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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2712.
Published online 2009 October 10. doi:  10.1107/S1600536809040884
PMCID: PMC2971193

7,11,18,21-Tetra­oxatrispiro­[5.2.2.5.2.2]heneicosa­ne

Abstract

The four six-membered rings all adopt chair conformations in the two independent mol­ecules of the title cyclo­hexa­none cyclic diacetal with penta­erythritol, C17H28O4.

Related literature

For low-temperature manifestation of chirality as evidenced by solution NMR, see: Dodziuk et al. (1991 [triangle]). For the crystal structure of 6,10,16,19-tetra­oxatrispiro­[4.2.2.4.2.2]nona­decane, see: Wang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2712-scheme1.jpg

Experimental

Crystal data

  • C17H28O4
  • M r = 296.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2712-efi1.jpg
  • a = 11.1256 (5) Å
  • b = 13.9106 (7) Å
  • c = 11.6500 (6) Å
  • β = 118.002 (1)°
  • V = 1591.92 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.48 × 0.42 × 0.26 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: none
  • 11846 measured reflections
  • 3620 independent reflections
  • 3268 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.110
  • S = 1.01
  • 3620 reflections
  • 380 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 2003 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809040884/tk2552sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040884/tk2552Isup2.hkl

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

Acknowledgments

We thank the Key Subject Construction Project of Hunan Province (No. 2006–180), the Key Scientific Research Project of Hunan Provincial Education Department (No. 08 A023), the NSF of Hunan Province (No. 09 J J3028) and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Pentaerythritol (2 g, 0.014 mol), cyclohexanone (3.2 g, 0.033 mol), toluene (12 ml) and a catalytic amount (0.2 g) of p-toluenesulfonic acid were heated for four hours. The mixture was cooled and then filtered. The organic phase was washed with water and 5% sodium bicarbonate (20 ml). The solvent was evaporated and the product recrystallized from ethanol to afford colorless crystals (yield 60%); m.p. 386–387 K.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.97 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). In the absence of significant anomalous scattering effects, 3068 Friedel pairs were averaged in the final refinement.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C17H28O4 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H28O4F(000) = 648
Mr = 296.39Dx = 1.237 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6307 reflections
a = 11.1256 (5) Åθ = 2.1–27.1°
b = 13.9106 (7) ŵ = 0.09 mm1
c = 11.6500 (6) ÅT = 293 K
β = 118.002 (1)°Block, colorless
V = 1591.92 (14) Å30.48 × 0.42 × 0.26 mm
Z = 4

Data collection

Bruker SMART diffractometer3268 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 27.1°, θmin = 2.1°
[var phi] and ω scansh = −14→14
11846 measured reflectionsk = −17→17
3620 independent reflectionsl = −13→14

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039w = 1/[σ2(Fo2) + (0.0742P)2 + 0.1289P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.23 e Å3
3620 reflectionsΔρmin = −0.22 e Å3
380 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.118 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: nd
Secondary atom site location: difference Fourier map

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.23696 (16)0.49997 (11)0.73537 (14)0.0470 (4)
O20.42168 (15)0.47553 (13)0.93942 (16)0.0553 (4)
O30.25850 (16)0.23362 (13)0.67497 (16)0.0512 (4)
O40.10089 (15)0.21168 (13)0.75154 (18)0.0570 (4)
O50.69505 (15)0.27388 (10)0.85086 (14)0.0425 (3)
O60.83677 (14)0.33303 (11)0.76920 (15)0.0422 (3)
O70.75739 (13)0.02803 (10)0.76038 (13)0.0395 (3)
O80.56565 (13)0.04986 (11)0.55912 (14)0.0450 (4)
C10.3257 (2)0.54471 (16)0.8557 (2)0.0442 (5)
C20.4058 (2)0.61848 (19)0.8249 (3)0.0575 (6)
H2A0.44680.58780.77690.069*
H2B0.47870.64300.90550.069*
C30.3178 (3)0.7017 (2)0.7456 (3)0.0658 (7)
H3A0.25210.67860.66050.079*
H3B0.37470.74930.73360.079*
C40.2428 (3)0.7485 (2)0.8119 (3)0.0658 (7)
H4A0.30790.77800.89280.079*
H4B0.18280.79850.75630.079*
C50.1607 (3)0.6742 (2)0.8389 (3)0.0612 (6)
H5A0.09030.64910.75720.073*
H5B0.11640.70430.88430.073*
C60.2487 (2)0.59221 (18)0.9201 (2)0.0516 (5)
H6A0.19190.54470.93230.062*
H6B0.31350.61631.00500.062*
C70.1655 (2)0.41903 (17)0.7462 (2)0.0486 (5)
H7A0.11300.39040.66100.058*
H7B0.10240.43990.77690.058*
C80.2615 (2)0.34349 (16)0.8395 (2)0.0430 (5)
C90.3594 (3)0.39432 (18)0.9644 (2)0.0560 (6)
H9A0.31040.41511.01020.067*
H9B0.42950.34951.01990.067*
C100.3419 (2)0.29263 (18)0.7810 (2)0.0487 (5)
H10A0.38560.34040.75240.058*
H10B0.41260.25370.84750.058*
C110.1797 (3)0.26731 (19)0.8654 (2)0.0555 (6)
H11A0.24100.22540.93470.067*
H11B0.11970.29800.89350.067*
C120.1781 (2)0.16498 (17)0.7002 (2)0.0464 (5)
C130.0764 (2)0.1282 (2)0.5673 (3)0.0613 (6)
H13A0.03170.18250.51100.074*
H13B0.00730.09070.57540.074*
C140.1431 (3)0.0666 (2)0.5054 (3)0.0661 (7)
H14A0.07350.04190.42310.079*
H14B0.20440.10620.48790.079*
C150.2212 (3)−0.0162 (2)0.5910 (3)0.0666 (7)
H15A0.2670−0.05120.55070.080*
H15B0.1587−0.05990.60080.080*
C160.3257 (3)0.0201 (2)0.7239 (3)0.0648 (7)
H16A0.3704−0.03440.77970.078*
H16B0.39450.05720.71470.078*
C170.2613 (3)0.0820 (2)0.7872 (2)0.0567 (6)
H17A0.33230.10780.86790.068*
H17B0.20260.04230.80810.068*
C180.75704 (19)0.35744 (14)0.83150 (18)0.0361 (4)
C190.8575 (3)0.39214 (17)0.9659 (2)0.0539 (6)
H19A0.92740.34371.00790.065*
H19B0.81060.40041.01750.065*
C200.9240 (3)0.4863 (2)0.9620 (2)0.0642 (7)
H20A0.98290.50781.05010.077*
H20B0.97990.47630.91940.077*
C210.8190 (3)0.56338 (17)0.8899 (3)0.0608 (6)
H21A0.86450.62140.88460.073*
H21B0.76930.57840.93740.073*
C220.7201 (3)0.52960 (17)0.7538 (2)0.0544 (6)
H22A0.76860.52080.70380.065*
H22B0.65090.57840.71090.065*
C230.6521 (2)0.43532 (15)0.7575 (2)0.0447 (5)
H23A0.59400.41370.66930.054*
H23B0.59530.44590.79890.054*
C240.61688 (19)0.21936 (15)0.7364 (2)0.0396 (4)
H24A0.53950.25710.67650.047*
H24B0.58250.16210.75870.047*
C250.70167 (19)0.19016 (14)0.67041 (18)0.0351 (4)
C260.7655 (2)0.28130 (15)0.6507 (2)0.0425 (4)
H26A0.82800.26450.61750.051*
H26B0.69480.32180.58680.051*
C270.81339 (19)0.11917 (14)0.7551 (2)0.0413 (4)
H27A0.87640.11110.72000.050*
H27B0.86370.14490.84240.050*
C280.6117 (2)0.14090 (16)0.54104 (19)0.0461 (5)
H28A0.53370.18140.48970.055*
H28B0.66260.13280.49320.055*
C290.67397 (18)−0.01425 (14)0.63682 (18)0.0366 (4)
C300.6074 (2)−0.10035 (16)0.6639 (2)0.0470 (5)
H30A0.5378−0.12600.58220.056*
H30B0.5634−0.07980.71460.056*
C310.7096 (3)−0.17909 (17)0.7372 (3)0.0558 (6)
H31A0.7735−0.15590.82300.067*
H31B0.6622−0.23410.74800.067*
C320.7866 (3)−0.20990 (19)0.6659 (3)0.0644 (7)
H32A0.7241−0.23910.58360.077*
H32B0.8543−0.25760.71700.077*
C330.8567 (2)−0.1242 (2)0.6411 (3)0.0594 (6)
H33A0.9014−0.14500.59120.071*
H33B0.9257−0.09910.72350.071*
C340.7545 (2)−0.04497 (18)0.5671 (2)0.0503 (5)
H34A0.6920−0.06780.48070.060*
H34B0.80270.01020.55790.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0574 (8)0.0422 (8)0.0368 (7)0.0038 (7)0.0184 (6)−0.0055 (6)
O20.0457 (8)0.0503 (9)0.0531 (9)0.0017 (7)0.0093 (7)−0.0022 (7)
O30.0559 (8)0.0485 (9)0.0580 (9)−0.0039 (7)0.0342 (7)−0.0076 (7)
O40.0471 (8)0.0576 (10)0.0765 (11)−0.0064 (8)0.0374 (8)−0.0121 (9)
O50.0531 (7)0.0372 (7)0.0417 (7)−0.0100 (6)0.0259 (6)−0.0030 (6)
O60.0378 (7)0.0359 (7)0.0567 (9)−0.0033 (5)0.0252 (6)−0.0010 (6)
O70.0428 (7)0.0305 (7)0.0361 (7)0.0007 (5)0.0109 (6)−0.0003 (5)
O80.0398 (7)0.0402 (8)0.0405 (8)0.0027 (6)0.0068 (6)−0.0029 (6)
C10.0425 (10)0.0443 (11)0.0419 (11)0.0033 (9)0.0167 (8)−0.0069 (9)
C20.0565 (13)0.0526 (14)0.0706 (16)0.0012 (11)0.0358 (12)−0.0052 (12)
C30.0844 (17)0.0558 (15)0.0697 (16)0.0028 (14)0.0466 (15)0.0019 (13)
C40.0810 (17)0.0470 (13)0.0732 (17)0.0114 (12)0.0393 (14)−0.0044 (12)
C50.0609 (14)0.0569 (14)0.0657 (15)0.0082 (11)0.0297 (12)−0.0168 (12)
C60.0628 (13)0.0508 (13)0.0480 (12)−0.0052 (11)0.0317 (11)−0.0145 (10)
C70.0448 (10)0.0462 (11)0.0457 (11)0.0041 (9)0.0138 (9)−0.0080 (9)
C80.0419 (10)0.0433 (11)0.0440 (11)0.0022 (8)0.0204 (9)−0.0023 (9)
C90.0634 (13)0.0496 (13)0.0433 (12)0.0041 (11)0.0153 (10)0.0026 (10)
C100.0414 (10)0.0476 (11)0.0613 (13)0.0006 (9)0.0277 (10)−0.0051 (10)
C110.0643 (14)0.0541 (14)0.0638 (14)−0.0017 (11)0.0432 (12)−0.0046 (11)
C120.0419 (10)0.0477 (12)0.0524 (12)−0.0039 (9)0.0245 (9)−0.0042 (10)
C130.0524 (13)0.0555 (14)0.0600 (14)−0.0031 (11)0.0131 (11)−0.0059 (11)
C140.0867 (18)0.0547 (15)0.0515 (14)−0.0116 (13)0.0282 (13)−0.0115 (12)
C150.0853 (17)0.0449 (13)0.0734 (17)−0.0066 (13)0.0405 (15)−0.0127 (12)
C160.0620 (14)0.0519 (14)0.0736 (17)0.0106 (12)0.0262 (13)−0.0016 (12)
C170.0630 (14)0.0546 (13)0.0470 (12)0.0037 (11)0.0213 (11)0.0035 (11)
C180.0372 (9)0.0320 (9)0.0378 (9)−0.0028 (7)0.0165 (7)0.0003 (7)
C190.0617 (13)0.0437 (12)0.0401 (11)−0.0114 (10)0.0105 (10)0.0020 (9)
C200.0660 (14)0.0536 (14)0.0496 (13)−0.0235 (12)0.0078 (11)−0.0037 (11)
C210.0843 (17)0.0354 (11)0.0634 (15)−0.0142 (11)0.0351 (13)−0.0067 (10)
C220.0659 (13)0.0351 (11)0.0575 (14)0.0025 (10)0.0251 (11)0.0080 (10)
C230.0407 (10)0.0385 (10)0.0508 (11)0.0033 (8)0.0181 (9)−0.0012 (9)
C240.0359 (8)0.0354 (9)0.0475 (10)−0.0046 (8)0.0196 (8)−0.0041 (8)
C250.0363 (8)0.0320 (9)0.0337 (9)0.0022 (7)0.0136 (7)0.0021 (7)
C260.0497 (10)0.0369 (10)0.0476 (11)0.0022 (9)0.0285 (9)0.0042 (9)
C270.0345 (9)0.0329 (9)0.0453 (11)−0.0001 (7)0.0096 (8)−0.0014 (8)
C280.0529 (11)0.0410 (11)0.0342 (10)0.0057 (9)0.0119 (9)0.0028 (8)
C290.0362 (8)0.0347 (9)0.0338 (9)0.0012 (7)0.0121 (7)−0.0029 (8)
C300.0464 (10)0.0383 (11)0.0557 (12)−0.0057 (9)0.0236 (9)−0.0058 (9)
C310.0662 (14)0.0373 (11)0.0626 (15)0.0018 (10)0.0291 (12)0.0051 (10)
C320.0745 (16)0.0414 (12)0.0745 (17)0.0155 (12)0.0326 (13)−0.0014 (12)
C330.0556 (12)0.0603 (15)0.0696 (15)0.0125 (11)0.0354 (11)−0.0042 (12)
C340.0559 (12)0.0496 (13)0.0518 (12)0.0006 (10)0.0307 (10)−0.0039 (10)

Geometric parameters (Å, °)

O1—C71.417 (3)C15—C161.521 (4)
O1—C11.424 (2)C15—H15A0.9700
O2—C91.424 (3)C15—H15B0.9700
O2—C11.428 (3)C16—C171.514 (4)
O3—C101.409 (3)C16—H16A0.9700
O3—C121.430 (3)C16—H16B0.9700
O4—C121.414 (3)C17—H17A0.9700
O4—C111.426 (3)C17—H17B0.9700
O5—C241.421 (2)C18—C191.513 (3)
O5—C181.423 (2)C18—C231.528 (3)
O6—C261.423 (3)C19—C201.516 (3)
O6—C181.426 (2)C19—H19A0.9700
O7—C291.423 (2)C19—H19B0.9700
O7—C271.427 (2)C20—C211.515 (4)
O8—C281.418 (3)C20—H20A0.9700
O8—C291.429 (2)C20—H20B0.9700
C1—C21.509 (3)C21—C221.519 (3)
C1—C61.529 (3)C21—H21A0.9700
C2—C31.518 (4)C21—H21B0.9700
C2—H2A0.9700C22—C231.525 (3)
C2—H2B0.9700C22—H22A0.9700
C3—C41.524 (4)C22—H22B0.9700
C3—H3A0.9700C23—H23A0.9700
C3—H3B0.9700C23—H23B0.9700
C4—C51.508 (4)C24—C251.525 (3)
C4—H4A0.9700C24—H24A0.9700
C4—H4B0.9700C24—H24B0.9700
C5—C61.511 (4)C25—C261.522 (3)
C5—H5A0.9700C25—C281.525 (3)
C5—H5B0.9700C25—C271.530 (3)
C6—H6A0.9700C26—H26A0.9700
C6—H6B0.9700C26—H26B0.9700
C7—C81.528 (3)C27—H27A0.9700
C7—H7A0.9700C27—H27B0.9700
C7—H7B0.9700C28—H28A0.9700
C8—C111.517 (3)C28—H28B0.9700
C8—C91.522 (3)C29—C301.517 (3)
C8—C101.528 (3)C29—C341.526 (3)
C9—H9A0.9700C30—C311.520 (3)
C9—H9B0.9700C30—H30A0.9700
C10—H10A0.9700C30—H30B0.9700
C10—H10B0.9700C31—C321.509 (4)
C11—H11A0.9700C31—H31A0.9700
C11—H11B0.9700C31—H31B0.9700
C12—C131.515 (3)C32—C331.523 (4)
C12—C171.528 (3)C32—H32A0.9700
C13—C141.519 (4)C32—H32B0.9700
C13—H13A0.9700C33—C341.527 (3)
C13—H13B0.9700C33—H33A0.9700
C14—C151.504 (4)C33—H33B0.9700
C14—H14A0.9700C34—H34A0.9700
C14—H14B0.9700C34—H34B0.9700
C7—O1—C1114.73 (17)C12—C17—H17A109.1
C9—O2—C1113.24 (16)C16—C17—H17B109.1
C10—O3—C12115.24 (17)C12—C17—H17B109.1
C12—O4—C11114.35 (16)H17A—C17—H17B107.8
C24—O5—C18114.58 (14)O5—C18—O6110.48 (15)
C26—O6—C18114.70 (14)O5—C18—C19105.91 (15)
C29—O7—C27114.47 (15)O6—C18—C19105.59 (16)
C28—O8—C29113.29 (15)O5—C18—C23111.72 (15)
O1—C1—O2109.17 (17)O6—C18—C23111.99 (16)
O1—C1—C2106.11 (18)C19—C18—C23110.81 (17)
O2—C1—C2106.56 (17)C18—C19—C20112.22 (19)
O1—C1—C6112.50 (17)C18—C19—H19A109.2
O2—C1—C6111.55 (18)C20—C19—H19A109.2
C2—C1—C6110.64 (19)C18—C19—H19B109.2
C1—C2—C3112.3 (2)C20—C19—H19B109.2
C1—C2—H2A109.1H19A—C19—H19B107.9
C3—C2—H2A109.1C21—C20—C19111.6 (2)
C1—C2—H2B109.1C21—C20—H20A109.3
C3—C2—H2B109.1C19—C20—H20A109.3
H2A—C2—H2B107.9C21—C20—H20B109.3
C2—C3—C4111.6 (2)C19—C20—H20B109.3
C2—C3—H3A109.3H20A—C20—H20B108.0
C4—C3—H3A109.3C20—C21—C22110.6 (2)
C2—C3—H3B109.3C20—C21—H21A109.5
C4—C3—H3B109.3C22—C21—H21A109.5
H3A—C3—H3B108.0C20—C21—H21B109.5
C5—C4—C3110.0 (2)C22—C21—H21B109.5
C5—C4—H4A109.7H21A—C21—H21B108.1
C3—C4—H4A109.7C21—C22—C23111.3 (2)
C5—C4—H4B109.7C21—C22—H22A109.4
C3—C4—H4B109.7C23—C22—H22A109.4
H4A—C4—H4B108.2C21—C22—H22B109.4
C4—C5—C6111.7 (2)C23—C22—H22B109.4
C4—C5—H5A109.3H22A—C22—H22B108.0
C6—C5—H5A109.3C22—C23—C18111.61 (17)
C4—C5—H5B109.3C22—C23—H23A109.3
C6—C5—H5B109.3C18—C23—H23A109.3
H5A—C5—H5B107.9C22—C23—H23B109.3
C5—C6—C1111.52 (19)C18—C23—H23B109.3
C5—C6—H6A109.3H23A—C23—H23B108.0
C1—C6—H6A109.3O5—C24—C25111.35 (15)
C5—C6—H6B109.3O5—C24—H24A109.4
C1—C6—H6B109.3C25—C24—H24A109.4
H6A—C6—H6B108.0O5—C24—H24B109.4
O1—C7—C8112.05 (17)C25—C24—H24B109.4
O1—C7—H7A109.2H24A—C24—H24B108.0
C8—C7—H7A109.2C26—C25—C24107.28 (16)
O1—C7—H7B109.2C26—C25—C28111.19 (16)
C8—C7—H7B109.2C24—C25—C28110.07 (16)
H7A—C7—H7B107.9C26—C25—C27109.84 (15)
C11—C8—C9111.17 (19)C24—C25—C27110.74 (16)
C11—C8—C10107.25 (19)C28—C25—C27107.74 (16)
C9—C8—C10109.61 (18)O6—C26—C25111.19 (16)
C11—C8—C7109.71 (18)O6—C26—H26A109.4
C9—C8—C7107.93 (18)C25—C26—H26A109.4
C10—C8—C7111.18 (19)O6—C26—H26B109.4
O2—C9—C8111.81 (19)C25—C26—H26B109.4
O2—C9—H9A109.3H26A—C26—H26B108.0
C8—C9—H9A109.3O7—C27—C25111.24 (15)
O2—C9—H9B109.3O7—C27—H27A109.4
C8—C9—H9B109.3C25—C27—H27A109.4
H9A—C9—H9B107.9O7—C27—H27B109.4
O3—C10—C8112.26 (16)C25—C27—H27B109.4
O3—C10—H10A109.2H27A—C27—H27B108.0
C8—C10—H10A109.2O8—C28—C25111.70 (16)
O3—C10—H10B109.2O8—C28—H28A109.3
C8—C10—H10B109.2C25—C28—H28A109.3
H10A—C10—H10B107.9O8—C28—H28B109.3
O4—C11—C8110.98 (18)C25—C28—H28B109.3
O4—C11—H11A109.4H28A—C28—H28B107.9
C8—C11—H11A109.4O7—C29—O8109.78 (15)
O4—C11—H11B109.4O7—C29—C30105.44 (16)
C8—C11—H11B109.4O8—C29—C30105.98 (15)
H11A—C11—H11B108.0O7—C29—C34112.77 (15)
O4—C12—O3110.06 (18)O8—C29—C34111.65 (17)
O4—C12—C13106.08 (18)C30—C29—C34110.83 (17)
O3—C12—C13104.72 (19)C29—C30—C31112.07 (17)
O4—C12—C17111.48 (19)C29—C30—H30A109.2
O3—C12—C17113.44 (18)C31—C30—H30A109.2
C13—C12—C17110.6 (2)C29—C30—H30B109.2
C12—C13—C14112.3 (2)C31—C30—H30B109.2
C12—C13—H13A109.2H30A—C30—H30B107.9
C14—C13—H13A109.2C32—C31—C30111.3 (2)
C12—C13—H13B109.2C32—C31—H31A109.4
C14—C13—H13B109.2C30—C31—H31A109.4
H13A—C13—H13B107.9C32—C31—H31B109.4
C15—C14—C13112.1 (2)C30—C31—H31B109.4
C15—C14—H14A109.2H31A—C31—H31B108.0
C13—C14—H14A109.2C31—C32—C33110.8 (2)
C15—C14—H14B109.2C31—C32—H32A109.5
C13—C14—H14B109.2C33—C32—H32A109.5
H14A—C14—H14B107.9C31—C32—H32B109.5
C14—C15—C16110.4 (2)C33—C32—H32B109.5
C14—C15—H15A109.6H32A—C32—H32B108.1
C16—C15—H15A109.6C32—C33—C34111.14 (19)
C14—C15—H15B109.6C32—C33—H33A109.4
C16—C15—H15B109.6C34—C33—H33A109.4
H15A—C15—H15B108.1C32—C33—H33B109.4
C17—C16—C15112.0 (2)C34—C33—H33B109.4
C17—C16—H16A109.2H33A—C33—H33B108.0
C15—C16—H16A109.2C33—C34—C29111.66 (19)
C17—C16—H16B109.2C33—C34—H34A109.3
C15—C16—H16B109.2C29—C34—H34A109.3
H16A—C16—H16B107.9C33—C34—H34B109.3
C16—C17—C12112.6 (2)C29—C34—H34B109.3
C16—C17—H17A109.1H34A—C34—H34B107.9
C7—O1—C1—O257.4 (2)C24—O5—C18—O6−54.30 (19)
C7—O1—C1—C2171.85 (17)C24—O5—C18—C19−168.18 (17)
C7—O1—C1—C6−67.0 (2)C24—O5—C18—C2371.1 (2)
C9—O2—C1—O1−58.4 (2)C26—O6—C18—O554.3 (2)
C9—O2—C1—C2−172.63 (18)C26—O6—C18—C19168.41 (16)
C9—O2—C1—C666.5 (2)C26—O6—C18—C23−70.9 (2)
O1—C1—C2—C368.8 (2)O5—C18—C19—C20−175.2 (2)
O2—C1—C2—C3−174.9 (2)O6—C18—C19—C2067.6 (2)
C6—C1—C2—C3−53.5 (3)C23—C18—C19—C20−53.9 (3)
C1—C2—C3—C454.9 (3)C18—C19—C20—C2155.4 (3)
C2—C3—C4—C5−55.4 (3)C19—C20—C21—C22−55.8 (3)
C3—C4—C5—C656.6 (3)C20—C21—C22—C2356.0 (3)
C4—C5—C6—C1−56.6 (3)C21—C22—C23—C18−55.5 (3)
O1—C1—C6—C5−64.3 (3)O5—C18—C23—C22171.80 (17)
O2—C1—C6—C5172.62 (18)O6—C18—C23—C22−63.7 (2)
C2—C1—C6—C554.2 (3)C19—C18—C23—C2254.0 (2)
C1—O1—C7—C8−54.7 (2)C18—O5—C24—C2555.9 (2)
O1—C7—C8—C11170.23 (17)O5—C24—C25—C26−53.1 (2)
O1—C7—C8—C949.0 (2)O5—C24—C25—C28−174.18 (15)
O1—C7—C8—C10−71.3 (2)O5—C24—C25—C2766.8 (2)
C1—O2—C9—C857.6 (2)C18—O6—C26—C25−55.9 (2)
C11—C8—C9—O2−171.00 (18)C24—C25—C26—O652.9 (2)
C10—C8—C9—O270.6 (2)C28—C25—C26—O6173.35 (16)
C7—C8—C9—O2−50.6 (2)C27—C25—C26—O6−67.5 (2)
C12—O3—C10—C8−53.6 (3)C29—O7—C27—C2555.4 (2)
C11—C8—C10—O351.2 (2)C26—C25—C27—O7−171.77 (16)
C9—C8—C10—O3171.96 (19)C24—C25—C27—O769.9 (2)
C7—C8—C10—O3−68.8 (2)C28—C25—C27—O7−50.5 (2)
C12—O4—C11—C857.9 (3)C29—O8—C28—C25−57.5 (2)
C9—C8—C11—O4−172.61 (18)C26—C25—C28—O8172.47 (16)
C10—C8—C11—O4−52.8 (2)C24—C25—C28—O8−68.8 (2)
C7—C8—C11—O468.1 (2)C27—C25—C28—O852.1 (2)
C11—O4—C12—O3−55.6 (2)C27—O7—C29—O8−57.0 (2)
C11—O4—C12—C13−168.4 (2)C27—O7—C29—C30−170.75 (15)
C11—O4—C12—C1771.1 (3)C27—O7—C29—C3468.2 (2)
C10—O3—C12—O453.6 (2)C28—O8—C29—O757.7 (2)
C10—O3—C12—C13167.21 (18)C28—O8—C29—C30171.09 (16)
C10—O3—C12—C17−72.1 (2)C28—O8—C29—C34−68.1 (2)
O4—C12—C13—C14−173.8 (2)O7—C29—C30—C31−68.2 (2)
O3—C12—C13—C1469.8 (3)O8—C29—C30—C31175.39 (18)
C17—C12—C13—C14−52.8 (3)C34—C29—C30—C3154.1 (2)
C12—C13—C14—C1555.6 (3)C29—C30—C31—C32−55.7 (3)
C13—C14—C15—C16−55.5 (3)C30—C31—C32—C3356.2 (3)
C14—C15—C16—C1754.8 (3)C31—C32—C33—C34−56.1 (3)
C15—C16—C17—C12−53.9 (3)C32—C33—C34—C2955.2 (3)
O4—C12—C17—C16170.1 (2)O7—C29—C34—C3364.1 (2)
O3—C12—C17—C16−65.0 (3)O8—C29—C34—C33−171.77 (18)
C13—C12—C17—C1652.3 (3)C30—C29—C34—C33−53.9 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2552).

References

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