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The configurations of four of the six chiral centers in the title compound, C18H30O6, are the same as those in pinnatoxin A, while one is inverted. The configuration of the sixth chiral center, which has no equivalent in pinnatoxin A, has also been determined. The overall mol­ecular structure is stabilized by intra­molecular O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032454/bi2053sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032454/bi2053Isup2.hkl
Contains datablock I

CCDC reference: 620667

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.040
  • wR factor = 0.041
  • Data-to-parameter ratio = 7.8

checkCIF/PLATON results

No syntax errors found



Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.6497 Proportion of unique data used 0.7110 Ratio reflections to parameters 7.7880 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.79 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT354_ALERT_3_C Short O-H Bond (0.82A) O5 - H18 ... 0.71 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2377 Count of symmetry unique reflns 2380 Completeness (_total/calc) 99.87% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Molecular Structure Corporation and Rigaku, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CrystalStructure; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

(3S,2'S,5'S,6'R,8'R,10'R)-3-Hydroxy-4-[5'-hydroxy-10'-hydroxymethyl-5'-methyl- 1',7',9'-trioxadispiro[5.1.5.2]pentadec-2'-yl]but-1-ene top
Crystal data top
C18H30O6F(000) = 744.00
Mr = 342.42Dx = 1.253 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2abCell parameters from 22 reflections
a = 11.822 (5) Åθ = 10.3–13.5°
b = 16.841 (8) ŵ = 0.09 mm1
c = 9.117 (5) ÅT = 296 K
V = 1815.1 (15) Å3Block, colourless
Z = 40.55 × 0.45 × 0.35 mm
Data collection top
Rigaku AFC-5S
diffractometer
Rint = 0.004
ω–2θ scansθmax = 27.5°
Absorption correction: ψ scan
(North et al., 1968)
h = 150
Tmin = 0.941, Tmax = 0.968k = 021
2380 measured reflectionsl = 011
2377 independent reflections3 standard reflections every 150 reflections
1690 reflections with I > 2σ(I) intensity decay: 0.3%
Refinement top
Refinement on FH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[0.0002Fo2 + σ2(Fo)]
wR(F2) = 0.041(Δ/σ)max = 0.0004
S = 1.53Δρmax = 0.15 e Å3
1690 reflectionsΔρmin = 0.22 e Å3
217 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5398 (2)0.0851 (1)0.4989 (2)0.0535 (7)
O20.4279 (2)0.0567 (1)0.5956 (2)0.0364 (5)
O30.3771 (2)0.1529 (1)0.4227 (2)0.0358 (5)
O40.5642 (2)0.1840 (1)0.3619 (2)0.0358 (5)
O50.4761 (2)0.3352 (1)0.2654 (3)0.0505 (6)
O60.6813 (2)0.0529 (1)0.4718 (2)0.0495 (6)
C10.4318 (3)0.0815 (2)0.5654 (4)0.0494 (9)
C20.3665 (3)0.0072 (2)0.5276 (3)0.0402 (8)
C30.2446 (3)0.0107 (2)0.5794 (4)0.053 (1)
C40.1877 (2)0.0694 (2)0.5609 (4)0.053 (1)
C50.2579 (3)0.1338 (2)0.6331 (4)0.0459 (9)
C60.3793 (3)0.1328 (2)0.5776 (3)0.0354 (8)
C70.4571 (3)0.1932 (2)0.6498 (3)0.0410 (8)
C80.4666 (3)0.2599 (2)0.5378 (3)0.0409 (8)
C90.4541 (3)0.2159 (2)0.3926 (3)0.0343 (8)
C100.4077 (3)0.2652 (1)0.2637 (3)0.0376 (8)
C110.2841 (3)0.2870 (2)0.2831 (4)0.057 (1)
C120.4239 (3)0.2209 (2)0.1184 (3)0.0458 (9)
C130.5441 (3)0.1916 (2)0.0984 (3)0.049 (1)
C140.5756 (3)0.1393 (2)0.2271 (3)0.0392 (8)
C150.6961 (3)0.1088 (2)0.2253 (3)0.0422 (9)
C160.7150 (3)0.0370 (2)0.3233 (3)0.0403 (8)
C170.8341 (3)0.0078 (2)0.3209 (4)0.0476 (9)
C180.9079 (3)0.0149 (2)0.4240 (4)0.059 (1)
H10.57290.04420.49730.064*
H20.38920.12630.53410.059*
H30.44070.08320.66890.059*
H40.36780.00080.42410.048*
H50.20510.04970.52430.063*
H60.24320.02460.68030.063*
H70.18250.08070.45900.063*
H80.11400.06820.60230.063*
H90.22580.18430.61250.055*
H100.25790.12510.73600.055*
H110.52950.17070.66770.049*
H120.42590.21170.73950.049*
H130.53750.28630.54310.049*
H140.40740.29730.55110.049*
H150.26140.32030.20430.069*
H160.27470.31450.37330.069*
H170.23880.24030.28370.069*
H180.46390.36090.20580.061*
H190.40530.25560.03980.055*
H200.37460.17640.11720.055*
H210.59410.23570.09500.059*
H220.55050.16190.01030.059*
H230.52600.09490.22990.047*
H240.74400.15000.26020.050*
H250.71640.09570.12740.051*
H260.66800.00430.28730.048*
H270.63990.08910.47580.059*
H280.85980.01600.23710.057*
H290.88900.04080.50770.071*
H300.98600.01320.42370.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.058 (1)0.043 (1)0.060 (1)0.006 (1)0.003 (1)0.013 (1)
O20.039 (1)0.0323 (9)0.038 (1)0.0032 (9)0.0001 (9)0.0013 (9)
O30.042 (1)0.032 (1)0.033 (1)0.0062 (9)0.001 (1)0.0008 (9)
O40.036 (1)0.039 (1)0.032 (1)0.0028 (9)0.0000 (9)0.0028 (9)
O50.071 (2)0.031 (1)0.050 (1)0.010 (1)0.009 (1)0.007 (1)
O60.054 (1)0.058 (1)0.036 (1)0.016 (1)0.009 (1)0.003 (1)
C10.061 (2)0.038 (2)0.049 (2)0.001 (2)0.006 (2)0.004 (2)
C20.047 (2)0.038 (2)0.036 (2)0.002 (1)0.002 (2)0.001 (1)
C30.052 (2)0.049 (2)0.058 (2)0.011 (2)0.010 (2)0.002 (2)
C40.036 (2)0.056 (2)0.066 (2)0.005 (2)0.008 (2)0.001 (2)
C50.044 (2)0.045 (2)0.049 (2)0.005 (2)0.013 (2)0.000 (2)
C60.041 (2)0.032 (1)0.033 (1)0.001 (1)0.003 (1)0.002 (1)
C70.048 (2)0.042 (2)0.033 (2)0.000 (1)0.001 (1)0.006 (1)
C80.047 (2)0.034 (1)0.042 (2)0.002 (1)0.001 (2)0.006 (1)
C90.038 (2)0.029 (1)0.036 (2)0.003 (1)0.001 (1)0.003 (1)
C100.041 (2)0.028 (1)0.044 (2)0.004 (1)0.004 (1)0.001 (1)
C110.053 (2)0.054 (2)0.065 (2)0.008 (2)0.007 (2)0.009 (2)
C120.058 (2)0.038 (2)0.041 (2)0.001 (2)0.014 (2)0.003 (1)
C130.067 (2)0.046 (2)0.035 (2)0.007 (2)0.000 (2)0.001 (2)
C140.049 (2)0.036 (1)0.032 (2)0.002 (1)0.002 (1)0.004 (1)
C150.049 (2)0.044 (2)0.033 (2)0.001 (2)0.009 (2)0.002 (1)
C160.044 (2)0.044 (2)0.033 (2)0.002 (1)0.004 (1)0.001 (1)
C170.049 (2)0.050 (2)0.044 (2)0.007 (2)0.011 (2)0.003 (2)
C180.055 (2)0.060 (2)0.062 (2)0.003 (2)0.001 (2)0.009 (2)
Geometric parameters (Å, º) top
O1—C11.415 (4)O6—H270.782
O2—C21.438 (3)C1—H20.950
O2—C61.414 (3)C1—H30.950
O3—C61.452 (3)C2—H40.950
O3—C91.426 (3)C3—H50.950
O4—C91.436 (4)C3—H60.950
O4—C141.447 (3)C4—H70.950
O5—C101.430 (3)C4—H80.950
O6—C161.436 (4)C5—H90.950
C1—C21.511 (4)C5—H100.950
C2—C31.517 (4)C7—H110.950
C3—C41.516 (4)C7—H120.950
C4—C51.516 (4)C8—H130.950
C5—C61.522 (4)C8—H140.950
C6—C71.521 (4)C11—H150.950
C7—C81.522 (4)C11—H160.950
C9—C101.540 (4)C11—H170.950
C10—C111.517 (4)C12—H190.950
C10—C121.532 (4)C12—H200.950
C8—C91.524 (4)C13—H210.950
C12—C131.515 (5)C13—H220.950
C13—C141.514 (4)C14—H230.950
C14—C151.515 (4)C15—H240.950
C15—C161.520 (4)C15—H250.950
C16—C171.491 (4)C16—H260.950
C17—C181.288 (5)C17—H280.915
O1—H10.792C18—H290.906
O5—H180.710C18—H301.038
O1···O5i2.764 (3)O1···H18i2.08
O1···C10i3.532 (4)O1···H19i2.78
O1···C12i3.463 (4)O2···H28ii2.90
O1···C17ii3.541 (4)O4···H9iv2.94
O5···C1iii3.500 (4)O5···H8iv2.60
O5···C4iv3.369 (4)O6···H16iv2.86
O5···C5iv3.497 (4)O6···H28ii2.54
O6···C17ii3.349 (4)C1···H18i2.93
C2—O2—C6115.0 (2)C4—C3—H6108.6
C6—O3—C9110.4 (2)H5—C3—H6109.5
C9—O4—C14116.4 (2)C3—C4—H7108.4
O1—C1—C2113.5 (2)C5—C4—H7108.4
O2—C2—C1105.3 (2)C3—C4—H8110.1
O2—C2—C3112.0 (2)C5—C4—H8110.2
C1—C2—C3112.5 (3)H7—C4—H8109.5
C2—C3—C4110.6 (3)C4—C5—H9109.6
C3—C4—C5110.2 (3)C6—C5—H9108.7
C4—C5—C6111.4 (3)C4—C5—H10108.6
O2—C6—O3109.4 (2)C6—C5—H10109.1
O2—C6—C5110.8 (2)H9—C5—H10109.5
O3—C6—C5107.6 (2)C6—C7—H11110.7
O2—C6—C7108.1 (2)C8—C7—H11110.0
O3—C6—C7106.0 (2)C6—C7—H12110.9
C5—C6—C7114.8 (2)C8—C7—H12111.3
C6—C7—C8104.3 (2)H11—C7—H12109.5
C7—C8—C9102.6 (2)C7—C8—H13112.1
O3—C9—O4109.7 (2)C9—C8—H13110.9
O3—C9—C8104.8 (2)C7—C8—H14110.5
O4—C9—C8105.3 (2)C9—C8—H14111.2
O3—C9—C10108.7 (2)H13—C8—H14109.5
O4—C9—C10112.1 (2)C10—C11—H15109.0
C8—C9—C10115.9 (2)C10—C11—H16109.3
O5—C10—C9103.5 (2)H15—C11—H16109.5
O5—C10—C11110.1 (2)C10—C11—H17110.1
C9—C10—C11112.6 (3)H15—C11—H17109.5
O5—C10—C12109.8 (2)H16—C11—H17109.5
C9—C10—C12110.7 (2)C10—C12—H19108.9
C11—C10—C12109.8 (3)C13—C12—H19109.1
C10—C12—C13112.3 (3)C10—C12—H20108.4
C12—C13—C14109.1 (3)C13—C12—H20108.5
O4—C14—C13109.4 (2)H19—C12—H20109.5
O4—C14—C15105.8 (2)C12—C13—H21109.4
C13—C14—C15114.8 (3)C14—C13—H21109.1
C14—C15—C16113.7 (2)C12—C13—H22110.4
O6—C16—C15111.4 (2)C14—C13—H22109.3
O6—C16—C17109.7 (3)H21—C13—H22109.5
C15—C16—C17113.1 (3)O4—C14—H23109.2
C16—C17—C18126.7 (3)C13—C14—H23109.1
C1—O1—H1114.6C15—C14—H23108.3
C10—O5—H18112.4C14—C15—H24108.0
C16—O6—H27111.3C16—C15—H24107.2
O1—C1—H2108.4C14—C15—H25109.1
C2—C1—H2108.6C16—C15—H25109.3
O1—C1—H3108.9H24—C15—H25109.5
C2—C1—H3108.0O6—C16—H26107.5
H2—C1—H3109.5C15—C16—H26107.0
O2—C2—H4109.6C17—C16—H26107.8
C1—C2—H4108.2C16—C17—H28118.1
C3—C2—H4109.2C18—C17—H28115.2
C2—C3—H5109.2C17—C18—H29119.5
C4—C3—H5109.8C17—C18—H30123.9
C2—C3—H6109.1H29—C18—H30116.2
C6—O2—C2—C1178.2 (4)C5—C6—C7—C8101.8 (4)
C6—O2—C2—C355.7 (5)C6—C7—C8—C930.7 (4)
C2—O2—C6—O362.6 (4)C7—C8—C9—O334.1 (4)
C2—O2—C6—C555.9 (5)C7—C8—C9—O481.7 (4)
C2—O2—C6—C7177.6 (3)C7—C8—C9—C10153.8 (4)
C9—O3—C6—O2111.3 (4)O3—C9—C10—O5167.3 (3)
C9—O3—C6—C5128.2 (4)O3—C9—C10—C1148.4 (4)
C9—O3—C6—C74.9 (5)O3—C9—C10—C1275.1 (4)
C6—O3—C9—O487.9 (4)O4—C9—C10—O571.3 (3)
C6—O3—C9—C824.7 (4)O4—C9—C10—C11169.8 (3)
C6—O3—C9—C10149.2 (3)O4—C9—C10—C1246.4 (4)
C14—O4—C9—O368.1 (4)C8—C9—C10—O549.6 (5)
C14—O4—C9—C8179.6 (3)C8—C9—C10—C1169.3 (5)
C14—O4—C9—C1052.7 (5)C8—C9—C10—C12167.3 (4)
C9—O4—C14—C1358.8 (5)O5—C10—C12—C1363.4 (4)
C9—O4—C14—C15177.0 (3)C9—C10—C12—C1350.3 (5)
O1—C1—C2—O267.1 (4)C11—C10—C12—C13175.3 (4)
O1—C1—C2—C3170.7 (3)C10—C12—C13—C1456.6 (5)
O2—C2—C3—C452.8 (4)C12—C13—C14—O458.4 (5)
C1—C2—C3—C4171.1 (4)C12—C13—C14—C15177.2 (4)
C2—C3—C4—C552.6 (5)O4—C14—C15—C1678.1 (4)
C3—C4—C5—C653.7 (5)C13—C14—C15—C16161.1 (4)
C4—C5—C6—O254.6 (5)C14—C15—C16—O655.6 (5)
C4—C5—C6—O365.0 (5)C14—C15—C16—C17179.8 (4)
C4—C5—C6—C7177.3 (4)O6—C16—C17—C1817.7 (6)
O2—C6—C7—C8134.0 (3)C15—C16—C17—C18107.4 (5)
O3—C6—C7—C816.8 (4)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x+3/2, y, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.792.582.869 (3)103.8
O1—H1···O60.792.092.875 (3)170.0
O6—H27···O40.782.112.791 (3)146.4
O5—H18···O1iii0.712.082.764 (3)163.7
Symmetry code: (iii) x+1, y+1/2, z+1/2.
 

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