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The crystal structure of the title compound, C17H24O9, was determined to confirm its identity. The pyran ring adopts the 7C4 chair form in which all substituents adopt equatorial orientations, except for the one bearing the allyl group, which is axial. The conformation about the bond connecting the allyl group to the ring places the internal alkene C atom gauche to the ring O atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804024407/lh6268sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804024407/lh6268Isup2.hkl
Contains datablock I

CCDC reference: 255869

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.053
  • wR factor = 0.100
  • Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.95 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 26.43 From the CIF: _reflns_number_total 2286 Count of symmetry unique reflns 2308 Completeness (_total/calc) 99.05% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

5,6,7,9-Tetra-O-acetyl-4,8-anhydro-1,2,3-trideoxy-D-glycero-D-gulo- non-1-enitol top
Crystal data top
C17H24O9Dx = 1.289 Mg m3
Mr = 372.36Melting point: 376 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1490 reflections
a = 5.4608 (6) Åθ = 2.9–25.9°
b = 14.4068 (17) ŵ = 0.11 mm1
c = 24.392 (3) ÅT = 193 K
V = 1919.0 (4) Å3Needle, colourless
Z = 40.60 × 0.06 × 0.05 mm
F(000) = 792
Data collection top
Bruker PLATFORM
diffractometer/SMART 1000 CCD area-detector
2286 independent reflections
Radiation source: fine-focus sealed tube1581 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.084
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 1.6°
ω scansh = 56
Absorption correction: integration
(SHELXTL; Sheldrick, 1997b)
k = 1517
Tmin = 0.964, Tmax = 0.995l = 3030
10431 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0331P)2 + 0.5928P]
where P = (Fo2 + 2Fc2)/3
2286 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.20 e Å3
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.

Hydrogen atoms were refined with fixed C—H distances and with isotropic displacement parameters 20% (for C—H) greater than those for their attached atoms. The absolute structure could not be determined from the X-ray data (light atoms only), but was assigned on the basis of the established stereochemistry of the precursor compound. Friedel pairs were merged before the final least-squares refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O50.3586 (5)0.26661 (15)0.16644 (10)0.0305 (6)
O60.3876 (4)0.42836 (18)0.23409 (8)0.0272 (5)
O70.3567 (4)0.59133 (15)0.16453 (9)0.0282 (6)
O80.7388 (4)0.42879 (18)0.08715 (9)0.0333 (6)
O90.8465 (5)0.58918 (18)0.02816 (9)0.0426 (7)
O100.6694 (5)0.16661 (18)0.17619 (12)0.0472 (8)
O120.0232 (4)0.4330 (2)0.23480 (10)0.0419 (7)
O140.6421 (5)0.68568 (18)0.20089 (11)0.0409 (7)
O161.1120 (7)0.7039 (3)0.04274 (13)0.0698 (10)
C10.2802 (11)0.3987 (3)0.03443 (19)0.0711 (16)
H1A0.12640.42140.02210.085*
H1B0.32770.40700.07160.085*
C20.4240 (10)0.3569 (3)0.00082 (16)0.0544 (13)
H20.57630.33520.01460.065*
C30.3692 (9)0.3399 (3)0.05840 (14)0.0425 (11)
H3A0.29680.27730.06240.051*
H3B0.24570.38560.07080.051*
C40.5948 (7)0.3469 (2)0.09554 (14)0.0321 (10)
H40.70170.29230.08730.039*
C50.5286 (7)0.3425 (2)0.15654 (14)0.0280 (9)
H50.68020.33340.17890.034*
C60.3975 (6)0.4292 (3)0.17484 (12)0.0259 (8)
H60.22740.42950.15970.031*
C70.5296 (7)0.5167 (2)0.15750 (13)0.0240 (8)
H70.67450.52710.18180.029*
C80.6125 (7)0.5132 (2)0.09782 (14)0.0282 (9)
H80.46710.51820.07310.034*
C90.7888 (7)0.5907 (3)0.08583 (14)0.0366 (10)
H9A0.71420.65110.09570.044*
H9B0.94000.58260.10770.044*
C100.4540 (7)0.1818 (3)0.17389 (15)0.0315 (9)
C110.2579 (8)0.1101 (3)0.17786 (18)0.0422 (11)
H11A0.31040.06070.20290.051*
H11B0.22690.08370.14150.051*
H11C0.10750.13860.19190.051*
C120.1676 (6)0.4288 (3)0.25898 (13)0.0258 (8)
C130.1981 (7)0.4258 (3)0.31954 (13)0.0354 (9)
H13A0.03730.41950.33700.042*
H13B0.27620.48330.33200.042*
H13C0.30100.37270.32950.042*
C140.4334 (8)0.6725 (3)0.18686 (14)0.0288 (9)
C150.2287 (7)0.7399 (3)0.19053 (17)0.0377 (10)
H15A0.29160.80000.20300.045*
H15B0.10640.71710.21670.045*
H15C0.15290.74710.15440.045*
C161.0150 (9)0.6504 (3)0.01198 (18)0.0482 (12)
C171.0608 (10)0.6452 (3)0.04807 (17)0.0657 (15)
H17A0.97410.69590.06650.079*
H17B1.00170.58550.06210.079*
H17C1.23690.65070.05510.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O50.0256 (15)0.0216 (13)0.0444 (15)0.0001 (12)0.0010 (13)0.0049 (12)
O60.0203 (13)0.0336 (13)0.0277 (12)0.0004 (13)0.0003 (10)0.0037 (12)
O70.0254 (14)0.0219 (14)0.0372 (13)0.0006 (12)0.0049 (12)0.0044 (11)
O80.0323 (14)0.0259 (14)0.0417 (14)0.0034 (14)0.0104 (11)0.0003 (12)
O90.0588 (18)0.0361 (16)0.0330 (14)0.0077 (16)0.0144 (13)0.0014 (12)
O100.0257 (17)0.0293 (16)0.087 (2)0.0062 (13)0.0026 (16)0.0083 (15)
O120.0236 (14)0.0610 (19)0.0411 (15)0.0025 (16)0.0019 (12)0.0010 (15)
O140.0245 (16)0.0399 (16)0.0585 (17)0.0020 (14)0.0034 (14)0.0179 (14)
O160.081 (3)0.069 (2)0.060 (2)0.036 (2)0.016 (2)0.0036 (18)
C10.102 (4)0.069 (4)0.042 (3)0.005 (3)0.002 (3)0.001 (3)
C20.076 (4)0.052 (3)0.035 (2)0.008 (3)0.004 (2)0.010 (2)
C30.057 (3)0.033 (2)0.038 (2)0.011 (2)0.002 (2)0.0057 (18)
C40.035 (3)0.021 (2)0.040 (2)0.0045 (18)0.009 (2)0.0001 (17)
C50.022 (2)0.022 (2)0.040 (2)0.0023 (17)0.0015 (17)0.0042 (17)
C60.0245 (19)0.0298 (19)0.0233 (17)0.004 (2)0.0012 (14)0.0013 (17)
C70.024 (2)0.020 (2)0.0283 (19)0.0038 (16)0.0036 (17)0.0009 (15)
C80.032 (2)0.024 (2)0.0282 (19)0.0025 (18)0.0023 (18)0.0005 (16)
C90.044 (3)0.034 (2)0.031 (2)0.004 (2)0.0095 (18)0.0002 (17)
C100.031 (2)0.028 (2)0.036 (2)0.0027 (19)0.0006 (19)0.0012 (17)
C110.035 (3)0.029 (2)0.063 (3)0.0013 (18)0.002 (2)0.005 (2)
C120.024 (2)0.0229 (18)0.0300 (18)0.001 (2)0.0035 (17)0.0014 (17)
C130.034 (2)0.037 (2)0.035 (2)0.003 (2)0.0028 (17)0.0009 (19)
C140.032 (2)0.026 (2)0.0280 (19)0.0035 (18)0.0039 (18)0.0019 (16)
C150.026 (2)0.031 (2)0.056 (3)0.0026 (19)0.002 (2)0.0067 (19)
C160.061 (3)0.035 (3)0.049 (3)0.004 (2)0.021 (2)0.008 (2)
C170.089 (4)0.055 (3)0.053 (3)0.000 (3)0.032 (3)0.009 (2)
Geometric parameters (Å, º) top
O5—C51.454 (4)C5—H51.0000
O5—C101.341 (4)C6—C71.513 (5)
O6—C61.446 (4)C6—H61.0000
O6—C121.346 (4)C7—C81.525 (5)
O7—C71.441 (4)C7—H71.0000
O7—C141.356 (4)C8—C91.504 (5)
O8—C41.432 (4)C8—H81.0000
O8—C81.422 (4)C9—H9A0.9900
O9—C91.442 (4)C9—H9B0.9900
O9—C161.334 (5)C10—C111.491 (5)
O10—C101.197 (5)C11—H11A0.9800
O12—C121.199 (4)C11—H11B0.9800
O14—C141.205 (4)C11—H11C0.9800
O16—C161.200 (5)C12—C131.487 (4)
C1—C21.286 (6)C13—H13A0.9800
C1—H1A0.9500C13—H13B0.9800
C1—H1B0.9500C13—H13C0.9800
C2—C31.495 (5)C14—C151.483 (5)
C2—H20.9500C15—H15A0.9800
C3—C41.533 (6)C15—H15B0.9800
C3—H3A0.9900C15—H15C0.9800
C3—H3B0.9900C16—C171.488 (6)
C4—C51.533 (5)C17—H17A0.9800
C4—H41.0000C17—H17B0.9800
C5—C61.508 (5)C17—H17C0.9800
C10—O5—C5117.4 (3)C9—C8—H8109.7
C12—O6—C6119.0 (2)C7—C8—H8109.7
C14—O7—C7119.3 (3)O9—C9—C8108.5 (3)
C8—O8—C4114.3 (2)O9—C9—H9A110.0
C16—O9—C9115.4 (3)C8—C9—H9A110.0
C2—C1—H1A120.0O9—C9—H9B110.0
C2—C1—H1B120.0C8—C9—H9B110.0
H1A—C1—H1B120.0H9A—C9—H9B108.4
C1—C2—C3124.8 (5)O10—C10—O5123.6 (3)
C1—C2—H2117.6O10—C10—C11125.2 (4)
C3—C2—H2117.6O5—C10—C11111.2 (3)
C2—C3—C4113.5 (4)C10—C11—H11A109.5
C2—C3—H3A108.9C10—C11—H11B109.5
C4—C3—H3A108.9H11A—C11—H11B109.5
C2—C3—H3B108.9C10—C11—H11C109.5
C4—C3—H3B108.9H11A—C11—H11C109.5
H3A—C3—H3B107.7H11B—C11—H11C109.5
O8—C4—C5107.6 (3)O12—C12—O6123.6 (3)
O8—C4—C3114.3 (3)O12—C12—C13126.0 (3)
C5—C4—C3112.4 (3)O6—C12—C13110.4 (3)
O8—C4—H4107.4C12—C13—H13A109.5
C5—C4—H4107.4C12—C13—H13B109.5
C3—C4—H4107.4H13A—C13—H13B109.5
O5—C5—C6105.7 (3)C12—C13—H13C109.5
O5—C5—C4110.1 (3)H13A—C13—H13C109.5
C6—C5—C4111.4 (3)H13B—C13—H13C109.5
O5—C5—H5109.9O14—C14—O7122.8 (4)
C6—C5—H5109.9O14—C14—C15126.3 (3)
C4—C5—H5109.9O7—C14—C15110.9 (3)
O6—C6—C5107.8 (3)C14—C15—H15A109.5
O6—C6—C7107.7 (3)C14—C15—H15B109.5
C5—C6—C7112.4 (3)H15A—C15—H15B109.5
O6—C6—H6109.6C14—C15—H15C109.5
C5—C6—H6109.6H15A—C15—H15C109.5
C7—C6—H6109.6H15B—C15—H15C109.5
O7—C7—C6106.0 (3)O16—C16—O9123.0 (4)
O7—C7—C8109.4 (3)O16—C16—C17125.0 (4)
C6—C7—C8112.4 (3)O9—C16—C17112.0 (4)
O7—C7—H7109.6C16—C17—H17A109.5
C6—C7—H7109.6C16—C17—H17B109.5
C8—C7—H7109.6H17A—C17—H17B109.5
O8—C8—C9106.8 (3)C16—C17—H17C109.5
O8—C8—C7110.3 (3)H17A—C17—H17C109.5
C9—C8—C7110.5 (3)H17B—C17—H17C109.5
O8—C8—H8109.7
C1—C2—C3—C4144.1 (5)C5—C6—C7—O7165.3 (3)
C8—O8—C4—C564.0 (3)O6—C6—C7—C8164.5 (3)
C8—O8—C4—C361.6 (4)C5—C6—C7—C845.8 (4)
C2—C3—C4—O849.2 (5)C4—O8—C8—C9178.9 (3)
C2—C3—C4—C5172.2 (3)C4—O8—C8—C761.0 (3)
C10—O5—C5—C6155.1 (3)O7—C7—C8—O8167.1 (3)
C10—O5—C5—C484.5 (4)C6—C7—C8—O849.6 (4)
O8—C4—C5—O5173.4 (3)O7—C7—C8—C975.0 (4)
C3—C4—C5—O546.7 (4)C6—C7—C8—C9167.5 (3)
O8—C4—C5—C656.5 (4)C16—O9—C9—C8175.5 (3)
C3—C4—C5—C670.2 (4)O8—C8—C9—O964.6 (4)
C12—O6—C6—C5119.7 (3)C7—C8—C9—O9175.4 (3)
C12—O6—C6—C7118.7 (3)C5—O5—C10—O104.8 (5)
O5—C5—C6—O672.3 (3)C5—O5—C10—C11174.2 (3)
C4—C5—C6—O6168.2 (3)C6—O6—C12—O122.7 (6)
O5—C5—C6—C7169.1 (3)C6—O6—C12—C13178.9 (3)
C4—C5—C6—C749.6 (4)C7—O7—C14—O140.6 (5)
C14—O7—C7—C6137.5 (3)C7—O7—C14—C15180.0 (3)
C14—O7—C7—C8101.1 (3)C9—O9—C16—O160.6 (6)
O6—C6—C7—O776.0 (3)C9—O9—C16—C17179.1 (4)
 

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