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The title compound, C22H24O6, has been prepared in nine synthetic steps from 1,2:5,6-di-O-isopropyl­idene-α-D-gluco­furan­ose. It is expected to constitute a binding pocket for metal ions. The hydr­oxy group at the 9-position is involved in an intra­molecular hydrogen bond with an O atom of the (benz­yloxy)­methyl substituent, forming a pseudo-six-membered ring. In the crystal structure, the benzene ring of the (benz­yloxy)methyl substituent approaches the tricylic binding pocket of a neighbouring mol­ecule, forming a C—H...O contact.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053536/kp2133sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053536/kp2133Isup2.hkl
Contains datablock I

CCDC reference: 672813

Key indicators

  • Single-crystal X-ray study
  • T = 180 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.063
  • Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.865 0.980 Tmin(prime) and Tmax expected: 0.965 0.980 RR(prime) = 0.897 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.90 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.68 PLAT480_ALERT_4_C Long H...A H-Bond Reported H15A .. O2 .. 2.64 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 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 25.61 From the CIF: _reflns_number_total 1975 Count of symmetry unique reflns 1998 Completeness (_total/calc) 98.85% 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 C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1' = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 6 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

As a part of our ongoing research on conformationally restricted nucleosides and related compounds (Freitag et al., 2004; Sharma & Nielsen, 2004) the title compound was prepared in nine synthetic steps from commercially available 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. The compound is expected to constitute a binding pocket for metal ions. The hydroxyl group at the 9-position is involved in an intramolecular hydrogen bond with an O atom of the (benzyloxy)methyl substituent. In the crystal, the benzene ring of the (benzyloxy)methyl substituent approaches the tricylic binding pocket of a neighbouring molecule in a side-on manner, forming a C—H···O contact [H···O, 2.64 and H···O 3.468 (3) Å].

Related literature top

For related literature, see: Freitag et al. (2004); Sekiguchi et al. (2006); Sharma & Nielsen (2004).

Experimental top

The title compound was prepared in nine synthetic steps from commercially available 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. From this starting material, the known compound 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-3-C-vinyl-α-D-ribofuranose was obtained in five steps (Sekiguchi et al., 2006). Benzylation of the pro-S hydroxymethyl group followed by mesylation of the remaining free hydroxymethyl group yielded 3-O-benzyl-4-C-benzyloxymethyl-1,2-O-isopropylidene-5-O-methansulfunyl-3-C– vinyl-α-D-ribofuranose, which was successively treated with RuCl3.xH2O/NaIO4 and NaBH4 (Sharma & Nielsen, 2004) to yield the tricyclic title compound.

Refinement top

H atoms bound to C atoms were placed geometrically and refined using a riding model with C—H = 0.95–1.00 Å and with Uiso(H) = 1.2Ueq(C). The H atom of the hydroxyl group was located in a difference Fourier map and refined with an isotropic displacement parameter, without restraint. In the absence of significant anomalous scattering effects, Friedel pairs (1570 measured) were merged as equivalent data. The absolute structure is assigned on the basis of unchanging chirality of the 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose starting material.

Computing details top

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2000); program(s) used to refine structure: SHELXTL (Sheldrick, 2000); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at the 50% probability level for non-H atoms. The dashed line indicates an intramolecular O—H···O hydrogen bond.
(1R,4R,7R,8R,9R)-8-(Benzyloxy)-7- (benzyloxymethyl)-2,5,10-trioxatricyclo[5.2.1.04,8]decan-9-ol top
Crystal data top
C22H24O6F(000) = 816
Mr = 384.41Dx = 1.384 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4020 reflections
a = 9.4559 (3) Åθ = 2.4–21.1°
b = 10.8048 (4) ŵ = 0.10 mm1
c = 18.0620 (6) ÅT = 180 K
V = 1845.38 (11) Å3Block, colourless
Z = 40.35 × 0.35 × 0.20 mm
Data collection top
Bruker–Nonius X8 APEXII CCD
diffractometer
1975 independent reflections
Radiation source: fine-focus sealed tube1554 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
thin–slice ω and ϕ scansθmax = 25.6°, θmin = 3.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1111
Tmin = 0.865, Tmax = 0.980k = 1310
16553 measured reflectionsl = 1521
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063 w = 1/[σ2(Fo2) + (0.0389P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
1975 reflectionsΔρmax = 0.11 e Å3
257 parametersΔρmin = 0.18 e Å3
0 restraintsAbsolute structure: In the absence of significant anomalous scattering effects, Friedel opposites (1570 measured) have been merged.
Primary atom site location: structure-invariant direct methods
Crystal data top
C22H24O6V = 1845.38 (11) Å3
Mr = 384.41Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 9.4559 (3) ŵ = 0.10 mm1
b = 10.8048 (4) ÅT = 180 K
c = 18.0620 (6) Å0.35 × 0.35 × 0.20 mm
Data collection top
Bruker–Nonius X8 APEXII CCD
diffractometer
1975 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1554 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.980Rint = 0.044
16553 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.063H atoms treated by a mixture of independent and constrained refinement
S = 0.97Δρmax = 0.11 e Å3
1975 reflectionsΔρmin = 0.18 e Å3
257 parametersAbsolute structure: In the absence of significant anomalous scattering effects, Friedel opposites (1570 measured) have been merged.
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.31999 (14)0.32447 (13)0.38560 (7)0.0337 (4)
O20.32776 (16)0.58002 (15)0.31636 (7)0.0407 (4)
O30.36347 (17)0.31654 (16)0.25819 (8)0.0468 (4)
O40.62645 (16)0.25576 (13)0.40265 (9)0.0372 (4)
H40.590 (3)0.275 (3)0.4471 (15)0.080 (10)*
O50.61495 (14)0.52440 (12)0.40763 (7)0.0264 (3)
O60.48368 (14)0.33819 (13)0.51986 (7)0.0299 (4)
C10.4084 (2)0.2757 (2)0.32887 (11)0.0378 (6)
H1A0.40670.18320.33070.045*
C20.5564 (2)0.3221 (2)0.34630 (11)0.0312 (5)
H2A0.61510.32240.30030.037*
C30.5156 (2)0.45471 (18)0.36712 (10)0.0239 (5)
C40.3784 (2)0.43887 (18)0.41337 (10)0.0241 (5)
C50.2874 (2)0.5486 (2)0.39023 (10)0.0327 (5)
H5A0.18600.52620.39200.039*
H5B0.30360.61960.42380.039*
C1'0.4575 (2)0.5201 (2)0.29674 (10)0.0320 (5)
H1'A0.52710.58360.27970.038*
C2'0.4298 (2)0.4292 (2)0.23455 (11)0.0442 (7)
H2'A0.36870.46960.19710.053*
H2'B0.52070.40880.21030.053*
C5'0.3885 (2)0.43260 (18)0.49704 (10)0.0268 (5)
H5'A0.42120.51340.51640.032*
H5'B0.29360.41590.51800.032*
C60.7473 (2)0.5465 (2)0.37005 (11)0.0414 (6)
H6A0.73690.61580.33460.050*
H6B0.77630.47180.34220.050*
C70.8564 (2)0.5779 (2)0.42712 (10)0.0271 (5)
C80.9042 (2)0.4876 (2)0.47596 (11)0.0306 (5)
H8A0.86920.40540.47200.037*
C91.0021 (2)0.5159 (2)0.53018 (11)0.0330 (5)
H9A1.03290.45370.56370.040*
C101.0549 (2)0.6345 (2)0.53563 (12)0.0345 (6)
H10A1.12100.65460.57340.041*
C111.0120 (2)0.7231 (2)0.48650 (12)0.0354 (6)
H11A1.05060.80410.48930.043*
C120.9124 (2)0.6955 (2)0.43248 (11)0.0317 (5)
H12A0.88250.75810.39900.038*
C130.4875 (2)0.3209 (2)0.59906 (10)0.0320 (5)
H13A0.55450.25330.61090.038*
H13B0.39260.29510.61630.038*
C140.5312 (2)0.4361 (2)0.64016 (10)0.0271 (5)
C150.4519 (2)0.4825 (2)0.69786 (11)0.0355 (5)
H15A0.36910.43980.71320.043*
C160.4912 (3)0.5904 (2)0.73382 (12)0.0437 (6)
H16A0.43570.62110.77360.052*
C170.6106 (3)0.6533 (2)0.71189 (13)0.0459 (7)
H17A0.63720.72790.73600.055*
C180.6916 (3)0.6072 (2)0.65464 (13)0.0417 (6)
H18A0.77420.65010.63920.050*
C190.6526 (2)0.4986 (2)0.61982 (11)0.0341 (5)
H19A0.71010.46650.58120.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0280 (8)0.0360 (8)0.0371 (8)0.0061 (7)0.0051 (7)0.0152 (7)
O20.0394 (9)0.0570 (10)0.0256 (7)0.0191 (8)0.0011 (7)0.0061 (8)
O30.0424 (10)0.0617 (11)0.0362 (9)0.0018 (9)0.0029 (8)0.0199 (9)
O40.0391 (9)0.0341 (9)0.0384 (9)0.0112 (8)0.0040 (8)0.0006 (8)
O50.0220 (7)0.0313 (8)0.0257 (7)0.0031 (7)0.0034 (6)0.0003 (6)
O60.0349 (8)0.0301 (8)0.0247 (7)0.0081 (7)0.0007 (7)0.0005 (6)
C10.0371 (14)0.0399 (14)0.0364 (13)0.0029 (12)0.0030 (11)0.0161 (11)
C20.0305 (12)0.0343 (13)0.0289 (11)0.0034 (11)0.0043 (10)0.0056 (10)
C30.0209 (11)0.0281 (12)0.0226 (10)0.0007 (10)0.0013 (9)0.0022 (9)
C40.0235 (11)0.0222 (11)0.0265 (10)0.0012 (10)0.0014 (9)0.0056 (9)
C50.0313 (12)0.0420 (14)0.0247 (10)0.0079 (11)0.0015 (10)0.0003 (10)
C1'0.0278 (12)0.0429 (13)0.0253 (11)0.0062 (11)0.0010 (10)0.0006 (10)
C2'0.0373 (14)0.0697 (18)0.0258 (12)0.0115 (14)0.0030 (11)0.0041 (13)
C5'0.0249 (11)0.0277 (11)0.0276 (11)0.0019 (10)0.0031 (9)0.0006 (10)
C60.0296 (12)0.0633 (17)0.0315 (12)0.0118 (13)0.0074 (10)0.0002 (11)
C70.0199 (11)0.0339 (12)0.0273 (11)0.0025 (10)0.0070 (9)0.0003 (10)
C80.0307 (12)0.0237 (12)0.0375 (12)0.0032 (10)0.0124 (10)0.0011 (10)
C90.0304 (12)0.0350 (13)0.0335 (12)0.0043 (11)0.0033 (10)0.0087 (11)
C100.0302 (12)0.0442 (15)0.0292 (12)0.0018 (12)0.0028 (10)0.0031 (11)
C110.0340 (13)0.0260 (12)0.0463 (14)0.0078 (11)0.0082 (12)0.0064 (11)
C120.0277 (12)0.0312 (13)0.0361 (12)0.0032 (10)0.0071 (11)0.0074 (10)
C130.0349 (13)0.0342 (12)0.0270 (11)0.0012 (11)0.0008 (10)0.0069 (11)
C140.0257 (12)0.0325 (12)0.0230 (10)0.0026 (10)0.0023 (9)0.0073 (10)
C150.0309 (12)0.0436 (14)0.0320 (12)0.0031 (12)0.0042 (10)0.0067 (12)
C160.0538 (16)0.0460 (16)0.0314 (13)0.0147 (14)0.0023 (12)0.0061 (12)
C170.0557 (17)0.0391 (15)0.0430 (14)0.0059 (14)0.0209 (13)0.0020 (12)
C180.0371 (14)0.0421 (15)0.0458 (14)0.0062 (12)0.0124 (12)0.0068 (12)
C190.0273 (12)0.0449 (14)0.0302 (11)0.0015 (11)0.0017 (10)0.0018 (11)
Geometric parameters (Å, º) top
O1—C11.423 (2)C6—C71.497 (3)
O1—C41.444 (2)C6—H6A0.9900
O2—C51.428 (2)C6—H6B0.9900
O2—C1'1.432 (3)C7—C121.380 (3)
O3—C11.416 (2)C7—C81.391 (3)
O3—C2'1.435 (3)C8—C91.382 (3)
O4—C21.410 (2)C8—H8A0.9500
O4—H40.90 (3)C9—C101.380 (3)
O5—C31.409 (2)C9—H9A0.9500
O5—C61.444 (2)C10—C111.367 (3)
O6—C5'1.422 (2)C10—H10A0.9500
O6—C131.443 (2)C11—C121.389 (3)
C1—C21.519 (3)C11—H11A0.9500
C1—H1A1.0000C12—H12A0.9500
C2—C31.531 (3)C13—C141.507 (3)
C2—H2A1.0000C13—H13A0.9900
C3—C41.552 (3)C13—H13B0.9900
C3—C1'1.555 (3)C14—C151.378 (3)
C4—C5'1.516 (3)C14—C191.381 (3)
C4—C51.524 (3)C15—C161.386 (3)
C5—H5A0.9900C15—H15A0.9500
C5—H5B0.9900C16—C171.376 (3)
C1'—C2'1.514 (3)C16—H16A0.9500
C1'—H1'A1.0000C17—C181.380 (3)
C2'—H2'A0.9900C17—H17A0.9500
C2'—H2'B0.9900C18—C191.381 (3)
C5'—H5'A0.9900C18—H18A0.9500
C5'—H5'B0.9900C19—H19A0.9500
C1—O1—C4110.02 (15)O6—C5'—H5'B109.4
C5—O2—C1'110.63 (15)C4—C5'—H5'B109.4
C1—O3—C2'113.70 (16)H5'A—C5'—H5'B108.0
C2—O4—H4110.6 (18)O5—C6—C7108.11 (15)
C3—O5—C6114.99 (14)O5—C6—H6A110.1
C5'—O6—C13113.35 (15)C7—C6—H6A110.1
O3—C1—O1110.96 (17)O5—C6—H6B110.1
O3—C1—C2111.12 (18)C7—C6—H6B110.1
O1—C1—C2105.63 (16)H6A—C6—H6B108.4
O3—C1—H1A109.7C12—C7—C8118.48 (19)
O1—C1—H1A109.7C12—C7—C6121.38 (19)
C2—C1—H1A109.7C8—C7—C6120.14 (19)
O4—C2—C1114.52 (18)C9—C8—C7120.8 (2)
O4—C2—C3114.62 (16)C9—C8—H8A119.6
C1—C2—C397.33 (17)C7—C8—H8A119.6
O4—C2—H2A109.9C10—C9—C8119.9 (2)
C1—C2—H2A109.9C10—C9—H9A120.0
C3—C2—H2A109.9C8—C9—H9A120.0
O5—C3—C2117.39 (17)C11—C10—C9119.8 (2)
O5—C3—C4109.67 (14)C11—C10—H10A120.1
C2—C3—C4103.84 (16)C9—C10—H10A120.1
O5—C3—C1'114.69 (16)C10—C11—C12120.5 (2)
C2—C3—C1'108.27 (16)C10—C11—H11A119.8
C4—C3—C1'101.21 (15)C12—C11—H11A119.8
O1—C4—C5'109.39 (16)C7—C12—C11120.5 (2)
O1—C4—C5110.78 (15)C7—C12—H12A119.8
C5'—C4—C5110.10 (16)C11—C12—H12A119.8
O1—C4—C3103.14 (14)O6—C13—C14112.82 (16)
C5'—C4—C3119.30 (16)O6—C13—H13A109.0
C5—C4—C3103.79 (15)C14—C13—H13A109.0
O2—C5—C4106.88 (16)O6—C13—H13B109.0
O2—C5—H5A110.3C14—C13—H13B109.0
C4—C5—H5A110.3H13A—C13—H13B107.8
O2—C5—H5B110.3C15—C14—C19118.3 (2)
C4—C5—H5B110.3C15—C14—C13121.56 (19)
H5A—C5—H5B108.6C19—C14—C13120.09 (18)
O2—C1'—C2'109.19 (17)C14—C15—C16121.0 (2)
O2—C1'—C3107.83 (15)C14—C15—H15A119.5
C2'—C1'—C3111.92 (18)C16—C15—H15A119.5
O2—C1'—H1'A109.3C17—C16—C15120.0 (2)
C2'—C1'—H1'A109.3C17—C16—H16A120.0
C3—C1'—H1'A109.3C15—C16—H16A120.0
O3—C2'—C1'113.87 (17)C16—C17—C18119.6 (2)
O3—C2'—H2'A108.8C16—C17—H17A120.2
C1'—C2'—H2'A108.8C18—C17—H17A120.2
O3—C2'—H2'B108.8C17—C18—C19119.9 (2)
C1'—C2'—H2'B108.8C17—C18—H18A120.0
H2'A—C2'—H2'B107.7C19—C18—H18A120.0
O6—C5'—C4111.14 (16)C18—C19—C14121.1 (2)
O6—C5'—H5'A109.4C18—C19—H19A119.4
C4—C5'—H5'A109.4C14—C19—H19A119.4
C2'—O3—C1—O190.9 (2)O5—C3—C1'—O294.83 (19)
C2'—O3—C1—C226.4 (2)C2—C3—C1'—O2131.93 (17)
C4—O1—C1—O392.53 (19)C4—C3—C1'—O223.1 (2)
C4—O1—C1—C228.0 (2)O5—C3—C1'—C2'145.06 (17)
O3—C1—C2—O4160.61 (17)C2—C3—C1'—C2'11.8 (2)
O1—C1—C2—O479.0 (2)C4—C3—C1'—C2'96.99 (19)
O3—C1—C2—C378.03 (18)C1—O3—C2'—C1'35.5 (2)
O1—C1—C2—C342.4 (2)O2—C1'—C2'—O376.8 (2)
C6—O5—C3—C262.4 (2)C3—C1'—C2'—O342.5 (2)
C6—O5—C3—C4179.48 (16)C13—O6—C5'—C4174.74 (17)
C6—O5—C3—C1'66.4 (2)O1—C4—C5'—O663.6 (2)
O4—C2—C3—O541.1 (2)C5—C4—C5'—O6174.41 (15)
C1—C2—C3—O5162.37 (16)C3—C4—C5'—O654.6 (2)
O4—C2—C3—C480.1 (2)C3—O5—C6—C7159.43 (16)
C1—C2—C3—C441.16 (17)O5—C6—C7—C12111.0 (2)
O4—C2—C3—C1'172.89 (17)O5—C6—C7—C869.4 (2)
C1—C2—C3—C1'65.83 (18)C12—C7—C8—C92.1 (3)
C1—O1—C4—C5'128.44 (18)C6—C7—C8—C9178.29 (17)
C1—O1—C4—C5110.02 (17)C7—C8—C9—C100.9 (3)
C1—O1—C4—C30.50 (18)C8—C9—C10—C111.1 (3)
O5—C3—C4—O1152.95 (14)C9—C10—C11—C121.9 (3)
C2—C3—C4—O126.70 (17)C8—C7—C12—C111.3 (3)
C1'—C3—C4—O185.51 (17)C6—C7—C12—C11179.11 (18)
O5—C3—C4—C5'31.5 (2)C10—C11—C12—C70.7 (3)
C2—C3—C4—C5'94.8 (2)C5'—O6—C13—C1459.5 (2)
C1'—C3—C4—C5'153.03 (17)O6—C13—C14—C15128.2 (2)
O5—C3—C4—C591.43 (16)O6—C13—C14—C1951.1 (2)
C2—C3—C4—C5142.33 (16)C19—C14—C15—C161.1 (3)
C1'—C3—C4—C530.12 (18)C13—C14—C15—C16178.16 (19)
C1'—O2—C5—C413.6 (2)C14—C15—C16—C170.3 (3)
O1—C4—C5—O282.16 (19)C15—C16—C17—C180.8 (3)
C5'—C4—C5—O2156.71 (17)C16—C17—C18—C190.0 (3)
C3—C4—C5—O227.93 (19)C17—C18—C19—C141.5 (3)
C5—O2—C1'—C2'115.25 (19)C15—C14—C19—C182.0 (3)
C5—O2—C1'—C36.6 (2)C13—C14—C19—C18177.30 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O60.90 (3)1.79 (3)2.664 (2)163 (3)
C15—H15A···O2i0.952.643.468 (3)146
Symmetry code: (i) x+1/2, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC22H24O6
Mr384.41
Crystal system, space groupOrthorhombic, P212121
Temperature (K)180
a, b, c (Å)9.4559 (3), 10.8048 (4), 18.0620 (6)
V3)1845.38 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.35 × 0.35 × 0.20
Data collection
DiffractometerBruker–Nonius X8 APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.865, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
16553, 1975, 1554
Rint0.044
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.063, 0.97
No. of reflections1975
No. of parameters257
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.11, 0.18
Absolute structureIn the absence of significant anomalous scattering effects, Friedel opposites (1570 measured) have been merged.

Computer programs: APEX2 (Bruker–Nonius, 2004), SAINT (Bruker, 2003), SHELXTL (Sheldrick, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O60.90 (3)1.79 (3)2.664 (2)163 (3)
C15—H15A···O2i0.952.643.468 (3)146
Symmetry code: (i) x+1/2, y+1, z+1/2.
 

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