An octa­nuclear iron(III) isobutyrate wheel

The reaction of the [mu]₃-oxido-centred trinuclear isobutyrate cluster [Fe₃O(O₂CCHMe₂)₆(H₂O)₃]⁺ with an excess of phenol (PhOH) in chloro­form produces a novel octa­nuclear Fe^III cluster, cyclo-tetra-[mu]₂-hydroxido-dodeca-[mu]₂-isobutyrato-[kappa]²⁴O:O'-octa-[mu]₂-phenolato-[kappa]¹⁶O:O'-octa­iron(III) phenol hexa­solvate monohydrate, [Fe₈(C₄H₇O₂)₁₂(C₆H₅O)₈(OH)₄]·6C₆H₅OH·H₂O. The neutral cluster is located about a centre of inversion and consists of a planar ring of eight Fe^III centres with two types of bridges between adjacent Fe atoms: each Fe atom is bridged to one of its neighbours by a [mu]-hydroxide and two 1,3-bridging carboxyl­ates, or by two phenolate and one 1,3-bridging isobutyrate ligand. The cavity within the {Fe₈} wheel is occupied by a disordered water mol­ecule. Inter­molecular O-H...O hydrogen bonds and C-H...[pi] interactions connect the clusters and the phenol solvent mol­ecules to form a three-dimensional network.

S1. Comment

The design of new polynuclear iron(III) cluster complexes has garnered substantial interest due to their archetypal role as single-molecule magnets (SMMs), since initial reports on {Fe₈} cages by Wieghardt et al. (1984) and Gatteschi et al. (2000), followed by the discovery of other ferric {Fe₁₀} (Benelli et al., 2001) and {Fe₁₉} (Goodwin et al., 2000) SMMs. Of special interest are the wheel-shaped high-nuclearity iron cluster complexes, which can magnetically be regarded as chains with a finite number of spin centres. Several iron wheels, ranging from {Fe₆} (Caneschi et al., 1995; Saalfrank et al. 1997; Hoshino et al., 2009) to {Fe₈} (Saalfrank et al., 1997; Canada-Vilalta, O'Brien et al., 2003; Canada-Vilalta, Pink & Christou, 2003; Jones et al., 2006), {Fe₉} (Yao et al., 2006), {Fe₁₀} (Taft & Lippard, 1990; Taft et al., 1994; Benelli et al., 1996; Liu et al., 2001; Jones et al., 2002), {Fe₁₂} (Abbati et al., 2000; Raptopoulou et al., 2002; Abu-Nawwas et al., 2004), {Fe₁₆} (Jones et al., 2002, 2006) and {Fe₁₈} (King et al., 2006), have been reported so far. Compared with other polynuclear metal clusters comprising paramagnetic metal ions, wheel-type clusters generally reveal interesting physical properties, e.g. soliton excitations, and can be a model compounds for studying one-dimensional magnetic materials [see, for example, Gatteschi et al. (2006) and Timco et al. (2009, 2011)]. Here, we report the title novel iron(III) isobutyrate-based wheel with phenolate (PhO) ligands, (I).

Single-crystal X-ray diffraction analysis reveals that (I) crystallizes in the triclinic space group P1, and consists of a wheel-shaped octanuclear [Fe₈(OH)₄(O₂CCHMe₂)₁₂(PhO)₈] neutral cluster unit, six solvate phenol molecules and one water molecule per formula unit (Fig. 1). The asymmetric unit of (I) contains half of the eight Fe^III ions, five carboxylate residues, four phenolate groups, two phenol molecules and one half-molecule of water. The eight Fe^III ions are bridged by a combination of isobutyrate, phenolate and hydroxide groups into a cyclic structure of ~ 8.5 Å in diameter (measured between opposite Fe^III ions). The isobutyrate groups link neighbouring Fe^III ions in the usual manner, adopting a µ₂-η¹:η¹ bridging mode. The distances between two Fe^III ions bridged by two phenolate groups and one isobutyrate are in the range 3.108 (6)–3.115 (6) Å, shorter than the distances of 3.426 (6)–3.435 (6) Å between Fe^III ions linked by a µ-hydroxide and two bridging carboxylate groups. Each Fe^III ion adopts a distorted octahedral arrangement formed by three O atoms from three bridging carboxylate ligands [Fe—O_carb bond lengths 1.972 (2)–2.065 (2) Å, two O atoms from two phenolate groups [Fe—O_PhO = 1.998 (2)–2.031 (2) Å] and one hydroxide [Fe—O_OH = 1.959 (2)–1.977 (2) Å].

The structure of (I) is comparable with that of the {Fe₈} rings based on pivalate or benzoate ligands (Canada-Vilalta, Pink & Christou, 2003), with small differences in the Fe—O distances: Fe—O_carb = 1.830 (2)–2.15 (1) (pivalate) and 1.964 (6)–2.050 (6) Å (benzoate); Fe—O_PhO = 2.007 (2)–2.015 (2) (pivalate) and 2.005 (6)–2.022 (6) Å (benzoate); and Fe—OH = 1.961 (2)–1.982 (2) (pivalate) and 1.969 (6)–1.976 (6) Å (benzoate).

The ferric isobutyrate wheel in (I) contains a cavity which can be occupied by small guest molecules. The inner rims of the wheel are geometrically constricted by the opposite aromatic phenol ligands, resulting in a distance of ca 5.5 Å and a depth of 10.7 Å. A single water molecule (atom O22) resides in the central cavity of (I) and forms O—H···O hydrogen bonds with µ-hydroxide groups (atoms O1 and O14) of the ring, with distances of 2.977 (5) and 2.984 (5) Å (Table 1), respectively, as shown in Fig. 1(b). The Fe^III wheels are stacked on top of each other to form channels along the a axis. The crystal packing of (I) is illustrated in Fig. 2.

All the phenol solvate molecules of (I) participate in the formation of extensive O—H···O hydrogen bonding with the Fe^III clusters. Thus, phenol atoms O19 and O20 form hydrogen bonds of 2.945 (3) and 2.795 (3) Å with coordinated carboxylate atoms O8 and O18(x + 1, y + 1, z) of the {Fe₈} ring, respectively. Further, the oxygen site O20 is bound to atom O21 from a third phenol molecule with a shorter O—H···O distance of 2.773 (4) Å. The complete set of parameters for the O—H···O hydrogen-bonding interactions in (I) are summarized in Table 1. Additionally, neighbouring {Fe₈} rings are associated through aliphatic–aromatic C—H···π hydrogen bonds between the methyl groups (C15—H15C and C8—H8A) of the isobutyrates and a phenol solvate molecule (C61–C66/O21) to generate a hydrogen-bonded one-dimensional chain (Fig. 3). The C—H···π distances involved in this contact are 2.63 and 2.87 Å, respectively, which are shorter than the value of 3.05 Å considered to be relevant for the presence of a C—H···π interaction [see, for example, Nishio (2004) and Suezawa et al. (2001)]. Moreover, significant intermolecular aromatic–aromatic edge-to-face C—H···π contacts are present between the phenol solvate molecules, influencing the assembly of a supramolecular three-dimensional network.

Related literature

For related literature, see: Abbati et al. (2000); Abu-Nawwas, Cano, Christian, Mallah, Rajaramm, Teat, Winpenny & Yukawa (2004); Benelli et al. (1996, 2001); Canada-Vilalta, O'Brien, Pink, Davidson & Christou (2003); Canada-Vilalta, Pink & Christou (2003); Caneschi et al. (1995); Gatteschi et al. (2000, 2006); Goodwin et al. (2000); Hoshino et al. (2009); Jones et al. (2002, 2006); King et al. (2006); Liu et al. (2001); Malaestean et al. (2010); Nishio (2004); Raptopoulou et al. (2002); Saalfrank et al. (1997); Suezawa et al. (2001); Taft & Lippard (1990); Taft et al. (1994); Timco et al. (2009, 2011); Wieghardt et al. (1984); Yao et al. (2006).

S2. Experimental

Solvents and reagents were obtained commercially and used without further purification. The precursor [Fe₃O(O₂CCHMe₂)₆(H₂O)₃]NO₃ was prepared according to a previously reported procedure (Malaestean et al., 2010). Phenol (0.40 g, 4.25 mmol) was added to a chloroform solution (10 ml) of [Fe₃O(O₂CCHMe₂)₆(H₂O)₃]NO₃ (0.168 g, 0.204 mmol). The reaction mixture was stirred for 10 min at room temperature and then filtered. Red crystals of (I) suitable for X-ray diffraction analysis were obtained within a week by slow evaporation of the reaction solution.

S3. Refinement

A total of 59 similarity restraints (C—C distances and displacement parameters for disordered atoms) were used to model the disordered isobutyrate groups. The H atoms of the main cluster were treated using a riding model, with fixed distances of C—H = 0.95–1.00 Å and O—H = 0.80–0.92 Å [Please check added text], and with U_iso(H) = 1.2 or 1.5U_eq(C,O). The H atoms of the disordered (via the inversion centre) water molecule were not located or included in the refinement. However, they were taken into account for the final formula to obtain true metric data.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 displacement ellipsoid plot at the ??% probability level of the contents of the asymmetric unit of (I). Only one conformation of disordered components is depicted.
	Fig. 2. The molecular structure of (I), showing (a) a side view and (b) a top view, displaying the hydrogen-bonding interactions (dashed lines). H atoms, except those participating in hydrogen bonding, and disordered Me3C groups have been omitted for clarity. (Colour scheme in the electronic version of the journal: Fe green spheres, O red sticks, C grey sticks, H blue spheres and water molecule red sphere.)
	Fig. 3. The stacked packing of {Fe8} wheels extended within the bc plane in the lattice of (I) (the viewing direction is approximately along a). Isobutyrate and phenolate ligands and solvent phenol molecules have been omitted for clarity.
	Fig. 4. Intermolecular C—H···π contacts (dashed lines) between neighbouring {Fe8} wheel clusters in the solid-state lattice of (I). (Colour scheme in the electronic version of the journal: O red spheres, C grey sticks and H white spheres.)

cyclo-tetra-µ₂-hydroxido-dodeca-µ₂-isobutyrato- κ²⁴O:O'-octa-µ₂-phenolato-octairon(III) phenol hexasolvate monohydrate

Crystal data

[Fe8(C4H7O2)12(C6H5O)8(OH)4]·6C6H6O·H2O	Z = 1
Mr = 2887.45	F(000) = 1510
Triclinic, P1	Dx = 1.396 Mg m^−3
a = 13.2648 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 16.6182 (9) Å	Cell parameters from 7771 reflections
c = 17.679 (1) Å	θ = 2.4–26.7°
α = 90.557 (1)°	µ = 0.90 mm^−1
β = 110.485 (1)°	T = 153 K
γ = 108.261 (1)°	Needle, red
V = 3435.5 (3) Å^3	0.27 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	12041 independent reflections
Radiation source: fine-focus sealed tube	9628 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ϕ and ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.161, Tmax = 0.931	k = −19→19
27326 measured reflections	l = −20→21

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.14	w = 1/[σ^2(Fo^2) + (0.0334P)^2 + 4.9888P] where P = (Fo^2 + 2Fc^2)/3
12041 reflections	(Δ/σ)max = 0.001
867 parameters	Δρmax = 1.03 e Å^−3
59 restraints	Δρmin = −1.05 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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)
Fe1	0.29989 (4)	0.41781 (3)	0.24308 (3)	0.01663 (11)
Fe2	0.45790 (4)	0.60789 (3)	0.27745 (3)	0.01677 (11)
Fe3	0.65118 (4)	0.74718 (3)	0.44863 (3)	0.01695 (11)
Fe4	0.25286 (4)	0.26246 (3)	0.36501 (3)	0.01663 (11)
C1	0.8176 (3)	0.9030 (2)	0.5665 (2)	0.0203 (7)
C2	0.8700 (3)	0.9996 (2)	0.5818 (2)	0.0251 (8)
H2A	0.9522	1.0153	0.6184	0.030*
C3	0.8646 (4)	1.0383 (2)	0.5040 (2)	0.0420 (10)
H3A	0.9045	1.0149	0.4770	0.063*
H3B	0.9014	1.1006	0.5169	0.063*
H3C	0.7846	1.0246	0.4677	0.063*
C4	0.8085 (4)	1.0341 (3)	0.6266 (3)	0.0448 (11)
H4A	0.8140	1.0080	0.6768	0.067*
H4B	0.7278	1.0199	0.5915	0.067*
H4C	0.8443	1.0963	0.6403	0.067*
C5	0.4592 (3)	0.7839 (2)	0.3166 (2)	0.0264 (8)
C6	0.4069 (4)	0.8515 (3)	0.2863 (3)	0.0500 (12)
H6A	0.4118	0.8579	0.2314	0.060*
C7	0.4703 (5)	0.9376 (3)	0.3330 (3)	0.0638 (15)
H7A	0.5508	0.9538	0.3394	0.096*
H7B	0.4646	0.9374	0.3868	0.096*
H7C	0.4375	0.9788	0.3038	0.096*
C8	0.2808 (4)	0.8172 (3)	0.2695 (4)	0.0679 (16)
H8A	0.2467	0.8610	0.2493	0.102*
H8B	0.2690	0.8018	0.3199	0.102*
H8C	0.2446	0.7664	0.2284	0.102*
C9	0.3051 (3)	0.5220 (2)	0.1070 (2)	0.0311 (9)
C10	0.2447 (8)	0.5270 (7)	0.0191 (5)	0.049 (2)	0.570 (5)
H10	0.2739	0.5871	0.0080	0.059*	0.570 (5)
C10'	0.2890 (13)	0.5195 (10)	0.0145 (7)	0.050 (2)	0.430 (5)
H10'	0.2998	0.5791	0.0009	0.060*	0.430 (5)
C11	0.2761 (9)	0.4691 (5)	−0.0288 (5)	0.059 (2)	0.570 (5)
H11A	0.2651	0.4137	−0.0083	0.088*	0.570 (5)
H11B	0.3563	0.4954	−0.0225	0.088*	0.570 (5)
H11C	0.2271	0.4608	−0.0866	0.088*	0.570 (5)
C11'	0.3780 (12)	0.4917 (8)	−0.0015 (7)	0.064 (2)	0.430 (5)
H11D	0.4533	0.5222	0.0403	0.096*	0.430 (5)
H11E	0.3786	0.5048	−0.0553	0.096*	0.430 (5)
H11F	0.3600	0.4300	0.0000	0.096*	0.430 (5)
C12	0.1169 (7)	0.4992 (6)	−0.0069 (5)	0.062 (3)	0.570 (5)
H12A	0.0826	0.5009	−0.0655	0.093*	0.570 (5)
H12B	0.0968	0.5379	0.0229	0.093*	0.570 (5)
H12C	0.0879	0.4409	0.0050	0.093*	0.570 (5)
C12'	0.1664 (13)	0.4635 (8)	−0.0392 (7)	0.086 (4)	0.430 (5)
H12D	0.1514	0.4739	−0.0959	0.128*	0.430 (5)
H12E	0.1120	0.4778	−0.0205	0.128*	0.430 (5)
H12F	0.1579	0.4031	−0.0354	0.128*	0.430 (5)
C13	0.3063 (3)	0.2404 (2)	0.2169 (2)	0.0292 (8)
C14	0.3573 (8)	0.1883 (5)	0.1753 (5)	0.0317 (18)	0.570 (5)
H14	0.4378	0.2275	0.1896	0.038*	0.570 (5)
C14'	0.2905 (10)	0.1693 (5)	0.1508 (5)	0.024 (2)	0.430 (5)
H14'	0.2100	0.1297	0.1353	0.029*	0.430 (5)
C15	0.3009 (4)	0.1918 (3)	0.0808 (3)	0.0536 (9)
H15A	0.3172	0.1513	0.0501	0.080*
H15B	0.3326	0.2497	0.0689	0.080*
H15C	0.2180	0.1765	0.0649	0.080*
C16	0.3715 (5)	0.1168 (4)	0.2050 (3)	0.0691 (11)
H16A	0.3853	0.0834	0.1661	0.104*
H16B	0.3024	0.0827	0.2138	0.104*
H16C	0.4371	0.1322	0.2569	0.104*
C17	0.0687 (3)	0.3140 (2)	0.2441 (2)	0.0266 (8)
C18	−0.0545 (4)	0.3084 (5)	0.2158 (4)	0.100 (3)
H18A	−0.0396	0.3643	0.2468	0.120*
C19	−0.1015 (4)	0.3326 (3)	0.1348 (3)	0.0536 (9)
H19A	−0.1786	0.3334	0.1247	0.080*
H19B	−0.1048	0.2911	0.0935	0.080*
H19C	−0.0524	0.3896	0.1320	0.080*
C20	−0.1237 (5)	0.2586 (4)	0.2533 (3)	0.0691 (11)
H20A	−0.1981	0.2671	0.2334	0.104*
H20B	−0.0873	0.2754	0.3124	0.104*
H20C	−0.1348	0.1982	0.2404	0.104*
C21	0.6975 (3)	0.7152 (2)	0.2985 (2)	0.0303 (9)
C22	0.8024 (6)	0.7119 (5)	0.2768 (4)	0.0365 (15)	0.570 (5)
H22	0.8386	0.6749	0.3132	0.044*	0.570 (5)
C22'	0.7672 (7)	0.7523 (5)	0.2459 (5)	0.0209 (15)	0.430 (5)
H22'	0.7310	0.7888	0.2086	0.025*	0.430 (5)
C23	0.8901 (4)	0.8049 (3)	0.3001 (3)	0.0557 (14)
H23A	0.9373	0.8136	0.2669	0.083*
H23B	0.9391	0.8137	0.3579	0.083*
H23C	0.8489	0.8459	0.2902	0.083*
C24	0.7684 (4)	0.6755 (3)	0.1955 (3)	0.0719 (18)
H24A	0.8305	0.7000	0.1757	0.108*
H24B	0.7003	0.6879	0.1612	0.108*
H24C	0.7508	0.6135	0.1931	0.108*
C25	0.5498 (3)	0.4265 (2)	0.1975 (2)	0.0319 (9)
H25A	0.4789	0.4058	0.1527	0.038*
C26	0.6459 (4)	0.4111 (3)	0.1944 (3)	0.0493 (12)
H26A	0.6401	0.3786	0.1476	0.059*
C27	0.7495 (4)	0.4429 (3)	0.2589 (3)	0.0532 (13)
H27A	0.8148	0.4331	0.2557	0.064*
C28	0.7588 (4)	0.4880 (3)	0.3270 (3)	0.0468 (11)
H28A	0.8304	0.5094	0.3712	0.056*
C29	0.6639 (3)	0.5028 (2)	0.3317 (2)	0.0312 (9)
H29A	0.6703	0.5339	0.3795	0.037*
C30	0.5593 (3)	0.4722 (2)	0.2669 (2)	0.0214 (7)
C31	0.0647 (3)	0.2693 (2)	0.4915 (2)	0.0246 (8)
H31A	0.0684	0.2155	0.5071	0.030*
C32	−0.0258 (3)	0.2938 (3)	0.4897 (2)	0.0324 (9)
H32A	−0.0845	0.2565	0.5045	0.039*
C33	−0.0332 (3)	0.3715 (2)	0.4668 (2)	0.0329 (9)
H33A	−0.0963	0.3876	0.4658	0.039*
C34	0.0524 (3)	0.4256 (2)	0.4454 (2)	0.0333 (9)
H34A	0.0479	0.4791	0.4292	0.040*
C35	0.1444 (3)	0.4024 (2)	0.4475 (2)	0.0257 (8)
H35A	0.2035	0.4402	0.4333	0.031*
C36	0.1502 (3)	0.3238 (2)	0.47019 (19)	0.0191 (7)
C37	0.1284 (3)	0.5534 (2)	0.2409 (2)	0.0299 (8)
H37A	0.1078	0.5233	0.1888	0.036*
C38	0.0527 (3)	0.5853 (3)	0.2578 (3)	0.0396 (10)
H38A	−0.0207	0.5758	0.2170	0.048*
C39	0.0816 (3)	0.6304 (3)	0.3323 (3)	0.0388 (10)
H39A	0.0290	0.6523	0.3428	0.047*
C40	0.1879 (3)	0.6436 (3)	0.3915 (2)	0.0353 (9)
H40A	0.2088	0.6746	0.4432	0.042*
C41	0.2642 (3)	0.6116 (2)	0.3759 (2)	0.0263 (8)
H41A	0.3375	0.6212	0.4168	0.032*
C42	0.2347 (3)	0.5659 (2)	0.3011 (2)	0.0206 (7)
C43	0.4563 (3)	0.7104 (2)	0.5999 (2)	0.0292 (8)
H43A	0.4704	0.6590	0.6146	0.035*
C44	0.3726 (3)	0.7309 (3)	0.6167 (3)	0.0417 (10)
H44A	0.3305	0.6942	0.6442	0.050*
C45	0.3499 (3)	0.8042 (3)	0.5938 (3)	0.0444 (11)
H45A	0.2919	0.8181	0.6051	0.053*
C46	0.4115 (3)	0.8569 (3)	0.5546 (2)	0.0387 (10)
H46A	0.3948	0.9070	0.5381	0.046*
C47	0.4974 (3)	0.8388 (2)	0.5387 (2)	0.0289 (8)
H47A	0.5405	0.8766	0.5125	0.035*
C48	0.5199 (3)	0.7647 (2)	0.56143 (19)	0.0210 (7)
C49	0.3497 (4)	0.7764 (3)	0.0729 (2)	0.0441 (11)
H49A	0.3384	0.7433	0.1146	0.053*
C50	0.2937 (5)	0.8347 (3)	0.0486 (3)	0.0626 (14)
H50A	0.2437	0.8412	0.0739	0.075*
C51	0.3090 (5)	0.8831 (4)	−0.0112 (3)	0.0739 (17)
H51A	0.2705	0.9232	−0.0274	0.089*
C52	0.3802 (5)	0.8727 (4)	−0.0469 (3)	0.0708 (17)
H52A	0.3925	0.9072	−0.0875	0.085*
C53	0.4357 (4)	0.8133 (4)	−0.0258 (3)	0.0611 (15)
H53A	0.4822	0.8048	−0.0534	0.073*
C54	0.4212 (4)	0.7666 (3)	0.0364 (3)	0.0430 (11)
C55	0.8250 (4)	0.9572 (3)	0.1477 (2)	0.0433 (11)
H55A	0.8503	0.9416	0.1075	0.052*
C56	0.7136 (4)	0.9206 (4)	0.1397 (3)	0.0720 (17)
H56A	0.6613	0.8789	0.0944	0.086*
C57	0.6775 (5)	0.9440 (6)	0.1973 (4)	0.118 (3)
H57A	0.5999	0.9192	0.1917	0.141*
C58	0.7540 (5)	1.0037 (6)	0.2637 (4)	0.117 (3)
H58A	0.7285	1.0198	0.3035	0.140*
C59	0.8662 (4)	1.0401 (4)	0.2727 (3)	0.0615 (14)
H59A	0.9189	1.0805	0.3189	0.074*
C60	0.9013 (3)	1.0174 (2)	0.2145 (2)	0.0345 (9)
C61	0.9606 (4)	0.0935 (3)	0.9967 (3)	0.0445 (11)
H61A	0.9405	0.0438	1.0218	0.053*
C62	0.9418 (4)	0.0867 (3)	0.9142 (3)	0.0529 (12)
H62A	0.9099	0.0318	0.8829	0.063*
C63	0.9687 (4)	0.1580 (4)	0.8778 (3)	0.0543 (13)
H63A	0.9559	0.1527	0.8213	0.065*
C64	1.0141 (4)	0.2372 (3)	0.9226 (3)	0.0549 (13)
H64A	1.0311	0.2869	0.8968	0.066*
C65	1.0354 (4)	0.2456 (3)	1.0051 (3)	0.0513 (12)
H65A	1.0680	0.3006	1.0362	0.062*
C66	1.0090 (4)	0.1734 (3)	1.0415 (2)	0.0383 (10)
O1	0.54041 (18)	0.63380 (13)	0.39681 (13)	0.0183 (5)
H1A	0.5259	0.5859	0.4223	0.022*
O2	0.60505 (18)	0.74488 (14)	0.54685 (13)	0.0183 (5)
O3	0.75836 (19)	0.86821 (14)	0.49442 (13)	0.0237 (5)
O4	0.5436 (2)	0.80308 (15)	0.38310 (14)	0.0283 (6)
O5	0.4173 (2)	0.71356 (15)	0.27137 (14)	0.0260 (5)
O6	0.7265 (2)	0.75087 (15)	0.36927 (14)	0.0257 (5)
O7	0.5993 (2)	0.66425 (15)	0.25651 (14)	0.0271 (6)
O8	0.3798 (2)	0.58826 (14)	0.15280 (13)	0.0250 (5)
O9	0.31182 (18)	0.53531 (13)	0.28661 (13)	0.0189 (5)
O10	0.46764 (18)	0.48992 (13)	0.27276 (13)	0.0180 (5)
O11	0.2640 (2)	0.45254 (14)	0.13090 (13)	0.0254 (5)
O12	0.3143 (2)	0.31393 (14)	0.19809 (14)	0.0243 (5)
O13	0.2803 (2)	0.21169 (14)	0.27598 (13)	0.0242 (5)
O14	0.33077 (18)	0.38053 (13)	0.35228 (13)	0.0188 (5)
H14A	0.3828	0.4153	0.3875	0.023*
O15	0.13339 (18)	0.36893 (14)	0.21791 (13)	0.0227 (5)
O16	0.10135 (19)	0.26583 (15)	0.29517 (14)	0.0240 (5)
O17	0.24035 (18)	0.30004 (14)	0.46907 (13)	0.0181 (5)
O18	0.16603 (19)	0.13744 (14)	0.37207 (13)	0.0233 (5)
O19	0.4817 (3)	0.7111 (2)	0.0586 (2)	0.0547 (8)
H19D	0.4531	0.6759	0.0855	0.082*
O20	1.0109 (2)	1.05344 (17)	0.21791 (15)	0.0394 (7)
H20D	1.0544	1.0748	0.2661	0.059*
O21	1.0328 (3)	0.1850 (2)	1.12324 (18)	0.0675 (11)
H21A	1.0210	0.1373	1.1405	0.101*
O22	0.5377 (4)	0.4870 (3)	0.4922 (3)	0.0350 (12)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0174 (2)	0.0149 (2)	0.0151 (2)	0.00410 (19)	0.00440 (19)	0.00091 (18)
Fe2	0.0181 (2)	0.0146 (2)	0.0143 (2)	0.00379 (19)	0.00370 (19)	0.00067 (18)
Fe3	0.0181 (2)	0.0155 (2)	0.0142 (2)	0.00441 (19)	0.00354 (19)	0.00091 (18)
Fe4	0.0163 (2)	0.0160 (2)	0.0142 (2)	0.00320 (19)	0.00371 (19)	0.00127 (18)
C1	0.0181 (17)	0.0179 (17)	0.0219 (18)	0.0027 (14)	0.0068 (14)	0.0023 (14)
C2	0.0245 (18)	0.0184 (18)	0.0260 (19)	0.0042 (15)	0.0046 (15)	0.0025 (14)
C3	0.054 (3)	0.021 (2)	0.041 (2)	0.0026 (19)	0.015 (2)	0.0103 (18)
C4	0.049 (3)	0.031 (2)	0.051 (3)	0.012 (2)	0.017 (2)	−0.004 (2)
C5	0.031 (2)	0.0226 (19)	0.0224 (19)	0.0132 (16)	0.0031 (16)	0.0044 (15)
C6	0.054 (3)	0.035 (2)	0.044 (3)	0.027 (2)	−0.011 (2)	−0.005 (2)
C7	0.080 (4)	0.036 (3)	0.086 (4)	0.034 (3)	0.030 (3)	0.020 (3)
C8	0.062 (3)	0.049 (3)	0.114 (5)	0.041 (3)	0.038 (3)	0.020 (3)
C9	0.040 (2)	0.025 (2)	0.0183 (18)	0.0074 (18)	0.0030 (17)	0.0029 (15)
C10	0.085 (6)	0.031 (3)	0.013 (2)	0.003 (4)	0.012 (3)	0.004 (2)
C10'	0.086 (6)	0.035 (3)	0.014 (3)	0.005 (4)	0.015 (3)	0.001 (2)
C11	0.088 (5)	0.053 (4)	0.018 (3)	0.001 (4)	0.018 (3)	−0.004 (3)
C11'	0.095 (6)	0.060 (4)	0.025 (4)	0.013 (4)	0.022 (4)	−0.006 (3)
C12	0.073 (6)	0.042 (5)	0.033 (5)	0.016 (4)	−0.023 (4)	0.011 (4)
C12'	0.090 (8)	0.066 (7)	0.040 (6)	−0.002 (5)	−0.020 (5)	0.008 (5)
C13	0.042 (2)	0.023 (2)	0.0252 (19)	0.0105 (17)	0.0157 (18)	0.0026 (15)
C14	0.055 (5)	0.023 (4)	0.022 (4)	0.015 (4)	0.018 (4)	0.003 (3)
C14'	0.026 (5)	0.018 (5)	0.022 (5)	0.004 (4)	0.005 (4)	−0.003 (4)
C15	0.0414 (18)	0.082 (3)	0.0369 (18)	0.0292 (18)	0.0063 (15)	−0.0060 (17)
C16	0.060 (2)	0.095 (3)	0.064 (2)	0.047 (2)	0.018 (2)	0.004 (2)
C17	0.0220 (18)	0.035 (2)	0.0184 (18)	0.0072 (16)	0.0040 (15)	0.0039 (16)
C18	0.025 (2)	0.198 (7)	0.091 (4)	0.046 (4)	0.029 (3)	0.113 (5)
C19	0.0414 (18)	0.082 (3)	0.0369 (18)	0.0292 (18)	0.0063 (15)	−0.0060 (17)
C20	0.060 (2)	0.095 (3)	0.064 (2)	0.047 (2)	0.018 (2)	0.004 (2)
C21	0.031 (2)	0.0226 (19)	0.033 (2)	−0.0052 (16)	0.0200 (18)	−0.0059 (16)
C22	0.032 (3)	0.038 (4)	0.035 (3)	0.002 (3)	0.015 (3)	0.000 (3)
C22'	0.023 (3)	0.023 (4)	0.020 (3)	0.006 (3)	0.014 (3)	0.006 (3)
C23	0.039 (3)	0.069 (3)	0.041 (3)	−0.016 (2)	0.024 (2)	−0.003 (2)
C24	0.062 (3)	0.062 (3)	0.093 (4)	−0.012 (3)	0.061 (3)	−0.027 (3)
C25	0.036 (2)	0.024 (2)	0.039 (2)	0.0052 (17)	0.0227 (19)	−0.0011 (16)
C26	0.062 (3)	0.030 (2)	0.075 (3)	0.014 (2)	0.050 (3)	−0.002 (2)
C27	0.039 (3)	0.046 (3)	0.097 (4)	0.023 (2)	0.042 (3)	0.019 (3)
C28	0.026 (2)	0.047 (3)	0.069 (3)	0.015 (2)	0.018 (2)	0.018 (2)
C29	0.025 (2)	0.032 (2)	0.035 (2)	0.0107 (17)	0.0088 (17)	0.0072 (17)
C30	0.0233 (18)	0.0154 (17)	0.0296 (19)	0.0064 (14)	0.0148 (16)	0.0079 (14)
C31	0.0237 (18)	0.0245 (19)	0.0266 (19)	0.0090 (15)	0.0096 (16)	0.0082 (15)
C32	0.025 (2)	0.037 (2)	0.040 (2)	0.0107 (17)	0.0189 (18)	0.0106 (18)
C33	0.035 (2)	0.039 (2)	0.037 (2)	0.0231 (19)	0.0174 (18)	0.0052 (18)
C34	0.044 (2)	0.028 (2)	0.039 (2)	0.0211 (18)	0.0196 (19)	0.0087 (17)
C35	0.0261 (19)	0.0229 (19)	0.0272 (19)	0.0046 (15)	0.0123 (16)	0.0041 (15)
C36	0.0182 (17)	0.0234 (18)	0.0136 (16)	0.0073 (14)	0.0034 (14)	0.0024 (13)
C37	0.027 (2)	0.030 (2)	0.028 (2)	0.0136 (17)	0.0017 (16)	−0.0048 (16)
C38	0.022 (2)	0.041 (2)	0.050 (3)	0.0152 (18)	0.0036 (19)	−0.001 (2)
C39	0.031 (2)	0.035 (2)	0.059 (3)	0.0153 (18)	0.023 (2)	0.001 (2)
C40	0.039 (2)	0.037 (2)	0.036 (2)	0.0141 (19)	0.0211 (19)	−0.0032 (18)
C41	0.0242 (19)	0.029 (2)	0.0236 (19)	0.0081 (16)	0.0080 (16)	0.0018 (15)
C42	0.0194 (17)	0.0173 (17)	0.0256 (18)	0.0068 (14)	0.0082 (15)	0.0037 (14)
C43	0.0256 (19)	0.029 (2)	0.030 (2)	0.0045 (16)	0.0102 (16)	0.0038 (16)
C44	0.027 (2)	0.058 (3)	0.040 (2)	0.009 (2)	0.0178 (19)	0.002 (2)
C45	0.027 (2)	0.070 (3)	0.040 (2)	0.024 (2)	0.0109 (19)	−0.008 (2)
C46	0.039 (2)	0.044 (2)	0.037 (2)	0.027 (2)	0.0067 (19)	0.0014 (19)
C47	0.032 (2)	0.028 (2)	0.027 (2)	0.0130 (17)	0.0087 (17)	0.0022 (16)
C48	0.0164 (16)	0.0228 (18)	0.0173 (17)	0.0048 (14)	0.0006 (14)	−0.0040 (14)
C49	0.055 (3)	0.039 (2)	0.026 (2)	0.009 (2)	0.007 (2)	0.0039 (18)
C50	0.072 (4)	0.072 (4)	0.043 (3)	0.036 (3)	0.011 (3)	0.016 (3)
C51	0.067 (4)	0.074 (4)	0.066 (4)	0.026 (3)	0.005 (3)	0.027 (3)
C52	0.050 (3)	0.074 (4)	0.062 (3)	0.006 (3)	0.002 (3)	0.039 (3)
C53	0.035 (3)	0.077 (4)	0.051 (3)	−0.004 (3)	0.012 (2)	0.021 (3)
C54	0.032 (2)	0.039 (2)	0.036 (2)	−0.0011 (19)	−0.0008 (19)	0.0064 (19)
C55	0.039 (2)	0.042 (3)	0.029 (2)	−0.001 (2)	0.0034 (19)	0.0015 (19)
C56	0.039 (3)	0.098 (4)	0.038 (3)	−0.017 (3)	0.003 (2)	0.001 (3)
C57	0.028 (3)	0.215 (9)	0.069 (4)	−0.003 (4)	0.009 (3)	−0.018 (5)
C58	0.044 (3)	0.233 (10)	0.062 (4)	0.034 (5)	0.019 (3)	−0.024 (5)
C59	0.044 (3)	0.094 (4)	0.039 (3)	0.030 (3)	0.000 (2)	−0.011 (3)
C60	0.036 (2)	0.033 (2)	0.026 (2)	0.0097 (18)	0.0030 (18)	0.0078 (17)
C61	0.045 (3)	0.039 (3)	0.045 (3)	0.010 (2)	0.015 (2)	0.003 (2)
C62	0.055 (3)	0.050 (3)	0.047 (3)	0.012 (2)	0.017 (2)	−0.012 (2)
C63	0.048 (3)	0.082 (4)	0.036 (3)	0.022 (3)	0.019 (2)	0.005 (3)
C64	0.062 (3)	0.060 (3)	0.045 (3)	0.016 (3)	0.025 (3)	0.018 (2)
C65	0.068 (3)	0.039 (3)	0.038 (3)	0.007 (2)	0.019 (2)	0.007 (2)
C66	0.040 (2)	0.040 (2)	0.027 (2)	0.0067 (19)	0.0081 (18)	0.0033 (18)
O1	0.0178 (11)	0.0147 (11)	0.0169 (11)	0.0004 (9)	0.0045 (9)	0.0014 (9)
O2	0.0166 (11)	0.0213 (12)	0.0171 (11)	0.0080 (10)	0.0050 (9)	0.0017 (9)
O3	0.0272 (13)	0.0181 (12)	0.0173 (12)	0.0016 (10)	0.0036 (10)	0.0017 (10)
O4	0.0328 (14)	0.0225 (13)	0.0225 (13)	0.0140 (11)	−0.0020 (11)	−0.0005 (10)
O5	0.0335 (14)	0.0197 (13)	0.0187 (12)	0.0118 (11)	−0.0001 (11)	0.0010 (10)
O6	0.0247 (13)	0.0257 (13)	0.0204 (13)	−0.0015 (10)	0.0103 (11)	−0.0009 (10)
O7	0.0278 (14)	0.0259 (13)	0.0217 (13)	−0.0028 (11)	0.0129 (11)	−0.0019 (10)
O8	0.0313 (14)	0.0195 (13)	0.0159 (12)	0.0032 (11)	0.0039 (11)	0.0022 (10)
O9	0.0176 (11)	0.0174 (12)	0.0221 (12)	0.0070 (9)	0.0070 (10)	0.0010 (9)
O10	0.0163 (11)	0.0187 (12)	0.0187 (12)	0.0051 (9)	0.0069 (9)	0.0016 (9)
O11	0.0306 (13)	0.0196 (13)	0.0176 (12)	0.0046 (11)	0.0026 (10)	0.0006 (10)
O12	0.0336 (14)	0.0191 (13)	0.0228 (12)	0.0083 (11)	0.0143 (11)	0.0018 (10)
O13	0.0333 (14)	0.0198 (12)	0.0199 (12)	0.0074 (11)	0.0117 (11)	0.0018 (10)
O14	0.0162 (11)	0.0151 (11)	0.0163 (11)	−0.0015 (9)	0.0017 (9)	−0.0004 (9)
O15	0.0175 (12)	0.0236 (13)	0.0214 (12)	0.0047 (10)	0.0024 (10)	0.0049 (10)
O16	0.0164 (12)	0.0282 (13)	0.0207 (12)	0.0032 (10)	0.0026 (10)	0.0048 (10)
O17	0.0175 (11)	0.0232 (12)	0.0153 (11)	0.0094 (10)	0.0060 (9)	0.0030 (9)
O18	0.0256 (13)	0.0168 (12)	0.0186 (12)	−0.0004 (10)	0.0044 (10)	0.0008 (10)
O19	0.0494 (19)	0.056 (2)	0.060 (2)	0.0081 (16)	0.0300 (17)	0.0131 (17)
O20	0.0378 (16)	0.0360 (16)	0.0236 (14)	−0.0045 (13)	0.0023 (12)	−0.0021 (12)
O21	0.098 (3)	0.0382 (19)	0.0319 (17)	−0.0086 (18)	0.0124 (18)	0.0047 (14)
O22	0.040 (3)	0.032 (3)	0.031 (3)	0.013 (2)	0.011 (3)	0.007 (2)

Geometric parameters (Å, º)

Fe1—O14	1.977 (2)	C22—H22	1.0000
Fe1—O15	1.979 (2)	C22'—C23	1.528 (9)
Fe1—O12	1.984 (2)	C22'—C24	1.557 (9)
Fe1—O11	2.007 (2)	C22'—H22'	1.0000
Fe1—O9	2.030 (2)	C23—H23A	0.9800
Fe1—O10	2.040 (2)	C23—H23B	0.9800
Fe2—O1	1.976 (2)	C23—H23C	0.9800
Fe2—O7	1.981 (2)	C24—H24A	0.9800
Fe2—O5	1.985 (2)	C24—H24B	0.9800
Fe2—O9	1.999 (2)	C24—H24C	0.9800
Fe2—O10	2.007 (2)	C25—C30	1.381 (5)
Fe2—O8	2.052 (2)	C25—C26	1.396 (6)
Fe3—O1	1.959 (2)	C25—H25A	0.9500
Fe3—O6	1.978 (2)	C26—C27	1.379 (7)
Fe3—O4	1.984 (2)	C26—H26A	0.9500
Fe3—O17^i	2.017 (2)	C27—C28	1.358 (7)
Fe3—O3	2.023 (2)	C27—H27A	0.9500
Fe3—O2	2.030 (2)	C28—C29	1.386 (5)
Fe4—O14	1.967 (2)	C28—H28A	0.9500
Fe4—O13	1.972 (2)	C29—C30	1.390 (5)
Fe4—O16	1.975 (2)	C29—H29A	0.9500
Fe4—O17	2.014 (2)	C30—O10	1.374 (4)
Fe4—O2^i	2.022 (2)	C31—C32	1.374 (5)
Fe4—O18	2.065 (2)	C31—C36	1.381 (5)
C1—O3	1.256 (4)	C31—H31A	0.9500
C1—O18^i	1.272 (4)	C32—C33	1.378 (5)
C1—C2	1.515 (5)	C32—H32A	0.9500
C2—C3	1.513 (5)	C33—C34	1.381 (5)
C2—C4	1.535 (5)	C33—H33A	0.9500
C2—H2A	1.0000	C34—C35	1.380 (5)
C3—H3A	0.9800	C34—H34A	0.9500
C3—H3B	0.9800	C35—C36	1.389 (5)
C3—H3C	0.9800	C35—H35A	0.9500
C4—H4A	0.9800	C36—O17	1.378 (4)
C4—H4B	0.9800	C37—C38	1.385 (5)
C4—H4C	0.9800	C37—C42	1.387 (5)
C5—O5	1.257 (4)	C37—H37A	0.9500
C5—O4	1.259 (4)	C38—C39	1.376 (6)
C5—C6	1.507 (5)	C38—H38A	0.9500
C6—C7	1.473 (6)	C39—C40	1.379 (6)
C6—C8	1.504 (7)	C39—H39A	0.9500
C6—H6A	1.0000	C40—C41	1.383 (5)
C7—H7A	0.9800	C40—H40A	0.9500
C7—H7B	0.9800	C41—C42	1.381 (5)
C7—H7C	0.9800	C41—H41A	0.9500
C8—H8A	0.9800	C42—O9	1.371 (4)
C8—H8B	0.9800	C43—C44	1.380 (5)
C8—H8C	0.9800	C43—C48	1.388 (5)
C9—O11	1.259 (4)	C43—H43A	0.9500
C9—O8	1.260 (4)	C44—C45	1.376 (6)
C9—C10	1.496 (9)	C44—H44A	0.9500
C9—C10'	1.571 (11)	C45—C46	1.369 (6)
C10—C12	1.502 (11)	C45—H45A	0.9500
C10—C11	1.517 (11)	C46—C47	1.381 (5)
C10—H10	1.0000	C46—H46A	0.9500
C10'—C11'	1.503 (13)	C47—C48	1.386 (5)
C10'—C12'	1.538 (19)	C47—H47A	0.9500
C10'—H10'	1.0000	C48—O2	1.373 (4)
C11—H11A	0.9800	C49—C54	1.366 (6)
C11—H11B	0.9800	C49—C50	1.382 (6)
C11—H11C	0.9800	C49—H49A	0.9500
C11'—H11D	0.9800	C50—C51	1.367 (7)
C11'—H11E	0.9800	C50—H50A	0.9500
C11'—H11F	0.9800	C51—C52	1.355 (8)
C12—H12A	0.9800	C51—H51A	0.9500
C12—H12B	0.9800	C52—C53	1.388 (8)
C12—H12C	0.9800	C52—H52A	0.9500
C12'—H12D	0.9800	C53—C54	1.386 (6)
C12'—H12E	0.9800	C53—H53A	0.9500
C12'—H12F	0.9800	C54—O19	1.378 (5)
C13—O12	1.251 (4)	C55—C56	1.366 (6)
C13—O13	1.263 (4)	C55—C60	1.387 (5)
C13—C14'	1.566 (6)	C55—H55A	0.9500
C13—C14	1.567 (6)	C56—C57	1.366 (8)
C14—C16	1.343 (9)	C56—H56A	0.9500
C14—C15	1.583 (9)	C57—C58	1.380 (9)
C14—H14	1.0000	C57—H57A	0.9500
C14'—C15	1.336 (10)	C58—C59	1.369 (8)
C14'—C16	1.648 (11)	C58—H58A	0.9500
C14'—H14'	1.0000	C59—C60	1.362 (6)
C15—H15A	0.9800	C59—H59A	0.9500
C15—H15B	0.9800	C60—O20	1.367 (5)
C15—H15C	0.9800	C61—C66	1.376 (6)
C16—H16A	0.9800	C61—C62	1.387 (6)
C16—H16B	0.9800	C61—H61A	0.9500
C16—H16C	0.9800	C62—C63	1.363 (7)
C17—O15	1.256 (4)	C62—H62A	0.9500
C17—O16	1.266 (4)	C63—C64	1.369 (7)
C17—C18	1.504 (5)	C63—H63A	0.9500
C18—C20	1.388 (7)	C64—C65	1.381 (6)
C18—C19	1.464 (6)	C64—H64A	0.9500
C18—H18A	1.0000	C65—C66	1.373 (6)
C19—H19A	0.9800	C65—H65A	0.9500
C19—H19B	0.9800	C66—O21	1.364 (5)
C19—H19C	0.9800	O1—H1A	0.9195
C20—H20A	0.9800	O2—Fe4^i	2.022 (2)
C20—H20B	0.9800	O14—H14A	0.8004
C20—H20C	0.9800	O17—Fe3^i	2.017 (2)
C21—O6	1.253 (4)	O18—C1^i	1.272 (4)
C21—O7	1.259 (4)	O19—H19D	0.8400
C21—C22'	1.535 (8)	O20—H20D	0.8400
C21—C22	1.583 (8)	O21—H21A	0.8400
C22—C24	1.412 (8)	O22—O22^i	1.313 (10)
C22—C23	1.561 (8)
O14—Fe1—O15	90.24 (9)	O6—C21—C22	113.3 (4)
O14—Fe1—O12	91.70 (9)	O7—C21—C22	118.5 (4)
O15—Fe1—O12	96.01 (10)	C22'—C21—C22	37.2 (4)
O14—Fe1—O11	178.22 (9)	C24—C22—C23	115.2 (5)
O15—Fe1—O11	88.22 (10)	C24—C22—C21	112.3 (5)
O12—Fe1—O11	87.57 (9)	C23—C22—C21	106.1 (5)
O14—Fe1—O9	91.83 (9)	C24—C22—H22	107.6
O15—Fe1—O9	93.61 (9)	C23—C22—H22	107.6
O12—Fe1—O9	169.74 (9)	C21—C22—H22	107.6
O11—Fe1—O9	89.16 (9)	C23—C22'—C21	110.2 (5)
O14—Fe1—O10	91.96 (9)	C23—C22'—C24	109.0 (6)
O15—Fe1—O10	169.08 (9)	C21—C22'—C24	107.3 (5)
O12—Fe1—O10	94.62 (9)	C23—C22'—H22'	110.1
O11—Fe1—O10	89.73 (9)	C21—C22'—H22'	110.1
O9—Fe1—O10	75.63 (8)	C24—C22'—H22'	110.1
O1—Fe2—O7	92.35 (9)	C22'—C23—C22	37.6 (4)
O1—Fe2—O5	92.72 (9)	C22'—C23—H23A	108.2
O7—Fe2—O5	92.78 (10)	C22—C23—H23A	109.5
O1—Fe2—O9	93.34 (9)	C22'—C23—H23B	137.4
O7—Fe2—O9	170.94 (9)	C22—C23—H23B	109.5
O5—Fe2—O9	93.98 (10)	H23A—C23—H23B	109.5
O1—Fe2—O10	93.56 (9)	C22'—C23—H23C	75.2
O7—Fe2—O10	95.55 (9)	C22—C23—H23C	109.5
O5—Fe2—O10	169.34 (9)	H23A—C23—H23C	109.5
O9—Fe2—O10	77.07 (8)	H23B—C23—H23C	109.5
O1—Fe2—O8	176.23 (9)	C22—C24—C22'	38.8 (4)
O7—Fe2—O8	84.42 (10)	C22—C24—H24A	109.5
O5—Fe2—O8	85.50 (9)	C22'—C24—H24A	104.9
O9—Fe2—O8	90.10 (9)	C22—C24—H24B	109.5
O10—Fe2—O8	88.71 (9)	C22'—C24—H24B	75.5
O1—Fe3—O6	91.57 (9)	H24A—C24—H24B	109.5
O1—Fe3—O4	91.07 (10)	C22—C24—H24C	109.5
O6—Fe3—O4	94.22 (10)	C22'—C24—H24C	140.6
O1—Fe3—O17^i	93.65 (9)	H24A—C24—H24C	109.5
O6—Fe3—O17^i	93.57 (9)	H24B—C24—H24C	109.5
O4—Fe3—O17^i	170.77 (9)	C30—C25—C26	119.0 (4)
O1—Fe3—O3	175.34 (9)	C30—C25—H25A	120.5
O6—Fe3—O3	87.24 (9)	C26—C25—H25A	120.5
O4—Fe3—O3	84.52 (10)	C27—C26—C25	120.4 (4)
O17^i—Fe3—O3	90.93 (9)	C27—C26—H26A	119.8
O1—Fe3—O2	93.90 (9)	C25—C26—H26A	119.8
O6—Fe3—O2	168.46 (9)	C28—C27—C26	120.6 (4)
O4—Fe3—O2	95.83 (10)	C28—C27—H27A	119.7
O17^i—Fe3—O2	75.95 (8)	C26—C27—H27A	119.7
O3—Fe3—O2	88.09 (9)	C27—C28—C29	119.9 (4)
O14—Fe4—O13	93.68 (9)	C27—C28—H28A	120.1
O14—Fe4—O16	92.35 (9)	C29—C28—H28A	120.1
O13—Fe4—O16	94.90 (10)	C28—C29—C30	120.3 (4)
O14—Fe4—O17	92.50 (9)	C28—C29—H29A	119.9
O13—Fe4—O17	168.94 (9)	C30—C29—H29A	119.9
O16—Fe4—O17	94.00 (9)	O10—C30—C25	121.4 (3)
O14—Fe4—O2^i	92.98 (9)	O10—C30—C29	118.7 (3)
O13—Fe4—O2^i	94.32 (9)	C25—C30—C29	119.8 (3)
O16—Fe4—O2^i	169.03 (9)	C32—C31—C36	119.3 (3)
O17—Fe4—O2^i	76.19 (8)	C32—C31—H31A	120.3
O14—Fe4—O18	177.06 (9)	C36—C31—H31A	120.3
O13—Fe4—O18	84.53 (9)	C31—C32—C33	121.3 (3)
O16—Fe4—O18	85.48 (9)	C31—C32—H32A	119.3
O17—Fe4—O18	89.65 (9)	C33—C32—H32A	119.3
O2^i—Fe4—O18	89.49 (9)	C34—C33—C32	119.2 (3)
O3—C1—O18^i	124.2 (3)	C34—C33—H33A	120.4
O3—C1—C2	118.0 (3)	C32—C33—H33A	120.4
O18^i—C1—C2	117.8 (3)	C33—C34—C35	120.4 (3)
C3—C2—C1	112.2 (3)	C33—C34—H34A	119.8
C3—C2—C4	111.7 (3)	C35—C34—H34A	119.8
C1—C2—C4	108.1 (3)	C34—C35—C36	119.8 (3)
C3—C2—H2A	108.2	C34—C35—H35A	120.1
C1—C2—H2A	108.2	C36—C35—H35A	120.1
C4—C2—H2A	108.2	O17—C36—C31	120.7 (3)
C2—C3—H3A	109.5	O17—C36—C35	119.2 (3)
C2—C3—H3B	109.5	C31—C36—C35	120.1 (3)
H3A—C3—H3B	109.5	C38—C37—C42	119.1 (3)
C2—C3—H3C	109.5	C38—C37—H37A	120.4
H3A—C3—H3C	109.5	C42—C37—H37A	120.4
H3B—C3—H3C	109.5	C39—C38—C37	121.4 (4)
C2—C4—H4A	109.5	C39—C38—H38A	119.3
C2—C4—H4B	109.5	C37—C38—H38A	119.3
H4A—C4—H4B	109.5	C38—C39—C40	119.2 (4)
C2—C4—H4C	109.5	C38—C39—H39A	120.4
H4A—C4—H4C	109.5	C40—C39—H39A	120.4
H4B—C4—H4C	109.5	C39—C40—C41	120.2 (4)
O5—C5—O4	125.2 (3)	C39—C40—H40A	119.9
O5—C5—C6	116.8 (3)	C41—C40—H40A	119.9
O4—C5—C6	118.0 (3)	C42—C41—C40	120.5 (3)
C7—C6—C8	116.5 (4)	C42—C41—H41A	119.8
C7—C6—C5	115.4 (4)	C40—C41—H41A	119.8
C8—C6—C5	109.5 (4)	O9—C42—C41	119.6 (3)
C7—C6—H6A	104.7	O9—C42—C37	120.8 (3)
C8—C6—H6A	104.7	C41—C42—C37	119.6 (3)
C5—C6—H6A	104.7	C44—C43—C48	120.1 (4)
C6—C7—H7A	109.5	C44—C43—H43A	120.0
C6—C7—H7B	109.5	C48—C43—H43A	120.0
H7A—C7—H7B	109.5	C45—C44—C43	120.3 (4)
C6—C7—H7C	109.5	C45—C44—H44A	119.9
H7A—C7—H7C	109.5	C43—C44—H44A	119.9
H7B—C7—H7C	109.5	C46—C45—C44	119.5 (4)
C6—C8—H8A	109.5	C46—C45—H45A	120.3
C6—C8—H8B	109.5	C44—C45—H45A	120.3
H8A—C8—H8B	109.5	C45—C46—C47	121.3 (4)
C6—C8—H8C	109.5	C45—C46—H46A	119.4
H8A—C8—H8C	109.5	C47—C46—H46A	119.4
H8B—C8—H8C	109.5	C46—C47—C48	119.2 (4)
O11—C9—O8	125.0 (3)	C46—C47—H47A	120.4
O11—C9—C10	114.7 (5)	C48—C47—H47A	120.4
O8—C9—C10	119.5 (5)	O2—C48—C47	120.7 (3)
O11—C9—C10'	117.4 (7)	O2—C48—C43	119.7 (3)
O8—C9—C10'	115.4 (7)	C47—C48—C43	119.6 (3)
C10—C9—C10'	25.0 (6)	C54—C49—C50	119.5 (4)
C12—C10—C11	109.7 (8)	C54—C49—H49A	120.2
C12—C10—C9	113.7 (7)	C50—C49—H49A	120.2
C11—C10—C9	106.0 (7)	C51—C50—C49	121.1 (5)
C12—C10—H10	109.1	C51—C50—H50A	119.4
C11—C10—H10	109.1	C49—C50—H50A	119.4
C9—C10—H10	109.1	C52—C51—C50	118.7 (6)
C11'—C10'—C12'	112.5 (13)	C52—C51—H51A	120.6
C11'—C10'—C9	111.4 (9)	C50—C51—H51A	120.6
C12'—C10'—C9	110.3 (10)	C51—C52—C53	122.0 (5)
C11'—C10'—H10'	107.4	C51—C52—H52A	119.0
C12'—C10'—H10'	107.4	C53—C52—H52A	119.0
C9—C10'—H10'	107.4	C54—C53—C52	118.2 (5)
C10'—C11'—H11D	109.5	C54—C53—H53A	120.9
C10'—C11'—H11E	109.5	C52—C53—H53A	120.9
H11D—C11'—H11E	109.5	C49—C54—O19	122.7 (4)
C10'—C11'—H11F	109.5	C49—C54—C53	120.4 (5)
H11D—C11'—H11F	109.5	O19—C54—C53	116.9 (4)
H11E—C11'—H11F	109.5	C56—C55—C60	119.9 (5)
C10'—C12'—H12D	109.5	C56—C55—H55A	120.1
C10'—C12'—H12E	109.5	C60—C55—H55A	120.1
H12D—C12'—H12E	109.5	C57—C56—C55	119.7 (5)
C10'—C12'—H12F	109.5	C57—C56—H56A	120.1
H12D—C12'—H12F	109.5	C55—C56—H56A	120.1
H12E—C12'—H12F	109.5	C56—C57—C58	120.0 (5)
O12—C13—O13	125.3 (3)	C56—C57—H57A	120.0
O12—C13—C14'	118.2 (4)	C58—C57—H57A	120.0
O13—C13—C14'	113.9 (4)	C59—C58—C57	120.8 (6)
O12—C13—C14	116.0 (4)	C59—C58—H58A	119.6
O13—C13—C14	117.4 (4)	C57—C58—H58A	119.6
C14'—C13—C14	29.2 (3)	C60—C59—C58	119.0 (5)
C16—C14—C13	118.1 (5)	C60—C59—H59A	120.5
C16—C14—C15	122.5 (6)	C58—C59—H59A	120.5
C13—C14—C15	105.1 (5)	C59—C60—O20	122.2 (4)
C16—C14—H14	102.7	C59—C60—C55	120.6 (4)
C13—C14—H14	102.7	O20—C60—C55	117.1 (4)
C15—C14—H14	102.7	C66—C61—C62	119.0 (4)
C15—C14'—C13	118.8 (6)	C66—C61—H61A	120.5
C15—C14'—C16	118.4 (7)	C62—C61—H61A	120.5
C13—C14'—C16	102.0 (5)	C63—C62—C61	120.6 (4)
C15—C14'—H14'	105.4	C63—C62—H62A	119.7
C13—C14'—H14'	105.4	C61—C62—H62A	119.7
C16—C14'—H14'	105.4	C62—C63—C64	119.9 (4)
C14'—C15—C14	29.9 (4)	C62—C63—H63A	120.1
C14'—C15—H15A	115.7	C64—C63—H63A	120.1
C14—C15—H15A	109.5	C63—C64—C65	120.5 (5)
C14'—C15—H15B	127.2	C63—C64—H64A	119.7
C14—C15—H15B	109.5	C65—C64—H64A	119.7
H15A—C15—H15B	109.5	C66—C65—C64	119.3 (4)
C14'—C15—H15C	80.1	C66—C65—H65A	120.4
C14—C15—H15C	109.5	C64—C65—H65A	120.4
H15A—C15—H15C	109.5	O21—C66—C65	117.1 (4)
H15B—C15—H15C	109.5	O21—C66—C61	122.3 (4)
C14—C16—C14'	28.4 (4)	C65—C66—C61	120.7 (4)
C14—C16—H16A	109.5	Fe3—O1—Fe2	121.62 (11)
C14'—C16—H16A	106.3	Fe3—O1—H1A	126.1
C14—C16—H16B	109.5	Fe2—O1—H1A	112.0
C14'—C16—H16B	84.9	C48—O2—Fe4^i	124.28 (19)
H16A—C16—H16B	109.5	C48—O2—Fe3	133.30 (19)
C14—C16—H16C	109.5	Fe4^i—O2—Fe3	100.49 (9)
C14'—C16—H16C	133.4	C1—O3—Fe3	131.2 (2)
H16A—C16—H16C	109.5	C5—O4—Fe3	136.5 (2)
H16B—C16—H16C	109.5	C5—O5—Fe2	133.6 (2)
O15—C17—O16	124.4 (3)	C21—O6—Fe3	135.5 (2)
O15—C17—C18	117.5 (3)	C21—O7—Fe2	134.9 (2)
O16—C17—C18	118.0 (3)	C9—O8—Fe2	129.0 (2)
C20—C18—C19	122.3 (4)	C42—O9—Fe2	124.91 (19)
C20—C18—C17	118.9 (4)	C42—O9—Fe1	132.54 (19)
C19—C18—C17	115.8 (4)	Fe2—O9—Fe1	100.98 (9)
C20—C18—H18A	95.8	C30—O10—Fe2	123.94 (19)
C19—C18—H18A	95.8	C30—O10—Fe1	132.86 (19)
C17—C18—H18A	95.8	Fe2—O10—Fe1	100.34 (9)
C18—C19—H19A	109.5	C9—O11—Fe1	130.8 (2)
C18—C19—H19B	109.5	C13—O12—Fe1	135.9 (2)
H19A—C19—H19B	109.5	C13—O13—Fe4	133.8 (2)
C18—C19—H19C	109.5	Fe4—O14—Fe1	120.65 (11)
H19A—C19—H19C	109.5	Fe4—O14—H14A	125.5
H19B—C19—H19C	109.5	Fe1—O14—H14A	113.2
C18—C20—H20A	109.5	C17—O15—Fe1	136.5 (2)
C18—C20—H20B	109.5	C17—O16—Fe4	133.8 (2)
H20A—C20—H20B	109.5	C36—O17—Fe4	122.71 (18)
C18—C20—H20C	109.5	C36—O17—Fe3^i	132.57 (19)
H20A—C20—H20C	109.5	Fe4—O17—Fe3^i	101.19 (9)
H20B—C20—H20C	109.5	C1^i—O18—Fe4	128.4 (2)
O6—C21—O7	124.9 (3)	C54—O19—H19D	109.5
O6—C21—C22'	120.3 (4)	C60—O20—H20D	109.5
O7—C21—C22'	112.1 (4)	C66—O21—H21A	109.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O22	0.92	2.08	2.977 (6)	166
O1—H1A···O22^i	0.92	2.18	3.025 (6)	152
O14—H14A···O22	0.80	2.20	2.983 (6)	168
O14—H14A···O22^i	0.80	2.36	3.094 (6)	153
O19—H19D···O8	0.84	2.11	2.946 (4)	179
O20—H20D···O18^ii	0.84	1.96	2.795 (3)	172
O21—H21A···O20^iii	0.84	1.97	2.771 (4)	159

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, y+1, z; (iii) x, y−1, z+1.