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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961701124X/yf3122sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701124X/yf3122Isup2.hkl
Contains datablock I

CCDC reference: 1553140

Computing details top

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 top
Crystal data top
[Fe2(C5H5)2(C12H8O3)]F(000) = 2712
Mr = 442.06Dx = 1.661 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 5.9758 (5) ÅCell parameters from 9522 reflections
b = 36.456 (3) Åθ = 2.2–27.5°
c = 24.363 (2) ŵ = 1.66 mm1
β = 91.997 (3)°T = 150 K
V = 5304.4 (8) Å3Prism, red
Z = 120.56 × 0.36 × 0.30 mm
Data collection top
Bruker APEXII
diffractometer
10804 independent reflections
Radiation source: fine-focus sealed tube10350 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
CCD rotation images, thin slices scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2014)
h = 67
Tmin = 0.466, Tmax = 0.608k = 4641
16323 measured reflectionsl = 3131
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.049 w = 1/[σ2(Fo2) + (0.0346P)2 + 44.5361P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.119(Δ/σ)max = 0.004
S = 1.11Δρmax = 0.97 e Å3
10804 reflectionsΔρmin = 0.86 e Å3
731 parametersAbsolute structure: Refined as an inversion twin.
32 restraintsAbsolute structure parameter: 0.21 (3)
Special details top

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 (Å2) top
xyzUiso*/Ueq
Fe10.66892 (17)0.25136 (3)0.87909 (4)0.0139 (2)
Fe20.77528 (18)0.42693 (3)0.87935 (4)0.0148 (2)
C10.9175 (15)0.2316 (3)0.9297 (3)0.0214 (18)
H11.0398040.2170480.9184810.026*
C20.9157 (18)0.2706 (3)0.9328 (4)0.027 (2)
H21.0353370.2867140.9247910.033*
C30.6988 (17)0.2808 (3)0.9502 (3)0.026 (2)
H30.6473000.3051840.9553720.031*
C40.5740 (17)0.2487 (3)0.9584 (3)0.029 (2)
H40.4242570.2477390.9702020.034*
C50.7093 (16)0.2178 (2)0.9460 (3)0.0210 (18)
H50.6673520.1927330.9483270.025*
C60.4810 (14)0.2821 (2)0.8246 (3)0.0200 (17)
H60.4146180.3051630.8319030.024*
C70.3812 (15)0.2473 (3)0.8311 (4)0.0233 (19)
H70.2350630.2428250.8437890.028*
C80.5414 (16)0.2194 (2)0.8151 (3)0.0219 (19)
H80.5168610.1936810.8148550.026*
C90.7366 (14)0.2372 (2)0.8001 (3)0.0162 (16)
H90.8695740.2255870.7886350.019*
C100.7016 (14)0.2760 (2)0.8050 (3)0.0160 (16)
C110.8735 (14)0.3030 (2)0.7922 (3)0.0163 (16)
O121.0359 (10)0.29726 (16)0.7668 (2)0.0207 (12)
O130.8141 (10)0.33825 (15)0.8093 (3)0.0216 (13)
C140.9835 (14)0.3631 (2)0.8213 (3)0.0194 (17)
O151.1652 (11)0.35399 (18)0.8384 (3)0.0303 (15)
C160.9037 (14)0.4008 (2)0.8148 (3)0.0171 (16)
C171.0423 (15)0.4320 (2)0.8294 (3)0.0195 (17)
H171.1962120.4314700.8404790.023*
C180.9051 (17)0.4634 (2)0.8240 (4)0.0243 (19)
H180.9514230.4879040.8308040.029*
C190.6851 (17)0.4521 (3)0.8065 (3)0.025 (2)
H190.5603810.4678340.7997030.030*
C200.6853 (17)0.4136 (2)0.8010 (3)0.0223 (19)
H200.5608550.3988000.7898670.027*
C210.7724 (19)0.3908 (3)0.9427 (4)0.030 (2)
H210.8284770.3664360.9409630.036*
C220.8980 (18)0.4225 (3)0.9591 (4)0.029 (2)
H221.0506310.4230190.9712810.035*
C230.752 (2)0.4529 (3)0.9536 (4)0.034 (2)
H230.7897980.4777260.9613460.040*
C240.5450 (18)0.4402 (3)0.9351 (4)0.032 (2)
H240.4176180.4551360.9274000.038*
C250.5506 (17)0.4018 (3)0.9295 (4)0.030 (2)
H250.4288280.3862820.9188330.036*
Fe30.46792 (17)0.31132 (3)0.63680 (4)0.0133 (2)
Fe40.57218 (18)0.40600 (3)0.37638 (5)0.0153 (2)
C310.7070 (15)0.2726 (2)0.6569 (4)0.0227 (18)
H310.8287580.2753260.6827490.027*
C320.4891 (15)0.2595 (2)0.6684 (4)0.0200 (18)
H320.4390450.2520740.7032950.024*
C330.3616 (16)0.2594 (2)0.6191 (4)0.028 (2)
H330.2103270.2514980.6149240.033*
C340.4936 (16)0.2728 (2)0.5763 (4)0.026 (2)
H340.4471310.2759640.5389000.031*
C350.7096 (15)0.2808 (2)0.6001 (4)0.0207 (17)
H350.8339200.2899690.5811250.025*
C360.5523 (15)0.3609 (2)0.6721 (3)0.0164 (16)
H360.6921690.3674720.6890550.020*
C370.3663 (15)0.3455 (2)0.6989 (3)0.0190 (17)
H370.3602170.3398980.7369400.023*
C380.1900 (14)0.3400 (2)0.6585 (3)0.0187 (17)
H380.0474100.3296890.6650070.022*
C390.2629 (13)0.3525 (2)0.6073 (3)0.0168 (16)
H390.1765420.3528530.5737790.020*
C400.4903 (14)0.3646 (2)0.6147 (3)0.0164 (16)
C410.6414 (14)0.3784 (2)0.5741 (3)0.0160 (16)
O420.8139 (10)0.39414 (16)0.5815 (2)0.0215 (12)
O430.5497 (9)0.37180 (16)0.5205 (2)0.0189 (12)
C440.6920 (14)0.3607 (2)0.4809 (3)0.0194 (17)
O450.8791 (11)0.3501 (2)0.4903 (3)0.0338 (16)
C460.5811 (14)0.3618 (2)0.4260 (3)0.0153 (16)
C470.6960 (15)0.3536 (2)0.3771 (3)0.0194 (17)
H470.8484020.3464460.3751780.023*
C480.5422 (16)0.3582 (2)0.3315 (3)0.0220 (18)
H480.5733950.3549490.2938700.026*
C490.3297 (15)0.3686 (2)0.3535 (3)0.0210 (17)
H490.1956960.3732210.3325500.025*
C500.3544 (15)0.3708 (2)0.4115 (3)0.0184 (16)
H500.2408950.3771150.4361070.022*
C510.728 (2)0.4484 (3)0.4167 (5)0.041 (3)
H510.7938850.4475900.4527530.050*
C520.8335 (18)0.4405 (2)0.3678 (5)0.040 (2)
H520.9853470.4332110.3652140.048*
C530.6819 (17)0.4449 (2)0.3231 (4)0.030 (2)
H530.7117290.4412800.2854090.036*
C540.4798 (17)0.4557 (2)0.3444 (4)0.029 (2)
H540.3459050.4607060.3235810.035*
C550.5060 (19)0.4578 (2)0.4023 (4)0.033 (2)
H550.3933240.4644990.4270240.039*
Fe50.33502 (18)0.34823 (3)0.12474 (4)0.0149 (2)
Fe60.23842 (17)0.51994 (3)0.12024 (5)0.0141 (2)
C610.0970 (16)0.3689 (3)0.0707 (4)0.027 (2)
H610.0203130.3852840.0793960.032*
C620.0845 (17)0.3301 (3)0.0715 (4)0.027 (2)
H620.0417950.3158500.0807880.033*
C630.2935 (19)0.3165 (3)0.0559 (4)0.029 (2)
H630.3312050.2912370.0528400.035*
C640.4396 (16)0.3463 (3)0.0456 (3)0.0232 (19)
H640.5905840.3448010.0347720.028*
C650.3134 (17)0.3792 (3)0.0547 (4)0.025 (2)
H650.3662590.4036400.0507030.030*
C660.2658 (15)0.3323 (2)0.2028 (3)0.0185 (17)
H660.1339890.3201920.2138290.022*
C670.4667 (17)0.3153 (2)0.1860 (3)0.0232 (19)
H670.4927920.2896890.1838710.028*
C680.6207 (14)0.3432 (2)0.1732 (4)0.0194 (17)
H680.7682880.3393050.1611180.023*
C690.5190 (14)0.3778 (2)0.1813 (3)0.0165 (16)
H690.5856700.4010110.1754160.020*
C700.3006 (14)0.3715 (2)0.1998 (3)0.0146 (16)
C710.1346 (14)0.3983 (2)0.2153 (3)0.0168 (16)
O720.0277 (10)0.39262 (16)0.2416 (2)0.0227 (13)
O730.1944 (10)0.43342 (15)0.1985 (3)0.0213 (13)
C740.0267 (14)0.4584 (2)0.1851 (3)0.0178 (17)
O750.1612 (12)0.45021 (19)0.1717 (3)0.0355 (17)
C760.1159 (15)0.4959 (2)0.1878 (3)0.0193 (18)
C770.0157 (15)0.5279 (2)0.1725 (4)0.0203 (17)
H770.1708760.5279990.1626380.024*
C780.1250 (16)0.5585 (2)0.1748 (4)0.0243 (19)
H780.0820880.5831400.1671080.029*
C790.3462 (16)0.5462 (2)0.1907 (4)0.0224 (19)
H790.4750600.5612800.1951720.027*
C800.3403 (15)0.5079 (2)0.1987 (3)0.0204 (18)
H800.4637340.4928400.2095220.024*
C810.2521 (17)0.5454 (3)0.0460 (4)0.0248 (19)
H810.2175170.5703290.0385380.030*
C820.0982 (16)0.5157 (3)0.0433 (4)0.028 (2)
H820.0568040.5172410.0335350.034*
C830.2177 (18)0.4835 (3)0.0577 (4)0.028 (2)
H830.1552110.4595540.0593950.034*
C840.4430 (17)0.4923 (3)0.0691 (4)0.028 (2)
H840.5584310.4755310.0796040.033*
C850.4681 (17)0.5313 (3)0.0619 (4)0.026 (2)
H850.6024640.5450070.0668790.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0178 (6)0.0130 (5)0.0110 (5)0.0014 (4)0.0012 (4)0.0008 (4)
Fe20.0194 (6)0.0126 (5)0.0123 (5)0.0006 (5)0.0034 (4)0.0006 (4)
C10.022 (4)0.025 (5)0.017 (4)0.004 (4)0.002 (3)0.007 (3)
C20.036 (5)0.024 (5)0.021 (4)0.001 (4)0.007 (4)0.000 (4)
C30.040 (6)0.021 (4)0.016 (4)0.003 (4)0.001 (4)0.007 (3)
C40.030 (5)0.043 (6)0.014 (4)0.001 (4)0.007 (4)0.002 (4)
C50.034 (5)0.018 (4)0.011 (4)0.002 (4)0.002 (3)0.004 (3)
C60.015 (4)0.028 (5)0.017 (4)0.003 (3)0.002 (3)0.003 (3)
C70.019 (4)0.033 (5)0.018 (4)0.006 (4)0.002 (3)0.008 (4)
C80.032 (5)0.018 (4)0.016 (4)0.009 (4)0.002 (4)0.003 (3)
C90.022 (4)0.020 (4)0.007 (3)0.003 (3)0.002 (3)0.000 (3)
C100.021 (4)0.016 (4)0.011 (3)0.006 (3)0.001 (3)0.001 (3)
C110.024 (4)0.012 (4)0.013 (4)0.000 (3)0.000 (3)0.002 (3)
O120.022 (3)0.020 (3)0.020 (3)0.001 (2)0.003 (2)0.002 (2)
O130.018 (3)0.014 (3)0.032 (3)0.001 (2)0.001 (3)0.002 (2)
C140.019 (4)0.021 (4)0.017 (4)0.000 (3)0.003 (3)0.009 (3)
O150.024 (4)0.023 (3)0.043 (4)0.004 (3)0.013 (3)0.010 (3)
C160.023 (4)0.014 (4)0.015 (4)0.002 (3)0.002 (3)0.005 (3)
C170.020 (4)0.022 (4)0.017 (4)0.008 (3)0.002 (3)0.000 (3)
C180.036 (5)0.017 (4)0.020 (4)0.009 (4)0.001 (4)0.005 (3)
C190.037 (5)0.027 (5)0.010 (4)0.011 (4)0.005 (4)0.005 (3)
C200.033 (5)0.017 (4)0.016 (4)0.007 (4)0.007 (4)0.007 (3)
C210.045 (6)0.028 (5)0.018 (4)0.004 (4)0.004 (4)0.008 (4)
C220.039 (6)0.031 (5)0.016 (4)0.001 (4)0.005 (4)0.001 (4)
C230.054 (7)0.031 (5)0.016 (4)0.006 (5)0.003 (4)0.011 (4)
C240.038 (6)0.044 (6)0.013 (4)0.014 (5)0.005 (4)0.002 (4)
C250.029 (5)0.039 (6)0.022 (4)0.013 (4)0.005 (4)0.003 (4)
Fe30.0150 (5)0.0121 (5)0.0125 (5)0.0012 (4)0.0014 (4)0.0003 (4)
Fe40.0190 (6)0.0115 (5)0.0153 (5)0.0025 (4)0.0014 (4)0.0001 (4)
C310.026 (5)0.018 (4)0.023 (4)0.008 (3)0.011 (4)0.007 (3)
C320.028 (5)0.008 (4)0.024 (4)0.004 (3)0.006 (4)0.003 (3)
C330.027 (5)0.011 (4)0.044 (6)0.002 (3)0.011 (4)0.001 (4)
C340.028 (5)0.025 (5)0.023 (4)0.006 (4)0.005 (4)0.005 (4)
C350.021 (4)0.016 (4)0.025 (4)0.005 (3)0.002 (3)0.000 (3)
C360.024 (4)0.013 (4)0.013 (3)0.004 (3)0.001 (3)0.005 (3)
C370.031 (5)0.013 (4)0.013 (4)0.002 (3)0.002 (3)0.001 (3)
C380.022 (4)0.017 (4)0.018 (4)0.002 (3)0.014 (3)0.007 (3)
C390.010 (4)0.021 (4)0.020 (4)0.001 (3)0.003 (3)0.009 (3)
C400.015 (4)0.024 (4)0.010 (3)0.005 (3)0.001 (3)0.004 (3)
C410.018 (4)0.019 (4)0.011 (3)0.005 (3)0.003 (3)0.002 (3)
O420.019 (3)0.023 (3)0.023 (3)0.005 (2)0.001 (2)0.003 (2)
O430.016 (3)0.029 (3)0.012 (3)0.001 (2)0.001 (2)0.003 (2)
C440.023 (4)0.021 (4)0.015 (4)0.008 (3)0.005 (3)0.005 (3)
O450.029 (4)0.050 (4)0.022 (3)0.024 (3)0.002 (3)0.002 (3)
C460.019 (4)0.009 (3)0.018 (4)0.003 (3)0.004 (3)0.000 (3)
C470.025 (4)0.010 (3)0.023 (4)0.002 (3)0.004 (3)0.001 (3)
C480.037 (5)0.014 (4)0.015 (4)0.006 (4)0.002 (4)0.000 (3)
C490.020 (4)0.021 (4)0.022 (4)0.008 (3)0.008 (3)0.001 (3)
C500.022 (4)0.013 (4)0.020 (4)0.006 (3)0.003 (3)0.000 (3)
C510.060 (7)0.021 (5)0.042 (5)0.015 (5)0.015 (5)0.007 (4)
C520.031 (5)0.013 (4)0.076 (7)0.012 (4)0.002 (5)0.005 (4)
C530.042 (5)0.014 (4)0.035 (5)0.006 (4)0.015 (4)0.003 (4)
C540.028 (5)0.020 (4)0.040 (5)0.007 (4)0.010 (4)0.004 (4)
C550.053 (6)0.007 (4)0.039 (5)0.002 (4)0.015 (4)0.008 (4)
Fe50.0181 (6)0.0135 (5)0.0133 (5)0.0010 (5)0.0030 (4)0.0004 (4)
Fe60.0159 (5)0.0120 (5)0.0143 (5)0.0006 (4)0.0026 (4)0.0012 (4)
C610.022 (5)0.036 (5)0.023 (4)0.006 (4)0.003 (4)0.003 (4)
C620.028 (5)0.036 (5)0.018 (4)0.006 (4)0.004 (4)0.001 (4)
C630.047 (6)0.022 (5)0.018 (4)0.004 (4)0.003 (4)0.009 (4)
C640.027 (5)0.033 (5)0.010 (4)0.004 (4)0.011 (3)0.001 (3)
C650.036 (5)0.022 (5)0.017 (4)0.003 (4)0.002 (4)0.004 (3)
C660.025 (5)0.014 (4)0.017 (4)0.001 (3)0.003 (3)0.001 (3)
C670.038 (5)0.016 (4)0.016 (4)0.004 (4)0.000 (4)0.004 (3)
C680.015 (4)0.019 (4)0.024 (4)0.003 (3)0.004 (3)0.001 (3)
C690.021 (4)0.011 (4)0.017 (4)0.006 (3)0.003 (3)0.001 (3)
C700.020 (4)0.011 (4)0.013 (3)0.003 (3)0.002 (3)0.001 (3)
C710.021 (4)0.016 (4)0.014 (3)0.003 (3)0.002 (3)0.001 (3)
O720.022 (3)0.024 (3)0.022 (3)0.004 (2)0.007 (2)0.005 (2)
O730.019 (3)0.010 (3)0.035 (3)0.002 (2)0.003 (3)0.003 (2)
C740.016 (4)0.017 (4)0.020 (4)0.001 (3)0.001 (3)0.005 (3)
O750.027 (4)0.028 (4)0.050 (4)0.010 (3)0.013 (3)0.019 (3)
C760.028 (5)0.021 (4)0.009 (3)0.003 (4)0.003 (3)0.000 (3)
C770.020 (4)0.016 (4)0.025 (4)0.008 (3)0.008 (4)0.002 (3)
C780.034 (5)0.018 (4)0.021 (4)0.005 (4)0.002 (4)0.002 (3)
C790.029 (5)0.020 (4)0.018 (4)0.003 (4)0.006 (4)0.007 (3)
C800.021 (4)0.024 (5)0.015 (4)0.001 (3)0.006 (3)0.001 (3)
C810.034 (5)0.024 (5)0.017 (4)0.003 (4)0.000 (4)0.002 (3)
C820.022 (5)0.045 (6)0.017 (4)0.005 (4)0.005 (3)0.008 (4)
C830.039 (6)0.022 (5)0.023 (4)0.010 (4)0.003 (4)0.008 (4)
C840.032 (5)0.024 (5)0.027 (5)0.013 (4)0.008 (4)0.001 (4)
C850.027 (5)0.030 (5)0.022 (4)0.005 (4)0.006 (4)0.005 (4)
Geometric parameters (Å, º) top
Fe1—C12.030 (9)C36—H360.9500
Fe1—C102.031 (8)C37—C381.432 (12)
Fe1—C42.035 (9)C37—H370.9500
Fe1—C32.041 (8)C38—C391.411 (10)
Fe1—C62.042 (8)C38—H380.9500
Fe1—C52.046 (8)C39—C401.434 (11)
Fe1—C92.047 (7)C39—H390.9500
Fe1—C72.050 (9)C40—C411.453 (11)
Fe1—C22.060 (10)C41—O421.188 (10)
Fe1—C82.070 (9)C41—O431.419 (9)
Fe2—C162.012 (8)O43—C441.368 (9)
Fe2—C202.026 (8)C44—O451.198 (10)
Fe2—C242.026 (10)C44—C461.474 (11)
Fe2—C212.030 (9)C46—C471.427 (11)
Fe2—C172.049 (9)C46—C501.426 (12)
Fe2—C232.051 (9)C47—C481.425 (12)
Fe2—C192.054 (8)C47—H470.9500
Fe2—C222.058 (9)C48—C491.446 (13)
Fe2—C252.061 (10)C48—H480.9500
Fe2—C182.064 (9)C49—C501.416 (12)
C1—C51.411 (13)C49—H490.9500
C1—C21.427 (13)C50—H500.9500
C1—H10.9500C51—C521.398 (16)
C2—C31.427 (14)C51—C551.403 (16)
C2—H20.9500C51—H510.9500
C3—C41.406 (14)C52—C531.402 (15)
C3—H30.9500C52—H520.9500
C4—C51.424 (13)C53—C541.387 (13)
C4—H40.9500C53—H530.9500
C5—H50.9500C54—C551.417 (14)
C6—C71.412 (13)C54—H540.9500
C6—C101.435 (12)C55—H550.9500
C6—H60.9500Fe5—C702.032 (8)
C7—C81.459 (13)Fe5—C692.040 (8)
C7—H70.9500Fe5—C662.044 (8)
C8—C91.393 (12)Fe5—C632.046 (9)
C8—H80.9500Fe5—C652.047 (9)
C9—C101.436 (11)Fe5—C612.049 (9)
C9—H90.9500Fe5—C642.049 (8)
C10—C111.464 (11)Fe5—C682.050 (9)
C11—O121.187 (10)Fe5—C672.051 (9)
C11—O131.402 (9)Fe5—C622.056 (10)
O13—C141.382 (10)Fe6—C832.023 (9)
C14—O151.195 (10)Fe6—C762.024 (8)
C14—C161.463 (11)Fe6—C822.033 (9)
C16—C201.415 (12)Fe6—C802.034 (8)
C16—C171.443 (11)Fe6—C772.036 (8)
C17—C181.411 (13)Fe6—C812.036 (9)
C17—H170.9500Fe6—C842.042 (9)
C18—C191.428 (14)Fe6—C792.050 (8)
C18—H180.9500Fe6—C852.052 (9)
C19—C201.411 (12)Fe6—C782.065 (9)
C19—H190.9500C61—C651.414 (13)
C20—H200.9500C61—C621.418 (14)
C21—C251.411 (15)C61—H610.9500
C21—C221.427 (14)C62—C631.408 (14)
C21—H210.9500C62—H620.9500
C22—C231.414 (15)C63—C641.423 (14)
C22—H220.9500C63—H630.9500
C23—C241.383 (16)C64—C651.439 (13)
C23—H230.9500C64—H640.9500
C24—C251.407 (15)C65—H650.9500
C24—H240.9500C66—C671.423 (13)
C25—H250.9500C66—C701.446 (11)
Fe3—C402.020 (8)C66—H660.9500
Fe3—C332.040 (8)C67—C681.411 (12)
Fe3—C322.044 (8)C67—H670.9500
Fe3—C342.045 (9)C68—C691.417 (11)
Fe3—C382.048 (8)C68—H680.9500
Fe3—C392.052 (8)C69—C701.414 (11)
Fe3—C352.053 (8)C69—H690.9500
Fe3—C362.056 (8)C70—C711.450 (11)
Fe3—C312.057 (9)C71—O721.199 (10)
Fe3—C372.068 (8)C71—O731.396 (9)
Fe4—C462.015 (8)O73—C741.385 (10)
Fe4—C522.022 (9)C74—O751.196 (10)
Fe4—C552.036 (8)C74—C761.467 (12)
Fe4—C502.037 (8)C76—C801.427 (13)
Fe4—C542.039 (9)C76—C771.448 (11)
Fe4—C512.040 (9)C77—C781.399 (13)
Fe4—C532.047 (9)C77—H770.9500
Fe4—C472.048 (8)C78—C791.437 (13)
Fe4—C492.052 (8)C78—H780.9500
Fe4—C482.062 (8)C79—C801.408 (12)
C31—C351.417 (12)C79—H790.9500
C31—C321.424 (13)C80—H800.9500
C31—H310.9500C81—C821.419 (14)
C32—C331.401 (12)C81—C851.430 (14)
C32—H320.9500C81—H810.9500
C33—C341.416 (14)C82—C831.413 (14)
C33—H330.9500C82—H820.9500
C34—C351.427 (13)C83—C841.402 (14)
C34—H340.9500C83—H830.9500
C35—H350.9500C84—C851.440 (13)
C36—C371.423 (12)C84—H840.9500
C36—C401.441 (10)C85—H850.9500
C1—Fe1—C10127.3 (4)C33—C34—Fe369.5 (5)
C1—Fe1—C468.2 (4)C35—C34—Fe369.9 (5)
C10—Fe1—C4154.6 (4)C33—C34—H34126.6
C1—Fe1—C368.3 (4)C35—C34—H34126.6
C10—Fe1—C3120.9 (3)Fe3—C34—H34125.6
C4—Fe1—C340.4 (4)C31—C35—C34108.3 (8)
C1—Fe1—C6164.5 (4)C31—C35—Fe370.0 (5)
C10—Fe1—C641.3 (3)C34—C35—Fe369.3 (5)
C4—Fe1—C6118.5 (4)C31—C35—H35125.8
C3—Fe1—C6107.0 (4)C34—C35—H35125.8
C1—Fe1—C540.5 (4)Fe3—C35—H35126.5
C10—Fe1—C5163.7 (4)C37—C36—C40107.7 (7)
C4—Fe1—C540.9 (4)C37—C36—Fe370.3 (5)
C3—Fe1—C568.5 (4)C40—C36—Fe368.0 (5)
C6—Fe1—C5153.2 (4)C37—C36—H36126.2
C1—Fe1—C9108.5 (3)C40—C36—H36126.2
C10—Fe1—C941.2 (3)Fe3—C36—H36127.1
C4—Fe1—C9162.1 (4)C36—C37—C38107.9 (7)
C3—Fe1—C9156.5 (4)C36—C37—Fe369.3 (5)
C6—Fe1—C969.5 (3)C38—C37—Fe368.9 (4)
C5—Fe1—C9125.2 (3)C36—C37—H37126.1
C1—Fe1—C7154.4 (4)C38—C37—H37126.1
C10—Fe1—C768.3 (3)Fe3—C37—H37127.3
C4—Fe1—C7106.3 (4)C39—C38—C37108.7 (7)
C3—Fe1—C7124.6 (4)C39—C38—Fe370.0 (4)
C6—Fe1—C740.4 (3)C37—C38—Fe370.4 (5)
C5—Fe1—C7119.0 (4)C39—C38—H38125.6
C9—Fe1—C768.6 (4)C37—C38—H38125.6
C1—Fe1—C240.8 (4)Fe3—C38—H38125.5
C10—Fe1—C2109.0 (4)C38—C39—C40107.9 (7)
C4—Fe1—C268.3 (4)C38—C39—Fe369.7 (5)
C3—Fe1—C240.7 (4)C40—C39—Fe368.2 (4)
C6—Fe1—C2126.2 (4)C38—C39—H39126.0
C5—Fe1—C268.7 (4)C40—C39—H39126.0
C9—Fe1—C2121.5 (4)Fe3—C39—H39127.6
C7—Fe1—C2162.5 (4)C39—C40—C36107.7 (7)
C1—Fe1—C8120.0 (4)C39—C40—C41129.0 (7)
C10—Fe1—C867.8 (3)C36—C40—C41123.3 (8)
C4—Fe1—C8125.5 (4)C39—C40—Fe370.6 (5)
C3—Fe1—C8162.6 (4)C36—C40—Fe370.6 (5)
C6—Fe1—C868.8 (4)C41—C40—Fe3124.3 (6)
C5—Fe1—C8107.1 (3)O42—C41—O43121.8 (7)
C9—Fe1—C839.6 (3)O42—C41—C40128.3 (7)
C7—Fe1—C841.5 (4)O43—C41—C40109.8 (7)
C2—Fe1—C8155.0 (4)C44—O43—C41117.9 (6)
C16—Fe2—C2041.0 (4)O45—C44—O43124.0 (7)
C16—Fe2—C24157.4 (4)O45—C44—C46124.7 (7)
C20—Fe2—C24121.7 (4)O43—C44—C46111.2 (7)
C16—Fe2—C21107.5 (4)C47—C46—C50108.8 (7)
C20—Fe2—C21123.5 (4)C47—C46—C44122.6 (7)
C24—Fe2—C2167.7 (4)C50—C46—C44128.6 (7)
C16—Fe2—C1741.6 (3)C47—C46—Fe470.7 (5)
C20—Fe2—C1769.4 (4)C50—C46—Fe470.2 (4)
C24—Fe2—C17159.8 (4)C44—C46—Fe4124.5 (6)
C21—Fe2—C17122.5 (4)C48—C47—C46108.0 (8)
C16—Fe2—C23161.2 (4)C48—C47—Fe470.3 (5)
C20—Fe2—C23156.8 (4)C46—C47—Fe468.2 (4)
C24—Fe2—C2339.6 (4)C48—C47—H47126.0
C21—Fe2—C2368.1 (4)C46—C47—H47126.0
C17—Fe2—C23124.1 (4)Fe4—C47—H47127.1
C16—Fe2—C1968.4 (4)C47—C48—C49107.0 (7)
C20—Fe2—C1940.5 (3)C47—C48—Fe469.2 (5)
C24—Fe2—C19108.0 (4)C49—C48—Fe469.1 (5)
C21—Fe2—C19159.8 (4)C47—C48—H48126.5
C17—Fe2—C1968.4 (4)C49—C48—H48126.5
C23—Fe2—C19122.2 (4)Fe4—C48—H48126.9
C16—Fe2—C22124.5 (4)C50—C49—C48108.8 (8)
C20—Fe2—C22160.9 (4)C50—C49—Fe469.1 (5)
C24—Fe2—C2267.3 (4)C48—C49—Fe469.8 (5)
C21—Fe2—C2240.9 (4)C50—C49—H49125.6
C17—Fe2—C22108.0 (4)C48—C49—H49125.6
C23—Fe2—C2240.3 (4)Fe4—C49—H49127.0
C19—Fe2—C22157.7 (4)C49—C50—C46107.4 (8)
C16—Fe2—C25121.7 (4)C49—C50—Fe470.3 (5)
C20—Fe2—C25107.1 (4)C46—C50—Fe468.6 (5)
C24—Fe2—C2540.3 (4)C49—C50—H50126.3
C21—Fe2—C2540.3 (4)C46—C50—H50126.3
C17—Fe2—C25158.3 (4)Fe4—C50—H50126.4
C23—Fe2—C2567.5 (4)C52—C51—C55106.7 (10)
C19—Fe2—C25123.7 (4)C52—C51—Fe469.2 (5)
C22—Fe2—C2567.9 (4)C55—C51—Fe469.7 (5)
C16—Fe2—C1868.4 (4)C52—C51—H51126.6
C20—Fe2—C1868.4 (4)C55—C51—H51126.6
C24—Fe2—C18124.4 (4)Fe4—C51—H51126.0
C21—Fe2—C18158.2 (4)C51—C52—C53109.9 (10)
C17—Fe2—C1840.1 (4)C51—C52—Fe470.6 (6)
C23—Fe2—C18108.6 (4)C53—C52—Fe470.8 (5)
C19—Fe2—C1840.6 (4)C51—C52—H52125.0
C22—Fe2—C18122.6 (4)C53—C52—H52125.0
C25—Fe2—C18160.2 (4)Fe4—C52—H52125.2
C5—C1—C2109.4 (8)C54—C53—C52106.8 (9)
C5—C1—Fe170.3 (5)C54—C53—Fe469.9 (5)
C2—C1—Fe170.7 (5)C52—C53—Fe468.9 (5)
C5—C1—H1125.3C54—C53—H53126.6
C2—C1—H1125.3C52—C53—H53126.6
Fe1—C1—H1125.2Fe4—C53—H53126.2
C1—C2—C3106.5 (9)C53—C54—C55108.7 (10)
C1—C2—Fe168.5 (5)C53—C54—Fe470.4 (5)
C3—C2—Fe168.9 (5)C55—C54—Fe469.5 (5)
C1—C2—H2126.8C53—C54—H54125.6
C3—C2—H2126.8C55—C54—H54125.6
Fe1—C2—H2127.4Fe4—C54—H54126.0
C4—C3—C2108.5 (8)C51—C55—C54107.8 (9)
C4—C3—Fe169.6 (5)C51—C55—Fe470.0 (5)
C2—C3—Fe170.4 (5)C54—C55—Fe469.8 (5)
C4—C3—H3125.8C51—C55—H55126.1
C2—C3—H3125.8C54—C55—H55126.1
Fe1—C3—H3125.9Fe4—C55—H55125.7
C3—C4—C5108.7 (9)C70—Fe5—C6940.6 (3)
C3—C4—Fe170.0 (5)C70—Fe5—C6641.6 (3)
C5—C4—Fe170.0 (5)C69—Fe5—C6669.1 (3)
C3—C4—H4125.7C70—Fe5—C63163.8 (4)
C5—C4—H4125.7C69—Fe5—C63154.1 (4)
Fe1—C4—H4125.9C66—Fe5—C63125.4 (4)
C1—C5—C4106.9 (8)C70—Fe5—C65120.9 (3)
C1—C5—Fe169.2 (5)C69—Fe5—C65106.8 (4)
C4—C5—Fe169.1 (5)C66—Fe5—C65157.4 (4)
C1—C5—H5126.5C63—Fe5—C6568.1 (4)
C4—C5—H5126.5C70—Fe5—C61109.6 (4)
Fe1—C5—H5126.7C69—Fe5—C61125.9 (4)
C7—C6—C10107.1 (8)C66—Fe5—C61123.0 (4)
C7—C6—Fe170.1 (5)C63—Fe5—C6167.7 (4)
C10—C6—Fe169.0 (5)C65—Fe5—C6140.4 (4)
C7—C6—H6126.4C70—Fe5—C64154.8 (3)
C10—C6—H6126.4C69—Fe5—C64118.6 (3)
Fe1—C6—H6126.1C66—Fe5—C64160.7 (4)
C6—C7—C8108.1 (8)C63—Fe5—C6440.7 (4)
C6—C7—Fe169.5 (5)C65—Fe5—C6441.1 (4)
C8—C7—Fe170.0 (5)C61—Fe5—C6468.6 (4)
C6—C7—H7125.9C70—Fe5—C6868.2 (3)
C8—C7—H7125.9C69—Fe5—C6840.5 (3)
Fe1—C7—H7126.1C66—Fe5—C6868.3 (4)
C9—C8—C7108.1 (8)C63—Fe5—C68119.7 (4)
C9—C8—Fe169.3 (5)C65—Fe5—C68123.8 (4)
C7—C8—Fe168.5 (5)C61—Fe5—C68161.7 (4)
C9—C8—H8125.9C64—Fe5—C68105.3 (4)
C7—C8—H8125.9C70—Fe5—C6768.7 (3)
Fe1—C8—H8127.8C69—Fe5—C6768.4 (3)
C8—C9—C10108.0 (8)C66—Fe5—C6740.7 (4)
C8—C9—Fe171.1 (5)C63—Fe5—C67107.4 (4)
C10—C9—Fe168.8 (4)C65—Fe5—C67160.3 (4)
C8—C9—H9126.0C61—Fe5—C67157.5 (4)
C10—C9—H9126.0C64—Fe5—C67122.9 (4)
Fe1—C9—H9125.7C68—Fe5—C6740.3 (3)
C6—C10—C9108.6 (7)C70—Fe5—C62127.4 (4)
C6—C10—C11128.7 (8)C69—Fe5—C62163.7 (4)
C9—C10—C11122.6 (8)C66—Fe5—C62109.2 (4)
C6—C10—Fe169.8 (5)C63—Fe5—C6240.2 (4)
C9—C10—Fe170.0 (4)C65—Fe5—C6268.2 (4)
C11—C10—Fe1125.1 (6)C61—Fe5—C6240.4 (4)
O12—C11—O13122.4 (7)C64—Fe5—C6268.5 (4)
O12—C11—C10125.8 (7)C68—Fe5—C62155.2 (4)
O13—C11—C10111.5 (7)C67—Fe5—C62121.6 (4)
C14—O13—C11118.2 (6)C83—Fe6—C76108.3 (4)
O15—C14—O13122.7 (8)C83—Fe6—C8240.8 (4)
O15—C14—C16126.0 (8)C76—Fe6—C82124.6 (4)
O13—C14—C16111.1 (7)C83—Fe6—C80125.1 (4)
C20—C16—C17108.5 (7)C76—Fe6—C8041.2 (4)
C20—C16—C14129.0 (8)C82—Fe6—C80162.0 (4)
C17—C16—C14122.1 (8)C83—Fe6—C77122.5 (4)
C20—C16—Fe270.0 (5)C76—Fe6—C7741.8 (3)
C17—C16—Fe270.5 (5)C82—Fe6—C77107.2 (4)
C14—C16—Fe2119.5 (6)C80—Fe6—C7769.4 (4)
C18—C17—C16106.8 (8)C83—Fe6—C8168.5 (4)
C18—C17—Fe270.5 (5)C76—Fe6—C81161.1 (4)
C16—C17—Fe267.8 (4)C82—Fe6—C8140.8 (4)
C18—C17—H17126.6C80—Fe6—C81155.9 (4)
C16—C17—H17126.6C77—Fe6—C81123.0 (4)
Fe2—C17—H17126.6C83—Fe6—C8440.4 (4)
C17—C18—C19108.7 (8)C76—Fe6—C84121.6 (4)
C17—C18—Fe269.4 (5)C82—Fe6—C8468.6 (4)
C19—C18—Fe269.4 (5)C80—Fe6—C84107.6 (4)
C17—C18—H18125.6C77—Fe6—C84158.0 (4)
C19—C18—H18125.6C81—Fe6—C8468.8 (4)
Fe2—C18—H18127.2C83—Fe6—C79161.3 (4)
C20—C19—C18108.1 (8)C76—Fe6—C7968.5 (4)
C20—C19—Fe268.7 (5)C82—Fe6—C79156.3 (4)
C18—C19—Fe270.1 (5)C80—Fe6—C7940.3 (3)
C20—C19—H19126.0C77—Fe6—C7968.2 (4)
C18—C19—H19126.0C81—Fe6—C79120.7 (4)
Fe2—C19—H19126.9C84—Fe6—C79124.4 (4)
C19—C20—C16108.0 (8)C83—Fe6—C8568.6 (4)
C19—C20—Fe270.9 (5)C76—Fe6—C85156.9 (4)
C16—C20—Fe269.0 (5)C82—Fe6—C8569.0 (4)
C19—C20—H20126.0C80—Fe6—C85120.6 (4)
C16—C20—H20126.0C77—Fe6—C85159.4 (4)
Fe2—C20—H20125.7C81—Fe6—C8541.0 (4)
C25—C21—C22108.3 (9)C84—Fe6—C8541.2 (4)
C25—C21—Fe271.0 (6)C79—Fe6—C85106.7 (4)
C22—C21—Fe270.6 (5)C83—Fe6—C78156.8 (4)
C25—C21—H21125.8C76—Fe6—C7868.7 (3)
C22—C21—H21125.8C82—Fe6—C78120.7 (4)
Fe2—C21—H21124.1C80—Fe6—C7868.7 (4)
C23—C22—C21107.0 (10)C77—Fe6—C7839.9 (4)
C23—C22—Fe269.6 (5)C81—Fe6—C78106.6 (4)
C21—C22—Fe268.5 (5)C84—Fe6—C78161.0 (4)
C23—C22—H22126.5C79—Fe6—C7840.9 (4)
C21—C22—H22126.5C85—Fe6—C78123.4 (4)
Fe2—C22—H22126.9C65—C61—C62108.6 (8)
C24—C23—C22108.0 (9)C65—C61—Fe569.7 (5)
C24—C23—Fe269.2 (5)C62—C61—Fe570.1 (5)
C22—C23—Fe270.1 (5)C65—C61—H61125.7
C24—C23—H23126.0C62—C61—H61125.7
C22—C23—H23126.0Fe5—C61—H61126.1
Fe2—C23—H23126.2C63—C62—C61107.5 (9)
C23—C24—C25110.0 (9)C63—C62—Fe569.5 (5)
C23—C24—Fe271.2 (6)C61—C62—Fe569.5 (5)
C25—C24—Fe271.2 (5)C63—C62—H62126.2
C23—C24—H24125.0C61—C62—H62126.2
C25—C24—H24125.0Fe5—C62—H62126.3
Fe2—C24—H24124.2C62—C63—C64109.5 (9)
C24—C25—C21106.6 (9)C62—C63—Fe570.3 (5)
C24—C25—Fe268.5 (6)C64—C63—Fe569.8 (5)
C21—C25—Fe268.6 (5)C62—C63—H63125.3
C24—C25—H25126.7C64—C63—H63125.3
C21—C25—H25126.7Fe5—C63—H63126.2
Fe2—C25—H25127.7C63—C64—C65106.4 (8)
C40—Fe3—C33149.2 (3)C63—C64—Fe569.5 (5)
C40—Fe3—C32170.3 (3)C65—C64—Fe569.4 (5)
C33—Fe3—C3240.1 (3)C63—C64—H64126.8
C40—Fe3—C34117.4 (3)C65—C64—H64126.8
C33—Fe3—C3440.6 (4)Fe5—C64—H64125.9
C32—Fe3—C3468.4 (4)C61—C65—C64108.1 (8)
C40—Fe3—C3868.9 (3)C61—C65—Fe569.9 (5)
C33—Fe3—C38106.2 (4)C64—C65—Fe569.5 (5)
C32—Fe3—C38114.6 (3)C61—C65—H65126.0
C34—Fe3—C38128.2 (4)C64—C65—H65126.0
C40—Fe3—C3941.2 (3)Fe5—C65—H65126.2
C33—Fe3—C39115.3 (4)C67—C66—C70106.9 (8)
C32—Fe3—C39146.8 (3)C67—C66—Fe569.9 (5)
C34—Fe3—C39107.9 (4)C70—C66—Fe568.8 (4)
C38—Fe3—C3940.3 (3)C67—C66—H66126.6
C40—Fe3—C35110.6 (3)C70—C66—H66126.6
C33—Fe3—C3567.8 (4)Fe5—C66—H66126.3
C32—Fe3—C3568.1 (4)C68—C67—C66108.3 (8)
C34—Fe3—C3540.7 (4)C68—C67—Fe569.8 (5)
C38—Fe3—C35168.1 (3)C66—C67—Fe569.4 (5)
C39—Fe3—C35131.7 (3)C68—C67—H67125.8
C40—Fe3—C3641.4 (3)C66—C67—H67125.8
C33—Fe3—C36167.1 (4)Fe5—C67—H67126.5
C32—Fe3—C36130.1 (3)C67—C68—C69108.8 (8)
C34—Fe3—C36151.8 (4)C67—C68—Fe569.9 (5)
C38—Fe3—C3668.4 (3)C69—C68—Fe569.4 (5)
C39—Fe3—C3668.8 (3)C67—C68—H68125.6
C35—Fe3—C36119.5 (4)C69—C68—H68125.6
C40—Fe3—C31132.2 (4)Fe5—C68—H68126.7
C33—Fe3—C3167.8 (4)C70—C69—C68107.8 (7)
C32—Fe3—C3140.6 (4)C70—C69—Fe569.4 (5)
C34—Fe3—C3168.4 (3)C68—C69—Fe570.1 (5)
C38—Fe3—C31148.5 (3)C70—C69—H69126.1
C39—Fe3—C31171.0 (3)C68—C69—H69126.1
C35—Fe3—C3140.3 (3)Fe5—C69—H69126.0
C36—Fe3—C31110.2 (3)C69—C70—C66108.1 (7)
C40—Fe3—C3768.9 (3)C69—C70—C71128.4 (7)
C33—Fe3—C37128.1 (4)C66—C70—C71123.4 (8)
C32—Fe3—C37107.3 (3)C69—C70—Fe570.0 (5)
C34—Fe3—C37166.5 (4)C66—C70—Fe569.7 (4)
C38—Fe3—C3740.7 (3)C71—C70—Fe5127.3 (6)
C39—Fe3—C3768.2 (3)O72—C71—O73122.2 (7)
C35—Fe3—C37151.0 (4)O72—C71—C70126.7 (8)
C36—Fe3—C3740.4 (3)O73—C71—C70111.0 (7)
C31—Fe3—C37117.3 (3)C74—O73—C71118.9 (6)
C46—Fe4—C52123.8 (4)O75—C74—O73124.3 (8)
C46—Fe4—C55123.9 (4)O75—C74—C76125.6 (8)
C52—Fe4—C5567.3 (4)O73—C74—C76110.1 (7)
C46—Fe4—C5041.2 (3)C80—C76—C77107.4 (8)
C52—Fe4—C50160.5 (4)C80—C76—C74129.2 (8)
C55—Fe4—C50108.7 (4)C77—C76—C74123.0 (8)
C46—Fe4—C54160.2 (4)C80—C76—Fe669.8 (5)
C52—Fe4—C5466.9 (4)C77—C76—Fe669.6 (5)
C55—Fe4—C5440.7 (4)C74—C76—Fe6120.5 (6)
C50—Fe4—C54123.5 (4)C78—C77—C76108.2 (8)
C46—Fe4—C51108.4 (4)C78—C77—Fe671.2 (5)
C52—Fe4—C5140.3 (5)C76—C77—Fe668.7 (4)
C55—Fe4—C5140.3 (5)C78—C77—H77125.9
C50—Fe4—C51124.3 (4)C76—C77—H77125.9
C54—Fe4—C5167.9 (4)Fe6—C77—H77125.8
C46—Fe4—C53158.9 (4)C77—C78—C79107.8 (8)
C52—Fe4—C5340.3 (4)C77—C78—Fe668.9 (5)
C55—Fe4—C5367.9 (4)C79—C78—Fe669.0 (5)
C50—Fe4—C53157.9 (4)C77—C78—H78126.1
C54—Fe4—C5339.7 (4)C79—C78—H78126.1
C51—Fe4—C5368.2 (4)Fe6—C78—H78127.6
C46—Fe4—C4741.1 (3)C80—C79—C78108.7 (8)
C52—Fe4—C47107.5 (4)C80—C79—Fe669.2 (5)
C55—Fe4—C47159.6 (4)C78—C79—Fe670.1 (5)
C50—Fe4—C4769.2 (3)C80—C79—H79125.6
C54—Fe4—C47157.5 (4)C78—C79—H79125.6
C51—Fe4—C47123.0 (4)Fe6—C79—H79126.6
C53—Fe4—C47121.9 (4)C79—C80—C76107.9 (8)
C46—Fe4—C4968.6 (3)C79—C80—Fe670.4 (5)
C52—Fe4—C49157.8 (4)C76—C80—Fe669.0 (4)
C55—Fe4—C49123.9 (4)C79—C80—H80126.1
C50—Fe4—C4940.5 (3)C76—C80—H80126.1
C54—Fe4—C49107.9 (4)Fe6—C80—H80126.1
C51—Fe4—C49160.1 (4)C82—C81—C85108.5 (8)
C53—Fe4—C49121.8 (4)C82—C81—Fe669.5 (5)
C47—Fe4—C4968.5 (4)C85—C81—Fe670.1 (5)
C46—Fe4—C4868.9 (3)C82—C81—H81125.8
C52—Fe4—C48121.6 (4)C85—C81—H81125.8
C55—Fe4—C48159.3 (4)Fe6—C81—H81126.3
C50—Fe4—C4869.2 (3)C83—C82—C81107.5 (8)
C54—Fe4—C48122.1 (4)C83—C82—Fe669.2 (5)
C51—Fe4—C48157.8 (5)C81—C82—Fe669.7 (5)
C53—Fe4—C48105.9 (4)C83—C82—H82126.3
C47—Fe4—C4840.6 (3)C81—C82—H82126.3
C49—Fe4—C4841.1 (4)Fe6—C82—H82126.4
C35—C31—C32107.6 (8)C84—C83—C82109.4 (8)
C35—C31—Fe369.7 (5)C84—C83—Fe670.6 (5)
C32—C31—Fe369.2 (5)C82—C83—Fe670.0 (5)
C35—C31—H31126.2C84—C83—H83125.3
C32—C31—H31126.2C82—C83—H83125.3
Fe3—C31—H31126.5Fe6—C83—H83125.7
C33—C32—C31107.9 (8)C83—C84—C85107.8 (8)
C33—C32—Fe369.8 (5)C83—C84—Fe669.1 (5)
C31—C32—Fe370.2 (5)C85—C84—Fe669.7 (5)
C33—C32—H32126.1C83—C84—H84126.1
C31—C32—H32126.1C85—C84—H84126.1
Fe3—C32—H32125.6Fe6—C84—H84126.6
C32—C33—C34109.3 (8)C81—C85—C84106.8 (9)
C32—C33—Fe370.1 (5)C81—C85—Fe668.9 (5)
C34—C33—Fe369.9 (5)C84—C85—Fe669.1 (5)
C32—C33—H33125.4C81—C85—H85126.6
C34—C33—H33125.4C84—C85—H85126.6
Fe3—C33—H33126.2Fe6—C85—H85127.0
C33—C34—C35106.9 (8)
C5—C1—C2—C31.3 (10)C41—O43—C44—O4513.6 (12)
Fe1—C1—C2—C358.6 (6)C41—O43—C44—C46169.4 (6)
C5—C1—C2—Fe160.0 (6)O45—C44—C46—C476.8 (13)
C1—C2—C3—C41.0 (10)O43—C44—C46—C47176.2 (7)
Fe1—C2—C3—C459.4 (6)O45—C44—C46—C50173.9 (9)
C1—C2—C3—Fe158.4 (6)O43—C44—C46—C503.1 (12)
C2—C3—C4—C50.3 (10)O45—C44—C46—Fe494.7 (10)
Fe1—C3—C4—C559.5 (6)O43—C44—C46—Fe488.3 (8)
C2—C3—C4—Fe159.8 (6)C50—C46—C47—C481.0 (9)
C2—C1—C5—C41.1 (10)C44—C46—C47—C48178.4 (7)
Fe1—C1—C5—C459.0 (6)Fe4—C46—C47—C4859.2 (6)
C2—C1—C5—Fe160.2 (6)C50—C46—C47—Fe460.1 (5)
C3—C4—C5—C10.5 (10)C44—C46—C47—Fe4119.3 (8)
Fe1—C4—C5—C159.0 (6)C46—C47—C48—C491.0 (9)
C3—C4—C5—Fe159.6 (6)Fe4—C47—C48—C4958.9 (6)
C10—C6—C7—C80.3 (10)C46—C47—C48—Fe457.9 (5)
Fe1—C6—C7—C859.6 (6)C47—C48—C49—C500.7 (9)
C10—C6—C7—Fe159.3 (6)Fe4—C48—C49—C5058.3 (6)
C6—C7—C8—C91.1 (10)C47—C48—C49—Fe458.9 (6)
Fe1—C7—C8—C958.2 (6)C48—C49—C50—C460.1 (9)
C6—C7—C8—Fe159.3 (6)Fe4—C49—C50—C4658.7 (5)
C7—C8—C9—C101.5 (9)C48—C49—C50—Fe458.7 (6)
Fe1—C8—C9—C1059.1 (5)C47—C46—C50—C490.6 (9)
C7—C8—C9—Fe157.7 (6)C44—C46—C50—C49178.8 (8)
C7—C6—C10—C90.6 (9)Fe4—C46—C50—C4959.9 (6)
Fe1—C6—C10—C959.4 (5)C47—C46—C50—Fe460.4 (5)
C7—C6—C10—C11179.4 (8)C44—C46—C50—Fe4118.9 (8)
Fe1—C6—C10—C11119.4 (8)C55—C51—C52—C530.2 (11)
C7—C6—C10—Fe160.0 (6)Fe4—C51—C52—C5360.1 (7)
C8—C9—C10—C61.3 (9)C55—C51—C52—Fe459.9 (7)
Fe1—C9—C10—C659.3 (6)C51—C52—C53—C540.1 (11)
C8—C9—C10—C11179.8 (7)Fe4—C52—C53—C5459.9 (6)
Fe1—C9—C10—C11119.6 (7)C51—C52—C53—Fe460.0 (7)
C8—C9—C10—Fe160.6 (6)C52—C53—C54—C550.1 (10)
C6—C10—C11—O12165.2 (8)Fe4—C53—C54—C5559.2 (6)
C9—C10—C11—O1216.1 (13)C52—C53—C54—Fe459.2 (6)
Fe1—C10—C11—O12103.5 (9)C52—C51—C55—C540.3 (11)
C6—C10—C11—O139.1 (12)Fe4—C51—C55—C5459.8 (6)
C9—C10—C11—O13169.5 (7)C52—C51—C55—Fe459.5 (6)
Fe1—C10—C11—O1382.2 (8)C53—C54—C55—C510.2 (11)
O12—C11—O13—C1431.4 (11)Fe4—C54—C55—C5159.9 (6)
C10—C11—O13—C14154.0 (7)C53—C54—C55—Fe459.7 (7)
C11—O13—C14—O1529.7 (12)C65—C61—C62—C630.0 (10)
C11—O13—C14—C16155.1 (7)Fe5—C61—C62—C6359.4 (6)
O15—C14—C16—C20172.2 (9)C65—C61—C62—Fe559.3 (6)
O13—C14—C16—C202.8 (12)C61—C62—C63—C640.4 (11)
O15—C14—C16—C170.4 (13)Fe5—C62—C63—C6459.0 (6)
O13—C14—C16—C17174.6 (7)C61—C62—C63—Fe559.4 (6)
O15—C14—C16—Fe284.9 (11)C62—C63—C64—C650.5 (10)
O13—C14—C16—Fe290.1 (8)Fe5—C63—C64—C6559.8 (6)
C20—C16—C17—C180.1 (9)C62—C63—C64—Fe559.3 (6)
C14—C16—C17—C18173.3 (7)C62—C61—C65—C640.3 (10)
Fe2—C16—C17—C1860.1 (6)Fe5—C61—C65—C6459.2 (6)
C20—C16—C17—Fe260.0 (6)C62—C61—C65—Fe559.5 (6)
C14—C16—C17—Fe2113.3 (8)C63—C64—C65—C610.5 (10)
C16—C17—C18—C190.1 (10)Fe5—C64—C65—C6159.4 (6)
Fe2—C17—C18—C1958.3 (6)C63—C64—C65—Fe560.0 (6)
C16—C17—C18—Fe258.4 (5)C70—C66—C67—C680.1 (10)
C17—C18—C19—C200.0 (10)Fe5—C66—C67—C6859.2 (6)
Fe2—C18—C19—C2058.3 (6)C70—C66—C67—Fe559.1 (6)
C17—C18—C19—Fe258.3 (6)C66—C67—C68—C690.4 (10)
C18—C19—C20—C160.0 (10)Fe5—C67—C68—C6958.6 (6)
Fe2—C19—C20—C1659.2 (6)C66—C67—C68—Fe558.9 (6)
C18—C19—C20—Fe259.2 (6)C67—C68—C69—C700.5 (10)
C17—C16—C20—C190.1 (10)Fe5—C68—C69—C7059.4 (6)
C14—C16—C20—C19172.7 (8)C67—C68—C69—Fe558.9 (6)
Fe2—C16—C20—C1960.4 (6)C68—C69—C70—C660.4 (9)
C17—C16—C20—Fe260.3 (6)Fe5—C69—C70—C6659.4 (6)
C14—C16—C20—Fe2112.3 (9)C68—C69—C70—C71177.9 (8)
C25—C21—C22—C232.2 (10)Fe5—C69—C70—C71122.3 (9)
Fe2—C21—C22—C2359.2 (7)C68—C69—C70—Fe559.8 (6)
C25—C21—C22—Fe261.4 (6)C67—C66—C70—C690.2 (9)
C21—C22—C23—C240.5 (11)Fe5—C66—C70—C6959.6 (6)
Fe2—C22—C23—C2459.0 (7)C67—C66—C70—C71178.2 (7)
C21—C22—C23—Fe258.5 (6)Fe5—C66—C70—C71122.0 (8)
C22—C23—C24—C251.3 (11)C67—C66—C70—Fe559.8 (6)
Fe2—C23—C24—C2560.9 (7)C69—C70—C71—O72162.6 (9)
C22—C23—C24—Fe259.6 (7)C66—C70—C71—O7215.4 (13)
C23—C24—C25—C212.6 (11)Fe5—C70—C71—O72104.2 (9)
Fe2—C24—C25—C2158.3 (6)C69—C70—C71—O7313.3 (12)
C23—C24—C25—Fe260.9 (7)C66—C70—C71—O73168.6 (7)
C22—C21—C25—C242.9 (10)Fe5—C70—C71—O7379.8 (8)
Fe2—C21—C25—C2458.2 (6)O72—C71—O73—C7434.5 (11)
C22—C21—C25—Fe261.1 (6)C70—C71—O73—C74149.4 (7)
C35—C31—C32—C330.5 (10)C71—O73—C74—O7521.9 (12)
Fe3—C31—C32—C3359.9 (6)C71—O73—C74—C76160.0 (7)
C35—C31—C32—Fe359.3 (6)O75—C74—C76—C80174.3 (9)
C31—C32—C33—C341.0 (10)O73—C74—C76—C803.8 (12)
Fe3—C32—C33—C3459.1 (6)O75—C74—C76—C772.1 (14)
C31—C32—C33—Fe360.1 (6)O73—C74—C76—C77176.0 (7)
C32—C33—C34—C351.0 (10)O75—C74—C76—Fe686.3 (11)
Fe3—C33—C34—C3560.3 (6)O73—C74—C76—Fe691.7 (8)
C32—C33—C34—Fe359.2 (6)C80—C76—C77—C780.6 (9)
C32—C31—C35—C340.1 (10)C74—C76—C77—C78174.3 (8)
Fe3—C31—C35—C3458.9 (6)Fe6—C76—C77—C7860.5 (6)
C32—C31—C35—Fe359.0 (6)C80—C76—C77—Fe659.8 (6)
C33—C34—C35—C310.7 (10)C74—C76—C77—Fe6113.8 (7)
Fe3—C34—C35—C3159.3 (6)C76—C77—C78—C790.7 (10)
C33—C34—C35—Fe360.0 (6)Fe6—C77—C78—C7958.2 (6)
C40—C36—C37—C380.4 (9)C76—C77—C78—Fe658.9 (6)
Fe3—C36—C37—C3858.2 (6)C77—C78—C79—C800.5 (10)
C40—C36—C37—Fe357.8 (5)Fe6—C78—C79—C8058.7 (6)
C36—C37—C38—C391.2 (9)C77—C78—C79—Fe658.1 (6)
Fe3—C37—C38—C3959.8 (6)C78—C79—C80—C760.1 (10)
C36—C37—C38—Fe358.5 (6)Fe6—C79—C80—C7659.1 (6)
C37—C38—C39—C402.4 (9)C78—C79—C80—Fe659.2 (6)
Fe3—C38—C39—C4057.6 (6)C77—C76—C80—C790.3 (9)
C37—C38—C39—Fe360.0 (6)C74—C76—C80—C79173.4 (8)
C38—C39—C40—C362.7 (9)Fe6—C76—C80—C7960.0 (6)
Fe3—C39—C40—C3661.2 (6)C77—C76—C80—Fe659.7 (6)
C38—C39—C40—C41177.4 (8)C74—C76—C80—Fe6113.5 (9)
Fe3—C39—C40—C41118.9 (9)C85—C81—C82—C830.3 (11)
C38—C39—C40—Fe358.5 (6)Fe6—C81—C82—C8359.2 (6)
C37—C36—C40—C391.9 (9)C85—C81—C82—Fe659.4 (6)
Fe3—C36—C40—C3961.2 (6)C81—C82—C83—C840.3 (11)
C37—C36—C40—C41178.2 (7)Fe6—C82—C83—C8459.8 (7)
Fe3—C36—C40—C41118.9 (8)C81—C82—C83—Fe659.4 (6)
C37—C36—C40—Fe359.3 (6)C82—C83—C84—C850.2 (11)
C39—C40—C41—O42165.6 (9)Fe6—C83—C84—C8559.2 (6)
C36—C40—C41—O4214.3 (14)C82—C83—C84—Fe659.4 (7)
Fe3—C40—C41—O42102.5 (9)C82—C81—C85—C840.2 (10)
C39—C40—C41—O4312.0 (12)Fe6—C81—C85—C8458.9 (6)
C36—C40—C41—O43168.1 (7)C82—C81—C85—Fe659.1 (6)
Fe3—C40—C41—O4380.0 (8)C83—C84—C85—C810.0 (10)
O42—C41—O43—C4442.5 (11)Fe6—C84—C85—C8158.8 (6)
C40—C41—O43—C44139.8 (7)C83—C84—C85—Fe658.8 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C49—H49···O720.952.643.516 (10)153
C31—H31···O120.952.493.387 (10)158
C5—H5···O45i0.952.563.367 (11)142
C85—H85···O42ii0.952.573.438 (12)152
C6—H6···O12iii0.952.733.017 (10)98
C6—H6···O15iii0.952.333.255 (11)164
C39—H39···O42iii0.952.653.127 (10)112
C39—H39···O45iii0.952.663.595 (10)170
C69—H69···O72iv0.952.793.084 (10)99
C69—H69···O75iv0.952.353.273 (10)164
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x, y+1, z1/2; (iii) x1, y, z; (iv) x+1, y, z.
Experimental details top
(1B) (This work)(1A) (McAdam & Simpson, 2016)
Crystal data
Chemical formula[Fe2(C5H5)2(C12H8O3)][Fe2(C5H5)2(C12H8O3)]
Mr442.06442.06
Crystal system, space groupMonoclinic, CcOrthorhombic, Pbca
Temperature (K)150100
a, b, c (Å)5.9758 (5), 36.456 (3), 24.363 (2)14.8773 (2), 12.2499 (2), 19.3288 (3)
β (°)91.997 (3)
V3)5304.4 (8)3522.59 (9)
Z128
Radiation typeMo KαCu Kα
µ (mm-1)1.6613.38
Crystal size (mm)0.56 × 0.36 × 0.300.16 × 0.13 × 0.11
Data collection
DiffractometerBruker APEXIIAgilent SuperNova Dual Source diffractometer with an Atlas detector
Absorption correctionMulti-scan (Sheldrick, 2014)Gaussian (CrysAlis PRO; Agilent, 2014)
Tmin, Tmax0.486, 0.6080.267, 0.456
No. of measured, independent and observed [I > 2σ(I)] reflections16323, 10804, 1035013584, 3468, 3262
Rint0.0230.040
(sin θ/λ)max-1)0.6490.621
Refinement
R[F2 > 2σ(F2)], wR(F2), S0.049, 0.120, 1.110.030, 0.090, 0.84
No. of reflections108043468
No. of parameters730244
No. of restraints320
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Weighting schemew = 1/[σ2(Fo2) + (0.0346P)2 + 44.5361P] where P = (Fo2 + 2Fc2)/3w = 1/[σ2(Fo2) + (0.089P)2 + 0.2107P] where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å-3)0.96, -0.870.31, -0.68
Absolute structureFlack x determined using 4113 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter0.204 (11)
Computer programs: APEX2 (Bruker, 2014), SHELXT (Sheldrick, 2015a), SHELXL2016 (Sheldrick, 2015b), SXGRAPH (Farrugia, 1999), Mercury (Macrae et al., 2008) and CRYSCALC (T. Roisnel, local program).
Comparison of selected geometric parameters (°) of Cp-based carboxylic anhydrides top
CompoundAnhydride torsion angleFc/Fc torsion angleCp/Cp eclipse angleCp/Cp planes angleO—C—C—C torsion angle
(1A)57.4 (2)72.26.3 – 5.32.84 – 1.7512.1 (3) – 2.1 (3)
(2)62.4 (5)75.1*1.96 – 2.5211.7 (9) – 6.2 (9)
(2)66.7 (5)103.7*2.61 – 2.719.8 (9) – 6.2 (9)
(3)57.0 (2)85.918.9 – 7.02.31 – 4.550.7 (4) – 19.4 (5)
(4)62.3 (3)72.912.8 – 3.22.19 – 2.033.6 (5) – 4.2 (5)
(5)27.5 (2)1.50.6 – 0.42.51 – 2.518.3 (4) – 21.7 (4)
(1B)50.9 (7)33.67.3 – 2.51.33 – 1.7216 (1) – 1 (1)
(1B)46.6 (7)146.317.1 – 0.70.89 – 2.5114 (1) – 7 (1)
(1B)47.0 (7)30.13.9 – 6.20.39 – 2.222 (1) – 16 (1)
Note: (*) not applicable.
 

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