Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050416/hb2581sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050416/hb2581Isup2.hkl |
CCDC reference: 667406
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (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
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.
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).
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).
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).
Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids for the non-hydrogen atoms. |
C15H12O8·2H2O | F(000) = 1488 |
Mr = 356.28 | Dx = 1.613 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4298 reflections |
a = 15.391 (3) Å | θ = 1.7–27.9° |
b = 7.9002 (16) Å | µ = 0.14 mm−1 |
c = 24.161 (5) Å | T = 113 K |
β = 92.57 (3)° | Needle, yellow |
V = 2934.8 (10) Å3 | 0.06 × 0.02 × 0.02 mm |
Z = 8 |
Rigaku saturn diffractometer | 5189 independent reflections |
Radiation source: rotating anode | 3433 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.077 |
ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan CrystalClear (Rigaku/MSC, 2005) | h = −18→18 |
Tmin = 0.992, Tmax = 0.997 | k = −8→9 |
17668 measured reflections | l = −28→28 |
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)] = 0.059 | Hydrogen site location: difmap and geom |
wR(F2) = 0.155 | H 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 parameters | Δρmax = 0.29 e Å−3 |
11 restraints | Δρmin = −0.29 e Å−3 |
C15H12O8·2H2O | V = 2934.8 (10) Å3 |
Mr = 356.28 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.391 (3) Å | µ = 0.14 mm−1 |
b = 7.9002 (16) Å | T = 113 K |
c = 24.161 (5) Å | 0.06 × 0.02 × 0.02 mm |
β = 92.57 (3)° |
Rigaku saturn diffractometer | 5189 independent reflections |
Absorption correction: multi-scan CrystalClear (Rigaku/MSC, 2005) | 3433 reflections with I > 2σ(I) |
Tmin = 0.992, Tmax = 0.997 | Rint = 0.077 |
17668 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 11 restraints |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.29 e Å−3 |
5189 reflections | Δρmin = −0.29 e Å−3 |
495 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 | 0.48728 (14) | 0.6070 (3) | 0.21760 (8) | 0.0199 (5) | |
O2 | 0.28387 (15) | 0.4841 (3) | 0.07021 (9) | 0.0251 (6) | |
H2 | 0.2566 | 0.4476 | 0.0960 | 0.038* | |
O3 | 0.52593 (15) | 0.8135 (3) | 0.03286 (9) | 0.0251 (6) | |
H3 | 0.5704 | 0.8524 | 0.0479 | 0.038* | |
O4 | 0.63802 (15) | 0.8827 (3) | 0.11563 (9) | 0.0243 (5) | |
O5 | 0.69897 (13) | 0.8183 (2) | 0.22252 (9) | 0.0185 (5) | |
H5 | 0.7107 | 0.9194 | 0.2213 | 0.028* | |
O6 | 0.75720 (15) | 0.4186 (3) | 0.39160 (9) | 0.0247 (6) | |
H6 | 0.7769 | 0.3522 | 0.3693 | 0.037* | |
O7 | 0.64803 (14) | 0.5739 (3) | 0.46089 (8) | 0.0232 (5) | |
H7 | 0.6861 | 0.5041 | 0.4685 | 0.035* | |
O8 | 0.50042 (14) | 0.7283 (3) | 0.42033 (9) | 0.0229 (5) | |
H8 | 0.5173 | 0.7084 | 0.4523 | 0.034* | |
O9 | 1.04347 (13) | 0.4302 (2) | 0.32245 (8) | 0.0184 (5) | |
O10 | 1.23667 (15) | 0.5948 (3) | 0.47101 (9) | 0.0237 (6) | |
H10 | 1.2592 | 0.6436 | 0.4454 | 0.036* | |
O11 | 1.00809 (15) | 0.2216 (3) | 0.50702 (9) | 0.0230 (5) | |
H11 | 0.9676 | 0.1725 | 0.4907 | 0.034* | |
O12 | 0.90634 (14) | 0.1260 (3) | 0.42278 (9) | 0.0235 (5) | |
O13 | 0.83770 (14) | 0.2020 (3) | 0.31889 (9) | 0.0205 (5) | |
H13 | 0.8260 | 0.1021 | 0.3238 | 0.031* | |
O14 | 1.02685 (14) | 0.2668 (3) | 0.12043 (8) | 0.0192 (5) | |
H14 | 1.0096 | 0.2804 | 0.0881 | 0.029* | |
O15 | 0.88587 (14) | 0.4432 (3) | 0.07755 (8) | 0.0204 (5) | |
H15 | 0.8415 | 0.4972 | 0.0698 | 0.031* | |
O16 | 0.78232 (15) | 0.6215 (3) | 0.14812 (9) | 0.0238 (6) | |
H16 | 0.7661 | 0.6889 | 0.1713 | 0.036* | |
C1 | 0.4610 (2) | 0.6266 (4) | 0.16291 (12) | 0.0181 (7) | |
C2 | 0.3831 (2) | 0.5538 (4) | 0.14623 (12) | 0.0182 (7) | |
H2A | 0.3486 | 0.5006 | 0.1716 | 0.022* | |
C3 | 0.3571 (2) | 0.5617 (4) | 0.09030 (13) | 0.0182 (7) | |
C4 | 0.4049 (2) | 0.6483 (4) | 0.05253 (13) | 0.0208 (7) | |
H4 | 0.3858 | 0.6544 | 0.0155 | 0.025* | |
C5 | 0.4813 (2) | 0.7257 (4) | 0.07043 (13) | 0.0198 (7) | |
C6 | 0.5117 (2) | 0.7172 (4) | 0.12640 (12) | 0.0158 (7) | |
C7 | 0.5897 (2) | 0.8035 (4) | 0.14589 (13) | 0.0172 (7) | |
C8 | 0.6089 (2) | 0.7946 (4) | 0.20853 (13) | 0.0177 (7) | |
H8A | 0.5757 | 0.8834 | 0.2264 | 0.021* | |
C9 | 0.5800 (2) | 0.6225 (4) | 0.22990 (12) | 0.0174 (7) | |
H9 | 0.6106 | 0.5328 | 0.2106 | 0.021* | |
C10 | 0.5945 (2) | 0.5996 (3) | 0.29144 (13) | 0.0170 (7) | |
C11 | 0.6674 (2) | 0.5096 (4) | 0.31149 (13) | 0.0188 (7) | |
H11A | 0.7033 | 0.4564 | 0.2869 | 0.023* | |
C12 | 0.68601 (19) | 0.4995 (4) | 0.36771 (13) | 0.0173 (7) | |
C13 | 0.6313 (2) | 0.5766 (4) | 0.40477 (12) | 0.0178 (7) | |
C14 | 0.5570 (2) | 0.6582 (4) | 0.38456 (12) | 0.0168 (7) | |
C15 | 0.5388 (2) | 0.6715 (4) | 0.32809 (13) | 0.0187 (7) | |
H15A | 0.4892 | 0.7285 | 0.3149 | 0.022* | |
C16 | 1.0682 (2) | 0.4205 (4) | 0.37772 (12) | 0.0159 (7) | |
C17 | 1.1410 (2) | 0.5098 (3) | 0.39515 (12) | 0.0166 (7) | |
H17 | 1.1724 | 0.5718 | 0.3701 | 0.020* | |
C18 | 1.1667 (2) | 0.5052 (4) | 0.45111 (13) | 0.0174 (7) | |
C19 | 1.1219 (2) | 0.4107 (4) | 0.48920 (13) | 0.0184 (7) | |
H19 | 1.1396 | 0.4105 | 0.5265 | 0.022* | |
C20 | 1.0511 (2) | 0.3177 (4) | 0.47055 (13) | 0.0196 (7) | |
C21 | 1.0212 (2) | 0.3215 (3) | 0.41395 (12) | 0.0158 (7) | |
C22 | 0.9487 (2) | 0.2199 (4) | 0.39350 (13) | 0.0185 (7) | |
C23 | 0.9280 (2) | 0.2292 (4) | 0.33132 (13) | 0.0189 (7) | |
H23 | 0.9617 | 0.1426 | 0.3127 | 0.023* | |
C24 | 0.9522 (2) | 0.4026 (4) | 0.30964 (12) | 0.0183 (7) | |
H24 | 0.9183 | 0.4893 | 0.3281 | 0.022* | |
C25 | 0.9363 (2) | 0.4173 (4) | 0.24804 (13) | 0.0183 (7) | |
C26 | 0.8671 (2) | 0.5154 (4) | 0.22711 (13) | 0.0183 (7) | |
H26 | 0.8327 | 0.5740 | 0.2513 | 0.022* | |
C27 | 0.8491 (2) | 0.5263 (4) | 0.17056 (13) | 0.0179 (7) | |
C28 | 0.8997 (2) | 0.4385 (4) | 0.13371 (12) | 0.0159 (7) | |
C29 | 0.9709 (2) | 0.3463 (3) | 0.15507 (13) | 0.0164 (7) | |
C30 | 0.9886 (2) | 0.3341 (3) | 0.21165 (13) | 0.0175 (7) | |
H30 | 1.0356 | 0.2700 | 0.2252 | 0.021* | |
O17 | 0.72397 (17) | 0.1553 (3) | 0.21376 (10) | 0.0299 (6) | |
O18 | 0.72867 (17) | 0.5768 (3) | 0.04143 (10) | 0.0281 (6) | |
O19 | 0.19398 (15) | 0.3605 (3) | 0.15503 (10) | 0.0245 (6) | |
O20 | 0.32106 (16) | 0.7871 (3) | 0.39567 (10) | 0.0261 (6) | |
H17A | 0.7710 (15) | 0.189 (4) | 0.2298 (14) | 0.040 (12)* | |
H17B | 0.710 (3) | 0.207 (5) | 0.1826 (15) | 0.061 (15)* | |
H18A | 0.726 (3) | 0.677 (2) | 0.0545 (15) | 0.067 (15)* | |
H18B | 0.723 (4) | 0.569 (5) | 0.0062 (5) | 0.13 (2)* | |
H19A | 0.1449 (11) | 0.319 (3) | 0.1445 (13) | 0.024 (10)* | |
H19B | 0.2265 (18) | 0.297 (3) | 0.1754 (15) | 0.053 (13)* | |
H20A | 0.3757 (8) | 0.766 (4) | 0.3997 (15) | 0.034 (11)* | |
H20B | 0.307 (2) | 0.887 (3) | 0.407 (2) | 0.10 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0192 (12) | 0.0287 (12) | 0.0117 (12) | −0.0050 (10) | −0.0003 (9) | 0.0043 (9) |
O2 | 0.0233 (14) | 0.0370 (13) | 0.0150 (12) | −0.0092 (11) | 0.0005 (10) | 0.0004 (10) |
O3 | 0.0229 (14) | 0.0361 (13) | 0.0164 (13) | −0.0100 (11) | 0.0011 (10) | 0.0057 (10) |
O4 | 0.0232 (13) | 0.0289 (12) | 0.0208 (13) | −0.0050 (11) | 0.0009 (10) | 0.0048 (10) |
O5 | 0.0162 (12) | 0.0192 (11) | 0.0201 (12) | −0.0022 (9) | −0.0007 (10) | −0.0004 (9) |
O6 | 0.0223 (13) | 0.0324 (13) | 0.0192 (13) | 0.0100 (11) | −0.0016 (11) | −0.0029 (9) |
O7 | 0.0234 (14) | 0.0322 (13) | 0.0136 (12) | 0.0078 (10) | −0.0022 (10) | −0.0003 (9) |
O8 | 0.0224 (13) | 0.0339 (12) | 0.0125 (12) | 0.0081 (10) | 0.0011 (10) | −0.0020 (10) |
O9 | 0.0185 (12) | 0.0233 (11) | 0.0133 (12) | −0.0033 (9) | −0.0008 (9) | 0.0028 (9) |
O10 | 0.0232 (13) | 0.0286 (13) | 0.0188 (13) | −0.0056 (10) | −0.0051 (11) | 0.0048 (9) |
O11 | 0.0270 (14) | 0.0273 (12) | 0.0146 (12) | −0.0068 (10) | 0.0014 (10) | 0.0032 (9) |
O12 | 0.0258 (14) | 0.0281 (12) | 0.0167 (12) | −0.0047 (10) | 0.0010 (10) | 0.0058 (9) |
O13 | 0.0180 (12) | 0.0213 (11) | 0.0221 (13) | −0.0034 (9) | −0.0019 (10) | 0.0027 (9) |
O14 | 0.0225 (13) | 0.0223 (11) | 0.0126 (12) | 0.0026 (10) | 0.0000 (10) | −0.0006 (9) |
O15 | 0.0226 (13) | 0.0265 (12) | 0.0118 (12) | 0.0038 (10) | −0.0020 (10) | 0.0010 (9) |
O16 | 0.0222 (13) | 0.0287 (13) | 0.0202 (13) | 0.0073 (10) | −0.0004 (11) | −0.0030 (9) |
C1 | 0.0196 (18) | 0.0197 (15) | 0.0149 (17) | 0.0021 (14) | 0.0009 (14) | 0.0010 (12) |
C2 | 0.0195 (18) | 0.0220 (15) | 0.0133 (16) | 0.0017 (14) | 0.0020 (13) | 0.0040 (12) |
C3 | 0.0155 (17) | 0.0210 (15) | 0.0181 (17) | 0.0010 (14) | −0.0009 (14) | −0.0007 (13) |
C4 | 0.0201 (18) | 0.0293 (17) | 0.0130 (17) | −0.0013 (14) | 0.0003 (14) | −0.0026 (13) |
C5 | 0.0207 (18) | 0.0239 (16) | 0.0148 (17) | 0.0021 (14) | 0.0010 (14) | 0.0024 (13) |
C6 | 0.0173 (17) | 0.0184 (15) | 0.0117 (16) | −0.0008 (13) | 0.0006 (13) | −0.0008 (12) |
C7 | 0.0210 (18) | 0.0173 (15) | 0.0133 (17) | 0.0047 (14) | 0.0020 (14) | 0.0013 (12) |
C8 | 0.0171 (17) | 0.0190 (15) | 0.0169 (17) | 0.0012 (13) | 0.0000 (14) | 0.0007 (12) |
C9 | 0.0174 (17) | 0.0228 (16) | 0.0120 (16) | 0.0034 (14) | 0.0002 (13) | 0.0010 (12) |
C10 | 0.0177 (18) | 0.0165 (15) | 0.0168 (17) | −0.0024 (13) | 0.0018 (14) | −0.0011 (12) |
C11 | 0.0167 (17) | 0.0211 (15) | 0.0187 (17) | −0.0006 (14) | 0.0031 (14) | 0.0001 (12) |
C12 | 0.0128 (17) | 0.0195 (15) | 0.0195 (17) | −0.0012 (13) | −0.0002 (13) | −0.0011 (12) |
C13 | 0.0213 (18) | 0.0189 (15) | 0.0130 (17) | −0.0010 (13) | −0.0017 (14) | 0.0015 (12) |
C14 | 0.0167 (18) | 0.0178 (15) | 0.0164 (17) | −0.0011 (13) | 0.0048 (14) | −0.0013 (12) |
C15 | 0.0173 (17) | 0.0186 (15) | 0.0197 (18) | 0.0019 (13) | −0.0027 (14) | 0.0025 (12) |
C16 | 0.0179 (17) | 0.0162 (14) | 0.0137 (16) | 0.0035 (13) | 0.0016 (13) | −0.0016 (11) |
C17 | 0.0187 (17) | 0.0169 (14) | 0.0140 (16) | 0.0011 (13) | 0.0005 (14) | 0.0042 (12) |
C18 | 0.0149 (17) | 0.0157 (14) | 0.0214 (18) | 0.0003 (13) | −0.0017 (14) | −0.0015 (12) |
C19 | 0.0203 (18) | 0.0214 (16) | 0.0132 (16) | 0.0033 (14) | −0.0032 (14) | 0.0011 (12) |
C20 | 0.0205 (18) | 0.0193 (15) | 0.0193 (18) | 0.0032 (14) | 0.0045 (14) | 0.0023 (12) |
C21 | 0.0181 (17) | 0.0169 (14) | 0.0125 (16) | 0.0020 (13) | 0.0017 (13) | −0.0010 (11) |
C22 | 0.0189 (18) | 0.0164 (15) | 0.0205 (18) | 0.0026 (13) | 0.0029 (14) | 0.0035 (13) |
C23 | 0.0149 (17) | 0.0240 (16) | 0.0175 (17) | −0.0021 (14) | −0.0021 (14) | −0.0001 (13) |
C24 | 0.0157 (17) | 0.0240 (16) | 0.0151 (17) | −0.0008 (14) | −0.0013 (14) | −0.0010 (12) |
C25 | 0.0209 (18) | 0.0184 (15) | 0.0153 (17) | −0.0052 (14) | −0.0015 (14) | 0.0020 (12) |
C26 | 0.0191 (18) | 0.0202 (15) | 0.0162 (17) | −0.0031 (13) | 0.0053 (14) | −0.0034 (12) |
C27 | 0.0171 (17) | 0.0174 (15) | 0.0190 (17) | 0.0000 (13) | −0.0008 (14) | −0.0018 (12) |
C28 | 0.0182 (17) | 0.0178 (14) | 0.0117 (16) | −0.0054 (13) | −0.0004 (13) | −0.0009 (12) |
C29 | 0.0174 (17) | 0.0137 (14) | 0.0182 (17) | −0.0024 (13) | 0.0011 (14) | −0.0024 (12) |
C30 | 0.0188 (17) | 0.0149 (14) | 0.0186 (17) | −0.0035 (13) | −0.0027 (14) | 0.0016 (12) |
O17 | 0.0335 (16) | 0.0297 (13) | 0.0261 (15) | −0.0047 (12) | −0.0009 (13) | −0.0019 (11) |
O18 | 0.0337 (15) | 0.0293 (13) | 0.0207 (14) | −0.0005 (12) | −0.0041 (12) | −0.0009 (10) |
O19 | 0.0188 (13) | 0.0254 (12) | 0.0292 (14) | −0.0023 (11) | −0.0009 (11) | 0.0034 (10) |
O20 | 0.0216 (14) | 0.0259 (13) | 0.0309 (15) | 0.0022 (11) | 0.0020 (11) | −0.0007 (10) |
O1—C1 | 1.373 (3) | C8—H8A | 0.9800 |
O1—C9 | 1.450 (4) | C9—C10 | 1.505 (4) |
O2—C3 | 1.354 (3) | C9—H9 | 0.9800 |
O2—H2 | 0.8200 | C10—C15 | 1.383 (5) |
O3—C5 | 1.353 (4) | C10—C11 | 1.396 (4) |
O3—H3 | 0.8200 | C11—C12 | 1.378 (4) |
O4—C7 | 1.236 (4) | C11—H11A | 0.9300 |
O5—C8 | 1.424 (3) | C12—C13 | 1.396 (5) |
O5—H5 | 0.8200 | C13—C14 | 1.382 (4) |
O6—C12 | 1.373 (3) | C14—C15 | 1.385 (4) |
O6—H6 | 0.8200 | C15—H15A | 0.9300 |
O7—C13 | 1.369 (3) | C16—C17 | 1.374 (4) |
O7—H7 | 0.8200 | C16—C21 | 1.399 (4) |
O8—C14 | 1.371 (4) | C17—C18 | 1.392 (4) |
O8—H8 | 0.8200 | C17—H17 | 0.9300 |
O9—C16 | 1.374 (3) | C18—C19 | 1.392 (5) |
O9—C24 | 1.441 (3) | C19—C20 | 1.373 (4) |
O10—C18 | 1.359 (3) | C19—H19 | 0.9300 |
O10—H10 | 0.8200 | C20—C21 | 1.423 (4) |
O11—C20 | 1.358 (4) | C21—C22 | 1.444 (4) |
O11—H11 | 0.8200 | C22—C23 | 1.523 (4) |
O12—C22 | 1.232 (4) | C23—C24 | 1.519 (4) |
O13—C23 | 1.425 (3) | C23—H23 | 0.9800 |
O13—H13 | 0.8200 | C24—C25 | 1.502 (4) |
O14—C29 | 1.379 (4) | C24—H24 | 0.9800 |
O14—H14 | 0.8200 | C25—C30 | 1.384 (5) |
O15—C28 | 1.364 (3) | C25—C26 | 1.394 (4) |
O15—H15 | 0.8200 | C26—C27 | 1.385 (4) |
O16—C27 | 1.366 (3) | C26—H26 | 0.9300 |
O16—H16 | 0.8200 | C27—C28 | 1.394 (4) |
C1—C2 | 1.374 (4) | C28—C29 | 1.395 (4) |
C1—C6 | 1.400 (4) | C29—C30 | 1.385 (4) |
C2—C3 | 1.393 (4) | C30—H30 | 0.9300 |
C2—H2A | 0.9300 | O17—H17A | 0.847 (10) |
C3—C4 | 1.379 (5) | O17—H17B | 0.88 (3) |
C4—C5 | 1.378 (4) | O18—H18A | 0.852 (10) |
C4—H4 | 0.9300 | O18—H18B | 0.855 (10) |
C5—C6 | 1.412 (4) | O19—H19A | 0.853 (10) |
C6—C7 | 1.442 (4) | O19—H19B | 0.849 (10) |
C7—C8 | 1.530 (4) | O20—H20A | 0.859 (10) |
C8—C9 | 1.528 (4) | O20—H20B | 0.862 (10) |
C1—O1—C9 | 115.6 (2) | O8—C14—C15 | 118.9 (3) |
C3—O2—H2 | 109.5 | C13—C14—C15 | 120.8 (3) |
C5—O3—H3 | 109.5 | C10—C15—C14 | 119.7 (3) |
C8—O5—H5 | 109.5 | C10—C15—H15A | 120.2 |
C12—O6—H6 | 109.5 | C14—C15—H15A | 120.2 |
C13—O7—H7 | 109.5 | C17—C16—O9 | 117.1 (3) |
C14—O8—H8 | 109.5 | C17—C16—C21 | 122.2 (3) |
C16—O9—C24 | 115.2 (2) | O9—C16—C21 | 120.7 (3) |
C18—O10—H10 | 109.5 | C16—C17—C18 | 118.4 (3) |
C20—O11—H11 | 109.5 | C16—C17—H17 | 120.8 |
C23—O13—H13 | 109.5 | C18—C17—H17 | 120.8 |
C29—O14—H14 | 109.5 | O10—C18—C19 | 117.0 (3) |
C28—O15—H15 | 109.5 | O10—C18—C17 | 121.1 (3) |
C27—O16—H16 | 109.5 | C19—C18—C17 | 121.9 (3) |
O1—C1—C2 | 116.8 (3) | C20—C19—C18 | 118.6 (3) |
O1—C1—C6 | 121.0 (3) | C20—C19—H19 | 120.7 |
C2—C1—C6 | 122.2 (3) | C18—C19—H19 | 120.7 |
C1—C2—C3 | 118.3 (3) | O11—C20—C19 | 119.3 (3) |
C1—C2—H2A | 120.8 | O11—C20—C21 | 119.3 (3) |
C3—C2—H2A | 120.8 | C19—C20—C21 | 121.4 (3) |
O2—C3—C4 | 116.6 (3) | C16—C21—C20 | 117.3 (3) |
O2—C3—C2 | 121.7 (3) | C16—C21—C22 | 120.7 (3) |
C4—C3—C2 | 121.7 (3) | C20—C21—C22 | 121.9 (3) |
C5—C4—C3 | 119.0 (3) | O12—C22—C21 | 124.0 (3) |
C5—C4—H4 | 120.5 | O12—C22—C23 | 120.2 (3) |
C3—C4—H4 | 120.5 | C21—C22—C23 | 115.8 (3) |
O3—C5—C4 | 117.9 (3) | O13—C23—C24 | 108.4 (2) |
O3—C5—C6 | 120.7 (3) | O13—C23—C22 | 111.1 (3) |
C4—C5—C6 | 121.4 (3) | C24—C23—C22 | 109.9 (2) |
C1—C6—C5 | 117.3 (3) | O13—C23—H23 | 109.2 |
C1—C6—C7 | 121.0 (3) | C24—C23—H23 | 109.2 |
C5—C6—C7 | 121.7 (3) | C22—C23—H23 | 109.2 |
O4—C7—C6 | 124.1 (3) | O9—C24—C25 | 108.3 (3) |
O4—C7—C8 | 120.9 (3) | O9—C24—C23 | 108.3 (2) |
C6—C7—C8 | 115.0 (3) | C25—C24—C23 | 112.3 (2) |
O5—C8—C9 | 109.4 (2) | O9—C24—H24 | 109.3 |
O5—C8—C7 | 111.8 (3) | C25—C24—H24 | 109.3 |
C9—C8—C7 | 109.2 (2) | C23—C24—H24 | 109.3 |
O5—C8—H8A | 108.8 | C30—C25—C26 | 119.4 (3) |
C9—C8—H8A | 108.8 | C30—C25—C24 | 121.3 (3) |
C7—C8—H8A | 108.8 | C26—C25—C24 | 119.3 (3) |
O1—C9—C10 | 107.1 (3) | C27—C26—C25 | 120.6 (3) |
O1—C9—C8 | 107.7 (2) | C27—C26—H26 | 119.7 |
C10—C9—C8 | 114.1 (2) | C25—C26—H26 | 119.7 |
O1—C9—H9 | 109.3 | O16—C27—C26 | 122.7 (3) |
C10—C9—H9 | 109.3 | O16—C27—C28 | 116.9 (3) |
C8—C9—H9 | 109.3 | C26—C27—C28 | 120.4 (3) |
C15—C10—C11 | 120.0 (3) | O15—C28—C27 | 123.7 (3) |
C15—C10—C9 | 120.9 (3) | O15—C28—C29 | 117.8 (3) |
C11—C10—C9 | 119.1 (3) | C27—C28—C29 | 118.4 (3) |
C12—C11—C10 | 120.0 (3) | O14—C29—C30 | 117.8 (3) |
C12—C11—H11A | 120.0 | O14—C29—C28 | 121.0 (3) |
C10—C11—H11A | 120.0 | C30—C29—C28 | 121.2 (3) |
O6—C12—C11 | 124.6 (3) | C25—C30—C29 | 119.9 (3) |
O6—C12—C13 | 115.2 (3) | C25—C30—H30 | 120.0 |
C11—C12—C13 | 120.1 (3) | C29—C30—H30 | 120.0 |
O7—C13—C14 | 118.2 (3) | H17A—O17—H17B | 115 (3) |
O7—C13—C12 | 122.4 (3) | H18A—O18—H18B | 115.6 (19) |
C14—C13—C12 | 119.3 (3) | H19A—O19—H19B | 115.8 (18) |
O8—C14—C13 | 120.3 (3) | H20A—O20—H20B | 113.4 (18) |
C9—O1—C1—C2 | 156.6 (3) | C24—O9—C16—C17 | −153.9 (3) |
C9—O1—C1—C6 | −23.6 (4) | C24—O9—C16—C21 | 27.0 (4) |
O1—C1—C2—C3 | −175.9 (3) | O9—C16—C17—C18 | 178.7 (3) |
C6—C1—C2—C3 | 4.3 (5) | C21—C16—C17—C18 | −2.2 (4) |
C1—C2—C3—O2 | 176.0 (3) | C16—C17—C18—O10 | −178.1 (3) |
C1—C2—C3—C4 | −3.8 (5) | C16—C17—C18—C19 | 1.3 (4) |
O2—C3—C4—C5 | −178.2 (3) | O10—C18—C19—C20 | −179.6 (3) |
C2—C3—C4—C5 | 1.5 (5) | C17—C18—C19—C20 | 0.9 (5) |
C3—C4—C5—O3 | −178.4 (3) | C18—C19—C20—O11 | 178.4 (3) |
C3—C4—C5—C6 | 0.4 (5) | C18—C19—C20—C21 | −2.3 (5) |
O1—C1—C6—C5 | 177.7 (3) | C17—C16—C21—C20 | 0.8 (4) |
C2—C1—C6—C5 | −2.5 (5) | O9—C16—C21—C20 | 179.9 (3) |
O1—C1—C6—C7 | −4.7 (4) | C17—C16—C21—C22 | −175.6 (3) |
C2—C1—C6—C7 | 175.1 (3) | O9—C16—C21—C22 | 3.5 (4) |
O3—C5—C6—C1 | 178.8 (3) | O11—C20—C21—C16 | −179.2 (3) |
C4—C5—C6—C1 | 0.1 (5) | C19—C20—C21—C16 | 1.5 (4) |
O3—C5—C6—C7 | 1.3 (5) | O11—C20—C21—C22 | −2.8 (4) |
C4—C5—C6—C7 | −177.5 (3) | C19—C20—C21—C22 | 177.9 (3) |
C1—C6—C7—O4 | 178.6 (3) | C16—C21—C22—O12 | 177.7 (3) |
C5—C6—C7—O4 | −3.9 (5) | C20—C21—C22—O12 | 1.4 (5) |
C1—C6—C7—C8 | −2.9 (4) | C16—C21—C22—C23 | −0.1 (4) |
C5—C6—C7—C8 | 174.6 (3) | C20—C21—C22—C23 | −176.3 (3) |
O4—C7—C8—O5 | −25.1 (4) | O12—C22—C23—O13 | 31.7 (4) |
C6—C7—C8—O5 | 156.3 (2) | C21—C22—C23—O13 | −150.5 (3) |
O4—C7—C8—C9 | −146.2 (3) | O12—C22—C23—C24 | 151.5 (3) |
C6—C7—C8—C9 | 35.1 (4) | C21—C22—C23—C24 | −30.6 (4) |
C1—O1—C9—C10 | 179.2 (2) | C16—O9—C24—C25 | −179.9 (2) |
C1—O1—C9—C8 | 56.0 (3) | C16—O9—C24—C23 | −57.8 (3) |
O5—C8—C9—O1 | 176.9 (2) | O13—C23—C24—O9 | 179.8 (2) |
C7—C8—C9—O1 | −60.5 (3) | C22—C23—C24—O9 | 58.3 (3) |
O5—C8—C9—C10 | 58.2 (4) | O13—C23—C24—C25 | −60.6 (3) |
C7—C8—C9—C10 | −179.2 (3) | C22—C23—C24—C25 | 177.9 (3) |
O1—C9—C10—C15 | −41.0 (4) | O9—C24—C25—C30 | 47.9 (4) |
C8—C9—C10—C15 | 78.1 (4) | C23—C24—C25—C30 | −71.7 (4) |
O1—C9—C10—C11 | 141.4 (3) | O9—C24—C25—C26 | −132.7 (3) |
C8—C9—C10—C11 | −99.4 (3) | C23—C24—C25—C26 | 107.7 (3) |
C15—C10—C11—C12 | −3.2 (4) | C30—C25—C26—C27 | 1.7 (4) |
C9—C10—C11—C12 | 174.4 (3) | C24—C25—C26—C27 | −177.7 (3) |
C10—C11—C12—O6 | −178.0 (3) | C25—C26—C27—O16 | −179.6 (3) |
C10—C11—C12—C13 | 1.2 (4) | C25—C26—C27—C28 | 0.4 (4) |
O6—C12—C13—O7 | 1.0 (4) | O16—C27—C28—O15 | 0.0 (4) |
C11—C12—C13—O7 | −178.3 (3) | C26—C27—C28—O15 | −180.0 (3) |
O6—C12—C13—C14 | −178.7 (3) | O16—C27—C28—C29 | 177.1 (3) |
C11—C12—C13—C14 | 2.0 (4) | C26—C27—C28—C29 | −2.9 (4) |
O7—C13—C14—O8 | −2.6 (4) | O15—C28—C29—O14 | 1.9 (4) |
C12—C13—C14—O8 | 177.2 (3) | C27—C28—C29—O14 | −175.4 (3) |
O7—C13—C14—C15 | 177.1 (3) | O15—C28—C29—C30 | −179.3 (3) |
C12—C13—C14—C15 | −3.2 (4) | C27—C28—C29—C30 | 3.4 (4) |
C11—C10—C15—C14 | 2.0 (4) | C26—C25—C30—C29 | −1.2 (4) |
C9—C10—C15—C14 | −175.5 (3) | C24—C25—C30—C29 | 178.2 (3) |
O8—C14—C15—C10 | −179.1 (3) | O14—C29—C30—C25 | 177.5 (3) |
C13—C14—C15—C10 | 1.2 (4) | C28—C29—C30—C25 | −1.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O19 | 0.82 | 1.89 | 2.706 (3) | 179 |
O3—H3···O4 | 0.82 | 1.91 | 2.639 (3) | 147 |
O5—H5···O17i | 0.82 | 1.88 | 2.700 (3) | 173 |
O6—H6···O13 | 0.82 | 1.97 | 2.783 (3) | 173 |
O7—H7···O6 | 0.82 | 2.30 | 2.717 (3) | 112 |
O7—H7···O10ii | 0.82 | 2.00 | 2.715 (3) | 145 |
O8—H8···O3iii | 0.82 | 1.95 | 2.749 (3) | 164 |
O8—H8···O7 | 0.82 | 2.28 | 2.722 (3) | 115 |
O10—H10···O20iv | 0.82 | 1.93 | 2.742 (4) | 169 |
O11—H11···O12 | 0.82 | 1.89 | 2.623 (3) | 148 |
O13—H13···O19v | 0.82 | 2.00 | 2.818 (3) | 173 |
O14—H14···O11vi | 0.82 | 1.96 | 2.744 (3) | 160 |
O14—H14···O15 | 0.82 | 2.30 | 2.743 (3) | 114 |
O15—H15···O18 | 0.82 | 1.94 | 2.746 (3) | 166 |
O15—H15···O16 | 0.82 | 2.35 | 2.770 (3) | 112 |
O16—H16···O5 | 0.82 | 1.94 | 2.739 (3) | 165 |
O17—H17A···O13 | 0.85 (3) | 2.35 (3) | 3.042 (3) | 140 (3) |
O17—H17B···O20v | 0.88 (3) | 2.03 (3) | 2.896 (3) | 170 (4) |
O18—H18A···O4 | 0.85 (1) | 2.62 (3) | 3.350 (3) | 145 (4) |
O18—H18B···O2vii | 0.86 (1) | 1.89 (1) | 2.738 (3) | 171 (4) |
O19—H19A···O14viii | 0.85 (1) | 1.93 (1) | 2.770 (3) | 169 (3) |
O20—H20A···O8 | 0.86 (1) | 1.98 (2) | 2.836 (3) | 172 (3) |
O20—H20B···O18ix | 0.87 (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, y−1/2, −z+1/2; (vi) x, −y+1/2, z−1/2; (vii) −x+1, −y+1, −z; (viii) x−1, y, z; (ix) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H12O8·2H2O |
Mr | 356.28 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 15.391 (3), 7.9002 (16), 24.161 (5) |
β (°) | 92.57 (3) |
V (Å3) | 2934.8 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.06 × 0.02 × 0.02 |
Data collection | |
Diffractometer | Rigaku saturn |
Absorption correction | Multi-scan CrystalClear (Rigaku/MSC, 2005) |
Tmin, Tmax | 0.992, 0.997 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17668, 5189, 3433 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.155, 1.03 |
No. of reflections | 5189 |
No. of parameters | 495 |
No. of restraints | 11 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.29 |
Computer programs: CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O19 | 0.82 | 1.89 | 2.706 (3) | 179 |
O3—H3···O4 | 0.82 | 1.91 | 2.639 (3) | 147 |
O5—H5···O17i | 0.82 | 1.88 | 2.700 (3) | 173 |
O6—H6···O13 | 0.82 | 1.97 | 2.783 (3) | 173 |
O7—H7···O6 | 0.82 | 2.30 | 2.717 (3) | 112 |
O7—H7···O10ii | 0.82 | 2.00 | 2.715 (3) | 145 |
O8—H8···O3iii | 0.82 | 1.95 | 2.749 (3) | 164 |
O8—H8···O7 | 0.82 | 2.28 | 2.722 (3) | 115 |
O10—H10···O20iv | 0.82 | 1.93 | 2.742 (4) | 169 |
O11—H11···O12 | 0.82 | 1.89 | 2.623 (3) | 148 |
O13—H13···O19v | 0.82 | 2.00 | 2.818 (3) | 173 |
O14—H14···O11vi | 0.82 | 1.96 | 2.744 (3) | 160 |
O14—H14···O15 | 0.82 | 2.30 | 2.743 (3) | 114 |
O15—H15···O18 | 0.82 | 1.94 | 2.746 (3) | 166 |
O15—H15···O16 | 0.82 | 2.35 | 2.770 (3) | 112 |
O16—H16···O5 | 0.82 | 1.94 | 2.739 (3) | 165 |
O17—H17A···O13 | 0.85 (3) | 2.35 (3) | 3.042 (3) | 140 (3) |
O17—H17B···O20v | 0.88 (3) | 2.03 (3) | 2.896 (3) | 170 (4) |
O18—H18A···O4 | 0.852 (10) | 2.62 (3) | 3.350 (3) | 145 (4) |
O18—H18B···O2vii | 0.855 (10) | 1.891 (11) | 2.738 (3) | 171 (4) |
O19—H19A···O14viii | 0.853 (10) | 1.926 (11) | 2.770 (3) | 169 (3) |
O20—H20A···O8 | 0.859 (14) | 1.984 (16) | 2.836 (3) | 172 (3) |
O20—H20B···O18ix | 0.87 (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, y−1/2, −z+1/2; (vi) x, −y+1/2, z−1/2; (vii) −x+1, −y+1, −z; (viii) x−1, y, z; (ix) −x+1, y+1/2, −z+1/2. |
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).