Oxidative degradation of the organometallic iron(II) complex [Fe{bis­[3-(pyridin-2-yl)-1H-imidazol-1-yl]methane}(MeCN)(PMe₃)](PF₆)₂: structure of the ligand decomposition product trapped via coordination to iron(II)

Iron is of inter­est as a catalyst because of its established use in the Haber–Bosch process and because of its high abundance and low toxicity. Nitro­gen-heterocyclic carbenes (NHC) are important ligands in homogeneous catalysis and iron–NHC complexes have attracted increasing attention in recent years but still face problems in terms of stability under oxidative conditions. The structure of the iron(II) complex [1,1′-bis­(pyridin-2-yl)-2,2-bi(1H-imidazole)-κN³][3,3′-bis­(pyridin-2-yl-κN)-1,1′-methane­diylbi(1H-imidazol-2-yl-κC²)](tri­methyl­phos­phane-κP)iron(II) bis­(hexa­fluorido­phosphate), [Fe(C₁₇H₁₄N₆)(C₁₆H₁₂N₆)(C₃H₉P)](PF₆)₂, features coordination by an organic decomposition product of a tetra­dentate NHC ligand in an axial position. The decomposition product, a C—C-coupled bi­imidazole, is trapped by coordination to still-intact iron(II) complexes. Insights into the structural features of the organic decomposition products might help to improve the stability of oxidation catalysts under harsh conditions.

S1. Introduction

\ Iron is of inter­est as catalyst material, not only because of its established use in the Haber–Bosch process, but also because of its high abundance and low toxicity (Bauer & Knölker, 2015; Riener et al., 2014). With the rise of N-heterocyclic carbenes (NHCs) as a ligand class in homogeneous catalysis, iron–NHC complexes have also attracted increasing attention in recent years (Riener et al., 2014). However, especially in the field of homogeneous oxidation catalysis, iron-based catalysts, including iron–NHC complexes, still face problems in terms of stability under oxidative conditions (Talsi & Bryliakov, 2012).

Decomposition of the respective catalysts can be caused by self-oxidation of the ligand environment, leading to degradation of the organic ligand structure (England et al., 2008). It is not only strong oxidants, such as hydrogen peroxide or alkyl peroxides, that can cause ligand degradation. Depending on the solvent and reaction conditions, di­oxy­gen can also induce undesired side reactions.

In this work, a previously reported Fe^II–NHC complex, [Fe(NCCN)(MeCN)(PMe₃)](PF₆)₂ {NCCN is bis­[3-(pyridin-2-yl)-1H-imidazol-1-yl]methane}, with one labile coordination site (Haslinger et al., 2014), is exposed to air in acetone solution, leading to slow degradation of the ligand environment (Scheme 1). The decomposition product of the organic ligand is trapped by coordination to the still-intact Fe^II–NHC complexes in solution via the aforementioned labile coordination site. The resulting structure was identified by single-crystal X-ray diffraction as [1,1'-bis­(pyridin-2-yl)-2,2-bi(1H-imidazole)-κN³][3,3'-\ bis­(pyridin-2-yl-κN)-1,1'-methane­diylbi(1H-imidazol-2-yl-\ κC²)](tri­methyl­phosphane-κP)iron(II) bis­(hexafluoridophosphate), (I). It is of inter­est that, in the organic decomposition product of the former NCCN ligand, a new C—C bond is formed between the NHC groups and, in addition, the methyl­ene bridge is cleaved.

S2. Experimental

S2.1. General considerations

The chemicals used were purchased from commercial suppliers and used without further purification. For the preparation of [Fe(NCCN)(MeCN)(PMe₃)](PF₆)₂, water- and oxygen-free aceto­nitrile was obtained from a solvent purification system by MBraun. Single crystals of (I) were measured in the SC–XRD laboratory of the Catalysis Research Center at Technische Universität München.

S2.2. Synthesis and crystallization

The synthesis of [Fe(NCCN)(MeCN)(PMe₃)](PF₆)₂ was performed according to known literature procedures [References needed unless the reaction is routine].

[Fe(NCCN)(MeCN)(PMe₃)](PF₆)₂ (10 mg) was dissolved in acetone (HPLC grade, 2 ml) under air and a fraction of the solution was transferred into an NMR tube. The NMR tube was placed in a Schlenk tube filled with di­ethyl ether (10 ml) and the Schlenk tube was sealed tightly under air. Within six weeks, single crystals of (I) suitable for X-ray diffraction were collected after slow diffusion of the di­ethyl ether into the solution of [Fe(NCCN)(MeCN)(PMe₃)](PF₆)₂ in acetone. A crystal was selected, fixed on top of a glass fibre using perfluorinated ether and transferred to the diffractometer.

S2.3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms could not be located in difference Fourier maps and were calculated in ideal positions (riding model), with C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C) for CH₃ groups, C—H = 0.99 Å and U_iso(H) = 1.2U_eq(C) for CH₂ groups, and C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C) for CH groups. Split-layer position refinement was used for atoms F7, F8, F9, F10, F11, F12, C34, C35 and C36. SIMU and DELU [Please rephrase using non-software-specific terms] restraints were applied to the following atoms to ensure reasonable ellipsoids: C34, C35, C36, C34A, C35A, C36A, F7, F8, F9, F10, F11, F12, F7A, F8A, F9A, F10A, F11A and F12A.

S3. Results and discussion

In the title compound, (I) (Fig. 1), the Fe^II cation is coordinated in an o­cta­hedral manner by an equatorial tetra­dentate NCCN ligand, one PMe₃ ligand in an axial position and the N-bound decomposition product of the former NCCN ligand in the other axial position trans to PMe₃. For the equatorial coordination of the tetra­dentate ligand, the Fe—N_py (py is pyridine) bond lengths are 2.080 (3) and 2.067 (3) Å, and the Fe—C_NHC bond lengths are 1.818 (4) and 1.812 (4) Å (Table 2).

The four equatorially coordinating atoms, N3, N6, C1 and C10, and atom Fe1 are located in one plane. These findings are in accordance with other Fe^II complexes bearing the same equatorial NCCN ligand (Haslinger et al., 2014; Raba et al., 2012).

The Fe1—P1 bond length [2.2179 (13) Å; Table 2] is slightly shorter than in the related Fe^II complex [Revised text OK?] with both axial positions coordinated by PMe₃ ligands (Haslinger et al., 2014).

The imidazole group trans to the PMe₃ ligand of (I) is coordinated with an Fe1—N8 bond length of 2.047 (3) Å (Table 2).

A P1—Fe1—N8 angle of 171.70 (8)° (Table 2) indicates repulsion of the axial ligands by the H atoms of the methyl­ene bridge of the equatorial NCCN ligand.

The planes spanned by the two C-coupled imidazole rings are twisted with an angle of 72.72(s.u.?)° and the bond length of the coupled C atoms [C18—C26 = 1.458 (5) Å] is slightly shorter than expected for a single bond, but still significantly longer than a double bond (Clayden et al., 2001).

As the axial di­imidazole ligand is not charged and two PF₆^- anions per Fe atom are found, Fe is in the +II oxidation state.

The packing of (I) is shown in Fig. 2, with no relevant packing effects dete­cta­ble.

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009) and enCIFer (Allen et al., 2004).

Figures

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are shown at the 50% probability level. Minor disordered components are indicated by dashed bonds [OK?] H atoms have been omitted for clarity.
	Fig. 2. The crystal packing of (I), along the a axis.

[1,1'-Bis(pyridin-2-yl)-2,2-bi(1H-imidazole)-κN³][3,3'-bis(pyridin-2-yl-κN)-1,1'-methanediylbi(1H-imidazol-2-yl-κC²)](trimethylphosphane-κP)iron(II) bis(hexafluoridophosphate)

Crystal data

[Fe(C17H14N6)(C16H12N6)(C3H9P)](PF6)2	Z = 2
Mr = 1012.52	F(000) = 1028
Triclinic, P1	Dx = 1.611 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.1146 (4) Å	Cell parameters from 9982 reflections
b = 12.1591 (5) Å	θ = 2.4–25.4°
c = 17.7002 (7) Å	µ = 0.58 mm^−1
α = 97.219 (2)°	T = 123 K
β = 97.020 (2)°	Fragment, red
γ = 102.060 (2)°	0.25 × 0.22 × 0.13 mm
V = 2087.05 (15) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	7607 independent reflections
Radiation source: rotating anode FR591	5543 reflections with I > 2σ(I)
MONTEL optic monochromator	Rint = 0.095
Detector resolution: 16 pixels mm^-1	θmax = 25.4°, θmin = 1.7°
φ and ω rotation scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −14→14
Tmin = 0.414, Tmax = 0.745	l = −21→21
52121 measured reflections

Refinement

Refinement on F^2	120 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0432P)^2 + 3.9609P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
7607 reflections	Δρmax = 0.75 e Å^−3
666 parameters	Δρmin = −0.73 e Å^−3

Special details

Experimental. Diffractometer operator S. Haslinger scanspeed 20 s per frame dx 35 mm 2822 frames measured in 7 data sets phi-scans with delta_phi = 0.5 omega-scans with delta_omega = 0.5

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Fe1	0.55140 (5)	0.10589 (4)	0.25424 (3)	0.0219 (2)
P1	0.67882 (11)	0.00708 (10)	0.31566 (6)	0.0344 (3)
P3	−0.01542 (11)	0.81332 (9)	0.10108 (7)	0.0396 (3)
P2	0.07282 (11)	0.29379 (9)	0.55139 (6)	0.0327 (3)
N1	0.5022 (3)	0.2190 (3)	0.38906 (16)	0.0270 (10)
N2	0.6876 (3)	0.3151 (3)	0.36119 (17)	0.0323 (10)
N3	0.3927 (3)	0.0490 (2)	0.31436 (16)	0.0236 (9)
N4	0.8024 (3)	0.2768 (3)	0.25216 (18)	0.0355 (10)
N5	0.7366 (3)	0.1440 (3)	0.15325 (17)	0.0322 (10)
N6	0.5477 (3)	0.0014 (3)	0.15205 (16)	0.0261 (10)
N7	0.2937 (3)	0.2808 (2)	0.13328 (16)	0.0221 (9)
F7	0.1493 (8)	0.8291 (8)	0.1094 (6)	0.082 (3)	0.534 (5)
F7A	0.0457 (10)	0.8292 (10)	0.0319 (5)	0.103 (3)	0.466 (5)
F8	−0.1712 (10)	0.7998 (10)	0.0866 (7)	0.085 (3)	0.534 (5)
N8	0.4136 (3)	0.1751 (2)	0.19260 (15)	0.0187 (8)
F8A	−0.0924 (11)	0.7881 (9)	0.1750 (6)	0.117 (3)	0.466 (5)
F9	−0.0138 (6)	0.7203 (7)	0.0257 (4)	0.086 (2)	0.534 (5)
N9	0.1581 (3)	0.4128 (3)	0.1295 (2)	0.0370 (11)
F9A	−0.0511 (6)	0.6775 (5)	0.0789 (6)	0.062 (2)	0.466 (5)
N10	0.6340 (3)	0.3993 (3)	0.1547 (2)	0.0382 (11)
F10	0.0192 (9)	0.9099 (8)	0.0428 (5)	0.110 (3)	0.534 (5)
F10A	0.1230 (11)	0.8118 (10)	0.1460 (6)	0.094 (3)	0.466 (5)
N11	0.5226 (3)	0.4747 (3)	0.2416 (2)	0.0380 (11)
F11	0.0114 (10)	0.9165 (8)	0.1648 (5)	0.076 (3)	0.534 (5)
F11A	−0.0035 (11)	0.9437 (8)	0.1289 (6)	0.072 (3)	0.466 (5)
F12	−0.0259 (8)	0.7246 (7)	0.1498 (5)	0.096 (3)	0.534 (5)
N12	0.3521 (4)	0.3951 (3)	0.3105 (2)	0.0477 (14)
F12A	−0.1504 (15)	0.8144 (12)	0.0531 (7)	0.090 (3)	0.466 (5)
C1	0.5884 (4)	0.2197 (3)	0.3362 (2)	0.0253 (11)
C2	0.5467 (4)	0.3137 (3)	0.4470 (2)	0.0377 (14)
C3	0.6619 (5)	0.3729 (4)	0.4291 (2)	0.0413 (14)
C4	0.3895 (4)	0.1258 (3)	0.3764 (2)	0.0259 (11)
C5	0.2874 (4)	0.1134 (4)	0.4222 (2)	0.0369 (14)
C6	0.1842 (4)	0.0159 (4)	0.4042 (2)	0.0456 (14)
C7	0.1856 (4)	−0.0653 (4)	0.3428 (2)	0.0403 (14)
C8	0.2901 (4)	−0.0451 (3)	0.2996 (2)	0.0316 (12)
C9	0.8082 (4)	0.3503 (4)	0.3251 (2)	0.0430 (14)
C10	0.7024 (4)	0.1832 (3)	0.2222 (2)	0.0289 (11)
C11	0.8981 (4)	0.2959 (4)	0.2020 (2)	0.0443 (16)
C12	0.8581 (4)	0.2144 (4)	0.1404 (3)	0.0429 (14)
C13	0.6523 (4)	0.0415 (4)	0.1142 (2)	0.0322 (14)
C14	0.6751 (5)	−0.0147 (4)	0.0456 (2)	0.0412 (16)
C15	0.5850 (5)	−0.1151 (4)	0.0138 (2)	0.0477 (16)
C16	0.4760 (5)	−0.1578 (4)	0.0498 (2)	0.0443 (16)
C17	0.4610 (4)	−0.0974 (3)	0.1187 (2)	0.0335 (12)
C18	0.4167 (3)	0.2779 (3)	0.17353 (19)	0.0205 (10)
C19	0.2092 (4)	0.1756 (3)	0.1274 (2)	0.0261 (11)
C20	0.2832 (3)	0.1115 (3)	0.1626 (2)	0.0252 (11)
C21	0.2604 (4)	0.3781 (3)	0.1030 (2)	0.0241 (11)
C22	0.3324 (4)	0.4256 (3)	0.0501 (2)	0.0365 (12)
C23	0.2959 (5)	0.5189 (4)	0.0231 (3)	0.0468 (17)
C24	0.1919 (4)	0.5585 (4)	0.0506 (3)	0.0463 (17)
C25	0.1251 (5)	0.5033 (4)	0.1019 (3)	0.0506 (17)
C26	0.5270 (4)	0.3802 (3)	0.1912 (2)	0.0283 (12)
C27	0.7017 (4)	0.5101 (4)	0.1843 (3)	0.0504 (16)
C28	0.6354 (5)	0.5568 (4)	0.2357 (3)	0.0550 (18)
C29	0.4156 (4)	0.4881 (4)	0.2852 (2)	0.0402 (12)
C30	0.3829 (5)	0.5910 (4)	0.2979 (4)	0.069 (2)
C31	0.2781 (6)	0.5994 (5)	0.3397 (4)	0.083 (3)
C32	0.2092 (5)	0.5060 (5)	0.3659 (3)	0.0644 (19)
C33	0.2483 (5)	0.4067 (5)	0.3499 (2)	0.0540 (18)
C34	0.6995 (11)	0.0397 (9)	0.4198 (5)	0.066 (3)	0.579 (6)
C34A	0.8074 (14)	0.0709 (13)	0.3919 (8)	0.073 (4)	0.421 (6)
C35	0.8628 (8)	0.0394 (8)	0.3039 (5)	0.060 (3)	0.579 (6)
C35A	0.7525 (15)	−0.0962 (12)	0.2578 (8)	0.070 (3)	0.421 (6)
C36	0.6293 (12)	−0.1364 (8)	0.2904 (7)	0.084 (3)	0.579 (6)
C36A	0.5800 (12)	−0.1131 (11)	0.3649 (9)	0.068 (4)	0.421 (6)
F1	0.0786 (3)	0.1645 (2)	0.55023 (19)	0.0654 (10)
F2	0.0693 (3)	0.4234 (2)	0.5525 (2)	0.0898 (16)
F3	−0.0877 (2)	0.2619 (2)	0.54952 (15)	0.0485 (8)
F4	0.0922 (3)	0.3122 (4)	0.64204 (16)	0.1022 (16)
F5	0.2353 (3)	0.3262 (2)	0.55336 (18)	0.0633 (10)
F6	0.0548 (3)	0.2751 (3)	0.46073 (14)	0.0690 (11)
H2	0.50370	0.33200	0.49020	0.0450*
H3	0.71700	0.44220	0.45760	0.0500*
H5	0.28840	0.17010	0.46450	0.0450*
H6	0.11220	0.00480	0.43420	0.0550*
H7	0.11620	−0.13360	0.33050	0.0480*
H8	0.28980	−0.10080	0.25680	0.0380*
H9A	0.89090	0.34820	0.36050	0.0520*
H9B	0.81550	0.42970	0.31560	0.0520*
H11	0.97760	0.35610	0.21010	0.0530*
H12	0.90290	0.20580	0.09660	0.0520*
H14	0.75060	0.01550	0.02150	0.0500*
H15	0.59760	−0.15570	−0.03330	0.0570*
H16	0.41260	−0.22700	0.02780	0.0530*
H17	0.38620	−0.12690	0.14350	0.0410*
H19	0.11650	0.15230	0.10320	0.0320*
H20	0.25060	0.03360	0.16640	0.0300*
H22	0.40470	0.39570	0.03250	0.0440*
H23	0.34260	0.55460	−0.01390	0.0560*
H24	0.16650	0.62360	0.03420	0.0560*
H25	0.05070	0.53020	0.11930	0.0600*
H27	0.78460	0.54810	0.16980	0.0610*
H28	0.66120	0.63230	0.26310	0.0660*
H30	0.43060	0.65490	0.27860	0.0830*
H31	0.25350	0.67040	0.35040	0.1000*
H32	0.13630	0.51060	0.39440	0.0770*
H33	0.19990	0.34140	0.36750	0.0640*
H34A	0.61020	0.01900	0.43680	0.1000*	0.579 (6)
H34B	0.73820	0.12140	0.43610	0.1000*	0.579 (6)
H34C	0.76110	−0.00360	0.44270	0.1000*	0.579 (6)
H34D	0.84830	0.01250	0.41250	0.1090*	0.421 (6)
H34E	0.76890	0.11080	0.43230	0.1090*	0.421 (6)
H34F	0.87780	0.12540	0.37380	0.1090*	0.421 (6)
H35A	0.91090	−0.00740	0.33330	0.0910*	0.579 (6)
H35B	0.90340	0.12020	0.32300	0.0910*	0.579 (6)
H35C	0.87080	0.02250	0.24930	0.0910*	0.579 (6)
H35D	0.79260	−0.14240	0.29170	0.1050*	0.421 (6)
H35E	0.82360	−0.05490	0.23220	0.1050*	0.421 (6)
H35F	0.68020	−0.14580	0.21890	0.1050*	0.421 (6)
H36A	0.68150	−0.17290	0.32610	0.1250*	0.579 (6)
H36B	0.64650	−0.15790	0.23790	0.1250*	0.579 (6)
H36C	0.53150	−0.16130	0.29270	0.1250*	0.579 (6)
H36D	0.64310	−0.15750	0.38470	0.1020*	0.421 (6)
H36E	0.50630	−0.16310	0.32700	0.1020*	0.421 (6)
H36F	0.54100	−0.07890	0.40750	0.1020*	0.421 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0148 (3)	0.0302 (3)	0.0199 (3)	0.0069 (2)	0.0007 (2)	−0.0004 (2)
P1	0.0286 (6)	0.0484 (7)	0.0281 (5)	0.0186 (5)	−0.0030 (4)	0.0041 (5)
P3	0.0369 (6)	0.0320 (6)	0.0437 (6)	0.0079 (5)	−0.0113 (5)	−0.0003 (5)
P2	0.0304 (6)	0.0307 (6)	0.0344 (6)	0.0011 (4)	0.0095 (5)	0.0010 (4)
N1	0.0285 (17)	0.0310 (18)	0.0201 (15)	0.0079 (14)	0.0039 (13)	−0.0029 (13)
N2	0.0251 (17)	0.0367 (19)	0.0273 (16)	−0.0037 (15)	−0.0022 (14)	−0.0006 (14)
N3	0.0217 (16)	0.0253 (17)	0.0229 (15)	0.0058 (13)	0.0001 (13)	0.0032 (13)
N4	0.0134 (16)	0.055 (2)	0.0335 (18)	−0.0009 (15)	−0.0009 (14)	0.0083 (16)
N5	0.0195 (17)	0.053 (2)	0.0289 (17)	0.0167 (16)	0.0074 (14)	0.0067 (16)
N6	0.0237 (17)	0.0366 (19)	0.0220 (15)	0.0190 (14)	0.0016 (13)	0.0013 (14)
N7	0.0169 (15)	0.0224 (16)	0.0287 (16)	0.0064 (12)	0.0066 (13)	0.0045 (13)
F7	0.039 (3)	0.075 (4)	0.117 (6)	0.006 (3)	0.015 (4)	−0.031 (5)
F7A	0.123 (5)	0.106 (5)	0.083 (4)	0.018 (5)	0.051 (4)	0.001 (4)
F8	0.032 (3)	0.056 (4)	0.156 (8)	0.014 (3)	−0.006 (5)	−0.010 (6)
N8	0.0128 (14)	0.0216 (16)	0.0211 (14)	0.0034 (12)	0.0040 (12)	0.0001 (12)
F8A	0.123 (5)	0.109 (5)	0.121 (5)	0.003 (4)	0.063 (4)	0.024 (4)
F9	0.054 (3)	0.088 (5)	0.091 (4)	0.012 (3)	−0.013 (3)	−0.045 (4)
N9	0.0306 (19)	0.039 (2)	0.052 (2)	0.0187 (16)	0.0179 (16)	0.0180 (17)
F9A	0.035 (3)	0.028 (3)	0.119 (5)	0.013 (2)	−0.008 (4)	0.008 (3)
N10	0.0231 (18)	0.042 (2)	0.050 (2)	0.0039 (15)	0.0119 (16)	0.0090 (17)
F10	0.132 (5)	0.089 (4)	0.110 (5)	0.019 (4)	0.006 (4)	0.040 (4)
F10A	0.065 (5)	0.087 (4)	0.105 (6)	0.014 (4)	−0.058 (4)	−0.007 (5)
N11	0.0302 (19)	0.0279 (19)	0.050 (2)	−0.0011 (15)	0.0080 (16)	−0.0049 (16)
F11	0.058 (3)	0.071 (5)	0.086 (5)	0.016 (3)	0.002 (4)	−0.033 (4)
F11A	0.052 (4)	0.036 (4)	0.117 (7)	0.001 (3)	0.017 (5)	−0.022 (4)
F12	0.098 (4)	0.081 (4)	0.126 (5)	0.027 (3)	0.023 (4)	0.066 (4)
N12	0.053 (2)	0.054 (3)	0.037 (2)	0.014 (2)	0.0098 (18)	0.0047 (18)
F12A	0.084 (6)	0.054 (4)	0.123 (7)	0.040 (4)	−0.052 (5)	0.007 (5)
C1	0.0193 (19)	0.028 (2)	0.0265 (19)	0.0049 (16)	−0.0010 (15)	0.0015 (16)
C2	0.045 (3)	0.037 (2)	0.027 (2)	0.007 (2)	0.0045 (19)	−0.0051 (18)
C3	0.050 (3)	0.034 (2)	0.029 (2)	0.000 (2)	−0.005 (2)	−0.0093 (18)
C4	0.025 (2)	0.030 (2)	0.0232 (18)	0.0095 (16)	0.0009 (16)	0.0037 (16)
C5	0.035 (2)	0.053 (3)	0.025 (2)	0.014 (2)	0.0085 (18)	0.0043 (19)
C6	0.033 (2)	0.068 (3)	0.036 (2)	0.003 (2)	0.0092 (19)	0.019 (2)
C7	0.033 (2)	0.047 (3)	0.036 (2)	−0.006 (2)	0.0039 (19)	0.015 (2)
C8	0.032 (2)	0.031 (2)	0.029 (2)	0.0028 (18)	−0.0009 (17)	0.0065 (17)
C9	0.030 (2)	0.054 (3)	0.034 (2)	−0.007 (2)	−0.0060 (19)	0.004 (2)
C10	0.0161 (19)	0.049 (2)	0.0220 (18)	0.0097 (18)	0.0001 (15)	0.0063 (17)
C11	0.014 (2)	0.076 (3)	0.045 (3)	0.006 (2)	0.0078 (19)	0.021 (2)
C12	0.020 (2)	0.077 (3)	0.041 (2)	0.020 (2)	0.0147 (19)	0.020 (2)
C13	0.030 (2)	0.048 (3)	0.028 (2)	0.030 (2)	0.0034 (18)	0.0067 (18)
C14	0.047 (3)	0.060 (3)	0.030 (2)	0.038 (2)	0.012 (2)	0.008 (2)
C15	0.071 (3)	0.055 (3)	0.029 (2)	0.044 (3)	0.009 (2)	0.000 (2)
C16	0.060 (3)	0.041 (3)	0.033 (2)	0.027 (2)	−0.003 (2)	−0.0064 (19)
C17	0.039 (2)	0.034 (2)	0.030 (2)	0.0199 (19)	−0.0012 (18)	0.0007 (18)
C18	0.0177 (18)	0.0223 (19)	0.0213 (17)	0.0039 (15)	0.0076 (15)	−0.0007 (15)
C19	0.0161 (18)	0.024 (2)	0.038 (2)	0.0032 (15)	0.0031 (16)	0.0072 (17)
C20	0.0188 (19)	0.0214 (19)	0.034 (2)	0.0017 (15)	0.0022 (16)	0.0053 (16)
C21	0.0213 (19)	0.0234 (19)	0.0287 (19)	0.0051 (15)	0.0076 (16)	0.0048 (16)
C22	0.030 (2)	0.035 (2)	0.049 (2)	0.0105 (19)	0.014 (2)	0.011 (2)
C23	0.045 (3)	0.042 (3)	0.059 (3)	0.005 (2)	0.018 (2)	0.028 (2)
C24	0.038 (3)	0.037 (3)	0.073 (3)	0.015 (2)	0.015 (2)	0.026 (2)
C25	0.042 (3)	0.045 (3)	0.079 (3)	0.026 (2)	0.020 (3)	0.026 (3)
C26	0.023 (2)	0.027 (2)	0.034 (2)	0.0061 (16)	0.0035 (17)	0.0011 (16)
C27	0.027 (2)	0.040 (3)	0.079 (3)	−0.006 (2)	0.013 (2)	0.008 (2)
C28	0.035 (3)	0.029 (2)	0.090 (4)	−0.008 (2)	0.009 (3)	−0.006 (2)
C29	0.036 (2)	0.031 (2)	0.047 (2)	0.0031 (19)	0.008 (2)	−0.013 (2)
C30	0.055 (3)	0.030 (3)	0.121 (5)	0.006 (2)	0.037 (3)	−0.009 (3)
C31	0.072 (4)	0.053 (4)	0.123 (5)	0.022 (3)	0.038 (4)	−0.024 (4)
C32	0.045 (3)	0.083 (4)	0.055 (3)	0.008 (3)	0.014 (2)	−0.023 (3)
C33	0.051 (3)	0.074 (4)	0.036 (2)	0.010 (3)	0.014 (2)	0.005 (2)
C34	0.078 (6)	0.100 (7)	0.039 (4)	0.055 (5)	0.003 (4)	0.026 (4)
C34A	0.063 (6)	0.087 (7)	0.070 (6)	0.032 (6)	−0.017 (5)	0.023 (6)
C35	0.042 (4)	0.089 (5)	0.072 (5)	0.046 (4)	0.012 (4)	0.040 (4)
C35A	0.072 (6)	0.086 (6)	0.073 (6)	0.057 (5)	0.004 (5)	0.028 (5)
C36	0.078 (6)	0.059 (5)	0.109 (7)	0.024 (5)	−0.034 (5)	0.029 (5)
C36A	0.048 (6)	0.059 (6)	0.108 (8)	0.018 (5)	0.002 (6)	0.053 (7)
F1	0.0556 (17)	0.0430 (16)	0.110 (2)	0.0157 (13)	0.0321 (17)	0.0318 (16)
F2	0.067 (2)	0.0316 (16)	0.176 (4)	0.0073 (14)	0.060 (2)	0.0024 (19)
F3	0.0311 (13)	0.0480 (15)	0.0651 (16)	0.0049 (11)	0.0147 (12)	0.0041 (13)
F4	0.073 (2)	0.178 (4)	0.0367 (16)	0.005 (2)	0.0046 (15)	−0.011 (2)
F5	0.0311 (14)	0.0582 (18)	0.092 (2)	−0.0020 (12)	0.0145 (14)	−0.0045 (15)
F6	0.072 (2)	0.101 (2)	0.0359 (14)	0.0151 (17)	0.0152 (14)	0.0188 (15)

Geometric parameters (Å, º)

Fe1—P1	2.2179 (13)	C6—C7	1.377 (6)
Fe1—N3	2.080 (3)	C7—C8	1.378 (6)
Fe1—N6	2.067 (3)	C11—C12	1.337 (6)
Fe1—N8	2.047 (3)	C13—C14	1.386 (5)
Fe1—C1	1.818 (4)	C14—C15	1.369 (7)
Fe1—C10	1.812 (4)	C15—C16	1.381 (7)
P1—C34	1.813 (9)	C16—C17	1.384 (5)
P1—C35	1.863 (9)	C18—C26	1.458 (5)
P1—C36	1.697 (10)	C19—C20	1.345 (5)
P1—C34A	1.732 (14)	C21—C22	1.367 (5)
P1—C35A	1.854 (15)	C22—C23	1.386 (6)
P1—C36A	1.954 (14)	C23—C24	1.361 (7)
P3—F7A	1.454 (10)	C24—C25	1.358 (7)
P3—F7	1.623 (9)	C27—C28	1.334 (7)
P3—F8	1.536 (11)	C29—C30	1.359 (7)
P3—F9	1.641 (7)	C30—C31	1.378 (9)
P3—F10	1.669 (9)	C31—C32	1.368 (8)
P3—F11	1.532 (9)	C32—C33	1.355 (8)
P3—F12	1.458 (9)	C2—H2	0.9500
P3—F10A	1.528 (11)	C3—H3	0.9500
P3—F8A	1.632 (11)	C5—H5	0.9500
P3—F9A	1.602 (7)	C6—H6	0.9500
P3—F11A	1.575 (10)	C7—H7	0.9500
P3—F12A	1.521 (15)	C8—H8	0.9500
P2—F3	1.584 (2)	C9—H9A	0.9900
P2—F1	1.583 (3)	C9—H9B	0.9900
P2—F2	1.582 (3)	C11—H11	0.9500
P2—F6	1.575 (3)	C12—H12	0.9500
P2—F4	1.574 (3)	C14—H14	0.9500
P2—F5	1.603 (3)	C15—H15	0.9500
N1—C1	1.354 (5)	C16—H16	0.9500
N1—C4	1.403 (5)	C17—H17	0.9500
N1—C2	1.398 (5)	C19—H19	0.9500
N2—C3	1.395 (5)	C20—H20	0.9500
N2—C9	1.456 (5)	C22—H22	0.9500
N2—C1	1.351 (5)	C23—H23	0.9500
N3—C4	1.357 (4)	C24—H24	0.9500
N3—C8	1.348 (5)	C25—H25	0.9500
N4—C9	1.462 (5)	C27—H27	0.9500
N4—C11	1.395 (5)	C28—H28	0.9500
N4—C10	1.355 (5)	C30—H30	0.9500
N5—C12	1.404 (6)	C31—H31	0.9500
N5—C10	1.365 (5)	C32—H32	0.9500
N5—C13	1.398 (6)	C33—H33	0.9500
N6—C17	1.348 (5)	C34—H34B	0.9800
N6—C13	1.359 (5)	C34—H34A	0.9800
N7—C21	1.443 (4)	C34—H34C	0.9800
N7—C19	1.366 (5)	C34A—H34D	0.9800
N7—C18	1.366 (4)	C34A—H34E	0.9800
N8—C18	1.330 (4)	C34A—H34F	0.9800
N8—C20	1.385 (4)	C35—H35C	0.9800
N9—C21	1.312 (5)	C35—H35B	0.9800
N9—C25	1.345 (6)	C35—H35A	0.9800
N10—C26	1.321 (5)	C35A—H35F	0.9800
N10—C27	1.381 (6)	C35A—H35E	0.9800
N11—C29	1.428 (5)	C35A—H35D	0.9800
N11—C26	1.375 (5)	C36—H36C	0.9800
N11—C28	1.374 (6)	C36—H36B	0.9800
N12—C29	1.336 (6)	C36—H36A	0.9800
N12—C33	1.351 (6)	C36A—H36D	0.9800
C2—C3	1.332 (6)	C36A—H36E	0.9800
C4—C5	1.384 (6)	C36A—H36F	0.9800
C5—C6	1.380 (6)
P1—Fe1—N3	89.96 (8)	N6—C13—C14	123.7 (4)
P1—Fe1—N6	89.56 (10)	N5—C13—N6	112.5 (3)
P1—Fe1—N8	171.70 (8)	N5—C13—C14	123.8 (4)
P1—Fe1—C1	91.85 (12)	C13—C14—C15	117.7 (4)
P1—Fe1—C10	89.64 (13)	C14—C15—C16	120.4 (4)
N3—Fe1—N6	114.09 (12)	C15—C16—C17	118.5 (4)
N3—Fe1—N8	85.49 (11)	N6—C17—C16	122.9 (4)
N3—Fe1—C1	79.63 (14)	N7—C18—C26	120.1 (3)
N3—Fe1—C10	165.82 (14)	N7—C18—N8	110.5 (3)
N6—Fe1—N8	85.98 (12)	N8—C18—C26	129.5 (3)
N6—Fe1—C1	166.22 (16)	N7—C19—C20	106.4 (3)
N6—Fe1—C10	80.08 (15)	N8—C20—C19	110.5 (3)
N8—Fe1—C1	94.15 (14)	N7—C21—C22	120.1 (3)
N8—Fe1—C10	96.47 (14)	N9—C21—C22	125.2 (4)
C1—Fe1—C10	86.22 (17)	N7—C21—N9	114.7 (3)
Fe1—P1—C34	114.2 (4)	C21—C22—C23	117.5 (4)
Fe1—P1—C35	115.2 (3)	C22—C23—C24	118.8 (5)
Fe1—P1—C36	115.4 (4)	C23—C24—C25	118.9 (5)
Fe1—P1—C34A	122.1 (5)	N9—C25—C24	123.9 (5)
Fe1—P1—C35A	118.5 (4)	N11—C26—C18	123.2 (3)
Fe1—P1—C36A	115.8 (4)	N10—C26—C18	124.7 (3)
C34—P1—C35	98.6 (5)	N10—C26—N11	111.6 (3)
C34—P1—C36	108.0 (5)	N10—C27—C28	111.2 (4)
C35—P1—C36	103.5 (5)	N11—C28—C27	106.8 (4)
C34A—P1—C35A	104.7 (7)	N12—C29—C30	124.0 (4)
C34A—P1—C36A	98.7 (7)	N11—C29—N12	116.2 (4)
C35A—P1—C36A	91.5 (6)	N11—C29—C30	119.8 (4)
F8A—P3—F11A	87.4 (5)	C29—C30—C31	117.6 (5)
F8A—P3—F12A	90.8 (6)	C30—C31—C32	120.3 (5)
F9A—P3—F10A	90.9 (5)	C31—C32—C33	117.9 (5)
F9A—P3—F11A	170.3 (5)	N12—C33—C32	123.8 (5)
F9A—P3—F12A	88.7 (6)	N1—C2—H2	127.00
F10A—P3—F11A	94.4 (6)	C3—C2—H2	127.00
F10A—P3—F12A	177.5 (7)	C2—C3—H3	126.00
F11A—P3—F12A	86.3 (7)	N2—C3—H3	126.00
F10—P3—F12	171.2 (5)	C4—C5—H5	121.00
F11—P3—F12	98.2 (5)	C6—C5—H5	121.00
F7—P3—F8	175.5 (6)	C7—C6—H6	120.00
F7—P3—F9	82.9 (4)	C5—C6—H6	120.00
F7—P3—F10	80.6 (5)	C6—C7—H7	121.00
F7—P3—F11	87.1 (5)	C8—C7—H7	121.00
F7—P3—F12	91.2 (5)	N3—C8—H8	118.00
F8—P3—F9	94.3 (5)	C7—C8—H8	118.00
F8—P3—F10	95.7 (6)	N2—C9—H9B	109.00
F8—P3—F11	95.2 (6)	N2—C9—H9A	109.00
F8—P3—F12	92.3 (6)	H9A—C9—H9B	108.00
F9—P3—F10	84.9 (4)	N4—C9—H9A	109.00
F9—P3—F11	166.7 (5)	N4—C9—H9B	109.00
F9—P3—F12	90.7 (4)	N4—C11—H11	126.00
F10—P3—F11	84.9 (5)	C12—C11—H11	126.00
F8A—P3—F9A	84.3 (5)	C11—C12—H12	127.00
F8A—P3—F10A	91.7 (6)	N5—C12—H12	127.00
F7A—P3—F8A	175.9 (6)	C13—C14—H14	121.00
F7A—P3—F9A	92.5 (6)	C15—C14—H14	121.00
F7A—P3—F10A	91.0 (6)	C16—C15—H15	120.00
F7A—P3—F11A	95.5 (6)	C14—C15—H15	120.00
F7A—P3—F12A	86.5 (6)	C15—C16—H16	121.00
F1—P2—F2	179.19 (18)	C17—C16—H16	121.00
F1—P2—F3	90.56 (15)	N6—C17—H17	119.00
F2—P2—F6	90.30 (19)	C16—C17—H17	118.00
F3—P2—F4	89.27 (16)	C20—C19—H19	127.00
F3—P2—F5	179.93 (17)	N7—C19—H19	127.00
F3—P2—F6	91.22 (16)	N8—C20—H20	125.00
F4—P2—F5	90.69 (17)	C19—C20—H20	125.00
F4—P2—F6	179.46 (18)	C21—C22—H22	121.00
F5—P2—F6	88.83 (17)	C23—C22—H22	121.00
F2—P2—F5	89.70 (15)	C22—C23—H23	121.00
F1—P2—F6	89.64 (18)	C24—C23—H23	121.00
F1—P2—F4	90.1 (2)	C23—C24—H24	121.00
F1—P2—F5	89.49 (15)	C25—C24—H24	121.00
F2—P2—F3	90.25 (15)	N9—C25—H25	118.00
F2—P2—F4	89.9 (2)	C24—C25—H25	118.00
C1—N1—C2	111.4 (3)	N10—C27—H27	124.00
C2—N1—C4	132.8 (3)	C28—C27—H27	124.00
C1—N1—C4	115.7 (3)	N11—C28—H28	127.00
C1—N2—C3	110.3 (3)	C27—C28—H28	127.00
C3—N2—C9	124.4 (4)	C31—C30—H30	121.00
C1—N2—C9	125.2 (3)	C29—C30—H30	121.00
C4—N3—C8	115.9 (3)	C32—C31—H31	120.00
Fe1—N3—C8	131.6 (2)	C30—C31—H31	120.00
Fe1—N3—C4	112.3 (2)	C33—C32—H32	121.00
C9—N4—C10	125.5 (3)	C31—C32—H32	121.00
C9—N4—C11	124.3 (3)	N12—C33—H33	118.00
C10—N4—C11	110.2 (3)	C32—C33—H33	118.00
C10—N5—C13	115.4 (3)	P1—C34—H34C	109.00
C12—N5—C13	134.1 (3)	H34A—C34—H34B	109.00
C10—N5—C12	110.3 (3)	P1—C34—H34A	109.00
Fe1—N6—C13	112.4 (3)	P1—C34—H34B	109.00
Fe1—N6—C17	130.8 (3)	H34A—C34—H34C	110.00
C13—N6—C17	116.7 (3)	H34B—C34—H34C	110.00
C18—N7—C19	107.5 (3)	P1—C34A—H34F	109.00
C19—N7—C21	126.8 (3)	P1—C34A—H34D	109.00
C18—N7—C21	125.7 (3)	P1—C34A—H34E	109.00
Fe1—N8—C20	120.9 (2)	H34E—C34A—H34F	110.00
Fe1—N8—C18	133.9 (2)	H34D—C34A—H34F	109.00
C18—N8—C20	105.1 (3)	H34D—C34A—H34E	110.00
C21—N9—C25	115.7 (4)	P1—C35—H35C	109.00
C26—N10—C27	104.5 (3)	P1—C35—H35B	109.00
C28—N11—C29	127.0 (4)	H35B—C35—H35C	110.00
C26—N11—C28	105.9 (3)	H35A—C35—H35B	109.00
C26—N11—C29	126.8 (4)	H35A—C35—H35C	109.00
C29—N12—C33	116.4 (4)	P1—C35—H35A	109.00
N1—C1—N2	104.6 (3)	P1—C35A—H35D	109.00
Fe1—C1—N1	119.8 (3)	P1—C35A—H35E	109.00
Fe1—C1—N2	135.6 (3)	P1—C35A—H35F	109.00
N1—C2—C3	105.7 (3)	H35D—C35A—H35E	109.00
N2—C3—C2	107.9 (4)	H35E—C35A—H35F	109.00
N1—C4—N3	112.2 (3)	H35D—C35A—H35F	110.00
N1—C4—C5	123.9 (3)	P1—C36—H36C	109.00
N3—C4—C5	124.0 (4)	H36A—C36—H36B	109.00
C4—C5—C6	117.7 (4)	P1—C36—H36B	109.00
C5—C6—C7	120.0 (4)	H36B—C36—H36C	110.00
C6—C7—C8	118.4 (4)	H36A—C36—H36C	109.00
N3—C8—C7	124.0 (3)	P1—C36—H36A	109.00
N2—C9—N4	111.8 (3)	H36E—C36A—H36F	110.00
Fe1—C10—N5	119.5 (3)	P1—C36A—H36D	109.00
Fe1—C10—N4	135.2 (3)	P1—C36A—H36E	109.00
N4—C10—N5	105.3 (3)	P1—C36A—H36F	109.00
N4—C11—C12	107.9 (4)	H36D—C36A—H36E	109.00
N5—C12—C11	106.4 (4)	H36D—C36A—H36F	110.00
N3—Fe1—P1—C34	−55.4 (4)	C9—N4—C10—Fe1	−4.1 (6)
N6—Fe1—P1—C34	−169.4 (4)	C9—N4—C11—C12	−177.9 (4)
C1—Fe1—P1—C34	24.3 (4)	C13—N5—C10—Fe1	−2.9 (5)
C10—Fe1—P1—C34	110.5 (4)	C12—N5—C10—N4	−0.4 (4)
N3—Fe1—P1—C35	−168.5 (3)	C13—N5—C10—N4	175.3 (3)
N6—Fe1—P1—C35	77.4 (3)	C12—N5—C10—Fe1	−178.6 (3)
C1—Fe1—P1—C35	−88.9 (3)	C13—N5—C12—C11	−174.1 (4)
C10—Fe1—P1—C35	−2.7 (3)	C10—N5—C13—N6	1.9 (5)
N3—Fe1—P1—C36	70.8 (5)	C10—N5—C12—C11	0.5 (5)
N6—Fe1—P1—C36	−43.3 (5)	C12—N5—C13—C14	−2.0 (7)
C1—Fe1—P1—C36	150.4 (5)	C12—N5—C13—N6	176.3 (4)
C10—Fe1—P1—C36	−123.4 (5)	C10—N5—C13—C14	−176.3 (4)
N8—Fe1—C10—N5	−82.7 (3)	Fe1—N6—C13—C14	177.9 (3)
C1—Fe1—C10—N5	−176.5 (3)	C17—N6—C13—N5	−179.9 (3)
C1—Fe1—N8—C20	−127.3 (3)	C17—N6—C13—C14	−1.6 (6)
P1—Fe1—N3—C4	97.4 (2)	Fe1—N6—C13—N5	−0.4 (4)
N6—Fe1—N3—C4	−173.1 (2)	C13—N6—C17—C16	0.8 (6)
N8—Fe1—N3—C4	−89.5 (2)	Fe1—N6—C17—C16	−178.6 (3)
C1—Fe1—N3—C4	5.6 (3)	C18—N7—C21—N9	−120.2 (4)
P1—Fe1—N3—C8	−87.6 (3)	C18—N7—C21—C22	60.7 (5)
N6—Fe1—N3—C8	1.9 (4)	C18—N7—C19—C20	−1.2 (4)
N8—Fe1—N3—C8	85.5 (3)	C19—N7—C18—C26	−178.0 (3)
C1—Fe1—N3—C8	−179.5 (3)	C21—N7—C19—C20	179.0 (3)
N3—Fe1—N8—C18	129.7 (3)	C19—N7—C21—N9	59.6 (5)
N6—Fe1—N8—C18	−115.8 (3)	C19—N7—C21—C22	−119.5 (4)
C1—Fe1—N8—C18	50.4 (3)	C19—N7—C18—N8	0.6 (4)
C10—Fe1—N8—C18	−36.2 (3)	C21—N7—C18—N8	−179.6 (3)
N3—Fe1—N8—C20	−48.1 (3)	C21—N7—C18—C26	1.9 (5)
N6—Fe1—N8—C20	66.5 (3)	C20—N8—C18—C26	178.6 (3)
N6—Fe1—C10—N5	2.0 (3)	Fe1—N8—C18—C26	0.6 (6)
P1—Fe1—C1—N2	87.4 (4)	Fe1—N8—C20—C19	177.4 (2)
N3—Fe1—C1—N2	177.0 (4)	C20—N8—C18—N7	0.2 (4)
P1—Fe1—N6—C13	−90.6 (3)	Fe1—N8—C18—N7	−177.8 (2)
N3—Fe1—N6—C13	179.7 (3)	C18—N8—C20—C19	−1.0 (4)
N8—Fe1—N6—C13	96.4 (3)	C25—N9—C21—C22	−0.8 (6)
C10—Fe1—N6—C13	−0.9 (3)	C25—N9—C21—N7	−179.9 (4)
P1—Fe1—N6—C17	88.9 (3)	C21—N9—C25—C24	−0.8 (7)
N3—Fe1—N6—C17	−0.9 (4)	C26—N10—C27—C28	−1.4 (5)
C10—Fe1—N6—C17	178.6 (4)	C27—N10—C26—N11	1.1 (4)
P1—Fe1—C10—N4	−85.8 (4)	C27—N10—C26—C18	173.3 (4)
N6—Fe1—C10—N4	−175.5 (4)	C26—N11—C29—N12	35.1 (5)
N8—Fe1—C10—N4	99.8 (4)	C28—N11—C26—N10	−0.4 (5)
C1—Fe1—C10—N4	6.0 (4)	C28—N11—C26—C18	−172.8 (4)
P1—Fe1—C10—N5	91.6 (3)	C26—N11—C28—C27	−0.5 (5)
C10—Fe1—C1—N1	177.1 (3)	C29—N11—C28—C27	−174.8 (4)
C10—Fe1—N8—C20	146.0 (3)	C26—N11—C29—C30	−144.1 (5)
N8—Fe1—N6—C17	−84.1 (3)	C28—N11—C29—N12	−151.7 (4)
C10—Fe1—C1—N2	−2.1 (4)	C28—N11—C29—C30	29.1 (7)
N8—Fe1—C1—N1	80.9 (3)	C29—N11—C26—C18	1.6 (6)
N8—Fe1—C1—N2	−98.3 (4)	C29—N11—C26—N10	173.9 (4)
P1—Fe1—C1—N1	−93.4 (3)	C33—N12—C29—C30	1.0 (6)
N3—Fe1—C1—N1	−3.8 (3)	C33—N12—C29—N11	−178.2 (3)
C4—N1—C1—Fe1	1.4 (5)	C29—N12—C33—C32	−1.6 (6)
C4—N1—C2—C3	179.1 (4)	N1—C2—C3—N2	−0.1 (5)
C4—N1—C1—N2	−179.2 (3)	N1—C4—C5—C6	−178.4 (4)
C2—N1—C4—C5	4.1 (7)	N3—C4—C5—C6	1.2 (6)
C1—N1—C2—C3	−0.1 (5)	C4—C5—C6—C7	0.4 (6)
C2—N1—C1—N2	0.2 (4)	C5—C6—C7—C8	−1.4 (6)
C1—N1—C4—C5	−176.8 (4)	C6—C7—C8—N3	0.9 (6)
C2—N1—C4—N3	−175.6 (4)	N4—C11—C12—N5	−0.4 (5)
C2—N1—C1—Fe1	−179.3 (3)	N5—C13—C14—C15	179.4 (4)
C1—N1—C4—N3	3.5 (5)	N6—C13—C14—C15	1.4 (7)
C3—N2—C1—N1	−0.2 (4)	C13—C14—C15—C16	−0.2 (7)
C3—N2—C1—Fe1	179.1 (3)	C14—C15—C16—C17	−0.6 (7)
C9—N2—C3—C2	−176.9 (4)	C15—C16—C17—N6	0.3 (7)
C3—N2—C9—N4	−176.5 (4)	N7—C18—C26—N10	−103.1 (4)
C9—N2—C1—N1	176.8 (3)	N7—C18—C26—N11	68.2 (5)
C1—N2—C3—C2	0.2 (5)	N8—C18—C26—N10	78.6 (5)
C1—N2—C9—N4	6.9 (5)	N8—C18—C26—N11	−110.0 (4)
C9—N2—C1—Fe1	−3.9 (6)	N7—C19—C20—N8	1.3 (4)
Fe1—N3—C4—N1	−6.2 (4)	N7—C21—C22—C23	−180.0 (4)
Fe1—N3—C4—C5	174.2 (3)	N9—C21—C22—C23	1.0 (6)
C8—N3—C4—N1	178.0 (3)	C21—C22—C23—C24	0.4 (6)
C8—N3—C4—C5	−1.7 (5)	C22—C23—C24—C25	−1.8 (7)
Fe1—N3—C8—C7	−174.3 (3)	C23—C24—C25—N9	2.1 (8)
C4—N3—C8—C7	0.6 (5)	N10—C27—C28—N11	1.2 (6)
C10—N4—C9—N2	−3.4 (5)	N11—C29—C30—C31	179.4 (5)
C9—N4—C10—N5	178.2 (3)	N12—C29—C30—C31	0.3 (8)
C11—N4—C10—Fe1	177.9 (3)	C29—C30—C31—C32	−1.0 (9)
C11—N4—C10—N5	0.2 (4)	C30—C31—C32—C33	0.5 (9)
C10—N4—C11—C12	0.1 (5)	C31—C32—C33—N12	0.8 (8)
C11—N4—C9—N2	174.4 (4)