Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053536/kp2133sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053536/kp2133Isup2.hkl |
CCDC reference: 672813
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.
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.
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).
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. |
C22H24O6 | F(000) = 816 |
Mr = 384.41 | Dx = 1.384 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4020 reflections |
a = 9.4559 (3) Å | θ = 2.4–21.1° |
b = 10.8048 (4) Å | µ = 0.10 mm−1 |
c = 18.0620 (6) Å | T = 180 K |
V = 1845.38 (11) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.35 × 0.20 mm |
Bruker–Nonius X8 APEXII CCD diffractometer | 1975 independent reflections |
Radiation source: fine-focus sealed tube | 1554 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
thin–slice ω and ϕ scans | θmax = 25.6°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −11→11 |
Tmin = 0.865, Tmax = 0.980 | k = −13→10 |
16553 measured reflections | l = −15→21 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H 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 reflections | Δρmax = 0.11 e Å−3 |
257 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Absolute structure: In the absence of significant anomalous scattering effects, Friedel opposites (1570 measured) have been merged. |
Primary atom site location: structure-invariant direct methods |
C22H24O6 | V = 1845.38 (11) Å3 |
Mr = 384.41 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.4559 (3) Å | µ = 0.10 mm−1 |
b = 10.8048 (4) Å | T = 180 K |
c = 18.0620 (6) Å | 0.35 × 0.35 × 0.20 mm |
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 = 0.980 | Rint = 0.044 |
16553 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.11 e Å−3 |
1975 reflections | Δρmin = −0.18 e Å−3 |
257 parameters | Absolute structure: In the absence of significant anomalous scattering effects, Friedel opposites (1570 measured) have been merged. |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.31999 (14) | 0.32447 (13) | 0.38560 (7) | 0.0337 (4) | |
O2 | 0.32776 (16) | 0.58002 (15) | 0.31636 (7) | 0.0407 (4) | |
O3 | 0.36347 (17) | 0.31654 (16) | 0.25819 (8) | 0.0468 (4) | |
O4 | 0.62645 (16) | 0.25576 (13) | 0.40265 (9) | 0.0372 (4) | |
H4 | 0.590 (3) | 0.275 (3) | 0.4471 (15) | 0.080 (10)* | |
O5 | 0.61495 (14) | 0.52440 (12) | 0.40763 (7) | 0.0264 (3) | |
O6 | 0.48368 (14) | 0.33819 (13) | 0.51986 (7) | 0.0299 (4) | |
C1 | 0.4084 (2) | 0.2757 (2) | 0.32887 (11) | 0.0378 (6) | |
H1A | 0.4067 | 0.1832 | 0.3307 | 0.045* | |
C2 | 0.5564 (2) | 0.3221 (2) | 0.34630 (11) | 0.0312 (5) | |
H2A | 0.6151 | 0.3224 | 0.3003 | 0.037* | |
C3 | 0.5156 (2) | 0.45471 (18) | 0.36712 (10) | 0.0239 (5) | |
C4 | 0.3784 (2) | 0.43887 (18) | 0.41337 (10) | 0.0241 (5) | |
C5 | 0.2874 (2) | 0.5486 (2) | 0.39023 (10) | 0.0327 (5) | |
H5A | 0.1860 | 0.5262 | 0.3920 | 0.039* | |
H5B | 0.3036 | 0.6196 | 0.4238 | 0.039* | |
C1' | 0.4575 (2) | 0.5201 (2) | 0.29674 (10) | 0.0320 (5) | |
H1'A | 0.5271 | 0.5836 | 0.2797 | 0.038* | |
C2' | 0.4298 (2) | 0.4292 (2) | 0.23455 (11) | 0.0442 (7) | |
H2'A | 0.3687 | 0.4696 | 0.1971 | 0.053* | |
H2'B | 0.5207 | 0.4088 | 0.2103 | 0.053* | |
C5' | 0.3885 (2) | 0.43260 (18) | 0.49704 (10) | 0.0268 (5) | |
H5'A | 0.4212 | 0.5134 | 0.5164 | 0.032* | |
H5'B | 0.2936 | 0.4159 | 0.5180 | 0.032* | |
C6 | 0.7473 (2) | 0.5465 (2) | 0.37005 (11) | 0.0414 (6) | |
H6A | 0.7369 | 0.6158 | 0.3346 | 0.050* | |
H6B | 0.7763 | 0.4718 | 0.3422 | 0.050* | |
C7 | 0.8564 (2) | 0.5779 (2) | 0.42712 (10) | 0.0271 (5) | |
C8 | 0.9042 (2) | 0.4876 (2) | 0.47596 (11) | 0.0306 (5) | |
H8A | 0.8692 | 0.4054 | 0.4720 | 0.037* | |
C9 | 1.0021 (2) | 0.5159 (2) | 0.53018 (11) | 0.0330 (5) | |
H9A | 1.0329 | 0.4537 | 0.5637 | 0.040* | |
C10 | 1.0549 (2) | 0.6345 (2) | 0.53563 (12) | 0.0345 (6) | |
H10A | 1.1210 | 0.6546 | 0.5734 | 0.041* | |
C11 | 1.0120 (2) | 0.7231 (2) | 0.48650 (12) | 0.0354 (6) | |
H11A | 1.0506 | 0.8041 | 0.4893 | 0.043* | |
C12 | 0.9124 (2) | 0.6955 (2) | 0.43248 (11) | 0.0317 (5) | |
H12A | 0.8825 | 0.7581 | 0.3990 | 0.038* | |
C13 | 0.4875 (2) | 0.3209 (2) | 0.59906 (10) | 0.0320 (5) | |
H13A | 0.5545 | 0.2533 | 0.6109 | 0.038* | |
H13B | 0.3926 | 0.2951 | 0.6163 | 0.038* | |
C14 | 0.5312 (2) | 0.4361 (2) | 0.64016 (10) | 0.0271 (5) | |
C15 | 0.4519 (2) | 0.4825 (2) | 0.69786 (11) | 0.0355 (5) | |
H15A | 0.3691 | 0.4398 | 0.7132 | 0.043* | |
C16 | 0.4912 (3) | 0.5904 (2) | 0.73382 (12) | 0.0437 (6) | |
H16A | 0.4357 | 0.6211 | 0.7736 | 0.052* | |
C17 | 0.6106 (3) | 0.6533 (2) | 0.71189 (13) | 0.0459 (7) | |
H17A | 0.6372 | 0.7279 | 0.7360 | 0.055* | |
C18 | 0.6916 (3) | 0.6072 (2) | 0.65464 (13) | 0.0417 (6) | |
H18A | 0.7742 | 0.6501 | 0.6392 | 0.050* | |
C19 | 0.6526 (2) | 0.4986 (2) | 0.61982 (11) | 0.0341 (5) | |
H19A | 0.7101 | 0.4665 | 0.5812 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0280 (8) | 0.0360 (8) | 0.0371 (8) | −0.0061 (7) | 0.0051 (7) | −0.0152 (7) |
O2 | 0.0394 (9) | 0.0570 (10) | 0.0256 (7) | 0.0191 (8) | 0.0011 (7) | 0.0061 (8) |
O3 | 0.0424 (10) | 0.0617 (11) | 0.0362 (9) | −0.0018 (9) | −0.0029 (8) | −0.0199 (9) |
O4 | 0.0391 (9) | 0.0341 (9) | 0.0384 (9) | 0.0112 (8) | 0.0040 (8) | 0.0006 (8) |
O5 | 0.0220 (7) | 0.0313 (8) | 0.0257 (7) | −0.0031 (7) | 0.0034 (6) | −0.0003 (6) |
O6 | 0.0349 (8) | 0.0301 (8) | 0.0247 (7) | 0.0081 (7) | 0.0007 (7) | 0.0005 (6) |
C1 | 0.0371 (14) | 0.0399 (14) | 0.0364 (13) | 0.0029 (12) | 0.0030 (11) | −0.0161 (11) |
C2 | 0.0305 (12) | 0.0343 (13) | 0.0289 (11) | 0.0034 (11) | 0.0043 (10) | −0.0056 (10) |
C3 | 0.0209 (11) | 0.0281 (12) | 0.0226 (10) | −0.0007 (10) | 0.0013 (9) | −0.0022 (9) |
C4 | 0.0235 (11) | 0.0222 (11) | 0.0265 (10) | −0.0012 (10) | 0.0014 (9) | −0.0056 (9) |
C5 | 0.0313 (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) |
C6 | 0.0296 (12) | 0.0633 (17) | 0.0315 (12) | −0.0118 (13) | 0.0074 (10) | 0.0002 (11) |
C7 | 0.0199 (11) | 0.0339 (12) | 0.0273 (11) | −0.0025 (10) | 0.0070 (9) | 0.0003 (10) |
C8 | 0.0307 (12) | 0.0237 (12) | 0.0375 (12) | −0.0032 (10) | 0.0124 (10) | −0.0011 (10) |
C9 | 0.0304 (12) | 0.0350 (13) | 0.0335 (12) | 0.0043 (11) | 0.0033 (10) | 0.0087 (11) |
C10 | 0.0302 (12) | 0.0442 (15) | 0.0292 (12) | −0.0018 (12) | 0.0028 (10) | −0.0031 (11) |
C11 | 0.0340 (13) | 0.0260 (12) | 0.0463 (14) | −0.0078 (11) | 0.0082 (12) | −0.0064 (11) |
C12 | 0.0277 (12) | 0.0312 (13) | 0.0361 (12) | 0.0032 (10) | 0.0071 (11) | 0.0074 (10) |
C13 | 0.0349 (13) | 0.0342 (12) | 0.0270 (11) | −0.0012 (11) | 0.0008 (10) | 0.0069 (11) |
C14 | 0.0257 (12) | 0.0325 (12) | 0.0230 (10) | 0.0026 (10) | −0.0023 (9) | 0.0073 (10) |
C15 | 0.0309 (12) | 0.0436 (14) | 0.0320 (12) | 0.0031 (12) | 0.0042 (10) | 0.0067 (12) |
C16 | 0.0538 (16) | 0.0460 (16) | 0.0314 (13) | 0.0147 (14) | 0.0023 (12) | −0.0061 (12) |
C17 | 0.0557 (17) | 0.0391 (15) | 0.0430 (14) | 0.0059 (14) | −0.0209 (13) | −0.0020 (12) |
C18 | 0.0371 (14) | 0.0421 (15) | 0.0458 (14) | −0.0062 (12) | −0.0124 (12) | 0.0068 (12) |
C19 | 0.0273 (12) | 0.0449 (14) | 0.0302 (11) | 0.0015 (11) | 0.0017 (10) | 0.0018 (11) |
O1—C1 | 1.423 (2) | C6—C7 | 1.497 (3) |
O1—C4 | 1.444 (2) | C6—H6A | 0.9900 |
O2—C5 | 1.428 (2) | C6—H6B | 0.9900 |
O2—C1' | 1.432 (3) | C7—C12 | 1.380 (3) |
O3—C1 | 1.416 (2) | C7—C8 | 1.391 (3) |
O3—C2' | 1.435 (3) | C8—C9 | 1.382 (3) |
O4—C2 | 1.410 (2) | C8—H8A | 0.9500 |
O4—H4 | 0.90 (3) | C9—C10 | 1.380 (3) |
O5—C3 | 1.409 (2) | C9—H9A | 0.9500 |
O5—C6 | 1.444 (2) | C10—C11 | 1.367 (3) |
O6—C5' | 1.422 (2) | C10—H10A | 0.9500 |
O6—C13 | 1.443 (2) | C11—C12 | 1.389 (3) |
C1—C2 | 1.519 (3) | C11—H11A | 0.9500 |
C1—H1A | 1.0000 | C12—H12A | 0.9500 |
C2—C3 | 1.531 (3) | C13—C14 | 1.507 (3) |
C2—H2A | 1.0000 | C13—H13A | 0.9900 |
C3—C4 | 1.552 (3) | C13—H13B | 0.9900 |
C3—C1' | 1.555 (3) | C14—C15 | 1.378 (3) |
C4—C5' | 1.516 (3) | C14—C19 | 1.381 (3) |
C4—C5 | 1.524 (3) | C15—C16 | 1.386 (3) |
C5—H5A | 0.9900 | C15—H15A | 0.9500 |
C5—H5B | 0.9900 | C16—C17 | 1.376 (3) |
C1'—C2' | 1.514 (3) | C16—H16A | 0.9500 |
C1'—H1'A | 1.0000 | C17—C18 | 1.380 (3) |
C2'—H2'A | 0.9900 | C17—H17A | 0.9500 |
C2'—H2'B | 0.9900 | C18—C19 | 1.381 (3) |
C5'—H5'A | 0.9900 | C18—H18A | 0.9500 |
C5'—H5'B | 0.9900 | C19—H19A | 0.9500 |
C1—O1—C4 | 110.02 (15) | O6—C5'—H5'B | 109.4 |
C5—O2—C1' | 110.63 (15) | C4—C5'—H5'B | 109.4 |
C1—O3—C2' | 113.70 (16) | H5'A—C5'—H5'B | 108.0 |
C2—O4—H4 | 110.6 (18) | O5—C6—C7 | 108.11 (15) |
C3—O5—C6 | 114.99 (14) | O5—C6—H6A | 110.1 |
C5'—O6—C13 | 113.35 (15) | C7—C6—H6A | 110.1 |
O3—C1—O1 | 110.96 (17) | O5—C6—H6B | 110.1 |
O3—C1—C2 | 111.12 (18) | C7—C6—H6B | 110.1 |
O1—C1—C2 | 105.63 (16) | H6A—C6—H6B | 108.4 |
O3—C1—H1A | 109.7 | C12—C7—C8 | 118.48 (19) |
O1—C1—H1A | 109.7 | C12—C7—C6 | 121.38 (19) |
C2—C1—H1A | 109.7 | C8—C7—C6 | 120.14 (19) |
O4—C2—C1 | 114.52 (18) | C9—C8—C7 | 120.8 (2) |
O4—C2—C3 | 114.62 (16) | C9—C8—H8A | 119.6 |
C1—C2—C3 | 97.33 (17) | C7—C8—H8A | 119.6 |
O4—C2—H2A | 109.9 | C10—C9—C8 | 119.9 (2) |
C1—C2—H2A | 109.9 | C10—C9—H9A | 120.0 |
C3—C2—H2A | 109.9 | C8—C9—H9A | 120.0 |
O5—C3—C2 | 117.39 (17) | C11—C10—C9 | 119.8 (2) |
O5—C3—C4 | 109.67 (14) | C11—C10—H10A | 120.1 |
C2—C3—C4 | 103.84 (16) | C9—C10—H10A | 120.1 |
O5—C3—C1' | 114.69 (16) | C10—C11—C12 | 120.5 (2) |
C2—C3—C1' | 108.27 (16) | C10—C11—H11A | 119.8 |
C4—C3—C1' | 101.21 (15) | C12—C11—H11A | 119.8 |
O1—C4—C5' | 109.39 (16) | C7—C12—C11 | 120.5 (2) |
O1—C4—C5 | 110.78 (15) | C7—C12—H12A | 119.8 |
C5'—C4—C5 | 110.10 (16) | C11—C12—H12A | 119.8 |
O1—C4—C3 | 103.14 (14) | O6—C13—C14 | 112.82 (16) |
C5'—C4—C3 | 119.30 (16) | O6—C13—H13A | 109.0 |
C5—C4—C3 | 103.79 (15) | C14—C13—H13A | 109.0 |
O2—C5—C4 | 106.88 (16) | O6—C13—H13B | 109.0 |
O2—C5—H5A | 110.3 | C14—C13—H13B | 109.0 |
C4—C5—H5A | 110.3 | H13A—C13—H13B | 107.8 |
O2—C5—H5B | 110.3 | C15—C14—C19 | 118.3 (2) |
C4—C5—H5B | 110.3 | C15—C14—C13 | 121.56 (19) |
H5A—C5—H5B | 108.6 | C19—C14—C13 | 120.09 (18) |
O2—C1'—C2' | 109.19 (17) | C14—C15—C16 | 121.0 (2) |
O2—C1'—C3 | 107.83 (15) | C14—C15—H15A | 119.5 |
C2'—C1'—C3 | 111.92 (18) | C16—C15—H15A | 119.5 |
O2—C1'—H1'A | 109.3 | C17—C16—C15 | 120.0 (2) |
C2'—C1'—H1'A | 109.3 | C17—C16—H16A | 120.0 |
C3—C1'—H1'A | 109.3 | C15—C16—H16A | 120.0 |
O3—C2'—C1' | 113.87 (17) | C16—C17—C18 | 119.6 (2) |
O3—C2'—H2'A | 108.8 | C16—C17—H17A | 120.2 |
C1'—C2'—H2'A | 108.8 | C18—C17—H17A | 120.2 |
O3—C2'—H2'B | 108.8 | C17—C18—C19 | 119.9 (2) |
C1'—C2'—H2'B | 108.8 | C17—C18—H18A | 120.0 |
H2'A—C2'—H2'B | 107.7 | C19—C18—H18A | 120.0 |
O6—C5'—C4 | 111.14 (16) | C18—C19—C14 | 121.1 (2) |
O6—C5'—H5'A | 109.4 | C18—C19—H19A | 119.4 |
C4—C5'—H5'A | 109.4 | C14—C19—H19A | 119.4 |
C2'—O3—C1—O1 | 90.9 (2) | O5—C3—C1'—O2 | −94.83 (19) |
C2'—O3—C1—C2 | −26.4 (2) | C2—C3—C1'—O2 | 131.93 (17) |
C4—O1—C1—O3 | −92.53 (19) | C4—C3—C1'—O2 | 23.1 (2) |
C4—O1—C1—C2 | 28.0 (2) | O5—C3—C1'—C2' | 145.06 (17) |
O3—C1—C2—O4 | −160.61 (17) | C2—C3—C1'—C2' | 11.8 (2) |
O1—C1—C2—O4 | 79.0 (2) | C4—C3—C1'—C2' | −96.99 (19) |
O3—C1—C2—C3 | 78.03 (18) | C1—O3—C2'—C1' | −35.5 (2) |
O1—C1—C2—C3 | −42.4 (2) | O2—C1'—C2'—O3 | −76.8 (2) |
C6—O5—C3—C2 | 62.4 (2) | C3—C1'—C2'—O3 | 42.5 (2) |
C6—O5—C3—C4 | −179.48 (16) | C13—O6—C5'—C4 | −174.74 (17) |
C6—O5—C3—C1' | −66.4 (2) | O1—C4—C5'—O6 | 63.6 (2) |
O4—C2—C3—O5 | 41.1 (2) | C5—C4—C5'—O6 | −174.41 (15) |
C1—C2—C3—O5 | 162.37 (16) | C3—C4—C5'—O6 | −54.6 (2) |
O4—C2—C3—C4 | −80.1 (2) | C3—O5—C6—C7 | −159.43 (16) |
C1—C2—C3—C4 | 41.16 (17) | O5—C6—C7—C12 | −111.0 (2) |
O4—C2—C3—C1' | 172.89 (17) | O5—C6—C7—C8 | 69.4 (2) |
C1—C2—C3—C1' | −65.83 (18) | C12—C7—C8—C9 | 2.1 (3) |
C1—O1—C4—C5' | −128.44 (18) | C6—C7—C8—C9 | −178.29 (17) |
C1—O1—C4—C5 | 110.02 (17) | C7—C8—C9—C10 | −0.9 (3) |
C1—O1—C4—C3 | −0.50 (18) | C8—C9—C10—C11 | −1.1 (3) |
O5—C3—C4—O1 | −152.95 (14) | C9—C10—C11—C12 | 1.9 (3) |
C2—C3—C4—O1 | −26.70 (17) | C8—C7—C12—C11 | −1.3 (3) |
C1'—C3—C4—O1 | 85.51 (17) | C6—C7—C12—C11 | 179.11 (18) |
O5—C3—C4—C5' | −31.5 (2) | C10—C11—C12—C7 | −0.7 (3) |
C2—C3—C4—C5' | 94.8 (2) | C5'—O6—C13—C14 | −59.5 (2) |
C1'—C3—C4—C5' | −153.03 (17) | O6—C13—C14—C15 | 128.2 (2) |
O5—C3—C4—C5 | 91.43 (16) | O6—C13—C14—C19 | −51.1 (2) |
C2—C3—C4—C5 | −142.33 (16) | C19—C14—C15—C16 | 1.1 (3) |
C1'—C3—C4—C5 | −30.12 (18) | C13—C14—C15—C16 | −178.16 (19) |
C1'—O2—C5—C4 | −13.6 (2) | C14—C15—C16—C17 | 0.3 (3) |
O1—C4—C5—O2 | −82.16 (19) | C15—C16—C17—C18 | −0.8 (3) |
C5'—C4—C5—O2 | 156.71 (17) | C16—C17—C18—C19 | 0.0 (3) |
C3—C4—C5—O2 | 27.93 (19) | C17—C18—C19—C14 | 1.5 (3) |
C5—O2—C1'—C2' | 115.25 (19) | C15—C14—C19—C18 | −2.0 (3) |
C5—O2—C1'—C3 | −6.6 (2) | C13—C14—C19—C18 | 177.30 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O6 | 0.90 (3) | 1.79 (3) | 2.664 (2) | 163 (3) |
C15—H15A···O2i | 0.95 | 2.64 | 3.468 (3) | 146 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H24O6 |
Mr | 384.41 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 180 |
a, b, c (Å) | 9.4559 (3), 10.8048 (4), 18.0620 (6) |
V (Å3) | 1845.38 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.35 × 0.35 × 0.20 |
Data collection | |
Diffractometer | Bruker–Nonius X8 APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.865, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16553, 1975, 1554 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.608 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.063, 0.97 |
No. of reflections | 1975 |
No. of parameters | 257 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.11, −0.18 |
Absolute structure | In 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O6 | 0.90 (3) | 1.79 (3) | 2.664 (2) | 163 (3) |
C15—H15A···O2i | 0.95 | 2.64 | 3.468 (3) | 146 |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
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].