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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 3| March 2009| Pages m332-m333
doi:10.1107/S1600536809006278

2-Ferrocenyl-N-(2-ferrocenylbenzo­yl)-N-(4-methyl-2-pyrid­yl)benzamide

John F. Gallagher,a* Steven Alleya and Alan J. Loughb‡

aSchool of Chemical Sciences, Dublin City University, Dublin 9, Ireland, and bDepartment of Chemistry, 80 St. George Street, University of Toronto, Toronto, Ontario, Canada M5S 3H6
*Correspondence e-mail: john.gallagher@dcu.ie

(Received 6 February 2009; accepted 20 February 2009; online 28 February 2009)

The title compound, [Fe2(C5H5)2(C30H22N2O2)], a 2:1 product of the reaction of 2-ferrocenylbenzoic acid and 2-amino-4-methyl­pyridine, forms a twisted mol­ecular structure in the solid state due to steric effects from the two benzene rings ortho-substituted with ferrocenyl and carbonyl-derived groups. A short intra­molecular C—H⋯π interaction is observed involving a substituted η5-C5H4 ring and an ortho H atom of the benzene ring on the opposite side of the mol­ecule. In the crystal structure, there are no classical hydrogen bonds: inter­actions comprise a short C6—H⋯π(C6) inter­action involving substituted benzene rings and two C—H⋯O=C inter­actions per mol­ecule.

Related literature

For background information, see: Gallagher et al. (2008[Gallagher, J. F., McMahon, J., Anderson, F. P. & Lough, A. J. (2008). Acta Cryst. E64, o2394.], 2009a[Gallagher, J. F., Donnelly, K. & Lough, A. J. (2009a). Acta Cryst. E65, o102-o103.],b[Gallagher, J. F., Donnelly, K. & Lough, A. J. (2009b). Acta Cryst. E65, o486-o487.]). For the parent compound, 2-(dibenzoyl­amino)pyridine, see: Weng et al. (2006[Weng, Y.-B., Wang, J.-K. & Wang, Y.-F. (2006). Acta Cryst. E62, o1868-o1869.]). For a related ferrocene derivative, see: Moriuchi & Hirao (2007[Moriuchi, T. & Hirao, T. (2007). Tetrahedron Lett. 48, 5099-5101.]). For related structures, see: Akinboye et al. (2009a[Akinboye, E. S., Butcher, R. J., Brandy, Y., Adesiyun, T. A. & Bakare, O. (2009a). Acta Cryst. E65, o24.],b[Akinboye, E. S., Butcher, R. J., Wright, D. A., Brandy, Y. & Bakare, O. (2009b). Acta Cryst. E65, o277.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe2(C5H5)2(C30H22N2O2)]

  • Mr = 684.38

  • Triclinic, [P \overline 1]

  • a = 12.0861 (7) Å

  • b = 12.4935 (8) Å

  • c = 12.5028 (8) Å

  • α = 65.159 (3)°

  • β = 62.696 (3)°

  • γ = 81.580 (3)°

  • V = 1519.83 (16) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.00 mm−1

  • T = 150 K

  • 0.22 × 0.22 × 0.14 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.811, Tmax = 0.873

  • 10819 measured reflections

  • 6865 independent reflections

  • 3530 reflections with I > 2σ(I)

  • Rint = 0.107
Refinement

  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.154

  • S = 0.95

  • 6865 reflections

  • 417 parameters

  • H-atom parameters constrained

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.87 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C9—H9B⋯O1i 0.98 2.36 3.188 (6) 142
C13B—H13B⋯O2ii 0.95 2.58 3.510 (6) 167
C33B—H33B⋯Cg1 0.95 2.58 3.387 (5) 144
C35A—H35A⋯Cg2iii 0.95 2.61 3.489 (6) 154
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+2. Cg1 and Cg2 are the centroids of the C11A–C15A, C31B–C36B rings, respectively.

Data collection: KappaCCD Server Software (Nonius, 1997[Nonius (1997). KappaCCD Server Software. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and SORTX (McArdle, 1995[McArdle, P. (1995). J. Appl. Cryst. 28, 65.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97 and PREP8 (Ferguson, 1998[Ferguson, G. (1998). PREP8. University of Guelph, Canada.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006278/bg2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006278/bg2237Isup2.hkl

checkCIF report


Comment top

In the condensation reactions of benzoyl chlorides and amino derivatives containing an ortho-aromatic ring N atom (such as ortho-aminopyridine), two products can be isolated as either the 1:1 or 2:1 benzoyl:pyridine components and with yields and ratios depending on the reaction conditions. We have reported on the structure of the 1:1 derivative namely 2,3-difluoro-N-(2-pyridyl)benzamide (Gallagher et al., 2008) and two examples of a 2:1 relative namely the mono-fluoro derivatives, 2-Fluoro-N-(2-fluorobenzoyl)-N-(2-pyridyl)benzamide and 3-Fluoro-N-(3-fluorobenzoyl)-N-(2-pyridyl)benzamide (Gallagher et al., 2009a,b). Herein, we report an organometallic analogue of these systems where a sterically bulky ferrocenyl group has replaced the fluoro and a different pyridine ring system is used in the molecular scaffold, namely the electroactive molecular system 2-Ferrocenyl-N-(2-ferrocenylbenzoyl)-N-(4-methyl-2-pyridyl)benzamide (I).

The parent compound 2-(Dibenzoylamino)pyridine has been reported previously (Weng et al., 2006). A review of the literature suggests that structures of this type are rare despite the large number of substituted benzamides reported in the literature. Recently, the crystal structures of two compounds N-(3-Br-1,4-dioxo-1,4-dihydro-2-naphthyl)-2-Cl—N-(2-chlorobenzoyl)benzamide & N-(3-Br-1,4-dioxo-1,4-dihydro-2-naphthyl)-4-F—N-(4-fluorobenzoyl)benzamide have been reported (Akinboye et al., 2009a,b), but these differ substantially from (I) in the quinone scaffold or more specifically in the chloro-1,4-naphthoquinone skeleton. The molecular structure of a related compound which has been examined for protonation-controlled regulation of electronic communication, namely, N-Ferrocenecarbonyl-N-(2-pyridyl)ferrocenecarboxamide (Moriuchi & Hirao, 2007) is of interest for comparisons with (I) and also the parent compound (Weng et al., 2006).

(I) crystallizes in the triclinic system in space group P1 (No. 2) and forms an interesting twisted molecular structure in the solid state due to the steric demands of two ortho-substituted benzene rings (Figs. 1–2).

A short intramolecular hydrogen bond is present in (I) involving a substituted η5-(C5H4) ring and an ortho-H atom of the benzene ring on the opposite side of the molecule. The geometric data are H33B···Cg1 of 2.58 Å, C33B—H33B···Cg1 144° and C33B···Cg1 3.387 (5) Å (Cg1 is the centroid of the C11A-C15A ring). This is quite short and comparable to intramolecular arC—H···η5-(C5) ring interactions present in ferrocene-derived crystal structures deposited on the CSD (Allen, 2002). However, in the vast majority of crystal structures analysed (for such intramolecular interactions) the C—H is only 4/5 bonds from the C5 ring and oriented on steric grounds to overlap with the cp ring whether this is energetically favourable or not. The intramolecular interaction in (I) is such that the C—H and substituted cyclopentadienyl ring can be considered to be 8 bonds from each other. However, given the steric demands within (I) a similar situation exists whereby the C—H is oriented towards the ring on steric grounds.

The crystal structure also contains three intermolecular interactions comprising a short C—H···π-(C6) interaction {C6 is the C31B-C36B ring system, with centroid Cg2} and two C—H···O=C weak interactions per molecule. The former is centrosymmetric and has the effect of (I) joining to form a dimer: the other interactions are less significant in terms of crystal structure packing.

Related literature top

For background information, see: Gallagher et al. (2008, 2009a,b). For the parent compound, 2-(dibenzoylamino)pyridine, see: Weng et al. (2006). For a related ferrocene derivative, see: Moriuchi & Hirao (2007). For related structures, see: Akinboye et al. (2009a,b). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Compound (I) was synthesized via standard condensation procedures and similar to the related syntheses reported (Gallagher et al., 2009a,b). 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 2:1 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 top

Molecule (I) crystallized in the triclinic system; space group P1 (No. 2) and confirmed by the analysis.

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular C—H···η(C5H4) interaction is depicted with a dashed line.
[Figure 2] Fig. 2. A view of (I) with atoms displayed at the 30% probability level with the intramolecular C—H···π interaction (top centre) and enveloped with an azure coloured van der Waals surface.
2-Ferrocenyl-N-(2-ferrocenylbenzoyl)-N-(4-methyl-2- pyridyl)benzamide top
Crystal data top
[Fe2(C5H5)2(C30H22N2O2)]Z = 2
Mr = 684.38F(000) = 708
Triclinic, P1Dx = 1.495 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.0861 (7) ÅCell parameters from 6725 reflections
b = 12.4935 (8) Åθ = 2.6–27.5°
c = 12.5028 (8) ŵ = 1.00 mm−1
α = 65.159 (3)°T = 150 K
β = 62.696 (3)°Block, red
γ = 81.580 (3)°0.22 × 0.22 × 0.14 mm
V = 1519.83 (16) Å3
Data collection top
Nonius KappaCCD
diffractometer		6865 independent reflections
Radiation source: fine-focus sealed X-ray tube3530 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.107
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		h = −15→15
Tmin = 0.811, Tmax = 0.873k = −16→13
10819 measured reflectionsl = −16→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.154 w = 1/[σ2(Fo2) + (0.0548P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
6865 reflectionsΔρmax = 0.77 e Å−3
417 parametersΔρmin = −0.87 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0030 (7)
Crystal data top
[Fe2(C5H5)2(C30H22N2O2)]γ = 81.580 (3)°
Mr = 684.38V = 1519.83 (16) Å3
Triclinic, P1Z = 2
a = 12.0861 (7) ÅMo Kα radiation
b = 12.4935 (8) ŵ = 1.00 mm−1
c = 12.5028 (8) ÅT = 150 K
α = 65.159 (3)°0.22 × 0.22 × 0.14 mm
β = 62.696 (3)°
Data collection top
Nonius KappaCCD
diffractometer		6865 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)		3530 reflections with I > 2σ(I)
Tmin = 0.811, Tmax = 0.873Rint = 0.107
10819 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.154H-atom parameters constrained
S = 0.95Δρmax = 0.77 e Å−3
6865 reflectionsΔρmin = −0.87 e Å−3
417 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.38802 (6)0.20628 (6)1.36143 (6)0.0257 (2)
O10.8865 (3)0.2456 (3)1.0313 (3)0.0413 (9)
C10.8036 (4)0.2902 (4)1.0009 (4)0.0267 (10)
N10.7691 (3)0.2461 (3)0.9319 (3)0.0222 (8)
O20.7368 (3)0.4272 (2)0.7970 (3)0.0269 (7)
C20.7216 (4)0.3217 (4)0.8421 (4)0.0218 (10)
C11A0.5234 (4)0.2876 (4)1.1694 (4)0.0246 (10)
C12A0.4007 (4)0.2944 (4)1.1760 (4)0.0258 (10)
C13A0.3477 (4)0.1788 (4)1.2333 (4)0.0298 (11)
C14A0.4342 (4)0.0979 (4)1.2652 (4)0.0294 (11)
C15A0.5410 (4)0.1638 (4)1.2281 (4)0.0262 (10)
C21A0.4104 (5)0.2759 (4)1.4716 (4)0.0334 (11)
C22A0.2951 (5)0.3064 (5)1.4670 (5)0.0413 (13)
C23A0.2237 (5)0.2030 (5)1.5185 (5)0.0436 (14)
C24A0.2935 (5)0.1042 (4)1.5574 (4)0.0431 (13)
C25A0.4084 (5)0.1506 (4)1.5293 (4)0.0370 (12)
C31A0.6109 (4)0.3872 (4)1.1173 (4)0.0240 (10)
C32A0.7384 (4)0.3898 (4)1.0371 (4)0.0218 (10)
C33A0.8175 (4)0.4840 (4)0.9981 (4)0.0292 (11)
C34A0.7710 (4)0.5758 (4)1.0373 (4)0.0311 (11)
C35A0.6437 (4)0.5756 (4)1.1144 (4)0.0315 (11)
C36A0.5655 (4)0.4834 (4)1.1526 (4)0.0261 (10)
C30.8172 (4)0.1348 (4)0.9253 (4)0.0220 (10)
C40.8075 (4)0.0369 (4)1.0373 (4)0.0245 (10)
C50.8552 (4)−0.0678 (4)1.0271 (4)0.0234 (10)
C60.9085 (4)−0.0681 (4)0.9013 (5)0.0294 (11)
C70.9117 (4)0.0326 (4)0.7980 (4)0.0320 (11)
N80.8687 (3)0.1363 (3)0.8062 (3)0.0249 (8)
C90.8491 (4)−0.1758 (4)1.1449 (5)0.0343 (12)
Fe20.87164 (6)0.32188 (6)0.41312 (6)0.0268 (2)
C11B0.7582 (4)0.3693 (4)0.5670 (4)0.0258 (10)
C12B0.8869 (4)0.3777 (4)0.5378 (4)0.0277 (10)
C13B0.9534 (5)0.4581 (4)0.4067 (4)0.0344 (12)
C14B0.8681 (5)0.5003 (4)0.3509 (5)0.0371 (12)
C15B0.7481 (4)0.4470 (4)0.4484 (4)0.0307 (11)
C21B0.8314 (5)0.1487 (4)0.4675 (5)0.0463 (14)
C22B0.9594 (5)0.1666 (4)0.4273 (5)0.0379 (12)
C23B1.0115 (4)0.2511 (4)0.2970 (5)0.0340 (12)
C24B0.9152 (5)0.2837 (4)0.2551 (5)0.0388 (13)
C25B0.8035 (5)0.2207 (5)0.3618 (6)0.0441 (14)
C31B0.6561 (4)0.2927 (4)0.6881 (4)0.0240 (10)
C32B0.6445 (4)0.2603 (4)0.8159 (4)0.0215 (10)
C33B0.5501 (4)0.1792 (4)0.9251 (4)0.0245 (10)
C34B0.4630 (4)0.1321 (4)0.9116 (4)0.0276 (10)
C35B0.4702 (4)0.1654 (4)0.7884 (4)0.0275 (10)
C36B0.5650 (4)0.2440 (4)0.6797 (4)0.0276 (11)
H12A0.36170.36511.14670.031*
H13A0.26780.15861.24790.036*
H14A0.42250.01421.30470.035*
H15A0.61280.13151.24000.031*
H21A0.47700.32921.44180.040*
H22A0.27020.38461.43410.050*
H23A0.14220.19901.52650.052*
H24A0.26770.02311.59490.052*
H25A0.47340.10541.54610.044*
H33A0.90420.48470.94400.035*
H34A0.82550.63871.01180.037*
H35A0.61090.63911.14060.038*
H36A0.47850.48491.20420.031*
H40.76830.04171.12050.029*
H60.9421−0.13770.88830.035*
H70.94680.02960.71410.038*
H9A0.8143−0.15641.22200.052*
H9B0.9332−0.20351.12880.052*
H9C0.7958−0.23821.16090.052*
H12B0.92180.33570.59730.033*
H13B1.03990.48020.36330.041*
H14B0.88810.55480.26320.045*
H15B0.67380.46030.43750.037*
H21B0.77350.09670.55170.056*
H22B1.00270.12820.47920.045*
H23B1.09580.28120.24580.041*
H24B0.92440.33820.17060.047*
H25B0.72410.22580.36220.053*
H33B0.54550.15601.00980.029*
H34B0.39860.07720.98670.033*
H35B0.41000.13440.77840.033*
H36B0.56840.26590.59570.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0273 (4)0.0268 (4)0.0221 (4)0.0010 (3)−0.0087 (3)−0.0113 (3)
O10.043 (2)0.050 (2)0.062 (2)0.0242 (18)−0.037 (2)−0.041 (2)
C10.025 (2)0.032 (3)0.023 (2)−0.003 (2)−0.007 (2)−0.013 (2)
N10.026 (2)0.024 (2)0.0210 (19)0.0063 (16)−0.0123 (18)−0.0124 (16)
O20.0359 (19)0.0180 (17)0.0278 (17)−0.0006 (14)−0.0155 (16)−0.0077 (14)
C20.019 (2)0.026 (3)0.017 (2)−0.002 (2)−0.002 (2)−0.011 (2)
C11A0.031 (3)0.021 (2)0.019 (2)0.000 (2)−0.008 (2)−0.009 (2)
C12A0.025 (2)0.034 (3)0.019 (2)0.004 (2)−0.012 (2)−0.010 (2)
C13A0.028 (3)0.034 (3)0.025 (3)−0.004 (2)−0.010 (2)−0.011 (2)
C14A0.036 (3)0.026 (3)0.026 (3)0.000 (2)−0.008 (2)−0.015 (2)
C15A0.025 (2)0.027 (3)0.025 (2)0.008 (2)−0.008 (2)−0.015 (2)
C21A0.047 (3)0.031 (3)0.026 (3)−0.005 (2)−0.016 (2)−0.012 (2)
C22A0.049 (3)0.041 (3)0.036 (3)0.014 (3)−0.012 (3)−0.028 (3)
C23A0.034 (3)0.065 (4)0.030 (3)0.001 (3)−0.002 (3)−0.031 (3)
C24A0.062 (4)0.029 (3)0.021 (3)−0.014 (3)−0.002 (3)−0.008 (2)
C25A0.050 (3)0.041 (3)0.022 (3)0.003 (3)−0.020 (3)−0.010 (2)
C31A0.029 (3)0.022 (2)0.018 (2)0.005 (2)−0.009 (2)−0.009 (2)
C32A0.026 (2)0.021 (2)0.021 (2)0.0012 (19)−0.011 (2)−0.0094 (19)
C33A0.029 (3)0.033 (3)0.026 (3)0.001 (2)−0.009 (2)−0.016 (2)
C34A0.038 (3)0.023 (3)0.031 (3)−0.003 (2)−0.014 (2)−0.010 (2)
C35A0.040 (3)0.025 (3)0.031 (3)0.012 (2)−0.016 (3)−0.016 (2)
C36A0.025 (2)0.025 (3)0.023 (2)0.004 (2)−0.003 (2)−0.012 (2)
C30.023 (2)0.022 (2)0.028 (3)0.0018 (19)−0.013 (2)−0.015 (2)
C40.028 (3)0.024 (2)0.023 (2)0.003 (2)−0.011 (2)−0.011 (2)
C50.019 (2)0.028 (3)0.021 (2)0.0017 (19)−0.007 (2)−0.010 (2)
C60.034 (3)0.024 (2)0.040 (3)0.011 (2)−0.020 (2)−0.020 (2)
C70.037 (3)0.034 (3)0.021 (2)0.007 (2)−0.007 (2)−0.016 (2)
N80.032 (2)0.023 (2)0.020 (2)0.0079 (17)−0.0117 (18)−0.0112 (17)
C90.033 (3)0.029 (3)0.035 (3)0.006 (2)−0.011 (2)−0.012 (2)
Fe20.0320 (4)0.0261 (4)0.0212 (4)−0.0022 (3)−0.0092 (3)−0.0104 (3)
C11B0.031 (3)0.021 (2)0.024 (2)−0.004 (2)−0.009 (2)−0.011 (2)
C12B0.035 (3)0.027 (3)0.022 (2)−0.008 (2)−0.009 (2)−0.012 (2)
C13B0.038 (3)0.035 (3)0.026 (3)−0.012 (2)−0.005 (2)−0.015 (2)
C14B0.060 (4)0.020 (3)0.021 (3)−0.005 (2)−0.009 (3)−0.007 (2)
C15B0.041 (3)0.026 (3)0.025 (3)0.006 (2)−0.013 (2)−0.013 (2)
C21B0.058 (4)0.023 (3)0.042 (3)−0.012 (3)−0.006 (3)−0.012 (3)
C22B0.049 (3)0.033 (3)0.038 (3)0.009 (3)−0.024 (3)−0.017 (2)
C23B0.033 (3)0.039 (3)0.026 (3)0.007 (2)−0.010 (2)−0.015 (2)
C24B0.058 (4)0.040 (3)0.038 (3)0.015 (3)−0.027 (3)−0.029 (3)
C25B0.039 (3)0.052 (4)0.062 (4)0.006 (3)−0.025 (3)−0.038 (3)
C31B0.028 (3)0.021 (2)0.028 (2)0.006 (2)−0.014 (2)−0.015 (2)
C32B0.024 (2)0.021 (2)0.020 (2)0.0021 (19)−0.008 (2)−0.0102 (19)
C33B0.029 (3)0.022 (2)0.023 (2)0.003 (2)−0.011 (2)−0.011 (2)
C34B0.024 (2)0.021 (2)0.033 (3)0.002 (2)−0.008 (2)−0.011 (2)
C35B0.022 (2)0.030 (3)0.035 (3)0.000 (2)−0.011 (2)−0.018 (2)
C36B0.029 (3)0.031 (3)0.029 (3)0.003 (2)−0.016 (2)−0.015 (2)
Geometric parameters (Å, º) top
Fe1—C11A2.075 (4)Fe2—C25B2.040 (5)
Fe1—C12A2.046 (4)C11B—C12B1.434 (6)
Fe1—C13A2.037 (4)C11B—C15B1.442 (6)
Fe1—C14A2.030 (4)C11B—C31B1.464 (6)
Fe1—C15A2.027 (4)C12B—C13B1.409 (6)
Fe1—C21A2.036 (4)C13B—C14B1.420 (6)
Fe1—C22A2.046 (5)C14B—C15B1.418 (6)
Fe1—C23A2.045 (5)C21B—C22B1.411 (7)
Fe1—C24A2.042 (5)C21B—C25B1.411 (7)
Fe1—C25A2.036 (4)C22B—C23B1.405 (6)
O1—C11.211 (4)C23B—C24B1.427 (6)
O2—C21.200 (5)C24B—C25B1.413 (7)
N1—C11.422 (5)C31B—C32B1.416 (5)
N1—C21.422 (5)C31B—C36B1.397 (6)
N1—C31.446 (5)C32B—C33B1.392 (6)
C1—C32A1.494 (6)C33B—C34B1.383 (6)
C2—C32B1.504 (6)C34B—C35B1.379 (6)
C11A—C12A1.439 (6)C35B—C36B1.380 (6)
C11A—C15A1.439 (6)C12A—H12A0.9500
C11A—C31A1.471 (6)C13A—H13A0.9500
C12A—C13A1.410 (6)C14A—H14A0.9500
C13A—C14A1.417 (6)C15A—H15A0.9500
C14A—C15A1.413 (6)C21A—H21A0.9500
C21A—C22A1.411 (6)C22A—H22A0.9500
C21A—C25A1.420 (6)C23A—H23A0.9500
C22A—C23A1.395 (7)C24A—H24A0.9500
C23A—C24A1.428 (7)C25A—H25A0.9500
C24A—C25A1.416 (7)C33A—H33A0.9500
C31A—C32A1.397 (6)C34A—H34A0.9500
C31A—C36A1.405 (6)C35A—H35A0.9500
C32A—C33A1.399 (6)C36A—H36A0.9500
C33A—C34A1.379 (6)C4—H40.9500
C34A—C35A1.391 (6)C6—H60.9500
C35A—C36A1.375 (6)C7—H70.9500
C3—N81.318 (5)C9—H9A0.9800
C3—C41.386 (5)C9—H9B0.9800
C4—C51.382 (6)C9—H9C0.9800
C5—C61.401 (6)C12B—H12B0.9500
C5—C91.503 (6)C13B—H13B0.9500
C6—C71.362 (6)C14B—H14B0.9500
C7—N81.352 (5)C15B—H15B0.9500
Fe2—C11B2.057 (4)C21B—H21B0.9500
Fe2—C12B2.041 (4)C22B—H22B0.9500
Fe2—C13B2.045 (5)C23B—H23B0.9500
Fe2—C14B2.030 (4)C24B—H24B0.9500
Fe2—C15B2.039 (4)C25B—H25B0.9500
Fe2—C21B2.037 (5)C33B—H33B0.9500
Fe2—C22B2.050 (5)C34B—H34B0.9500
Fe2—C23B2.034 (5)C35B—H35B0.9500
Fe2—C24B2.042 (5)C36B—H36B0.9500
C15A—Fe1—C14A40.78 (17)C5—C6—C7119.2 (4)
C15A—Fe1—C25A107.92 (19)N8—C7—C6124.8 (4)
C14A—Fe1—C25A118.78 (19)C3—N8—C7115.3 (4)
C15A—Fe1—C21A118.95 (19)C5—C4—H4120.2
C14A—Fe1—C21A153.06 (18)C3—C4—H4120.2
C25A—Fe1—C21A40.83 (18)C7—C6—H6120.4
C15A—Fe1—C13A68.56 (17)C5—C6—H6120.4
C14A—Fe1—C13A40.78 (16)N8—C7—H7117.6
C25A—Fe1—C13A152.84 (19)C6—C7—H7117.6
C21A—Fe1—C13A164.92 (18)C5—C9—H9A109.5
C15A—Fe1—C24A126.79 (19)C5—C9—H9B109.5
C14A—Fe1—C24A107.23 (19)H9A—C9—H9B109.5
C25A—Fe1—C24A40.64 (19)C5—C9—H9C109.5
C21A—Fe1—C24A68.8 (2)H9A—C9—H9C109.5
C13A—Fe1—C24A118.5 (2)H9B—C9—H9C109.5
C15A—Fe1—C23A165.2 (2)C14B—Fe2—C23B119.0 (2)
C14A—Fe1—C23A127.4 (2)C14B—Fe2—C21B163.9 (2)
C25A—Fe1—C23A68.0 (2)C23B—Fe2—C21B68.0 (2)
C21A—Fe1—C23A68.0 (2)C14B—Fe2—C15B40.80 (18)
C13A—Fe1—C23A108.17 (19)C23B—Fe2—C15B154.61 (18)
C24A—Fe1—C23A40.89 (19)C21B—Fe2—C15B127.2 (2)
C15A—Fe1—C22A153.4 (2)C14B—Fe2—C25B125.9 (2)
C14A—Fe1—C22A164.9 (2)C23B—Fe2—C25B68.6 (2)
C25A—Fe1—C22A67.9 (2)C21B—Fe2—C25B40.5 (2)
C21A—Fe1—C22A40.45 (18)C15B—Fe2—C25B108.59 (19)
C13A—Fe1—C22A127.43 (19)C14B—Fe2—C12B68.41 (18)
C24A—Fe1—C22A68.2 (2)C23B—Fe2—C12B124.29 (18)
C23A—Fe1—C22A39.9 (2)C21B—Fe2—C12B121.2 (2)
C15A—Fe1—C12A68.63 (16)C15B—Fe2—C12B68.65 (18)
C14A—Fe1—C12A68.43 (18)C25B—Fe2—C12B156.3 (2)
C25A—Fe1—C12A165.56 (19)C14B—Fe2—C24B107.0 (2)
C21A—Fe1—C12A127.45 (18)C23B—Fe2—C24B40.98 (17)
C13A—Fe1—C12A40.40 (17)C21B—Fe2—C24B67.9 (2)
C24A—Fe1—C12A152.6 (2)C15B—Fe2—C24B120.34 (18)
C23A—Fe1—C12A118.94 (19)C25B—Fe2—C24B40.5 (2)
C22A—Fe1—C12A108.50 (19)C12B—Fe2—C24B161.6 (2)
C15A—Fe1—C11A41.04 (16)C14B—Fe2—C13B40.79 (18)
C14A—Fe1—C11A68.86 (18)C23B—Fe2—C13B106.1 (2)
C25A—Fe1—C11A127.46 (19)C21B—Fe2—C13B154.7 (2)
C21A—Fe1—C11A107.71 (18)C15B—Fe2—C13B68.59 (19)
C13A—Fe1—C11A68.60 (17)C25B—Fe2—C13B162.5 (2)
C24A—Fe1—C11A165.06 (19)C12B—Fe2—C13B40.36 (17)
C23A—Fe1—C11A152.7 (2)C24B—Fe2—C13B124.8 (2)
C22A—Fe1—C11A119.2 (2)C14B—Fe2—C22B153.7 (2)
C12A—Fe1—C11A40.88 (16)C23B—Fe2—C22B40.25 (18)
O1—C1—N1119.3 (4)C21B—Fe2—C22B40.37 (19)
O1—C1—C32A119.8 (4)C15B—Fe2—C22B164.1 (2)
N1—C1—C32A120.9 (3)C25B—Fe2—C22B68.2 (2)
C1—N1—C2120.8 (3)C12B—Fe2—C22B107.68 (18)
C1—N1—C3117.2 (3)C24B—Fe2—C22B68.04 (19)
C2—N1—C3119.5 (3)C13B—Fe2—C22B119.3 (2)
O2—C2—N1121.6 (4)C14B—Fe2—C11B69.11 (18)
O2—C2—C32B123.0 (4)C23B—Fe2—C11B162.10 (17)
N1—C2—C32B115.2 (4)C21B—Fe2—C11B108.8 (2)
C15A—C11A—C12A105.9 (4)C15B—Fe2—C11B41.21 (16)
C15A—C11A—C31A127.2 (4)C25B—Fe2—C11B121.3 (2)
C12A—C11A—C31A126.9 (4)C12B—Fe2—C11B40.97 (17)
C15A—C11A—Fe167.7 (2)C24B—Fe2—C11B155.85 (19)
C12A—C11A—Fe168.5 (2)C13B—Fe2—C11B68.81 (18)
C31A—C11A—Fe1126.8 (3)C22B—Fe2—C11B126.01 (18)
C13A—C12A—C11A108.8 (4)C12B—C11B—C15B106.2 (4)
C13A—C12A—Fe169.5 (2)C12B—C11B—C31B128.6 (4)
C11A—C12A—Fe170.6 (2)C15B—C11B—C31B125.1 (4)
C13A—C12A—H12A125.6C12B—C11B—Fe268.9 (2)
C11A—C12A—H12A125.6C15B—C11B—Fe268.7 (2)
Fe1—C12A—H12A125.9C31B—C11B—Fe2124.0 (3)
C12A—C13A—C14A108.4 (4)C13B—C12B—C11B109.2 (4)
C12A—C13A—Fe170.2 (2)C13B—C12B—Fe270.0 (2)
C14A—C13A—Fe169.3 (2)C11B—C12B—Fe270.1 (2)
C12A—C13A—H13A125.8C13B—C12B—H12B125.4
C14A—C13A—H13A125.8C11B—C12B—H12B125.4
Fe1—C13A—H13A126.3Fe2—C12B—H12B126.1
C15A—C14A—C13A107.9 (4)C12B—C13B—C14B107.9 (4)
C15A—C14A—Fe169.5 (2)C12B—C13B—Fe269.7 (2)
C13A—C14A—Fe169.9 (3)C14B—C13B—Fe269.0 (3)
C15A—C14A—H14A126.0C12B—C13B—H13B126.0
C13A—C14A—H14A126.0C14B—C13B—H13B126.0
Fe1—C14A—H14A126.2Fe2—C13B—H13B126.9
C14A—C15A—C11A109.0 (4)C15B—C14B—C13B108.3 (4)
C14A—C15A—Fe169.7 (2)C15B—C14B—Fe270.0 (3)
C11A—C15A—Fe171.3 (2)C13B—C14B—Fe270.2 (3)
C14A—C15A—H15A125.5C15B—C14B—H14B125.8
C11A—C15A—H15A125.5C13B—C14B—H14B125.8
Fe1—C15A—H15A125.1Fe2—C14B—H14B125.6
C22A—C21A—C25A107.2 (4)C14B—C15B—C11B108.3 (4)
C22A—C21A—Fe170.1 (3)C14B—C15B—Fe269.2 (3)
C25A—C21A—Fe169.6 (3)C11B—C15B—Fe270.1 (2)
C22A—C21A—H21A126.4C14B—C15B—H15B125.9
C25A—C21A—H21A126.4C11B—C15B—H15B125.9
Fe1—C21A—H21A125.5Fe2—C15B—H15B126.4
C23A—C22A—C21A108.8 (4)C22B—C21B—C25B108.7 (5)
C23A—C22A—Fe170.0 (3)C22B—C21B—Fe270.3 (3)
C21A—C22A—Fe169.4 (3)C25B—C21B—Fe269.9 (3)
C23A—C22A—H22A125.6C22B—C21B—H21B125.6
C21A—C22A—H22A125.6C25B—C21B—H21B125.6
Fe1—C22A—H22A126.5Fe2—C21B—H21B125.8
C22A—C23A—C24A108.6 (5)C23B—C22B—C21B108.0 (4)
C22A—C23A—Fe170.1 (3)C23B—C22B—Fe269.3 (3)
C24A—C23A—Fe169.4 (3)C21B—C22B—Fe269.3 (3)
C22A—C23A—H23A125.7C23B—C22B—H22B126.0
C24A—C23A—H23A125.7C21B—C22B—H22B126.0
Fe1—C23A—H23A126.4Fe2—C22B—H22B126.9
C25A—C24A—C23A106.7 (4)C22B—C23B—C24B107.9 (4)
C25A—C24A—Fe169.5 (3)C22B—C23B—Fe270.5 (3)
C23A—C24A—Fe169.7 (3)C24B—C23B—Fe269.8 (3)
C25A—C24A—H24A126.7C22B—C23B—H23B126.1
C23A—C24A—H24A126.7C24B—C23B—H23B126.1
Fe1—C24A—H24A125.8Fe2—C23B—H23B125.2
C24A—C25A—C21A108.7 (4)C25B—C24B—C23B107.9 (4)
C24A—C25A—Fe169.9 (3)C25B—C24B—Fe269.7 (3)
C21A—C25A—Fe169.6 (2)C23B—C24B—Fe269.2 (3)
C24A—C25A—H25A125.6C25B—C24B—H24B126.1
C21A—C25A—H25A125.6C23B—C24B—H24B126.1
Fe1—C25A—H25A126.5Fe2—C24B—H24B126.7
C32A—C31A—C36A117.9 (4)C21B—C25B—C24B107.6 (4)
C32A—C31A—C11A123.4 (4)C21B—C25B—Fe269.7 (3)
C36A—C31A—C11A118.7 (4)C24B—C25B—Fe269.8 (3)
C31A—C32A—C33A120.2 (4)C21B—C25B—H25B126.2
C31A—C32A—C1124.6 (4)C24B—C25B—H25B126.2
C33A—C32A—C1114.7 (4)Fe2—C25B—H25B125.9
C34A—C33A—C32A120.7 (4)C36B—C31B—C32B116.4 (4)
C34A—C33A—H33A119.6C36B—C31B—C11B119.2 (4)
C32A—C33A—H33A119.6C32B—C31B—C11B124.4 (4)
C33A—C34A—C35A119.5 (4)C33B—C32B—C31B120.6 (4)
C33A—C34A—H34A120.2C33B—C32B—C2116.9 (4)
C35A—C34A—H34A120.2C31B—C32B—C2122.1 (4)
C36A—C35A—C34A120.0 (4)C34B—C33B—C32B120.8 (4)
C36A—C35A—H35A120.0C34B—C33B—H33B119.6
C34A—C35A—H35A120.0C32B—C33B—H33B119.6
C35A—C36A—C31A121.6 (4)C35B—C34B—C33B119.5 (4)
C35A—C36A—H36A119.2C35B—C34B—H34B120.2
C31A—C36A—H36A119.2C33B—C34B—H34B120.2
N8—C3—C4124.5 (4)C34B—C35B—C36B119.9 (4)
N8—C3—N1114.2 (4)C34B—C35B—H35B120.1
C4—C3—N1121.3 (4)C36B—C35B—H35B120.1
C3—C4—C5119.6 (4)C35B—C36B—C31B122.7 (4)
C4—C5—C6116.5 (4)C35B—C36B—H36B118.6
C4—C5—C9121.7 (4)C31B—C36B—H36B118.6
C6—C5—C9121.8 (4)
O1—C1—N1—C2−149.6 (4)C2—N1—C3—C4−148.0 (4)
C32A—C1—N1—C230.9 (6)N8—C3—C4—C50.7 (6)
O1—C1—N1—C312.4 (6)N1—C3—C4—C5−179.6 (4)
C32A—C1—N1—C3−167.1 (4)C3—C4—C5—C6−1.6 (6)
C1—N1—C2—O218.5 (6)C3—C4—C5—C9178.9 (4)
C3—N1—C2—O2−143.1 (4)C4—C5—C6—C70.7 (6)
C1—N1—C2—C32B−157.5 (4)C9—C5—C6—C7−179.8 (4)
C3—N1—C2—C32B40.9 (5)C5—C6—C7—N81.3 (7)
C14A—Fe1—C11A—C15A−37.6 (2)C4—C3—N8—C71.2 (6)
C25A—Fe1—C11A—C15A73.1 (3)N1—C3—N8—C7−178.5 (4)
C21A—Fe1—C11A—C15A114.0 (3)C6—C7—N8—C3−2.2 (7)
C13A—Fe1—C11A—C15A−81.5 (3)C14B—Fe2—C11B—C12B−80.7 (3)
C24A—Fe1—C11A—C15A39.9 (8)C23B—Fe2—C11B—C12B39.7 (7)
C23A—Fe1—C11A—C15A−169.8 (4)C21B—Fe2—C11B—C12B116.3 (3)
C22A—Fe1—C11A—C15A156.6 (3)C15B—Fe2—C11B—C12B−118.2 (4)
C12A—Fe1—C11A—C15A−118.6 (4)C25B—Fe2—C11B—C12B159.2 (3)
C15A—Fe1—C11A—C12A118.6 (4)C24B—Fe2—C11B—C12B−165.9 (4)
C14A—Fe1—C11A—C12A81.1 (3)C13B—Fe2—C11B—C12B−36.9 (3)
C25A—Fe1—C11A—C12A−168.2 (3)C22B—Fe2—C11B—C12B74.7 (3)
C21A—Fe1—C11A—C12A−127.3 (3)C14B—Fe2—C11B—C15B37.4 (3)
C13A—Fe1—C11A—C12A37.1 (2)C23B—Fe2—C11B—C15B157.8 (6)
C24A—Fe1—C11A—C12A158.5 (7)C21B—Fe2—C11B—C15B−125.5 (3)
C23A—Fe1—C11A—C12A−51.2 (5)C25B—Fe2—C11B—C15B−82.7 (3)
C22A—Fe1—C11A—C12A−84.8 (3)C12B—Fe2—C11B—C15B118.2 (4)
C15A—Fe1—C11A—C31A−120.6 (4)C24B—Fe2—C11B—C15B−47.7 (6)
C14A—Fe1—C11A—C31A−158.2 (4)C13B—Fe2—C11B—C15B81.3 (3)
C25A—Fe1—C11A—C31A−47.5 (4)C22B—Fe2—C11B—C15B−167.2 (3)
C21A—Fe1—C11A—C31A−6.6 (4)C14B—Fe2—C11B—C31B156.2 (4)
C13A—Fe1—C11A—C31A157.9 (4)C23B—Fe2—C11B—C31B−83.4 (7)
C24A—Fe1—C11A—C31A−80.7 (8)C21B—Fe2—C11B—C31B−6.8 (4)
C23A—Fe1—C11A—C31A69.6 (6)C15B—Fe2—C11B—C31B118.8 (5)
C22A—Fe1—C11A—C31A36.0 (4)C25B—Fe2—C11B—C31B36.1 (4)
C12A—Fe1—C11A—C31A120.7 (4)C12B—Fe2—C11B—C31B−123.1 (5)
C15A—C11A—C12A—C13A−1.6 (5)C24B—Fe2—C11B—C31B71.0 (6)
C31A—C11A—C12A—C13A−179.7 (4)C13B—Fe2—C11B—C31B−160.0 (4)
Fe1—C11A—C12A—C13A−59.1 (3)C22B—Fe2—C11B—C31B−48.4 (4)
C15A—C11A—C12A—Fe157.6 (3)C15B—C11B—C12B—C13B0.4 (5)
C31A—C11A—C12A—Fe1−120.6 (4)C31B—C11B—C12B—C13B176.6 (4)
C15A—Fe1—C12A—C13A81.6 (3)Fe2—C11B—C12B—C13B59.3 (3)
C14A—Fe1—C12A—C13A37.6 (3)C15B—C11B—C12B—Fe2−58.8 (3)
C25A—Fe1—C12A—C13A160.4 (7)C31B—C11B—C12B—Fe2117.3 (5)
C21A—Fe1—C12A—C13A−167.6 (3)C14B—Fe2—C12B—C13B−37.7 (3)
C24A—Fe1—C12A—C13A−48.3 (5)C23B—Fe2—C12B—C13B73.5 (3)
C23A—Fe1—C12A—C13A−84.3 (3)C21B—Fe2—C12B—C13B156.8 (3)
C22A—Fe1—C12A—C13A−126.6 (3)C15B—Fe2—C12B—C13B−81.7 (3)
C11A—Fe1—C12A—C13A119.8 (4)C25B—Fe2—C12B—C13B−169.4 (4)
C15A—Fe1—C12A—C11A−38.2 (2)C24B—Fe2—C12B—C13B41.3 (7)
C14A—Fe1—C12A—C11A−82.2 (3)C22B—Fe2—C12B—C13B114.7 (3)
C25A—Fe1—C12A—C11A40.6 (8)C11B—Fe2—C12B—C13B−120.2 (4)
C21A—Fe1—C12A—C11A72.6 (3)C14B—Fe2—C12B—C11B82.6 (3)
C13A—Fe1—C12A—C11A−119.8 (4)C23B—Fe2—C12B—C11B−166.3 (3)
C24A—Fe1—C12A—C11A−168.2 (4)C21B—Fe2—C12B—C11B−82.9 (3)
C23A—Fe1—C12A—C11A155.9 (3)C15B—Fe2—C12B—C11B38.6 (3)
C22A—Fe1—C12A—C11A113.6 (3)C25B—Fe2—C12B—C11B−49.2 (6)
C11A—C12A—C13A—C14A0.9 (5)C24B—Fe2—C12B—C11B161.5 (5)
Fe1—C12A—C13A—C14A−59.0 (3)C13B—Fe2—C12B—C11B120.2 (4)
C11A—C12A—C13A—Fe159.9 (3)C22B—Fe2—C12B—C11B−125.0 (3)
C15A—Fe1—C13A—C12A−81.8 (3)C11B—C12B—C13B—C14B−0.8 (5)
C14A—Fe1—C13A—C12A−119.6 (4)Fe2—C12B—C13B—C14B58.6 (3)
C25A—Fe1—C13A—C12A−169.4 (4)C11B—C12B—C13B—Fe2−59.4 (3)
C21A—Fe1—C13A—C12A41.0 (8)C14B—Fe2—C13B—C12B119.6 (4)
C24A—Fe1—C13A—C12A156.9 (3)C23B—Fe2—C13B—C12B−124.5 (3)
C23A—Fe1—C13A—C12A113.6 (3)C21B—Fe2—C13B—C12B−52.0 (6)
C22A—Fe1—C13A—C12A73.6 (3)C15B—Fe2—C13B—C12B81.8 (3)
C11A—Fe1—C13A—C12A−37.6 (2)C25B—Fe2—C13B—C12B165.8 (6)
C15A—Fe1—C13A—C14A37.8 (3)C24B—Fe2—C13B—C12B−165.3 (3)
C25A—Fe1—C13A—C14A−49.8 (5)C22B—Fe2—C13B—C12B−83.0 (3)
C21A—Fe1—C13A—C14A160.6 (7)C11B—Fe2—C13B—C12B37.4 (3)
C24A—Fe1—C13A—C14A−83.5 (3)C23B—Fe2—C13B—C14B115.9 (3)
C23A—Fe1—C13A—C14A−126.8 (3)C21B—Fe2—C13B—C14B−171.6 (4)
C22A—Fe1—C13A—C14A−166.8 (3)C15B—Fe2—C13B—C14B−37.8 (3)
C12A—Fe1—C13A—C14A119.6 (4)C25B—Fe2—C13B—C14B46.2 (8)
C11A—Fe1—C13A—C14A82.0 (3)C12B—Fe2—C13B—C14B−119.6 (4)
C12A—C13A—C14A—C15A0.2 (5)C24B—Fe2—C13B—C14B75.1 (3)
Fe1—C13A—C14A—C15A−59.3 (3)C22B—Fe2—C13B—C14B157.5 (3)
C12A—C13A—C14A—Fe159.5 (3)C11B—Fe2—C13B—C14B−82.2 (3)
C25A—Fe1—C14A—C15A−84.3 (3)C12B—C13B—C14B—C15B0.8 (5)
C21A—Fe1—C14A—C15A−49.8 (5)Fe2—C13B—C14B—C15B59.8 (3)
C13A—Fe1—C14A—C15A119.2 (4)C12B—C13B—C14B—Fe2−59.0 (3)
C24A—Fe1—C14A—C15A−126.9 (3)C23B—Fe2—C14B—C15B159.8 (3)
C23A—Fe1—C14A—C15A−167.5 (3)C21B—Fe2—C14B—C15B47.8 (8)
C22A—Fe1—C14A—C15A163.0 (7)C25B—Fe2—C14B—C15B76.4 (3)
C12A—Fe1—C14A—C15A81.9 (3)C12B—Fe2—C14B—C15B−81.9 (3)
C11A—Fe1—C14A—C15A37.8 (2)C24B—Fe2—C14B—C15B117.0 (3)
C15A—Fe1—C14A—C13A−119.2 (4)C13B—Fe2—C14B—C15B−119.2 (4)
C25A—Fe1—C14A—C13A156.5 (3)C22B—Fe2—C14B—C15B−168.2 (4)
C21A—Fe1—C14A—C13A−169.0 (4)C11B—Fe2—C14B—C15B−37.8 (2)
C24A—Fe1—C14A—C13A113.9 (3)C23B—Fe2—C14B—C13B−81.0 (3)
C23A—Fe1—C14A—C13A73.4 (3)C21B—Fe2—C14B—C13B167.0 (7)
C22A—Fe1—C14A—C13A43.8 (8)C15B—Fe2—C14B—C13B119.2 (4)
C12A—Fe1—C14A—C13A−37.3 (3)C25B—Fe2—C14B—C13B−164.4 (3)
C11A—Fe1—C14A—C13A−81.3 (3)C12B—Fe2—C14B—C13B37.3 (3)
C13A—C14A—C15A—C11A−1.2 (5)C24B—Fe2—C14B—C13B−123.9 (3)
Fe1—C14A—C15A—C11A−60.8 (3)C22B—Fe2—C14B—C13B−49.1 (5)
C13A—C14A—C15A—Fe159.5 (3)C11B—Fe2—C14B—C13B81.4 (3)
C12A—C11A—C15A—C14A1.7 (5)C13B—C14B—C15B—C11B−0.6 (5)
C31A—C11A—C15A—C14A179.9 (4)Fe2—C14B—C15B—C11B59.4 (3)
Fe1—C11A—C15A—C14A59.8 (3)C13B—C14B—C15B—Fe2−59.9 (3)
C12A—C11A—C15A—Fe1−58.1 (3)C12B—C11B—C15B—C14B0.1 (5)
C31A—C11A—C15A—Fe1120.1 (4)C31B—C11B—C15B—C14B−176.2 (4)
C25A—Fe1—C15A—C14A113.6 (3)Fe2—C11B—C15B—C14B−58.8 (3)
C21A—Fe1—C15A—C14A156.7 (3)C12B—C11B—C15B—Fe259.0 (3)
C13A—Fe1—C15A—C14A−37.8 (3)C31B—C11B—C15B—Fe2−117.4 (4)
C24A—Fe1—C15A—C14A72.5 (3)C23B—Fe2—C15B—C14B−44.7 (5)
C23A—Fe1—C15A—C14A42.2 (8)C21B—Fe2—C15B—C14B−165.0 (3)
C22A—Fe1—C15A—C14A−170.2 (4)C25B—Fe2—C15B—C14B−123.8 (3)
C12A—Fe1—C15A—C14A−81.3 (3)C12B—Fe2—C15B—C14B81.3 (3)
C11A—Fe1—C15A—C14A−119.4 (4)C24B—Fe2—C15B—C14B−80.9 (3)
C14A—Fe1—C15A—C11A119.4 (4)C13B—Fe2—C15B—C14B37.8 (3)
C25A—Fe1—C15A—C11A−127.0 (3)C22B—Fe2—C15B—C14B160.7 (6)
C21A—Fe1—C15A—C11A−83.9 (3)C11B—Fe2—C15B—C14B119.6 (4)
C13A—Fe1—C15A—C11A81.6 (3)C14B—Fe2—C15B—C11B−119.6 (4)
C24A—Fe1—C15A—C11A−168.1 (3)C23B—Fe2—C15B—C11B−164.3 (4)
C23A—Fe1—C15A—C11A161.6 (7)C21B—Fe2—C15B—C11B75.4 (3)
C22A—Fe1—C15A—C11A−50.8 (5)C25B—Fe2—C15B—C11B116.6 (3)
C12A—Fe1—C15A—C11A38.1 (2)C12B—Fe2—C15B—C11B−38.4 (3)
C15A—Fe1—C21A—C22A157.8 (3)C24B—Fe2—C15B—C11B159.5 (3)
C14A—Fe1—C21A—C22A−167.4 (4)C13B—Fe2—C15B—C11B−81.9 (3)
C25A—Fe1—C21A—C22A−118.1 (4)C22B—Fe2—C15B—C11B41.1 (8)
C13A—Fe1—C21A—C22A41.3 (8)C14B—Fe2—C21B—C22B156.3 (6)
C24A—Fe1—C21A—C22A−80.9 (3)C23B—Fe2—C21B—C22B37.3 (3)
C23A—Fe1—C21A—C22A−36.7 (3)C15B—Fe2—C21B—C22B−166.3 (3)
C12A—Fe1—C21A—C22A73.6 (4)C25B—Fe2—C21B—C22B119.6 (4)
C11A—Fe1—C21A—C22A114.6 (3)C12B—Fe2—C21B—C22B−80.5 (3)
C15A—Fe1—C21A—C25A−84.1 (3)C24B—Fe2—C21B—C22B81.6 (3)
C14A—Fe1—C21A—C25A−49.3 (6)C13B—Fe2—C21B—C22B−43.9 (6)
C13A—Fe1—C21A—C25A159.3 (7)C11B—Fe2—C21B—C22B−123.9 (3)
C24A—Fe1—C21A—C25A37.2 (3)C14B—Fe2—C21B—C25B36.7 (9)
C23A—Fe1—C21A—C25A81.3 (3)C23B—Fe2—C21B—C25B−82.4 (3)
C22A—Fe1—C21A—C25A118.1 (4)C15B—Fe2—C21B—C25B74.1 (4)
C12A—Fe1—C21A—C25A−168.3 (3)C12B—Fe2—C21B—C25B159.9 (3)
C11A—Fe1—C21A—C25A−127.4 (3)C24B—Fe2—C21B—C25B−38.0 (3)
C25A—C21A—C22A—C23A−0.8 (5)C13B—Fe2—C21B—C25B−163.5 (4)
Fe1—C21A—C22A—C23A59.1 (3)C22B—Fe2—C21B—C25B−119.6 (4)
C25A—C21A—C22A—Fe1−60.0 (3)C11B—Fe2—C21B—C25B116.4 (3)
C15A—Fe1—C22A—C23A−167.7 (4)C25B—C21B—C22B—C23B0.8 (6)
C14A—Fe1—C22A—C23A37.6 (9)Fe2—C21B—C22B—C23B−58.7 (3)
C25A—Fe1—C22A—C23A−81.6 (3)C25B—C21B—C22B—Fe259.5 (3)
C21A—Fe1—C22A—C23A−120.2 (4)C14B—Fe2—C22B—C23B−45.7 (5)
C13A—Fe1—C22A—C23A72.3 (4)C21B—Fe2—C22B—C23B119.7 (4)
C24A—Fe1—C22A—C23A−37.7 (3)C15B—Fe2—C22B—C23B163.5 (6)
C12A—Fe1—C22A—C23A113.3 (3)C25B—Fe2—C22B—C23B82.2 (3)
C11A—Fe1—C22A—C23A156.7 (3)C12B—Fe2—C22B—C23B−122.6 (3)
C15A—Fe1—C22A—C21A−47.5 (5)C24B—Fe2—C22B—C23B38.4 (3)
C14A—Fe1—C22A—C21A157.8 (7)C13B—Fe2—C22B—C23B−80.2 (3)
C25A—Fe1—C22A—C21A38.5 (3)C11B—Fe2—C22B—C23B−164.2 (3)
C13A—Fe1—C22A—C21A−167.5 (3)C14B—Fe2—C22B—C21B−165.4 (4)
C24A—Fe1—C22A—C21A82.5 (3)C23B—Fe2—C22B—C21B−119.7 (4)
C23A—Fe1—C22A—C21A120.2 (4)C15B—Fe2—C22B—C21B43.8 (8)
C12A—Fe1—C22A—C21A−126.6 (3)C25B—Fe2—C22B—C21B−37.4 (3)
C11A—Fe1—C22A—C21A−83.2 (3)C12B—Fe2—C22B—C21B117.7 (3)
C21A—C22A—C23A—C24A0.2 (6)C24B—Fe2—C22B—C21B−81.3 (3)
Fe1—C22A—C23A—C24A58.9 (3)C13B—Fe2—C22B—C21B160.2 (3)
C21A—C22A—C23A—Fe1−58.8 (3)C11B—Fe2—C22B—C21B76.2 (3)
C15A—Fe1—C23A—C22A158.0 (6)C21B—C22B—C23B—C24B−1.4 (5)
C14A—Fe1—C23A—C22A−168.4 (3)Fe2—C22B—C23B—C24B−60.1 (3)
C25A—Fe1—C23A—C22A81.4 (3)C21B—C22B—C23B—Fe258.7 (3)
C21A—Fe1—C23A—C22A37.2 (3)C14B—Fe2—C23B—C22B158.8 (3)
C13A—Fe1—C23A—C22A−127.2 (3)C21B—Fe2—C23B—C22B−37.4 (3)
C24A—Fe1—C23A—C22A119.9 (4)C15B—Fe2—C23B—C22B−169.6 (4)
C12A—Fe1—C23A—C22A−84.5 (3)C25B—Fe2—C23B—C22B−81.1 (3)
C11A—Fe1—C23A—C22A−48.8 (5)C12B—Fe2—C23B—C22B76.3 (3)
C15A—Fe1—C23A—C24A38.1 (8)C24B—Fe2—C23B—C22B−118.5 (4)
C14A—Fe1—C23A—C24A71.7 (3)C13B—Fe2—C23B—C22B116.6 (3)
C25A—Fe1—C23A—C24A−38.5 (3)C11B—Fe2—C23B—C22B45.9 (7)
C21A—Fe1—C23A—C24A−82.7 (3)C14B—Fe2—C23B—C24B−82.7 (3)
C13A—Fe1—C23A—C24A112.9 (3)C21B—Fe2—C23B—C24B81.1 (3)
C22A—Fe1—C23A—C24A−119.9 (4)C15B—Fe2—C23B—C24B−51.1 (6)
C12A—Fe1—C23A—C24A155.6 (3)C25B—Fe2—C23B—C24B37.4 (3)
C11A—Fe1—C23A—C24A−168.7 (4)C12B—Fe2—C23B—C24B−165.2 (3)
C22A—C23A—C24A—C25A0.6 (5)C13B—Fe2—C23B—C24B−124.9 (3)
Fe1—C23A—C24A—C25A59.9 (3)C22B—Fe2—C23B—C24B118.5 (4)
C22A—C23A—C24A—Fe1−59.3 (3)C11B—Fe2—C23B—C24B164.4 (6)
C15A—Fe1—C24A—C25A73.7 (3)C22B—C23B—C24B—C25B1.4 (5)
C14A—Fe1—C24A—C25A114.4 (3)Fe2—C23B—C24B—C25B−59.1 (3)
C21A—Fe1—C24A—C25A−37.4 (3)C22B—C23B—C24B—Fe260.5 (3)
C13A—Fe1—C24A—C25A157.2 (3)C14B—Fe2—C24B—C25B−125.8 (3)
C23A—Fe1—C24A—C25A−117.7 (4)C23B—Fe2—C24B—C25B119.4 (4)
C22A—Fe1—C24A—C25A−81.0 (3)C21B—Fe2—C24B—C25B38.0 (3)
C12A—Fe1—C24A—C25A−169.4 (4)C15B—Fe2—C24B—C25B−83.3 (3)
C11A—Fe1—C24A—C25A41.9 (8)C12B—Fe2—C24B—C25B161.6 (5)
C15A—Fe1—C24A—C23A−168.6 (3)C13B—Fe2—C24B—C25B−167.1 (3)
C14A—Fe1—C24A—C23A−127.9 (3)C22B—Fe2—C24B—C25B81.7 (3)
C25A—Fe1—C24A—C23A117.7 (4)C11B—Fe2—C24B—C25B−48.9 (6)
C21A—Fe1—C24A—C23A80.4 (3)C14B—Fe2—C24B—C23B114.8 (3)
C13A—Fe1—C24A—C23A−85.1 (3)C21B—Fe2—C24B—C23B−81.5 (3)
C22A—Fe1—C24A—C23A36.8 (3)C15B—Fe2—C24B—C23B157.3 (3)
C12A—Fe1—C24A—C23A−51.7 (5)C25B—Fe2—C24B—C23B−119.4 (4)
C11A—Fe1—C24A—C23A159.7 (6)C12B—Fe2—C24B—C23B42.2 (7)
C23A—C24A—C25A—C21A−1.1 (5)C13B—Fe2—C24B—C23B73.5 (3)
Fe1—C24A—C25A—C21A58.9 (3)C22B—Fe2—C24B—C23B−37.7 (3)
C23A—C24A—C25A—Fe1−60.0 (3)C11B—Fe2—C24B—C23B−168.3 (4)
C22A—C21A—C25A—C24A1.2 (5)C22B—C21B—C25B—C24B0.0 (6)
Fe1—C21A—C25A—C24A−59.1 (3)Fe2—C21B—C25B—C24B59.8 (3)
C22A—C21A—C25A—Fe160.3 (3)C22B—C21B—C25B—Fe2−59.8 (3)
C15A—Fe1—C25A—C24A−126.1 (3)C23B—C24B—C25B—C21B−0.9 (5)
C14A—Fe1—C25A—C24A−83.1 (3)Fe2—C24B—C25B—C21B−59.7 (3)
C21A—Fe1—C25A—C24A120.0 (4)C23B—C24B—C25B—Fe258.8 (3)
C13A—Fe1—C25A—C24A−48.3 (5)C14B—Fe2—C25B—C21B−168.2 (3)
C23A—Fe1—C25A—C24A38.7 (3)C23B—Fe2—C25B—C21B80.8 (3)
C22A—Fe1—C25A—C24A81.9 (3)C15B—Fe2—C25B—C21B−126.1 (3)
C12A—Fe1—C25A—C24A160.1 (7)C12B—Fe2—C25B—C21B−47.0 (6)
C11A—Fe1—C25A—C24A−167.5 (3)C24B—Fe2—C25B—C21B118.6 (4)
C15A—Fe1—C25A—C21A113.8 (3)C13B—Fe2—C25B—C21B156.2 (6)
C14A—Fe1—C25A—C21A156.9 (3)C22B—Fe2—C25B—C21B37.3 (3)
C13A—Fe1—C25A—C21A−168.4 (4)C11B—Fe2—C25B—C21B−82.5 (3)
C24A—Fe1—C25A—C21A−120.0 (4)C14B—Fe2—C25B—C24B73.2 (3)
C23A—Fe1—C25A—C21A−81.4 (3)C23B—Fe2—C25B—C24B−37.8 (3)
C22A—Fe1—C25A—C21A−38.2 (3)C21B—Fe2—C25B—C24B−118.6 (4)
C12A—Fe1—C25A—C21A40.1 (9)C15B—Fe2—C25B—C24B115.3 (3)
C11A—Fe1—C25A—C21A72.5 (3)C12B—Fe2—C25B—C24B−165.7 (4)
C15A—C11A—C31A—C32A45.1 (6)C13B—Fe2—C25B—C24B37.6 (8)
C12A—C11A—C31A—C32A−137.1 (4)C22B—Fe2—C25B—C24B−81.3 (3)
Fe1—C11A—C31A—C32A133.5 (4)C11B—Fe2—C25B—C24B158.9 (3)
C15A—C11A—C31A—C36A−132.9 (4)C12B—C11B—C31B—C36B−142.6 (5)
C12A—C11A—C31A—C36A44.8 (6)C15B—C11B—C31B—C36B32.9 (6)
Fe1—C11A—C31A—C36A−44.5 (5)Fe2—C11B—C31B—C36B−53.6 (5)
C36A—C31A—C32A—C33A2.2 (6)C12B—C11B—C31B—C32B35.2 (7)
C11A—C31A—C32A—C33A−175.8 (4)C15B—C11B—C31B—C32B−149.3 (4)
C36A—C31A—C32A—C1174.0 (4)Fe2—C11B—C31B—C32B124.2 (4)
C11A—C31A—C32A—C1−4.1 (6)C36B—C31B—C32B—C33B3.2 (6)
O1—C1—C32A—C31A−119.4 (5)C11B—C31B—C32B—C33B−174.6 (4)
N1—C1—C32A—C31A60.1 (6)C36B—C31B—C32B—C2−169.0 (4)
O1—C1—C32A—C33A52.7 (6)C11B—C31B—C32B—C213.1 (6)
N1—C1—C32A—C33A−127.8 (4)O2—C2—C32B—C33B−126.6 (4)
C31A—C32A—C33A—C34A−0.4 (6)N1—C2—C32B—C33B49.4 (5)
C1—C32A—C33A—C34A−173.0 (4)O2—C2—C32B—C31B46.0 (6)
C32A—C33A—C34A—C35A−1.2 (6)N1—C2—C32B—C31B−138.1 (4)
C33A—C34A—C35A—C36A1.0 (6)C31B—C32B—C33B—C34B−2.5 (6)
C34A—C35A—C36A—C31A0.9 (6)C2—C32B—C33B—C34B170.2 (4)
C32A—C31A—C36A—C35A−2.5 (6)C32B—C33B—C34B—C35B0.4 (6)
C11A—C31A—C36A—C35A175.6 (4)C33B—C34B—C35B—C36B0.9 (6)
C1—N1—C3—N8−130.6 (4)C34B—C35B—C36B—C31B0.0 (7)
C2—N1—C3—N831.6 (5)C32B—C31B—C36B—C35B−2.0 (6)
C1—N1—C3—C449.7 (5)C11B—C31B—C36B—C35B176.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···O1i0.982.363.188 (6)142
C13B—H13B···O2ii0.952.583.510 (6)167
C33B—H33B···Cg10.952.583.387 (5)144
C35A—H35A···Cg2iii0.952.613.489 (6)154
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula[Fe2(C5H5)2(C30H22N2O2)]
Mr684.38
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)12.0861 (7), 12.4935 (8), 12.5028 (8)
α, β, γ (°)65.159 (3), 62.696 (3), 81.580 (3)
V (Å3)1519.83 (16)
Z2
Radiation typeMo Kα
µ (mm−1)1.00
Crystal size (mm)0.22 × 0.22 × 0.14
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.811, 0.873
No. of measured, independent and
observed [I > 2σ(I)] reflections		10819, 6865, 3530
Rint0.107
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.154, 0.95
No. of reflections6865
No. of parameters417
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.77, −0.87

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PREP8 (Ferguson, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9B···O1i0.982.363.188 (6)142
C13B—H13B···O2ii0.952.583.510 (6)167
C33B—H33B···Cg10.952.583.387 (5)144
C35A—H35A···Cg2iii0.952.613.489 (6)154
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+2.
 

Footnotes

‡Additional correspondence author, e-mail address: alough@chem.utoronto.ca.

Acknowledgements

JFG thanks Dublin City University and PRTLI-3 (NICB) for grants in aid of chemical research.

References

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ISSN: 2056-9890
Volume 65| Part 3| March 2009| Pages m332-m333
doi:10.1107/S1600536809006278
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