supplementary materials


is5208 scheme

Acta Cryst. (2012). E68, o3423    [ doi:10.1107/S1600536812047435 ]

31-Benzyloxy-5,11,17,23,29-penta-tert-butylcalix[5]arene-32,33,34,35-tetraol

C. Gargiulli, G. Gattuso, A. Notti, F. Nicoló and A. Pappalardo

Abstract top

The title compound, C62H76O5, known to be one of the most versatile synthetic precursors/intermediates of calix[5]arene derivatives, adopts an approximate Cs-symmetric cone-in conformation. The aryloxybenzyl ring is tilted in such a way that the p-tert-butyl group fills the macrocycle cavity, while the benzyl group moves away from the cavity axis. In the crystal, this conformational arrangement is secured by intra- and intermolecular O-H...O hydrogen bonds forming inversion dimers. Four tert-butyl groups are disordered over two orientations, with occupancy ratios of 0.745 (6):0.255 (6), 0.837 (5):0.163 (5), 0.850 (5):0.150 (5) and 0.845 (8):0.155 (8).

Comment top

In the solid state the title compound adopts an approximate Cs-symmetric cone-in conformation, best described by (i) the leaning of the p-tert-butyl group of the benzylated ring inside the macrocycle cavity (defined by the four remaining p-tert-butylphenolic rings) and (ii) the concomitant tilting of the benzyl pendant group away from the cavity axis. The crystal packing shows the presence of pairs of centrosymmetric cone-shaped calix[5]arene molecules glued together –via their narrow rims– by several intra- and intermolecular hydrogen-bonding interactions involving the four hydroxyl groups present on each molecule. In addition, the benzyl (C22–C27) moiety and the p-tert-butylphenolic ring (C12–C14/C44/C43/C42) of each pair of centrosymmetric molecules lie on roughly parallel planes and their edges (C23/C24 and C12/C14, respectively) are seen at a spatial proximity of 3.5 Å (centroid-centroid = 4.47 (2) Å). In analogy with previously reported calixarene structures, collected at low temperature, four tert-butyl groups are disordered over two rotated orientations with refined occupancy factors.

Related literature top

For the synthesis of the title compound, see: Stewart et al. (1995). For calix[5]arene molecules derived from the title compound, see: Garozzo et al. (2005); Capici et al. (2011); Pappalardo et al. (2012). For the structures of calix[5]arene/alkylammonium complexes, see: Gattuso et al. (2012).

Experimental top

The title compound was prepared according to the procedure described by Stewart et al. (1995). p-tert-Butylcalix[5]arene (5.00 g, 6.17 mmol) and anhydrous KHCO3 (1.23 g, 12.32 mmol) were suspended in anhydrous MeCN (125 ml). The mixture was heated at reflux for 1 h under an inert atmosphere. Benzyl chloride (0.262 g, 2.09 mmol) was added, and heating was continued for 24 h. The mixture was then allowed to cool, and the solvent was removed under reduced pressure. The resulting residue was partitioned between CHCl3 (100 ml) and aqueous HCl (1 M, 75 ml). The organic layer was washed with H2O (2 × 100 ml) and dried over anhydrous MgSO4. The solvent was evaporated under reduced pressure, and the resulting residue was subjected to column chromatography (SiO2, toluene/n-hexane 1:1 v/v), to yield the title compound (68%, 1.15 g). Single crystals were obtained by slow evaporation from a CHCl3/MeOH solution. Spectral data are in full agreement with those reported in the literature (Stewart et al., 1995).

Refinement top

H atoms were included in the refinement via the "riding model" method, with C—H = 0.93–0.97 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O, Cmethyl). Four of the five tert-butyl groups showed a rotational disorder. As a result, they were individually treated as an overlap of two rotated conformations and the occupancy factors of the methyl groups were then refined. Owing to the significant disorder, suitable bond and displacement restraints (DFIX and ISOR) were applied and the C atoms of minor components were refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XPW (Siemens, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of the title molecule with the corresponding atom labelling. Displacement ellipsoids are plotted at a 30% probability level while H atom size is arbitrary.
[Figure 2] Fig. 2. Side view of a centrosymmetric molecular pair (1 - x, -y, 1 - z) showing the sandwiched arrangement of two molecules of the title compound with the hydroxyl group layer located in the middle and the benzyl pendant moieties on the outer surface. Minor components of the disordered tert-butyl groups and H atoms not involved in hydrogen bond interactions have been omitted for clarity. Displacement ellipsoids are plotted at a 50% probability level.
31-Benzyloxy-5,11,17,23,29-penta-tert-butylcalix[5]arene- 32,33,34,35-tetraol top
Crystal data top
C62H76O5Z = 2
Mr = 901.23F(000) = 976
Triclinic, P1Dx = 1.090 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 14.1467 (8) ÅCell parameters from 9983 reflections
b = 14.3235 (9) Åθ = 2.8–22.1°
c = 15.2179 (9) ŵ = 0.07 mm1
α = 70.653 (3)°T = 296 K
β = 78.776 (3)°Irregular, colourless
γ = 71.573 (3)°0.38 × 0.18 × 0.10 mm
V = 2746.3 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer
5343 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 26.0°, θmin = 2.0°
φ and ω scansh = 1717
75089 measured reflectionsk = 1717
10532 independent reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.161 w = 1/[σ2(Fo2) + (0.0863P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
10532 reflectionsΔρmax = 0.45 e Å3
677 parametersΔρmin = 0.16 e Å3
120 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0062 (10)
Crystal data top
C62H76O5γ = 71.573 (3)°
Mr = 901.23V = 2746.3 (3) Å3
Triclinic, P1Z = 2
a = 14.1467 (8) ÅMo Kα radiation
b = 14.3235 (9) ŵ = 0.07 mm1
c = 15.2179 (9) ÅT = 296 K
α = 70.653 (3)°0.38 × 0.18 × 0.10 mm
β = 78.776 (3)°
Data collection top
Bruker APEXII CCD
diffractometer
5343 reflections with I > 2σ(I)
75089 measured reflectionsRint = 0.044
10532 independent reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.161Δρmax = 0.45 e Å3
S = 0.96Δρmin = 0.16 e Å3
10532 reflectionsAbsolute structure: ?
677 parametersFlack parameter: ?
120 restraintsRogers parameter: ?
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.36078 (11)0.28637 (11)0.59304 (10)0.0549 (4)
O20.62075 (12)0.12493 (12)0.56199 (12)0.0650 (5)
H20.56690.16780.55060.098*
O30.71031 (12)0.05203 (12)0.43351 (10)0.0543 (4)
H30.69720.05090.48810.081*
O40.55263 (11)0.01224 (12)0.32381 (10)0.0575 (4)
H40.60240.03110.35190.086*
O50.37944 (11)0.11640 (11)0.39079 (9)0.0521 (4)
H50.42430.07490.36930.078*
C10.41318 (16)0.32444 (16)0.50767 (14)0.0458 (5)
C20.50301 (17)0.34459 (17)0.50671 (15)0.0520 (6)
C30.54754 (17)0.3264 (2)0.59638 (16)0.0641 (7)
H3A0.54170.39210.60510.077*
H3B0.50970.28960.64920.077*
C40.65643 (17)0.26538 (18)0.59418 (14)0.0513 (6)
C50.68675 (17)0.17104 (17)0.57534 (14)0.0477 (6)
C60.78683 (16)0.11664 (16)0.56911 (14)0.0448 (5)
C70.81837 (17)0.01950 (16)0.54016 (14)0.0481 (6)
H7A0.76930.01910.56850.058*
H7B0.88200.02250.56370.058*
C80.82882 (15)0.03977 (15)0.43458 (14)0.0415 (5)
C90.78124 (15)0.00094 (15)0.38942 (14)0.0416 (5)
C100.80587 (15)0.00926 (15)0.29388 (14)0.0430 (5)
C110.76412 (16)0.04627 (17)0.24796 (15)0.0495 (6)
H11A0.81780.07700.20730.059*
H11B0.74330.10190.29650.059*
C120.67691 (16)0.01793 (16)0.19121 (15)0.0455 (5)
C130.57818 (16)0.02790 (16)0.22883 (14)0.0443 (5)
C140.49976 (16)0.07443 (15)0.17293 (15)0.0450 (5)
C150.39230 (16)0.07875 (16)0.21118 (15)0.0488 (6)
H15A0.39110.02270.26830.059*
H15B0.35920.06860.16630.059*
C160.33380 (15)0.17948 (15)0.23208 (14)0.0412 (5)
C170.33033 (15)0.19305 (16)0.31852 (14)0.0414 (5)
C180.27617 (15)0.28567 (16)0.33713 (14)0.0430 (5)
C190.28254 (16)0.30445 (17)0.42731 (14)0.0482 (6)
H19A0.28010.24310.47880.058*
H19B0.22530.35980.43820.058*
C200.37805 (16)0.33231 (15)0.42491 (14)0.0448 (5)
C210.2932 (2)0.3616 (2)0.63292 (17)0.0727 (8)
H21A0.23590.39670.59710.087*
H21B0.32580.41220.63220.087*
C220.25972 (19)0.3090 (2)0.73196 (17)0.0613 (7)
C230.3257 (2)0.2356 (2)0.79098 (19)0.0747 (8)
H230.39330.21790.76940.090*
C240.2951 (3)0.1873 (2)0.8811 (2)0.0867 (9)
H240.34180.13780.91970.104*
C250.1978 (4)0.2110 (3)0.9140 (2)0.1052 (12)
H250.17750.17860.97540.126*
C260.1291 (3)0.2826 (3)0.8570 (3)0.1205 (13)
H260.06140.29790.87880.145*
C270.1609 (2)0.3329 (3)0.7654 (2)0.0993 (10)
H270.11440.38310.72700.119*
C280.73001 (18)0.30385 (18)0.60666 (15)0.0562 (6)
H280.71070.36750.61800.067*
C290.83081 (18)0.25165 (18)0.60289 (16)0.0550 (6)
C300.85644 (17)0.15751 (17)0.58484 (14)0.0514 (6)
H300.92340.12010.58320.062*
C310.91070 (19)0.29486 (19)0.61607 (19)0.0754 (8)
C320.9620 (4)0.2200 (4)0.7031 (4)0.162 (3)0.745 (6)
H32A0.98910.15270.69460.243*0.745 (6)
H32B0.91380.21700.75730.243*0.745 (6)
H32C1.01500.24350.71180.243*0.745 (6)
C330.8703 (3)0.3968 (3)0.6352 (5)0.126 (3)0.745 (6)
H33A0.92370.41600.64890.189*0.745 (6)
H33B0.82020.39220.68780.189*0.745 (6)
H33C0.84110.44760.58120.189*0.745 (6)
C340.9895 (5)0.2986 (7)0.5337 (5)0.200 (5)0.745 (6)
H34A1.04500.31460.54740.300*0.745 (6)
H34B0.96170.35060.47960.300*0.745 (6)
H34C1.01220.23300.52150.300*0.745 (6)
C32'0.8858 (11)0.3258 (13)0.7054 (7)0.116 (6)*0.255 (6)
H32D0.89040.26550.75830.173*0.255 (6)
H32E0.81900.37040.70700.173*0.255 (6)
H32F0.93230.36110.70790.173*0.255 (6)
C33'0.9007 (11)0.3965 (8)0.5359 (8)0.114 (6)*0.255 (6)
H33D0.95000.42870.53810.172*0.255 (6)
H33E0.83490.44170.54300.172*0.255 (6)
H33F0.91090.38230.47690.172*0.255 (6)
C34'1.0182 (5)0.2400 (10)0.5963 (9)0.085 (5)*0.255 (6)
H34D1.02840.23030.53530.128*0.255 (6)
H34E1.03470.17430.64250.128*0.255 (6)
H34F1.06020.28020.59830.128*0.255 (6)
C350.89385 (16)0.09669 (16)0.37994 (15)0.0483 (6)
H350.92420.12550.40940.058*
C360.91619 (16)0.11311 (17)0.28425 (15)0.0502 (6)
C370.87201 (16)0.06520 (17)0.24414 (15)0.0511 (6)
H370.88800.07130.18060.061*
C380.98979 (18)0.17462 (19)0.22501 (16)0.0619 (7)
C391.0147 (2)0.2362 (2)0.2786 (2)0.0927 (9)
H39A1.04450.19000.33410.139*
H39B0.95450.28370.29560.139*
H39C1.06090.27340.23960.139*
C401.0877 (2)0.1008 (2)0.1996 (2)0.0897 (9)
H40A1.07510.06240.16420.135*
H40B1.11600.05440.25580.135*
H40C1.13390.13920.16290.135*
C410.9457 (2)0.2485 (2)0.1357 (2)0.0993 (10)
H41A0.99120.28830.10020.149*
H41B0.88300.29380.15140.149*
H41C0.93520.21020.09900.149*
C420.69514 (17)0.06404 (17)0.09611 (15)0.0522 (6)
H420.76110.06050.07060.063*
C430.61966 (18)0.11512 (17)0.03748 (15)0.0512 (6)
C440.52328 (17)0.11696 (17)0.07761 (15)0.0509 (6)
H440.47140.14810.03930.061*
C450.64528 (17)0.16541 (18)0.06686 (15)0.0620 (7)
C460.7301 (3)0.0902 (3)0.1089 (2)0.0960 (15)0.837 (5)
H46A0.71370.02620.09410.144*0.837 (5)
H46B0.79120.07840.08330.144*0.837 (5)
H46C0.73870.11880.17560.144*0.837 (5)
C470.6761 (4)0.2596 (3)0.0760 (2)0.1068 (16)0.837 (5)
H47A0.73490.24010.04430.160*0.837 (5)
H47B0.62280.30550.04860.160*0.837 (5)
H47C0.69050.29350.14100.160*0.837 (5)
C480.5569 (3)0.1925 (4)0.1228 (2)0.1080 (17)0.837 (5)
H48A0.57640.21990.18810.162*0.837 (5)
H48B0.50220.24290.10210.162*0.837 (5)
H48C0.53630.13180.11330.162*0.837 (5)
C46'0.7528 (6)0.1730 (16)0.0891 (14)0.102 (7)*0.163 (5)
H46D0.76100.21960.06000.153*0.163 (5)
H46E0.76760.19780.15570.153*0.163 (5)
H46F0.79770.10620.06580.153*0.163 (5)
C47'0.5730 (12)0.2719 (8)0.0950 (13)0.099 (7)*0.163 (5)
H47D0.58470.30260.16110.149*0.163 (5)
H47E0.58320.31390.06180.149*0.163 (5)
H47F0.50540.26650.07980.149*0.163 (5)
C48'0.6344 (15)0.0990 (12)0.1214 (12)0.094 (7)*0.163 (5)
H48D0.65560.12610.18640.141*0.163 (5)
H48E0.56560.09860.11450.141*0.163 (5)
H48F0.67520.03010.09790.141*0.163 (5)
C490.28559 (15)0.26181 (17)0.16264 (14)0.0464 (5)
H490.28920.25320.10400.056*
C500.23254 (16)0.35584 (17)0.17608 (15)0.0467 (5)
C510.22843 (16)0.36418 (17)0.26557 (15)0.0487 (6)
H510.19160.42590.27760.058*
C520.18700 (18)0.44912 (17)0.09701 (15)0.0588 (6)
C530.0794 (3)0.4987 (3)0.1274 (3)0.1048 (16)0.850 (5)
H53A0.05260.55860.07810.157*0.850 (5)
H53B0.07690.51810.18260.157*0.850 (5)
H53C0.04040.45070.14070.157*0.850 (5)
C540.1829 (3)0.4194 (2)0.0103 (2)0.0907 (14)0.850 (5)
H54A0.14980.36580.02810.136*0.850 (5)
H54B0.24970.39540.01700.136*0.850 (5)
H54C0.14650.47830.03440.136*0.850 (5)
C550.2503 (4)0.5231 (3)0.0704 (3)0.125 (2)0.850 (5)
H55A0.22620.57920.01710.187*0.850 (5)
H55B0.31860.48830.05510.187*0.850 (5)
H55C0.24650.54910.12200.187*0.850 (5)
C53'0.0982 (12)0.4379 (19)0.0641 (17)0.122 (10)*0.150 (5)
H53D0.07170.49890.01560.183*0.150 (5)
H53E0.04750.42810.11570.183*0.150 (5)
H53F0.11900.37960.04020.183*0.150 (5)
C54'0.2703 (14)0.462 (2)0.0183 (14)0.142 (11)*0.150 (5)
H54D0.30290.39750.00570.212*0.150 (5)
H54E0.31810.48570.03630.212*0.150 (5)
H54F0.24270.51180.03700.212*0.150 (5)
C55'0.1526 (15)0.5447 (10)0.1309 (13)0.084 (7)*0.150 (5)
H55D0.11990.60250.08280.126*0.150 (5)
H55E0.20960.55810.14480.126*0.150 (5)
H55F0.10660.53370.18620.126*0.150 (5)
C560.43687 (17)0.36095 (16)0.34192 (15)0.0508 (6)
H560.41430.36710.28630.061*
C570.52754 (17)0.38087 (17)0.33753 (15)0.0519 (6)
C580.55820 (18)0.37356 (18)0.42081 (17)0.0573 (6)
H580.61790.38850.41950.069*
C590.59229 (18)0.40210 (19)0.24439 (16)0.0663 (7)
C600.6308 (5)0.3040 (3)0.2156 (4)0.134 (2)0.845 (8)
H60A0.66930.31670.15560.202*0.845 (8)
H60B0.57520.28120.21170.202*0.845 (8)
H60C0.67230.25180.26120.202*0.845 (8)
C610.6830 (4)0.4321 (6)0.2516 (3)0.145 (3)0.845 (8)
H61A0.72160.44450.19160.218*0.845 (8)
H61B0.72330.37750.29660.218*0.845 (8)
H61C0.66180.49350.27100.218*0.845 (8)
C620.5313 (3)0.4880 (6)0.1718 (3)0.189 (4)0.845 (8)
H62A0.50490.54800.19330.284*0.845 (8)
H62B0.47710.46700.16180.284*0.845 (8)
H62C0.57310.50350.11410.284*0.845 (8)
C60'0.6857 (12)0.3130 (14)0.2529 (16)0.113 (10)*0.155 (8)
H60D0.71620.30930.19160.169*0.155 (8)
H60E0.66830.25020.28730.169*0.155 (8)
H60F0.73200.32290.28530.169*0.155 (8)
C61'0.6164 (19)0.5021 (11)0.2300 (15)0.091 (8)*0.155 (8)
H61D0.65690.49360.27740.136*0.155 (8)
H61E0.55530.55500.23420.136*0.155 (8)
H61F0.65220.52120.16940.136*0.155 (8)
C62'0.5416 (13)0.4107 (16)0.1617 (9)0.065 (6)*0.155 (8)
H62D0.47930.46340.15860.097*0.155 (8)
H62E0.52930.34620.16920.097*0.155 (8)
H62F0.58430.42810.10490.097*0.155 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0611 (10)0.0554 (10)0.0425 (9)0.0073 (8)0.0004 (7)0.0183 (7)
O20.0566 (11)0.0627 (11)0.0809 (12)0.0222 (8)0.0185 (9)0.0150 (9)
O30.0653 (11)0.0633 (10)0.0404 (9)0.0316 (8)0.0003 (8)0.0124 (8)
O40.0513 (10)0.0703 (11)0.0436 (9)0.0118 (8)0.0040 (7)0.0119 (8)
O50.0561 (10)0.0479 (9)0.0418 (9)0.0060 (7)0.0028 (7)0.0086 (7)
C10.0486 (14)0.0435 (13)0.0394 (13)0.0040 (10)0.0044 (10)0.0126 (10)
C20.0489 (14)0.0572 (14)0.0487 (15)0.0046 (11)0.0097 (11)0.0205 (11)
C30.0549 (16)0.0833 (18)0.0576 (16)0.0056 (13)0.0125 (12)0.0336 (14)
C40.0521 (15)0.0582 (15)0.0427 (13)0.0078 (12)0.0096 (10)0.0176 (11)
C50.0495 (14)0.0564 (15)0.0392 (13)0.0180 (12)0.0099 (10)0.0099 (11)
C60.0515 (14)0.0464 (13)0.0366 (12)0.0138 (11)0.0098 (10)0.0083 (10)
C70.0578 (14)0.0451 (13)0.0407 (13)0.0147 (11)0.0118 (10)0.0071 (10)
C80.0425 (12)0.0370 (12)0.0406 (12)0.0075 (10)0.0058 (10)0.0078 (10)
C90.0408 (12)0.0368 (12)0.0411 (13)0.0097 (10)0.0027 (10)0.0053 (10)
C100.0418 (13)0.0425 (13)0.0406 (13)0.0052 (10)0.0044 (10)0.0126 (10)
C110.0483 (14)0.0520 (14)0.0460 (13)0.0054 (11)0.0017 (10)0.0209 (11)
C120.0482 (14)0.0471 (13)0.0429 (13)0.0073 (10)0.0064 (10)0.0194 (11)
C130.0496 (14)0.0447 (13)0.0363 (13)0.0090 (10)0.0014 (10)0.0139 (10)
C140.0460 (13)0.0434 (13)0.0484 (14)0.0095 (10)0.0037 (11)0.0200 (11)
C150.0499 (14)0.0511 (14)0.0505 (13)0.0159 (11)0.0070 (10)0.0182 (11)
C160.0381 (12)0.0472 (13)0.0406 (13)0.0158 (10)0.0006 (9)0.0136 (11)
C170.0388 (12)0.0452 (13)0.0373 (13)0.0141 (10)0.0053 (9)0.0048 (10)
C180.0440 (13)0.0460 (13)0.0387 (12)0.0147 (10)0.0020 (10)0.0108 (10)
C190.0515 (14)0.0486 (13)0.0428 (13)0.0111 (11)0.0036 (10)0.0140 (10)
C200.0489 (14)0.0409 (13)0.0423 (13)0.0070 (10)0.0073 (10)0.0124 (10)
C210.0689 (18)0.0747 (18)0.0664 (18)0.0004 (14)0.0017 (14)0.0332 (15)
C220.0600 (17)0.0704 (17)0.0572 (16)0.0131 (14)0.0031 (13)0.0329 (14)
C230.0705 (19)0.093 (2)0.0608 (18)0.0297 (16)0.0067 (15)0.0147 (16)
C240.105 (3)0.103 (2)0.064 (2)0.044 (2)0.0059 (18)0.0268 (18)
C250.144 (4)0.109 (3)0.067 (2)0.043 (3)0.026 (2)0.043 (2)
C260.100 (3)0.134 (3)0.102 (3)0.012 (3)0.042 (2)0.049 (3)
C270.081 (2)0.108 (2)0.087 (2)0.0032 (19)0.0102 (18)0.038 (2)
C280.0598 (16)0.0561 (15)0.0588 (15)0.0097 (12)0.0154 (12)0.0247 (12)
C290.0571 (16)0.0549 (15)0.0587 (15)0.0120 (12)0.0155 (12)0.0214 (12)
C300.0473 (14)0.0562 (15)0.0513 (14)0.0101 (11)0.0111 (11)0.0168 (12)
C310.0654 (18)0.0744 (19)0.104 (2)0.0210 (15)0.0191 (16)0.0402 (17)
C320.151 (6)0.123 (5)0.249 (8)0.036 (4)0.144 (6)0.032 (4)
C330.100 (4)0.087 (4)0.234 (7)0.020 (3)0.052 (4)0.088 (4)
C340.172 (7)0.322 (12)0.228 (9)0.194 (8)0.091 (6)0.182 (9)
C350.0466 (14)0.0514 (14)0.0469 (14)0.0146 (11)0.0096 (10)0.0104 (11)
C360.0424 (13)0.0524 (14)0.0485 (14)0.0123 (11)0.0027 (10)0.0070 (11)
C370.0452 (14)0.0609 (15)0.0382 (13)0.0087 (12)0.0001 (10)0.0107 (11)
C380.0568 (16)0.0661 (16)0.0555 (15)0.0265 (13)0.0014 (12)0.0027 (13)
C390.102 (2)0.096 (2)0.089 (2)0.0631 (19)0.0056 (17)0.0130 (18)
C400.0609 (19)0.114 (2)0.082 (2)0.0322 (17)0.0139 (15)0.0171 (18)
C410.098 (2)0.105 (2)0.078 (2)0.0536 (19)0.0187 (17)0.0263 (18)
C420.0497 (14)0.0626 (15)0.0461 (14)0.0143 (12)0.0014 (11)0.0208 (12)
C430.0562 (16)0.0551 (14)0.0434 (13)0.0122 (11)0.0039 (11)0.0192 (11)
C440.0512 (15)0.0573 (14)0.0446 (14)0.0092 (11)0.0099 (11)0.0176 (11)
C450.0644 (17)0.0718 (17)0.0448 (14)0.0175 (13)0.0060 (12)0.0113 (13)
C460.105 (3)0.123 (3)0.052 (2)0.021 (2)0.0083 (19)0.033 (2)
C470.162 (5)0.093 (3)0.066 (2)0.068 (3)0.006 (2)0.005 (2)
C480.091 (3)0.173 (5)0.046 (2)0.043 (3)0.0165 (18)0.001 (2)
C490.0450 (13)0.0565 (15)0.0404 (13)0.0173 (11)0.0035 (10)0.0144 (11)
C500.0468 (13)0.0493 (14)0.0434 (13)0.0146 (11)0.0076 (10)0.0094 (11)
C510.0472 (14)0.0454 (13)0.0511 (14)0.0087 (10)0.0066 (11)0.0138 (11)
C520.0687 (17)0.0534 (15)0.0483 (14)0.0135 (13)0.0164 (12)0.0038 (12)
C530.095 (3)0.089 (3)0.089 (3)0.025 (2)0.030 (2)0.008 (2)
C540.126 (4)0.075 (2)0.063 (2)0.010 (2)0.048 (2)0.0056 (18)
C550.180 (5)0.095 (3)0.105 (3)0.092 (3)0.070 (3)0.046 (3)
C560.0562 (15)0.0547 (14)0.0409 (13)0.0146 (11)0.0096 (11)0.0108 (11)
C570.0550 (15)0.0488 (14)0.0487 (14)0.0138 (11)0.0046 (11)0.0106 (11)
C580.0504 (15)0.0621 (16)0.0617 (16)0.0155 (12)0.0092 (12)0.0189 (12)
C590.0623 (17)0.0794 (19)0.0546 (16)0.0277 (14)0.0027 (13)0.0126 (14)
C600.148 (5)0.153 (4)0.127 (4)0.080 (4)0.081 (4)0.089 (3)
C610.138 (5)0.248 (8)0.103 (3)0.143 (6)0.052 (3)0.071 (4)
C620.122 (4)0.198 (7)0.096 (4)0.010 (4)0.027 (3)0.081 (4)
Geometric parameters (Å, º) top
O1—C11.395 (2)C38—C401.524 (4)
O1—C211.414 (3)C38—C391.534 (4)
O2—C51.379 (3)C39—H39A0.9600
O2—H20.8200C39—H39B0.9600
O3—C91.384 (2)C39—H39C0.9600
O3—H30.8200C40—H40A0.9600
O4—C131.388 (2)C40—H40B0.9600
O4—H40.8200C40—H40C0.9600
O5—C171.383 (2)C41—H41A0.9600
O5—H50.8200C41—H41B0.9600
C1—C21.386 (3)C41—H41C0.9600
C1—C201.400 (3)C42—C431.384 (3)
C2—C581.392 (3)C42—H420.9300
C2—C31.524 (3)C43—C441.377 (3)
C3—C41.512 (3)C43—C451.534 (3)
C3—H3A0.9700C44—H440.9300
C3—H3B0.9700C45—C471.502 (3)
C4—C281.390 (3)C45—C48'1.511 (5)
C4—C51.391 (3)C45—C47'1.519 (5)
C5—C61.386 (3)C45—C481.526 (3)
C6—C301.385 (3)C45—C46'1.523 (5)
C6—C71.505 (3)C45—C461.533 (3)
C7—C81.521 (3)C46—H46A0.9600
C7—H7A0.9700C46—H46B0.9600
C7—H7B0.9700C46—H46C0.9600
C8—C91.380 (3)C47—H47A0.9600
C8—C351.389 (3)C47—H47B0.9600
C9—C101.401 (3)C47—H47C0.9600
C10—C371.374 (3)C48—H48A0.9600
C10—C111.515 (3)C48—H48B0.9600
C11—C121.512 (3)C48—H48C0.9600
C11—H11A0.9700C46'—H46D0.9600
C11—H11B0.9700C46'—H46E0.9600
C12—C131.384 (3)C46'—H46F0.9600
C12—C421.388 (3)C47'—H47D0.9600
C13—C141.387 (3)C47'—H47E0.9600
C14—C441.393 (3)C47'—H47F0.9600
C14—C151.508 (3)C48'—H48D0.9600
C15—C161.521 (3)C48'—H48E0.9600
C15—H15A0.9700C48'—H48F0.9600
C15—H15B0.9700C49—C501.379 (3)
C16—C171.382 (3)C49—H490.9300
C16—C491.385 (3)C50—C511.395 (3)
C17—C181.396 (3)C50—C521.530 (3)
C18—C511.379 (3)C51—H510.9300
C18—C191.507 (3)C52—C551.505 (3)
C19—C201.516 (3)C52—C53'1.510 (5)
C19—H19A0.9700C52—C531.515 (3)
C19—H19B0.9700C52—C54'1.517 (5)
C20—C561.385 (3)C52—C55'1.525 (5)
C21—C221.503 (3)C52—C541.531 (3)
C21—H21A0.9700C53—H53A0.9600
C21—H21B0.9700C53—H53B0.9600
C22—C271.366 (4)C53—H53C0.9600
C22—C231.365 (3)C54—H54A0.9600
C23—C241.369 (4)C54—H54B0.9600
C23—H230.9300C54—H54C0.9600
C24—C251.345 (4)C55—H55A0.9600
C24—H240.9300C55—H55B0.9600
C25—C261.363 (5)C55—H55C0.9600
C25—H250.9300C53'—H53D0.9600
C26—C271.400 (4)C53'—H53E0.9600
C26—H260.9300C53'—H53F0.9600
C27—H270.9300C54'—H54D0.9600
C28—C291.385 (3)C54'—H54E0.9600
C28—H280.9300C54'—H54F0.9600
C29—C301.387 (3)C55'—H55D0.9600
C29—C311.521 (3)C55'—H55E0.9600
C30—H300.9300C55'—H55F0.9600
C31—C34'1.498 (5)C56—C571.384 (3)
C31—C331.494 (4)C56—H560.9300
C31—C341.506 (4)C57—C581.379 (3)
C31—C32'1.511 (5)C57—C591.525 (3)
C31—C321.541 (4)C58—H580.9300
C31—C33'1.545 (5)C59—C61'1.513 (5)
C32—H32A0.9600C59—C601.515 (3)
C32—H32B0.9600C59—C621.509 (4)
C32—H32C0.9600C59—C60'1.511 (5)
C33—H33A0.9600C59—C611.510 (4)
C33—H33B0.9600C59—C62'1.518 (5)
C33—H33C0.9600C60—H60A0.9600
C34—H34A0.9600C60—H60B0.9600
C34—H34B0.9600C60—H60C0.9600
C34—H34C0.9600C61—H61A0.9600
C32'—H32D0.9600C61—H61B0.9600
C32'—H32E0.9600C61—H61C0.9600
C32'—H32F0.9600C62—H62A0.9600
C33'—H33D0.9600C62—H62B0.9600
C33'—H33E0.9600C62—H62C0.9600
C33'—H33F0.9600C60'—H60D0.9600
C34'—H34D0.9600C60'—H60E0.9600
C34'—H34E0.9600C60'—H60F0.9600
C34'—H34F0.9600C61'—H61D0.9600
C35—C361.384 (3)C61'—H61E0.9600
C35—H350.9300C61'—H61F0.9600
C36—C371.390 (3)C62'—H62D0.9600
C36—C381.537 (3)C62'—H62E0.9600
C37—H370.9300C62'—H62F0.9600
C38—C411.522 (3)
C1—O1—C21115.40 (17)C39—C38—C36111.8 (2)
C5—O2—H2109.5C38—C39—H39A109.5
C9—O3—H3109.5C38—C39—H39B109.5
C13—O4—H4109.5H39A—C39—H39B109.5
C17—O5—H5109.5C38—C39—H39C109.5
C2—C1—O1119.59 (19)H39A—C39—H39C109.5
C2—C1—C20121.4 (2)H39B—C39—H39C109.5
O1—C1—C20118.7 (2)C38—C40—H40A109.5
C1—C2—C58118.4 (2)C38—C40—H40B109.5
C1—C2—C3122.2 (2)H40A—C40—H40B109.5
C58—C2—C3119.2 (2)C38—C40—H40C109.5
C4—C3—C2112.05 (18)H40A—C40—H40C109.5
C4—C3—H3A109.2H40B—C40—H40C109.5
C2—C3—H3A109.2C38—C41—H41A109.5
C4—C3—H3B109.2C38—C41—H41B109.5
C2—C3—H3B109.2H41A—C41—H41B109.5
H3A—C3—H3B107.9C38—C41—H41C109.5
C28—C4—C5117.8 (2)H41A—C41—H41C109.5
C28—C4—C3121.1 (2)H41B—C41—H41C109.5
C5—C4—C3121.0 (2)C43—C42—C12123.0 (2)
O2—C5—C6115.4 (2)C43—C42—H42118.5
O2—C5—C4123.1 (2)C12—C42—H42118.5
C6—C5—C4121.5 (2)C44—C43—C42116.7 (2)
C30—C6—C5118.0 (2)C44—C43—C45123.2 (2)
C30—C6—C7121.5 (2)C42—C43—C45120.1 (2)
C5—C6—C7120.31 (19)C43—C44—C14123.1 (2)
C6—C7—C8112.92 (16)C43—C44—H44118.4
C6—C7—H7A109.0C14—C44—H44118.4
C8—C7—H7A109.0C48'—C45—C47'110.7 (9)
C6—C7—H7B109.0C47—C45—C48111.0 (3)
C8—C7—H7B109.0C48'—C45—C46'107.1 (9)
H7A—C7—H7B107.8C47'—C45—C46'110.1 (9)
C9—C8—C35117.42 (19)C48—C45—C46'136.0 (8)
C9—C8—C7124.07 (19)C47—C45—C43108.1 (2)
C35—C8—C7118.43 (19)C48'—C45—C43108.2 (7)
C8—C9—O3124.07 (18)C47'—C45—C43108.3 (8)
C8—C9—C10121.02 (19)C48—C45—C43111.5 (2)
O3—C9—C10114.86 (18)C46'—C45—C43112.5 (8)
C37—C10—C9118.3 (2)C47—C45—C46110.4 (3)
C37—C10—C11121.01 (19)C48—C45—C46105.5 (3)
C9—C10—C11120.61 (19)C43—C45—C46110.5 (2)
C12—C11—C10116.47 (17)C45—C46—H46A109.5
C12—C11—H11A108.2C45—C46—H46B109.5
C10—C11—H11A108.2C45—C46—H46C109.5
C12—C11—H11B108.2C45—C47—H47A109.5
C10—C11—H11B108.2C45—C47—H47B109.5
H11A—C11—H11B107.3C45—C47—H47C109.5
C13—C12—C42117.8 (2)C45—C48—H48A109.5
C13—C12—C11122.67 (19)C45—C48—H48B109.5
C42—C12—C11119.4 (2)C45—C48—H48C109.5
C12—C13—C14121.65 (19)C45—C46'—H46D109.5
C12—C13—O4121.84 (19)C45—C46'—H46E109.5
C14—C13—O4116.45 (19)H46D—C46'—H46E109.5
C13—C14—C44117.6 (2)C45—C46'—H46F109.5
C13—C14—C15122.64 (19)H46D—C46'—H46F109.5
C44—C14—C15119.80 (19)H46E—C46'—H46F109.5
C14—C15—C16113.64 (17)C45—C47'—H47D109.5
C14—C15—H15A108.8C45—C47'—H47E109.5
C16—C15—H15A108.8H47D—C47'—H47E109.5
C14—C15—H15B108.8C45—C47'—H47F109.5
C16—C15—H15B108.8H47D—C47'—H47F109.5
H15A—C15—H15B107.7H47E—C47'—H47F109.5
C17—C16—C49118.26 (19)C45—C48'—H48D109.5
C17—C16—C15121.58 (18)C45—C48'—H48E109.5
C49—C16—C15120.11 (18)H48D—C48'—H48E109.5
C16—C17—O5122.21 (19)C45—C48'—H48F109.5
C16—C17—C18121.16 (18)H48D—C48'—H48F109.5
O5—C17—C18116.63 (18)H48E—C48'—H48F109.5
C51—C18—C17117.78 (19)C50—C49—C16123.32 (19)
C51—C18—C19120.78 (19)C50—C49—H49118.3
C17—C18—C19120.81 (18)C16—C49—H49118.3
C18—C19—C20111.67 (17)C49—C50—C51116.04 (19)
C18—C19—H19A109.3C49—C50—C52123.01 (19)
C20—C19—H19A109.3C51—C50—C52120.8 (2)
C18—C19—H19B109.3C18—C51—C50123.4 (2)
C20—C19—H19B109.3C18—C51—H51118.3
H19A—C19—H19B107.9C50—C51—H51118.3
C56—C20—C1117.3 (2)C55—C52—C53111.6 (3)
C56—C20—C19121.72 (19)C53'—C52—C54'111.4 (11)
C1—C20—C19120.92 (19)C55—C52—C50108.4 (2)
O1—C21—C22108.4 (2)C53'—C52—C50112.9 (10)
O1—C21—H21A110.0C53—C52—C50110.3 (2)
C22—C21—H21A110.0C54'—C52—C50106.6 (11)
O1—C21—H21B110.0C53'—C52—C55'108.2 (10)
C22—C21—H21B110.0C54'—C52—C55'108.5 (10)
H21A—C21—H21B108.4C50—C52—C55'109.3 (7)
C27—C22—C23117.8 (3)C55—C52—C54108.8 (3)
C27—C22—C21120.5 (3)C53—C52—C54105.5 (2)
C23—C22—C21121.8 (2)C50—C52—C54112.1 (2)
C22—C23—C24121.7 (3)C55'—C52—C54138.4 (7)
C22—C23—H23119.1C52—C53—H53A109.5
C24—C23—H23119.1C52—C53—H53B109.5
C25—C24—C23120.4 (3)C52—C53—H53C109.5
C25—C24—H24119.8C52—C54—H54A109.5
C23—C24—H24119.8C52—C54—H54B109.5
C24—C25—C26119.8 (3)C52—C54—H54C109.5
C24—C25—H25120.1C52—C55—H55A109.5
C26—C25—H25120.1C52—C55—H55B109.5
C25—C26—C27119.5 (3)C52—C55—H55C109.5
C25—C26—H26120.2C52—C53'—H53D109.5
C27—C26—H26120.2C52—C53'—H53E109.5
C22—C27—C26120.7 (3)H53D—C53'—H53E109.5
C22—C27—H27119.7C52—C53'—H53F109.5
C26—C27—H27119.7H53D—C53'—H53F109.5
C29—C28—C4123.0 (2)H53E—C53'—H53F109.5
C29—C28—H28118.5C52—C54'—H54D109.5
C4—C28—H28118.5C52—C54'—H54E109.5
C30—C29—C28116.6 (2)H54D—C54'—H54E109.5
C30—C29—C31120.9 (2)C52—C54'—H54F109.5
C28—C29—C31122.5 (2)H54D—C54'—H54F109.5
C29—C30—C6123.0 (2)H54E—C54'—H54F109.5
C29—C30—H30118.5C52—C55'—H55D109.5
C6—C30—H30118.5C52—C55'—H55E109.5
C33—C31—C34111.3 (4)H55D—C55'—H55E109.5
C34'—C31—C32'115.3 (7)C52—C55'—H55F109.5
C34'—C31—C29117.9 (6)H55D—C55'—H55F109.5
C33—C31—C29114.0 (3)H55E—C55'—H55F109.5
C34—C31—C29110.3 (3)C57—C56—C20123.4 (2)
C32'—C31—C29111.2 (6)C57—C56—H56118.3
C33—C31—C32106.0 (3)C20—C56—H56118.3
C34—C31—C32107.5 (5)C58—C57—C56117.2 (2)
C29—C31—C32107.4 (2)C58—C57—C59122.7 (2)
C34'—C31—C33'100.9 (7)C56—C57—C59120.0 (2)
C32'—C31—C33'105.5 (8)C57—C58—C2122.4 (2)
C29—C31—C33'103.8 (6)C57—C58—H58118.8
C31—C32—H32A109.5C2—C58—H58118.8
C31—C32—H32B109.5C60—C59—C62111.2 (4)
C31—C32—H32C109.5C61'—C59—C60'111.6 (10)
C31—C33—H33A109.5C61'—C59—C57107.1 (9)
C31—C33—H33B109.5C60—C59—C57108.3 (2)
C31—C33—H33C109.5C62—C59—C57109.7 (2)
C31—C34—H34A109.5C60'—C59—C57106.8 (9)
C31—C34—H34B109.5C60—C59—C61106.8 (3)
C31—C34—H34C109.5C62—C59—C61108.6 (4)
C31—C32'—H32D109.5C57—C59—C61112.3 (2)
C31—C32'—H32E109.5C61'—C59—C62'109.4 (9)
H32D—C32'—H32E109.5C60'—C59—C62'108.6 (9)
C31—C32'—H32F109.5C57—C59—C62'113.4 (7)
H32D—C32'—H32F109.5C59—C60—H60A109.5
H32E—C32'—H32F109.5C59—C60—H60B109.5
C31—C33'—H33D109.5C59—C60—H60C109.5
C31—C33'—H33E109.5C59—C61—H61A109.5
H33D—C33'—H33E109.5C59—C61—H61B109.5
C31—C33'—H33F109.5C59—C61—H61C109.5
H33D—C33'—H33F109.5C59—C62—H62A109.5
H33E—C33'—H33F109.5C59—C62—H62B109.5
C31—C34'—H34D109.5C59—C62—H62C109.5
C31—C34'—H34E109.5C59—C60'—H60D109.5
H34D—C34'—H34E109.5C59—C60'—H60E109.5
C31—C34'—H34F109.5H60D—C60'—H60E109.5
H34D—C34'—H34F109.5C59—C60'—H60F109.5
H34E—C34'—H34F109.5H60D—C60'—H60F109.5
C36—C35—C8123.9 (2)H60E—C60'—H60F109.5
C36—C35—H35118.0C59—C61'—H61D109.5
C8—C35—H35118.0C59—C61'—H61E109.5
C35—C36—C37115.8 (2)H61D—C61'—H61E109.5
C35—C36—C38123.3 (2)C59—C61'—H61F109.5
C37—C36—C38120.8 (2)H61D—C61'—H61F109.5
C10—C37—C36123.1 (2)H61E—C61'—H61F109.5
C10—C37—H37118.4C59—C62'—H62D109.5
C36—C37—H37118.4C59—C62'—H62E109.5
C41—C38—C40109.3 (2)H62D—C62'—H62E109.5
C41—C38—C39108.8 (2)C59—C62'—H62F109.5
C40—C38—C39107.3 (2)H62D—C62'—H62F109.5
C41—C38—C36110.1 (2)H62E—C62'—H62F109.5
C40—C38—C36109.4 (2)
C21—O1—C1—C288.0 (2)C28—C29—C31—C331.2 (4)
C21—O1—C1—C2097.9 (2)C30—C29—C31—C3454.1 (5)
O1—C1—C2—C58174.25 (18)C28—C29—C31—C34124.9 (5)
C20—C1—C2—C580.2 (3)C30—C29—C31—C32'128.4 (7)
O1—C1—C2—C30.1 (3)C28—C29—C31—C32'52.6 (8)
C20—C1—C2—C3173.9 (2)C30—C29—C31—C3262.7 (4)
C1—C2—C3—C4130.4 (2)C28—C29—C31—C32118.3 (4)
C58—C2—C3—C443.7 (3)C30—C29—C31—C33'118.6 (6)
C2—C3—C4—C28123.0 (2)C28—C29—C31—C33'60.3 (7)
C2—C3—C4—C554.0 (3)C9—C8—C35—C362.5 (3)
C28—C4—C5—O2179.8 (2)C7—C8—C35—C36174.43 (19)
C3—C4—C5—O23.1 (3)C8—C35—C36—C372.4 (3)
C28—C4—C5—C60.0 (3)C8—C35—C36—C38178.8 (2)
C3—C4—C5—C6177.1 (2)C9—C10—C37—C360.6 (3)
O2—C5—C6—C30177.98 (18)C11—C10—C37—C36176.65 (19)
C4—C5—C6—C301.8 (3)C35—C36—C37—C103.4 (3)
O2—C5—C6—C75.7 (3)C38—C36—C37—C10179.9 (2)
C4—C5—C6—C7174.50 (18)C35—C36—C38—C41135.0 (3)
C30—C6—C7—C893.9 (2)C37—C36—C38—C4148.7 (3)
C5—C6—C7—C882.3 (2)C35—C36—C38—C40104.9 (3)
C6—C7—C8—C9126.2 (2)C37—C36—C38—C4071.4 (3)
C6—C7—C8—C3557.0 (3)C35—C36—C38—C3913.9 (3)
C35—C8—C9—O3176.16 (18)C37—C36—C38—C39169.9 (2)
C7—C8—C9—O37.1 (3)C13—C12—C42—C432.8 (3)
C35—C8—C9—C106.7 (3)C11—C12—C42—C43173.2 (2)
C7—C8—C9—C10170.06 (18)C12—C42—C43—C441.2 (3)
C8—C9—C10—C375.8 (3)C12—C42—C43—C45179.3 (2)
O3—C9—C10—C37176.79 (18)C42—C43—C44—C142.9 (3)
C8—C9—C10—C11171.38 (18)C45—C43—C44—C14177.67 (19)
O3—C9—C10—C116.0 (3)C13—C14—C44—C430.3 (3)
C37—C10—C11—C1281.4 (3)C15—C14—C44—C43179.39 (19)
C9—C10—C11—C12101.4 (2)C44—C43—C45—C47108.0 (3)
C10—C11—C12—C1392.6 (3)C42—C43—C45—C4772.5 (3)
C10—C11—C12—C4291.6 (2)C44—C43—C45—C48'74.4 (8)
C42—C12—C13—C145.5 (3)C42—C43—C45—C48'105.0 (8)
C11—C12—C13—C14170.40 (19)C44—C43—C45—C47'45.6 (9)
C42—C12—C13—O4177.51 (18)C42—C43—C45—C47'134.9 (9)
C11—C12—C13—O46.6 (3)C44—C43—C45—C4814.2 (4)
C12—C13—C14—C444.0 (3)C42—C43—C45—C48165.3 (3)
O4—C13—C14—C44178.87 (17)C44—C43—C45—C46'167.5 (9)
C12—C13—C14—C15175.02 (19)C42—C43—C45—C46'13.1 (9)
O4—C13—C14—C152.1 (3)C44—C43—C45—C46131.1 (3)
C13—C14—C15—C1697.2 (2)C42—C43—C45—C4648.4 (3)
C44—C14—C15—C1683.8 (2)C17—C16—C49—C501.5 (3)
C14—C15—C16—C1789.7 (2)C15—C16—C49—C50179.0 (2)
C14—C15—C16—C4987.8 (2)C16—C49—C50—C510.8 (3)
C49—C16—C17—O5177.51 (18)C16—C49—C50—C52174.7 (2)
C15—C16—C17—O50.0 (3)C17—C18—C51—C500.7 (3)
C49—C16—C17—C182.7 (3)C19—C18—C51—C50170.31 (19)
C15—C16—C17—C18179.79 (19)C49—C50—C51—C181.9 (3)
C16—C17—C18—C511.7 (3)C52—C50—C51—C18173.7 (2)
O5—C17—C18—C51178.52 (18)C49—C50—C52—C55105.1 (3)
C16—C17—C18—C19172.71 (18)C51—C50—C52—C5570.1 (3)
O5—C17—C18—C197.5 (3)C49—C50—C52—C53'70.9 (11)
C51—C18—C19—C2092.5 (2)C51—C50—C52—C53'113.8 (11)
C17—C18—C19—C2078.2 (2)C49—C50—C52—C53132.3 (3)
C2—C1—C20—C560.1 (3)C51—C50—C52—C5352.4 (3)
O1—C1—C20—C56173.96 (17)C49—C50—C52—C54'51.6 (11)
C2—C1—C20—C19176.6 (2)C51—C50—C52—C54'123.6 (11)
O1—C1—C20—C192.6 (3)C49—C50—C52—C55'168.6 (9)
C18—C19—C20—C5614.7 (3)C51—C50—C52—C55'6.6 (9)
C18—C19—C20—C1161.70 (19)C49—C50—C52—C5415.0 (3)
C1—O1—C21—C22168.44 (19)C51—C50—C52—C54169.7 (2)
O1—C21—C22—C27134.9 (3)C1—C20—C56—C570.6 (3)
O1—C21—C22—C2344.4 (3)C19—C20—C56—C57175.9 (2)
C27—C22—C23—C240.4 (4)C20—C56—C57—C581.5 (3)
C21—C22—C23—C24179.7 (2)C20—C56—C57—C59174.23 (19)
C22—C23—C24—C250.3 (4)C56—C57—C58—C21.8 (3)
C23—C24—C25—C260.8 (5)C59—C57—C58—C2173.8 (2)
C24—C25—C26—C271.8 (6)C1—C2—C58—C571.3 (3)
C23—C22—C27—C260.6 (5)C3—C2—C58—C57173.0 (2)
C21—C22—C27—C26178.7 (3)C58—C57—C59—C61'57.1 (10)
C25—C26—C27—C221.7 (5)C56—C57—C59—C61'127.4 (10)
C5—C4—C28—C291.3 (3)C58—C57—C59—C60107.6 (4)
C3—C4—C28—C29178.4 (2)C56—C57—C59—C6067.9 (4)
C4—C28—C29—C300.6 (3)C58—C57—C59—C62130.8 (5)
C4—C28—C29—C31179.6 (2)C56—C57—C59—C6253.7 (5)
C28—C29—C30—C61.3 (3)C58—C57—C59—C60'62.5 (11)
C31—C29—C30—C6177.7 (2)C56—C57—C59—C60'113.0 (11)
C5—C6—C30—C292.5 (3)C58—C57—C59—C6110.1 (5)
C7—C6—C30—C29173.72 (19)C56—C57—C59—C61174.5 (4)
C30—C29—C31—C34'8.1 (7)C58—C57—C59—C62'177.9 (9)
C28—C29—C31—C34'170.9 (6)C56—C57—C59—C62'6.6 (9)
C30—C29—C31—C33179.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O5i0.822.042.7197 (19)140
O4—H4···O30.822.042.847 (2)168
O5—H5···O40.822.002.803 (2)168
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O5i0.822.042.7197 (19)140
O4—H4···O30.822.042.847 (2)168
O5—H5···O40.822.002.803 (2)168
Symmetry code: (i) x+1, y, z+1.
Acknowledgements top

MIUR (PRIN-2009 A5Y3N9 project) is gratefully acknowledged for financial support.

references
References top

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