), organic or organometallic synthesis and materials, non-linear optical (NLO) materials (Long, 1995; Roberto et al., 2000), and medicinal materials. As a part of our ongoing investigations of ferrocene derivatives we have prepared the title compound and report herein on its structure in the solid state.

The molecular structure of the title compound is illustrated in Fig. 1, and the geometrical parameters are given in the archived CIF. The cyclopentadienyl rings in the two ferrocene moieties (involving atoms Fe1 and Fe2) are almost parallel, with dihedral angles of 0.7 (4) ° and 1.0 (4) °, respectively, and eclipsed as viewed down the normal to the Cp ring. The cyclohexane ring has a chair configuration and the two ferrocenemethylamino groups are equatorially bonded to it, as expected. The dihedral angle formed by the two benzene rings is 20.2 (3)°. The Fe—C bond lengths to the two substituted Cp ring vary from 2.014 (4) to 2.070 (3) Å, and are in agreement with the values reported for related compounds (Hess et al., 1999; Base et al., 2002).

In the crystal the molecules are linked by C-H···N interactions, involving the nitrile N-atoms, so forming an infinite two-dimensional network (Table 1).

Related literature top

For the applications of ferrocene derivatives, see: Yang et al. (2002); Roberto et al. (2000); Long (1995). For related structures, see: Hess et al. (1999); Base et al. (2002); For the synthetic strategy, see: Cho et al. (1999); Sutcliffe et al. (2002).

Experimental top

The preparation of the precursors of the title compound has been reported on previously (Cho et al., 1999; Sutcliffe et al., 2002). For the preparation of the title compound, K2CO3 (10 mmol) was added to a mixture of (R,R)-N,N'-Bis(ferrocenylmethyl)cyclohexane-1, 2-diamine (5 mmol) and 3-(bromomethyl)benzonitrile (10 mmol) in acetone (40 ml), and the mixture was heated to reflux for 6 h. The mixture was then cooled, filtered, and the filtrate evaporated to dryness. The yellow solid obtained was recrystallized from a mixture of acetone and petroleum ether (yield: 68%). Yellow crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of a dichloromethane solution at rt after 3 days.

Refinement top

The H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.93 - 0.98 Å, with Uiso(H) = 1.2Ueq(parent C-atom). The EADP's of certain atoms were made equal during the refinement [EADP C1 C2 C3 C4 C5; EADP C36 C37 C38 C39 C35; EADP C22 C23 C21].

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level [H-atoms have been omitted for clarity].
(R,R)-(N,N'-Diferrocenylcyclohexane-1,2- diyldiimino)dibenzonitrile top
Crystal data top
[Fe2(C5H5)2(C34H34N4)]F(000) = 776
Mr = 740.53Dx = 1.332 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4276 reflections
a = 10.302 (2) Åθ = 3.0–27.5°
b = 17.573 (4) ŵ = 0.82 mm−1
c = 10.746 (2) ÅT = 298 K
β = 108.40 (3)°Prism, yellow
V = 1846.0 (7) Å30.50 × 0.40 × 0.40 mm
Z = 2
Data collection top
Rigaku SCXmini
diffractometer		8770 independent reflections
Radiation source: fine-focus sealed tube6719 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
Detector resolution: 13.6612 pixels mm-1θmax = 28.0°, θmin = 2.3°
ω scansh = −13→13
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		k = −22→23
Tmin = 0.606, Tmax = 0.720l = −14→14
19480 measured reflections
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)] = 0.063All H-atom parameters refined
wR(F2) = 0.171 w = 1/[σ2(Fo2) + (0.0734P)2 + 0.5789P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
8770 reflectionsΔρmax = 0.64 e Å−3
391 parametersΔρmin = −0.39 e Å−3
1 restraintAbsolute structure: Flack (1983), 4183 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.004 (21)
Crystal data top
[Fe2(C5H5)2(C34H34N4)]V = 1846.0 (7) Å3
Mr = 740.53Z = 2
Monoclinic, P21Mo Kα radiation
a = 10.302 (2) ŵ = 0.82 mm−1
b = 17.573 (4) ÅT = 298 K
c = 10.746 (2) Å0.50 × 0.40 × 0.40 mm
β = 108.40 (3)°
Data collection top
Rigaku SCXmini
diffractometer		8770 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		6719 reflections with I > 2σ(I)
Tmin = 0.606, Tmax = 0.720Rint = 0.039
19480 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.063All H-atom parameters refined
wR(F2) = 0.171Δρmax = 0.64 e Å−3
S = 1.08Δρmin = −0.39 e Å−3
8770 reflectionsAbsolute structure: Flack (1983), 4183 Friedel pairs
391 parametersAbsolute structure parameter: 0.004 (21)
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. A certain number of restraints were set during the refinement: EADP C1 C2 C3 C4 C5 EADP C36 C37 C38 C39 C35 EADP C22 C23 C21

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe1−0.16586 (6)0.33985 (4)0.47266 (6)0.05329 (18)
Fe20.50851 (7)0.00203 (4)1.22726 (8)0.0603 (2)
N1−0.0020 (8)0.1299 (6)1.2572 (6)0.140 (4)
N2−0.2109 (7)0.2738 (5)0.9801 (8)0.117 (2)
N30.3525 (4)0.1855 (2)0.9336 (3)0.0521 (9)
N40.1016 (4)0.1619 (2)0.7196 (3)0.0494 (8)
C1−0.3415 (7)0.3997 (4)0.3903 (7)0.0823 (7)
H1−0.35870.44960.40960.099*
C2−0.2836 (7)0.3759 (4)0.2921 (7)0.0823 (7)
H2−0.25480.40730.23620.099*
C3−0.2784 (7)0.2946 (4)0.2961 (8)0.0823 (7)
H3−0.24620.26340.24230.099*
C4−0.3287 (6)0.2709 (4)0.3918 (7)0.0823 (7)
H4−0.33620.22030.41400.099*
C5−0.3675 (6)0.3333 (4)0.4524 (6)0.0823 (7)
H5−0.40400.33140.52130.099*
C6−0.0596 (6)0.3356 (4)0.6669 (5)0.0695 (13)
H6−0.09630.32980.73500.083*
C7−0.0367 (8)0.4062 (4)0.6129 (8)0.097 (3)
H7−0.05660.45420.63850.116*
C80.0208 (7)0.3905 (4)0.5145 (8)0.091 (2)
H80.04600.42660.46320.109*
C90.0343 (5)0.3130 (4)0.5051 (6)0.0694 (15)
H90.07070.28840.44710.083*
C10−0.0180 (5)0.2758 (3)0.6010 (4)0.0499 (10)
C11−0.0209 (5)0.1914 (3)0.6200 (5)0.0563 (11)
H11A−0.10070.17860.64520.068*
H11B−0.03020.16640.53710.068*
C120.0791 (6)0.0808 (3)0.7416 (5)0.0613 (12)
H12A0.16590.05740.78890.074*
H12B0.04370.05540.65750.074*
C13−0.0177 (5)0.0698 (3)0.8166 (6)0.0618 (13)
C14−0.1466 (6)0.0366 (3)0.7607 (7)0.0781 (17)
H14−0.17490.02190.67300.094*
C15−0.2331 (6)0.0254 (4)0.8373 (7)0.0851 (19)
H15A−0.31700.00140.80050.102*
C16−0.1963 (6)0.0492 (4)0.9657 (7)0.0804 (17)
H16−0.25500.04261.01520.097*
C17−0.0707 (6)0.0830 (4)1.0190 (6)0.0722 (15)
C180.0171 (6)0.0936 (3)0.9461 (5)0.0655 (13)
H180.10110.11710.98470.079*
C19−0.0319 (7)0.1082 (5)1.1527 (7)0.092 (2)
C200.2301 (5)0.1777 (3)0.6915 (4)0.0537 (11)
H200.23150.23260.67640.064*
C210.2416 (7)0.1391 (5)0.5673 (6)0.0954 (13)
H21A0.15930.14880.49450.114*
H21B0.25070.08460.58080.114*
C220.3673 (7)0.1703 (6)0.5344 (6)0.0954 (13)
H22A0.37370.14590.45560.114*
H22B0.35690.22460.51830.114*
C230.4977 (7)0.1548 (5)0.6485 (6)0.0954 (13)
H23A0.51130.10040.66060.114*
H23B0.57580.17590.62850.114*
C240.4874 (6)0.1900 (4)0.7722 (6)0.0777 (17)
H24A0.48050.24480.76170.093*
H24B0.57010.17880.84370.093*
C250.3603 (5)0.1596 (3)0.8077 (4)0.0556 (11)
H250.36870.10410.81300.067*
C260.3528 (5)0.2688 (3)0.9502 (5)0.0571 (11)
H26A0.31440.29300.86530.068*
H26B0.44600.28670.98850.068*
C270.2695 (5)0.2898 (3)1.0380 (4)0.0527 (10)
C280.1312 (5)0.2788 (3)0.9918 (5)0.0616 (12)
H280.09110.25850.90850.074*
C290.0497 (6)0.2980 (3)1.0697 (5)0.0688 (14)
C300.1084 (7)0.3275 (4)1.1928 (5)0.0799 (17)
H300.05390.34161.24350.096*
C310.2463 (8)0.3362 (5)1.2407 (6)0.094 (2)
H310.28670.35391.32570.113*
C320.3277 (6)0.3185 (3)1.1620 (5)0.0689 (15)
H320.42170.32631.19390.083*
C33−0.0945 (8)0.2853 (4)1.0194 (7)0.0866 (19)
C340.4532 (5)0.1489 (3)1.0455 (4)0.0566 (11)
H34A0.47170.18221.12110.068*
H34B0.53790.14231.02550.068*
C350.4078 (6)0.0744 (4)1.0789 (7)0.0799 (8)
C360.4293 (5)0.0010 (5)1.0245 (6)0.0799 (8)
H360.4760−0.00660.96420.096*
C370.3679 (6)−0.0560 (4)1.0781 (7)0.0799 (8)
H370.3688−0.10791.06140.096*
C380.3064 (6)−0.0217 (4)1.1597 (7)0.0799 (8)
H380.2570−0.04711.20600.096*
C390.3300 (6)0.0607 (4)1.1635 (7)0.0799 (8)
H390.29980.09661.21180.096*
C400.6277 (7)0.0454 (4)1.4035 (6)0.0726 (15)
H400.60970.08811.44640.087*
C410.5881 (7)−0.0292 (4)1.4178 (7)0.089 (2)
H410.5370−0.04471.47080.106*
C420.6371 (8)−0.0758 (4)1.3407 (7)0.088 (2)
H420.6265−0.12841.33390.106*
C430.7059 (7)−0.0309 (5)1.2735 (7)0.087 (2)
H430.7477−0.04841.21390.104*
C440.7007 (6)0.0440 (4)1.3113 (6)0.0706 (15)
H440.73800.08581.28180.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0469 (3)0.0523 (3)0.0521 (3)0.0031 (3)0.0033 (3)0.0070 (3)
Fe20.0492 (4)0.0593 (4)0.0643 (4)0.0012 (3)0.0063 (3)0.0189 (3)
N10.116 (6)0.244 (11)0.061 (4)−0.045 (6)0.029 (4)−0.002 (5)
N20.070 (4)0.130 (6)0.141 (6)0.014 (4)0.021 (4)−0.009 (5)
N30.0495 (19)0.055 (2)0.0442 (18)0.0088 (17)0.0038 (15)0.0059 (16)
N40.053 (2)0.0478 (19)0.0429 (18)0.0076 (16)0.0096 (15)0.0047 (15)
C10.0626 (14)0.0828 (17)0.0867 (17)0.0045 (16)0.0025 (12)0.0040 (17)
C20.0626 (14)0.0828 (17)0.0867 (17)0.0045 (16)0.0025 (12)0.0040 (17)
C30.0626 (14)0.0828 (17)0.0867 (17)0.0045 (16)0.0025 (12)0.0040 (17)
C40.0626 (14)0.0828 (17)0.0867 (17)0.0045 (16)0.0025 (12)0.0040 (17)
C50.0626 (14)0.0828 (17)0.0867 (17)0.0045 (16)0.0025 (12)0.0040 (17)
C60.077 (3)0.069 (3)0.050 (2)0.020 (3)0.002 (2)−0.007 (3)
C70.090 (5)0.058 (4)0.106 (6)0.003 (3)−0.020 (4)−0.009 (4)
C80.061 (4)0.072 (4)0.110 (6)−0.013 (3)−0.016 (4)0.034 (4)
C90.052 (3)0.082 (4)0.070 (3)0.009 (2)0.013 (2)0.028 (3)
C100.046 (2)0.056 (3)0.039 (2)0.008 (2)0.0001 (17)0.0040 (19)
C110.052 (2)0.062 (3)0.048 (2)0.005 (2)0.006 (2)−0.001 (2)
C120.066 (3)0.054 (3)0.060 (3)0.008 (2)0.014 (2)−0.001 (2)
C130.056 (3)0.047 (3)0.070 (3)0.005 (2)0.002 (2)0.007 (2)
C140.076 (4)0.057 (3)0.084 (4)0.001 (3)0.002 (3)−0.006 (3)
C150.060 (3)0.080 (4)0.105 (5)−0.019 (3)0.011 (3)−0.007 (4)
C160.061 (3)0.072 (4)0.104 (5)−0.004 (3)0.020 (3)0.018 (3)
C170.062 (3)0.073 (3)0.072 (3)−0.007 (3)0.008 (3)0.020 (3)
C180.055 (3)0.077 (3)0.057 (3)−0.004 (3)0.006 (2)0.007 (2)
C190.070 (4)0.134 (6)0.068 (4)−0.019 (4)0.017 (3)0.020 (4)
C200.053 (2)0.062 (3)0.043 (2)0.012 (2)0.0108 (19)0.006 (2)
C210.087 (2)0.143 (4)0.063 (2)0.035 (3)0.0324 (18)0.006 (2)
C220.087 (2)0.143 (4)0.063 (2)0.035 (3)0.0324 (18)0.006 (2)
C230.087 (2)0.143 (4)0.063 (2)0.035 (3)0.0324 (18)0.006 (2)
C240.055 (3)0.110 (5)0.072 (4)0.022 (3)0.027 (3)0.019 (3)
C250.048 (2)0.066 (3)0.052 (2)0.017 (2)0.0137 (19)0.005 (2)
C260.057 (3)0.054 (3)0.060 (3)0.001 (2)0.018 (2)0.004 (2)
C270.057 (3)0.047 (2)0.047 (2)0.009 (2)0.0076 (19)0.0108 (18)
C280.058 (3)0.073 (3)0.047 (2)0.014 (2)0.007 (2)0.005 (2)
C290.070 (3)0.071 (3)0.062 (3)0.009 (3)0.017 (3)−0.003 (3)
C300.102 (4)0.087 (4)0.054 (3)0.016 (4)0.029 (3)−0.005 (3)
C310.128 (6)0.087 (4)0.050 (3)0.002 (5)0.002 (3)−0.017 (3)
C320.072 (3)0.059 (3)0.059 (3)0.000 (2)−0.004 (3)−0.004 (2)
C330.082 (4)0.090 (5)0.092 (5)0.022 (4)0.033 (4)0.003 (4)
C340.058 (3)0.054 (3)0.049 (2)0.008 (2)0.005 (2)0.004 (2)
C350.0567 (14)0.0802 (17)0.0893 (19)−0.0014 (13)0.0037 (12)0.0219 (16)
C360.0567 (14)0.0802 (17)0.0893 (19)−0.0014 (13)0.0037 (12)0.0219 (16)
C370.0567 (14)0.0802 (17)0.0893 (19)−0.0014 (13)0.0037 (12)0.0219 (16)
C380.0567 (14)0.0802 (17)0.0893 (19)−0.0014 (13)0.0037 (12)0.0219 (16)
C390.0567 (14)0.0802 (17)0.0893 (19)−0.0014 (13)0.0037 (12)0.0219 (16)
C400.081 (4)0.074 (4)0.062 (3)−0.003 (3)0.020 (3)0.009 (3)
C410.082 (4)0.104 (5)0.070 (4)−0.011 (4)0.010 (3)0.048 (4)
C420.091 (5)0.062 (3)0.083 (4)0.021 (3)−0.015 (4)0.023 (3)
C430.067 (4)0.107 (5)0.079 (4)0.035 (4)0.014 (3)0.012 (4)
C440.049 (3)0.089 (4)0.067 (3)−0.005 (3)0.008 (2)0.015 (3)
Geometric parameters (Å, º) top
Fe1—C52.023 (6)C15—H15A0.9300
Fe1—C62.029 (5)C16—C171.374 (8)
Fe1—C42.029 (7)C16—H160.9300
Fe1—C72.033 (7)C17—C181.383 (8)
Fe1—C92.035 (5)C17—C191.435 (10)
Fe1—C82.036 (7)C18—H180.9300
Fe1—C12.038 (7)C20—C211.535 (8)
Fe1—C22.038 (7)C20—C251.550 (6)
Fe1—C102.041 (4)C20—H200.9800
Fe1—C32.047 (7)C21—C221.545 (10)
Fe2—C432.019 (6)C21—H21A0.9700
Fe2—C382.020 (6)C21—H21B0.9700
Fe2—C422.023 (5)C22—C231.530 (9)
Fe2—C412.026 (6)C22—H22A0.9700
Fe2—C392.030 (6)C22—H22B0.9700
Fe2—C442.037 (6)C23—C241.499 (9)
Fe2—C352.046 (6)C23—H23A0.9700
Fe2—C402.051 (7)C23—H23B0.9700
Fe2—C372.059 (7)C24—C251.569 (7)
Fe2—C362.072 (6)C24—H24A0.9700
N1—C191.133 (9)C24—H24B0.9700
N2—C331.156 (9)C25—H250.9800
N3—C251.453 (6)C26—C271.508 (7)
N3—C341.465 (5)C26—H26A0.9700
N3—C261.475 (6)C26—H26B0.9700
N4—C111.468 (5)C27—C281.366 (7)
N4—C121.474 (6)C27—C321.373 (7)
N4—C201.474 (6)C28—C291.401 (8)
C1—C51.412 (10)C28—H280.9300
C1—C21.429 (11)C29—C301.372 (8)
C1—H10.9300C29—C331.429 (10)
C2—C31.430 (9)C30—C311.358 (10)
C2—H20.9300C30—H300.9300
C3—C41.355 (10)C31—C321.401 (9)
C3—H30.9300C31—H310.9300
C4—C51.397 (10)C32—H320.9300
C4—H40.9300C34—C351.473 (8)
C5—H50.9300C34—H34A0.9700
C6—C101.408 (7)C34—H34B0.9700
C6—C71.420 (10)C35—C391.410 (10)
C6—H60.9300C35—C361.461 (11)
C7—C81.393 (11)C36—C371.402 (9)
C7—H70.9300C36—H360.9300
C8—C91.375 (10)C37—C381.372 (10)
C8—H80.9300C37—H370.9300
C9—C101.460 (7)C38—C391.467 (10)
C9—H90.9300C38—H380.9300
C10—C111.498 (7)C39—H390.9300
C11—H11A0.9700C40—C411.395 (9)
C11—H11B0.9700C40—C441.420 (9)
C12—C131.479 (8)C40—H400.9300
C12—H12A0.9700C41—C421.370 (11)
C12—H12B0.9700C41—H410.9300
C13—C181.388 (8)C42—C431.403 (11)
C13—C141.402 (8)C42—H420.9300
C14—C151.405 (9)C43—C441.384 (10)
C14—H140.9300C43—H430.9300
C15—C161.376 (10)C44—H440.9300
C5—Fe1—C6108.1 (3)N4—C11—H11A108.9
C5—Fe1—C440.4 (3)C10—C11—H11A108.9
C6—Fe1—C4121.5 (3)N4—C11—H11B108.9
C5—Fe1—C7121.5 (3)C10—C11—H11B108.9
C6—Fe1—C740.9 (3)H11A—C11—H11B107.7
C4—Fe1—C7156.8 (4)N4—C12—C13112.4 (4)
C5—Fe1—C9162.9 (3)N4—C12—H12A109.1
C6—Fe1—C968.1 (2)C13—C12—H12A109.1
C4—Fe1—C9126.2 (3)N4—C12—H12B109.1
C7—Fe1—C967.4 (3)C13—C12—H12B109.1
C5—Fe1—C8156.2 (3)H12A—C12—H12B107.9
C6—Fe1—C867.9 (3)C18—C13—C14117.7 (6)
C4—Fe1—C8162.0 (4)C18—C13—C12120.2 (5)
C7—Fe1—C840.1 (3)C14—C13—C12122.1 (6)
C9—Fe1—C839.5 (3)C13—C14—C15119.9 (6)
C5—Fe1—C140.7 (3)C13—C14—H14120.1
C6—Fe1—C1125.6 (3)C15—C14—H14120.1
C4—Fe1—C167.8 (3)C16—C15—C14121.4 (6)
C7—Fe1—C1108.0 (3)C16—C15—H15A119.3
C9—Fe1—C1155.1 (3)C14—C15—H15A119.3
C8—Fe1—C1121.2 (3)C17—C16—C15118.3 (7)
C5—Fe1—C268.5 (3)C17—C16—H16120.8
C6—Fe1—C2163.1 (3)C15—C16—H16120.8
C4—Fe1—C267.3 (3)C16—C17—C18121.4 (6)
C7—Fe1—C2125.5 (3)C16—C17—C19118.6 (6)
C9—Fe1—C2120.1 (3)C18—C17—C19120.0 (6)
C8—Fe1—C2108.1 (3)C17—C18—C13121.3 (5)
C1—Fe1—C241.1 (3)C17—C18—H18119.4
C5—Fe1—C10124.3 (2)C13—C18—H18119.4
C6—Fe1—C1040.5 (2)N1—C19—C17178.4 (10)
C4—Fe1—C10107.4 (3)N4—C20—C21114.6 (5)
C7—Fe1—C1069.0 (2)N4—C20—C25113.7 (4)
C9—Fe1—C1042.0 (2)C21—C20—C25109.0 (4)
C8—Fe1—C1068.9 (2)N4—C20—H20106.3
C1—Fe1—C10161.7 (3)C21—C20—H20106.3
C2—Fe1—C10155.3 (3)C25—C20—H20106.3
C5—Fe1—C367.4 (3)C20—C21—C22110.1 (6)
C6—Fe1—C3154.6 (3)C20—C21—H21A109.6
C4—Fe1—C338.8 (3)C22—C21—H21A109.6
C7—Fe1—C3163.1 (3)C20—C21—H21B109.6
C9—Fe1—C3108.4 (3)C22—C21—H21B109.6
C8—Fe1—C3126.4 (4)H21A—C21—H21B108.2
C1—Fe1—C368.4 (3)C23—C22—C21110.0 (6)
C2—Fe1—C341.0 (2)C23—C22—H22A109.7
C10—Fe1—C3119.7 (2)C21—C22—H22A109.7
C43—Fe2—C38150.8 (3)C23—C22—H22B109.7
C43—Fe2—C4240.6 (3)C21—C22—H22B109.7
C38—Fe2—C42118.8 (3)H22A—C22—H22B108.2
C43—Fe2—C4167.6 (3)C24—C23—C22110.3 (5)
C38—Fe2—C41110.5 (3)C24—C23—H23A109.6
C42—Fe2—C4139.6 (3)C22—C23—H23A109.6
C43—Fe2—C39164.4 (3)C24—C23—H23B109.6
C38—Fe2—C3942.5 (3)C22—C23—H23B109.6
C42—Fe2—C39153.9 (3)H23A—C23—H23B108.1
C41—Fe2—C39120.9 (3)C23—C24—C25111.9 (6)
C43—Fe2—C4439.9 (3)C23—C24—H24A109.2
C38—Fe2—C44168.8 (3)C25—C24—H24A109.2
C42—Fe2—C4467.6 (3)C23—C24—H24B109.2
C41—Fe2—C4467.9 (3)C25—C24—H24B109.2
C39—Fe2—C44128.0 (3)H24A—C24—H24B107.9
C43—Fe2—C35126.4 (3)N3—C25—C20113.4 (4)
C38—Fe2—C3568.7 (2)N3—C25—C24114.6 (4)
C42—Fe2—C35164.5 (3)C20—C25—C24108.1 (4)
C41—Fe2—C35154.0 (3)N3—C25—H25106.7
C39—Fe2—C3540.5 (3)C20—C25—H25106.7
C44—Fe2—C35107.6 (2)C24—C25—H25106.7
C43—Fe2—C4067.4 (3)N3—C26—C27109.8 (4)
C38—Fe2—C40131.1 (3)N3—C26—H26A109.7
C42—Fe2—C4066.9 (3)C27—C26—H26A109.7
C41—Fe2—C4040.0 (3)N3—C26—H26B109.7
C39—Fe2—C40109.7 (3)C27—C26—H26B109.7
C44—Fe2—C4040.6 (3)H26A—C26—H26B108.2
C35—Fe2—C40119.8 (3)C28—C27—C32119.4 (5)
C43—Fe2—C37117.1 (3)C28—C27—C26118.2 (4)
C38—Fe2—C3739.3 (3)C32—C27—C26122.5 (5)
C42—Fe2—C37107.5 (3)C27—C28—C29120.1 (5)
C41—Fe2—C37127.8 (3)C27—C28—H28119.9
C39—Fe2—C3769.5 (3)C29—C28—H28119.9
C44—Fe2—C37150.5 (3)C30—C29—C28120.2 (6)
C35—Fe2—C3769.0 (3)C30—C29—C33120.8 (6)
C40—Fe2—C37166.3 (3)C28—C29—C33119.0 (5)
C43—Fe2—C36106.7 (3)C31—C30—C29119.8 (6)
C38—Fe2—C3666.5 (3)C31—C30—H30120.1
C42—Fe2—C36126.4 (3)C29—C30—H30120.1
C41—Fe2—C36163.7 (3)C30—C31—C32120.0 (5)
C39—Fe2—C3668.6 (3)C30—C31—H31120.0
C44—Fe2—C36118.3 (2)C32—C31—H31120.0
C35—Fe2—C3641.6 (3)C27—C32—C31120.4 (5)
C40—Fe2—C36153.7 (2)C27—C32—H32119.8
C37—Fe2—C3639.7 (3)C31—C32—H32119.8
C25—N3—C34113.2 (4)N2—C33—C29178.7 (8)
C25—N3—C26115.1 (4)N3—C34—C35113.2 (4)
C34—N3—C26111.3 (4)N3—C34—H34A108.9
C11—N4—C12108.4 (4)C35—C34—H34A108.9
C11—N4—C20113.9 (3)N3—C34—H34B108.9
C12—N4—C20114.3 (4)C35—C34—H34B108.9
C5—C1—C2107.0 (7)H34A—C34—H34B107.8
C5—C1—Fe169.1 (4)C39—C35—C36107.3 (6)
C2—C1—Fe169.5 (4)C39—C35—C34126.7 (7)
C5—C1—H1126.5C36—C35—C34126.0 (6)
C2—C1—H1126.5C39—C35—Fe269.1 (4)
Fe1—C1—H1126.5C36—C35—Fe270.1 (3)
C1—C2—C3106.9 (8)C34—C35—Fe2128.4 (4)
C1—C2—Fe169.5 (4)C37—C36—C35108.7 (6)
C3—C2—Fe169.8 (5)C37—C36—Fe269.7 (4)
C1—C2—H2126.5C35—C36—Fe268.3 (4)
C3—C2—H2126.5C37—C36—H36125.7
Fe1—C2—H2125.7C35—C36—H36125.6
C4—C3—C2108.1 (8)Fe2—C36—H36128.0
C4—C3—Fe169.9 (4)C38—C37—C36108.0 (7)
C2—C3—Fe169.2 (5)C38—C37—Fe268.8 (4)
C4—C3—H3126.0C36—C37—Fe270.6 (4)
C2—C3—H3126.0C38—C37—H37126.0
Fe1—C3—H3126.6C36—C37—H37126.0
C3—C4—C5110.3 (7)Fe2—C37—H37126.1
C3—C4—Fe171.3 (4)C37—C38—C39110.2 (7)
C5—C4—Fe169.6 (4)C37—C38—Fe271.9 (4)
C3—C4—H4124.8C39—C38—Fe269.1 (4)
C5—C4—H4124.8C37—C38—H38124.9
Fe1—C4—H4125.9C39—C38—H38124.9
C4—C5—C1107.7 (6)Fe2—C38—H38125.7
C4—C5—Fe170.1 (4)C35—C39—C38105.8 (7)
C1—C5—Fe170.2 (4)C35—C39—Fe270.4 (4)
C4—C5—H5126.2C38—C39—Fe268.4 (4)
C1—C5—H5126.2C35—C39—H39127.1
Fe1—C5—H5125.1C38—C39—H39127.1
C10—C6—C7109.3 (6)Fe2—C39—H39125.7
C10—C6—Fe170.2 (3)C41—C40—C44107.4 (7)
C7—C6—Fe169.7 (4)C41—C40—Fe269.1 (4)
C10—C6—H6125.3C44—C40—Fe269.2 (4)
C7—C6—H6125.3C41—C40—H40126.3
Fe1—C6—H6126.4C44—C40—H40126.3
C8—C7—C6107.6 (6)Fe2—C40—H40127.0
C8—C7—Fe170.1 (4)C42—C41—C40108.6 (6)
C6—C7—Fe169.4 (3)C42—C41—Fe270.1 (4)
C8—C7—H7126.2C40—C41—Fe270.9 (4)
C6—C7—H7126.2C42—C41—H41125.7
Fe1—C7—H7125.9C40—C41—H41125.7
C9—C8—C7109.2 (7)Fe2—C41—H41124.9
C9—C8—Fe170.2 (4)C41—C42—C43108.5 (6)
C7—C8—Fe169.9 (4)C41—C42—Fe270.4 (3)
C9—C8—H8125.4C43—C42—Fe269.5 (3)
C7—C8—H8125.4C41—C42—H42125.8
Fe1—C8—H8126.1C43—C42—H42125.8
C8—C9—C10108.9 (7)Fe2—C42—H42125.9
C8—C9—Fe170.3 (4)C44—C43—C42108.2 (7)
C10—C9—Fe169.2 (3)C44—C43—Fe270.8 (4)
C8—C9—H9125.6C42—C43—Fe269.8 (4)
C10—C9—H9125.6C44—C43—H43125.9
Fe1—C9—H9126.5C42—C43—H43125.9
C6—C10—C9105.0 (5)Fe2—C43—H43125.1
C6—C10—C11130.5 (5)C43—C44—C40107.4 (6)
C9—C10—C11124.6 (5)C43—C44—Fe269.3 (4)
C6—C10—Fe169.3 (3)C40—C44—Fe270.2 (4)
C9—C10—Fe168.8 (3)C43—C44—H44126.3
C11—C10—Fe1126.5 (3)C40—C44—H44126.3
N4—C11—C10113.6 (4)Fe2—C44—H44125.7
C6—Fe1—C1—C5−75.7 (5)C26—N3—C25—C20−68.4 (6)
C4—Fe1—C1—C538.0 (4)C34—N3—C25—C24−73.0 (5)
C7—Fe1—C1—C5−117.6 (5)C26—N3—C25—C2456.5 (5)
C9—Fe1—C1—C5167.4 (6)N4—C20—C25—N3−43.6 (6)
C8—Fe1—C1—C5−159.5 (5)C21—C20—C25—N3−172.8 (5)
C2—Fe1—C1—C5118.6 (6)N4—C20—C25—C24−171.8 (4)
C10—Fe1—C1—C5−40.1 (10)C21—C20—C25—C2459.0 (6)
C3—Fe1—C1—C580.0 (5)C23—C24—C25—N3173.9 (5)
C5—Fe1—C1—C2−118.6 (6)C23—C24—C25—C20−58.5 (7)
C6—Fe1—C1—C2165.7 (4)C25—N3—C26—C27148.3 (4)
C4—Fe1—C1—C2−80.5 (5)C34—N3—C26—C27−81.2 (5)
C7—Fe1—C1—C2123.8 (5)N3—C26—C27—C28−68.3 (5)
C9—Fe1—C1—C248.9 (8)N3—C26—C27—C32111.0 (5)
C8—Fe1—C1—C281.9 (5)C32—C27—C28—C291.1 (8)
C10—Fe1—C1—C2−158.7 (7)C26—C27—C28—C29−179.6 (5)
C3—Fe1—C1—C2−38.5 (4)C27—C28—C29—C30−0.3 (9)
C5—C1—C2—C31.0 (7)C27—C28—C29—C33−179.5 (5)
Fe1—C1—C2—C360.1 (5)C28—C29—C30—C31−1.8 (10)
C5—C1—C2—Fe1−59.1 (4)C33—C29—C30—C31177.4 (7)
C5—Fe1—C2—C138.0 (4)C29—C30—C31—C323.1 (11)
C6—Fe1—C2—C1−43.4 (12)C28—C27—C32—C310.2 (8)
C4—Fe1—C2—C181.7 (5)C26—C27—C32—C31−179.1 (5)
C7—Fe1—C2—C1−76.0 (6)C30—C31—C32—C27−2.3 (10)
C9—Fe1—C2—C1−158.5 (4)C25—N3—C34—C35−83.8 (6)
C8—Fe1—C2—C1−116.9 (5)C26—N3—C34—C35144.7 (5)
C10—Fe1—C2—C1164.2 (5)N3—C34—C35—C39−87.6 (7)
C3—Fe1—C2—C1117.9 (7)N3—C34—C35—C3688.8 (6)
C5—Fe1—C2—C3−79.9 (5)N3—C34—C35—Fe2−178.9 (4)
C6—Fe1—C2—C3−161.3 (8)C43—Fe2—C35—C39−168.5 (4)
C4—Fe1—C2—C3−36.2 (5)C38—Fe2—C35—C3940.3 (4)
C7—Fe1—C2—C3166.0 (5)C42—Fe2—C35—C39162.2 (10)
C9—Fe1—C2—C383.6 (5)C41—Fe2—C35—C39−53.0 (8)
C8—Fe1—C2—C3125.1 (5)C44—Fe2—C35—C39−128.5 (4)
C1—Fe1—C2—C3−117.9 (7)C40—Fe2—C35—C39−85.9 (5)
C10—Fe1—C2—C346.3 (9)C37—Fe2—C35—C3982.6 (4)
C1—C2—C3—C4−0.6 (8)C36—Fe2—C35—C39118.4 (5)
Fe1—C2—C3—C459.2 (5)C43—Fe2—C35—C3673.1 (5)
C1—C2—C3—Fe1−59.9 (5)C38—Fe2—C35—C36−78.1 (4)
C5—Fe1—C3—C4−36.9 (4)C42—Fe2—C35—C3643.8 (12)
C6—Fe1—C3—C447.9 (8)C41—Fe2—C35—C36−171.4 (5)
C7—Fe1—C3—C4−162.0 (10)C39—Fe2—C35—C36−118.4 (5)
C9—Fe1—C3—C4125.4 (4)C44—Fe2—C35—C36113.1 (4)
C8—Fe1—C3—C4165.5 (4)C40—Fe2—C35—C36155.7 (3)
C1—Fe1—C3—C4−80.9 (4)C37—Fe2—C35—C36−35.9 (4)
C2—Fe1—C3—C4−119.5 (7)C43—Fe2—C35—C34−47.6 (8)
C10—Fe1—C3—C480.8 (5)C38—Fe2—C35—C34161.2 (7)
C5—Fe1—C3—C282.7 (5)C42—Fe2—C35—C34−76.9 (13)
C6—Fe1—C3—C2167.5 (5)C41—Fe2—C35—C3467.9 (9)
C4—Fe1—C3—C2119.5 (7)C39—Fe2—C35—C34120.9 (8)
C7—Fe1—C3—C2−42.4 (13)C44—Fe2—C35—C34−7.6 (7)
C9—Fe1—C3—C2−115.0 (5)C40—Fe2—C35—C3435.1 (7)
C8—Fe1—C3—C2−75.0 (6)C37—Fe2—C35—C34−156.5 (7)
C1—Fe1—C3—C238.6 (5)C36—Fe2—C35—C34−120.7 (8)
C10—Fe1—C3—C2−159.6 (4)C39—C35—C36—C37−1.4 (6)
C2—C3—C4—C50.0 (8)C34—C35—C36—C37−178.4 (5)
Fe1—C3—C4—C558.8 (4)Fe2—C35—C36—C3758.0 (4)
C2—C3—C4—Fe1−58.8 (5)C39—C35—C36—Fe2−59.4 (4)
C5—Fe1—C4—C3121.1 (6)C34—C35—C36—Fe2123.6 (6)
C6—Fe1—C4—C3−158.0 (4)C43—Fe2—C36—C37112.5 (5)
C7—Fe1—C4—C3166.8 (6)C38—Fe2—C36—C37−37.1 (4)
C9—Fe1—C4—C3−73.4 (5)C42—Fe2—C36—C3772.2 (5)
C8—Fe1—C4—C3−40.6 (11)C41—Fe2—C36—C3745.5 (11)
C1—Fe1—C4—C382.8 (5)C39—Fe2—C36—C37−83.2 (4)
C2—Fe1—C4—C338.2 (4)C44—Fe2—C36—C37154.1 (4)
C10—Fe1—C4—C3−116.0 (4)C35—Fe2—C36—C37−121.0 (5)
C6—Fe1—C4—C580.8 (5)C40—Fe2—C36—C37−174.7 (6)
C7—Fe1—C4—C545.7 (9)C43—Fe2—C36—C35−126.4 (4)
C9—Fe1—C4—C5165.5 (4)C38—Fe2—C36—C3583.9 (4)
C8—Fe1—C4—C5−161.8 (8)C42—Fe2—C36—C35−166.7 (4)
C1—Fe1—C4—C5−38.3 (4)C41—Fe2—C36—C35166.5 (9)
C2—Fe1—C4—C5−82.9 (4)C39—Fe2—C36—C3537.8 (4)
C10—Fe1—C4—C5122.9 (4)C44—Fe2—C36—C35−84.9 (4)
C3—Fe1—C4—C5−121.1 (6)C40—Fe2—C36—C35−53.7 (7)
C3—C4—C5—C10.6 (7)C37—Fe2—C36—C35121.0 (5)
Fe1—C4—C5—C160.5 (4)C35—C36—C37—C381.7 (7)
C3—C4—C5—Fe1−59.8 (5)Fe2—C36—C37—C3858.9 (4)
C2—C1—C5—C4−1.0 (6)C35—C36—C37—Fe2−57.2 (4)
Fe1—C1—C5—C4−60.4 (4)C43—Fe2—C37—C38157.2 (4)
C2—C1—C5—Fe159.4 (4)C42—Fe2—C37—C38114.3 (5)
C6—Fe1—C5—C4−117.7 (4)C41—Fe2—C37—C3875.5 (5)
C7—Fe1—C5—C4−160.7 (4)C39—Fe2—C37—C38−38.2 (4)
C9—Fe1—C5—C4−43.5 (10)C44—Fe2—C37—C38−170.6 (5)
C8—Fe1—C5—C4166.1 (7)C35—Fe2—C37—C38−81.6 (4)
C1—Fe1—C5—C4118.2 (6)C40—Fe2—C37—C3850.9 (13)
C2—Fe1—C5—C479.9 (4)C36—Fe2—C37—C38−119.1 (6)
C10—Fe1—C5—C4−76.0 (5)C43—Fe2—C37—C36−83.6 (5)
C3—Fe1—C5—C435.5 (4)C38—Fe2—C37—C36119.1 (6)
C6—Fe1—C5—C1124.0 (4)C42—Fe2—C37—C36−126.5 (5)
C4—Fe1—C5—C1−118.2 (6)C41—Fe2—C37—C36−165.3 (5)
C7—Fe1—C5—C181.1 (5)C39—Fe2—C37—C3680.9 (4)
C9—Fe1—C5—C1−161.8 (8)C44—Fe2—C37—C36−51.4 (7)
C8—Fe1—C5—C147.9 (9)C35—Fe2—C37—C3637.5 (4)
C2—Fe1—C5—C1−38.3 (4)C40—Fe2—C37—C36170.1 (11)
C10—Fe1—C5—C1165.8 (4)C36—C37—C38—C39−1.4 (7)
C3—Fe1—C5—C1−82.7 (5)Fe2—C37—C38—C3958.7 (4)
C5—Fe1—C6—C10122.0 (4)C36—C37—C38—Fe2−60.0 (4)
C4—Fe1—C6—C1079.7 (4)C43—Fe2—C38—C37−44.9 (7)
C7—Fe1—C6—C10−120.5 (6)C42—Fe2—C38—C37−82.5 (5)
C9—Fe1—C6—C10−40.3 (3)C41—Fe2—C38—C37−125.3 (4)
C8—Fe1—C6—C10−83.0 (4)C39—Fe2—C38—C37120.9 (6)
C1—Fe1—C6—C10163.7 (4)C44—Fe2—C38—C37155.4 (12)
C2—Fe1—C6—C10−162.6 (9)C35—Fe2—C38—C3782.5 (4)
C3—Fe1—C6—C1046.6 (8)C40—Fe2—C38—C37−165.9 (4)
C5—Fe1—C6—C7−117.4 (5)C36—Fe2—C38—C3737.4 (4)
C4—Fe1—C6—C7−159.7 (5)C43—Fe2—C38—C39−165.8 (5)
C9—Fe1—C6—C780.3 (5)C42—Fe2—C38—C39156.6 (5)
C8—Fe1—C6—C737.5 (4)C41—Fe2—C38—C39113.8 (5)
C1—Fe1—C6—C7−75.8 (5)C44—Fe2—C38—C3934.5 (16)
C2—Fe1—C6—C7−42.1 (12)C35—Fe2—C38—C39−38.4 (4)
C10—Fe1—C6—C7120.5 (6)C40—Fe2—C38—C3973.2 (5)
C3—Fe1—C6—C7167.2 (7)C37—Fe2—C38—C39−120.9 (6)
C10—C6—C7—C8−0.7 (7)C36—Fe2—C38—C39−83.5 (5)
Fe1—C6—C7—C8−59.9 (5)C36—C35—C39—C380.5 (6)
C10—C6—C7—Fe159.2 (4)C34—C35—C39—C38177.5 (5)
C5—Fe1—C7—C8−159.9 (4)Fe2—C35—C39—C38−59.5 (4)
C6—Fe1—C7—C8118.7 (6)C36—C35—C39—Fe260.0 (4)
C4—Fe1—C7—C8167.2 (6)C34—C35—C39—Fe2−123.0 (6)
C9—Fe1—C7—C836.5 (4)C37—C38—C39—C350.5 (7)
C1—Fe1—C7—C8−117.3 (4)Fe2—C38—C39—C3560.8 (4)
C2—Fe1—C7—C8−75.2 (5)C37—C38—C39—Fe2−60.3 (4)
C10—Fe1—C7—C881.9 (4)C43—Fe2—C39—C3536.6 (13)
C3—Fe1—C7—C8−42.3 (12)C38—Fe2—C39—C35−116.9 (6)
C5—Fe1—C7—C681.4 (5)C42—Fe2—C39—C35−169.3 (6)
C4—Fe1—C7—C648.5 (9)C41—Fe2—C39—C35156.0 (4)
C9—Fe1—C7—C6−82.2 (4)C44—Fe2—C39—C3571.1 (5)
C8—Fe1—C7—C6−118.7 (6)C40—Fe2—C39—C35113.2 (4)
C1—Fe1—C7—C6124.0 (4)C37—Fe2—C39—C35−81.4 (4)
C2—Fe1—C7—C6166.1 (4)C36—Fe2—C39—C35−38.8 (4)
C10—Fe1—C7—C6−36.8 (3)C43—Fe2—C39—C38153.5 (10)
C3—Fe1—C7—C6−160.9 (9)C42—Fe2—C39—C38−52.4 (9)
C6—C7—C8—C90.1 (8)C41—Fe2—C39—C38−87.1 (5)
Fe1—C7—C8—C9−59.4 (5)C44—Fe2—C39—C38−172.0 (4)
C6—C7—C8—Fe159.5 (4)C35—Fe2—C39—C38116.9 (6)
C5—Fe1—C8—C9166.8 (6)C40—Fe2—C39—C38−130.0 (4)
C6—Fe1—C8—C981.9 (4)C37—Fe2—C39—C3835.5 (4)
C4—Fe1—C8—C9−43.3 (11)C36—Fe2—C39—C3878.1 (5)
C7—Fe1—C8—C9120.3 (6)C43—Fe2—C40—C41−81.6 (5)
C1—Fe1—C8—C9−158.8 (4)C38—Fe2—C40—C4171.5 (6)
C2—Fe1—C8—C9−115.6 (4)C42—Fe2—C40—C41−37.3 (5)
C10—Fe1—C8—C938.3 (4)C39—Fe2—C40—C41114.9 (5)
C3—Fe1—C8—C9−73.8 (5)C44—Fe2—C40—C41−119.2 (6)
C5—Fe1—C8—C746.5 (9)C35—Fe2—C40—C41158.3 (5)
C6—Fe1—C8—C7−38.3 (4)C37—Fe2—C40—C4130.7 (14)
C4—Fe1—C8—C7−163.6 (8)C36—Fe2—C40—C41−163.7 (6)
C9—Fe1—C8—C7−120.3 (6)C43—Fe2—C40—C4437.7 (4)
C1—Fe1—C8—C780.9 (5)C38—Fe2—C40—C44−169.3 (4)
C2—Fe1—C8—C7124.1 (4)C42—Fe2—C40—C4481.9 (5)
C10—Fe1—C8—C7−82.0 (4)C41—Fe2—C40—C44119.2 (6)
C3—Fe1—C8—C7165.9 (4)C39—Fe2—C40—C44−125.9 (4)
C7—C8—C9—C100.6 (7)C35—Fe2—C40—C44−82.4 (5)
Fe1—C8—C9—C10−58.6 (4)C37—Fe2—C40—C44150.0 (11)
C7—C8—C9—Fe159.2 (5)C36—Fe2—C40—C44−44.4 (8)
C5—Fe1—C9—C8−161.7 (8)C44—C40—C41—C421.5 (8)
C6—Fe1—C9—C8−81.4 (5)Fe2—C40—C41—C4260.2 (5)
C4—Fe1—C9—C8164.7 (5)C44—C40—C41—Fe2−58.7 (4)
C7—Fe1—C9—C8−37.0 (5)C43—Fe2—C41—C42−37.8 (5)
C1—Fe1—C9—C847.2 (9)C38—Fe2—C41—C42110.8 (5)
C2—Fe1—C9—C882.1 (6)C39—Fe2—C41—C42156.8 (4)
C10—Fe1—C9—C8−120.2 (6)C44—Fe2—C41—C42−81.1 (5)
C3—Fe1—C9—C8125.5 (5)C35—Fe2—C41—C42−166.0 (6)
C5—Fe1—C9—C10−41.5 (10)C40—Fe2—C41—C42−118.9 (6)
C6—Fe1—C9—C1038.8 (3)C37—Fe2—C41—C4269.9 (5)
C4—Fe1—C9—C10−75.0 (4)C36—Fe2—C41—C4234.7 (11)
C7—Fe1—C9—C1083.2 (4)C43—Fe2—C41—C4081.1 (5)
C8—Fe1—C9—C10120.2 (6)C38—Fe2—C41—C40−130.3 (4)
C1—Fe1—C9—C10167.4 (6)C42—Fe2—C41—C40118.9 (6)
C2—Fe1—C9—C10−157.7 (3)C39—Fe2—C41—C40−84.2 (5)
C3—Fe1—C9—C10−114.3 (4)C44—Fe2—C41—C4037.8 (4)
C7—C6—C10—C91.0 (5)C35—Fe2—C41—C40−47.1 (8)
Fe1—C6—C10—C959.9 (3)C37—Fe2—C41—C40−171.2 (4)
C7—C6—C10—C11−179.8 (5)C36—Fe2—C41—C40153.6 (8)
Fe1—C6—C10—C11−121.0 (5)C40—C41—C42—C43−1.5 (8)
C7—C6—C10—Fe1−58.9 (4)Fe2—C41—C42—C4359.3 (4)
C8—C9—C10—C6−1.0 (6)C40—C41—C42—Fe2−60.8 (5)
Fe1—C9—C10—C6−60.3 (3)C43—Fe2—C42—C41119.5 (6)
C8—C9—C10—C11179.8 (5)C38—Fe2—C42—C41−87.8 (5)
Fe1—C9—C10—C11120.6 (4)C39—Fe2—C42—C41−50.1 (8)
C8—C9—C10—Fe159.3 (4)C44—Fe2—C42—C4182.0 (5)
C5—Fe1—C10—C6−77.3 (5)C35—Fe2—C42—C41156.7 (9)
C4—Fe1—C10—C6−118.5 (4)C40—Fe2—C42—C4137.7 (4)
C7—Fe1—C10—C637.2 (5)C37—Fe2—C42—C41−129.0 (4)
C9—Fe1—C10—C6116.3 (5)C36—Fe2—C42—C41−168.6 (4)
C8—Fe1—C10—C680.2 (5)C38—Fe2—C42—C43152.8 (5)
C1—Fe1—C10—C6−46.7 (9)C41—Fe2—C42—C43−119.5 (6)
C2—Fe1—C10—C6168.0 (6)C39—Fe2—C42—C43−169.6 (6)
C3—Fe1—C10—C6−158.9 (4)C44—Fe2—C42—C43−37.5 (4)
C5—Fe1—C10—C9166.4 (4)C35—Fe2—C42—C4337.2 (13)
C6—Fe1—C10—C9−116.3 (5)C40—Fe2—C42—C43−81.7 (5)
C4—Fe1—C10—C9125.2 (4)C37—Fe2—C42—C43111.6 (5)
C7—Fe1—C10—C9−79.1 (5)C36—Fe2—C42—C4372.0 (5)
C8—Fe1—C10—C9−36.1 (5)C41—C42—C43—C440.8 (8)
C1—Fe1—C10—C9−163.0 (8)Fe2—C42—C43—C4460.7 (5)
C2—Fe1—C10—C951.7 (7)C41—C42—C43—Fe2−59.8 (5)
C3—Fe1—C10—C984.8 (4)C38—Fe2—C43—C44−174.0 (5)
C5—Fe1—C10—C1148.4 (5)C42—Fe2—C43—C44−118.7 (6)
C6—Fe1—C10—C11125.7 (6)C41—Fe2—C43—C44−81.8 (5)
C4—Fe1—C10—C117.2 (5)C39—Fe2—C43—C4444.1 (13)
C7—Fe1—C10—C11162.9 (6)C35—Fe2—C43—C4472.9 (5)
C9—Fe1—C10—C11−118.0 (6)C40—Fe2—C43—C44−38.4 (4)
C8—Fe1—C10—C11−154.1 (6)C37—Fe2—C43—C44155.9 (4)
C1—Fe1—C10—C1179.0 (9)C36—Fe2—C43—C44114.4 (4)
C2—Fe1—C10—C11−66.3 (8)C38—Fe2—C43—C42−55.3 (7)
C3—Fe1—C10—C11−33.3 (6)C41—Fe2—C43—C4236.9 (4)
C12—N4—C11—C10172.7 (4)C39—Fe2—C43—C42162.8 (10)
C20—N4—C11—C10−58.8 (5)C44—Fe2—C43—C42118.7 (6)
C6—C10—C11—N4−87.2 (6)C35—Fe2—C43—C42−168.4 (4)
C9—C10—C11—N491.7 (5)C40—Fe2—C43—C4280.3 (5)
Fe1—C10—C11—N4179.7 (3)C37—Fe2—C43—C42−85.4 (5)
C11—N4—C12—C13−73.5 (5)C36—Fe2—C43—C42−126.9 (5)
C20—N4—C12—C13158.3 (4)C42—C43—C44—C400.1 (7)
N4—C12—C13—C18−66.0 (6)Fe2—C43—C44—C4060.2 (4)
N4—C12—C13—C14113.2 (5)C42—C43—C44—Fe2−60.1 (5)
C18—C13—C14—C15−2.7 (8)C41—C40—C44—C43−1.0 (7)
C12—C13—C14—C15178.1 (5)Fe2—C40—C44—C43−59.6 (5)
C13—C14—C15—C162.6 (9)C41—C40—C44—Fe258.6 (5)
C14—C15—C16—C17−1.4 (10)C38—Fe2—C44—C43164.7 (13)
C15—C16—C17—C180.5 (9)C42—Fe2—C44—C4338.2 (4)
C15—C16—C17—C19179.7 (6)C41—Fe2—C44—C4381.1 (5)
C16—C17—C18—C13−0.7 (9)C39—Fe2—C44—C43−166.3 (4)
C19—C17—C18—C13−179.9 (6)C35—Fe2—C44—C43−126.2 (4)
C14—C13—C18—C171.8 (8)C40—Fe2—C44—C43118.3 (6)
C12—C13—C18—C17−179.0 (5)C37—Fe2—C44—C43−47.7 (7)
C11—N4—C20—C21−64.2 (6)C36—Fe2—C44—C43−82.3 (5)
C12—N4—C20—C2161.2 (5)C43—Fe2—C44—C40−118.3 (6)
C11—N4—C20—C25169.6 (4)C38—Fe2—C44—C4046.4 (15)
C12—N4—C20—C25−65.0 (5)C42—Fe2—C44—C40−80.2 (5)
N4—C20—C21—C22170.3 (5)C41—Fe2—C44—C40−37.3 (4)
C25—C20—C21—C22−61.1 (7)C39—Fe2—C44—C4075.4 (5)
C20—C21—C22—C2359.6 (8)C35—Fe2—C44—C40115.5 (4)
C21—C22—C23—C24−57.5 (9)C37—Fe2—C44—C40−166.1 (5)
C22—C23—C24—C2557.8 (8)C36—Fe2—C44—C40159.4 (4)
C34—N3—C25—C20162.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21A···N1i0.972.593.486 (9)154
C37—H37···N2ii0.932.593.364 (11)141
Symmetry codes: (i) x, y, z−1; (ii) −x, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula[Fe2(C5H5)2(C34H34N4)]
Mr740.53
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)10.302 (2), 17.573 (4), 10.746 (2)
β (°) 108.40 (3)
V (Å3)1846.0 (7)
Z2
Radiation typeMo Kα
µ (mm−1)0.82
Crystal size (mm)0.50 × 0.40 × 0.40
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.606, 0.720
No. of measured, independent and
observed [I > 2σ(I)] reflections		19480, 8770, 6719
Rint0.039
(sin θ/λ)max (Å−1)0.659
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.171, 1.08
No. of reflections8770
No. of parameters391
No. of restraints1
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.64, −0.39
Absolute structureFlack (1983), 4183 Friedel pairs
Absolute structure parameter0.004 (21)

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21A···N1i0.972.593.486 (9)154
C37—H37···N2ii0.932.593.364 (11)141
Symmetry codes: (i) x, y, z−1; (ii) −x, y−1/2, −z+2.
 

Acknowledgements

This work was supported by a start-up grant from Southeast University.

References

First citationBase, T., Cisarova, I. & Stepnicka, P. (2002). Inorg. Chem. Commun. 5, 46–50.  Web of Science CSD CrossRef CAS Google Scholar
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 First citationSutcliffe, O. B., Bryce, M. R. & Batsanov, A. S. (2002). J. Organomet. Chem. 656, 211–216.  Web of Science CSD CrossRef CAS Google Scholar
 First citationYang, J.-X., Tian, Y.-P., Liu, Q.-L., Xie, Y.-S., Fun, H.-K., Chantrapromma, S. & Razak, I. A. (2002). Acta Cryst. C58, m43–m44.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 65| Part 10| October 2009| Page m1201
doi:10.1107/S1600536809035788
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