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Acta Cryst. (2008). E64, o712    [ doi:10.1107/S1600536808006843 ]

Partial cone conformer of 25,27-bis[(methoxycarbonyl)methoxy]-26,28-dipropoxycalix[4]arene

G.-Z. Zhang, M. Zhao, X.-L. Zhang, J.-P. Ma and D.-S. Guo

Abstract top

Molecules of the title compound, C40H44O8, adopt a partial cone conformation. The dihedral angles between the planes of the aromatic rings and the mean plane through the methylene C atoms bridging the aromatic rings are 35.74 (7), 85.86 (5), 87.77 (4) and 89.95 (5)°. Two opposite aryl rings are approximately parallel to each other; the others are at an interplanar angle of 52.41 (6)°. Intra- and intermolecular C-H...O hydrogen bonds stabilize the molecular conformation and the crystal packing. Two C atoms of one propoxy chain are disordered over two positions; the site occupancy factors are ca 0.66 and 0.34.

Comment top

Substituted calix[4]arenes, as the most fascinating macrocyclic receptors in supramolecular chemistry, have attracted much interest in recent years due to the high affinity and ion selectivity (Gutsche, 1998). In particular, much attention was paid to the ethyl ester derivatives of the calix[4]arene (Iwamoto & Shinkai, 1992; Arena et al., 1997) since they are one of the most versatile intermediates for building highly preorganized receptors. It has been shown that the conformational distribution in the exhaustive O-alkylation of the calix[4]arene depends upon the reaction conditions, the para substituent of the calix[4]arene, and the steric requirement of the agent (Pappalardo et al., 1992; Ferguson et al., 1993). In the O-alkylation, the cone and 1,3-alternate conformers are often obtained via the metal template effect using potassium and caesium ions, respectively (Yamato et al., 1998). However, both partial cone and cone conformers were isolated instead of the 1,3-alternate conformer when treatment 25,27-dihydroxy-26,28-dipropoxycalix[4]arene with methyl bromoacetate using caesium carbonate as a base in acetone.

The title calix[4]arene compound adopts a partial cone conformation (Ferguson et al., 1993) (Fig. 1). The dihedral angles between the planes of the aromatic rings and the mean plane through the methylene C atoms bridging the aromatic rings are 35.74 (7), 85.86 (5), 87.77 (4) and 89.95 (5)°. The C2–C7 and C22–C27 rings make an interplanar angle of 52.41 (6)°. However the C12–C17 and C32–C37 rings are almost parallel to each other, with a dihedral angle of 4.17 (11)°. The O···O separations of ethereal O atoms are O1···O4 3.017 (2), O1···O5 3.365 (2), O4···O9 4.693 (2), and O5···O9 4.588 (2) Å. This conformation precludes any solvent molecule being enclathrated within the small molecular cavity.

In the crystal structure there are intra- and intermolecular C—H···O hydrogen bonds (Table 1), which stabilize the partial cone conformation and the crystal packing.

Related literature top

For related literature, see: Arena et al. (1997); Ferguson et al. (1993); Gutsche (1998); Iwamoto & Shinkai (1992); Pappalardo et al. (1992); Yamato et al. (1998).

Experimental top

A mixture of 25,27-dihydroxy-26,28-dipropoxycalix[4]arene (0.200 g, 0.39 mmol), anhydrous caesium carbonate (0.190 g, 0.59 mmol) and methyl bromoacetate (0.11 ml, 1.17 mmol) in dry acetone (10 ml) was refluxed under nitrogen for 8 h and cooled to room temperature. After removal of the solvent under reduced pressure, the residue was treated with 5% aqueous hydrochloric acid and extracted with dichloromethane. The organic layer was washed with saturated sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash column (silica gel, EtOAc/petroleum ether = 1:5) to give conformer (I) (Rf = 0.7) and comformer (II) (Rf = 0.4) in 48% and 39% yields, respectively. Single crystals suitable for X-ray diffraction analysis were obtained by slow diffusion of methanol into a dichloromethane solution at 273 K.

Refinement top

Hydrogen atoms were placed in geometrically idealized positions and refined using a riding model with Caromatic—H = 0.93Å [Uiso(H) = 1.2Ueq(C)], Cmethylene—H = 0.96Å [Uiso(H) = 1.2Ueq(C)] or Cmethyl—H = 0.97Å [Uiso(H) = 1.5Ueq(C)]. Atoms C19 and C20 are disordered over two positions (C19/C19' and C20/C20'), with refined occupancies of 0.337 (5) and 0.663 (5). One of the two CH2—CH3 distances of the disordered C-atoms (C18—C19) was restrained to 1.54 (1) Å.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme and displacement ellipsoids drawn at the 30% probability level for non-H atoms. The major occupied site of the disordered side chain is drawn with dashed bonds.
25,27-bis[(methoxycarbonyl)methoxy]-26,28-dipropoxycalix[4]arene top
Crystal data top
C40H44O8F000 = 1392
Mr = 652.75Dx = 1.264 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
a = 9.3007 (18) ÅCell parameters from 4185 reflections
b = 18.114 (4) Åθ = 2.3–28.2º
c = 20.768 (4) ŵ = 0.09 mm−1
β = 101.334 (3)ºT = 298 (2) K
V = 3430.6 (11) Å3Block, colourless
Z = 40.37 × 0.18 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		4677 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Monochromator: graphiteθmax = 25.5º
T = 298(2) Kθmin = 2.0º
φ and ω scansh = −11→10
Absorption correction: nonek = −21→21
17798 measured reflectionsl = −25→21
6362 independent reflections
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) = 0.113  w = 1/[σ2(Fo2) + (0.0427P)2 + 0.8294P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6362 reflectionsΔρmax = 0.23 e Å−3
457 parametersΔρmin = −0.21 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C40H44O8V = 3430.6 (11) Å3
Mr = 652.75Z = 4
Monoclinic, P21/cMo Kα
a = 9.3007 (18) ŵ = 0.09 mm−1
b = 18.114 (4) ÅT = 298 (2) K
c = 20.768 (4) Å0.37 × 0.18 × 0.08 mm
β = 101.334 (3)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		6362 independent reflections
Absorption correction: none4677 reflections with I > 2σ(I)
17798 measured reflectionsRint = 0.038
Refinement top
R[F2 > 2σ(F2)] = 0.0521 restraint
wR(F2) = 0.113H-atom parameters constrained
S = 1.04Δρmax = 0.23 e Å−3
6362 reflectionsΔρmin = −0.21 e Å−3
457 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.4972 (2)0.73848 (11)0.02361 (9)0.0283 (5)
H1A0.46640.7738−0.01150.034*
H1B0.55280.70000.00710.034*
C20.5945 (2)0.77685 (10)0.08095 (9)0.0246 (4)
C30.7334 (2)0.75018 (11)0.10761 (10)0.0301 (5)
H30.77100.71060.08760.036*
C40.8167 (2)0.78136 (11)0.16329 (10)0.0326 (5)
H40.91050.76370.18010.039*
C50.7595 (2)0.83898 (11)0.19370 (9)0.0288 (5)
H50.81470.85880.23200.035*
C60.6214 (2)0.86838 (10)0.16860 (9)0.0237 (4)
C70.5431 (2)0.83749 (10)0.11086 (9)0.0230 (4)
C80.4144 (2)0.92188 (11)0.03600 (10)0.0297 (5)
H8A0.47170.90410.00490.036*
H8B0.46290.96510.05780.036*
C90.2634 (2)0.94198 (11)0.00053 (9)0.0268 (5)
C100.1375 (2)1.02558 (13)−0.07828 (11)0.0430 (6)
H10A0.10190.9897−0.11160.065*
H10B0.15501.0714−0.09860.065*
H10C0.06591.0329−0.05130.065*
C110.5597 (2)0.93063 (10)0.20352 (10)0.0277 (5)
H11A0.63290.94580.24110.033*
H11B0.53940.97250.17400.033*
C120.4208 (2)0.90960 (10)0.22657 (9)0.0244 (4)
C130.2855 (2)0.93849 (11)0.19661 (9)0.0292 (5)
H130.28140.97360.16370.035*
C140.1574 (2)0.91623 (11)0.21461 (10)0.0328 (5)
H140.06850.93750.19510.039*
C150.1615 (2)0.86226 (11)0.26167 (9)0.0294 (5)
H150.07430.84590.27240.035*
C160.2935 (2)0.83180 (10)0.29339 (9)0.0239 (4)
C170.4221 (2)0.85832 (10)0.27674 (9)0.0232 (4)
C180.6063 (2)0.87236 (11)0.36982 (10)0.0322 (5)
H18A0.55930.85490.40470.039*0.337 (5)
H18B0.58810.92480.36340.039*0.337 (5)
C190.7747 (8)0.8551 (5)0.3847 (4)0.0331 (19)0.337 (5)
H19A0.79150.80260.39190.040*0.337 (5)
H19B0.81900.87040.34830.040*0.337 (5)
C200.8404 (8)0.8985 (4)0.4468 (3)0.044 (2)0.337 (5)
H20A0.82080.95020.43930.067*0.337 (5)
H20B0.94440.89060.45740.067*0.337 (5)
H20C0.79700.88200.48260.067*0.337 (5)
C210.2928 (2)0.76960 (11)0.34205 (9)0.0287 (5)
H21A0.39290.75820.36320.034*
H21B0.24070.78550.37580.034*
C220.2207 (2)0.70070 (10)0.30918 (9)0.0256 (5)
C230.0867 (2)0.67571 (11)0.32014 (10)0.0327 (5)
H230.04140.70060.34990.039*
C240.0191 (2)0.61448 (12)0.28763 (11)0.0359 (5)
H24−0.06970.59770.29630.043*
C250.0841 (2)0.57875 (11)0.24254 (10)0.0318 (5)
H250.03800.53780.22060.038*
C260.2170 (2)0.60219 (10)0.22883 (9)0.0250 (4)
C270.2867 (2)0.66187 (10)0.26456 (9)0.0246 (4)
C280.5503 (2)0.65411 (12)0.27113 (9)0.0310 (5)
H28A0.62630.68160.25550.037*
H28B0.54330.60600.25030.037*
C290.5965 (2)0.64378 (11)0.34452 (10)0.0282 (5)
C300.8024 (3)0.63060 (15)0.42966 (11)0.0500 (7)
H30A0.76300.66420.45750.075*
H30B0.90710.63560.43740.075*
H30C0.77740.58090.43920.075*
C310.2738 (2)0.56959 (10)0.17147 (9)0.0283 (5)
H31A0.22030.52470.15700.034*
H31B0.37660.55690.18540.034*
C320.2563 (2)0.62392 (10)0.11495 (9)0.0258 (5)
C330.1197 (2)0.65398 (12)0.08963 (10)0.0337 (5)
H330.03810.63770.10520.040*
C340.1031 (2)0.70765 (12)0.04169 (10)0.0352 (5)
H340.01060.72670.02450.042*
C350.2239 (2)0.73306 (11)0.01923 (9)0.0305 (5)
H350.21210.7699−0.01250.037*
C360.3630 (2)0.70474 (10)0.04306 (9)0.0250 (5)
C370.3764 (2)0.64870 (10)0.09015 (9)0.0247 (4)
C380.5595 (2)0.56049 (11)0.08040 (10)0.0312 (5)
H38A0.57300.57760.03770.037*
H38B0.48470.52240.07370.037*
C390.7012 (2)0.52970 (12)0.11846 (11)0.0407 (6)
H39A0.68360.50770.15880.049*
H39B0.77070.56970.13030.049*
C400.7671 (3)0.47225 (15)0.07997 (13)0.0624 (8)
H40A0.69790.43300.06730.094*
H40B0.85480.45270.10680.094*
H40C0.79050.49460.04140.094*
H18C0.52790.87380.39440.075*0.663 (5)
H18D0.62760.92270.35890.075*0.663 (5)
C19'0.7406 (4)0.8397 (2)0.41222 (19)0.0274 (9)0.663 (5)
H19C0.72020.78950.42400.033*0.663 (5)
H19D0.76710.86810.45240.033*0.663 (5)
C20'0.8681 (4)0.8398 (2)0.37574 (16)0.0386 (10)0.663 (5)
H20D0.84570.80750.33840.058*0.663 (5)
H20E0.95540.82290.40460.058*0.663 (5)
H20F0.88320.88890.36120.058*0.663 (5)
O10.41503 (14)0.69143 (7)0.25091 (6)0.0268 (3)
O20.51744 (17)0.63185 (10)0.38196 (7)0.0542 (5)
O30.74159 (15)0.64726 (9)0.36180 (7)0.0397 (4)
O40.55748 (14)0.83184 (7)0.31032 (6)0.0275 (3)
O50.51464 (14)0.62042 (7)0.11647 (6)0.0281 (3)
O70.27257 (15)0.99957 (8)−0.03810 (7)0.0366 (4)
O80.15084 (17)0.91286 (9)0.00548 (8)0.0484 (4)
O90.40569 (14)0.86619 (7)0.08311 (6)0.0251 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0350 (13)0.0289 (11)0.0214 (11)0.0030 (9)0.0069 (9)−0.0009 (8)
C20.0250 (12)0.0298 (11)0.0205 (10)−0.0020 (9)0.0079 (8)0.0026 (8)
C30.0294 (13)0.0302 (12)0.0325 (12)0.0026 (9)0.0106 (10)0.0014 (9)
C40.0236 (12)0.0392 (13)0.0338 (12)0.0045 (9)0.0029 (9)0.0064 (10)
C50.0255 (12)0.0356 (12)0.0237 (11)−0.0040 (9)0.0009 (9)0.0018 (9)
C60.0229 (11)0.0256 (11)0.0233 (11)−0.0044 (8)0.0061 (8)0.0038 (8)
C70.0181 (11)0.0276 (11)0.0236 (11)−0.0006 (8)0.0051 (8)0.0062 (8)
C80.0246 (12)0.0328 (12)0.0315 (12)−0.0004 (9)0.0050 (9)0.0081 (9)
C90.0239 (12)0.0282 (11)0.0289 (12)0.0000 (9)0.0065 (9)0.0028 (9)
C100.0336 (14)0.0488 (14)0.0409 (14)0.0029 (11)−0.0070 (11)0.0170 (11)
C110.0312 (13)0.0252 (11)0.0265 (11)−0.0046 (9)0.0051 (9)0.0004 (8)
C120.0280 (12)0.0218 (10)0.0232 (11)0.0009 (8)0.0046 (9)−0.0039 (8)
C130.0345 (14)0.0264 (11)0.0254 (11)0.0058 (9)0.0032 (9)0.0028 (8)
C140.0238 (12)0.0398 (13)0.0318 (12)0.0089 (9)−0.0022 (9)0.0002 (10)
C150.0214 (12)0.0364 (12)0.0306 (12)−0.0014 (9)0.0058 (9)−0.0045 (9)
C160.0247 (12)0.0256 (10)0.0216 (10)0.0004 (8)0.0046 (8)−0.0044 (8)
C170.0219 (11)0.0229 (10)0.0237 (11)0.0050 (8)0.0020 (8)−0.0025 (8)
C180.0298 (13)0.0291 (11)0.0342 (12)−0.0016 (9)−0.0023 (9)−0.0022 (9)
C190.034 (6)0.047 (5)0.019 (5)0.002 (4)0.009 (4)0.000 (3)
C200.041 (5)0.051 (5)0.034 (4)−0.007 (3)−0.009 (3)0.011 (3)
C210.0304 (13)0.0338 (12)0.0234 (11)−0.0001 (9)0.0084 (9)−0.0020 (9)
C220.0293 (12)0.0281 (11)0.0200 (10)0.0001 (9)0.0064 (9)0.0051 (8)
C230.0343 (14)0.0351 (12)0.0320 (12)0.0018 (10)0.0149 (10)0.0020 (9)
C240.0287 (13)0.0376 (13)0.0441 (14)−0.0059 (10)0.0136 (10)0.0052 (10)
C250.0309 (13)0.0270 (11)0.0373 (13)−0.0047 (9)0.0066 (10)0.0020 (9)
C260.0261 (12)0.0233 (10)0.0252 (11)0.0004 (8)0.0037 (9)0.0053 (8)
C270.0224 (11)0.0267 (11)0.0243 (11)−0.0008 (8)0.0039 (8)0.0100 (8)
C280.0210 (12)0.0428 (13)0.0301 (12)0.0020 (9)0.0069 (9)−0.0027 (9)
C290.0237 (13)0.0299 (11)0.0317 (12)0.0022 (9)0.0070 (9)−0.0002 (9)
C300.0363 (15)0.0685 (18)0.0392 (14)0.0008 (12)−0.0072 (11)0.0119 (12)
C310.0286 (12)0.0246 (11)0.0310 (12)−0.0023 (9)0.0040 (9)−0.0010 (8)
C320.0277 (12)0.0259 (11)0.0230 (11)0.0001 (9)0.0028 (9)−0.0053 (8)
C330.0245 (13)0.0423 (13)0.0337 (12)−0.0021 (10)0.0043 (9)−0.0015 (10)
C340.0251 (13)0.0438 (13)0.0342 (13)0.0066 (10)−0.0006 (10)0.0026 (10)
C350.0335 (13)0.0331 (12)0.0223 (11)0.0020 (9)−0.0010 (9)0.0014 (9)
C360.0279 (12)0.0281 (11)0.0187 (10)−0.0012 (9)0.0038 (8)−0.0056 (8)
C370.0235 (12)0.0270 (11)0.0222 (11)0.0022 (8)0.0009 (8)−0.0058 (8)
C380.0336 (13)0.0315 (12)0.0300 (12)0.0061 (9)0.0099 (10)−0.0004 (9)
C390.0349 (14)0.0402 (13)0.0462 (14)0.0098 (10)0.0058 (11)0.0035 (11)
C400.0541 (19)0.0661 (19)0.0696 (19)0.0306 (14)0.0189 (15)0.0068 (14)
C19'0.027 (2)0.040 (2)0.015 (2)0.0010 (16)0.0051 (16)0.0017 (16)
C20'0.026 (2)0.058 (2)0.031 (2)0.0047 (18)0.0038 (16)0.0048 (16)
O10.0213 (8)0.0311 (8)0.0285 (8)−0.0024 (6)0.0064 (6)0.0033 (6)
O20.0285 (10)0.1005 (14)0.0341 (9)0.0036 (9)0.0076 (8)0.0224 (9)
O30.0220 (9)0.0618 (11)0.0336 (9)0.0012 (7)0.0013 (7)0.0087 (7)
O40.0218 (8)0.0291 (8)0.0294 (8)0.0035 (6)−0.0001 (6)−0.0004 (6)
O50.0245 (8)0.0312 (8)0.0272 (8)0.0039 (6)0.0020 (6)−0.0022 (6)
O70.0266 (9)0.0423 (9)0.0380 (9)−0.0003 (7)−0.0005 (7)0.0187 (7)
O80.0233 (9)0.0494 (10)0.0688 (12)−0.0035 (8)0.0001 (8)0.0252 (8)
O90.0202 (8)0.0296 (7)0.0251 (7)0.0006 (6)0.0031 (6)0.0065 (6)
Geometric parameters (Å, °) top
C1—C361.514 (3)C21—H21A0.9700
C1—C21.516 (3)C21—H21B0.9700
C1—H1A0.9700C22—C231.386 (3)
C1—H1B0.9700C22—C271.398 (3)
C2—C31.388 (3)C23—C241.384 (3)
C2—C71.392 (3)C23—H230.9300
C3—C41.380 (3)C24—C251.372 (3)
C3—H30.9300C24—H240.9300
C4—C51.380 (3)C25—C261.388 (3)
C4—H40.9300C25—H250.9300
C5—C61.394 (3)C26—C271.396 (3)
C5—H50.9300C26—C311.515 (3)
C6—C71.392 (3)C27—O11.388 (2)
C6—C111.514 (3)C28—O11.417 (2)
C7—O91.395 (2)C28—C291.512 (3)
C8—O91.419 (2)C28—H28A0.9700
C8—C91.498 (3)C28—H28B0.9700
C8—H8A0.9700C29—O21.190 (2)
C8—H8B0.9700C29—O31.328 (2)
C9—O81.194 (2)C30—O31.443 (2)
C9—O71.329 (2)C30—H30A0.9600
C10—O71.443 (2)C30—H30B0.9600
C10—H10A0.9600C30—H30C0.9600
C10—H10B0.9600C31—C321.516 (3)
C10—H10C0.9600C31—H31A0.9700
C11—C121.512 (3)C31—H31B0.9700
C11—H11A0.9700C32—C331.387 (3)
C11—H11B0.9700C32—C371.393 (3)
C12—C131.392 (3)C33—C341.378 (3)
C12—C171.394 (3)C33—H330.9300
C13—C141.377 (3)C34—C351.378 (3)
C13—H130.9300C34—H340.9300
C14—C151.377 (3)C35—C361.390 (3)
C14—H140.9300C35—H350.9300
C15—C161.389 (3)C36—C371.398 (3)
C15—H150.9300C37—O51.392 (2)
C16—C171.393 (3)C38—O51.427 (2)
C16—C211.514 (3)C38—C391.504 (3)
C17—O41.399 (2)C38—H38A0.9700
C18—O41.432 (2)C38—H38B0.9700
C18—C19'1.501 (4)C39—C401.514 (3)
C18—C191.567 (7)C39—H39A0.9700
C18—H18A0.9700C39—H39B0.9700
C18—H18B0.9700C40—H40A0.9600
C18—H18C0.9694C40—H40B0.9600
C18—H18D0.9691C40—H40C0.9600
C19—C201.531 (10)C19'—C20'1.527 (5)
C19—H19A0.9700C19'—H19C0.9700
C19—H19B0.9700C19'—H19D0.9700
C20—H20A0.9600C20'—H20D0.9600
C20—H20B0.9600C20'—H20E0.9600
C20—H20C0.9600C20'—H20F0.9600
C21—C221.514 (3)
C36—C1—C2111.84 (15)H21A—C21—H21B107.9
C36—C1—H1A109.2C23—C22—C27118.06 (18)
C2—C1—H1A109.2C23—C22—C21121.86 (18)
C36—C1—H1B109.2C27—C22—C21120.04 (18)
C2—C1—H1B109.2C24—C23—C22121.24 (19)
H1A—C1—H1B107.9C24—C23—H23119.4
C3—C2—C7118.10 (18)C22—C23—H23119.4
C3—C2—C1121.28 (18)C25—C24—C23119.5 (2)
C7—C2—C1120.51 (18)C25—C24—H24120.3
C4—C3—C2121.13 (19)C23—C24—H24120.3
C4—C3—H3119.4C24—C25—C26121.7 (2)
C2—C3—H3119.4C24—C25—H25119.2
C5—C4—C3119.31 (19)C26—C25—H25119.2
C5—C4—H4120.3C25—C26—C27117.82 (18)
C3—C4—H4120.3C25—C26—C31120.29 (18)
C4—C5—C6121.87 (19)C27—C26—C31121.50 (18)
C4—C5—H5119.1O1—C27—C26121.21 (17)
C6—C5—H5119.1O1—C27—C22116.65 (17)
C7—C6—C5117.16 (18)C26—C27—C22121.58 (18)
C7—C6—C11121.91 (18)O1—C28—C29114.66 (16)
C5—C6—C11120.93 (17)O1—C28—H28A108.6
C6—C7—C2122.27 (18)C29—C28—H28A108.6
C6—C7—O9119.21 (17)O1—C28—H28B108.6
C2—C7—O9118.48 (17)C29—C28—H28B108.6
O9—C8—C9109.68 (16)H28A—C28—H28B107.6
O9—C8—H8A109.7O2—C29—O3123.88 (19)
C9—C8—H8A109.7O2—C29—C28126.29 (19)
O9—C8—H8B109.7O3—C29—C28109.79 (17)
C9—C8—H8B109.7O3—C30—H30A109.5
H8A—C8—H8B108.2O3—C30—H30B109.5
O8—C9—O7124.08 (19)H30A—C30—H30B109.5
O8—C9—C8127.12 (18)O3—C30—H30C109.5
O7—C9—C8108.80 (17)H30A—C30—H30C109.5
O7—C10—H10A109.5H30B—C30—H30C109.5
O7—C10—H10B109.5C26—C31—C32110.78 (16)
H10A—C10—H10B109.5C26—C31—H31A109.5
O7—C10—H10C109.5C32—C31—H31A109.5
H10A—C10—H10C109.5C26—C31—H31B109.5
H10B—C10—H10C109.5C32—C31—H31B109.5
C12—C11—C6113.08 (15)H31A—C31—H31B108.1
C12—C11—H11A109.0C33—C32—C37118.33 (18)
C6—C11—H11A109.0C33—C32—C31119.97 (18)
C12—C11—H11B109.0C37—C32—C31121.56 (18)
C6—C11—H11B109.0C34—C33—C32121.0 (2)
H11A—C11—H11B107.8C34—C33—H33119.5
C13—C12—C17117.29 (18)C32—C33—H33119.5
C13—C12—C11121.17 (18)C35—C34—C33119.8 (2)
C17—C12—C11121.49 (17)C35—C34—H34120.1
C14—C13—C12121.53 (19)C33—C34—H34120.1
C14—C13—H13119.2C34—C35—C36121.37 (19)
C12—C13—H13119.2C34—C35—H35119.3
C13—C14—C15119.73 (19)C36—C35—H35119.3
C13—C14—H14120.1C35—C36—C37117.75 (18)
C15—C14—H14120.1C35—C36—C1120.98 (18)
C14—C15—C16121.12 (19)C37—C36—C1121.01 (17)
C14—C15—H15119.4O5—C37—C32118.83 (17)
C16—C15—H15119.4O5—C37—C36119.34 (17)
C15—C16—C17117.85 (18)C32—C37—C36121.67 (18)
C15—C16—C21119.51 (18)O5—C38—C39108.81 (17)
C17—C16—C21122.59 (17)O5—C38—H38A109.9
C16—C17—C12122.25 (17)C39—C38—H38A109.9
C16—C17—O4119.35 (17)O5—C38—H38B109.9
C12—C17—O4118.39 (17)C39—C38—H38B109.9
O4—C18—C19'113.0 (2)H38A—C38—H38B108.3
O4—C18—C19101.7 (3)C38—C39—C40112.44 (19)
C19'—C18—C1928.5 (3)C38—C39—H39A109.1
O4—C18—H18A111.4C40—C39—H39A109.1
C19'—C18—H18A83.0C38—C39—H39B109.1
C19—C18—H18A111.5C40—C39—H39B109.1
O4—C18—H18B111.4H39A—C39—H39B107.8
C19'—C18—H18B124.8C39—C40—H40A109.5
C19—C18—H18B111.3C39—C40—H40B109.5
H18A—C18—H18B109.3H40A—C40—H40B109.5
O4—C18—H18C109.0C39—C40—H40C109.5
C19'—C18—H18C109.1H40A—C40—H40C109.5
C19—C18—H18C136.7H40B—C40—H40C109.5
H18A—C18—H18C28.2C18—C19'—C20'110.2 (3)
H18B—C18—H18C85.2C18—C19'—H19C109.6
O4—C18—H18D108.9C20'—C19'—H19C109.6
C19'—C18—H18D108.9C18—C19'—H19D109.6
C19—C18—H18D89.5C20'—C19'—H19D109.6
H18A—C18—H18D128.6H19C—C19'—H19D108.1
H18B—C18—H18D23.7C19'—C20'—H20D109.5
H18C—C18—H18D107.9C19'—C20'—H20E109.5
C20—C19—C18106.3 (5)H20D—C20'—H20E109.5
C20—C19—H19A110.5C19'—C20'—H20F109.5
C18—C19—H19A110.5H20D—C20'—H20F109.5
C20—C19—H19B110.5H20E—C20'—H20F109.5
C18—C19—H19B110.5C27—O1—C28120.32 (15)
H19A—C19—H19B108.7C29—O3—C30115.85 (17)
C22—C21—C16111.84 (15)C17—O4—C18110.87 (14)
C22—C21—H21A109.2C37—O5—C38114.62 (14)
C16—C21—H21A109.2C9—O7—C10116.94 (16)
C22—C21—H21B109.2C7—O9—C8112.20 (14)
C16—C21—H21B109.2
C36—C1—C2—C3113.1 (2)C31—C26—C27—O1−3.2 (3)
C36—C1—C2—C7−63.0 (2)C25—C26—C27—C22−4.8 (3)
C7—C2—C3—C41.9 (3)C31—C26—C27—C22167.99 (17)
C1—C2—C3—C4−174.32 (18)C23—C22—C27—O1175.26 (17)
C2—C3—C4—C51.4 (3)C21—C22—C27—O1−2.5 (3)
C3—C4—C5—C6−2.1 (3)C23—C22—C27—C263.7 (3)
C4—C5—C6—C7−0.5 (3)C21—C22—C27—C26−174.02 (17)
C4—C5—C6—C11178.82 (18)O1—C28—C29—O235.9 (3)
C5—C6—C7—C23.9 (3)O1—C28—C29—O3−146.37 (17)
C11—C6—C7—C2−175.35 (17)C25—C26—C31—C32105.4 (2)
C5—C6—C7—O9−178.60 (16)C27—C26—C31—C32−67.2 (2)
C11—C6—C7—O92.1 (3)C26—C31—C32—C33−54.8 (2)
C3—C2—C7—C6−4.6 (3)C26—C31—C32—C37120.8 (2)
C1—C2—C7—C6171.58 (17)C37—C32—C33—C34−0.7 (3)
C3—C2—C7—O9177.88 (16)C31—C32—C33—C34175.00 (18)
C1—C2—C7—O9−5.9 (3)C32—C33—C34—C35−1.2 (3)
O9—C8—C9—O8−6.0 (3)C33—C34—C35—C361.2 (3)
O9—C8—C9—O7173.24 (15)C34—C35—C36—C370.8 (3)
C7—C6—C11—C1261.6 (2)C34—C35—C36—C1−173.37 (18)
C5—C6—C11—C12−117.6 (2)C2—C1—C36—C35111.4 (2)
C6—C11—C12—C13−109.1 (2)C2—C1—C36—C37−62.6 (2)
C6—C11—C12—C1768.2 (2)C33—C32—C37—O5178.23 (16)
C17—C12—C13—C14−1.4 (3)C31—C32—C37—O52.6 (3)
C11—C12—C13—C14175.98 (18)C33—C32—C37—C362.8 (3)
C12—C13—C14—C15−2.3 (3)C31—C32—C37—C36−172.84 (17)
C13—C14—C15—C162.6 (3)C35—C36—C37—O5−178.24 (16)
C14—C15—C16—C170.9 (3)C1—C36—C37—O5−4.1 (3)
C14—C15—C16—C21−176.59 (18)C35—C36—C37—C32−2.9 (3)
C15—C16—C17—C12−4.9 (3)C1—C36—C37—C32171.33 (17)
C21—C16—C17—C12172.51 (17)O5—C38—C39—C40−172.66 (19)
C15—C16—C17—O4176.45 (16)O4—C18—C19'—C20'61.2 (3)
C21—C16—C17—O4−6.2 (3)C19—C18—C19'—C20'−10.4 (6)
C13—C12—C17—C165.1 (3)C26—C27—O1—C28−75.8 (2)
C11—C12—C17—C16−172.29 (17)C22—C27—O1—C28112.63 (19)
C13—C12—C17—O4−176.18 (16)C29—C28—O1—C27−61.1 (2)
C11—C12—C17—O46.4 (3)O2—C29—O3—C304.0 (3)
O4—C18—C19—C20177.9 (5)C28—C29—O3—C30−173.75 (18)
C19'—C18—C19—C20−65.2 (7)C16—C17—O4—C18−85.1 (2)
C15—C16—C21—C2265.0 (2)C12—C17—O4—C1896.18 (19)
C17—C16—C21—C22−112.3 (2)C19'—C18—O4—C17172.2 (2)
C16—C21—C22—C23−110.7 (2)C19—C18—O4—C17−160.3 (4)
C16—C21—C22—C2767.0 (2)C32—C37—O5—C3896.2 (2)
C27—C22—C23—C24−0.5 (3)C36—C37—O5—C38−88.3 (2)
C21—C22—C23—C24177.19 (19)C39—C38—O5—C37−173.18 (17)
C22—C23—C24—C25−1.5 (3)O8—C9—O7—C10−2.8 (3)
C23—C24—C25—C260.4 (3)C8—C9—O7—C10177.92 (17)
C24—C25—C26—C272.7 (3)C6—C7—O9—C892.3 (2)
C24—C25—C26—C31−170.17 (19)C2—C7—O9—C8−90.1 (2)
C25—C26—C27—O1−175.94 (16)C9—C8—O9—C7171.14 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C30—H30B···O8i0.962.583.406 (3)144
C31—H31B···O50.972.402.859 (2)109
C24—H24···O3ii0.932.583.309 (3)135
C21—H21A···O40.972.452.899 (2)108
C21—H21A···O20.972.563.255 (3)129
C10—H10C···O8iii0.962.593.510 (3)161
Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x−1, y, z; (iii) −x, −y+2, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C30—H30B···O8i0.962.583.406 (3)144
C31—H31B···O50.972.402.859 (2)109
C24—H24···O3ii0.932.583.309 (3)135
C21—H21A···O40.972.452.899 (2)108
C21—H21A···O20.972.563.255 (3)129
C10—H10C···O8iii0.962.593.510 (3)161
Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x−1, y, z; (iii) −x, −y+2, −z.
Acknowledgements top

Financial support from the National Natural Science Foundation of China (No. 20572064) and Shandong Province Natural Science Foundation (Y2006B30) is gratefully acknowledged.

references
References top

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