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The title compound, C15H12O8·2H2O, crystallizes with two organic mol­ecules and four water mol­ecules in the asymmetric unit. Crystal symmetry generates a racemic mixture of the chiral organic mol­ecules. An extensive network of intra­molecular and inter­molecular O—H...O hydrogen bonds helps to establish the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050416/hb2581sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050416/hb2581Isup2.hkl
Contains datablock I

CCDC reference: 667406

Key indicators

  • Single-crystal X-ray study
  • T = 113 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.059
  • wR factor = 0.155
  • Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O19 - H19B ... ?
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H18A .. O4 .. 2.62 Ang. PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.847(10) ...... 3.00 su-Ra O17 -H17A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.849(10) ...... 3.00 su-Ra O19 -H19B 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.87(3), Rep 0.862(10) ...... 3.00 su-Ra O20 -H20B 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 116(4), Rep 115.6(19) ...... 2.11 su-Ra H18A -O18 -H18B 1.555 1.555 1.555
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C23 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C24 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 11
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check

Comment top

The asymmetric unit of (I) contains of two dihydromyricetin molecules and four water molecules (Fig. 1). In the arbitrarily chosen asymmetric unit, the C1-containing dihydromyricetin molecule has an (R, R) configuration, and the C16 molecule has an (S, S) configuration. In any event, crystal symmetry generates racemic mixture of molecules. The pyran ring exists as a twisted chair conformation in both molecules. The resorcinol ring makes angles of 64.01 (15)° and 74.42 (13)° with the triol ring in the two molecules.

As well as a number of intramolecular O—H···O links, strong intermolecular O—H···O interactions (Table 1) link the component species into a three-dmiensional network in the crystal of (I).

Experimental top

Leaves of Ampelopsis grossedentata (about 200 g) was extracted with 3.5 l boiling water for 1.5 h and then filtered. The filtrate was left for 24 h at ambient temperature and then filtered through a porous filter. The filtered precipitate (about 41.87 g) was collected and purified to yield yellow needles of (I) (about 3.90 g) by recrystallizing 5 times from water.

Refinement top

The H atoms of the water molecules were located in difference maps and refined freely, while the other H atoms were positioned geometrically (C—H = 0.93–0.98 Å, O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Structure description top

The asymmetric unit of (I) contains of two dihydromyricetin molecules and four water molecules (Fig. 1). In the arbitrarily chosen asymmetric unit, the C1-containing dihydromyricetin molecule has an (R, R) configuration, and the C16 molecule has an (S, S) configuration. In any event, crystal symmetry generates racemic mixture of molecules. The pyran ring exists as a twisted chair conformation in both molecules. The resorcinol ring makes angles of 64.01 (15)° and 74.42 (13)° with the triol ring in the two molecules.

As well as a number of intramolecular O—H···O links, strong intermolecular O—H···O interactions (Table 1) link the component species into a three-dmiensional network in the crystal of (I).

Computing details top

Data collection: CrystalClear; cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
(I) top
Crystal data top
C15H12O8·2H2OF(000) = 1488
Mr = 356.28Dx = 1.613 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4298 reflections
a = 15.391 (3) Åθ = 1.7–27.9°
b = 7.9002 (16) ŵ = 0.14 mm1
c = 24.161 (5) ÅT = 113 K
β = 92.57 (3)°Needle, yellow
V = 2934.8 (10) Å30.06 × 0.02 × 0.02 mm
Z = 8
Data collection top
Rigaku saturn
diffractometer
5189 independent reflections
Radiation source: rotating anode3433 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.077
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
CrystalClear (Rigaku/MSC, 2005)
h = 1818
Tmin = 0.992, Tmax = 0.997k = 89
17668 measured reflectionsl = 2828
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)] = 0.059Hydrogen site location: difmap and geom
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0774P)2]
where P = (Fo2 + 2Fc2)/3
5189 reflections(Δ/σ)max < 0.001
495 parametersΔρmax = 0.29 e Å3
11 restraintsΔρmin = 0.29 e Å3
Crystal data top
C15H12O8·2H2OV = 2934.8 (10) Å3
Mr = 356.28Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.391 (3) ŵ = 0.14 mm1
b = 7.9002 (16) ÅT = 113 K
c = 24.161 (5) Å0.06 × 0.02 × 0.02 mm
β = 92.57 (3)°
Data collection top
Rigaku saturn
diffractometer
5189 independent reflections
Absorption correction: multi-scan
CrystalClear (Rigaku/MSC, 2005)
3433 reflections with I > 2σ(I)
Tmin = 0.992, Tmax = 0.997Rint = 0.077
17668 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05911 restraints
wR(F2) = 0.155H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.29 e Å3
5189 reflectionsΔρmin = 0.29 e Å3
495 parameters
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
O10.48728 (14)0.6070 (3)0.21760 (8)0.0199 (5)
O20.28387 (15)0.4841 (3)0.07021 (9)0.0251 (6)
H20.25660.44760.09600.038*
O30.52593 (15)0.8135 (3)0.03286 (9)0.0251 (6)
H30.57040.85240.04790.038*
O40.63802 (15)0.8827 (3)0.11563 (9)0.0243 (5)
O50.69897 (13)0.8183 (2)0.22252 (9)0.0185 (5)
H50.71070.91940.22130.028*
O60.75720 (15)0.4186 (3)0.39160 (9)0.0247 (6)
H60.77690.35220.36930.037*
O70.64803 (14)0.5739 (3)0.46089 (8)0.0232 (5)
H70.68610.50410.46850.035*
O80.50042 (14)0.7283 (3)0.42033 (9)0.0229 (5)
H80.51730.70840.45230.034*
O91.04347 (13)0.4302 (2)0.32245 (8)0.0184 (5)
O101.23667 (15)0.5948 (3)0.47101 (9)0.0237 (6)
H101.25920.64360.44540.036*
O111.00809 (15)0.2216 (3)0.50702 (9)0.0230 (5)
H110.96760.17250.49070.034*
O120.90634 (14)0.1260 (3)0.42278 (9)0.0235 (5)
O130.83770 (14)0.2020 (3)0.31889 (9)0.0205 (5)
H130.82600.10210.32380.031*
O141.02685 (14)0.2668 (3)0.12043 (8)0.0192 (5)
H141.00960.28040.08810.029*
O150.88587 (14)0.4432 (3)0.07755 (8)0.0204 (5)
H150.84150.49720.06980.031*
O160.78232 (15)0.6215 (3)0.14812 (9)0.0238 (6)
H160.76610.68890.17130.036*
C10.4610 (2)0.6266 (4)0.16291 (12)0.0181 (7)
C20.3831 (2)0.5538 (4)0.14623 (12)0.0182 (7)
H2A0.34860.50060.17160.022*
C30.3571 (2)0.5617 (4)0.09030 (13)0.0182 (7)
C40.4049 (2)0.6483 (4)0.05253 (13)0.0208 (7)
H40.38580.65440.01550.025*
C50.4813 (2)0.7257 (4)0.07043 (13)0.0198 (7)
C60.5117 (2)0.7172 (4)0.12640 (12)0.0158 (7)
C70.5897 (2)0.8035 (4)0.14589 (13)0.0172 (7)
C80.6089 (2)0.7946 (4)0.20853 (13)0.0177 (7)
H8A0.57570.88340.22640.021*
C90.5800 (2)0.6225 (4)0.22990 (12)0.0174 (7)
H90.61060.53280.21060.021*
C100.5945 (2)0.5996 (3)0.29144 (13)0.0170 (7)
C110.6674 (2)0.5096 (4)0.31149 (13)0.0188 (7)
H11A0.70330.45640.28690.023*
C120.68601 (19)0.4995 (4)0.36771 (13)0.0173 (7)
C130.6313 (2)0.5766 (4)0.40477 (12)0.0178 (7)
C140.5570 (2)0.6582 (4)0.38456 (12)0.0168 (7)
C150.5388 (2)0.6715 (4)0.32809 (13)0.0187 (7)
H15A0.48920.72850.31490.022*
C161.0682 (2)0.4205 (4)0.37772 (12)0.0159 (7)
C171.1410 (2)0.5098 (3)0.39515 (12)0.0166 (7)
H171.17240.57180.37010.020*
C181.1667 (2)0.5052 (4)0.45111 (13)0.0174 (7)
C191.1219 (2)0.4107 (4)0.48920 (13)0.0184 (7)
H191.13960.41050.52650.022*
C201.0511 (2)0.3177 (4)0.47055 (13)0.0196 (7)
C211.0212 (2)0.3215 (3)0.41395 (12)0.0158 (7)
C220.9487 (2)0.2199 (4)0.39350 (13)0.0185 (7)
C230.9280 (2)0.2292 (4)0.33132 (13)0.0189 (7)
H230.96170.14260.31270.023*
C240.9522 (2)0.4026 (4)0.30964 (12)0.0183 (7)
H240.91830.48930.32810.022*
C250.9363 (2)0.4173 (4)0.24804 (13)0.0183 (7)
C260.8671 (2)0.5154 (4)0.22711 (13)0.0183 (7)
H260.83270.57400.25130.022*
C270.8491 (2)0.5263 (4)0.17056 (13)0.0179 (7)
C280.8997 (2)0.4385 (4)0.13371 (12)0.0159 (7)
C290.9709 (2)0.3463 (3)0.15507 (13)0.0164 (7)
C300.9886 (2)0.3341 (3)0.21165 (13)0.0175 (7)
H301.03560.27000.22520.021*
O170.72397 (17)0.1553 (3)0.21376 (10)0.0299 (6)
O180.72867 (17)0.5768 (3)0.04143 (10)0.0281 (6)
O190.19398 (15)0.3605 (3)0.15503 (10)0.0245 (6)
O200.32106 (16)0.7871 (3)0.39567 (10)0.0261 (6)
H17A0.7710 (15)0.189 (4)0.2298 (14)0.040 (12)*
H17B0.710 (3)0.207 (5)0.1826 (15)0.061 (15)*
H18A0.726 (3)0.677 (2)0.0545 (15)0.067 (15)*
H18B0.723 (4)0.569 (5)0.0062 (5)0.13 (2)*
H19A0.1449 (11)0.319 (3)0.1445 (13)0.024 (10)*
H19B0.2265 (18)0.297 (3)0.1754 (15)0.053 (13)*
H20A0.3757 (8)0.766 (4)0.3997 (15)0.034 (11)*
H20B0.307 (2)0.887 (3)0.407 (2)0.10 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0192 (12)0.0287 (12)0.0117 (12)0.0050 (10)0.0003 (9)0.0043 (9)
O20.0233 (14)0.0370 (13)0.0150 (12)0.0092 (11)0.0005 (10)0.0004 (10)
O30.0229 (14)0.0361 (13)0.0164 (13)0.0100 (11)0.0011 (10)0.0057 (10)
O40.0232 (13)0.0289 (12)0.0208 (13)0.0050 (11)0.0009 (10)0.0048 (10)
O50.0162 (12)0.0192 (11)0.0201 (12)0.0022 (9)0.0007 (10)0.0004 (9)
O60.0223 (13)0.0324 (13)0.0192 (13)0.0100 (11)0.0016 (11)0.0029 (9)
O70.0234 (14)0.0322 (13)0.0136 (12)0.0078 (10)0.0022 (10)0.0003 (9)
O80.0224 (13)0.0339 (12)0.0125 (12)0.0081 (10)0.0011 (10)0.0020 (10)
O90.0185 (12)0.0233 (11)0.0133 (12)0.0033 (9)0.0008 (9)0.0028 (9)
O100.0232 (13)0.0286 (13)0.0188 (13)0.0056 (10)0.0051 (11)0.0048 (9)
O110.0270 (14)0.0273 (12)0.0146 (12)0.0068 (10)0.0014 (10)0.0032 (9)
O120.0258 (14)0.0281 (12)0.0167 (12)0.0047 (10)0.0010 (10)0.0058 (9)
O130.0180 (12)0.0213 (11)0.0221 (13)0.0034 (9)0.0019 (10)0.0027 (9)
O140.0225 (13)0.0223 (11)0.0126 (12)0.0026 (10)0.0000 (10)0.0006 (9)
O150.0226 (13)0.0265 (12)0.0118 (12)0.0038 (10)0.0020 (10)0.0010 (9)
O160.0222 (13)0.0287 (13)0.0202 (13)0.0073 (10)0.0004 (11)0.0030 (9)
C10.0196 (18)0.0197 (15)0.0149 (17)0.0021 (14)0.0009 (14)0.0010 (12)
C20.0195 (18)0.0220 (15)0.0133 (16)0.0017 (14)0.0020 (13)0.0040 (12)
C30.0155 (17)0.0210 (15)0.0181 (17)0.0010 (14)0.0009 (14)0.0007 (13)
C40.0201 (18)0.0293 (17)0.0130 (17)0.0013 (14)0.0003 (14)0.0026 (13)
C50.0207 (18)0.0239 (16)0.0148 (17)0.0021 (14)0.0010 (14)0.0024 (13)
C60.0173 (17)0.0184 (15)0.0117 (16)0.0008 (13)0.0006 (13)0.0008 (12)
C70.0210 (18)0.0173 (15)0.0133 (17)0.0047 (14)0.0020 (14)0.0013 (12)
C80.0171 (17)0.0190 (15)0.0169 (17)0.0012 (13)0.0000 (14)0.0007 (12)
C90.0174 (17)0.0228 (16)0.0120 (16)0.0034 (14)0.0002 (13)0.0010 (12)
C100.0177 (18)0.0165 (15)0.0168 (17)0.0024 (13)0.0018 (14)0.0011 (12)
C110.0167 (17)0.0211 (15)0.0187 (17)0.0006 (14)0.0031 (14)0.0001 (12)
C120.0128 (17)0.0195 (15)0.0195 (17)0.0012 (13)0.0002 (13)0.0011 (12)
C130.0213 (18)0.0189 (15)0.0130 (17)0.0010 (13)0.0017 (14)0.0015 (12)
C140.0167 (18)0.0178 (15)0.0164 (17)0.0011 (13)0.0048 (14)0.0013 (12)
C150.0173 (17)0.0186 (15)0.0197 (18)0.0019 (13)0.0027 (14)0.0025 (12)
C160.0179 (17)0.0162 (14)0.0137 (16)0.0035 (13)0.0016 (13)0.0016 (11)
C170.0187 (17)0.0169 (14)0.0140 (16)0.0011 (13)0.0005 (14)0.0042 (12)
C180.0149 (17)0.0157 (14)0.0214 (18)0.0003 (13)0.0017 (14)0.0015 (12)
C190.0203 (18)0.0214 (16)0.0132 (16)0.0033 (14)0.0032 (14)0.0011 (12)
C200.0205 (18)0.0193 (15)0.0193 (18)0.0032 (14)0.0045 (14)0.0023 (12)
C210.0181 (17)0.0169 (14)0.0125 (16)0.0020 (13)0.0017 (13)0.0010 (11)
C220.0189 (18)0.0164 (15)0.0205 (18)0.0026 (13)0.0029 (14)0.0035 (13)
C230.0149 (17)0.0240 (16)0.0175 (17)0.0021 (14)0.0021 (14)0.0001 (13)
C240.0157 (17)0.0240 (16)0.0151 (17)0.0008 (14)0.0013 (14)0.0010 (12)
C250.0209 (18)0.0184 (15)0.0153 (17)0.0052 (14)0.0015 (14)0.0020 (12)
C260.0191 (18)0.0202 (15)0.0162 (17)0.0031 (13)0.0053 (14)0.0034 (12)
C270.0171 (17)0.0174 (15)0.0190 (17)0.0000 (13)0.0008 (14)0.0018 (12)
C280.0182 (17)0.0178 (14)0.0117 (16)0.0054 (13)0.0004 (13)0.0009 (12)
C290.0174 (17)0.0137 (14)0.0182 (17)0.0024 (13)0.0011 (14)0.0024 (12)
C300.0188 (17)0.0149 (14)0.0186 (17)0.0035 (13)0.0027 (14)0.0016 (12)
O170.0335 (16)0.0297 (13)0.0261 (15)0.0047 (12)0.0009 (13)0.0019 (11)
O180.0337 (15)0.0293 (13)0.0207 (14)0.0005 (12)0.0041 (12)0.0009 (10)
O190.0188 (13)0.0254 (12)0.0292 (14)0.0023 (11)0.0009 (11)0.0034 (10)
O200.0216 (14)0.0259 (13)0.0309 (15)0.0022 (11)0.0020 (11)0.0007 (10)
Geometric parameters (Å, º) top
O1—C11.373 (3)C8—H8A0.9800
O1—C91.450 (4)C9—C101.505 (4)
O2—C31.354 (3)C9—H90.9800
O2—H20.8200C10—C151.383 (5)
O3—C51.353 (4)C10—C111.396 (4)
O3—H30.8200C11—C121.378 (4)
O4—C71.236 (4)C11—H11A0.9300
O5—C81.424 (3)C12—C131.396 (5)
O5—H50.8200C13—C141.382 (4)
O6—C121.373 (3)C14—C151.385 (4)
O6—H60.8200C15—H15A0.9300
O7—C131.369 (3)C16—C171.374 (4)
O7—H70.8200C16—C211.399 (4)
O8—C141.371 (4)C17—C181.392 (4)
O8—H80.8200C17—H170.9300
O9—C161.374 (3)C18—C191.392 (5)
O9—C241.441 (3)C19—C201.373 (4)
O10—C181.359 (3)C19—H190.9300
O10—H100.8200C20—C211.423 (4)
O11—C201.358 (4)C21—C221.444 (4)
O11—H110.8200C22—C231.523 (4)
O12—C221.232 (4)C23—C241.519 (4)
O13—C231.425 (3)C23—H230.9800
O13—H130.8200C24—C251.502 (4)
O14—C291.379 (4)C24—H240.9800
O14—H140.8200C25—C301.384 (5)
O15—C281.364 (3)C25—C261.394 (4)
O15—H150.8200C26—C271.385 (4)
O16—C271.366 (3)C26—H260.9300
O16—H160.8200C27—C281.394 (4)
C1—C21.374 (4)C28—C291.395 (4)
C1—C61.400 (4)C29—C301.385 (4)
C2—C31.393 (4)C30—H300.9300
C2—H2A0.9300O17—H17A0.847 (10)
C3—C41.379 (5)O17—H17B0.88 (3)
C4—C51.378 (4)O18—H18A0.852 (10)
C4—H40.9300O18—H18B0.855 (10)
C5—C61.412 (4)O19—H19A0.853 (10)
C6—C71.442 (4)O19—H19B0.849 (10)
C7—C81.530 (4)O20—H20A0.859 (10)
C8—C91.528 (4)O20—H20B0.862 (10)
C1—O1—C9115.6 (2)O8—C14—C15118.9 (3)
C3—O2—H2109.5C13—C14—C15120.8 (3)
C5—O3—H3109.5C10—C15—C14119.7 (3)
C8—O5—H5109.5C10—C15—H15A120.2
C12—O6—H6109.5C14—C15—H15A120.2
C13—O7—H7109.5C17—C16—O9117.1 (3)
C14—O8—H8109.5C17—C16—C21122.2 (3)
C16—O9—C24115.2 (2)O9—C16—C21120.7 (3)
C18—O10—H10109.5C16—C17—C18118.4 (3)
C20—O11—H11109.5C16—C17—H17120.8
C23—O13—H13109.5C18—C17—H17120.8
C29—O14—H14109.5O10—C18—C19117.0 (3)
C28—O15—H15109.5O10—C18—C17121.1 (3)
C27—O16—H16109.5C19—C18—C17121.9 (3)
O1—C1—C2116.8 (3)C20—C19—C18118.6 (3)
O1—C1—C6121.0 (3)C20—C19—H19120.7
C2—C1—C6122.2 (3)C18—C19—H19120.7
C1—C2—C3118.3 (3)O11—C20—C19119.3 (3)
C1—C2—H2A120.8O11—C20—C21119.3 (3)
C3—C2—H2A120.8C19—C20—C21121.4 (3)
O2—C3—C4116.6 (3)C16—C21—C20117.3 (3)
O2—C3—C2121.7 (3)C16—C21—C22120.7 (3)
C4—C3—C2121.7 (3)C20—C21—C22121.9 (3)
C5—C4—C3119.0 (3)O12—C22—C21124.0 (3)
C5—C4—H4120.5O12—C22—C23120.2 (3)
C3—C4—H4120.5C21—C22—C23115.8 (3)
O3—C5—C4117.9 (3)O13—C23—C24108.4 (2)
O3—C5—C6120.7 (3)O13—C23—C22111.1 (3)
C4—C5—C6121.4 (3)C24—C23—C22109.9 (2)
C1—C6—C5117.3 (3)O13—C23—H23109.2
C1—C6—C7121.0 (3)C24—C23—H23109.2
C5—C6—C7121.7 (3)C22—C23—H23109.2
O4—C7—C6124.1 (3)O9—C24—C25108.3 (3)
O4—C7—C8120.9 (3)O9—C24—C23108.3 (2)
C6—C7—C8115.0 (3)C25—C24—C23112.3 (2)
O5—C8—C9109.4 (2)O9—C24—H24109.3
O5—C8—C7111.8 (3)C25—C24—H24109.3
C9—C8—C7109.2 (2)C23—C24—H24109.3
O5—C8—H8A108.8C30—C25—C26119.4 (3)
C9—C8—H8A108.8C30—C25—C24121.3 (3)
C7—C8—H8A108.8C26—C25—C24119.3 (3)
O1—C9—C10107.1 (3)C27—C26—C25120.6 (3)
O1—C9—C8107.7 (2)C27—C26—H26119.7
C10—C9—C8114.1 (2)C25—C26—H26119.7
O1—C9—H9109.3O16—C27—C26122.7 (3)
C10—C9—H9109.3O16—C27—C28116.9 (3)
C8—C9—H9109.3C26—C27—C28120.4 (3)
C15—C10—C11120.0 (3)O15—C28—C27123.7 (3)
C15—C10—C9120.9 (3)O15—C28—C29117.8 (3)
C11—C10—C9119.1 (3)C27—C28—C29118.4 (3)
C12—C11—C10120.0 (3)O14—C29—C30117.8 (3)
C12—C11—H11A120.0O14—C29—C28121.0 (3)
C10—C11—H11A120.0C30—C29—C28121.2 (3)
O6—C12—C11124.6 (3)C25—C30—C29119.9 (3)
O6—C12—C13115.2 (3)C25—C30—H30120.0
C11—C12—C13120.1 (3)C29—C30—H30120.0
O7—C13—C14118.2 (3)H17A—O17—H17B115 (3)
O7—C13—C12122.4 (3)H18A—O18—H18B115.6 (19)
C14—C13—C12119.3 (3)H19A—O19—H19B115.8 (18)
O8—C14—C13120.3 (3)H20A—O20—H20B113.4 (18)
C9—O1—C1—C2156.6 (3)C24—O9—C16—C17153.9 (3)
C9—O1—C1—C623.6 (4)C24—O9—C16—C2127.0 (4)
O1—C1—C2—C3175.9 (3)O9—C16—C17—C18178.7 (3)
C6—C1—C2—C34.3 (5)C21—C16—C17—C182.2 (4)
C1—C2—C3—O2176.0 (3)C16—C17—C18—O10178.1 (3)
C1—C2—C3—C43.8 (5)C16—C17—C18—C191.3 (4)
O2—C3—C4—C5178.2 (3)O10—C18—C19—C20179.6 (3)
C2—C3—C4—C51.5 (5)C17—C18—C19—C200.9 (5)
C3—C4—C5—O3178.4 (3)C18—C19—C20—O11178.4 (3)
C3—C4—C5—C60.4 (5)C18—C19—C20—C212.3 (5)
O1—C1—C6—C5177.7 (3)C17—C16—C21—C200.8 (4)
C2—C1—C6—C52.5 (5)O9—C16—C21—C20179.9 (3)
O1—C1—C6—C74.7 (4)C17—C16—C21—C22175.6 (3)
C2—C1—C6—C7175.1 (3)O9—C16—C21—C223.5 (4)
O3—C5—C6—C1178.8 (3)O11—C20—C21—C16179.2 (3)
C4—C5—C6—C10.1 (5)C19—C20—C21—C161.5 (4)
O3—C5—C6—C71.3 (5)O11—C20—C21—C222.8 (4)
C4—C5—C6—C7177.5 (3)C19—C20—C21—C22177.9 (3)
C1—C6—C7—O4178.6 (3)C16—C21—C22—O12177.7 (3)
C5—C6—C7—O43.9 (5)C20—C21—C22—O121.4 (5)
C1—C6—C7—C82.9 (4)C16—C21—C22—C230.1 (4)
C5—C6—C7—C8174.6 (3)C20—C21—C22—C23176.3 (3)
O4—C7—C8—O525.1 (4)O12—C22—C23—O1331.7 (4)
C6—C7—C8—O5156.3 (2)C21—C22—C23—O13150.5 (3)
O4—C7—C8—C9146.2 (3)O12—C22—C23—C24151.5 (3)
C6—C7—C8—C935.1 (4)C21—C22—C23—C2430.6 (4)
C1—O1—C9—C10179.2 (2)C16—O9—C24—C25179.9 (2)
C1—O1—C9—C856.0 (3)C16—O9—C24—C2357.8 (3)
O5—C8—C9—O1176.9 (2)O13—C23—C24—O9179.8 (2)
C7—C8—C9—O160.5 (3)C22—C23—C24—O958.3 (3)
O5—C8—C9—C1058.2 (4)O13—C23—C24—C2560.6 (3)
C7—C8—C9—C10179.2 (3)C22—C23—C24—C25177.9 (3)
O1—C9—C10—C1541.0 (4)O9—C24—C25—C3047.9 (4)
C8—C9—C10—C1578.1 (4)C23—C24—C25—C3071.7 (4)
O1—C9—C10—C11141.4 (3)O9—C24—C25—C26132.7 (3)
C8—C9—C10—C1199.4 (3)C23—C24—C25—C26107.7 (3)
C15—C10—C11—C123.2 (4)C30—C25—C26—C271.7 (4)
C9—C10—C11—C12174.4 (3)C24—C25—C26—C27177.7 (3)
C10—C11—C12—O6178.0 (3)C25—C26—C27—O16179.6 (3)
C10—C11—C12—C131.2 (4)C25—C26—C27—C280.4 (4)
O6—C12—C13—O71.0 (4)O16—C27—C28—O150.0 (4)
C11—C12—C13—O7178.3 (3)C26—C27—C28—O15180.0 (3)
O6—C12—C13—C14178.7 (3)O16—C27—C28—C29177.1 (3)
C11—C12—C13—C142.0 (4)C26—C27—C28—C292.9 (4)
O7—C13—C14—O82.6 (4)O15—C28—C29—O141.9 (4)
C12—C13—C14—O8177.2 (3)C27—C28—C29—O14175.4 (3)
O7—C13—C14—C15177.1 (3)O15—C28—C29—C30179.3 (3)
C12—C13—C14—C153.2 (4)C27—C28—C29—C303.4 (4)
C11—C10—C15—C142.0 (4)C26—C25—C30—C291.2 (4)
C9—C10—C15—C14175.5 (3)C24—C25—C30—C29178.2 (3)
O8—C14—C15—C10179.1 (3)O14—C29—C30—C25177.5 (3)
C13—C14—C15—C101.2 (4)C28—C29—C30—C251.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O190.821.892.706 (3)179
O3—H3···O40.821.912.639 (3)147
O5—H5···O17i0.821.882.700 (3)173
O6—H6···O130.821.972.783 (3)173
O7—H7···O60.822.302.717 (3)112
O7—H7···O10ii0.822.002.715 (3)145
O8—H8···O3iii0.821.952.749 (3)164
O8—H8···O70.822.282.722 (3)115
O10—H10···O20iv0.821.932.742 (4)169
O11—H11···O120.821.892.623 (3)148
O13—H13···O19v0.822.002.818 (3)173
O14—H14···O11vi0.821.962.744 (3)160
O14—H14···O150.822.302.743 (3)114
O15—H15···O180.821.942.746 (3)166
O15—H15···O160.822.352.770 (3)112
O16—H16···O50.821.942.739 (3)165
O17—H17A···O130.85 (3)2.35 (3)3.042 (3)140 (3)
O17—H17B···O20v0.88 (3)2.03 (3)2.896 (3)170 (4)
O18—H18A···O40.85 (1)2.62 (3)3.350 (3)145 (4)
O18—H18B···O2vii0.86 (1)1.89 (1)2.738 (3)171 (4)
O19—H19A···O14viii0.85 (1)1.93 (1)2.770 (3)169 (3)
O20—H20A···O80.86 (1)1.98 (2)2.836 (3)172 (3)
O20—H20B···O18ix0.87 (3)2.04 (4)2.870 (3)160 (4)
Symmetry codes: (i) x, y+1, z; (ii) x+2, y+1, z+1; (iii) x, y+3/2, z+1/2; (iv) x+1, y, z; (v) x+1, y1/2, z+1/2; (vi) x, y+1/2, z1/2; (vii) x+1, y+1, z; (viii) x1, y, z; (ix) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H12O8·2H2O
Mr356.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)15.391 (3), 7.9002 (16), 24.161 (5)
β (°) 92.57 (3)
V3)2934.8 (10)
Z8
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.06 × 0.02 × 0.02
Data collection
DiffractometerRigaku saturn
Absorption correctionMulti-scan
CrystalClear (Rigaku/MSC, 2005)
Tmin, Tmax0.992, 0.997
No. of measured, independent and
observed [I > 2σ(I)] reflections
17668, 5189, 3433
Rint0.077
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.155, 1.03
No. of reflections5189
No. of parameters495
No. of restraints11
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.29

Computer programs: CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O190.821.892.706 (3)179
O3—H3···O40.821.912.639 (3)147
O5—H5···O17i0.821.882.700 (3)173
O6—H6···O130.821.972.783 (3)173
O7—H7···O60.822.302.717 (3)112
O7—H7···O10ii0.822.002.715 (3)145
O8—H8···O3iii0.821.952.749 (3)164
O8—H8···O70.822.282.722 (3)115
O10—H10···O20iv0.821.932.742 (4)169
O11—H11···O120.821.892.623 (3)148
O13—H13···O19v0.822.002.818 (3)173
O14—H14···O11vi0.821.962.744 (3)160
O14—H14···O150.822.302.743 (3)114
O15—H15···O180.821.942.746 (3)166
O15—H15···O160.822.352.770 (3)112
O16—H16···O50.821.942.739 (3)165
O17—H17A···O130.85 (3)2.35 (3)3.042 (3)140 (3)
O17—H17B···O20v0.88 (3)2.03 (3)2.896 (3)170 (4)
O18—H18A···O40.852 (10)2.62 (3)3.350 (3)145 (4)
O18—H18B···O2vii0.855 (10)1.891 (11)2.738 (3)171 (4)
O19—H19A···O14viii0.853 (10)1.926 (11)2.770 (3)169 (3)
O20—H20A···O80.859 (14)1.984 (16)2.836 (3)172 (3)
O20—H20B···O18ix0.87 (3)2.04 (4)2.870 (3)160 (4)
Symmetry codes: (i) x, y+1, z; (ii) x+2, y+1, z+1; (iii) x, y+3/2, z+1/2; (iv) x+1, y, z; (v) x+1, y1/2, z+1/2; (vi) x, y+1/2, z1/2; (vii) x+1, y+1, z; (viii) x1, y, z; (ix) x+1, y+1/2, z+1/2.
 

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