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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m989.
Published online 2010 July 21. doi:  10.1107/S1600536810024293
PMCID: PMC3007283

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

Abstract

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 [triangle]); Bâse et al. (2002 [triangle]); Wang (2009 [triangle]).

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Object name is e-66-0m989-scheme1.jpg

Experimental

Crystal data

  • [Fe2(C5H5)2(C26H26N2)]
  • M r = 608.37
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m989-efi1.jpg
  • 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 [triangle]) T min = 0.712, T max = 0.839
  • 45235 measured reflections
  • 6726 independent reflections
  • 5515 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 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 [triangle]), 2915 Friedel pairs
  • Flack parameter: −0.006 (14)

Data collection: PROCESS-AUTO (Rigaku, 2006 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024293/im2210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024293/im2210Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

Fig. 1.
Molecular structure of the title compound, displacement ellipsoids are drawn at the 40% probability level.

Crystal data

[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

Rigaku R-AXIS RAPID/ZJUG diffractometer6726 independent reflections
Radiation source: rolling anode5515 reflections with I > 2σ(I)
graphiteRint = 0.036
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 3.0°
ω scansh = −12→11
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −12→12
Tmin = 0.712, Tmax = 0.839l = −41→41
45235 measured reflections

Refinement

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) = 0.077w = 1/[σ2(Fo2) + (0.0379P)2 + 0.4974P] where P = (Fo2 + 2Fc2)/3
S = 1.00(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 methodsFlack parameter: −0.006 (14)

Special details

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)

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)

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, °)

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—C9−85.0 (2)C27—Fe2—C30—C3137.41 (16)
C26—N2—C2—C1153.26 (18)C28—Fe2—C30—C3181.77 (17)
C15—N1—C1—C3−58.8 (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—N1−51.6 (3)C25—Fe1—C24—C23120.6 (4)
C8—C3—C1—C2−102.1 (3)C18—Fe1—C24—C23−75.2 (3)
C4—C3—C1—C271.9 (3)C20—Fe1—C24—C23−158.4 (2)
N2—C2—C1—N1−64.2 (2)C19—Fe1—C24—C23−116.8 (3)
C9—C2—C1—N1173.44 (18)C17—Fe1—C24—C23−44.4 (5)
N2—C2—C1—C3167.55 (17)C16—Fe1—C24—C23169.8 (3)
C9—C2—C1—C345.1 (2)C21—Fe1—C24—C25−38.8 (3)
N2—C2—C9—C10144.6 (2)C22—Fe1—C24—C25−84.4 (3)
C1—C2—C9—C10−95.0 (3)C18—Fe1—C24—C25164.2 (3)
N2—C2—C9—C14−40.9 (3)C23—Fe1—C24—C25−120.6 (4)
C1—C2—C9—C1479.5 (2)C20—Fe1—C24—C2581.0 (3)
C4—C3—C8—C7−1.7 (4)C19—Fe1—C24—C25122.6 (3)
C1—C3—C8—C7172.5 (3)C17—Fe1—C24—C25−165.0 (4)
C10—C9—C14—C131.6 (4)C16—Fe1—C24—C2549.3 (5)
C2—C9—C14—C13−173.0 (2)C16—C17—C18—C19−1.1 (3)
C1—N1—C15—C16−179.8 (2)Fe1—C17—C18—C19−60.3 (2)
C2—N2—C26—C27−76.0 (2)C16—C17—C18—Fe159.21 (19)
C14—C9—C10—C11−1.8 (4)C21—Fe1—C18—C19172.9 (3)
C2—C9—C10—C11172.8 (2)C22—Fe1—C18—C19−156.3 (2)
C32—Fe2—C31—C27−87.9 (2)C25—Fe1—C18—C19−49.6 (5)
C36—Fe2—C31—C27−51.8 (3)C23—Fe1—C18—C19−115.6 (2)
C34—Fe2—C31—C27−170.57 (18)C20—Fe1—C18—C1937.27 (18)
C33—Fe2—C31—C27−131.48 (17)C24—Fe1—C18—C19−77.0 (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—C30−171.5 (3)C25—Fe1—C18—C17−168.2 (4)
C34—Fe2—C31—C3069.7 (3)C23—Fe1—C18—C17125.9 (2)
C33—Fe2—C31—C30108.8 (2)C20—Fe1—C18—C17−81.3 (2)
C27—Fe2—C31—C30−119.7 (2)C19—Fe1—C18—C17−118.6 (3)
C28—Fe2—C31—C30−80.83 (19)C24—Fe1—C18—C17164.4 (2)
C29—Fe2—C31—C30−37.38 (19)C16—Fe1—C18—C17−37.34 (18)
N1—C15—C16—C1728.7 (4)C16—C20—C19—C18−1.0 (3)
N1—C15—C16—C20−154.4 (2)Fe1—C20—C19—C1858.6 (2)
N1—C15—C16—Fe1−64.0 (3)C16—C20—C19—Fe1−59.64 (18)
C21—Fe1—C16—C17−118.2 (2)C17—C18—C19—C201.3 (3)
C22—Fe1—C16—C17−74.3 (3)Fe1—C18—C19—C20−59.0 (2)
C25—Fe1—C16—C17−162.2 (2)C17—C18—C19—Fe160.3 (2)
C18—Fe1—C16—C1737.69 (18)C21—Fe1—C19—C20−51.6 (5)
C23—Fe1—C16—C17−39.9 (5)C22—Fe1—C19—C20171.4 (3)
C20—Fe1—C16—C17119.1 (2)C25—Fe1—C19—C20−80.0 (2)
C19—Fe1—C16—C1781.59 (18)C18—Fe1—C19—C20119.8 (3)
C24—Fe1—C16—C17162.7 (3)C23—Fe1—C19—C20−158.24 (19)
C21—Fe1—C16—C20122.7 (2)C24—Fe1—C19—C20−119.1 (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—C20−81.43 (18)C21—Fe1—C19—C18−171.4 (4)
C23—Fe1—C16—C20−159.0 (4)C22—Fe1—C19—C1851.6 (4)
C19—Fe1—C16—C20−37.54 (18)C25—Fe1—C19—C18160.29 (19)
C24—Fe1—C16—C2043.5 (4)C23—Fe1—C19—C1882.0 (2)
C17—Fe1—C16—C20−119.1 (2)C20—Fe1—C19—C18−119.8 (3)
C21—Fe1—C16—C153.7 (3)C24—Fe1—C19—C18121.18 (19)
C22—Fe1—C16—C1547.5 (3)C17—Fe1—C19—C18−38.20 (17)
C25—Fe1—C16—C15−40.3 (3)C16—Fe1—C19—C18−81.92 (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—C15−119.0 (3)C25—C24—C23—C220.1 (4)
C19—Fe1—C16—C15−156.5 (3)Fe1—C24—C23—C22−58.9 (3)
C24—Fe1—C16—C15−75.5 (4)C25—C24—C23—Fe159.0 (3)
C17—Fe1—C16—C15121.9 (3)C21—Fe1—C23—C24−81.5 (3)
C30—C31—C27—C28−0.8 (3)C22—Fe1—C23—C24−121.6 (4)
Fe2—C31—C27—C28−60.00 (16)C25—Fe1—C23—C24−36.4 (2)
C30—C31—C27—C26−179.8 (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—C28−75.1 (3)C16—Fe1—C23—C24−166.3 (4)
N2—C26—C27—Fe2−164.03 (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—C22−116.7 (3)
C33—Fe2—C27—C3170.4 (2)C20—Fe1—C23—C22167.5 (3)
C35—Fe2—C27—C31−174.9 (2)C19—Fe1—C23—C22−159.2 (3)
C28—Fe2—C27—C31−117.6 (2)C24—Fe1—C23—C22121.6 (4)
C29—Fe2—C27—C31−80.80 (18)C17—Fe1—C23—C22−75.7 (3)
C30—Fe2—C27—C31−37.56 (17)C16—Fe1—C23—C22−44.7 (6)
C32—Fe2—C27—C28−133.82 (18)C23—C24—C25—C210.0 (4)
C36—Fe2—C27—C28−91.2 (2)Fe1—C24—C25—C2159.5 (2)
C33—Fe2—C27—C28−172.0 (2)C23—C24—C25—Fe1−59.5 (3)
C35—Fe2—C27—C28−57.3 (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—C24−38.2 (5)
C30—Fe2—C27—C2880.04 (18)C23—Fe1—C25—C2435.7 (2)
C32—Fe2—C27—C26−15.3 (2)C20—Fe1—C25—C24−117.0 (2)
C36—Fe2—C27—C2627.3 (3)C19—Fe1—C25—C24−74.6 (3)
C33—Fe2—C27—C26−53.5 (3)C17—Fe1—C25—C24164.9 (4)
C35—Fe2—C27—C2661.2 (3)C16—Fe1—C25—C24−159.6 (2)
C31—Fe2—C27—C26−123.9 (3)C22—Fe1—C25—C21−40.2 (2)
C28—Fe2—C27—C26118.5 (3)C18—Fe1—C25—C21−156.9 (4)
C29—Fe2—C27—C26155.3 (2)C23—Fe1—C25—C21−83.0 (2)
C30—Fe2—C27—C26−161.5 (2)C20—Fe1—C25—C21124.3 (2)
C9—C14—C13—C12−0.5 (4)C19—Fe1—C25—C21166.8 (2)
C14—C13—C12—C11−0.4 (4)C24—Fe1—C25—C21−118.7 (3)
C31—C27—C28—C291.0 (3)C17—Fe1—C25—C2146.3 (5)
C26—C27—C28—C29−179.9 (2)C16—Fe1—C25—C2181.8 (3)
Fe2—C27—C28—C29−59.04 (18)C32—Fe2—C35—C34−81.0 (3)
C31—C27—C28—Fe260.08 (16)C36—Fe2—C35—C34−118.5 (4)
C26—C27—C28—Fe2−120.9 (2)C33—Fe2—C35—C34−37.3 (2)
C32—Fe2—C28—C29−173.3 (2)C27—Fe2—C35—C34−170.1 (2)
C36—Fe2—C28—C29−134.7 (2)C28—Fe2—C35—C34152.2 (2)
C34—Fe2—C28—C29−58.0 (3)C29—Fe2—C35—C34109.0 (2)
C35—Fe2—C28—C29−91.3 (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—C36−51.6 (3)
C36—Fe2—C28—C27105.22 (19)C28—Fe2—C35—C36−89.2 (3)
C34—Fe2—C28—C27−178.1 (2)C29—Fe2—C35—C36−132.5 (3)
C35—Fe2—C28—C27148.59 (17)C30—Fe2—C35—C36−171.6 (2)
C31—Fe2—C28—C27−38.51 (14)C36—C32—C33—C340.0 (4)
C29—Fe2—C28—C27−120.1 (2)Fe2—C32—C33—C34−59.8 (2)
C30—Fe2—C28—C27−82.77 (16)C36—C32—C33—Fe259.9 (2)
C13—C12—C11—C100.3 (5)C36—Fe2—C33—C32−37.3 (2)
C9—C10—C11—C120.8 (4)C34—Fe2—C33—C32−118.0 (3)
C8—C3—C4—C51.4 (4)C35—Fe2—C33—C32−81.4 (2)
C1—C3—C4—C5−172.8 (3)C31—Fe2—C33—C32106.1 (2)
C17—C16—C20—C190.4 (3)C27—Fe2—C33—C3265.3 (3)
C15—C16—C20—C19−177.0 (2)C29—Fe2—C33—C32−173.6 (2)
Fe1—C16—C20—C1959.57 (19)C30—Fe2—C33—C32150.2 (2)
C17—C16—C20—Fe1−59.21 (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—C19−164.9 (5)C31—Fe2—C33—C34−135.9 (2)
C25—Fe1—C20—C19119.5 (2)C27—Fe2—C33—C34−176.7 (2)
C18—Fe1—C20—C19−37.48 (18)C29—Fe2—C33—C34−55.6 (4)
C23—Fe1—C20—C1947.4 (4)C30—Fe2—C33—C34−91.8 (2)
C24—Fe1—C20—C1978.6 (2)C36—C35—C34—C33−0.3 (4)
C17—Fe1—C20—C19−81.61 (19)Fe2—C35—C34—C3359.2 (2)
C16—Fe1—C20—C19−119.2 (3)C36—C35—C34—Fe2−59.5 (2)
C21—Fe1—C20—C16−78.8 (2)C32—C33—C34—C350.2 (4)
C22—Fe1—C20—C16−45.7 (6)Fe2—C33—C34—C35−59.4 (2)
C25—Fe1—C20—C16−121.3 (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—C16−162.13 (17)C31—Fe2—C34—C35−173.9 (2)
C17—Fe1—C20—C1637.62 (15)C28—Fe2—C34—C35−50.9 (4)
C20—C16—C17—C180.4 (3)C29—Fe2—C34—C35−88.8 (3)
C15—C16—C17—C18177.8 (3)C30—Fe2—C34—C35−132.6 (2)
Fe1—C16—C17—C18−58.6 (2)C32—Fe2—C34—C33−38.2 (2)
C20—C16—C17—Fe159.03 (18)C36—Fe2—C34—C33−81.9 (3)
C15—C16—C17—Fe1−123.6 (3)C35—Fe2—C34—C33−120.2 (3)
C21—Fe1—C17—C1682.3 (2)C31—Fe2—C34—C3365.9 (3)
C22—Fe1—C17—C16126.5 (2)C28—Fe2—C34—C33−171.1 (2)
C25—Fe1—C17—C1647.6 (5)C29—Fe2—C34—C33151.0 (2)
C18—Fe1—C17—C16−119.6 (3)C30—Fe2—C34—C33107.1 (2)
C23—Fe1—C17—C16167.03 (19)C24—C25—C21—C22−0.1 (4)
C20—Fe1—C17—C16−37.88 (15)Fe1—C25—C21—C2260.9 (2)
C19—Fe1—C17—C16−81.56 (18)C24—C25—C21—Fe1−61.0 (2)
C24—Fe1—C17—C16−160.7 (4)C22—Fe1—C21—C25115.8 (3)
C21—Fe1—C17—C18−158.1 (3)C18—Fe1—C21—C25157.7 (3)
C22—Fe1—C17—C18−113.9 (3)C23—Fe1—C21—C2578.0 (2)
C25—Fe1—C17—C18167.1 (4)C20—Fe1—C21—C25−76.3 (2)
C23—Fe1—C17—C18−73.4 (3)C19—Fe1—C21—C25−37.1 (5)
C20—Fe1—C17—C1881.7 (2)C24—Fe1—C21—C2536.7 (2)
C19—Fe1—C17—C1838.0 (2)C17—Fe1—C21—C25−162.8 (2)
C24—Fe1—C17—C18−41.2 (5)C16—Fe1—C21—C25−119.4 (2)
C16—Fe1—C17—C18119.6 (3)C25—Fe1—C21—C22−115.8 (3)
C27—C28—C29—C30−0.9 (3)C18—Fe1—C21—C2241.9 (4)
Fe2—C28—C29—C30−59.6 (2)C23—Fe1—C21—C22−37.8 (2)
C27—C28—C29—Fe258.75 (17)C20—Fe1—C21—C22167.9 (2)
C36—Fe2—C29—C30−174.9 (2)C19—Fe1—C21—C22−152.9 (4)
C34—Fe2—C29—C30−91.7 (2)C24—Fe1—C21—C22−79.1 (2)
C33—Fe2—C29—C30−54.7 (3)C17—Fe1—C21—C2281.4 (2)
C35—Fe2—C29—C30−134.5 (2)C16—Fe1—C21—C22124.8 (2)
C31—Fe2—C29—C3038.01 (17)C33—C32—C36—C35−0.2 (4)
C27—Fe2—C29—C3081.91 (17)Fe2—C32—C36—C3559.8 (2)
C28—Fe2—C29—C30119.5 (2)C33—C32—C36—Fe2−60.0 (2)
C36—Fe2—C29—C2865.6 (2)C34—C35—C36—C320.3 (4)
C34—Fe2—C29—C28148.84 (19)Fe2—C35—C36—C32−59.6 (2)
C33—Fe2—C29—C28−174.2 (2)C34—C35—C36—Fe259.9 (2)
C35—Fe2—C29—C28106.0 (2)C34—Fe2—C36—C3281.4 (3)
C31—Fe2—C29—C28−81.48 (17)C33—Fe2—C36—C3237.5 (2)
C27—Fe2—C29—C28−37.58 (15)C35—Fe2—C36—C32118.9 (4)
C30—Fe2—C29—C28−119.5 (2)C31—Fe2—C36—C32−55.7 (4)
C34—Fe2—C32—C36−81.2 (3)C27—Fe2—C36—C32−89.7 (2)
C33—Fe2—C32—C36−119.5 (3)C28—Fe2—C36—C32−133.5 (2)
C35—Fe2—C32—C36−38.0 (2)C29—Fe2—C36—C32−171.7 (2)
C31—Fe2—C32—C36149.1 (2)C32—Fe2—C36—C35−118.9 (4)
C27—Fe2—C32—C36106.0 (2)C34—Fe2—C36—C35−37.5 (2)
C28—Fe2—C32—C3666.7 (3)C33—Fe2—C36—C35−81.5 (3)
C30—Fe2—C32—C36−176.0 (2)C31—Fe2—C36—C35−174.7 (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—C33−91.4 (2)C24—C23—C22—C21−0.2 (4)
C27—Fe2—C32—C33−134.5 (2)Fe1—C23—C22—C21−60.0 (2)
C28—Fe2—C32—C33−173.7 (2)C24—C23—C22—Fe159.8 (3)
C30—Fe2—C32—C33−56.5 (3)C25—C21—C22—C230.2 (4)
C7—C6—C5—C4−1.0 (5)Fe1—C21—C22—C2361.3 (3)
C3—C4—C5—C60.0 (5)C25—C21—C22—Fe1−61.1 (2)
C28—C29—C30—C310.4 (3)C21—Fe1—C22—C23−116.9 (3)
Fe2—C29—C30—C31−59.20 (19)C25—Fe1—C22—C23−77.3 (2)
C28—C29—C30—Fe259.56 (19)C18—Fe1—C22—C2380.2 (3)
C27—C31—C30—C290.3 (3)C20—Fe1—C22—C23−158.3 (5)
Fe2—C31—C30—C2959.5 (2)C19—Fe1—C22—C2344.1 (4)
C27—C31—C30—Fe2−59.16 (17)C24—Fe1—C22—C23−35.0 (2)
C32—Fe2—C30—C29−171.3 (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—C21−162.8 (2)
C31—Fe2—C30—C29−119.1 (3)C23—Fe1—C22—C21116.9 (3)
C27—Fe2—C30—C29−81.71 (18)C20—Fe1—C22—C21−41.3 (7)
C28—Fe2—C30—C29−37.36 (16)C19—Fe1—C22—C21161.0 (3)
C32—Fe2—C30—C31−52.2 (3)C24—Fe1—C22—C2181.9 (2)
C34—Fe2—C30—C31−133.8 (2)C17—Fe1—C22—C21−119.1 (2)
C33—Fe2—C30—C31−89.6 (2)C16—Fe1—C22—C21−77.7 (3)
C35—Fe2—C30—C31−174.0 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2210).

References

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