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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o2001.
Published online 2008 September 24. doi:  10.1107/S1600536808030250
PMCID: PMC2959367

Dibenzo-18-crown-6

Abstract

The asymmetric unit of the title compound, C20H24O6, contains two mol­ecules that are identical within standard deviations concerning bond lengths and angles as well as their conformations. In the crystal structure, weak C—H(...)O inter­actions help to consolidate the packing.

Related literature

For background, see: Hutton & Oakes (1976 [triangle]); Baur & Kassner (1992 [triangle]); Grotjahn et al. (2001 [triangle]); Barranikov et al. (2002 [triangle]); Su et al. (2003 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-o2001-scheme1.jpg

Experimental

Crystal data

  • C20H24O6
  • M r = 360.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2001-efi1.jpg
  • a = 4.902 (3) Å
  • b = 28.58 (2) Å
  • c = 25.06 (2) Å
  • β = 92.049 (8)°
  • V = 3509 (4) Å3
  • Z = 8
  • Synchrotron radiation
  • λ = 0.6946 Å
  • μ = 0.10 mm−1
  • T = 120 (2) K
  • 0.04 × 0.02 × 0.02 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: none
  • 13644 measured reflections
  • 3564 independent reflections
  • 2972 reflections with I > 2σ(I)
  • R int = 0.054

Refinement

  • R[F 2 > 2σ(F 2)] = 0.098
  • wR(F 2) = 0.294
  • S = 1.15
  • 3564 reflections
  • 470 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030250/im2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030250/im2081Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Professor Bill Clegg (University of Newcastle/Daresbury Laboratory) for collecting the diffraction data and performing the initial processing.

supplementary crystallographic information

Comment

The relationship between the conformations of crown ethers and their coordinating abilities has been the subject of many crystallographic, spectroscopic, thermochemical and theoretical studies (e.g. Grotjahn et al., 2001; Barranikov et al., 2002; Su et al., 2003). The crystal structures of a large number of complexes containing the title crown ether have been determined, but the structure of the title compound, (I), the free crown ether, has remained undetermined until now.

There are two molecules in the asymmetric unit of (I) (Fig. 1) with very similar conformations, with both possessing local approximate C2 symmetry. This is also reflected in the trans—gauche—trans—gauche sequence of conformation angles about the four O—C—C—O bonds in the 18-membered ring. The dihedral angles between the mean planes of the aromatic rings are 65.5 (3)° for the C1 molecule and 66.1 (3)° for the C21 molecule. Otherwise, the geometrical paramaters for (I) may be regarded as normal (Allen et al., 1987).

In the crystal of (I), two weak intermolecular C—H···O interactions (Table 1) may help to consolidate the packing. There are no π-π stacking interactions in (I), the minimum ring centroid separation being greater than 5.6 Å. The packing (Fig. 3) for (I) results in (001) pseudo layers of the two asymmetric molecules.

Experimental

The unreacted title compound was obtained from the attempted complexation with 3-(trichlorostannyl)propanamide (Hutton & Oakes, 1976). Slow evaporation of dibenzo-18-crown-6 and 3-(trichlorostannyl)propanamide (0.2 mmol of each) in ethanol solution (15 ml) led to isolation of tiny colourless shards of (I).

Refinement

The situation of two asymmetric molecules in space group Cc is a suspicious one (Baur & Kassner, 1992) and careful checks for additional or missed crystal symmetry were made, but none was found. No starting models could be established in space groups C2/c, C2/m or any lower symmetry centrosymmetric space groups. Structure solutions in lower-symmetry non-centrosymmetric space groups were easily achieved and could all be transformed to the model described above.

Even with the use of synchrotron radiation, the small crystal size resulted in weak diffraction and a poor data to parameter ratio of 7.6:1. The residuals are also high. Anomalous dispersion was negligible and Friedel pairs were merged before refinement. The hydrogen atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
View of the molecular structure of (I) showing 50% displacement ellipsoids. The H atoms are drawn as spheres of arbitrary radius.
Fig. 2.
The packing in (I), viewed down [100] with H atoms omitted for clarity. Bonds in the C1 and C21 molecules are coloured red and blue, respectively.

Crystal data

C20H24O6F(000) = 1536
Mr = 360.39Dx = 1.365 Mg m3
Monoclinic, CcSynchrotron radiation, λ = 0.6946 Å
Hall symbol: C -2ycCell parameters from 982 reflections
a = 4.902 (3) Åθ = 2.9–25.3°
b = 28.58 (2) ŵ = 0.10 mm1
c = 25.06 (2) ÅT = 120 K
β = 92.049 (8)°Shard, colourless
V = 3509 (4) Å30.04 × 0.02 × 0.02 mm
Z = 8

Data collection

Bruker SMART APEX2 CCD diffractometer2972 reflections with I > 2σ(I)
Radiation source: Daresbury SRS station 9.8Rint = 0.054
silicon 111θmax = 25.8°, θmin = 2.9°
Fine–slice ω scansh = −6→6
13644 measured reflectionsk = −35→35
3564 independent reflectionsl = −30→31

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.098H-atom parameters constrained
wR(F2) = 0.294w = 1/[σ2(Fo2) + (0.1469P)2 + 19.0455P] where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
3564 reflectionsΔρmax = 0.50 e Å3
470 parametersΔρmin = −0.52 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.067 (7)

Special details

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)

xyzUiso*/Ueq
C1−0.212 (2)0.0826 (4)0.4641 (4)0.033 (2)
H1A−0.32590.11070.46950.039*
H1B−0.09440.07760.49650.039*
C2−0.394 (2)0.0398 (4)0.4538 (4)0.036 (2)
H2A−0.53940.03930.48020.043*
H2B−0.48280.04240.41780.043*
C3−0.127 (2)−0.0154 (3)0.4094 (4)0.035 (2)
H3A0.00100.00930.39820.042*
H3B−0.2696−0.01940.38070.042*
C40.0261 (18)−0.0614 (3)0.4193 (4)0.0295 (19)
H4A0.1473−0.05910.45160.035*
H4B−0.1041−0.08750.42410.035*
C50.3565 (19)−0.1064 (3)0.3725 (4)0.032 (2)
C60.3652 (19)−0.1415 (3)0.4119 (4)0.033 (2)
H60.2444−0.14070.44070.040*
C70.555 (2)−0.1773 (3)0.4076 (4)0.040 (2)
H70.5648−0.20130.43390.048*
C80.728 (2)−0.1785 (3)0.3663 (5)0.043 (3)
H80.8561−0.20330.36400.051*
C90.719 (2)−0.1436 (4)0.3272 (4)0.038 (2)
H90.8412−0.14470.29860.046*
C100.532 (2)−0.1076 (3)0.3302 (4)0.035 (2)
C110.707 (2)−0.0650 (3)0.2567 (4)0.032 (2)
H11A0.7199−0.09250.23290.039*
H11B0.8852−0.06040.27560.039*
C120.630 (2)−0.0222 (3)0.2247 (4)0.041 (2)
H12A0.7406−0.02150.19240.049*
H12B0.4361−0.02480.21280.049*
C130.427 (2)0.0340 (3)0.2823 (4)0.033 (2)
H13A0.39570.01130.31130.040*
H13B0.26270.03530.25840.040*
C140.4934 (19)0.0814 (4)0.3048 (4)0.033 (2)
H14A0.67100.08110.32490.039*
H14B0.50020.10510.27610.039*
C150.2997 (17)0.1272 (3)0.3756 (4)0.0277 (18)
C160.4900 (18)0.1624 (3)0.3713 (4)0.0294 (19)
H160.61000.16280.34240.035*
C170.505 (2)0.1984 (3)0.4110 (4)0.038 (2)
H170.63280.22310.40820.045*
C180.3359 (19)0.1972 (3)0.4526 (4)0.035 (2)
H180.34610.22110.47900.042*
C190.144 (2)0.1603 (3)0.4566 (4)0.032 (2)
H190.02740.15910.48610.038*
C200.1258 (18)0.1265 (3)0.4179 (4)0.031 (2)
O1−0.0471 (13)0.0889 (2)0.4184 (3)0.0334 (15)
O2−0.2456 (14)−0.0028 (2)0.4572 (3)0.0379 (16)
O30.1848 (13)−0.0692 (2)0.3723 (3)0.0350 (16)
O40.4961 (14)−0.0723 (2)0.2945 (3)0.0381 (17)
O50.6677 (15)0.0207 (3)0.2526 (3)0.0414 (18)
O60.2725 (13)0.0911 (2)0.3399 (3)0.0325 (15)
C210.274 (2)0.2188 (4)0.7537 (5)0.041 (2)
H21A0.25700.19070.77650.049*
H21B0.09670.22450.73480.049*
C220.354 (2)0.2602 (3)0.7869 (4)0.035 (2)
H22A0.23640.26140.81820.043*
H22B0.54480.25590.80050.043*
C230.5683 (18)0.3155 (3)0.7319 (4)0.0294 (19)
H23A0.59790.29250.70310.035*
H23B0.73030.31530.75660.035*
C240.526 (2)0.3640 (3)0.7083 (4)0.032 (2)
H24A0.34900.36560.68810.038*
H24B0.52580.38770.73710.038*
C250.724 (2)0.4109 (3)0.6399 (4)0.031 (2)
C260.5268 (19)0.4460 (3)0.6442 (4)0.032 (2)
H260.40390.44570.67270.038*
C270.5145 (17)0.4811 (4)0.6062 (4)0.032 (2)
H270.38010.50490.60820.039*
C280.6990 (19)0.4818 (3)0.5647 (4)0.032 (2)
H280.69010.50650.53940.038*
C290.8951 (18)0.4469 (3)0.5600 (4)0.0307 (19)
H291.02020.44780.53190.037*
C300.9041 (18)0.4109 (3)0.5970 (4)0.0283 (19)
C311.2366 (19)0.3687 (3)0.5498 (4)0.031 (2)
H31A1.36390.39530.54650.037*
H31B1.11400.36780.51760.037*
C321.3939 (19)0.3235 (3)0.5552 (4)0.033 (2)
H32A1.52970.32210.52690.040*
H32B1.49480.32320.59010.040*
C331.1119 (19)0.2686 (3)0.6009 (4)0.032 (2)
H33A0.99530.29360.61520.038*
H33B1.25940.26140.62770.038*
C340.9432 (19)0.2249 (3)0.5878 (4)0.034 (2)
H34A0.81740.23020.55660.041*
H34B1.06240.19790.58030.041*
C350.625 (2)0.1796 (4)0.6351 (4)0.037 (2)
C360.604 (2)0.1462 (4)0.5958 (5)0.038 (2)
H360.71480.14840.56570.046*
C370.420 (2)0.1088 (4)0.5998 (5)0.044 (3)
H370.41480.08500.57330.053*
C380.246 (2)0.1064 (4)0.6417 (5)0.043 (3)
H380.11580.08190.64360.051*
C390.266 (2)0.1413 (3)0.6819 (5)0.039 (2)
H390.14820.14010.71130.046*
C400.453 (2)0.1766 (3)0.6787 (4)0.037 (2)
O70.4850 (14)0.2117 (2)0.7157 (3)0.0348 (15)
O80.3343 (15)0.3040 (2)0.7592 (3)0.0386 (16)
O90.7442 (12)0.3724 (2)0.6740 (3)0.0312 (15)
O101.0815 (13)0.3740 (2)0.5963 (3)0.0339 (15)
O111.2235 (14)0.2826 (2)0.5513 (3)0.0365 (16)
O120.7963 (14)0.2174 (2)0.6350 (3)0.0361 (16)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.031 (5)0.030 (5)0.037 (5)0.006 (4)0.004 (4)−0.002 (4)
C20.031 (5)0.034 (5)0.043 (5)0.006 (4)0.007 (4)0.001 (4)
C30.038 (5)0.028 (5)0.040 (5)−0.007 (4)0.006 (4)−0.001 (4)
C40.027 (4)0.027 (4)0.035 (5)−0.005 (3)0.003 (4)−0.002 (4)
C50.029 (5)0.021 (4)0.047 (6)0.001 (3)0.000 (4)0.003 (4)
C60.032 (5)0.024 (4)0.042 (5)−0.002 (4)−0.002 (4)0.002 (4)
C70.049 (6)0.026 (5)0.045 (6)0.003 (4)−0.010 (5)0.004 (4)
C80.047 (6)0.021 (5)0.059 (7)0.007 (4)−0.005 (5)−0.006 (4)
C90.034 (5)0.034 (5)0.046 (6)0.008 (4)0.003 (4)−0.007 (4)
C100.036 (5)0.031 (5)0.038 (5)0.000 (4)−0.005 (4)−0.001 (4)
C110.040 (5)0.020 (4)0.037 (5)0.001 (4)0.005 (4)−0.005 (4)
C120.057 (7)0.024 (5)0.042 (6)−0.002 (4)0.014 (5)−0.007 (4)
C130.037 (5)0.025 (4)0.037 (5)0.003 (4)0.008 (4)0.000 (4)
C140.026 (5)0.036 (5)0.036 (5)0.000 (4)0.003 (4)−0.003 (4)
C150.022 (4)0.030 (5)0.031 (4)−0.002 (3)0.006 (3)−0.002 (4)
C160.027 (4)0.028 (4)0.033 (5)−0.002 (4)0.003 (4)0.003 (4)
C170.057 (6)0.016 (4)0.040 (5)0.002 (4)0.000 (5)0.000 (4)
C180.029 (5)0.032 (5)0.043 (5)0.010 (4)0.001 (4)−0.001 (4)
C190.034 (5)0.022 (4)0.039 (5)0.007 (4)0.005 (4)−0.005 (4)
C200.028 (5)0.031 (5)0.034 (5)0.001 (4)−0.002 (4)−0.001 (4)
O10.030 (3)0.029 (3)0.042 (4)0.001 (3)0.005 (3)−0.005 (3)
O20.043 (4)0.033 (4)0.038 (4)0.008 (3)0.005 (3)0.003 (3)
O30.026 (3)0.040 (4)0.039 (4)−0.001 (3)0.009 (3)0.003 (3)
O40.041 (4)0.031 (4)0.043 (4)0.003 (3)0.012 (3)0.003 (3)
O50.045 (4)0.032 (4)0.049 (4)0.009 (3)0.018 (3)−0.013 (3)
O60.030 (3)0.030 (3)0.038 (4)−0.007 (3)0.006 (3)−0.008 (3)
C210.043 (6)0.032 (5)0.049 (6)0.003 (4)0.013 (5)0.004 (4)
C220.043 (5)0.031 (5)0.033 (5)0.001 (4)0.008 (4)0.007 (4)
C230.023 (4)0.027 (4)0.039 (5)−0.001 (3)0.002 (4)0.004 (4)
C240.036 (5)0.030 (5)0.029 (4)−0.005 (4)0.003 (4)−0.001 (4)
C250.038 (5)0.018 (4)0.037 (5)−0.005 (4)−0.008 (4)0.001 (3)
C260.028 (4)0.030 (5)0.036 (5)−0.006 (4)−0.005 (4)−0.002 (4)
C270.013 (4)0.042 (5)0.042 (5)−0.003 (3)−0.002 (3)0.000 (4)
C280.034 (5)0.025 (4)0.037 (5)0.003 (4)0.000 (4)0.005 (4)
C290.023 (4)0.033 (5)0.036 (5)−0.002 (4)0.002 (3)−0.001 (4)
C300.023 (4)0.021 (4)0.041 (5)−0.006 (3)−0.005 (4)−0.002 (4)
C310.027 (5)0.033 (5)0.034 (5)−0.011 (4)0.006 (4)−0.007 (4)
C320.026 (4)0.038 (5)0.037 (5)0.002 (4)0.013 (4)−0.008 (4)
C330.027 (4)0.024 (4)0.045 (5)−0.005 (3)0.000 (4)0.000 (4)
C340.028 (4)0.027 (4)0.048 (6)0.000 (4)−0.003 (4)−0.007 (4)
C350.036 (5)0.031 (5)0.046 (6)−0.004 (4)0.000 (4)0.006 (4)
C360.024 (4)0.039 (5)0.052 (6)0.001 (4)0.006 (4)−0.007 (5)
C370.035 (5)0.031 (5)0.066 (7)−0.003 (4)−0.005 (5)−0.012 (5)
C380.044 (6)0.027 (5)0.057 (7)0.000 (4)0.004 (5)−0.004 (5)
C390.042 (6)0.020 (4)0.054 (6)0.005 (4)0.007 (5)0.004 (4)
C400.038 (5)0.016 (4)0.057 (6)0.013 (4)0.005 (5)0.002 (4)
O70.036 (3)0.025 (3)0.043 (4)−0.006 (3)0.003 (3)0.000 (3)
O80.042 (4)0.029 (3)0.045 (4)0.006 (3)0.012 (3)0.006 (3)
O90.031 (3)0.028 (3)0.034 (3)0.000 (3)−0.002 (3)0.005 (3)
O100.031 (3)0.034 (4)0.037 (4)0.006 (3)0.004 (3)0.003 (3)
O110.040 (4)0.030 (3)0.040 (4)−0.005 (3)0.014 (3)−0.007 (3)
O120.045 (4)0.018 (3)0.045 (4)−0.011 (3)0.007 (3)−0.003 (3)

Geometric parameters (Å, °)

C1—O11.437 (12)C21—O71.443 (13)
C1—C21.530 (14)C21—C221.491 (15)
C1—H1A0.9900C21—H21A0.9900
C1—H1B0.9900C21—H21B0.9900
C2—O21.420 (12)C22—O81.435 (12)
C2—H2A0.9900C22—H22A0.9900
C2—H2B0.9900C22—H22B0.9900
C3—O21.397 (12)C23—O81.396 (11)
C3—C41.532 (13)C23—C241.518 (13)
C3—H3A0.9900C23—H23A0.9900
C3—H3B0.9900C23—H23B0.9900
C4—O31.452 (12)C24—O91.418 (11)
C4—H4A0.9900C24—H24A0.9900
C4—H4B0.9900C24—H24B0.9900
C5—O31.355 (11)C25—O91.394 (11)
C5—C101.391 (15)C25—C261.402 (13)
C5—C61.406 (14)C25—C301.414 (14)
C6—C71.392 (14)C26—C271.384 (14)
C6—H60.9500C26—H260.9500
C7—C81.361 (16)C27—C281.402 (13)
C7—H70.9500C27—H270.9500
C8—C91.397 (16)C28—C291.393 (13)
C8—H80.9500C28—H280.9500
C9—C101.383 (14)C29—C301.383 (13)
C9—H90.9500C29—H290.9500
C10—O41.355 (12)C30—O101.368 (11)
C11—O41.441 (12)C31—O101.420 (12)
C11—C121.502 (14)C31—C321.508 (14)
C11—H11A0.9900C31—H31A0.9900
C11—H11B0.9900C31—H31B0.9900
C12—O51.419 (12)C32—O111.437 (12)
C12—H12A0.9900C32—H32A0.9900
C12—H12B0.9900C32—H32B0.9900
C13—O51.466 (11)C33—O111.435 (12)
C13—C141.500 (13)C33—C341.528 (12)
C13—H13A0.9900C33—H33A0.9900
C13—H13B0.9900C33—H33B0.9900
C14—O61.446 (11)C34—O121.423 (13)
C14—H14A0.9900C34—H34A0.9900
C14—H14B0.9900C34—H34B0.9900
C15—O61.368 (11)C35—O121.370 (12)
C15—C161.379 (12)C35—C361.371 (15)
C15—C201.384 (13)C35—C401.407 (15)
C16—C171.429 (14)C36—C371.405 (15)
C16—H160.9500C36—H360.9500
C17—C181.353 (15)C37—C381.376 (17)
C17—H170.9500C37—H370.9500
C18—C191.422 (14)C38—C391.419 (16)
C18—H180.9500C38—H380.9500
C19—C201.371 (13)C39—C401.367 (15)
C19—H190.9500C39—H390.9500
C20—O11.369 (11)C40—O71.372 (12)
O1—C1—C2107.9 (8)O7—C21—C22107.4 (9)
O1—C1—H1A110.1O7—C21—H21A110.2
C2—C1—H1A110.1C22—C21—H21A110.2
O1—C1—H1B110.1O7—C21—H21B110.2
C2—C1—H1B110.1C22—C21—H21B110.2
H1A—C1—H1B108.4H21A—C21—H21B108.5
O2—C2—C1112.4 (8)O8—C22—C21114.2 (9)
O2—C2—H2A109.1O8—C22—H22A108.7
C1—C2—H2A109.1C21—C22—H22A108.7
O2—C2—H2B109.1O8—C22—H22B108.7
C1—C2—H2B109.1C21—C22—H22B108.7
H2A—C2—H2B107.9H22A—C22—H22B107.6
O2—C3—C4107.3 (8)O8—C23—C24107.5 (7)
O2—C3—H3A110.3O8—C23—H23A110.2
C4—C3—H3A110.3C24—C23—H23A110.2
O2—C3—H3B110.3O8—C23—H23B110.2
C4—C3—H3B110.3C24—C23—H23B110.2
H3A—C3—H3B108.5H23A—C23—H23B108.5
O3—C4—C3105.9 (7)O9—C24—C23107.1 (8)
O3—C4—H4A110.6O9—C24—H24A110.3
C3—C4—H4A110.6C23—C24—H24A110.3
O3—C4—H4B110.6O9—C24—H24B110.3
C3—C4—H4B110.6C23—C24—H24B110.3
H4A—C4—H4B108.7H24A—C24—H24B108.6
O3—C5—C10114.6 (8)O9—C25—C26123.4 (9)
O3—C5—C6124.5 (9)O9—C25—C30115.8 (8)
C10—C5—C6120.9 (9)C26—C25—C30120.6 (8)
C7—C6—C5118.3 (10)C27—C26—C25118.6 (9)
C7—C6—H6120.8C27—C26—H26120.7
C5—C6—H6120.8C25—C26—H26120.7
C8—C7—C6120.9 (10)C26—C27—C28120.4 (9)
C8—C7—H7119.6C26—C27—H27119.8
C6—C7—H7119.6C28—C27—H27119.8
C7—C8—C9120.8 (9)C29—C28—C27121.3 (9)
C7—C8—H8119.6C29—C28—H28119.4
C9—C8—H8119.6C27—C28—H28119.4
C10—C9—C8119.8 (10)C30—C29—C28118.7 (9)
C10—C9—H9120.1C30—C29—H29120.7
C8—C9—H9120.1C28—C29—H29120.7
O4—C10—C9126.2 (10)O10—C30—C29124.7 (9)
O4—C10—C5114.5 (9)O10—C30—C25115.0 (8)
C9—C10—C5119.3 (9)C29—C30—C25120.3 (8)
O4—C11—C12107.3 (8)O10—C31—C32107.8 (8)
O4—C11—H11A110.2O10—C31—H31A110.1
C12—C11—H11A110.2C32—C31—H31A110.1
O4—C11—H11B110.2O10—C31—H31B110.1
C12—C11—H11B110.2C32—C31—H31B110.1
H11A—C11—H11B108.5H31A—C31—H31B108.5
O5—C12—C11114.6 (9)O11—C32—C31113.3 (8)
O5—C12—H12A108.6O11—C32—H32A108.9
C11—C12—H12A108.6C31—C32—H32A108.9
O5—C12—H12B108.6O11—C32—H32B108.9
C11—C12—H12B108.6C31—C32—H32B108.9
H12A—C12—H12B107.6H32A—C32—H32B107.7
O5—C13—C14105.0 (8)O11—C33—C34105.2 (8)
O5—C13—H13A110.7O11—C33—H33A110.7
C14—C13—H13A110.7C34—C33—H33A110.7
O5—C13—H13B110.7O11—C33—H33B110.7
C14—C13—H13B110.7C34—C33—H33B110.7
H13A—C13—H13B108.8H33A—C33—H33B108.8
O6—C14—C13104.3 (7)O12—C34—C33103.2 (7)
O6—C14—H14A110.9O12—C34—H34A111.1
C13—C14—H14A110.9C33—C34—H34A111.1
O6—C14—H14B110.9O12—C34—H34B111.1
C13—C14—H14B110.9C33—C34—H34B111.1
H14A—C14—H14B108.9H34A—C34—H34B109.1
O6—C15—C16123.4 (8)O12—C35—C36125.4 (10)
O6—C15—C20116.1 (8)O12—C35—C40115.8 (9)
C16—C15—C20120.5 (9)C36—C35—C40118.8 (9)
C15—C16—C17119.2 (9)C35—C36—C37120.8 (11)
C15—C16—H16120.4C35—C36—H36119.6
C17—C16—H16120.4C37—C36—H36119.6
C18—C17—C16120.1 (9)C38—C37—C36120.5 (10)
C18—C17—H17119.9C38—C37—H37119.8
C16—C17—H17119.9C36—C37—H37119.8
C17—C18—C19119.9 (9)C37—C38—C39118.7 (10)
C17—C18—H18120.1C37—C38—H38120.7
C19—C18—H18120.1C39—C38—H38120.7
C20—C19—C18119.9 (9)C40—C39—C38120.3 (10)
C20—C19—H19120.1C40—C39—H39119.9
C18—C19—H19120.1C38—C39—H39119.9
O1—C20—C19124.8 (9)C39—C40—O7124.1 (10)
O1—C20—C15114.7 (8)C39—C40—C35120.9 (10)
C19—C20—C15120.4 (9)O7—C40—C35115.0 (9)
C20—O1—C1118.2 (7)C40—O7—C21118.7 (8)
C3—O2—C2113.4 (8)C23—O8—C22113.6 (7)
C5—O3—C4117.8 (8)C25—O9—C24117.9 (7)
C10—O4—C11117.5 (8)C30—O10—C31117.0 (8)
C12—O5—C13112.4 (8)C33—O11—C32114.0 (7)
C15—O6—C14119.0 (7)C35—O12—C34116.6 (7)
O1—C1—C2—O272.6 (10)O7—C21—C22—O871.1 (11)
O2—C3—C4—O3−170.3 (7)O8—C23—C24—O9−171.1 (7)
O3—C5—C6—C7−179.0 (9)O9—C25—C26—C27−175.9 (8)
C10—C5—C6—C70.4 (14)C30—C25—C26—C27−1.1 (12)
C5—C6—C7—C8−0.2 (15)C25—C26—C27—C28−1.0 (13)
C6—C7—C8—C90.1 (16)C26—C27—C28—C291.3 (14)
C7—C8—C9—C10−0.3 (16)C27—C28—C29—C300.5 (14)
C8—C9—C10—O4−178.2 (10)C28—C29—C30—O10178.4 (8)
C8—C9—C10—C50.5 (15)C28—C29—C30—C25−2.5 (13)
O3—C5—C10—O4−2.2 (12)O9—C25—C30—O10−2.7 (11)
C6—C5—C10—O4178.3 (9)C26—C25—C30—O10−178.0 (8)
O3—C5—C10—C9178.9 (9)O9—C25—C30—C29178.1 (8)
C6—C5—C10—C9−0.6 (14)C26—C25—C30—C292.8 (12)
O4—C11—C12—O574.0 (11)O10—C31—C32—O1169.6 (10)
O5—C13—C14—O6−172.4 (7)O11—C33—C34—O12−169.3 (7)
O6—C15—C16—C17−179.3 (9)O12—C35—C36—C37−179.8 (10)
C20—C15—C16—C17−0.4 (14)C40—C35—C36—C37−1.9 (15)
C15—C16—C17—C181.0 (14)C35—C36—C37—C383.6 (16)
C16—C17—C18—C19−0.2 (14)C36—C37—C38—C39−2.8 (16)
C17—C18—C19—C20−1.3 (14)C37—C38—C39—C400.4 (16)
C18—C19—C20—O1178.4 (9)C38—C39—C40—O7179.9 (9)
C18—C19—C20—C152.0 (14)C38—C39—C40—C351.3 (15)
O6—C15—C20—O11.1 (12)O12—C35—C40—C39177.5 (9)
C16—C15—C20—O1−177.9 (8)C36—C35—C40—C39−0.6 (14)
O6—C15—C20—C19177.9 (9)O12—C35—C40—O7−1.2 (12)
C16—C15—C20—C19−1.1 (14)C36—C35—C40—O7−179.2 (9)
C19—C20—O1—C1−3.7 (13)C39—C40—O7—C21−14.8 (14)
C15—C20—O1—C1172.9 (8)C35—C40—O7—C21163.8 (9)
C2—C1—O1—C20177.6 (8)C22—C21—O7—C40−177.2 (8)
C4—C3—O2—C2179.7 (8)C24—C23—O8—C22−175.7 (8)
C1—C2—O2—C3−86.0 (10)C21—C22—O8—C23−86.7 (11)
C10—C5—O3—C4−170.4 (8)C26—C25—O9—C2411.6 (12)
C6—C5—O3—C49.0 (13)C30—C25—O9—C24−163.5 (8)
C3—C4—O3—C5175.2 (8)C23—C24—O9—C25168.2 (7)
C9—C10—O4—C11−14.9 (14)C29—C30—O10—C31−10.2 (12)
C5—C10—O4—C11166.3 (8)C25—C30—O10—C31170.6 (7)
C12—C11—O4—C10−175.8 (8)C32—C31—O10—C30−174.1 (7)
C11—C12—O5—C13−88.0 (11)C34—C33—O11—C32−179.3 (7)
C14—C13—O5—C12−175.2 (8)C31—C32—O11—C33−86.3 (10)
C16—C15—O6—C1417.5 (13)C36—C35—O12—C346.7 (14)
C20—C15—O6—C14−161.4 (8)C40—C35—O12—C34−171.2 (8)
C13—C14—O6—C15166.0 (8)C33—C34—O12—C35−179.7 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16···O8i0.952.573.46 (1)157
C26—H26···O5ii0.952.543.42 (1)155

Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x−1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2081).

References

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