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ISSN: 2056-9890

Ranunculin

aDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
*Correspondence e-mail: parvez@ucalgary.ca

(Received 17 August 2010; accepted 29 August 2010; online 4 September 2010)

In the title mol­ecule {systematic name: (5S)-5-[(β-D-gluco­pyranos­yloxy)meth­yl]furan-2(5H)-one}, C11H16O8, the five-membered ring is essentially planar, the maximum deviation being 0.0151 (13) Å for the O atom. The six-membered ring adopts a chair conformation with puckering parameters Q = 0.581 (2) Å, θ = 9.0 (2)° and φ = 39.7 (13)°, and with all of the substituents of the glucoside unit having normal equatorial orientations. The crystal structure is stabilized by extensive O—H⋯O and C—H⋯O hydrogen bonding, resulting in a three-dimensional network.

Related literature

For background to ranunculin, see: Hill & van Heyningen (1951[Hill, R. & van Heyningen, R. (1951). Biochem. J. 49, 332-335.]); Bai et al. (1996[Bai, Y., Benn, M. H., Majak, W. & McDiarmid, R. (1996). J. Agric. Food Chem. 44, 2235-2238.]); Benn & Yelland (1968[Benn, M. H. & Yelland, L. J. (1968). Can. J. Chem. 46, 729-732.]); Boll (1968[Boll, P. M. (1968). Acta Chem. Scand. 22, 3245-3250.]); Camps et al. (1982[Camps, P., Cardellach, J., Font, J., Ortuno, R. M. & Ponsati, O. (1982). Tetrahedron, 38, 2395-2402.]); Fang et al. (1989[Fang, Z., Zhou, J. & Huang, L. (1989). Yaoxue Xuebao, 24, 182-188.]). For chemical and spectrometric data for closely related, simple butenolides, see: Perry et al. (1996[Perry, N. B., Benn, M. H., Forster, L. M., Routledge, A. & Weavers, R. T. (1996). Phytochemistry, 42, 453-459.]). For comparison bond distances, see: Allen et al. (1987[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.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C11H16O8

  • Mr = 276.24

  • Monoclinic, P 21

  • a = 5.7944 (4) Å

  • b = 6.9359 (3) Å

  • c = 15.0491 (10) Å

  • β = 97.895 (2)°

  • V = 599.08 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 173 K

  • 0.30 × 0.24 × 0.02 mm

Data collection
  • Nonius KappaCCD diffractometer with APEXII CCD

  • Absorption correction: multi-scan (SORTAV; Blessing, 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.961, Tmax = 0.997

  • 1926 measured reflections

  • 1133 independent reflections

  • 1112 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.069

  • S = 1.04

  • 1133 reflections

  • 184 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H5O⋯O8i 0.86 (3) 2.17 (3) 2.910 (2) 144 (3)
O6—H6O⋯O5ii 0.92 (3) 1.94 (3) 2.824 (2) 162 (3)
O7—H7O⋯O6ii 0.84 (3) 1.84 (3) 2.668 (2) 173 (3)
O8—H8O⋯O2iii 0.88 (3) 1.96 (3) 2.830 (2) 167 (3)
O6—H6O⋯O7 0.92 (3) 2.56 (3) 2.894 (2) 102 (2)
Symmetry codes: (i) x-1, y-1, z; (ii) [-x, y+{\script{1\over 2}}, -z+1]; (iii) [-x+2, y+{\script{1\over 2}}, -z+2].

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Ranunculin (I) is the glycosidic precursor of the vesicant protoanemonin present in numerous species of Rannunculaceae and is especially associated with the burning sensation on chewing leaves of buttercup plants. It was first obtained in crystalline form by Hill and van Heyningen (1951) who established its gross structure and showed that it undergoes enzymatic cleavage by β-glucosidase to yield the aglucone, which underwent easy dehydration to protoanemonin. These processes were shown to occur readily under autolytic conditions (Bai et al., 1996). The S-stereochemistry of the dihydrofuranone ring was deduced by Benn and Yelland (1968), and Boll (1968), as shown in the schematic diagram, and later confirmed by synthesis (Camps et al., 1982; Fang et al., 1989). Our sample of (I) was a natural product, and as such had been biosynthesised in the plant (and not made in a laboratory). The only stereoisomer which occurs naturally is the D-isomer, and both that and the anomeric configuration of the glycoosidic bond in (I) were established by cleavage of the glycoside by β-D-glucosidases. The X-ray structure reported here provides the simplest unequivocal proof of that stereochemistry since the chirality follows from that of the D-glucopyranosyl moiety.

The molecular structure of (I) is presented in Fig. 1. The five membered ring, O1/C2—C5, is essentially planar with the maximum deviation of any atom being 0.0151 (13) Å for O1. The six-membered ring adopts a chair conformation with puckering parameters (Cremer & Pople, 1975): Q = 0.581 (2) Å, θ = 9.0 (2)° and ϕ = 39.7 (13)°, with all of the substituents of the glucoside unit having normal equatorial orientations. The 5-membered ring folds back away from the six-membered ring as reflected by the torsion angle C6—O3—C1—C5 -162.86 (17)°. The bond distances and angles are as expected (Allen, 2002). The structure is stabilized by extensive O—H···O and C—H···O hydrogen bonding resulting in a three diemsional network (Table 1 & Fig. 2).

There are two other, closely related, simple butenolides known, though their structures rest on chemical and spectrometric data, i.e., without X-ray crystallographic support. They are the (5R,6R) and (5S,6R) steeroisomers of 5-([1-β-D-glucopyranosyloxy]ethyl)-2(5H)-furanone (Perry et al., 1996); the glycosidic precursor of (Z)-5-ethylidene-2(5H)-furanone, a homologue of protoanemonin in Halocarpus biformis juvenile foliage.

Related literature top

For background to ranunculin, see: Hill & van Heyningen (1951); Bai et al. (1996); Benn & Yelland (1968); Boll (1968); Camps et al. (1982); Fang et al. (1989). For chemical and spectrometric data for closely related, simple butenolides, see: Perry et al. (1996). For comparison of bond distances and angles, see: Allen et al. (1987). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The details of the isolation, and some of the physical properties, of our sample of (I) have been reported previously (Benn & Yelland 1968). Suitable crystals of the title compound for X-ray study were grown from a solution in aqueous ethanol (ca 1:20) in the form of plates.

Refinement top

An absolute structure could not be established reliably because of insufficient anomalous scattering effects. Therefore, 792 Friedel pairs were merged. The H-atoms were located from difference maps and were included in the refinements at geometrically idealized positions with C—H distances = 0.95, 0.99 and 1.00 Å for aryl, methylene and methine type H-atoms, respectively; the positions of hydroxyl H-atoms were allowed to refine freely. The H-atoms were assigned Uiso = 1.2 and 1.5 × Ueq of the parent C and O-atoms, respectively. The final difference map was free of chemically significant features.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of the title compound with displacement ellipsoids plotted at 50% probability level.
[Figure 2] Fig. 2. Unit cell packing of the title compound showing intermolecular hydrogen bonds of O—H···O; H-atoms not involved in hydrogen bonds have been excluded.
(5S)-5-[(β-D-glucopyranosyloxy)methyl]furan-2(5H)-one top
Crystal data top
C11H16O8F(000) = 292
Mr = 276.24Dx = 1.531 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1560 reflections
a = 5.7944 (4) Åθ = 1.0–30.0°
b = 6.9359 (3) ŵ = 0.13 mm1
c = 15.0491 (10) ÅT = 173 K
β = 97.895 (2)°Plate, colorless
V = 599.08 (6) Å30.30 × 0.24 × 0.02 mm
Z = 2
Data collection top
Nonius APEXII CCD [APEXII is a Bruker machine - is this a KappaCCD upgraded with an APEXII CCD?]
diffractometer
1133 independent reflections
Radiation source: fine-focus sealed tube1112 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ϕ & ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 66
Tmin = 0.961, Tmax = 0.997k = 68
1926 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: difference Fourier map
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.040P)2 + 0.1617P]
where P = (Fo2 + 2Fc2)/3
1133 reflections(Δ/σ)max = 0.002
184 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = 0.16 e Å3
Crystal data top
C11H16O8V = 599.08 (6) Å3
Mr = 276.24Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.7944 (4) ŵ = 0.13 mm1
b = 6.9359 (3) ÅT = 173 K
c = 15.0491 (10) Å0.30 × 0.24 × 0.02 mm
β = 97.895 (2)°
Data collection top
Nonius APEXII CCD [APEXII is a Bruker machine - is this a KappaCCD upgraded with an APEXII CCD?]
diffractometer
1133 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
1112 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.997Rint = 0.018
1926 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0261 restraint
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.18 e Å3
1133 reflectionsΔρmin = 0.16 e Å3
184 parameters
Special details top

Experimental. NMR data (400 MHz, 1H; 100 MHz 13C) for a solution in D2O containing sodium 3-trimethylsilylpropionate-2,3 - d4 as reference: δH (400 MHz) 7.77 (1H, dd, J = 1.5 and 5.8 Hz, H-4), 6.3 (1H, dd, J = 2.1 and 5.8 Hz, H-3), 5.47 (1H, m), 4.48 (1H, d, J = 7.9 Hz, H-1'), 4.30 (1H, dd, J = 3.2 and 12.2 Hz, H-6 A), 3.95 (1H, dd, J = 5.8 and 12.2 Hz, H-6B), 3.91 (1H, dd, J = 2.1 and 12.5 Hz, H-6A'), 3.72 (1H, dd, J = 5.8 and 12.5 Hz, H-6B'), 3.48 (1H, dd, dd, J = ca 9 Hz H-3'), 3.43 (1H, m, H-5'), 3.37 (1H, dd, J = ca 9 Hz, H=4'), and 3.25 (1H, dd, J = 7.9 and 9.2 Hz, H-2'); δC 179.2 s (C-2), 158.5 d (C-4), 124.7 d (C-3), 105.6 d (C-1'), 86.9 d (C-5), 78.7 d (C-5'), 78.3 d (C-3'), 75.6 d (C-2'), 72.2 d (C-4'), 71.7 t (C-6), 63.3 t (C-6').

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
O10.9146 (3)0.1112 (2)0.96815 (9)0.0225 (4)
O21.0618 (3)0.0493 (3)1.11025 (10)0.0309 (4)
O30.4499 (2)0.0377 (2)0.79524 (9)0.0200 (3)
O40.5209 (2)0.3269 (2)0.73224 (9)0.0188 (3)
O50.1227 (3)0.0568 (2)0.63887 (10)0.0241 (4)
H5O0.085 (5)0.121 (5)0.6833 (19)0.036*
O60.0241 (2)0.2692 (2)0.53178 (10)0.0208 (4)
H6O0.025 (5)0.336 (5)0.479 (2)0.031*
O70.3667 (3)0.5126 (3)0.50561 (9)0.0215 (3)
H7O0.259 (5)0.591 (5)0.4895 (18)0.032*
O80.8805 (3)0.6376 (3)0.72096 (10)0.0277 (4)
H8O0.893 (5)0.563 (5)0.769 (2)0.042*
C10.6798 (3)0.0332 (4)0.84401 (13)0.0216 (5)
H1A0.71910.16010.87210.026*
H1B0.79470.00360.80300.026*
C20.8918 (4)0.0724 (3)1.05518 (13)0.0225 (5)
C30.6434 (4)0.0666 (4)1.06406 (14)0.0252 (5)
H30.57940.04861.11830.030*
C40.5229 (4)0.0912 (3)0.98301 (14)0.0243 (5)
H40.35780.08950.96990.029*
C50.6862 (4)0.1216 (3)0.91570 (13)0.0204 (5)
H50.66090.25170.88740.025*
C60.4469 (4)0.1343 (3)0.71336 (13)0.0178 (4)
H60.55520.06940.67650.021*
C70.2004 (3)0.1338 (3)0.66293 (13)0.0176 (4)
H70.09060.19800.69940.021*
C80.2093 (3)0.2433 (3)0.57590 (13)0.0167 (4)
H80.29850.16520.53630.020*
C90.3238 (3)0.4413 (3)0.59065 (13)0.0172 (4)
H90.21640.53100.61700.021*
C100.5559 (3)0.4305 (3)0.65204 (13)0.0180 (4)
H100.67380.36220.62080.022*
C110.6423 (4)0.6302 (3)0.67948 (14)0.0218 (5)
H11A0.62480.71370.62560.026*
H11B0.54240.68400.72170.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0203 (7)0.0294 (9)0.0169 (7)0.0038 (6)0.0002 (5)0.0024 (6)
O20.0327 (8)0.0329 (10)0.0233 (8)0.0036 (8)0.0095 (7)0.0014 (8)
O30.0212 (7)0.0242 (8)0.0137 (7)0.0011 (7)0.0005 (5)0.0038 (6)
O40.0226 (7)0.0190 (8)0.0143 (7)0.0026 (6)0.0005 (5)0.0001 (6)
O50.0317 (8)0.0223 (8)0.0172 (7)0.0077 (7)0.0007 (6)0.0020 (7)
O60.0177 (7)0.0259 (8)0.0174 (7)0.0007 (6)0.0027 (6)0.0030 (7)
O70.0218 (7)0.0257 (8)0.0172 (7)0.0016 (7)0.0036 (6)0.0063 (7)
O80.0262 (8)0.0330 (9)0.0227 (8)0.0102 (8)0.0010 (6)0.0034 (8)
C10.0200 (10)0.0262 (12)0.0175 (10)0.0020 (10)0.0010 (8)0.0041 (9)
C20.0302 (11)0.0188 (10)0.0175 (9)0.0063 (10)0.0000 (9)0.0026 (9)
C30.0306 (11)0.0257 (11)0.0201 (10)0.0037 (10)0.0064 (8)0.0025 (10)
C40.0235 (10)0.0234 (12)0.0264 (12)0.0004 (10)0.0044 (9)0.0071 (10)
C50.0217 (10)0.0214 (11)0.0168 (10)0.0001 (9)0.0023 (8)0.0016 (9)
C60.0216 (10)0.0179 (10)0.0138 (9)0.0003 (9)0.0020 (7)0.0016 (9)
C70.0190 (10)0.0188 (10)0.0151 (9)0.0014 (9)0.0025 (7)0.0003 (9)
C80.0152 (10)0.0207 (10)0.0135 (9)0.0003 (9)0.0001 (8)0.0008 (8)
C90.0185 (10)0.0191 (10)0.0143 (9)0.0010 (9)0.0038 (7)0.0010 (9)
C100.0180 (10)0.0216 (10)0.0147 (9)0.0004 (10)0.0038 (8)0.0017 (9)
C110.0253 (11)0.0206 (11)0.0189 (10)0.0016 (9)0.0004 (8)0.0006 (10)
Geometric parameters (Å, º) top
O1—C21.361 (2)C2—C31.464 (3)
O1—C51.447 (2)C3—C41.331 (3)
O2—C21.208 (3)C3—H30.9500
O3—C61.401 (2)C4—C51.493 (3)
O3—C11.430 (2)C4—H40.9500
O4—C61.419 (3)C5—H51.0000
O4—C101.443 (2)C6—C71.523 (3)
O5—C71.427 (3)C6—H61.0000
O5—H5O0.86 (3)C7—C81.521 (3)
O6—C81.434 (2)C7—H71.0000
O6—H6O0.92 (3)C8—C91.528 (3)
O7—C91.425 (2)C8—H81.0000
O7—H7O0.84 (3)C9—C101.525 (2)
O8—C111.435 (3)C9—H91.0000
O8—H8O0.88 (3)C10—C111.511 (3)
C1—C51.519 (3)C10—H101.0000
C1—H1A0.9900C11—H11A0.9900
C1—H1B0.9900C11—H11B0.9900
C2—O1—C5109.40 (15)O4—C6—H6109.9
C6—O3—C1111.09 (15)C7—C6—H6109.9
C6—O4—C10112.00 (15)O5—C7—C8106.92 (16)
C7—O5—H5O113 (2)O5—C7—C6111.72 (17)
C8—O6—H6O110.7 (18)C8—C7—C6106.69 (16)
C9—O7—H7O105.7 (19)O5—C7—H7110.5
C11—O8—H8O107 (2)C8—C7—H7110.5
O3—C1—C5108.08 (17)C6—C7—H7110.5
O3—C1—H1A110.1O6—C8—C7108.63 (16)
C5—C1—H1A110.1O6—C8—C9108.56 (17)
O3—C1—H1B110.1C7—C8—C9112.90 (16)
C5—C1—H1B110.1O6—C8—H8108.9
H1A—C1—H1B108.4C7—C8—H8108.9
O2—C2—O1120.56 (19)C9—C8—H8108.9
O2—C2—C3130.8 (2)O7—C9—C10108.24 (15)
O1—C2—C3108.66 (17)O7—C9—C8107.89 (16)
C4—C3—C2108.1 (2)C10—C9—C8111.93 (17)
C4—C3—H3125.9O7—C9—H9109.6
C2—C3—H3125.9C10—C9—H9109.6
C3—C4—C5109.8 (2)C8—C9—H9109.6
C3—C4—H4125.1O4—C10—C11107.91 (16)
C5—C4—H4125.1O4—C10—C9108.49 (15)
O1—C5—C4103.91 (16)C11—C10—C9110.63 (17)
O1—C5—C1106.48 (16)O4—C10—H10109.9
C4—C5—C1115.19 (19)C11—C10—H10109.9
O1—C5—H5110.3C9—C10—H10109.9
C4—C5—H5110.3O8—C11—C10114.47 (18)
C1—C5—H5110.3O8—C11—H11A108.6
O3—C6—O4107.90 (15)C10—C11—H11A108.6
O3—C6—C7109.54 (16)O8—C11—H11B108.6
O4—C6—C7109.80 (16)C10—C11—H11B108.6
O3—C6—H6109.9H11A—C11—H11B107.6
C6—O3—C1—C5162.86 (17)O3—C6—C7—C8179.11 (17)
C5—O1—C2—O2176.8 (2)O4—C6—C7—C860.8 (2)
C5—O1—C2—C33.2 (2)O5—C7—C8—O668.0 (2)
O2—C2—C3—C4176.8 (3)C6—C7—C8—O6172.30 (16)
O1—C2—C3—C43.3 (3)O5—C7—C8—C9171.50 (16)
C2—C3—C4—C52.0 (3)C6—C7—C8—C951.8 (2)
C2—O1—C5—C42.0 (2)O6—C8—C9—O771.42 (19)
C2—O1—C5—C1120.06 (19)C7—C8—C9—O7168.07 (16)
C3—C4—C5—O10.1 (3)O6—C8—C9—C10169.60 (14)
C3—C4—C5—C1116.2 (2)C7—C8—C9—C1049.1 (2)
O3—C1—C5—O1175.41 (16)C6—O4—C10—C11177.97 (16)
O3—C1—C5—C460.8 (2)C6—O4—C10—C962.1 (2)
C1—O3—C6—O461.2 (2)O7—C9—C10—O4169.84 (18)
C1—O3—C6—C7179.26 (17)C8—C9—C10—O451.1 (2)
C10—O4—C6—O3171.64 (15)O7—C9—C10—C1172.0 (2)
C10—O4—C6—C769.02 (19)C8—C9—C10—C11169.25 (17)
O3—C6—C7—O564.4 (2)O4—C10—C11—O874.2 (2)
O4—C6—C7—O5177.31 (17)C9—C10—C11—O8167.27 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O8i0.86 (3)2.17 (3)2.910 (2)144 (3)
O6—H6O···O5ii0.92 (3)1.94 (3)2.824 (2)162 (3)
O7—H7O···O6ii0.84 (3)1.84 (3)2.668 (2)173 (3)
O8—H8O···O2iii0.88 (3)1.96 (3)2.830 (2)167 (3)
C3—H3···O4iv0.952.553.413 (3)151
C4—H4···O1v0.952.573.504 (3)168
C8—H8···O7vi1.002.373.306 (3)155
C1—H1A···O2iii0.992.383.289 (3)153
C10—H10···O6vii1.002.433.415 (3)167
O6—H6O···O70.92 (3)2.56 (3)2.894 (2)102 (2)
C11—H11A···O70.992.592.986 (3)104
Symmetry codes: (i) x1, y1, z; (ii) x, y+1/2, z+1; (iii) x+2, y+1/2, z+2; (iv) x+1, y1/2, z+2; (v) x1, y, z; (vi) x+1, y1/2, z+1; (vii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC11H16O8
Mr276.24
Crystal system, space groupMonoclinic, P21
Temperature (K)173
a, b, c (Å)5.7944 (4), 6.9359 (3), 15.0491 (10)
β (°) 97.895 (2)
V3)599.08 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.30 × 0.24 × 0.02
Data collection
DiffractometerNonius APEXII CCD [APEXII is a Bruker machine - is this a KappaCCD upgraded with an APEXII CCD?]
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.961, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
1926, 1133, 1112
Rint0.018
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.069, 1.04
No. of reflections1133
No. of parameters184
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.16

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5O···O8i0.86 (3)2.17 (3)2.910 (2)144 (3)
O6—H6O···O5ii0.92 (3)1.94 (3)2.824 (2)162 (3)
O7—H7O···O6ii0.84 (3)1.84 (3)2.668 (2)173 (3)
O8—H8O···O2iii0.88 (3)1.96 (3)2.830 (2)167 (3)
O6—H6O···O70.92 (3)2.56 (3)2.894 (2)102 (2)
Symmetry codes: (i) x1, y1, z; (ii) x, y+1/2, z+1; (iii) x+2, y+1/2, z+2.
 

References

First citationAllen, 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
First citationBai, Y., Benn, M. H., Majak, W. & McDiarmid, R. (1996). J. Agric. Food Chem. 44, 2235–2238.  CrossRef CAS Web of Science Google Scholar
First citationBenn, M. H. & Yelland, L. J. (1968). Can. J. Chem. 46, 729–732.  CrossRef CAS Web of Science Google Scholar
First citationBlessing, R. H. (1997). J. Appl. Cryst. 30, 421–426.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBoll, P. M. (1968). Acta Chem. Scand. 22, 3245–3250.  CrossRef CAS Web of Science Google Scholar
First citationCamps, P., Cardellach, J., Font, J., Ortuno, R. M. & Ponsati, O. (1982). Tetrahedron, 38, 2395–2402.  CrossRef CAS Web of Science Google Scholar
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
First citationFang, Z., Zhou, J. & Huang, L. (1989). Yaoxue Xuebao, 24, 182–188.  CAS Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationHill, R. & van Heyningen, R. (1951). Biochem. J. 49, 332–335.  PubMed CAS Web of Science Google Scholar
First citationHooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationPerry, N. B., Benn, M. H., Forster, L. M., Routledge, A. & Weavers, R. T. (1996). Phytochemistry, 42, 453–459.  CrossRef CAS PubMed Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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