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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 70| Part 8| August 2014| Pages m286-m287

Crystal structure of 1,1-di­acetyl­ferrocene dihydrazone

aBaku State University, Z. Khalilov St 23, Baku, AZ-1148, Azerbaijan, bChemistry Department, M.V. Lomonosov Moscow State University, Leninskie gory 1/3, Moscow, 119991, Russian Federation, and cX-Ray Structural Centre, A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov St, B-334, Moscow 119991, Russian Federation
*Correspondence e-mail: namiq155@yahoo.com

(Received 13 June 2014; accepted 18 June 2014; online 2 July 2014)

The title compound, [Fe(C7H9N2)2], crystallizes with two crystallographically independent mol­ecules in the unit cell. These represent the chiral atropoisomers distinguished by the mutual arrangement of the two acet­yl–hydrazone groups with a cis conformation of the C=N bonds. The two cyclo­penta­dienyl (Cp) rings are planar and nearly parallel, the tilt between the two rings being 3.16 (16)° [4.40 (18)° for the second independent mol­ecule]. The conformation of the Cp rings is close to eclipsed, the twist angle being 0.1 (2)° [3.3 (2)°]. The two acet­yl–hydrazone substituents are also planar and are inclined at 13.99 (15)/9.17 (16)° [6.83 (17)/14.59 (15)°] relative to the Cp rings. The Fe—C bond lengths range from 2.035 (3) to 2.065 (2) Å, with an average of 2.050 (3) Å [2.036 (3) to 2.069 (2), average 2.046 (3) Å], which agrees well with those reported for most ferrocene derivatives. In the crystal, the mol­ecules form dimers via two strong N—H⋯N hydrogen bonds. The dimers are linked into a three-dimensional framework by weak N—H⋯N hydrogen bonds.

Related literature

For a new catalytic olefination reaction and synthesis of 1,1-di­acetyl­ferrocene dihydrazone, see: Korotchenko et al. (2001[Korotchenko, V. N., Shastin, A. V., Nenajdenko, V. G. & Balenkova, E. S. (2001). Synthesis, pp. 2081-2084.]); Nenajdenko et al. (2004[Nenajdenko, V. G., Korotchenko, V. N., Shastin, A. V. & Balenkova, E. S. (2004). Russ. Chem. Bull. Int. Ed. 53, 1034-1064.]); Abd-Elzaher et al. (2005[Abd-Elzaher, M. M., Hegazy, W. H. & Gaafar, A. E.-D. M. (2005). Appl. Organomet. Chem. 19, 911-916.]). For related compounds, see: Xiao et al. (1999[Xiao, W., Lu, Z.-L., Li, R.-Y., Su, C.-Y., Kang, B.-S., Shanmuga Sundara Raj, S. & Fun, H.-K. (1999). Acta Cryst. C55, 1762-1764.]); Fang et al. (2001[Fang, C.-J., Duan, C.-Y., Mo, H., He, C., Meng, Q.-J., Liu, Y.-J., Mei, Y.-H. & Wang, Z.-M. (2001). Organometallics, 20, 2525-2532.]); Lopez et al. (2003[Lopez, C., Bosque, R., Arias, J., Evangelio, E., Solans, X. & Font-Bardia, M. (2003). J. Organomet. Chem. 672, 34-42.]); Zhang et al. (2006[Zhang, B.-G., Xu, J., Zhao, Y.-G., Duan, C.-Y., Cao, X. & Meng, Q.-J. (2006). Dalton Trans. pp. 1271-1276.]); Zhou et al. (2007[Zhou, J., Zheng, L.-P., Chen, C.-L. & Li, M.-X. (2007). Acta Cryst. E63, m3079.]); Qiao et al. (2009[Qiao, C., Li, J., Xu, Y., Guo, S., Qi, X. & Fan, Y. (2009). Appl. Organomet. Chem. 23, 421-424.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe(C7H9N2)2]

  • Mr = 298.17

  • Orthorhombic, P n a 21

  • a = 9.2647 (3) Å

  • b = 12.9260 (4) Å

  • c = 22.0729 (7) Å

  • V = 2643.35 (15) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.13 mm−1

  • T = 295 K

  • 0.26 × 0.22 × 0.18 mm

Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.757, Tmax = 0.822

  • 38476 measured reflections

  • 6542 independent reflections

  • 6096 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement

  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.080

  • S = 1.08

  • 6542 reflections

  • 347 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.43 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3181 Friedel pairs

  • Absolute structure parameter: 0.475 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2A⋯N7i 0.90 2.53 3.287 (5) 142
N4—H4A⋯N5ii 0.90 2.29 3.137 (4) 157
N4—H4B⋯N2iii 0.90 2.61 3.421 (4) 150
N6—H6A⋯N3iv 0.90 2.24 3.073 (4) 154
N8—H8B⋯N1v 0.90 2.60 3.497 (5) 178
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) x-1, y, z; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (iv) x+1, y, z; (v) [-x+1, -y+1, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The Nenajdenko–Shastin catalytic olefination reaction discovered by us recently is a facile approach to functionally substituted halogen–alkenes (Korotchenko et al., 2001; Nenajdenko et al., 2004) (Fig. 1). To study the further synthetic potential of this reaction, we have investigated the olefination of 1,1–diacetylferrocene as a representative of metallocenes. The structure of the reaction product, C14H18FeN4, I, has been unambiguously established by X–ray diffraction analysis. It has been revealed that the olefination of 1,1–diacetylferrocene allows the developing of a simple and convenient way to obtain the halogen–substituted ferrocene–alkenes IIV (Fig. 2).

The I crystallizes in the non–centrosymmetric orthorhombic space group Pna21 with two crystallographically independent molecules in the unit cell. The two crystallographically independent molecules of I represent the chiral atropoisomers (Fig. 3). The atropoisomers are distinguished by the mutual arrangement of the two acetyl–hydrazone groups having the cis–configuration of the CN bonds (the disposition of the hydrazone groups is right/left and left/right, respectively). The two Cp rings are planar (r.m.s. deviations are 0.001, 0.003 and 0.003, 0.002 for the two crystallographically independent molecules, respectively) and nearly parallel, the ring–tilt between the two rings being 3.16 (16)° and 4.40 (18)° for the two crystallographically independent molecules, respectively. The conformation of the Cp rings is close to eclipsed, which is common for ferrocene derivatives. The twist angle of the Cp rings is defined as the torsion angle between a ring C atom, the two ring centers and the corresponding C atom on the opposite ring. The value of the twist angle in I is 0.1 (2)° and 3.3 (2)° for the two crystallographically independent molecules, respectively. The two acetyl–hydrazone substituents are also planar (r.m.s. deviations are 0.012, 0.026 and 0.018, 0.027 for the two crystallographically independent molecules, respectively) and are inclined relative to the Cp rings at 13.99 (15)°, 9.17 (16)° and 6.83 (17)°, 14.59 (15)° for the two crystallographically independent molecules, respectively. The Fe–C distances are as expected for a ferrocene derivative, ranging from 2.035 (3)Å to 2.065 (2)Å, with an average of 2.050 (3)Å and 2.046 (3)Å (for the two crystallographically independent molecules, respectively), which agree well with those reported for most of ferrocene derivatives (Xiao et al., 1999; Fang et al., 2001; Lopez et al., 2003; Zhang et al., 2006; Zhou et al., 2007; Qiao et al., 2009).

In the crystal, the molecules of I form a dimers via the two strong intermolecular N—H···N hydrogen bonds (Fig. 4, Table 1). Further, the dimers are linked into three–dimensional framework by the additional weak intermolecular N—H···N hydrogen bonds (Fig. 5, Table 1).

Related literature top

For a new catalytic olefination reaction and synthesis of 1,1-diacetylferrocene dihydrazone, see: Korotchenko et al. (2001); Nenajdenko et al. (2004); Abd-Elzaher et al. (2005). For related compounds, see: Xiao et al. (1999); Fang et al. (2001); Lopez et al. (2003); Zhang et al. (2006); Zhou et al. (2007); Qiao et al. (2009).

Experimental top

The product I was prepared by use of the methodics described in Abd-Elzaher et al., 2005. The single crystals of I were obtained by slow crystallization from C2H5OH. M.p. = 452–454 K.

Refinement top

The value of Flack parameter 0.475 (16) (3181 Friedel pairs measured, 99%) indicates that, in this case, the absolute structure cannot be objectively determined due to the specifical (pseudo–centrosymmetrical) arrangement of heavy Fe atoms.

The hydrogen atoms of the amino–groups were localized in the difference Fourier maps and refined isotropically with fixed displacement parameters (Uiso(H) = 1.2Ueq(N)). The other hydrogen atoms were placed in calculated positions with with C—H = 0.96Å (Cp H) and 0.98Å (methyl H) and refined within the riding model with fixed isotropic displacement parameters (Uiso(H) = 1.2Ueq(C)).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The Nenajdenko–Shastin catalytic olefination reaction as a general method for the preparation of alkenes.
[Figure 2] Fig. 2. Reaction of 1,1'–diacetylferrocene with hydrazone in C2H5OH.
[Figure 3] Fig. 3. Molecular structure of I with the atom numbering scheme. The two crystallographically independent molecules are presented. Displacement ellipsoids are shown at the 40% probability level. H atoms are depicted as a small spheres of arbitrary radius.
[Figure 4] Fig. 4. The H–bonded dimers of I. Dashed lines indicate the intermolecular hydrogen bonds.
[Figure 5] Fig. 5. A portion of the crystal packing of I along the a axis. Dashed lines indicate the intermolecular hydrogen bonds.
1,1-Diacetylferrocene dihydrazone top
Crystal data top
[Fe(C7H9N2)2]Dx = 1.498 Mg m3
Mr = 298.17Melting point = 452–454 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 9951 reflections
a = 9.2647 (3) Åθ = 2.7–28.3°
b = 12.9260 (4) ŵ = 1.13 mm1
c = 22.0729 (7) ÅT = 295 K
V = 2643.35 (15) Å3Prism, colourless
Z = 80.26 × 0.22 × 0.18 mm
F(000) = 1248
Data collection top
Bruker APEXII CCD
diffractometer
6542 independent reflections
Radiation source: fine–focus sealed tube6096 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ϕ and ω scansθmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1212
Tmin = 0.757, Tmax = 0.822k = 1717
38476 measured reflectionsl = 2929
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0361P)2 + 1.3943P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.002
6542 reflectionsΔρmax = 0.43 e Å3
347 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 3181 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.475 (16)
Crystal data top
[Fe(C7H9N2)2]V = 2643.35 (15) Å3
Mr = 298.17Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 9.2647 (3) ŵ = 1.13 mm1
b = 12.9260 (4) ÅT = 295 K
c = 22.0729 (7) Å0.26 × 0.22 × 0.18 mm
Data collection top
Bruker APEXII CCD
diffractometer
6542 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
6096 reflections with I > 2σ(I)
Tmin = 0.757, Tmax = 0.822Rint = 0.017
38476 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.080Δρmax = 0.43 e Å3
S = 1.08Δρmin = 0.25 e Å3
6542 reflectionsAbsolute structure: Flack (1983), 3181 Friedel pairs
347 parametersAbsolute structure parameter: 0.475 (16)
1 restraint
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
Fe10.34263 (3)0.58615 (2)0.871244 (14)0.03239 (8)
N10.2664 (3)0.29657 (18)0.92124 (12)0.0476 (5)
N20.1723 (3)0.2109 (2)0.92300 (16)0.0639 (8)
H2A0.14290.24010.95790.077*
H2B0.12360.22190.88830.077*
N30.0469 (3)0.50928 (18)0.81874 (11)0.0417 (5)
N40.1449 (3)0.4276 (2)0.81548 (14)0.0526 (6)
H4A0.19340.43830.78070.063*
H4B0.20170.41610.84790.063*
C10.3861 (2)0.42947 (18)0.87079 (14)0.0351 (5)
C20.4474 (3)0.4795 (2)0.81904 (14)0.0454 (7)
H20.42600.46340.77660.054*
C30.5449 (3)0.5561 (3)0.83974 (16)0.0500 (7)
H30.60230.60210.81390.060*
C40.5453 (3)0.5555 (2)0.90370 (15)0.0462 (7)
H40.60290.60050.93000.055*
C50.4472 (3)0.4772 (2)0.92296 (13)0.0359 (5)
H50.42440.45980.96510.043*
C60.1226 (2)0.61015 (17)0.87053 (13)0.0344 (4)
C70.1880 (3)0.6567 (2)0.81897 (13)0.0397 (6)
H70.16630.64020.77660.048*
C80.2910 (3)0.7300 (2)0.83914 (18)0.0520 (8)
H60.35200.77340.81320.062*
C90.2912 (3)0.7293 (2)0.90302 (17)0.0521 (8)
H90.35160.77250.92930.062*
C100.1877 (3)0.6548 (2)0.92278 (13)0.0421 (6)
H100.16470.63780.96500.051*
C110.2823 (2)0.34326 (16)0.87073 (14)0.0384 (5)
C120.2072 (4)0.3174 (3)0.81283 (16)0.0613 (9)
H12A0.22650.24660.80230.092*
H12B0.24180.36190.78120.092*
H12C0.10510.32700.81780.092*
C130.0107 (2)0.52915 (16)0.86991 (14)0.0354 (4)
C140.0273 (4)0.4756 (3)0.92816 (15)0.0536 (8)
H14A0.03650.40270.92100.080*
H14B0.11710.50240.94320.080*
H14C0.04740.48760.95750.080*
Fe20.39440 (3)0.41401 (2)0.617696 (15)0.03361 (8)
N50.7745 (2)0.4900 (2)0.68237 (11)0.0429 (5)
N60.8748 (3)0.5680 (2)0.68788 (14)0.0566 (7)
H6A0.92320.56240.72310.068*
H6B0.94490.57820.66030.068*
N70.4742 (3)0.6966 (2)0.55835 (14)0.0597 (7)
N80.5659 (4)0.7824 (3)0.5554 (2)0.0937 (13)
H8A0.65120.77840.57470.112*
H8B0.61170.76170.52150.112*
C150.6146 (2)0.38990 (18)0.62404 (13)0.0355 (5)
C160.5409 (3)0.3428 (2)0.67357 (13)0.0389 (5)
H160.55620.35880.71650.047*
C170.4408 (4)0.2695 (2)0.65045 (16)0.0487 (7)
H170.37610.22590.67460.058*
C180.4501 (4)0.2712 (3)0.58659 (16)0.0528 (8)
H180.39350.22860.55860.063*
C190.5564 (3)0.3450 (2)0.56992 (13)0.0448 (6)
H190.58520.36230.52840.054*
C200.3500 (2)0.5705 (2)0.61202 (14)0.0377 (6)
C210.2817 (3)0.5239 (3)0.66391 (14)0.0484 (7)
H210.29830.54370.70620.058*
C220.1879 (3)0.4450 (3)0.64422 (18)0.0571 (8)
H220.12760.40130.67020.069*
C230.1963 (3)0.4401 (3)0.58071 (16)0.0516 (7)
H230.14280.39200.55470.062*
C240.2954 (3)0.5164 (2)0.56057 (14)0.0414 (6)
H240.32250.52940.51830.050*
C250.7274 (2)0.4692 (2)0.62853 (12)0.0378 (5)
C260.7826 (4)0.5208 (3)0.57320 (15)0.0534 (8)
H26A0.88590.51550.57210.080*
H26B0.75520.59250.57370.080*
H26C0.74240.48800.53800.080*
C270.4541 (3)0.6555 (2)0.61029 (14)0.0459 (6)
C280.5251 (4)0.6872 (3)0.66867 (18)0.0707 (11)
H28A0.61080.72630.66000.106*
H28B0.55040.62660.69150.106*
H28C0.45960.72900.69190.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02844 (15)0.02768 (14)0.04106 (17)0.00246 (11)0.00040 (14)0.00025 (17)
N10.0393 (11)0.0360 (11)0.0674 (15)0.0054 (9)0.0021 (11)0.0015 (11)
N20.0499 (14)0.0445 (14)0.097 (2)0.0114 (11)0.0001 (14)0.0051 (14)
N30.0365 (11)0.0384 (11)0.0504 (12)0.0030 (9)0.0059 (9)0.0025 (10)
N40.0412 (12)0.0508 (14)0.0660 (16)0.0094 (10)0.0077 (11)0.0048 (12)
C10.0322 (11)0.0333 (11)0.0398 (12)0.0096 (7)0.0016 (13)0.0027 (11)
C20.0478 (15)0.0489 (17)0.0395 (13)0.0177 (13)0.0081 (12)0.0014 (12)
C30.0342 (13)0.0475 (17)0.068 (2)0.0055 (13)0.0156 (13)0.0129 (15)
C40.0313 (12)0.0405 (14)0.0667 (19)0.0007 (11)0.0069 (13)0.0046 (13)
C50.0355 (12)0.0323 (12)0.0399 (13)0.0030 (10)0.0034 (10)0.0019 (10)
C60.0293 (9)0.0324 (10)0.0415 (12)0.0068 (7)0.0003 (12)0.0012 (11)
C70.0369 (13)0.0358 (13)0.0465 (14)0.0081 (11)0.0014 (10)0.0053 (11)
C80.0413 (16)0.0286 (13)0.086 (2)0.0005 (12)0.0000 (15)0.0107 (15)
C90.0460 (17)0.0325 (14)0.078 (2)0.0036 (13)0.0045 (16)0.0140 (15)
C100.0382 (13)0.0437 (14)0.0446 (14)0.0076 (11)0.0024 (11)0.0113 (11)
C110.0365 (10)0.0282 (9)0.0505 (12)0.0065 (8)0.0044 (12)0.0049 (12)
C120.073 (2)0.0441 (16)0.0671 (19)0.0066 (15)0.0256 (17)0.0143 (14)
C130.0272 (9)0.0361 (11)0.0429 (11)0.0053 (8)0.0025 (11)0.0009 (12)
C140.0494 (16)0.064 (2)0.0471 (16)0.0102 (15)0.0060 (13)0.0088 (15)
Fe20.02893 (15)0.03346 (16)0.03846 (16)0.00323 (11)0.00165 (14)0.00044 (17)
N50.0377 (10)0.0441 (12)0.0469 (12)0.0003 (9)0.0073 (9)0.0050 (10)
N60.0481 (13)0.0602 (16)0.0615 (16)0.0142 (12)0.0100 (12)0.0059 (13)
N70.0462 (13)0.0500 (15)0.0828 (19)0.0088 (11)0.0112 (13)0.0192 (14)
N80.0643 (19)0.060 (2)0.156 (4)0.0189 (17)0.021 (2)0.030 (2)
C150.0294 (9)0.0360 (10)0.0411 (12)0.0088 (9)0.0039 (10)0.0062 (11)
C160.0398 (13)0.0327 (12)0.0442 (13)0.0082 (10)0.0013 (10)0.0039 (10)
C170.0455 (16)0.0312 (12)0.070 (2)0.0040 (12)0.0037 (14)0.0037 (13)
C180.0478 (17)0.0392 (15)0.071 (2)0.0039 (14)0.0113 (15)0.0182 (15)
C190.0422 (14)0.0487 (15)0.0436 (14)0.0091 (12)0.0010 (11)0.0120 (12)
C200.0332 (12)0.0370 (12)0.0427 (14)0.0122 (8)0.0009 (11)0.0019 (12)
C210.0515 (16)0.0501 (17)0.0436 (15)0.0243 (13)0.0083 (12)0.0032 (12)
C220.0354 (13)0.0590 (19)0.077 (2)0.0086 (14)0.0124 (14)0.0185 (17)
C230.0310 (13)0.0541 (17)0.070 (2)0.0031 (12)0.0100 (13)0.0107 (15)
C240.0342 (12)0.0465 (16)0.0435 (14)0.0023 (11)0.0069 (11)0.0051 (12)
C250.0303 (10)0.0422 (12)0.0410 (14)0.0077 (9)0.0012 (10)0.0013 (11)
C260.0465 (15)0.067 (2)0.0473 (15)0.0066 (14)0.0024 (12)0.0045 (15)
C270.0417 (12)0.0357 (12)0.0603 (17)0.0104 (10)0.0149 (13)0.0058 (13)
C280.080 (2)0.0457 (17)0.087 (3)0.0142 (17)0.032 (2)0.0236 (17)
Geometric parameters (Å, º) top
Fe1—C102.035 (3)Fe2—C182.036 (3)
Fe1—C92.035 (3)Fe2—C212.037 (3)
Fe1—C32.036 (3)Fe2—C232.037 (3)
Fe1—C22.042 (3)Fe2—C192.040 (3)
Fe1—C82.046 (3)Fe2—C222.040 (3)
Fe1—C42.049 (3)Fe2—C242.045 (3)
Fe1—C72.053 (3)Fe2—C172.048 (3)
Fe1—C52.055 (3)Fe2—C162.052 (3)
Fe1—C62.0624 (19)Fe2—C202.067 (3)
Fe1—C12.065 (2)Fe2—C152.069 (2)
N1—C111.276 (4)N5—C251.294 (4)
N1—N21.410 (3)N5—N61.377 (3)
N2—H2A0.8996N6—H6A0.9003
N2—H2B0.9002N6—H6B0.8993
N3—C131.276 (4)N7—C271.277 (4)
N3—N41.394 (3)N7—N81.398 (4)
N4—H4A0.9002N8—H8A0.8998
N4—H4B0.9004N8—H8B0.9005
C1—C51.424 (4)C15—C161.425 (4)
C1—C21.430 (4)C15—C191.433 (4)
C1—C111.472 (3)C15—C251.466 (3)
C2—C31.416 (5)C16—C171.421 (4)
C2—H20.9800C16—H160.9800
C3—C41.412 (4)C17—C181.413 (4)
C3—H30.9800C17—H170.9800
C4—C51.426 (4)C18—C191.420 (5)
C4—H40.9800C18—H180.9800
C5—H50.9800C19—H190.9800
C6—C71.423 (4)C20—C241.426 (4)
C6—C101.424 (4)C20—C211.440 (4)
C6—C131.473 (3)C20—C271.463 (4)
C7—C81.417 (4)C21—C221.409 (5)
C7—H70.9800C21—H210.9800
C8—C91.410 (4)C22—C231.405 (5)
C8—H60.9800C22—H220.9800
C9—C101.427 (5)C23—C241.419 (4)
C9—H90.9800C23—H230.9800
C10—H100.9800C24—H240.9800
C11—C121.493 (4)C25—C261.483 (4)
C12—H12A0.9600C26—H26A0.9600
C12—H12B0.9600C26—H26B0.9600
C12—H12C0.9600C26—H26C0.9600
C13—C141.502 (4)C27—C281.504 (4)
C14—H14A0.9600C28—H28A0.9600
C14—H14B0.9600C28—H28B0.9600
C14—H14C0.9600C28—H28C0.9600
C10—Fe1—C941.05 (13)C18—Fe2—C21158.63 (15)
C10—Fe1—C3157.39 (13)C18—Fe2—C23104.11 (14)
C9—Fe1—C3120.43 (14)C21—Fe2—C2367.87 (14)
C10—Fe1—C2160.90 (13)C18—Fe2—C1940.77 (14)
C9—Fe1—C2156.84 (14)C21—Fe2—C19160.22 (14)
C3—Fe1—C240.63 (14)C23—Fe2—C19121.90 (13)
C10—Fe1—C868.45 (14)C18—Fe2—C22120.85 (15)
C9—Fe1—C840.42 (12)C21—Fe2—C2240.42 (15)
C3—Fe1—C8105.66 (13)C23—Fe2—C2240.32 (14)
C2—Fe1—C8121.94 (14)C19—Fe2—C22157.55 (15)
C10—Fe1—C4122.37 (12)C18—Fe2—C24119.51 (14)
C9—Fe1—C4105.66 (13)C21—Fe2—C2468.13 (12)
C3—Fe1—C440.44 (12)C23—Fe2—C2440.68 (12)
C2—Fe1—C468.35 (13)C19—Fe2—C24107.11 (13)
C8—Fe1—C4120.73 (13)C22—Fe2—C2468.24 (13)
C10—Fe1—C768.20 (9)C18—Fe2—C1740.47 (12)
C9—Fe1—C768.08 (13)C21—Fe2—C17124.51 (13)
C3—Fe1—C7122.33 (13)C23—Fe2—C17118.79 (13)
C2—Fe1—C7108.31 (12)C19—Fe2—C1768.27 (14)
C8—Fe1—C740.44 (12)C22—Fe2—C17105.93 (14)
C4—Fe1—C7157.23 (12)C24—Fe2—C17154.40 (13)
C10—Fe1—C5108.69 (12)C18—Fe2—C1668.19 (12)
C9—Fe1—C5122.80 (13)C21—Fe2—C16110.53 (12)
C3—Fe1—C568.01 (12)C23—Fe2—C16155.69 (12)
C2—Fe1—C568.10 (10)C19—Fe2—C1668.16 (10)
C8—Fe1—C5157.67 (13)C22—Fe2—C16122.40 (13)
C4—Fe1—C540.66 (11)C24—Fe2—C16163.21 (11)
C7—Fe1—C5160.95 (11)C17—Fe2—C1640.56 (12)
C10—Fe1—C640.67 (10)C18—Fe2—C20156.46 (14)
C9—Fe1—C668.55 (11)C21—Fe2—C2041.08 (12)
C3—Fe1—C6159.37 (13)C23—Fe2—C2068.55 (12)
C2—Fe1—C6124.55 (12)C19—Fe2—C20122.86 (12)
C8—Fe1—C668.26 (11)C22—Fe2—C2068.83 (13)
C4—Fe1—C6159.72 (12)C24—Fe2—C2040.57 (12)
C7—Fe1—C640.46 (11)C17—Fe2—C20162.74 (13)
C5—Fe1—C6124.97 (11)C16—Fe2—C20127.34 (11)
C10—Fe1—C1124.59 (12)C18—Fe2—C1568.66 (12)
C9—Fe1—C1159.87 (14)C21—Fe2—C15125.21 (12)
C3—Fe1—C168.40 (11)C23—Fe2—C15160.19 (13)
C2—Fe1—C140.76 (12)C19—Fe2—C1540.83 (11)
C8—Fe1—C1159.23 (14)C22—Fe2—C15159.21 (13)
C4—Fe1—C168.48 (11)C24—Fe2—C15125.55 (11)
C7—Fe1—C1124.67 (11)C17—Fe2—C1568.41 (12)
C5—Fe1—C140.42 (11)C16—Fe2—C1540.48 (11)
C6—Fe1—C1109.90 (9)C20—Fe2—C15110.34 (9)
C11—N1—N2117.8 (3)C25—N5—N6117.5 (3)
N1—N2—H2A83.2N5—N6—H6A110.7
N1—N2—H2B99.3N5—N6—H6B122.4
H2A—N2—H2B120.7H6A—N6—H6B103.7
C13—N3—N4118.1 (3)C27—N7—N8117.4 (3)
N3—N4—H4A104.7N7—N8—H8A117.7
N3—N4—H4B117.7N7—N8—H8B95.2
H4A—N4—H4B114.2H8A—N8—H8B87.9
C5—C1—C2107.0 (2)C16—C15—C19106.6 (2)
C5—C1—C11126.0 (3)C16—C15—C25126.0 (2)
C2—C1—C11127.0 (3)C19—C15—C25127.4 (3)
C5—C1—Fe169.42 (14)C16—C15—Fe269.11 (14)
C2—C1—Fe168.76 (15)C19—C15—Fe268.49 (14)
C11—C1—Fe1127.97 (14)C25—C15—Fe2127.00 (16)
C3—C2—C1108.2 (3)C17—C16—C15108.8 (3)
C3—C2—Fe169.44 (18)C17—C16—Fe269.59 (16)
C1—C2—Fe170.48 (15)C15—C16—Fe270.41 (14)
C3—C2—H2125.9C17—C16—H16125.6
C1—C2—H2125.9C15—C16—H16125.6
Fe1—C2—H2125.9Fe2—C16—H16125.6
C4—C3—C2108.7 (3)C18—C17—C16107.9 (3)
C4—C3—Fe170.27 (19)C18—C17—Fe269.3 (2)
C2—C3—Fe169.93 (17)C16—C17—Fe269.86 (16)
C4—C3—H3125.6C18—C17—H17126.0
C2—C3—H3125.6C16—C17—H17126.0
Fe1—C3—H3125.6Fe2—C17—H17126.0
C3—C4—C5107.5 (3)C17—C18—C19108.2 (3)
C3—C4—Fe169.29 (19)C17—C18—Fe270.2 (2)
C5—C4—Fe169.92 (15)C19—C18—Fe269.76 (17)
C3—C4—H4126.3C17—C18—H18125.9
C5—C4—H4126.3C19—C18—H18125.9
Fe1—C4—H4126.3Fe2—C18—H18125.9
C1—C5—C4108.7 (3)C18—C19—C15108.5 (3)
C1—C5—Fe170.15 (14)C18—C19—Fe269.47 (18)
C4—C5—Fe169.42 (16)C15—C19—Fe270.68 (14)
C1—C5—H5125.7C18—C19—H19125.8
C4—C5—H5125.7C15—C19—H19125.8
Fe1—C5—H5125.7Fe2—C19—H19125.8
C7—C6—C10107.2 (2)C24—C20—C21105.8 (2)
C7—C6—C13126.4 (3)C24—C20—C27125.5 (3)
C10—C6—C13126.4 (3)C21—C20—C27128.6 (3)
C7—C6—Fe169.40 (13)C24—C20—Fe268.89 (16)
C10—C6—Fe168.63 (13)C21—C20—Fe268.31 (16)
C13—C6—Fe1126.05 (15)C27—C20—Fe2127.28 (16)
C8—C7—C6108.6 (3)C22—C21—C20109.2 (3)
C8—C7—Fe169.54 (17)C22—C21—Fe269.94 (18)
C6—C7—Fe170.14 (13)C20—C21—Fe270.61 (15)
C8—C7—H7125.7C22—C21—H21125.4
C6—C7—H7125.7C20—C21—H21125.4
Fe1—C7—H7125.7Fe2—C21—H21125.4
C9—C8—C7108.1 (3)C23—C22—C21107.8 (3)
C9—C8—Fe169.4 (2)C23—C22—Fe269.72 (19)
C7—C8—Fe170.02 (16)C21—C22—Fe269.64 (17)
C9—C8—H6126.0C23—C22—H22126.1
C7—C8—H6126.0C21—C22—H22126.1
Fe1—C8—H6126.0Fe2—C22—H22126.1
C8—C9—C10108.0 (3)C22—C23—C24108.5 (3)
C8—C9—Fe170.2 (2)C22—C23—Fe269.96 (19)
C10—C9—Fe169.47 (16)C24—C23—Fe269.97 (16)
C8—C9—H9126.0C22—C23—H23125.8
C10—C9—H9126.0C24—C23—H23125.8
Fe1—C9—H9126.0Fe2—C23—H23125.8
C6—C10—C9108.1 (3)C23—C24—C20108.7 (3)
C6—C10—Fe170.71 (13)C23—C24—Fe269.35 (17)
C9—C10—Fe169.48 (17)C20—C24—Fe270.54 (15)
C6—C10—H10126.0C23—C24—H24125.7
C9—C10—H10126.0C20—C24—H24125.7
Fe1—C10—H10126.0Fe2—C24—H24125.7
N1—C11—C1115.7 (3)N5—C25—C15116.6 (3)
N1—C11—C12126.0 (2)N5—C25—C26123.1 (3)
C1—C11—C12118.3 (3)C15—C25—C26120.3 (3)
C11—C12—H12A109.5C25—C26—H26A109.5
C11—C12—H12B109.5C25—C26—H26B109.5
H12A—C12—H12B109.5H26A—C26—H26B109.5
C11—C12—H12C109.5C25—C26—H26C109.5
H12A—C12—H12C109.5H26A—C26—H26C109.5
H12B—C12—H12C109.5H26B—C26—H26C109.5
N3—C13—C6116.5 (3)N7—C27—C20115.6 (3)
N3—C13—C14124.5 (2)N7—C27—C28126.3 (3)
C6—C13—C14119.0 (3)C20—C27—C28118.1 (3)
C13—C14—H14A109.5C27—C28—H28A109.5
C13—C14—H14B109.5C27—C28—H28B109.5
H14A—C14—H14B109.5H28A—C28—H28B109.5
C13—C14—H14C109.5C27—C28—H28C109.5
H14A—C14—H14C109.5H28A—C28—H28C109.5
H14B—C14—H14C109.5H28B—C28—H28C109.5
C10—Fe1—C1—C577.91 (18)C18—Fe2—C15—C1680.99 (18)
C9—Fe1—C1—C539.2 (4)C21—Fe2—C15—C1680.46 (19)
C3—Fe1—C1—C581.00 (19)C23—Fe2—C15—C16152.8 (3)
C2—Fe1—C1—C5118.7 (2)C19—Fe2—C15—C16118.7 (2)
C8—Fe1—C1—C5158.0 (3)C22—Fe2—C15—C1640.5 (4)
C4—Fe1—C1—C537.37 (17)C24—Fe2—C15—C16167.25 (17)
C7—Fe1—C1—C5163.81 (16)C17—Fe2—C15—C1637.35 (17)
C6—Fe1—C1—C5121.00 (16)C20—Fe2—C15—C16124.21 (16)
C10—Fe1—C1—C2163.35 (18)C18—Fe2—C15—C1937.68 (19)
C9—Fe1—C1—C2157.9 (3)C21—Fe2—C15—C19160.88 (18)
C3—Fe1—C1—C237.74 (19)C23—Fe2—C15—C1934.1 (4)
C8—Fe1—C1—C239.3 (4)C22—Fe2—C15—C19159.1 (3)
C4—Fe1—C1—C281.4 (2)C24—Fe2—C15—C1974.1 (2)
C7—Fe1—C1—C277.4 (2)C17—Fe2—C15—C1981.3 (2)
C5—Fe1—C1—C2118.7 (2)C16—Fe2—C15—C19118.7 (2)
C6—Fe1—C1—C2120.26 (18)C20—Fe2—C15—C19117.13 (18)
C10—Fe1—C1—C1142.4 (3)C18—Fe2—C15—C25159.0 (3)
C9—Fe1—C1—C1181.1 (4)C21—Fe2—C15—C2539.5 (3)
C3—Fe1—C1—C11158.7 (3)C23—Fe2—C15—C2587.2 (4)
C2—Fe1—C1—C11121.0 (4)C19—Fe2—C15—C25121.3 (3)
C8—Fe1—C1—C1181.7 (4)C22—Fe2—C15—C2579.5 (4)
C4—Fe1—C1—C11157.6 (3)C24—Fe2—C15—C2547.2 (3)
C7—Fe1—C1—C1143.5 (3)C17—Fe2—C15—C25157.4 (3)
C5—Fe1—C1—C11120.3 (3)C16—Fe2—C15—C25120.0 (3)
C6—Fe1—C1—C110.7 (3)C20—Fe2—C15—C254.2 (3)
C5—C1—C2—C30.3 (3)C19—C15—C16—C170.8 (3)
C11—C1—C2—C3178.3 (2)C25—C15—C16—C17179.6 (2)
Fe1—C1—C2—C359.4 (2)Fe2—C15—C16—C1759.19 (19)
C5—C1—C2—Fe159.13 (15)C19—C15—C16—Fe258.43 (15)
C11—C1—C2—Fe1122.2 (2)C25—C15—C16—Fe2121.3 (2)
C10—Fe1—C2—C3165.2 (3)C18—Fe2—C16—C1737.6 (2)
C9—Fe1—C2—C341.7 (4)C21—Fe2—C16—C17119.5 (2)
C8—Fe1—C2—C376.2 (2)C23—Fe2—C16—C1738.1 (4)
C4—Fe1—C2—C337.36 (18)C19—Fe2—C16—C1781.6 (2)
C7—Fe1—C2—C3118.65 (19)C22—Fe2—C16—C1776.0 (2)
C5—Fe1—C2—C381.3 (2)C24—Fe2—C16—C17158.3 (4)
C6—Fe1—C2—C3160.46 (18)C20—Fe2—C16—C17162.92 (19)
C1—Fe1—C2—C3119.1 (3)C15—Fe2—C16—C17119.8 (2)
C10—Fe1—C2—C146.1 (4)C18—Fe2—C16—C1582.25 (18)
C9—Fe1—C2—C1160.8 (3)C21—Fe2—C16—C15120.64 (17)
C3—Fe1—C2—C1119.1 (3)C23—Fe2—C16—C15157.9 (3)
C8—Fe1—C2—C1164.67 (16)C19—Fe2—C16—C1538.17 (15)
C4—Fe1—C2—C181.73 (18)C22—Fe2—C16—C15164.17 (17)
C7—Fe1—C2—C1122.26 (16)C24—Fe2—C16—C1538.5 (5)
C5—Fe1—C2—C137.79 (15)C17—Fe2—C16—C15119.8 (2)
C6—Fe1—C2—C180.44 (19)C20—Fe2—C16—C1577.26 (18)
C1—C2—C3—C40.3 (4)C15—C16—C17—C180.7 (3)
Fe1—C2—C3—C459.8 (2)Fe2—C16—C17—C1859.0 (2)
C1—C2—C3—Fe160.09 (18)C15—C16—C17—Fe259.70 (17)
C10—Fe1—C3—C447.9 (4)C21—Fe2—C17—C18159.3 (2)
C9—Fe1—C3—C478.1 (2)C23—Fe2—C17—C1877.6 (3)
C2—Fe1—C3—C4119.6 (3)C19—Fe2—C17—C1837.9 (2)
C8—Fe1—C3—C4119.3 (2)C22—Fe2—C17—C18119.1 (2)
C7—Fe1—C3—C4160.00 (19)C24—Fe2—C17—C1846.4 (4)
C5—Fe1—C3—C438.06 (19)C16—Fe2—C17—C18119.3 (3)
C6—Fe1—C3—C4171.0 (2)C20—Fe2—C17—C18171.2 (3)
C1—Fe1—C3—C481.7 (2)C15—Fe2—C17—C1882.0 (2)
C10—Fe1—C3—C2167.5 (3)C18—Fe2—C17—C16119.3 (3)
C9—Fe1—C3—C2162.33 (19)C21—Fe2—C17—C1681.4 (2)
C8—Fe1—C3—C2121.1 (2)C23—Fe2—C17—C16163.17 (18)
C4—Fe1—C3—C2119.6 (3)C19—Fe2—C17—C1681.37 (18)
C7—Fe1—C3—C280.4 (2)C22—Fe2—C17—C16121.6 (2)
C5—Fe1—C3—C281.54 (17)C24—Fe2—C17—C16165.7 (3)
C6—Fe1—C3—C251.4 (4)C20—Fe2—C17—C1651.9 (5)
C1—Fe1—C3—C237.85 (18)C15—Fe2—C17—C1637.28 (17)
C2—C3—C4—C50.2 (4)C16—C17—C18—C190.3 (4)
Fe1—C3—C4—C559.7 (2)Fe2—C17—C18—C1959.7 (2)
C2—C3—C4—Fe159.6 (2)C16—C17—C18—Fe259.4 (2)
C10—Fe1—C4—C3160.3 (2)C21—Fe2—C18—C1753.1 (5)
C9—Fe1—C4—C3118.8 (2)C23—Fe2—C18—C17118.1 (2)
C2—Fe1—C4—C337.5 (2)C19—Fe2—C18—C17119.1 (3)
C8—Fe1—C4—C377.7 (3)C22—Fe2—C18—C1778.0 (3)
C7—Fe1—C4—C348.3 (4)C24—Fe2—C18—C17158.9 (2)
C5—Fe1—C4—C3118.7 (3)C16—Fe2—C18—C1737.7 (2)
C6—Fe1—C4—C3170.9 (3)C20—Fe2—C18—C17173.5 (2)
C1—Fe1—C4—C381.5 (2)C15—Fe2—C18—C1781.3 (2)
C10—Fe1—C4—C581.0 (2)C21—Fe2—C18—C19172.2 (3)
C9—Fe1—C4—C5122.49 (19)C23—Fe2—C18—C19122.88 (19)
C3—Fe1—C4—C5118.7 (3)C22—Fe2—C18—C19162.92 (18)
C2—Fe1—C4—C581.15 (18)C24—Fe2—C18—C1982.0 (2)
C8—Fe1—C4—C5163.63 (19)C17—Fe2—C18—C19119.1 (3)
C7—Fe1—C4—C5167.0 (3)C16—Fe2—C18—C1981.41 (18)
C6—Fe1—C4—C552.2 (4)C20—Fe2—C18—C1954.4 (4)
C1—Fe1—C4—C537.17 (17)C15—Fe2—C18—C1937.73 (17)
C2—C1—C5—C40.2 (3)C17—C18—C19—C150.2 (4)
C11—C1—C5—C4178.4 (2)Fe2—C18—C19—C1560.16 (18)
Fe1—C1—C5—C458.92 (18)C17—C18—C19—Fe260.0 (3)
C2—C1—C5—Fe158.72 (16)C16—C15—C19—C180.6 (3)
C11—C1—C5—Fe1122.6 (2)C25—C15—C19—C18179.7 (2)
C3—C4—C5—C10.0 (3)Fe2—C15—C19—C1859.4 (2)
Fe1—C4—C5—C159.37 (18)C16—C15—C19—Fe258.82 (15)
C3—C4—C5—Fe159.3 (2)C25—C15—C19—Fe2120.9 (2)
C10—Fe1—C5—C1121.82 (15)C21—Fe2—C19—C18171.6 (3)
C9—Fe1—C5—C1165.00 (16)C23—Fe2—C19—C1873.6 (2)
C3—Fe1—C5—C182.07 (19)C22—Fe2—C19—C1841.3 (4)
C2—Fe1—C5—C138.10 (15)C24—Fe2—C19—C18115.6 (2)
C8—Fe1—C5—C1159.5 (3)C17—Fe2—C19—C1837.65 (19)
C4—Fe1—C5—C1119.9 (2)C16—Fe2—C19—C1881.5 (2)
C7—Fe1—C5—C144.6 (4)C20—Fe2—C19—C18157.25 (18)
C6—Fe1—C5—C179.60 (18)C15—Fe2—C19—C18119.3 (3)
C10—Fe1—C5—C4118.26 (19)C18—Fe2—C19—C15119.3 (3)
C9—Fe1—C5—C475.1 (2)C21—Fe2—C19—C1552.3 (4)
C3—Fe1—C5—C437.85 (19)C23—Fe2—C19—C15167.06 (16)
C2—Fe1—C5—C481.8 (2)C22—Fe2—C19—C15160.7 (3)
C8—Fe1—C5—C439.6 (4)C24—Fe2—C19—C15125.05 (17)
C7—Fe1—C5—C4164.5 (3)C17—Fe2—C19—C1581.68 (18)
C6—Fe1—C5—C4160.48 (18)C16—Fe2—C19—C1537.85 (15)
C1—Fe1—C5—C4119.9 (2)C20—Fe2—C19—C1583.42 (19)
C10—Fe1—C6—C7119.1 (2)C18—Fe2—C20—C2438.3 (3)
C9—Fe1—C6—C780.95 (18)C21—Fe2—C20—C24117.9 (2)
C3—Fe1—C6—C739.1 (4)C23—Fe2—C20—C2437.44 (18)
C2—Fe1—C6—C777.31 (18)C19—Fe2—C20—C2477.53 (19)
C8—Fe1—C6—C737.32 (18)C22—Fe2—C20—C2480.86 (19)
C4—Fe1—C6—C7157.9 (3)C17—Fe2—C20—C24156.1 (4)
C5—Fe1—C6—C7163.23 (16)C16—Fe2—C20—C24163.84 (17)
C1—Fe1—C6—C7120.52 (17)C15—Fe2—C20—C24121.37 (17)
C9—Fe1—C6—C1038.18 (19)C18—Fe2—C20—C21156.2 (3)
C3—Fe1—C6—C10158.3 (3)C23—Fe2—C20—C2180.5 (2)
C2—Fe1—C6—C10163.56 (18)C19—Fe2—C20—C21164.55 (18)
C8—Fe1—C6—C1081.8 (2)C22—Fe2—C20—C2137.1 (2)
C4—Fe1—C6—C1038.7 (4)C24—Fe2—C20—C21117.9 (2)
C7—Fe1—C6—C10119.1 (2)C17—Fe2—C20—C2138.2 (4)
C5—Fe1—C6—C1077.64 (19)C16—Fe2—C20—C2178.2 (2)
C1—Fe1—C6—C10120.35 (18)C15—Fe2—C20—C21120.71 (18)
C10—Fe1—C6—C13120.2 (3)C18—Fe2—C20—C2781.0 (4)
C9—Fe1—C6—C13158.4 (3)C21—Fe2—C20—C27122.8 (4)
C3—Fe1—C6—C1381.5 (4)C23—Fe2—C20—C27156.7 (3)
C2—Fe1—C6—C1343.3 (3)C19—Fe2—C20—C2741.8 (3)
C8—Fe1—C6—C13158.0 (3)C22—Fe2—C20—C27159.9 (3)
C4—Fe1—C6—C1381.5 (4)C24—Fe2—C20—C27119.3 (4)
C7—Fe1—C6—C13120.6 (3)C17—Fe2—C20—C2784.6 (5)
C5—Fe1—C6—C1342.6 (3)C16—Fe2—C20—C2744.6 (3)
C1—Fe1—C6—C130.1 (3)C15—Fe2—C20—C272.1 (3)
C10—C6—C7—C80.7 (3)C24—C20—C21—C220.6 (3)
C13—C6—C7—C8179.4 (2)C27—C20—C21—C22179.4 (2)
Fe1—C6—C7—C859.12 (19)Fe2—C20—C21—C2259.5 (2)
C10—C6—C7—Fe158.39 (15)C24—C20—C21—Fe258.96 (17)
C13—C6—C7—Fe1120.3 (2)C27—C20—C21—Fe2121.1 (2)
C10—Fe1—C7—C881.9 (2)C18—Fe2—C21—C2233.9 (4)
C9—Fe1—C7—C837.5 (2)C23—Fe2—C21—C2237.6 (2)
C3—Fe1—C7—C875.5 (2)C19—Fe2—C21—C22161.3 (3)
C2—Fe1—C7—C8118.1 (2)C24—Fe2—C21—C2281.7 (2)
C4—Fe1—C7—C840.5 (4)C17—Fe2—C21—C2272.9 (2)
C5—Fe1—C7—C8166.1 (3)C16—Fe2—C21—C22116.3 (2)
C6—Fe1—C7—C8119.7 (3)C20—Fe2—C21—C22119.9 (3)
C1—Fe1—C7—C8160.25 (19)C15—Fe2—C21—C22159.41 (19)
C10—Fe1—C7—C637.81 (14)C18—Fe2—C21—C20153.8 (3)
C9—Fe1—C7—C682.21 (18)C23—Fe2—C21—C2082.29 (18)
C3—Fe1—C7—C6164.74 (16)C19—Fe2—C21—C2041.4 (4)
C2—Fe1—C7—C6122.18 (17)C22—Fe2—C21—C20119.9 (3)
C8—Fe1—C7—C6119.7 (3)C24—Fe2—C21—C2038.26 (16)
C4—Fe1—C7—C6160.3 (3)C17—Fe2—C21—C20167.15 (17)
C5—Fe1—C7—C646.4 (4)C16—Fe2—C21—C20123.79 (16)
C1—Fe1—C7—C680.02 (18)C15—Fe2—C21—C2080.66 (19)
C6—C7—C8—C90.4 (3)C20—C21—C22—C230.4 (3)
Fe1—C7—C8—C959.1 (2)Fe2—C21—C22—C2359.5 (2)
C6—C7—C8—Fe159.48 (17)C20—C21—C22—Fe259.93 (18)
C10—Fe1—C8—C938.1 (2)C18—Fe2—C22—C2374.6 (3)
C3—Fe1—C8—C9118.8 (2)C21—Fe2—C22—C23119.0 (3)
C2—Fe1—C8—C9159.9 (2)C19—Fe2—C22—C2344.5 (4)
C4—Fe1—C8—C977.7 (3)C24—Fe2—C22—C2337.7 (2)
C7—Fe1—C8—C9119.4 (3)C17—Fe2—C22—C23116.0 (2)
C5—Fe1—C8—C948.8 (5)C16—Fe2—C22—C23156.96 (19)
C6—Fe1—C8—C982.0 (2)C20—Fe2—C22—C2381.4 (2)
C1—Fe1—C8—C9171.0 (2)C15—Fe2—C22—C23173.1 (3)
C10—Fe1—C8—C781.24 (18)C18—Fe2—C22—C21166.33 (19)
C9—Fe1—C8—C7119.4 (3)C23—Fe2—C22—C21119.0 (3)
C3—Fe1—C8—C7121.8 (2)C19—Fe2—C22—C21163.5 (3)
C2—Fe1—C8—C780.8 (2)C24—Fe2—C22—C2181.37 (19)
C4—Fe1—C8—C7162.98 (18)C17—Fe2—C22—C21125.0 (2)
C5—Fe1—C8—C7168.1 (3)C16—Fe2—C22—C2184.0 (2)
C6—Fe1—C8—C737.34 (17)C20—Fe2—C22—C2137.64 (18)
C1—Fe1—C8—C751.6 (4)C15—Fe2—C22—C2154.1 (4)
C7—C8—C9—C100.1 (4)C21—C22—C23—C240.2 (4)
Fe1—C8—C9—C1059.4 (2)Fe2—C22—C23—C2459.6 (2)
C7—C8—C9—Fe159.5 (2)C21—C22—C23—Fe259.4 (2)
C10—Fe1—C9—C8119.1 (3)C18—Fe2—C23—C22121.4 (2)
C3—Fe1—C9—C878.1 (3)C21—Fe2—C23—C2237.7 (2)
C2—Fe1—C9—C847.9 (4)C19—Fe2—C23—C22161.6 (2)
C4—Fe1—C9—C8119.3 (2)C24—Fe2—C23—C22119.5 (3)
C7—Fe1—C9—C837.5 (2)C17—Fe2—C23—C2280.6 (3)
C5—Fe1—C9—C8160.1 (2)C16—Fe2—C23—C2253.4 (4)
C6—Fe1—C9—C881.2 (2)C20—Fe2—C23—C2282.1 (2)
C1—Fe1—C9—C8170.7 (2)C15—Fe2—C23—C22172.8 (3)
C3—Fe1—C9—C10162.88 (17)C18—Fe2—C23—C24119.1 (2)
C2—Fe1—C9—C10167.0 (3)C21—Fe2—C23—C2481.7 (2)
C8—Fe1—C9—C10119.1 (3)C19—Fe2—C23—C2478.9 (2)
C4—Fe1—C9—C10121.65 (18)C22—Fe2—C23—C24119.5 (3)
C7—Fe1—C9—C1081.52 (17)C17—Fe2—C23—C24159.94 (19)
C5—Fe1—C9—C1080.8 (2)C16—Fe2—C23—C24172.8 (3)
C6—Fe1—C9—C1037.83 (17)C20—Fe2—C23—C2437.34 (19)
C1—Fe1—C9—C1051.6 (4)C15—Fe2—C23—C2453.3 (4)
C7—C6—C10—C90.8 (3)C22—C23—C24—C200.2 (4)
C13—C6—C10—C9179.4 (2)Fe2—C23—C24—C2059.78 (19)
Fe1—C6—C10—C959.67 (19)C22—C23—C24—Fe259.6 (2)
C7—C6—C10—Fe158.88 (15)C21—C20—C24—C230.5 (3)
C13—C6—C10—Fe1119.8 (2)C27—C20—C24—C23179.5 (2)
C8—C9—C10—C60.6 (4)Fe2—C20—C24—C2359.0 (2)
Fe1—C9—C10—C660.44 (18)C21—C20—C24—Fe258.58 (16)
C8—C9—C10—Fe159.9 (2)C27—C20—C24—Fe2121.5 (2)
C9—Fe1—C10—C6118.8 (3)C18—Fe2—C24—C2376.8 (2)
C3—Fe1—C10—C6160.2 (3)C21—Fe2—C24—C2381.0 (2)
C2—Fe1—C10—C645.4 (4)C19—Fe2—C24—C23119.3 (2)
C8—Fe1—C10—C681.29 (18)C22—Fe2—C24—C2337.3 (2)
C4—Fe1—C10—C6165.12 (15)C17—Fe2—C24—C2344.1 (4)
C7—Fe1—C10—C637.62 (14)C16—Fe2—C24—C23169.8 (4)
C5—Fe1—C10—C6122.32 (16)C20—Fe2—C24—C23119.8 (3)
C1—Fe1—C10—C680.30 (19)C15—Fe2—C24—C23160.48 (19)
C3—Fe1—C10—C941.3 (4)C18—Fe2—C24—C20163.47 (17)
C2—Fe1—C10—C9164.3 (3)C21—Fe2—C24—C2038.73 (16)
C8—Fe1—C10—C937.54 (19)C23—Fe2—C24—C20119.8 (3)
C4—Fe1—C10—C976.0 (2)C19—Fe2—C24—C20120.89 (17)
C7—Fe1—C10—C981.2 (2)C22—Fe2—C24—C2082.4 (2)
C5—Fe1—C10—C9118.8 (2)C17—Fe2—C24—C20163.8 (3)
C6—Fe1—C10—C9118.8 (3)C16—Fe2—C24—C2050.0 (5)
C1—Fe1—C10—C9160.86 (19)C15—Fe2—C24—C2079.75 (19)
N2—N1—C11—C1177.6 (2)N6—N5—C25—C15176.7 (2)
N2—N1—C11—C121.7 (4)N6—N5—C25—C263.7 (4)
C5—C1—C11—N112.9 (3)C16—C15—C25—N57.8 (4)
C2—C1—C11—N1165.4 (2)C19—C15—C25—N5172.6 (2)
Fe1—C1—C11—N1103.9 (3)Fe2—C15—C25—N597.6 (3)
C5—C1—C11—C12167.7 (2)C16—C15—C25—C26172.5 (2)
C2—C1—C11—C1214.0 (3)C19—C15—C25—C267.1 (4)
Fe1—C1—C11—C1276.7 (3)Fe2—C15—C25—C2682.8 (3)
N4—N3—C13—C6175.0 (2)N8—N7—C27—C20176.1 (3)
N4—N3—C13—C144.6 (4)N8—N7—C27—C283.1 (5)
C7—C6—C13—N310.5 (3)C24—C20—C27—N714.5 (4)
C10—C6—C13—N3171.1 (2)C21—C20—C27—N7165.5 (3)
Fe1—C6—C13—N3100.2 (3)Fe2—C20—C27—N7103.8 (3)
C7—C6—C13—C14169.2 (2)C24—C20—C27—C28166.3 (3)
C10—C6—C13—C149.2 (3)C21—C20—C27—C2813.8 (4)
Fe1—C6—C13—C1479.5 (3)Fe2—C20—C27—C2877.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N7i0.902.533.287 (5)142
N4—H4A···N5ii0.902.293.137 (4)157
N4—H4B···N2iii0.902.613.421 (4)150
N6—H6A···N3iv0.902.243.073 (4)154
N8—H8B···N1v0.902.603.497 (5)178
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x1, y, z; (iii) x1/2, y+1/2, z; (iv) x+1, y, z; (v) x+1, y+1, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···N7i0.902.533.287 (5)142
N4—H4A···N5ii0.902.293.137 (4)157
N4—H4B···N2iii0.902.613.421 (4)150
N6—H6A···N3iv0.902.243.073 (4)154
N8—H8B···N1v0.902.603.497 (5)178
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x1, y, z; (iii) x1/2, y+1/2, z; (iv) x+1, y, z; (v) x+1, y+1, z1/2.
 

Acknowledgements

We thank Professor Abel M. Maharramov for fruitful discussions and help with this work.

References

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Volume 70| Part 8| August 2014| Pages m286-m287
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