Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109035847/fn3032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270109035847/fn3032Isup2.hkl |
CCDC reference: 763585
The title complex salt was obtained as a yellow–orange powder in 78% yield following the method of Sutherland et al. (1982) in a reaction of 1,2-benzenedithiol with (η6-2,3-dichlorotoluene)(η5-Cp)iron(II) hexafluoridophosphate. Analytical data: elemental analysis, calculated: C 43.57, H 3.05%; found: C 43.62, H 3.15%; 1H NMR (300.133 MHz, acetone-d6, δ, p.p.m.): 2.86 (s, methyl), 4.87 (s, Cp), 6.49 (t, 1H, complexed benzene ring, J = 6.2 Hz), 6.57 (d, 1H, complexed benzene ring, J = 6.2 Hz), 6.91 (d, 1H, complexed benzene ring, J = 6.2 Hz), 7.63 (m, 2H, uncomplexed benzene ring), 7.81 (m, 2H, uncomplexed benzene ring); 13C NMR (75.469 MHz, acetone-d6; δ, p.p.m.): 20.4 (methyl), 79.4 (Cp), 86.4, 88.0, 88.2 (C of complexed benzene ring), 104.1, 105.2, 106.0 (quaternary C of complexed benzene ring), 130.4, 130.5, 130.7, 130.9 (C of uncomplexed benzene ring), 133.3, 134.0 (quaternary C of uncomplexed benzene ring). The crystal used for data collection was grown by slow evaporation of the solvents from a solution of the complex in an acetone–diethyl ether–dichloromethane mixture [Solvent ratio?] at 280 (2) K.
The H atoms were placed in geometrically idealized positions with C—H distances of 0.93Å (aromatic), 0.98Å (idealized CH) and 0.96Å (idealized CH3) and were constrained to ride on the parent C atom with Uiso(H) = 1.2Ueq(C) for the aromatic and C—H protons and Uiso(H) = 1.5Ueq(C) for the idealized CH3 protons. The carbon atoms in the disordered cyclopentadienyl rings were restrained to be regular pentagons with C—C distances of 1.42Å and were refined to a 68:32 ratio. For each of the disordered cyclopentadienyl rings carbon ellipsods were constrained to be equal in size. For all of the PF6 groups the equatorial P—F distances were restrained to 1.55Å and the cis F—F distances were restrained to be 2.19 Å. The ellipsoids on the three PF6 groups were restrained to be similar in size. All three PF6 groups were found to have rotational disorder and were refined to have occupancies of 59:41 (P1), 51:49 (P2) and 50:50 (P3).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Fe(C5H5)(C13H10S2)]PF6·0.33C3H6O | Z = 2 |
Mr = 515.60 | F(000) = 1564 |
Triclinic, P1 | Dx = 1.682 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.5598 (10) Å | Cell parameters from 3081 reflections |
b = 15.4984 (15) Å | θ = 2.3–21.3° |
c = 19.4769 (19) Å | µ = 1.08 mm−1 |
α = 83.508 (1)° | T = 296 K |
β = 75.251 (1)° | Amorphous, brown |
γ = 84.088 (1)° | 0.46 × 0.32 × 0.13 mm |
V = 3053.6 (5) Å3 |
Bruker APEXII CCD diffractometer | 10509 independent reflections |
Radiation source: sealed tube | 6357 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −12→12 |
Tmin = 0.643, Tmax = 0.746 | k = −18→18 |
20371 measured reflections | l = −19→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0782P)2 + 3.5P] where P = (Fo2 + 2Fc2)/3 |
10509 reflections | (Δ/σ)max = 0.001 |
884 parameters | Δρmax = 0.93 e Å−3 |
498 restraints | Δρmin = −0.77 e Å−3 |
[Fe(C5H5)(C13H10S2)]PF6·0.33C3H6O | γ = 84.088 (1)° |
Mr = 515.60 | V = 3053.6 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.5598 (10) Å | Mo Kα radiation |
b = 15.4984 (15) Å | µ = 1.08 mm−1 |
c = 19.4769 (19) Å | T = 296 K |
α = 83.508 (1)° | 0.46 × 0.32 × 0.13 mm |
β = 75.251 (1)° |
Bruker APEXII CCD diffractometer | 10509 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | 6357 reflections with I > 2σ(I) |
Tmin = 0.643, Tmax = 0.746 | Rint = 0.041 |
20371 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 498 restraints |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.93 e Å−3 |
10509 reflections | Δρmin = −0.77 e Å−3 |
884 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.9272 (6) | 0.4080 (4) | 0.2205 (4) | 0.0402 (16) | |
C2 | 0.9698 (6) | 0.3920 (5) | 0.2840 (4) | 0.0493 (19) | |
H2 | 0.9913 | 0.3314 | 0.3004 | 0.059* | |
C3 | 0.9500 (6) | 0.4545 (5) | 0.3325 (4) | 0.0468 (18) | |
H3 | 0.9596 | 0.4365 | 0.3810 | 0.056* | |
C4 | 0.8890 (6) | 0.5369 (5) | 0.3184 (4) | 0.0413 (17) | |
H4 | 0.8567 | 0.5752 | 0.3569 | 0.050* | |
C4A | 0.8450 (6) | 0.5548 (4) | 0.2546 (4) | 0.0358 (15) | |
C5A | 0.8021 (6) | 0.6830 (4) | 0.1519 (4) | 0.0387 (16) | |
C6 | 0.8102 (7) | 0.7710 (5) | 0.1269 (5) | 0.056 (2) | |
H6 | 0.8009 | 0.8128 | 0.1589 | 0.068* | |
C7 | 0.8320 (8) | 0.7956 (6) | 0.0553 (5) | 0.067 (2) | |
H7 | 0.8359 | 0.8543 | 0.0391 | 0.080* | |
C8 | 0.8480 (9) | 0.7346 (6) | 0.0070 (5) | 0.070 (2) | |
H8 | 0.8601 | 0.7519 | −0.0414 | 0.084* | |
C9 | 0.8459 (8) | 0.6472 (5) | 0.0311 (4) | 0.058 (2) | |
H9 | 0.8616 | 0.6056 | −0.0016 | 0.069* | |
C10A | 0.8651 (6) | 0.4911 (4) | 0.2054 (4) | 0.0397 (16) | |
C11 | 0.9415 (8) | 0.3374 (5) | 0.1719 (4) | 0.061 (2) | |
H11A | 0.9749 | 0.2840 | 0.1934 | 0.092* | |
H11B | 1.0015 | 0.3533 | 0.1272 | 0.092* | |
H11C | 0.8575 | 0.3298 | 0.1640 | 0.092* | |
C12 | 0.6279 (8) | 0.4391 (6) | 0.4005 (4) | 0.062 (2) | |
H12 | 0.6269 | 0.4693 | 0.4422 | 0.074* | |
C13 | 0.6797 (7) | 0.3546 (6) | 0.3888 (5) | 0.059 (2) | |
H13 | 0.7213 | 0.3149 | 0.4210 | 0.071* | |
C14 | 0.6613 (8) | 0.3354 (6) | 0.3241 (5) | 0.065 (2) | |
H14 | 0.6862 | 0.2799 | 0.3027 | 0.078* | |
C15 | 0.5981 (7) | 0.4100 (7) | 0.2960 (5) | 0.066 (3) | |
H15 | 0.5708 | 0.4160 | 0.2512 | 0.080* | |
C16 | 0.5781 (7) | 0.4732 (6) | 0.3436 (5) | 0.062 (2) | |
H16 | 0.5347 | 0.5317 | 0.3380 | 0.074* | |
C9A | 0.8210 (7) | 0.6213 (4) | 0.1023 (4) | 0.0428 (17) | |
Fe1 | 0.77381 (8) | 0.43924 (6) | 0.30810 (5) | 0.0351 (3) | |
S10 | 0.8013 (2) | 0.50990 (12) | 0.12923 (10) | 0.0511 (5) | |
S5 | 0.75385 (19) | 0.65572 (12) | 0.24398 (10) | 0.0489 (5) | |
C21 | 0.0882 (6) | 0.2215 (4) | 0.5073 (4) | 0.0437 (17) | |
C22 | 0.0990 (7) | 0.2556 (5) | 0.4359 (4) | 0.053 (2) | |
H22 | 0.0483 | 0.2303 | 0.4085 | 0.063* | |
C23 | 0.2024 (8) | 0.3062 (5) | 0.3978 (4) | 0.055 (2) | |
H23 | 0.2192 | 0.3161 | 0.3458 | 0.066* | |
C24 | 0.2960 (7) | 0.3251 (5) | 0.4313 (4) | 0.0518 (19) | |
H24 | 0.3779 | 0.3480 | 0.4025 | 0.062* | |
C24A | 0.2865 (7) | 0.2946 (4) | 0.5032 (4) | 0.0462 (18) | |
C25A | 0.4330 (7) | 0.2288 (5) | 0.5980 (4) | 0.0466 (18) | |
C26 | 0.5587 (8) | 0.2042 (6) | 0.6043 (5) | 0.067 (2) | |
H26 | 0.6284 | 0.2344 | 0.5764 | 0.080* | |
C27 | 0.5819 (10) | 0.1356 (7) | 0.6516 (6) | 0.085 (3) | |
H27 | 0.6665 | 0.1216 | 0.6574 | 0.102* | |
C28 | 0.4805 (10) | 0.0871 (6) | 0.6907 (6) | 0.078 (3) | |
H28 | 0.4968 | 0.0401 | 0.7223 | 0.094* | |
C29 | 0.3550 (9) | 0.1091 (5) | 0.6824 (4) | 0.061 (2) | |
H29 | 0.2867 | 0.0760 | 0.7077 | 0.073* | |
C29A | 0.3305 (7) | 0.1796 (5) | 0.6369 (4) | 0.0458 (18) | |
C30A | 0.1835 (6) | 0.2437 (4) | 0.5414 (4) | 0.0403 (16) | |
C31 | −0.0183 (7) | 0.1641 (5) | 0.5451 (4) | 0.055 (2) | |
H31A | −0.0764 | 0.1931 | 0.5835 | 0.082* | |
H31B | 0.0198 | 0.1106 | 0.5639 | 0.082* | |
H31C | −0.0668 | 0.1518 | 0.5123 | 0.082* | |
C32 | 0.3709 (12) | 0.0766 (6) | 0.4729 (6) | 0.082 (3) | |
H32 | 0.3736 | 0.0540 | 0.5216 | 0.099* | |
C33 | 0.2764 (10) | 0.0622 (6) | 0.4375 (8) | 0.085 (3) | |
H33 | 0.2011 | 0.0270 | 0.4565 | 0.102* | |
C34 | 0.3113 (12) | 0.1045 (7) | 0.3698 (6) | 0.084 (3) | |
H34 | 0.2642 | 0.1050 | 0.3324 | 0.101* | |
C35 | 0.4237 (11) | 0.1432 (7) | 0.3633 (6) | 0.087 (3) | |
H35 | 0.4707 | 0.1773 | 0.3207 | 0.104* | |
C36 | 0.4609 (9) | 0.1265 (7) | 0.4263 (7) | 0.081 (3) | |
H36 | 0.5388 | 0.1467 | 0.4363 | 0.098* | |
Fe2 | 0.27857 (9) | 0.19144 (6) | 0.44355 (5) | 0.0396 (3) | |
S30 | 0.16657 (18) | 0.20821 (14) | 0.63178 (10) | 0.0547 (5) | |
S25 | 0.4053 (2) | 0.32401 (13) | 0.54403 (12) | 0.0570 (5) | |
C54 | 0.4542 (7) | 0.7622 (4) | 0.1444 (6) | 0.065 (2) | 0.683 (18) |
H54 | 0.4454 | 0.8225 | 0.1448 | 0.078* | 0.683 (18) |
C55 | 0.4394 (6) | 0.7007 (8) | 0.2051 (4) | 0.065 (2) | 0.683 (18) |
H55 | 0.4192 | 0.7136 | 0.2524 | 0.078* | 0.683 (18) |
C53 | 0.4608 (6) | 0.6160 (5) | 0.1811 (6) | 0.065 (2) | 0.683 (18) |
H53 | 0.4571 | 0.5637 | 0.2099 | 0.078* | 0.683 (18) |
C52 | 0.4889 (6) | 0.6252 (6) | 0.1055 (6) | 0.065 (2) | 0.683 (18) |
H52 | 0.5068 | 0.5800 | 0.0760 | 0.078* | 0.683 (18) |
C56 | 0.4848 (7) | 0.7156 (7) | 0.0828 (4) | 0.065 (2) | 0.683 (18) |
H56 | 0.4996 | 0.7400 | 0.0358 | 0.078* | 0.683 (18) |
C52B | 0.4778 (6) | 0.6093 (4) | 0.1469 (6) | 0.063 (5) | 0.317 (18) |
H52B | 0.4913 | 0.5490 | 0.1468 | 0.076* | 0.317 (18) |
C53B | 0.4356 (6) | 0.6470 (8) | 0.2101 (4) | 0.063 (5) | 0.317 (18) |
H53B | 0.4079 | 0.6225 | 0.2568 | 0.076* | 0.317 (18) |
C54B | 0.4483 (6) | 0.7393 (6) | 0.1806 (5) | 0.063 (5) | 0.317 (18) |
H54B | 0.4308 | 0.7879 | 0.2064 | 0.076* | 0.317 (18) |
C55B | 0.4947 (6) | 0.7389 (5) | 0.1008 (5) | 0.063 (5) | 0.317 (18) |
H55B | 0.5163 | 0.7881 | 0.0696 | 0.076* | 0.317 (18) |
C56B | 0.5007 (6) | 0.6631 (8) | 0.0817 (4) | 0.063 (5) | 0.317 (18) |
H56B | 0.5163 | 0.6464 | 0.0357 | 0.076* | 0.317 (18) |
C50A | 0.1666 (7) | 0.7604 (5) | 0.1034 (4) | 0.0449 (17) | |
C41 | 0.1957 (7) | 0.6792 (5) | 0.0725 (4) | 0.053 (2) | |
C42 | 0.1888 (7) | 0.6019 (5) | 0.1196 (6) | 0.063 (2) | |
H42 | 0.2301 | 0.5477 | 0.0996 | 0.076* | |
C43 | 0.1584 (7) | 0.6032 (5) | 0.1934 (5) | 0.063 (2) | |
H43 | 0.1770 | 0.5504 | 0.2230 | 0.076* | |
C44 | 0.1313 (7) | 0.6832 (5) | 0.2232 (4) | 0.054 (2) | |
H44 | 0.1313 | 0.6851 | 0.2733 | 0.065* | |
C44A | 0.1327 (6) | 0.7624 (5) | 0.1782 (4) | 0.0440 (17) | |
C45A | 0.1930 (7) | 0.9321 (5) | 0.1642 (4) | 0.0498 (19) | |
C46 | 0.2372 (8) | 0.9960 (6) | 0.1945 (6) | 0.071 (3) | |
H46 | 0.2167 | 0.9960 | 0.2439 | 0.085* | |
C47 | 0.3102 (10) | 1.0590 (6) | 0.1532 (7) | 0.088 (3) | |
H47 | 0.3343 | 1.1035 | 0.1744 | 0.106* | |
C48 | 0.3482 (11) | 1.0569 (7) | 0.0809 (7) | 0.094 (3) | |
H48 | 0.3999 | 1.0992 | 0.0531 | 0.113* | |
C49 | 0.3100 (9) | 0.9921 (6) | 0.0489 (5) | 0.076 (3) | |
H49 | 0.3375 | 0.9898 | −0.0002 | 0.092* | |
C49A | 0.2298 (7) | 0.9304 (5) | 0.0910 (5) | 0.055 (2) | |
C51 | 0.2370 (10) | 0.6739 (6) | −0.0065 (5) | 0.080 (3) | |
H51A | 0.2708 | 0.6154 | −0.0163 | 0.120* | |
H51B | 0.3041 | 0.7131 | −0.0274 | 0.120* | |
H51C | 0.1627 | 0.6896 | −0.0265 | 0.120* | |
Fe3 | 0.30849 (9) | 0.68399 (7) | 0.14612 (6) | 0.0443 (3) | |
S45 | 0.0871 (2) | 0.85913 (14) | 0.21993 (12) | 0.0597 (6) | |
S50 | 0.1694 (2) | 0.85654 (14) | 0.04635 (12) | 0.0629 (6) | |
P1 | 0.3736 (2) | 0.34007 (14) | 0.15460 (12) | 0.0693 (6) | |
F11 | 0.4260 (7) | 0.2721 (3) | 0.0994 (3) | 0.1181 (19) | |
F12 | 0.3268 (5) | 0.4076 (3) | 0.2106 (2) | 0.133 (2) | |
F13A | 0.2612 (8) | 0.2830 (5) | 0.1957 (5) | 0.109 (3) | 0.586 (6) |
F14A | 0.4610 (12) | 0.2896 (6) | 0.2011 (5) | 0.107 (3) | 0.586 (6) |
F15A | 0.4849 (10) | 0.3981 (6) | 0.1137 (5) | 0.116 (3) | 0.586 (6) |
F16A | 0.2858 (11) | 0.3911 (6) | 0.1084 (4) | 0.112 (3) | 0.586 (6) |
F14B | 0.5175 (3) | 0.3453 (10) | 0.1582 (8) | 0.100 (3) | 0.414 (6) |
F15B | 0.4042 (19) | 0.4151 (3) | 0.0946 (3) | 0.107 (3) | 0.414 (6) |
F13B | 0.360 (2) | 0.2656 (3) | 0.2156 (3) | 0.107 (3) | 0.414 (6) |
F16B | 0.2355 (7) | 0.3499 (10) | 0.1393 (8) | 0.115 (3) | 0.414 (6) |
P2 | 0.20247 (18) | 0.58365 (12) | 0.42021 (10) | 0.0548 (5) | |
F21 | 0.2379 (6) | 0.5270 (4) | 0.3562 (2) | 0.1053 (18) | |
F22 | 0.1676 (4) | 0.6409 (2) | 0.48378 (15) | 0.0903 (16) | |
F23A | 0.1930 (15) | 0.5007 (2) | 0.4732 (2) | 0.092 (3) | 0.492 (11) |
F24A | 0.3505 (2) | 0.5882 (10) | 0.4155 (6) | 0.086 (3) | 0.492 (11) |
F25A | 0.2108 (15) | 0.6673 (2) | 0.3678 (2) | 0.083 (3) | 0.492 (11) |
F26A | 0.0556 (3) | 0.5899 (8) | 0.4189 (6) | 0.082 (3) | 0.492 (11) |
F23B | 0.3238 (10) | 0.5404 (8) | 0.4455 (5) | 0.088 (3) | 0.508 (11) |
F24B | 0.2795 (13) | 0.6573 (5) | 0.3722 (3) | 0.090 (3) | 0.508 (11) |
F25B | 0.0780 (8) | 0.6241 (7) | 0.3967 (5) | 0.082 (3) | 0.508 (11) |
F26B | 0.1239 (13) | 0.5105 (5) | 0.4680 (4) | 0.102 (3) | 0.508 (11) |
P3 | 0.1131 (2) | 0.90440 (12) | 0.65271 (11) | 0.0626 (6) | |
F31 | 0.1619 (7) | 0.8322 (3) | 0.6010 (3) | 0.1207 (18) | |
F32 | 0.0636 (4) | 0.9746 (2) | 0.7061 (2) | 0.1150 (17) | |
F33A | 0.2349 (8) | 0.8802 (7) | 0.6837 (6) | 0.087 (2) | 0.504 (11) |
F34A | 0.1899 (13) | 0.9731 (4) | 0.5981 (4) | 0.103 (2) | 0.504 (11) |
F35A | −0.0069 (8) | 0.9304 (7) | 0.6205 (6) | 0.092 (2) | 0.504 (11) |
F36A | 0.0369 (13) | 0.8360 (4) | 0.7078 (4) | 0.110 (3) | 0.504 (11) |
F33B | 0.1814 (14) | 0.8499 (6) | 0.7068 (4) | 0.093 (2) | 0.496 (11) |
F34B | 0.2402 (7) | 0.9517 (6) | 0.6205 (6) | 0.096 (2) | 0.496 (11) |
F35B | 0.0393 (12) | 0.9568 (5) | 0.6001 (4) | 0.093 (2) | 0.496 (11) |
F36B | −0.0135 (7) | 0.8567 (6) | 0.6856 (6) | 0.102 (2) | 0.496 (11) |
C60 | 0.2240 (16) | 0.9463 (8) | 0.8637 (6) | 0.103 (4) | |
C61 | 0.0866 (14) | 0.9280 (12) | 0.8785 (8) | 0.170 (8) | |
H61A | 0.0562 | 0.9410 | 0.8358 | 0.255* | |
H61B | 0.0352 | 0.9634 | 0.9146 | 0.255* | |
H61C | 0.0780 | 0.8677 | 0.8949 | 0.255* | |
C62 | 0.3229 (12) | 0.8804 (9) | 0.8318 (7) | 0.124 (4) | |
H62A | 0.3196 | 0.8772 | 0.7834 | 0.187* | |
H62B | 0.3062 | 0.8249 | 0.8583 | 0.187* | |
H62C | 0.4083 | 0.8956 | 0.8327 | 0.187* | |
O1 | 0.2560 (17) | 1.0104 (7) | 0.8765 (7) | 0.217 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.035 (4) | 0.047 (4) | 0.036 (4) | −0.002 (3) | −0.002 (3) | −0.004 (3) |
C2 | 0.035 (4) | 0.055 (5) | 0.051 (5) | 0.001 (3) | −0.005 (3) | 0.006 (4) |
C3 | 0.036 (4) | 0.060 (5) | 0.046 (5) | −0.007 (3) | −0.016 (3) | 0.005 (4) |
C4 | 0.036 (4) | 0.053 (4) | 0.039 (4) | −0.007 (3) | −0.011 (3) | −0.009 (3) |
C4A | 0.036 (4) | 0.038 (4) | 0.035 (4) | −0.005 (3) | −0.011 (3) | −0.006 (3) |
C5A | 0.042 (4) | 0.034 (4) | 0.041 (4) | −0.002 (3) | −0.014 (3) | 0.003 (3) |
C6 | 0.060 (5) | 0.045 (5) | 0.066 (6) | −0.004 (4) | −0.021 (4) | −0.002 (4) |
C7 | 0.072 (6) | 0.053 (5) | 0.065 (6) | −0.004 (4) | −0.007 (5) | 0.014 (5) |
C8 | 0.084 (6) | 0.072 (6) | 0.045 (5) | −0.004 (5) | −0.007 (4) | 0.014 (5) |
C9 | 0.074 (6) | 0.050 (5) | 0.043 (5) | −0.002 (4) | −0.006 (4) | 0.001 (4) |
C10A | 0.035 (4) | 0.045 (4) | 0.038 (4) | −0.003 (3) | −0.007 (3) | −0.003 (3) |
C11 | 0.076 (6) | 0.044 (5) | 0.054 (5) | 0.009 (4) | −0.002 (4) | −0.011 (4) |
C12 | 0.062 (5) | 0.073 (6) | 0.041 (5) | −0.022 (4) | 0.011 (4) | −0.002 (4) |
C13 | 0.048 (5) | 0.068 (6) | 0.051 (5) | −0.010 (4) | −0.003 (4) | 0.021 (4) |
C14 | 0.054 (5) | 0.054 (5) | 0.083 (7) | −0.023 (4) | 0.003 (5) | −0.019 (5) |
C15 | 0.040 (4) | 0.110 (8) | 0.051 (5) | −0.031 (5) | −0.015 (4) | 0.014 (5) |
C16 | 0.036 (4) | 0.059 (5) | 0.076 (7) | 0.001 (3) | 0.005 (4) | 0.010 (5) |
C9A | 0.046 (4) | 0.046 (4) | 0.035 (4) | −0.008 (3) | −0.011 (3) | 0.006 (3) |
Fe1 | 0.0323 (5) | 0.0403 (6) | 0.0323 (6) | −0.0018 (4) | −0.0076 (4) | −0.0029 (4) |
S10 | 0.0770 (13) | 0.0426 (11) | 0.0396 (11) | −0.0078 (9) | −0.0233 (10) | −0.0045 (9) |
S5 | 0.0626 (12) | 0.0427 (11) | 0.0419 (11) | 0.0075 (8) | −0.0154 (9) | −0.0108 (9) |
C21 | 0.036 (4) | 0.043 (4) | 0.051 (5) | 0.002 (3) | −0.011 (3) | −0.004 (4) |
C22 | 0.041 (4) | 0.056 (5) | 0.061 (6) | 0.006 (3) | −0.020 (4) | −0.001 (4) |
C23 | 0.058 (5) | 0.059 (5) | 0.044 (5) | 0.004 (4) | −0.011 (4) | 0.007 (4) |
C24 | 0.054 (5) | 0.044 (4) | 0.050 (5) | −0.004 (3) | −0.002 (4) | 0.005 (4) |
C24A | 0.045 (4) | 0.035 (4) | 0.056 (5) | −0.002 (3) | −0.004 (3) | −0.009 (4) |
C25A | 0.050 (4) | 0.053 (5) | 0.040 (4) | −0.009 (3) | −0.011 (3) | −0.013 (4) |
C26 | 0.056 (5) | 0.068 (6) | 0.081 (7) | −0.015 (4) | −0.021 (5) | −0.003 (5) |
C27 | 0.066 (6) | 0.078 (7) | 0.123 (10) | 0.000 (5) | −0.045 (6) | −0.017 (7) |
C28 | 0.090 (7) | 0.061 (6) | 0.095 (8) | −0.009 (5) | −0.047 (6) | 0.001 (5) |
C29 | 0.075 (6) | 0.060 (5) | 0.052 (5) | −0.017 (4) | −0.020 (4) | 0.002 (4) |
C29A | 0.057 (5) | 0.048 (4) | 0.036 (4) | −0.007 (3) | −0.011 (3) | −0.013 (4) |
C30A | 0.039 (4) | 0.034 (4) | 0.042 (4) | 0.001 (3) | 0.001 (3) | −0.008 (3) |
C31 | 0.045 (4) | 0.060 (5) | 0.059 (5) | −0.008 (4) | −0.009 (4) | −0.006 (4) |
C32 | 0.108 (8) | 0.055 (6) | 0.068 (7) | 0.040 (6) | −0.009 (7) | −0.013 (5) |
C33 | 0.065 (6) | 0.043 (5) | 0.133 (11) | −0.004 (4) | 0.013 (7) | −0.033 (6) |
C34 | 0.100 (8) | 0.081 (7) | 0.081 (8) | 0.029 (6) | −0.037 (7) | −0.050 (6) |
C35 | 0.084 (7) | 0.079 (7) | 0.075 (8) | 0.002 (6) | 0.026 (6) | −0.028 (6) |
C36 | 0.044 (5) | 0.085 (7) | 0.114 (10) | 0.025 (5) | −0.015 (6) | −0.041 (7) |
Fe2 | 0.0392 (5) | 0.0393 (6) | 0.0370 (6) | 0.0017 (4) | −0.0045 (4) | −0.0060 (5) |
S30 | 0.0472 (11) | 0.0758 (14) | 0.0366 (11) | −0.0126 (9) | 0.0015 (8) | −0.0071 (10) |
S25 | 0.0642 (13) | 0.0507 (12) | 0.0591 (14) | −0.0231 (9) | −0.0132 (10) | −0.0042 (10) |
C54 | 0.042 (4) | 0.087 (5) | 0.068 (5) | −0.007 (3) | −0.019 (3) | −0.002 (3) |
C55 | 0.042 (4) | 0.087 (5) | 0.068 (5) | −0.007 (3) | −0.019 (3) | −0.002 (3) |
C53 | 0.042 (4) | 0.087 (5) | 0.068 (5) | −0.007 (3) | −0.019 (3) | −0.002 (3) |
C52 | 0.042 (4) | 0.087 (5) | 0.068 (5) | −0.007 (3) | −0.019 (3) | −0.002 (3) |
C56 | 0.042 (4) | 0.087 (5) | 0.068 (5) | −0.007 (3) | −0.019 (3) | −0.002 (3) |
C52B | 0.042 (8) | 0.088 (11) | 0.063 (9) | −0.003 (6) | −0.025 (6) | 0.012 (7) |
C53B | 0.042 (8) | 0.088 (11) | 0.063 (9) | −0.003 (6) | −0.025 (6) | 0.012 (7) |
C54B | 0.042 (8) | 0.088 (11) | 0.063 (9) | −0.003 (6) | −0.025 (6) | 0.012 (7) |
C55B | 0.042 (8) | 0.088 (11) | 0.063 (9) | −0.003 (6) | −0.025 (6) | 0.012 (7) |
C56B | 0.042 (8) | 0.088 (11) | 0.063 (9) | −0.003 (6) | −0.025 (6) | 0.012 (7) |
C50A | 0.041 (4) | 0.049 (4) | 0.047 (5) | −0.002 (3) | −0.017 (3) | −0.001 (4) |
C41 | 0.042 (4) | 0.060 (5) | 0.062 (5) | −0.005 (3) | −0.019 (4) | −0.011 (4) |
C42 | 0.043 (4) | 0.053 (5) | 0.097 (8) | −0.006 (4) | −0.022 (5) | −0.009 (5) |
C43 | 0.045 (5) | 0.055 (5) | 0.082 (7) | −0.011 (4) | −0.005 (4) | 0.008 (5) |
C44 | 0.037 (4) | 0.066 (5) | 0.049 (5) | 0.000 (3) | 0.001 (3) | 0.004 (4) |
C44A | 0.036 (4) | 0.048 (4) | 0.044 (5) | −0.002 (3) | −0.006 (3) | 0.002 (4) |
C45A | 0.044 (4) | 0.044 (4) | 0.055 (5) | 0.001 (3) | −0.006 (4) | 0.001 (4) |
C46 | 0.065 (6) | 0.066 (6) | 0.085 (7) | 0.002 (5) | −0.019 (5) | −0.028 (5) |
C47 | 0.085 (7) | 0.064 (7) | 0.119 (10) | −0.020 (5) | −0.022 (7) | −0.016 (7) |
C48 | 0.101 (8) | 0.067 (7) | 0.110 (10) | −0.032 (6) | −0.015 (7) | 0.010 (7) |
C49 | 0.087 (7) | 0.074 (7) | 0.059 (6) | −0.001 (5) | −0.010 (5) | 0.007 (5) |
C49A | 0.053 (5) | 0.047 (5) | 0.059 (6) | 0.006 (3) | −0.011 (4) | 0.006 (4) |
C51 | 0.098 (7) | 0.090 (7) | 0.063 (6) | 0.002 (5) | −0.034 (5) | −0.032 (5) |
Fe3 | 0.0330 (5) | 0.0509 (6) | 0.0468 (7) | −0.0005 (4) | −0.0090 (5) | 0.0006 (5) |
S45 | 0.0581 (12) | 0.0592 (13) | 0.0519 (13) | 0.0005 (9) | 0.0029 (10) | −0.0056 (10) |
S50 | 0.0838 (15) | 0.0592 (13) | 0.0502 (13) | −0.0012 (11) | −0.0300 (11) | 0.0036 (10) |
P1 | 0.0776 (15) | 0.0619 (14) | 0.0708 (16) | −0.0020 (11) | −0.0209 (12) | −0.0127 (11) |
F11 | 0.165 (5) | 0.097 (4) | 0.088 (4) | −0.011 (3) | −0.010 (4) | −0.036 (3) |
F12 | 0.174 (5) | 0.101 (4) | 0.114 (4) | 0.024 (4) | −0.014 (4) | −0.051 (4) |
F13A | 0.091 (5) | 0.094 (5) | 0.123 (6) | −0.012 (4) | 0.004 (4) | 0.011 (4) |
F14A | 0.112 (5) | 0.107 (5) | 0.106 (5) | 0.010 (5) | −0.045 (4) | 0.001 (4) |
F15A | 0.099 (5) | 0.093 (5) | 0.138 (6) | −0.023 (4) | 0.002 (5) | 0.003 (5) |
F16A | 0.120 (5) | 0.104 (5) | 0.119 (5) | −0.011 (4) | −0.053 (4) | 0.024 (4) |
F14B | 0.091 (4) | 0.111 (6) | 0.105 (6) | −0.014 (5) | −0.031 (5) | −0.012 (5) |
F15B | 0.102 (6) | 0.084 (5) | 0.120 (5) | −0.003 (5) | −0.012 (5) | 0.020 (4) |
F13B | 0.117 (6) | 0.093 (5) | 0.096 (5) | −0.006 (5) | −0.008 (6) | 0.015 (4) |
F16B | 0.085 (4) | 0.138 (6) | 0.121 (6) | −0.026 (5) | −0.028 (5) | 0.014 (5) |
P2 | 0.0523 (11) | 0.0636 (13) | 0.0489 (12) | −0.0009 (9) | −0.0127 (9) | −0.0098 (10) |
F21 | 0.127 (4) | 0.108 (4) | 0.086 (4) | 0.009 (3) | −0.026 (3) | −0.048 (3) |
F22 | 0.109 (4) | 0.105 (4) | 0.060 (3) | 0.031 (3) | −0.031 (3) | −0.031 (3) |
F23A | 0.093 (6) | 0.080 (4) | 0.089 (5) | 0.012 (4) | −0.014 (5) | 0.014 (4) |
F24A | 0.055 (4) | 0.112 (6) | 0.086 (6) | −0.009 (4) | −0.006 (4) | −0.013 (5) |
F25A | 0.093 (6) | 0.094 (4) | 0.071 (5) | −0.028 (4) | −0.034 (4) | 0.010 (4) |
F26A | 0.062 (4) | 0.092 (6) | 0.099 (6) | −0.023 (4) | −0.028 (4) | 0.000 (5) |
F23B | 0.070 (4) | 0.119 (6) | 0.065 (5) | 0.028 (4) | −0.016 (4) | −0.007 (5) |
F24B | 0.087 (5) | 0.110 (5) | 0.080 (5) | −0.056 (4) | −0.020 (4) | 0.001 (4) |
F25B | 0.073 (4) | 0.096 (6) | 0.082 (5) | 0.000 (4) | −0.036 (4) | 0.006 (4) |
F26B | 0.084 (6) | 0.090 (5) | 0.109 (5) | −0.007 (4) | 0.003 (5) | 0.023 (4) |
P3 | 0.0679 (13) | 0.0480 (12) | 0.0782 (16) | −0.0036 (9) | −0.0300 (11) | −0.0060 (10) |
F31 | 0.150 (4) | 0.103 (3) | 0.125 (4) | 0.034 (3) | −0.059 (3) | −0.059 (3) |
F32 | 0.124 (4) | 0.100 (3) | 0.118 (4) | 0.020 (3) | −0.017 (3) | −0.051 (3) |
F33A | 0.079 (4) | 0.091 (5) | 0.101 (5) | −0.008 (3) | −0.044 (3) | −0.001 (4) |
F34A | 0.092 (4) | 0.100 (4) | 0.108 (5) | −0.015 (4) | −0.021 (4) | 0.031 (3) |
F35A | 0.085 (4) | 0.079 (5) | 0.122 (5) | −0.010 (3) | −0.052 (3) | 0.016 (4) |
F36A | 0.102 (5) | 0.093 (4) | 0.126 (5) | −0.017 (4) | −0.030 (4) | 0.043 (3) |
F33B | 0.101 (5) | 0.085 (4) | 0.098 (4) | −0.004 (4) | −0.047 (4) | 0.015 (3) |
F34B | 0.077 (4) | 0.106 (5) | 0.106 (5) | −0.022 (3) | −0.025 (4) | 0.010 (4) |
F35B | 0.092 (4) | 0.080 (4) | 0.110 (4) | −0.007 (4) | −0.043 (4) | 0.026 (4) |
F36B | 0.092 (4) | 0.097 (4) | 0.119 (5) | −0.030 (3) | −0.039 (4) | 0.029 (4) |
C60 | 0.182 (11) | 0.072 (8) | 0.063 (7) | 0.015 (7) | −0.058 (8) | 0.003 (6) |
C61 | 0.123 (9) | 0.28 (2) | 0.091 (10) | 0.076 (11) | −0.038 (9) | −0.011 (11) |
C62 | 0.115 (9) | 0.148 (12) | 0.108 (11) | 0.021 (8) | −0.030 (8) | −0.027 (9) |
O1 | 0.42 (2) | 0.084 (7) | 0.170 (12) | −0.007 (10) | −0.115 (13) | −0.019 (7) |
C1—C2 | 1.409 (10) | C54—H54 | 0.9300 |
C1—C10A | 1.418 (9) | C55—C53 | 1.4200 |
C1—C11 | 1.497 (10) | C55—Fe3 | 2.061 (6) |
C1—Fe1 | 2.095 (6) | C55—H55 | 0.9300 |
C2—C3 | 1.393 (10) | C53—C52 | 1.4200 |
C2—Fe1 | 2.076 (7) | C53—Fe3 | 2.052 (6) |
C2—H2 | 0.9800 | C53—H53 | 0.9300 |
C3—C4 | 1.401 (9) | C52—C56 | 1.4200 |
C3—Fe1 | 2.077 (6) | C52—Fe3 | 2.031 (6) |
C3—H3 | 0.9800 | C52—H52 | 0.9300 |
C4—C4A | 1.424 (9) | C56—Fe3 | 2.027 (7) |
C4—Fe1 | 2.094 (6) | C56—H56 | 0.9300 |
C4—H4 | 0.9800 | C52B—C53B | 1.3738 |
C4A—C10A | 1.417 (9) | C52B—C56B | 1.4182 |
C4A—S5 | 1.770 (6) | C52B—Fe3 | 2.030 (6) |
C4A—Fe1 | 2.078 (7) | C52B—H52B | 0.9300 |
C5A—C9A | 1.398 (9) | C53B—C54B | 1.4860 |
C5A—C6 | 1.399 (9) | C53B—Fe3 | 2.054 (6) |
C5A—S5 | 1.750 (7) | C53B—H53B | 0.9300 |
C6—C7 | 1.370 (11) | C54B—C55B | 1.5072 |
C6—H6 | 0.9300 | C54B—Fe3 | 2.064 (6) |
C7—C8 | 1.377 (12) | C54B—H54B | 0.9300 |
C7—H7 | 0.9300 | C55B—C56B | 1.2623 |
C8—C9 | 1.382 (11) | C55B—Fe3 | 2.159 (6) |
C8—H8 | 0.9300 | C55B—H55B | 0.9300 |
C9—C9A | 1.365 (10) | C56B—Fe3 | 2.111 (6) |
C9—H9 | 0.9300 | C56B—H56B | 0.9300 |
C10A—S10 | 1.764 (7) | C50A—C44A | 1.411 (10) |
C10A—Fe1 | 2.095 (7) | C50A—C41 | 1.426 (10) |
C11—H11A | 0.9600 | C50A—S50 | 1.754 (7) |
C11—H11B | 0.9600 | C50A—Fe3 | 2.093 (7) |
C11—H11C | 0.9600 | C41—C42 | 1.420 (11) |
C12—C16 | 1.375 (12) | C41—C51 | 1.500 (11) |
C12—C13 | 1.386 (11) | C41—Fe3 | 2.095 (7) |
C12—Fe1 | 2.049 (8) | C42—C43 | 1.393 (12) |
C12—H12 | 0.9800 | C42—Fe3 | 2.073 (8) |
C13—C14 | 1.392 (12) | C42—H42 | 0.9800 |
C13—Fe1 | 2.046 (7) | C43—C44 | 1.400 (11) |
C13—H13 | 0.9800 | C43—Fe3 | 2.081 (8) |
C14—C15 | 1.402 (12) | C43—H43 | 0.9800 |
C14—Fe1 | 2.047 (7) | C44—C44A | 1.425 (10) |
C14—H14 | 0.9800 | C44—Fe3 | 2.080 (7) |
C15—C16 | 1.388 (12) | C44—H44 | 0.9800 |
C15—Fe1 | 2.031 (7) | C44A—S45 | 1.752 (7) |
C15—H15 | 0.9800 | C44A—Fe3 | 2.105 (7) |
C16—Fe1 | 2.039 (7) | C45A—C49A | 1.382 (11) |
C16—H16 | 0.9800 | C45A—C46 | 1.385 (11) |
C9A—S10 | 1.765 (7) | C45A—S45 | 1.753 (8) |
C21—C22 | 1.411 (10) | C46—C47 | 1.362 (13) |
C21—C30A | 1.426 (9) | C46—H46 | 0.9300 |
C21—C31 | 1.495 (10) | C47—C48 | 1.366 (15) |
C21—Fe2 | 2.114 (7) | C47—H47 | 0.9300 |
C22—C23 | 1.411 (10) | C48—C49 | 1.383 (13) |
C22—Fe2 | 2.081 (7) | C48—H48 | 0.9300 |
C22—H22 | 0.9800 | C49—C49A | 1.393 (11) |
C23—C24 | 1.385 (11) | C49—H49 | 0.9300 |
C23—Fe2 | 2.077 (7) | C49A—S50 | 1.768 (9) |
C23—H23 | 0.9800 | C51—H51A | 0.9600 |
C24—C24A | 1.408 (10) | C51—H51B | 0.9600 |
C24—Fe2 | 2.080 (7) | C51—H51C | 0.9600 |
C24—H24 | 0.9800 | P1—F16B | 1.5499 (12) |
C24A—C30A | 1.410 (9) | P1—F13B | 1.5500 (12) |
C24A—S25 | 1.768 (7) | P1—F15B | 1.5500 (12) |
C24A—Fe2 | 2.099 (7) | P1—F14B | 1.5501 (12) |
C25A—C26 | 1.375 (10) | P1—F14A | 1.5502 (12) |
C25A—C29A | 1.396 (10) | P1—F13A | 1.550 (3) |
C25A—S25 | 1.756 (8) | P1—F11 | 1.550 (4) |
C26—C27 | 1.370 (13) | P1—F16A | 1.551 (3) |
C26—H26 | 0.9300 | P1—F15A | 1.5507 (12) |
C27—C28 | 1.383 (13) | P1—F12 | 1.551 (4) |
C27—H27 | 0.9300 | P2—F24B | 1.5494 (12) |
C28—C29 | 1.379 (11) | P2—F25B | 1.5500 (12) |
C28—H28 | 0.9300 | P2—F23A | 1.5502 (12) |
C29—C29A | 1.374 (10) | P2—F26A | 1.5502 (12) |
C29—H29 | 0.9300 | P2—F23B | 1.5502 (12) |
C29A—S30 | 1.767 (7) | P2—F26B | 1.5504 (12) |
C30A—S30 | 1.754 (7) | P2—F22 | 1.551 (3) |
C30A—Fe2 | 2.121 (7) | P2—F21 | 1.551 (3) |
C31—H31A | 0.9600 | P2—F24A | 1.5513 (12) |
C31—H31B | 0.9600 | P2—F25A | 1.5515 (12) |
C31—H31C | 0.9600 | P3—F32 | 1.549 (3) |
C32—C36 | 1.370 (14) | P3—F35B | 1.5496 (12) |
C32—C33 | 1.397 (14) | P3—F36A | 1.5497 (12) |
C32—Fe2 | 2.034 (8) | P3—F34B | 1.5498 (12) |
C32—H32 | 0.9800 | P3—F31 | 1.550 (3) |
C33—C34 | 1.382 (14) | P3—F35A | 1.5503 (12) |
C33—Fe2 | 2.023 (8) | P3—F36B | 1.5504 (12) |
C33—H33 | 0.9800 | P3—F33A | 1.5504 (12) |
C34—C35 | 1.356 (14) | P3—F33B | 1.5507 (12) |
C34—Fe2 | 2.022 (9) | P3—F34A | 1.5509 (12) |
C34—H34 | 0.9800 | C60—O1 | 1.155 (14) |
C35—C36 | 1.371 (14) | C60—C62 | 1.453 (15) |
C35—Fe2 | 2.039 (9) | C60—C61 | 1.456 (19) |
C35—H35 | 0.9800 | C61—H61A | 0.9600 |
C36—Fe2 | 2.045 (8) | C61—H61B | 0.9600 |
C36—H36 | 0.9800 | C61—H61C | 0.9600 |
C54—C55 | 1.4200 | C62—H62A | 0.9600 |
C54—C56 | 1.4200 | C62—H62B | 0.9600 |
C54—Fe3 | 2.047 (6) | C62—H62C | 0.9600 |
C2—C1—C10A | 118.5 (6) | C30A—S30—C29A | 103.0 (3) |
C2—C1—C11 | 120.6 (6) | C25A—S25—C24A | 102.4 (3) |
C10A—C1—C11 | 120.9 (6) | C55—C54—C56 | 108.0 |
C2—C1—Fe1 | 69.6 (4) | C55—C54—Fe3 | 70.3 (2) |
C10A—C1—Fe1 | 70.2 (4) | C56—C54—Fe3 | 68.9 (2) |
C11—C1—Fe1 | 129.8 (5) | C55—C54—H54 | 126.0 |
C3—C2—C1 | 121.9 (7) | C56—C54—H54 | 126.0 |
C3—C2—Fe1 | 70.4 (4) | Fe3—C54—H54 | 126.4 |
C1—C2—Fe1 | 71.0 (4) | C54—C55—C53 | 108.0 |
C3—C2—H2 | 118.0 | C54—C55—Fe3 | 69.2 (3) |
C1—C2—H2 | 118.0 | C53—C55—Fe3 | 69.4 (2) |
Fe1—C2—H2 | 118.0 | C54—C55—H55 | 126.0 |
C2—C3—C4 | 120.3 (7) | C53—C55—H55 | 126.0 |
C2—C3—Fe1 | 70.4 (4) | Fe3—C55—H55 | 126.9 |
C4—C3—Fe1 | 71.0 (4) | C55—C53—C52 | 108.0 |
C2—C3—H3 | 119.1 | C55—C53—Fe3 | 70.2 (2) |
C4—C3—H3 | 119.1 | C52—C53—Fe3 | 68.8 (3) |
Fe1—C3—H3 | 119.1 | C55—C53—H53 | 126.0 |
C3—C4—C4A | 119.0 (6) | C52—C53—H53 | 126.0 |
C3—C4—Fe1 | 69.7 (4) | Fe3—C53—H53 | 126.5 |
C4A—C4—Fe1 | 69.4 (4) | C56—C52—C53 | 108.0 |
C3—C4—H4 | 119.5 | C56—C52—Fe3 | 69.4 (3) |
C4A—C4—H4 | 119.5 | C53—C52—Fe3 | 70.4 (2) |
Fe1—C4—H4 | 119.5 | C56—C52—H52 | 126.0 |
C10A—C4A—C4 | 120.6 (6) | C53—C52—H52 | 126.0 |
C10A—C4A—S5 | 122.4 (5) | Fe3—C52—H52 | 125.7 |
C4—C4A—S5 | 116.9 (5) | C52—C56—C54 | 108.0 |
C10A—C4A—Fe1 | 70.8 (4) | C52—C56—Fe3 | 69.6 (2) |
C4—C4A—Fe1 | 70.7 (4) | C54—C56—Fe3 | 70.3 (2) |
S5—C4A—Fe1 | 127.3 (3) | C52—C56—H56 | 126.0 |
C9A—C5A—C6 | 118.6 (7) | C54—C56—H56 | 126.0 |
C9A—C5A—S5 | 122.7 (5) | Fe3—C56—H56 | 125.6 |
C6—C5A—S5 | 118.5 (6) | C53B—C52B—C56B | 119.3 |
C7—C6—C5A | 120.1 (8) | C53B—C52B—Fe3 | 71.3 (3) |
C7—C6—H6 | 120.0 | C56B—C52B—Fe3 | 73.1 (3) |
C5A—C6—H6 | 120.0 | C53B—C52B—H52B | 120.3 |
C6—C7—C8 | 120.8 (8) | C56B—C52B—H52B | 120.3 |
C6—C7—H7 | 119.6 | Fe3—C52B—H52B | 127.3 |
C8—C7—H7 | 119.6 | C52B—C53B—C54B | 97.9 |
C7—C8—C9 | 119.3 (8) | C52B—C53B—Fe3 | 69.4 (2) |
C7—C8—H8 | 120.3 | C54B—C53B—Fe3 | 69.2 (2) |
C9—C8—H8 | 120.3 | C52B—C53B—H53B | 131.1 |
C9A—C9—C8 | 120.8 (8) | C54B—C53B—H53B | 131.1 |
C9A—C9—H9 | 119.6 | Fe3—C53B—H53B | 122.5 |
C8—C9—H9 | 119.6 | C53B—C54B—C55B | 106.8 |
C4A—C10A—C1 | 119.8 (6) | C53B—C54B—Fe3 | 68.5 (3) |
C4A—C10A—S10 | 120.9 (5) | C55B—C54B—Fe3 | 72.5 (2) |
C1—C10A—S10 | 119.1 (5) | C53B—C54B—H54B | 126.6 |
C4A—C10A—Fe1 | 69.5 (4) | C55B—C54B—H54B | 126.6 |
C1—C10A—Fe1 | 70.2 (4) | Fe3—C54B—H54B | 124.0 |
S10—C10A—Fe1 | 128.6 (3) | C56B—C55B—C54B | 111.3 |
C1—C11—H11A | 109.5 | C56B—C55B—Fe3 | 70.7 (2) |
C1—C11—H11B | 109.5 | C54B—C55B—Fe3 | 65.8 (2) |
H11A—C11—H11B | 109.5 | C56B—C55B—H55B | 124.3 |
C1—C11—H11C | 109.5 | C54B—C55B—H55B | 124.3 |
H11A—C11—H11C | 109.5 | Fe3—C55B—H55B | 131.0 |
H11B—C11—H11C | 109.5 | C55B—C56B—C52B | 103.8 |
C16—C12—C13 | 108.4 (8) | C55B—C56B—Fe3 | 74.9 (2) |
C16—C12—Fe1 | 69.9 (5) | C52B—C56B—Fe3 | 66.9 (2) |
C13—C12—Fe1 | 70.1 (4) | C55B—C56B—H56B | 128.1 |
C16—C12—H12 | 125.8 | C52B—C56B—H56B | 128.1 |
C13—C12—H12 | 125.8 | Fe3—C56B—H56B | 121.9 |
Fe1—C12—H12 | 125.8 | C44A—C50A—C41 | 120.4 (7) |
C12—C13—C14 | 108.4 (8) | C44A—C50A—S50 | 121.2 (6) |
C12—C13—Fe1 | 70.3 (4) | C41—C50A—S50 | 118.3 (6) |
C14—C13—Fe1 | 70.2 (5) | C44A—C50A—Fe3 | 70.8 (4) |
C12—C13—H13 | 125.8 | C41—C50A—Fe3 | 70.2 (4) |
C14—C13—H13 | 125.8 | S50—C50A—Fe3 | 133.9 (4) |
Fe1—C13—H13 | 125.8 | C42—C41—C50A | 117.6 (8) |
C13—C14—C15 | 106.9 (8) | C42—C41—C51 | 120.0 (8) |
C13—C14—Fe1 | 70.1 (4) | C50A—C41—C51 | 122.3 (8) |
C15—C14—Fe1 | 69.3 (5) | C42—C41—Fe3 | 69.2 (5) |
C13—C14—H14 | 126.5 | C50A—C41—Fe3 | 70.0 (4) |
C15—C14—H14 | 126.5 | C51—C41—Fe3 | 130.4 (6) |
Fe1—C14—H14 | 126.5 | C43—C42—C41 | 122.4 (8) |
C16—C15—C14 | 108.2 (8) | C43—C42—Fe3 | 70.7 (5) |
C16—C15—Fe1 | 70.4 (4) | C41—C42—Fe3 | 70.9 (4) |
C14—C15—Fe1 | 70.5 (4) | C43—C42—H42 | 117.7 |
C16—C15—H15 | 125.9 | C41—C42—H42 | 117.7 |
C14—C15—H15 | 125.9 | Fe3—C42—H42 | 117.7 |
Fe1—C15—H15 | 125.9 | C42—C43—C44 | 119.5 (8) |
C12—C16—C15 | 108.1 (8) | C42—C43—Fe3 | 70.1 (5) |
C12—C16—Fe1 | 70.7 (4) | C44—C43—Fe3 | 70.3 (4) |
C15—C16—Fe1 | 69.7 (4) | C42—C43—H43 | 119.4 |
C12—C16—H16 | 125.9 | C44—C43—H43 | 119.4 |
C15—C16—H16 | 125.9 | Fe3—C43—H43 | 119.4 |
Fe1—C16—H16 | 125.9 | C43—C44—C44A | 120.0 (8) |
C9—C9A—C5A | 120.3 (7) | C43—C44—Fe3 | 70.4 (4) |
C9—C9A—S10 | 117.9 (6) | C44A—C44—Fe3 | 71.0 (4) |
C5A—C9A—S10 | 121.7 (5) | C43—C44—H44 | 119.3 |
C15—Fe1—C16 | 39.9 (3) | C44A—C44—H44 | 119.3 |
C15—Fe1—C13 | 66.8 (3) | Fe3—C44—H44 | 119.3 |
C16—Fe1—C13 | 66.5 (3) | C50A—C44A—C44 | 120.0 (7) |
C15—Fe1—C14 | 40.2 (3) | C50A—C44A—S45 | 122.9 (5) |
C16—Fe1—C14 | 67.1 (3) | C44—C44A—S45 | 117.1 (6) |
C13—Fe1—C14 | 39.7 (3) | C50A—C44A—Fe3 | 69.9 (4) |
C15—Fe1—C12 | 66.5 (4) | C44—C44A—Fe3 | 69.2 (4) |
C16—Fe1—C12 | 39.3 (3) | S45—C44A—Fe3 | 135.6 (4) |
C13—Fe1—C12 | 39.6 (3) | C49A—C45A—C46 | 118.8 (8) |
C14—Fe1—C12 | 66.7 (3) | C49A—C45A—S45 | 122.5 (6) |
C15—Fe1—C2 | 139.7 (4) | C46—C45A—S45 | 118.6 (7) |
C16—Fe1—C2 | 172.1 (3) | C47—C46—C45A | 121.0 (10) |
C13—Fe1—C2 | 105.7 (3) | C47—C46—H46 | 119.5 |
C14—Fe1—C2 | 108.0 (3) | C45A—C46—H46 | 119.5 |
C12—Fe1—C2 | 133.6 (3) | C46—C47—C48 | 120.2 (10) |
C15—Fe1—C3 | 171.6 (3) | C46—C47—H47 | 119.9 |
C16—Fe1—C3 | 139.5 (4) | C48—C47—H47 | 119.9 |
C13—Fe1—C3 | 104.9 (3) | C47—C48—C49 | 120.3 (10) |
C14—Fe1—C3 | 132.2 (3) | C47—C48—H48 | 119.9 |
C12—Fe1—C3 | 108.3 (3) | C49—C48—H48 | 119.9 |
C2—Fe1—C3 | 39.2 (3) | C48—C49—C49A | 119.3 (10) |
C15—Fe1—C4A | 116.6 (3) | C48—C49—H49 | 120.3 |
C16—Fe1—C4A | 102.4 (3) | C49A—C49—H49 | 120.3 |
C13—Fe1—C4A | 159.5 (3) | C45A—C49A—C49 | 120.2 (8) |
C14—Fe1—C4A | 153.8 (3) | C45A—C49A—S50 | 122.4 (6) |
C12—Fe1—C4A | 121.2 (3) | C49—C49A—S50 | 117.2 (7) |
C2—Fe1—C4A | 84.5 (3) | C41—C51—H51A | 109.5 |
C3—Fe1—C4A | 71.7 (3) | C41—C51—H51B | 109.5 |
C15—Fe1—C4 | 146.7 (4) | H51A—C51—H51B | 109.5 |
C16—Fe1—C4 | 112.0 (3) | C41—C51—H51C | 109.5 |
C13—Fe1—C4 | 126.1 (3) | H51A—C51—H51C | 109.5 |
C14—Fe1—C4 | 165.7 (4) | H51B—C51—H51C | 109.5 |
C12—Fe1—C4 | 103.1 (3) | C56—Fe3—C52B | 57.37 (13) |
C2—Fe1—C4 | 71.1 (3) | C56—Fe3—C52 | 40.97 (11) |
C3—Fe1—C4 | 39.3 (3) | C52B—Fe3—C52 | 22.68 (6) |
C4A—Fe1—C4 | 39.9 (2) | C56—Fe3—C54 | 40.79 (12) |
C15—Fe1—C1 | 111.5 (3) | C52B—Fe3—C54 | 70.56 (12) |
C16—Fe1—C1 | 146.2 (3) | C52—Fe3—C54 | 68.60 (13) |
C13—Fe1—C1 | 127.0 (3) | C56—Fe3—C53 | 68.56 (13) |
C14—Fe1—C1 | 102.8 (3) | C52B—Fe3—C53 | 18.66 (5) |
C12—Fe1—C1 | 166.6 (3) | C52—Fe3—C53 | 40.71 (10) |
C2—Fe1—C1 | 39.5 (3) | C54—Fe3—C53 | 68.20 (12) |
C3—Fe1—C1 | 71.9 (3) | C56—Fe3—C53B | 76.71 (12) |
C4A—Fe1—C1 | 72.0 (3) | C52B—Fe3—C53B | 39.31 (10) |
C4—Fe1—C1 | 85.6 (3) | C52—Fe3—C53B | 59.57 (13) |
C15—Fe1—C10A | 102.4 (3) | C54—Fe3—C53B | 60.73 (14) |
C16—Fe1—C10A | 116.5 (3) | C53—Fe3—C53B | 21.36 (6) |
C13—Fe1—C10A | 160.4 (3) | C56—Fe3—C55 | 68.37 (13) |
C14—Fe1—C10A | 121.6 (3) | C52B—Fe3—C55 | 54.17 (12) |
C12—Fe1—C10A | 153.0 (3) | C52—Fe3—C55 | 68.31 (12) |
C2—Fe1—C10A | 71.2 (3) | C54—Fe3—C55 | 40.44 (11) |
C3—Fe1—C10A | 85.1 (3) | C53—Fe3—C55 | 40.39 (10) |
C4A—Fe1—C10A | 39.7 (2) | C53B—Fe3—C55 | 23.30 (7) |
C4—Fe1—C10A | 72.1 (3) | C56—Fe3—C54B | 55.82 (13) |
C1—Fe1—C10A | 39.6 (3) | C52B—Fe3—C54B | 63.60 (11) |
C10A—S10—C9A | 103.6 (3) | C52—Fe3—C54B | 70.31 (11) |
C5A—S5—C4A | 102.4 (3) | C54—Fe3—C54B | 20.86 (6) |
C22—C21—C30A | 117.2 (6) | C53—Fe3—C54B | 55.00 (12) |
C22—C21—C31 | 121.1 (7) | C53B—Fe3—C54B | 42.31 (11) |
C30A—C21—C31 | 121.7 (7) | C55—Fe3—C54B | 20.10 (6) |
C22—C21—Fe2 | 69.1 (4) | C56—Fe3—C42 | 123.9 (4) |
C30A—C21—Fe2 | 70.6 (4) | C52B—Fe3—C42 | 104.5 (3) |
C31—C21—Fe2 | 131.0 (5) | C52—Fe3—C42 | 101.0 (3) |
C23—C22—C21 | 122.3 (7) | C54—Fe3—C42 | 164.5 (4) |
C23—C22—Fe2 | 70.0 (4) | C53—Fe3—C42 | 111.9 (3) |
C21—C22—Fe2 | 71.6 (4) | C53B—Fe3—C42 | 124.9 (4) |
C23—C22—H22 | 117.8 | C55—Fe3—C42 | 147.9 (4) |
C21—C22—H22 | 117.8 | C54B—Fe3—C42 | 166.8 (4) |
Fe2—C22—H22 | 117.8 | C56—Fe3—C44 | 164.1 (4) |
C24—C23—C22 | 119.6 (7) | C52B—Fe3—C44 | 128.2 (4) |
C24—C23—Fe2 | 70.7 (4) | C52—Fe3—C44 | 148.9 (4) |
C22—C23—Fe2 | 70.3 (4) | C54—Fe3—C44 | 123.9 (4) |
C24—C23—H23 | 119.4 | C53—Fe3—C44 | 112.9 (3) |
C22—C23—H23 | 119.4 | C53B—Fe3—C44 | 99.5 (3) |
Fe2—C23—H23 | 119.4 | C55—Fe3—C44 | 102.0 (3) |
C23—C24—C24A | 119.9 (7) | C54B—Fe3—C44 | 111.1 (3) |
C23—C24—Fe2 | 70.4 (4) | C42—Fe3—C44 | 71.0 (4) |
C24A—C24—Fe2 | 71.0 (4) | C56—Fe3—C43 | 156.2 (4) |
C23—C24—H24 | 119.4 | C52B—Fe3—C43 | 105.4 (3) |
C24A—C24—H24 | 119.4 | C52—Fe3—C43 | 117.1 (4) |
Fe2—C24—H24 | 119.4 | C54—Fe3—C43 | 155.6 (4) |
C24—C24A—C30A | 120.7 (7) | C53—Fe3—C43 | 100.0 (3) |
C24—C24A—S25 | 117.8 (6) | C53B—Fe3—C43 | 100.3 (3) |
C30A—C24A—S25 | 121.4 (6) | C55—Fe3—C43 | 117.1 (4) |
C24—C24A—Fe2 | 69.6 (4) | C54B—Fe3—C43 | 135.3 (4) |
C30A—C24A—Fe2 | 71.3 (4) | C42—Fe3—C43 | 39.2 (3) |
S25—C24A—Fe2 | 133.6 (4) | C44—Fe3—C43 | 39.3 (3) |
C26—C25A—C29A | 119.2 (7) | C56—Fe3—C50A | 106.0 (3) |
C26—C25A—S25 | 118.8 (6) | C52B—Fe3—C50A | 157.9 (4) |
C29A—C25A—S25 | 121.9 (6) | C52—Fe3—C50A | 135.3 (4) |
C27—C26—C25A | 120.4 (8) | C54—Fe3—C50A | 107.3 (3) |
C27—C26—H26 | 119.8 | C53—Fe3—C50A | 174.5 (3) |
C25A—C26—H26 | 119.8 | C53B—Fe3—C50A | 159.0 (4) |
C26—C27—C28 | 120.6 (9) | C55—Fe3—C50A | 137.7 (4) |
C26—C27—H27 | 119.7 | C54B—Fe3—C50A | 121.6 (3) |
C28—C27—H27 | 119.7 | C42—Fe3—C50A | 71.5 (3) |
C29—C28—C27 | 119.3 (9) | C44—Fe3—C50A | 72.1 (3) |
C29—C28—H28 | 120.3 | C43—Fe3—C50A | 85.4 (3) |
C27—C28—H28 | 120.3 | C44A—S45—C45A | 102.7 (4) |
C29A—C29—C28 | 120.3 (8) | C50A—S50—C49A | 102.8 (4) |
C29A—C29—H29 | 119.8 | F16B—P1—F13B | 102.5 (10) |
C28—C29—H29 | 119.8 | F16B—P1—F15B | 84.4 (9) |
C29—C29A—C25A | 120.1 (7) | F13B—P1—F15B | 173.1 (11) |
C29—C29A—S30 | 118.4 (6) | F16B—P1—F14B | 168.7 (10) |
C25A—C29A—S30 | 121.5 (6) | F13B—P1—F14B | 88.8 (10) |
C24A—C30A—C21 | 120.3 (7) | F15B—P1—F14B | 84.3 (9) |
C24A—C30A—S30 | 121.4 (6) | F14A—P1—F13A | 88.0 (7) |
C21—C30A—S30 | 118.3 (5) | F16B—P1—F11 | 92.6 (4) |
C24A—C30A—Fe2 | 69.6 (4) | F13B—P1—F11 | 89.6 (4) |
C21—C30A—Fe2 | 70.1 (4) | F15B—P1—F11 | 90.3 (4) |
S30—C30A—Fe2 | 135.2 (4) | F14B—P1—F11 | 87.7 (4) |
C21—C31—H31A | 109.5 | F14A—P1—F11 | 88.2 (4) |
C21—C31—H31B | 109.5 | F13A—P1—F11 | 91.4 (4) |
H31A—C31—H31B | 109.5 | F14A—P1—F16A | 179.6 (2) |
C21—C31—H31C | 109.5 | F13A—P1—F16A | 92.1 (7) |
H31A—C31—H31C | 109.5 | F11—P1—F16A | 92.3 (4) |
H31B—C31—H31C | 109.5 | F14A—P1—F15A | 92.4 (7) |
C36—C32—C33 | 107.3 (10) | F13A—P1—F15A | 179.3 (4) |
C36—C32—Fe2 | 70.8 (5) | F11—P1—F15A | 89.2 (4) |
C33—C32—Fe2 | 69.4 (5) | F16A—P1—F15A | 87.5 (7) |
C36—C32—H32 | 126.3 | F16B—P1—F12 | 89.83 (13) |
C33—C32—H32 | 126.3 | F13B—P1—F12 | 89.79 (13) |
Fe2—C32—H32 | 126.3 | F15B—P1—F12 | 89.98 (13) |
C34—C33—C32 | 107.2 (9) | F14B—P1—F12 | 89.92 (13) |
C34—C33—Fe2 | 70.0 (5) | F14A—P1—F12 | 89.85 (13) |
C32—C33—Fe2 | 70.3 (5) | F13A—P1—F12 | 89.88 (13) |
C34—C33—H33 | 126.4 | F11—P1—F12 | 177.6 (4) |
C32—C33—H33 | 126.4 | F16A—P1—F12 | 89.73 (13) |
Fe2—C33—H33 | 126.4 | F15A—P1—F12 | 89.58 (13) |
C35—C34—C33 | 108.4 (10) | F24B—P2—F25B | 88.4 (6) |
C35—C34—Fe2 | 71.2 (6) | F23A—P2—F26A | 94.4 (7) |
C33—C34—Fe2 | 70.1 (5) | F24B—P2—F23B | 93.8 (7) |
C35—C34—H34 | 125.8 | F25B—P2—F23B | 177.8 (7) |
C33—C34—H34 | 125.8 | F24B—P2—F26B | 179.3 (7) |
Fe2—C34—H34 | 125.8 | F25B—P2—F26B | 90.9 (7) |
C34—C35—C36 | 108.6 (10) | F23B—P2—F26B | 86.9 (7) |
C34—C35—Fe2 | 69.8 (5) | F24B—P2—F22 | 90.06 (13) |
C36—C35—Fe2 | 70.6 (5) | F25B—P2—F22 | 89.98 (13) |
C34—C35—H35 | 125.7 | F23A—P2—F22 | 89.81 (13) |
C36—C35—H35 | 125.7 | F26A—P2—F22 | 89.89 (13) |
Fe2—C35—H35 | 125.7 | F23B—P2—F22 | 90.01 (13) |
C32—C36—C35 | 108.4 (10) | F26B—P2—F22 | 89.87 (13) |
C32—C36—Fe2 | 70.0 (5) | F24B—P2—F21 | 89.4 (3) |
C35—C36—Fe2 | 70.1 (5) | F25B—P2—F21 | 90.0 (3) |
C32—C36—H36 | 125.8 | F23A—P2—F21 | 90.6 (3) |
C35—C36—H36 | 125.8 | F26A—P2—F21 | 90.3 (3) |
Fe2—C36—H36 | 125.8 | F23B—P2—F21 | 90.0 (3) |
C34—Fe2—C33 | 39.9 (4) | F26B—P2—F21 | 90.6 (3) |
C34—Fe2—C32 | 66.9 (4) | F22—P2—F21 | 179.5 (3) |
C33—Fe2—C32 | 40.3 (4) | F23A—P2—F24A | 92.7 (7) |
C34—Fe2—C35 | 39.0 (4) | F26A—P2—F24A | 172.9 (7) |
C33—Fe2—C35 | 66.3 (4) | F22—P2—F24A | 89.60 (13) |
C32—Fe2—C35 | 66.2 (4) | F21—P2—F24A | 90.2 (3) |
C34—Fe2—C36 | 66.0 (4) | F23A—P2—F25A | 179.3 (4) |
C33—Fe2—C36 | 66.5 (4) | F26A—P2—F25A | 85.3 (6) |
C32—Fe2—C36 | 39.3 (4) | F22—P2—F25A | 89.60 (13) |
C35—Fe2—C36 | 39.2 (4) | F21—P2—F25A | 90.0 (3) |
C34—Fe2—C23 | 106.0 (4) | F24A—P2—F25A | 87.6 (7) |
C33—Fe2—C23 | 136.9 (5) | F32—P3—F35B | 90.13 (13) |
C32—Fe2—C23 | 171.1 (4) | F32—P3—F36A | 90.01 (13) |
C35—Fe2—C23 | 104.9 (4) | F32—P3—F34B | 89.95 (13) |
C36—Fe2—C23 | 133.7 (4) | F35B—P3—F34B | 92.9 (7) |
C34—Fe2—C24 | 130.4 (5) | F32—P3—F31 | 178.4 (3) |
C33—Fe2—C24 | 170.2 (4) | F35B—P3—F31 | 91.0 (3) |
C32—Fe2—C24 | 141.7 (5) | F36A—P3—F31 | 88.5 (4) |
C35—Fe2—C24 | 104.9 (4) | F34B—P3—F31 | 91.0 (4) |
C36—Fe2—C24 | 109.8 (4) | F32—P3—F35A | 89.90 (13) |
C23—Fe2—C24 | 38.9 (3) | F36A—P3—F35A | 91.6 (7) |
C34—Fe2—C22 | 102.9 (4) | F31—P3—F35A | 90.7 (3) |
C33—Fe2—C22 | 110.3 (4) | F32—P3—F36B | 89.95 (13) |
C32—Fe2—C22 | 145.2 (5) | F35B—P3—F36B | 87.7 (7) |
C35—Fe2—C22 | 127.5 (5) | F34B—P3—F36B | 179.4 (7) |
C36—Fe2—C22 | 166.7 (4) | F31—P3—F36B | 89.1 (4) |
C23—Fe2—C22 | 39.7 (3) | F32—P3—F33A | 89.96 (13) |
C24—Fe2—C22 | 71.0 (3) | F36A—P3—F33A | 89.7 (7) |
C34—Fe2—C24A | 165.7 (5) | F31—P3—F33A | 89.5 (3) |
C33—Fe2—C24A | 149.4 (5) | F35A—P3—F33A | 178.6 (7) |
C32—Fe2—C24A | 114.7 (4) | F32—P3—F33B | 89.88 (13) |
C35—Fe2—C24A | 127.3 (4) | F35B—P3—F33B | 177.5 (7) |
C36—Fe2—C24A | 105.7 (4) | F34B—P3—F33B | 89.6 (7) |
C23—Fe2—C24A | 70.7 (3) | F31—P3—F33B | 88.9 (3) |
C24—Fe2—C24A | 39.4 (3) | F36B—P3—F33B | 89.8 (7) |
C22—Fe2—C24A | 83.5 (3) | F32—P3—F34A | 89.71 (13) |
C34—Fe2—C21 | 121.5 (4) | F36A—P3—F34A | 179.6 (6) |
C33—Fe2—C21 | 101.6 (3) | F31—P3—F34A | 91.7 (4) |
C32—Fe2—C21 | 115.8 (4) | F35A—P3—F34A | 88.7 (7) |
C35—Fe2—C21 | 159.8 (4) | F33A—P3—F34A | 89.9 (7) |
C36—Fe2—C21 | 152.5 (4) | O1—C60—C62 | 119.6 (17) |
C23—Fe2—C21 | 72.3 (3) | O1—C60—C61 | 122.4 (16) |
C24—Fe2—C21 | 85.6 (3) | C62—C60—C61 | 118.0 (13) |
C22—Fe2—C21 | 39.3 (3) | C60—C61—H61A | 109.5 |
C24A—Fe2—C21 | 71.5 (3) | C60—C61—H61B | 109.5 |
C34—Fe2—C30A | 155.2 (5) | H61A—C61—H61B | 109.5 |
C33—Fe2—C30A | 118.4 (4) | C60—C61—H61C | 109.5 |
C32—Fe2—C30A | 104.3 (3) | H61A—C61—H61C | 109.5 |
C35—Fe2—C30A | 160.5 (4) | H61B—C61—H61C | 109.5 |
C36—Fe2—C30A | 122.8 (4) | C60—C62—H62A | 109.5 |
C23—Fe2—C30A | 84.3 (3) | C60—C62—H62B | 109.5 |
C24—Fe2—C30A | 71.3 (3) | H62A—C62—H62B | 109.5 |
C22—Fe2—C30A | 70.4 (3) | C60—C62—H62C | 109.5 |
C24A—Fe2—C30A | 39.0 (3) | H62A—C62—H62C | 109.5 |
C21—Fe2—C30A | 39.4 (3) | H62B—C62—H62C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H5)(C13H10S2)]PF6·0.33C3H6O |
Mr | 515.60 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 10.5598 (10), 15.4984 (15), 19.4769 (19) |
α, β, γ (°) | 83.508 (1), 75.251 (1), 84.088 (1) |
V (Å3) | 3053.6 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.08 |
Crystal size (mm) | 0.46 × 0.32 × 0.13 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2008) |
Tmin, Tmax | 0.643, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20371, 10509, 6357 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.180, 1.08 |
No. of reflections | 10509 |
No. of parameters | 884 |
No. of restraints | 498 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.93, −0.77 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
The title compound, (I), was obtained in work extending earlier studies of the synthesis of polycyclic heteroaromatic systems in a double nucleophilic aromatic substitution reaction using 1,2-dichlorobenzene FeCp complexes (Sutherland et al., 1982, 1988). This study is a continuation of the combined influence of methyl substitution and FeCp complexation on the geometry of the thianthrene molecule. The crystal structure of (I) contains three cationic molecules (A–C) of the CpFe(1-methylthianthrene) complex, three hexafluoridophosphate counteranion molecules and one acetone molecule in the asymmetric unit. This is the first time that the formation of both FeCp-out-of-fold and FeCp-in-fold molecules of folded tricyclic heterocycles resulting from a double nucleophilic aromatic substitution reaction have been observed. Our earlier studies of the synthesis of dibenzodioxin and thianthrene FeCp complexes using the same reaction suggested that only FeCp-in-fold molecules are formed in such a reaction, as crystals of the dibenzodioxins and thianthrenes studied by X-ray crystallography have shown the presence of only FeCp-in-fold species (Simonsen et al., 1985; Abboud et al., 1990, 1991; Christie et al., 1994; Piórko et al., 1994, 1995). Conversely, phenoxathiin [-thiene?] complexes obtained in a similar reaction have shown the presence of only out-of-fold molecules in the solid state, as determined from examination of their crystal structures (Lynch et al., 1986; Sutherland et al., 1988). The only previous case in which the presence of both FeCp-out-of- and in-fold molecules was observed in the solid state came from the monodemetallation of the thianthrene bis(FeCp) dication obtained in a ligand-exchange reaction from thianthrene (Abboud et al., 1990). Thus, it appears that both in- and out-of-fold molecules may be formed in a nucleophilic aromatic substitution reaction.
The complexed Cp and benzene rings of (I) are nearly coplanar in all three molecules, with the dihedral angles 0.2 (5)° for A, 2.8 (5)° for B, and 2.19 (4)° and 6.86 (6)° for disordered Cp in C. These values are in the range observed for other thianthrene and dibenzodioxin FeCp complexes in our previous studies (see, for example, Simonsen et al., 1985; Lynch et al., 1986; Abboud et al., 1990, 1991; Christie et al., 1994; Piórko et al., 1995). The Cp–Fe–benzene ring centroid vectors are nearly collinear, with angles 179.65 (8)°, 178.42 (7)° for molecules A and B, and 178.69 (7)° ans 176.39 (7)° for disordered Cp in C. These values are typically found in the literature for FeCp–arene complexes (see, for example, Manzur et al., 2000; Fuentealba et al., 2007).
The distances from Fe ion to the Cp plane and to the complexed benzene ring plane are 1.666 (3)Å and 1.537 (3)Å in A, 1.662 (3)Å and 1.551 (3)Å in B, and 1.648 (4)Å and 1.538 (3)Å and 1.701 (4) and 1.538 (3)Å in the two disordered Cp in C. These values are close to those reported in the literature for similar complexes (see, for example, Lynch et al., 1986; Abboud et al., 1990; Piórko et al., 1995; Fuentealba et al., 2007; Manzur et al., 2007; Jenkins et al., 2008).
The Fe—C distances of the complexed benzene ring are in the range 2.073 (6)–2.121 (7) Å, with all three distances to quaternary C atoms being the longest in the two FeCp-in molecules, B and C, while in the FeCp-out molecule, A, one of these distances is among the shorter ones. In all four thianthrene molecules studied previously, the distances from the Fe atom to the quaternary C atoms of the complexed benzene ring are longer than those to the non-quaternary C atoms, with the thianthrene FeCp-out-of-fold molecule showing the narrowest range for these distances (Simonsen et al., 1985; Abboud et al., 1990; Christie et al., 1994). Overall, the average Fe—C distances of the complexed ring are 2.086, 2.095 and 2.088 Å for molecules A, B and C, respectively, and again these are within the range of reported distances for FeCp complexes (Abboud et al., 1990; Piórko et al., 1995; Fuentealba et al., 2007; Manzur et al., 2007; Jenkins et al., 2008).
The C—C distances in the complexed ring of the thianthrene show a tendency to be longer than those in the uncomplexed ring, with averages of 1.410 versus 1.382 Å for molecule A, 1.409 versus 1.380 Å for molecule B, and 1.413 versus 1.379 Å for molecule C. The S—C distances to both complexed and uncomplexed ring C atoms are quite similar and in the rather narrow range of 1.750 (7)–1.770 (6) Å. Both these observations agree with our earlier findings for thianthrene and isomeric methylthianthrene FeCp complexes (Simonsen et al., 1985; Abboud et al., 1990; Christie et al., 1994).
The dihedral angle between the two benzene rings of the thianthrene molecule has been reported to be insensitive to changes in substitution in or on one of the aromatic rings compared with thianthrene itself (for thianthrene, see: Larson et al., 1984; for other alkylthianthrenes, see: Wei, 1971; Lynch et al., 1984; Ogawa et al., 1999; Yamamoto et al., 2006). In our previous studies, we concluded that complexation of the thianthrene molecule with FeCp changes the dihedral angle between the two external benzene rings of this heterocycle. We reported that FeCp complexation of thianthrene flattens its structure and we found that the dihedral angle changes from 128.28 (7)° in thianthrene (Larson et al., 1984) to 136.3 (2)° for FeCp-out-of-fold and to 143.1 (2)° for FeCp-in-fold molecules (Abboud et al., 1990), and to 137.7 (3)° for the 2-methylthianthrene FeCp-in-fold molecule (Christie et al., 1994). We noted, however, that this angle was slightly smaller [127.4 (3)°] for the 2-methylthianthrene molecule with FeCp complexed on the unsubstituted benzene ring (Simonsen et al., 1985). In the current study, we have found that complexation flattens the heterocycle indeed, and that the dihedral angles for molecules A, B and C are 146.5 (2), 139.0 (3) and 142.5 (3)°, respectively. It is surprising that, unlike in the case of thianthrene–FeCp complexes, the molecule is flattened more by an FeCp moiety located out-of-fold. Also, the magnitude of this influence is notable, as such a value of the dihedral angle has not been reported previously.
Our results indicate that more studies are required in order to understand the joint influence of the presence and position of a methyl substituent and FeCp complexation on the geometry of a thianthrene molecule. In addition, the presence of two distinct structures in which FeCp is located inside the thianthrene fold signifies the importance of packing forces as another, yet difficult to evaluate, factor, which influences the geometry of thianthrene in FeCp complexes in crystals.