Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039176/hg6274sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039176/hg6274Isup2.hkl |
CCDC reference: 296570
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.008 Å
- R factor = 0.088
- wR factor = 0.163
- Data-to-parameter ratio = 11.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
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 27.28 From the CIF: _reflns_number_total 4688 Count of symmetry unique reflns 2795 Completeness (_total/calc) 167.73% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1893 Fraction of Friedel pairs measured 0.677 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 3 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
To a vigorously stirred solution of p-tolylsulfanyl-β-d-glucopyronoside (0.286 g, 1 mmol) in acetonitrile (20 ml) was added dropwise benzaldehyde dimethyl acetal (0.30 ml, 2 mmol) and p-tolylsulfonic acid (0.018 g, 0.1 mmol) in turn at room temperature. The reaction solution was stirred for 30 min at this temperature and concentrated. The resulting mixture was dissolved in CH2Cl2 (20 ml), washed with saturated NaHCO3 and water, then dried over anhydrous Na2SO4 and concentrated. The crude residue was dissolved in pyridine (10 ml) and acetic anhydride (7.5 ml) and stirred overnight at room temperature. The resulting mixture was concentrated, dissolved with CH2Cl2 (20 ml), washed with saturated aqueous NaHCO3 and water. The organic phase was dried over Na2SO4. After removal of the solvent in vacuo, the solid was purified by silica-gel column chromatography (hexane/ethyl acetate 4:1) to give the desired product (yield 83% over two steps). Colorless crystals were obtained from acetone solution after allowing it to stand for 4 d. 1H NMR (500 MHz, CDCl3): δ 7.38 (m, 8H), 7.16 (d, J = 8.0 Hz, 2H), 5.50 (s, 1H), 5.34 (t, J = 9.5 Hz, 1H), 4.99 (t, J = 9.0 Hz, 1H), 4.75 (d, J = 10.0 Hz, 1H), 4.39 (m, 1H), 3.79 (t, J = 10.0 Hz, 1H), 3.65 (t, J = 9.5 Hz, 1H), 3.57 (m, 1H), 2.37 (s, 3H), 2.12 (s, 3H), 2.04 (s, 3H). 13C NMR (125 MHz, CDCl3): δ 170.3, 169.7, 139.0, 137.0, 133.9, 130.0, 129.4, 128.5, 127.9, 126.4, 101.7, 87.0, 78.3, 73.2, 71.0, 70.9, 68.7, 21.4, 21.0. MS (EI): m/z = 481 [M + Na]+.
All H atoms were placed in calculated positions, with C—H = 0.96–0.98 Å, and were refined as riding on their carrier atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: PROCESS-AUTO (V1.06; Rigaku,1998); cell refinement: PROCESS-AUTO (V1.06; Rigaku,1998); data reduction: CrystalStructure (Version 3.60; Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Version 3.60; Rigaku/MSC, 2004) and PLATON (Spek, 2003).
C24H26O7S | F(000) = 484.00 |
Mr = 458.53 | Dx = 1.316 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: P 2yb | Cell parameters from 8131 reflections |
a = 5.6530 (7) Å | θ = 2.5–27.3° |
b = 8.0292 (9) Å | µ = 0.18 mm−1 |
c = 25.490 (3) Å | T = 295 K |
β = 90.906 (5)° | Block, colorless |
V = 1156.8 (2) Å3 | 0.31 × 0.19 × 0.14 mm |
Z = 2 |
Rigaku R-AXISRAPID diffractometer | 3140 reflections with F2 > 2.0σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.097 |
ω scans | θmax = 27.3° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −7→7 |
Tmin = 0.893, Tmax = 0.975 | k = −10→10 |
8608 measured reflections | l = −32→32 |
4688 independent reflections |
Refinement on F2 | w = 1/[0.0006Fo2 + 3σ(Fo2) + 0.5]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.088 | (Δ/σ)max < 0.001 |
wR(F2) = 0.163 | Δρmax = 0.55 e Å−3 |
S = 1.00 | Δρmin = −0.47 e Å−3 |
4583 reflections | Absolute structure: Flack (1983), 1922 Friedel Pairs |
390 parameters | Absolute structure parameter: 0.04 (2) |
H-atom parameters constrained |
C24H26O7S | V = 1156.8 (2) Å3 |
Mr = 458.53 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.6530 (7) Å | µ = 0.18 mm−1 |
b = 8.0292 (9) Å | T = 295 K |
c = 25.490 (3) Å | 0.31 × 0.19 × 0.14 mm |
β = 90.906 (5)° |
Rigaku R-AXISRAPID diffractometer | 4688 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3140 reflections with F2 > 2.0σ(F2) |
Tmin = 0.893, Tmax = 0.975 | Rint = 0.097 |
8608 measured reflections |
R[F2 > 2σ(F2)] = 0.088 | H-atom parameters constrained |
wR(F2) = 0.163 | Δρmax = 0.55 e Å−3 |
S = 1.00 | Δρmin = −0.47 e Å−3 |
4583 reflections | Absolute structure: Flack (1983), 1922 Friedel Pairs |
390 parameters | Absolute structure parameter: 0.04 (2) |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.4063 (2) | 0.3771 (2) | 0.36505 (5) | 0.0603 (4) | |
O1 | 0.6612 (7) | 0.5070 (5) | 0.2901 (1) | 0.062 (1) | |
O2 | 0.4861 (6) | 0.0705 (5) | 0.2913 (1) | 0.058 (1) | |
O3 | 0.0915 (7) | 0.0660 (6) | 0.2976 (2) | 0.085 (2) | |
O4 | 0.4337 (5) | 0.1658 (5) | 0.1823 (1) | 0.053 (1) | |
O5 | 0.684 (1) | −0.0286 (7) | 0.1530 (2) | 0.110 (2) | |
O6 | 0.8052 (6) | 0.4040 (4) | 0.1557 (1) | 0.050 (1) | |
O7 | 1.0129 (8) | 0.6417 (5) | 0.1809 (1) | 0.075 (1) | |
C1 | 0.6060 (9) | 0.3449 (7) | 0.3113 (2) | 0.052 (2) | |
C2 | 0.4858 (9) | 0.2389 (6) | 0.2711 (2) | 0.046 (1) | |
C3 | 0.6061 (9) | 0.2360 (7) | 0.2182 (2) | 0.048 (1) | |
C4 | 0.6724 (8) | 0.4055 (7) | 0.2017 (2) | 0.048 (1) | |
C5 | 0.810 (1) | 0.4889 (7) | 0.2457 (2) | 0.053 (2) | |
C6 | 0.884 (2) | 0.6606 (9) | 0.2278 (2) | 0.094 (3) | |
C7 | 0.593 (1) | 0.4348 (6) | 0.4180 (2) | 0.051 (2) | |
C8 | 0.800 (1) | 0.5245 (8) | 0.4132 (2) | 0.062 (2) | |
C9 | 0.936 (1) | 0.5605 (8) | 0.4575 (2) | 0.067 (2) | |
C10 | 0.868 (1) | 0.5128 (7) | 0.5072 (2) | 0.057 (2) | |
C11 | 1.022 (1) | 0.5562 (9) | 0.5544 (2) | 0.078 (2) | |
C12 | 0.662 (1) | 0.4294 (7) | 0.5114 (2) | 0.063 (2) | |
C13 | 0.5194 (9) | 0.3892 (8) | 0.4679 (2) | 0.061 (2) | |
C14 | 0.281 (1) | 0.0029 (8) | 0.3051 (2) | 0.060 (2) | |
C15 | 0.322 (1) | −0.1642 (8) | 0.3293 (3) | 0.087 (2) | |
C16 | 0.493 (1) | 0.0309 (8) | 0.1530 (2) | 0.064 (2) | |
C17 | 0.290 (1) | −0.0244 (9) | 0.1196 (3) | 0.082 (2) | |
C18 | 0.873 (1) | 0.5648 (7) | 0.1409 (2) | 0.055 (2) | |
C19 | 1.0189 (9) | 0.5586 (7) | 0.0926 (2) | 0.050 (1) | |
C20 | 1.218 (1) | 0.4636 (7) | 0.0904 (2) | 0.061 (2) | |
C21 | 1.356 (1) | 0.4627 (8) | 0.0473 (3) | 0.074 (2) | |
C22 | 1.297 (1) | 0.5600 (8) | 0.0043 (2) | 0.079 (2) | |
C23 | 1.098 (1) | 0.6599 (8) | 0.0066 (2) | 0.073 (2) | |
C24 | 0.956 (1) | 0.6575 (8) | 0.0501 (2) | 0.064 (2) | |
H1 | 0.7504 | 0.2892 | 0.3238 | 0.063* | |
H2 | 0.3229 | 0.2783 | 0.2662 | 0.054* | |
H3 | 0.7471 | 0.1653 | 0.2205 | 0.057* | |
H4 | 0.5269 | 0.4696 | 0.1957 | 0.057* | |
H5 | 0.9503 | 0.4229 | 0.2547 | 0.064* | |
H6 | 0.9812 | 0.7159 | 0.2543 | 0.113* | |
H7 | 0.7428 | 0.7258 | 0.2209 | 0.113* | |
H9 | 0.8470 | 0.5643 | 0.3786 | 0.075* | |
H10 | 1.0861 | 0.6202 | 0.4533 | 0.080* | |
H11 | 1.1321 | 0.4669 | 0.5605 | 0.093* | |
H12 | 0.9261 | 0.5706 | 0.5848 | 0.093* | |
H13 | 1.1073 | 0.6572 | 0.5478 | 0.093* | |
H14 | 0.6082 | 0.3972 | 0.5464 | 0.076* | |
H15 | 0.3687 | 0.3304 | 0.4717 | 0.073* | |
H16 | 0.3226 | −0.2484 | 0.3026 | 0.105* | |
H17 | 0.1988 | −0.1874 | 0.3537 | 0.105* | |
H18 | 0.4722 | −0.1636 | 0.3474 | 0.105* | |
H19 | 0.1979 | −0.1040 | 0.1385 | 0.099* | |
H20 | 0.3434 | −0.0736 | 0.0876 | 0.099* | |
H21 | 0.1954 | 0.0717 | 0.1117 | 0.099* | |
H22 | 1.2604 | 0.3927 | 0.1204 | 0.073* | |
H23 | 1.4998 | 0.3942 | 0.0471 | 0.089* | |
H24 | 1.3950 | 0.5582 | −0.0271 | 0.095* | |
H25 | 1.0587 | 0.7322 | −0.0232 | 0.088* | |
H26 | 0.8130 | 0.7265 | 0.0508 | 0.076* | |
H27 | 0.7318 | 0.6326 | 0.1341 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0555 (7) | 0.079 (1) | 0.0467 (7) | 0.0000 (8) | 0.0074 (6) | −0.0003 (8) |
O1 | 0.091 (3) | 0.051 (2) | 0.045 (2) | −0.012 (2) | 0.014 (2) | 0.000 (2) |
O2 | 0.060 (2) | 0.051 (2) | 0.062 (2) | 0.004 (2) | 0.006 (2) | 0.006 (2) |
O3 | 0.057 (3) | 0.092 (4) | 0.108 (3) | −0.016 (2) | 0.005 (2) | 0.010 (3) |
O4 | 0.051 (2) | 0.050 (2) | 0.059 (2) | 0.001 (2) | −0.003 (2) | −0.004 (2) |
O5 | 0.102 (4) | 0.097 (4) | 0.130 (4) | 0.022 (3) | −0.004 (3) | −0.061 (3) |
O6 | 0.065 (2) | 0.050 (2) | 0.036 (2) | −0.013 (2) | 0.006 (1) | 0.001 (2) |
O7 | 0.109 (3) | 0.070 (3) | 0.048 (2) | −0.040 (2) | 0.010 (2) | −0.004 (2) |
C1 | 0.051 (3) | 0.058 (4) | 0.048 (3) | 0.005 (3) | 0.008 (2) | 0.005 (3) |
C2 | 0.053 (3) | 0.032 (3) | 0.052 (3) | 0.005 (2) | 0.002 (2) | 0.005 (2) |
C3 | 0.041 (3) | 0.058 (4) | 0.044 (3) | 0.000 (2) | −0.004 (2) | 0.000 (2) |
C4 | 0.048 (3) | 0.054 (3) | 0.041 (2) | −0.001 (3) | 0.004 (2) | 0.004 (2) |
C5 | 0.063 (3) | 0.056 (4) | 0.041 (3) | −0.010 (3) | 0.005 (2) | −0.001 (2) |
C6 | 0.168 (7) | 0.071 (5) | 0.043 (3) | −0.054 (5) | 0.022 (4) | −0.006 (3) |
C7 | 0.063 (3) | 0.047 (3) | 0.044 (3) | 0.004 (3) | 0.010 (2) | 0.002 (2) |
C8 | 0.072 (4) | 0.073 (4) | 0.041 (3) | −0.005 (3) | 0.012 (3) | 0.003 (3) |
C9 | 0.064 (4) | 0.071 (4) | 0.066 (4) | −0.017 (3) | 0.011 (3) | −0.001 (3) |
C10 | 0.066 (4) | 0.055 (4) | 0.051 (3) | 0.008 (3) | 0.003 (3) | −0.007 (3) |
C11 | 0.089 (4) | 0.086 (5) | 0.058 (3) | 0.002 (4) | 0.002 (3) | −0.011 (3) |
C12 | 0.075 (4) | 0.071 (4) | 0.043 (3) | 0.000 (3) | 0.008 (3) | 0.002 (3) |
C13 | 0.061 (3) | 0.067 (4) | 0.056 (3) | −0.006 (3) | 0.012 (2) | 0.005 (3) |
C14 | 0.070 (4) | 0.062 (4) | 0.049 (3) | −0.020 (3) | 0.005 (3) | 0.001 (3) |
C15 | 0.119 (6) | 0.070 (5) | 0.073 (4) | −0.009 (4) | 0.006 (4) | 0.004 (4) |
C16 | 0.084 (4) | 0.049 (4) | 0.059 (3) | −0.012 (3) | 0.012 (3) | −0.003 (3) |
C17 | 0.097 (5) | 0.077 (5) | 0.073 (4) | −0.030 (4) | −0.002 (4) | −0.004 (4) |
C18 | 0.069 (3) | 0.057 (4) | 0.040 (3) | −0.012 (3) | 0.001 (2) | −0.002 (3) |
C19 | 0.051 (3) | 0.058 (3) | 0.040 (3) | −0.011 (3) | −0.000 (2) | −0.002 (2) |
C20 | 0.062 (4) | 0.066 (4) | 0.056 (3) | 0.002 (3) | −0.003 (3) | 0.002 (3) |
C21 | 0.066 (4) | 0.073 (5) | 0.083 (4) | 0.004 (3) | 0.018 (3) | −0.014 (4) |
C22 | 0.098 (5) | 0.087 (5) | 0.053 (4) | −0.016 (4) | 0.026 (3) | −0.011 (4) |
C23 | 0.083 (4) | 0.091 (5) | 0.045 (3) | −0.019 (4) | 0.006 (3) | 0.012 (3) |
C24 | 0.066 (4) | 0.075 (4) | 0.050 (3) | −0.004 (3) | −0.006 (3) | 0.013 (3) |
S1—C1 | 1.807 (5) | C19—C20 | 1.359 (8) |
S1—C7 | 1.761 (5) | C19—C24 | 1.385 (7) |
O1—C1 | 1.446 (7) | C20—C21 | 1.360 (9) |
O1—C5 | 1.427 (6) | C21—C22 | 1.385 (9) |
O2—C2 | 1.447 (6) | C22—C23 | 1.383 (9) |
O2—C14 | 1.334 (7) | C23—C24 | 1.378 (8) |
O3—C14 | 1.196 (8) | C1—H1 | 0.9800 |
O4—C3 | 1.442 (6) | C2—H2 | 0.9800 |
O4—C16 | 1.359 (7) | C3—H3 | 0.9800 |
O5—C16 | 1.182 (9) | C4—H4 | 0.9800 |
O6—C4 | 1.403 (5) | C5—H5 | 0.9800 |
O6—C18 | 1.400 (7) | C6—H6 | 0.9700 |
O7—C6 | 1.416 (7) | C6—H7 | 0.9700 |
O7—C18 | 1.421 (6) | C8—H9 | 0.9800 |
C1—C2 | 1.488 (7) | C9—H10 | 0.9800 |
C2—C3 | 1.519 (7) | C11—H11 | 0.9600 |
C3—C4 | 1.474 (8) | C11—H12 | 0.9600 |
C4—C5 | 1.509 (7) | C11—H13 | 0.9600 |
C5—C6 | 1.515 (9) | C12—H14 | 0.9800 |
C7—C8 | 1.384 (8) | C13—H15 | 0.9800 |
C7—C13 | 1.393 (7) | C15—H16 | 0.9600 |
C8—C9 | 1.386 (8) | C15—H17 | 0.9600 |
C9—C10 | 1.385 (8) | C15—H18 | 0.9600 |
C10—C11 | 1.516 (8) | C17—H19 | 0.9600 |
C10—C12 | 1.348 (8) | C17—H20 | 0.9600 |
C12—C13 | 1.398 (7) | C17—H21 | 0.9600 |
C14—C15 | 1.494 (9) | C18—H27 | 0.9800 |
C16—O4 | 1.359 (7) | C20—H22 | 0.9800 |
C16—O5 | 1.182 (9) | C21—H23 | 0.9800 |
C16—C17 | 1.484 (9) | C22—H24 | 0.9800 |
C17—C16 | 1.484 (9) | C23—H25 | 0.9800 |
C18—C19 | 1.493 (7) | C24—H26 | 0.9800 |
S1—C1—O1 | 107.2 (3) | O6—C4—H4 | 109.4365 |
S1—C1—C2 | 108.7 (3) | O6—C18—H27 | 109.4544 |
C7—S1—C1 | 104.2 (2) | O7—C6—H6 | 110.1562 |
S1—C7—C8 | 124.5 (4) | O7—C6—H7 | 109.8343 |
S1—C7—C13 | 116.6 (4) | O7—C18—H27 | 109.1342 |
O1—C1—C2 | 110.9 (4) | H1—C1—C2 | 109.4260 |
C5—O1—C1 | 109.7 (4) | C1—C2—H2 | 108.7816 |
O1—C5—C4 | 109.4 (4) | H2—C2—C3 | 108.8829 |
O1—C5—C6 | 108.4 (4) | C2—C3—H3 | 109.2629 |
O2—C2—C1 | 106.9 (4) | H3—C3—C4 | 110.0142 |
C14—O2—C2 | 118.5 (4) | C3—C4—H4 | 108.2282 |
O2—C2—C3 | 107.7 (4) | H4—C4—C5 | 107.6374 |
O2—C14—O3 | 124.5 (6) | C4—C5—H5 | 109.9155 |
O2—C14—C15 | 110.1 (5) | H5—C5—C6 | 109.4749 |
O3—C14—C15 | 125.4 (6) | C5—C6—H6 | 111.3337 |
O4—C3—C2 | 105.2 (4) | C5—C6—H7 | 108.2020 |
O4—C3—C4 | 110.6 (4) | H7—C6—H6 | 109.4630 |
C16—O4—C3 | 119.4 (4) | C7—C8—H9 | 119.3896 |
O4—C16—O5 | 123.7 (6) | C7—C13—H15 | 119.1234 |
O4—C16—C17 | 111.1 (5) | H9—C8—C9 | 120.7555 |
O5—C16—C17 | 125.1 (6) | C8—C9—H10 | 118.8550 |
O6—C4—C3 | 111.9 (4) | H10—C9—C10 | 119.3694 |
O6—C4—C5 | 110.4 (4) | C10—C11—H11 | 108.6084 |
C18—O6—C4 | 111.7 (4) | C10—C11—H12 | 110.0558 |
O6—C18—O7 | 111.1 (4) | C10—C11—H13 | 109.7317 |
O6—C18—C19 | 110.4 (4) | C10—C12—H14 | 118.9514 |
O7—C6—C5 | 107.8 (5) | H12—C11—H11 | 109.4781 |
C18—O7—C6 | 111.4 (5) | H13—C11—H11 | 109.4722 |
O7—C18—C19 | 107.4 (4) | H13—C11—H12 | 109.4775 |
C1—C2—C3 | 114.5 (4) | C12—C13—H15 | 121.6936 |
C2—C3—C4 | 111.0 (4) | H14—C12—C13 | 118.4209 |
C3—C4—C5 | 109.1 (4) | C14—C15—H16 | 109.9696 |
C4—C5—C6 | 108.8 (4) | C14—C15—H17 | 109.3972 |
C13—C7—C8 | 118.8 (5) | C14—C15—H18 | 109.0354 |
C7—C8—C9 | 119.8 (5) | H17—C15—H16 | 109.4742 |
C7—C13—C12 | 119.2 (5) | H18—C15—H16 | 109.4671 |
C8—C9—C10 | 121.8 (5) | H18—C15—H17 | 109.4824 |
C9—C10—C12 | 117.7 (5) | C16—C17—H19 | 109.3788 |
C9—C10—C11 | 119.8 (5) | C16—C17—H20 | 111.3354 |
C12—C10—C11 | 122.5 (5) | C16—C17—H21 | 107.6749 |
C10—C12—C13 | 122.6 (5) | H20—C17—H19 | 109.4703 |
C18—C19—C20 | 121.3 (5) | H21—C17—H19 | 109.4672 |
C18—C19—C24 | 119.2 (5) | H21—C17—H20 | 109.4800 |
C24—C19—C20 | 119.4 (5) | H27—C18—C19 | 109.3413 |
C19—C20—C21 | 121.6 (5) | C19—C20—H22 | 119.2273 |
C19—C24—C23 | 119.4 (5) | C19—C24—H26 | 120.7072 |
C20—C21—C22 | 120.1 (6) | H22—C20—C21 | 119.1854 |
C21—C22—C23 | 118.6 (6) | C20—C21—H23 | 119.7209 |
C22—C23—C24 | 120.8 (5) | H23—C21—C22 | 120.1962 |
S1—C1—H1 | 110.2219 | C21—C22—H24 | 120.3011 |
O1—C1—H1 | 110.3858 | C22—C23—H25 | 118.9026 |
O1—C5—H5 | 110.7066 | H24—C22—C23 | 121.0484 |
O2—C2—H2 | 110.0478 | C23—C24—H26 | 119.8778 |
O4—C3—H3 | 110.6427 | H25—C23—C24 | 120.3155 |
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H19···O7i | 0.96 | 2.54 | 3.487 (8) | 168 |
C20—H22···O4ii | 0.98 | 2.59 | 3.550 (6) | 166 |
Symmetry codes: (i) x−1, y−1, z; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C24H26O7S |
Mr | 458.53 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 295 |
a, b, c (Å) | 5.6530 (7), 8.0292 (9), 25.490 (3) |
β (°) | 90.906 (5) |
V (Å3) | 1156.8 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.31 × 0.19 × 0.14 |
Data collection | |
Diffractometer | Rigaku R-AXISRAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.893, 0.975 |
No. of measured, independent and observed [F2 > 2.0σ(F2)] reflections | 8608, 4688, 3140 |
Rint | 0.097 |
(sin θ/λ)max (Å−1) | 0.645 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.088, 0.163, 1.00 |
No. of reflections | 4583 |
No. of parameters | 390 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.47 |
Absolute structure | Flack (1983), 1922 Friedel Pairs |
Absolute structure parameter | 0.04 (2) |
Computer programs: PROCESS-AUTO (V1.06; Rigaku,1998), SIR97 (Altomare et al., 1999), CRYSTALS (Watkin et al., 1996), ORTEP-3 for Windows (Farrugia, 1997), CrystalStructure (Version 3.60; Rigaku/MSC, 2004) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H19···O7i | 0.96 | 2.54 | 3.487 (8) | 168 |
C20—H22···O4ii | 0.98 | 2.59 | 3.550 (6) | 166 |
Symmetry codes: (i) x−1, y−1, z; (ii) x+1, y, z. |
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Carbohydrates often exist on cell surface as glycoprotein or glycolipid conjugates, and play important structural and functional roles in numerous biological recognition processes. The synthesis of saccharides has attracted much more interest in recent years. As part of a program to construct a phenylpropanoid glycosides library, our group has synthesized several monosaccharide building blocks. We report here the crystal structure of one of them, (I).
The molecular structure of (I) is shown in Fig. 1. In the crystal structure, non-classical C—H···O hydrogen bonds link the moleculese into infinite sheets (Fig. 2).