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Acta Cryst. (2008). E64, o616    [ doi:10.1107/S1600536808004698 ]

2,3,4,6-Tetra-O-acetyl-1-O-(4-methoxycinnamoyl)-[beta]-D-glucopyranose

Y.-Y. Liu, S. Liu, Q.-Y. Chu and H.-J. Zhu

Abstract top

Molecules of the title compound, C24H28O12, are linked by intermolecular C-H...O hydrogen bonds. Bond lengths and angles are normal.

Comment top

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.

Related literature top

For related literature, see: Loganathan & Trivedi (1987); Yu et al. (1991). For bond-length data, see: Allen et al. (1987).

Experimental top

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.

Refinement top

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 anomalous scattering effects 82 Friedel pairs have been merged.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: 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).

Figures top
[Figure 1] 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.
2,3,4,6-Tetra-O-acetyl-1-O-(4-methoxycinnamoyl)-β-D-glucopyranose top
Crystal data top
C24H28O12F000 = 536
Mr = 508.46Dx = 1.300 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 9.972 (2) Åθ = 9–12º
b = 6.0580 (12) ŵ = 0.11 mm−1
c = 21.680 (4) ÅT = 298 (2) K
β = 97.19 (3)ºNeedle, colourless
V = 1299.4 (4) Å30.40 × 0.10 × 0.10 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.062
Radiation source: fine-focus sealed tubeθmax = 26.0º
Monochromator: graphiteθmin = 1.9º
T = 298(2) Kh = −11→11
ω/2θ scansk = 0→7
Absorption correction: ψ scan
(North et al., 1968)		l = 0→26
Tmin = 0.959, Tmax = 0.9903 standard reflections
2955 measured reflections every 200 reflections
2790 independent reflections intensity decay: none
1578 reflections with I > 2σ(I)
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)] = 0.070H-atom parameters constrained
wR(F2) = 0.189  w = 1/[σ2(Fo2) + (0.09P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2790 reflectionsΔρmax = 0.43 e Å−3
319 parametersΔρmin = −0.40 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C24H28O12V = 1299.4 (4) Å3
Mr = 508.46Z = 2
Monoclinic, P21Mo Kα
a = 9.972 (2) ŵ = 0.11 mm−1
b = 6.0580 (12) ÅT = 298 (2) K
c = 21.680 (4) Å0.40 × 0.10 × 0.10 mm
β = 97.19 (3)º
Data collection top
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 = 0.9903 standard reflections
2955 measured reflections every 200 reflections
2790 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.070H-atom parameters constrained
wR(F2) = 0.189Δρmax = 0.43 e Å−3
S = 1.02Δρmin = −0.40 e Å−3
2790 reflectionsAbsolute structure: ?
319 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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
O10.5843 (6)0.1875 (12)0.2849 (3)0.089
C10.6777 (7)0.468 (2)0.3547 (4)0.099 (3)
H1A0.76430.42700.34330.148*
H1B0.68040.46170.39900.148*
H1C0.65590.61530.34050.148*
O20.4512 (4)0.3681 (9)0.3422 (2)0.0591 (13)
C20.5738 (7)0.3138 (18)0.3256 (4)0.084 (3)
O30.2760 (6)0.0744 (11)0.4807 (2)0.0799 (17)
C30.3974 (9)−0.2530 (17)0.4674 (4)0.090 (3)
H3A0.3975−0.27270.51130.135*
H3B0.4888−0.24450.45800.135*
H3C0.3526−0.37580.44570.135*
O40.3228 (5)−0.0182 (9)0.38543 (19)0.0567 (12)
C40.3267 (7)−0.0507 (14)0.4480 (3)0.0567 (18)
O50.0717 (7)−0.2870 (10)0.3886 (3)0.0846 (18)
C5−0.0937 (9)−0.123 (2)0.4448 (4)0.116 (4)
H5A−0.1026−0.26750.46190.174*
H5B−0.1795−0.07580.42390.174*
H5C−0.0641−0.02120.47760.174*
O60.0213 (4)0.0758 (8)0.3744 (2)0.0512 (12)
C60.0086 (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−0.0739−0.41810.15280.106*
H7B0.0305−0.23820.13810.106*
H7C−0.1224−0.21370.11160.106*
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)
O90.1321 (4)0.3455 (8)0.24191 (19)0.0492 (11)
C9−0.0883 (6)0.2144 (13)0.2493 (3)0.0539 (18)
H9A−0.14310.13880.27670.065*
H9B−0.13680.34580.23370.065*
O100.3339 (4)0.4790 (8)0.2226 (2)0.0546 (12)
C100.0445 (6)0.2813 (12)0.2859 (3)0.0521 (18)
H10A0.02880.40980.31150.062*
C110.1097 (6)0.1011 (11)0.3280 (3)0.0482 (17)
H11A0.1150−0.03660.30470.058*
O110.2593 (5)0.8310 (8)0.2125 (2)0.0652 (14)
O120.8530 (5)0.5383 (9)−0.0491 (2)0.0678 (15)
C120.2491 (6)0.1706 (11)0.3578 (3)0.0436 (15)
H12A0.24080.28260.38970.052*
C130.3322 (6)0.2602 (11)0.3099 (3)0.0455 (16)
H13A0.35880.14080.28350.055*
C140.2546 (6)0.4380 (12)0.2704 (3)0.0523 (18)
H14A0.24000.57100.29440.063*
C150.3289 (7)0.6851 (15)0.1968 (3)0.058 (2)
C160.4170 (7)0.7047 (14)0.1476 (3)0.0594 (19)
H16A0.41470.83490.12480.071*
C170.4991 (7)0.5466 (15)0.1343 (3)0.062 (2)
H17A0.49990.41890.15820.074*
C180.5902 (6)0.5500 (11)0.0855 (3)0.0448 (15)
C190.6731 (7)0.3730 (13)0.0785 (3)0.0558 (18)
H19A0.67200.25240.10490.067*
C200.7586 (6)0.3706 (13)0.0325 (3)0.0527 (17)
H20A0.81180.24740.02750.063*
C210.7641 (6)0.5531 (13)−0.0059 (3)0.0499 (17)
C220.6811 (6)0.7313 (13)0.0001 (3)0.0547 (18)
H22A0.68260.8520−0.02630.066*
C230.5952 (6)0.7300 (13)0.0457 (3)0.0534 (18)
H23A0.53990.85130.04980.064*
C240.8593 (8)0.7190 (19)−0.0897 (4)0.088 (3)
H24A0.92510.6896−0.11740.132*
H24B0.88480.8495−0.06590.132*
H24C0.77230.7410−0.11340.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0890.0890.0890.0000.0110.000
C10.062 (5)0.131 (8)0.109 (7)−0.030 (6)0.033 (5)−0.042 (7)
O20.049 (3)0.071 (3)0.061 (3)−0.011 (3)0.019 (2)−0.012 (3)
C20.051 (4)0.126 (8)0.079 (5)−0.008 (5)0.027 (4)−0.054 (6)
O30.088 (4)0.104 (5)0.049 (3)0.037 (4)0.014 (3)−0.006 (3)
C30.113 (7)0.090 (7)0.066 (5)0.025 (7)0.006 (5)−0.001 (5)
O40.067 (3)0.060 (3)0.046 (3)0.009 (3)0.017 (2)−0.005 (3)
C40.055 (4)0.060 (5)0.055 (4)0.001 (4)0.007 (3)−0.009 (4)
O50.119 (5)0.050 (4)0.086 (4)−0.014 (4)0.016 (3)0.008 (3)
C50.118 (8)0.143 (10)0.095 (7)−0.048 (8)0.050 (6)0.023 (7)
O60.051 (3)0.052 (3)0.054 (3)−0.008 (2)0.021 (2)−0.010 (2)
C60.075 (5)0.052 (5)0.058 (4)−0.030 (5)0.011 (4)0.001 (4)
O70.132 (5)0.074 (4)0.084 (4)−0.025 (4)0.033 (4)0.005 (4)
C70.077 (5)0.069 (6)0.061 (4)−0.003 (5)−0.006 (4)−0.010 (5)
O80.056 (3)0.046 (3)0.061 (3)−0.005 (2)0.004 (2)0.000 (3)
C80.052 (4)0.059 (5)0.068 (5)0.002 (4)0.003 (4)−0.005 (5)
O90.044 (2)0.049 (3)0.058 (3)−0.005 (2)0.020 (2)0.009 (2)
C90.042 (4)0.051 (4)0.070 (5)0.000 (4)0.011 (3)0.000 (4)
O100.060 (3)0.042 (2)0.069 (3)−0.009 (2)0.038 (2)0.006 (3)
C100.046 (4)0.058 (5)0.057 (4)−0.002 (3)0.023 (3)0.001 (4)
C110.054 (4)0.042 (4)0.054 (4)0.001 (3)0.029 (3)0.000 (3)
O110.086 (4)0.044 (3)0.073 (3)0.012 (3)0.037 (3)−0.003 (3)
O120.073 (3)0.074 (4)0.063 (3)0.023 (3)0.033 (3)0.015 (3)
C120.050 (4)0.033 (3)0.048 (3)0.002 (3)0.010 (3)−0.005 (3)
C130.048 (4)0.043 (4)0.046 (3)−0.006 (3)0.012 (3)−0.011 (3)
C140.054 (4)0.047 (4)0.061 (4)−0.011 (3)0.028 (3)−0.021 (4)
C150.049 (4)0.073 (5)0.056 (4)−0.018 (4)0.026 (3)−0.010 (4)
C160.061 (4)0.063 (5)0.059 (4)−0.016 (4)0.025 (3)0.002 (4)
C170.052 (4)0.089 (6)0.047 (4)0.001 (4)0.013 (3)0.005 (4)
C180.042 (3)0.049 (4)0.045 (3)−0.006 (3)0.012 (3)0.002 (3)
C190.055 (4)0.060 (5)0.051 (4)−0.006 (4)0.003 (3)0.003 (4)
C200.048 (4)0.058 (4)0.053 (4)0.004 (4)0.013 (3)−0.004 (4)
C210.044 (3)0.062 (4)0.045 (4)0.002 (4)0.012 (3)−0.005 (4)
C220.059 (4)0.053 (4)0.054 (4)0.002 (4)0.016 (3)0.010 (4)
C230.043 (4)0.066 (5)0.054 (4)0.001 (4)0.015 (3)0.001 (4)
C240.083 (5)0.127 (8)0.064 (5)−0.001 (7)0.048 (4)−0.002 (6)
Geometric parameters (Å, °) top
O1—C21.183 (9)O10—C151.366 (9)
C1—C21.475 (12)O10—C141.403 (7)
C1—H1A0.9600C10—C111.516 (9)
C1—H1B0.9600C10—H10A0.9800
C1—H1C0.9600C11—C121.518 (9)
O2—C21.358 (8)C11—H11A0.9800
O2—C131.456 (7)O11—C151.199 (8)
O3—C41.193 (8)O12—C211.372 (7)
C3—C41.450 (12)O12—C241.411 (11)
C3—H3A0.9600C12—C131.509 (8)
C3—H3B0.9600C12—H12A0.9800
C3—H3C0.9600C13—C141.525 (9)
O4—C41.367 (8)C13—H13A0.9800
O4—C121.448 (8)C14—H14A0.9800
O5—C61.182 (10)C15—C161.469 (8)
C5—C61.509 (10)C16—C171.315 (10)
C5—H5A0.9600C16—H16A0.9300
C5—H5B0.9600C17—C181.479 (8)
C5—H5C0.9600C17—H17A0.9300
O6—C61.365 (9)C18—C191.375 (9)
O6—C111.425 (7)C18—C231.396 (9)
O7—C81.253 (9)C19—C201.390 (8)
C7—C81.477 (10)C19—H19A0.9300
C7—H7A0.9600C20—C211.389 (10)
C7—H7B0.9600C20—H20A0.9300
C7—H7C0.9600C21—C221.376 (9)
O8—C81.305 (9)C22—C231.386 (8)
O8—C91.431 (8)C22—H22A0.9300
O9—C141.413 (7)C23—H23A0.9300
O9—C101.426 (7)C24—H24A0.9600
C9—C101.512 (9)C24—H24B0.9600
C9—H9A0.9700C24—H24C0.9600
C9—H9B0.9700
C2—C1—H1A109.5C10—C11—C12110.9 (5)
C2—C1—H1B109.5O6—C11—H11A110.5
H1A—C1—H1B109.5C10—C11—H11A110.5
C2—C1—H1C109.5C12—C11—H11A110.5
H1A—C1—H1C109.5C21—O12—C24117.3 (6)
H1B—C1—H1C109.5O4—C12—C13106.0 (5)
C2—O2—C13118.1 (5)O4—C12—C11110.3 (5)
O1—C2—O2121.4 (7)C13—C12—C11111.0 (5)
O1—C2—C1127.2 (7)O4—C12—H12A109.8
O2—C2—C1109.9 (7)C13—C12—H12A109.8
C4—C3—H3A109.5C11—C12—H12A109.8
C4—C3—H3B109.5O2—C13—C12108.3 (5)
H3A—C3—H3B109.5O2—C13—C14106.2 (5)
C4—C3—H3C109.5C12—C13—C14110.9 (5)
H3A—C3—H3C109.5O2—C13—H13A110.4
H3B—C3—H3C109.5C12—C13—H13A110.4
C4—O4—C12118.3 (5)C14—C13—H13A110.4
O3—C4—O4122.5 (7)O10—C14—O9106.4 (5)
O3—C4—C3126.3 (7)O10—C14—C13104.3 (5)
O4—C4—C3111.2 (7)O9—C14—C13108.4 (5)
C6—C5—H5A109.5O10—C14—H14A112.4
C6—C5—H5B109.5O9—C14—H14A112.4
H5A—C5—H5B109.5C13—C14—H14A112.4
C6—C5—H5C109.5O11—C15—O10123.4 (5)
H5A—C5—H5C109.5O11—C15—C16124.5 (7)
H5B—C5—H5C109.5O10—C15—C16112.1 (7)
C6—O6—C11118.1 (5)C17—C16—C15123.1 (7)
O5—C6—O6125.7 (6)C17—C16—H16A118.5
O5—C6—C5124.5 (9)C15—C16—H16A118.5
O6—C6—C5109.8 (8)C16—C17—C18127.0 (7)
C8—C7—H7A109.5C16—C17—H17A116.5
C8—C7—H7B109.5C18—C17—H17A116.5
H7A—C7—H7B109.5C19—C18—C23118.2 (6)
C8—C7—H7C109.5C19—C18—C17120.1 (7)
H7A—C7—H7C109.5C23—C18—C17121.8 (6)
H7B—C7—H7C109.5C18—C19—C20121.3 (7)
C8—O8—C9120.5 (6)C18—C19—H19A119.4
O7—C8—O8121.9 (7)C20—C19—H19A119.4
O7—C8—C7124.1 (8)C19—C20—C21119.6 (7)
O8—C8—C7113.9 (7)C19—C20—H20A120.2
C14—O9—C10112.6 (5)C21—C20—H20A120.2
O8—C9—C10112.0 (5)O12—C21—C22124.3 (6)
O8—C9—H9A109.2O12—C21—C20115.7 (6)
C10—C9—H9A109.2C22—C21—C20119.9 (6)
O8—C9—H9B109.2C21—C22—C23119.7 (7)
C10—C9—H9B109.2C21—C22—H22A120.2
H9A—C9—H9B107.9C23—C22—H22A120.2
C15—O10—C14117.9 (5)C22—C23—C18121.3 (7)
O9—C10—C9107.0 (5)C22—C23—H23A119.4
O9—C10—C11110.3 (5)C18—C23—H23A119.4
C9—C10—C11113.8 (6)O12—C24—H24A109.5
O9—C10—H10A108.5O12—C24—H24B109.5
C9—C10—H10A108.5H24A—C24—H24B109.5
C11—C10—H10A108.5O12—C24—H24C109.5
O6—C11—C10104.2 (5)H24A—C24—H24C109.5
O6—C11—C12110.1 (5)H24B—C24—H24C109.5
C13—O2—C2—O12.2 (13)O4—C12—C13—C14171.1 (5)
C13—O2—C2—C1169.5 (7)C11—C12—C13—C1451.3 (7)
C12—O4—C4—O3−2.7 (10)C15—O10—C14—O994.4 (7)
C12—O4—C4—C3176.6 (6)C15—O10—C14—C13−151.1 (5)
C11—O6—C6—O55.5 (11)C10—O9—C14—O10176.0 (5)
C11—O6—C6—C5−177.4 (6)C10—O9—C14—C1364.4 (6)
C9—O8—C8—O7−0.6 (11)O2—C13—C14—O1071.6 (5)
C9—O8—C8—C7−179.3 (5)C12—C13—C14—O10−170.9 (5)
C8—O8—C9—C10100.3 (8)O2—C13—C14—O9−175.3 (4)
C14—O9—C10—C9172.6 (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—O946.1 (8)C14—O10—C15—C16179.8 (6)
O8—C9—C10—C11−76.0 (7)O11—C15—C16—C17175.3 (7)
C6—O6—C11—C10147.6 (6)O10—C15—C16—C17−5.5 (10)
C6—O6—C11—C12−93.3 (7)C15—C16—C17—C18179.4 (7)
O9—C10—C11—O6172.1 (5)C16—C17—C18—C19178.2 (7)
C9—C10—C11—O6−67.7 (7)C16—C17—C18—C23−1.7 (11)
O9—C10—C11—C1253.6 (7)C23—C18—C19—C20−0.8 (10)
C9—C10—C11—C12173.9 (5)C17—C18—C19—C20179.2 (6)
C4—O4—C12—C13140.7 (6)C18—C19—C20—C212.1 (10)
C4—O4—C12—C11−99.0 (6)C24—O12—C21—C220.3 (10)
O6—C11—C12—O478.9 (6)C24—O12—C21—C20178.8 (7)
C10—C11—C12—O4−166.2 (5)C19—C20—C21—O12178.8 (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—C12129.9 (7)C20—C21—C22—C231.9 (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—C220.1 (10)
C11—C12—C13—O2167.5 (5)C17—C18—C23—C22180.0 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O3i0.962.453.164 (12)131
C10—H10A···O5ii0.982.483.423 (9)160
C13—H13A···O11iii0.982.553.371 (8)142
C24—H24A···O8iv0.962.513.457 (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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5A···O3i0.962.453.164 (12)131
C10—H10A···O5ii0.982.483.423 (9)160
C13—H13A···O11iii0.982.553.371 (8)142
C24—H24A···O8iv0.962.513.457 (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.
Acknowledgements top

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

references
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