(η⁵-Cyclo­penta­dien­yl)[(1,2,3,4,4a,10a-η)-1-methyl­thia­nthrene]iron(II) hexa­fluoridophosphate acetone 0.33-solvate

The title complex salt, [Fe(C₅H₅)(C₁₃H₁₀S₂)]PF₆·0.33C₃H₆O, obtained from an acetone–diethyl ether–dichloro­methane mixture at 280 (2) K, has three cationic mol­ecules (A–C), three hexa­fluoridophosphate counter-anions and one acetone solvent mol­ecule in the asymmetric unit. Two of the three cations contain FeCp (Cp is cyclo­penta­dienyl) inside the fold of the heterocycle. The dihedral angles between the planes of the external (complexed and uncomplexed) benzene rings in the thia­nthrene mol­ecule are 146.5 (2)° for FeCp-out-of-fold mol­ecule A, and 139.0 (3) and 142.5 (2)° for the two FeCp-in-fold mol­ecules B and C, respectively. The complexed Cp and benzene rings in each mol­ecule are almost parallel, with a dihedral angle between the planes of 0.2 (5)° for molecule A, 2.8 (5)° for B, and 2.19 (4) and 6.86 (6)° for the disordered Cp ring in C.

S1. Comment

The title compound, (I), was obtained in work extending earlier studies of the synthesis of polycyclic heteroaromatic systems in a double nucleophilic aromatic substitution reaction using 1,2-dichlorobenzene FeCp complexes (Sutherland et al., 1982, 1988). This study is a continuation of the combined influence of methyl substitution and FeCp complexation on the geometry of the thianthrene molecule. The crystal structure of (I) contains three cationic molecules (A–C) of the CpFe(1-methylthianthrene) complex, three hexafluoridophosphate counteranion molecules and one acetone molecule in the asymmetric unit. This is the first time that the formation of both FeCp-out-of-fold and FeCp-in-fold molecules of folded tricyclic heterocycles resulting from a double nucleophilic aromatic substitution reaction have been observed. Our earlier studies of the synthesis of dibenzodioxin and thianthrene FeCp complexes using the same reaction suggested that only FeCp-in-fold molecules are formed in such a reaction, as crystals of the dibenzodioxins and thianthrenes studied by X-ray crystallography have shown the presence of only FeCp-in-fold species (Simonsen et al., 1985; Abboud et al., 1990, 1991; Christie et al., 1994; Piórko et al., 1994, 1995). Conversely, phenoxathiin [-thiene?] complexes obtained in a similar reaction have shown the presence of only out-of-fold molecules in the solid state, as determined from examination of their crystal structures (Lynch et al., 1986; Sutherland et al., 1988). The only previous case in which the presence of both FeCp-out-of- and in-fold molecules was observed in the solid state came from the monodemetallation of the thianthrene bis(FeCp) dication obtained in a ligand-exchange reaction from thianthrene (Abboud et al., 1990). Thus, it appears that both in- and out-of-fold molecules may be formed in a nucleophilic aromatic substitution reaction.

The complexed Cp and benzene rings of (I) are nearly coplanar in all three molecules, with the dihedral angles 0.2 (5)° for A, 2.8 (5)° for B, and 2.19 (4)° and 6.86 (6)° for disordered Cp in C. These values are in the range observed for other thianthrene and dibenzodioxin FeCp complexes in our previous studies (see, for example, Simonsen et al., 1985; Lynch et al., 1986; Abboud et al., 1990, 1991; Christie et al., 1994; Piórko et al., 1995). The Cp–Fe–benzene ring centroid vectors are nearly collinear, with angles 179.65 (8)°, 178.42 (7)° for molecules A and B, and 178.69 (7)° ans 176.39 (7)° for disordered Cp in C. These values are typically found in the literature for FeCp–arene complexes (see, for example, Manzur et al., 2000; Fuentealba et al., 2007).

The distances from Fe ion to the Cp plane and to the complexed benzene ring plane are 1.666 (3)Å and 1.537 (3)Å in A, 1.662 (3)Å and 1.551 (3)Å in B, and 1.648 (4)Å and 1.538 (3)Å and 1.701 (4) and 1.538 (3)Å in the two disordered Cp in C. These values are close to those reported in the literature for similar complexes (see, for example, Lynch et al., 1986; Abboud et al., 1990; Piórko et al., 1995; Fuentealba et al., 2007; Manzur et al., 2007; Jenkins et al., 2008).

The Fe—C distances of the complexed benzene ring are in the range 2.073 (6)–2.121 (7) Å, with all three distances to quaternary C atoms being the longest in the two FeCp-in molecules, B and C, while in the FeCp-out molecule, A, one of these distances is among the shorter ones. In all four thianthrene molecules studied previously, the distances from the Fe atom to the quaternary C atoms of the complexed benzene ring are longer than those to the non-quaternary C atoms, with the thianthrene FeCp-out-of-fold molecule showing the narrowest range for these distances (Simonsen et al., 1985; Abboud et al., 1990; Christie et al., 1994). Overall, the average Fe—C distances of the complexed ring are 2.086, 2.095 and 2.088 Å for molecules A, B and C, respectively, and again these are within the range of reported distances for FeCp complexes (Abboud et al., 1990; Piórko et al., 1995; Fuentealba et al., 2007; Manzur et al., 2007; Jenkins et al., 2008).

The C—C distances in the complexed ring of the thianthrene show a tendency to be longer than those in the uncomplexed ring, with averages of 1.410 versus 1.382 Å for molecule A, 1.409 versus 1.380 Å for molecule B, and 1.413 versus 1.379 Å for molecule C. The S—C distances to both complexed and uncomplexed ring C atoms are quite similar and in the rather narrow range of 1.750 (7)–1.770 (6) Å. Both these observations agree with our earlier findings for thianthrene and isomeric methylthianthrene FeCp complexes (Simonsen et al., 1985; Abboud et al., 1990; Christie et al., 1994).

The dihedral angle between the two benzene rings of the thianthrene molecule has been reported to be insensitive to changes in substitution in or on one of the aromatic rings compared with thianthrene itself (for thianthrene, see: Larson et al., 1984; for other alkylthianthrenes, see: Wei, 1971; Lynch et al., 1984; Ogawa et al., 1999; Yamamoto et al., 2006). In our previous studies, we concluded that complexation of the thianthrene molecule with FeCp changes the dihedral angle between the two external benzene rings of this heterocycle. We reported that FeCp complexation of thianthrene flattens its structure and we found that the dihedral angle changes from 128.28 (7)° in thianthrene (Larson et al., 1984) to 136.3 (2)° for FeCp-out-of-fold and to 143.1 (2)° for FeCp-in-fold molecules (Abboud et al., 1990), and to 137.7 (3)° for the 2-methylthianthrene FeCp-in-fold molecule (Christie et al., 1994). We noted, however, that this angle was slightly smaller [127.4 (3)°] for the 2-methylthianthrene molecule with FeCp complexed on the unsubstituted benzene ring (Simonsen et al., 1985). In the current study, we have found that complexation flattens the heterocycle indeed, and that the dihedral angles for molecules A, B and C are 146.5 (2), 139.0 (3) and 142.5 (3)°, respectively. It is surprising that, unlike in the case of thianthrene–FeCp complexes, the molecule is flattened more by an FeCp moiety located out-of-fold. Also, the magnitude of this influence is notable, as such a value of the dihedral angle has not been reported previously.

Our results indicate that more studies are required in order to understand the joint influence of the presence and position of a methyl substituent and FeCp complexation on the geometry of a thianthrene molecule. In addition, the presence of two distinct structures in which FeCp is located inside the thianthrene fold signifies the importance of packing forces as another, yet difficult to evaluate, factor, which influences the geometry of thianthrene in FeCp complexes in crystals.

S2. Experimental

The title complex salt was obtained as a yellow–orange powder in 78% yield following the method of Sutherland et al. (1982) in a reaction of 1,2-benzenedithiol with (η⁶-2,3-dichlorotoluene)(η⁵-Cp)iron(II) hexafluoridophosphate. Analytical data: elemental analysis, calculated: C 43.57, H 3.05%; found: C 43.62, H 3.15%; ¹H NMR (300.133 MHz, acetone-d₆, δ, p.p.m.): 2.86 (s, methyl), 4.87 (s, Cp), 6.49 (t, 1H, complexed benzene ring, J = 6.2 Hz), 6.57 (d, 1H, complexed benzene ring, J = 6.2 Hz), 6.91 (d, 1H, complexed benzene ring, J = 6.2 Hz), 7.63 (m, 2H, uncomplexed benzene ring), 7.81 (m, 2H, uncomplexed benzene ring); ¹³C NMR (75.469 MHz, acetone-d₆; δ, p.p.m.): 20.4 (methyl), 79.4 (Cp), 86.4, 88.0, 88.2 (C of complexed benzene ring), 104.1, 105.2, 106.0 (quaternary C of complexed benzene ring), 130.4, 130.5, 130.7, 130.9 (C of uncomplexed benzene ring), 133.3, 134.0 (quaternary C of uncomplexed benzene ring). The crystal used for data collection was grown by slow evaporation of the solvents from a solution of the complex in an acetone–diethyl ether–dichloromethane mixture [Solvent ratio?] at 280 (2) K.

S3. Refinement

The H atoms were placed in geometrically idealized positions with C—H distances of 0.93Å (aromatic), 0.98Å (idealized CH) and 0.96Å (idealized CH₃) and were constrained to ride on the parent C atom with U_iso(H) = 1.2Ueq(C) for the aromatic and C—H protons and U_iso(H) = 1.5Ueq(C) for the idealized CH₃ protons. The carbon atoms in the disordered cyclopentadienyl rings were restrained to be regular pentagons with C—C distances of 1.42Å and were refined to a 68:32 ratio. For each of the disordered cyclopentadienyl rings carbon ellipsods were constrained to be equal in size. For all of the PF₆ groups the equatorial P—F distances were restrained to 1.55Å and the cis F—F distances were restrained to be 2.19 Å. The ellipsoids on the three PF₆ groups were restrained to be similar in size. All three PF₆ groups were found to have rotational disorder and were refined to have occupancies of 59:41 (P1), 51:49 (P2) and 50:50 (P3).

Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. A view of the cation of (I), showing the atom-labelling scheme for molecule A (Fe1). Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. A view of the cation of (I), showing the atom-labelling scheme for molecule B (Fe2). Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 3. View of the cation showing the labelling of non-H atoms of molecule C (Fe3) and disorder of Cp ring with the thermal ellipsoids shown at 50% probability levels. Hydrogen atoms are omitted for clarity.
	Fig. 4. A view of the asymmetric unit of (I), showing the positions of the three cations, A (out-of-fold FeCp), B and C, the three hexafluoridophosphate anions and the acetone molecule in the unit.

(η⁵-Cyclopentadienyl)[(1,2,3,4,4a,10a-η)-1-methylthianthrene]iron(II) hexafluoridophosphate acetone 0.33-solvate

Crystal data

[Fe(C5H5)(C13H10S2)]PF6·0.33C3H6O	Z = 2
Mr = 515.60	F(000) = 1564
Triclinic, P1	Dx = 1.682 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.5598 (10) Å	Cell parameters from 3081 reflections
b = 15.4984 (15) Å	θ = 2.3–21.3°
c = 19.4769 (19) Å	µ = 1.08 mm^−1
α = 83.508 (1)°	T = 296 K
β = 75.251 (1)°	Amorphous, brown
γ = 84.088 (1)°	0.46 × 0.32 × 0.13 mm
V = 3053.6 (5) Å^3

Data collection

Bruker APEXII CCD diffractometer	10509 independent reflections
Radiation source: sealed tube	6357 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
ϕ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −12→12
Tmin = 0.643, Tmax = 0.746	k = −18→18
20371 measured reflections	l = −19→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.180	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0782P)^2 + 3.5P] where P = (Fo^2 + 2Fc^2)/3
10509 reflections	(Δ/σ)max = 0.001
884 parameters	Δρmax = 0.93 e Å^−3
498 restraints	Δρmin = −0.77 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.9272 (6)	0.4080 (4)	0.2205 (4)	0.0402 (16)
C2	0.9698 (6)	0.3920 (5)	0.2840 (4)	0.0493 (19)
H2	0.9913	0.3314	0.3004	0.059*
C3	0.9500 (6)	0.4545 (5)	0.3325 (4)	0.0468 (18)
H3	0.9596	0.4365	0.3810	0.056*
C4	0.8890 (6)	0.5369 (5)	0.3184 (4)	0.0413 (17)
H4	0.8567	0.5752	0.3569	0.050*
C4A	0.8450 (6)	0.5548 (4)	0.2546 (4)	0.0358 (15)
C5A	0.8021 (6)	0.6830 (4)	0.1519 (4)	0.0387 (16)
C6	0.8102 (7)	0.7710 (5)	0.1269 (5)	0.056 (2)
H6	0.8009	0.8128	0.1589	0.068*
C7	0.8320 (8)	0.7956 (6)	0.0553 (5)	0.067 (2)
H7	0.8359	0.8543	0.0391	0.080*
C8	0.8480 (9)	0.7346 (6)	0.0070 (5)	0.070 (2)
H8	0.8601	0.7519	−0.0414	0.084*
C9	0.8459 (8)	0.6472 (5)	0.0311 (4)	0.058 (2)
H9	0.8616	0.6056	−0.0016	0.069*
C10A	0.8651 (6)	0.4911 (4)	0.2054 (4)	0.0397 (16)
C11	0.9415 (8)	0.3374 (5)	0.1719 (4)	0.061 (2)
H11A	0.9749	0.2840	0.1934	0.092*
H11B	1.0015	0.3533	0.1272	0.092*
H11C	0.8575	0.3298	0.1640	0.092*
C12	0.6279 (8)	0.4391 (6)	0.4005 (4)	0.062 (2)
H12	0.6269	0.4693	0.4422	0.074*
C13	0.6797 (7)	0.3546 (6)	0.3888 (5)	0.059 (2)
H13	0.7213	0.3149	0.4210	0.071*
C14	0.6613 (8)	0.3354 (6)	0.3241 (5)	0.065 (2)
H14	0.6862	0.2799	0.3027	0.078*
C15	0.5981 (7)	0.4100 (7)	0.2960 (5)	0.066 (3)
H15	0.5708	0.4160	0.2512	0.080*
C16	0.5781 (7)	0.4732 (6)	0.3436 (5)	0.062 (2)
H16	0.5347	0.5317	0.3380	0.074*
C9A	0.8210 (7)	0.6213 (4)	0.1023 (4)	0.0428 (17)
Fe1	0.77381 (8)	0.43924 (6)	0.30810 (5)	0.0351 (3)
S10	0.8013 (2)	0.50990 (12)	0.12923 (10)	0.0511 (5)
S5	0.75385 (19)	0.65572 (12)	0.24398 (10)	0.0489 (5)
C21	0.0882 (6)	0.2215 (4)	0.5073 (4)	0.0437 (17)
C22	0.0990 (7)	0.2556 (5)	0.4359 (4)	0.053 (2)
H22	0.0483	0.2303	0.4085	0.063*
C23	0.2024 (8)	0.3062 (5)	0.3978 (4)	0.055 (2)
H23	0.2192	0.3161	0.3458	0.066*
C24	0.2960 (7)	0.3251 (5)	0.4313 (4)	0.0518 (19)
H24	0.3779	0.3480	0.4025	0.062*
C24A	0.2865 (7)	0.2946 (4)	0.5032 (4)	0.0462 (18)
C25A	0.4330 (7)	0.2288 (5)	0.5980 (4)	0.0466 (18)
C26	0.5587 (8)	0.2042 (6)	0.6043 (5)	0.067 (2)
H26	0.6284	0.2344	0.5764	0.080*
C27	0.5819 (10)	0.1356 (7)	0.6516 (6)	0.085 (3)
H27	0.6665	0.1216	0.6574	0.102*
C28	0.4805 (10)	0.0871 (6)	0.6907 (6)	0.078 (3)
H28	0.4968	0.0401	0.7223	0.094*
C29	0.3550 (9)	0.1091 (5)	0.6824 (4)	0.061 (2)
H29	0.2867	0.0760	0.7077	0.073*
C29A	0.3305 (7)	0.1796 (5)	0.6369 (4)	0.0458 (18)
C30A	0.1835 (6)	0.2437 (4)	0.5414 (4)	0.0403 (16)
C31	−0.0183 (7)	0.1641 (5)	0.5451 (4)	0.055 (2)
H31A	−0.0764	0.1931	0.5835	0.082*
H31B	0.0198	0.1106	0.5639	0.082*
H31C	−0.0668	0.1518	0.5123	0.082*
C32	0.3709 (12)	0.0766 (6)	0.4729 (6)	0.082 (3)
H32	0.3736	0.0540	0.5216	0.099*
C33	0.2764 (10)	0.0622 (6)	0.4375 (8)	0.085 (3)
H33	0.2011	0.0270	0.4565	0.102*
C34	0.3113 (12)	0.1045 (7)	0.3698 (6)	0.084 (3)
H34	0.2642	0.1050	0.3324	0.101*
C35	0.4237 (11)	0.1432 (7)	0.3633 (6)	0.087 (3)
H35	0.4707	0.1773	0.3207	0.104*
C36	0.4609 (9)	0.1265 (7)	0.4263 (7)	0.081 (3)
H36	0.5388	0.1467	0.4363	0.098*
Fe2	0.27857 (9)	0.19144 (6)	0.44355 (5)	0.0396 (3)
S30	0.16657 (18)	0.20821 (14)	0.63178 (10)	0.0547 (5)
S25	0.4053 (2)	0.32401 (13)	0.54403 (12)	0.0570 (5)
C54	0.4542 (7)	0.7622 (4)	0.1444 (6)	0.065 (2)	0.683 (18)
H54	0.4454	0.8225	0.1448	0.078*	0.683 (18)
C55	0.4394 (6)	0.7007 (8)	0.2051 (4)	0.065 (2)	0.683 (18)
H55	0.4192	0.7136	0.2524	0.078*	0.683 (18)
C53	0.4608 (6)	0.6160 (5)	0.1811 (6)	0.065 (2)	0.683 (18)
H53	0.4571	0.5637	0.2099	0.078*	0.683 (18)
C52	0.4889 (6)	0.6252 (6)	0.1055 (6)	0.065 (2)	0.683 (18)
H52	0.5068	0.5800	0.0760	0.078*	0.683 (18)
C56	0.4848 (7)	0.7156 (7)	0.0828 (4)	0.065 (2)	0.683 (18)
H56	0.4996	0.7400	0.0358	0.078*	0.683 (18)
C52B	0.4778 (6)	0.6093 (4)	0.1469 (6)	0.063 (5)	0.317 (18)
H52B	0.4913	0.5490	0.1468	0.076*	0.317 (18)
C53B	0.4356 (6)	0.6470 (8)	0.2101 (4)	0.063 (5)	0.317 (18)
H53B	0.4079	0.6225	0.2568	0.076*	0.317 (18)
C54B	0.4483 (6)	0.7393 (6)	0.1806 (5)	0.063 (5)	0.317 (18)
H54B	0.4308	0.7879	0.2064	0.076*	0.317 (18)
C55B	0.4947 (6)	0.7389 (5)	0.1008 (5)	0.063 (5)	0.317 (18)
H55B	0.5163	0.7881	0.0696	0.076*	0.317 (18)
C56B	0.5007 (6)	0.6631 (8)	0.0817 (4)	0.063 (5)	0.317 (18)
H56B	0.5163	0.6464	0.0357	0.076*	0.317 (18)
C50A	0.1666 (7)	0.7604 (5)	0.1034 (4)	0.0449 (17)
C41	0.1957 (7)	0.6792 (5)	0.0725 (4)	0.053 (2)
C42	0.1888 (7)	0.6019 (5)	0.1196 (6)	0.063 (2)
H42	0.2301	0.5477	0.0996	0.076*
C43	0.1584 (7)	0.6032 (5)	0.1934 (5)	0.063 (2)
H43	0.1770	0.5504	0.2230	0.076*
C44	0.1313 (7)	0.6832 (5)	0.2232 (4)	0.054 (2)
H44	0.1313	0.6851	0.2733	0.065*
C44A	0.1327 (6)	0.7624 (5)	0.1782 (4)	0.0440 (17)
C45A	0.1930 (7)	0.9321 (5)	0.1642 (4)	0.0498 (19)
C46	0.2372 (8)	0.9960 (6)	0.1945 (6)	0.071 (3)
H46	0.2167	0.9960	0.2439	0.085*
C47	0.3102 (10)	1.0590 (6)	0.1532 (7)	0.088 (3)
H47	0.3343	1.1035	0.1744	0.106*
C48	0.3482 (11)	1.0569 (7)	0.0809 (7)	0.094 (3)
H48	0.3999	1.0992	0.0531	0.113*
C49	0.3100 (9)	0.9921 (6)	0.0489 (5)	0.076 (3)
H49	0.3375	0.9898	−0.0002	0.092*
C49A	0.2298 (7)	0.9304 (5)	0.0910 (5)	0.055 (2)
C51	0.2370 (10)	0.6739 (6)	−0.0065 (5)	0.080 (3)
H51A	0.2708	0.6154	−0.0163	0.120*
H51B	0.3041	0.7131	−0.0274	0.120*
H51C	0.1627	0.6896	−0.0265	0.120*
Fe3	0.30849 (9)	0.68399 (7)	0.14612 (6)	0.0443 (3)
S45	0.0871 (2)	0.85913 (14)	0.21993 (12)	0.0597 (6)
S50	0.1694 (2)	0.85654 (14)	0.04635 (12)	0.0629 (6)
P1	0.3736 (2)	0.34007 (14)	0.15460 (12)	0.0693 (6)
F11	0.4260 (7)	0.2721 (3)	0.0994 (3)	0.1181 (19)
F12	0.3268 (5)	0.4076 (3)	0.2106 (2)	0.133 (2)
F13A	0.2612 (8)	0.2830 (5)	0.1957 (5)	0.109 (3)	0.586 (6)
F14A	0.4610 (12)	0.2896 (6)	0.2011 (5)	0.107 (3)	0.586 (6)
F15A	0.4849 (10)	0.3981 (6)	0.1137 (5)	0.116 (3)	0.586 (6)
F16A	0.2858 (11)	0.3911 (6)	0.1084 (4)	0.112 (3)	0.586 (6)
F14B	0.5175 (3)	0.3453 (10)	0.1582 (8)	0.100 (3)	0.414 (6)
F15B	0.4042 (19)	0.4151 (3)	0.0946 (3)	0.107 (3)	0.414 (6)
F13B	0.360 (2)	0.2656 (3)	0.2156 (3)	0.107 (3)	0.414 (6)
F16B	0.2355 (7)	0.3499 (10)	0.1393 (8)	0.115 (3)	0.414 (6)
P2	0.20247 (18)	0.58365 (12)	0.42021 (10)	0.0548 (5)
F21	0.2379 (6)	0.5270 (4)	0.3562 (2)	0.1053 (18)
F22	0.1676 (4)	0.6409 (2)	0.48378 (15)	0.0903 (16)
F23A	0.1930 (15)	0.5007 (2)	0.4732 (2)	0.092 (3)	0.492 (11)
F24A	0.3505 (2)	0.5882 (10)	0.4155 (6)	0.086 (3)	0.492 (11)
F25A	0.2108 (15)	0.6673 (2)	0.3678 (2)	0.083 (3)	0.492 (11)
F26A	0.0556 (3)	0.5899 (8)	0.4189 (6)	0.082 (3)	0.492 (11)
F23B	0.3238 (10)	0.5404 (8)	0.4455 (5)	0.088 (3)	0.508 (11)
F24B	0.2795 (13)	0.6573 (5)	0.3722 (3)	0.090 (3)	0.508 (11)
F25B	0.0780 (8)	0.6241 (7)	0.3967 (5)	0.082 (3)	0.508 (11)
F26B	0.1239 (13)	0.5105 (5)	0.4680 (4)	0.102 (3)	0.508 (11)
P3	0.1131 (2)	0.90440 (12)	0.65271 (11)	0.0626 (6)
F31	0.1619 (7)	0.8322 (3)	0.6010 (3)	0.1207 (18)
F32	0.0636 (4)	0.9746 (2)	0.7061 (2)	0.1150 (17)
F33A	0.2349 (8)	0.8802 (7)	0.6837 (6)	0.087 (2)	0.504 (11)
F34A	0.1899 (13)	0.9731 (4)	0.5981 (4)	0.103 (2)	0.504 (11)
F35A	−0.0069 (8)	0.9304 (7)	0.6205 (6)	0.092 (2)	0.504 (11)
F36A	0.0369 (13)	0.8360 (4)	0.7078 (4)	0.110 (3)	0.504 (11)
F33B	0.1814 (14)	0.8499 (6)	0.7068 (4)	0.093 (2)	0.496 (11)
F34B	0.2402 (7)	0.9517 (6)	0.6205 (6)	0.096 (2)	0.496 (11)
F35B	0.0393 (12)	0.9568 (5)	0.6001 (4)	0.093 (2)	0.496 (11)
F36B	−0.0135 (7)	0.8567 (6)	0.6856 (6)	0.102 (2)	0.496 (11)
C60	0.2240 (16)	0.9463 (8)	0.8637 (6)	0.103 (4)
C61	0.0866 (14)	0.9280 (12)	0.8785 (8)	0.170 (8)
H61A	0.0562	0.9410	0.8358	0.255*
H61B	0.0352	0.9634	0.9146	0.255*
H61C	0.0780	0.8677	0.8949	0.255*
C62	0.3229 (12)	0.8804 (9)	0.8318 (7)	0.124 (4)
H62A	0.3196	0.8772	0.7834	0.187*
H62B	0.3062	0.8249	0.8583	0.187*
H62C	0.4083	0.8956	0.8327	0.187*
O1	0.2560 (17)	1.0104 (7)	0.8765 (7)	0.217 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.035 (4)	0.047 (4)	0.036 (4)	−0.002 (3)	−0.002 (3)	−0.004 (3)
C2	0.035 (4)	0.055 (5)	0.051 (5)	0.001 (3)	−0.005 (3)	0.006 (4)
C3	0.036 (4)	0.060 (5)	0.046 (5)	−0.007 (3)	−0.016 (3)	0.005 (4)
C4	0.036 (4)	0.053 (4)	0.039 (4)	−0.007 (3)	−0.011 (3)	−0.009 (3)
C4A	0.036 (4)	0.038 (4)	0.035 (4)	−0.005 (3)	−0.011 (3)	−0.006 (3)
C5A	0.042 (4)	0.034 (4)	0.041 (4)	−0.002 (3)	−0.014 (3)	0.003 (3)
C6	0.060 (5)	0.045 (5)	0.066 (6)	−0.004 (4)	−0.021 (4)	−0.002 (4)
C7	0.072 (6)	0.053 (5)	0.065 (6)	−0.004 (4)	−0.007 (5)	0.014 (5)
C8	0.084 (6)	0.072 (6)	0.045 (5)	−0.004 (5)	−0.007 (4)	0.014 (5)
C9	0.074 (6)	0.050 (5)	0.043 (5)	−0.002 (4)	−0.006 (4)	0.001 (4)
C10A	0.035 (4)	0.045 (4)	0.038 (4)	−0.003 (3)	−0.007 (3)	−0.003 (3)
C11	0.076 (6)	0.044 (5)	0.054 (5)	0.009 (4)	−0.002 (4)	−0.011 (4)
C12	0.062 (5)	0.073 (6)	0.041 (5)	−0.022 (4)	0.011 (4)	−0.002 (4)
C13	0.048 (5)	0.068 (6)	0.051 (5)	−0.010 (4)	−0.003 (4)	0.021 (4)
C14	0.054 (5)	0.054 (5)	0.083 (7)	−0.023 (4)	0.003 (5)	−0.019 (5)
C15	0.040 (4)	0.110 (8)	0.051 (5)	−0.031 (5)	−0.015 (4)	0.014 (5)
C16	0.036 (4)	0.059 (5)	0.076 (7)	0.001 (3)	0.005 (4)	0.010 (5)
C9A	0.046 (4)	0.046 (4)	0.035 (4)	−0.008 (3)	−0.011 (3)	0.006 (3)
Fe1	0.0323 (5)	0.0403 (6)	0.0323 (6)	−0.0018 (4)	−0.0076 (4)	−0.0029 (4)
S10	0.0770 (13)	0.0426 (11)	0.0396 (11)	−0.0078 (9)	−0.0233 (10)	−0.0045 (9)
S5	0.0626 (12)	0.0427 (11)	0.0419 (11)	0.0075 (8)	−0.0154 (9)	−0.0108 (9)
C21	0.036 (4)	0.043 (4)	0.051 (5)	0.002 (3)	−0.011 (3)	−0.004 (4)
C22	0.041 (4)	0.056 (5)	0.061 (6)	0.006 (3)	−0.020 (4)	−0.001 (4)
C23	0.058 (5)	0.059 (5)	0.044 (5)	0.004 (4)	−0.011 (4)	0.007 (4)
C24	0.054 (5)	0.044 (4)	0.050 (5)	−0.004 (3)	−0.002 (4)	0.005 (4)
C24A	0.045 (4)	0.035 (4)	0.056 (5)	−0.002 (3)	−0.004 (3)	−0.009 (4)
C25A	0.050 (4)	0.053 (5)	0.040 (4)	−0.009 (3)	−0.011 (3)	−0.013 (4)
C26	0.056 (5)	0.068 (6)	0.081 (7)	−0.015 (4)	−0.021 (5)	−0.003 (5)
C27	0.066 (6)	0.078 (7)	0.123 (10)	0.000 (5)	−0.045 (6)	−0.017 (7)
C28	0.090 (7)	0.061 (6)	0.095 (8)	−0.009 (5)	−0.047 (6)	0.001 (5)
C29	0.075 (6)	0.060 (5)	0.052 (5)	−0.017 (4)	−0.020 (4)	0.002 (4)
C29A	0.057 (5)	0.048 (4)	0.036 (4)	−0.007 (3)	−0.011 (3)	−0.013 (4)
C30A	0.039 (4)	0.034 (4)	0.042 (4)	0.001 (3)	0.001 (3)	−0.008 (3)
C31	0.045 (4)	0.060 (5)	0.059 (5)	−0.008 (4)	−0.009 (4)	−0.006 (4)
C32	0.108 (8)	0.055 (6)	0.068 (7)	0.040 (6)	−0.009 (7)	−0.013 (5)
C33	0.065 (6)	0.043 (5)	0.133 (11)	−0.004 (4)	0.013 (7)	−0.033 (6)
C34	0.100 (8)	0.081 (7)	0.081 (8)	0.029 (6)	−0.037 (7)	−0.050 (6)
C35	0.084 (7)	0.079 (7)	0.075 (8)	0.002 (6)	0.026 (6)	−0.028 (6)
C36	0.044 (5)	0.085 (7)	0.114 (10)	0.025 (5)	−0.015 (6)	−0.041 (7)
Fe2	0.0392 (5)	0.0393 (6)	0.0370 (6)	0.0017 (4)	−0.0045 (4)	−0.0060 (5)
S30	0.0472 (11)	0.0758 (14)	0.0366 (11)	−0.0126 (9)	0.0015 (8)	−0.0071 (10)
S25	0.0642 (13)	0.0507 (12)	0.0591 (14)	−0.0231 (9)	−0.0132 (10)	−0.0042 (10)
C54	0.042 (4)	0.087 (5)	0.068 (5)	−0.007 (3)	−0.019 (3)	−0.002 (3)
C55	0.042 (4)	0.087 (5)	0.068 (5)	−0.007 (3)	−0.019 (3)	−0.002 (3)
C53	0.042 (4)	0.087 (5)	0.068 (5)	−0.007 (3)	−0.019 (3)	−0.002 (3)
C52	0.042 (4)	0.087 (5)	0.068 (5)	−0.007 (3)	−0.019 (3)	−0.002 (3)
C56	0.042 (4)	0.087 (5)	0.068 (5)	−0.007 (3)	−0.019 (3)	−0.002 (3)
C52B	0.042 (8)	0.088 (11)	0.063 (9)	−0.003 (6)	−0.025 (6)	0.012 (7)
C53B	0.042 (8)	0.088 (11)	0.063 (9)	−0.003 (6)	−0.025 (6)	0.012 (7)
C54B	0.042 (8)	0.088 (11)	0.063 (9)	−0.003 (6)	−0.025 (6)	0.012 (7)
C55B	0.042 (8)	0.088 (11)	0.063 (9)	−0.003 (6)	−0.025 (6)	0.012 (7)
C56B	0.042 (8)	0.088 (11)	0.063 (9)	−0.003 (6)	−0.025 (6)	0.012 (7)
C50A	0.041 (4)	0.049 (4)	0.047 (5)	−0.002 (3)	−0.017 (3)	−0.001 (4)
C41	0.042 (4)	0.060 (5)	0.062 (5)	−0.005 (3)	−0.019 (4)	−0.011 (4)
C42	0.043 (4)	0.053 (5)	0.097 (8)	−0.006 (4)	−0.022 (5)	−0.009 (5)
C43	0.045 (5)	0.055 (5)	0.082 (7)	−0.011 (4)	−0.005 (4)	0.008 (5)
C44	0.037 (4)	0.066 (5)	0.049 (5)	0.000 (3)	0.001 (3)	0.004 (4)
C44A	0.036 (4)	0.048 (4)	0.044 (5)	−0.002 (3)	−0.006 (3)	0.002 (4)
C45A	0.044 (4)	0.044 (4)	0.055 (5)	0.001 (3)	−0.006 (4)	0.001 (4)
C46	0.065 (6)	0.066 (6)	0.085 (7)	0.002 (5)	−0.019 (5)	−0.028 (5)
C47	0.085 (7)	0.064 (7)	0.119 (10)	−0.020 (5)	−0.022 (7)	−0.016 (7)
C48	0.101 (8)	0.067 (7)	0.110 (10)	−0.032 (6)	−0.015 (7)	0.010 (7)
C49	0.087 (7)	0.074 (7)	0.059 (6)	−0.001 (5)	−0.010 (5)	0.007 (5)
C49A	0.053 (5)	0.047 (5)	0.059 (6)	0.006 (3)	−0.011 (4)	0.006 (4)
C51	0.098 (7)	0.090 (7)	0.063 (6)	0.002 (5)	−0.034 (5)	−0.032 (5)
Fe3	0.0330 (5)	0.0509 (6)	0.0468 (7)	−0.0005 (4)	−0.0090 (5)	0.0006 (5)
S45	0.0581 (12)	0.0592 (13)	0.0519 (13)	0.0005 (9)	0.0029 (10)	−0.0056 (10)
S50	0.0838 (15)	0.0592 (13)	0.0502 (13)	−0.0012 (11)	−0.0300 (11)	0.0036 (10)
P1	0.0776 (15)	0.0619 (14)	0.0708 (16)	−0.0020 (11)	−0.0209 (12)	−0.0127 (11)
F11	0.165 (5)	0.097 (4)	0.088 (4)	−0.011 (3)	−0.010 (4)	−0.036 (3)
F12	0.174 (5)	0.101 (4)	0.114 (4)	0.024 (4)	−0.014 (4)	−0.051 (4)
F13A	0.091 (5)	0.094 (5)	0.123 (6)	−0.012 (4)	0.004 (4)	0.011 (4)
F14A	0.112 (5)	0.107 (5)	0.106 (5)	0.010 (5)	−0.045 (4)	0.001 (4)
F15A	0.099 (5)	0.093 (5)	0.138 (6)	−0.023 (4)	0.002 (5)	0.003 (5)
F16A	0.120 (5)	0.104 (5)	0.119 (5)	−0.011 (4)	−0.053 (4)	0.024 (4)
F14B	0.091 (4)	0.111 (6)	0.105 (6)	−0.014 (5)	−0.031 (5)	−0.012 (5)
F15B	0.102 (6)	0.084 (5)	0.120 (5)	−0.003 (5)	−0.012 (5)	0.020 (4)
F13B	0.117 (6)	0.093 (5)	0.096 (5)	−0.006 (5)	−0.008 (6)	0.015 (4)
F16B	0.085 (4)	0.138 (6)	0.121 (6)	−0.026 (5)	−0.028 (5)	0.014 (5)
P2	0.0523 (11)	0.0636 (13)	0.0489 (12)	−0.0009 (9)	−0.0127 (9)	−0.0098 (10)
F21	0.127 (4)	0.108 (4)	0.086 (4)	0.009 (3)	−0.026 (3)	−0.048 (3)
F22	0.109 (4)	0.105 (4)	0.060 (3)	0.031 (3)	−0.031 (3)	−0.031 (3)
F23A	0.093 (6)	0.080 (4)	0.089 (5)	0.012 (4)	−0.014 (5)	0.014 (4)
F24A	0.055 (4)	0.112 (6)	0.086 (6)	−0.009 (4)	−0.006 (4)	−0.013 (5)
F25A	0.093 (6)	0.094 (4)	0.071 (5)	−0.028 (4)	−0.034 (4)	0.010 (4)
F26A	0.062 (4)	0.092 (6)	0.099 (6)	−0.023 (4)	−0.028 (4)	0.000 (5)
F23B	0.070 (4)	0.119 (6)	0.065 (5)	0.028 (4)	−0.016 (4)	−0.007 (5)
F24B	0.087 (5)	0.110 (5)	0.080 (5)	−0.056 (4)	−0.020 (4)	0.001 (4)
F25B	0.073 (4)	0.096 (6)	0.082 (5)	0.000 (4)	−0.036 (4)	0.006 (4)
F26B	0.084 (6)	0.090 (5)	0.109 (5)	−0.007 (4)	0.003 (5)	0.023 (4)
P3	0.0679 (13)	0.0480 (12)	0.0782 (16)	−0.0036 (9)	−0.0300 (11)	−0.0060 (10)
F31	0.150 (4)	0.103 (3)	0.125 (4)	0.034 (3)	−0.059 (3)	−0.059 (3)
F32	0.124 (4)	0.100 (3)	0.118 (4)	0.020 (3)	−0.017 (3)	−0.051 (3)
F33A	0.079 (4)	0.091 (5)	0.101 (5)	−0.008 (3)	−0.044 (3)	−0.001 (4)
F34A	0.092 (4)	0.100 (4)	0.108 (5)	−0.015 (4)	−0.021 (4)	0.031 (3)
F35A	0.085 (4)	0.079 (5)	0.122 (5)	−0.010 (3)	−0.052 (3)	0.016 (4)
F36A	0.102 (5)	0.093 (4)	0.126 (5)	−0.017 (4)	−0.030 (4)	0.043 (3)
F33B	0.101 (5)	0.085 (4)	0.098 (4)	−0.004 (4)	−0.047 (4)	0.015 (3)
F34B	0.077 (4)	0.106 (5)	0.106 (5)	−0.022 (3)	−0.025 (4)	0.010 (4)
F35B	0.092 (4)	0.080 (4)	0.110 (4)	−0.007 (4)	−0.043 (4)	0.026 (4)
F36B	0.092 (4)	0.097 (4)	0.119 (5)	−0.030 (3)	−0.039 (4)	0.029 (4)
C60	0.182 (11)	0.072 (8)	0.063 (7)	0.015 (7)	−0.058 (8)	0.003 (6)
C61	0.123 (9)	0.28 (2)	0.091 (10)	0.076 (11)	−0.038 (9)	−0.011 (11)
C62	0.115 (9)	0.148 (12)	0.108 (11)	0.021 (8)	−0.030 (8)	−0.027 (9)
O1	0.42 (2)	0.084 (7)	0.170 (12)	−0.007 (10)	−0.115 (13)	−0.019 (7)

Geometric parameters (Å, º)

C1—C2	1.409 (10)	C54—H54	0.9300
C1—C10A	1.418 (9)	C55—C53	1.4200
C1—C11	1.497 (10)	C55—Fe3	2.061 (6)
C1—Fe1	2.095 (6)	C55—H55	0.9300
C2—C3	1.393 (10)	C53—C52	1.4200
C2—Fe1	2.076 (7)	C53—Fe3	2.052 (6)
C2—H2	0.9800	C53—H53	0.9300
C3—C4	1.401 (9)	C52—C56	1.4200
C3—Fe1	2.077 (6)	C52—Fe3	2.031 (6)
C3—H3	0.9800	C52—H52	0.9300
C4—C4A	1.424 (9)	C56—Fe3	2.027 (7)
C4—Fe1	2.094 (6)	C56—H56	0.9300
C4—H4	0.9800	C52B—C53B	1.3738
C4A—C10A	1.417 (9)	C52B—C56B	1.4182
C4A—S5	1.770 (6)	C52B—Fe3	2.030 (6)
C4A—Fe1	2.078 (7)	C52B—H52B	0.9300
C5A—C9A	1.398 (9)	C53B—C54B	1.4860
C5A—C6	1.399 (9)	C53B—Fe3	2.054 (6)
C5A—S5	1.750 (7)	C53B—H53B	0.9300
C6—C7	1.370 (11)	C54B—C55B	1.5072
C6—H6	0.9300	C54B—Fe3	2.064 (6)
C7—C8	1.377 (12)	C54B—H54B	0.9300
C7—H7	0.9300	C55B—C56B	1.2623
C8—C9	1.382 (11)	C55B—Fe3	2.159 (6)
C8—H8	0.9300	C55B—H55B	0.9300
C9—C9A	1.365 (10)	C56B—Fe3	2.111 (6)
C9—H9	0.9300	C56B—H56B	0.9300
C10A—S10	1.764 (7)	C50A—C44A	1.411 (10)
C10A—Fe1	2.095 (7)	C50A—C41	1.426 (10)
C11—H11A	0.9600	C50A—S50	1.754 (7)
C11—H11B	0.9600	C50A—Fe3	2.093 (7)
C11—H11C	0.9600	C41—C42	1.420 (11)
C12—C16	1.375 (12)	C41—C51	1.500 (11)
C12—C13	1.386 (11)	C41—Fe3	2.095 (7)
C12—Fe1	2.049 (8)	C42—C43	1.393 (12)
C12—H12	0.9800	C42—Fe3	2.073 (8)
C13—C14	1.392 (12)	C42—H42	0.9800
C13—Fe1	2.046 (7)	C43—C44	1.400 (11)
C13—H13	0.9800	C43—Fe3	2.081 (8)
C14—C15	1.402 (12)	C43—H43	0.9800
C14—Fe1	2.047 (7)	C44—C44A	1.425 (10)
C14—H14	0.9800	C44—Fe3	2.080 (7)
C15—C16	1.388 (12)	C44—H44	0.9800
C15—Fe1	2.031 (7)	C44A—S45	1.752 (7)
C15—H15	0.9800	C44A—Fe3	2.105 (7)
C16—Fe1	2.039 (7)	C45A—C49A	1.382 (11)
C16—H16	0.9800	C45A—C46	1.385 (11)
C9A—S10	1.765 (7)	C45A—S45	1.753 (8)
C21—C22	1.411 (10)	C46—C47	1.362 (13)
C21—C30A	1.426 (9)	C46—H46	0.9300
C21—C31	1.495 (10)	C47—C48	1.366 (15)
C21—Fe2	2.114 (7)	C47—H47	0.9300
C22—C23	1.411 (10)	C48—C49	1.383 (13)
C22—Fe2	2.081 (7)	C48—H48	0.9300
C22—H22	0.9800	C49—C49A	1.393 (11)
C23—C24	1.385 (11)	C49—H49	0.9300
C23—Fe2	2.077 (7)	C49A—S50	1.768 (9)
C23—H23	0.9800	C51—H51A	0.9600
C24—C24A	1.408 (10)	C51—H51B	0.9600
C24—Fe2	2.080 (7)	C51—H51C	0.9600
C24—H24	0.9800	P1—F16B	1.5499 (12)
C24A—C30A	1.410 (9)	P1—F13B	1.5500 (12)
C24A—S25	1.768 (7)	P1—F15B	1.5500 (12)
C24A—Fe2	2.099 (7)	P1—F14B	1.5501 (12)
C25A—C26	1.375 (10)	P1—F14A	1.5502 (12)
C25A—C29A	1.396 (10)	P1—F13A	1.550 (3)
C25A—S25	1.756 (8)	P1—F11	1.550 (4)
C26—C27	1.370 (13)	P1—F16A	1.551 (3)
C26—H26	0.9300	P1—F15A	1.5507 (12)
C27—C28	1.383 (13)	P1—F12	1.551 (4)
C27—H27	0.9300	P2—F24B	1.5494 (12)
C28—C29	1.379 (11)	P2—F25B	1.5500 (12)
C28—H28	0.9300	P2—F23A	1.5502 (12)
C29—C29A	1.374 (10)	P2—F26A	1.5502 (12)
C29—H29	0.9300	P2—F23B	1.5502 (12)
C29A—S30	1.767 (7)	P2—F26B	1.5504 (12)
C30A—S30	1.754 (7)	P2—F22	1.551 (3)
C30A—Fe2	2.121 (7)	P2—F21	1.551 (3)
C31—H31A	0.9600	P2—F24A	1.5513 (12)
C31—H31B	0.9600	P2—F25A	1.5515 (12)
C31—H31C	0.9600	P3—F32	1.549 (3)
C32—C36	1.370 (14)	P3—F35B	1.5496 (12)
C32—C33	1.397 (14)	P3—F36A	1.5497 (12)
C32—Fe2	2.034 (8)	P3—F34B	1.5498 (12)
C32—H32	0.9800	P3—F31	1.550 (3)
C33—C34	1.382 (14)	P3—F35A	1.5503 (12)
C33—Fe2	2.023 (8)	P3—F36B	1.5504 (12)
C33—H33	0.9800	P3—F33A	1.5504 (12)
C34—C35	1.356 (14)	P3—F33B	1.5507 (12)
C34—Fe2	2.022 (9)	P3—F34A	1.5509 (12)
C34—H34	0.9800	C60—O1	1.155 (14)
C35—C36	1.371 (14)	C60—C62	1.453 (15)
C35—Fe2	2.039 (9)	C60—C61	1.456 (19)
C35—H35	0.9800	C61—H61A	0.9600
C36—Fe2	2.045 (8)	C61—H61B	0.9600
C36—H36	0.9800	C61—H61C	0.9600
C54—C55	1.4200	C62—H62A	0.9600
C54—C56	1.4200	C62—H62B	0.9600
C54—Fe3	2.047 (6)	C62—H62C	0.9600
C2—C1—C10A	118.5 (6)	C30A—S30—C29A	103.0 (3)
C2—C1—C11	120.6 (6)	C25A—S25—C24A	102.4 (3)
C10A—C1—C11	120.9 (6)	C55—C54—C56	108.0
C2—C1—Fe1	69.6 (4)	C55—C54—Fe3	70.3 (2)
C10A—C1—Fe1	70.2 (4)	C56—C54—Fe3	68.9 (2)
C11—C1—Fe1	129.8 (5)	C55—C54—H54	126.0
C3—C2—C1	121.9 (7)	C56—C54—H54	126.0
C3—C2—Fe1	70.4 (4)	Fe3—C54—H54	126.4
C1—C2—Fe1	71.0 (4)	C54—C55—C53	108.0
C3—C2—H2	118.0	C54—C55—Fe3	69.2 (3)
C1—C2—H2	118.0	C53—C55—Fe3	69.4 (2)
Fe1—C2—H2	118.0	C54—C55—H55	126.0
C2—C3—C4	120.3 (7)	C53—C55—H55	126.0
C2—C3—Fe1	70.4 (4)	Fe3—C55—H55	126.9
C4—C3—Fe1	71.0 (4)	C55—C53—C52	108.0
C2—C3—H3	119.1	C55—C53—Fe3	70.2 (2)
C4—C3—H3	119.1	C52—C53—Fe3	68.8 (3)
Fe1—C3—H3	119.1	C55—C53—H53	126.0
C3—C4—C4A	119.0 (6)	C52—C53—H53	126.0
C3—C4—Fe1	69.7 (4)	Fe3—C53—H53	126.5
C4A—C4—Fe1	69.4 (4)	C56—C52—C53	108.0
C3—C4—H4	119.5	C56—C52—Fe3	69.4 (3)
C4A—C4—H4	119.5	C53—C52—Fe3	70.4 (2)
Fe1—C4—H4	119.5	C56—C52—H52	126.0
C10A—C4A—C4	120.6 (6)	C53—C52—H52	126.0
C10A—C4A—S5	122.4 (5)	Fe3—C52—H52	125.7
C4—C4A—S5	116.9 (5)	C52—C56—C54	108.0
C10A—C4A—Fe1	70.8 (4)	C52—C56—Fe3	69.6 (2)
C4—C4A—Fe1	70.7 (4)	C54—C56—Fe3	70.3 (2)
S5—C4A—Fe1	127.3 (3)	C52—C56—H56	126.0
C9A—C5A—C6	118.6 (7)	C54—C56—H56	126.0
C9A—C5A—S5	122.7 (5)	Fe3—C56—H56	125.6
C6—C5A—S5	118.5 (6)	C53B—C52B—C56B	119.3
C7—C6—C5A	120.1 (8)	C53B—C52B—Fe3	71.3 (3)
C7—C6—H6	120.0	C56B—C52B—Fe3	73.1 (3)
C5A—C6—H6	120.0	C53B—C52B—H52B	120.3
C6—C7—C8	120.8 (8)	C56B—C52B—H52B	120.3
C6—C7—H7	119.6	Fe3—C52B—H52B	127.3
C8—C7—H7	119.6	C52B—C53B—C54B	97.9
C7—C8—C9	119.3 (8)	C52B—C53B—Fe3	69.4 (2)
C7—C8—H8	120.3	C54B—C53B—Fe3	69.2 (2)
C9—C8—H8	120.3	C52B—C53B—H53B	131.1
C9A—C9—C8	120.8 (8)	C54B—C53B—H53B	131.1
C9A—C9—H9	119.6	Fe3—C53B—H53B	122.5
C8—C9—H9	119.6	C53B—C54B—C55B	106.8
C4A—C10A—C1	119.8 (6)	C53B—C54B—Fe3	68.5 (3)
C4A—C10A—S10	120.9 (5)	C55B—C54B—Fe3	72.5 (2)
C1—C10A—S10	119.1 (5)	C53B—C54B—H54B	126.6
C4A—C10A—Fe1	69.5 (4)	C55B—C54B—H54B	126.6
C1—C10A—Fe1	70.2 (4)	Fe3—C54B—H54B	124.0
S10—C10A—Fe1	128.6 (3)	C56B—C55B—C54B	111.3
C1—C11—H11A	109.5	C56B—C55B—Fe3	70.7 (2)
C1—C11—H11B	109.5	C54B—C55B—Fe3	65.8 (2)
H11A—C11—H11B	109.5	C56B—C55B—H55B	124.3
C1—C11—H11C	109.5	C54B—C55B—H55B	124.3
H11A—C11—H11C	109.5	Fe3—C55B—H55B	131.0
H11B—C11—H11C	109.5	C55B—C56B—C52B	103.8
C16—C12—C13	108.4 (8)	C55B—C56B—Fe3	74.9 (2)
C16—C12—Fe1	69.9 (5)	C52B—C56B—Fe3	66.9 (2)
C13—C12—Fe1	70.1 (4)	C55B—C56B—H56B	128.1
C16—C12—H12	125.8	C52B—C56B—H56B	128.1
C13—C12—H12	125.8	Fe3—C56B—H56B	121.9
Fe1—C12—H12	125.8	C44A—C50A—C41	120.4 (7)
C12—C13—C14	108.4 (8)	C44A—C50A—S50	121.2 (6)
C12—C13—Fe1	70.3 (4)	C41—C50A—S50	118.3 (6)
C14—C13—Fe1	70.2 (5)	C44A—C50A—Fe3	70.8 (4)
C12—C13—H13	125.8	C41—C50A—Fe3	70.2 (4)
C14—C13—H13	125.8	S50—C50A—Fe3	133.9 (4)
Fe1—C13—H13	125.8	C42—C41—C50A	117.6 (8)
C13—C14—C15	106.9 (8)	C42—C41—C51	120.0 (8)
C13—C14—Fe1	70.1 (4)	C50A—C41—C51	122.3 (8)
C15—C14—Fe1	69.3 (5)	C42—C41—Fe3	69.2 (5)
C13—C14—H14	126.5	C50A—C41—Fe3	70.0 (4)
C15—C14—H14	126.5	C51—C41—Fe3	130.4 (6)
Fe1—C14—H14	126.5	C43—C42—C41	122.4 (8)
C16—C15—C14	108.2 (8)	C43—C42—Fe3	70.7 (5)
C16—C15—Fe1	70.4 (4)	C41—C42—Fe3	70.9 (4)
C14—C15—Fe1	70.5 (4)	C43—C42—H42	117.7
C16—C15—H15	125.9	C41—C42—H42	117.7
C14—C15—H15	125.9	Fe3—C42—H42	117.7
Fe1—C15—H15	125.9	C42—C43—C44	119.5 (8)
C12—C16—C15	108.1 (8)	C42—C43—Fe3	70.1 (5)
C12—C16—Fe1	70.7 (4)	C44—C43—Fe3	70.3 (4)
C15—C16—Fe1	69.7 (4)	C42—C43—H43	119.4
C12—C16—H16	125.9	C44—C43—H43	119.4
C15—C16—H16	125.9	Fe3—C43—H43	119.4
Fe1—C16—H16	125.9	C43—C44—C44A	120.0 (8)
C9—C9A—C5A	120.3 (7)	C43—C44—Fe3	70.4 (4)
C9—C9A—S10	117.9 (6)	C44A—C44—Fe3	71.0 (4)
C5A—C9A—S10	121.7 (5)	C43—C44—H44	119.3
C15—Fe1—C16	39.9 (3)	C44A—C44—H44	119.3
C15—Fe1—C13	66.8 (3)	Fe3—C44—H44	119.3
C16—Fe1—C13	66.5 (3)	C50A—C44A—C44	120.0 (7)
C15—Fe1—C14	40.2 (3)	C50A—C44A—S45	122.9 (5)
C16—Fe1—C14	67.1 (3)	C44—C44A—S45	117.1 (6)
C13—Fe1—C14	39.7 (3)	C50A—C44A—Fe3	69.9 (4)
C15—Fe1—C12	66.5 (4)	C44—C44A—Fe3	69.2 (4)
C16—Fe1—C12	39.3 (3)	S45—C44A—Fe3	135.6 (4)
C13—Fe1—C12	39.6 (3)	C49A—C45A—C46	118.8 (8)
C14—Fe1—C12	66.7 (3)	C49A—C45A—S45	122.5 (6)
C15—Fe1—C2	139.7 (4)	C46—C45A—S45	118.6 (7)
C16—Fe1—C2	172.1 (3)	C47—C46—C45A	121.0 (10)
C13—Fe1—C2	105.7 (3)	C47—C46—H46	119.5
C14—Fe1—C2	108.0 (3)	C45A—C46—H46	119.5
C12—Fe1—C2	133.6 (3)	C46—C47—C48	120.2 (10)
C15—Fe1—C3	171.6 (3)	C46—C47—H47	119.9
C16—Fe1—C3	139.5 (4)	C48—C47—H47	119.9
C13—Fe1—C3	104.9 (3)	C47—C48—C49	120.3 (10)
C14—Fe1—C3	132.2 (3)	C47—C48—H48	119.9
C12—Fe1—C3	108.3 (3)	C49—C48—H48	119.9
C2—Fe1—C3	39.2 (3)	C48—C49—C49A	119.3 (10)
C15—Fe1—C4A	116.6 (3)	C48—C49—H49	120.3
C16—Fe1—C4A	102.4 (3)	C49A—C49—H49	120.3
C13—Fe1—C4A	159.5 (3)	C45A—C49A—C49	120.2 (8)
C14—Fe1—C4A	153.8 (3)	C45A—C49A—S50	122.4 (6)
C12—Fe1—C4A	121.2 (3)	C49—C49A—S50	117.2 (7)
C2—Fe1—C4A	84.5 (3)	C41—C51—H51A	109.5
C3—Fe1—C4A	71.7 (3)	C41—C51—H51B	109.5
C15—Fe1—C4	146.7 (4)	H51A—C51—H51B	109.5
C16—Fe1—C4	112.0 (3)	C41—C51—H51C	109.5
C13—Fe1—C4	126.1 (3)	H51A—C51—H51C	109.5
C14—Fe1—C4	165.7 (4)	H51B—C51—H51C	109.5
C12—Fe1—C4	103.1 (3)	C56—Fe3—C52B	57.37 (13)
C2—Fe1—C4	71.1 (3)	C56—Fe3—C52	40.97 (11)
C3—Fe1—C4	39.3 (3)	C52B—Fe3—C52	22.68 (6)
C4A—Fe1—C4	39.9 (2)	C56—Fe3—C54	40.79 (12)
C15—Fe1—C1	111.5 (3)	C52B—Fe3—C54	70.56 (12)
C16—Fe1—C1	146.2 (3)	C52—Fe3—C54	68.60 (13)
C13—Fe1—C1	127.0 (3)	C56—Fe3—C53	68.56 (13)
C14—Fe1—C1	102.8 (3)	C52B—Fe3—C53	18.66 (5)
C12—Fe1—C1	166.6 (3)	C52—Fe3—C53	40.71 (10)
C2—Fe1—C1	39.5 (3)	C54—Fe3—C53	68.20 (12)
C3—Fe1—C1	71.9 (3)	C56—Fe3—C53B	76.71 (12)
C4A—Fe1—C1	72.0 (3)	C52B—Fe3—C53B	39.31 (10)
C4—Fe1—C1	85.6 (3)	C52—Fe3—C53B	59.57 (13)
C15—Fe1—C10A	102.4 (3)	C54—Fe3—C53B	60.73 (14)
C16—Fe1—C10A	116.5 (3)	C53—Fe3—C53B	21.36 (6)
C13—Fe1—C10A	160.4 (3)	C56—Fe3—C55	68.37 (13)
C14—Fe1—C10A	121.6 (3)	C52B—Fe3—C55	54.17 (12)
C12—Fe1—C10A	153.0 (3)	C52—Fe3—C55	68.31 (12)
C2—Fe1—C10A	71.2 (3)	C54—Fe3—C55	40.44 (11)
C3—Fe1—C10A	85.1 (3)	C53—Fe3—C55	40.39 (10)
C4A—Fe1—C10A	39.7 (2)	C53B—Fe3—C55	23.30 (7)
C4—Fe1—C10A	72.1 (3)	C56—Fe3—C54B	55.82 (13)
C1—Fe1—C10A	39.6 (3)	C52B—Fe3—C54B	63.60 (11)
C10A—S10—C9A	103.6 (3)	C52—Fe3—C54B	70.31 (11)
C5A—S5—C4A	102.4 (3)	C54—Fe3—C54B	20.86 (6)
C22—C21—C30A	117.2 (6)	C53—Fe3—C54B	55.00 (12)
C22—C21—C31	121.1 (7)	C53B—Fe3—C54B	42.31 (11)
C30A—C21—C31	121.7 (7)	C55—Fe3—C54B	20.10 (6)
C22—C21—Fe2	69.1 (4)	C56—Fe3—C42	123.9 (4)
C30A—C21—Fe2	70.6 (4)	C52B—Fe3—C42	104.5 (3)
C31—C21—Fe2	131.0 (5)	C52—Fe3—C42	101.0 (3)
C23—C22—C21	122.3 (7)	C54—Fe3—C42	164.5 (4)
C23—C22—Fe2	70.0 (4)	C53—Fe3—C42	111.9 (3)
C21—C22—Fe2	71.6 (4)	C53B—Fe3—C42	124.9 (4)
C23—C22—H22	117.8	C55—Fe3—C42	147.9 (4)
C21—C22—H22	117.8	C54B—Fe3—C42	166.8 (4)
Fe2—C22—H22	117.8	C56—Fe3—C44	164.1 (4)
C24—C23—C22	119.6 (7)	C52B—Fe3—C44	128.2 (4)
C24—C23—Fe2	70.7 (4)	C52—Fe3—C44	148.9 (4)
C22—C23—Fe2	70.3 (4)	C54—Fe3—C44	123.9 (4)
C24—C23—H23	119.4	C53—Fe3—C44	112.9 (3)
C22—C23—H23	119.4	C53B—Fe3—C44	99.5 (3)
Fe2—C23—H23	119.4	C55—Fe3—C44	102.0 (3)
C23—C24—C24A	119.9 (7)	C54B—Fe3—C44	111.1 (3)
C23—C24—Fe2	70.4 (4)	C42—Fe3—C44	71.0 (4)
C24A—C24—Fe2	71.0 (4)	C56—Fe3—C43	156.2 (4)
C23—C24—H24	119.4	C52B—Fe3—C43	105.4 (3)
C24A—C24—H24	119.4	C52—Fe3—C43	117.1 (4)
Fe2—C24—H24	119.4	C54—Fe3—C43	155.6 (4)
C24—C24A—C30A	120.7 (7)	C53—Fe3—C43	100.0 (3)
C24—C24A—S25	117.8 (6)	C53B—Fe3—C43	100.3 (3)
C30A—C24A—S25	121.4 (6)	C55—Fe3—C43	117.1 (4)
C24—C24A—Fe2	69.6 (4)	C54B—Fe3—C43	135.3 (4)
C30A—C24A—Fe2	71.3 (4)	C42—Fe3—C43	39.2 (3)
S25—C24A—Fe2	133.6 (4)	C44—Fe3—C43	39.3 (3)
C26—C25A—C29A	119.2 (7)	C56—Fe3—C50A	106.0 (3)
C26—C25A—S25	118.8 (6)	C52B—Fe3—C50A	157.9 (4)
C29A—C25A—S25	121.9 (6)	C52—Fe3—C50A	135.3 (4)
C27—C26—C25A	120.4 (8)	C54—Fe3—C50A	107.3 (3)
C27—C26—H26	119.8	C53—Fe3—C50A	174.5 (3)
C25A—C26—H26	119.8	C53B—Fe3—C50A	159.0 (4)
C26—C27—C28	120.6 (9)	C55—Fe3—C50A	137.7 (4)
C26—C27—H27	119.7	C54B—Fe3—C50A	121.6 (3)
C28—C27—H27	119.7	C42—Fe3—C50A	71.5 (3)
C29—C28—C27	119.3 (9)	C44—Fe3—C50A	72.1 (3)
C29—C28—H28	120.3	C43—Fe3—C50A	85.4 (3)
C27—C28—H28	120.3	C44A—S45—C45A	102.7 (4)
C29A—C29—C28	120.3 (8)	C50A—S50—C49A	102.8 (4)
C29A—C29—H29	119.8	F16B—P1—F13B	102.5 (10)
C28—C29—H29	119.8	F16B—P1—F15B	84.4 (9)
C29—C29A—C25A	120.1 (7)	F13B—P1—F15B	173.1 (11)
C29—C29A—S30	118.4 (6)	F16B—P1—F14B	168.7 (10)
C25A—C29A—S30	121.5 (6)	F13B—P1—F14B	88.8 (10)
C24A—C30A—C21	120.3 (7)	F15B—P1—F14B	84.3 (9)
C24A—C30A—S30	121.4 (6)	F14A—P1—F13A	88.0 (7)
C21—C30A—S30	118.3 (5)	F16B—P1—F11	92.6 (4)
C24A—C30A—Fe2	69.6 (4)	F13B—P1—F11	89.6 (4)
C21—C30A—Fe2	70.1 (4)	F15B—P1—F11	90.3 (4)
S30—C30A—Fe2	135.2 (4)	F14B—P1—F11	87.7 (4)
C21—C31—H31A	109.5	F14A—P1—F11	88.2 (4)
C21—C31—H31B	109.5	F13A—P1—F11	91.4 (4)
H31A—C31—H31B	109.5	F14A—P1—F16A	179.6 (2)
C21—C31—H31C	109.5	F13A—P1—F16A	92.1 (7)
H31A—C31—H31C	109.5	F11—P1—F16A	92.3 (4)
H31B—C31—H31C	109.5	F14A—P1—F15A	92.4 (7)
C36—C32—C33	107.3 (10)	F13A—P1—F15A	179.3 (4)
C36—C32—Fe2	70.8 (5)	F11—P1—F15A	89.2 (4)
C33—C32—Fe2	69.4 (5)	F16A—P1—F15A	87.5 (7)
C36—C32—H32	126.3	F16B—P1—F12	89.83 (13)
C33—C32—H32	126.3	F13B—P1—F12	89.79 (13)
Fe2—C32—H32	126.3	F15B—P1—F12	89.98 (13)
C34—C33—C32	107.2 (9)	F14B—P1—F12	89.92 (13)
C34—C33—Fe2	70.0 (5)	F14A—P1—F12	89.85 (13)
C32—C33—Fe2	70.3 (5)	F13A—P1—F12	89.88 (13)
C34—C33—H33	126.4	F11—P1—F12	177.6 (4)
C32—C33—H33	126.4	F16A—P1—F12	89.73 (13)
Fe2—C33—H33	126.4	F15A—P1—F12	89.58 (13)
C35—C34—C33	108.4 (10)	F24B—P2—F25B	88.4 (6)
C35—C34—Fe2	71.2 (6)	F23A—P2—F26A	94.4 (7)
C33—C34—Fe2	70.1 (5)	F24B—P2—F23B	93.8 (7)
C35—C34—H34	125.8	F25B—P2—F23B	177.8 (7)
C33—C34—H34	125.8	F24B—P2—F26B	179.3 (7)
Fe2—C34—H34	125.8	F25B—P2—F26B	90.9 (7)
C34—C35—C36	108.6 (10)	F23B—P2—F26B	86.9 (7)
C34—C35—Fe2	69.8 (5)	F24B—P2—F22	90.06 (13)
C36—C35—Fe2	70.6 (5)	F25B—P2—F22	89.98 (13)
C34—C35—H35	125.7	F23A—P2—F22	89.81 (13)
C36—C35—H35	125.7	F26A—P2—F22	89.89 (13)
Fe2—C35—H35	125.7	F23B—P2—F22	90.01 (13)
C32—C36—C35	108.4 (10)	F26B—P2—F22	89.87 (13)
C32—C36—Fe2	70.0 (5)	F24B—P2—F21	89.4 (3)
C35—C36—Fe2	70.1 (5)	F25B—P2—F21	90.0 (3)
C32—C36—H36	125.8	F23A—P2—F21	90.6 (3)
C35—C36—H36	125.8	F26A—P2—F21	90.3 (3)
Fe2—C36—H36	125.8	F23B—P2—F21	90.0 (3)
C34—Fe2—C33	39.9 (4)	F26B—P2—F21	90.6 (3)
C34—Fe2—C32	66.9 (4)	F22—P2—F21	179.5 (3)
C33—Fe2—C32	40.3 (4)	F23A—P2—F24A	92.7 (7)
C34—Fe2—C35	39.0 (4)	F26A—P2—F24A	172.9 (7)
C33—Fe2—C35	66.3 (4)	F22—P2—F24A	89.60 (13)
C32—Fe2—C35	66.2 (4)	F21—P2—F24A	90.2 (3)
C34—Fe2—C36	66.0 (4)	F23A—P2—F25A	179.3 (4)
C33—Fe2—C36	66.5 (4)	F26A—P2—F25A	85.3 (6)
C32—Fe2—C36	39.3 (4)	F22—P2—F25A	89.60 (13)
C35—Fe2—C36	39.2 (4)	F21—P2—F25A	90.0 (3)
C34—Fe2—C23	106.0 (4)	F24A—P2—F25A	87.6 (7)
C33—Fe2—C23	136.9 (5)	F32—P3—F35B	90.13 (13)
C32—Fe2—C23	171.1 (4)	F32—P3—F36A	90.01 (13)
C35—Fe2—C23	104.9 (4)	F32—P3—F34B	89.95 (13)
C36—Fe2—C23	133.7 (4)	F35B—P3—F34B	92.9 (7)
C34—Fe2—C24	130.4 (5)	F32—P3—F31	178.4 (3)
C33—Fe2—C24	170.2 (4)	F35B—P3—F31	91.0 (3)
C32—Fe2—C24	141.7 (5)	F36A—P3—F31	88.5 (4)
C35—Fe2—C24	104.9 (4)	F34B—P3—F31	91.0 (4)
C36—Fe2—C24	109.8 (4)	F32—P3—F35A	89.90 (13)
C23—Fe2—C24	38.9 (3)	F36A—P3—F35A	91.6 (7)
C34—Fe2—C22	102.9 (4)	F31—P3—F35A	90.7 (3)
C33—Fe2—C22	110.3 (4)	F32—P3—F36B	89.95 (13)
C32—Fe2—C22	145.2 (5)	F35B—P3—F36B	87.7 (7)
C35—Fe2—C22	127.5 (5)	F34B—P3—F36B	179.4 (7)
C36—Fe2—C22	166.7 (4)	F31—P3—F36B	89.1 (4)
C23—Fe2—C22	39.7 (3)	F32—P3—F33A	89.96 (13)
C24—Fe2—C22	71.0 (3)	F36A—P3—F33A	89.7 (7)
C34—Fe2—C24A	165.7 (5)	F31—P3—F33A	89.5 (3)
C33—Fe2—C24A	149.4 (5)	F35A—P3—F33A	178.6 (7)
C32—Fe2—C24A	114.7 (4)	F32—P3—F33B	89.88 (13)
C35—Fe2—C24A	127.3 (4)	F35B—P3—F33B	177.5 (7)
C36—Fe2—C24A	105.7 (4)	F34B—P3—F33B	89.6 (7)
C23—Fe2—C24A	70.7 (3)	F31—P3—F33B	88.9 (3)
C24—Fe2—C24A	39.4 (3)	F36B—P3—F33B	89.8 (7)
C22—Fe2—C24A	83.5 (3)	F32—P3—F34A	89.71 (13)
C34—Fe2—C21	121.5 (4)	F36A—P3—F34A	179.6 (6)
C33—Fe2—C21	101.6 (3)	F31—P3—F34A	91.7 (4)
C32—Fe2—C21	115.8 (4)	F35A—P3—F34A	88.7 (7)
C35—Fe2—C21	159.8 (4)	F33A—P3—F34A	89.9 (7)
C36—Fe2—C21	152.5 (4)	O1—C60—C62	119.6 (17)
C23—Fe2—C21	72.3 (3)	O1—C60—C61	122.4 (16)
C24—Fe2—C21	85.6 (3)	C62—C60—C61	118.0 (13)
C22—Fe2—C21	39.3 (3)	C60—C61—H61A	109.5
C24A—Fe2—C21	71.5 (3)	C60—C61—H61B	109.5
C34—Fe2—C30A	155.2 (5)	H61A—C61—H61B	109.5
C33—Fe2—C30A	118.4 (4)	C60—C61—H61C	109.5
C32—Fe2—C30A	104.3 (3)	H61A—C61—H61C	109.5
C35—Fe2—C30A	160.5 (4)	H61B—C61—H61C	109.5
C36—Fe2—C30A	122.8 (4)	C60—C62—H62A	109.5
C23—Fe2—C30A	84.3 (3)	C60—C62—H62B	109.5
C24—Fe2—C30A	71.3 (3)	H62A—C62—H62B	109.5
C22—Fe2—C30A	70.4 (3)	C60—C62—H62C	109.5
C24A—Fe2—C30A	39.0 (3)	H62A—C62—H62C	109.5
C21—Fe2—C30A	39.4 (3)	H62B—C62—H62C	109.5