metal-organic compounds
(1,4,7,10,13,16-Hexaoxacyclooctadecane-κ6O)bis(tetrahydrofuran-κO)potassium bis[(1,2,3,4-η)-anthracene]cobalt(−I) tetrahydrofuran monosolvate
aTechnische Universität München, Department of Chemistry, Lichtenbergstrasse 4, 85747 Garching, Germany
*Correspondence e-mail: thomas.faessler@lrz.tum.de
The 12H24O6)(C4H8O)2][Co(C14H10)2]·C4H8O, consists of one cationic potassium complex, one anionic cobalt dianthracene complex and one tetrahydrofuran solvent molecule. The potassium cation is situated at the centre of an 18-crown-6 molecule and between two tetrahydrofuran molecules, the latter coordinating above and below the mean plane formed by the O atoms of the crown ether molecule. The Co atom is coordinated by eight C atoms of two anthracene molecules in an η4 manner. The third free tetrahydrofuran molecule shows orientational disorder on two partially occupied positions [occupancy ratio 0.561 (8):0.439 (8)].
of the title compound, [K(CCCDC reference: 974481
Related literature
For the synthesis, see: Brennessel, Young & Ellis (2002); Brennessel & Ellis (2012). Other homoleptic transition metal-anthracene complexes are reported by Elschenbroich et al. (1984); Brennessel, Ellis, Pomije et al. (2002), Brennessel, Ellis, Roush et al. (2002); Brennessel et al. (2007); Jilek et al. (2008). For related structures, see: Hanic & Mills (1968); Veauthier et al. (2000); Wang & Fässler (2009); Woolf et al. (2011); Zhu et al. (2006). Zintl compounds and their chemistry are reviewed by Scharfe et al. (2011). For a description of the Cambridge Structural database, see: Allen (2002).
Experimental
Crystal data
|
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2012); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 974481
https://doi.org/10.1107/S1600536813032510/hg5364sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032510/hg5364Isup2.hkl
To a deep-blue solution of K[C14H10] (3.43 mmol) in tetrahydrofuran (THF) (30 ml, -78°C) was added a bright-blue solution of CoBr2 (0.25 g, 1.15 mmol) in THF (30 ml, -78°C). The reaction was stirred overnight and warmed slowly to room temperature, the colour of the solution gradually changed to deep-pinkish-red. It was filtered to remove KBr, and 18-crown-6 (0.302 g, 1.15 mmol) in THF (10 ml) was added to the filtrate. Hexane (20 ml) was added and the volume was reduced to about 20 ml in vacuum. The brown-black needle-like product was crystallized at -40°C by diffusion of diethyl ether (50 ml) which yields the title compound (Yield: 41% based on CoBr2). The energy-dispersive X-ray analysis (EDX) shows an atomic ratio of Co/K close to 1:1 in all the analysed crystals of [K(C12H24O6)(C4H8O)2][Co(C14H10)2](C4H8O).
The H atoms were included in calculated positions and treated as riding atoms: C—H = 0.93 Å with Uiso(H) = 1.2 Ueq (parent C atom) for the aromatic, C—H = 0.97 Å with Uiso(H) = 1.2 Ueq (parent C atom) for the crown ether, and C—H = 0.97 Å with Uiso(H) = 1.5 Ueq (parent C atom) for the tetrahydrofuran H atoms. The free solvent molecule shows disorder and was refined at two positions with partial occupations of 56% and 44%, respectively. Two C atoms of the THF molecule with lower occupation have been refined with isotropic thermal displacement parameters.
Organometallic compounds with transition metals in a low η2 (Woolf et al., 2011), η4, and η6 (Hanic & Mills, 1968; Elschenbroich et al., 1984), in its monohydrogenated form even as a η5 (Veauthier et al., 2000) ligand. Regarding the entries of the Cambridge Structural Database (Allen, 2002), it is interesting that homoleptic anthracene complexes have been obtained exclusively with η4 coordination of the transition metals Ti, Zr, Hf (Jilek et al., 2008), Nb (Brennessel, Ellis, Roush et al., 2002), Ta (Brennessel, Ellis, Pomije et al., 2002), Fe ((Brennessel et al., 2007), and Co (Brennessel, Young & Ellis, 2002).
are important precursors for the formation of intermetalloid clusters from Zintl anions (Scharfe et al., 2011). Transition metal complexes with polycyclic aromatic hydrocarbons as ligands can serve as storable, but reactive sources of low-valent metal atoms or even anions (Brennessel & Ellis, 2012). Within this group of compounds, anthracene has been found as a prominent, sometimes favoured ligand (Zhu et al., 2006), which can act as aThe title compound was obtained via reduction of CoBr2 by potassium anthracene in THF. Although the reaction conditions were very similar to those described by Brennessel, Young & Ellis (2002), we found the compound to crystallize including an additional free solvent molecule (Fig.1). Consequently different from the literature, our indexation resulted in the orthorhombic, but acentric 1. Besides these differences, those structural entities, which are present in both compounds, show almost the same shape (Fig.2).
P212121 instead of PThe Co atom is sandwiched by two anthracene molecules in 1,2,3,4-η4 coordination, respectively, with a slight tilt of 10.2° for the two planes formed by the respective coordinating atoms C1—C4. The C6 rings, which are directly bond to the Co atom, are in eclipsed position, but the main molecule axes form an angle of about 65°. The anthracene molecules are folded at an axis running through the C1 and C4 atoms, the angles between the planes formed by C1, C2, C3, and C4 and by C1, and C4—C14 are almost identical (29.18° and 28.99° for both molecules).
For the synthesis, see: Brennessel, Young & Ellis (2002); Brennessel & Ellis (2012). Other homoleptic transition metal-anthracene complexes are reported by Elschenbroich et al. (1984); Brennessel, Ellis, Pomije et al. (2002), Brennessel, Ellis, Roush et al. (2002); Brennessel et al. (2007); Jilek et al. (2008). For other related structures, see: Hanic & Mills (1968); Veauthier et al. (2000); Wang & Fässler (2009), Woolf et al. (2011); Zhu et al. (2006). Zintl compounds and their chemistry are reviewed by Scharfe et al. (2011). For a description of the Cambridge Structural database, see: Allen (2002).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).[K(C12H24O6)(C4H8O)2][Co(C14H10)2]·C4H8O | F(000) = 1992 |
Mr = 935.09 | Dx = 1.297 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 8368 reflections |
a = 13.0428 (10) Å | θ = 3.0–37.0° |
b = 13.3557 (10) Å | µ = 0.50 mm−1 |
c = 27.4939 (17) Å | T = 150 K |
V = 4789.3 (6) Å3 | Plate, brown-black |
Z = 4 | 0.6 × 0.3 × 0.05 mm |
Oxford Diffraction Xcalibur 3 diffractometer | 9364 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4717 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.105 |
Detector resolution: 16.0238 pixels mm-1 | θmax = 26.0°, θmin = 3.0° |
ω and φ scans | h = −16→16 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | k = −16→16 |
Tmin = 0.787, Tmax = 0.975 | l = −33→33 |
62002 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0282P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.77 | (Δ/σ)max = 0.001 |
9364 reflections | Δρmax = 0.96 e Å−3 |
604 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 4164 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.005 (14) |
[K(C12H24O6)(C4H8O)2][Co(C14H10)2]·C4H8O | V = 4789.3 (6) Å3 |
Mr = 935.09 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 13.0428 (10) Å | µ = 0.50 mm−1 |
b = 13.3557 (10) Å | T = 150 K |
c = 27.4939 (17) Å | 0.6 × 0.3 × 0.05 mm |
Oxford Diffraction Xcalibur 3 diffractometer | 9364 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 4717 reflections with I > 2σ(I) |
Tmin = 0.787, Tmax = 0.975 | Rint = 0.105 |
62002 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.076 | Δρmax = 0.96 e Å−3 |
S = 0.77 | Δρmin = −0.37 e Å−3 |
9364 reflections | Absolute structure: Flack (1983), 4164 Friedel pairs |
604 parameters | Absolute structure parameter: −0.005 (14) |
0 restraints |
Experimental. Absorption correction: CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.34d (release 27-02-2009 CrysAlis171 .NET) (compiled Feb 27 2009,15:38:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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) | |
Co1 | 0.53937 (4) | 0.06723 (4) | 0.164895 (18) | 0.03905 (16) | |
C1 | 0.4723 (3) | −0.0533 (3) | 0.20524 (12) | 0.0363 (10) | |
H1A | 0.4912 | −0.0612 | 0.2395 | 0.044* | |
C2 | 0.4052 (3) | 0.0236 (3) | 0.19268 (15) | 0.0414 (11) | |
H2A | 0.3696 | 0.0632 | 0.2175 | 0.050* | |
C3 | 0.3975 (3) | 0.0471 (3) | 0.14262 (14) | 0.0406 (11) | |
H3A | 0.3554 | 0.1030 | 0.1310 | 0.049* | |
C4 | 0.4585 (3) | −0.0103 (3) | 0.11044 (13) | 0.0340 (10) | |
H4A | 0.4654 | 0.0129 | 0.0768 | 0.041* | |
C5 | 0.4841 (3) | −0.1143 (3) | 0.12119 (13) | 0.0312 (10) | |
C6 | 0.4895 (3) | −0.1372 (3) | 0.17228 (13) | 0.0317 (10) | |
C7 | 0.5148 (3) | −0.2325 (3) | 0.18608 (13) | 0.0357 (11) | |
H7A | 0.5188 | −0.2475 | 0.2191 | 0.043* | |
C8 | 0.5034 (3) | −0.1878 (3) | 0.08783 (13) | 0.0328 (11) | |
H8A | 0.4992 | −0.1723 | 0.0549 | 0.039* | |
C9 | 0.5291 (3) | −0.2855 (3) | 0.10141 (14) | 0.0347 (10) | |
C10 | 0.5349 (3) | −0.3083 (3) | 0.15194 (14) | 0.0353 (10) | |
C11 | 0.5544 (3) | −0.4078 (3) | 0.16562 (16) | 0.0463 (11) | |
H11 | 0.5552 | −0.4243 | 0.1985 | 0.056* | |
C12 | 0.5723 (3) | −0.4807 (3) | 0.13190 (18) | 0.0546 (13) | |
H12A | 0.5846 | −0.5463 | 0.1417 | 0.066* | |
C13 | 0.5719 (3) | −0.4563 (4) | 0.08267 (18) | 0.0560 (14) | |
H13A | 0.5872 | −0.5054 | 0.0598 | 0.067* | |
C14 | 0.5495 (3) | −0.3612 (3) | 0.06738 (15) | 0.0433 (11) | |
H14A | 0.5478 | −0.3467 | 0.0343 | 0.052* | |
C15 | 0.7000 (3) | 0.0552 (3) | 0.16042 (13) | 0.0359 (10) | |
H15A | 0.7317 | −0.0100 | 0.1670 | 0.043* | |
C16 | 0.6616 (3) | 0.1113 (4) | 0.20014 (14) | 0.0471 (13) | |
H16A | 0.6741 | 0.0902 | 0.2338 | 0.056* | |
C17 | 0.6016 (3) | 0.1934 (4) | 0.18996 (17) | 0.0517 (13) | |
H17A | 0.5691 | 0.2330 | 0.2157 | 0.062* | |
C18 | 0.5812 (3) | 0.2105 (3) | 0.14003 (16) | 0.0434 (12) | |
H18A | 0.5263 | 0.2575 | 0.1316 | 0.052* | |
C19 | 0.6563 (3) | 0.1875 (3) | 0.10353 (14) | 0.0324 (11) | |
C20 | 0.7222 (3) | 0.1040 (3) | 0.11462 (13) | 0.0308 (10) | |
C21 | 0.7949 (3) | 0.0757 (3) | 0.08149 (13) | 0.0300 (10) | |
H21A | 0.8382 | 0.0225 | 0.0890 | 0.036* | |
C22 | 0.6683 (3) | 0.2359 (3) | 0.05967 (15) | 0.0375 (11) | |
H22A | 0.6258 | 0.2897 | 0.0524 | 0.045* | |
C23 | 0.7429 (3) | 0.2064 (3) | 0.02550 (14) | 0.0311 (11) | |
C24 | 0.8064 (3) | 0.1245 (3) | 0.03617 (14) | 0.0294 (10) | |
C25 | 0.8818 (3) | 0.0975 (3) | 0.00161 (14) | 0.0383 (11) | |
H25A | 0.9247 | 0.0435 | 0.0081 | 0.046* | |
C26 | 0.8929 (4) | 0.1485 (4) | −0.04079 (15) | 0.0486 (13) | |
H26A | 0.9419 | 0.1279 | −0.0632 | 0.058* | |
C27 | 0.8327 (4) | 0.2301 (4) | −0.05085 (16) | 0.0530 (14) | |
H27A | 0.8427 | 0.2661 | −0.0794 | 0.064* | |
C28 | 0.7575 (4) | 0.2585 (3) | −0.01869 (15) | 0.0463 (12) | |
H28 | 0.7156 | 0.3128 | −0.0261 | 0.056* | |
K1 | 0.03957 (7) | 0.53903 (6) | 0.14969 (3) | 0.0335 (2) | |
O1 | −0.12066 (19) | 0.4278 (2) | 0.18781 (8) | 0.0373 (7) | |
O2 | −0.0500 (2) | 0.59109 (19) | 0.24092 (9) | 0.0443 (7) | |
O3 | 0.1468 (2) | 0.6590 (2) | 0.21494 (9) | 0.0417 (8) | |
O4 | 0.2056 (2) | 0.6488 (2) | 0.11633 (9) | 0.0398 (7) | |
O5 | 0.1262 (2) | 0.49597 (19) | 0.05842 (8) | 0.0378 (7) | |
O6 | −0.0561 (2) | 0.40644 (18) | 0.08827 (9) | 0.0394 (7) | |
C29 | −0.1834 (3) | 0.4796 (3) | 0.22131 (14) | 0.0486 (12) | |
H29A | −0.2346 | 0.4346 | 0.2346 | 0.058* | |
H29B | −0.2185 | 0.5342 | 0.2050 | 0.058* | |
C30 | −0.1184 (3) | 0.5193 (3) | 0.26089 (14) | 0.0446 (12) | |
H30A | −0.1609 | 0.5503 | 0.2856 | 0.054* | |
H30B | −0.0800 | 0.4653 | 0.2759 | 0.054* | |
C31 | 0.0203 (4) | 0.6271 (3) | 0.27595 (15) | 0.0577 (13) | |
H31A | 0.0613 | 0.5722 | 0.2884 | 0.069* | |
H31B | −0.0165 | 0.6570 | 0.3029 | 0.069* | |
C32 | 0.0879 (4) | 0.7032 (3) | 0.25261 (16) | 0.0653 (15) | |
H32A | 0.0463 | 0.7568 | 0.2393 | 0.078* | |
H32B | 0.1333 | 0.7318 | 0.2768 | 0.078* | |
C33 | 0.2139 (3) | 0.7294 (3) | 0.19290 (15) | 0.0485 (13) | |
H33A | 0.2603 | 0.7564 | 0.2172 | 0.058* | |
H33B | 0.1744 | 0.7843 | 0.1794 | 0.058* | |
C34 | 0.2738 (3) | 0.6798 (3) | 0.15356 (15) | 0.0459 (12) | |
H34A | 0.3239 | 0.7262 | 0.1404 | 0.055* | |
H34B | 0.3101 | 0.6223 | 0.1665 | 0.055* | |
C35 | 0.2594 (3) | 0.6084 (3) | 0.07566 (15) | 0.0487 (13) | |
H35A | 0.3005 | 0.5516 | 0.0858 | 0.058* | |
H35B | 0.3047 | 0.6587 | 0.0620 | 0.058* | |
C36 | 0.1829 (3) | 0.5760 (3) | 0.03834 (13) | 0.0429 (11) | |
H36A | 0.1376 | 0.6312 | 0.0302 | 0.051* | |
H36B | 0.2177 | 0.5545 | 0.0090 | 0.051* | |
C37 | 0.0553 (3) | 0.4539 (3) | 0.02498 (12) | 0.0390 (10) | |
H37A | 0.0910 | 0.4309 | −0.0039 | 0.047* | |
H37B | 0.0053 | 0.5038 | 0.0153 | 0.047* | |
C38 | 0.0032 (3) | 0.3683 (3) | 0.04914 (13) | 0.0419 (11) | |
H38A | −0.0408 | 0.3339 | 0.0261 | 0.050* | |
H38B | 0.0535 | 0.3210 | 0.0612 | 0.050* | |
C39 | −0.1043 (3) | 0.3312 (3) | 0.11580 (14) | 0.0431 (11) | |
H39A | −0.0533 | 0.2933 | 0.1337 | 0.052* | |
H39B | −0.1405 | 0.2856 | 0.0944 | 0.052* | |
C40 | −0.1786 (3) | 0.3792 (3) | 0.15067 (15) | 0.0447 (12) | |
H40A | −0.2210 | 0.4275 | 0.1337 | 0.054* | |
H40B | −0.2228 | 0.3287 | 0.1649 | 0.054* | |
O7 | 0.1415 (3) | 0.3777 (3) | 0.18754 (11) | 0.0738 (11) | |
C41 | 0.2195 (4) | 0.3313 (4) | 0.16068 (19) | 0.0842 (17) | |
H41A | 0.2307 | 0.3666 | 0.1303 | 0.101* | |
H41B | 0.2011 | 0.2625 | 0.1534 | 0.101* | |
C42 | 0.3122 (4) | 0.3344 (4) | 0.19089 (17) | 0.0776 (17) | |
H42A | 0.3499 | 0.3963 | 0.1861 | 0.093* | |
H42B | 0.3569 | 0.2781 | 0.1842 | 0.093* | |
C43 | 0.2681 (4) | 0.3285 (5) | 0.24082 (18) | 0.091 (2) | |
H43A | 0.2589 | 0.2595 | 0.2508 | 0.110* | |
H43B | 0.3117 | 0.3623 | 0.2642 | 0.110* | |
C44 | 0.1701 (4) | 0.3792 (4) | 0.23591 (16) | 0.0718 (16) | |
H44A | 0.1187 | 0.3456 | 0.2555 | 0.086* | |
H44B | 0.1760 | 0.4478 | 0.2471 | 0.086* | |
O8 | −0.0901 (3) | 0.6752 (3) | 0.11277 (14) | 0.1021 (15) | |
C45 | −0.1710 (6) | 0.7154 (5) | 0.1368 (2) | 0.147 (3) | |
H45A | −0.2255 | 0.6662 | 0.1395 | 0.176* | |
H45B | −0.1504 | 0.7345 | 0.1694 | 0.176* | |
C46 | −0.2049 (5) | 0.7953 (5) | 0.1129 (3) | 0.105 (2) | |
H46A | −0.1686 | 0.8548 | 0.1234 | 0.126* | |
H46B | −0.2775 | 0.8049 | 0.1188 | 0.126* | |
C47 | −0.1865 (5) | 0.7771 (4) | 0.0613 (2) | 0.097 (2) | |
H47A | −0.1581 | 0.8357 | 0.0453 | 0.116* | |
H47B | −0.2487 | 0.7568 | 0.0446 | 0.116* | |
C48 | −0.1109 (7) | 0.6943 (6) | 0.0635 (2) | 0.195 (5) | |
H48A | −0.1387 | 0.6348 | 0.0481 | 0.234* | |
H48B | −0.0485 | 0.7131 | 0.0467 | 0.234* | |
O9 | 0.1283 (5) | 1.0242 (5) | 0.0337 (2) | 0.074 (3) | 0.561 (8) |
C49 | 0.1160 (9) | 1.0277 (10) | 0.0850 (4) | 0.048 (4) | 0.561 (8) |
H49A | 0.0442 | 1.0360 | 0.0934 | 0.072* | 0.561 (8) |
H49B | 0.1542 | 1.0835 | 0.0985 | 0.072* | 0.561 (8) |
C50 | 0.1548 (17) | 0.9331 (15) | 0.1044 (5) | 0.128 (7) | 0.561 (8) |
H50A | 0.0989 | 0.8883 | 0.1126 | 0.192* | 0.561 (8) |
H50B | 0.1962 | 0.9443 | 0.1333 | 0.192* | 0.561 (8) |
C51 | 0.218 (2) | 0.892 (2) | 0.0643 (13) | 0.118 (12) | 0.561 (8) |
H51A | 0.2861 | 0.8754 | 0.0757 | 0.177* | 0.561 (8) |
H51B | 0.1864 | 0.8316 | 0.0512 | 0.177* | 0.561 (8) |
C52 | 0.2216 (7) | 0.9687 (8) | 0.0283 (4) | 0.068 (3) | 0.561 (8) |
H52A | 0.2262 | 0.9400 | −0.0040 | 0.102* | 0.561 (8) |
H52B | 0.2805 | 1.0117 | 0.0335 | 0.102* | 0.561 (8) |
O10 | 0.0540 (11) | 0.9506 (9) | 0.1099 (4) | 0.112 (4) | 0.439 (8) |
C53 | 0.095 (2) | 1.037 (3) | 0.0972 (11) | 0.169 (16)* | 0.439 (8) |
H53A | 0.1287 | 1.0707 | 0.1241 | 0.254* | 0.439 (8) |
H53B | 0.0461 | 1.0817 | 0.0818 | 0.254* | 0.439 (8) |
C54 | 0.1791 (13) | 0.9867 (11) | 0.0571 (6) | 0.056 (4)* | 0.439 (8) |
H54A | 0.1578 | 1.0026 | 0.0242 | 0.084* | 0.439 (8) |
H54B | 0.2465 | 1.0155 | 0.0623 | 0.084* | 0.439 (8) |
C55 | 0.185 (2) | 0.872 (3) | 0.0633 (11) | 0.066 (8) | 0.439 (8) |
H55A | 0.2372 | 0.8511 | 0.0860 | 0.099* | 0.439 (8) |
H55B | 0.1917 | 0.8368 | 0.0327 | 0.099* | 0.439 (8) |
C56 | 0.0744 (11) | 0.8671 (12) | 0.0848 (5) | 0.094 (5) | 0.439 (8) |
H56A | 0.0251 | 0.8596 | 0.0586 | 0.141* | 0.439 (8) |
H56B | 0.0685 | 0.8093 | 0.1060 | 0.141* | 0.439 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0313 (3) | 0.0510 (4) | 0.0348 (3) | −0.0066 (3) | 0.0057 (3) | −0.0050 (3) |
C1 | 0.034 (3) | 0.052 (3) | 0.023 (2) | 0.003 (3) | 0.0025 (19) | −0.007 (2) |
C2 | 0.042 (3) | 0.041 (3) | 0.041 (3) | −0.009 (2) | 0.006 (2) | −0.003 (2) |
C3 | 0.042 (3) | 0.039 (3) | 0.040 (3) | −0.001 (2) | 0.003 (2) | 0.007 (2) |
C4 | 0.029 (3) | 0.044 (3) | 0.028 (2) | −0.007 (3) | −0.002 (2) | 0.011 (2) |
C5 | 0.019 (3) | 0.047 (3) | 0.028 (2) | −0.008 (2) | 0.0011 (18) | 0.008 (2) |
C6 | 0.021 (2) | 0.044 (3) | 0.030 (2) | −0.0082 (19) | −0.0003 (18) | 0.005 (2) |
C7 | 0.028 (3) | 0.051 (3) | 0.028 (2) | −0.008 (2) | −0.0022 (19) | 0.005 (2) |
C8 | 0.030 (3) | 0.047 (3) | 0.021 (2) | −0.005 (2) | 0.0027 (18) | 0.001 (2) |
C9 | 0.031 (3) | 0.038 (3) | 0.035 (3) | −0.006 (2) | 0.001 (2) | 0.001 (2) |
C10 | 0.020 (2) | 0.039 (3) | 0.047 (3) | 0.002 (2) | 0.000 (2) | 0.015 (2) |
C11 | 0.028 (3) | 0.057 (3) | 0.054 (3) | −0.008 (2) | 0.000 (2) | 0.013 (3) |
C12 | 0.038 (3) | 0.042 (3) | 0.084 (4) | 0.005 (2) | 0.004 (3) | 0.013 (3) |
C13 | 0.042 (3) | 0.056 (4) | 0.069 (3) | −0.001 (3) | 0.012 (2) | −0.012 (3) |
C14 | 0.041 (3) | 0.045 (3) | 0.043 (3) | 0.002 (3) | 0.002 (2) | 0.001 (2) |
C15 | 0.032 (2) | 0.040 (3) | 0.035 (2) | −0.002 (2) | −0.002 (2) | 0.003 (2) |
C16 | 0.040 (3) | 0.073 (4) | 0.029 (3) | −0.010 (3) | 0.007 (2) | 0.006 (2) |
C17 | 0.035 (3) | 0.073 (4) | 0.047 (3) | −0.002 (3) | 0.012 (2) | −0.023 (3) |
C18 | 0.026 (3) | 0.044 (3) | 0.060 (3) | 0.001 (2) | 0.007 (2) | −0.010 (2) |
C19 | 0.035 (3) | 0.030 (3) | 0.033 (3) | −0.009 (2) | 0.001 (2) | −0.011 (2) |
C20 | 0.022 (2) | 0.039 (3) | 0.031 (2) | −0.006 (2) | −0.0011 (19) | −0.006 (2) |
C21 | 0.020 (2) | 0.027 (2) | 0.044 (2) | 0.004 (2) | 0.0037 (19) | −0.006 (2) |
C22 | 0.035 (3) | 0.026 (3) | 0.051 (3) | 0.005 (2) | −0.005 (2) | −0.001 (2) |
C23 | 0.034 (3) | 0.028 (3) | 0.031 (3) | −0.006 (2) | 0.001 (2) | −0.004 (2) |
C24 | 0.028 (3) | 0.027 (3) | 0.034 (2) | −0.008 (2) | 0.004 (2) | −0.005 (2) |
C25 | 0.036 (3) | 0.032 (3) | 0.047 (3) | −0.001 (2) | 0.004 (2) | −0.002 (2) |
C26 | 0.053 (3) | 0.058 (3) | 0.035 (3) | −0.022 (3) | 0.015 (2) | −0.006 (3) |
C27 | 0.069 (4) | 0.057 (4) | 0.033 (3) | −0.025 (3) | 0.006 (3) | 0.012 (3) |
C28 | 0.059 (4) | 0.040 (3) | 0.040 (3) | 0.000 (3) | −0.015 (3) | 0.009 (2) |
K1 | 0.0288 (5) | 0.0366 (5) | 0.0352 (5) | −0.0008 (5) | −0.0023 (4) | −0.0025 (4) |
O1 | 0.0298 (17) | 0.0412 (17) | 0.0408 (15) | −0.0051 (15) | 0.0016 (14) | −0.0076 (15) |
O2 | 0.0363 (19) | 0.0461 (19) | 0.0506 (17) | −0.0129 (17) | 0.0057 (16) | −0.0120 (14) |
O3 | 0.042 (2) | 0.041 (2) | 0.0417 (18) | −0.0060 (16) | 0.0012 (15) | −0.0150 (15) |
O4 | 0.0295 (19) | 0.0456 (19) | 0.0441 (18) | −0.0011 (15) | 0.0018 (15) | −0.0061 (15) |
O5 | 0.0342 (18) | 0.0434 (18) | 0.0357 (15) | −0.0048 (15) | 0.0004 (14) | 0.0001 (14) |
O6 | 0.0381 (19) | 0.0425 (18) | 0.0375 (16) | 0.0005 (16) | 0.0042 (14) | −0.0034 (14) |
C29 | 0.048 (3) | 0.049 (3) | 0.049 (3) | −0.009 (3) | 0.017 (3) | 0.001 (2) |
C30 | 0.034 (3) | 0.051 (3) | 0.049 (3) | 0.000 (3) | 0.005 (2) | −0.012 (2) |
C31 | 0.051 (3) | 0.073 (3) | 0.049 (3) | −0.012 (3) | 0.017 (3) | −0.034 (3) |
C32 | 0.052 (4) | 0.074 (4) | 0.070 (4) | −0.007 (3) | −0.002 (3) | −0.037 (3) |
C33 | 0.041 (3) | 0.052 (3) | 0.052 (3) | −0.018 (3) | −0.015 (3) | 0.002 (3) |
C34 | 0.034 (3) | 0.047 (3) | 0.057 (3) | −0.008 (2) | −0.001 (3) | −0.004 (3) |
C35 | 0.034 (3) | 0.054 (3) | 0.059 (3) | −0.005 (2) | 0.017 (2) | 0.002 (2) |
C36 | 0.043 (3) | 0.046 (3) | 0.039 (2) | 0.002 (3) | 0.014 (2) | 0.005 (2) |
C37 | 0.040 (3) | 0.045 (3) | 0.031 (2) | 0.006 (2) | 0.002 (2) | −0.005 (2) |
C38 | 0.032 (3) | 0.044 (3) | 0.049 (3) | 0.000 (2) | −0.007 (2) | −0.009 (2) |
C39 | 0.036 (3) | 0.041 (3) | 0.052 (3) | −0.013 (2) | −0.008 (2) | −0.010 (3) |
C40 | 0.028 (3) | 0.050 (3) | 0.055 (3) | −0.006 (2) | −0.002 (2) | 0.008 (2) |
O7 | 0.066 (3) | 0.109 (3) | 0.046 (2) | 0.044 (2) | −0.0049 (19) | 0.0008 (19) |
C41 | 0.093 (5) | 0.103 (5) | 0.056 (3) | 0.030 (4) | 0.005 (4) | −0.007 (4) |
C42 | 0.045 (4) | 0.130 (5) | 0.058 (3) | 0.021 (3) | 0.001 (3) | −0.034 (4) |
C43 | 0.072 (5) | 0.139 (6) | 0.063 (4) | 0.047 (4) | −0.010 (3) | −0.012 (4) |
C44 | 0.068 (4) | 0.100 (4) | 0.048 (3) | 0.011 (3) | −0.007 (3) | 0.005 (3) |
O8 | 0.105 (3) | 0.132 (3) | 0.069 (3) | 0.091 (3) | 0.007 (2) | 0.018 (3) |
C45 | 0.210 (9) | 0.127 (7) | 0.104 (6) | 0.107 (6) | 0.051 (6) | 0.044 (5) |
C46 | 0.086 (5) | 0.091 (5) | 0.138 (7) | 0.039 (4) | 0.013 (5) | 0.004 (5) |
C47 | 0.152 (7) | 0.091 (5) | 0.049 (4) | 0.045 (4) | −0.031 (4) | 0.007 (3) |
C48 | 0.290 (11) | 0.207 (9) | 0.088 (6) | 0.195 (8) | 0.016 (6) | 0.016 (5) |
O9 | 0.074 (6) | 0.076 (5) | 0.072 (5) | 0.019 (4) | −0.012 (4) | −0.008 (4) |
C49 | 0.048 (7) | 0.058 (8) | 0.037 (6) | −0.015 (6) | 0.028 (5) | −0.006 (6) |
C50 | 0.148 (19) | 0.148 (17) | 0.088 (11) | −0.058 (15) | −0.015 (11) | 0.071 (12) |
C51 | 0.10 (2) | 0.035 (11) | 0.22 (2) | −0.012 (13) | −0.087 (19) | −0.002 (13) |
C52 | 0.056 (8) | 0.058 (8) | 0.091 (8) | 0.022 (6) | −0.034 (6) | −0.015 (7) |
O10 | 0.106 (11) | 0.084 (8) | 0.146 (9) | 0.006 (8) | 0.012 (8) | −0.025 (7) |
C55 | 0.067 (18) | 0.07 (2) | 0.059 (12) | −0.014 (12) | −0.012 (10) | 0.020 (10) |
C56 | 0.059 (12) | 0.105 (14) | 0.119 (12) | −0.023 (10) | 0.007 (9) | −0.018 (10) |
Co1—C1 | 2.142 (4) | C29—H29A | 0.9700 |
Co1—C2 | 1.997 (4) | C29—H29B | 0.9700 |
Co1—C3 | 1.967 (4) | C30—H30A | 0.9700 |
Co1—C4 | 2.104 (4) | C30—H30B | 0.9700 |
Co1—C15 | 2.105 (4) | C31—C32 | 1.491 (5) |
Co1—C16 | 1.956 (4) | C31—H31A | 0.9700 |
Co1—C17 | 1.993 (4) | C31—H31B | 0.9700 |
Co1—C18 | 2.103 (4) | C32—H32A | 0.9700 |
C1—C2 | 1.393 (5) | C32—H32B | 0.9700 |
C1—C6 | 1.458 (5) | C33—C34 | 1.490 (5) |
C1—H1A | 0.9800 | C33—H33A | 0.9700 |
C2—C3 | 1.415 (5) | C33—H33B | 0.9700 |
C2—H2A | 0.9800 | C34—H34A | 0.9700 |
C3—C4 | 1.415 (5) | C34—H34B | 0.9700 |
C3—H3A | 0.9800 | C35—C36 | 1.495 (5) |
C4—C5 | 1.459 (5) | C35—H35A | 0.9700 |
C4—H4A | 0.9800 | C35—H35B | 0.9700 |
C5—C8 | 1.367 (5) | C36—H36A | 0.9700 |
C5—C6 | 1.439 (5) | C36—H36B | 0.9700 |
C6—C7 | 1.368 (5) | C37—C38 | 1.487 (4) |
C7—C10 | 1.406 (5) | C37—H37A | 0.9700 |
C7—H7A | 0.9300 | C37—H37B | 0.9700 |
C8—C9 | 1.398 (5) | C38—H38A | 0.9700 |
C8—H8A | 0.9300 | C38—H38B | 0.9700 |
C9—C14 | 1.402 (5) | C39—C40 | 1.506 (5) |
C9—C10 | 1.424 (5) | C39—H39A | 0.9700 |
C10—C11 | 1.404 (5) | C39—H39B | 0.9700 |
C11—C12 | 1.365 (5) | C40—H40A | 0.9700 |
C11—H11 | 0.9300 | C40—H40B | 0.9700 |
C12—C13 | 1.392 (5) | O7—C44 | 1.382 (4) |
C12—H12A | 0.9300 | O7—C41 | 1.401 (5) |
C13—C14 | 1.370 (5) | C41—C42 | 1.468 (6) |
C13—H13A | 0.9300 | C41—H41A | 0.9700 |
C14—H14A | 0.9300 | C41—H41B | 0.9700 |
C15—C16 | 1.416 (5) | C42—C43 | 1.490 (6) |
C15—C20 | 1.448 (5) | C42—H42A | 0.9700 |
C15—H15A | 0.9800 | C42—H42B | 0.9700 |
C16—C17 | 1.375 (5) | C43—C44 | 1.453 (6) |
C16—H16A | 0.9800 | C43—H43A | 0.9700 |
C17—C18 | 1.417 (5) | C43—H43B | 0.9700 |
C17—H17A | 0.9800 | C44—H44A | 0.9700 |
C18—C19 | 1.436 (5) | C44—H44B | 0.9700 |
C18—H18A | 0.9800 | O8—C45 | 1.356 (6) |
C19—C22 | 1.377 (5) | O8—C48 | 1.405 (6) |
C19—C20 | 1.441 (5) | C45—C46 | 1.329 (6) |
C20—C21 | 1.368 (4) | C45—H45A | 0.9700 |
C21—C24 | 1.414 (5) | C45—H45B | 0.9700 |
C21—H21A | 0.9300 | C46—C47 | 1.460 (6) |
C22—C23 | 1.409 (5) | C46—H46A | 0.9700 |
C22—H22A | 0.9300 | C46—H46B | 0.9700 |
C23—C24 | 1.403 (5) | C47—C48 | 1.482 (7) |
C23—C28 | 1.413 (5) | C47—H47A | 0.9700 |
C24—C25 | 1.414 (5) | C47—H47B | 0.9700 |
C25—C26 | 1.358 (5) | C48—H48A | 0.9700 |
C25—H25A | 0.9300 | C48—H48B | 0.9700 |
C26—C27 | 1.372 (6) | O9—C49 | 1.422 (13) |
C26—H26A | 0.9300 | O9—C52 | 1.433 (11) |
C27—C28 | 1.374 (6) | C49—C50 | 1.46 (2) |
C27—H27A | 0.9300 | C49—H49A | 0.9700 |
C28—H28 | 0.9300 | C49—H49B | 0.9700 |
K1—O8 | 2.683 (3) | C50—C51 | 1.48 (4) |
K1—O7 | 2.738 (3) | C50—H50A | 0.9700 |
K1—O6 | 2.746 (2) | C50—H50B | 0.9700 |
K1—O1 | 2.770 (3) | C51—C52 | 1.43 (3) |
K1—O4 | 2.771 (3) | C51—H51A | 0.9700 |
K1—O3 | 2.782 (3) | C51—H51B | 0.9700 |
K1—O5 | 2.811 (2) | C52—H52A | 0.9700 |
K1—O2 | 2.853 (3) | C52—H52B | 0.9700 |
O1—C40 | 1.426 (4) | O10—C53 | 1.32 (3) |
O1—C29 | 1.413 (4) | O10—C56 | 1.340 (16) |
O2—C30 | 1.420 (4) | C53—C54 | 1.69 (3) |
O2—C31 | 1.414 (4) | C53—H53A | 0.9700 |
O3—C32 | 1.418 (4) | C53—H53B | 0.9700 |
O3—C33 | 1.420 (4) | C54—C55 | 1.54 (4) |
O4—C34 | 1.419 (4) | C54—H54A | 0.9700 |
O4—C35 | 1.426 (4) | C54—H54B | 0.9700 |
O5—C36 | 1.413 (4) | C55—C56 | 1.56 (3) |
O5—C37 | 1.419 (4) | C55—H55A | 0.9700 |
O6—C38 | 1.419 (4) | C55—H55B | 0.9700 |
O6—C39 | 1.406 (4) | C56—H56A | 0.9700 |
C29—C30 | 1.477 (5) | C56—H56B | 0.9700 |
C16—Co1—C3 | 164.10 (19) | C36—O5—K1 | 113.8 (2) |
C16—Co1—C17 | 40.74 (16) | C37—O5—K1 | 113.4 (2) |
C3—Co1—C17 | 127.3 (2) | C39—O6—C38 | 113.3 (3) |
C16—Co1—C2 | 127.78 (16) | C39—O6—K1 | 109.4 (2) |
C3—Co1—C2 | 41.83 (14) | C38—O6—K1 | 116.8 (2) |
C17—Co1—C2 | 118.14 (17) | O1—C29—C30 | 108.9 (3) |
C16—Co1—C18 | 71.10 (17) | O1—C29—H29A | 109.9 |
C3—Co1—C18 | 105.48 (17) | C30—C29—H29A | 109.9 |
C17—Co1—C18 | 40.36 (15) | O1—C29—H29B | 109.9 |
C2—Co1—C18 | 128.11 (17) | C30—C29—H29B | 109.9 |
C16—Co1—C4 | 155.38 (18) | H29A—C29—H29B | 108.3 |
C3—Co1—C4 | 40.52 (14) | O2—C30—C29 | 108.5 (3) |
C17—Co1—C4 | 150.03 (18) | O2—C30—H30A | 110.0 |
C2—Co1—C4 | 71.89 (16) | C29—C30—H30A | 110.0 |
C18—Co1—C4 | 110.26 (16) | O2—C30—H30B | 110.0 |
C16—Co1—C15 | 40.61 (15) | C29—C30—H30B | 110.0 |
C3—Co1—C15 | 155.14 (16) | H30A—C30—H30B | 108.4 |
C17—Co1—C15 | 71.30 (16) | O2—C31—C32 | 108.8 (4) |
C2—Co1—C15 | 150.74 (17) | O2—C31—H31A | 109.9 |
C18—Co1—C15 | 78.04 (16) | C32—C31—H31A | 109.9 |
C4—Co1—C15 | 114.81 (15) | O2—C31—H31B | 109.9 |
C16—Co1—C1 | 107.61 (16) | C32—C31—H31B | 109.9 |
C3—Co1—C1 | 70.99 (15) | H31A—C31—H31B | 108.3 |
C17—Co1—C1 | 128.51 (17) | O3—C32—C31 | 110.5 (3) |
C2—Co1—C1 | 39.14 (14) | O3—C32—H32A | 109.5 |
C18—Co1—C1 | 163.30 (15) | C31—C32—H32A | 109.5 |
C4—Co1—C1 | 78.10 (13) | O3—C32—H32B | 109.5 |
C15—Co1—C1 | 112.28 (16) | C31—C32—H32B | 109.5 |
C2—C1—C6 | 120.6 (3) | H32A—C32—H32B | 108.1 |
C2—C1—Co1 | 64.8 (2) | O3—C33—C34 | 109.8 (3) |
C6—C1—Co1 | 101.1 (2) | O3—C33—H33A | 109.7 |
C2—C1—H1A | 118.4 | C34—C33—H33A | 109.7 |
C6—C1—H1A | 118.4 | O3—C33—H33B | 109.7 |
Co1—C1—H1A | 118.4 | C34—C33—H33B | 109.7 |
C1—C2—C3 | 116.7 (4) | H33A—C33—H33B | 108.2 |
C1—C2—Co1 | 76.1 (3) | O4—C34—C33 | 108.9 (3) |
C3—C2—Co1 | 68.0 (2) | O4—C34—H34A | 109.9 |
C1—C2—H2A | 121.6 | C33—C34—H34A | 109.9 |
C3—C2—H2A | 121.6 | O4—C34—H34B | 109.9 |
Co1—C2—H2A | 121.6 | C33—C34—H34B | 109.9 |
C4—C3—C2 | 116.6 (4) | H34A—C34—H34B | 108.3 |
C4—C3—Co1 | 74.9 (2) | O4—C35—C36 | 108.6 (3) |
C2—C3—Co1 | 70.2 (2) | O4—C35—H35A | 110.0 |
C4—C3—H3A | 121.6 | C36—C35—H35A | 110.0 |
C2—C3—H3A | 121.6 | O4—C35—H35B | 110.0 |
Co1—C3—H3A | 121.6 | C36—C35—H35B | 110.0 |
C3—C4—C5 | 121.2 (3) | H35A—C35—H35B | 108.4 |
C3—C4—Co1 | 64.6 (2) | O5—C36—C35 | 107.5 (3) |
C5—C4—Co1 | 102.1 (2) | O5—C36—H36A | 110.2 |
C3—C4—H4A | 118.1 | C35—C36—H36A | 110.2 |
C5—C4—H4A | 118.1 | O5—C36—H36B | 110.2 |
Co1—C4—H4A | 118.1 | C35—C36—H36B | 110.2 |
C8—C5—C6 | 119.5 (4) | H36A—C36—H36B | 108.5 |
C8—C5—C4 | 126.2 (3) | O5—C37—C38 | 108.2 (3) |
C6—C5—C4 | 114.3 (3) | O5—C37—H37A | 110.1 |
C7—C6—C5 | 118.7 (3) | C38—C37—H37A | 110.1 |
C7—C6—C1 | 125.4 (3) | O5—C37—H37B | 110.1 |
C5—C6—C1 | 115.8 (4) | C38—C37—H37B | 110.1 |
C6—C7—C10 | 122.0 (3) | H37A—C37—H37B | 108.4 |
C6—C7—H7A | 119.0 | O6—C38—C37 | 108.2 (3) |
C10—C7—H7A | 119.0 | O6—C38—H38A | 110.1 |
C5—C8—C9 | 122.4 (3) | C37—C38—H38A | 110.1 |
C5—C8—H8A | 118.8 | O6—C38—H38B | 110.1 |
C9—C8—H8A | 118.8 | C37—C38—H38B | 110.1 |
C8—C9—C14 | 122.6 (3) | H38A—C38—H38B | 108.4 |
C8—C9—C10 | 118.2 (3) | O6—C39—C40 | 109.1 (3) |
C14—C9—C10 | 119.2 (4) | O6—C39—K1 | 48.14 (16) |
C11—C10—C7 | 122.4 (4) | C40—C39—K1 | 80.6 (2) |
C11—C10—C9 | 118.2 (4) | O6—C39—H39A | 109.9 |
C7—C10—C9 | 119.2 (3) | C40—C39—H39A | 109.9 |
C12—C11—C10 | 121.6 (4) | K1—C39—H39A | 84.9 |
C12—C11—H11 | 119.2 | O6—C39—H39B | 109.9 |
C10—C11—H11 | 119.2 | C40—C39—H39B | 109.9 |
C11—C12—C13 | 119.5 (4) | K1—C39—H39B | 157.9 |
C11—C12—H12A | 120.3 | H39A—C39—H39B | 108.3 |
C13—C12—H12A | 120.3 | O1—C40—C39 | 108.0 (3) |
C14—C13—C12 | 121.1 (4) | O1—C40—H40A | 110.1 |
C14—C13—H13A | 119.5 | C39—C40—H40A | 110.1 |
C12—C13—H13A | 119.5 | O1—C40—H40B | 110.1 |
C13—C14—C9 | 120.2 (4) | C39—C40—H40B | 110.1 |
C13—C14—H14A | 119.9 | H40A—C40—H40B | 108.4 |
C9—C14—H14A | 119.9 | C44—O7—C41 | 108.5 (4) |
C16—C15—C20 | 120.2 (4) | C44—O7—K1 | 119.1 (3) |
C16—C15—Co1 | 64.0 (2) | C41—O7—K1 | 120.0 (3) |
C20—C15—Co1 | 102.5 (2) | O7—C41—C42 | 106.7 (4) |
C16—C15—H15A | 118.5 | O7—C41—H41A | 110.4 |
C20—C15—H15A | 118.5 | C42—C41—H41A | 110.4 |
Co1—C15—H15A | 118.5 | O7—C41—H41B | 110.4 |
C17—C16—C15 | 117.8 (4) | C42—C41—H41B | 110.4 |
C17—C16—Co1 | 71.1 (3) | H41A—C41—H41B | 108.6 |
C15—C16—Co1 | 75.3 (2) | C41—C42—C43 | 101.6 (4) |
C17—C16—H16A | 121.1 | C41—C42—H42A | 111.4 |
C15—C16—H16A | 121.1 | C43—C42—H42A | 111.4 |
Co1—C16—H16A | 121.1 | C41—C42—H42B | 111.4 |
C16—C17—C18 | 115.7 (4) | C43—C42—H42B | 111.4 |
C16—C17—Co1 | 68.2 (3) | H42A—C42—H42B | 109.3 |
C18—C17—Co1 | 74.0 (3) | C44—C43—C42 | 103.2 (4) |
C16—C17—H17A | 122.0 | C44—C43—H43A | 111.1 |
C18—C17—H17A | 122.0 | C42—C43—H43A | 111.1 |
Co1—C17—H17A | 122.0 | C44—C43—H43B | 111.1 |
C17—C18—C19 | 120.9 (4) | C42—C43—H43B | 111.1 |
C17—C18—Co1 | 65.6 (3) | H43A—C43—H43B | 109.1 |
C19—C18—Co1 | 102.1 (3) | O7—C44—C43 | 108.7 (4) |
C17—C18—H18A | 118.0 | O7—C44—H44A | 110.0 |
C19—C18—H18A | 118.0 | C43—C44—H44A | 110.0 |
Co1—C18—H18A | 118.0 | O7—C44—H44B | 110.0 |
C22—C19—C18 | 126.1 (4) | C43—C44—H44B | 110.0 |
C22—C19—C20 | 118.7 (4) | H44A—C44—H44B | 108.3 |
C18—C19—C20 | 115.1 (4) | C45—O8—C48 | 104.4 (5) |
C21—C20—C19 | 119.1 (4) | C45—O8—K1 | 125.1 (4) |
C21—C20—C15 | 126.4 (4) | C48—O8—K1 | 127.6 (4) |
C19—C20—C15 | 114.4 (3) | C46—C45—O8 | 109.6 (6) |
C20—C21—C24 | 122.2 (4) | C46—C45—H45A | 109.8 |
C20—C21—H21A | 118.9 | O8—C45—H45A | 109.8 |
C24—C21—H21A | 118.9 | C46—C45—H45B | 109.8 |
C19—C22—C23 | 122.1 (4) | O8—C45—H45B | 109.8 |
C19—C22—H22A | 118.9 | H45A—C45—H45B | 108.2 |
C23—C22—H22A | 118.9 | C45—C46—C47 | 107.0 (5) |
C24—C23—C22 | 119.1 (4) | C45—C46—H46A | 110.3 |
C24—C23—C28 | 119.0 (4) | C47—C46—H46A | 110.3 |
C22—C23—C28 | 121.9 (4) | C45—C46—H46B | 110.3 |
C23—C24—C25 | 118.0 (4) | C47—C46—H46B | 110.3 |
C23—C24—C21 | 118.8 (4) | H46A—C46—H46B | 108.6 |
C25—C24—C21 | 123.2 (4) | C46—C47—C48 | 101.1 (5) |
C26—C25—C24 | 121.5 (4) | C46—C47—H47A | 111.5 |
C26—C25—H25A | 119.2 | C48—C47—H47A | 111.5 |
C24—C25—H25A | 119.2 | C46—C47—H47B | 111.5 |
C25—C26—C27 | 120.7 (4) | C48—C47—H47B | 111.5 |
C25—C26—H26A | 119.7 | H47A—C47—H47B | 109.4 |
C27—C26—H26A | 119.7 | O8—C48—C47 | 107.7 (5) |
C26—C27—C28 | 119.9 (4) | O8—C48—H48A | 110.2 |
C26—C27—H27A | 120.0 | C47—C48—H48A | 110.2 |
C28—C27—H27A | 120.0 | O8—C48—H48B | 110.2 |
C27—C28—C23 | 120.9 (4) | C47—C48—H48B | 110.2 |
C27—C28—H28 | 119.6 | H48A—C48—H48B | 108.5 |
C23—C28—H28 | 119.6 | C49—O9—C52 | 102.5 (8) |
O8—K1—O7 | 169.58 (13) | O9—C49—C50 | 107.1 (12) |
O8—K1—O6 | 85.30 (11) | O9—C49—H49A | 110.3 |
O7—K1—O6 | 86.94 (9) | C50—C49—H49A | 110.3 |
O8—K1—O1 | 91.78 (11) | O9—C49—H49B | 110.3 |
O7—K1—O1 | 78.47 (9) | C50—C49—H49B | 110.3 |
O6—K1—O1 | 62.88 (8) | H49A—C49—H49B | 108.5 |
O8—K1—O4 | 90.50 (11) | C49—C50—C51 | 104.1 (17) |
O7—K1—O4 | 99.38 (9) | C49—C50—H50A | 110.9 |
O6—K1—O4 | 119.50 (8) | C51—C50—H50A | 110.9 |
O1—K1—O4 | 176.85 (8) | C49—C50—H50B | 110.9 |
O8—K1—O3 | 99.82 (11) | C51—C50—H50B | 110.9 |
O7—K1—O3 | 87.94 (9) | H50A—C50—H50B | 109.0 |
O6—K1—O3 | 174.87 (8) | C52—C51—C50 | 105 (2) |
O1—K1—O3 | 116.37 (8) | C52—C51—H51A | 110.7 |
O4—K1—O3 | 61.05 (8) | C50—C51—H51A | 110.7 |
O8—K1—O5 | 93.11 (10) | C52—C51—H51B | 110.7 |
O7—K1—O5 | 89.04 (9) | C50—C51—H51B | 110.7 |
O6—K1—O5 | 60.12 (8) | H51A—C51—H51B | 108.8 |
O1—K1—O5 | 122.08 (8) | C51—C52—O9 | 105.7 (17) |
O4—K1—O5 | 59.92 (8) | C51—C52—H52A | 110.6 |
O3—K1—O5 | 119.43 (9) | O9—C52—H52A | 110.6 |
O8—K1—O2 | 84.79 (10) | C51—C52—H52B | 110.6 |
O7—K1—O2 | 93.24 (9) | O9—C52—H52B | 110.6 |
O6—K1—O2 | 120.77 (9) | H52A—C52—H52B | 108.7 |
O1—K1—O2 | 59.27 (8) | C53—O10—C56 | 120.7 (16) |
O4—K1—O2 | 118.82 (8) | O10—C53—C54 | 95.1 (19) |
O3—K1—O2 | 59.92 (8) | O10—C53—H53A | 112.7 |
O5—K1—O2 | 177.58 (8) | C54—C53—H53A | 112.7 |
O8—K1—C39 | 95.71 (12) | O10—C53—H53B | 112.7 |
O7—K1—C39 | 74.66 (11) | C54—C53—H53B | 112.7 |
O6—K1—C39 | 22.42 (7) | H53A—C53—H53B | 110.2 |
O1—K1—C39 | 42.80 (8) | C55—C54—C53 | 111 (2) |
O4—K1—C39 | 139.04 (9) | C55—C54—H54A | 109.5 |
O3—K1—C39 | 154.63 (9) | C53—C54—H54A | 109.5 |
O5—K1—C39 | 79.30 (9) | C55—C54—H54B | 109.5 |
O2—K1—C39 | 102.07 (9) | C53—C54—H54B | 109.5 |
C29—O1—C40 | 112.5 (3) | H54A—C54—H54B | 108.1 |
C29—O1—K1 | 114.9 (2) | C54—C55—C56 | 92 (2) |
C40—O1—K1 | 111.9 (2) | C54—C55—H55A | 113.2 |
C31—O2—C30 | 111.9 (3) | C56—C55—H55A | 113.2 |
C31—O2—K1 | 114.6 (2) | C54—C55—H55B | 113.2 |
C30—O2—K1 | 115.6 (2) | C56—C55—H55B | 113.2 |
C32—O3—C33 | 111.7 (3) | H55A—C55—H55B | 110.6 |
C32—O3—K1 | 116.0 (2) | O10—C56—C55 | 110.1 (16) |
C33—O3—K1 | 114.6 (2) | O10—C56—H56A | 109.7 |
C34—O4—C35 | 111.5 (3) | C55—C56—H56A | 109.7 |
C34—O4—K1 | 114.0 (2) | O10—C56—H56B | 109.7 |
C35—O4—K1 | 116.4 (2) | C55—C56—H56B | 109.7 |
C36—O5—C37 | 112.8 (3) | H56A—C56—H56B | 108.2 |
C1—C2—C3—C4 | 0.3 (6) | C18—C19—C22—C23 | −178.4 (4) |
C6—C1—C2—C3 | −32.1 (5) | C20—C19—C22—C23 | −0.1 (6) |
C2—C3—C4—C5 | 30.9 (6) | C19—C22—C23—C24 | 0.7 (6) |
Co1—C1—C2—C3 | 56.2 (3) | C19—C22—C23—C28 | −177.6 (4) |
Co1—C2—C3—C4 | 60.7 (3) | C22—C23—C24—C25 | −179.0 (4) |
C1—C2—C3—Co1 | −60.4 (3) | C28—C23—C24—C25 | −0.6 (5) |
C2—C3—C4—Co1 | −58.2 (3) | C22—C23—C24—C21 | −1.5 (5) |
C6—C1—C2—Co1 | −88.2 (3) | C28—C23—C24—C21 | 176.9 (4) |
Co1—C3—C4—C5 | 89.1 (4) | C20—C21—C24—C23 | 1.8 (6) |
C2—C1—C6—C5 | 32.8 (5) | C20—C21—C24—C25 | 179.2 (4) |
C3—C4—C5—C6 | −29.3 (5) | C23—C24—C25—C26 | −0.1 (6) |
C2—C1—C6—C7 | −150.6 (4) | C21—C24—C25—C26 | −177.6 (4) |
C3—C4—C5—C8 | 151.3 (4) | C24—C25—C26—C27 | 1.7 (6) |
C4—C5—C6—C1 | −2.0 (5) | C25—C26—C27—C28 | −2.5 (7) |
C8—C5—C6—C7 | 0.6 (5) | C26—C27—C28—C23 | 1.8 (7) |
C4—C5—C6—C7 | −178.9 (3) | C24—C23—C28—C27 | −0.2 (6) |
C8—C5—C6—C1 | 177.4 (3) | C22—C23—C28—C27 | 178.2 (4) |
C5—C6—C7—C10 | −0.4 (5) | C40—O1—C29—C30 | 174.6 (3) |
C1—C6—C7—C10 | −177.0 (4) | C31—O2—C30—C29 | −175.5 (3) |
C6—C5—C8—C9 | −0.5 (6) | O1—C29—C30—O2 | 64.4 (4) |
C4—C5—C8—C9 | 178.9 (4) | C30—O2—C31—C32 | −178.9 (3) |
C5—C8—C9—C14 | −179.6 (4) | C33—O3—C32—C31 | −178.5 (4) |
C5—C8—C9—C10 | 0.2 (6) | O2—C31—C32—O3 | −63.1 (5) |
C6—C7—C10—C11 | −175.8 (4) | C32—O3—C33—C34 | −179.8 (3) |
C6—C7—C10—C9 | 0.2 (6) | C35—O4—C34—C33 | 175.0 (3) |
C8—C9—C10—C11 | 176.1 (4) | O3—C33—C34—O4 | 64.6 (4) |
C14—C9—C10—C11 | −4.0 (6) | C34—O4—C35—C36 | 179.2 (3) |
C8—C9—C10—C7 | −0.1 (6) | C37—O5—C36—C35 | −175.9 (3) |
C14—C9—C10—C7 | 179.8 (4) | O4—C35—C36—O5 | −65.6 (4) |
C7—C10—C11—C12 | 179.0 (4) | C36—O5—C37—C38 | 177.8 (3) |
C9—C10—C11—C12 | 3.0 (6) | C39—O6—C38—C37 | −176.4 (3) |
C10—C11—C12—C13 | 0.4 (6) | O5—C37—C38—O6 | 65.3 (4) |
C11—C12—C13—C14 | −2.9 (6) | C38—O6—C39—C40 | −170.6 (3) |
C12—C13—C14—C9 | 1.8 (7) | C29—O1—C40—C39 | 177.1 (3) |
C8—C9—C14—C13 | −178.4 (4) | O6—C39—C40—O1 | −72.0 (4) |
C10—C9—C14—C13 | 1.7 (6) | C44—O7—C41—C42 | −18.9 (6) |
C15—C16—C17—C18 | 2.5 (6) | O7—C41—C42—C43 | 31.5 (6) |
C20—C15—C16—C17 | 30.8 (6) | C41—C42—C43—C44 | −31.8 (6) |
C16—C17—C18—C19 | −34.3 (6) | C41—O7—C44—C43 | −2.3 (6) |
Co1—C15—C16—C17 | −58.9 (4) | C42—C43—C44—O7 | 22.0 (6) |
Co1—C16—C17—C18 | −58.6 (4) | C48—O8—C45—C46 | −32.4 (8) |
C15—C16—C17—Co1 | 61.1 (3) | O8—C45—C46—C47 | 31.7 (9) |
C16—C17—C18—Co1 | 55.5 (3) | C45—C46—C47—C48 | −17.0 (8) |
C20—C15—C16—Co1 | 89.7 (3) | C45—O8—C48—C47 | 20.0 (8) |
Co1—C17—C18—C19 | −89.8 (4) | C46—C47—C48—O8 | −2.1 (8) |
C16—C15—C20—C19 | −32.2 (5) | C52—O9—C49—C50 | −34.7 (11) |
C17—C18—C19—C20 | 31.7 (5) | O9—C49—C50—C51 | 17.2 (18) |
C16—C15—C20—C21 | 150.7 (4) | C49—C50—C51—C52 | 7 (2) |
C17—C18—C19—C22 | −149.9 (4) | C50—C51—C52—O9 | −29 (2) |
C18—C19—C20—C15 | 1.5 (5) | C49—O9—C52—C51 | 39.4 (15) |
C22—C19—C20—C21 | 0.4 (5) | C56—O10—C53—C54 | −11 (3) |
C18—C19—C20—C21 | 178.8 (3) | O10—C53—C54—C55 | −13 (3) |
C22—C19—C20—C15 | −177.0 (3) | C53—C54—C55—C56 | 26 (2) |
C19—C20—C21—C24 | −1.2 (6) | C53—O10—C56—C55 | 31 (3) |
C15—C20—C21—C24 | 175.8 (3) | C54—C55—C56—O10 | −32 (2) |
Experimental details
Crystal data | |
Chemical formula | [K(C12H24O6)(C4H8O)2][Co(C14H10)2]·C4H8O |
Mr | 935.09 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 150 |
a, b, c (Å) | 13.0428 (10), 13.3557 (10), 27.4939 (17) |
V (Å3) | 4789.3 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.50 |
Crystal size (mm) | 0.6 × 0.3 × 0.05 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur 3 |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.787, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 62002, 9364, 4717 |
Rint | 0.105 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.076, 0.77 |
No. of reflections | 9364 |
No. of parameters | 604 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.96, −0.37 |
Absolute structure | Flack (1983), 4164 Friedel pairs |
Absolute structure parameter | −0.005 (14) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2012).
Acknowledgements
This work was supported by the Deutsche Forschungsgemeinschaft. HH thanks the Chinese Scholarship Council for support.
References
Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Brennessel, W. W. & Ellis, J. E. (2012). Inorg. Chem. 51, 9076–9094. Web of Science CSD CrossRef CAS PubMed Google Scholar
Brennessel, W. W., Ellis, J. E., Pomije, M. K., Sussman, V. J., Urnezius, E. & Young, V. G. Jr (2002). J. Am. Chem. Soc. 124, 10258–10259. Web of Science CSD CrossRef PubMed CAS Google Scholar
Brennessel, W. W., Ellis, J. E., Roush, S. N., Strandberg, B. R., Woisetschläger, O. E. & Young, V. G. Jr (2002). Chem. Commun. pp. 2356–2357. Web of Science CSD CrossRef Google Scholar
Brennessel, W. W., Jilek, R. E. & Ellis, J. E. (2007). Angew. Chem. Int. Ed. 46, 6132–6136. Web of Science CSD CrossRef CAS Google Scholar
Brennessel, W. W., Young, V. G. Jr & Ellis, J. E. (2002). Angew. Chem. Int. Ed. 41, 1211–1215. CrossRef CAS Google Scholar
Elschenbroich, C., Möckel, R. & Bilger, L. (1984). Z. Naturforsch. Teil B, 39, 375–383. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Hanic, F. & Mills, O. S. (1968). J. Organomet. Chem. 11, 151–158. CSD CrossRef CAS Web of Science Google Scholar
Jilek, R. E., Jang, M., Smolensky, E. D., Britton, J. D. & Ellis, J. E. (2008). Angew. Chem. Int. Ed. 47, 8692–8695. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Scharfe, S., Kraus, F., Stegmaier, S., Schier, A. & Fässler, T. F. (2011). Angew. Chem. Int. Ed. 50, 3630–3670. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Veauthier, J. M., Chow, A., Fraenkel, G., Geib, S. J. & Cooper, N. J. (2000). Organometallics, 19, 661–671. Web of Science CSD CrossRef CAS Google Scholar
Wang, J. Q. & Fässler, T. F. (2009). Z. Naturforsch. Teil B, 64, 985–988. CAS Google Scholar
Woolf, A., Chaplin, A. B., McGrady, J. E., Alibadi, M. A. M., Rees, N., Draper, S., Murphy, F. & Weller, A. S. (2011). Eur. J. Inorg. Chem. pp. 1614–1625. Web of Science CSD CrossRef Google Scholar
Zhu, G., Janak, K. E., Figueroa, J. S. & Parkin, G. (2006). J. Am. Chem. Soc. 128, 5452–5461. Web of Science CSD CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Organometallic compounds with transition metals in a low oxidation state are important precursors for the formation of intermetalloid clusters from Zintl anions (Scharfe et al., 2011). Transition metal complexes with polycyclic aromatic hydrocarbons as ligands can serve as storable, but reactive sources of low-valent metal atoms or even anions (Brennessel & Ellis, 2012). Within this group of compounds, anthracene has been found as a prominent, sometimes favoured ligand (Zhu et al., 2006), which can act as a η2 (Woolf et al., 2011), η4, and η6 (Hanic & Mills, 1968; Elschenbroich et al., 1984), in its monohydrogenated form even as a η5 (Veauthier et al., 2000) ligand. Regarding the entries of the Cambridge Structural Database (Allen, 2002), it is interesting that homoleptic anthracene complexes have been obtained exclusively with η4 coordination of the transition metals Ti, Zr, Hf (Jilek et al., 2008), Nb (Brennessel, Ellis, Roush et al., 2002), Ta (Brennessel, Ellis, Pomije et al., 2002), Fe ((Brennessel et al., 2007), and Co (Brennessel, Young & Ellis, 2002).
The title compound was obtained via reduction of CoBr2 by potassium anthracene in THF. Although the reaction conditions were very similar to those described by Brennessel, Young & Ellis (2002), we found the compound to crystallize including an additional free solvent molecule (Fig.1). Consequently different from the literature, our indexation resulted in the orthorhombic, but acentric space group P212121 instead of P1. Besides these differences, those structural entities, which are present in both compounds, show almost the same shape (Fig.2).
The Co atom is sandwiched by two anthracene molecules in 1,2,3,4-η4 coordination, respectively, with a slight tilt of 10.2° for the two planes formed by the respective coordinating atoms C1—C4. The C6 rings, which are directly bond to the Co atom, are in eclipsed position, but the main molecule axes form an angle of about 65°. The anthracene molecules are folded at an axis running through the C1 and C4 atoms, the angles between the planes formed by C1, C2, C3, and C4 and by C1, and C4—C14 are almost identical (29.18° and 28.99° for both molecules).