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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
CCDC reference: 1553140
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 = 442.06 | 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) Å3 | Prism, red |
Z = 12 | 0.56 × 0.36 × 0.30 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.11 | 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 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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O45i | 0.95 | 2.56 | 3.367 (11) | 142 |
C85—H85···O42ii | 0.95 | 2.57 | 3.438 (12) | 152 |
C6—H6···O12iii | 0.95 | 2.73 | 3.017 (10) | 98 |
C6—H6···O15iii | 0.95 | 2.33 | 3.255 (11) | 164 |
C39—H39···O42iii | 0.95 | 2.65 | 3.127 (10) | 112 |
C39—H39···O45iii | 0.95 | 2.66 | 3.595 (10) | 170 |
C69—H69···O72iv | 0.95 | 2.79 | 3.084 (10) | 99 |
C69—H69···O75iv | 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. |
Experimental details top | (1B) (This work) | (1A) (McAdam & Simpson, 2016) |
Crystal data | | |
Chemical formula | [Fe2(C5H5)2(C12H8O3)] | [Fe2(C5H5)2(C12H8O3)] |
Mr | 442.06 | 442.06 |
Crystal system, space group | Monoclinic, Cc | Orthorhombic, Pbca |
Temperature (K) | 150 | 100 |
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) | |
V (Å3) | 5304.4 (8) | 3522.59 (9) |
Z | 12 | 8 |
Radiation type | Mo Kα | Cu Kα |
µ (mm-1) | 1.66 | 13.38 |
Crystal size (mm) | 0.56 × 0.36 × 0.30 | 0.16 × 0.13 × 0.11 |
Data collection | | |
Diffractometer | Bruker APEXII | Agilent SuperNova Dual Source diffractometer with an Atlas detector |
Absorption correction | Multi-scan (Sheldrick, 2014) | Gaussian (CrysAlis PRO; Agilent, 2014) |
Tmin, Tmax | 0.486, 0.608 | 0.267, 0.456 |
No. of measured, independent and
observed [I > 2σ(I)] reflections | 16323, 10804, 10350 | 13584, 3468, 3262 |
Rint | 0.023 | 0.040 |
(sin θ/λ)max (Å-1) | 0.649 | 0.621 |
Refinement | | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.120, 1.11 | 0.030, 0.090, 0.84 |
No. of reflections | 10804 | 3468 |
No. of parameters | 730 | 244 |
No. of restraints | 32 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Weighting scheme | w = 1/[σ2(Fo2) + (0.0346P)2 + 44.5361P]
where P = (Fo2 + 2Fc2)/3 | w = 1/[σ2(Fo2) + (0.089P)2 + 0.2107P]
where P = (Fo2 + 2Fc2)/3 |
Δρmax, Δρmin (e Å-3) | 0.96, -0.87 | 0.31, -0.68 |
Absolute structure | Flack x determined using 4113 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) | |
Absolute structure parameter | 0.204 (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 topCompound | Anhydride torsion angle | Fc/Fc torsion angle | Cp/Cp eclipse angle | Cp/Cp planes angle | O—C—C—C torsion angle |
(1A) | 57.4 (2) | 72.2 | 6.3 – 5.3 | 2.84 – 1.75 | 12.1 (3) – 2.1 (3) |
(2) | 62.4 (5) | 75.1 | * | 1.96 – 2.52 | 11.7 (9) – 6.2 (9) |
(2) | 66.7 (5) | 103.7 | * | 2.61 – 2.71 | 9.8 (9) – 6.2 (9) |
(3) | 57.0 (2) | 85.9 | 18.9 – 7.0 | 2.31 – 4.55 | 0.7 (4) – 19.4 (5) |
(4) | 62.3 (3) | 72.9 | 12.8 – 3.2 | 2.19 – 2.03 | 3.6 (5) – 4.2 (5) |
(5) | 27.5 (2) | 1.5 | 0.6 – 0.4 | 2.51 – 2.51 | 8.3 (4) – 21.7 (4) |
(1B) | 50.9 (7) | 33.6 | 7.3 – 2.5 | 1.33 – 1.72 | 16 (1) – 1 (1) |
(1B) | 46.6 (7) | 146.3 | 17.1 – 0.7 | 0.89 – 2.51 | 14 (1) – 7 (1) |
(1B) | 47.0 (7) | 30.1 | 3.9 – 6.2 | 0.39 – 2.22 | 2 (1) – 16 (1) |
Note: (*) not applicable. |
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