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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m396.
Published online 2010 March 13. doi:  10.1107/S1600536810008342
PMCID: PMC2983907

2-Ferrocenyl-N-(6-methyl-2-pyrid­yl)benzamide

Abstract

The title compound, [Fe(C5H5)(C18H15N2O)], a product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-6-methyl­pyridine, crystallizes with two dissimilar mol­ecules in the asymmetric unit. In one mol­ecule, the picoline amide group is directed away from the 2-ferrocenylbenzene moiety (anti) whereas in the other, these are proximate (syn). In the crystal structure, mol­ecules aggregate into dimers via cyclic, asymmetric N—H(...)N inter­actions with graph set R 2 2(8), and are further augmented via intra­molecular C—H(...)O=C and inter­dimer C—H(...)π(arene) inter­actions. Dimers are linked into chains along the [102] direction via weak C—H(...)O hydrogen bonds.

Related literature

For background information and related structures, see: Donnelly et al. (2008 [triangle]); Gallagher et al. (2008 [triangle], 2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m396-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C18H15N2O)]
  • M r = 396.26
  • Trigonal, An external file that holds a picture, illustration, etc.
Object name is e-66-0m396-efi1.jpg
  • a = 22.8234 (9) Å
  • c = 36.9342 (15) Å
  • V = 16661.7 (11) Å3
  • Z = 36
  • Mo Kα radiation
  • μ = 0.83 mm−1
  • T = 150 K
  • 0.30 × 0.25 × 0.20 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: multi-scan (SORTAV; Blessing, 1995 [triangle]) T min = 0.788, T max = 0.851
  • 16925 measured reflections
  • 6243 independent reflections
  • 4606 reflections with I > 2σ(I)
  • R int = 0.085

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.099
  • S = 1.01
  • 6243 reflections
  • 490 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.32 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2941 Friedel pairs
  • Flack parameter: 0.016 (18)

Data collection: KappaCCD Server Software (Nonius, 1997 [triangle]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]) and SORTX (McArdle, 1995 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97 and PREP8 (Ferguson, 1998 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008342/tk2637sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008342/tk2637Isup2.hkl

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

Acknowledgments

JFG thanks Dublin City University for grants in aid of research and the PRTLI-3 program for funding of a postdoctoral fellowship for SA.

supplementary crystallographic information

Comment

The condensation reactions of benzoic acids and benzoyl chlorides with aromatic amino derivatives are well established. For those amines containing an ortho-ring N atom (such as ortho-aminopyridine), two products can be isolated having either the 1:1 or 2:1 benzoyl:pyridine components, and with yields and product ratios depending on the reaction conditions. Herein, we report the molecular and crystal structure of the ferrocene derivative, 2-ferrocenylbenzoyl-N-(3-methyl-2-pyridine), (I).

We have reported on the structure of a 1:1 derivative recently namely 2,3-difluoro-N-(2-pyridyl)benzamide (II) (Gallagher et al., 2008) together with related fluoro(pyridyl)benzamides (Donnelly et al., 2008) and an example of a 2:1 organometallic ferrocenyl analogue of these systems where a sterically bulky ferrocenyl group is a substituent on the aromatic ring namely, 2-ferrocenyl-N-(2-ferrocenylbenzoyl)-N-(5-methyl-2-pyridyl)benzamide (III) (Gallagher et al., 2009).

Compound (I), a product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-6-methylpyridine, crystallises with two dissimilar molecules (A; Fig. 1) and (B; Fig. 2) in the asymmetric unit of space group R3c. Molecules aggregate into dimers via cyclic, asymmetric N—H···N interactions with graph set R22(8), Fig. 3, further augmented via intramolecular C—H···O=C and interdimer C—H···π(arene) interactions, Table 1. Dimers are linked into chains via weak C—H···O contacts, Table 1.

The individual molecules do not exhibit any disorder and no rotational disorder was detected in the methyl-H atoms. Although the five carbon atoms in the unsubstituted η-C5H5 ring of molecule B show increased librational motion, there is no evidence for disorder in this group. The molecules of (A) and (B) are distinctly different and differ principally due to the orientation of the picoline amide group in relation to the 2-ferrocenylbenzene moiety. Differences between molecules (A) and (B) can be highlighted by analysis and comparison of the geometric data. The O1—C1—C32—C31 torsion angle is -123.4 (5)° (syn) in (A) and 51.5 (7)° (anti) in (B), whereas, the Fe1···O1A distance is 5.364 (4) Å as compared to Fe2···O1B with 4.841 (4) Å; the Fe1···N6A, Fe2···N6B distances are 6.544 (4) and 7.334 (4) Å, respectively. The interplanar angles between the seven atom picoline group [C2–C7] and the substituted η-C5H4 ring are 60.71 (17) ° (A) and 39.73 (19) ° (B). In fact, the superposition of molecule (A) and molecule (B) via a best atom fit in PLATON (Spek, 2009) produces a superposition whereby the aromatic chain has a reasonable fit but the ferrocene moieties are rotated by ca. 90° with respect to one another (Fig. 4).

Experimental

Compound (I) was synthesized via standard condensation procedures and similar to the related syntheses reported by us (Gallagher et al., 2008, 2009). Separation of the 1:1 and 2:1 derivatives was undertaken by using flash chromatography using CHCl3:ethyl acetate. Typical organic workup and washing gave the product (I) in modest yield of 30-40% as a 1:1 component of the mixture. Crystals suitable for X-ray diffraction were grown from CHCl3 as colourless blocks over a period of 1-2 weeks. The compounds gave clean 1H and 13C NMR spectra in CDCl3 and infrared spectra (in CHCl3 solution, and as KBr disks).

Refinement

H atoms attached to C atoms were treated as riding using the SHELXL97 (Sheldrick, 2008) defaults at 150 (1) K with C—H = 0.95 Å (aromatic) and 0.98 Å (CH3) and Uiso(H) = 1.2Ueq(C) (aromatic) and 1.5Ueq(CH3).

Figures

Fig. 1.
A view of molecule (A) in (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A view of molecule (B) in (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 3.
A view of the cyclic, asymmetric hydrogen bonded dimer in (I). Displacement ellipsoids are drawn at the 30% probability level. Intramolecular N–H···N and C–H···O contacts are shown as dashed ...
Fig. 4.
A best fit of molecules (A) and (B) with atoms drawn as their van der Waals spheres.

Crystal data

[Fe(C5H5)(C18H15N2O)]? #Insert any comments here.
Mr = 396.26Dx = 1.422 Mg m3
Trigonal, R3cMo Kα radiation, λ = 0.71073 Å
Hall symbol: R 3 -2"cCell parameters from 7571 reflections
a = 22.8234 (9) Åθ = 2.5–27.5°
c = 36.9342 (15) ŵ = 0.83 mm1
V = 16661.7 (11) Å3T = 150 K
Z = 36Block, red
F(000) = 74160.30 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer6243 independent reflections
Radiation source: fine-focus sealed X-ray tube4606 reflections with I > 2σ(I)
graphiteRint = 0.085
[var phi], ω scans with κ offsetsθmax = 25.1°, θmin = 2.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)h = −26→27
Tmin = 0.788, Tmax = 0.851k = −22→27
16925 measured reflectionsl = −44→44

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047w = 1/[σ2(Fo2) + (0.0293P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.099(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.34 e Å3
6243 reflectionsΔρmin = −0.32 e Å3
490 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.000083 (13)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2941 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.016 (18)

Special details

Experimental. ? #Insert any special details here.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Fe10.50804 (4)−0.14058 (4)0.366994 (17)0.03041 (18)
O1A0.57964 (17)0.06331 (18)0.46101 (8)0.0400 (9)
C1A0.5487 (2)0.0564 (2)0.43285 (12)0.0307 (12)
N1A0.5742 (2)0.1010 (2)0.40451 (10)0.0329 (10)
C2A0.6361 (2)0.1619 (2)0.40334 (13)0.0304 (11)
C3A0.6777 (3)0.1920 (3)0.43291 (14)0.0402 (13)
C4A0.7357 (3)0.2530 (3)0.42786 (15)0.0463 (14)
C5A0.7516 (3)0.2829 (3)0.39425 (16)0.0479 (15)
C6A0.7084 (3)0.2492 (3)0.36536 (14)0.0364 (12)
N6A0.6509 (2)0.1895 (2)0.36968 (10)0.0325 (10)
C7A0.7260 (3)0.2778 (3)0.32778 (14)0.0483 (15)
C11A0.5034 (2)−0.0544 (2)0.37597 (12)0.0295 (11)
C12A0.5684 (2)−0.0443 (3)0.38589 (13)0.0359 (12)
C13A0.5978 (2)−0.0558 (3)0.35475 (12)0.0343 (12)
C14A0.5515 (3)−0.0723 (2)0.32600 (13)0.0371 (13)
C15A0.4937 (3)−0.0716 (2)0.33915 (13)0.0334 (11)
C21A0.4454 (3)−0.2125 (3)0.40302 (17)0.0564 (17)
C22A0.5093 (3)−0.2068 (3)0.40364 (15)0.0520 (16)
C23A0.5234 (3)−0.2213 (3)0.36932 (15)0.0438 (14)
C24A0.4697 (3)−0.2356 (3)0.34657 (15)0.0463 (15)
C25A0.4201 (3)−0.2311 (3)0.3679 (2)0.0579 (17)
C31A0.4549 (2)−0.0484 (2)0.40025 (12)0.0304 (11)
C32A0.4772 (2)−0.0007 (2)0.42779 (12)0.0313 (12)
C33A0.4314 (3)−0.0013 (3)0.45290 (13)0.0386 (13)
C34A0.3634 (3)−0.0454 (3)0.44892 (14)0.0420 (14)
C35A0.3401 (3)−0.0903 (3)0.42023 (13)0.0427 (14)
C36A0.3853 (2)−0.0928 (3)0.39645 (13)0.0351 (12)
Fe20.75675 (4)0.24247 (4)0.20017 (2)0.0447 (2)
O1B0.59914 (18)0.03559 (17)0.26183 (8)0.0401 (9)
C1B0.6231 (3)0.0788 (2)0.28568 (12)0.0337 (12)
N1B0.5843 (2)0.0959 (2)0.30677 (10)0.0327 (10)
C2B0.5134 (3)0.0664 (2)0.30552 (13)0.0325 (12)
C3B0.4736 (3)0.0285 (3)0.27629 (13)0.0395 (13)
C4B0.4048 (3)0.0016 (3)0.27882 (13)0.0435 (14)
C5B0.3770 (3)0.0133 (3)0.30940 (13)0.0437 (14)
C6B0.4198 (3)0.0534 (3)0.33658 (13)0.0370 (13)
N6B0.4872 (2)0.0781 (2)0.33541 (10)0.0310 (10)
C7B0.3923 (3)0.0691 (3)0.36966 (13)0.0444 (14)
C11B0.7250 (3)0.1543 (3)0.22829 (13)0.0360 (12)
C12B0.7609 (3)0.1553 (3)0.19618 (14)0.0408 (13)
C13B0.7272 (3)0.1624 (3)0.16588 (15)0.0509 (15)
C14B0.6697 (3)0.1647 (3)0.17836 (14)0.0488 (15)
C15B0.6687 (3)0.1612 (3)0.21681 (13)0.0369 (13)
C21B0.8174 (3)0.3209 (3)0.23378 (19)0.0610 (18)
C22B0.8532 (3)0.3239 (3)0.20214 (18)0.0612 (18)
C23B0.7597 (3)0.3296 (3)0.1862 (3)0.078 (2)
C24B0.8179 (3)0.3297 (3)0.1727 (2)0.069 (2)
C25B0.7593 (4)0.3239 (3)0.2240 (3)0.076 (2)
C31B0.7450 (3)0.1491 (3)0.26582 (13)0.0366 (13)
C32B0.6971 (3)0.1165 (3)0.29373 (12)0.0344 (12)
C33B0.7189 (3)0.1147 (3)0.32885 (14)0.0396 (13)
C34B0.7865 (3)0.1428 (3)0.33625 (14)0.0445 (15)
C35B0.8341 (3)0.1738 (3)0.30914 (15)0.0493 (15)
C36B0.8138 (3)0.1777 (3)0.27450 (14)0.0423 (13)
H1A0.54900.09010.38490.040*
H3A0.66650.17100.45600.048*
H4A0.76510.27470.44770.056*
H5A0.79120.32570.39080.058*
H7A10.74110.25170.31340.072*
H7A20.76230.32520.32900.072*
H7A30.68600.27540.31640.072*
H12A0.5884−0.03190.40920.043*
H13A0.6407−0.05290.35350.041*
H14A0.5580−0.08220.30190.045*
H15A0.4548−0.08120.32530.040*
H21A0.4233−0.20500.42280.068*
H22A0.5382−0.19510.42410.062*
H23A0.5635−0.22150.36250.053*
H24A0.4665−0.24630.32150.056*
H25A0.3772−0.23940.35960.069*
H33A0.44740.02900.47290.046*
H34A0.3323−0.04500.46590.050*
H35A0.2929−0.11940.41690.051*
H36A0.3691−0.12500.37730.042*
H1B0.60600.12850.32260.039*
H3B0.49350.02160.25530.047*
H4B0.3763−0.02520.25960.052*
H5B0.3294−0.00580.31160.052*
H7B10.41030.05880.39130.067*
H7B20.34280.04160.36960.067*
H7B30.40580.11710.36970.067*
H12B0.80070.15190.19540.049*
H13B0.74070.16510.14130.061*
H14B0.63740.16800.16360.059*
H15B0.63640.16310.23220.044*
H21B0.83040.31740.25780.073*
H22B0.89390.32230.20100.073*
H23B0.72660.33280.17210.093*
H24B0.83070.33320.14800.083*
H25B0.72610.32240.24010.092*
H33B0.68660.09390.34770.047*
H34B0.80080.14100.36020.053*
H35B0.88090.19240.31440.059*
H36B0.84690.20010.25620.051*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Fe10.0272 (4)0.0289 (4)0.0357 (3)0.0144 (4)0.0013 (3)−0.0019 (3)
O1A0.038 (2)0.044 (2)0.0380 (19)0.0196 (19)−0.0092 (17)−0.0015 (17)
C1A0.032 (3)0.028 (3)0.037 (3)0.019 (3)0.005 (2)−0.005 (2)
N1A0.032 (3)0.028 (2)0.033 (2)0.011 (2)−0.0009 (19)−0.0044 (19)
C2A0.029 (3)0.023 (3)0.039 (3)0.012 (2)−0.003 (2)−0.007 (2)
C3A0.037 (3)0.035 (3)0.047 (3)0.017 (3)−0.013 (3)−0.013 (3)
C4A0.037 (4)0.038 (3)0.055 (3)0.013 (3)−0.017 (3)−0.012 (3)
C5A0.034 (3)0.030 (3)0.073 (4)0.011 (3)−0.009 (3)−0.008 (3)
C6A0.036 (3)0.028 (3)0.049 (3)0.019 (3)0.004 (3)−0.001 (2)
N6A0.031 (3)0.029 (2)0.038 (2)0.016 (2)0.0023 (19)−0.006 (2)
C7A0.046 (4)0.040 (4)0.054 (3)0.017 (3)0.009 (3)0.003 (3)
C11A0.022 (3)0.026 (3)0.037 (3)0.010 (2)0.006 (2)−0.004 (2)
C12A0.025 (3)0.032 (3)0.045 (3)0.010 (2)−0.001 (2)−0.013 (2)
C13A0.021 (3)0.034 (3)0.045 (3)0.012 (2)0.006 (2)−0.007 (2)
C14A0.041 (3)0.035 (3)0.038 (3)0.021 (3)0.012 (3)0.001 (2)
C15A0.033 (3)0.030 (3)0.039 (3)0.017 (3)0.000 (2)0.000 (2)
C21A0.060 (5)0.045 (4)0.069 (4)0.030 (4)0.021 (4)0.011 (3)
C22A0.062 (4)0.040 (4)0.053 (4)0.024 (3)−0.005 (3)0.006 (3)
C23A0.040 (4)0.043 (3)0.056 (3)0.026 (3)0.008 (3)0.009 (3)
C24A0.055 (4)0.030 (3)0.050 (3)0.018 (3)−0.003 (3)−0.005 (3)
C25A0.032 (4)0.028 (4)0.111 (5)0.013 (3)−0.003 (4)0.007 (3)
C31A0.026 (3)0.027 (3)0.039 (3)0.014 (2)0.004 (2)−0.003 (2)
C32A0.031 (3)0.030 (3)0.039 (3)0.019 (3)0.003 (2)−0.003 (2)
C33A0.040 (3)0.041 (3)0.040 (3)0.024 (3)0.009 (3)−0.007 (2)
C34A0.045 (4)0.038 (3)0.047 (3)0.023 (3)0.016 (3)0.000 (3)
C35A0.025 (3)0.050 (4)0.054 (3)0.020 (3)0.009 (2)−0.002 (3)
C36A0.027 (3)0.033 (3)0.043 (3)0.014 (3)0.000 (2)−0.011 (2)
Fe20.0383 (5)0.0357 (5)0.0649 (5)0.0220 (4)0.0165 (4)0.0114 (4)
O1B0.037 (2)0.033 (2)0.0414 (19)0.0103 (18)0.0025 (17)−0.0091 (17)
C1B0.043 (3)0.028 (3)0.031 (3)0.018 (3)0.008 (2)0.002 (2)
N1B0.030 (3)0.029 (2)0.033 (2)0.009 (2)−0.0003 (18)−0.0051 (18)
C2B0.035 (3)0.025 (3)0.037 (3)0.015 (3)0.002 (2)0.002 (2)
C3B0.044 (3)0.037 (3)0.034 (3)0.018 (3)−0.002 (2)−0.003 (2)
C4B0.039 (4)0.049 (4)0.040 (3)0.021 (3)−0.011 (3)−0.007 (3)
C5B0.033 (3)0.044 (4)0.047 (3)0.014 (3)−0.007 (3)−0.008 (3)
C6B0.031 (3)0.040 (3)0.045 (3)0.021 (3)−0.002 (3)0.000 (3)
N6B0.036 (3)0.032 (2)0.029 (2)0.019 (2)0.0030 (18)0.0023 (18)
C7B0.045 (4)0.055 (4)0.042 (3)0.031 (3)0.003 (3)−0.002 (3)
C11B0.039 (3)0.030 (3)0.044 (3)0.022 (3)0.009 (2)0.004 (2)
C12B0.040 (3)0.038 (3)0.050 (3)0.023 (3)0.017 (3)0.002 (3)
C13B0.064 (4)0.051 (4)0.045 (3)0.034 (4)0.014 (3)0.006 (3)
C14B0.053 (4)0.047 (4)0.050 (3)0.027 (3)0.001 (3)0.005 (3)
C15B0.033 (3)0.034 (3)0.046 (3)0.018 (3)0.007 (2)0.001 (2)
C21B0.043 (4)0.035 (4)0.097 (5)0.014 (3)0.024 (4)0.008 (3)
C22B0.037 (4)0.040 (4)0.102 (5)0.016 (3)0.021 (4)0.016 (4)
C23B0.040 (4)0.040 (4)0.158 (8)0.023 (4)0.023 (5)0.039 (5)
C24B0.049 (4)0.044 (4)0.108 (5)0.018 (4)0.024 (4)0.029 (4)
C25B0.057 (5)0.023 (4)0.138 (7)0.011 (3)0.044 (5)0.009 (4)
C31B0.038 (3)0.028 (3)0.047 (3)0.019 (3)0.006 (2)−0.003 (2)
C32B0.031 (3)0.029 (3)0.045 (3)0.016 (3)0.002 (2)−0.001 (2)
C33B0.046 (4)0.029 (3)0.042 (3)0.018 (3)0.004 (3)0.002 (2)
C34B0.055 (4)0.042 (4)0.042 (3)0.029 (3)−0.007 (3)−0.006 (3)
C35B0.043 (4)0.049 (4)0.062 (4)0.027 (3)−0.010 (3)−0.014 (3)
C36B0.042 (4)0.033 (3)0.055 (3)0.021 (3)0.010 (3)−0.002 (3)

Geometric parameters (Å, °)

Fe1—C11A2.048 (5)Fe2—C11B2.048 (5)
Fe1—C12A2.047 (5)Fe2—C12B2.044 (5)
Fe1—C13A2.045 (5)Fe2—C13B2.041 (6)
Fe1—C14A2.040 (5)Fe2—C14B2.054 (6)
Fe1—C15A2.039 (5)Fe2—C15B2.031 (5)
Fe1—C21A2.040 (6)Fe2—C21B2.045 (7)
Fe1—C22A2.040 (5)Fe2—C22B2.053 (6)
Fe1—C23A2.043 (5)Fe2—C23B2.023 (6)
Fe1—C24A2.035 (5)Fe2—C24B2.041 (6)
Fe1—C25A2.037 (6)Fe2—C25B2.031 (7)
O1A—C1A1.222 (5)O1B—C1B1.229 (5)
C1A—N1A1.370 (6)C1B—N1B1.373 (6)
C1A—C32A1.506 (7)C1B—C32B1.493 (7)
N1A—C2A1.402 (6)N1B—C2B1.409 (6)
N1A—H1A0.8800N1B—H1B0.8800
C2A—N6A1.357 (6)C2B—N6B1.345 (6)
C2A—C3A1.384 (6)C2B—C3B1.398 (7)
C3A—C4A1.372 (7)C3B—C4B1.373 (7)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.375 (7)C4B—C5B1.386 (7)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.394 (7)C5B—C6B1.381 (7)
C5A—H5A0.9500C5B—H5B0.9500
C6A—N6A1.349 (6)C6B—N6B1.348 (6)
C6A—C7A1.501 (7)C6B—C7B1.496 (6)
C7A—H7A10.9800C7B—H7B10.9800
C7A—H7A20.9800C7B—H7B20.9800
C7A—H7A30.9800C7B—H7B30.9800
C11A—C15A1.402 (6)C11B—C15B1.434 (7)
C11A—C12A1.430 (7)C11B—C12B1.435 (7)
C11A—C31A1.483 (6)C11B—C31B1.483 (7)
C12A—C13A1.420 (6)C12B—C13B1.413 (8)
C12A—H12A0.9500C12B—H12B0.9500
C13A—C14A1.410 (7)C13B—C14B1.415 (8)
C13A—H13A0.9500C13B—H13B0.9500
C14A—C15A1.412 (7)C14B—C15B1.422 (7)
C14A—H14A0.9500C14B—H14B0.9500
C15A—H15A0.9500C15B—H15B0.9500
C21A—C25A1.397 (8)C21B—C22B1.407 (8)
C21A—C22A1.400 (8)C21B—C25B1.409 (9)
C21A—H21A0.9500C21B—H21B0.9500
C22A—C23A1.388 (7)C22B—C24B1.399 (9)
C22A—H22A0.9500C22B—H22B0.9500
C23A—C24A1.385 (8)C23B—C25B1.403 (10)
C23A—H23A0.9500C23B—C24B1.417 (9)
C24A—C25A1.423 (8)C23B—H23B0.9500
C24A—H24A0.9500C24B—H24B0.9500
C25A—H25A0.9500C25B—H25B0.9500
C31A—C32A1.387 (6)C31B—C36B1.403 (7)
C31A—C36A1.400 (7)C31B—C32B1.413 (7)
C32A—C33A1.393 (6)C32B—C33B1.397 (6)
C33A—C34A1.372 (7)C33B—C34B1.371 (8)
C33A—H33A0.9500C33B—H33B0.9500
C34A—C35A1.382 (7)C34B—C35B1.384 (7)
C34A—H34A0.9500C34B—H34B0.9500
C35A—C36A1.378 (6)C35B—C36B1.379 (7)
C35A—H35A0.9500C35B—H35B0.9500
C36A—H36A0.9500C36B—H36B0.9500
C24A—Fe1—C25A40.9 (2)C23B—Fe2—C25B40.5 (3)
C24A—Fe1—C15A119.1 (2)C23B—Fe2—C15B120.4 (2)
C25A—Fe1—C15A109.5 (2)C25B—Fe2—C15B105.5 (2)
C24A—Fe1—C14A109.0 (2)C23B—Fe2—C24B40.8 (2)
C25A—Fe1—C14A130.0 (3)C25B—Fe2—C24B68.3 (3)
C15A—Fe1—C14A40.51 (19)C15B—Fe2—C24B157.3 (3)
C24A—Fe1—C21A68.3 (3)C23B—Fe2—C13B123.8 (3)
C25A—Fe1—C21A40.1 (2)C25B—Fe2—C13B159.1 (3)
C15A—Fe1—C21A129.1 (2)C15B—Fe2—C13B68.7 (2)
C14A—Fe1—C21A167.5 (3)C24B—Fe2—C13B108.9 (3)
C24A—Fe1—C22A67.3 (2)C23B—Fe2—C12B160.7 (3)
C25A—Fe1—C22A67.0 (3)C25B—Fe2—C12B158.1 (3)
C15A—Fe1—C22A166.9 (2)C15B—Fe2—C12B68.9 (2)
C14A—Fe1—C22A151.3 (2)C24B—Fe2—C12B124.9 (3)
C21A—Fe1—C22A40.1 (2)C13B—Fe2—C12B40.5 (2)
C24A—Fe1—C23A39.7 (2)C23B—Fe2—C21B67.6 (3)
C25A—Fe1—C23A67.1 (2)C25B—Fe2—C21B40.4 (3)
C15A—Fe1—C23A152.1 (2)C15B—Fe2—C21B122.9 (2)
C14A—Fe1—C23A118.9 (2)C24B—Fe2—C21B67.3 (3)
C21A—Fe1—C23A67.3 (2)C13B—Fe2—C21B159.4 (3)
C22A—Fe1—C23A39.7 (2)C12B—Fe2—C21B123.7 (3)
C24A—Fe1—C13A128.3 (2)C23B—Fe2—C11B156.5 (3)
C25A—Fe1—C13A167.4 (2)C25B—Fe2—C11B120.9 (3)
C15A—Fe1—C13A68.2 (2)C15B—Fe2—C11B41.15 (19)
C14A—Fe1—C13A40.40 (19)C24B—Fe2—C11B160.8 (2)
C21A—Fe1—C13A150.8 (2)C13B—Fe2—C11B68.8 (2)
C22A—Fe1—C13A118.0 (2)C12B—Fe2—C11B41.07 (19)
C23A—Fe1—C13A108.7 (2)C21B—Fe2—C11B107.7 (2)
C24A—Fe1—C12A166.2 (2)C23B—Fe2—C22B68.0 (3)
C25A—Fe1—C12A151.2 (2)C25B—Fe2—C22B68.2 (3)
C15A—Fe1—C12A67.9 (2)C15B—Fe2—C22B159.9 (2)
C14A—Fe1—C12A67.9 (2)C24B—Fe2—C22B40.0 (2)
C21A—Fe1—C12A117.8 (2)C13B—Fe2—C22B123.9 (3)
C22A—Fe1—C12A108.6 (2)C12B—Fe2—C22B109.5 (2)
C23A—Fe1—C12A128.9 (2)C21B—Fe2—C22B40.2 (2)
C13A—Fe1—C12A40.62 (18)C11B—Fe2—C22B124.4 (3)
C24A—Fe1—C11A151.9 (2)C23B—Fe2—C14B107.0 (3)
C25A—Fe1—C11A118.3 (2)C25B—Fe2—C14B122.3 (3)
C15A—Fe1—C11A40.12 (18)C15B—Fe2—C14B40.73 (19)
C14A—Fe1—C11A67.99 (19)C24B—Fe2—C14B122.8 (3)
C21A—Fe1—C11A108.3 (2)C13B—Fe2—C14B40.4 (2)
C22A—Fe1—C11A129.1 (2)C12B—Fe2—C14B68.1 (2)
C23A—Fe1—C11A166.9 (2)C21B—Fe2—C14B159.0 (2)
C13A—Fe1—C11A68.60 (19)C11B—Fe2—C14B68.6 (2)
C12A—Fe1—C11A40.87 (19)C22B—Fe2—C14B158.8 (2)
O1A—C1A—N1A123.4 (5)O1B—C1B—N1B122.9 (5)
O1A—C1A—C32A121.5 (4)O1B—C1B—C32B121.8 (4)
N1A—C1A—C32A115.0 (4)N1B—C1B—C32B115.3 (4)
C1A—N1A—C2A127.1 (4)C1B—N1B—C2B126.5 (4)
C1A—N1A—H1A116.4C1B—N1B—H1B116.7
C2A—N1A—H1A116.4C2B—N1B—H1B116.7
N6A—C2A—C3A122.9 (5)N6B—C2B—C3B122.7 (5)
N6A—C2A—N1A112.4 (4)N6B—C2B—N1B113.4 (4)
C3A—C2A—N1A124.7 (4)C3B—C2B—N1B123.9 (4)
C4A—C3A—C2A118.1 (5)C4B—C3B—C2B117.9 (5)
C4A—C3A—H3A121.0C4B—C3B—H3B121.0
C2A—C3A—H3A121.0C2B—C3B—H3B121.0
C3A—C4A—C5A120.6 (5)C3B—C4B—C5B120.1 (5)
C3A—C4A—H4A119.7C3B—C4B—H4B120.0
C5A—C4A—H4A119.7C5B—C4B—H4B120.0
C4A—C5A—C6A118.6 (5)C6B—C5B—C4B118.6 (5)
C4A—C5A—H5A120.7C6B—C5B—H5B120.7
C6A—C5A—H5A120.7C4B—C5B—H5B120.7
N6A—C6A—C5A122.0 (5)N6B—C6B—C5B122.4 (5)
N6A—C6A—C7A117.6 (5)N6B—C6B—C7B117.0 (4)
C5A—C6A—C7A120.4 (5)C5B—C6B—C7B120.6 (5)
C6A—N6A—C2A117.9 (4)C2B—N6B—C6B118.1 (4)
C6A—C7A—H7A1109.5C6B—C7B—H7B1109.5
C6A—C7A—H7A2109.5C6B—C7B—H7B2109.5
H7A1—C7A—H7A2109.5H7B1—C7B—H7B2109.5
C6A—C7A—H7A3109.5C6B—C7B—H7B3109.5
H7A1—C7A—H7A3109.5H7B1—C7B—H7B3109.5
H7A2—C7A—H7A3109.5H7B2—C7B—H7B3109.5
C15A—C11A—C12A107.4 (4)C15B—C11B—C12B106.8 (4)
C15A—C11A—C31A126.3 (5)C15B—C11B—C31B127.9 (4)
C12A—C11A—C31A126.3 (4)C12B—C11B—C31B125.2 (5)
C15A—C11A—Fe169.6 (3)C15B—C11B—Fe268.8 (3)
C12A—C11A—Fe169.5 (3)C12B—C11B—Fe269.3 (3)
C31A—C11A—Fe1125.9 (3)C31B—C11B—Fe2125.5 (4)
C13A—C12A—C11A108.1 (4)C13B—C12B—C11B108.4 (5)
C13A—C12A—Fe169.6 (3)C13B—C12B—Fe269.7 (3)
C11A—C12A—Fe169.6 (3)C11B—C12B—Fe269.6 (3)
C13A—C12A—H12A126.0C13B—C12B—H12B125.8
C11A—C12A—H12A126.0C11B—C12B—H12B125.8
Fe1—C12A—H12A126.4Fe2—C12B—H12B126.5
C14A—C13A—C12A107.4 (4)C12B—C13B—C14B108.3 (5)
C14A—C13A—Fe169.6 (3)C12B—C13B—Fe269.9 (3)
C12A—C13A—Fe169.8 (3)C14B—C13B—Fe270.3 (3)
C14A—C13A—H13A126.3C12B—C13B—H13B125.8
C12A—C13A—H13A126.3C14B—C13B—H13B125.8
Fe1—C13A—H13A125.9Fe2—C13B—H13B125.6
C13A—C14A—C15A108.5 (4)C13B—C14B—C15B108.2 (5)
C13A—C14A—Fe170.0 (3)C13B—C14B—Fe269.3 (3)
C15A—C14A—Fe169.7 (3)C15B—C14B—Fe268.8 (3)
C13A—C14A—H14A125.8C13B—C14B—H14B125.9
C15A—C14A—H14A125.8C15B—C14B—H14B125.9
Fe1—C14A—H14A126.1Fe2—C14B—H14B127.6
C11A—C15A—C14A108.6 (5)C14B—C15B—C11B108.2 (5)
C11A—C15A—Fe170.3 (3)C14B—C15B—Fe270.5 (3)
C14A—C15A—Fe169.8 (3)C11B—C15B—Fe270.1 (3)
C11A—C15A—H15A125.7C14B—C15B—H15B125.9
C14A—C15A—H15A125.7C11B—C15B—H15B125.9
Fe1—C15A—H15A125.8Fe2—C15B—H15B125.1
C25A—C21A—C22A107.2 (5)C22B—C21B—C25B108.8 (7)
C25A—C21A—Fe169.9 (3)C22B—C21B—Fe270.2 (4)
C22A—C21A—Fe170.0 (3)C25B—C21B—Fe269.2 (4)
C25A—C21A—H21A126.4C22B—C21B—H21B125.6
C22A—C21A—H21A126.4C25B—C21B—H21B125.6
Fe1—C21A—H21A125.4Fe2—C21B—H21B126.5
C23A—C22A—C21A108.6 (5)C24B—C22B—C21B107.7 (6)
C23A—C22A—Fe170.2 (3)C24B—C22B—Fe269.6 (4)
C21A—C22A—Fe169.9 (3)C21B—C22B—Fe269.6 (4)
C23A—C22A—H22A125.7C24B—C22B—H22B126.2
C21A—C22A—H22A125.7C21B—C22B—H22B126.2
Fe1—C22A—H22A125.7Fe2—C22B—H22B126.2
C24A—C23A—C22A109.1 (5)C25B—C23B—C24B108.2 (7)
C24A—C23A—Fe169.8 (3)C25B—C23B—Fe270.1 (4)
C22A—C23A—Fe170.0 (3)C24B—C23B—Fe270.3 (4)
C24A—C23A—H23A125.5C25B—C23B—H23B125.9
C22A—C23A—H23A125.5C24B—C23B—H23B125.9
Fe1—C23A—H23A126.3Fe2—C23B—H23B125.4
C23A—C24A—C25A106.8 (5)C22B—C24B—C23B108.0 (7)
C23A—C24A—Fe170.5 (3)C22B—C24B—Fe270.5 (4)
C25A—C24A—Fe169.6 (3)C23B—C24B—Fe268.9 (4)
C23A—C24A—H24A126.6C22B—C24B—H24B126.0
C25A—C24A—H24A126.6C23B—C24B—H24B126.0
Fe1—C24A—H24A124.9Fe2—C24B—H24B126.2
C21A—C25A—C24A108.3 (6)C23B—C25B—C21B107.3 (6)
C21A—C25A—Fe170.1 (4)C23B—C25B—Fe269.4 (4)
C24A—C25A—Fe169.5 (3)C21B—C25B—Fe270.3 (4)
C21A—C25A—H25A125.8C23B—C25B—H25B126.4
C24A—C25A—H25A125.8C21B—C25B—H25B126.4
Fe1—C25A—H25A126.2Fe2—C25B—H25B125.5
C32A—C31A—C36A118.6 (4)C36B—C31B—C32B118.0 (5)
C32A—C31A—C11A121.2 (4)C36B—C31B—C11B119.6 (5)
C36A—C31A—C11A120.1 (4)C32B—C31B—C11B122.4 (5)
C31A—C32A—C33A120.1 (5)C33B—C32B—C31B120.0 (5)
C31A—C32A—C1A125.7 (4)C33B—C32B—C1B119.0 (4)
C33A—C32A—C1A114.1 (4)C31B—C32B—C1B120.8 (4)
C34A—C33A—C32A120.3 (5)C34B—C33B—C32B120.3 (5)
C34A—C33A—H33A119.8C34B—C33B—H33B119.8
C32A—C33A—H33A119.8C32B—C33B—H33B119.8
C33A—C34A—C35A120.0 (5)C33B—C34B—C35B120.5 (5)
C33A—C34A—H34A120.0C33B—C34B—H34B119.7
C35A—C34A—H34A120.0C35B—C34B—H34B119.7
C36A—C35A—C34A120.1 (5)C36B—C35B—C34B120.0 (5)
C36A—C35A—H35A120.0C36B—C35B—H35B120.0
C34A—C35A—H35A120.0C34B—C35B—H35B120.0
C35A—C36A—C31A120.6 (5)C35B—C36B—C31B121.1 (5)
C35A—C36A—H36A119.7C35B—C36B—H36B119.4
C31A—C36A—H36A119.7C31B—C36B—H36B119.4
O1A—C1A—N1A—C2A−3.8 (7)O1B—C1B—N1B—C2B2.2 (8)
C32A—C1A—N1A—C2A173.0 (4)C32B—C1B—N1B—C2B−177.6 (4)
C1A—N1A—C2A—N6A171.1 (4)C1B—N1B—C2B—N6B161.5 (4)
C1A—N1A—C2A—C3A−9.6 (8)C1B—N1B—C2B—C3B−18.4 (8)
N6A—C2A—C3A—C4A1.4 (8)N6B—C2B—C3B—C4B−1.0 (8)
N1A—C2A—C3A—C4A−177.8 (5)N1B—C2B—C3B—C4B178.9 (5)
C2A—C3A—C4A—C5A−0.1 (8)C2B—C3B—C4B—C5B1.2 (8)
C3A—C4A—C5A—C6A−1.5 (8)C3B—C4B—C5B—C6B1.2 (8)
C4A—C5A—C6A—N6A2.0 (8)C4B—C5B—C6B—N6B−4.0 (8)
C4A—C5A—C6A—C7A−176.2 (5)C4B—C5B—C6B—C7B178.4 (5)
C5A—C6A—N6A—C2A−0.8 (7)C3B—C2B—N6B—C6B−1.6 (7)
C7A—C6A—N6A—C2A177.4 (4)N1B—C2B—N6B—C6B178.4 (4)
C3A—C2A—N6A—C6A−0.9 (7)C5B—C6B—N6B—C2B4.2 (7)
N1A—C2A—N6A—C6A178.4 (4)C7B—C6B—N6B—C2B−178.1 (4)
C24A—Fe1—C11A—C15A−51.7 (5)C23B—Fe2—C11B—C15B45.6 (8)
C25A—Fe1—C11A—C15A−87.2 (4)C25B—Fe2—C11B—C15B77.8 (4)
C14A—Fe1—C11A—C15A37.5 (3)C24B—Fe2—C11B—C15B−168.3 (8)
C21A—Fe1—C11A—C15A−129.7 (3)C13B—Fe2—C11B—C15B−81.5 (3)
C22A—Fe1—C11A—C15A−169.5 (3)C12B—Fe2—C11B—C15B−118.6 (4)
C23A—Fe1—C11A—C15A161.8 (9)C21B—Fe2—C11B—C15B120.1 (3)
C13A—Fe1—C11A—C15A81.2 (3)C22B—Fe2—C11B—C15B161.2 (3)
C12A—Fe1—C11A—C15A118.7 (4)C14B—Fe2—C11B—C15B−37.9 (3)
C24A—Fe1—C11A—C12A−170.4 (4)C23B—Fe2—C11B—C12B164.2 (7)
C25A—Fe1—C11A—C12A154.1 (3)C25B—Fe2—C11B—C12B−163.6 (4)
C15A—Fe1—C11A—C12A−118.7 (4)C15B—Fe2—C11B—C12B118.6 (4)
C14A—Fe1—C11A—C12A−81.2 (3)C24B—Fe2—C11B—C12B−49.6 (10)
C21A—Fe1—C11A—C12A111.6 (3)C13B—Fe2—C11B—C12B37.2 (3)
C22A—Fe1—C11A—C12A71.8 (4)C21B—Fe2—C11B—C12B−121.3 (3)
C23A—Fe1—C11A—C12A43.1 (10)C22B—Fe2—C11B—C12B−80.2 (4)
C13A—Fe1—C11A—C12A−37.5 (3)C14B—Fe2—C11B—C12B80.7 (3)
C24A—Fe1—C11A—C31A69.0 (6)C23B—Fe2—C11B—C31B−76.6 (9)
C25A—Fe1—C11A—C31A33.5 (5)C25B—Fe2—C11B—C31B−44.3 (6)
C15A—Fe1—C11A—C31A120.7 (6)C15B—Fe2—C11B—C31B−122.2 (5)
C14A—Fe1—C11A—C31A158.2 (5)C24B—Fe2—C11B—C31B69.6 (10)
C21A—Fe1—C11A—C31A−9.0 (5)C13B—Fe2—C11B—C31B156.4 (5)
C22A—Fe1—C11A—C31A−48.8 (5)C12B—Fe2—C11B—C31B119.2 (6)
C23A—Fe1—C11A—C31A−77.5 (11)C21B—Fe2—C11B—C31B−2.1 (5)
C13A—Fe1—C11A—C31A−158.1 (5)C22B—Fe2—C11B—C31B39.0 (5)
C12A—Fe1—C11A—C31A−120.6 (5)C14B—Fe2—C11B—C31B−160.1 (5)
C15A—C11A—C12A—C13A−0.3 (5)C15B—C11B—C12B—C13B−0.3 (6)
C31A—C11A—C12A—C13A179.3 (5)C31B—C11B—C12B—C13B−178.6 (5)
Fe1—C11A—C12A—C13A59.2 (3)Fe2—C11B—C12B—C13B−59.0 (4)
C15A—C11A—C12A—Fe1−59.5 (3)C15B—C11B—C12B—Fe258.8 (4)
C31A—C11A—C12A—Fe1120.1 (5)C31B—C11B—C12B—Fe2−119.6 (5)
C24A—Fe1—C12A—C13A41.4 (11)C23B—Fe2—C12B—C13B−41.0 (9)
C25A—Fe1—C12A—C13A−172.5 (5)C25B—Fe2—C12B—C13B160.4 (6)
C15A—Fe1—C12A—C13A−81.8 (3)C15B—Fe2—C12B—C13B81.6 (4)
C14A—Fe1—C12A—C13A−37.9 (3)C24B—Fe2—C12B—C13B−78.0 (5)
C21A—Fe1—C12A—C13A154.4 (3)C21B—Fe2—C12B—C13B−162.2 (4)
C22A—Fe1—C12A—C13A111.7 (3)C11B—Fe2—C12B—C13B119.8 (5)
C23A—Fe1—C12A—C13A72.1 (4)C22B—Fe2—C12B—C13B−119.8 (4)
C11A—Fe1—C12A—C13A−119.4 (4)C14B—Fe2—C12B—C13B37.6 (3)
C24A—Fe1—C12A—C11A160.8 (9)C23B—Fe2—C12B—C11B−160.8 (7)
C25A—Fe1—C12A—C11A−53.1 (6)C25B—Fe2—C12B—C11B40.6 (8)
C15A—Fe1—C12A—C11A37.6 (3)C15B—Fe2—C12B—C11B−38.3 (3)
C14A—Fe1—C12A—C11A81.5 (3)C24B—Fe2—C12B—C11B162.2 (4)
C21A—Fe1—C12A—C11A−86.2 (3)C13B—Fe2—C12B—C11B−119.8 (5)
C22A—Fe1—C12A—C11A−128.9 (3)C21B—Fe2—C12B—C11B78.0 (4)
C23A—Fe1—C12A—C11A−168.5 (3)C22B—Fe2—C12B—C11B120.4 (3)
C13A—Fe1—C12A—C11A119.4 (4)C14B—Fe2—C12B—C11B−82.2 (3)
C11A—C12A—C13A—C14A0.5 (6)C11B—C12B—C13B—C14B−0.9 (6)
Fe1—C12A—C13A—C14A59.7 (4)Fe2—C12B—C13B—C14B−60.0 (4)
C11A—C12A—C13A—Fe1−59.2 (3)C11B—C12B—C13B—Fe259.0 (4)
C24A—Fe1—C13A—C14A73.1 (4)C23B—Fe2—C13B—C12B164.9 (3)
C25A—Fe1—C13A—C14A44.7 (12)C25B—Fe2—C13B—C12B−159.5 (7)
C15A—Fe1—C13A—C14A−37.5 (3)C15B—Fe2—C13B—C12B−82.0 (3)
C21A—Fe1—C13A—C14A−170.2 (4)C24B—Fe2—C13B—C12B122.0 (4)
C22A—Fe1—C13A—C14A155.3 (3)C21B—Fe2—C13B—C12B46.3 (9)
C23A—Fe1—C13A—C14A113.0 (3)C11B—Fe2—C13B—C12B−37.7 (3)
C12A—Fe1—C13A—C14A−118.5 (4)C22B—Fe2—C13B—C12B80.3 (4)
C11A—Fe1—C13A—C14A−80.7 (3)C14B—Fe2—C13B—C12B−119.2 (5)
C24A—Fe1—C13A—C12A−168.4 (3)C23B—Fe2—C13B—C14B−75.9 (4)
C25A—Fe1—C13A—C12A163.2 (10)C25B—Fe2—C13B—C14B−40.3 (9)
C15A—Fe1—C13A—C12A81.0 (3)C15B—Fe2—C13B—C14B37.2 (3)
C14A—Fe1—C13A—C12A118.5 (4)C24B—Fe2—C13B—C14B−118.8 (4)
C21A—Fe1—C13A—C12A−51.7 (6)C12B—Fe2—C13B—C14B119.2 (5)
C22A—Fe1—C13A—C12A−86.2 (4)C21B—Fe2—C13B—C14B165.5 (7)
C23A—Fe1—C13A—C12A−128.5 (3)C11B—Fe2—C13B—C14B81.5 (3)
C11A—Fe1—C13A—C12A37.8 (3)C22B—Fe2—C13B—C14B−160.5 (3)
C12A—C13A—C14A—C15A−0.5 (6)C12B—C13B—C14B—C15B1.8 (7)
Fe1—C13A—C14A—C15A59.3 (3)Fe2—C13B—C14B—C15B−57.9 (4)
C12A—C13A—C14A—Fe1−59.8 (3)C12B—C13B—C14B—Fe259.7 (4)
C24A—Fe1—C14A—C13A−127.5 (3)C23B—Fe2—C14B—C13B122.5 (4)
C25A—Fe1—C14A—C13A−168.5 (3)C25B—Fe2—C14B—C13B164.1 (4)
C15A—Fe1—C14A—C13A119.6 (4)C15B—Fe2—C14B—C13B−120.3 (5)
C21A—Fe1—C14A—C13A157.6 (10)C24B—Fe2—C14B—C13B80.7 (4)
C22A—Fe1—C14A—C13A−50.3 (6)C12B—Fe2—C14B—C13B−37.7 (3)
C23A—Fe1—C14A—C13A−85.2 (3)C21B—Fe2—C14B—C13B−165.8 (7)
C12A—Fe1—C14A—C13A38.1 (3)C11B—Fe2—C14B—C13B−82.0 (3)
C11A—Fe1—C14A—C13A82.4 (3)C22B—Fe2—C14B—C13B49.8 (8)
C24A—Fe1—C14A—C15A112.9 (3)C23B—Fe2—C14B—C15B−117.2 (4)
C25A—Fe1—C14A—C15A71.9 (4)C25B—Fe2—C14B—C15B−75.6 (4)
C21A—Fe1—C14A—C15A38.0 (12)C24B—Fe2—C14B—C15B−159.0 (3)
C22A—Fe1—C14A—C15A−169.9 (4)C13B—Fe2—C14B—C15B120.3 (5)
C23A—Fe1—C14A—C15A155.2 (3)C12B—Fe2—C14B—C15B82.6 (3)
C13A—Fe1—C14A—C15A−119.6 (4)C21B—Fe2—C14B—C15B−45.5 (8)
C12A—Fe1—C14A—C15A−81.5 (3)C11B—Fe2—C14B—C15B38.3 (3)
C11A—Fe1—C14A—C15A−37.2 (3)C22B—Fe2—C14B—C15B170.1 (6)
C12A—C11A—C15A—C14A0.0 (5)C13B—C14B—C15B—C11B−2.0 (6)
C31A—C11A—C15A—C14A−179.6 (4)Fe2—C14B—C15B—C11B−60.2 (4)
Fe1—C11A—C15A—C14A−59.4 (3)C13B—C14B—C15B—Fe258.2 (4)
C12A—C11A—C15A—Fe159.5 (3)C12B—C11B—C15B—C14B1.4 (6)
C31A—C11A—C15A—Fe1−120.2 (5)C31B—C11B—C15B—C14B179.7 (5)
C13A—C14A—C15A—C11A0.3 (6)Fe2—C11B—C15B—C14B60.5 (4)
Fe1—C14A—C15A—C11A59.8 (3)C12B—C11B—C15B—Fe2−59.1 (4)
C13A—C14A—C15A—Fe1−59.5 (4)C31B—C11B—C15B—Fe2119.2 (5)
C24A—Fe1—C15A—C11A154.9 (3)C23B—Fe2—C15B—C14B80.6 (5)
C25A—Fe1—C15A—C11A111.0 (3)C25B—Fe2—C15B—C14B121.8 (4)
C14A—Fe1—C15A—C11A−119.6 (4)C24B—Fe2—C15B—C14B51.3 (8)
C21A—Fe1—C15A—C11A70.3 (4)C13B—Fe2—C15B—C14B−36.9 (3)
C22A—Fe1—C15A—C11A38.7 (11)C12B—Fe2—C15B—C14B−80.5 (3)
C23A—Fe1—C15A—C11A−171.3 (4)C21B—Fe2—C15B—C14B162.2 (4)
C13A—Fe1—C15A—C11A−82.2 (3)C11B—Fe2—C15B—C14B−118.7 (4)
C12A—Fe1—C15A—C11A−38.3 (3)C22B—Fe2—C15B—C14B−169.6 (6)
C24A—Fe1—C15A—C14A−85.5 (4)C23B—Fe2—C15B—C11B−160.7 (4)
C25A—Fe1—C15A—C14A−129.4 (3)C25B—Fe2—C15B—C11B−119.5 (4)
C21A—Fe1—C15A—C14A−170.1 (3)C24B—Fe2—C15B—C11B170.0 (7)
C22A—Fe1—C15A—C14A158.3 (10)C13B—Fe2—C15B—C11B81.8 (3)
C23A—Fe1—C15A—C14A−51.7 (6)C12B—Fe2—C15B—C11B38.2 (3)
C13A—Fe1—C15A—C14A37.4 (3)C21B—Fe2—C15B—C11B−79.1 (4)
C12A—Fe1—C15A—C14A81.3 (3)C22B—Fe2—C15B—C11B−50.9 (8)
C11A—Fe1—C15A—C14A119.6 (4)C14B—Fe2—C15B—C11B118.7 (4)
C24A—Fe1—C21A—C25A−37.8 (4)C23B—Fe2—C21B—C22B−81.9 (4)
C15A—Fe1—C21A—C25A72.7 (4)C25B—Fe2—C21B—C22B−120.2 (6)
C14A—Fe1—C21A—C25A41.7 (12)C15B—Fe2—C21B—C22B165.4 (4)
C22A—Fe1—C21A—C25A−117.9 (5)C24B—Fe2—C21B—C22B−37.5 (4)
C23A—Fe1—C21A—C25A−80.8 (4)C13B—Fe2—C21B—C22B45.9 (9)
C13A—Fe1—C21A—C25A−168.8 (4)C12B—Fe2—C21B—C22B80.3 (4)
C12A—Fe1—C21A—C25A155.9 (3)C11B—Fe2—C21B—C22B122.7 (4)
C11A—Fe1—C21A—C25A112.4 (4)C14B—Fe2—C21B—C22B−160.9 (6)
C24A—Fe1—C21A—C22A80.1 (4)C23B—Fe2—C21B—C25B38.3 (4)
C25A—Fe1—C21A—C22A117.9 (5)C15B—Fe2—C21B—C25B−74.4 (5)
C15A—Fe1—C21A—C22A−169.4 (3)C24B—Fe2—C21B—C25B82.6 (5)
C14A—Fe1—C21A—C22A159.6 (10)C13B—Fe2—C21B—C25B166.1 (7)
C23A—Fe1—C21A—C22A37.1 (3)C12B—Fe2—C21B—C25B−159.5 (4)
C13A—Fe1—C21A—C22A−50.9 (6)C11B—Fe2—C21B—C25B−117.1 (4)
C12A—Fe1—C21A—C22A−86.2 (4)C22B—Fe2—C21B—C25B120.2 (6)
C11A—Fe1—C21A—C22A−129.6 (4)C14B—Fe2—C21B—C25B−40.7 (9)
C25A—C21A—C22A—C23A0.4 (7)C25B—C21B—C22B—C24B0.8 (7)
Fe1—C21A—C22A—C23A−59.8 (4)Fe2—C21B—C22B—C24B59.4 (5)
C25A—C21A—C22A—Fe160.2 (4)C25B—C21B—C22B—Fe2−58.6 (4)
C24A—Fe1—C22A—C23A36.7 (3)C23B—Fe2—C22B—C24B−38.0 (4)
C25A—Fe1—C22A—C23A81.3 (4)C25B—Fe2—C22B—C24B−81.8 (5)
C15A—Fe1—C22A—C23A158.6 (9)C15B—Fe2—C22B—C24B−156.9 (6)
C14A—Fe1—C22A—C23A−51.5 (6)C13B—Fe2—C22B—C24B78.8 (5)
C21A—Fe1—C22A—C23A119.5 (5)C12B—Fe2—C22B—C24B121.5 (4)
C13A—Fe1—C22A—C23A−85.9 (4)C21B—Fe2—C22B—C24B−118.9 (6)
C12A—Fe1—C22A—C23A−129.2 (3)C11B—Fe2—C22B—C24B164.9 (4)
C11A—Fe1—C22A—C23A−170.2 (3)C14B—Fe2—C22B—C24B42.1 (9)
C24A—Fe1—C22A—C21A−82.7 (4)C23B—Fe2—C22B—C21B81.0 (5)
C25A—Fe1—C22A—C21A−38.2 (4)C25B—Fe2—C22B—C21B37.2 (4)
C15A—Fe1—C22A—C21A39.1 (12)C15B—Fe2—C22B—C21B−38.0 (9)
C14A—Fe1—C22A—C21A−171.0 (4)C24B—Fe2—C22B—C21B118.9 (6)
C23A—Fe1—C22A—C21A−119.5 (5)C13B—Fe2—C22B—C21B−162.3 (4)
C13A—Fe1—C22A—C21A154.6 (4)C12B—Fe2—C22B—C21B−119.5 (4)
C12A—Fe1—C22A—C21A111.4 (4)C11B—Fe2—C22B—C21B−76.2 (4)
C11A—Fe1—C22A—C21A70.4 (4)C14B—Fe2—C22B—C21B161.1 (6)
C21A—C22A—C23A—C24A0.6 (7)C15B—Fe2—C23B—C25B77.9 (5)
Fe1—C22A—C23A—C24A−59.1 (4)C24B—Fe2—C23B—C25B−118.9 (7)
C21A—C22A—C23A—Fe159.6 (4)C13B—Fe2—C23B—C25B161.3 (4)
C25A—Fe1—C23A—C24A39.2 (4)C12B—Fe2—C23B—C25B−167.9 (7)
C15A—Fe1—C23A—C24A−49.5 (6)C21B—Fe2—C23B—C25B−38.2 (4)
C14A—Fe1—C23A—C24A−85.2 (4)C11B—Fe2—C23B—C25B44.8 (9)
C21A—Fe1—C23A—C24A82.8 (4)C22B—Fe2—C23B—C25B−81.7 (4)
C22A—Fe1—C23A—C24A120.3 (5)C14B—Fe2—C23B—C25B120.2 (4)
C13A—Fe1—C23A—C24A−128.1 (3)C25B—Fe2—C23B—C24B118.9 (7)
C12A—Fe1—C23A—C24A−169.0 (3)C15B—Fe2—C23B—C24B−163.2 (4)
C11A—Fe1—C23A—C24A156.0 (8)C13B—Fe2—C23B—C24B−79.8 (5)
C24A—Fe1—C23A—C22A−120.3 (5)C12B—Fe2—C23B—C24B−49.0 (10)
C25A—Fe1—C23A—C22A−81.1 (4)C21B—Fe2—C23B—C24B80.7 (5)
C15A—Fe1—C23A—C22A−169.8 (5)C11B—Fe2—C23B—C24B163.8 (6)
C14A—Fe1—C23A—C22A154.6 (4)C22B—Fe2—C23B—C24B37.2 (4)
C21A—Fe1—C23A—C22A−37.5 (4)C14B—Fe2—C23B—C24B−120.9 (5)
C13A—Fe1—C23A—C22A111.6 (4)C21B—C22B—C24B—C23B−0.6 (7)
C12A—Fe1—C23A—C22A70.7 (4)Fe2—C22B—C24B—C23B58.9 (5)
C11A—Fe1—C23A—C22A35.7 (11)C21B—C22B—C24B—Fe2−59.5 (4)
C22A—C23A—C24A—C25A−1.3 (6)C25B—C23B—C24B—C22B0.2 (8)
Fe1—C23A—C24A—C25A−60.5 (4)Fe2—C23B—C24B—C22B−59.8 (5)
C22A—C23A—C24A—Fe159.2 (4)C25B—C23B—C24B—Fe260.0 (5)
C25A—Fe1—C24A—C23A−117.3 (5)C23B—Fe2—C24B—C22B119.3 (7)
C15A—Fe1—C24A—C23A156.0 (3)C25B—Fe2—C24B—C22B81.5 (5)
C14A—Fe1—C24A—C23A112.8 (4)C15B—Fe2—C24B—C22B159.5 (6)
C21A—Fe1—C24A—C23A−80.3 (4)C13B—Fe2—C24B—C22B−120.6 (4)
C22A—Fe1—C24A—C23A−36.8 (3)C12B—Fe2—C24B—C22B−78.5 (5)
C13A—Fe1—C24A—C23A71.8 (4)C21B—Fe2—C24B—C22B37.7 (4)
C12A—Fe1—C24A—C23A38.4 (11)C11B—Fe2—C24B—C22B−40.8 (11)
C11A—Fe1—C24A—C23A−168.7 (4)C14B—Fe2—C24B—C22B−163.2 (4)
C15A—Fe1—C24A—C25A−86.7 (4)C25B—Fe2—C24B—C23B−37.7 (5)
C14A—Fe1—C24A—C25A−129.9 (4)C15B—Fe2—C24B—C23B40.2 (9)
C21A—Fe1—C24A—C25A37.1 (4)C13B—Fe2—C24B—C23B120.1 (5)
C22A—Fe1—C24A—C25A80.6 (4)C12B—Fe2—C24B—C23B162.3 (5)
C23A—Fe1—C24A—C25A117.3 (5)C21B—Fe2—C24B—C23B−81.6 (5)
C13A—Fe1—C24A—C25A−170.9 (4)C11B—Fe2—C24B—C23B−160.1 (8)
C12A—Fe1—C24A—C25A155.8 (9)C22B—Fe2—C24B—C23B−119.3 (7)
C11A—Fe1—C24A—C25A−51.3 (6)C14B—Fe2—C24B—C23B77.5 (6)
C22A—C21A—C25A—C24A−1.2 (7)C24B—C23B—C25B—C21B0.3 (8)
Fe1—C21A—C25A—C24A59.1 (4)Fe2—C23B—C25B—C21B60.4 (4)
C22A—C21A—C25A—Fe1−60.3 (4)C24B—C23B—C25B—Fe2−60.2 (5)
C23A—C24A—C25A—C21A1.5 (7)C22B—C21B—C25B—C23B−0.6 (7)
Fe1—C24A—C25A—C21A−59.5 (4)Fe2—C21B—C25B—C23B−59.9 (5)
C23A—C24A—C25A—Fe161.0 (4)C22B—C21B—C25B—Fe259.2 (4)
C24A—Fe1—C25A—C21A119.6 (5)C15B—Fe2—C25B—C23B−119.0 (4)
C15A—Fe1—C25A—C21A−128.2 (4)C24B—Fe2—C25B—C23B38.0 (4)
C14A—Fe1—C25A—C21A−169.2 (3)C13B—Fe2—C25B—C23B−48.2 (9)
C22A—Fe1—C25A—C21A38.2 (4)C12B—Fe2—C25B—C23B169.3 (6)
C23A—Fe1—C25A—C21A81.5 (4)C21B—Fe2—C25B—C23B118.1 (6)
C13A—Fe1—C25A—C21A154.3 (10)C11B—Fe2—C25B—C23B−160.8 (4)
C12A—Fe1—C25A—C21A−48.7 (6)C22B—Fe2—C25B—C23B81.2 (4)
C11A—Fe1—C25A—C21A−85.1 (4)C14B—Fe2—C25B—C23B−78.0 (4)
C15A—Fe1—C25A—C24A112.2 (4)C23B—Fe2—C25B—C21B−118.1 (6)
C14A—Fe1—C25A—C24A71.3 (4)C15B—Fe2—C25B—C21B122.9 (4)
C21A—Fe1—C25A—C24A−119.6 (5)C24B—Fe2—C25B—C21B−80.1 (4)
C22A—Fe1—C25A—C24A−81.4 (4)C13B—Fe2—C25B—C21B−166.3 (6)
C23A—Fe1—C25A—C24A−38.0 (3)C12B—Fe2—C25B—C21B51.2 (8)
C13A—Fe1—C25A—C24A34.7 (12)C11B—Fe2—C25B—C21B81.1 (4)
C12A—Fe1—C25A—C24A−168.3 (4)C22B—Fe2—C25B—C21B−36.9 (4)
C11A—Fe1—C25A—C24A155.3 (3)C14B—Fe2—C25B—C21B163.9 (3)
C15A—C11A—C31A—C32A−145.6 (5)C15B—C11B—C31B—C36B−145.8 (5)
C12A—C11A—C31A—C32A34.9 (7)C12B—C11B—C31B—C36B32.1 (8)
Fe1—C11A—C31A—C32A124.6 (4)Fe2—C11B—C31B—C36B−56.3 (6)
C15A—C11A—C31A—C36A36.6 (7)C15B—C11B—C31B—C32B33.6 (8)
C12A—C11A—C31A—C36A−142.9 (5)C12B—C11B—C31B—C32B−148.5 (5)
Fe1—C11A—C31A—C36A−53.2 (6)Fe2—C11B—C31B—C32B123.1 (5)
C36A—C31A—C32A—C33A5.5 (7)C36B—C31B—C32B—C33B1.2 (7)
C11A—C31A—C32A—C33A−172.3 (5)C11B—C31B—C32B—C33B−178.2 (5)
C36A—C31A—C32A—C1A−171.5 (5)C36B—C31B—C32B—C1B−173.6 (5)
C11A—C31A—C32A—C1A10.7 (7)C11B—C31B—C32B—C1B7.0 (7)
O1A—C1A—C32A—C31A−123.4 (5)O1B—C1B—C32B—C33B−123.3 (5)
N1A—C1A—C32A—C31A59.7 (6)N1B—C1B—C32B—C33B56.5 (6)
O1A—C1A—C32A—C33A59.4 (6)O1B—C1B—C32B—C31B51.5 (7)
N1A—C1A—C32A—C33A−117.5 (5)N1B—C1B—C32B—C31B−128.6 (5)
C31A—C32A—C33A—C34A−5.3 (8)C31B—C32B—C33B—C34B−1.7 (8)
C1A—C32A—C33A—C34A172.0 (5)C1B—C32B—C33B—C34B173.2 (5)
C32A—C33A—C34A—C35A1.1 (8)C32B—C33B—C34B—C35B0.5 (8)
C33A—C34A—C35A—C36A2.7 (8)C33B—C34B—C35B—C36B1.2 (8)
C34A—C35A—C36A—C31A−2.4 (8)C34B—C35B—C36B—C31B−1.7 (8)
C32A—C31A—C36A—C35A−1.7 (8)C32B—C31B—C36B—C35B0.5 (8)
C11A—C31A—C36A—C35A176.1 (5)C11B—C31B—C36B—C35B179.9 (5)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C31A–C36A, C31B–C36B rings, respectively.
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N6B0.882.243.113 (5)172
N1B—H1B···N6A0.882.143.004 (5)167
C3A—H3A···O1A0.952.262.853 (7)119
C3B—H3B···O1B0.952.282.839 (7)117
C7B—H7B2···O1Bi0.982.603.050 (6)108
C7A—H7A1···Cg10.982.783.688 (7)154
C7B—H7B1···Cg20.983.683.490 (7)140

Symmetry codes: (i) −y+1/3, −x+2/3, z+1/6.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2637).

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