metal-organic compounds
4,5-Diferrocenyl-1,2-dithiol-3-one
aFacultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, Ciudad de México, 04510, Mexico
*Correspondence e-mail: eiklimova@yahoo.com.mx
The title compound, [Fe2(C5H5)2(C13H8OS2)], crystallizes with two molecules in the Each molecule comprises a pair of ferrocenyl units bridged by a dithiol-3-one moiety. The dihedral angles between the dithiol-3-one ring and the substituted cyclopentadienyl rings are in the range 32.4 (3)–39.3 (3)°. One of the dithiol-3-one rings was refined as being disordered over two sets of sites while the same kind of disorder in the other molecule was negligible. The molecular packing is dominated by C—H⋯O hydrogen bonds and C—H⋯π interactions.
Keywords: crystal structure; 4,5-diferrocenyl-1,2-dithiol-3-one; disorder.
CCDC reference: 1841323
Structure description
Background to the chemistry of ferrocenes and their potential applications was compiled by Togni & Hayashi (1995). 1,2-Dithiole-3-one derivatives are of current interest since they have a broad spectrum of biological activities (He et al., 2004) and may be useful synthons for many sulfur-containing heterocycles (Konstantinova et al., 2007). An analogue of these compounds is Oltipraz (4-methyl-5-(2-pyrazinyl)-1,2-dithiole-3-thione) that has been clinically tested as a preventive agent against various types of cancer (Iida et al., 2004).
Each of the two molecules A and B in the of the title compound is constituted by a pair of ferrocenyl units bridged by a dithiol-3-one ring (Fig. 1). The cyclopentadienyl (Cp) rings are almost parallel, making dihedral angles of 1.3 (3) and 1.7 (2)° for molecule A containing Fe1 and Fe2, and 1.7 (2) and 2.7 (3)° for molecule B containing Fe3 and Fe4, respectively. The dihedral angles between the dithiol-3-one ring and the substituted cyclopentadienyl rings are 39.3 (3) and 32.6 (2)° for molecule A and 37.6 (2) and 32.4 (2)° for molecule B. The cyclopentadienyl rings of the ferrocenyl moieties in both molecules adopt eclipsed conformations. All bond lengths and angles for two crystallographically independent molecules are similar (Table 1).
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In the ), molecules B are linked via weak C—H⋯O hydrogen bonds between the Cp rings and the O atoms of the 1,2-dithiole-3-one moieties (Table 2) with a graph-set motif C11(8) forming a chain parallel to the a axis. Molecules A and B, on the other hand, show intermolecular interactions of the type C—H⋯π, with C1—H1⋯Cg10 and C43—H43⋯Cg6 distances of 3.04 and 3.12 Å, respectively, where Cg10 and Cg6 are the centroids of the rings C38–C42 and C20–24. These interactions form slabs lying parallel to the ac plane.
(Fig. 2Synthesis and crystallization
A mixture of sodium sulfide (10 mmol) and sulfur (5 mmol) in ethanol (80 ml) was added to 1,2-diferrocenylcyclopropenone (5 mmol) and stirred at 353 K for 4 h. The solvents were removed in vacuo, and the residues purified by with alumina and a mixture of hexane:diethyl ether (ratio 1:1 v/v) as Red crystals of 4,5-diferrocenyl-1,2-dithiol-3-one, suitable for single-crystal were obtained by slow evaporation of a saturated dichloromethane/hexane (ratio 1:1 v/v) solution. Yield (75%), mp. 468-470 K.
1H NMR (300 MHz, CDCl3) δ: 4.24 (5 H, s, C5H5), δ: 4.05 (5 H, s, C5H5), δ: 4.04 (4 H, s, C5H4), δ: 4.22 (2 H, m, C5H4), δ: 4.17 (2 H, s, C5H4) p.p.m., 13C NMR (75 MHz, CDCl3) δ: 79.45, 81.45 (2Cipso Fc), δ: 69.60 (C5H5), δ: 70.61 (C5H5), δ: 4.60, 69.55, 69.03, 67.96 (4C5H4), 136.15, 164.69, (2 C), 169.25 (C=O) p.p.m., MS: m/z 486 [M]+. Analysis calculated for C23H18Fe2OS2: C, 56.90, H, 3.68, S, 12.85, Found C, 56.70, H, 3.90, S, 13.05%.
Refinement
Crystal data, data collection and structure . Atoms C18, O1 and S1 of molecule A were refined as being disordered over two sets of sites with occupancies of 0.56: 0.44 using restraints so that the bond lengths and angles of the two components are comparable. Remaining electron densities close to the same type of atoms were also found for molecule B but to a much lesser extend (preliminary of the occupancies about 0.93:0.07). For the final model this type of disorder was neglected.
details are summarized in Table 3Structural data
CCDC reference: 1841323
https://doi.org/10.1107/S2414314618006855/wm4074sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618006855/wm4074Isup2.hkl
Data collection: CrysAlis PRO (Agilent, 2013); cell
?; data reduction: CrysAlis RED (Agilent, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and Mercury (Macrae et al., 2008).[Fe2(C5H5)2(C13H8OS2)] | Z = 4 |
Mr = 486.19 | F(000) = 992 |
Triclinic, P1 | Dx = 1.695 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8525 (4) Å | Cell parameters from 4380 reflections |
b = 10.6407 (6) Å | θ = 3.5–29.5° |
c = 19.2720 (9) Å | µ = 1.75 mm−1 |
α = 98.867 (4)° | T = 130 K |
β = 95.255 (4)° | Block, dark red |
γ = 105.512 (4)° | 0.16 × 0.13 × 0.06 mm |
V = 1904.76 (17) Å3 |
Agilent Xcalibur Atlas Gemini diffractometer | 7772 independent reflections |
Graphite monochromator | 5624 reflections with I > 2σ(I) |
Detector resolution: 10.4685 pixels mm-1 | Rint = 0.045 |
ω scans | θmax = 26.4°, θmin = 3.5° |
Absorption correction: analytical (CrysAlis RED; Agilent, 2013) | h = −12→12 |
Tmin = 0.856, Tmax = 0.937 | k = −13→13 |
19834 measured reflections | l = −24→24 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0398P)2 + 2.1419P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
7772 reflections | Δρmax = 0.91 e Å−3 |
515 parameters | Δρmin = −0.51 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.7650 (4) | −0.2765 (4) | 0.8413 (2) | 0.0277 (9) | |
H1 | 0.717766 | −0.361755 | 0.807503 | 0.033* | |
C2 | 0.9125 (4) | −0.2109 (4) | 0.8546 (2) | 0.0283 (9) | |
H2 | 0.987812 | −0.242726 | 0.83218 | 0.034* | |
C3 | 0.9362 (4) | −0.0949 (4) | 0.9059 (2) | 0.0264 (9) | |
H3 | 1.030954 | −0.030483 | 0.925819 | 0.032* | |
C4 | 0.8038 (4) | −0.0858 (4) | 0.9250 (2) | 0.0252 (9) | |
H4 | 0.788102 | −0.013583 | 0.960429 | 0.03* | |
C5 | 0.6954 (4) | −0.1981 (4) | 0.8841 (2) | 0.0246 (9) | |
C6 | 0.5408 (4) | −0.2258 (4) | 0.8849 (2) | 0.0259 (9) | |
C7 | 0.4686 (4) | −0.1333 (4) | 0.8899 (2) | 0.0248 (9) | |
C8 | 0.5258 (4) | 0.0088 (4) | 0.8901 (2) | 0.0242 (9) | |
C9 | 0.6355 (4) | 0.0713 (4) | 0.8529 (2) | 0.0241 (9) | |
H9 | 0.688804 | 0.024483 | 0.821315 | 0.029* | |
C10 | 0.6565 (4) | 0.2088 (4) | 0.8676 (2) | 0.0294 (9) | |
H10 | 0.727351 | 0.276738 | 0.848641 | 0.035* | |
C11 | 0.5580 (4) | 0.2346 (4) | 0.9140 (2) | 0.0334 (10) | |
H11 | 0.547666 | 0.323862 | 0.933131 | 0.04* | |
C12 | 0.4767 (4) | 0.1116 (4) | 0.9277 (2) | 0.0263 (9) | |
H12 | 0.399114 | 0.098759 | 0.958204 | 0.032* | |
C13 | 0.2404 (4) | 0.0579 (5) | 0.7823 (2) | 0.0341 (10) | |
H13 | 0.159834 | 0.019829 | 0.807937 | 0.041* | |
C14 | 0.3016 (5) | 0.1943 (5) | 0.7819 (2) | 0.0375 (11) | |
H14 | 0.272346 | 0.269719 | 0.807527 | 0.045* | |
C15 | 0.4120 (5) | 0.2050 (5) | 0.7387 (2) | 0.0381 (11) | |
H15 | 0.474338 | 0.289612 | 0.728965 | 0.046* | |
C16 | 0.4199 (5) | 0.0770 (5) | 0.7127 (2) | 0.0378 (11) | |
H16 | 0.488598 | 0.054851 | 0.681139 | 0.045* | |
C17 | 0.3151 (4) | −0.0157 (5) | 0.7394 (2) | 0.0362 (11) | |
H17 | 0.295695 | −0.114355 | 0.729435 | 0.043* | |
C20 | 0.8309 (6) | −0.2611 (5) | 1.0507 (2) | 0.0427 (12) | |
H20 | 0.808591 | −0.192404 | 1.085689 | 0.051* | |
C21 | 0.9678 (5) | −0.2604 (5) | 1.0344 (3) | 0.0482 (14) | |
H21 | 1.059139 | −0.19195 | 1.055888 | 0.058* | |
C22 | 0.9523 (5) | −0.3730 (5) | 0.9829 (3) | 0.0500 (14) | |
H22 | 1.031113 | −0.399257 | 0.960867 | 0.06* | |
C23 | 0.8068 (5) | −0.4429 (5) | 0.9671 (3) | 0.0432 (12) | |
H23 | 0.764202 | −0.527807 | 0.932351 | 0.052* | |
C24 | 0.7318 (5) | −0.3733 (5) | 1.0099 (2) | 0.0400 (11) | |
H24 | 0.626754 | −0.39954 | 1.010682 | 0.048* | |
Fe1 | 0.83868 (6) | −0.25721 (6) | 0.94571 (3) | 0.02384 (14) | |
Fe2 | 0.45226 (6) | 0.11315 (6) | 0.82134 (3) | 0.02371 (14) | |
S2 | 0.26696 (11) | −0.37118 (12) | 0.89084 (6) | 0.0378 (3) | |
C18 | 0.449 (3) | −0.364 (2) | 0.8800 (13) | 0.037 (6) | 0.566 (9) |
O1 | 0.4857 (6) | −0.4677 (9) | 0.8665 (4) | 0.0383 (17) | 0.566 (9) |
S1 | 0.2859 (4) | −0.1795 (5) | 0.8963 (3) | 0.0314 (14) | 0.566 (9) |
C18P | 0.316 (3) | −0.188 (3) | 0.8948 (15) | 0.037 (6) | 0.434 (9) |
O1P | 0.2338 (10) | −0.1248 (10) | 0.9115 (5) | 0.046 (2) | 0.434 (9) |
S1P | 0.4606 (8) | −0.3903 (8) | 0.8827 (5) | 0.033 (2) | 0.434 (9) |
C25 | 0.0640 (4) | −0.4890 (4) | 0.6256 (2) | 0.0303 (10) | |
H25 | 0.00186 | −0.439769 | 0.60492 | 0.036* | |
C26 | 0.1588 (4) | −0.4436 (4) | 0.6905 (2) | 0.0328 (10) | |
H26 | 0.175421 | −0.356539 | 0.723145 | 0.039* | |
C27 | 0.2257 (4) | −0.5430 (4) | 0.7008 (2) | 0.0312 (10) | |
H27 | 0.297464 | −0.53827 | 0.742071 | 0.037* | |
C28 | 0.1719 (4) | −0.6507 (4) | 0.6437 (2) | 0.0277 (9) | |
H28 | 0.199384 | −0.73527 | 0.637466 | 0.033* | |
C29 | 0.0714 (4) | −0.6183 (4) | 0.5959 (2) | 0.0240 (9) | |
C30 | −0.0088 (4) | −0.7010 (4) | 0.52902 (18) | 0.0218 (5) | |
C31 | 0.0423 (4) | −0.7819 (4) | 0.48323 (18) | 0.0218 (5) | |
C32 | −0.1611 (4) | −0.6994 (4) | 0.51047 (19) | 0.0218 (5) | |
C33 | 0.1864 (4) | −0.7976 (4) | 0.4869 (2) | 0.0288 (9) | |
C34 | 0.2209 (4) | −0.9175 (5) | 0.4626 (2) | 0.0351 (11) | |
H34 | 0.151723 | −1.004898 | 0.440025 | 0.042* | |
C35 | 0.3703 (5) | −0.8902 (6) | 0.4755 (3) | 0.0468 (14) | |
H35 | 0.4252 | −0.955266 | 0.463279 | 0.056* | |
C36 | 0.4291 (5) | −0.7560 (6) | 0.5073 (2) | 0.0517 (15) | |
H36 | 0.532815 | −0.709774 | 0.521739 | 0.062* | |
C37 | 0.3161 (4) | −0.6955 (5) | 0.5143 (2) | 0.0418 (12) | |
H37 | 0.325846 | −0.600954 | 0.535199 | 0.05* | |
C38 | 0.2421 (6) | −0.8212 (5) | 0.3059 (2) | 0.0507 (14) | |
H38 | 0.165484 | −0.902267 | 0.281206 | 0.061* | |
C39 | 0.3910 (7) | −0.8058 (7) | 0.3170 (3) | 0.0611 (18) | |
H39 | 0.438232 | −0.876079 | 0.302569 | 0.073* | |
C40 | 0.4575 (6) | −0.6801 (7) | 0.3507 (3) | 0.0631 (17) | |
H40 | 0.562468 | −0.643238 | 0.365739 | 0.076* | |
C41 | 0.3600 (6) | −0.6110 (5) | 0.3620 (3) | 0.0523 (14) | |
H41 | 0.381509 | −0.51599 | 0.385577 | 0.063* | |
C42 | 0.2260 (5) | −0.6961 (5) | 0.3344 (2) | 0.0389 (11) | |
H42 | 0.134159 | −0.672852 | 0.334469 | 0.047* | |
C43 | −0.0265 (4) | −0.6703 (5) | 0.7900 (2) | 0.0336 (10) | |
H43 | 0.04719 | −0.658521 | 0.831638 | 0.04* | |
C44 | −0.0753 (4) | −0.7821 (4) | 0.7351 (2) | 0.0347 (10) | |
H44 | −0.041558 | −0.863285 | 0.730826 | 0.042* | |
C45 | −0.1783 (4) | −0.7603 (4) | 0.6870 (2) | 0.0354 (11) | |
H45 | −0.231137 | −0.822922 | 0.642765 | 0.042* | |
C46 | −0.1940 (4) | −0.6329 (5) | 0.7123 (2) | 0.0352 (11) | |
H46 | −0.26021 | −0.590069 | 0.689252 | 0.042* | |
C47 | −0.1000 (4) | −0.5783 (4) | 0.7762 (2) | 0.0346 (10) | |
H47 | −0.087676 | −0.489549 | 0.806351 | 0.041* | |
Fe3 | 0.01045 (5) | −0.61637 (5) | 0.69496 (3) | 0.02121 (14) | |
Fe4 | 0.31671 (6) | −0.77061 (6) | 0.41095 (3) | 0.02489 (15) | |
O3 | −0.2167 (3) | −0.6240 (4) | 0.53877 (17) | 0.0477 (9) | |
S4 | −0.07427 (11) | −0.88197 (12) | 0.40941 (6) | 0.0358 (3) | |
S5 | −0.24512 (10) | −0.81968 (11) | 0.43199 (6) | 0.0323 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.035 (2) | 0.028 (2) | 0.020 (2) | 0.0103 (18) | 0.0017 (17) | 0.0019 (17) |
C2 | 0.029 (2) | 0.037 (3) | 0.022 (2) | 0.0097 (18) | 0.0093 (17) | 0.0097 (19) |
C3 | 0.0230 (19) | 0.031 (2) | 0.026 (2) | 0.0046 (16) | −0.0021 (17) | 0.0138 (18) |
C4 | 0.028 (2) | 0.023 (2) | 0.026 (2) | 0.0112 (16) | 0.0008 (17) | 0.0059 (17) |
C5 | 0.027 (2) | 0.030 (2) | 0.0192 (19) | 0.0106 (17) | −0.0003 (16) | 0.0079 (17) |
C6 | 0.028 (2) | 0.028 (2) | 0.021 (2) | 0.0068 (17) | 0.0011 (17) | 0.0052 (17) |
C7 | 0.0229 (19) | 0.030 (2) | 0.020 (2) | 0.0038 (16) | 0.0029 (16) | 0.0071 (17) |
C8 | 0.0201 (18) | 0.032 (2) | 0.020 (2) | 0.0088 (16) | −0.0035 (16) | 0.0035 (17) |
C9 | 0.0223 (19) | 0.030 (2) | 0.021 (2) | 0.0123 (16) | −0.0005 (16) | 0.0030 (17) |
C10 | 0.0201 (19) | 0.030 (2) | 0.035 (2) | 0.0054 (16) | −0.0003 (18) | 0.0041 (19) |
C11 | 0.030 (2) | 0.033 (3) | 0.031 (2) | 0.0089 (18) | −0.0028 (19) | −0.0066 (19) |
C12 | 0.0240 (19) | 0.034 (2) | 0.018 (2) | 0.0077 (17) | 0.0001 (16) | 0.0011 (17) |
C13 | 0.024 (2) | 0.054 (3) | 0.025 (2) | 0.0128 (19) | −0.0040 (18) | 0.012 (2) |
C14 | 0.041 (2) | 0.052 (3) | 0.035 (2) | 0.031 (2) | 0.008 (2) | 0.023 (2) |
C15 | 0.043 (3) | 0.049 (3) | 0.032 (2) | 0.019 (2) | 0.008 (2) | 0.023 (2) |
C16 | 0.041 (2) | 0.058 (3) | 0.020 (2) | 0.022 (2) | 0.0011 (19) | 0.012 (2) |
C17 | 0.039 (2) | 0.043 (3) | 0.023 (2) | 0.013 (2) | −0.0102 (19) | 0.002 (2) |
C20 | 0.078 (4) | 0.044 (3) | 0.019 (2) | 0.034 (3) | 0.010 (2) | 0.015 (2) |
C21 | 0.044 (3) | 0.050 (3) | 0.052 (3) | 0.010 (2) | −0.011 (2) | 0.032 (3) |
C22 | 0.049 (3) | 0.060 (4) | 0.071 (4) | 0.039 (3) | 0.031 (3) | 0.046 (3) |
C23 | 0.067 (3) | 0.023 (3) | 0.040 (3) | 0.010 (2) | 0.016 (2) | 0.009 (2) |
C24 | 0.040 (3) | 0.050 (3) | 0.039 (3) | 0.018 (2) | 0.012 (2) | 0.023 (2) |
Fe1 | 0.0270 (3) | 0.0243 (3) | 0.0221 (3) | 0.0099 (2) | 0.0033 (2) | 0.0056 (2) |
Fe2 | 0.0247 (3) | 0.0275 (3) | 0.0217 (3) | 0.0112 (2) | 0.0033 (2) | 0.0059 (2) |
S2 | 0.0268 (5) | 0.0408 (7) | 0.0401 (7) | −0.0004 (5) | 0.0029 (5) | 0.0091 (5) |
C18 | 0.047 (9) | 0.049 (10) | 0.018 (5) | 0.025 (6) | 0.006 (5) | −0.002 (5) |
O1 | 0.035 (3) | 0.023 (4) | 0.052 (4) | 0.005 (3) | −0.001 (3) | 0.002 (3) |
S1 | 0.0215 (18) | 0.033 (2) | 0.0409 (17) | 0.0053 (15) | 0.0072 (14) | 0.0124 (14) |
C18P | 0.047 (9) | 0.049 (10) | 0.018 (5) | 0.025 (6) | 0.006 (5) | −0.002 (5) |
O1P | 0.031 (4) | 0.047 (6) | 0.069 (6) | 0.023 (4) | 0.011 (4) | 0.015 (5) |
S1P | 0.024 (2) | 0.025 (3) | 0.044 (2) | −0.002 (2) | 0.0001 (17) | 0.004 (2) |
C25 | 0.033 (2) | 0.035 (3) | 0.027 (2) | 0.0073 (18) | 0.0118 (18) | 0.0153 (19) |
C26 | 0.034 (2) | 0.031 (2) | 0.025 (2) | −0.0053 (18) | 0.0078 (19) | 0.0041 (19) |
C27 | 0.022 (2) | 0.046 (3) | 0.023 (2) | 0.0059 (18) | 0.0014 (17) | 0.008 (2) |
C28 | 0.0223 (19) | 0.044 (3) | 0.021 (2) | 0.0147 (18) | 0.0094 (17) | 0.0064 (19) |
C29 | 0.0193 (18) | 0.036 (2) | 0.0201 (19) | 0.0089 (16) | 0.0126 (16) | 0.0081 (18) |
C30 | 0.0198 (11) | 0.0356 (14) | 0.0118 (10) | 0.0103 (9) | 0.0013 (9) | 0.0063 (9) |
C31 | 0.0198 (11) | 0.0356 (14) | 0.0118 (10) | 0.0103 (9) | 0.0013 (9) | 0.0063 (9) |
C32 | 0.0198 (11) | 0.0356 (14) | 0.0118 (10) | 0.0103 (9) | 0.0013 (9) | 0.0063 (9) |
C33 | 0.023 (2) | 0.048 (3) | 0.018 (2) | 0.0121 (18) | 0.0062 (17) | 0.0104 (19) |
C34 | 0.034 (2) | 0.048 (3) | 0.036 (2) | 0.018 (2) | 0.013 (2) | 0.027 (2) |
C35 | 0.036 (3) | 0.088 (4) | 0.038 (3) | 0.036 (3) | 0.018 (2) | 0.037 (3) |
C36 | 0.022 (2) | 0.113 (5) | 0.021 (2) | 0.023 (3) | 0.0027 (19) | 0.010 (3) |
C37 | 0.024 (2) | 0.070 (4) | 0.024 (2) | 0.009 (2) | 0.0053 (18) | −0.007 (2) |
C38 | 0.090 (4) | 0.036 (3) | 0.017 (2) | 0.003 (3) | 0.002 (2) | 0.007 (2) |
C39 | 0.103 (5) | 0.086 (5) | 0.038 (3) | 0.078 (4) | 0.043 (3) | 0.033 (3) |
C40 | 0.049 (3) | 0.094 (5) | 0.065 (4) | 0.026 (3) | 0.033 (3) | 0.050 (4) |
C41 | 0.066 (3) | 0.033 (3) | 0.061 (4) | 0.013 (3) | 0.003 (3) | 0.019 (3) |
C42 | 0.045 (3) | 0.062 (3) | 0.025 (2) | 0.032 (2) | 0.013 (2) | 0.018 (2) |
C43 | 0.031 (2) | 0.050 (3) | 0.023 (2) | 0.007 (2) | 0.0134 (18) | 0.018 (2) |
C44 | 0.035 (2) | 0.028 (2) | 0.048 (3) | 0.0095 (19) | 0.017 (2) | 0.019 (2) |
C45 | 0.030 (2) | 0.038 (3) | 0.031 (2) | −0.0026 (19) | 0.0128 (19) | 0.003 (2) |
C46 | 0.025 (2) | 0.052 (3) | 0.042 (3) | 0.018 (2) | 0.020 (2) | 0.026 (2) |
C47 | 0.037 (2) | 0.033 (3) | 0.035 (2) | 0.0073 (19) | 0.020 (2) | 0.004 (2) |
Fe3 | 0.0230 (3) | 0.0241 (3) | 0.0175 (3) | 0.0067 (2) | 0.0058 (2) | 0.0050 (2) |
Fe4 | 0.0263 (3) | 0.0316 (3) | 0.0211 (3) | 0.0128 (2) | 0.0091 (2) | 0.0063 (3) |
O3 | 0.0367 (17) | 0.066 (2) | 0.0414 (19) | 0.0227 (16) | −0.0037 (15) | 0.0030 (17) |
S4 | 0.0283 (5) | 0.0486 (7) | 0.0276 (6) | 0.0101 (5) | 0.0025 (5) | 0.0011 (5) |
S5 | 0.0214 (5) | 0.0456 (7) | 0.0278 (6) | 0.0062 (4) | −0.0025 (4) | 0.0104 (5) |
C1—C2 | 1.414 (6) | C18—O1 | 1.25 (3) |
C1—C5 | 1.430 (5) | C18P—O1P | 1.22 (3) |
C1—Fe1 | 2.036 (4) | C25—C26 | 1.425 (6) |
C1—H1 | 1 | C25—C29 | 1.430 (6) |
C2—C3 | 1.408 (6) | C25—Fe3 | 2.050 (4) |
C2—Fe1 | 2.041 (4) | C25—H25 | 1 |
C2—H2 | 1 | C26—C27 | 1.416 (6) |
C3—C4 | 1.412 (5) | C26—Fe3 | 2.039 (4) |
C3—Fe1 | 2.037 (4) | C26—H26 | 1 |
C3—H3 | 1 | C27—C28 | 1.409 (6) |
C4—C5 | 1.436 (5) | C27—Fe3 | 2.041 (4) |
C4—Fe1 | 2.035 (4) | C27—H27 | 1 |
C4—H4 | 1 | C28—C29 | 1.436 (5) |
C5—C6 | 1.474 (5) | C28—Fe3 | 2.031 (4) |
C5—Fe1 | 2.048 (4) | C28—H28 | 1 |
C6—C7 | 1.357 (6) | C29—C30 | 1.466 (5) |
C6—C18 | 1.49 (2) | C29—Fe3 | 2.052 (4) |
C6—S1P | 1.708 (8) | C30—C31 | 1.361 (5) |
C7—C8 | 1.465 (5) | C30—C32 | 1.516 (5) |
C7—C18P | 1.48 (2) | C31—C33 | 1.471 (5) |
C7—S1 | 1.756 (5) | C31—S4 | 1.748 (4) |
C8—C9 | 1.425 (5) | C32—O3 | 1.182 (5) |
C8—C12 | 1.434 (5) | C32—S5 | 1.794 (4) |
C8—Fe2 | 2.055 (4) | C33—C34 | 1.428 (6) |
C9—C10 | 1.401 (6) | C33—C37 | 1.431 (6) |
C9—Fe2 | 2.034 (4) | C33—Fe4 | 2.037 (4) |
C9—H9 | 1 | C34—C35 | 1.413 (6) |
C10—C11 | 1.430 (6) | C34—Fe4 | 2.046 (4) |
C10—Fe2 | 2.044 (4) | C34—H34 | 1 |
C10—H10 | 1 | C35—C36 | 1.405 (8) |
C11—C12 | 1.417 (6) | C35—Fe4 | 2.043 (4) |
C11—Fe2 | 2.042 (4) | C35—H35 | 1 |
C11—H11 | 1 | C36—C37 | 1.434 (7) |
C12—Fe2 | 2.044 (4) | C36—Fe4 | 2.036 (4) |
C12—H12 | 1 | C36—H36 | 1 |
C13—C14 | 1.416 (6) | C37—Fe4 | 2.029 (4) |
C13—C17 | 1.435 (6) | C37—H37 | 1 |
C13—Fe2 | 2.047 (4) | C38—C42 | 1.415 (7) |
C13—H13 | 1 | C38—C39 | 1.424 (8) |
C14—C15 | 1.420 (6) | C38—Fe4 | 2.026 (4) |
C14—Fe2 | 2.051 (4) | C38—H38 | 1 |
C14—H14 | 1 | C39—C40 | 1.350 (8) |
C15—C16 | 1.402 (6) | C39—Fe4 | 2.033 (5) |
C15—Fe2 | 2.055 (4) | C39—H39 | 1 |
C15—H15 | 1 | C40—C41 | 1.371 (8) |
C16—C17 | 1.419 (6) | C40—Fe4 | 2.031 (5) |
C16—Fe2 | 2.049 (4) | C40—H40 | 1 |
C16—H16 | 1 | C41—C42 | 1.388 (7) |
C17—Fe2 | 2.037 (4) | C41—Fe4 | 2.033 (5) |
C17—H17 | 1 | C41—H41 | 1 |
C20—C24 | 1.394 (7) | C42—Fe4 | 2.025 (4) |
C20—C21 | 1.410 (7) | C42—H42 | 1 |
C20—Fe1 | 2.037 (4) | C43—C47 | 1.406 (6) |
C20—H20 | 1 | C43—C44 | 1.407 (6) |
C21—C22 | 1.398 (7) | C43—Fe3 | 2.037 (4) |
C21—Fe1 | 2.045 (4) | C43—H43 | 1 |
C21—H21 | 1 | C44—C45 | 1.401 (6) |
C22—C23 | 1.408 (7) | C44—Fe3 | 2.041 (4) |
C22—Fe1 | 2.036 (4) | C44—H44 | 1 |
C22—H22 | 1 | C45—C46 | 1.421 (6) |
C23—C24 | 1.410 (6) | C45—Fe3 | 2.044 (4) |
C23—Fe1 | 2.029 (4) | C45—H45 | 1 |
C23—H23 | 1 | C46—C47 | 1.412 (6) |
C24—Fe1 | 2.044 (4) | C46—Fe3 | 2.038 (4) |
C24—H24 | 1 | C46—H46 | 1 |
S2—C18 | 1.80 (3) | C47—Fe3 | 2.038 (4) |
S2—C18P | 1.87 (3) | C47—H47 | 1 |
S2—S1 | 1.983 (6) | S4—S5 | 2.0259 (15) |
S2—S1P | 1.989 (9) | ||
C2—C1—C5 | 107.7 (4) | O1P—C18P—C7 | 127 (3) |
C2—C1—Fe1 | 69.9 (2) | O1P—C18P—S2 | 120.9 (19) |
C5—C1—Fe1 | 69.9 (2) | C7—C18P—S2 | 111.5 (16) |
C2—C1—H1 | 126.2 | C6—S1P—S2 | 95.8 (5) |
C5—C1—H1 | 126.2 | C26—C25—C29 | 108.1 (4) |
Fe1—C1—H1 | 126.2 | C26—C25—Fe3 | 69.2 (2) |
C3—C2—C1 | 108.7 (4) | C29—C25—Fe3 | 69.7 (2) |
C3—C2—Fe1 | 69.7 (2) | C26—C25—H25 | 126 |
C1—C2—Fe1 | 69.5 (2) | C29—C25—H25 | 126 |
C3—C2—H2 | 125.6 | Fe3—C25—H25 | 126 |
C1—C2—H2 | 125.6 | C27—C26—C25 | 108.1 (4) |
Fe1—C2—H2 | 125.6 | C27—C26—Fe3 | 69.7 (2) |
C2—C3—C4 | 108.5 (3) | C25—C26—Fe3 | 70.0 (2) |
C2—C3—Fe1 | 70.0 (2) | C27—C26—H26 | 125.9 |
C4—C3—Fe1 | 69.6 (2) | C25—C26—H26 | 125.9 |
C2—C3—H3 | 125.8 | Fe3—C26—H26 | 125.9 |
C4—C3—H3 | 125.8 | C28—C27—C26 | 108.4 (4) |
Fe1—C3—H3 | 125.8 | C28—C27—Fe3 | 69.4 (2) |
C3—C4—C5 | 107.7 (4) | C26—C27—Fe3 | 69.6 (2) |
C3—C4—Fe1 | 69.8 (2) | C28—C27—H27 | 125.8 |
C5—C4—Fe1 | 69.9 (2) | C26—C27—H27 | 125.8 |
C3—C4—H4 | 126.1 | Fe3—C27—H27 | 125.8 |
C5—C4—H4 | 126.1 | C27—C28—C29 | 108.5 (4) |
Fe1—C4—H4 | 126.1 | C27—C28—Fe3 | 70.1 (2) |
C1—C5—C4 | 107.4 (3) | C29—C28—Fe3 | 70.2 (2) |
C1—C5—C6 | 126.3 (4) | C27—C28—H28 | 125.8 |
C4—C5—C6 | 126.3 (4) | C29—C28—H28 | 125.8 |
C1—C5—Fe1 | 69.1 (2) | Fe3—C28—H28 | 125.8 |
C4—C5—Fe1 | 68.9 (2) | C25—C29—C28 | 107.0 (3) |
C6—C5—Fe1 | 128.4 (3) | C25—C29—C30 | 126.0 (3) |
C7—C6—C5 | 125.3 (4) | C28—C29—C30 | 127.0 (4) |
C7—C6—C18 | 113.7 (11) | C25—C29—Fe3 | 69.5 (2) |
C5—C6—C18 | 121.0 (11) | C28—C29—Fe3 | 68.6 (2) |
C7—C6—S1P | 122.7 (4) | C30—C29—Fe3 | 127.0 (3) |
C5—C6—S1P | 111.9 (4) | C31—C30—C29 | 124.8 (3) |
C6—C7—C8 | 127.1 (3) | C31—C30—C32 | 117.5 (3) |
C6—C7—C18P | 113.6 (13) | C29—C30—C32 | 117.7 (3) |
C8—C7—C18P | 119.2 (13) | C30—C31—C33 | 128.4 (3) |
C6—C7—S1 | 120.3 (4) | C30—C31—S4 | 117.9 (3) |
C8—C7—S1 | 112.6 (3) | C33—C31—S4 | 113.7 (3) |
C9—C8—C12 | 107.1 (3) | O3—C32—C30 | 126.5 (4) |
C9—C8—C7 | 127.7 (4) | O3—C32—S5 | 122.8 (3) |
C12—C8—C7 | 125.1 (3) | C30—C32—S5 | 110.5 (3) |
C9—C8—Fe2 | 68.8 (2) | C34—C33—C37 | 108.3 (4) |
C12—C8—Fe2 | 69.1 (2) | C34—C33—C31 | 125.6 (4) |
C7—C8—Fe2 | 125.9 (3) | C37—C33—C31 | 126.1 (4) |
C10—C9—C8 | 109.1 (4) | C34—C33—Fe4 | 69.9 (2) |
C10—C9—Fe2 | 70.3 (2) | C37—C33—Fe4 | 69.1 (2) |
C8—C9—Fe2 | 70.4 (2) | C31—C33—Fe4 | 126.0 (3) |
C10—C9—H9 | 125.5 | C35—C34—C33 | 107.7 (4) |
C8—C9—H9 | 125.5 | C35—C34—Fe4 | 69.7 (3) |
Fe2—C9—H9 | 125.5 | C33—C34—Fe4 | 69.2 (2) |
C9—C10—C11 | 107.8 (4) | C35—C34—H34 | 126.1 |
C9—C10—Fe2 | 69.5 (2) | C33—C34—H34 | 126.1 |
C11—C10—Fe2 | 69.5 (2) | Fe4—C34—H34 | 126.1 |
C9—C10—H10 | 126.1 | C36—C35—C34 | 108.7 (4) |
C11—C10—H10 | 126.1 | C36—C35—Fe4 | 69.6 (3) |
Fe2—C10—H10 | 126.1 | C34—C35—Fe4 | 69.9 (2) |
C12—C11—C10 | 108.2 (4) | C36—C35—H35 | 125.7 |
C12—C11—Fe2 | 69.8 (2) | C34—C35—H35 | 125.7 |
C10—C11—Fe2 | 69.6 (2) | Fe4—C35—H35 | 125.7 |
C12—C11—H11 | 125.9 | C35—C36—C37 | 108.7 (4) |
C10—C11—H11 | 125.9 | C35—C36—Fe4 | 70.1 (3) |
Fe2—C11—H11 | 125.9 | C37—C36—Fe4 | 69.1 (2) |
C11—C12—C8 | 107.8 (3) | C35—C36—H36 | 125.6 |
C11—C12—Fe2 | 69.6 (2) | C37—C36—H36 | 125.6 |
C8—C12—Fe2 | 69.9 (2) | Fe4—C36—H36 | 125.6 |
C11—C12—H12 | 126.1 | C33—C37—C36 | 106.6 (5) |
C8—C12—H12 | 126.1 | C33—C37—Fe4 | 69.7 (2) |
Fe2—C12—H12 | 126.1 | C36—C37—Fe4 | 69.6 (3) |
C14—C13—C17 | 107.6 (4) | C33—C37—H37 | 126.7 |
C14—C13—Fe2 | 69.9 (2) | C36—C37—H37 | 126.7 |
C17—C13—Fe2 | 69.1 (2) | Fe4—C37—H37 | 126.7 |
C14—C13—H13 | 126.2 | C42—C38—C39 | 105.5 (5) |
C17—C13—H13 | 126.2 | C42—C38—Fe4 | 69.5 (2) |
Fe2—C13—H13 | 126.2 | C39—C38—Fe4 | 69.7 (3) |
C13—C14—C15 | 108.0 (4) | C42—C38—H38 | 127.2 |
C13—C14—Fe2 | 69.6 (2) | C39—C38—H38 | 127.2 |
C15—C14—Fe2 | 69.9 (2) | Fe4—C38—H38 | 127.2 |
C13—C14—H14 | 126 | C40—C39—C38 | 108.4 (5) |
C15—C14—H14 | 126 | C40—C39—Fe4 | 70.5 (3) |
Fe2—C14—H14 | 126 | C38—C39—Fe4 | 69.2 (3) |
C16—C15—C14 | 108.4 (4) | C40—C39—H39 | 125.8 |
C16—C15—Fe2 | 69.8 (2) | C38—C39—H39 | 125.8 |
C14—C15—Fe2 | 69.6 (2) | Fe4—C39—H39 | 125.8 |
C16—C15—H15 | 125.8 | C39—C40—C41 | 110.0 (5) |
C14—C15—H15 | 125.8 | C39—C40—Fe4 | 70.7 (3) |
Fe2—C15—H15 | 125.8 | C41—C40—Fe4 | 70.4 (3) |
C15—C16—C17 | 108.5 (4) | C39—C40—H40 | 125 |
C15—C16—Fe2 | 70.2 (2) | C41—C40—H40 | 125 |
C17—C16—Fe2 | 69.2 (2) | Fe4—C40—H40 | 125 |
C15—C16—H16 | 125.8 | C40—C41—C42 | 107.9 (5) |
C17—C16—H16 | 125.8 | C40—C41—Fe4 | 70.2 (3) |
Fe2—C16—H16 | 125.8 | C42—C41—Fe4 | 69.7 (3) |
C16—C17—C13 | 107.5 (4) | C40—C41—H41 | 126.1 |
C16—C17—Fe2 | 70.1 (2) | C42—C41—H41 | 126.1 |
C13—C17—Fe2 | 69.8 (2) | Fe4—C41—H41 | 126.1 |
C16—C17—H17 | 126.2 | C41—C42—C38 | 108.1 (4) |
C13—C17—H17 | 126.2 | C41—C42—Fe4 | 70.3 (3) |
Fe2—C17—H17 | 126.2 | C38—C42—Fe4 | 69.6 (2) |
C24—C20—C21 | 108.8 (4) | C41—C42—H42 | 125.9 |
C24—C20—Fe1 | 70.3 (3) | C38—C42—H42 | 125.9 |
C21—C20—Fe1 | 70.1 (3) | Fe4—C42—H42 | 125.9 |
C24—C20—H20 | 125.6 | C47—C43—C44 | 108.0 (4) |
C21—C20—H20 | 125.6 | C47—C43—Fe3 | 69.8 (2) |
Fe1—C20—H20 | 125.6 | C44—C43—Fe3 | 69.9 (2) |
C22—C21—C20 | 107.4 (4) | C47—C43—H43 | 126 |
C22—C21—Fe1 | 69.6 (3) | C44—C43—H43 | 126 |
C20—C21—Fe1 | 69.5 (2) | Fe3—C43—H43 | 126 |
C22—C21—H21 | 126.3 | C45—C44—C43 | 108.6 (4) |
C20—C21—H21 | 126.3 | C45—C44—Fe3 | 70.1 (2) |
Fe1—C21—H21 | 126.3 | C43—C44—Fe3 | 69.7 (2) |
C21—C22—C23 | 108.3 (4) | C45—C44—H44 | 125.7 |
C21—C22—Fe1 | 70.3 (3) | C43—C44—H44 | 125.7 |
C23—C22—Fe1 | 69.4 (3) | Fe3—C44—H44 | 125.7 |
C21—C22—H22 | 125.9 | C44—C45—C46 | 107.7 (4) |
C23—C22—H22 | 125.9 | C44—C45—Fe3 | 69.8 (2) |
Fe1—C22—H22 | 125.9 | C46—C45—Fe3 | 69.4 (2) |
C22—C23—C24 | 107.9 (5) | C44—C45—H45 | 126.1 |
C22—C23—Fe1 | 70.0 (3) | C46—C45—H45 | 126.1 |
C24—C23—Fe1 | 70.3 (3) | Fe3—C45—H45 | 126.1 |
C22—C23—H23 | 126 | C47—C46—C45 | 107.7 (4) |
C24—C23—H23 | 126 | C47—C46—Fe3 | 69.8 (2) |
Fe1—C23—H23 | 126 | C45—C46—Fe3 | 69.9 (2) |
C20—C24—C23 | 107.5 (4) | C47—C46—H46 | 126.2 |
C20—C24—Fe1 | 69.8 (3) | C45—C46—H46 | 126.2 |
C23—C24—Fe1 | 69.2 (3) | Fe3—C46—H46 | 126.2 |
C20—C24—H24 | 126.2 | C43—C47—C46 | 108.1 (4) |
C23—C24—H24 | 126.2 | C43—C47—Fe3 | 69.8 (2) |
Fe1—C24—H24 | 126.2 | C46—C47—Fe3 | 69.7 (2) |
C23—Fe1—C4 | 161.96 (18) | C43—C47—H47 | 126 |
C23—Fe1—C1 | 107.29 (18) | C46—C47—H47 | 126 |
C4—Fe1—C1 | 69.13 (16) | Fe3—C47—H47 | 126 |
C23—Fe1—C22 | 40.5 (2) | C28—Fe3—C43 | 122.97 (17) |
C4—Fe1—C22 | 156.2 (2) | C28—Fe3—C46 | 157.75 (18) |
C1—Fe1—C22 | 123.4 (2) | C43—Fe3—C46 | 68.09 (17) |
C23—Fe1—C3 | 156.13 (18) | C28—Fe3—C47 | 159.62 (17) |
C4—Fe1—C3 | 40.58 (15) | C43—Fe3—C47 | 40.37 (17) |
C1—Fe1—C3 | 68.53 (16) | C46—Fe3—C47 | 40.55 (17) |
C22—Fe1—C3 | 120.75 (18) | C28—Fe3—C26 | 68.51 (18) |
C23—Fe1—C20 | 67.58 (19) | C43—Fe3—C26 | 120.59 (18) |
C4—Fe1—C20 | 108.75 (18) | C46—Fe3—C26 | 125.21 (19) |
C1—Fe1—C20 | 158.06 (19) | C47—Fe3—C26 | 107.64 (18) |
C22—Fe1—C20 | 67.5 (2) | C28—Fe3—C27 | 40.49 (16) |
C3—Fe1—C20 | 124.96 (19) | C43—Fe3—C27 | 106.40 (16) |
C23—Fe1—C2 | 121.21 (18) | C46—Fe3—C27 | 161.05 (19) |
C4—Fe1—C2 | 68.31 (17) | C47—Fe3—C27 | 123.67 (18) |
C1—Fe1—C2 | 40.58 (16) | C26—Fe3—C27 | 40.63 (17) |
C22—Fe1—C2 | 106.97 (18) | C28—Fe3—C44 | 106.95 (18) |
C3—Fe1—C2 | 40.39 (16) | C43—Fe3—C44 | 40.37 (18) |
C20—Fe1—C2 | 160.6 (2) | C46—Fe3—C44 | 67.93 (17) |
C23—Fe1—C24 | 40.51 (18) | C47—Fe3—C44 | 67.83 (18) |
C4—Fe1—C24 | 125.38 (17) | C26—Fe3—C44 | 155.64 (18) |
C1—Fe1—C24 | 122.32 (18) | C27—Fe3—C44 | 120.43 (17) |
C22—Fe1—C24 | 67.92 (18) | C28—Fe3—C45 | 121.42 (18) |
C3—Fe1—C24 | 161.50 (19) | C43—Fe3—C45 | 67.92 (17) |
C20—Fe1—C24 | 39.94 (19) | C46—Fe3—C45 | 40.75 (18) |
C2—Fe1—C24 | 157.27 (19) | C47—Fe3—C45 | 68.16 (17) |
C23—Fe1—C21 | 67.9 (2) | C26—Fe3—C45 | 162.63 (19) |
C4—Fe1—C21 | 121.7 (2) | C27—Fe3—C45 | 155.85 (19) |
C1—Fe1—C21 | 159.5 (2) | C44—Fe3—C45 | 40.10 (17) |
C22—Fe1—C21 | 40.1 (2) | C28—Fe3—C25 | 68.74 (17) |
C3—Fe1—C21 | 107.40 (17) | C43—Fe3—C25 | 156.72 (19) |
C20—Fe1—C21 | 40.42 (19) | C46—Fe3—C25 | 109.03 (17) |
C2—Fe1—C21 | 123.47 (18) | C47—Fe3—C25 | 122.29 (18) |
C24—Fe1—C21 | 67.80 (19) | C26—Fe3—C25 | 40.77 (16) |
C23—Fe1—C5 | 124.66 (19) | C27—Fe3—C25 | 68.43 (16) |
C4—Fe1—C5 | 41.20 (15) | C44—Fe3—C25 | 161.95 (18) |
C1—Fe1—C5 | 40.99 (15) | C45—Fe3—C25 | 126.01 (17) |
C22—Fe1—C5 | 160.8 (2) | C28—Fe3—C29 | 41.19 (15) |
C3—Fe1—C5 | 68.55 (15) | C43—Fe3—C29 | 160.50 (18) |
C20—Fe1—C5 | 123.00 (18) | C46—Fe3—C29 | 122.54 (16) |
C2—Fe1—C5 | 68.33 (16) | C47—Fe3—C29 | 157.92 (17) |
C24—Fe1—C5 | 108.79 (17) | C26—Fe3—C29 | 68.75 (16) |
C21—Fe1—C5 | 158.0 (2) | C27—Fe3—C29 | 68.67 (15) |
C9—Fe2—C17 | 117.78 (18) | C44—Fe3—C29 | 124.55 (18) |
C9—Fe2—C11 | 68.25 (17) | C45—Fe3—C29 | 108.41 (16) |
C17—Fe2—C11 | 169.18 (18) | C25—Fe3—C29 | 40.80 (16) |
C9—Fe2—C10 | 40.19 (16) | C42—Fe4—C38 | 40.90 (19) |
C17—Fe2—C10 | 149.26 (18) | C42—Fe4—C37 | 119.2 (2) |
C11—Fe2—C10 | 40.96 (16) | C38—Fe4—C37 | 155.9 (2) |
C9—Fe2—C12 | 68.65 (15) | C42—Fe4—C40 | 66.7 (2) |
C17—Fe2—C12 | 131.11 (17) | C38—Fe4—C40 | 67.4 (2) |
C11—Fe2—C12 | 40.59 (16) | C37—Fe4—C40 | 123.1 (3) |
C10—Fe2—C12 | 68.69 (16) | C42—Fe4—C39 | 67.71 (19) |
C9—Fe2—C13 | 152.24 (18) | C38—Fe4—C39 | 41.1 (2) |
C17—Fe2—C13 | 41.14 (17) | C37—Fe4—C39 | 159.4 (2) |
C11—Fe2—C13 | 129.68 (18) | C40—Fe4—C39 | 38.8 (2) |
C10—Fe2—C13 | 167.12 (18) | C42—Fe4—C41 | 40.0 (2) |
C12—Fe2—C13 | 109.75 (16) | C38—Fe4—C41 | 68.0 (2) |
C9—Fe2—C16 | 107.79 (17) | C37—Fe4—C41 | 105.4 (2) |
C17—Fe2—C16 | 40.63 (18) | C40—Fe4—C41 | 39.4 (2) |
C11—Fe2—C16 | 148.70 (19) | C39—Fe4—C41 | 66.5 (2) |
C10—Fe2—C16 | 115.62 (18) | C42—Fe4—C36 | 153.7 (2) |
C12—Fe2—C16 | 169.28 (18) | C38—Fe4—C36 | 162.5 (2) |
C13—Fe2—C16 | 68.36 (18) | C37—Fe4—C36 | 41.31 (19) |
C9—Fe2—C14 | 165.74 (17) | C40—Fe4—C36 | 106.6 (2) |
C17—Fe2—C14 | 68.49 (19) | C39—Fe4—C36 | 124.1 (2) |
C11—Fe2—C14 | 107.91 (19) | C41—Fe4—C36 | 118.5 (2) |
C10—Fe2—C14 | 128.07 (18) | C42—Fe4—C33 | 108.87 (16) |
C12—Fe2—C14 | 118.05 (17) | C38—Fe4—C33 | 122.4 (2) |
C13—Fe2—C14 | 40.43 (18) | C37—Fe4—C33 | 41.23 (17) |
C16—Fe2—C14 | 67.89 (18) | C40—Fe4—C33 | 161.0 (3) |
C9—Fe2—C15 | 127.67 (17) | C39—Fe4—C33 | 158.8 (3) |
C17—Fe2—C15 | 68.02 (19) | C41—Fe4—C33 | 125.3 (2) |
C11—Fe2—C15 | 116.4 (2) | C36—Fe4—C33 | 68.66 (16) |
C10—Fe2—C15 | 106.58 (18) | C42—Fe4—C35 | 165.2 (2) |
C12—Fe2—C15 | 150.17 (19) | C38—Fe4—C35 | 127.3 (2) |
C13—Fe2—C15 | 68.03 (18) | C37—Fe4—C35 | 69.0 (2) |
C16—Fe2—C15 | 39.95 (18) | C40—Fe4—C35 | 120.7 (2) |
C14—Fe2—C15 | 40.48 (17) | C39—Fe4—C35 | 109.2 (2) |
C9—Fe2—C8 | 40.77 (15) | C41—Fe4—C35 | 153.5 (2) |
C17—Fe2—C8 | 109.65 (17) | C36—Fe4—C35 | 40.3 (2) |
C11—Fe2—C8 | 68.42 (17) | C33—Fe4—C35 | 68.42 (17) |
C10—Fe2—C8 | 68.34 (16) | C42—Fe4—C34 | 128.16 (18) |
C12—Fe2—C8 | 40.94 (15) | C38—Fe4—C34 | 110.24 (19) |
C13—Fe2—C8 | 119.47 (16) | C37—Fe4—C34 | 69.3 (2) |
C16—Fe2—C8 | 129.93 (18) | C40—Fe4—C34 | 156.2 (2) |
C14—Fe2—C8 | 152.11 (16) | C39—Fe4—C34 | 123.5 (2) |
C15—Fe2—C8 | 166.75 (17) | C41—Fe4—C34 | 163.8 (2) |
C18—S2—S1 | 97.4 (7) | C36—Fe4—C34 | 68.2 (2) |
C18P—S2—S1P | 96.4 (7) | C33—Fe4—C34 | 40.94 (17) |
O1—C18—C6 | 126 (2) | C35—Fe4—C34 | 40.41 (17) |
O1—C18—S2 | 121.1 (17) | C31—S4—S5 | 96.09 (13) |
C6—C18—S2 | 112.8 (15) | C32—S5—S4 | 97.94 (13) |
C7—S1—S2 | 95.5 (3) | ||
C5—C1—C2—C3 | 1.2 (4) | C6—C7—C18P—O1P | 167 (2) |
Fe1—C1—C2—C3 | −58.8 (3) | C8—C7—C18P—O1P | −14 (3) |
C5—C1—C2—Fe1 | 60.0 (3) | C6—C7—C18P—S2 | −1.1 (19) |
C1—C2—C3—C4 | −0.4 (4) | C8—C7—C18P—S2 | 178.3 (8) |
Fe1—C2—C3—C4 | −59.1 (3) | S1P—S2—C18P—O1P | −168 (2) |
C1—C2—C3—Fe1 | 58.7 (3) | S1P—S2—C18P—C7 | 0.6 (18) |
C2—C3—C4—C5 | −0.5 (4) | C7—C6—S1P—S2 | −0.7 (6) |
Fe1—C3—C4—C5 | −59.9 (3) | C5—C6—S1P—S2 | 176.6 (3) |
C2—C3—C4—Fe1 | 59.3 (3) | C29—C25—C26—C27 | 0.5 (4) |
C2—C1—C5—C4 | −1.5 (4) | Fe3—C25—C26—C27 | 59.5 (3) |
Fe1—C1—C5—C4 | 58.5 (3) | C29—C25—C26—Fe3 | −59.0 (3) |
C2—C1—C5—C6 | 177.1 (4) | C25—C26—C27—C28 | −1.0 (4) |
Fe1—C1—C5—C6 | −122.9 (4) | Fe3—C26—C27—C28 | 58.7 (3) |
C2—C1—C5—Fe1 | −60.0 (3) | C25—C26—C27—Fe3 | −59.7 (3) |
C3—C4—C5—C1 | 1.2 (4) | C26—C27—C28—C29 | 1.1 (4) |
Fe1—C4—C5—C1 | −58.5 (3) | Fe3—C27—C28—C29 | 60.0 (2) |
C3—C4—C5—C6 | −177.4 (3) | C26—C27—C28—Fe3 | −58.9 (3) |
Fe1—C4—C5—C6 | 122.8 (4) | C26—C25—C29—C28 | 0.2 (4) |
C3—C4—C5—Fe1 | 59.8 (3) | Fe3—C25—C29—C28 | −58.6 (2) |
C1—C5—C6—C7 | −140.5 (4) | C26—C25—C29—C30 | −179.8 (3) |
C4—C5—C6—C7 | 37.8 (6) | Fe3—C25—C29—C30 | 121.5 (4) |
Fe1—C5—C6—C7 | 128.5 (4) | C26—C25—C29—Fe3 | 58.7 (3) |
C1—C5—C6—C18 | 39.5 (12) | C27—C28—C29—C25 | −0.8 (4) |
C4—C5—C6—C18 | −142.1 (11) | Fe3—C28—C29—C25 | 59.2 (2) |
Fe1—C5—C6—C18 | −51.4 (12) | C27—C28—C29—C30 | 179.2 (3) |
C1—C5—C6—S1P | 42.3 (6) | Fe3—C28—C29—C30 | −120.9 (4) |
C4—C5—C6—S1P | −139.4 (5) | C27—C28—C29—Fe3 | −59.9 (3) |
Fe1—C5—C6—S1P | −48.7 (5) | C25—C29—C30—C31 | 144.0 (4) |
C5—C6—C7—C8 | 4.9 (7) | C28—C29—C30—C31 | −35.9 (6) |
C18—C6—C7—C8 | −175.1 (11) | Fe3—C29—C30—C31 | −125.7 (4) |
S1P—C6—C7—C8 | −178.1 (5) | C25—C29—C30—C32 | −37.9 (5) |
C5—C6—C7—C18P | −175.6 (13) | C28—C29—C30—C32 | 142.2 (4) |
S1P—C6—C7—C18P | 1.3 (13) | Fe3—C29—C30—C32 | 52.5 (5) |
C5—C6—C7—S1 | −175.6 (4) | C29—C30—C31—C33 | −4.8 (6) |
C18—C6—C7—S1 | 4.3 (11) | C32—C30—C31—C33 | 177.0 (4) |
C6—C7—C8—C9 | 33.9 (6) | C29—C30—C31—S4 | 175.4 (3) |
C18P—C7—C8—C9 | −145.5 (13) | C32—C30—C31—S4 | −2.8 (5) |
S1—C7—C8—C9 | −145.6 (4) | C31—C30—C32—O3 | −169.7 (4) |
C6—C7—C8—C12 | −147.9 (4) | C29—C30—C32—O3 | 12.0 (6) |
C18P—C7—C8—C12 | 32.7 (14) | C31—C30—C32—S5 | 4.4 (4) |
S1—C7—C8—C12 | 32.6 (5) | C29—C30—C32—S5 | −173.9 (3) |
C6—C7—C8—Fe2 | 123.7 (4) | C30—C31—C33—C34 | 147.4 (4) |
C18P—C7—C8—Fe2 | −55.7 (14) | S4—C31—C33—C34 | −32.8 (5) |
S1—C7—C8—Fe2 | −55.8 (4) | C30—C31—C33—C37 | −33.7 (6) |
C12—C8—C9—C10 | 1.1 (4) | S4—C31—C33—C37 | 146.1 (4) |
C7—C8—C9—C10 | 179.6 (3) | C30—C31—C33—Fe4 | −122.7 (4) |
Fe2—C8—C9—C10 | 59.8 (3) | S4—C31—C33—Fe4 | 57.1 (4) |
C12—C8—C9—Fe2 | −58.7 (2) | C37—C33—C34—C35 | 0.7 (5) |
C7—C8—C9—Fe2 | 119.7 (4) | C31—C33—C34—C35 | 179.7 (4) |
C8—C9—C10—C11 | −0.8 (4) | Fe4—C33—C34—C35 | 59.2 (3) |
Fe2—C9—C10—C11 | 59.2 (3) | C37—C33—C34—Fe4 | −58.6 (3) |
C8—C9—C10—Fe2 | −59.9 (3) | C31—C33—C34—Fe4 | 120.5 (4) |
C9—C10—C11—C12 | 0.1 (4) | C33—C34—C35—C36 | 0.0 (5) |
Fe2—C10—C11—C12 | 59.3 (3) | Fe4—C34—C35—C36 | 58.9 (3) |
C9—C10—C11—Fe2 | −59.2 (3) | C33—C34—C35—Fe4 | −58.9 (3) |
C10—C11—C12—C8 | 0.6 (4) | C34—C35—C36—C37 | −0.7 (5) |
Fe2—C11—C12—C8 | 59.7 (3) | Fe4—C35—C36—C37 | 58.4 (3) |
C10—C11—C12—Fe2 | −59.2 (3) | C34—C35—C36—Fe4 | −59.2 (3) |
C9—C8—C12—C11 | −1.0 (4) | C34—C33—C37—C36 | −1.1 (5) |
C7—C8—C12—C11 | −179.5 (3) | C31—C33—C37—C36 | 179.9 (4) |
Fe2—C8—C12—C11 | −59.6 (3) | Fe4—C33—C37—C36 | −60.1 (3) |
C9—C8—C12—Fe2 | 58.5 (2) | C34—C33—C37—Fe4 | 59.1 (3) |
C7—C8—C12—Fe2 | −120.0 (4) | C31—C33—C37—Fe4 | −120.0 (4) |
C17—C13—C14—C15 | 0.6 (5) | C35—C36—C37—C33 | 1.1 (5) |
Fe2—C13—C14—C15 | 59.6 (3) | Fe4—C36—C37—C33 | 60.2 (3) |
C17—C13—C14—Fe2 | −59.0 (3) | C35—C36—C37—Fe4 | −59.1 (3) |
C13—C14—C15—C16 | −0.2 (5) | C42—C38—C39—C40 | 0.8 (5) |
Fe2—C14—C15—C16 | 59.2 (3) | Fe4—C38—C39—C40 | −59.9 (4) |
C13—C14—C15—Fe2 | −59.4 (3) | C42—C38—C39—Fe4 | 60.6 (3) |
C14—C15—C16—C17 | −0.2 (5) | C38—C39—C40—C41 | −0.5 (6) |
Fe2—C15—C16—C17 | 58.8 (3) | Fe4—C39—C40—C41 | −59.5 (4) |
C14—C15—C16—Fe2 | −59.1 (3) | C38—C39—C40—Fe4 | 59.1 (3) |
C15—C16—C17—C13 | 0.6 (4) | C39—C40—C41—C42 | 0.0 (6) |
Fe2—C16—C17—C13 | 60.1 (3) | Fe4—C40—C41—C42 | −59.7 (3) |
C15—C16—C17—Fe2 | −59.5 (3) | C39—C40—C41—Fe4 | 59.7 (4) |
C14—C13—C17—C16 | −0.7 (4) | C40—C41—C42—C38 | 0.5 (5) |
Fe2—C13—C17—C16 | −60.3 (3) | Fe4—C41—C42—C38 | −59.5 (3) |
C14—C13—C17—Fe2 | 59.6 (3) | C40—C41—C42—Fe4 | 60.1 (4) |
C24—C20—C21—C22 | 0.3 (5) | C39—C38—C42—C41 | −0.8 (5) |
Fe1—C20—C21—C22 | −59.6 (3) | Fe4—C38—C42—C41 | 60.0 (3) |
C24—C20—C21—Fe1 | 59.8 (3) | C39—C38—C42—Fe4 | −60.8 (3) |
C20—C21—C22—C23 | 0.2 (5) | C47—C43—C44—C45 | 0.3 (4) |
Fe1—C21—C22—C23 | −59.3 (3) | Fe3—C43—C44—C45 | −59.5 (3) |
C20—C21—C22—Fe1 | 59.5 (3) | C47—C43—C44—Fe3 | 59.7 (3) |
C21—C22—C23—C24 | −0.5 (5) | C43—C44—C45—C46 | 0.0 (4) |
Fe1—C22—C23—C24 | −60.4 (3) | Fe3—C44—C45—C46 | −59.3 (3) |
C21—C22—C23—Fe1 | 59.8 (3) | C43—C44—C45—Fe3 | 59.2 (3) |
C21—C20—C24—C23 | −0.6 (5) | C44—C45—C46—C47 | −0.2 (4) |
Fe1—C20—C24—C23 | 59.1 (3) | Fe3—C45—C46—C47 | −59.8 (3) |
C21—C20—C24—Fe1 | −59.7 (3) | C44—C45—C46—Fe3 | 59.5 (3) |
C22—C23—C24—C20 | 0.7 (5) | C44—C43—C47—C46 | −0.4 (4) |
Fe1—C23—C24—C20 | −59.5 (3) | Fe3—C43—C47—C46 | 59.4 (3) |
C22—C23—C24—Fe1 | 60.2 (3) | C44—C43—C47—Fe3 | −59.8 (3) |
C7—C6—C18—O1 | 170.8 (17) | C45—C46—C47—C43 | 0.4 (4) |
C5—C6—C18—O1 | −9 (3) | Fe3—C46—C47—C43 | −59.4 (3) |
C7—C6—C18—S2 | −5.7 (16) | C45—C46—C47—Fe3 | 59.8 (3) |
C5—C6—C18—S2 | 174.2 (7) | C30—C31—S4—S5 | 0.0 (3) |
S1—S2—C18—O1 | −172.3 (17) | C33—C31—S4—S5 | −179.8 (3) |
S1—S2—C18—C6 | 4.4 (15) | O3—C32—S5—S4 | 170.7 (3) |
C6—C7—S1—S2 | −1.0 (4) | C30—C32—S5—S4 | −3.7 (3) |
C8—C7—S1—S2 | 178.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C36S—H36···O3i | 1.00 | 2.36 | 3.354 (6) | 170 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
The authors thank PAPIIT-DGAPA-UNAM (IN 217318), and CONACyT (251437) for their financial support of this work.
Funding information
Funding for this research was provided by: Consejo Nacional de Ciencia y Tecnología (award No. 251437); PAPIIT-DGAPA-UNAM (award No. IN-217318). .
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