metal-organic compounds
Lithiation of the diaminopyridine protio-ligand MeC(2-C5H4N){CH2N(H)Mes}2 (Mes = 2,4,6-C6H2Me3)
aChemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England, and bInstitut für Anorganische Chemie, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
*Correspondence e-mail: philip.mountford@chem.ox.ac.uk
Reaction of the diamidopyridine protio-ligand MeC(2-C5H4N){CH2N(H)Mes}2 (Mes = 2,4,6-C6H2Me3) with butyllithium in diethyl ether affords the compound (diethyl ether)(μ4-2-{6-[1,3-dimethyl-3-(2-pyridyl)-1,4-bis(2,4,6-trimethylanilinio)butyl]-2-pyridyl}-2-methyl-1,3-bis(2,4,6-trimethylanilinio)propane)tetralithium(I), [Li4(C55H64N6)(C4H10O)] or Li4[MeC(2-C5H4N){CH2N(Mes)}CHN(2,4,6-C6H2-Me2C(Me)(2,2′-C5H3N){C(Me)}(CH2NMes)2](OEt2), which shows the methylation of the pyridyl ortho-position with a methyl group of one of the mesityl groups. The complex contains four Li atoms, each of which is chemically distinct. The tetraanionic ligand contains two protio-ligand units which are fused together into a single entity. The structure contains two disordered molecules of diethyl ether, one of which is coordinated to one of the Li atoms.
Comment
Diamidopyridine ligands of the general formula [MeC(C5H4N)(CH2NR)2]2− (R = silyl or aryl) have found a variety of uses in early transition metal chemistry and catalysis over the last decade (Gade & Mountford, 2001; Mehrkhodavandi et al., 2000). Whereas the silylated derivatives (R = SiMe3 or SiMe2tBu) are known as their dilithium salts (Friedrich et al., 1997), the corresponding N-arylated derivatives (R = 3,5-C6H3Cl2, 4-C6H4Me or 2,4,6-C6H2Me3) have remained elusive. In attempting to prepare such complexes in our laboratories, we have consistently observed degradation products, and we report here the structural characterization of a product, (I), arising from the reaction of the mesityl protio-ligand (Mehrkhodavandi et al., 2000) with butyllithium in diethyl ether.
The tetralithium complex, (I), crystallizes in P, and contains four Li environments which each occupy chemically different sites within the molecule. The Li atoms are arranged in two pairs, each occupying a bridging position between two amide N atoms. Each pair of Li atoms is capped at one end by a pyridyl group. At the other end, one pair of Li atoms is capped by one of the mesityl groups bonding in an η3 mode. The second pair is capped by a molecule of diethyl ether coordinated to one of the Li centres; one of the ethyl groups of this ligand was found to be disordered over two sites. The disorder was modelled by using an occupancy of 0.5 for each atom within the ethyl group for each of the two sites.
The structure clearly does not represent a stoichiometric dimerization of the dilithium compound, since it contains an `extra' methyl group (C29). The presence of this methyl group suggests that the structure arises from the rearrangement of three diamidopyridine units. The mechanistic details behind this rearrangement are not clear, and no other well defined product could be obtained from the reaction mixture. The structure also contains a disordered non-coordinated molecule of diethyl ether.
Experimental
The diaminopyridine protio-ligand MeC(2-C5H4N){CH2N(H)Mes}2 (0.50 g, 1.25 mmol) was dissolved in diethyl ether (20 ml) and cooled to 195 K, followed by the dropwise addition of butyllithium (1.56 ml of a 1.6 M solution in hexanes, 2.50 mmol, 2 equivalents). The colourless solution immediately turned bright yellow, and the reaction was allowed to warm slowly to ambient temperature and stirred for 1 h. The reaction mixture was concentrated to 5 ml, and crystals of (I) suitable for X-ray diffraction were formed on allowing the mixture to stand overnight.
Crystal data
|
Data collection
Refinement
The crystal was a weak diffractor. Although sufficient data were collected, the number of data with I > 3σ(I) was low. It is therefore inappropriate to compare bond lengths and angles with structures of higher precision, although the connectivity is thought to be reliable. The Comment has been written to take this into account.
The structure contains a coordinated molecule of diethyl ether, of which one ethyl group was disordered over two sites. The disorder was modelled with each C atom given 0.5 occupancy.
The i.e. the central region of the difference electron density phased on all the non-ether atoms was occupied by a `split' O atom. This model needed geometric restraints and led to atoms falling on regions of relatively low electron density. of the unrestrained isotropic displacement parameters led to unacceptable values. A second model displaced the ether molecule sideways along its longest axis, so that the central region of the difference-density map now contained a disordered O and C atom. This model also needed restraints, gave a similar R factor to the previous model, and also gave a poor (but different) fit to the difference density. An unrestrained model gave a good fit to the density, but unacceptable distances and angles. Based on this evidence, it was felt that an atomic model was unsuitable. The disordered region was modelled using SQUEEZE (van der Sluis & Spek, 1990) in its advanced mode, in which the A and B parts of the are passed back to CRYSTALS (Betteridge et al., 2003) for inclusion in Fc (rather than the term being subtracted from Fo).
also contains a non-coordinated molecule of diethyl ether lying close to a centre of symmetry. Attempts were made to model this using disordered ether molecules. One model consisted of a molecule of ether interpenetrating its image in a mirror plane perpendicular to the medial axis of the molecule,H atoms associated with the aryl-methyl groups were found in a difference Fourier map. All other H atoms were placed geometrically after each cycle of Uiso(H) = 1.3Ueq(C).
with C—H distances in the range 0.96–1.1 Å. All H atoms were treated with the riding model during the withData collection: COLLECT (Nonius, 2000); cell DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.
Supporting information
https://doi.org/10.1107/S1600536806004041/fl6217sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806004041/fl6217Isup2.hkl
Data collection: COLLECT (Nonius, 2000); cell
DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.[Li4(C55H64N6)(C4H10O)] | Z = 2 |
Mr = 911.04 | F(000) = 980 |
Triclinic, P1 | Dx = 1.123 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.607 (2) Å | Cell parameters from 22654 reflections |
b = 14.302 (3) Å | θ = 5–28° |
c = 17.477 (4) Å | µ = 0.07 mm−1 |
α = 78.18 (3)° | T = 173 K |
β = 72.68 (3)° | Block, yellow |
γ = 80.31 (3)° | 0.20 × 0.20 × 0.15 mm |
V = 2693.0 (11) Å3 |
Nonius KappaCCD area-detector diffractometer | 4760 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.026 |
CCD scans | θmax = 27.5°, θmin = 5.1° |
Absorption correction: multi-scan DENZO/SCALEPACK (Otwinowski & Minor, 1997) | h = −14→15 |
Tmin = 0.99, Tmax = 0.99 | k = −17→18 |
22654 measured reflections | l = 0→22 |
12141 independent reflections |
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.09 | w = [1-(Fo-Fc)2/36σ2(F)]2/[0.516To(x) + 0.342T1(x) + 0.252T2(x)], where Ti are the Chebychev polynomials and x = Fc/Fmax (Prince, 1982; Watkin, 1994) |
4760 reflections | (Δ/σ)max = 0.000236 |
649 parameters | Δρmax = 0.33 e Å−3 |
36 restraints | Δρmin = −0.23 e Å−3 |
Refinement. Loose vibration and thermal similarity restraints were applied to the coordinated molecule of diethyl ether. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Li1 | 0.7451 (4) | 0.2096 (3) | 0.7821 (3) | 0.0324 | |
Li2 | 0.6433 (5) | 0.0889 (3) | 0.7436 (3) | 0.0391 | |
Li3 | 0.6008 (5) | 0.6041 (3) | 0.8068 (3) | 0.0353 | |
Li4 | 0.5436 (5) | 0.4873 (3) | 0.7342 (3) | 0.0360 | |
N1 | 0.7888 (2) | 0.06762 (15) | 0.78459 (15) | 0.0304 | |
N2 | 0.6711 (2) | 0.22286 (16) | 0.68750 (15) | 0.0306 | |
N3 | 0.8956 (2) | 0.26499 (15) | 0.71481 (15) | 0.0310 | |
N4 | 0.6483 (2) | 0.46919 (15) | 0.81021 (14) | 0.0298 | |
N5 | 0.7514 (2) | 0.65913 (16) | 0.79263 (16) | 0.0350 | |
N6 | 0.5895 (2) | 0.62457 (16) | 0.69496 (15) | 0.0310 | |
O1 | 0.5815 (2) | 0.00686 (18) | 0.69246 (15) | 0.0554 | |
C1 | 0.9679 (3) | 0.1061 (2) | 0.5593 (2) | 0.0429 | |
C2 | 0.8928 (3) | 0.1430 (2) | 0.63835 (19) | 0.0347 | |
C3 | 0.8734 (3) | 0.05210 (19) | 0.70595 (18) | 0.0326 | |
C4 | 0.8107 (3) | 0.00375 (18) | 0.85267 (18) | 0.0295 | |
C5 | 0.7140 (3) | −0.04321 (19) | 0.90868 (18) | 0.0303 | |
C6 | 0.7307 (3) | −0.1085 (2) | 0.97646 (19) | 0.0343 | |
C7 | 0.8424 (3) | −0.1300 (2) | 0.99362 (19) | 0.0364 | |
C8 | 0.9358 (3) | −0.0813 (2) | 0.9414 (2) | 0.0369 | |
C9 | 0.9243 (3) | −0.01446 (19) | 0.87250 (19) | 0.0331 | |
C10 | 0.5890 (3) | −0.0244 (2) | 0.8962 (2) | 0.0404 | |
C11 | 0.8586 (3) | −0.2023 (3) | 1.0674 (2) | 0.0517 | |
C12 | 1.0298 (3) | 0.0404 (2) | 0.8250 (2) | 0.0408 | |
C13 | 0.7737 (3) | 0.1982 (2) | 0.61890 (19) | 0.0389 | |
C14 | 0.5879 (2) | 0.30074 (18) | 0.67972 (17) | 0.0261 | |
C15 | 0.4828 (3) | 0.30696 (19) | 0.74838 (18) | 0.0308 | |
C16 | 0.3866 (3) | 0.37940 (19) | 0.74953 (19) | 0.0315 | |
C17 | 0.3853 (2) | 0.45402 (19) | 0.68461 (18) | 0.0294 | |
C18 | 0.4878 (3) | 0.45240 (19) | 0.61887 (18) | 0.0305 | |
C19 | 0.5878 (3) | 0.3806 (2) | 0.61350 (17) | 0.0295 | |
C20 | 0.4723 (3) | 0.2288 (2) | 0.82212 (19) | 0.0388 | |
C21 | 0.2785 (3) | 0.5309 (2) | 0.6854 (2) | 0.0379 | |
C22 | 0.6898 (3) | 0.3941 (2) | 0.5356 (2) | 0.0408 | |
C23 | 0.9626 (3) | 0.20880 (19) | 0.66114 (19) | 0.0333 | |
C24 | 1.0893 (3) | 0.2105 (2) | 0.6328 (2) | 0.0423 | |
C25 | 1.1430 (3) | 0.2677 (2) | 0.6633 (2) | 0.0464 | |
C26 | 1.0729 (3) | 0.3261 (2) | 0.7180 (2) | 0.0412 | |
C27 | 0.9478 (3) | 0.32595 (19) | 0.74035 (19) | 0.0325 | |
C28 | 0.8583 (3) | 0.39146 (19) | 0.79394 (19) | 0.0313 | |
C29 | 0.9203 (3) | 0.4466 (2) | 0.8343 (2) | 0.0383 | |
C30 | 0.7659 (3) | 0.33536 (19) | 0.86184 (18) | 0.0298 | |
C31 | 0.7846 (3) | 0.2525 (2) | 0.91553 (19) | 0.0333 | |
C32 | 0.6893 (3) | 0.2212 (2) | 0.98112 (19) | 0.0345 | |
C33 | 0.5763 (3) | 0.2774 (2) | 0.99052 (19) | 0.0342 | |
C34 | 0.5541 (3) | 0.3617 (2) | 0.93692 (19) | 0.0336 | |
C35 | 0.6509 (3) | 0.39003 (19) | 0.87025 (18) | 0.0289 | |
C36 | 0.7091 (3) | 0.1318 (2) | 1.0415 (2) | 0.0418 | |
C37 | 0.4317 (3) | 0.4200 (2) | 0.9504 (2) | 0.0406 | |
C38 | 0.7665 (3) | 0.45829 (18) | 0.74766 (18) | 0.0294 | |
C39 | 0.8086 (3) | 0.55284 (19) | 0.68906 (18) | 0.0311 | |
C40 | 0.8384 (3) | 0.62864 (19) | 0.72886 (19) | 0.0329 | |
C41 | 0.9478 (3) | 0.6686 (2) | 0.6995 (2) | 0.0428 | |
C42 | 0.9702 (3) | 0.7369 (2) | 0.7376 (3) | 0.0536 | |
C43 | 0.8824 (3) | 0.7654 (2) | 0.8041 (2) | 0.0528 | |
C44 | 0.7749 (3) | 0.7260 (2) | 0.8286 (2) | 0.0429 | |
C45 | 0.9204 (3) | 0.5227 (2) | 0.62126 (19) | 0.0372 | |
C46 | 0.7103 (3) | 0.6012 (2) | 0.64285 (18) | 0.0323 | |
C47 | 0.5060 (3) | 0.69239 (19) | 0.66532 (18) | 0.0307 | |
C48 | 0.4053 (3) | 0.72876 (19) | 0.72614 (19) | 0.0328 | |
C49 | 0.3128 (3) | 0.7954 (2) | 0.7067 (2) | 0.0366 | |
C50 | 0.3128 (3) | 0.8325 (2) | 0.6266 (2) | 0.0386 | |
C51 | 0.4093 (3) | 0.7973 (2) | 0.5678 (2) | 0.0403 | |
C52 | 0.5054 (3) | 0.7288 (2) | 0.58290 (19) | 0.0331 | |
C53 | 0.4016 (3) | 0.6961 (2) | 0.8141 (2) | 0.0441 | |
C54 | 0.2146 (3) | 0.9079 (3) | 0.6061 (3) | 0.0564 | |
C55 | 0.5987 (3) | 0.6981 (2) | 0.50957 (19) | 0.0419 | |
C56 | 0.7084 (6) | −0.1091 (4) | 0.6073 (4) | 0.1115 | |
C57 | 0.6320 (6) | −0.0917 (3) | 0.6879 (3) | 0.1025 | |
C58 | 0.4671 (12) | 0.0682 (10) | 0.6657 (6) | 0.0516 | 0.5000 |
C59 | 0.3535 (8) | 0.0419 (6) | 0.7316 (7) | 0.0633 | 0.5000 |
C62 | 0.4962 (9) | 0.0113 (9) | 0.6502 (7) | 0.0654 | 0.5000 |
C63 | 0.4024 (17) | 0.0866 (12) | 0.6824 (13) | 0.0971 | 0.5000 |
O2 | 1.0339 | 0.4814 | −0.0072 | 0.0500* | 0.0000 |
C60 | 1.0944 | 0.5482 | −0.0728 | 0.0500* | 0.0000 |
C61 | 1.0743 | 0.6558 | −0.0664 | 0.0500* | 0.0000 |
C64 | 0.9068 | 0.4760 | 0.0202 | 0.0500* | 0.0000 |
C65 | 0.8849 | 0.3908 | 0.0907 | 0.0500* | 0.0000 |
H2 | 0.7784 | 0.3979 | 0.5445 | 0.0500* | |
H3 | 0.1393 | 0.9136 | 0.6524 | 0.0500* | |
H4 | 0.6230 | 0.6246 | 0.5197 | 0.0500* | |
H5 | 0.5641 | 0.7150 | 0.4590 | 0.0500* | |
H6 | 0.6738 | 0.7308 | 0.4965 | 0.0500* | |
H7 | 0.6550 | 0.4579 | 0.5033 | 0.0500* | |
H8 | 0.2348 | 0.5183 | 0.6531 | 0.0500* | |
H9 | 0.3037 | 0.5916 | 0.6578 | 0.0500* | |
H11 | 0.9210 | 0.0627 | 0.5451 | 0.0536* | |
H12 | 1.0462 | 0.0697 | 0.5671 | 0.0536* | |
H13 | 0.9853 | 0.1620 | 0.5144 | 0.0536* | |
H14 | 0.3726 | 0.3858 | 0.9984 | 0.0500* | |
H15 | 0.8173 | −0.1822 | 1.1252 | 0.0500* | |
H16 | 1.0859 | 0.0451 | 0.8621 | 0.0500* | |
H17 | 0.3840 | 0.4291 | 0.9027 | 0.0500* | |
H18 | 1.0834 | 0.0026 | 0.7819 | 0.0500* | |
H19 | 1.0012 | 0.1168 | 0.8026 | 0.0500* | |
H20 | 0.6970 | 0.3352 | 0.5056 | 0.0500* | |
H21 | 0.5360 | −0.0650 | 0.9467 | 0.0500* | |
H22 | 0.2270 | 0.5283 | 0.7460 | 0.0500* | |
H23 | 0.9468 | −0.2157 | 1.0649 | 0.0500* | |
H24 | 0.4415 | 0.4958 | 0.9506 | 0.0500* | |
H25 | 0.6307 | 0.1233 | 1.0888 | 0.0500* | |
H27 | 0.8426 | −0.2703 | 1.0604 | 0.0500* | |
H28 | 0.5585 | 0.0456 | 0.8936 | 0.0500* | |
H29 | 0.5907 | −0.0419 | 0.8392 | 0.0500* | |
H30 | 0.7438 | 0.0698 | 1.0140 | 0.0500* | |
H31 | 0.9541 | 0.0251 | 0.7156 | 0.0406* | |
H32 | 0.8423 | 0.0041 | 0.6851 | 0.0406* | |
H33 | 0.4032 | 0.2499 | 0.8727 | 0.0500* | |
H34 | 0.4821 | 0.7152 | 0.8279 | 0.0500* | |
H35 | 0.4066 | 0.6265 | 0.8286 | 0.0500* | |
H36 | 0.4587 | 0.1634 | 0.8022 | 0.0500* | |
H37 | 0.5468 | 0.2199 | 0.8409 | 0.0500* | |
H38 | 0.3246 | 0.7150 | 0.8502 | 0.0500* | |
H61 | 0.6601 | −0.1414 | 1.0136 | 0.0449* | |
H81 | 1.0167 | −0.0948 | 0.9532 | 0.0460* | |
H131 | 0.7949 | 0.2596 | 0.5815 | 0.0489* | |
H132 | 0.7446 | 0.1568 | 0.5905 | 0.0489* | |
H161 | 0.3154 | 0.3778 | 0.7989 | 0.0422* | |
H181 | 0.4909 | 0.5057 | 0.5715 | 0.0431* | |
H241 | 1.1391 | 0.1708 | 0.5910 | 0.0527* | |
H251 | 1.2333 | 0.2673 | 0.6451 | 0.0562* | |
H261 | 1.1113 | 0.3671 | 0.7412 | 0.0508* | |
H291 | 0.8572 | 0.4889 | 0.8686 | 0.0517* | |
H292 | 0.9658 | 0.4000 | 0.8691 | 0.0517* | |
H293 | 0.9781 | 0.4870 | 0.7914 | 0.0517* | |
H311 | 0.8672 | 0.2153 | 0.9075 | 0.0452* | |
H331 | 0.5075 | 0.2565 | 1.0380 | 0.0456* | |
H361 | 0.7762 | 0.1443 | 1.0670 | 0.0499* | |
H381 | 0.7529 | 0.4177 | 0.7116 | 0.0368* | |
H411 | 1.0098 | 0.6482 | 0.6505 | 0.0570* | |
H421 | 1.0492 | 0.7649 | 0.7174 | 0.0701* | |
H431 | 0.8972 | 0.8133 | 0.8335 | 0.0671* | |
H441 | 0.7103 | 0.7476 | 0.8760 | 0.0630* | |
H451 | 0.8997 | 0.4733 | 0.5959 | 0.0473* | |
H452 | 0.9898 | 0.4948 | 0.6448 | 0.0473* | |
H453 | 0.9438 | 0.5800 | 0.5790 | 0.0473* | |
H461 | 0.7389 | 0.6618 | 0.6075 | 0.0432* | |
H462 | 0.7042 | 0.5556 | 0.6082 | 0.0432* | |
H491 | 0.2438 | 0.8175 | 0.7517 | 0.0476* | |
H511 | 0.4117 | 0.8228 | 0.5097 | 0.0507* | |
H541 | 0.2496 | 0.9752 | 0.5874 | 0.0673* | |
H542 | 0.1897 | 0.8903 | 0.5557 | 0.0673* | |
H561 | 0.7410 | −0.1786 | 0.6082 | 0.1308* | |
H562 | 0.7775 | −0.0692 | 0.5905 | 0.1308* | |
H563 | 0.6584 | −0.0896 | 0.5676 | 0.1308* | |
H571 | 0.6828 | −0.1120 | 0.7270 | 0.1343* | |
H572 | 0.5637 | −0.1324 | 0.7041 | 0.1343* | |
H581 | 0.4735 | 0.1387 | 0.6566 | 0.0638* | 0.5000 |
H582 | 0.4593 | 0.0502 | 0.6153 | 0.0638* | 0.5000 |
H591 | 0.2766 | 0.0772 | 0.7205 | 0.0995* | 0.5000 |
H592 | 0.3638 | 0.0596 | 0.7814 | 0.0995* | 0.5000 |
H593 | 0.3496 | −0.0289 | 0.7402 | 0.0995* | 0.5000 |
H621 | 0.4681 | −0.0527 | 0.6555 | 0.0938* | 0.5000 |
H622 | 0.5282 | 0.0379 | 0.5914 | 0.0938* | 0.5000 |
H631 | 0.3333 | 0.0974 | 0.6573 | 0.1803* | 0.5000 |
H632 | 0.3737 | 0.0587 | 0.7412 | 0.1803* | 0.5000 |
H633 | 0.4338 | 0.1493 | 0.6771 | 0.1803* | 0.5000 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Li1 | 0.032 (3) | 0.027 (2) | 0.038 (3) | −0.0029 (19) | −0.009 (2) | −0.006 (2) |
Li2 | 0.041 (3) | 0.028 (2) | 0.051 (3) | 0.001 (2) | −0.022 (3) | −0.005 (2) |
Li3 | 0.036 (3) | 0.037 (3) | 0.034 (3) | −0.003 (2) | −0.011 (2) | −0.008 (2) |
Li4 | 0.037 (3) | 0.033 (2) | 0.039 (3) | −0.006 (2) | −0.011 (2) | −0.005 (2) |
N1 | 0.0310 (14) | 0.0261 (12) | 0.0344 (14) | −0.0009 (10) | −0.0110 (11) | −0.0045 (10) |
N2 | 0.0271 (13) | 0.0293 (12) | 0.0337 (14) | 0.0035 (10) | −0.0085 (11) | −0.0066 (10) |
N3 | 0.0288 (13) | 0.0233 (11) | 0.0394 (15) | −0.0019 (10) | −0.0083 (11) | −0.0045 (10) |
N4 | 0.0287 (13) | 0.0277 (12) | 0.0314 (14) | −0.0026 (10) | −0.0084 (11) | −0.0018 (10) |
N5 | 0.0372 (15) | 0.0293 (12) | 0.0420 (16) | −0.0036 (10) | −0.0147 (13) | −0.0082 (11) |
N6 | 0.0296 (14) | 0.0301 (12) | 0.0312 (14) | −0.0012 (10) | −0.0065 (11) | −0.0047 (10) |
O1 | 0.0483 (15) | 0.0715 (16) | 0.0548 (15) | −0.0224 (12) | −0.0179 (12) | −0.0106 (12) |
C1 | 0.0414 (19) | 0.0418 (18) | 0.0404 (19) | 0.0116 (14) | −0.0080 (15) | −0.0138 (15) |
C2 | 0.0333 (17) | 0.0318 (15) | 0.0331 (17) | 0.0064 (12) | −0.0036 (14) | −0.0085 (13) |
C3 | 0.0353 (17) | 0.0281 (14) | 0.0353 (17) | 0.0014 (12) | −0.0109 (14) | −0.0095 (12) |
C4 | 0.0344 (17) | 0.0192 (13) | 0.0368 (17) | −0.0005 (11) | −0.0132 (14) | −0.0061 (12) |
C5 | 0.0296 (16) | 0.0282 (14) | 0.0348 (17) | −0.0026 (12) | −0.0130 (13) | −0.0034 (13) |
C6 | 0.0330 (17) | 0.0324 (15) | 0.0381 (18) | −0.0073 (12) | −0.0091 (14) | −0.0048 (13) |
C7 | 0.0394 (19) | 0.0337 (16) | 0.0384 (18) | −0.0050 (13) | −0.0177 (15) | 0.0004 (13) |
C8 | 0.0328 (17) | 0.0354 (16) | 0.046 (2) | 0.0019 (13) | −0.0200 (15) | −0.0066 (14) |
C9 | 0.0334 (17) | 0.0266 (14) | 0.0402 (18) | −0.0013 (12) | −0.0114 (14) | −0.0075 (13) |
C10 | 0.0349 (18) | 0.0439 (18) | 0.0414 (19) | −0.0086 (14) | −0.0158 (15) | 0.0066 (14) |
C11 | 0.041 (2) | 0.054 (2) | 0.059 (2) | −0.0085 (16) | −0.0257 (18) | 0.0129 (17) |
C12 | 0.0335 (18) | 0.0427 (17) | 0.049 (2) | −0.0081 (14) | −0.0136 (15) | −0.0076 (15) |
C13 | 0.0383 (18) | 0.0425 (17) | 0.0333 (18) | 0.0077 (14) | −0.0114 (15) | −0.0079 (14) |
C14 | 0.0244 (15) | 0.0296 (14) | 0.0271 (15) | −0.0028 (11) | −0.0091 (13) | −0.0079 (12) |
C15 | 0.0278 (16) | 0.0297 (14) | 0.0352 (17) | −0.0028 (12) | −0.0112 (13) | −0.0027 (12) |
C16 | 0.0234 (15) | 0.0339 (15) | 0.0350 (17) | −0.0051 (12) | −0.0035 (13) | −0.0063 (13) |
C17 | 0.0258 (16) | 0.0299 (14) | 0.0351 (17) | −0.0009 (11) | −0.0130 (13) | −0.0061 (13) |
C18 | 0.0332 (17) | 0.0302 (14) | 0.0317 (17) | −0.0024 (12) | −0.0156 (14) | −0.0042 (12) |
C19 | 0.0266 (15) | 0.0341 (15) | 0.0297 (17) | −0.0053 (12) | −0.0069 (13) | −0.0090 (12) |
C20 | 0.0326 (17) | 0.0383 (16) | 0.0370 (18) | 0.0008 (13) | −0.0040 (14) | 0.0008 (14) |
C21 | 0.0319 (17) | 0.0364 (16) | 0.0452 (19) | −0.0013 (13) | −0.0137 (15) | −0.0040 (14) |
C22 | 0.0410 (19) | 0.0354 (16) | 0.0403 (19) | 0.0015 (13) | −0.0070 (15) | −0.0042 (14) |
C23 | 0.0320 (17) | 0.0266 (14) | 0.0343 (17) | 0.0003 (12) | −0.0020 (13) | −0.0024 (12) |
C24 | 0.0308 (18) | 0.0443 (18) | 0.045 (2) | 0.0000 (14) | −0.0007 (15) | −0.0099 (15) |
C25 | 0.0266 (17) | 0.0456 (19) | 0.059 (2) | −0.0045 (14) | −0.0026 (16) | −0.0038 (16) |
C26 | 0.0297 (18) | 0.0354 (16) | 0.054 (2) | −0.0060 (13) | −0.0084 (15) | −0.0003 (15) |
C27 | 0.0263 (16) | 0.0259 (14) | 0.0416 (18) | −0.0018 (11) | −0.0069 (13) | −0.0015 (12) |
C28 | 0.0271 (16) | 0.0297 (15) | 0.0396 (18) | −0.0029 (11) | −0.0123 (13) | −0.0071 (12) |
C29 | 0.0381 (18) | 0.0344 (16) | 0.050 (2) | −0.0056 (13) | −0.0214 (15) | −0.0078 (14) |
C30 | 0.0330 (17) | 0.0286 (14) | 0.0300 (16) | −0.0047 (12) | −0.0105 (13) | −0.0060 (12) |
C31 | 0.0325 (17) | 0.0314 (15) | 0.0398 (18) | 0.0006 (12) | −0.0162 (14) | −0.0088 (13) |
C32 | 0.0400 (18) | 0.0309 (15) | 0.0343 (18) | −0.0066 (13) | −0.0135 (14) | −0.0023 (13) |
C33 | 0.0326 (17) | 0.0389 (16) | 0.0305 (17) | −0.0032 (13) | −0.0078 (14) | −0.0060 (13) |
C34 | 0.0292 (16) | 0.0345 (16) | 0.0373 (18) | −0.0029 (12) | −0.0104 (14) | −0.0050 (13) |
C35 | 0.0288 (16) | 0.0291 (14) | 0.0315 (16) | −0.0020 (12) | −0.0118 (13) | −0.0069 (12) |
C36 | 0.047 (2) | 0.0354 (16) | 0.0431 (19) | −0.0047 (14) | −0.0140 (16) | −0.0038 (14) |
C37 | 0.0318 (17) | 0.0447 (17) | 0.0382 (19) | 0.0004 (13) | −0.0059 (15) | 0.0001 (14) |
C38 | 0.0301 (16) | 0.0250 (14) | 0.0354 (17) | −0.0021 (11) | −0.0107 (13) | −0.0083 (12) |
C39 | 0.0272 (16) | 0.0314 (15) | 0.0341 (17) | −0.0045 (12) | −0.0065 (13) | −0.0064 (12) |
C40 | 0.0323 (17) | 0.0269 (14) | 0.0395 (18) | −0.0039 (12) | −0.0107 (15) | −0.0037 (13) |
C41 | 0.0385 (19) | 0.0363 (17) | 0.052 (2) | −0.0099 (14) | −0.0085 (16) | −0.0059 (15) |
C42 | 0.051 (2) | 0.0421 (18) | 0.075 (3) | −0.0195 (16) | −0.019 (2) | −0.0118 (18) |
C43 | 0.061 (2) | 0.0404 (19) | 0.067 (3) | −0.0123 (16) | −0.021 (2) | −0.0205 (17) |
C44 | 0.052 (2) | 0.0334 (16) | 0.050 (2) | −0.0039 (14) | −0.0206 (17) | −0.0133 (14) |
C45 | 0.0362 (18) | 0.0362 (16) | 0.0382 (18) | −0.0042 (13) | −0.0079 (14) | −0.0070 (13) |
C46 | 0.0360 (17) | 0.0303 (15) | 0.0309 (16) | −0.0041 (12) | −0.0092 (14) | −0.0057 (12) |
C47 | 0.0340 (17) | 0.0254 (14) | 0.0353 (17) | −0.0077 (12) | −0.0120 (14) | −0.0037 (12) |
C48 | 0.0338 (17) | 0.0289 (14) | 0.0360 (18) | −0.0036 (12) | −0.0106 (14) | −0.0047 (12) |
C49 | 0.0308 (17) | 0.0328 (15) | 0.044 (2) | −0.0011 (12) | −0.0072 (14) | −0.0072 (14) |
C50 | 0.0370 (18) | 0.0355 (16) | 0.043 (2) | −0.0035 (13) | −0.0144 (16) | −0.0021 (14) |
C51 | 0.046 (2) | 0.0411 (17) | 0.0356 (19) | −0.0091 (14) | −0.0176 (16) | 0.0027 (14) |
C52 | 0.0317 (17) | 0.0326 (15) | 0.0347 (18) | −0.0049 (12) | −0.0111 (14) | −0.0011 (13) |
C53 | 0.0426 (19) | 0.0457 (18) | 0.0372 (19) | 0.0100 (14) | −0.0078 (15) | −0.0088 (14) |
C54 | 0.049 (2) | 0.057 (2) | 0.058 (2) | 0.0109 (17) | −0.0210 (19) | −0.0021 (18) |
C55 | 0.0450 (19) | 0.0490 (19) | 0.0307 (18) | −0.0052 (15) | −0.0106 (15) | −0.0036 (14) |
C56 | 0.135 (5) | 0.091 (4) | 0.108 (4) | −0.057 (3) | 0.010 (4) | −0.045 (3) |
C57 | 0.165 (5) | 0.056 (3) | 0.077 (3) | −0.061 (3) | 0.017 (3) | −0.027 (2) |
C58 | 0.065 (7) | 0.051 (7) | 0.044 (5) | −0.013 (6) | −0.018 (5) | −0.009 (4) |
C59 | 0.042 (5) | 0.055 (5) | 0.092 (7) | −0.021 (4) | −0.021 (5) | 0.005 (5) |
C62 | 0.067 (6) | 0.062 (5) | 0.083 (6) | −0.011 (5) | −0.051 (5) | 0.002 (5) |
C63 | 0.093 (12) | 0.076 (9) | 0.134 (14) | 0.023 (9) | −0.053 (11) | −0.038 (8) |
N1—C3 | 1.466 (4) | C30—C35 | 1.412 (4) |
N1—C4 | 1.404 (4) | C31—C32 | 1.392 (4) |
N2—C13 | 1.470 (4) | C31—H311 | 1.000 |
N2—C14 | 1.359 (3) | C32—C33 | 1.401 (4) |
N3—C23 | 1.339 (4) | C32—C36 | 1.514 (4) |
N3—C27 | 1.351 (4) | C33—C34 | 1.406 (4) |
N4—C35 | 1.380 (4) | C33—H331 | 1.000 |
N4—C38 | 1.485 (4) | C34—C35 | 1.402 (4) |
N5—C40 | 1.354 (4) | C34—C37 | 1.500 (4) |
N5—C44 | 1.350 (4) | C36—H25 | 1.037 |
N6—C46 | 1.453 (4) | C36—H30 | 1.058 |
N6—C47 | 1.388 (4) | C36—H361 | 1.060 |
O1—C57 | 1.441 (5) | C37—H14 | 1.009 |
O1—C58 | 1.600 (14) | C37—H17 | 1.107 |
O1—C62 | 1.388 (9) | C37—H24 | 1.109 |
C1—C2 | 1.541 (4) | C38—C39 | 1.573 (4) |
C1—H11 | 1.000 | C38—H381 | 1.000 |
C1—H12 | 1.000 | C39—C40 | 1.535 (4) |
C1—H13 | 1.000 | C39—C45 | 1.542 (4) |
C2—C3 | 1.564 (4) | C39—C46 | 1.577 (4) |
C2—C13 | 1.565 (4) | C40—C41 | 1.393 (4) |
C2—C23 | 1.518 (4) | C41—C42 | 1.386 (5) |
C3—H31 | 1.000 | C41—H411 | 1.000 |
C3—H32 | 1.000 | C42—C43 | 1.380 (6) |
C4—C5 | 1.414 (4) | C42—H421 | 1.000 |
C4—C9 | 1.430 (4) | C43—C44 | 1.370 (5) |
C5—C6 | 1.391 (4) | C43—H431 | 1.000 |
C5—C10 | 1.503 (4) | C44—H441 | 1.000 |
C6—C7 | 1.388 (4) | C45—H451 | 1.000 |
C6—H61 | 1.000 | C45—H452 | 1.000 |
C7—C8 | 1.377 (4) | C45—H453 | 1.000 |
C7—C11 | 1.517 (5) | C46—H461 | 1.000 |
C8—C9 | 1.401 (4) | C46—H462 | 1.000 |
C8—H81 | 1.000 | C47—C48 | 1.431 (4) |
C9—C12 | 1.502 (4) | C47—C52 | 1.430 (4) |
C10—H21 | 1.041 | C48—C49 | 1.385 (4) |
C10—H28 | 1.000 | C48—C53 | 1.503 (5) |
C10—H29 | 1.070 | C49—C50 | 1.392 (5) |
C11—H15 | 1.057 | C49—H491 | 1.000 |
C11—H23 | 0.998 | C50—C51 | 1.379 (5) |
C11—H27 | 1.057 | C50—C54 | 1.504 (5) |
C12—H16 | 1.065 | C51—C52 | 1.406 (4) |
C12—H18 | 1.010 | C51—H511 | 1.000 |
C12—H19 | 1.112 | C52—C55 | 1.501 (5) |
C13—H131 | 1.000 | C53—H34 | 1.119 |
C13—H132 | 1.000 | C53—H35 | 0.972 |
C14—C15 | 1.439 (4) | C53—H38 | 0.961 |
C14—C19 | 1.450 (4) | C54—H3 | 1.003 |
C15—C16 | 1.388 (4) | C54—H541 | 1.060 |
C15—C20 | 1.513 (4) | C54—H542 | 1.090 |
C16—C17 | 1.391 (4) | C55—H4 | 1.034 |
C16—H161 | 1.000 | C55—H5 | 1.045 |
C17—C18 | 1.387 (4) | C55—H6 | 1.004 |
C17—C21 | 1.512 (4) | C56—C57 | 1.470 (7) |
C18—C19 | 1.408 (4) | C56—H561 | 1.000 |
C18—H181 | 1.000 | C56—H562 | 1.000 |
C19—C22 | 1.518 (4) | C56—H563 | 1.000 |
C20—H33 | 1.059 | C57—H571 | 1.000 |
C20—H36 | 1.112 | C57—H572 | 1.000 |
C20—H37 | 0.993 | C58—C59 | 1.514 (15) |
C21—H8 | 0.923 | C58—H581 | 1.000 |
C21—H9 | 0.950 | C58—H582 | 1.000 |
C21—H22 | 1.046 | C59—H591 | 1.000 |
C22—H2 | 1.096 | C59—H592 | 1.000 |
C22—H7 | 1.056 | C59—H593 | 1.000 |
C22—H20 | 1.060 | C62—C63 | 1.467 (16) |
C23—C24 | 1.408 (4) | C62—H621 | 1.000 |
C24—C25 | 1.373 (5) | C62—H622 | 1.000 |
C24—H241 | 1.000 | C63—H631 | 1.000 |
C25—C26 | 1.382 (5) | C63—H632 | 1.000 |
C25—H251 | 1.000 | C63—H633 | 1.000 |
C26—C27 | 1.387 (4) | O2—C60i | 1.7553 (7) |
C26—H261 | 1.000 | O2—C64i | 0.9421 (3) |
C27—C28 | 1.512 (4) | O2—O2i | 0.8722 (3) |
C28—C29 | 1.536 (4) | O2—C60 | 1.4205 (6) |
C28—C30 | 1.531 (4) | O2—C64 | 1.4197 (3) |
C28—C38 | 1.599 (4) | C60—C65i | 0.9122 (3) |
C29—H291 | 1.000 | C60—C64i | 0.9092 (3) |
C29—H292 | 1.000 | C60—C61 | 1.5398 (3) |
C29—H293 | 1.000 | C61—C65i | 0.8594 (3) |
C30—C31 | 1.383 (4) | C64—C65 | 1.5396 (6) |
C3—N1—C4 | 115.8 (2) | H25—C36—H30 | 113.529 |
C13—N2—C14 | 122.3 (2) | C32—C36—H361 | 106.537 |
C23—N3—C27 | 120.7 (3) | H25—C36—H361 | 106.592 |
C35—N4—C38 | 105.6 (2) | H30—C36—H361 | 106.592 |
C40—N5—C44 | 118.6 (3) | C34—C37—H14 | 109.350 |
C46—N6—C47 | 120.6 (2) | C34—C37—H17 | 117.537 |
C57—O1—C58 | 130.7 (6) | H14—C37—H17 | 101.091 |
C57—O1—C62 | 97.6 (6) | C34—C37—H24 | 109.678 |
C2—C1—H11 | 109.446 | H14—C37—H24 | 118.077 |
C2—C1—H12 | 109.615 | H17—C37—H24 | 101.108 |
H11—C1—H12 | 109.476 | N4—C38—C28 | 105.9 (2) |
C2—C1—H13 | 109.339 | N4—C38—C39 | 116.2 (2) |
H11—C1—H13 | 109.476 | C28—C38—C39 | 119.0 (2) |
H12—C1—H13 | 109.476 | N4—C38—H381 | 104.737 |
C1—C2—C3 | 106.2 (2) | C28—C38—H381 | 104.926 |
C1—C2—C13 | 104.9 (3) | C39—C38—H381 | 104.631 |
C3—C2—C13 | 114.8 (3) | C38—C39—C40 | 115.8 (2) |
C1—C2—C23 | 110.3 (3) | C38—C39—C45 | 107.2 (2) |
C3—C2—C23 | 108.9 (2) | C40—C39—C45 | 110.0 (2) |
C13—C2—C23 | 111.5 (2) | C38—C39—C46 | 110.3 (2) |
C2—C3—N1 | 116.2 (2) | C40—C39—C46 | 108.7 (2) |
C2—C3—H31 | 107.856 | C45—C39—C46 | 104.1 (2) |
N1—C3—H31 | 107.572 | C39—C40—N5 | 117.4 (2) |
C2—C3—H32 | 107.739 | C39—C40—C41 | 122.3 (3) |
N1—C3—H32 | 107.888 | N5—C40—C41 | 120.2 (3) |
H31—C3—H32 | 109.467 | C40—C41—C42 | 120.1 (3) |
N1—C4—C5 | 119.2 (2) | C40—C41—H411 | 119.683 |
N1—C4—C9 | 124.4 (3) | C42—C41—H411 | 120.255 |
C5—C4—C9 | 116.3 (3) | C41—C42—C43 | 119.3 (3) |
C4—C5—C6 | 121.8 (3) | C41—C42—H421 | 120.416 |
C4—C5—C10 | 120.6 (2) | C43—C42—H421 | 120.315 |
C6—C5—C10 | 117.7 (3) | C42—C43—C44 | 118.1 (3) |
C5—C6—C7 | 121.9 (3) | C42—C43—H431 | 120.785 |
C5—C6—H61 | 118.912 | C44—C43—H431 | 121.118 |
C7—C6—H61 | 119.160 | C43—C44—N5 | 123.6 (3) |
C6—C7—C8 | 116.7 (3) | C43—C44—H441 | 118.411 |
C6—C7—C11 | 120.9 (3) | N5—C44—H441 | 117.944 |
C8—C7—C11 | 122.3 (3) | C39—C45—H451 | 109.124 |
C7—C8—C9 | 123.8 (3) | C39—C45—H452 | 109.650 |
C7—C8—H81 | 118.020 | H451—C45—H452 | 109.475 |
C9—C8—H81 | 118.135 | C39—C45—H453 | 109.625 |
C4—C9—C8 | 119.3 (3) | H451—C45—H453 | 109.477 |
C4—C9—C12 | 122.2 (3) | H452—C45—H453 | 109.475 |
C8—C9—C12 | 118.4 (3) | C39—C46—N6 | 115.0 (2) |
C5—C10—H21 | 104.472 | C39—C46—H461 | 108.127 |
C5—C10—H28 | 110.553 | N6—C46—H461 | 108.328 |
H21—C10—H28 | 110.838 | C39—C46—H462 | 107.732 |
C5—C10—H29 | 110.748 | N6—C46—H462 | 108.089 |
H21—C10—H29 | 114.436 | H461—C46—H462 | 109.467 |
H28—C10—H29 | 105.877 | N6—C47—C48 | 115.0 (3) |
C7—C11—H15 | 117.562 | N6—C47—C52 | 129.0 (3) |
C7—C11—H23 | 109.217 | C48—C47—C52 | 116.0 (3) |
H15—C11—H23 | 103.878 | C47—C48—C49 | 122.3 (3) |
C7—C11—H27 | 108.389 | C47—C48—C53 | 119.0 (3) |
H15—C11—H27 | 116.128 | C49—C48—C53 | 118.7 (3) |
H23—C11—H27 | 99.862 | C48—C49—C50 | 122.0 (3) |
C9—C12—H16 | 111.273 | C48—C49—H491 | 118.971 |
C9—C12—H18 | 108.312 | C50—C49—H491 | 119.020 |
H16—C12—H18 | 105.104 | C49—C50—C51 | 115.9 (3) |
C9—C12—H19 | 112.757 | C49—C50—C54 | 121.7 (3) |
H16—C12—H19 | 103.679 | C51—C50—C54 | 122.4 (3) |
H18—C12—H19 | 115.387 | C50—C51—C52 | 125.2 (3) |
C2—C13—N2 | 117.8 (3) | C50—C51—H511 | 117.676 |
C2—C13—H131 | 107.901 | C52—C51—H511 | 117.154 |
N2—C13—H131 | 107.427 | C47—C52—C51 | 118.6 (3) |
C2—C13—H132 | 107.130 | C47—C52—C55 | 125.2 (3) |
N2—C13—H132 | 106.950 | C51—C52—C55 | 116.2 (3) |
H131—C13—H132 | 109.467 | C48—C53—H34 | 111.414 |
N2—C14—C15 | 115.7 (2) | C48—C53—H35 | 111.663 |
N2—C14—C19 | 130.6 (3) | H34—C53—H35 | 104.529 |
C15—C14—C19 | 113.7 (2) | C48—C53—H38 | 112.697 |
C14—C15—C16 | 123.3 (3) | H34—C53—H38 | 114.636 |
C14—C15—C20 | 119.1 (2) | H35—C53—H38 | 101.133 |
C16—C15—C20 | 117.5 (3) | C50—C54—H3 | 113.934 |
C15—C16—C17 | 122.5 (3) | C50—C54—H541 | 108.541 |
C15—C16—H161 | 118.754 | H3—C54—H541 | 108.679 |
C17—C16—H161 | 118.765 | C50—C54—H542 | 108.587 |
C16—C17—C18 | 115.6 (3) | H3—C54—H542 | 108.312 |
C16—C17—C21 | 122.1 (3) | H541—C54—H542 | 108.679 |
C18—C17—C21 | 122.3 (3) | C52—C55—H4 | 110.286 |
C17—C18—C19 | 124.8 (3) | C52—C55—H5 | 110.507 |
C17—C18—H181 | 117.857 | H4—C55—H5 | 108.207 |
C19—C18—H181 | 117.376 | C52—C55—H6 | 111.175 |
C14—C19—C18 | 120.0 (3) | H4—C55—H6 | 108.320 |
C14—C19—C22 | 124.6 (2) | H5—C55—H6 | 108.254 |
C18—C19—C22 | 115.4 (3) | C57—C56—H561 | 111.023 |
C15—C20—H33 | 111.311 | C57—C56—H562 | 108.617 |
C15—C20—H36 | 105.509 | H561—C56—H562 | 109.476 |
H33—C20—H36 | 114.811 | C57—C56—H563 | 108.749 |
C15—C20—H37 | 109.936 | H561—C56—H563 | 109.476 |
H33—C20—H37 | 102.833 | H562—C56—H563 | 109.476 |
H36—C20—H37 | 112.531 | C56—C57—O1 | 114.9 (4) |
C17—C21—H8 | 108.560 | C56—C57—H571 | 107.950 |
C17—C21—H9 | 111.728 | O1—C57—H571 | 107.987 |
H8—C21—H9 | 101.456 | C56—C57—H572 | 107.818 |
C17—C21—H22 | 106.811 | O1—C57—H572 | 108.603 |
H8—C21—H22 | 111.941 | H571—C57—H572 | 109.467 |
H9—C21—H22 | 116.180 | O1—C58—C59 | 107.9 (8) |
C19—C22—H2 | 114.440 | O1—C58—H581 | 111.049 |
C19—C22—H7 | 101.608 | C59—C58—H581 | 111.346 |
H2—C22—H7 | 113.884 | O1—C58—H582 | 111.158 |
C19—C22—H20 | 107.382 | C59—C58—H582 | 105.834 |
H2—C22—H20 | 108.913 | H581—C58—H582 | 109.467 |
H7—C22—H20 | 110.282 | C58—C59—H591 | 113.835 |
C2—C23—N3 | 115.3 (2) | C58—C59—H592 | 104.478 |
C2—C23—C24 | 124.7 (3) | H591—C59—H592 | 109.476 |
N3—C23—C24 | 120.0 (3) | C58—C59—H593 | 109.947 |
C23—C24—C25 | 119.1 (3) | H591—C59—H593 | 109.476 |
C23—C24—H241 | 120.173 | H592—C59—H593 | 109.476 |
C25—C24—H241 | 120.773 | O1—C62—C63 | 102.9 (10) |
C24—C25—C26 | 120.4 (3) | O1—C62—H621 | 112.365 |
C24—C25—H251 | 119.507 | C63—C62—H621 | 115.945 |
C26—C25—H251 | 120.074 | O1—C62—H622 | 111.383 |
C25—C26—C27 | 118.2 (3) | C63—C62—H622 | 104.364 |
C25—C26—H261 | 121.011 | H621—C62—H622 | 109.467 |
C27—C26—H261 | 120.744 | C62—C63—H631 | 111.868 |
C26—C27—N3 | 121.3 (3) | C62—C63—H632 | 102.419 |
C26—C27—C28 | 124.7 (3) | H631—C63—H632 | 109.476 |
N3—C27—C28 | 114.0 (2) | C62—C63—H633 | 113.860 |
C27—C28—C29 | 112.7 (2) | H631—C63—H633 | 109.476 |
C27—C28—C30 | 111.6 (2) | H632—C63—H633 | 109.476 |
C29—C28—C30 | 107.4 (2) | C60i—O2—C64i | 137.69 (2) |
C27—C28—C38 | 111.6 (2) | C60i—O2—O2i | 53.44 (3) |
C29—C28—C38 | 114.0 (2) | C64i—O2—O2i | 102.91 (3) |
C30—C28—C38 | 98.6 (2) | C60i—O2—C60 | 150.449 (18) |
C28—C29—H291 | 109.328 | C64i—O2—C60 | 39.05 (2) |
C28—C29—H292 | 109.616 | O2i—O2—C60 | 97.01 (4) |
H291—C29—H292 | 109.475 | C60i—O2—C64 | 31.049 (14) |
C28—C29—H293 | 109.456 | C64i—O2—C64 | 143.213 (15) |
H291—C29—H293 | 109.476 | O2i—O2—C64 | 40.300 (13) |
H292—C29—H293 | 109.476 | C60—O2—C64 | 126.18 (3) |
C28—C30—C31 | 129.7 (3) | O2—C60—O2i | 29.551 (17) |
C28—C30—C35 | 107.9 (2) | O2—C60—C65i | 147.255 (17) |
C31—C30—C35 | 121.9 (3) | O2i—C60—C65i | 123.59 (3) |
C30—C31—C32 | 120.3 (3) | O2—C60—C64i | 40.746 (16) |
C30—C31—H311 | 119.736 | O2i—C60—C64i | 53.643 (19) |
C32—C31—H311 | 119.946 | C65i—C60—C64i | 115.40 (3) |
C31—C32—C33 | 117.5 (3) | O2—C60—C61 | 119.78 (3) |
C31—C32—C36 | 120.9 (3) | O2i—C60—C61 | 94.97 (4) |
C33—C32—C36 | 121.6 (3) | C65i—C60—C61 | 28.684 (13) |
C32—C33—C34 | 123.7 (3) | C64i—C60—C61 | 98.22 (3) |
C32—C33—H331 | 118.299 | C60—C61—C65i | 30.627 (18) |
C34—C33—H331 | 117.999 | O2—C64—O2i | 36.79 (2) |
C33—C34—C35 | 117.5 (3) | O2—C64—C60i | 95.31 (3) |
C33—C34—C37 | 121.6 (3) | O2i—C64—C60i | 100.21 (3) |
C35—C34—C37 | 120.9 (3) | O2—C64—C65 | 107.28 (4) |
C30—C35—C34 | 119.0 (3) | O2i—C64—C65 | 127.64 (2) |
C30—C35—N4 | 114.1 (2) | C60i—C64—C65 | 32.357 (16) |
C34—C35—N4 | 126.9 (2) | C64—C65—C60i | 32.240 (13) |
C32—C36—H25 | 110.027 | C64—C65—C61i | 100.65 (4) |
C32—C36—H30 | 113.047 | C60i—C65—C61i | 120.69 (3) |
Symmetry code: (i) −x+2, −y+1, −z. |
Acknowledgements
The authors thank B. R. Tyrrell for help with the data collection, and Dr D. J. Watkin for help in modelling the disorder.
References
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, C. K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Friedrich, S., Schubart, M., Gade, L. H., Scowen, I. J., Edwards, A. J. & McPartlin, M. (1997). Chem. Ber./Recueil, 130, 1751–1759. CrossRef CAS Google Scholar
Gade, L. H. & Mountford, P. (2001). Coord. Chem. Rev. 216–217, 65–97. Web of Science CrossRef CAS Google Scholar
Mehrkhodavandi, P., Bonitatebus, P. J. Jr & Schrock, R. R. (2000). J. Am. Chem. Soc. 122, 7841–7842. Web of Science CSD CrossRef CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Prince, E. (1982). Mathematical Techniques in Crystallography and Materials Science, pp. 80–82. New York, Heidelberg, Berlin: Springer-Verlag. Google Scholar
Sheldrick, G. M. (1985). SHELXS86. University of Göttingen, Germany. Google Scholar
Sluis, P. van der & Spek, A. L. (1990). Acta Cryst. A46, 194–201. CrossRef Web of Science IUCr Journals Google Scholar
Watkin, D. (1994). Acta Cryst. A50, 411–437. CrossRef CAS Web of Science IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. Google Scholar
© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.