Download citation
Download citation
link to html
The title compound, 6-C-gluco­pyran­osyl-7-O-methyl­apigenin dihydrate, C22H22O10·2H2O, is a natural C-glu­cosyl­flavone. The flavone skeleton is almost planar, the dihedral angle between the pyran moiety and the 4-hydroxy­phenyl ring being 9.8 (3)°. The basal plane of the pyran­osyl ring of the glucose moiety is almost perpendicular to the benzo­pyran ring system. The flavone skeletons are stacked along the a axis, forming layers parallel to (001). Between these hydro­phobic layers, the glucose groups and water mol­ecules of crystallization are connected via O-H...O hydrogen bonds, forming hydro­philic layers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104028355/sx1162sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104028355/sx1162Isup2.hkl
Contains datablock I

CCDC reference: 259048

Comment top

Flavonoid compounds make up a large group of secondary plant metabolites. Some of them exist as glycosides and show various biological functions, such as co-pigment effects on flower pigmentation, screening effects from solar UV radiation, signaling between micro-organisms and chemo-attraction between insects (Harborne & Williams, 2000). Swertisin (7-O-methylisovitexin) is a C-glucosylflavone isolated from the whole herb of Swertia japonica (Komatsu et al., 1966, 1967), from the seeds of ziziphus jujuba Mill var. spinosa (Cheng et al., 2000), Piper elongatum (Masuoka et al., 2003) and other plants. This compound has also been obtained by acid hydrolysis of flavocommelin, which was isolated from the blue petals of Commelina communis (Takeda et al., 1966).

In the supramolecular metal complex pigment (commelinin) of the blue flowers of Commelina communis (Kondo et al., 1992), six molecules of anthocyanin (malonylawobanin) and six molecules of flavone (flavocommelin) form a flattened spherical cluster with two metal atoms and chiral ππ stacking interactions inside the cluster. Chiral self-association of flavocommelin in aqueous solution was also deduced on the basis of CD (circular dichroism) spectra (Goto et al., 1990). In these chiral molecular stacking phenomena, the conformation of glucosyl moieties and intermolecular hydrogen bonding involving the sugar groups must play very important roles (Kondo et al., 2001). The octaacetate derivative of flavocommelin does not show any ππ stacking in the crystal (Ohsawa et al., 1994), which may result from there being no intermolecular hydrogen bonding. The crystal structures of flavone glycosides may give some features of the self-association. However, X-ray structural analyses of flavone glycosides are very rare (Jin, Yamagata et al., 1990; Jin, Fujii et al., 1990; Hirakura et al., 1997). We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The basal plane of the hexopyranosyl glucose ring (defined by atoms O6, C33, C31 and C30) is almost perpendicular to the plane of the benzene ring A (atoms C13–C18), the dihedral angle being 87.3 (3)°. Cheng et al. (2000) reported the existence of rotamers of (I) on the basis of the temperature dependence of 1H and 13C NMR spectra in DMSO-d6 solution, and described the contribution of the methyl group (atom C28) to the rotational energy barrier around the C-glucopyranosyl bond (C14—C29 bond) on the basis of a conformational analysis. The nearly perpendicular arrangement of the basal plane of the glucose moitey and ring A may be the result of non-bonded interatomic repulsions around the C-glucopyranosyl bond.

Phenyl ring B (atoms C22–C27) is slightly rotated out of the plane of the pyran ring (ring C; atoms O3/C17–C21), the O3—C21—C22—C23 torsion angle being 8.3 (9)°. In addition, there is a slight bending of ring B with respect to ring C, as measured by the 0.24 (1) Å shift of the center of phenyl ring B from the plane of pyran ring C. Similar bending has been observed in flavocommelin octaacetate and other flavone crystals (Ohsawa et al., 1994). The dihedral angles between the planes of rings A and C, and between the planes of rings B and C, are 3.0 (2) and 9.8 (3)°, respectively.

The roughly planar 4-hydroxyphenylbenzopyranone skeltons are stacked along the a axis, forming hydrophobic layers (Fig. 2). Fig. 3 shows the ππ stacking in detail by illustrating the neighboring π systems below and above the molecule at (x, y, z), where 0 < x < 1/4. There are two π systems above (related by the 21 screw axis parallel to b) and one π-system below the flavone plane (related by the twofold axis parallel to b). The shortest intermolecular distances between the flavone skeltones are 3.263 (9) Å for O2···C21i and 3.399 (10) Å for C19···C20iii [symmetry codes: (i) 1/2 − x, y − 1/2, 1 − z; (iii) −x, y, 1 − z].

The glucose groups and water molecules of crystallization are connected via O—H···O hydrogen bonds (Table 2), forming hydrophilic layers parallel to (001) (Fig. 2). There is positional disorder of the H atoms in a hydroxyl group (O8) and the water molecules (O11 and O12), as the result of two possible hydrogen-bond linkages. In Fig. 4, one of two possible linkages is shown, i.e. O8iii—H8Aiii···O11—H11B···O12—H12C···O12iv—H12Biv (for symmetry codes see Table 2). The other possible linkage is H8Biii—O8iii···H11C—O11···H12B—O12···H12Civ—O12iv.

In the supramolecular blue pigment, commelinin (Kondo et al., 1992), the C-glucosyl moiety of flavocommelin is a rotamer of (I), suggesting the flexibility of the relative orientation of the glucose moiety. In commelinin, two molecules of flavocommelin are stacked anticlockwise, the torsion angle between the C=O bond axes of the flavone moieties being ca −100°. The C=O bond direction is roughly the direction of electric transition moment of the main absorption band of the flavone compound, and the chiral arrangement of the exciton coupling will cause the CD activity (Nakanishi et al., 1994). On the other hand, in (I), the C=O bond axes are approximately parallel to one other. This configuration may be the result of the two-dimensional arrangement of the flavone skeltons in (I), which is supported by a two-dimensional hydrogen-bonding network of the sugar groups and water molecules.

Experimental top

Compound (I) was obtained by acid hydrolysis of the O-glucopyranosyloxy group bonded to ring B of flavocommelin isolated from Commelina communis. To flavocommelin (500 mg) was added 10% HCl–methanol (500 ml), which was warmed at 333 K for 12 h. The reaction mixture was concentrated in vacuo, and the syrup was recrystallized from an aqueous methanol solution [yield of (I) 140 mg, 38%]. The powder of (I) (280 mg) was dissolved in an aqueous methanol solution (500 ml) at room temperature, and left to stand for slow evaporation of the solvent for five months. At the bottom of the beaker, spherical micelle-like particles were obtained on a curved thin film of (I). Inside the spherical particles, were found very thin plate-like crystals of (I) with well developed (001) faces.

Refinement top

H atoms bonded to C atoms were positioned geometrically, with C—H distances of 0.96 (methyl group) and 0.95 Å (other H atoms), and fixed with Uiso(H) values of 1.2Ueq(C) [Ueq(C) for methyl groups]. The positions of these H atoms were recalculated after each set of refinement cycles, except for the last. About half of the H atoms bonded to O atoms were located from difference syntheses, and positional disorder of the water H atoms was observed, suggesting two possible hydrogen-bond patterns, viz. O11—H11B···O12 and O11···H12B—O12. The positions of the remaining hydroxy and water H atoms were calculated by assuming an intermolecular hydrogen-bond network, with O—H distances of 0.82 Å. The site occupancy factors of atoms H8A, H8B, H11B, H11C, H12B and H12C are 50% each. Atom H11C was introduced as one of two possible positions, assuming sp3 hybridization of atom O11, on the basis of the positions of atoms H11A and H11B; the other position was rejected because of a short contact, 1.86 Å, to atom H34A(1/2 − x, y − 1/2, −z). In order to account for the disorder of the hydrogen bond, O8—H8A···O11iii [symmetry code: (iii) −x, y, −z] and O8···H11Ciii—O11Ciii, two geometrically possible positions were calculated, assuming sp3 hybridization of atom O8, on the basis of the positions of atoms C31 and H8A. The position close to atom H9iii was rejected. The other position, which was assigned to atom H8B, has no H···H short contact, although there is no hydrogen-bond acceptor. Atoms H1, H5, H7 and H9 were refined as riding on the parent O atom, with Uiso(H) values of Ueq(O). The positions of atoms H10, H11A and H12A were refined for several cycles and ?then fixed to maintain a? reasonable hydrogen-bonding geometry. Restraints were applied for the C31···H8A/H8B (1.88 Å), H11A···H11B/H11C (1.31 Å) and H12A···H12B/H12C (1.31 Å) distances. Friedel pairs were merged before the final refinement, since anomalous scattering effects were negligible. The absolute structure was assigned on the basis of the absolute configuration of D-(+)-glucose.

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 50% probability level. The H atoms bonded to atoms O8, O11 and O12 show positional disorder, and atoms H8B, H11C and H12B have been omitted for clarity.
[Figure 2] Fig. 2. The crystal structure of (I), projected along the b axis. Thin lines indicate hydrogen bonds. H atoms bonded to C atoms, and atoms H8B, H11C and H12B, have been omitted for clarity.
[Figure 3] Fig. 3. The ππ stacking between the flavone moiety at (x, y, z) (0<x<1/4; hatched) and those of the neighboring molecules above (1/4<x<1/2) and below (−1/4<x<0). The substituents such as glucose groups, have been omitted for clarity. Rings, A, B and C are labeled. [Symmetry codes: (i) 1/2 − x, y − 1/2, 1 − z; (ii) 1/2 − x, y + 1/2, 1 − z; (iii) −x, y, 1 − z.]
[Figure 4] Fig. 4. The hydrogen-bond network of glucose groups and water molecules. The flavone moieties, some atoms bonded to the suger rings and some of the disordered H atoms have been omitted for clarity. [Symmetry codes: (iii) −x, y, −z; (iv) 1 − x, y, −z. SYM CODE iii DIFFERS FROM THAT IN FIG 3.]
6-C-glucopyranosyl-7-O-methylapigenin dihydrate top
Crystal data top
C22H22O10·2H2OF(000) = 1016
Mr = 482.44Dx = 1.507 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
a = 12.950 (3) ÅCell parameters from 25 reflections
b = 8.036 (3) Åθ = 10.0–13.5°
c = 20.436 (6) ŵ = 0.12 mm1
β = 90.14 (2)°T = 296 K
V = 2126.7 (11) Å3Plate, pale yellow
Z = 40.40 × 0.20 × 0.03 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.014
ω scansθmax = 25.0°
Absorption correction: integration
(ABSCOR; Higashi, 1999)
h = 615
Tmin = 0.980, Tmax = 0.997k = 09
2235 measured reflectionsl = 2424
2017 independent reflections3 standard reflections every 150 reflections
1063 reflections with I > 2σ(I) intensity decay: 0.7%
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.0633P)2 + 0.191P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.135(Δ/σ)max = 0.007
S = 1.01Δρmax = 0.21 e Å3
2017 reflectionsΔρmin = 0.29 e Å3
330 parametersAbsolute structure: see text
Crystal data top
C22H22O10·2H2OV = 2126.7 (11) Å3
Mr = 482.44Z = 4
Monoclinic, C2Mo Kα radiation
a = 12.950 (3) ŵ = 0.12 mm1
b = 8.036 (3) ÅT = 296 K
c = 20.436 (6) Å0.40 × 0.20 × 0.03 mm
β = 90.14 (2)°
Data collection top
Rigaku AFC-7R
diffractometer
1063 reflections with I > 2σ(I)
Absorption correction: integration
(ABSCOR; Higashi, 1999)
Rint = 0.014
Tmin = 0.980, Tmax = 0.9973 standard reflections every 150 reflections
2235 measured reflections intensity decay: 0.7%
2017 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.135Δρmax = 0.21 e Å3
S = 1.01Δρmin = 0.29 e Å3
2017 reflectionsAbsolute structure: see text
330 parameters
Special details top

Refinement. The atoms H1, H5, H8A, H9, H11A, H11B and H12B were located from difference syntheses. Other H atoms bonded to the O atoms were calculated assuming intermolecular hydrogen bond network. The H11C was introduced as one of two possible positions assuming sp3 hybridization of the atom O11 based on the positions of H11A and H11B, where the other one was rejected because of short distance, 1.86 Å, to the atom H34A (1/2 − x, y − 1/2, −z). In order to take account for the disorder of the hydrogen bond, O8—H8A···O11iii (symmetry code: (iii) −x, y, −z) and O8···H11Ciii—O11Ciii, two geometrically possible positions were calculated assuming sp3 hybridization of the atom O8 based on the positions of C31 and H8A, and the one close to H9iii was rejected. The other, which is H8B, has no H···H short contact, although there is no hydrogen-bond acceptor. The atoms H1, H5, H7 and H9 were ride on the parent O atom. The atoms H10, H11A and H12A were once ride on the parent atom and their positions were fixed. The restraints of the distance were applied for C31···H8A/H8B of 1.88 Å, H11A···H11B/H11C of 1.31 Å, and H12A···H12B/H12C of 1.31 Å.

Refinement using reflections with F2 > 0.0 σ(F2). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1084 (4)0.0045 (8)0.3441 (2)0.043 (1)
O20.1212 (4)0.0148 (9)0.4681 (2)0.049 (1)
O30.1354 (3)0.4906 (8)0.4715 (2)0.037 (1)
O40.1305 (4)0.5128 (8)0.2394 (2)0.044 (1)
O50.1150 (4)0.8215 (8)0.7484 (2)0.053 (1)
O60.1956 (3)0.2055 (8)0.1843 (2)0.037 (1)
O70.0801 (3)0.1730 (8)0.2266 (2)0.045 (1)
O80.0783 (4)0.1544 (7)0.0845 (2)0.058 (2)
O90.1086 (4)0.0004 (9)0.0352 (2)0.056 (1)
O100.3823 (4)0.123 (1)0.1341 (3)0.118 (3)
O110.2688 (4)0.0262 (8)0.1104 (2)0.081 (2)
O120.4448 (4)0.1697 (2)0.0600 (2)0.074 (2)
C130.1172 (5)0.162 (1)0.3478 (3)0.032 (2)
C140.1200 (5)0.257 (1)0.2907 (3)0.029 (2)
C150.1296 (5)0.4299 (9)0.2968 (3)0.032 (2)
C160.1390 (5)0.508 (1)0.3571 (3)0.033 (2)
C170.1342 (5)0.409 (1)0.4125 (3)0.033 (2)
C180.1249 (5)0.238 (1)0.4099 (3)0.032 (2)
C190.1256 (5)0.140 (1)0.4698 (3)0.035 (2)
C200.1301 (5)0.236 (1)0.5286 (3)0.041 (2)
C210.1322 (5)0.402 (1)0.5290 (3)0.038 (2)
C220.1279 (5)0.513 (1)0.5861 (3)0.034 (2)
C230.1141 (5)0.684 (1)0.5790 (3)0.037 (2)
C240.1094 (5)0.787 (1)0.6331 (3)0.042 (2)
C250.1196 (5)0.716 (1)0.6952 (3)0.037 (2)
C260.1319 (6)0.547 (1)0.7031 (3)0.046 (2)
C270.1362 (5)0.446 (1)0.6487 (3)0.043 (2)
C280.1413 (6)0.690 (1)0.2419 (3)0.051 (2)
C290.1081 (5)0.167 (1)0.2258 (3)0.036 (2)
C300.0094 (5)0.205 (1)0.1883 (3)0.035 (2)
C310.0072 (5)0.1047 (9)0.1250 (3)0.040 (2)
C320.1063 (5)0.120 (1)0.0864 (3)0.041 (2)
C330.1990 (5)0.094 (1)0.1295 (3)0.041 (2)
C340.3007 (5)0.131 (1)0.0918 (3)0.060 (3)
H10.10450.04350.38110.0429*
H50.11930.76710.78220.0530*
H70.08260.07360.23560.0450*
H8A0.13250.14150.10450.0582*0.50
H8B0.06670.24630.06860.0582*0.50
H90.09430.04460.00030.0560*
H100.43420.13840.11190.1182*
H11A0.27010.02140.14590.0814*
H11B0.32870.02740.09720.0814*0.50
H11C0.21160.00790.09500.0814*0.50
H12A0.43440.26530.04770.0740*
H12B0.38770.12640.06360.0740*0.50
H12C0.46890.12010.02840.0740*0.50
H160.14840.62460.36020.0394*
H200.13170.17870.56920.0491*
H230.10780.73040.53640.0446*
H240.09940.90350.62820.0502*
H260.13740.50060.74570.0551*
H270.14480.32930.65400.0518*
H28A0.20790.71760.25950.0514*
H28B0.08850.73560.26940.0514*
H28C0.13480.73470.19860.0514*
H290.10920.05060.23430.0438*
H300.00980.32020.17730.0419*
H310.00190.00910.13620.0477*
H320.10970.22800.06770.0495*
H330.20000.01740.14480.0497*
H34A0.29730.23940.07320.0724*
H34B0.30940.05140.05800.0724*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.062 (3)0.036 (3)0.031 (2)0.003 (3)0.001 (2)0.000 (3)
O20.075 (4)0.036 (4)0.035 (3)0.003 (3)0.003 (2)0.001 (3)
O30.049 (3)0.036 (3)0.025 (2)0.002 (3)0.002 (2)0.002 (3)
O40.070 (3)0.030 (3)0.031 (3)0.004 (3)0.002 (2)0.003 (2)
O50.081 (4)0.050 (3)0.028 (3)0.008 (3)0.002 (3)0.011 (3)
O60.034 (2)0.053 (3)0.025 (2)0.003 (2)0.002 (2)0.003 (2)
O70.044 (3)0.047 (3)0.044 (3)0.003 (3)0.008 (2)0.006 (3)
O80.051 (3)0.083 (5)0.041 (3)0.004 (3)0.010 (2)0.005 (3)
O90.074 (4)0.067 (4)0.026 (2)0.010 (3)0.003 (2)0.008 (3)
O100.062 (4)0.22 (1)0.069 (4)0.005 (5)0.008 (3)0.032 (6)
O110.068 (4)0.094 (5)0.083 (4)0.004 (4)0.016 (3)0.019 (4)
O120.074 (4)0.080 (5)0.068 (4)0.002 (4)0.006 (3)0.004 (4)
C130.032 (4)0.027 (4)0.039 (4)0.005 (3)0.003 (3)0.001 (3)
C140.033 (4)0.036 (5)0.020 (3)0.000 (3)0.002 (3)0.002 (3)
C150.039 (4)0.026 (4)0.030 (4)0.005 (3)0.003 (3)0.005 (3)
C160.040 (4)0.032 (4)0.026 (3)0.002 (4)0.005 (3)0.005 (3)
C170.030 (4)0.043 (5)0.026 (4)0.005 (3)0.004 (3)0.009 (3)
C180.031 (4)0.040 (5)0.025 (3)0.004 (3)0.004 (3)0.000 (3)
C190.043 (4)0.026 (5)0.036 (4)0.004 (4)0.006 (3)0.009 (3)
C200.047 (5)0.048 (6)0.027 (4)0.001 (4)0.003 (3)0.004 (4)
C210.042 (5)0.045 (6)0.027 (4)0.001 (4)0.006 (3)0.002 (4)
C220.033 (4)0.042 (5)0.026 (3)0.005 (4)0.001 (3)0.002 (4)
C230.047 (4)0.032 (4)0.032 (4)0.004 (4)0.003 (3)0.002 (4)
C240.043 (4)0.043 (5)0.039 (4)0.009 (4)0.001 (3)0.002 (4)
C250.034 (4)0.045 (5)0.033 (4)0.000 (4)0.003 (3)0.013 (4)
C260.055 (5)0.057 (6)0.025 (4)0.002 (4)0.002 (3)0.004 (4)
C270.053 (5)0.045 (5)0.032 (4)0.000 (4)0.003 (3)0.001 (4)
C280.077 (6)0.041 (5)0.037 (4)0.004 (5)0.003 (4)0.001 (4)
C290.041 (4)0.041 (5)0.027 (3)0.002 (4)0.001 (3)0.000 (3)
C300.037 (4)0.036 (4)0.032 (3)0.002 (4)0.003 (3)0.004 (3)
C310.043 (4)0.045 (5)0.031 (3)0.002 (4)0.009 (3)0.004 (4)
C320.047 (4)0.047 (5)0.029 (3)0.009 (4)0.005 (3)0.002 (4)
C330.048 (4)0.046 (5)0.031 (3)0.001 (4)0.007 (3)0.006 (4)
C340.039 (4)0.111 (8)0.031 (4)0.006 (5)0.004 (3)0.004 (5)
Geometric parameters (Å, º) top
O1—C131.345 (11)C16—H160.950
O1—H10.820C17—C181.377 (12)
O2—C191.249 (11)C18—C191.456 (10)
O3—C171.372 (8)C19—C201.426 (10)
O3—C211.375 (9)C20—C211.337 (13)
O4—C151.349 (8)C20—H200.950
O4—C281.429 (11)C21—C221.467 (10)
O5—C251.381 (9)C22—C231.395 (12)
O5—H50.820C22—C271.392 (10)
O6—C291.450 (7)C23—C241.384 (10)
O6—C331.434 (8)C23—H230.950
O7—C301.423 (7)C24—C251.397 (10)
O7—H70.820C24—H240.950
O8—C311.438 (8)C25—C261.374 (13)
O8—H8A0.820C26—C271.378 (11)
O8—H8B0.820C26—H260.950
O9—C321.424 (9)C27—H270.950
O9—H90.820C28—H28A0.960
O10—C341.365 (9)C28—H28B0.960
O10—H100.822C28—H28C0.960
O11—H11A0.820C29—C301.520 (9)
O11—H11B0.820C29—H290.950
O11—H11C0.820C30—C311.526 (9)
O12—H12A0.820C30—H300.950
O12—H12B0.820C31—C321.513 (9)
O12—H12C0.820C31—H310.950
C13—C141.394 (9)C32—C331.502 (9)
C13—C181.413 (9)C32—H320.950
C14—C151.404 (11)C33—C341.556 (10)
C14—C291.518 (9)C33—H330.950
C15—C161.385 (9)C34—H34A0.950
C16—C171.383 (10)C34—H34B0.950
C13—O1—H1109.5O5—C25—C26121.3 (6)
C17—O3—C21120.3 (7)C24—C25—C26121.4 (7)
C15—O4—C28117.5 (5)C25—C26—C27119.5 (7)
C25—O5—H5109.5C25—C26—H26120.2
C29—O6—C33110.4 (5)C27—C26—H26120.3
C30—O7—H7109.5C22—C27—C26120.7 (8)
C31—O8—H8A109.7C22—C27—H27119.7
C31—O8—H8B109.7C26—C27—H27119.7
C32—O9—H9109.5O4—C28—H28A109.5
C34—O10—H10106.0O4—C28—H28B109.5
H11A—O11—H11B106.0O4—C28—H28C109.5
H11A—O11—H11C106.0H28A—C28—H28B109.5
H12A—O12—H12B106.0H28A—C28—H28C109.5
H12A—O12—H12C106.0H28B—C28—H28C109.5
O1—C13—C14119.9 (6)O6—C29—C14109.3 (5)
O1—C13—C18119.3 (6)O6—C29—C30108.6 (5)
C14—C13—C18120.9 (7)O6—C29—H29107.8
C13—C14—C15117.9 (6)C14—C29—C30115.3 (6)
C13—C14—C29118.0 (7)C14—C29—H29107.8
C15—C14—C29124.0 (6)C30—C29—H29107.8
O4—C15—C14114.4 (6)O7—C30—C29111.7 (5)
O4—C15—C16123.3 (7)O7—C30—C31110.8 (5)
C14—C15—C16122.3 (6)O7—C30—H30108.2
C15—C16—C17117.7 (7)C29—C30—C31109.4 (5)
C15—C16—H16121.1C29—C30—H30108.2
C17—C16—H16121.1C31—C30—H30108.3
O3—C17—C16116.4 (7)O8—C31—C30110.7 (5)
O3—C17—C18120.7 (6)O8—C31—C32109.2 (5)
C16—C17—C18122.9 (6)O8—C31—H31108.0
C13—C18—C17118.2 (6)C30—C31—C32112.7 (5)
C13—C18—C19121.3 (7)C30—C31—H31108.0
C17—C18—C19120.4 (6)C32—C31—H31108.0
O2—C19—C18121.2 (6)O9—C32—C31110.4 (6)
O2—C19—C20124.2 (6)O9—C32—C33108.6 (6)
C18—C19—C20114.6 (7)O9—C32—H32108.9
C19—C20—C21123.1 (7)C31—C32—C33111.1 (5)
C19—C20—H20118.5C31—C32—H32108.9
C21—C20—H20118.5C33—C32—H32108.9
O3—C21—C20120.7 (6)O6—C33—C32110.3 (6)
O3—C21—C22111.6 (7)O6—C33—C34107.2 (6)
C20—C21—C22127.7 (6)O6—C33—H33109.4
C21—C22—C23121.3 (6)C32—C33—C34111.1 (5)
C21—C22—C27119.6 (8)C32—C33—H33109.4
C23—C22—C27119.1 (7)C34—C33—H33109.4
C22—C23—C24120.8 (6)O10—C34—C33109.4 (5)
C22—C23—H23119.6O10—C34—H34A109.5
C24—C23—H23119.6O10—C34—H34B109.5
C23—C24—C25118.4 (8)C33—C34—H34A109.5
C23—C24—H24120.8C33—C34—H34B109.5
C25—C24—H24120.8H34A—C34—H34B109.5
O5—C25—C24117.3 (7)
O1—C13—C14—C15179.8 (6)C14—C13—C18—C170.7 (9)
O1—C13—C14—C292.8 (9)C14—C13—C18—C19177.8 (6)
O1—C13—C18—C17179.8 (6)C14—C15—O4—C28179.2 (6)
O1—C13—C18—C191.2 (9)C14—C15—C16—C172.8 (10)
O2—C19—C18—C131.3 (10)C14—C29—O6—C33166.7 (6)
O2—C19—C18—C17177.2 (6)C14—C29—C30—C31179.1 (6)
O2—C19—C20—C21178.3 (7)C15—C14—C13—C180.7 (9)
O3—C17—C16—C15174.9 (6)C15—C14—C29—C3064.5 (9)
O3—C17—C18—C13175.9 (5)C15—C16—C17—C182.7 (10)
O3—C17—C18—C195.6 (9)C16—C15—O4—C280.4 (9)
O3—C21—C20—C193 (1)C16—C15—C14—C29179.1 (6)
O3—C21—C22—C238.3 (9)C16—C17—O3—C21179.2 (6)
O3—C21—C22—C27172.7 (6)C16—C17—C18—C19176.8 (6)
O4—C15—C14—C13179.3 (5)C17—O3—C21—C201.5 (9)
O4—C15—C14—C292.0 (9)C17—O3—C21—C22176.6 (5)
O4—C15—C16—C17178.4 (6)C17—C18—C19—C203.6 (9)
O5—C25—C24—C23179.8 (6)C18—C13—C14—C29178.2 (6)
O5—C25—C26—C27180.0 (6)C18—C17—O3—C213.1 (9)
O6—C29—C14—C13124.6 (6)C18—C19—C20—C210.8 (10)
O6—C29—C14—C1558.1 (8)C19—C20—C21—C22174.3 (6)
O6—C29—C30—O7179.0 (6)C20—C21—C22—C23169.6 (7)
O6—C29—C30—C3157.9 (8)C20—C21—C22—C279 (1)
O6—C33—C32—O9175.9 (5)C21—C22—C23—C24179.5 (6)
O6—C33—C32—C3154.3 (8)C21—C22—C27—C26179.7 (6)
O6—C33—C34—O1053.5 (10)C22—C23—C24—C250.5 (10)
O7—C30—C29—C1456.0 (9)C22—C27—C26—C250 (1)
O7—C30—C31—O863.9 (7)C23—C22—C27—C260 (1)
O7—C30—C31—C32173.5 (6)C23—C24—C25—C261.4 (10)
O8—C31—C30—C29172.4 (5)C24—C23—C22—C270.5 (10)
O8—C31—C32—O968.0 (7)C24—C25—C26—C271 (1)
O8—C31—C32—C33171.4 (6)C29—O6—C33—C3264.9 (7)
O9—C32—C31—C30168.5 (6)C29—O6—C33—C34174.1 (6)
O9—C32—C33—C3465.4 (8)C29—C30—C31—C3249.8 (8)
O10—C34—C33—C32174.1 (8)C30—C29—O6—C3366.8 (7)
C13—C14—C15—C161.8 (9)C30—C31—C32—C3347.9 (9)
C13—C14—C29—C30112.7 (7)C31—C32—C33—C34173.1 (7)
C13—C18—C17—C161.7 (10)C31—C32—C33—C34173.1 (7)
C13—C18—C19—C20177.9 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.812.542 (6)148
O5—H5···O10i0.822.072.886 (9)175
O5—H5···O6i0.822.542.961 (6)113
O7—H7···O5ii0.822.102.907 (9)170
O8—H8A···O11iii0.822.002.728 (7)148
O8—H8A···O70.822.602.909 (6)104
O9—H9···O8iii0.821.962.771 (7)173
O9—H9···O9iii0.822.753.157 (6)113
O10—H10···O12iv0.821.912.732 (8)179
O11—H11A···O4v0.822.322.945 (6)133
O11—H11A···O6v0.822.373.023 (8)137
O11—H11B···O120.822.032.751 (7)146
O11—H11C···O8iii0.822.102.728 (7)133
O12—H12A···O9vi0.821.982.787 (7)168
O12—H12B···O110.821.982.751 (7)156
O12—H12C···O12iv0.822.162.837 (10)140
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x, y1, z+1; (iii) x, y, z; (iv) x+1, y, z; (v) x+1/2, y1/2, z; (vi) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC22H22O10·2H2O
Mr482.44
Crystal system, space groupMonoclinic, C2
Temperature (K)296
a, b, c (Å)12.950 (3), 8.036 (3), 20.436 (6)
β (°) 90.14 (2)
V3)2126.7 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.40 × 0.20 × 0.03
Data collection
DiffractometerRigaku AFC-7R
diffractometer
Absorption correctionIntegration
(ABSCOR; Higashi, 1999)
Tmin, Tmax0.980, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
2235, 2017, 1063
Rint0.014
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.135, 1.01
No. of reflections2017
No. of parameters330
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.29
Absolute structureSee text

Computer programs: WinAFC Diffractometer Control Software (Rigaku, 1999), WinAFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 2001), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top
O1—C131.345 (11)C14—C151.404 (11)
O2—C191.249 (11)C14—C291.518 (9)
O3—C171.372 (8)C15—C161.385 (9)
O3—C211.375 (9)C16—C171.383 (10)
O4—C151.349 (8)C17—C181.377 (12)
O5—C251.381 (9)C18—C191.456 (10)
C13—C141.394 (9)C19—C201.426 (10)
C13—C181.413 (9)C20—C211.337 (13)
C13—C14—C29118.0 (7)O4—C15—C14114.4 (6)
C15—C14—C29124.0 (6)O4—C15—C16123.3 (7)
O3—C21—C22—C238.3 (9)C15—C14—C29—C3064.5 (9)
O6—C29—C14—C1558.1 (8)C16—C15—O4—C280.4 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.812.542 (6)148
O5—H5···O10i0.822.072.886 (9)175
O7—H7···O5ii0.822.102.907 (9)170
O8—H8A···O11iii0.822.002.728 (7)148
O9—H9···O8iii0.821.962.771 (7)173
O10—H10···O12iv0.821.912.732 (8)179
O11—H11A···O4v0.822.322.945 (6)133
O11—H11A···O6v0.822.373.023 (8)137
O11—H11B···O120.822.032.751 (7)146
O11—H11C···O8iii0.822.102.728 (7)133
O12—H12A···O9vi0.821.982.787 (7)168
O12—H12B···O110.821.982.751 (7)156
O12—H12C···O12iv0.822.162.837 (10)140
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x, y1, z+1; (iii) x, y, z; (iv) x+1, y, z; (v) x+1/2, y1/2, z; (vi) x+1/2, y+1/2, z.
 

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds