supplementary materials


rk2273 scheme

Acta Cryst. (2011). E67, o1128-o1129    [ doi:10.1107/S1600536811013201 ]

(2E,25E)-11,14,17,33,36,39,42-Heptaoxapentacyclo[41.4.0.05,10.018,23.027,32]heptatetraconta-1(43),2,5(10),6,8,18,20,22,25,27,29,31,44,46-tetradecaene-4,24-dione

L. T. Anh, T. H. Hieu, A. T. Soldatenkov, S. A. Soldatova and V. N. Khrustalev

Abstract top

The title compound, C40H40O9, is a product of the double crotonic condensation of bis(2-acetylphenoxy)-3-oxapentane with bis(2-formylphenoxy)-3,6-dioxaoctane. The title macromolecule includes the 31-crown-7-ether skeletal unit and adopts a saddle-like conformation. The two ethylene fragments have E configurations. The volume of the internal cavity of the macrocycle is approximately 125 Å3. In the crystal, the molecules are arranged at van der Waals distances.

Comment top

Design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry draw very great attention of investigators during the last forty years (Hiraoka, 1978; Pedersen, 1988; Gokel & Murillo, 1996; Bradshaw & Izatt, 1997). Recently, we have developed an effective method of synthesis of 14- and 17-membered azacrown (Levov et al., 2006; 2008) and crown (Anh et al., 2008) ethers. This method is based on domino reaction of three components - dialkyl ketone, bis(2-formylphenoxy)-3-oxapentane and ammonium acetate, i.e., the modified Petrenko–Kritchenko reaction (Levov, 2008).

In attempts to apply this chemistry for obtaining of a ditopic ligand, in which two azacrown units are connected to each other by polyether chain, we studied the similar condensation of bis(2-formylphenoxy)-3,6-dioxaoctane with bis(2-acetylphenoxy)-3-oxapentane and ammonium acetate, the latter being both a source of nitrogen and a template agent. However, instead of the expected azacrown system, tetrakis(benzo)-31-crown-7-ether (I) was formed.

The obtained compound I, C40H40O9, includes the 31–crown–7–ether skeletal moiety and adopts a saddle-like conformation (Fig. 1). The two ethylene fragments have Econfigurations. The dihedral angles between the benzene planes of C1,C43–C47/C5–C10, C5–C10/C18–C23, C18–C23/C27–C32 and C27–C32/C1,C43–C47 are 64.91 (8), 65.14 (8), 61.64 (8) and 56.67 (9)°, respectively. The volume of the internal cavity of macrocycle I is approximately equal to 125 Å3. The distances from the center of macrocycle cavity, defined as centroid of O11/O14/O17/O33/O36/O39/O42 oxygen donor atoms, to the O11, O14, O17, O33, O36, O39 and O42 oxygen atoms are 3.286 (3), 3.638 (3), 3.460 (3), 3.308 (3), 3.486 (3), 3.524 (3) and 2.533 (3) Å, respectively.

In the crystal, the molecules of I are arranged at van der Waals distances.

Related literature top

For general background to the design, synthesis and applications of macrocyclic ligands for coordination and supramolecular chemistry, see: Hiraoka (1978); Pedersen (1988); Bradshaw & Izatt (1997); Gokel & Murillo (1996). For related compounds, see: Levov et al. (2006); Anh et al. (2008); Levov et al. (2008).

Experimental top

Ammonium acetate (2.0 g, 26 mmol) was added to a solution of bis(2-formylphenoxy)-3,6-dioxaoctane (1.38 g, 4.40 mmol) with bis(2-acetylphenoxy)-3-oxapentane (1.50 g, 4.40 mmol) in ethanol (50 ml). The reaction mixture was stirred at 323 K for 2 h (monitoring by TLC until disappearance of the starting organic compounds spots). At the end of the reaction, the formed wax-like precipitate was separated, washed with cold ethanol (50 ml) and re-crystallized from ethanol to give 0.82 g of light-yellow crystals of I (Fig. 2). Yield is 28%. M.p. = 400–402 K. IR (KBr), ν/cm-1: 1618, 1682. 1H NMR (CDCl3 , 400 MHz, 300 K): δ = 3.54, 3.62, 3.85 and 4.11 (all m, 6H, 5H, 5H and 4H, respectively, OCH2CH2O), 6.70–7.23 and 7.28–7.55 (both m, 10H and 6H, respectively, Harom), 7.27 and 7.87 (both d, 2H each, OC—CHtransCH, J = 16.0). Anal. Calcd for C40H40O9: C, 72.29; H, 6.03. Found: C, 72.31; H, 6.12.

Refinement top

The 4537 Friedel pairs were merged in the refinement procedure. The hydrogen atoms were placed in calculated positions with C—H = 0.95–0.99Å and refined in the riding model with fixed isotropic displacement parameters Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of I with the atom numbering scheme. Displacement ellipsoids are shown at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
[Figure 2] Fig. 2. Domino cyclocondensation of bis(2-acetylphenoxy)-3-oxapentane with bis(2-formylphenoxy)-3,6-dioxaoctane.
(2E,25E)-11,14,17,33,36,39,42- Heptaoxapentacyclo[41.4.0.05,10.018,23.027,32]heptatetraconta- 1(43),2,5(10),6,8,18,20,22,25,27,29,31,44,46-tetradecaene-4,24-dione top
Crystal data top
C40H40O9F(000) = 704
Mr = 664.72Dx = 1.294 Mg m3
Monoclinic, P21Melting point = 400–402 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 12.3268 (6) ÅCell parameters from 7007 reflections
b = 11.0271 (6) Åθ = 2.5–29.6°
c = 13.1142 (7) ŵ = 0.09 mm1
β = 106.933 (1)°T = 120 K
V = 1705.32 (15) Å3Prism, light–yellow
Z = 20.30 × 0.30 × 0.20 mm
Data collection top
Bruker SMART 1K CCD
diffractometer
5222 independent reflections
Radiation source: fine-focus sealed tube4511 reflections with I > 2σ(I)
graphiteRint = 0.027
φ and ω scansθmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 1617
Tmin = 0.973, Tmax = 0.982k = 1515
19455 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.06P)2 + 0.86P]
where P = (Fo2 + 2Fc2)/3
5222 reflections(Δ/σ)max < 0.001
442 parametersΔρmax = 0.33 e Å3
1 restraintΔρmin = 0.20 e Å3
Crystal data top
C40H40O9V = 1705.32 (15) Å3
Mr = 664.72Z = 2
Monoclinic, P21Mo Kα radiation
a = 12.3268 (6) ŵ = 0.09 mm1
b = 11.0271 (6) ÅT = 120 K
c = 13.1142 (7) Å0.30 × 0.30 × 0.20 mm
β = 106.933 (1)°
Data collection top
Bruker SMART 1K CCD
diffractometer
5222 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
4511 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.982Rint = 0.027
19455 measured reflectionsθmax = 30.0°
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.128Δρmax = 0.33 e Å3
S = 1.01Δρmin = 0.20 e Å3
5222 reflectionsAbsolute structure: ?
442 parametersFlack parameter: ?
1 restraintRogers 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*/Ueq
C10.4588 (2)0.6322 (2)0.41234 (19)0.0280 (5)
C20.3718 (2)0.6146 (3)0.46784 (18)0.0280 (5)
H20.33470.53810.46030.034*
C30.3411 (2)0.6979 (3)0.5280 (2)0.0330 (5)
H30.37860.77420.53750.040*
C40.2520 (2)0.6771 (3)0.5802 (2)0.0325 (5)
O40.2392 (2)0.7497 (3)0.64613 (19)0.0559 (7)
C50.1818 (2)0.5638 (3)0.55711 (19)0.0290 (5)
C60.1917 (2)0.4805 (3)0.6388 (2)0.0359 (6)
H60.24160.49750.70750.043*
C70.1304 (3)0.3732 (3)0.6222 (3)0.0422 (7)
H70.13920.31650.67860.051*
C80.0566 (3)0.3495 (3)0.5232 (3)0.0438 (7)
H80.01490.27590.51120.053*
C90.0426 (3)0.4326 (3)0.4402 (2)0.0371 (6)
H90.00990.41630.37260.044*
C100.1056 (2)0.5392 (2)0.4565 (2)0.0295 (5)
O110.09816 (16)0.62631 (18)0.38125 (13)0.0306 (4)
C120.0157 (2)0.6097 (3)0.2789 (2)0.0321 (5)
H12A0.06070.59920.28790.039*
H12B0.03420.53630.24380.039*
C130.0177 (2)0.7199 (3)0.2117 (2)0.0309 (5)
H13A0.05820.72980.15980.037*
H13B0.03220.79230.25850.037*
O140.10022 (15)0.71629 (19)0.15489 (13)0.0313 (4)
C150.2133 (2)0.7259 (3)0.22173 (19)0.0305 (5)
H15A0.23410.65200.26600.037*
H15B0.22040.79650.26980.037*
C160.2910 (2)0.7410 (2)0.15298 (19)0.0294 (5)
H16A0.26470.80820.10160.035*
H16B0.36920.75890.19740.035*
O170.28744 (16)0.62817 (17)0.09792 (14)0.0308 (4)
C180.34907 (19)0.6155 (2)0.02800 (18)0.0257 (4)
C190.4309 (2)0.6979 (3)0.0181 (2)0.0314 (5)
H190.44290.77090.05830.038*
C200.4949 (2)0.6732 (3)0.0504 (2)0.0369 (6)
H200.55070.72980.05670.044*
C210.4791 (2)0.5674 (3)0.1099 (2)0.0368 (6)
H210.52340.55150.15680.044*
C220.3976 (2)0.4848 (3)0.1002 (2)0.0305 (5)
H220.38810.41100.13920.037*
C230.32910 (19)0.5088 (2)0.03355 (18)0.0248 (4)
C240.2399 (2)0.4172 (2)0.03145 (19)0.0266 (5)
O240.25237 (16)0.31193 (18)0.05580 (17)0.0365 (4)
C250.1368 (2)0.4551 (2)0.00417 (19)0.0258 (4)
H250.11640.53840.00790.031*
C260.07174 (19)0.3731 (2)0.02578 (18)0.0246 (4)
H260.09630.29100.03140.030*
C270.03407 (19)0.4002 (2)0.05046 (18)0.0238 (4)
C280.0994 (2)0.5025 (2)0.0089 (2)0.0275 (5)
H280.07360.55710.03510.033*
C290.2012 (2)0.5259 (2)0.0307 (2)0.0310 (5)
H290.24470.59550.00160.037*
C300.2387 (2)0.4466 (3)0.0954 (2)0.0328 (5)
H300.30850.46200.11000.039*
C310.1751 (2)0.3444 (3)0.13935 (19)0.0298 (5)
H310.20120.29090.18390.036*
C320.0731 (2)0.3219 (2)0.11732 (18)0.0263 (5)
O330.00317 (15)0.22654 (18)0.15923 (14)0.0312 (4)
C340.0337 (2)0.1520 (2)0.2361 (2)0.0304 (5)
H34A0.10300.10490.20130.036*
H34B0.04890.20310.29250.036*
C350.0637 (2)0.0675 (3)0.2836 (2)0.0346 (5)
H35A0.03970.00260.32460.042*
H35B0.08970.02940.22650.042*
O360.15233 (17)0.1363 (2)0.35162 (16)0.0397 (5)
C370.2517 (2)0.0645 (3)0.3974 (2)0.0430 (7)
H37A0.22800.01890.40910.052*
H37B0.29290.09870.46790.052*
C380.3315 (3)0.0587 (3)0.3289 (3)0.0433 (7)
H38A0.38750.00660.35610.052*
H38B0.28730.03700.25520.052*
O390.39042 (17)0.1687 (2)0.32615 (17)0.0398 (5)
C400.3283 (2)0.2565 (3)0.2534 (2)0.0355 (6)
H40A0.26390.28670.27700.043*
H40B0.29780.22020.18170.043*
C410.4075 (2)0.3590 (3)0.2498 (2)0.0335 (5)
H41A0.48250.32650.25030.040*
H41B0.37690.40660.18360.040*
O420.41902 (17)0.43507 (18)0.34075 (15)0.0338 (4)
C430.4779 (2)0.5409 (2)0.3452 (2)0.0291 (5)
C440.5554 (2)0.5598 (3)0.2867 (2)0.0375 (6)
H440.56870.49780.24160.045*
C450.6126 (2)0.6697 (3)0.2950 (2)0.0399 (6)
H450.66400.68310.25440.048*
C460.5952 (2)0.7595 (3)0.3620 (2)0.0402 (6)
H460.63540.83400.36810.048*
C470.5192 (2)0.7412 (3)0.4201 (2)0.0339 (5)
H470.50770.80350.46590.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0239 (10)0.0335 (13)0.0271 (10)0.0007 (10)0.0083 (8)0.0022 (10)
C20.0250 (10)0.0333 (12)0.0254 (10)0.0011 (9)0.0068 (8)0.0013 (10)
C30.0306 (12)0.0400 (15)0.0298 (11)0.0059 (11)0.0110 (9)0.0065 (11)
C40.0299 (11)0.0424 (15)0.0266 (11)0.0012 (11)0.0106 (9)0.0046 (11)
O40.0670 (15)0.0603 (16)0.0529 (13)0.0158 (13)0.0372 (12)0.0260 (12)
C50.0264 (10)0.0362 (13)0.0286 (11)0.0054 (10)0.0148 (9)0.0008 (10)
C60.0312 (12)0.0477 (16)0.0329 (12)0.0137 (12)0.0156 (10)0.0084 (12)
C70.0428 (15)0.0457 (17)0.0458 (16)0.0144 (13)0.0252 (13)0.0179 (13)
C80.0499 (17)0.0360 (15)0.0527 (17)0.0003 (13)0.0264 (14)0.0066 (13)
C90.0418 (14)0.0332 (14)0.0385 (14)0.0047 (12)0.0154 (11)0.0005 (11)
C100.0324 (11)0.0319 (12)0.0275 (11)0.0007 (10)0.0137 (9)0.0015 (10)
O110.0372 (9)0.0307 (9)0.0228 (7)0.0078 (8)0.0071 (7)0.0014 (7)
C120.0358 (12)0.0325 (13)0.0257 (11)0.0056 (10)0.0051 (9)0.0024 (10)
C130.0315 (12)0.0341 (13)0.0291 (11)0.0037 (10)0.0118 (9)0.0036 (10)
O140.0298 (8)0.0393 (10)0.0261 (8)0.0015 (8)0.0101 (6)0.0012 (8)
C150.0306 (12)0.0336 (12)0.0275 (11)0.0016 (10)0.0087 (9)0.0029 (10)
C160.0322 (12)0.0271 (12)0.0291 (11)0.0037 (10)0.0095 (9)0.0045 (9)
O170.0362 (9)0.0279 (9)0.0334 (9)0.0060 (8)0.0184 (7)0.0049 (7)
C180.0238 (10)0.0283 (11)0.0254 (10)0.0002 (9)0.0076 (8)0.0027 (9)
C190.0294 (11)0.0316 (13)0.0334 (12)0.0070 (10)0.0096 (9)0.0020 (10)
C200.0267 (11)0.0442 (15)0.0403 (13)0.0087 (11)0.0108 (10)0.0056 (12)
C210.0284 (12)0.0488 (17)0.0373 (13)0.0010 (12)0.0158 (10)0.0035 (13)
C220.0254 (11)0.0375 (13)0.0301 (11)0.0028 (10)0.0103 (9)0.0036 (10)
C230.0205 (9)0.0283 (11)0.0260 (10)0.0010 (9)0.0076 (8)0.0027 (9)
C240.0239 (10)0.0280 (11)0.0286 (11)0.0001 (9)0.0087 (8)0.0029 (9)
O240.0329 (9)0.0272 (9)0.0522 (12)0.0004 (8)0.0169 (8)0.0042 (8)
C250.0266 (10)0.0236 (11)0.0281 (11)0.0014 (9)0.0093 (8)0.0020 (9)
C260.0254 (10)0.0237 (11)0.0261 (10)0.0018 (9)0.0098 (8)0.0005 (8)
C270.0244 (10)0.0241 (11)0.0240 (10)0.0031 (9)0.0089 (8)0.0016 (8)
C280.0287 (11)0.0249 (11)0.0302 (11)0.0022 (9)0.0105 (9)0.0012 (9)
C290.0293 (11)0.0277 (12)0.0364 (13)0.0014 (10)0.0105 (9)0.0012 (10)
C300.0288 (11)0.0361 (14)0.0363 (13)0.0003 (10)0.0140 (10)0.0044 (11)
C310.0295 (11)0.0331 (13)0.0300 (11)0.0038 (10)0.0137 (9)0.0012 (10)
C320.0293 (11)0.0255 (11)0.0261 (10)0.0036 (9)0.0111 (9)0.0015 (9)
O330.0317 (9)0.0336 (9)0.0317 (9)0.0023 (8)0.0145 (7)0.0088 (8)
C340.0329 (12)0.0295 (12)0.0316 (12)0.0031 (10)0.0139 (9)0.0046 (10)
C350.0382 (13)0.0329 (13)0.0336 (12)0.0050 (11)0.0118 (10)0.0026 (11)
O360.0379 (10)0.0381 (11)0.0405 (10)0.0052 (9)0.0074 (8)0.0026 (9)
C370.0390 (14)0.0422 (16)0.0427 (15)0.0061 (13)0.0042 (12)0.0122 (13)
C380.0405 (15)0.0318 (14)0.0543 (17)0.0010 (12)0.0088 (13)0.0054 (13)
O390.0334 (9)0.0371 (11)0.0448 (11)0.0034 (8)0.0051 (8)0.0071 (9)
C400.0351 (13)0.0358 (14)0.0324 (12)0.0018 (11)0.0048 (10)0.0008 (11)
C410.0403 (13)0.0349 (13)0.0270 (11)0.0023 (11)0.0126 (10)0.0025 (10)
O420.0402 (10)0.0333 (10)0.0333 (9)0.0066 (8)0.0190 (8)0.0048 (8)
C430.0260 (11)0.0337 (13)0.0305 (11)0.0014 (10)0.0126 (9)0.0002 (10)
C440.0354 (13)0.0450 (16)0.0385 (13)0.0044 (12)0.0208 (11)0.0052 (12)
C450.0312 (12)0.0495 (17)0.0437 (14)0.0076 (12)0.0182 (11)0.0005 (13)
C460.0343 (13)0.0412 (16)0.0471 (15)0.0120 (12)0.0149 (12)0.0015 (13)
C470.0313 (12)0.0373 (14)0.0333 (12)0.0032 (11)0.0097 (10)0.0012 (11)
Geometric parameters (Å, °) top
C1—C471.401 (4)C24—C251.477 (3)
C1—C431.402 (4)C25—C261.341 (3)
C1—C21.474 (3)C25—H250.9500
C2—C31.335 (4)C26—C271.463 (3)
C2—H20.9500C26—H260.9500
C3—C41.472 (3)C27—C281.402 (3)
C3—H30.9500C27—C321.411 (3)
C4—O41.222 (3)C28—C291.389 (3)
C4—C51.500 (4)C28—H280.9500
C5—C61.389 (4)C29—C301.389 (4)
C5—C101.405 (3)C29—H290.9500
C6—C71.387 (5)C30—C311.397 (4)
C6—H60.9500C30—H300.9500
C7—C81.376 (5)C31—C321.392 (3)
C7—H70.9500C31—H310.9500
C8—C91.394 (4)C32—O331.369 (3)
C8—H80.9500O33—C341.433 (3)
C9—C101.391 (4)C34—C351.504 (4)
C9—H90.9500C34—H34A0.9900
C10—O111.361 (3)C34—H34B0.9900
O11—C121.440 (3)C35—O361.413 (3)
C12—C131.505 (4)C35—H35A0.9900
C12—H12A0.9900C35—H35B0.9900
C12—H12B0.9900O36—C371.435 (4)
C13—O141.426 (3)C37—C381.515 (5)
C13—H13A0.9900C37—H37A0.9900
C13—H13B0.9900C37—H37B0.9900
O14—C151.418 (3)C38—O391.420 (4)
C15—C161.504 (3)C38—H38A0.9900
C15—H15A0.9900C38—H38B0.9900
C15—H15B0.9900O39—C401.417 (3)
C16—O171.433 (3)C40—C411.504 (4)
C16—H16A0.9900C40—H40A0.9900
C16—H16B0.9900C40—H40B0.9900
O17—C181.358 (3)C41—O421.431 (3)
C18—C191.391 (3)C41—H41A0.9900
C18—C231.407 (3)C41—H41B0.9900
C19—C201.384 (4)O42—C431.366 (3)
C19—H190.9500C43—C441.405 (3)
C20—C211.386 (4)C44—C451.390 (4)
C20—H200.9500C44—H440.9500
C21—C221.388 (4)C45—C461.382 (4)
C21—H210.9500C45—H450.9500
C22—C231.407 (3)C46—C471.384 (4)
C22—H220.9500C46—H460.9500
C23—C241.499 (3)C47—H470.9500
C24—O241.226 (3)
C47—C1—C43118.6 (2)C26—C25—H25119.7
C47—C1—C2121.7 (2)C24—C25—H25119.7
C43—C1—C2119.6 (2)C25—C26—C27125.1 (2)
C3—C2—C1124.9 (2)C25—C26—H26117.5
C3—C2—H2117.5C27—C26—H26117.5
C1—C2—H2117.5C28—C27—C32118.2 (2)
C2—C3—C4123.1 (3)C28—C27—C26121.8 (2)
C2—C3—H3118.5C32—C27—C26120.0 (2)
C4—C3—H3118.5C29—C28—C27121.3 (2)
O4—C4—C3119.7 (3)C29—C28—H28119.3
O4—C4—C5120.2 (2)C27—C28—H28119.3
C3—C4—C5120.0 (2)C30—C29—C28119.4 (2)
C6—C5—C10118.7 (3)C30—C29—H29120.3
C6—C5—C4118.6 (2)C28—C29—H29120.3
C10—C5—C4122.6 (2)C29—C30—C31120.8 (2)
C7—C6—C5121.5 (3)C29—C30—H30119.6
C7—C6—H6119.3C31—C30—H30119.6
C5—C6—H6119.3C32—C31—C30119.4 (2)
C8—C7—C6119.3 (3)C32—C31—H31120.3
C8—C7—H7120.3C30—C31—H31120.3
C6—C7—H7120.3O33—C32—C31123.7 (2)
C7—C8—C9120.7 (3)O33—C32—C27115.5 (2)
C7—C8—H8119.7C31—C32—C27120.8 (2)
C9—C8—H8119.7C32—O33—C34117.32 (19)
C10—C9—C8119.9 (3)O33—C34—C35107.8 (2)
C10—C9—H9120.1O33—C34—H34A110.2
C8—C9—H9120.1C35—C34—H34A110.2
O11—C10—C9124.6 (2)O33—C34—H34B110.2
O11—C10—C5115.5 (2)C35—C34—H34B110.2
C9—C10—C5119.9 (2)H34A—C34—H34B108.5
C10—O11—C12117.8 (2)O36—C35—C34107.8 (2)
O11—C12—C13108.4 (2)O36—C35—H35A110.1
O11—C12—H12A110.0C34—C35—H35A110.1
C13—C12—H12A110.0O36—C35—H35B110.1
O11—C12—H12B110.0C34—C35—H35B110.1
C13—C12—H12B110.0H35A—C35—H35B108.5
H12A—C12—H12B108.4C35—O36—C37112.1 (2)
O14—C13—C12114.8 (2)O36—C37—C38113.4 (2)
O14—C13—H13A108.6O36—C37—H37A108.9
C12—C13—H13A108.6C38—C37—H37A108.9
O14—C13—H13B108.6O36—C37—H37B108.9
C12—C13—H13B108.6C38—C37—H37B108.9
H13A—C13—H13B107.6H37A—C37—H37B107.7
C15—O14—C13113.40 (18)O39—C38—C37113.9 (3)
O14—C15—C16108.72 (19)O39—C38—H38A108.8
O14—C15—H15A109.9C37—C38—H38A108.8
C16—C15—H15A109.9O39—C38—H38B108.8
O14—C15—H15B109.9C37—C38—H38B108.8
C16—C15—H15B109.9H38A—C38—H38B107.7
H15A—C15—H15B108.3C40—O39—C38114.8 (2)
O17—C16—C15105.9 (2)O39—C40—C41107.8 (2)
O17—C16—H16A110.6O39—C40—H40A110.1
C15—C16—H16A110.6C41—C40—H40A110.1
O17—C16—H16B110.6O39—C40—H40B110.1
C15—C16—H16B110.6C41—C40—H40B110.1
H16A—C16—H16B108.7H40A—C40—H40B108.5
C18—O17—C16119.23 (19)O42—C41—C40108.8 (2)
O17—C18—C19124.0 (2)O42—C41—H41A109.9
O17—C18—C23115.7 (2)C40—C41—H41A109.9
C19—C18—C23120.2 (2)O42—C41—H41B109.9
C20—C19—C18119.8 (3)C40—C41—H41B109.9
C20—C19—H19120.1H41A—C41—H41B108.3
C18—C19—H19120.1C43—O42—C41117.28 (19)
C19—C20—C21121.2 (3)O42—C43—C1117.1 (2)
C19—C20—H20119.4O42—C43—C44122.8 (2)
C21—C20—H20119.4C1—C43—C44120.1 (2)
C20—C21—C22119.1 (2)C45—C44—C43119.8 (3)
C20—C21—H21120.4C45—C44—H44120.1
C22—C21—H21120.4C43—C44—H44120.1
C21—C22—C23121.0 (3)C46—C45—C44120.3 (3)
C21—C22—H22119.5C46—C45—H45119.8
C23—C22—H22119.5C44—C45—H45119.8
C22—C23—C18118.5 (2)C45—C46—C47120.1 (3)
C22—C23—C24117.5 (2)C45—C46—H46120.0
C18—C23—C24124.0 (2)C47—C46—H46120.0
O24—C24—C25120.9 (2)C46—C47—C1121.1 (3)
O24—C24—C23119.0 (2)C46—C47—H47119.5
C25—C24—C23120.1 (2)C1—C47—H47119.5
C26—C25—C24120.7 (2)
C47—C1—C2—C31.0 (4)C22—C23—C24—C25153.5 (2)
C43—C1—C2—C3175.4 (3)C18—C23—C24—C2527.4 (3)
C1—C2—C3—C4178.7 (2)O24—C24—C25—C2620.1 (4)
C2—C3—C4—O4169.5 (3)C23—C24—C25—C26162.1 (2)
C2—C3—C4—C57.0 (4)C24—C25—C26—C27177.5 (2)
O4—C4—C5—C662.2 (4)C25—C26—C27—C2824.2 (4)
C3—C4—C5—C6114.2 (3)C25—C26—C27—C32156.2 (2)
O4—C4—C5—C10117.0 (3)C32—C27—C28—C291.2 (4)
C3—C4—C5—C1066.5 (3)C26—C27—C28—C29178.4 (2)
C10—C5—C6—C71.7 (4)C27—C28—C29—C300.3 (4)
C4—C5—C6—C7179.1 (2)C28—C29—C30—C310.5 (4)
C5—C6—C7—C81.1 (4)C29—C30—C31—C320.3 (4)
C6—C7—C8—C90.5 (4)C30—C31—C32—O33177.9 (2)
C7—C8—C9—C101.6 (5)C30—C31—C32—C270.6 (4)
C8—C9—C10—O11179.8 (3)C28—C27—C32—O33177.2 (2)
C8—C9—C10—C51.0 (4)C26—C27—C32—O333.1 (3)
C6—C5—C10—O11178.3 (2)C28—C27—C32—C311.4 (3)
C4—C5—C10—O110.9 (3)C26—C27—C32—C31178.3 (2)
C6—C5—C10—C90.6 (4)C31—C32—O33—C344.8 (3)
C4—C5—C10—C9179.8 (2)C27—C32—O33—C34173.7 (2)
C9—C10—O11—C123.0 (4)C32—O33—C34—C35170.8 (2)
C5—C10—O11—C12175.9 (2)O33—C34—C35—O3672.6 (3)
C10—O11—C12—C13176.5 (2)C34—C35—O36—C37177.4 (2)
O11—C12—C13—O1486.1 (3)C35—O36—C37—C3888.0 (3)
C12—C13—O14—C1569.8 (3)O36—C37—C38—O3971.8 (3)
C13—O14—C15—C16171.1 (2)C37—C38—O39—C4081.9 (3)
O14—C15—C16—O1767.8 (3)C38—O39—C40—C41172.4 (2)
C15—C16—O17—C18179.1 (2)O39—C40—C41—O4279.6 (3)
C16—O17—C18—C1911.0 (3)C40—C41—O42—C43172.9 (2)
C16—O17—C18—C23171.5 (2)C41—O42—C43—C1159.6 (2)
O17—C18—C19—C20175.6 (2)C41—O42—C43—C4420.9 (4)
C23—C18—C19—C201.7 (4)C47—C1—C43—O42179.0 (2)
C18—C19—C20—C210.0 (4)C2—C1—C43—O424.5 (3)
C19—C20—C21—C220.2 (4)C47—C1—C43—C440.6 (4)
C20—C21—C22—C231.9 (4)C2—C1—C43—C44175.9 (2)
C21—C22—C23—C183.5 (4)O42—C43—C44—C45179.9 (3)
C21—C22—C23—C24177.4 (2)C1—C43—C44—C450.4 (4)
O17—C18—C23—C22174.1 (2)C43—C44—C45—C461.2 (5)
C19—C18—C23—C223.4 (3)C44—C45—C46—C471.0 (5)
O17—C18—C23—C244.9 (3)C45—C46—C47—C10.0 (4)
C19—C18—C23—C24177.6 (2)C43—C1—C47—C460.8 (4)
C22—C23—C24—O2424.2 (3)C2—C1—C47—C46175.7 (3)
C18—C23—C24—O24154.8 (2)
references
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