The Knoevenagel product of indolin-2-one and ferrocene-1,1′-di­carb­alde­hyde

Indolin-2-one (oxindole), (I), undergoes a Knoevenagel con­densation with ferrocene-1,1′-dicarb­aldehyde, (II), to afford the title complex 3,3′-[(E,E)-ferrocene-1,1′-diyl­di­methyl­idyne]diindolin-2-one dichloro­methane disolvate, [Fe(C₂₈H₂₀N₂O₂)]·2CH₂Cl₂, (IV). The structure of (IV) contains two ferrocene complex molecules in the asymmetric unit and displays, as expected, inter­molecular hydrogen bonding (N—H...O=C) between the indolin-2-one units. Inter­molecular π–π stacking inter­actions are also observed.

S1. Comment

The chemistry of ferrocenes continues to flourish (van Staveren & Metzler-Nolte, 2004; Ren, 2008; Diallo et al., 2009, and references therein) and spans a plethora of disciplines, including medicinal chemistry (Dubar et al., 2008; Auzias et al., 2009; Higgins & Gellett, 2009), catalysis (Togni & Hayashi, 1995), novel materials (Shoji et al., 2009), sensors (Oton et al., 2006; Qing et al., 2009), supramolecular chemistry (Tan et al., 2008) and the design of extended molecular architectures, which often exploit intra- or intermolecular hydrogen bonding (Stepnicka et al., 2008; Hirao, 2009, and references therein; Lataifeh et al., 2009). We and others have recently published the synthesis of the isomeric ferrocenyl oxindoles, (E)- and (Z)-(III), which are readily separated and have excellent anticancer properties (see scheme). We have shown that (E)- and (Z)-(III) display intermolecular hydrogen bonding in the solid state of the type NH···O═C (Silva et al., 2008; Spencer et al., 2009).

To extend the hydrogen-bond capability in related systems, we have now reacted (I) with ferrocene-1,1'-dicarbaldehyde, (II), with a view to synthesizing 1,1'-ferrocenyl oxindoles (see scheme; Connell et al., 2009). Analysis of the reaction mixture by ¹H NMR spectroscopy revealed a complex spectroscopic pattern, indicating fluxionality or a mixture of isomers (see Experimental). Single crystals suitable for X-ray crystallographic analysis were obtained from solution in dichloromethane–hexane and the structure of the remarkable title complex, (IV), was determined (Figs. 1 and 2). Analysis of the single crystals by ¹H NMR spectroscopy gave a similar complex spectrum to that of the reaction mixture and thin-layer chromatographic analysis revealed one spot, distinct from either the starting aldehyde or oxindole.

The crystal structure of (IV) contains two crystallographically independent ferrocene complexes with two molecules of dichloromethane per molecule (Fig. 1). Of interest, three of a set of seven substituted 3-methylidene-indolin-2-ones (Spencer et al., 2010) and one of the two isomeric ferrocenyl oxindoles (Spencer et al., 2009) previously reported by us also have Z' > 1. The geometry of both crystallographically independent ferrocene species in (IV) compares closely with the ferrocenyl oxindoles and substituted oxindoles previously reported by us and others (Silva et al., 2008; Spencer et al., 2009, 2010) and with fragments found in a search of the Cambridge Structural Database (CSD, Version 5.32; Allen, 2002). All four oxindole units in (IV) exist as the E isomers, with the average of the four bond angles C11/C111—C12/C112—C13/C113 and C20/C120—C21/C121—C22/C122 being 118.8 (5)°. This is in excellent agreement with the equivalent bond angles in previously reported E isomers [averages of 118.5 (6)° from Spencer et al. (2009) and 118.9 (2)° from Spencer et al. (2010)].

While the bond lengths and angles in the two crystallographically independent ferrocene complexes of (IV) are very similar, differences are found in the interplanar distances and angles between the two oxindole units of each complex. The perpendicular separation between the mean plane through the oxindole unit O1/N1/C12–C19 and the centroid of the oxindole unit O2/N2/C21–C28 is 3.0 Å, and the angle between the two planes is 4.2 (1)°. The equivalent separation in the other complex, between the mean plane through O101/N101/C112–C119 and the centroid of O102/N102/C121–C128, is a little longer at 3.2 Å and the angle between the planes is much larger at 15.2 (1)°. The crystallographically independent molecules also show differences in the angles between the planes of the oxindole units and the cyclopentadienyl units to which they are bonded. The angle between the mean plane through the oxindole unit O1/N1/C12–C19 and that of the C1–C5 ring is 32.2 (2)°, and that between O2/N2/C21–C28 and C6–C10 is 30.2 (2)°. By contrast, the equivalent angles in the other complex are much smaller, with the angle between O101/N101/C112–C119 and C101–C105 being 22.3 (2)° and that between O102/N102/C121–C128 and C106–C110 being 19.5 (2)°.

In common with all the previously reported oxindole-based structures (Spencer et al., 2009, 2010), molecular dimers are formed through intermolecular N—H···O═C hydrogen bonding. In the case of (IV), the crystallographically independent molecules form molecular dimers through intermolecular N—H···O═C hydrogen bonding between two pairs of adjacent oxindole units (Figs. 1 and 2; Table 1). The hydrogen-bonding motif leading to the formation of the molecular dimers can be described as an R²₂(8) ring (Etter et al., 1990). The dimers are packed into double columns along the (100) direction through π–π stacking interactions (Hunter & Sanders, 1990) between the oxindole units N1/O1/C12–C19 and N102/O102/C121–C128, with an interplanar separation of approximately 3.3 Å (Fig. 2).

One of the dichloromethane molecules, Cl51—C501—Cl52, forms a short C—H···π(arene) interaction with the C123–C128 phenyl ring (Mocilac et al., 2010) (Fig. 3 and Table 2). In addition, three of the four dichloromethane molecules form some kind of weak C—H···Cl or C—H···O interaction with the ferrocene residues (Table 2).

In conclusion, the condensation of ferrocene-1,1'-dicarbaldehyde, (II), with oxindole (I) affords a 1,1'-disubstituted ferrocene, (IV), which displays intermolecular hydrogen bonding (NH···O═C) between two adjacent ferrocenes and four oxindole units. The possibility of engineering further extended hydrogen-bonded networks is currently under investigation in our laboratory.

Related literature

For related literature, see: Allen (2002); Auzias et al. (2009); Connell et al. (2009); Diallo et al. (2009); Dubar et al. (2008); Etter et al. (1990); Higgins & Gellett (2009); Hirao (2009); Hunter & Sanders (1990); Lataifeh et al. (2009); Mocilac et al. (2010); Oton et al. (2006); Qing et al. (2009); Ren (2008); Shoji et al. (2009); Silva et al. (2008); Spencer et al. (2009, 2010); Staveren & Metzler-Nolte (2004); Stepnicka et al. (2008); Tan et al. (2008); Togni & Hayashi (1995).

S2. Experimental

All experiments were conducted in air using reagent-grade solvents, and all chemicals were from commercial sources and used without further purification. CHN elemental analysis was performed on a CE Instruments Eager 300 apparatus. Crystals of (IV) of sufficient quality for X-ray diffraction analysis were obtained by the diffusion of hexane into a CH₂Cl₂ solution.

The synthesis and purification procedure for (IV) were carried out as follows. Oxindole (I) (?mg, ?mmol) and ferrocene-1,1'-dicarbaldehyde, (II) (?mg, ?mmol), were combined in ethanol (10 ml) and piperidine (3 drops), and heated for 3 h at 353 K. After cooling, the reaction mixture was concentrated in vacuo. The resulting residue was dissolved in ethyl acetate (20 ml), washed with brine solution (10 ml) and then dried (MgSO₄). Removal of the MgSO₄ followed by concentration of the solvent afforded an oil, which was taken up in CH₂Cl₂ (5 ml), and a dark-brown precipitate formed upon addition of hexane (20 ml). The precipitate, (IV), was collected by filtration and dried in vacuo. Analysis, found: C 68.48; H 4.39, N 6.02%; C₂₈H₂₀FeN₂O₂.0.25CH₂Cl₂ requires: C 68.75, H 4.19, N 5.68%. HRMS: m/z calculated for C₂₈H₂₀FeN₂O₂.0.25CH₂Cl₂ ([M+Na for ⁵⁶Fe]⁺): 493.0815; found: 493.0815. While the empirical formula was found to contain only 0.25 molecules of CH₂Cl₂ per ferrocene complex by elemental analysis and HRMS, the crystal structure was found to contain two molecules of dichloromethane per ferrocene unit. NMR spectra were measured on a JEOL EX270 spectrometer at 270 MHz (1H). ¹H NMR (probable mixture of isomers; δ, p.p.m.): 10.49 (1H, m), 8.19 (1H, m), 7.80 (1H, m), 7.38–6.68 (5H, m), 5.39 (3H, m), 4.96 (2H, m), 4.60 (1H, m),4.56 (6H, m).

S3. Refinement

All H atoms were added at calculated positions and refined using a riding model, with C—H = 0.95 for aromatic H or 0.99 Å for methylene H, and N—H = 0.88 Å, with U_iso(H) = 1.2U_eq(C,N).

The R factor is rather high, at 0.085. It is thought that this may be the result of the long unit-cell axis (c is nearly 50 Å) and the low intensity of the diffraction data, especially at higher 2θ angles. In an effort to deal with these issues, this was the second data set collected on this compound. The data were collected with a molybdenum rotating-anode X-ray source that is approximately ten times more intense than a normal laboratory X-ray source, and the crystal-to-detector distance used was 75 mm, to ensure separation of the reflections. This longer distance obviously led to even lower intensity at the detector. There was no access to a copper X-ray source. To ensure the maximum possible intensity, the data collection was completed in approximately 17 h. The data reduction was carried out carefully to maximize the quality of the data set, but the low intensity of the diffraction at higher angles frustrated these efforts to some degree, leading to the rather high agreement statistics.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: WinGX (Farrugia, 1999), Mercury (Version 2.4; Macrae et al., 2008) and PARST95 (Nardelli, 1995).

Figures

	Fig. 1. The molecular structure of (IV), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dichloromethane molecules have been omitted for clarity. Dashed lines indicate hydrogen bonds.
	Fig. 2. The packing of the hydrogen-bonded dimers (dashed lines) in (IV). Shaded areas indicate the least-squares planes involved in π–π stacking interactions. Dichloromethane molecules have been omitted for clarity and only those H atoms involved in hydrogen bonding are shown. [Symmetry codes: (i) 1 + x, y, z; (ii) 2 + x, y, z.]
	Fig. 3. Illustration of the C—H···π(arene) interaction between the dichloromethane group Cl51—C501—Cl52 and the C123–C128 phenyl ring. The other three dichloromethane molecules and most H atoms have been omitted for clarity. Dashed lines indicate hydrogen bonds.

3,3'-[(E,E)-ferrocene-1,1'-diyldimethylidyne]diindolin-2-one dichloromethane disolvate

Crystal data

[Fe(C28H20N2O2)]·2CH2Cl2	F(000) = 2624
Mr = 642.16	Dx = 1.544 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 95670 reflections
a = 7.8609 (2) Å	θ = 2.9–27.5°
b = 14.1905 (4) Å	µ = 0.97 mm^−1
c = 49.5413 (12) Å	T = 120 K
β = 90.099 (1)°	Lath, red
V = 5526.3 (2) Å^3	0.17 × 0.04 × 0.03 mm
Z = 8

Data collection

Bruker Nonius APEX II CCD camera on κ-goniostat diffractometer	9612 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	7846 reflections with I > 2σ(I)
10cm confocal mirrors monochromator	Rint = 0.063
Detector resolution: 4096x4096pixels/62x62mm pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −16→16
Tmin = 0.853, Tmax = 0.972	l = −58→58
54405 measured reflections

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)] = 0.085	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.173	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + 47.692P] where P = (Fo^2 + 2Fc^2)/3
9612 reflections	(Δ/σ)max < 0.001
703 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

Experimental. SADABS was used to perform the absorption correction. Estimated minimum and maximum transmission from SADABS: 0.6446 and 0.7456. The given Tmin and Tmax were generated using the SHELX SIZE command. NMR spectra were measured on a JEOL EX270 spectrometer at 270 MHz (1H). 1H NMR (probable mixture of isomers) 10.49 (1H, m), 8.19 (1H,m), 7.80 (1H, m), 7.38–6.68 (5H, m), 5.39 (3H, m), 4.96 (2H, m), 4.60 (1H, m),4.56 (6H, m). HRMS: m/z calculated for C₂₈H₂₀FeN₂O₂.0.25CH₂Cl₂ ([M+Na for ⁵⁶Fe]⁺): 493.0815; found: 493.0815.

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(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
C1	−0.5988 (8)	0.4197 (4)	0.08115 (12)	0.0233 (14)
C2	−0.6071 (8)	0.5072 (5)	0.09587 (13)	0.0275 (15)
H2	−0.5666	0.5178	0.1137	0.033*
C3	−0.6862 (8)	0.5745 (5)	0.07901 (13)	0.0323 (16)
H3	−0.7101	0.6380	0.0838	0.039*
C4	−0.7240 (8)	0.5329 (5)	0.05401 (14)	0.0325 (16)
H4	−0.7781	0.5631	0.0392	0.039*
C5	−0.6675 (7)	0.4378 (5)	0.05466 (13)	0.0245 (14)
H5	−0.6738	0.3939	0.0402	0.029*
C6	−0.2115 (8)	0.5003 (5)	0.06288 (13)	0.0245 (14)
C7	−0.2498 (8)	0.5954 (5)	0.07069 (14)	0.0307 (15)
H7	−0.2240	0.6231	0.0877	0.037*
C8	−0.3324 (9)	0.6411 (5)	0.04894 (14)	0.0342 (17)
H8	−0.3694	0.7048	0.0487	0.041*
C9	−0.3502 (8)	0.5750 (5)	0.02754 (14)	0.0328 (16)
H9	−0.4023	0.5866	0.0105	0.039*
C10	−0.2764 (8)	0.4883 (5)	0.03610 (13)	0.0292 (15)
H10	−0.2710	0.4320	0.0258	0.035*
C11	−0.5185 (8)	0.3302 (5)	0.08846 (13)	0.0263 (14)
H11	−0.4730	0.2954	0.0738	0.032*
C12	−0.4996 (7)	0.2899 (4)	0.11263 (12)	0.0211 (13)
C13	−0.3977 (8)	0.2006 (5)	0.11450 (13)	0.0252 (14)
C14	−0.4774 (7)	0.2393 (4)	0.15674 (12)	0.0222 (13)
C15	−0.5502 (8)	0.3095 (4)	0.14043 (13)	0.0241 (14)
C16	−0.6580 (8)	0.3751 (4)	0.15251 (13)	0.0266 (15)
H16	−0.7124	0.4221	0.1419	0.032*
C17	−0.6848 (9)	0.3710 (5)	0.18001 (14)	0.0316 (16)
H17	−0.7582	0.4157	0.1882	0.038*
C18	−0.6075 (9)	0.3035 (5)	0.19581 (14)	0.0326 (16)
H18	−0.6268	0.3031	0.2147	0.039*
C19	−0.5007 (8)	0.2356 (4)	0.18424 (12)	0.0251 (14)
H19	−0.4466	0.1888	0.1950	0.030*
C20	−0.1402 (7)	0.4322 (5)	0.08138 (13)	0.0241 (14)
H20	−0.1537	0.4478	0.0999	0.029*
C21	−0.0586 (8)	0.3511 (5)	0.07691 (12)	0.0261 (15)
C22	−0.0083 (8)	0.2928 (5)	0.10055 (13)	0.0252 (14)
C23	0.0934 (8)	0.2208 (5)	0.06279 (13)	0.0291 (15)
C24	0.0082 (8)	0.3024 (5)	0.05309 (13)	0.0275 (15)
C25	0.0160 (8)	0.3213 (5)	0.02561 (13)	0.0282 (15)
H25	−0.0367	0.3762	0.0185	0.034*
C26	0.1005 (8)	0.2602 (5)	0.00865 (13)	0.0306 (16)
H26	0.1051	0.2733	−0.0101	0.037*
C27	0.1784 (9)	0.1804 (5)	0.01854 (14)	0.0348 (17)
H27	0.2340	0.1389	0.0064	0.042*
C28	0.1777 (8)	0.1591 (5)	0.04594 (14)	0.0320 (16)
H28	0.2329	0.1045	0.0528	0.038*
N1	−0.3842 (7)	0.1777 (4)	0.14070 (11)	0.0264 (12)
H1	−0.3242	0.1300	0.1469	0.032*
N2	0.0794 (6)	0.2164 (4)	0.09089 (10)	0.0275 (12)
H2A	0.1212	0.1709	0.1010	0.033*
O1	−0.3339 (6)	0.1574 (3)	0.09524 (9)	0.0305 (11)
O2	−0.0382 (6)	0.3068 (3)	0.12460 (9)	0.0311 (11)
Fe1	−0.46894 (12)	0.52616 (6)	0.061441 (18)	0.0243 (2)
C101	0.0718 (8)	−0.2528 (4)	0.16621 (12)	0.0212 (13)
C102	0.2059 (8)	−0.2991 (4)	0.15215 (12)	0.0222 (13)
H102	0.2482	−0.2825	0.1348	0.027*
C103	0.2656 (8)	−0.3747 (5)	0.16857 (13)	0.0267 (15)
H103	0.3530	−0.4180	0.1639	0.032*
C104	0.1730 (8)	−0.3741 (5)	0.19281 (13)	0.0282 (15)
H104	0.1875	−0.4168	0.2074	0.034*
C105	0.0551 (8)	−0.2995 (4)	0.19180 (12)	0.0252 (14)
H105	−0.0224	−0.2828	0.2057	0.030*
C106	0.3907 (8)	−0.1135 (4)	0.18866 (12)	0.0242 (14)
C107	0.5210 (8)	−0.1812 (5)	0.18140 (13)	0.0255 (14)
H107	0.5825	−0.1820	0.1649	0.031*
C108	0.5413 (8)	−0.2456 (5)	0.20282 (13)	0.0295 (15)
H108	0.6200	−0.2963	0.2035	0.035*
C109	0.4239 (8)	−0.2213 (5)	0.22311 (13)	0.0278 (15)
H109	0.4107	−0.2534	0.2398	0.033*
C110	0.3293 (8)	−0.1421 (4)	0.21490 (12)	0.0236 (14)
H110	0.2408	−0.1127	0.2248	0.028*
C111	−0.0271 (7)	−0.1694 (4)	0.15994 (12)	0.0202 (13)
H111	−0.0775	−0.1401	0.1752	0.024*
C112	−0.0605 (7)	−0.1258 (4)	0.13626 (12)	0.0211 (13)
C113	−0.1531 (7)	−0.0335 (4)	0.13666 (12)	0.0210 (13)
C114	−0.0697 (8)	−0.0634 (4)	0.09344 (12)	0.0225 (13)
C115	−0.0179 (7)	−0.1437 (4)	0.10791 (12)	0.0206 (13)
C116	0.0432 (7)	−0.2202 (5)	0.09347 (13)	0.0245 (14)
H116	0.0711	−0.2772	0.1025	0.029*
C117	0.0630 (8)	−0.2129 (5)	0.06578 (13)	0.0313 (16)
H117	0.1058	−0.2650	0.0558	0.038*
C118	0.0210 (8)	−0.1305 (5)	0.05244 (13)	0.0306 (16)
H118	0.0401	−0.1261	0.0336	0.037*
C119	−0.0485 (8)	−0.0540 (5)	0.06607 (13)	0.0286 (15)
H119	−0.0798	0.0022	0.0569	0.034*
C120	0.3356 (8)	−0.0402 (4)	0.17034 (12)	0.0215 (13)
H120	0.3717	−0.0494	0.1522	0.026*
C121	0.2430 (7)	0.0384 (4)	0.17404 (12)	0.0216 (13)
C122	0.1908 (8)	0.0958 (4)	0.15007 (12)	0.0234 (14)
C123	0.0609 (8)	0.1587 (4)	0.18659 (12)	0.0248 (14)
C124	0.1585 (8)	0.0847 (4)	0.19714 (12)	0.0218 (13)
C125	0.1695 (8)	0.0746 (5)	0.22498 (12)	0.0254 (14)
H125	0.2414	0.0278	0.2326	0.031*
C126	0.0757 (8)	0.1329 (5)	0.24150 (13)	0.0275 (15)
H126	0.0813	0.1251	0.2605	0.033*
C127	−0.0278 (8)	0.2035 (5)	0.23048 (14)	0.0298 (15)
H127	−0.0935	0.2424	0.2420	0.036*
C128	−0.0349 (8)	0.2168 (5)	0.20264 (14)	0.0301 (15)
H128	−0.1042	0.2648	0.1950	0.036*
N101	−0.1470 (7)	0.0011 (4)	0.11117 (10)	0.0246 (12)
H101	−0.1862	0.0567	0.1063	0.029*
N102	0.0832 (6)	0.1625 (4)	0.15876 (10)	0.0250 (12)
H10A	0.0328	0.2037	0.1481	0.030*
O101	−0.2215 (5)	0.0043 (3)	0.15619 (8)	0.0276 (10)
O102	0.2362 (5)	0.0845 (3)	0.12643 (8)	0.0286 (10)
Fe11	0.29568 (11)	−0.24844 (6)	0.187934 (17)	0.0210 (2)
C201	0.4288 (10)	−0.0732 (6)	0.09020 (14)	0.0385 (18)
H20A	0.3033	−0.0776	0.0913	0.046*
H20B	0.4652	−0.0172	0.1006	0.046*
Cl21	0.4894 (3)	−0.05986 (15)	0.05659 (4)	0.0478 (5)
Cl22	0.5211 (2)	−0.17618 (14)	0.10453 (4)	0.0403 (4)
C301	0.3279 (10)	−0.1579 (5)	−0.02580 (15)	0.0421 (19)
H30A	0.4234	−0.1427	−0.0381	0.050*
H30B	0.2310	−0.1799	−0.0369	0.050*
Cl31	0.3906 (3)	−0.24859 (15)	−0.00332 (5)	0.0568 (6)
Cl32	0.2683 (3)	−0.05626 (14)	−0.00801 (4)	0.0467 (5)
C401	−0.2004 (15)	0.4667 (8)	0.1677 (2)	0.084 (4)
H40A	−0.2741	0.4146	0.1614	0.101*
H40B	−0.0818	0.4503	0.1630	0.101*
Cl41	−0.2570 (3)	0.56897 (19)	0.15025 (5)	0.0639 (6)
Cl42	−0.2150 (4)	0.47350 (19)	0.20177 (5)	0.0823 (9)
C501	−0.2521 (9)	−0.0170 (5)	0.22222 (13)	0.0307 (15)
H50A	−0.3145	−0.0452	0.2069	0.037*
H50B	−0.1683	0.0283	0.2149	0.037*
Cl51	−0.1450 (2)	−0.10604 (13)	0.24014 (4)	0.0413 (4)
Cl52	−0.3971 (2)	0.04349 (14)	0.24338 (4)	0.0435 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.019 (3)	0.024 (3)	0.027 (3)	−0.002 (3)	0.000 (3)	0.003 (3)
C2	0.028 (4)	0.029 (4)	0.026 (3)	0.004 (3)	0.005 (3)	0.007 (3)
C3	0.032 (4)	0.033 (4)	0.032 (4)	0.013 (3)	0.010 (3)	0.006 (3)
C4	0.028 (4)	0.034 (4)	0.035 (4)	0.005 (3)	−0.002 (3)	0.013 (3)
C5	0.018 (3)	0.024 (3)	0.031 (3)	−0.005 (3)	−0.002 (3)	0.001 (3)
C6	0.018 (3)	0.026 (4)	0.029 (3)	0.002 (3)	0.003 (3)	0.006 (3)
C7	0.028 (4)	0.028 (4)	0.036 (4)	−0.005 (3)	0.002 (3)	0.001 (3)
C8	0.038 (4)	0.024 (4)	0.041 (4)	−0.001 (3)	0.011 (3)	0.008 (3)
C9	0.030 (4)	0.039 (4)	0.030 (4)	0.009 (3)	0.007 (3)	0.017 (3)
C10	0.026 (4)	0.031 (4)	0.031 (4)	0.005 (3)	0.003 (3)	0.002 (3)
C11	0.023 (3)	0.030 (4)	0.026 (3)	−0.003 (3)	−0.002 (3)	−0.003 (3)
C12	0.016 (3)	0.021 (3)	0.026 (3)	−0.003 (3)	0.000 (2)	−0.001 (3)
C13	0.020 (3)	0.023 (4)	0.032 (4)	0.000 (3)	−0.003 (3)	−0.002 (3)
C14	0.014 (3)	0.021 (3)	0.032 (3)	0.000 (3)	0.001 (2)	0.002 (3)
C15	0.021 (3)	0.021 (3)	0.030 (3)	0.000 (3)	−0.003 (3)	0.002 (3)
C16	0.030 (4)	0.010 (3)	0.040 (4)	−0.001 (3)	0.004 (3)	0.002 (3)
C17	0.037 (4)	0.022 (4)	0.036 (4)	0.004 (3)	0.007 (3)	−0.002 (3)
C18	0.034 (4)	0.033 (4)	0.031 (4)	−0.011 (3)	0.011 (3)	0.000 (3)
C19	0.024 (3)	0.022 (3)	0.029 (3)	−0.003 (3)	−0.001 (3)	0.007 (3)
C20	0.017 (3)	0.030 (4)	0.025 (3)	−0.003 (3)	−0.004 (2)	−0.003 (3)
C21	0.020 (3)	0.035 (4)	0.023 (3)	−0.007 (3)	−0.002 (3)	0.003 (3)
C22	0.016 (3)	0.028 (4)	0.031 (4)	−0.005 (3)	−0.003 (3)	0.004 (3)
C23	0.023 (3)	0.034 (4)	0.030 (4)	−0.008 (3)	0.003 (3)	0.001 (3)
C24	0.020 (3)	0.031 (4)	0.032 (4)	−0.002 (3)	0.001 (3)	0.002 (3)
C25	0.019 (3)	0.037 (4)	0.028 (4)	−0.006 (3)	0.000 (3)	−0.001 (3)
C26	0.025 (3)	0.039 (4)	0.028 (3)	−0.008 (3)	0.004 (3)	−0.002 (3)
C27	0.029 (4)	0.043 (5)	0.033 (4)	−0.002 (3)	0.004 (3)	−0.005 (3)
C28	0.029 (4)	0.031 (4)	0.036 (4)	0.001 (3)	−0.001 (3)	0.001 (3)
N1	0.025 (3)	0.017 (3)	0.037 (3)	0.004 (2)	−0.002 (2)	0.001 (2)
N2	0.022 (3)	0.031 (3)	0.029 (3)	0.004 (2)	0.000 (2)	0.005 (2)
O1	0.036 (3)	0.025 (3)	0.030 (2)	0.009 (2)	0.006 (2)	0.001 (2)
O2	0.029 (3)	0.040 (3)	0.024 (2)	0.004 (2)	−0.0014 (19)	0.002 (2)
Fe1	0.0259 (5)	0.0219 (5)	0.0251 (5)	0.0021 (4)	0.0007 (4)	0.0026 (4)
C101	0.022 (3)	0.020 (3)	0.022 (3)	−0.001 (3)	−0.001 (2)	−0.003 (3)
C102	0.024 (3)	0.023 (3)	0.021 (3)	−0.006 (3)	−0.001 (2)	−0.005 (3)
C103	0.020 (3)	0.029 (4)	0.031 (4)	0.002 (3)	−0.006 (3)	0.000 (3)
C104	0.030 (4)	0.029 (4)	0.026 (3)	−0.005 (3)	−0.004 (3)	0.007 (3)
C105	0.025 (3)	0.025 (4)	0.025 (3)	−0.003 (3)	−0.002 (3)	0.001 (3)
C106	0.027 (3)	0.019 (3)	0.027 (3)	−0.002 (3)	−0.003 (3)	−0.003 (3)
C107	0.019 (3)	0.030 (4)	0.027 (3)	−0.003 (3)	−0.006 (3)	−0.006 (3)
C108	0.018 (3)	0.032 (4)	0.038 (4)	0.001 (3)	−0.010 (3)	−0.001 (3)
C109	0.028 (4)	0.026 (4)	0.029 (3)	−0.007 (3)	−0.009 (3)	0.002 (3)
C110	0.024 (3)	0.023 (3)	0.024 (3)	0.002 (3)	−0.001 (3)	−0.005 (3)
C111	0.013 (3)	0.026 (3)	0.022 (3)	−0.005 (3)	0.001 (2)	−0.006 (3)
C112	0.012 (3)	0.028 (4)	0.023 (3)	0.001 (3)	−0.001 (2)	−0.004 (3)
C113	0.014 (3)	0.020 (3)	0.028 (3)	−0.002 (3)	0.001 (2)	0.004 (3)
C114	0.020 (3)	0.022 (3)	0.026 (3)	0.002 (3)	0.000 (3)	0.001 (3)
C115	0.014 (3)	0.023 (3)	0.025 (3)	−0.002 (3)	−0.005 (2)	−0.004 (3)
C116	0.017 (3)	0.025 (4)	0.031 (4)	0.005 (3)	−0.006 (3)	−0.001 (3)
C117	0.028 (4)	0.038 (4)	0.028 (4)	0.010 (3)	−0.006 (3)	−0.007 (3)
C118	0.029 (4)	0.041 (4)	0.023 (3)	0.001 (3)	−0.002 (3)	−0.004 (3)
C119	0.026 (3)	0.029 (4)	0.031 (4)	0.001 (3)	−0.009 (3)	0.005 (3)
C120	0.028 (3)	0.012 (3)	0.025 (3)	0.001 (3)	0.006 (3)	−0.002 (2)
C121	0.020 (3)	0.024 (3)	0.020 (3)	−0.006 (3)	0.002 (2)	0.000 (3)
C122	0.023 (3)	0.023 (3)	0.025 (3)	−0.005 (3)	−0.001 (3)	−0.003 (3)
C123	0.028 (3)	0.020 (3)	0.026 (3)	−0.006 (3)	0.005 (3)	0.000 (3)
C124	0.020 (3)	0.016 (3)	0.029 (3)	−0.004 (3)	0.002 (3)	0.001 (3)
C125	0.020 (3)	0.031 (4)	0.026 (3)	−0.005 (3)	0.001 (3)	−0.002 (3)
C126	0.030 (4)	0.025 (4)	0.027 (3)	−0.003 (3)	0.004 (3)	−0.008 (3)
C127	0.029 (4)	0.025 (4)	0.036 (4)	−0.008 (3)	0.010 (3)	−0.009 (3)
C128	0.027 (4)	0.020 (3)	0.044 (4)	−0.001 (3)	0.005 (3)	−0.004 (3)
N101	0.030 (3)	0.016 (3)	0.028 (3)	0.002 (2)	0.000 (2)	0.002 (2)
N102	0.023 (3)	0.025 (3)	0.027 (3)	0.006 (2)	0.001 (2)	0.001 (2)
O101	0.028 (2)	0.028 (3)	0.027 (2)	0.006 (2)	0.0018 (19)	−0.0006 (19)
O102	0.027 (2)	0.033 (3)	0.026 (2)	0.005 (2)	−0.0019 (19)	−0.001 (2)
Fe11	0.0213 (5)	0.0196 (5)	0.0220 (4)	0.0003 (4)	−0.0007 (3)	−0.0001 (4)
C201	0.039 (4)	0.046 (5)	0.031 (4)	0.001 (4)	0.001 (3)	0.005 (3)
Cl21	0.0476 (12)	0.0593 (13)	0.0365 (10)	0.0051 (10)	0.0064 (8)	0.0128 (9)
Cl22	0.0356 (10)	0.0483 (12)	0.0369 (10)	−0.0023 (9)	−0.0016 (8)	0.0078 (8)
C301	0.047 (5)	0.038 (5)	0.041 (4)	−0.003 (4)	−0.001 (4)	−0.002 (3)
Cl31	0.0431 (12)	0.0392 (12)	0.0880 (16)	0.0005 (10)	−0.0180 (11)	0.0063 (11)
Cl32	0.0659 (13)	0.0402 (11)	0.0342 (10)	0.0066 (10)	0.0049 (9)	0.0049 (8)
C401	0.098 (8)	0.083 (8)	0.070 (7)	0.055 (7)	−0.040 (6)	−0.031 (6)
Cl41	0.0548 (14)	0.0768 (17)	0.0599 (14)	−0.0060 (12)	−0.0022 (11)	−0.0203 (12)
Cl42	0.123 (2)	0.0540 (15)	0.0697 (17)	−0.0297 (16)	0.0208 (16)	−0.0127 (13)
C501	0.031 (4)	0.035 (4)	0.026 (3)	−0.001 (3)	−0.003 (3)	−0.002 (3)
Cl51	0.0337 (10)	0.0381 (11)	0.0521 (11)	0.0045 (8)	0.0028 (8)	0.0081 (9)
Cl52	0.0294 (9)	0.0422 (11)	0.0587 (12)	0.0053 (8)	−0.0001 (8)	−0.0174 (9)

Geometric parameters (Å, º)

C1—C5	1.441 (8)	C103—Fe11	2.045 (7)
C1—C2	1.442 (9)	C103—H103	0.9500
C1—C11	1.464 (9)	C104—C105	1.408 (9)
C1—Fe1	2.070 (6)	C104—Fe11	2.042 (7)
C2—C3	1.412 (9)	C104—H104	0.9500
C2—Fe1	2.041 (6)	C105—Fe11	2.034 (6)
C2—H2	0.9500	C105—H105	0.9500
C3—C4	1.404 (10)	C106—C110	1.446 (9)
C3—Fe1	2.038 (6)	C106—C120	1.446 (8)
C3—H3	0.9500	C106—C107	1.450 (9)
C4—C5	1.421 (9)	C106—Fe11	2.056 (6)
C4—Fe1	2.040 (7)	C107—C108	1.410 (9)
C4—H4	0.9500	C107—Fe11	2.038 (6)
C5—Fe1	2.030 (6)	C107—H107	0.9500
C5—H5	0.9500	C108—C109	1.408 (9)
C6—C10	1.430 (9)	C108—Fe11	2.066 (6)
C6—C7	1.437 (9)	C108—H108	0.9500
C6—C20	1.444 (9)	C109—C110	1.406 (9)
C6—Fe1	2.058 (6)	C109—Fe11	2.048 (6)
C7—C8	1.415 (10)	C109—H109	0.9500
C7—Fe1	2.035 (7)	C110—Fe11	2.032 (6)
C7—H7	0.9500	C110—H110	0.9500
C8—C9	1.423 (10)	C111—C112	1.352 (8)
C8—Fe1	2.049 (7)	C111—H111	0.9500
C8—H8	0.9500	C112—C115	1.466 (8)
C9—C10	1.424 (9)	C112—C113	1.498 (8)
C9—Fe1	2.044 (6)	C113—O101	1.231 (7)
C9—H9	0.9500	C113—N101	1.356 (8)
C10—Fe1	2.040 (6)	C114—C119	1.373 (9)
C10—H10	0.9500	C114—C115	1.405 (8)
C11—C12	1.335 (9)	C114—N101	1.408 (8)
C11—H11	0.9500	C115—C116	1.387 (8)
C12—C15	1.461 (9)	C116—C117	1.385 (9)
C12—C13	1.501 (9)	C116—H116	0.9500
C13—O1	1.241 (7)	C117—C118	1.383 (10)
C13—N1	1.342 (8)	C117—H117	0.9500
C14—C19	1.376 (9)	C118—C119	1.391 (9)
C14—N1	1.390 (8)	C118—H118	0.9500
C14—C15	1.405 (8)	C119—H119	0.9500
C15—C16	1.394 (9)	C120—C121	1.345 (8)
C16—C17	1.380 (9)	C120—H120	0.9500
C16—H16	0.9500	C121—C124	1.478 (8)
C17—C18	1.377 (10)	C121—C122	1.497 (8)
C17—H17	0.9500	C122—O102	1.236 (7)
C18—C19	1.402 (9)	C122—N102	1.341 (8)
C18—H18	0.9500	C123—C128	1.372 (9)
C19—H19	0.9500	C123—N102	1.392 (8)
C20—C21	1.336 (9)	C123—C124	1.401 (9)
C20—H20	0.9500	C124—C125	1.389 (8)
C21—C24	1.466 (9)	C125—C126	1.378 (9)
C21—C22	1.487 (9)	C125—H125	0.9500
C22—O2	1.231 (7)	C126—C127	1.401 (9)
C22—N2	1.372 (8)	C126—H126	0.9500
C23—C28	1.380 (9)	C127—C128	1.393 (9)
C23—N2	1.398 (8)	C127—H127	0.9500
C23—C24	1.421 (9)	C128—H128	0.9500
C24—C25	1.389 (9)	N101—H101	0.8800
C25—C26	1.379 (9)	N102—H10A	0.8800
C25—H25	0.9500	C201—Cl21	1.743 (7)
C26—C27	1.376 (10)	C201—Cl22	1.779 (8)
C26—H26	0.9500	C201—H20A	0.9900
C27—C28	1.391 (9)	C201—H20B	0.9900
C27—H27	0.9500	C301—Cl32	1.754 (8)
C28—H28	0.9500	C301—Cl31	1.771 (8)
N1—H1	0.8800	C301—H30A	0.9900
N2—H2A	0.8800	C301—H30B	0.9900
C101—C102	1.425 (8)	C401—Cl42	1.694 (10)
C101—C105	1.436 (8)	C401—Cl41	1.747 (11)
C101—C111	1.450 (9)	C401—H40A	0.9900
C101—Fe11	2.062 (6)	C401—H40B	0.9900
C102—C103	1.424 (9)	C501—Cl51	1.759 (7)
C102—Fe11	2.038 (6)	C501—Cl52	1.771 (7)
C102—H102	0.9500	C501—H50A	0.9900
C103—C104	1.405 (9)	C501—H50B	0.9900
C5—C1—C2	106.9 (5)	C104—C103—C102	108.2 (6)
C5—C1—C11	122.7 (6)	C104—C103—Fe11	69.7 (4)
C2—C1—C11	130.0 (6)	C102—C103—Fe11	69.3 (4)
C5—C1—Fe1	67.9 (3)	C104—C103—H103	125.9
C2—C1—Fe1	68.4 (3)	C102—C103—H103	125.9
C11—C1—Fe1	122.5 (4)	Fe11—C103—H103	126.6
C3—C2—C1	107.7 (6)	C103—C104—C105	108.4 (6)
C3—C2—Fe1	69.6 (4)	C103—C104—Fe11	70.0 (4)
C1—C2—Fe1	70.5 (3)	C105—C104—Fe11	69.5 (4)
C3—C2—H2	126.2	C103—C104—H104	125.8
C1—C2—H2	126.2	C105—C104—H104	125.8
Fe1—C2—H2	125.3	Fe11—C104—H104	126.2
C4—C3—C2	109.2 (6)	C104—C105—C101	108.5 (6)
C4—C3—Fe1	70.0 (4)	C104—C105—Fe11	70.1 (4)
C2—C3—Fe1	69.9 (4)	C101—C105—Fe11	70.5 (4)
C4—C3—H3	125.4	C104—C105—H105	125.8
C2—C3—H3	125.4	C101—C105—H105	125.8
Fe1—C3—H3	126.4	Fe11—C105—H105	125.2
C3—C4—C5	108.3 (6)	C110—C106—C120	131.8 (6)
C3—C4—Fe1	69.8 (4)	C110—C106—C107	105.9 (5)
C5—C4—Fe1	69.2 (4)	C120—C106—C107	122.1 (6)
C3—C4—H4	125.8	C110—C106—Fe11	68.4 (3)
C5—C4—H4	125.8	C120—C106—Fe11	123.4 (4)
Fe1—C4—H4	126.8	C107—C106—Fe11	68.6 (3)
C4—C5—C1	107.8 (6)	C108—C107—C106	108.8 (6)
C4—C5—Fe1	69.9 (4)	C108—C107—Fe11	71.0 (4)
C1—C5—Fe1	70.9 (3)	C106—C107—Fe11	69.9 (3)
C4—C5—H5	126.1	C108—C107—H107	125.6
C1—C5—H5	126.1	C106—C107—H107	125.6
Fe1—C5—H5	124.7	Fe11—C107—H107	125.1
C10—C6—C7	106.7 (6)	C109—C108—C107	107.7 (6)
C10—C6—C20	130.3 (6)	C109—C108—Fe11	69.3 (4)
C7—C6—C20	122.6 (6)	C107—C108—Fe11	68.8 (3)
C10—C6—Fe1	68.9 (3)	C109—C108—H108	126.1
C7—C6—Fe1	68.6 (4)	C107—C108—H108	126.1
C20—C6—Fe1	121.5 (4)	Fe11—C108—H108	127.3
C8—C7—C6	108.8 (6)	C110—C109—C108	109.6 (6)
C8—C7—Fe1	70.3 (4)	C110—C109—Fe11	69.2 (3)
C6—C7—Fe1	70.3 (4)	C108—C109—Fe11	70.7 (4)
C8—C7—H7	125.6	C110—C109—H109	125.2
C6—C7—H7	125.6	C108—C109—H109	125.2
Fe1—C7—H7	125.4	Fe11—C109—H109	126.5
C7—C8—C9	108.0 (6)	C109—C110—C106	107.9 (6)
C7—C8—Fe1	69.2 (4)	C109—C110—Fe11	70.5 (4)
C9—C8—Fe1	69.4 (4)	C106—C110—Fe11	70.2 (3)
C7—C8—H8	126.0	C109—C110—H110	126.0
C9—C8—H8	126.0	C106—C110—H110	126.0
Fe1—C8—H8	127.0	Fe11—C110—H110	124.9
C8—C9—C10	107.9 (6)	C112—C111—C101	131.5 (6)
C8—C9—Fe1	69.9 (4)	C112—C111—H111	114.2
C10—C9—Fe1	69.5 (4)	C101—C111—H111	114.2
C8—C9—H9	126.0	C111—C112—C115	135.1 (6)
C10—C9—H9	126.0	C111—C112—C113	118.8 (5)
Fe1—C9—H9	126.2	C115—C112—C113	106.0 (5)
C9—C10—C6	108.6 (6)	O101—C113—N101	126.1 (6)
C9—C10—Fe1	69.7 (4)	O101—C113—C112	127.2 (5)
C6—C10—Fe1	70.2 (4)	N101—C113—C112	106.7 (5)
C9—C10—H10	125.7	C119—C114—C115	123.2 (6)
C6—C10—H10	125.7	C119—C114—N101	127.3 (6)
Fe1—C10—H10	125.9	C115—C114—N101	109.5 (5)
C12—C11—C1	129.9 (6)	C116—C115—C114	118.1 (6)
C12—C11—H11	115.1	C116—C115—C112	135.2 (6)
C1—C11—H11	115.1	C114—C115—C112	106.4 (5)
C11—C12—C15	137.2 (6)	C117—C116—C115	119.5 (6)
C11—C12—C13	118.4 (6)	C117—C116—H116	120.3
C15—C12—C13	104.4 (5)	C115—C116—H116	120.3
O1—C13—N1	126.4 (6)	C118—C117—C116	120.6 (6)
O1—C13—C12	125.8 (6)	C118—C117—H117	119.7
N1—C13—C12	107.8 (5)	C116—C117—H117	119.7
C19—C14—N1	127.8 (6)	C117—C118—C119	121.4 (6)
C19—C14—C15	122.8 (6)	C117—C118—H118	119.3
N1—C14—C15	109.4 (5)	C119—C118—H118	119.3
C16—C15—C14	118.3 (6)	C114—C119—C118	116.8 (6)
C16—C15—C12	134.3 (6)	C114—C119—H119	121.6
C14—C15—C12	107.2 (5)	C118—C119—H119	121.6
C17—C16—C15	119.3 (6)	C121—C120—C106	132.3 (6)
C17—C16—H16	120.4	C121—C120—H120	113.9
C15—C16—H16	120.4	C106—C120—H120	113.9
C18—C17—C16	121.5 (6)	C120—C121—C124	135.9 (6)
C18—C17—H17	119.2	C120—C121—C122	119.4 (5)
C16—C17—H17	119.2	C124—C121—C122	104.4 (5)
C17—C18—C19	120.7 (6)	O102—C122—N102	125.4 (6)
C17—C18—H18	119.7	O102—C122—C121	127.0 (6)
C19—C18—H18	119.7	N102—C122—C121	107.6 (5)
C14—C19—C18	117.3 (6)	C128—C123—N102	128.4 (6)
C14—C19—H19	121.3	C128—C123—C124	122.4 (6)
C18—C19—H19	121.3	N102—C123—C124	109.2 (5)
C21—C20—C6	131.0 (6)	C125—C124—C123	118.7 (6)
C21—C20—H20	114.5	C125—C124—C121	134.1 (6)
C6—C20—H20	114.5	C123—C124—C121	106.9 (5)
C20—C21—C24	135.4 (6)	C126—C125—C124	119.7 (6)
C20—C21—C22	118.4 (6)	C126—C125—H125	120.2
C24—C21—C22	106.1 (6)	C124—C125—H125	120.2
O2—C22—N2	124.2 (6)	C125—C126—C127	120.6 (6)
O2—C22—C21	128.4 (6)	C125—C126—H126	119.7
N2—C22—C21	107.3 (5)	C127—C126—H126	119.7
C28—C23—N2	127.8 (6)	C128—C127—C126	120.4 (6)
C28—C23—C24	122.6 (6)	C128—C127—H127	119.8
N2—C23—C24	109.6 (6)	C126—C127—H127	119.8
C25—C24—C23	117.9 (6)	C123—C128—C127	118.1 (6)
C25—C24—C21	135.6 (6)	C123—C128—H128	121.0
C23—C24—C21	106.3 (6)	C127—C128—H128	121.0
C26—C25—C24	119.8 (7)	C113—N101—C114	111.2 (5)
C26—C25—H25	120.1	C113—N101—H101	124.4
C24—C25—H25	120.1	C114—N101—H101	124.4
C27—C26—C25	121.0 (6)	C122—N102—C123	111.8 (5)
C27—C26—H26	119.5	C122—N102—H10A	124.1
C25—C26—H26	119.5	C123—N102—H10A	124.1
C26—C27—C28	121.6 (7)	C110—Fe11—C105	108.8 (3)
C26—C27—H27	119.2	C110—Fe11—C102	151.4 (3)
C28—C27—H27	119.2	C105—Fe11—C102	68.6 (2)
C23—C28—C27	117.1 (7)	C110—Fe11—C107	69.2 (3)
C23—C28—H28	121.5	C105—Fe11—C107	171.8 (3)
C27—C28—H28	121.5	C102—Fe11—C107	109.1 (2)
C13—N1—C14	111.1 (5)	C110—Fe11—C104	129.2 (3)
C13—N1—H1	124.5	C105—Fe11—C104	40.4 (3)
C14—N1—H1	124.5	C102—Fe11—C104	68.4 (3)
C22—N2—C23	110.7 (5)	C107—Fe11—C104	147.0 (3)
C22—N2—H2A	124.7	C110—Fe11—C103	166.7 (3)
C23—N2—H2A	124.7	C105—Fe11—C103	68.0 (3)
C5—Fe1—C7	170.4 (3)	C102—Fe11—C103	40.8 (2)
C5—Fe1—C3	68.5 (3)	C107—Fe11—C103	115.8 (3)
C7—Fe1—C3	116.8 (3)	C104—Fe11—C103	40.2 (3)
C5—Fe1—C10	107.9 (3)	C110—Fe11—C109	40.3 (2)
C7—Fe1—C10	68.7 (3)	C105—Fe11—C109	116.3 (3)
C3—Fe1—C10	167.2 (3)	C102—Fe11—C109	167.3 (3)
C5—Fe1—C4	40.9 (3)	C107—Fe11—C109	67.7 (3)
C7—Fe1—C4	148.1 (3)	C104—Fe11—C109	107.2 (3)
C3—Fe1—C4	40.3 (3)	C103—Fe11—C109	128.3 (3)
C10—Fe1—C4	129.1 (3)	C110—Fe11—C106	41.4 (2)
C5—Fe1—C2	69.3 (3)	C105—Fe11—C106	131.9 (3)
C7—Fe1—C2	109.1 (3)	C102—Fe11—C106	118.0 (2)
C3—Fe1—C2	40.5 (3)	C107—Fe11—C106	41.5 (2)
C10—Fe1—C2	151.2 (3)	C104—Fe11—C106	169.5 (3)
C4—Fe1—C2	68.5 (3)	C103—Fe11—C106	149.9 (3)
C5—Fe1—C9	115.2 (3)	C109—Fe11—C106	68.4 (3)
C7—Fe1—C9	68.5 (3)	C110—Fe11—C101	118.4 (2)
C3—Fe1—C9	128.4 (3)	C105—Fe11—C101	41.0 (2)
C10—Fe1—C9	40.8 (3)	C102—Fe11—C101	40.7 (2)
C4—Fe1—C9	106.6 (3)	C107—Fe11—C101	132.2 (2)
C2—Fe1—C9	167.3 (3)	C104—Fe11—C101	68.4 (2)
C5—Fe1—C8	147.7 (3)	C103—Fe11—C101	68.3 (2)
C7—Fe1—C8	40.5 (3)	C109—Fe11—C101	150.2 (3)
C3—Fe1—C8	107.5 (3)	C106—Fe11—C101	110.3 (2)
C10—Fe1—C8	68.5 (3)	C110—Fe11—C108	68.3 (3)
C4—Fe1—C8	115.0 (3)	C105—Fe11—C108	147.3 (3)
C2—Fe1—C8	129.6 (3)	C102—Fe11—C108	129.7 (3)
C9—Fe1—C8	40.7 (3)	C107—Fe11—C108	40.2 (3)
C5—Fe1—C6	130.6 (3)	C104—Fe11—C108	114.6 (3)
C7—Fe1—C6	41.1 (3)	C103—Fe11—C108	107.0 (3)
C3—Fe1—C6	150.5 (3)	C109—Fe11—C108	40.0 (3)
C10—Fe1—C6	40.9 (2)	C106—Fe11—C108	68.7 (3)
C4—Fe1—C6	168.7 (3)	C101—Fe11—C108	169.4 (3)
C2—Fe1—C6	118.2 (3)	Cl21—C201—Cl22	111.0 (4)
C9—Fe1—C6	68.8 (3)	Cl21—C201—H20A	109.4
C8—Fe1—C6	68.7 (3)	Cl22—C201—H20A	109.4
C5—Fe1—C1	41.2 (2)	Cl21—C201—H20B	109.4
C7—Fe1—C1	131.6 (3)	Cl22—C201—H20B	109.4
C3—Fe1—C1	68.3 (3)	H20A—C201—H20B	108.0
C10—Fe1—C1	117.7 (3)	Cl32—C301—Cl31	110.8 (4)
C4—Fe1—C1	68.5 (3)	Cl32—C301—H30A	109.5
C2—Fe1—C1	41.1 (3)	Cl31—C301—H30A	109.5
C9—Fe1—C1	149.5 (3)	Cl32—C301—H30B	109.5
C8—Fe1—C1	169.4 (3)	Cl31—C301—H30B	109.5
C6—Fe1—C1	109.8 (2)	H30A—C301—H30B	108.1
C102—C101—C105	106.7 (5)	Cl42—C401—Cl41	115.4 (5)
C102—C101—C111	132.0 (6)	Cl42—C401—H40A	108.4
C105—C101—C111	121.0 (5)	Cl41—C401—H40A	108.4
C102—C101—Fe11	68.7 (3)	Cl42—C401—H40B	108.4
C105—C101—Fe11	68.4 (3)	Cl41—C401—H40B	108.4
C111—C101—Fe11	123.0 (4)	H40A—C401—H40B	107.5
C103—C102—C101	108.1 (5)	Cl51—C501—Cl52	110.9 (4)
C103—C102—Fe11	69.9 (4)	Cl51—C501—H50A	109.5
C101—C102—Fe11	70.6 (3)	Cl52—C501—H50A	109.5
C103—C102—H102	125.9	Cl51—C501—H50B	109.5
C101—C102—H102	125.9	Cl52—C501—H50B	109.5
Fe11—C102—H102	125.2	H50A—C501—H50B	108.0
C5—C1—C2—C3	2.7 (7)	C105—C101—C102—C103	1.9 (7)
C11—C1—C2—C3	174.9 (6)	C111—C101—C102—C103	175.8 (6)
Fe1—C1—C2—C3	59.9 (4)	Fe11—C101—C102—C103	60.0 (4)
C5—C1—C2—Fe1	−57.2 (4)	C105—C101—C102—Fe11	−58.1 (4)
C11—C1—C2—Fe1	115.0 (7)	C111—C101—C102—Fe11	115.8 (7)
C1—C2—C3—C4	−1.5 (7)	C101—C102—C103—C104	−1.4 (7)
Fe1—C2—C3—C4	59.0 (5)	Fe11—C102—C103—C104	59.1 (4)
C1—C2—C3—Fe1	−60.5 (4)	C101—C102—C103—Fe11	−60.5 (4)
C2—C3—C4—C5	−0.4 (8)	C102—C103—C104—C105	0.3 (7)
Fe1—C3—C4—C5	58.6 (5)	Fe11—C103—C104—C105	59.1 (4)
C2—C3—C4—Fe1	−59.0 (5)	C102—C103—C104—Fe11	−58.8 (4)
C3—C4—C5—C1	2.1 (7)	C103—C104—C105—C101	0.9 (7)
Fe1—C4—C5—C1	61.1 (4)	Fe11—C104—C105—C101	60.3 (4)
C3—C4—C5—Fe1	−59.0 (5)	C103—C104—C105—Fe11	−59.4 (5)
C2—C1—C5—C4	−3.0 (7)	C102—C101—C105—C104	−1.8 (7)
C11—C1—C5—C4	−175.9 (6)	C111—C101—C105—C104	−176.5 (5)
Fe1—C1—C5—C4	−60.5 (4)	Fe11—C101—C105—C104	−60.0 (4)
C2—C1—C5—Fe1	57.5 (4)	C102—C101—C105—Fe11	58.3 (4)
C11—C1—C5—Fe1	−115.4 (6)	C111—C101—C105—Fe11	−116.4 (5)
C10—C6—C7—C8	−1.4 (7)	C110—C106—C107—C108	−2.1 (7)
C20—C6—C7—C8	−174.5 (6)	C120—C106—C107—C108	−177.5 (6)
Fe1—C6—C7—C8	−60.0 (5)	Fe11—C106—C107—C108	−60.6 (4)
C10—C6—C7—Fe1	58.6 (4)	C110—C106—C107—Fe11	58.5 (4)
C20—C6—C7—Fe1	−114.5 (6)	C120—C106—C107—Fe11	−116.9 (6)
C6—C7—C8—C9	1.3 (8)	C106—C107—C108—C109	1.4 (7)
Fe1—C7—C8—C9	−58.7 (5)	Fe11—C107—C108—C109	−58.6 (4)
C6—C7—C8—Fe1	60.0 (4)	C106—C107—C108—Fe11	59.9 (4)
C7—C8—C9—C10	−0.7 (8)	C107—C108—C109—C110	−0.1 (7)
Fe1—C8—C9—C10	−59.2 (5)	Fe11—C108—C109—C110	−58.4 (4)
C7—C8—C9—Fe1	58.6 (5)	C107—C108—C109—Fe11	58.3 (4)
C8—C9—C10—C6	−0.2 (7)	C108—C109—C110—C106	−1.2 (7)
Fe1—C9—C10—C6	−59.7 (4)	Fe11—C109—C110—C106	−60.5 (4)
C8—C9—C10—Fe1	59.5 (5)	C108—C109—C110—Fe11	59.2 (5)
C7—C6—C10—C9	1.0 (7)	C120—C106—C110—C109	176.8 (6)
C20—C6—C10—C9	173.4 (6)	C107—C106—C110—C109	2.0 (7)
Fe1—C6—C10—C9	59.4 (4)	Fe11—C106—C110—C109	60.7 (4)
C7—C6—C10—Fe1	−58.4 (4)	C120—C106—C110—Fe11	116.2 (7)
C20—C6—C10—Fe1	114.0 (7)	C107—C106—C110—Fe11	−58.7 (4)
C5—C1—C11—C12	−155.5 (7)	C102—C101—C111—C112	22.6 (11)
C2—C1—C11—C12	33.4 (11)	C105—C101—C111—C112	−164.2 (6)
Fe1—C1—C11—C12	121.4 (7)	Fe11—C101—C111—C112	112.7 (7)
C1—C11—C12—C15	3.5 (13)	C101—C111—C112—C115	1.8 (12)
C1—C11—C12—C13	−174.8 (6)	C101—C111—C112—C113	−173.4 (6)
C11—C12—C13—O1	−3.3 (10)	C111—C112—C113—O101	−8.9 (9)
C15—C12—C13—O1	177.9 (6)	C115—C112—C113—O101	174.6 (6)
C11—C12—C13—N1	175.0 (6)	C111—C112—C113—N101	171.0 (5)
C15—C12—C13—N1	−3.9 (7)	C115—C112—C113—N101	−5.5 (6)
C19—C14—C15—C16	−3.6 (9)	C119—C114—C115—C116	−6.1 (9)
N1—C14—C15—C16	176.0 (5)	N101—C114—C115—C116	172.6 (5)
C19—C14—C15—C12	−179.3 (6)	C119—C114—C115—C112	179.3 (6)
N1—C14—C15—C12	0.3 (7)	N101—C114—C115—C112	−2.0 (7)
C11—C12—C15—C16	8.9 (13)	C111—C112—C115—C116	15.7 (12)
C13—C12—C15—C16	−172.6 (7)	C113—C112—C115—C116	−168.7 (7)
C11—C12—C15—C14	−176.4 (7)	C111—C112—C115—C114	−171.1 (7)
C13—C12—C15—C14	2.1 (6)	C113—C112—C115—C114	4.6 (6)
C14—C15—C16—C17	2.2 (9)	C114—C115—C116—C117	4.8 (9)
C12—C15—C16—C17	176.5 (7)	C112—C115—C116—C117	177.4 (6)
C15—C16—C17—C18	0.0 (10)	C115—C116—C117—C118	−0.6 (10)
C16—C17—C18—C19	−1.1 (10)	C116—C117—C118—C119	−2.6 (10)
N1—C14—C19—C18	−177.0 (6)	C115—C114—C119—C118	3.0 (9)
C15—C14—C19—C18	2.5 (9)	N101—C114—C119—C118	−175.5 (6)
C17—C18—C19—C14	−0.1 (10)	C117—C118—C119—C114	1.5 (10)
C10—C6—C20—C21	27.5 (11)	C110—C106—C120—C121	19.8 (12)
C7—C6—C20—C21	−161.1 (7)	C107—C106—C120—C121	−166.1 (7)
Fe1—C6—C20—C21	115.6 (7)	Fe11—C106—C120—C121	109.7 (7)
C6—C20—C21—C24	7.8 (13)	C106—C120—C121—C124	0.0 (13)
C6—C20—C21—C22	−176.4 (6)	C106—C120—C121—C122	−173.4 (6)
C20—C21—C22—O2	3.4 (10)	C120—C121—C122—O102	−7.2 (10)
C24—C21—C22—O2	−179.7 (6)	C124—C121—C122—O102	177.5 (6)
C20—C21—C22—N2	−177.3 (6)	C120—C121—C122—N102	172.3 (6)
C24—C21—C22—N2	−0.3 (7)	C124—C121—C122—N102	−2.9 (6)
C28—C23—C24—C25	−2.0 (10)	C128—C123—C124—C125	−5.3 (9)
N2—C23—C24—C25	176.7 (6)	N102—C123—C124—C125	173.1 (5)
C28—C23—C24—C21	−177.7 (6)	C128—C123—C124—C121	−180.0 (6)
N2—C23—C24—C21	1.1 (7)	N102—C123—C124—C121	−1.5 (7)
C20—C21—C24—C25	1.2 (13)	C120—C121—C124—C125	15.2 (12)
C22—C21—C24—C25	−174.9 (7)	C122—C121—C124—C125	−170.8 (7)
C20—C21—C24—C23	175.7 (7)	C120—C121—C124—C123	−171.4 (7)
C22—C21—C24—C23	−0.4 (7)	C122—C121—C124—C123	2.6 (6)
C23—C24—C25—C26	1.8 (9)	C123—C124—C125—C126	4.5 (9)
C21—C24—C25—C26	175.8 (7)	C121—C124—C125—C126	177.3 (6)
C24—C25—C26—C27	−0.3 (10)	C124—C125—C126—C127	−1.4 (9)
C25—C26—C27—C28	−1.1 (10)	C125—C126—C127—C128	−1.2 (10)
N2—C23—C28—C27	−177.8 (6)	N102—C123—C128—C127	−175.3 (6)
C24—C23—C28—C27	0.7 (10)	C124—C123—C128—C127	2.8 (10)
C26—C27—C28—C23	0.9 (10)	C126—C127—C128—C123	0.4 (10)
O1—C13—N1—C14	−177.6 (6)	O101—C113—N101—C114	−175.7 (6)
C12—C13—N1—C14	4.2 (7)	C112—C113—N101—C114	4.5 (7)
C19—C14—N1—C13	176.6 (6)	C119—C114—N101—C113	177.0 (6)
C15—C14—N1—C13	−2.9 (7)	C115—C114—N101—C113	−1.6 (7)
O2—C22—N2—C23	−179.6 (6)	O102—C122—N102—C123	−178.3 (6)
C21—C22—N2—C23	1.0 (7)	C121—C122—N102—C123	2.1 (7)
C28—C23—N2—C22	177.3 (6)	C128—C123—N102—C122	177.9 (6)
C24—C23—N2—C22	−1.3 (7)	C124—C123—N102—C122	−0.4 (7)
C4—C5—Fe1—C3	37.0 (4)	C109—C110—Fe11—C105	108.8 (4)
C1—C5—Fe1—C3	−81.1 (4)	C106—C110—Fe11—C105	−132.9 (4)
C4—C5—Fe1—C10	−129.9 (4)	C109—C110—Fe11—C102	−171.5 (5)
C1—C5—Fe1—C10	112.0 (4)	C106—C110—Fe11—C102	−53.2 (7)
C1—C5—Fe1—C4	−118.1 (5)	C109—C110—Fe11—C107	−79.7 (4)
C4—C5—Fe1—C2	80.6 (4)	C106—C110—Fe11—C107	38.7 (4)
C1—C5—Fe1—C2	−37.5 (4)	C109—C110—Fe11—C104	68.2 (5)
C4—C5—Fe1—C9	−86.5 (4)	C106—C110—Fe11—C104	−173.4 (4)
C1—C5—Fe1—C9	155.4 (4)	C109—C110—Fe11—C103	34.9 (13)
C4—C5—Fe1—C8	−52.0 (7)	C106—C110—Fe11—C103	153.3 (10)
C1—C5—Fe1—C8	−170.2 (5)	C106—C110—Fe11—C109	118.4 (5)
C4—C5—Fe1—C6	−169.5 (4)	C109—C110—Fe11—C106	−118.4 (5)
C1—C5—Fe1—C6	72.4 (5)	C109—C110—Fe11—C101	152.6 (4)
C4—C5—Fe1—C1	118.1 (5)	C106—C110—Fe11—C101	−89.0 (4)
C8—C7—Fe1—C3	−85.9 (5)	C109—C110—Fe11—C108	−36.4 (4)
C6—C7—Fe1—C3	154.7 (4)	C106—C110—Fe11—C108	81.9 (4)
C8—C7—Fe1—C10	81.4 (4)	C104—C105—Fe11—C110	−129.0 (4)
C6—C7—Fe1—C10	−38.0 (4)	C101—C105—Fe11—C110	112.0 (4)
C8—C7—Fe1—C4	−49.6 (7)	C104—C105—Fe11—C102	81.3 (4)
C6—C7—Fe1—C4	−169.0 (5)	C101—C105—Fe11—C102	−37.7 (4)
C8—C7—Fe1—C2	−129.3 (4)	C101—C105—Fe11—C104	−119.1 (5)
C6—C7—Fe1—C2	111.3 (4)	C104—C105—Fe11—C103	37.2 (4)
C8—C7—Fe1—C9	37.4 (4)	C101—C105—Fe11—C103	−81.8 (4)
C6—C7—Fe1—C9	−82.0 (4)	C104—C105—Fe11—C109	−85.9 (4)
C6—C7—Fe1—C8	−119.4 (6)	C101—C105—Fe11—C109	155.1 (4)
C8—C7—Fe1—C6	119.4 (6)	C104—C105—Fe11—C106	−169.6 (4)
C8—C7—Fe1—C1	−169.8 (4)	C101—C105—Fe11—C106	71.3 (5)
C6—C7—Fe1—C1	70.8 (5)	C104—C105—Fe11—C101	119.1 (5)
C4—C3—Fe1—C5	−37.6 (4)	C104—C105—Fe11—C108	−50.1 (6)
C2—C3—Fe1—C5	82.9 (4)	C101—C105—Fe11—C108	−169.1 (5)
C4—C3—Fe1—C7	151.1 (4)	C103—C102—Fe11—C110	−171.0 (5)
C2—C3—Fe1—C7	−88.4 (5)	C101—C102—Fe11—C110	−52.3 (7)
C4—C3—Fe1—C10	38.4 (15)	C103—C102—Fe11—C105	−80.7 (4)
C2—C3—Fe1—C10	158.9 (12)	C101—C102—Fe11—C105	38.1 (4)
C2—C3—Fe1—C4	120.5 (6)	C103—C102—Fe11—C107	107.7 (4)
C4—C3—Fe1—C2	−120.5 (6)	C101—C102—Fe11—C107	−133.5 (4)
C4—C3—Fe1—C9	68.2 (5)	C103—C102—Fe11—C104	−37.1 (4)
C2—C3—Fe1—C9	−171.3 (4)	C101—C102—Fe11—C104	81.6 (4)
C4—C3—Fe1—C8	108.3 (4)	C101—C102—Fe11—C103	118.7 (5)
C2—C3—Fe1—C8	−131.2 (4)	C103—C102—Fe11—C109	34.7 (13)
C4—C3—Fe1—C6	−174.1 (5)	C101—C102—Fe11—C109	153.5 (11)
C2—C3—Fe1—C6	−53.6 (7)	C103—C102—Fe11—C106	152.2 (4)
C4—C3—Fe1—C1	−82.0 (4)	C101—C102—Fe11—C106	−89.1 (4)
C2—C3—Fe1—C1	38.5 (4)	C103—C102—Fe11—C101	−118.7 (5)
C9—C10—Fe1—C5	108.1 (4)	C103—C102—Fe11—C108	67.5 (5)
C6—C10—Fe1—C5	−132.3 (4)	C101—C102—Fe11—C108	−173.7 (4)
C9—C10—Fe1—C7	−81.4 (4)	C108—C107—Fe11—C110	80.6 (4)
C6—C10—Fe1—C7	38.2 (4)	C106—C107—Fe11—C110	−38.6 (4)
C9—C10—Fe1—C3	36.5 (15)	C108—C107—Fe11—C102	−129.7 (4)
C6—C10—Fe1—C3	156.1 (12)	C106—C107—Fe11—C102	111.0 (4)
C9—C10—Fe1—C4	67.7 (5)	C108—C107—Fe11—C104	−50.3 (6)
C6—C10—Fe1—C4	−172.7 (4)	C106—C107—Fe11—C104	−169.5 (4)
C9—C10—Fe1—C2	−172.5 (5)	C108—C107—Fe11—C103	−86.0 (4)
C6—C10—Fe1—C2	−52.9 (7)	C106—C107—Fe11—C103	154.8 (4)
C6—C10—Fe1—C9	119.6 (6)	C108—C107—Fe11—C109	37.2 (4)
C9—C10—Fe1—C8	−37.7 (4)	C106—C107—Fe11—C109	−82.1 (4)
C6—C10—Fe1—C8	81.9 (4)	C108—C107—Fe11—C106	119.3 (5)
C9—C10—Fe1—C6	−119.6 (6)	C108—C107—Fe11—C101	−169.4 (4)
C9—C10—Fe1—C1	151.7 (4)	C106—C107—Fe11—C101	71.4 (5)
C6—C10—Fe1—C1	−88.7 (4)	C106—C107—Fe11—C108	−119.3 (5)
C3—C4—Fe1—C5	119.9 (6)	C103—C104—Fe11—C110	−168.7 (4)
C3—C4—Fe1—C7	−54.7 (7)	C105—C104—Fe11—C110	71.6 (5)
C5—C4—Fe1—C7	−174.6 (5)	C103—C104—Fe11—C105	119.6 (5)
C5—C4—Fe1—C3	−119.9 (6)	C103—C104—Fe11—C102	37.6 (4)
C3—C4—Fe1—C10	−169.7 (4)	C105—C104—Fe11—C102	−82.0 (4)
C5—C4—Fe1—C10	70.4 (5)	C103—C104—Fe11—C107	−54.4 (6)
C3—C4—Fe1—C2	37.0 (4)	C105—C104—Fe11—C107	−174.0 (4)
C5—C4—Fe1—C2	−82.9 (4)	C105—C104—Fe11—C103	−119.6 (5)
C3—C4—Fe1—C9	−130.6 (4)	C103—C104—Fe11—C109	−129.8 (4)
C5—C4—Fe1—C9	109.5 (4)	C105—C104—Fe11—C109	110.6 (4)
C3—C4—Fe1—C8	−87.8 (4)	C103—C104—Fe11—C106	166.7 (13)
C5—C4—Fe1—C8	152.3 (4)	C105—C104—Fe11—C106	47.1 (15)
C3—C4—Fe1—C6	165.0 (12)	C103—C104—Fe11—C101	81.5 (4)
C5—C4—Fe1—C6	45.1 (15)	C105—C104—Fe11—C101	−38.1 (4)
C3—C4—Fe1—C1	81.3 (4)	C103—C104—Fe11—C108	−87.5 (4)
C5—C4—Fe1—C1	−38.6 (4)	C105—C104—Fe11—C108	152.9 (4)
C3—C2—Fe1—C5	−80.8 (4)	C104—C103—Fe11—C110	41.3 (12)
C1—C2—Fe1—C5	37.6 (4)	C102—C103—Fe11—C110	161.0 (10)
C3—C2—Fe1—C7	109.3 (4)	C104—C103—Fe11—C105	−37.4 (4)
C1—C2—Fe1—C7	−132.4 (4)	C102—C103—Fe11—C105	82.3 (4)
C1—C2—Fe1—C3	118.4 (6)	C104—C103—Fe11—C102	−119.7 (5)
C3—C2—Fe1—C10	−170.5 (5)	C104—C103—Fe11—C107	150.5 (4)
C1—C2—Fe1—C10	−52.1 (7)	C102—C103—Fe11—C107	−89.7 (4)
C3—C2—Fe1—C4	−36.8 (4)	C102—C103—Fe11—C104	119.7 (5)
C1—C2—Fe1—C4	81.6 (4)	C104—C103—Fe11—C109	69.4 (5)
C3—C2—Fe1—C9	32.5 (15)	C102—C103—Fe11—C109	−170.8 (4)
C1—C2—Fe1—C9	150.9 (12)	C104—C103—Fe11—C106	−175.2 (5)
C3—C2—Fe1—C8	68.5 (5)	C102—C103—Fe11—C106	−55.4 (6)
C1—C2—Fe1—C8	−173.1 (4)	C104—C103—Fe11—C101	−81.8 (4)
C3—C2—Fe1—C6	153.3 (4)	C102—C103—Fe11—C101	37.9 (4)
C1—C2—Fe1—C6	−88.4 (4)	C104—C103—Fe11—C108	108.2 (4)
C3—C2—Fe1—C1	−118.4 (6)	C102—C103—Fe11—C108	−132.0 (4)
C8—C9—Fe1—C5	152.3 (4)	C108—C109—Fe11—C110	−120.9 (6)
C10—C9—Fe1—C5	−88.5 (4)	C110—C109—Fe11—C105	−88.5 (4)
C8—C9—Fe1—C7	−37.3 (4)	C108—C109—Fe11—C105	150.6 (4)
C10—C9—Fe1—C7	81.9 (4)	C110—C109—Fe11—C102	161.3 (11)
C8—C9—Fe1—C3	70.5 (5)	C108—C109—Fe11—C102	40.3 (13)
C10—C9—Fe1—C3	−170.3 (4)	C110—C109—Fe11—C107	83.7 (4)
C8—C9—Fe1—C10	−119.2 (6)	C108—C109—Fe11—C107	−37.3 (4)
C8—C9—Fe1—C4	109.3 (4)	C110—C109—Fe11—C104	−131.1 (4)
C10—C9—Fe1—C4	−131.5 (4)	C108—C109—Fe11—C104	108.0 (4)
C8—C9—Fe1—C2	44.1 (14)	C110—C109—Fe11—C103	−170.4 (4)
C10—C9—Fe1—C2	163.3 (12)	C108—C109—Fe11—C103	68.7 (5)
C10—C9—Fe1—C8	119.2 (6)	C110—C109—Fe11—C106	38.8 (4)
C8—C9—Fe1—C6	−81.6 (4)	C108—C109—Fe11—C106	−82.2 (4)
C10—C9—Fe1—C6	37.6 (4)	C110—C109—Fe11—C101	−54.6 (7)
C8—C9—Fe1—C1	−175.0 (5)	C108—C109—Fe11—C101	−175.5 (5)
C10—C9—Fe1—C1	−55.8 (7)	C110—C109—Fe11—C108	120.9 (6)
C7—C8—Fe1—C5	−171.6 (5)	C120—C106—Fe11—C110	−126.7 (7)
C9—C8—Fe1—C5	−51.8 (7)	C107—C106—Fe11—C110	118.1 (5)
C9—C8—Fe1—C7	119.8 (6)	C110—C106—Fe11—C105	68.8 (5)
C7—C8—Fe1—C3	111.0 (4)	C120—C106—Fe11—C105	−58.0 (6)
C9—C8—Fe1—C3	−129.2 (4)	C107—C106—Fe11—C105	−173.1 (4)
C7—C8—Fe1—C10	−81.9 (4)	C110—C106—Fe11—C102	154.3 (4)
C9—C8—Fe1—C10	37.8 (4)	C120—C106—Fe11—C102	27.6 (6)
C7—C8—Fe1—C4	153.7 (4)	C107—C106—Fe11—C102	−87.6 (4)
C9—C8—Fe1—C4	−86.6 (4)	C110—C106—Fe11—C107	−118.1 (5)
C7—C8—Fe1—C2	71.7 (5)	C120—C106—Fe11—C107	115.2 (7)
C9—C8—Fe1—C2	−168.6 (4)	C110—C106—Fe11—C104	29.1 (15)
C7—C8—Fe1—C9	−119.8 (6)	C120—C106—Fe11—C104	−97.6 (14)
C7—C8—Fe1—C6	−37.9 (4)	C107—C106—Fe11—C104	147.3 (13)
C9—C8—Fe1—C6	81.9 (4)	C110—C106—Fe11—C103	−168.1 (5)
C7—C8—Fe1—C1	46.2 (16)	C120—C106—Fe11—C103	65.2 (8)
C9—C8—Fe1—C1	166.0 (13)	C107—C106—Fe11—C103	−50.0 (6)
C10—C6—Fe1—C5	68.0 (5)	C110—C106—Fe11—C109	−37.8 (4)
C7—C6—Fe1—C5	−173.2 (4)	C120—C106—Fe11—C109	−164.5 (6)
C20—C6—Fe1—C5	−57.2 (6)	C107—C106—Fe11—C109	80.3 (4)
C10—C6—Fe1—C7	−118.8 (5)	C110—C106—Fe11—C101	110.3 (4)
C20—C6—Fe1—C7	116.0 (7)	C120—C106—Fe11—C101	−16.4 (6)
C10—C6—Fe1—C3	−169.5 (5)	C107—C106—Fe11—C101	−131.6 (4)
C7—C6—Fe1—C3	−50.7 (7)	C110—C106—Fe11—C108	−80.9 (4)
C20—C6—Fe1—C3	65.3 (8)	C120—C106—Fe11—C108	152.3 (6)
C7—C6—Fe1—C10	118.8 (5)	C107—C106—Fe11—C108	37.2 (4)
C20—C6—Fe1—C10	−125.2 (7)	C102—C101—Fe11—C110	154.6 (4)
C10—C6—Fe1—C4	30.4 (15)	C105—C101—Fe11—C110	−86.4 (4)
C7—C6—Fe1—C4	149.1 (13)	C111—C101—Fe11—C110	27.5 (6)
C20—C6—Fe1—C4	−94.9 (14)	C102—C101—Fe11—C105	−119.1 (5)
C10—C6—Fe1—C2	154.1 (4)	C111—C101—Fe11—C105	113.9 (6)
C7—C6—Fe1—C2	−87.1 (4)	C105—C101—Fe11—C102	119.1 (5)
C20—C6—Fe1—C2	28.9 (6)	C111—C101—Fe11—C102	−127.1 (7)
C10—C6—Fe1—C9	−37.6 (4)	C102—C101—Fe11—C107	67.7 (5)
C7—C6—Fe1—C9	81.2 (4)	C105—C101—Fe11—C107	−173.2 (4)
C20—C6—Fe1—C9	−162.8 (6)	C111—C101—Fe11—C107	−59.4 (6)
C10—C6—Fe1—C8	−81.3 (4)	C102—C101—Fe11—C104	−81.5 (4)
C7—C6—Fe1—C8	37.4 (4)	C105—C101—Fe11—C104	37.6 (4)
C20—C6—Fe1—C8	153.4 (6)	C111—C101—Fe11—C104	151.4 (6)
C10—C6—Fe1—C1	109.9 (4)	C102—C101—Fe11—C103	−38.1 (4)
C7—C6—Fe1—C1	−131.4 (4)	C105—C101—Fe11—C103	81.0 (4)
C20—C6—Fe1—C1	−15.4 (6)	C111—C101—Fe11—C103	−165.2 (6)
C2—C1—Fe1—C5	−119.8 (5)	C102—C101—Fe11—C109	−168.6 (5)
C11—C1—Fe1—C5	115.7 (7)	C105—C101—Fe11—C109	−49.6 (7)
C5—C1—Fe1—C7	−171.0 (4)	C111—C101—Fe11—C109	64.3 (7)
C2—C1—Fe1—C7	69.2 (5)	C102—C101—Fe11—C106	109.7 (4)
C11—C1—Fe1—C7	−55.4 (6)	C105—C101—Fe11—C106	−131.2 (4)
C5—C1—Fe1—C3	81.8 (4)	C111—C101—Fe11—C106	−17.4 (6)
C2—C1—Fe1—C3	−38.0 (4)	C102—C101—Fe11—C108	27.3 (16)
C11—C1—Fe1—C3	−162.5 (6)	C105—C101—Fe11—C108	146.3 (13)
C5—C1—Fe1—C10	−85.7 (4)	C111—C101—Fe11—C108	−99.8 (14)
C2—C1—Fe1—C10	154.5 (4)	C109—C108—Fe11—C110	36.7 (4)
C11—C1—Fe1—C10	30.0 (6)	C107—C108—Fe11—C110	−83.0 (4)
C5—C1—Fe1—C4	38.3 (4)	C109—C108—Fe11—C105	−54.6 (7)
C2—C1—Fe1—C4	−81.4 (4)	C107—C108—Fe11—C105	−174.3 (5)
C11—C1—Fe1—C4	154.0 (6)	C109—C108—Fe11—C102	−169.3 (4)
C5—C1—Fe1—C2	119.8 (5)	C107—C108—Fe11—C102	71.0 (5)
C11—C1—Fe1—C2	−124.5 (7)	C109—C108—Fe11—C107	119.7 (6)
C5—C1—Fe1—C9	−48.0 (6)	C109—C108—Fe11—C104	−87.8 (4)
C2—C1—Fe1—C9	−167.8 (5)	C107—C108—Fe11—C104	152.5 (4)
C11—C1—Fe1—C9	67.6 (7)	C109—C108—Fe11—C103	−130.2 (4)
C5—C1—Fe1—C8	150.1 (14)	C107—C108—Fe11—C103	110.1 (4)
C2—C1—Fe1—C8	30.3 (16)	C107—C108—Fe11—C109	−119.7 (6)
C11—C1—Fe1—C8	−94.2 (15)	C109—C108—Fe11—C106	81.4 (4)
C5—C1—Fe1—C6	−129.7 (4)	C107—C108—Fe11—C106	−38.3 (4)
C2—C1—Fe1—C6	110.5 (4)	C109—C108—Fe11—C101	167.8 (13)
C11—C1—Fe1—C6	−14.1 (6)	C107—C108—Fe11—C101	48.1 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O101	0.88	2.01	2.876 (7)	168
N2—H2A···O102	0.88	1.98	2.849 (7)	171
N101—H101···O1	0.88	1.92	2.774 (7)	163
N102—H10A···O2	0.88	1.95	2.822 (7)	169