organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aCollege of Chemistry, Xiangtan University, Xiangtan 411105, People's Republic of China, bDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425100, People's Republic of China, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 6 October 2009; accepted 7 October 2009; online 10 October 2009)

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[Dodziuk, H., Sitkowski, J., Stefaniak, L., Mursakulov, I. G., Gasanov, I. G. & Kurbanova, V. A. (1991). Struct. Chem. 3, 269-276.]). For the crystal structure of 6,10,16,19-tetra­oxatrispiro­[4.2.2.4.2.2]nona­decane, see: Wang et al. (2008[Wang, J.-K., Wang, H.-B., Wu, C.-R. & Wang, J.-T. (2008). Acta Cryst. E64, o498.]).

[Scheme 1]

Experimental

Crystal data
  • C17H28O4

  • Mr = 296.39

  • Monoclinic, P 21

  • 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)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 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[Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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.

Structure description top

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] 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.
7,11,18,21-Tetraoxatrispiro[5.2.2.5.2.2]heneicosane top
Crystal data top
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 top
Bruker SMART
diffractometer
3268 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
Graphite monochromatorθmax = 27.1°, θmin = 2.1°
φ and ω scansh = 1414
11846 measured reflectionsk = 1717
3620 independent reflectionsl = 1314
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039 w = 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
Crystal data top
C17H28O4V = 1591.92 (14) Å3
Mr = 296.39Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.1256 (5) ŵ = 0.09 mm1
b = 13.9106 (7) ÅT = 293 K
c = 11.6500 (6) Å0.48 × 0.42 × 0.26 mm
β = 118.002 (1)°
Data collection top
Bruker SMART
diffractometer
3268 reflections with I > 2σ(I)
11846 measured reflectionsRint = 0.031
3620 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0391 restraint
wR(F2) = 0.110H-atom parameters constrained
S = 1.01Δρmax = 0.23 e Å3
3620 reflectionsΔρmin = 0.22 e Å3
380 parametersAbsolute structure: nd
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H15A0.26700.05120.55070.080*
H15B0.15870.05990.60080.080*
C160.3257 (3)0.0201 (2)0.7239 (3)0.0648 (7)
H16A0.37040.03440.77970.078*
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)
H30A0.53780.12600.58220.056*
H30B0.56340.07980.71460.056*
C310.7096 (3)0.17909 (17)0.7372 (3)0.0558 (6)
H31A0.77350.15590.82300.067*
H31B0.66220.23410.74800.067*
C320.7866 (3)0.20990 (19)0.6659 (3)0.0644 (7)
H32A0.72410.23910.58360.077*
H32B0.85430.25760.71700.077*
C330.8567 (2)0.1242 (2)0.6411 (3)0.0594 (6)
H33A0.90140.14500.59120.071*
H33B0.92570.09910.72350.071*
C340.7545 (2)0.04497 (18)0.5671 (2)0.0503 (5)
H34A0.69200.06780.48070.060*
H34B0.80270.01020.55790.060*
Atomic displacement parameters (Å2) top
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, º) top
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—O654.30 (19)
C7—O1—C1—C2171.85 (17)C24—O5—C18—C19168.18 (17)
C7—O1—C1—C667.0 (2)C24—O5—C18—C2371.1 (2)
C9—O2—C1—O158.4 (2)C26—O6—C18—O554.3 (2)
C9—O2—C1—C2172.63 (18)C26—O6—C18—C19168.41 (16)
C9—O2—C1—C666.5 (2)C26—O6—C18—C2370.9 (2)
O1—C1—C2—C368.8 (2)O5—C18—C19—C20175.2 (2)
O2—C1—C2—C3174.9 (2)O6—C18—C19—C2067.6 (2)
C6—C1—C2—C353.5 (3)C23—C18—C19—C2053.9 (3)
C1—C2—C3—C454.9 (3)C18—C19—C20—C2155.4 (3)
C2—C3—C4—C555.4 (3)C19—C20—C21—C2255.8 (3)
C3—C4—C5—C656.6 (3)C20—C21—C22—C2356.0 (3)
C4—C5—C6—C156.6 (3)C21—C22—C23—C1855.5 (3)
O1—C1—C6—C564.3 (3)O5—C18—C23—C22171.80 (17)
O2—C1—C6—C5172.62 (18)O6—C18—C23—C2263.7 (2)
C2—C1—C6—C554.2 (3)C19—C18—C23—C2254.0 (2)
C1—O1—C7—C854.7 (2)C18—O5—C24—C2555.9 (2)
O1—C7—C8—C11170.23 (17)O5—C24—C25—C2653.1 (2)
O1—C7—C8—C949.0 (2)O5—C24—C25—C28174.18 (15)
O1—C7—C8—C1071.3 (2)O5—C24—C25—C2766.8 (2)
C1—O2—C9—C857.6 (2)C18—O6—C26—C2555.9 (2)
C11—C8—C9—O2171.00 (18)C24—C25—C26—O652.9 (2)
C10—C8—C9—O270.6 (2)C28—C25—C26—O6173.35 (16)
C7—C8—C9—O250.6 (2)C27—C25—C26—O667.5 (2)
C12—O3—C10—C853.6 (3)C29—O7—C27—C2555.4 (2)
C11—C8—C10—O351.2 (2)C26—C25—C27—O7171.77 (16)
C9—C8—C10—O3171.96 (19)C24—C25—C27—O769.9 (2)
C7—C8—C10—O368.8 (2)C28—C25—C27—O750.5 (2)
C12—O4—C11—C857.9 (3)C29—O8—C28—C2557.5 (2)
C9—C8—C11—O4172.61 (18)C26—C25—C28—O8172.47 (16)
C10—C8—C11—O452.8 (2)C24—C25—C28—O868.8 (2)
C7—C8—C11—O468.1 (2)C27—C25—C28—O852.1 (2)
C11—O4—C12—O355.6 (2)C27—O7—C29—O857.0 (2)
C11—O4—C12—C13168.4 (2)C27—O7—C29—C30170.75 (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—C1772.1 (2)C28—O8—C29—C3468.1 (2)
O4—C12—C13—C14173.8 (2)O7—C29—C30—C3168.2 (2)
O3—C12—C13—C1469.8 (3)O8—C29—C30—C31175.39 (18)
C17—C12—C13—C1452.8 (3)C34—C29—C30—C3154.1 (2)
C12—C13—C14—C1555.6 (3)C29—C30—C31—C3255.7 (3)
C13—C14—C15—C1655.5 (3)C30—C31—C32—C3356.2 (3)
C14—C15—C16—C1754.8 (3)C31—C32—C33—C3456.1 (3)
C15—C16—C17—C1253.9 (3)C32—C33—C34—C2955.2 (3)
O4—C12—C17—C16170.1 (2)O7—C29—C34—C3364.1 (2)
O3—C12—C17—C1665.0 (3)O8—C29—C34—C33171.77 (18)
C13—C12—C17—C1652.3 (3)C30—C29—C34—C3353.9 (2)

Experimental details

Crystal data
Chemical formulaC17H28O4
Mr296.39
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)11.1256 (5), 13.9106 (7), 11.6500 (6)
β (°) 118.002 (1)
V3)1591.92 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.48 × 0.42 × 0.26
Data collection
DiffractometerBruker SMART
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11846, 3620, 3268
Rint0.031
(sin θ/λ)max1)0.641
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.110, 1.01
No. of reflections3620
No. of parameters380
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.23, 0.22
Absolute structureNd

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2003). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDodziuk, H., Sitkowski, J., Stefaniak, L., Mursakulov, I. G., Gasanov, I. G. & Kurbanova, V. A. (1991). Struct. Chem. 3, 269–276.  CrossRef Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, J.-K., Wang, H.-B., Wu, C.-R. & Wang, J.-T. (2008). Acta Cryst. E64, o498.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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