organic compounds
2,3,4,6-Tetra-O-acetyl-1-O-(4-methoxycinnamoyl)-β-D-glucopyranose
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: zhuhj@njut.edu.cn
Molecules of the title compound, C24H28O12, are linked by intermolecular C—H⋯O hydrogen bonds. Bond lengths and angles are normal.
Related literature
For related literature, see: Loganathan & Trivedi (1987); Yu et al. (1991). For bond-length data, see: Allen et al. (1987).
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808004698/ez2118sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808004698/ez2118Isup2.hkl
The title compound, (I), was prepared by a method similar to that reported previously (Yu et al., 1991). The crystals were obtained by dissolving compound I (1.5 g) in methanol (25 ml) and evaporating the solvent slowly at room temperature for about 10 d.
H atoms were positioned geometrically, with O—H = 0.82 and C—H = 0.93Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C/O), where x = 1.2 for aromatic H and x = 1.5 for other H. In the absence of significant
effects 82 Friedel pairs have been merged.Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell
CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. A drawing of the title molecular structure, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown by dashed lines. |
C24H28O12 | F(000) = 536 |
Mr = 508.46 | Dx = 1.300 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 9.972 (2) Å | θ = 9–12° |
b = 6.0580 (12) Å | µ = 0.11 mm−1 |
c = 21.680 (4) Å | T = 298 K |
β = 97.19 (3)° | Needle, colourless |
V = 1299.4 (4) Å3 | 0.40 × 0.10 × 0.10 mm |
Z = 2 |
Enraf–Nonius CAD-4 diffractometer | 1578 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
ω/2θ scans | h = −11→11 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→7 |
Tmin = 0.959, Tmax = 0.990 | l = 0→26 |
2955 measured reflections | 3 standard reflections every 200 reflections |
2790 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.070 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.09P)2] where P = (Fo2 + 2Fc2)/3 |
2790 reflections | (Δ/σ)max < 0.001 |
319 parameters | Δρmax = 0.43 e Å−3 |
1 restraint | Δρmin = −0.40 e Å−3 |
C24H28O12 | V = 1299.4 (4) Å3 |
Mr = 508.46 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.972 (2) Å | µ = 0.11 mm−1 |
b = 6.0580 (12) Å | T = 298 K |
c = 21.680 (4) Å | 0.40 × 0.10 × 0.10 mm |
β = 97.19 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1578 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.062 |
Tmin = 0.959, Tmax = 0.990 | 3 standard reflections every 200 reflections |
2955 measured reflections | intensity decay: none |
2790 independent reflections |
R[F2 > 2σ(F2)] = 0.070 | 1 restraint |
wR(F2) = 0.189 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.43 e Å−3 |
2790 reflections | Δρmin = −0.40 e Å−3 |
319 parameters |
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 | 0.5843 (6) | 0.1875 (12) | 0.2849 (3) | 0.089 | |
C1 | 0.6777 (7) | 0.468 (2) | 0.3547 (4) | 0.099 (3) | |
H1A | 0.7643 | 0.4270 | 0.3433 | 0.148* | |
H1B | 0.6804 | 0.4617 | 0.3990 | 0.148* | |
H1C | 0.6559 | 0.6153 | 0.3405 | 0.148* | |
O2 | 0.4512 (4) | 0.3681 (9) | 0.3422 (2) | 0.0591 (13) | |
C2 | 0.5738 (7) | 0.3138 (18) | 0.3256 (4) | 0.084 (3) | |
O3 | 0.2760 (6) | 0.0744 (11) | 0.4807 (2) | 0.0799 (17) | |
C3 | 0.3974 (9) | −0.2530 (17) | 0.4674 (4) | 0.090 (3) | |
H3A | 0.3975 | −0.2727 | 0.5113 | 0.135* | |
H3B | 0.4888 | −0.2445 | 0.4580 | 0.135* | |
H3C | 0.3526 | −0.3758 | 0.4457 | 0.135* | |
O4 | 0.3228 (5) | −0.0182 (9) | 0.38543 (19) | 0.0567 (12) | |
C4 | 0.3267 (7) | −0.0507 (14) | 0.4480 (3) | 0.0567 (18) | |
O5 | 0.0717 (7) | −0.2870 (10) | 0.3886 (3) | 0.0846 (18) | |
C5 | −0.0937 (9) | −0.123 (2) | 0.4448 (4) | 0.116 (4) | |
H5A | −0.1026 | −0.2675 | 0.4619 | 0.174* | |
H5B | −0.1795 | −0.0758 | 0.4239 | 0.174* | |
H5C | −0.0641 | −0.0212 | 0.4776 | 0.174* | |
O6 | 0.0213 (4) | 0.0758 (8) | 0.3744 (2) | 0.0512 (12) | |
C6 | 0.0086 (8) | −0.1292 (15) | 0.3991 (3) | 0.061 (2) | |
O7 | −0.1160 (7) | −0.2286 (11) | 0.2512 (3) | 0.095 (2) | |
C7 | −0.0606 (8) | −0.2633 (14) | 0.1464 (3) | 0.070 (2) | |
H7A | −0.0739 | −0.4181 | 0.1528 | 0.106* | |
H7B | 0.0305 | −0.2382 | 0.1381 | 0.106* | |
H7C | −0.1224 | −0.2137 | 0.1116 | 0.106* | |
O8 | −0.0694 (5) | 0.0730 (8) | 0.1983 (2) | 0.0547 (12) | |
C8 | −0.0852 (7) | −0.1400 (14) | 0.2026 (4) | 0.0600 (19) | |
O9 | 0.1321 (4) | 0.3455 (8) | 0.24191 (19) | 0.0492 (11) | |
C9 | −0.0883 (6) | 0.2144 (13) | 0.2493 (3) | 0.0539 (18) | |
H9A | −0.1431 | 0.1388 | 0.2767 | 0.065* | |
H9B | −0.1368 | 0.3458 | 0.2337 | 0.065* | |
O10 | 0.3339 (4) | 0.4790 (8) | 0.2226 (2) | 0.0546 (12) | |
C10 | 0.0445 (6) | 0.2813 (12) | 0.2859 (3) | 0.0521 (18) | |
H10A | 0.0288 | 0.4098 | 0.3115 | 0.062* | |
C11 | 0.1097 (6) | 0.1011 (11) | 0.3280 (3) | 0.0482 (17) | |
H11A | 0.1150 | −0.0366 | 0.3047 | 0.058* | |
O11 | 0.2593 (5) | 0.8310 (8) | 0.2125 (2) | 0.0652 (14) | |
O12 | 0.8530 (5) | 0.5383 (9) | −0.0491 (2) | 0.0678 (15) | |
C12 | 0.2491 (6) | 0.1706 (11) | 0.3578 (3) | 0.0436 (15) | |
H12A | 0.2408 | 0.2826 | 0.3897 | 0.052* | |
C13 | 0.3322 (6) | 0.2602 (11) | 0.3099 (3) | 0.0455 (16) | |
H13A | 0.3588 | 0.1408 | 0.2835 | 0.055* | |
C14 | 0.2546 (6) | 0.4380 (12) | 0.2704 (3) | 0.0523 (18) | |
H14A | 0.2400 | 0.5710 | 0.2944 | 0.063* | |
C15 | 0.3289 (7) | 0.6851 (15) | 0.1968 (3) | 0.058 (2) | |
C16 | 0.4170 (7) | 0.7047 (14) | 0.1476 (3) | 0.0594 (19) | |
H16A | 0.4147 | 0.8349 | 0.1248 | 0.071* | |
C17 | 0.4991 (7) | 0.5466 (15) | 0.1343 (3) | 0.062 (2) | |
H17A | 0.4999 | 0.4189 | 0.1582 | 0.074* | |
C18 | 0.5902 (6) | 0.5500 (11) | 0.0855 (3) | 0.0448 (15) | |
C19 | 0.6731 (7) | 0.3730 (13) | 0.0785 (3) | 0.0558 (18) | |
H19A | 0.6720 | 0.2524 | 0.1049 | 0.067* | |
C20 | 0.7586 (6) | 0.3706 (13) | 0.0325 (3) | 0.0527 (17) | |
H20A | 0.8118 | 0.2474 | 0.0275 | 0.063* | |
C21 | 0.7641 (6) | 0.5531 (13) | −0.0059 (3) | 0.0499 (17) | |
C22 | 0.6811 (6) | 0.7313 (13) | 0.0001 (3) | 0.0547 (18) | |
H22A | 0.6826 | 0.8520 | −0.0263 | 0.066* | |
C23 | 0.5952 (6) | 0.7300 (13) | 0.0457 (3) | 0.0534 (18) | |
H23A | 0.5399 | 0.8513 | 0.0498 | 0.064* | |
C24 | 0.8593 (8) | 0.7190 (19) | −0.0897 (4) | 0.088 (3) | |
H24A | 0.9251 | 0.6896 | −0.1174 | 0.132* | |
H24B | 0.8848 | 0.8495 | −0.0659 | 0.132* | |
H24C | 0.7723 | 0.7410 | −0.1134 | 0.132* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.089 | 0.089 | 0.089 | 0.000 | 0.011 | 0.000 |
C1 | 0.062 (5) | 0.131 (8) | 0.109 (7) | −0.030 (6) | 0.033 (5) | −0.042 (7) |
O2 | 0.049 (3) | 0.071 (3) | 0.061 (3) | −0.011 (3) | 0.019 (2) | −0.012 (3) |
C2 | 0.051 (4) | 0.126 (8) | 0.079 (5) | −0.008 (5) | 0.027 (4) | −0.054 (6) |
O3 | 0.088 (4) | 0.104 (5) | 0.049 (3) | 0.037 (4) | 0.014 (3) | −0.006 (3) |
C3 | 0.113 (7) | 0.090 (7) | 0.066 (5) | 0.025 (7) | 0.006 (5) | −0.001 (5) |
O4 | 0.067 (3) | 0.060 (3) | 0.046 (3) | 0.009 (3) | 0.017 (2) | −0.005 (3) |
C4 | 0.055 (4) | 0.060 (5) | 0.055 (4) | 0.001 (4) | 0.007 (3) | −0.009 (4) |
O5 | 0.119 (5) | 0.050 (4) | 0.086 (4) | −0.014 (4) | 0.016 (3) | 0.008 (3) |
C5 | 0.118 (8) | 0.143 (10) | 0.095 (7) | −0.048 (8) | 0.050 (6) | 0.023 (7) |
O6 | 0.051 (3) | 0.052 (3) | 0.054 (3) | −0.008 (2) | 0.021 (2) | −0.010 (2) |
C6 | 0.075 (5) | 0.052 (5) | 0.058 (4) | −0.030 (5) | 0.011 (4) | 0.001 (4) |
O7 | 0.132 (5) | 0.074 (4) | 0.084 (4) | −0.025 (4) | 0.033 (4) | 0.005 (4) |
C7 | 0.077 (5) | 0.069 (6) | 0.061 (4) | −0.003 (5) | −0.006 (4) | −0.010 (5) |
O8 | 0.056 (3) | 0.046 (3) | 0.061 (3) | −0.005 (2) | 0.004 (2) | 0.000 (3) |
C8 | 0.052 (4) | 0.059 (5) | 0.068 (5) | 0.002 (4) | 0.003 (4) | −0.005 (5) |
O9 | 0.044 (2) | 0.049 (3) | 0.058 (3) | −0.005 (2) | 0.020 (2) | 0.009 (2) |
C9 | 0.042 (4) | 0.051 (4) | 0.070 (5) | 0.000 (4) | 0.011 (3) | 0.000 (4) |
O10 | 0.060 (3) | 0.042 (2) | 0.069 (3) | −0.009 (2) | 0.038 (2) | 0.006 (3) |
C10 | 0.046 (4) | 0.058 (5) | 0.057 (4) | −0.002 (3) | 0.023 (3) | 0.001 (4) |
C11 | 0.054 (4) | 0.042 (4) | 0.054 (4) | 0.001 (3) | 0.029 (3) | 0.000 (3) |
O11 | 0.086 (4) | 0.044 (3) | 0.073 (3) | 0.012 (3) | 0.037 (3) | −0.003 (3) |
O12 | 0.073 (3) | 0.074 (4) | 0.063 (3) | 0.023 (3) | 0.033 (3) | 0.015 (3) |
C12 | 0.050 (4) | 0.033 (3) | 0.048 (3) | 0.002 (3) | 0.010 (3) | −0.005 (3) |
C13 | 0.048 (4) | 0.043 (4) | 0.046 (3) | −0.006 (3) | 0.012 (3) | −0.011 (3) |
C14 | 0.054 (4) | 0.047 (4) | 0.061 (4) | −0.011 (3) | 0.028 (3) | −0.021 (4) |
C15 | 0.049 (4) | 0.073 (5) | 0.056 (4) | −0.018 (4) | 0.026 (3) | −0.010 (4) |
C16 | 0.061 (4) | 0.063 (5) | 0.059 (4) | −0.016 (4) | 0.025 (3) | 0.002 (4) |
C17 | 0.052 (4) | 0.089 (6) | 0.047 (4) | 0.001 (4) | 0.013 (3) | 0.005 (4) |
C18 | 0.042 (3) | 0.049 (4) | 0.045 (3) | −0.006 (3) | 0.012 (3) | 0.002 (3) |
C19 | 0.055 (4) | 0.060 (5) | 0.051 (4) | −0.006 (4) | 0.003 (3) | 0.003 (4) |
C20 | 0.048 (4) | 0.058 (4) | 0.053 (4) | 0.004 (4) | 0.013 (3) | −0.004 (4) |
C21 | 0.044 (3) | 0.062 (4) | 0.045 (4) | 0.002 (4) | 0.012 (3) | −0.005 (4) |
C22 | 0.059 (4) | 0.053 (4) | 0.054 (4) | 0.002 (4) | 0.016 (3) | 0.010 (4) |
C23 | 0.043 (4) | 0.066 (5) | 0.054 (4) | 0.001 (4) | 0.015 (3) | 0.001 (4) |
C24 | 0.083 (5) | 0.127 (8) | 0.064 (5) | −0.001 (7) | 0.048 (4) | −0.002 (6) |
O1—C2 | 1.183 (9) | O10—C15 | 1.366 (9) |
C1—C2 | 1.475 (12) | O10—C14 | 1.403 (7) |
C1—H1A | 0.9600 | C10—C11 | 1.516 (9) |
C1—H1B | 0.9600 | C10—H10A | 0.9800 |
C1—H1C | 0.9600 | C11—C12 | 1.518 (9) |
O2—C2 | 1.358 (8) | C11—H11A | 0.9800 |
O2—C13 | 1.456 (7) | O11—C15 | 1.199 (8) |
O3—C4 | 1.193 (8) | O12—C21 | 1.372 (7) |
C3—C4 | 1.450 (12) | O12—C24 | 1.411 (11) |
C3—H3A | 0.9600 | C12—C13 | 1.509 (8) |
C3—H3B | 0.9600 | C12—H12A | 0.9800 |
C3—H3C | 0.9600 | C13—C14 | 1.525 (9) |
O4—C4 | 1.367 (8) | C13—H13A | 0.9800 |
O4—C12 | 1.448 (8) | C14—H14A | 0.9800 |
O5—C6 | 1.182 (10) | C15—C16 | 1.469 (8) |
C5—C6 | 1.509 (10) | C16—C17 | 1.315 (10) |
C5—H5A | 0.9600 | C16—H16A | 0.9300 |
C5—H5B | 0.9600 | C17—C18 | 1.479 (8) |
C5—H5C | 0.9600 | C17—H17A | 0.9300 |
O6—C6 | 1.365 (9) | C18—C19 | 1.375 (9) |
O6—C11 | 1.425 (7) | C18—C23 | 1.396 (9) |
O7—C8 | 1.253 (9) | C19—C20 | 1.390 (8) |
C7—C8 | 1.477 (10) | C19—H19A | 0.9300 |
C7—H7A | 0.9600 | C20—C21 | 1.389 (10) |
C7—H7B | 0.9600 | C20—H20A | 0.9300 |
C7—H7C | 0.9600 | C21—C22 | 1.376 (9) |
O8—C8 | 1.305 (9) | C22—C23 | 1.386 (8) |
O8—C9 | 1.431 (8) | C22—H22A | 0.9300 |
O9—C14 | 1.413 (7) | C23—H23A | 0.9300 |
O9—C10 | 1.426 (7) | C24—H24A | 0.9600 |
C9—C10 | 1.512 (9) | C24—H24B | 0.9600 |
C9—H9A | 0.9700 | C24—H24C | 0.9600 |
C9—H9B | 0.9700 | ||
C2—C1—H1A | 109.5 | C10—C11—C12 | 110.9 (5) |
C2—C1—H1B | 109.5 | O6—C11—H11A | 110.5 |
H1A—C1—H1B | 109.5 | C10—C11—H11A | 110.5 |
C2—C1—H1C | 109.5 | C12—C11—H11A | 110.5 |
H1A—C1—H1C | 109.5 | C21—O12—C24 | 117.3 (6) |
H1B—C1—H1C | 109.5 | O4—C12—C13 | 106.0 (5) |
C2—O2—C13 | 118.1 (5) | O4—C12—C11 | 110.3 (5) |
O1—C2—O2 | 121.4 (7) | C13—C12—C11 | 111.0 (5) |
O1—C2—C1 | 127.2 (7) | O4—C12—H12A | 109.8 |
O2—C2—C1 | 109.9 (7) | C13—C12—H12A | 109.8 |
C4—C3—H3A | 109.5 | C11—C12—H12A | 109.8 |
C4—C3—H3B | 109.5 | O2—C13—C12 | 108.3 (5) |
H3A—C3—H3B | 109.5 | O2—C13—C14 | 106.2 (5) |
C4—C3—H3C | 109.5 | C12—C13—C14 | 110.9 (5) |
H3A—C3—H3C | 109.5 | O2—C13—H13A | 110.4 |
H3B—C3—H3C | 109.5 | C12—C13—H13A | 110.4 |
C4—O4—C12 | 118.3 (5) | C14—C13—H13A | 110.4 |
O3—C4—O4 | 122.5 (7) | O10—C14—O9 | 106.4 (5) |
O3—C4—C3 | 126.3 (7) | O10—C14—C13 | 104.3 (5) |
O4—C4—C3 | 111.2 (7) | O9—C14—C13 | 108.4 (5) |
C6—C5—H5A | 109.5 | O10—C14—H14A | 112.4 |
C6—C5—H5B | 109.5 | O9—C14—H14A | 112.4 |
H5A—C5—H5B | 109.5 | C13—C14—H14A | 112.4 |
C6—C5—H5C | 109.5 | O11—C15—O10 | 123.4 (5) |
H5A—C5—H5C | 109.5 | O11—C15—C16 | 124.5 (7) |
H5B—C5—H5C | 109.5 | O10—C15—C16 | 112.1 (7) |
C6—O6—C11 | 118.1 (5) | C17—C16—C15 | 123.1 (7) |
O5—C6—O6 | 125.7 (6) | C17—C16—H16A | 118.5 |
O5—C6—C5 | 124.5 (9) | C15—C16—H16A | 118.5 |
O6—C6—C5 | 109.8 (8) | C16—C17—C18 | 127.0 (7) |
C8—C7—H7A | 109.5 | C16—C17—H17A | 116.5 |
C8—C7—H7B | 109.5 | C18—C17—H17A | 116.5 |
H7A—C7—H7B | 109.5 | C19—C18—C23 | 118.2 (6) |
C8—C7—H7C | 109.5 | C19—C18—C17 | 120.1 (7) |
H7A—C7—H7C | 109.5 | C23—C18—C17 | 121.8 (6) |
H7B—C7—H7C | 109.5 | C18—C19—C20 | 121.3 (7) |
C8—O8—C9 | 120.5 (6) | C18—C19—H19A | 119.4 |
O7—C8—O8 | 121.9 (7) | C20—C19—H19A | 119.4 |
O7—C8—C7 | 124.1 (8) | C19—C20—C21 | 119.6 (7) |
O8—C8—C7 | 113.9 (7) | C19—C20—H20A | 120.2 |
C14—O9—C10 | 112.6 (5) | C21—C20—H20A | 120.2 |
O8—C9—C10 | 112.0 (5) | O12—C21—C22 | 124.3 (6) |
O8—C9—H9A | 109.2 | O12—C21—C20 | 115.7 (6) |
C10—C9—H9A | 109.2 | C22—C21—C20 | 119.9 (6) |
O8—C9—H9B | 109.2 | C21—C22—C23 | 119.7 (7) |
C10—C9—H9B | 109.2 | C21—C22—H22A | 120.2 |
H9A—C9—H9B | 107.9 | C23—C22—H22A | 120.2 |
C15—O10—C14 | 117.9 (5) | C22—C23—C18 | 121.3 (7) |
O9—C10—C9 | 107.0 (5) | C22—C23—H23A | 119.4 |
O9—C10—C11 | 110.3 (5) | C18—C23—H23A | 119.4 |
C9—C10—C11 | 113.8 (6) | O12—C24—H24A | 109.5 |
O9—C10—H10A | 108.5 | O12—C24—H24B | 109.5 |
C9—C10—H10A | 108.5 | H24A—C24—H24B | 109.5 |
C11—C10—H10A | 108.5 | O12—C24—H24C | 109.5 |
O6—C11—C10 | 104.2 (5) | H24A—C24—H24C | 109.5 |
O6—C11—C12 | 110.1 (5) | H24B—C24—H24C | 109.5 |
C13—O2—C2—O1 | 2.2 (13) | O4—C12—C13—C14 | 171.1 (5) |
C13—O2—C2—C1 | 169.5 (7) | C11—C12—C13—C14 | 51.3 (7) |
C12—O4—C4—O3 | −2.7 (10) | C15—O10—C14—O9 | 94.4 (7) |
C12—O4—C4—C3 | 176.6 (6) | C15—O10—C14—C13 | −151.1 (5) |
C11—O6—C6—O5 | 5.5 (11) | C10—O9—C14—O10 | 176.0 (5) |
C11—O6—C6—C5 | −177.4 (6) | C10—O9—C14—C13 | 64.4 (6) |
C9—O8—C8—O7 | −0.6 (11) | O2—C13—C14—O10 | 71.6 (5) |
C9—O8—C8—C7 | −179.3 (5) | C12—C13—C14—O10 | −170.9 (5) |
C8—O8—C9—C10 | 100.3 (8) | O2—C13—C14—O9 | −175.3 (4) |
C14—O9—C10—C9 | 172.6 (6) | C12—C13—C14—O9 | −57.8 (6) |
C14—O9—C10—C11 | −63.1 (7) | C14—O10—C15—O11 | −0.9 (10) |
O8—C9—C10—O9 | 46.1 (8) | C14—O10—C15—C16 | 179.8 (6) |
O8—C9—C10—C11 | −76.0 (7) | O11—C15—C16—C17 | 175.3 (7) |
C6—O6—C11—C10 | 147.6 (6) | O10—C15—C16—C17 | −5.5 (10) |
C6—O6—C11—C12 | −93.3 (7) | C15—C16—C17—C18 | 179.4 (7) |
O9—C10—C11—O6 | 172.1 (5) | C16—C17—C18—C19 | 178.2 (7) |
C9—C10—C11—O6 | −67.7 (7) | C16—C17—C18—C23 | −1.7 (11) |
O9—C10—C11—C12 | 53.6 (7) | C23—C18—C19—C20 | −0.8 (10) |
C9—C10—C11—C12 | 173.9 (5) | C17—C18—C19—C20 | 179.2 (6) |
C4—O4—C12—C13 | 140.7 (6) | C18—C19—C20—C21 | 2.1 (10) |
C4—O4—C12—C11 | −99.0 (6) | C24—O12—C21—C22 | 0.3 (10) |
O6—C11—C12—O4 | 78.9 (6) | C24—O12—C21—C20 | 178.8 (7) |
C10—C11—C12—O4 | −166.2 (5) | C19—C20—C21—O12 | 178.8 (6) |
O6—C11—C12—C13 | −163.9 (5) | C19—C20—C21—C22 | −2.7 (10) |
C10—C11—C12—C13 | −49.0 (7) | O12—C21—C22—C23 | −179.7 (6) |
C2—O2—C13—C12 | 129.9 (7) | C20—C21—C22—C23 | 1.9 (10) |
C2—O2—C13—C14 | −110.9 (7) | C21—C22—C23—C18 | −0.6 (10) |
O4—C12—C13—O2 | −72.7 (6) | C19—C18—C23—C22 | 0.1 (10) |
C11—C12—C13—O2 | 167.5 (5) | C17—C18—C23—C22 | 180.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O3i | 0.96 | 2.45 | 3.164 (12) | 131 |
C10—H10A···O5ii | 0.98 | 2.48 | 3.423 (9) | 160 |
C13—H13A···O11iii | 0.98 | 2.55 | 3.371 (8) | 142 |
C24—H24A···O8iv | 0.96 | 2.51 | 3.457 (10) | 171 |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x, y+1, z; (iii) x, y−1, z; (iv) −x+1, y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C24H28O12 |
Mr | 508.46 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 9.972 (2), 6.0580 (12), 21.680 (4) |
β (°) | 97.19 (3) |
V (Å3) | 1299.4 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.40 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.959, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2955, 2790, 1578 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.070, 0.189, 1.02 |
No. of reflections | 2790 |
No. of parameters | 319 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.40 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5A···O3i | 0.9600 | 2.4500 | 3.164 (12) | 131.00 |
C10—H10A···O5ii | 0.9800 | 2.4800 | 3.423 (9) | 160.00 |
C13—H13A···O11iii | 0.9800 | 2.5500 | 3.371 (8) | 142.00 |
C24—H24A···O8iv | 0.9600 | 2.5100 | 3.457 (10) | 171.00 |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x, y+1, z; (iii) x, y−1, z; (iv) −x+1, y+1/2, −z. |
Acknowledgements
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Loganathan, D. & Trivedi, G. K. (1987). Carbohydr. Res. 162, 117–125. CrossRef CAS Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yu, C. F., Liu, Z. F. & Cai, M. S. (1991). Chem. Res. Chin. Univ. 12, 349–350. CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
1-O-(p-methoxycinnamoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose is a type of glycolipid derivative (Loganathan et al., 1987) that plays an important role in medical applications, such as anti-tumor and antibacterial applications. We report here the crystal structure of the title compound, (I).
The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987).
In the crystal, molecules are linked to each other to form a three dimensional framework via intermolecular C—H···O hydrogen bonds.