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

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ISSN: 2056-9890

(1R,2R)-N,N′-Bis(ferrocenylmeth­yl)-1,2-di­phenyl­ethane-1,2-di­amine

aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
*Correspondence e-mail: takefive5@163.com

(Received 7 June 2010; accepted 22 June 2010; online 21 July 2010)

The title compound, [Fe2(C5H5)2(C26H26N2)], was synthesized from a chiral diamine and ferrocenecarboxaldehyde and subsequent reduction with NaBH4. It has two chiral centers which both exhibit an R configuration. Two ferrocene groups are present in the mol­ecular structure, with their cyclo­penta­dienyl ring planes showing an almost perpen­dicular arrangement [dihedral angle 88.6 (1)°].

Related literature

For related compounds, see: Hess et al. (1999[Hess, A., Brosch, O., Weyhermüller, T. & Metzler-Nolte, N. (1999). J. Organomet. Chem. 589, 75-84.]); Bâse et al. (2002[Bâse, T., Císařová, I. & Štěpnička, P. (2002). Inorg. Chem. Commun. 5, 46-50.]); Wang (2009[Wang, Y. C. (2009). Acta Cryst. E65, m874.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe2(C5H5)2(C26H26N2)]

  • Mr = 608.37

  • Orthorhombic, P 21 21 21

  • a = 9.5080 (2) Å

  • b = 9.5700 (2) Å

  • c = 32.3680 (7) Å

  • V = 2945.21 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.01 mm−1

  • T = 295 K

  • 0.36 × 0.20 × 0.18 mm

Data collection
  • Rigaku R-AXIS RAPID/ZJUG diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.712, Tmax = 0.839

  • 45235 measured reflections

  • 6726 independent reflections

  • 5515 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.077

  • S = 1.01

  • 6726 reflections

  • 361 parameters

  • 30 restraints

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.23 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2915 Friedel pairs

  • Flack parameter: −0.006 (14)

Data collection: PROCESS-AUTO (Rigaku, 2006[Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007[Rigaku (2007). CrystalStructure. Rigaku Americas Corporation, The Woodlands, Texas, USA.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Due to the special structure and electronic properties of ferrocene, its derivatives have been widely used in material sciences, biology and asymmetric catalysis. The title compound, which could be readily synthesized from commercially available ferrocenecarboxaldehyde and a chiral diamine, is envisaged to potentially act as a chiral ligand in asymmetric catalysis.

The crystal structure of the title compound is shown in Fig. 1. It contains the (1R,2R)-(+)-1,2-diphenyl-1,2-ethanediamine subunit, meanwhile, the hydrogen atoms of the two amine groups have been substituted by ferrocenylmethyl units. The angle between the two benzene ring planes is 36.3 (1)°. The Cp ring planes (C21—C25 and C27—C31), are almost perpendicular to each other [dihedral angle 88.6 (1)°]. The intramolecular Fe—Fe distance is 7.064 Å.

Related literature top

For related compounds, see: Hess et al. (1999); Bâse et al. (2002); Wang (2009).

Experimental top

A solution of ferrocenecarboxaldehyde (5 mmol, 1070 mg) in 20 ml absolute methanol was added dropwise to a stirred solution of (1R,2R)-(+)-1,2-diphenyl-1,2-ethanediamine (2.5 mmol, 530 mg) in absolute methanol (10 ml). After stirring for 12 h, the reaction mixture was filtered obtaining brown crude imine. The imine was added to 25 ml absolute methanol and 25 ml THF. Solid NaBH4 (1.5 g, 40 mmol) was added in small portions over a period of 1 h. The resulting clear solution was allowed to stir at room temperature overnight. The solvent was removed in vacuo. Then 100 ml of water were added, extracted with dichloromethane. The combined organic layer was concentrated under reduced pressure to afford the crude product which was purified by flash chromatography (silica gel, Hex/AcOEt, v/v, 9:1), giving a yellow solid (overall yield 73%). Single crystals were obtained by slow evaporation of a dichloromethane solution.

Refinement top

H atoms were placed in calculated position with N—H=0.86 Å, C—H=0.93–0.97 Å and were included in the refinement in the riding model with Uiso(H) = 1.2Ueq of the carrier atoms.

Structure description top

Due to the special structure and electronic properties of ferrocene, its derivatives have been widely used in material sciences, biology and asymmetric catalysis. The title compound, which could be readily synthesized from commercially available ferrocenecarboxaldehyde and a chiral diamine, is envisaged to potentially act as a chiral ligand in asymmetric catalysis.

The crystal structure of the title compound is shown in Fig. 1. It contains the (1R,2R)-(+)-1,2-diphenyl-1,2-ethanediamine subunit, meanwhile, the hydrogen atoms of the two amine groups have been substituted by ferrocenylmethyl units. The angle between the two benzene ring planes is 36.3 (1)°. The Cp ring planes (C21—C25 and C27—C31), are almost perpendicular to each other [dihedral angle 88.6 (1)°]. The intramolecular Fe—Fe distance is 7.064 Å.

For related compounds, see: Hess et al. (1999); Bâse et al. (2002); Wang (2009).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); 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: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, displacement ellipsoids are drawn at the 40% probability level.
(1R,2R)-N,N'-Bis(ferrocenylmethyl)-1,2- diphenylethane-1,2-diamine top
Crystal data top
[Fe2(C5H5)2(C26H26N2)]F(000) = 1272
Mr = 608.37Dx = 1.372 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 36065 reflections
a = 9.5080 (2) Åθ = 3.0–27.4°
b = 9.5700 (2) ŵ = 1.01 mm1
c = 32.3680 (7) ÅT = 295 K
V = 2945.21 (11) Å3Chunk, yellow
Z = 40.36 × 0.20 × 0.18 mm
Data collection top
Rigaku R-AXIS RAPID/ZJUG
diffractometer
6726 independent reflections
Radiation source: rolling anode5515 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 3.0°
ω scansh = 1211
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1212
Tmin = 0.712, Tmax = 0.839l = 4141
45235 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)] = 0.030H-atom parameters constrained
wR(F2) = 0.077 w = 1/[σ2(Fo2) + (0.0379P)2 + 0.4974P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
6726 reflectionsΔρmax = 0.37 e Å3
361 parametersΔρmin = 0.23 e Å3
30 restraintsAbsolute structure: Flack (1983), 2915 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.006 (14)
Crystal data top
[Fe2(C5H5)2(C26H26N2)]V = 2945.21 (11) Å3
Mr = 608.37Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.5080 (2) ŵ = 1.01 mm1
b = 9.5700 (2) ÅT = 295 K
c = 32.3680 (7) Å0.36 × 0.20 × 0.18 mm
Data collection top
Rigaku R-AXIS RAPID/ZJUG
diffractometer
6726 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
5515 reflections with I > 2σ(I)
Tmin = 0.712, Tmax = 0.839Rint = 0.036
45235 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.077Δρmax = 0.37 e Å3
S = 1.01Δρmin = 0.23 e Å3
6726 reflectionsAbsolute structure: Flack (1983), 2915 Friedel pairs
361 parametersAbsolute structure parameter: 0.006 (14)
30 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.43233 (3)0.37036 (4)0.323961 (10)0.04776 (9)
Fe20.94810 (3)0.90157 (4)0.321361 (10)0.04747 (9)
N20.9684 (2)0.5571 (2)0.41297 (5)0.0485 (5)
H1020.94230.50720.39220.058*
N10.7154 (2)0.4016 (2)0.40061 (6)0.0503 (5)
H1010.65630.46700.39500.060*
C30.6747 (2)0.4068 (3)0.47784 (7)0.0452 (5)
C20.8515 (2)0.5632 (3)0.44242 (6)0.0409 (5)
H20.78530.63560.43350.049*
C10.7758 (2)0.4207 (3)0.44201 (6)0.0425 (5)
H10.84810.34860.44560.051*
C90.9024 (2)0.5980 (2)0.48587 (6)0.0401 (5)
C80.7111 (3)0.3287 (3)0.51228 (8)0.0598 (7)
H80.79310.27570.51210.072*
C141.0251 (3)0.5382 (3)0.50131 (7)0.0500 (6)
H141.08190.48470.48410.060*
C150.6487 (3)0.2668 (3)0.39368 (8)0.0548 (6)
H15A0.57340.25410.41350.066*
H15B0.71720.19300.39800.066*
C261.0090 (2)0.6932 (3)0.39546 (7)0.0471 (5)
H26A1.10220.68510.38350.057*
H26B1.01390.76130.41760.057*
C100.8224 (3)0.6798 (3)0.51214 (8)0.0521 (6)
H100.74150.72290.50230.063*
C310.8056 (2)0.8517 (3)0.36615 (8)0.0549 (6)
H310.78510.90720.39090.066*
C160.5904 (3)0.2557 (3)0.35076 (7)0.0508 (6)
C270.9096 (2)0.7459 (2)0.36297 (6)0.0422 (5)
C131.0632 (3)0.5577 (3)0.54203 (8)0.0601 (7)
H131.14500.51660.55200.072*
C120.9821 (3)0.6369 (4)0.56794 (8)0.0678 (8)
H121.00830.64890.59540.081*
C280.9022 (3)0.6931 (3)0.32162 (7)0.0543 (6)
H280.96140.61890.31010.065*
C110.8618 (3)0.6985 (3)0.55323 (9)0.0652 (8)
H110.80660.75270.57070.078*
C40.5492 (3)0.4811 (3)0.47917 (8)0.0598 (6)
H40.52180.53260.45620.072*
C60.5039 (4)0.4050 (4)0.54768 (10)0.0793 (10)
H60.44770.40530.57120.095*
C200.4766 (3)0.1674 (3)0.33873 (9)0.0592 (7)
H200.42120.10760.35720.071*
C170.6403 (3)0.3242 (3)0.31475 (8)0.0614 (7)
H170.71760.39180.31360.074*
C290.7979 (3)0.7670 (4)0.30013 (9)0.0698 (9)
H290.77200.75310.27110.084*
C321.1195 (4)1.0080 (4)0.34107 (11)0.0839 (10)
H321.16121.00170.36870.101*
C50.4645 (3)0.4805 (3)0.51363 (10)0.0715 (8)
H50.38090.53110.51380.086*
C300.7372 (3)0.8646 (3)0.32714 (10)0.0702 (8)
H300.66140.93020.32040.084*
C240.2309 (3)0.4341 (4)0.31180 (11)0.0801 (9)
H240.16060.37970.29660.096*
C180.5570 (3)0.2791 (4)0.28069 (8)0.0732 (9)
H180.56760.30940.25190.088*
C190.4575 (3)0.1810 (3)0.29560 (9)0.0710 (8)
H190.38660.13240.27900.085*
C70.6253 (4)0.3293 (4)0.54704 (9)0.0785 (9)
H70.65110.27750.57010.094*
C230.3212 (4)0.5237 (4)0.29493 (11)0.0834 (10)
H230.32700.54430.26530.100*
C250.2527 (4)0.4278 (5)0.35312 (12)0.0930 (12)
H250.19930.37070.37280.112*
C351.0710 (4)0.9670 (4)0.27345 (10)0.0883 (11)
H351.07290.92730.24560.106*
C331.0145 (4)1.1026 (4)0.32899 (12)0.0847 (10)
H330.97041.17420.34630.102*
C340.9860 (4)1.0758 (4)0.28695 (11)0.0871 (10)
H340.91631.12520.27010.104*
C210.3648 (5)0.5201 (5)0.36307 (12)0.1072 (15)
H210.40180.54180.39060.129*
C361.1550 (3)0.9248 (5)0.30731 (13)0.0906 (12)
H361.22590.85040.30700.109*
C220.4070 (4)0.5806 (4)0.32431 (17)0.1047 (13)
H220.48020.65120.32000.126*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.05325 (19)0.04715 (19)0.04286 (16)0.00223 (15)0.00165 (15)0.00436 (15)
Fe20.04937 (17)0.0520 (2)0.04101 (16)0.00561 (15)0.00362 (15)0.00793 (15)
N20.0538 (11)0.0516 (12)0.0402 (10)0.0026 (9)0.0066 (9)0.0041 (8)
N10.0605 (11)0.0488 (12)0.0416 (10)0.0036 (10)0.0095 (9)0.0006 (9)
C30.0511 (12)0.0417 (13)0.0426 (11)0.0078 (10)0.0028 (9)0.0007 (10)
C20.0410 (11)0.0424 (13)0.0395 (11)0.0026 (9)0.0006 (9)0.0067 (9)
C10.0450 (11)0.0431 (13)0.0393 (11)0.0010 (10)0.0028 (9)0.0029 (9)
C90.0372 (10)0.0403 (12)0.0427 (11)0.0056 (9)0.0007 (9)0.0022 (9)
C80.0799 (18)0.0500 (16)0.0495 (14)0.0002 (14)0.0017 (13)0.0085 (12)
C140.0457 (13)0.0517 (15)0.0528 (14)0.0016 (11)0.0024 (10)0.0005 (11)
C150.0597 (15)0.0459 (15)0.0588 (14)0.0028 (11)0.0106 (12)0.0009 (12)
C260.0458 (12)0.0544 (15)0.0413 (11)0.0063 (10)0.0005 (10)0.0051 (10)
C100.0434 (12)0.0559 (16)0.0572 (14)0.0022 (11)0.0015 (11)0.0082 (12)
C310.0498 (13)0.0582 (17)0.0565 (14)0.0026 (12)0.0170 (11)0.0018 (12)
C160.0503 (14)0.0485 (14)0.0535 (13)0.0061 (11)0.0017 (11)0.0110 (11)
C270.0425 (12)0.0466 (13)0.0374 (10)0.0068 (10)0.0061 (9)0.0022 (9)
C130.0526 (14)0.0753 (18)0.0523 (13)0.0063 (14)0.0145 (13)0.0087 (12)
C120.0673 (17)0.090 (2)0.0458 (14)0.0214 (16)0.0069 (12)0.0039 (14)
C280.0700 (15)0.0517 (14)0.0412 (11)0.0092 (12)0.0013 (12)0.0028 (12)
C110.0606 (17)0.075 (2)0.0603 (16)0.0106 (15)0.0087 (14)0.0234 (15)
C40.0498 (14)0.0714 (18)0.0582 (14)0.0008 (13)0.0009 (13)0.0028 (12)
C60.091 (2)0.076 (2)0.0701 (19)0.0240 (19)0.0350 (17)0.0107 (17)
C200.0592 (15)0.0398 (14)0.0786 (17)0.0041 (11)0.0131 (13)0.0091 (12)
C170.0529 (14)0.078 (2)0.0527 (15)0.0027 (13)0.0100 (12)0.0141 (14)
C290.0742 (19)0.084 (2)0.0510 (15)0.0227 (17)0.0184 (14)0.0103 (15)
C320.0736 (19)0.105 (3)0.0736 (19)0.0429 (19)0.0034 (16)0.0102 (19)
C50.0549 (17)0.080 (2)0.0794 (18)0.0115 (15)0.0153 (15)0.0085 (16)
C300.0423 (12)0.083 (2)0.086 (2)0.0008 (13)0.0033 (14)0.0305 (19)
C240.0648 (17)0.080 (2)0.096 (3)0.0132 (17)0.0069 (17)0.0020 (19)
C180.0751 (19)0.096 (2)0.0483 (14)0.0130 (19)0.0027 (15)0.0240 (14)
C190.0755 (19)0.0642 (19)0.0734 (18)0.0088 (17)0.0200 (16)0.0295 (15)
C70.117 (3)0.067 (2)0.0517 (15)0.013 (2)0.0089 (17)0.0135 (14)
C230.091 (2)0.079 (3)0.080 (2)0.013 (2)0.0009 (19)0.0228 (19)
C250.096 (2)0.097 (3)0.086 (2)0.045 (2)0.039 (2)0.023 (2)
C350.103 (3)0.100 (3)0.0622 (18)0.026 (2)0.026 (2)0.0171 (18)
C330.099 (2)0.0587 (18)0.096 (2)0.0257 (17)0.0102 (19)0.0013 (17)
C340.099 (2)0.077 (2)0.085 (2)0.020 (2)0.0014 (19)0.0404 (19)
C210.129 (3)0.111 (3)0.081 (2)0.075 (2)0.046 (2)0.057 (2)
C360.0541 (16)0.097 (3)0.121 (3)0.0101 (18)0.0260 (18)0.023 (2)
C220.088 (2)0.0461 (18)0.180 (4)0.0015 (16)0.009 (3)0.010 (2)
Geometric parameters (Å, º) top
Fe1—C212.017 (3)C31—H310.9800
Fe1—C222.027 (3)C16—C171.419 (4)
Fe1—C252.028 (3)C16—C201.427 (4)
Fe1—C182.032 (3)C27—C281.432 (3)
Fe1—C232.038 (3)C13—C121.368 (4)
Fe1—C202.044 (3)C13—H130.9300
Fe1—C192.045 (3)C12—C111.371 (4)
Fe1—C242.048 (3)C12—H120.9300
Fe1—C172.048 (3)C28—C291.403 (4)
Fe1—C162.053 (3)C28—H280.9800
Fe2—C322.025 (3)C11—H110.9300
Fe2—C362.031 (3)C4—C51.376 (4)
Fe2—C342.037 (3)C4—H40.9300
Fe2—C332.040 (3)C6—C71.363 (5)
Fe2—C352.040 (3)C6—C51.370 (5)
Fe2—C312.041 (2)C6—H60.9300
Fe2—C272.041 (2)C20—C191.414 (4)
Fe2—C282.043 (3)C20—H200.9800
Fe2—C292.042 (3)C17—C181.425 (4)
Fe2—C302.045 (3)C17—H170.9800
N2—C21.466 (3)C29—C301.403 (4)
N2—C261.472 (3)C29—H290.9800
N2—H1020.8600C32—C361.394 (5)
N1—C151.455 (3)C32—C331.403 (5)
N1—C11.469 (3)C32—H320.9800
N1—H1010.8599C5—H50.9300
C3—C81.386 (3)C30—H300.9800
C3—C41.389 (3)C24—C231.331 (5)
C3—C11.513 (3)C24—C251.355 (5)
C2—C91.524 (3)C24—H240.9800
C2—C11.542 (3)C18—C191.418 (4)
C2—H20.9800C18—H180.9800
C1—H10.9800C19—H190.9800
C9—C101.384 (3)C7—H70.9300
C9—C141.393 (3)C23—C221.366 (5)
C8—C71.389 (4)C23—H230.9800
C8—H80.9300C25—C211.422 (6)
C14—C131.379 (3)C25—H250.9800
C14—H140.9300C35—C341.388 (5)
C15—C161.500 (3)C35—C361.415 (5)
C15—H15A0.9700C35—H350.9800
C15—H15B0.9700C33—C341.411 (5)
C26—C271.501 (3)C33—H330.9800
C26—H26A0.9700C34—H340.9800
C26—H26B0.9700C21—C221.439 (6)
C10—C111.393 (4)C21—H210.9800
C10—H100.9300C36—H360.9800
C31—C271.419 (3)C22—H220.9800
C31—C301.426 (4)
C21—Fe1—C2241.69 (17)C27—C31—H31125.8
C21—Fe1—C2541.16 (17)C30—C31—H31125.8
C22—Fe1—C2568.18 (17)Fe2—C31—H31125.8
C21—Fe1—C18157.5 (2)C17—C16—C20107.6 (2)
C22—Fe1—C18119.99 (18)C17—C16—C15127.2 (2)
C25—Fe1—C18158.24 (17)C20—C16—C15125.1 (2)
C21—Fe1—C2367.22 (15)C17—C16—Fe169.57 (15)
C22—Fe1—C2339.29 (15)C20—C16—Fe169.28 (14)
C25—Fe1—C2365.34 (14)C15—C16—Fe1128.65 (18)
C18—Fe1—C23107.09 (14)C31—C27—C28106.6 (2)
C21—Fe1—C20126.43 (17)C31—C27—C26128.9 (2)
C22—Fe1—C20165.16 (17)C28—C27—C26124.6 (2)
C25—Fe1—C20108.78 (14)C31—C27—Fe269.63 (13)
C18—Fe1—C2068.46 (13)C28—C27—Fe269.51 (13)
C23—Fe1—C20154.00 (14)C26—C27—Fe2126.48 (16)
C21—Fe1—C19161.5 (2)C12—C13—C14120.8 (3)
C22—Fe1—C19153.65 (19)C12—C13—H13119.6
C25—Fe1—C19123.20 (17)C14—C13—H13119.6
C18—Fe1—C1940.69 (13)C13—C12—C11119.7 (2)
C23—Fe1—C19119.45 (14)C13—C12—H12120.2
C20—Fe1—C1940.45 (11)C11—C12—H12120.2
C21—Fe1—C2467.14 (15)C29—C28—C27108.7 (3)
C22—Fe1—C2466.07 (16)C29—C28—Fe269.90 (16)
C25—Fe1—C2438.83 (14)C27—C28—Fe269.43 (14)
C18—Fe1—C24122.74 (13)C29—C28—H28125.7
C23—Fe1—C2438.02 (14)C27—C28—H28125.7
C20—Fe1—C24121.35 (14)Fe2—C28—H28125.7
C19—Fe1—C24106.67 (14)C12—C11—C10120.0 (3)
C21—Fe1—C17123.49 (16)C12—C11—H11120.0
C22—Fe1—C17109.24 (15)C10—C11—H11120.0
C25—Fe1—C17160.00 (15)C5—C4—C3121.7 (3)
C18—Fe1—C1740.88 (11)C5—C4—H4119.1
C23—Fe1—C17126.06 (14)C3—C4—H4119.1
C20—Fe1—C1768.31 (12)C7—C6—C5120.0 (3)
C19—Fe1—C1768.33 (13)C7—C6—H6120.0
C24—Fe1—C17159.91 (13)C5—C6—H6120.0
C21—Fe1—C16110.33 (12)C19—C20—C16108.2 (3)
C22—Fe1—C16127.96 (15)C19—C20—Fe169.82 (17)
C25—Fe1—C16124.39 (13)C16—C20—Fe169.94 (15)
C18—Fe1—C1668.58 (11)C19—C20—H20125.9
C23—Fe1—C16163.57 (14)C16—C20—H20125.9
C20—Fe1—C1640.77 (10)Fe1—C20—H20125.9
C19—Fe1—C1668.32 (11)C16—C17—C18108.0 (3)
C24—Fe1—C16157.64 (13)C16—C17—Fe169.94 (14)
C17—Fe1—C1640.49 (11)C18—C17—Fe168.95 (15)
C32—Fe2—C3640.19 (15)C16—C17—H17126.0
C32—Fe2—C3467.56 (15)C18—C17—H17126.0
C36—Fe2—C3467.48 (16)Fe1—C17—H17126.0
C32—Fe2—C3340.38 (15)C30—C29—C28108.5 (2)
C36—Fe2—C3367.92 (17)C30—C29—Fe270.03 (17)
C34—Fe2—C3340.50 (14)C28—C29—Fe269.93 (15)
C32—Fe2—C3567.93 (14)C30—C29—H29125.7
C36—Fe2—C3540.68 (14)C28—C29—H29125.7
C34—Fe2—C3539.82 (14)Fe2—C29—H29125.7
C33—Fe2—C3567.99 (15)C36—C32—C33108.8 (3)
C32—Fe2—C31115.35 (13)C36—C32—Fe270.16 (19)
C36—Fe2—C31145.84 (14)C33—C32—Fe270.39 (19)
C34—Fe2—C31134.21 (15)C36—C32—H32125.6
C33—Fe2—C31109.89 (13)C33—C32—H32125.6
C35—Fe2—C31172.72 (14)Fe2—C32—H32125.6
C32—Fe2—C27107.67 (12)C6—C5—C4119.6 (3)
C36—Fe2—C27113.64 (14)C6—C5—H5120.2
C34—Fe2—C27171.77 (14)C4—C5—H5120.2
C33—Fe2—C27131.60 (12)C29—C30—C31107.8 (2)
C35—Fe2—C27145.91 (14)C29—C30—Fe269.81 (16)
C31—Fe2—C2740.68 (10)C31—C30—Fe269.40 (13)
C32—Fe2—C28131.46 (15)C29—C30—H30126.1
C36—Fe2—C28108.35 (15)C31—C30—H30126.1
C34—Fe2—C28147.09 (14)Fe2—C30—H30126.1
C33—Fe2—C28170.75 (14)C23—C24—C25109.6 (4)
C35—Fe2—C28115.18 (14)C23—C24—Fe170.6 (2)
C31—Fe2—C2868.07 (11)C25—C24—Fe169.8 (2)
C27—Fe2—C2841.06 (9)C23—C24—H24125.2
C32—Fe2—C29170.43 (17)C25—C24—H24125.2
C36—Fe2—C29132.14 (17)Fe1—C24—H24125.2
C34—Fe2—C29117.11 (13)C19—C18—C17108.0 (3)
C33—Fe2—C29148.42 (15)C19—C18—Fe170.17 (16)
C35—Fe2—C29109.77 (14)C17—C18—Fe170.18 (14)
C31—Fe2—C2968.11 (12)C19—C18—H18126.0
C27—Fe2—C2968.68 (10)C17—C18—H18126.0
C28—Fe2—C2940.17 (11)Fe1—C18—H18126.0
C32—Fe2—C30147.94 (16)C20—C19—C18108.2 (3)
C36—Fe2—C30171.54 (16)C20—C19—Fe169.73 (15)
C34—Fe2—C30111.41 (14)C18—C19—Fe169.14 (16)
C33—Fe2—C30117.11 (15)C20—C19—H19125.9
C35—Fe2—C30133.17 (14)C18—C19—H19125.9
C31—Fe2—C3040.85 (11)Fe1—C19—H19125.9
C27—Fe2—C3068.75 (10)C6—C7—C8120.8 (3)
C28—Fe2—C3067.72 (12)C6—C7—H7119.6
C29—Fe2—C3040.16 (13)C8—C7—H7119.6
C2—N2—C26114.44 (19)C24—C23—C22110.9 (4)
C2—N2—H102108.1C24—C23—Fe171.4 (2)
C26—N2—H102105.5C22—C23—Fe169.9 (2)
C15—N1—C1114.88 (19)C24—C23—H23124.6
C15—N1—H101109.1C22—C23—H23124.6
C1—N1—H101111.0Fe1—C23—H23124.6
C8—C3—C4117.7 (2)C24—C25—C21108.1 (4)
C8—C3—C1120.3 (2)C24—C25—Fe171.39 (19)
C4—C3—C1121.6 (2)C21—C25—Fe169.0 (2)
N2—C2—C9111.58 (17)C24—C25—H25126.0
N2—C2—C1108.22 (19)C21—C25—H25126.0
C9—C2—C1110.45 (17)Fe1—C25—H25126.0
N2—C2—H2108.8C34—C35—C36107.4 (3)
C9—C2—H2108.8C34—C35—Fe269.98 (18)
C1—C2—H2108.8C36—C35—Fe269.32 (17)
N1—C1—C3116.08 (19)C34—C35—H35126.3
N1—C1—C2107.45 (17)C36—C35—H35126.3
C3—C1—C2111.57 (19)Fe2—C35—H35126.3
N1—C1—H1107.1C32—C33—C34106.8 (3)
C3—C1—H1107.1C32—C33—Fe269.23 (19)
C2—C1—H1107.1C34—C33—Fe269.65 (19)
C10—C9—C14118.2 (2)C32—C33—H33126.6
C10—C9—C2121.1 (2)C34—C33—H33126.6
C14—C9—C2120.5 (2)Fe2—C33—H33126.6
C3—C8—C7120.2 (3)C35—C34—C33109.1 (3)
C3—C8—H8119.9C35—C34—Fe270.20 (19)
C7—C8—H8119.9C33—C34—Fe269.84 (17)
C13—C14—C9120.5 (2)C35—C34—H34125.4
C13—C14—H14119.8C33—C34—H34125.4
C9—C14—H14119.8Fe2—C34—H34125.4
N1—C15—C16111.5 (2)C25—C21—C22105.2 (3)
N1—C15—H15A109.3C25—C21—Fe169.81 (18)
C16—C15—H15A109.3C22—C21—Fe169.51 (19)
N1—C15—H15B109.3C25—C21—H21127.4
C16—C15—H15B109.3C22—C21—H21127.4
H15A—C15—H15B108.0Fe1—C21—H21127.4
N2—C26—C27113.71 (19)C32—C36—C35107.9 (4)
N2—C26—H26A108.8C32—C36—Fe269.65 (18)
C27—C26—H26A108.8C35—C36—Fe270.00 (18)
N2—C26—H26B108.8C32—C36—H36126.1
C27—C26—H26B108.8C35—C36—H36126.1
H26A—C26—H26B107.7Fe2—C36—H36126.1
C9—C10—C11120.8 (2)C23—C22—C21106.3 (3)
C9—C10—H10119.6C23—C22—Fe170.8 (2)
C11—C10—H10119.6C21—C22—Fe168.8 (2)
C27—C31—C30108.4 (2)C23—C22—H22126.9
C27—C31—Fe269.69 (12)C21—C22—H22126.9
C30—C31—Fe269.75 (14)Fe1—C22—H22126.9
C26—N2—C2—C985.0 (2)C27—Fe2—C30—C3137.41 (16)
C26—N2—C2—C1153.26 (18)C28—Fe2—C30—C3181.77 (17)
C15—N1—C1—C358.8 (3)C29—Fe2—C30—C31119.1 (3)
C15—N1—C1—C2175.5 (2)C21—Fe1—C24—C2381.8 (3)
C8—C3—C1—N1134.4 (2)C22—Fe1—C24—C2336.2 (3)
C4—C3—C1—N151.6 (3)C25—Fe1—C24—C23120.6 (4)
C8—C3—C1—C2102.1 (3)C18—Fe1—C24—C2375.2 (3)
C4—C3—C1—C271.9 (3)C20—Fe1—C24—C23158.4 (2)
N2—C2—C1—N164.2 (2)C19—Fe1—C24—C23116.8 (3)
C9—C2—C1—N1173.44 (18)C17—Fe1—C24—C2344.4 (5)
N2—C2—C1—C3167.55 (17)C16—Fe1—C24—C23169.8 (3)
C9—C2—C1—C345.1 (2)C21—Fe1—C24—C2538.8 (3)
N2—C2—C9—C10144.6 (2)C22—Fe1—C24—C2584.4 (3)
C1—C2—C9—C1095.0 (3)C18—Fe1—C24—C25164.2 (3)
N2—C2—C9—C1440.9 (3)C23—Fe1—C24—C25120.6 (4)
C1—C2—C9—C1479.5 (2)C20—Fe1—C24—C2581.0 (3)
C4—C3—C8—C71.7 (4)C19—Fe1—C24—C25122.6 (3)
C1—C3—C8—C7172.5 (3)C17—Fe1—C24—C25165.0 (4)
C10—C9—C14—C131.6 (4)C16—Fe1—C24—C2549.3 (5)
C2—C9—C14—C13173.0 (2)C16—C17—C18—C191.1 (3)
C1—N1—C15—C16179.8 (2)Fe1—C17—C18—C1960.3 (2)
C2—N2—C26—C2776.0 (2)C16—C17—C18—Fe159.21 (19)
C14—C9—C10—C111.8 (4)C21—Fe1—C18—C19172.9 (3)
C2—C9—C10—C11172.8 (2)C22—Fe1—C18—C19156.3 (2)
C32—Fe2—C31—C2787.9 (2)C25—Fe1—C18—C1949.6 (5)
C36—Fe2—C31—C2751.8 (3)C23—Fe1—C18—C19115.6 (2)
C34—Fe2—C31—C27170.57 (18)C20—Fe1—C18—C1937.27 (18)
C33—Fe2—C31—C27131.48 (17)C24—Fe1—C18—C1977.0 (2)
C28—Fe2—C31—C2738.86 (14)C17—Fe1—C18—C19118.6 (3)
C29—Fe2—C31—C2782.32 (17)C16—Fe1—C18—C1981.24 (19)
C30—Fe2—C31—C27119.7 (2)C21—Fe1—C18—C1754.3 (4)
C32—Fe2—C31—C30152.4 (2)C22—Fe1—C18—C1785.1 (2)
C36—Fe2—C31—C30171.5 (3)C25—Fe1—C18—C17168.2 (4)
C34—Fe2—C31—C3069.7 (3)C23—Fe1—C18—C17125.9 (2)
C33—Fe2—C31—C30108.8 (2)C20—Fe1—C18—C1781.3 (2)
C27—Fe2—C31—C30119.7 (2)C19—Fe1—C18—C17118.6 (3)
C28—Fe2—C31—C3080.83 (19)C24—Fe1—C18—C17164.4 (2)
C29—Fe2—C31—C3037.38 (19)C16—Fe1—C18—C1737.34 (18)
N1—C15—C16—C1728.7 (4)C16—C20—C19—C181.0 (3)
N1—C15—C16—C20154.4 (2)Fe1—C20—C19—C1858.6 (2)
N1—C15—C16—Fe164.0 (3)C16—C20—C19—Fe159.64 (18)
C21—Fe1—C16—C17118.2 (2)C17—C18—C19—C201.3 (3)
C22—Fe1—C16—C1774.3 (3)Fe1—C18—C19—C2059.0 (2)
C25—Fe1—C16—C17162.2 (2)C17—C18—C19—Fe160.3 (2)
C18—Fe1—C16—C1737.69 (18)C21—Fe1—C19—C2051.6 (5)
C23—Fe1—C16—C1739.9 (5)C22—Fe1—C19—C20171.4 (3)
C20—Fe1—C16—C17119.1 (2)C25—Fe1—C19—C2080.0 (2)
C19—Fe1—C16—C1781.59 (18)C18—Fe1—C19—C20119.8 (3)
C24—Fe1—C16—C17162.7 (3)C23—Fe1—C19—C20158.24 (19)
C21—Fe1—C16—C20122.7 (2)C24—Fe1—C19—C20119.1 (2)
C22—Fe1—C16—C20166.6 (2)C17—Fe1—C19—C2081.55 (19)
C25—Fe1—C16—C2078.7 (2)C16—Fe1—C19—C2037.83 (17)
C18—Fe1—C16—C2081.43 (18)C21—Fe1—C19—C18171.4 (4)
C23—Fe1—C16—C20159.0 (4)C22—Fe1—C19—C1851.6 (4)
C19—Fe1—C16—C2037.54 (18)C25—Fe1—C19—C18160.29 (19)
C24—Fe1—C16—C2043.5 (4)C23—Fe1—C19—C1882.0 (2)
C17—Fe1—C16—C20119.1 (2)C20—Fe1—C19—C18119.8 (3)
C21—Fe1—C16—C153.7 (3)C24—Fe1—C19—C18121.18 (19)
C22—Fe1—C16—C1547.5 (3)C17—Fe1—C19—C1838.20 (17)
C25—Fe1—C16—C1540.3 (3)C16—Fe1—C19—C1881.92 (19)
C18—Fe1—C16—C15159.6 (3)C5—C6—C7—C80.6 (5)
C23—Fe1—C16—C1581.9 (5)C3—C8—C7—C60.8 (5)
C20—Fe1—C16—C15119.0 (3)C25—C24—C23—C220.1 (4)
C19—Fe1—C16—C15156.5 (3)Fe1—C24—C23—C2258.9 (3)
C24—Fe1—C16—C1575.5 (4)C25—C24—C23—Fe159.0 (3)
C17—Fe1—C16—C15121.9 (3)C21—Fe1—C23—C2481.5 (3)
C30—C31—C27—C280.8 (3)C22—Fe1—C23—C24121.6 (4)
Fe2—C31—C27—C2860.00 (16)C25—Fe1—C23—C2436.4 (2)
C30—C31—C27—C26179.8 (2)C18—Fe1—C23—C24121.7 (2)
Fe2—C31—C27—C26121.0 (2)C20—Fe1—C23—C2445.9 (4)
C30—C31—C27—Fe259.19 (17)C19—Fe1—C23—C2479.2 (3)
N2—C26—C27—C31103.7 (3)C17—Fe1—C23—C24162.7 (2)
N2—C26—C27—C2875.1 (3)C16—Fe1—C23—C24166.3 (4)
N2—C26—C27—Fe2164.03 (15)C21—Fe1—C23—C2240.0 (3)
C32—Fe2—C27—C31108.58 (19)C25—Fe1—C23—C2285.1 (3)
C36—Fe2—C27—C31151.2 (2)C18—Fe1—C23—C22116.7 (3)
C33—Fe2—C27—C3170.4 (2)C20—Fe1—C23—C22167.5 (3)
C35—Fe2—C27—C31174.9 (2)C19—Fe1—C23—C22159.2 (3)
C28—Fe2—C27—C31117.6 (2)C24—Fe1—C23—C22121.6 (4)
C29—Fe2—C27—C3180.80 (18)C17—Fe1—C23—C2275.7 (3)
C30—Fe2—C27—C3137.56 (17)C16—Fe1—C23—C2244.7 (6)
C32—Fe2—C27—C28133.82 (18)C23—C24—C25—C210.0 (4)
C36—Fe2—C27—C2891.2 (2)Fe1—C24—C25—C2159.5 (2)
C33—Fe2—C27—C28172.0 (2)C23—C24—C25—Fe159.5 (3)
C35—Fe2—C27—C2857.3 (3)C21—Fe1—C25—C24118.7 (3)
C31—Fe2—C27—C28117.6 (2)C22—Fe1—C25—C2478.5 (3)
C29—Fe2—C27—C2836.80 (17)C18—Fe1—C25—C2438.2 (5)
C30—Fe2—C27—C2880.04 (18)C23—Fe1—C25—C2435.7 (2)
C32—Fe2—C27—C2615.3 (2)C20—Fe1—C25—C24117.0 (2)
C36—Fe2—C27—C2627.3 (3)C19—Fe1—C25—C2474.6 (3)
C33—Fe2—C27—C2653.5 (3)C17—Fe1—C25—C24164.9 (4)
C35—Fe2—C27—C2661.2 (3)C16—Fe1—C25—C24159.6 (2)
C31—Fe2—C27—C26123.9 (3)C22—Fe1—C25—C2140.2 (2)
C28—Fe2—C27—C26118.5 (3)C18—Fe1—C25—C21156.9 (4)
C29—Fe2—C27—C26155.3 (2)C23—Fe1—C25—C2183.0 (2)
C30—Fe2—C27—C26161.5 (2)C20—Fe1—C25—C21124.3 (2)
C9—C14—C13—C120.5 (4)C19—Fe1—C25—C21166.8 (2)
C14—C13—C12—C110.4 (4)C24—Fe1—C25—C21118.7 (3)
C31—C27—C28—C291.0 (3)C17—Fe1—C25—C2146.3 (5)
C26—C27—C28—C29179.9 (2)C16—Fe1—C25—C2181.8 (3)
Fe2—C27—C28—C2959.04 (18)C32—Fe2—C35—C3481.0 (3)
C31—C27—C28—Fe260.08 (16)C36—Fe2—C35—C34118.5 (4)
C26—C27—C28—Fe2120.9 (2)C33—Fe2—C35—C3437.3 (2)
C32—Fe2—C28—C29173.3 (2)C27—Fe2—C35—C34170.1 (2)
C36—Fe2—C28—C29134.7 (2)C28—Fe2—C35—C34152.2 (2)
C34—Fe2—C28—C2958.0 (3)C29—Fe2—C35—C34109.0 (2)
C35—Fe2—C28—C2991.3 (2)C30—Fe2—C35—C3469.9 (3)
C31—Fe2—C28—C2981.60 (18)C32—Fe2—C35—C3637.6 (2)
C27—Fe2—C28—C29120.1 (2)C34—Fe2—C35—C36118.5 (4)
C30—Fe2—C28—C2937.35 (17)C33—Fe2—C35—C3681.3 (3)
C32—Fe2—C28—C2766.6 (2)C27—Fe2—C35—C3651.6 (3)
C36—Fe2—C28—C27105.22 (19)C28—Fe2—C35—C3689.2 (3)
C34—Fe2—C28—C27178.1 (2)C29—Fe2—C35—C36132.5 (3)
C35—Fe2—C28—C27148.59 (17)C30—Fe2—C35—C36171.6 (2)
C31—Fe2—C28—C2738.51 (14)C36—C32—C33—C340.0 (4)
C29—Fe2—C28—C27120.1 (2)Fe2—C32—C33—C3459.8 (2)
C30—Fe2—C28—C2782.77 (16)C36—C32—C33—Fe259.9 (2)
C13—C12—C11—C100.3 (5)C36—Fe2—C33—C3237.3 (2)
C9—C10—C11—C120.8 (4)C34—Fe2—C33—C32118.0 (3)
C8—C3—C4—C51.4 (4)C35—Fe2—C33—C3281.4 (2)
C1—C3—C4—C5172.8 (3)C31—Fe2—C33—C32106.1 (2)
C17—C16—C20—C190.4 (3)C27—Fe2—C33—C3265.3 (3)
C15—C16—C20—C19177.0 (2)C29—Fe2—C33—C32173.6 (2)
Fe1—C16—C20—C1959.57 (19)C30—Fe2—C33—C32150.2 (2)
C17—C16—C20—Fe159.21 (19)C32—Fe2—C33—C34118.0 (3)
C15—C16—C20—Fe1123.4 (2)C36—Fe2—C33—C3480.7 (2)
C21—Fe1—C20—C19162.0 (2)C35—Fe2—C33—C3436.6 (2)
C22—Fe1—C20—C19164.9 (5)C31—Fe2—C33—C34135.9 (2)
C25—Fe1—C20—C19119.5 (2)C27—Fe2—C33—C34176.7 (2)
C18—Fe1—C20—C1937.48 (18)C29—Fe2—C33—C3455.6 (4)
C23—Fe1—C20—C1947.4 (4)C30—Fe2—C33—C3491.8 (2)
C24—Fe1—C20—C1978.6 (2)C36—C35—C34—C330.3 (4)
C17—Fe1—C20—C1981.61 (19)Fe2—C35—C34—C3359.2 (2)
C16—Fe1—C20—C19119.2 (3)C36—C35—C34—Fe259.5 (2)
C21—Fe1—C20—C1678.8 (2)C32—C33—C34—C350.2 (4)
C22—Fe1—C20—C1645.7 (6)Fe2—C33—C34—C3559.4 (2)
C25—Fe1—C20—C16121.3 (2)C32—C33—C34—Fe259.6 (2)
C18—Fe1—C20—C1681.75 (17)C32—Fe2—C34—C3582.0 (3)
C23—Fe1—C20—C16166.7 (3)C36—Fe2—C34—C3538.3 (2)
C19—Fe1—C20—C16119.2 (3)C33—Fe2—C34—C35120.2 (3)
C24—Fe1—C20—C16162.13 (17)C31—Fe2—C34—C35173.9 (2)
C17—Fe1—C20—C1637.62 (15)C28—Fe2—C34—C3550.9 (4)
C20—C16—C17—C180.4 (3)C29—Fe2—C34—C3588.8 (3)
C15—C16—C17—C18177.8 (3)C30—Fe2—C34—C35132.6 (2)
Fe1—C16—C17—C1858.6 (2)C32—Fe2—C34—C3338.2 (2)
C20—C16—C17—Fe159.03 (18)C36—Fe2—C34—C3381.9 (3)
C15—C16—C17—Fe1123.6 (3)C35—Fe2—C34—C33120.2 (3)
C21—Fe1—C17—C1682.3 (2)C31—Fe2—C34—C3365.9 (3)
C22—Fe1—C17—C16126.5 (2)C28—Fe2—C34—C33171.1 (2)
C25—Fe1—C17—C1647.6 (5)C29—Fe2—C34—C33151.0 (2)
C18—Fe1—C17—C16119.6 (3)C30—Fe2—C34—C33107.1 (2)
C23—Fe1—C17—C16167.03 (19)C24—C25—C21—C220.1 (4)
C20—Fe1—C17—C1637.88 (15)Fe1—C25—C21—C2260.9 (2)
C19—Fe1—C17—C1681.56 (18)C24—C25—C21—Fe161.0 (2)
C24—Fe1—C17—C16160.7 (4)C22—Fe1—C21—C25115.8 (3)
C21—Fe1—C17—C18158.1 (3)C18—Fe1—C21—C25157.7 (3)
C22—Fe1—C17—C18113.9 (3)C23—Fe1—C21—C2578.0 (2)
C25—Fe1—C17—C18167.1 (4)C20—Fe1—C21—C2576.3 (2)
C23—Fe1—C17—C1873.4 (3)C19—Fe1—C21—C2537.1 (5)
C20—Fe1—C17—C1881.7 (2)C24—Fe1—C21—C2536.7 (2)
C19—Fe1—C17—C1838.0 (2)C17—Fe1—C21—C25162.8 (2)
C24—Fe1—C17—C1841.2 (5)C16—Fe1—C21—C25119.4 (2)
C16—Fe1—C17—C18119.6 (3)C25—Fe1—C21—C22115.8 (3)
C27—C28—C29—C300.9 (3)C18—Fe1—C21—C2241.9 (4)
Fe2—C28—C29—C3059.6 (2)C23—Fe1—C21—C2237.8 (2)
C27—C28—C29—Fe258.75 (17)C20—Fe1—C21—C22167.9 (2)
C36—Fe2—C29—C30174.9 (2)C19—Fe1—C21—C22152.9 (4)
C34—Fe2—C29—C3091.7 (2)C24—Fe1—C21—C2279.1 (2)
C33—Fe2—C29—C3054.7 (3)C17—Fe1—C21—C2281.4 (2)
C35—Fe2—C29—C30134.5 (2)C16—Fe1—C21—C22124.8 (2)
C31—Fe2—C29—C3038.01 (17)C33—C32—C36—C350.2 (4)
C27—Fe2—C29—C3081.91 (17)Fe2—C32—C36—C3559.8 (2)
C28—Fe2—C29—C30119.5 (2)C33—C32—C36—Fe260.0 (2)
C36—Fe2—C29—C2865.6 (2)C34—C35—C36—C320.3 (4)
C34—Fe2—C29—C28148.84 (19)Fe2—C35—C36—C3259.6 (2)
C33—Fe2—C29—C28174.2 (2)C34—C35—C36—Fe259.9 (2)
C35—Fe2—C29—C28106.0 (2)C34—Fe2—C36—C3281.4 (3)
C31—Fe2—C29—C2881.48 (17)C33—Fe2—C36—C3237.5 (2)
C27—Fe2—C29—C2837.58 (15)C35—Fe2—C36—C32118.9 (4)
C30—Fe2—C29—C28119.5 (2)C31—Fe2—C36—C3255.7 (4)
C34—Fe2—C32—C3681.2 (3)C27—Fe2—C36—C3289.7 (2)
C33—Fe2—C32—C36119.5 (3)C28—Fe2—C36—C32133.5 (2)
C35—Fe2—C32—C3638.0 (2)C29—Fe2—C36—C32171.7 (2)
C31—Fe2—C32—C36149.1 (2)C32—Fe2—C36—C35118.9 (4)
C27—Fe2—C32—C36106.0 (2)C34—Fe2—C36—C3537.5 (2)
C28—Fe2—C32—C3666.7 (3)C33—Fe2—C36—C3581.5 (3)
C30—Fe2—C32—C36176.0 (2)C31—Fe2—C36—C35174.7 (2)
C36—Fe2—C32—C33119.5 (3)C27—Fe2—C36—C35151.3 (2)
C34—Fe2—C32—C3338.3 (2)C28—Fe2—C36—C35107.6 (2)
C35—Fe2—C32—C3381.5 (2)C29—Fe2—C36—C3569.3 (3)
C31—Fe2—C32—C3391.4 (2)C24—C23—C22—C210.2 (4)
C27—Fe2—C32—C33134.5 (2)Fe1—C23—C22—C2160.0 (2)
C28—Fe2—C32—C33173.7 (2)C24—C23—C22—Fe159.8 (3)
C30—Fe2—C32—C3356.5 (3)C25—C21—C22—C230.2 (4)
C7—C6—C5—C41.0 (5)Fe1—C21—C22—C2361.3 (3)
C3—C4—C5—C60.0 (5)C25—C21—C22—Fe161.1 (2)
C28—C29—C30—C310.4 (3)C21—Fe1—C22—C23116.9 (3)
Fe2—C29—C30—C3159.20 (19)C25—Fe1—C22—C2377.3 (2)
C28—C29—C30—Fe259.56 (19)C18—Fe1—C22—C2380.2 (3)
C27—C31—C30—C290.3 (3)C20—Fe1—C22—C23158.3 (5)
Fe2—C31—C30—C2959.5 (2)C19—Fe1—C22—C2344.1 (4)
C27—C31—C30—Fe259.16 (17)C24—Fe1—C22—C2335.0 (2)
C32—Fe2—C30—C29171.3 (3)C17—Fe1—C22—C23123.9 (2)
C34—Fe2—C30—C29107.1 (2)C16—Fe1—C22—C23165.4 (2)
C33—Fe2—C30—C29151.32 (19)C25—Fe1—C22—C2139.7 (2)
C35—Fe2—C30—C2966.9 (3)C18—Fe1—C22—C21162.8 (2)
C31—Fe2—C30—C29119.1 (3)C23—Fe1—C22—C21116.9 (3)
C27—Fe2—C30—C2981.71 (18)C20—Fe1—C22—C2141.3 (7)
C28—Fe2—C30—C2937.36 (16)C19—Fe1—C22—C21161.0 (3)
C32—Fe2—C30—C3152.2 (3)C24—Fe1—C22—C2181.9 (2)
C34—Fe2—C30—C31133.8 (2)C17—Fe1—C22—C21119.1 (2)
C33—Fe2—C30—C3189.6 (2)C16—Fe1—C22—C2177.7 (3)
C35—Fe2—C30—C31174.0 (2)

Experimental details

Crystal data
Chemical formula[Fe2(C5H5)2(C26H26N2)]
Mr608.37
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)9.5080 (2), 9.5700 (2), 32.3680 (7)
V3)2945.21 (11)
Z4
Radiation typeMo Kα
µ (mm1)1.01
Crystal size (mm)0.36 × 0.20 × 0.18
Data collection
DiffractometerRigaku R-AXIS RAPID/ZJUG
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.712, 0.839
No. of measured, independent and
observed [I > 2σ(I)] reflections
45235, 6726, 5515
Rint0.036
(sin θ/λ)max1)0.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.077, 1.01
No. of reflections6726
No. of parameters361
No. of restraints30
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.23
Absolute structureFlack (1983), 2915 Friedel pairs
Absolute structure parameter0.006 (14)

Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Acknowledgements

The authors are grateful to Mr. Jianming Gu for the crystal analysis.

References

First citationBâse, T., Císařová, I. & Štěpnička, P. (2002). Inorg. Chem. Commun. 5, 46–50.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHess, A., Brosch, O., Weyhermüller, T. & Metzler-Nolte, N. (1999). J. Organomet. Chem. 589, 75–84.  Web of Science CSD CrossRef CAS Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (2007). CrystalStructure. Rigaku Americas Corporation, The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, Y. C. (2009). Acta Cryst. E65, m874.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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