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
Key indicators
- Single-crystal X-ray study
- T = 180 K
- Mean (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
For related literature, see: Freitag et al. (2004); Sekiguchi et al. (2006); 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. 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. |
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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].