Ferrocene­carb­oxy­lic anhydride: identification of a new polymorph

A new monoclinic polymorph of ferrocene­carb­oxy­lic anhydride, [Fe₂(C₅H₅)₂(C₁₂H₈O₃)], was obtained. Three mol­ecules are present in the asymmetric unit, two of them being nearly identical (r.m.s. deviation = 0.11 Å), with the Fe atoms on the same side of the anhydride functional group. In the third mol­ecule, the two Fe atoms are located at opposite sides of the functional group (ferrocene–ferrocene pseudo-torsion angle = 146.2°), a very unsual feature in metallocene anhydrides. A network of weak inter­molecular hydrogen bonds was also disclosed.

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: APEX2 (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SXGRAPH (Farrugia, 1999) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CRYSCALC (T. Roisnel, local program).

Ferrocenecarboxylic anhydride

Crystal data

[Fe2(C5H5)2(C12H8O3)]	F(000) = 2712
Mr = 442.06	Dx = 1.661 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 5.9758 (5) Å	Cell parameters from 9522 reflections
b = 36.456 (3) Å	θ = 2.2–27.5°
c = 24.363 (2) Å	µ = 1.66 mm^−1
β = 91.997 (3)°	T = 150 K
V = 5304.4 (8) Å^3	Prism, red
Z = 12	0.56 × 0.36 × 0.30 mm

Data collection

Bruker APEXII diffractometer	10804 independent reflections
Radiation source: fine-focus sealed tube	10350 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2014)	h = −6→7
Tmin = 0.466, Tmax = 0.608	k = −46→41
16323 measured reflections	l = −31→31

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0346P)^2 + 44.5361P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.119	(Δ/σ)max = 0.004
S = 1.11	Δρmax = 0.97 e Å^−3
10804 reflections	Δρmin = −0.86 e Å^−3
731 parameters	Absolute structure: Refined as an inversion twin.
32 restraints	Absolute structure parameter: 0.21 (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.

The crystal structure was solved in the noncentrosymmetric Cc space group by a dual-space algorithm using the SHELXT program (Sheldrick, 2015a), and then refined with full-matrix least-square methods based on F² (SHELXL) (Sheldrick, 2015). The use of combined TWIN and BASF instructions led to a Flack parameter value of 0.21 (3), corresponding to a mixture of ~80% of a particular enantiomer and ~20% of the opposite one. All non-hydrogen atoms were refined with anisotropic atomic displacement parameters.

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

	x	y	z	Uiso*/Ueq
Fe1	0.66892 (17)	0.25136 (3)	0.87909 (4)	0.0139 (2)
Fe2	0.77528 (18)	0.42693 (3)	0.87935 (4)	0.0148 (2)
C1	0.9175 (15)	0.2316 (3)	0.9297 (3)	0.0214 (18)
H1	1.039804	0.217048	0.918481	0.026*
C2	0.9157 (18)	0.2706 (3)	0.9328 (4)	0.027 (2)
H2	1.035337	0.286714	0.924791	0.033*
C3	0.6988 (17)	0.2808 (3)	0.9502 (3)	0.026 (2)
H3	0.647300	0.305184	0.955372	0.031*
C4	0.5740 (17)	0.2487 (3)	0.9584 (3)	0.029 (2)
H4	0.424257	0.247739	0.970202	0.034*
C5	0.7093 (16)	0.2178 (2)	0.9460 (3)	0.0210 (18)
H5	0.667352	0.192733	0.948327	0.025*
C6	0.4810 (14)	0.2821 (2)	0.8246 (3)	0.0200 (17)
H6	0.414618	0.305163	0.831903	0.024*
C7	0.3812 (15)	0.2473 (3)	0.8311 (4)	0.0233 (19)
H7	0.235063	0.242825	0.843789	0.028*
C8	0.5414 (16)	0.2194 (2)	0.8151 (3)	0.0219 (19)
H8	0.516861	0.193681	0.814855	0.026*
C9	0.7366 (14)	0.2372 (2)	0.8001 (3)	0.0162 (16)
H9	0.869574	0.225587	0.788635	0.019*
C10	0.7016 (14)	0.2760 (2)	0.8050 (3)	0.0160 (16)
C11	0.8735 (14)	0.3030 (2)	0.7922 (3)	0.0163 (16)
O12	1.0359 (10)	0.29726 (16)	0.7668 (2)	0.0207 (12)
O13	0.8141 (10)	0.33825 (15)	0.8093 (3)	0.0216 (13)
C14	0.9835 (14)	0.3631 (2)	0.8213 (3)	0.0194 (17)
O15	1.1652 (11)	0.35399 (18)	0.8384 (3)	0.0303 (15)
C16	0.9037 (14)	0.4008 (2)	0.8148 (3)	0.0171 (16)
C17	1.0423 (15)	0.4320 (2)	0.8294 (3)	0.0195 (17)
H17	1.196212	0.431470	0.840479	0.023*
C18	0.9051 (17)	0.4634 (2)	0.8240 (4)	0.0243 (19)
H18	0.951423	0.487904	0.830804	0.029*
C19	0.6851 (17)	0.4521 (3)	0.8065 (3)	0.025 (2)
H19	0.560381	0.467834	0.799703	0.030*
C20	0.6853 (17)	0.4136 (2)	0.8010 (3)	0.0223 (19)
H20	0.560855	0.398800	0.789867	0.027*
C21	0.7724 (19)	0.3908 (3)	0.9427 (4)	0.030 (2)
H21	0.828477	0.366436	0.940963	0.036*
C22	0.8980 (18)	0.4225 (3)	0.9591 (4)	0.029 (2)
H22	1.050631	0.423019	0.971281	0.035*
C23	0.752 (2)	0.4529 (3)	0.9536 (4)	0.034 (2)
H23	0.789798	0.477726	0.961346	0.040*
C24	0.5450 (18)	0.4402 (3)	0.9351 (4)	0.032 (2)
H24	0.417618	0.455136	0.927400	0.038*
C25	0.5506 (17)	0.4018 (3)	0.9295 (4)	0.030 (2)
H25	0.428828	0.386282	0.918833	0.036*
Fe3	0.46792 (17)	0.31132 (3)	0.63680 (4)	0.0133 (2)
Fe4	0.57218 (18)	0.40600 (3)	0.37638 (5)	0.0153 (2)
C31	0.7070 (15)	0.2726 (2)	0.6569 (4)	0.0227 (18)
H31	0.828758	0.275326	0.682749	0.027*
C32	0.4891 (15)	0.2595 (2)	0.6684 (4)	0.0200 (18)
H32	0.439045	0.252074	0.703295	0.024*
C33	0.3616 (16)	0.2594 (2)	0.6191 (4)	0.028 (2)
H33	0.210327	0.251498	0.614924	0.033*
C34	0.4936 (16)	0.2728 (2)	0.5763 (4)	0.026 (2)
H34	0.447131	0.275964	0.538900	0.031*
C35	0.7096 (15)	0.2808 (2)	0.6001 (4)	0.0207 (17)
H35	0.833920	0.289969	0.581125	0.025*
C36	0.5523 (15)	0.3609 (2)	0.6721 (3)	0.0164 (16)
H36	0.692169	0.367472	0.689055	0.020*
C37	0.3663 (15)	0.3455 (2)	0.6989 (3)	0.0190 (17)
H37	0.360217	0.339898	0.736940	0.023*
C38	0.1900 (14)	0.3400 (2)	0.6585 (3)	0.0187 (17)
H38	0.047410	0.329689	0.665007	0.022*
C39	0.2629 (13)	0.3525 (2)	0.6073 (3)	0.0168 (16)
H39	0.176542	0.352853	0.573779	0.020*
C40	0.4903 (14)	0.3646 (2)	0.6147 (3)	0.0164 (16)
C41	0.6414 (14)	0.3784 (2)	0.5741 (3)	0.0160 (16)
O42	0.8139 (10)	0.39414 (16)	0.5815 (2)	0.0215 (12)
O43	0.5497 (9)	0.37180 (16)	0.5205 (2)	0.0189 (12)
C44	0.6920 (14)	0.3607 (2)	0.4809 (3)	0.0194 (17)
O45	0.8791 (11)	0.3501 (2)	0.4903 (3)	0.0338 (16)
C46	0.5811 (14)	0.3618 (2)	0.4260 (3)	0.0153 (16)
C47	0.6960 (15)	0.3536 (2)	0.3771 (3)	0.0194 (17)
H47	0.848402	0.346446	0.375178	0.023*
C48	0.5422 (16)	0.3582 (2)	0.3315 (3)	0.0220 (18)
H48	0.573395	0.354949	0.293870	0.026*
C49	0.3297 (15)	0.3686 (2)	0.3535 (3)	0.0210 (17)
H49	0.195696	0.373221	0.332550	0.025*
C50	0.3544 (15)	0.3708 (2)	0.4115 (3)	0.0184 (16)
H50	0.240895	0.377115	0.436107	0.022*
C51	0.728 (2)	0.4484 (3)	0.4167 (5)	0.041 (3)
H51	0.793885	0.447590	0.452753	0.050*
C52	0.8335 (18)	0.4405 (2)	0.3678 (5)	0.040 (2)
H52	0.985347	0.433211	0.365214	0.048*
C53	0.6819 (17)	0.4449 (2)	0.3231 (4)	0.030 (2)
H53	0.711729	0.441280	0.285409	0.036*
C54	0.4798 (17)	0.4557 (2)	0.3444 (4)	0.029 (2)
H54	0.345905	0.460706	0.323581	0.035*
C55	0.5060 (19)	0.4578 (2)	0.4023 (4)	0.033 (2)
H55	0.393324	0.464499	0.427024	0.039*
Fe5	0.33502 (18)	0.34823 (3)	0.12474 (4)	0.0149 (2)
Fe6	0.23842 (17)	0.51994 (3)	0.12024 (5)	0.0141 (2)
C61	0.0970 (16)	0.3689 (3)	0.0707 (4)	0.027 (2)
H61	−0.020313	0.385284	0.079396	0.032*
C62	0.0845 (17)	0.3301 (3)	0.0715 (4)	0.027 (2)
H62	−0.041795	0.315850	0.080788	0.033*
C63	0.2935 (19)	0.3165 (3)	0.0559 (4)	0.029 (2)
H63	0.331205	0.291237	0.052840	0.035*
C64	0.4396 (16)	0.3463 (3)	0.0456 (3)	0.0232 (19)
H64	0.590584	0.344801	0.034772	0.028*
C65	0.3134 (17)	0.3792 (3)	0.0547 (4)	0.025 (2)
H65	0.366259	0.403640	0.050703	0.030*
C66	0.2658 (15)	0.3323 (2)	0.2028 (3)	0.0185 (17)
H66	0.133989	0.320192	0.213829	0.022*
C67	0.4667 (17)	0.3153 (2)	0.1860 (3)	0.0232 (19)
H67	0.492792	0.289689	0.183871	0.028*
C68	0.6207 (14)	0.3432 (2)	0.1732 (4)	0.0194 (17)
H68	0.768288	0.339305	0.161118	0.023*
C69	0.5190 (14)	0.3778 (2)	0.1813 (3)	0.0165 (16)
H69	0.585670	0.401011	0.175416	0.020*
C70	0.3006 (14)	0.3715 (2)	0.1998 (3)	0.0146 (16)
C71	0.1346 (14)	0.3983 (2)	0.2153 (3)	0.0168 (16)
O72	−0.0277 (10)	0.39262 (16)	0.2416 (2)	0.0227 (13)
O73	0.1944 (10)	0.43342 (15)	0.1985 (3)	0.0213 (13)
C74	0.0267 (14)	0.4584 (2)	0.1851 (3)	0.0178 (17)
O75	−0.1612 (12)	0.45021 (19)	0.1717 (3)	0.0355 (17)
C76	0.1159 (15)	0.4959 (2)	0.1878 (3)	0.0193 (18)
C77	−0.0157 (15)	0.5279 (2)	0.1725 (4)	0.0203 (17)
H77	−0.170876	0.527999	0.162638	0.024*
C78	0.1250 (16)	0.5585 (2)	0.1748 (4)	0.0243 (19)
H78	0.082088	0.583140	0.167108	0.029*
C79	0.3462 (16)	0.5462 (2)	0.1907 (4)	0.0224 (19)
H79	0.475060	0.561280	0.195172	0.027*
C80	0.3403 (15)	0.5079 (2)	0.1987 (3)	0.0204 (18)
H80	0.463734	0.492840	0.209522	0.024*
C81	0.2521 (17)	0.5454 (3)	0.0460 (4)	0.0248 (19)
H81	0.217517	0.570329	0.038538	0.030*
C82	0.0982 (16)	0.5157 (3)	0.0433 (4)	0.028 (2)
H82	−0.056804	0.517241	0.033535	0.034*
C83	0.2177 (18)	0.4835 (3)	0.0577 (4)	0.028 (2)
H83	0.155211	0.459554	0.059395	0.034*
C84	0.4430 (17)	0.4923 (3)	0.0691 (4)	0.028 (2)
H84	0.558431	0.475531	0.079604	0.033*
C85	0.4681 (17)	0.5313 (3)	0.0619 (4)	0.026 (2)
H85	0.602464	0.545007	0.066879	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Fe1	0.0178 (6)	0.0130 (5)	0.0110 (5)	0.0014 (4)	0.0012 (4)	0.0008 (4)
Fe2	0.0194 (6)	0.0126 (5)	0.0123 (5)	0.0006 (5)	−0.0034 (4)	−0.0006 (4)
C1	0.022 (4)	0.025 (5)	0.017 (4)	0.004 (4)	−0.002 (3)	0.007 (3)
C2	0.036 (5)	0.024 (5)	0.021 (4)	0.001 (4)	−0.007 (4)	0.000 (4)
C3	0.040 (6)	0.021 (4)	0.016 (4)	0.003 (4)	0.001 (4)	−0.007 (3)
C4	0.030 (5)	0.043 (6)	0.014 (4)	0.001 (4)	0.007 (4)	−0.002 (4)
C5	0.034 (5)	0.018 (4)	0.011 (4)	0.002 (4)	0.002 (3)	0.004 (3)
C6	0.015 (4)	0.028 (5)	0.017 (4)	0.003 (3)	−0.002 (3)	0.003 (3)
C7	0.019 (4)	0.033 (5)	0.018 (4)	−0.006 (4)	0.002 (3)	0.008 (4)
C8	0.032 (5)	0.018 (4)	0.016 (4)	−0.009 (4)	−0.002 (4)	0.003 (3)
C9	0.022 (4)	0.020 (4)	0.007 (3)	0.003 (3)	0.002 (3)	0.000 (3)
C10	0.021 (4)	0.016 (4)	0.011 (3)	−0.006 (3)	0.001 (3)	0.001 (3)
C11	0.024 (4)	0.012 (4)	0.013 (4)	0.000 (3)	0.000 (3)	0.002 (3)
O12	0.022 (3)	0.020 (3)	0.020 (3)	−0.001 (2)	0.003 (2)	−0.002 (2)
O13	0.018 (3)	0.014 (3)	0.032 (3)	0.001 (2)	0.001 (3)	−0.002 (2)
C14	0.019 (4)	0.021 (4)	0.017 (4)	0.000 (3)	−0.003 (3)	−0.009 (3)
O15	0.024 (4)	0.023 (3)	0.043 (4)	0.004 (3)	−0.013 (3)	−0.010 (3)
C16	0.023 (4)	0.014 (4)	0.015 (4)	0.002 (3)	0.002 (3)	−0.005 (3)
C17	0.020 (4)	0.022 (4)	0.017 (4)	−0.008 (3)	0.002 (3)	0.000 (3)
C18	0.036 (5)	0.017 (4)	0.020 (4)	−0.009 (4)	0.001 (4)	0.005 (3)
C19	0.037 (5)	0.027 (5)	0.010 (4)	0.011 (4)	−0.005 (4)	0.005 (3)
C20	0.033 (5)	0.017 (4)	0.016 (4)	0.007 (4)	−0.007 (4)	−0.007 (3)
C21	0.045 (6)	0.028 (5)	0.018 (4)	−0.004 (4)	0.004 (4)	0.008 (4)
C22	0.039 (6)	0.031 (5)	0.016 (4)	−0.001 (4)	−0.005 (4)	0.001 (4)
C23	0.054 (7)	0.031 (5)	0.016 (4)	−0.006 (5)	−0.003 (4)	−0.011 (4)
C24	0.038 (6)	0.044 (6)	0.013 (4)	0.014 (5)	0.005 (4)	−0.002 (4)
C25	0.029 (5)	0.039 (6)	0.022 (4)	−0.013 (4)	0.005 (4)	−0.003 (4)
Fe3	0.0150 (5)	0.0121 (5)	0.0125 (5)	0.0012 (4)	−0.0014 (4)	−0.0003 (4)
Fe4	0.0190 (6)	0.0115 (5)	0.0153 (5)	−0.0025 (4)	0.0014 (4)	0.0001 (4)
C31	0.026 (5)	0.018 (4)	0.023 (4)	0.008 (3)	−0.011 (4)	−0.007 (3)
C32	0.028 (5)	0.008 (4)	0.024 (4)	0.004 (3)	−0.006 (4)	0.003 (3)
C33	0.027 (5)	0.011 (4)	0.044 (6)	−0.002 (3)	−0.011 (4)	−0.001 (4)
C34	0.028 (5)	0.025 (5)	0.023 (4)	0.006 (4)	−0.005 (4)	−0.005 (4)
C35	0.021 (4)	0.016 (4)	0.025 (4)	0.005 (3)	0.002 (3)	0.000 (3)
C36	0.024 (4)	0.013 (4)	0.013 (3)	0.004 (3)	−0.001 (3)	−0.005 (3)
C37	0.031 (5)	0.013 (4)	0.013 (4)	0.002 (3)	0.002 (3)	0.001 (3)
C38	0.022 (4)	0.017 (4)	0.018 (4)	0.002 (3)	0.014 (3)	0.007 (3)
C39	0.010 (4)	0.021 (4)	0.020 (4)	0.001 (3)	0.003 (3)	0.009 (3)
C40	0.015 (4)	0.024 (4)	0.010 (3)	0.005 (3)	−0.001 (3)	−0.004 (3)
C41	0.018 (4)	0.019 (4)	0.011 (3)	0.005 (3)	−0.003 (3)	0.002 (3)
O42	0.019 (3)	0.023 (3)	0.023 (3)	−0.005 (2)	0.001 (2)	0.003 (2)
O43	0.016 (3)	0.029 (3)	0.012 (3)	0.001 (2)	0.001 (2)	0.003 (2)
C44	0.023 (4)	0.021 (4)	0.015 (4)	0.008 (3)	0.005 (3)	0.005 (3)
O45	0.029 (4)	0.050 (4)	0.022 (3)	0.024 (3)	0.002 (3)	−0.002 (3)
C46	0.019 (4)	0.009 (3)	0.018 (4)	0.003 (3)	0.004 (3)	0.000 (3)
C47	0.025 (4)	0.010 (3)	0.023 (4)	−0.002 (3)	0.004 (3)	0.001 (3)
C48	0.037 (5)	0.014 (4)	0.015 (4)	−0.006 (4)	0.002 (4)	0.000 (3)
C49	0.020 (4)	0.021 (4)	0.022 (4)	−0.008 (3)	−0.008 (3)	−0.001 (3)
C50	0.022 (4)	0.013 (4)	0.020 (4)	−0.006 (3)	0.003 (3)	0.000 (3)
C51	0.060 (7)	0.021 (5)	0.042 (5)	−0.015 (5)	−0.015 (5)	−0.007 (4)
C52	0.031 (5)	0.013 (4)	0.076 (7)	−0.012 (4)	−0.002 (5)	0.005 (4)
C53	0.042 (5)	0.014 (4)	0.035 (5)	−0.006 (4)	0.015 (4)	0.003 (4)
C54	0.028 (5)	0.020 (4)	0.040 (5)	0.007 (4)	0.010 (4)	0.004 (4)
C55	0.053 (6)	0.007 (4)	0.039 (5)	−0.002 (4)	0.015 (4)	−0.008 (4)
Fe5	0.0181 (6)	0.0135 (5)	0.0133 (5)	−0.0010 (5)	0.0030 (4)	0.0004 (4)
Fe6	0.0159 (5)	0.0120 (5)	0.0143 (5)	−0.0006 (4)	−0.0026 (4)	−0.0012 (4)
C61	0.022 (5)	0.036 (5)	0.023 (4)	0.006 (4)	0.003 (4)	0.003 (4)
C62	0.028 (5)	0.036 (5)	0.018 (4)	−0.006 (4)	−0.004 (4)	0.001 (4)
C63	0.047 (6)	0.022 (5)	0.018 (4)	0.004 (4)	−0.003 (4)	−0.009 (4)
C64	0.027 (5)	0.033 (5)	0.010 (4)	−0.004 (4)	0.011 (3)	−0.001 (3)
C65	0.036 (5)	0.022 (5)	0.017 (4)	0.003 (4)	0.002 (4)	0.004 (3)
C66	0.025 (5)	0.014 (4)	0.017 (4)	−0.001 (3)	0.003 (3)	0.001 (3)
C67	0.038 (5)	0.016 (4)	0.016 (4)	−0.004 (4)	0.000 (4)	0.004 (3)
C68	0.015 (4)	0.019 (4)	0.024 (4)	0.003 (3)	0.004 (3)	0.001 (3)
C69	0.021 (4)	0.011 (4)	0.017 (4)	−0.006 (3)	0.003 (3)	−0.001 (3)
C70	0.020 (4)	0.011 (4)	0.013 (3)	−0.003 (3)	0.002 (3)	−0.001 (3)
C71	0.021 (4)	0.016 (4)	0.014 (3)	−0.003 (3)	−0.002 (3)	0.001 (3)
O72	0.022 (3)	0.024 (3)	0.022 (3)	0.004 (2)	0.007 (2)	0.005 (2)
O73	0.019 (3)	0.010 (3)	0.035 (3)	−0.002 (2)	0.003 (3)	0.003 (2)
C74	0.016 (4)	0.017 (4)	0.020 (4)	−0.001 (3)	−0.001 (3)	0.005 (3)
O75	0.027 (4)	0.028 (4)	0.050 (4)	−0.010 (3)	−0.013 (3)	0.019 (3)
C76	0.028 (5)	0.021 (4)	0.009 (3)	0.003 (4)	0.003 (3)	0.000 (3)
C77	0.020 (4)	0.016 (4)	0.025 (4)	0.008 (3)	0.008 (4)	0.002 (3)
C78	0.034 (5)	0.018 (4)	0.021 (4)	0.005 (4)	0.002 (4)	−0.002 (3)
C79	0.029 (5)	0.020 (4)	0.018 (4)	−0.003 (4)	−0.006 (4)	−0.007 (3)
C80	0.021 (4)	0.024 (5)	0.015 (4)	0.001 (3)	−0.006 (3)	−0.001 (3)
C81	0.034 (5)	0.024 (5)	0.017 (4)	0.003 (4)	0.000 (4)	0.002 (3)
C82	0.022 (5)	0.045 (6)	0.017 (4)	−0.005 (4)	−0.005 (3)	−0.008 (4)
C83	0.039 (6)	0.022 (5)	0.023 (4)	−0.010 (4)	−0.003 (4)	−0.008 (4)
C84	0.032 (5)	0.024 (5)	0.027 (5)	0.013 (4)	0.008 (4)	0.001 (4)
C85	0.027 (5)	0.030 (5)	0.022 (4)	−0.005 (4)	0.006 (4)	−0.005 (4)

Geometric parameters (Å, º)

Fe1—C1	2.030 (9)	C36—H36	0.9500
Fe1—C10	2.031 (8)	C37—C38	1.432 (12)
Fe1—C4	2.035 (9)	C37—H37	0.9500
Fe1—C3	2.041 (8)	C38—C39	1.411 (10)
Fe1—C6	2.042 (8)	C38—H38	0.9500
Fe1—C5	2.046 (8)	C39—C40	1.434 (11)
Fe1—C9	2.047 (7)	C39—H39	0.9500
Fe1—C7	2.050 (9)	C40—C41	1.453 (11)
Fe1—C2	2.060 (10)	C41—O42	1.188 (10)
Fe1—C8	2.070 (9)	C41—O43	1.419 (9)
Fe2—C16	2.012 (8)	O43—C44	1.368 (9)
Fe2—C20	2.026 (8)	C44—O45	1.198 (10)
Fe2—C24	2.026 (10)	C44—C46	1.474 (11)
Fe2—C21	2.030 (9)	C46—C47	1.427 (11)
Fe2—C17	2.049 (9)	C46—C50	1.426 (12)
Fe2—C23	2.051 (9)	C47—C48	1.425 (12)
Fe2—C19	2.054 (8)	C47—H47	0.9500
Fe2—C22	2.058 (9)	C48—C49	1.446 (13)
Fe2—C25	2.061 (10)	C48—H48	0.9500
Fe2—C18	2.064 (9)	C49—C50	1.416 (12)
C1—C5	1.411 (13)	C49—H49	0.9500
C1—C2	1.427 (13)	C50—H50	0.9500
C1—H1	0.9500	C51—C52	1.398 (16)
C2—C3	1.427 (14)	C51—C55	1.403 (16)
C2—H2	0.9500	C51—H51	0.9500
C3—C4	1.406 (14)	C52—C53	1.402 (15)
C3—H3	0.9500	C52—H52	0.9500
C4—C5	1.424 (13)	C53—C54	1.387 (13)
C4—H4	0.9500	C53—H53	0.9500
C5—H5	0.9500	C54—C55	1.417 (14)
C6—C7	1.412 (13)	C54—H54	0.9500
C6—C10	1.435 (12)	C55—H55	0.9500
C6—H6	0.9500	Fe5—C70	2.032 (8)
C7—C8	1.459 (13)	Fe5—C69	2.040 (8)
C7—H7	0.9500	Fe5—C66	2.044 (8)
C8—C9	1.393 (12)	Fe5—C63	2.046 (9)
C8—H8	0.9500	Fe5—C65	2.047 (9)
C9—C10	1.436 (11)	Fe5—C61	2.049 (9)
C9—H9	0.9500	Fe5—C64	2.049 (8)
C10—C11	1.464 (11)	Fe5—C68	2.050 (9)
C11—O12	1.187 (10)	Fe5—C67	2.051 (9)
C11—O13	1.402 (9)	Fe5—C62	2.056 (10)
O13—C14	1.382 (10)	Fe6—C83	2.023 (9)
C14—O15	1.195 (10)	Fe6—C76	2.024 (8)
C14—C16	1.463 (11)	Fe6—C82	2.033 (9)
C16—C20	1.415 (12)	Fe6—C80	2.034 (8)
C16—C17	1.443 (11)	Fe6—C77	2.036 (8)
C17—C18	1.411 (13)	Fe6—C81	2.036 (9)
C17—H17	0.9500	Fe6—C84	2.042 (9)
C18—C19	1.428 (14)	Fe6—C79	2.050 (8)
C18—H18	0.9500	Fe6—C85	2.052 (9)
C19—C20	1.411 (12)	Fe6—C78	2.065 (9)
C19—H19	0.9500	C61—C65	1.414 (13)
C20—H20	0.9500	C61—C62	1.418 (14)
C21—C25	1.411 (15)	C61—H61	0.9500
C21—C22	1.427 (14)	C62—C63	1.408 (14)
C21—H21	0.9500	C62—H62	0.9500
C22—C23	1.414 (15)	C63—C64	1.423 (14)
C22—H22	0.9500	C63—H63	0.9500
C23—C24	1.383 (16)	C64—C65	1.439 (13)
C23—H23	0.9500	C64—H64	0.9500
C24—C25	1.407 (15)	C65—H65	0.9500
C24—H24	0.9500	C66—C67	1.423 (13)
C25—H25	0.9500	C66—C70	1.446 (11)
Fe3—C40	2.020 (8)	C66—H66	0.9500
Fe3—C33	2.040 (8)	C67—C68	1.411 (12)
Fe3—C32	2.044 (8)	C67—H67	0.9500
Fe3—C34	2.045 (9)	C68—C69	1.417 (11)
Fe3—C38	2.048 (8)	C68—H68	0.9500
Fe3—C39	2.052 (8)	C69—C70	1.414 (11)
Fe3—C35	2.053 (8)	C69—H69	0.9500
Fe3—C36	2.056 (8)	C70—C71	1.450 (11)
Fe3—C31	2.057 (9)	C71—O72	1.199 (10)
Fe3—C37	2.068 (8)	C71—O73	1.396 (9)
Fe4—C46	2.015 (8)	O73—C74	1.385 (10)
Fe4—C52	2.022 (9)	C74—O75	1.196 (10)
Fe4—C55	2.036 (8)	C74—C76	1.467 (12)
Fe4—C50	2.037 (8)	C76—C80	1.427 (13)
Fe4—C54	2.039 (9)	C76—C77	1.448 (11)
Fe4—C51	2.040 (9)	C77—C78	1.399 (13)
Fe4—C53	2.047 (9)	C77—H77	0.9500
Fe4—C47	2.048 (8)	C78—C79	1.437 (13)
Fe4—C49	2.052 (8)	C78—H78	0.9500
Fe4—C48	2.062 (8)	C79—C80	1.408 (12)
C31—C35	1.417 (12)	C79—H79	0.9500
C31—C32	1.424 (13)	C80—H80	0.9500
C31—H31	0.9500	C81—C82	1.419 (14)
C32—C33	1.401 (12)	C81—C85	1.430 (14)
C32—H32	0.9500	C81—H81	0.9500
C33—C34	1.416 (14)	C82—C83	1.413 (14)
C33—H33	0.9500	C82—H82	0.9500
C34—C35	1.427 (13)	C83—C84	1.402 (14)
C34—H34	0.9500	C83—H83	0.9500
C35—H35	0.9500	C84—C85	1.440 (13)
C36—C37	1.423 (12)	C84—H84	0.9500
C36—C40	1.441 (10)	C85—H85	0.9500
C1—Fe1—C10	127.3 (4)	C33—C34—Fe3	69.5 (5)
C1—Fe1—C4	68.2 (4)	C35—C34—Fe3	69.9 (5)
C10—Fe1—C4	154.6 (4)	C33—C34—H34	126.6
C1—Fe1—C3	68.3 (4)	C35—C34—H34	126.6
C10—Fe1—C3	120.9 (3)	Fe3—C34—H34	125.6
C4—Fe1—C3	40.4 (4)	C31—C35—C34	108.3 (8)
C1—Fe1—C6	164.5 (4)	C31—C35—Fe3	70.0 (5)
C10—Fe1—C6	41.3 (3)	C34—C35—Fe3	69.3 (5)
C4—Fe1—C6	118.5 (4)	C31—C35—H35	125.8
C3—Fe1—C6	107.0 (4)	C34—C35—H35	125.8
C1—Fe1—C5	40.5 (4)	Fe3—C35—H35	126.5
C10—Fe1—C5	163.7 (4)	C37—C36—C40	107.7 (7)
C4—Fe1—C5	40.9 (4)	C37—C36—Fe3	70.3 (5)
C3—Fe1—C5	68.5 (4)	C40—C36—Fe3	68.0 (5)
C6—Fe1—C5	153.2 (4)	C37—C36—H36	126.2
C1—Fe1—C9	108.5 (3)	C40—C36—H36	126.2
C10—Fe1—C9	41.2 (3)	Fe3—C36—H36	127.1
C4—Fe1—C9	162.1 (4)	C36—C37—C38	107.9 (7)
C3—Fe1—C9	156.5 (4)	C36—C37—Fe3	69.3 (5)
C6—Fe1—C9	69.5 (3)	C38—C37—Fe3	68.9 (4)
C5—Fe1—C9	125.2 (3)	C36—C37—H37	126.1
C1—Fe1—C7	154.4 (4)	C38—C37—H37	126.1
C10—Fe1—C7	68.3 (3)	Fe3—C37—H37	127.3
C4—Fe1—C7	106.3 (4)	C39—C38—C37	108.7 (7)
C3—Fe1—C7	124.6 (4)	C39—C38—Fe3	70.0 (4)
C6—Fe1—C7	40.4 (3)	C37—C38—Fe3	70.4 (5)
C5—Fe1—C7	119.0 (4)	C39—C38—H38	125.6
C9—Fe1—C7	68.6 (4)	C37—C38—H38	125.6
C1—Fe1—C2	40.8 (4)	Fe3—C38—H38	125.5
C10—Fe1—C2	109.0 (4)	C38—C39—C40	107.9 (7)
C4—Fe1—C2	68.3 (4)	C38—C39—Fe3	69.7 (5)
C3—Fe1—C2	40.7 (4)	C40—C39—Fe3	68.2 (4)
C6—Fe1—C2	126.2 (4)	C38—C39—H39	126.0
C5—Fe1—C2	68.7 (4)	C40—C39—H39	126.0
C9—Fe1—C2	121.5 (4)	Fe3—C39—H39	127.6
C7—Fe1—C2	162.5 (4)	C39—C40—C36	107.7 (7)
C1—Fe1—C8	120.0 (4)	C39—C40—C41	129.0 (7)
C10—Fe1—C8	67.8 (3)	C36—C40—C41	123.3 (8)
C4—Fe1—C8	125.5 (4)	C39—C40—Fe3	70.6 (5)
C3—Fe1—C8	162.6 (4)	C36—C40—Fe3	70.6 (5)
C6—Fe1—C8	68.8 (4)	C41—C40—Fe3	124.3 (6)
C5—Fe1—C8	107.1 (3)	O42—C41—O43	121.8 (7)
C9—Fe1—C8	39.6 (3)	O42—C41—C40	128.3 (7)
C7—Fe1—C8	41.5 (4)	O43—C41—C40	109.8 (7)
C2—Fe1—C8	155.0 (4)	C44—O43—C41	117.9 (6)
C16—Fe2—C20	41.0 (4)	O45—C44—O43	124.0 (7)
C16—Fe2—C24	157.4 (4)	O45—C44—C46	124.7 (7)
C20—Fe2—C24	121.7 (4)	O43—C44—C46	111.2 (7)
C16—Fe2—C21	107.5 (4)	C47—C46—C50	108.8 (7)
C20—Fe2—C21	123.5 (4)	C47—C46—C44	122.6 (7)
C24—Fe2—C21	67.7 (4)	C50—C46—C44	128.6 (7)
C16—Fe2—C17	41.6 (3)	C47—C46—Fe4	70.7 (5)
C20—Fe2—C17	69.4 (4)	C50—C46—Fe4	70.2 (4)
C24—Fe2—C17	159.8 (4)	C44—C46—Fe4	124.5 (6)
C21—Fe2—C17	122.5 (4)	C48—C47—C46	108.0 (8)
C16—Fe2—C23	161.2 (4)	C48—C47—Fe4	70.3 (5)
C20—Fe2—C23	156.8 (4)	C46—C47—Fe4	68.2 (4)
C24—Fe2—C23	39.6 (4)	C48—C47—H47	126.0
C21—Fe2—C23	68.1 (4)	C46—C47—H47	126.0
C17—Fe2—C23	124.1 (4)	Fe4—C47—H47	127.1
C16—Fe2—C19	68.4 (4)	C47—C48—C49	107.0 (7)
C20—Fe2—C19	40.5 (3)	C47—C48—Fe4	69.2 (5)
C24—Fe2—C19	108.0 (4)	C49—C48—Fe4	69.1 (5)
C21—Fe2—C19	159.8 (4)	C47—C48—H48	126.5
C17—Fe2—C19	68.4 (4)	C49—C48—H48	126.5
C23—Fe2—C19	122.2 (4)	Fe4—C48—H48	126.9
C16—Fe2—C22	124.5 (4)	C50—C49—C48	108.8 (8)
C20—Fe2—C22	160.9 (4)	C50—C49—Fe4	69.1 (5)
C24—Fe2—C22	67.3 (4)	C48—C49—Fe4	69.8 (5)
C21—Fe2—C22	40.9 (4)	C50—C49—H49	125.6
C17—Fe2—C22	108.0 (4)	C48—C49—H49	125.6
C23—Fe2—C22	40.3 (4)	Fe4—C49—H49	127.0
C19—Fe2—C22	157.7 (4)	C49—C50—C46	107.4 (8)
C16—Fe2—C25	121.7 (4)	C49—C50—Fe4	70.3 (5)
C20—Fe2—C25	107.1 (4)	C46—C50—Fe4	68.6 (5)
C24—Fe2—C25	40.3 (4)	C49—C50—H50	126.3
C21—Fe2—C25	40.3 (4)	C46—C50—H50	126.3
C17—Fe2—C25	158.3 (4)	Fe4—C50—H50	126.4
C23—Fe2—C25	67.5 (4)	C52—C51—C55	106.7 (10)
C19—Fe2—C25	123.7 (4)	C52—C51—Fe4	69.2 (5)
C22—Fe2—C25	67.9 (4)	C55—C51—Fe4	69.7 (5)
C16—Fe2—C18	68.4 (4)	C52—C51—H51	126.6
C20—Fe2—C18	68.4 (4)	C55—C51—H51	126.6
C24—Fe2—C18	124.4 (4)	Fe4—C51—H51	126.0
C21—Fe2—C18	158.2 (4)	C51—C52—C53	109.9 (10)
C17—Fe2—C18	40.1 (4)	C51—C52—Fe4	70.6 (6)
C23—Fe2—C18	108.6 (4)	C53—C52—Fe4	70.8 (5)
C19—Fe2—C18	40.6 (4)	C51—C52—H52	125.0
C22—Fe2—C18	122.6 (4)	C53—C52—H52	125.0
C25—Fe2—C18	160.2 (4)	Fe4—C52—H52	125.2
C5—C1—C2	109.4 (8)	C54—C53—C52	106.8 (9)
C5—C1—Fe1	70.3 (5)	C54—C53—Fe4	69.9 (5)
C2—C1—Fe1	70.7 (5)	C52—C53—Fe4	68.9 (5)
C5—C1—H1	125.3	C54—C53—H53	126.6
C2—C1—H1	125.3	C52—C53—H53	126.6
Fe1—C1—H1	125.2	Fe4—C53—H53	126.2
C1—C2—C3	106.5 (9)	C53—C54—C55	108.7 (10)
C1—C2—Fe1	68.5 (5)	C53—C54—Fe4	70.4 (5)
C3—C2—Fe1	68.9 (5)	C55—C54—Fe4	69.5 (5)
C1—C2—H2	126.8	C53—C54—H54	125.6
C3—C2—H2	126.8	C55—C54—H54	125.6
Fe1—C2—H2	127.4	Fe4—C54—H54	126.0
C4—C3—C2	108.5 (8)	C51—C55—C54	107.8 (9)
C4—C3—Fe1	69.6 (5)	C51—C55—Fe4	70.0 (5)
C2—C3—Fe1	70.4 (5)	C54—C55—Fe4	69.8 (5)
C4—C3—H3	125.8	C51—C55—H55	126.1
C2—C3—H3	125.8	C54—C55—H55	126.1
Fe1—C3—H3	125.9	Fe4—C55—H55	125.7
C3—C4—C5	108.7 (9)	C70—Fe5—C69	40.6 (3)
C3—C4—Fe1	70.0 (5)	C70—Fe5—C66	41.6 (3)
C5—C4—Fe1	70.0 (5)	C69—Fe5—C66	69.1 (3)
C3—C4—H4	125.7	C70—Fe5—C63	163.8 (4)
C5—C4—H4	125.7	C69—Fe5—C63	154.1 (4)
Fe1—C4—H4	125.9	C66—Fe5—C63	125.4 (4)
C1—C5—C4	106.9 (8)	C70—Fe5—C65	120.9 (3)
C1—C5—Fe1	69.2 (5)	C69—Fe5—C65	106.8 (4)
C4—C5—Fe1	69.1 (5)	C66—Fe5—C65	157.4 (4)
C1—C5—H5	126.5	C63—Fe5—C65	68.1 (4)
C4—C5—H5	126.5	C70—Fe5—C61	109.6 (4)
Fe1—C5—H5	126.7	C69—Fe5—C61	125.9 (4)
C7—C6—C10	107.1 (8)	C66—Fe5—C61	123.0 (4)
C7—C6—Fe1	70.1 (5)	C63—Fe5—C61	67.7 (4)
C10—C6—Fe1	69.0 (5)	C65—Fe5—C61	40.4 (4)
C7—C6—H6	126.4	C70—Fe5—C64	154.8 (3)
C10—C6—H6	126.4	C69—Fe5—C64	118.6 (3)
Fe1—C6—H6	126.1	C66—Fe5—C64	160.7 (4)
C6—C7—C8	108.1 (8)	C63—Fe5—C64	40.7 (4)
C6—C7—Fe1	69.5 (5)	C65—Fe5—C64	41.1 (4)
C8—C7—Fe1	70.0 (5)	C61—Fe5—C64	68.6 (4)
C6—C7—H7	125.9	C70—Fe5—C68	68.2 (3)
C8—C7—H7	125.9	C69—Fe5—C68	40.5 (3)
Fe1—C7—H7	126.1	C66—Fe5—C68	68.3 (4)
C9—C8—C7	108.1 (8)	C63—Fe5—C68	119.7 (4)
C9—C8—Fe1	69.3 (5)	C65—Fe5—C68	123.8 (4)
C7—C8—Fe1	68.5 (5)	C61—Fe5—C68	161.7 (4)
C9—C8—H8	125.9	C64—Fe5—C68	105.3 (4)
C7—C8—H8	125.9	C70—Fe5—C67	68.7 (3)
Fe1—C8—H8	127.8	C69—Fe5—C67	68.4 (3)
C8—C9—C10	108.0 (8)	C66—Fe5—C67	40.7 (4)
C8—C9—Fe1	71.1 (5)	C63—Fe5—C67	107.4 (4)
C10—C9—Fe1	68.8 (4)	C65—Fe5—C67	160.3 (4)
C8—C9—H9	126.0	C61—Fe5—C67	157.5 (4)
C10—C9—H9	126.0	C64—Fe5—C67	122.9 (4)
Fe1—C9—H9	125.7	C68—Fe5—C67	40.3 (3)
C6—C10—C9	108.6 (7)	C70—Fe5—C62	127.4 (4)
C6—C10—C11	128.7 (8)	C69—Fe5—C62	163.7 (4)
C9—C10—C11	122.6 (8)	C66—Fe5—C62	109.2 (4)
C6—C10—Fe1	69.8 (5)	C63—Fe5—C62	40.2 (4)
C9—C10—Fe1	70.0 (4)	C65—Fe5—C62	68.2 (4)
C11—C10—Fe1	125.1 (6)	C61—Fe5—C62	40.4 (4)
O12—C11—O13	122.4 (7)	C64—Fe5—C62	68.5 (4)
O12—C11—C10	125.8 (7)	C68—Fe5—C62	155.2 (4)
O13—C11—C10	111.5 (7)	C67—Fe5—C62	121.6 (4)
C14—O13—C11	118.2 (6)	C83—Fe6—C76	108.3 (4)
O15—C14—O13	122.7 (8)	C83—Fe6—C82	40.8 (4)
O15—C14—C16	126.0 (8)	C76—Fe6—C82	124.6 (4)
O13—C14—C16	111.1 (7)	C83—Fe6—C80	125.1 (4)
C20—C16—C17	108.5 (7)	C76—Fe6—C80	41.2 (4)
C20—C16—C14	129.0 (8)	C82—Fe6—C80	162.0 (4)
C17—C16—C14	122.1 (8)	C83—Fe6—C77	122.5 (4)
C20—C16—Fe2	70.0 (5)	C76—Fe6—C77	41.8 (3)
C17—C16—Fe2	70.5 (5)	C82—Fe6—C77	107.2 (4)
C14—C16—Fe2	119.5 (6)	C80—Fe6—C77	69.4 (4)
C18—C17—C16	106.8 (8)	C83—Fe6—C81	68.5 (4)
C18—C17—Fe2	70.5 (5)	C76—Fe6—C81	161.1 (4)
C16—C17—Fe2	67.8 (4)	C82—Fe6—C81	40.8 (4)
C18—C17—H17	126.6	C80—Fe6—C81	155.9 (4)
C16—C17—H17	126.6	C77—Fe6—C81	123.0 (4)
Fe2—C17—H17	126.6	C83—Fe6—C84	40.4 (4)
C17—C18—C19	108.7 (8)	C76—Fe6—C84	121.6 (4)
C17—C18—Fe2	69.4 (5)	C82—Fe6—C84	68.6 (4)
C19—C18—Fe2	69.4 (5)	C80—Fe6—C84	107.6 (4)
C17—C18—H18	125.6	C77—Fe6—C84	158.0 (4)
C19—C18—H18	125.6	C81—Fe6—C84	68.8 (4)
Fe2—C18—H18	127.2	C83—Fe6—C79	161.3 (4)
C20—C19—C18	108.1 (8)	C76—Fe6—C79	68.5 (4)
C20—C19—Fe2	68.7 (5)	C82—Fe6—C79	156.3 (4)
C18—C19—Fe2	70.1 (5)	C80—Fe6—C79	40.3 (3)
C20—C19—H19	126.0	C77—Fe6—C79	68.2 (4)
C18—C19—H19	126.0	C81—Fe6—C79	120.7 (4)
Fe2—C19—H19	126.9	C84—Fe6—C79	124.4 (4)
C19—C20—C16	108.0 (8)	C83—Fe6—C85	68.6 (4)
C19—C20—Fe2	70.9 (5)	C76—Fe6—C85	156.9 (4)
C16—C20—Fe2	69.0 (5)	C82—Fe6—C85	69.0 (4)
C19—C20—H20	126.0	C80—Fe6—C85	120.6 (4)
C16—C20—H20	126.0	C77—Fe6—C85	159.4 (4)
Fe2—C20—H20	125.7	C81—Fe6—C85	41.0 (4)
C25—C21—C22	108.3 (9)	C84—Fe6—C85	41.2 (4)
C25—C21—Fe2	71.0 (6)	C79—Fe6—C85	106.7 (4)
C22—C21—Fe2	70.6 (5)	C83—Fe6—C78	156.8 (4)
C25—C21—H21	125.8	C76—Fe6—C78	68.7 (3)
C22—C21—H21	125.8	C82—Fe6—C78	120.7 (4)
Fe2—C21—H21	124.1	C80—Fe6—C78	68.7 (4)
C23—C22—C21	107.0 (10)	C77—Fe6—C78	39.9 (4)
C23—C22—Fe2	69.6 (5)	C81—Fe6—C78	106.6 (4)
C21—C22—Fe2	68.5 (5)	C84—Fe6—C78	161.0 (4)
C23—C22—H22	126.5	C79—Fe6—C78	40.9 (4)
C21—C22—H22	126.5	C85—Fe6—C78	123.4 (4)
Fe2—C22—H22	126.9	C65—C61—C62	108.6 (8)
C24—C23—C22	108.0 (9)	C65—C61—Fe5	69.7 (5)
C24—C23—Fe2	69.2 (5)	C62—C61—Fe5	70.1 (5)
C22—C23—Fe2	70.1 (5)	C65—C61—H61	125.7
C24—C23—H23	126.0	C62—C61—H61	125.7
C22—C23—H23	126.0	Fe5—C61—H61	126.1
Fe2—C23—H23	126.2	C63—C62—C61	107.5 (9)
C23—C24—C25	110.0 (9)	C63—C62—Fe5	69.5 (5)
C23—C24—Fe2	71.2 (6)	C61—C62—Fe5	69.5 (5)
C25—C24—Fe2	71.2 (5)	C63—C62—H62	126.2
C23—C24—H24	125.0	C61—C62—H62	126.2
C25—C24—H24	125.0	Fe5—C62—H62	126.3
Fe2—C24—H24	124.2	C62—C63—C64	109.5 (9)
C24—C25—C21	106.6 (9)	C62—C63—Fe5	70.3 (5)
C24—C25—Fe2	68.5 (6)	C64—C63—Fe5	69.8 (5)
C21—C25—Fe2	68.6 (5)	C62—C63—H63	125.3
C24—C25—H25	126.7	C64—C63—H63	125.3
C21—C25—H25	126.7	Fe5—C63—H63	126.2
Fe2—C25—H25	127.7	C63—C64—C65	106.4 (8)
C40—Fe3—C33	149.2 (3)	C63—C64—Fe5	69.5 (5)
C40—Fe3—C32	170.3 (3)	C65—C64—Fe5	69.4 (5)
C33—Fe3—C32	40.1 (3)	C63—C64—H64	126.8
C40—Fe3—C34	117.4 (3)	C65—C64—H64	126.8
C33—Fe3—C34	40.6 (4)	Fe5—C64—H64	125.9
C32—Fe3—C34	68.4 (4)	C61—C65—C64	108.1 (8)
C40—Fe3—C38	68.9 (3)	C61—C65—Fe5	69.9 (5)
C33—Fe3—C38	106.2 (4)	C64—C65—Fe5	69.5 (5)
C32—Fe3—C38	114.6 (3)	C61—C65—H65	126.0
C34—Fe3—C38	128.2 (4)	C64—C65—H65	126.0
C40—Fe3—C39	41.2 (3)	Fe5—C65—H65	126.2
C33—Fe3—C39	115.3 (4)	C67—C66—C70	106.9 (8)
C32—Fe3—C39	146.8 (3)	C67—C66—Fe5	69.9 (5)
C34—Fe3—C39	107.9 (4)	C70—C66—Fe5	68.8 (4)
C38—Fe3—C39	40.3 (3)	C67—C66—H66	126.6
C40—Fe3—C35	110.6 (3)	C70—C66—H66	126.6
C33—Fe3—C35	67.8 (4)	Fe5—C66—H66	126.3
C32—Fe3—C35	68.1 (4)	C68—C67—C66	108.3 (8)
C34—Fe3—C35	40.7 (4)	C68—C67—Fe5	69.8 (5)
C38—Fe3—C35	168.1 (3)	C66—C67—Fe5	69.4 (5)
C39—Fe3—C35	131.7 (3)	C68—C67—H67	125.8
C40—Fe3—C36	41.4 (3)	C66—C67—H67	125.8
C33—Fe3—C36	167.1 (4)	Fe5—C67—H67	126.5
C32—Fe3—C36	130.1 (3)	C67—C68—C69	108.8 (8)
C34—Fe3—C36	151.8 (4)	C67—C68—Fe5	69.9 (5)
C38—Fe3—C36	68.4 (3)	C69—C68—Fe5	69.4 (5)
C39—Fe3—C36	68.8 (3)	C67—C68—H68	125.6
C35—Fe3—C36	119.5 (4)	C69—C68—H68	125.6
C40—Fe3—C31	132.2 (4)	Fe5—C68—H68	126.7
C33—Fe3—C31	67.8 (4)	C70—C69—C68	107.8 (7)
C32—Fe3—C31	40.6 (4)	C70—C69—Fe5	69.4 (5)
C34—Fe3—C31	68.4 (3)	C68—C69—Fe5	70.1 (5)
C38—Fe3—C31	148.5 (3)	C70—C69—H69	126.1
C39—Fe3—C31	171.0 (3)	C68—C69—H69	126.1
C35—Fe3—C31	40.3 (3)	Fe5—C69—H69	126.0
C36—Fe3—C31	110.2 (3)	C69—C70—C66	108.1 (7)
C40—Fe3—C37	68.9 (3)	C69—C70—C71	128.4 (7)
C33—Fe3—C37	128.1 (4)	C66—C70—C71	123.4 (8)
C32—Fe3—C37	107.3 (3)	C69—C70—Fe5	70.0 (5)
C34—Fe3—C37	166.5 (4)	C66—C70—Fe5	69.7 (4)
C38—Fe3—C37	40.7 (3)	C71—C70—Fe5	127.3 (6)
C39—Fe3—C37	68.2 (3)	O72—C71—O73	122.2 (7)
C35—Fe3—C37	151.0 (4)	O72—C71—C70	126.7 (8)
C36—Fe3—C37	40.4 (3)	O73—C71—C70	111.0 (7)
C31—Fe3—C37	117.3 (3)	C74—O73—C71	118.9 (6)
C46—Fe4—C52	123.8 (4)	O75—C74—O73	124.3 (8)
C46—Fe4—C55	123.9 (4)	O75—C74—C76	125.6 (8)
C52—Fe4—C55	67.3 (4)	O73—C74—C76	110.1 (7)
C46—Fe4—C50	41.2 (3)	C80—C76—C77	107.4 (8)
C52—Fe4—C50	160.5 (4)	C80—C76—C74	129.2 (8)
C55—Fe4—C50	108.7 (4)	C77—C76—C74	123.0 (8)
C46—Fe4—C54	160.2 (4)	C80—C76—Fe6	69.8 (5)
C52—Fe4—C54	66.9 (4)	C77—C76—Fe6	69.6 (5)
C55—Fe4—C54	40.7 (4)	C74—C76—Fe6	120.5 (6)
C50—Fe4—C54	123.5 (4)	C78—C77—C76	108.2 (8)
C46—Fe4—C51	108.4 (4)	C78—C77—Fe6	71.2 (5)
C52—Fe4—C51	40.3 (5)	C76—C77—Fe6	68.7 (4)
C55—Fe4—C51	40.3 (5)	C78—C77—H77	125.9
C50—Fe4—C51	124.3 (4)	C76—C77—H77	125.9
C54—Fe4—C51	67.9 (4)	Fe6—C77—H77	125.8
C46—Fe4—C53	158.9 (4)	C77—C78—C79	107.8 (8)
C52—Fe4—C53	40.3 (4)	C77—C78—Fe6	68.9 (5)
C55—Fe4—C53	67.9 (4)	C79—C78—Fe6	69.0 (5)
C50—Fe4—C53	157.9 (4)	C77—C78—H78	126.1
C54—Fe4—C53	39.7 (4)	C79—C78—H78	126.1
C51—Fe4—C53	68.2 (4)	Fe6—C78—H78	127.6
C46—Fe4—C47	41.1 (3)	C80—C79—C78	108.7 (8)
C52—Fe4—C47	107.5 (4)	C80—C79—Fe6	69.2 (5)
C55—Fe4—C47	159.6 (4)	C78—C79—Fe6	70.1 (5)
C50—Fe4—C47	69.2 (3)	C80—C79—H79	125.6
C54—Fe4—C47	157.5 (4)	C78—C79—H79	125.6
C51—Fe4—C47	123.0 (4)	Fe6—C79—H79	126.6
C53—Fe4—C47	121.9 (4)	C79—C80—C76	107.9 (8)
C46—Fe4—C49	68.6 (3)	C79—C80—Fe6	70.4 (5)
C52—Fe4—C49	157.8 (4)	C76—C80—Fe6	69.0 (4)
C55—Fe4—C49	123.9 (4)	C79—C80—H80	126.1
C50—Fe4—C49	40.5 (3)	C76—C80—H80	126.1
C54—Fe4—C49	107.9 (4)	Fe6—C80—H80	126.1
C51—Fe4—C49	160.1 (4)	C82—C81—C85	108.5 (8)
C53—Fe4—C49	121.8 (4)	C82—C81—Fe6	69.5 (5)
C47—Fe4—C49	68.5 (4)	C85—C81—Fe6	70.1 (5)
C46—Fe4—C48	68.9 (3)	C82—C81—H81	125.8
C52—Fe4—C48	121.6 (4)	C85—C81—H81	125.8
C55—Fe4—C48	159.3 (4)	Fe6—C81—H81	126.3
C50—Fe4—C48	69.2 (3)	C83—C82—C81	107.5 (8)
C54—Fe4—C48	122.1 (4)	C83—C82—Fe6	69.2 (5)
C51—Fe4—C48	157.8 (5)	C81—C82—Fe6	69.7 (5)
C53—Fe4—C48	105.9 (4)	C83—C82—H82	126.3
C47—Fe4—C48	40.6 (3)	C81—C82—H82	126.3
C49—Fe4—C48	41.1 (4)	Fe6—C82—H82	126.4
C35—C31—C32	107.6 (8)	C84—C83—C82	109.4 (8)
C35—C31—Fe3	69.7 (5)	C84—C83—Fe6	70.6 (5)
C32—C31—Fe3	69.2 (5)	C82—C83—Fe6	70.0 (5)
C35—C31—H31	126.2	C84—C83—H83	125.3
C32—C31—H31	126.2	C82—C83—H83	125.3
Fe3—C31—H31	126.5	Fe6—C83—H83	125.7
C33—C32—C31	107.9 (8)	C83—C84—C85	107.8 (8)
C33—C32—Fe3	69.8 (5)	C83—C84—Fe6	69.1 (5)
C31—C32—Fe3	70.2 (5)	C85—C84—Fe6	69.7 (5)
C33—C32—H32	126.1	C83—C84—H84	126.1
C31—C32—H32	126.1	C85—C84—H84	126.1
Fe3—C32—H32	125.6	Fe6—C84—H84	126.6
C32—C33—C34	109.3 (8)	C81—C85—C84	106.8 (9)
C32—C33—Fe3	70.1 (5)	C81—C85—Fe6	68.9 (5)
C34—C33—Fe3	69.9 (5)	C84—C85—Fe6	69.1 (5)
C32—C33—H33	125.4	C81—C85—H85	126.6
C34—C33—H33	125.4	C84—C85—H85	126.6
Fe3—C33—H33	126.2	Fe6—C85—H85	127.0
C33—C34—C35	106.9 (8)
C5—C1—C2—C3	−1.3 (10)	C41—O43—C44—O45	13.6 (12)
Fe1—C1—C2—C3	58.6 (6)	C41—O43—C44—C46	−169.4 (6)
C5—C1—C2—Fe1	−60.0 (6)	O45—C44—C46—C47	−6.8 (13)
C1—C2—C3—C4	1.0 (10)	O43—C44—C46—C47	176.2 (7)
Fe1—C2—C3—C4	59.4 (6)	O45—C44—C46—C50	173.9 (9)
C1—C2—C3—Fe1	−58.4 (6)	O43—C44—C46—C50	−3.1 (12)
C2—C3—C4—C5	−0.3 (10)	O45—C44—C46—Fe4	−94.7 (10)
Fe1—C3—C4—C5	59.5 (6)	O43—C44—C46—Fe4	88.3 (8)
C2—C3—C4—Fe1	−59.8 (6)	C50—C46—C47—C48	1.0 (9)
C2—C1—C5—C4	1.1 (10)	C44—C46—C47—C48	−178.4 (7)
Fe1—C1—C5—C4	−59.0 (6)	Fe4—C46—C47—C48	−59.2 (6)
C2—C1—C5—Fe1	60.2 (6)	C50—C46—C47—Fe4	60.1 (5)
C3—C4—C5—C1	−0.5 (10)	C44—C46—C47—Fe4	−119.3 (8)
Fe1—C4—C5—C1	59.0 (6)	C46—C47—C48—C49	−1.0 (9)
C3—C4—C5—Fe1	−59.6 (6)	Fe4—C47—C48—C49	−58.9 (6)
C10—C6—C7—C8	−0.3 (10)	C46—C47—C48—Fe4	57.9 (5)
Fe1—C6—C7—C8	−59.6 (6)	C47—C48—C49—C50	0.7 (9)
C10—C6—C7—Fe1	59.3 (6)	Fe4—C48—C49—C50	−58.3 (6)
C6—C7—C8—C9	1.1 (10)	C47—C48—C49—Fe4	58.9 (6)
Fe1—C7—C8—C9	−58.2 (6)	C48—C49—C50—C46	−0.1 (9)
C6—C7—C8—Fe1	59.3 (6)	Fe4—C49—C50—C46	−58.7 (5)
C7—C8—C9—C10	−1.5 (9)	C48—C49—C50—Fe4	58.7 (6)
Fe1—C8—C9—C10	−59.1 (5)	C47—C46—C50—C49	−0.6 (9)
C7—C8—C9—Fe1	57.7 (6)	C44—C46—C50—C49	178.8 (8)
C7—C6—C10—C9	−0.6 (9)	Fe4—C46—C50—C49	59.9 (6)
Fe1—C6—C10—C9	59.4 (5)	C47—C46—C50—Fe4	−60.4 (5)
C7—C6—C10—C11	−179.4 (8)	C44—C46—C50—Fe4	118.9 (8)
Fe1—C6—C10—C11	−119.4 (8)	C55—C51—C52—C53	0.2 (11)
C7—C6—C10—Fe1	−60.0 (6)	Fe4—C51—C52—C53	60.1 (7)
C8—C9—C10—C6	1.3 (9)	C55—C51—C52—Fe4	−59.9 (7)
Fe1—C9—C10—C6	−59.3 (6)	C51—C52—C53—C54	−0.1 (11)
C8—C9—C10—C11	−179.8 (7)	Fe4—C52—C53—C54	59.9 (6)
Fe1—C9—C10—C11	119.6 (7)	C51—C52—C53—Fe4	−60.0 (7)
C8—C9—C10—Fe1	60.6 (6)	C52—C53—C54—C55	−0.1 (10)
C6—C10—C11—O12	−165.2 (8)	Fe4—C53—C54—C55	59.2 (6)
C9—C10—C11—O12	16.1 (13)	C52—C53—C54—Fe4	−59.2 (6)
Fe1—C10—C11—O12	103.5 (9)	C52—C51—C55—C54	−0.3 (11)
C6—C10—C11—O13	9.1 (12)	Fe4—C51—C55—C54	−59.8 (6)
C9—C10—C11—O13	−169.5 (7)	C52—C51—C55—Fe4	59.5 (6)
Fe1—C10—C11—O13	−82.2 (8)	C53—C54—C55—C51	0.2 (11)
O12—C11—O13—C14	−31.4 (11)	Fe4—C54—C55—C51	59.9 (6)
C10—C11—O13—C14	154.0 (7)	C53—C54—C55—Fe4	−59.7 (7)
C11—O13—C14—O15	−29.7 (12)	C65—C61—C62—C63	0.0 (10)
C11—O13—C14—C16	155.1 (7)	Fe5—C61—C62—C63	−59.4 (6)
O15—C14—C16—C20	−172.2 (9)	C65—C61—C62—Fe5	59.3 (6)
O13—C14—C16—C20	2.8 (12)	C61—C62—C63—C64	0.4 (11)
O15—C14—C16—C17	−0.4 (13)	Fe5—C62—C63—C64	−59.0 (6)
O13—C14—C16—C17	174.6 (7)	C61—C62—C63—Fe5	59.4 (6)
O15—C14—C16—Fe2	−84.9 (11)	C62—C63—C64—C65	−0.5 (10)
O13—C14—C16—Fe2	90.1 (8)	Fe5—C63—C64—C65	−59.8 (6)
C20—C16—C17—C18	−0.1 (9)	C62—C63—C64—Fe5	59.3 (6)
C14—C16—C17—C18	−173.3 (7)	C62—C61—C65—C64	−0.3 (10)
Fe2—C16—C17—C18	−60.1 (6)	Fe5—C61—C65—C64	59.2 (6)
C20—C16—C17—Fe2	60.0 (6)	C62—C61—C65—Fe5	−59.5 (6)
C14—C16—C17—Fe2	−113.3 (8)	C63—C64—C65—C61	0.5 (10)
C16—C17—C18—C19	0.1 (10)	Fe5—C64—C65—C61	−59.4 (6)
Fe2—C17—C18—C19	−58.3 (6)	C63—C64—C65—Fe5	60.0 (6)
C16—C17—C18—Fe2	58.4 (5)	C70—C66—C67—C68	0.1 (10)
C17—C18—C19—C20	0.0 (10)	Fe5—C66—C67—C68	59.2 (6)
Fe2—C18—C19—C20	−58.3 (6)	C70—C66—C67—Fe5	−59.1 (6)
C17—C18—C19—Fe2	58.3 (6)	C66—C67—C68—C69	−0.4 (10)
C18—C19—C20—C16	0.0 (10)	Fe5—C67—C68—C69	58.6 (6)
Fe2—C19—C20—C16	−59.2 (6)	C66—C67—C68—Fe5	−58.9 (6)
C18—C19—C20—Fe2	59.2 (6)	C67—C68—C69—C70	0.5 (10)
C17—C16—C20—C19	0.1 (10)	Fe5—C68—C69—C70	59.4 (6)
C14—C16—C20—C19	172.7 (8)	C67—C68—C69—Fe5	−58.9 (6)
Fe2—C16—C20—C19	60.4 (6)	C68—C69—C70—C66	−0.4 (9)
C17—C16—C20—Fe2	−60.3 (6)	Fe5—C69—C70—C66	59.4 (6)
C14—C16—C20—Fe2	112.3 (9)	C68—C69—C70—C71	177.9 (8)
C25—C21—C22—C23	−2.2 (10)	Fe5—C69—C70—C71	−122.3 (9)
Fe2—C21—C22—C23	59.2 (7)	C68—C69—C70—Fe5	−59.8 (6)
C25—C21—C22—Fe2	−61.4 (6)	C67—C66—C70—C69	0.2 (9)
C21—C22—C23—C24	0.5 (11)	Fe5—C66—C70—C69	−59.6 (6)
Fe2—C22—C23—C24	59.0 (7)	C67—C66—C70—C71	−178.2 (7)
C21—C22—C23—Fe2	−58.5 (6)	Fe5—C66—C70—C71	122.0 (8)
C22—C23—C24—C25	1.3 (11)	C67—C66—C70—Fe5	59.8 (6)
Fe2—C23—C24—C25	60.9 (7)	C69—C70—C71—O72	−162.6 (9)
C22—C23—C24—Fe2	−59.6 (7)	C66—C70—C71—O72	15.4 (13)
C23—C24—C25—C21	−2.6 (11)	Fe5—C70—C71—O72	104.2 (9)
Fe2—C24—C25—C21	58.3 (6)	C69—C70—C71—O73	13.3 (12)
C23—C24—C25—Fe2	−60.9 (7)	C66—C70—C71—O73	−168.6 (7)
C22—C21—C25—C24	2.9 (10)	Fe5—C70—C71—O73	−79.8 (8)
Fe2—C21—C25—C24	−58.2 (6)	O72—C71—O73—C74	−34.5 (11)
C22—C21—C25—Fe2	61.1 (6)	C70—C71—O73—C74	149.4 (7)
C35—C31—C32—C33	0.5 (10)	C71—O73—C74—O75	−21.9 (12)
Fe3—C31—C32—C33	59.9 (6)	C71—O73—C74—C76	160.0 (7)
C35—C31—C32—Fe3	−59.3 (6)	O75—C74—C76—C80	−174.3 (9)
C31—C32—C33—C34	−1.0 (10)	O73—C74—C76—C80	3.8 (12)
Fe3—C32—C33—C34	59.1 (6)	O75—C74—C76—C77	−2.1 (14)
C31—C32—C33—Fe3	−60.1 (6)	O73—C74—C76—C77	176.0 (7)
C32—C33—C34—C35	1.0 (10)	O75—C74—C76—Fe6	−86.3 (11)
Fe3—C33—C34—C35	60.3 (6)	O73—C74—C76—Fe6	91.7 (8)
C32—C33—C34—Fe3	−59.2 (6)	C80—C76—C77—C78	−0.6 (9)
C32—C31—C35—C34	0.1 (10)	C74—C76—C77—C78	−174.3 (8)
Fe3—C31—C35—C34	−58.9 (6)	Fe6—C76—C77—C78	−60.5 (6)
C32—C31—C35—Fe3	59.0 (6)	C80—C76—C77—Fe6	59.8 (6)
C33—C34—C35—C31	−0.7 (10)	C74—C76—C77—Fe6	−113.8 (7)
Fe3—C34—C35—C31	59.3 (6)	C76—C77—C78—C79	0.7 (10)
C33—C34—C35—Fe3	−60.0 (6)	Fe6—C77—C78—C79	−58.2 (6)
C40—C36—C37—C38	−0.4 (9)	C76—C77—C78—Fe6	58.9 (6)
Fe3—C36—C37—C38	−58.2 (6)	C77—C78—C79—C80	−0.5 (10)
C40—C36—C37—Fe3	57.8 (5)	Fe6—C78—C79—C80	−58.7 (6)
C36—C37—C38—C39	−1.2 (9)	C77—C78—C79—Fe6	58.1 (6)
Fe3—C37—C38—C39	−59.8 (6)	C78—C79—C80—C76	0.1 (10)
C36—C37—C38—Fe3	58.5 (6)	Fe6—C79—C80—C76	−59.1 (6)
C37—C38—C39—C40	2.4 (9)	C78—C79—C80—Fe6	59.2 (6)
Fe3—C38—C39—C40	−57.6 (6)	C77—C76—C80—C79	0.3 (9)
C37—C38—C39—Fe3	60.0 (6)	C74—C76—C80—C79	173.4 (8)
C38—C39—C40—C36	−2.7 (9)	Fe6—C76—C80—C79	60.0 (6)
Fe3—C39—C40—C36	−61.2 (6)	C77—C76—C80—Fe6	−59.7 (6)
C38—C39—C40—C41	177.4 (8)	C74—C76—C80—Fe6	113.5 (9)
Fe3—C39—C40—C41	118.9 (9)	C85—C81—C82—C83	0.3 (11)
C38—C39—C40—Fe3	58.5 (6)	Fe6—C81—C82—C83	−59.2 (6)
C37—C36—C40—C39	1.9 (9)	C85—C81—C82—Fe6	59.4 (6)
Fe3—C36—C40—C39	61.2 (6)	C81—C82—C83—C84	−0.3 (11)
C37—C36—C40—C41	−178.2 (7)	Fe6—C82—C83—C84	−59.8 (7)
Fe3—C36—C40—C41	−118.9 (8)	C81—C82—C83—Fe6	59.4 (6)
C37—C36—C40—Fe3	−59.3 (6)	C82—C83—C84—C85	0.2 (11)
C39—C40—C41—O42	165.6 (9)	Fe6—C83—C84—C85	−59.2 (6)
C36—C40—C41—O42	−14.3 (14)	C82—C83—C84—Fe6	59.4 (7)
Fe3—C40—C41—O42	−102.5 (9)	C82—C81—C85—C84	−0.2 (10)
C39—C40—C41—O43	−12.0 (12)	Fe6—C81—C85—C84	58.9 (6)
C36—C40—C41—O43	168.1 (7)	C82—C81—C85—Fe6	−59.1 (6)
Fe3—C40—C41—O43	80.0 (8)	C83—C84—C85—C81	0.0 (10)
O42—C41—O43—C44	42.5 (11)	Fe6—C84—C85—C81	−58.8 (6)
C40—C41—O43—C44	−139.8 (7)	C83—C84—C85—Fe6	58.8 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C49—H49···O72	0.95	2.64	3.516 (10)	153
C31—H31···O12	0.95	2.49	3.387 (10)	158
C5—H5···O45^i	0.95	2.56	3.367 (11)	142
C85—H85···O42^ii	0.95	2.57	3.438 (12)	152
C6—H6···O12^iii	0.95	2.73	3.017 (10)	98
C6—H6···O15^iii	0.95	2.33	3.255 (11)	164
C39—H39···O42^iii	0.95	2.65	3.127 (10)	112
C39—H39···O45^iii	0.95	2.66	3.595 (10)	170
C69—H69···O72^iv	0.95	2.79	3.084 (10)	99
C69—H69···O75^iv	0.95	2.35	3.273 (10)	164

Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) x, −y+1, z−1/2; (iii) x−1, y, z; (iv) x+1, y, z.