supplementary materials
5-{(2S,3R,4S,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydropyran-2-yloxy]tetrahydropyran-2-yloxy}-7-hydroxy-2-(4-hydroxyphenyl)chromen-4-one monohydrate
In the title compound, C27H30O14·H2O, the hydroxyphenyl ring makes a dihedral angle of 20.05 (11)° with the chromenone ring system. The crystal structure is stabilized by intra- and intermolecular O-H
O hydrogen bonds. The absolute configuration was assigned on the basis of an analagous structure.
- Related literature
- Experimental
- Refinement
- Computing details
- Figures
- 5-{(2S,3R,4S,5S,6R)-3,4-Dihydroxy-6-
hydroxymethyl-3-[(2S,3R,4R,5R,6S)-3,4,5-
trihydroxy-6-methyltetrahydropyran-2-yloxy]tetrahydropyran-2-yloxy}-7-hydroxy-
2-(4-hydroxyphenyl)chromen-4-one monohydrate
- References
Compound (II) was mixed with methanol and K2CO3. After stirring for 60 min at 40°C, hydrochloric acid was added to make pH 7.0. The mixture was kept
for 24 h at 4°C. The resultant white precipitate was separated by filtration,
washed with water and dried for X-ray analysis.
In the absence of anomalous scatterers Friedel pairs were merged. The absolute
configuration was set according to the literature (Li et al.,
2007). The
O-bound H atoms were located in a difference map and refined with the
restraint O—H = 0.85 (3) Å. All other H atoms were positioned geometrically
and refined as riding atoms, with Uiso(H) = 1.2 Ueq(CH and CH2) and
C—H ranging from 0.95–1.0Å or Uiso(H) = 1.5 Ueq(CH3) and
Cmethyl—H = 0.99 Å.
Data collection: Crystalclear (Rigaku/MSC, 2005); cell refinement: Crystalclear (Rigaku/MSC, 2005); data reduction: Crystalclear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
5-{(2
S,3
R,4
S,5
S,6
R)-3,4-Dihydroxy-6-
hydroxymethyl-3-[(2
S,3
R,4
R,5
R,6
S)-3,4,5-
trihydroxy-6-methyltetrahydropyran-2-yloxy]tetrahydropyran-2-yloxy}-7-hydroxy-
2-(4-hydroxyphenyl)chromen-4-one monohydrate
top
Crystal data top
| C27H30O14·H2O | F(000) = 1256 |
| Mr = 596.53 | Dx = 1.513 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 5367 reflections |
| a = 7.2392 (14) Å | θ = 2.1–27.1° |
| b = 9.832 (2) Å | µ = 0.13 mm−1 |
| c = 36.782 (7) Å | T = 113 K |
| V = 2618.1 (9) Å3 | Block, white |
| Z = 4 | 0.08 × 0.06 × 0.04 mm |
Data collection top
Rigaku Saturn CCD area-detector
diffractometer | 3332 independent reflections |
| Radiation source: rotating anode | 2875 reflections with I > 2σ(I) |
| confocal | Rint = 0.090 |
| ω scans | θmax = 27.1°, θmin = 2.1° |
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005) | h = −9→9 |
| Tmin = 0.990, Tmax = 0.995 | k = −12→12 |
| 20457 measured reflections | l = −30→47 |
Refinement top
| 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0614P)2 + 0.0488P]
where P = (Fo2 + 2Fc2)/3 |
| 3332 reflections | (Δ/σ)max = 0.001 |
| 410 parameters | Δρmax = 0.31 e Å−3 |
| 10 restraints | Δρmin = −0.29 e Å−3 |
Crystal data top
| C27H30O14·H2O | V = 2618.1 (9) Å3 |
| Mr = 596.53 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 7.2392 (14) Å | µ = 0.13 mm−1 |
| b = 9.832 (2) Å | T = 113 K |
| c = 36.782 (7) Å | 0.08 × 0.06 × 0.04 mm |
Data collection top
Rigaku Saturn CCD area-detector
diffractometer | 3332 independent reflections |
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005) | 2875 reflections with I > 2σ(I) |
| Tmin = 0.990, Tmax = 0.995 | Rint = 0.090 |
| 20457 measured reflections | θmax = 27.1° |
Refinement top
| R[F2 > 2σ(F2)] = 0.045 | 10 restraints |
| wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | Δρmax = 0.31 e Å−3 |
| 3332 reflections | Δρmin = −0.29 e Å−3 |
| 410 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| | x | y | z | Uiso*/Ueq | |
| O1 | 0.4843 (3) | 0.7580 (2) | 0.00818 (5) | 0.0211 (5) | |
| O2 | 0.5796 (3) | 0.9238 (2) | 0.10827 (5) | 0.0185 (5) | |
| O3 | 0.4249 (3) | 0.3145 (2) | 0.05153 (5) | 0.0241 (5) | |
| H3 | 0.407 (5) | 0.268 (4) | 0.0720 (8) | 0.036* | |
| O4 | 0.5902 (2) | 0.6692 (2) | 0.13500 (5) | 0.0165 (4) | |
| O5 | 0.4557 (2) | 0.5220 (2) | 0.17460 (5) | 0.0170 (4) | |
| O6 | 0.8762 (3) | 0.5651 (2) | 0.24894 (5) | 0.0205 (4) | |
| H6 | 0.909 (5) | 0.502 (3) | 0.2620 (8) | 0.031* | |
| O7 | 0.6098 (3) | 0.3398 (2) | 0.25491 (5) | 0.0231 (5) | |
| H7 | 0.622 (5) | 0.364 (4) | 0.2769 (7) | 0.035* | |
| O8 | 0.2114 (3) | 0.2890 (2) | 0.17453 (5) | 0.0252 (5) | |
| H8 | 0.140 (5) | 0.342 (4) | 0.1646 (9) | 0.038* | |
| O9 | 0.9173 (2) | 0.6586 (2) | 0.17330 (5) | 0.0167 (4) | |
| O10 | 0.9519 (2) | 0.8722 (2) | 0.20277 (5) | 0.0163 (4) | |
| O11 | 1.3189 (2) | 0.8698 (2) | 0.17022 (5) | 0.0189 (5) | |
| H11 | 1.403 (4) | 0.862 (4) | 0.1536 (7) | 0.028* | |
| O12 | 1.1740 (3) | 0.8979 (2) | 0.09786 (5) | 0.0224 (5) | |
| H12 | 1.155 (5) | 0.981 (3) | 0.0934 (9) | 0.034* | |
| O13 | 0.8811 (3) | 1.0723 (2) | 0.11859 (5) | 0.0219 (5) | |
| H13 | 0.779 (4) | 1.029 (4) | 0.1135 (9) | 0.033* | |
| O14 | 0.4369 (3) | 1.1650 (2) | −0.12150 (5) | 0.0212 (5) | |
| H14 | 0.406 (5) | 1.250 (3) | −0.1214 (9) | 0.032* | |
| O15 | 0.3844 (4) | 0.1713 (3) | 0.11315 (6) | 0.0375 (6) | |
| H15A | 0.358 (6) | 0.199 (5) | 0.1329 (8) | 0.056* | |
| H15B | 0.438 (6) | 0.096 (3) | 0.1150 (12) | 0.056* | |
| C2 | 0.5093 (4) | 0.8935 (3) | 0.01211 (7) | 0.0173 (6) | |
| C3 | 0.5473 (4) | 0.9489 (3) | 0.04519 (7) | 0.0190 (6) | |
| H3A | 0.5692 | 1.0439 | 0.0469 | 0.023* | |
| C4 | 0.5552 (3) | 0.8674 (3) | 0.07760 (7) | 0.0159 (6) | |
| C5 | 0.5377 (3) | 0.6235 (3) | 0.10095 (7) | 0.0149 (6) | |
| C6 | 0.4977 (4) | 0.4896 (3) | 0.09418 (7) | 0.0168 (6) | |
| H6A | 0.4939 | 0.4261 | 0.1136 | 0.020* | |
| C7 | 0.4621 (4) | 0.4463 (3) | 0.05842 (7) | 0.0186 (6) | |
| C8 | 0.4641 (4) | 0.5371 (3) | 0.02980 (7) | 0.0199 (6) | |
| H8A | 0.4449 | 0.5074 | 0.0055 | 0.024* | |
| C9 | 0.4948 (4) | 0.6725 (3) | 0.03761 (7) | 0.0178 (6) | |
| C13 | 0.5313 (4) | 0.7231 (3) | 0.07286 (7) | 0.0146 (6) | |
| C1'' | 0.6285 (4) | 0.5673 (3) | 0.16087 (7) | 0.0150 (5) | |
| H1'' | 0.6935 | 0.4899 | 0.1488 | 0.018* | |
| C2'' | 0.7487 (3) | 0.6234 (3) | 0.19134 (7) | 0.0154 (6) | |
| H2'' | 0.6905 | 0.7053 | 0.2027 | 0.019* | |
| C3'' | 0.7742 (4) | 0.5101 (3) | 0.21932 (7) | 0.0167 (6) | |
| H3'' | 0.8472 | 0.4347 | 0.2080 | 0.020* | |
| C4'' | 0.5868 (4) | 0.4542 (3) | 0.23160 (7) | 0.0167 (6) | |
| H4'' | 0.5165 | 0.5270 | 0.2446 | 0.020* | |
| C5'' | 0.4779 (4) | 0.4074 (3) | 0.19843 (7) | 0.0158 (6) | |
| H5'' | 0.5506 | 0.3357 | 0.1855 | 0.019* | |
| C6'' | 0.2879 (4) | 0.3529 (3) | 0.20634 (7) | 0.0203 (6) | |
| H6''1 | 0.2948 | 0.2860 | 0.2264 | 0.024* | |
| H6''2 | 0.2064 | 0.4283 | 0.2142 | 0.024* | |
| C1''' | 1.0404 (3) | 0.7556 (3) | 0.18874 (7) | 0.0146 (5) | |
| H1''' | 1.1133 | 0.7111 | 0.2085 | 0.018* | |
| C2''' | 1.1695 (3) | 0.7886 (3) | 0.15686 (7) | 0.0159 (6) | |
| H2''' | 1.2187 | 0.7025 | 0.1461 | 0.019* | |
| C3''' | 1.0581 (4) | 0.8670 (3) | 0.12806 (7) | 0.0170 (6) | |
| H3''' | 0.9544 | 0.8080 | 0.1195 | 0.020* | |
| C4''' | 0.9774 (4) | 0.9936 (3) | 0.14530 (7) | 0.0162 (6) | |
| H4''' | 1.0803 | 1.0497 | 0.1555 | 0.019* | |
| C5''' | 0.8485 (3) | 0.9518 (3) | 0.17625 (7) | 0.0163 (6) | |
| H5''' | 0.7459 | 0.8949 | 0.1662 | 0.020* | |
| C6''' | 0.7673 (4) | 1.0724 (4) | 0.19609 (8) | 0.0253 (7) | |
| H6''3 | 0.7005 | 1.0407 | 0.2177 | 0.038* | |
| H6''4 | 0.6819 | 1.1207 | 0.1800 | 0.038* | |
| H6''5 | 0.8668 | 1.1339 | 0.2035 | 0.038* | |
| C1' | 0.4910 (4) | 0.9672 (3) | −0.02252 (7) | 0.0182 (6) | |
| C2' | 0.5075 (4) | 0.8970 (3) | −0.05549 (7) | 0.0192 (6) | |
| H2' | 0.5297 | 0.8018 | −0.0555 | 0.023* | |
| C3' | 0.4916 (4) | 0.9662 (3) | −0.08794 (7) | 0.0190 (6) | |
| H3' | 0.5052 | 0.9185 | −0.1102 | 0.023* | |
| C4' | 0.4559 (4) | 1.1048 (3) | −0.08840 (7) | 0.0179 (6) | |
| C5' | 0.4378 (4) | 1.1761 (3) | −0.05556 (7) | 0.0202 (6) | |
| H5' | 0.4134 | 1.2710 | −0.0556 | 0.024* | |
| C6' | 0.4557 (4) | 1.1065 (3) | −0.02315 (7) | 0.0223 (6) | |
| H6' | 0.4439 | 1.1545 | −0.0009 | 0.027* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O1 | 0.0317 (11) | 0.0152 (12) | 0.0164 (9) | −0.0001 (9) | −0.0024 (8) | 0.0025 (9) |
| O2 | 0.0233 (10) | 0.0176 (13) | 0.0144 (9) | −0.0028 (8) | −0.0018 (7) | −0.0026 (8) |
| O3 | 0.0339 (12) | 0.0184 (14) | 0.0201 (10) | −0.0024 (9) | −0.0012 (8) | −0.0014 (9) |
| O4 | 0.0217 (9) | 0.0151 (12) | 0.0126 (8) | −0.0015 (8) | −0.0021 (7) | 0.0012 (8) |
| O5 | 0.0143 (8) | 0.0181 (12) | 0.0187 (9) | −0.0011 (8) | −0.0007 (7) | 0.0047 (9) |
| O6 | 0.0237 (10) | 0.0176 (12) | 0.0203 (10) | −0.0044 (9) | −0.0101 (8) | 0.0030 (9) |
| O7 | 0.0326 (11) | 0.0202 (12) | 0.0164 (9) | −0.0053 (10) | −0.0043 (8) | 0.0068 (9) |
| O8 | 0.0251 (11) | 0.0260 (14) | 0.0246 (10) | −0.0073 (9) | −0.0074 (8) | 0.0007 (10) |
| O9 | 0.0157 (9) | 0.0172 (12) | 0.0173 (9) | −0.0046 (8) | 0.0012 (7) | −0.0033 (8) |
| O10 | 0.0179 (9) | 0.0153 (12) | 0.0157 (8) | 0.0015 (8) | −0.0008 (7) | −0.0011 (8) |
| O11 | 0.0153 (9) | 0.0239 (13) | 0.0175 (9) | −0.0033 (8) | 0.0003 (7) | −0.0034 (9) |
| O12 | 0.0237 (10) | 0.0250 (14) | 0.0184 (10) | −0.0009 (9) | 0.0081 (7) | 0.0021 (10) |
| O13 | 0.0227 (10) | 0.0177 (13) | 0.0253 (10) | −0.0020 (9) | −0.0050 (8) | 0.0049 (9) |
| O14 | 0.0330 (11) | 0.0170 (13) | 0.0137 (9) | 0.0016 (10) | −0.0006 (7) | 0.0029 (9) |
| O15 | 0.0558 (16) | 0.0267 (17) | 0.0299 (12) | 0.0115 (13) | 0.0134 (11) | 0.0070 (12) |
| C2 | 0.0202 (13) | 0.0136 (16) | 0.0182 (12) | −0.0012 (11) | 0.0004 (9) | 0.0007 (12) |
| C3 | 0.0242 (13) | 0.0166 (17) | 0.0162 (12) | −0.0025 (12) | −0.0006 (10) | 0.0015 (11) |
| C4 | 0.0138 (11) | 0.0179 (17) | 0.0160 (12) | −0.0024 (11) | −0.0004 (9) | −0.0009 (11) |
| C5 | 0.0151 (11) | 0.0162 (16) | 0.0134 (11) | −0.0001 (11) | −0.0011 (9) | −0.0008 (11) |
| C6 | 0.0195 (13) | 0.0152 (17) | 0.0158 (13) | 0.0021 (11) | −0.0011 (9) | 0.0017 (12) |
| C7 | 0.0182 (12) | 0.0164 (17) | 0.0213 (13) | −0.0012 (11) | 0.0003 (10) | −0.0029 (12) |
| C8 | 0.0267 (14) | 0.0188 (18) | 0.0144 (12) | 0.0005 (12) | −0.0027 (10) | −0.0027 (11) |
| C9 | 0.0185 (13) | 0.0200 (18) | 0.0149 (12) | −0.0014 (11) | −0.0014 (9) | 0.0024 (12) |
| C13 | 0.0171 (12) | 0.0136 (16) | 0.0132 (12) | −0.0003 (11) | −0.0008 (9) | 0.0007 (11) |
| C1'' | 0.0172 (12) | 0.0134 (15) | 0.0143 (11) | −0.0002 (11) | −0.0005 (9) | 0.0013 (11) |
| C2'' | 0.0155 (12) | 0.0155 (17) | 0.0153 (12) | −0.0021 (11) | 0.0009 (9) | −0.0001 (11) |
| C3'' | 0.0189 (13) | 0.0154 (17) | 0.0160 (12) | −0.0011 (11) | −0.0039 (9) | −0.0017 (11) |
| C4'' | 0.0195 (12) | 0.0155 (16) | 0.0152 (12) | −0.0018 (11) | −0.0010 (9) | 0.0017 (11) |
| C5'' | 0.0210 (13) | 0.0121 (16) | 0.0143 (12) | −0.0006 (11) | −0.0006 (9) | 0.0025 (11) |
| C6'' | 0.0195 (12) | 0.0228 (18) | 0.0186 (13) | −0.0053 (13) | −0.0021 (9) | 0.0022 (13) |
| C1''' | 0.0147 (11) | 0.0114 (15) | 0.0178 (12) | −0.0007 (11) | −0.0007 (9) | −0.0048 (11) |
| C2''' | 0.0144 (12) | 0.0152 (16) | 0.0180 (12) | −0.0025 (10) | −0.0013 (9) | −0.0028 (11) |
| C3''' | 0.0166 (12) | 0.0195 (17) | 0.0150 (12) | −0.0038 (11) | 0.0007 (9) | 0.0019 (11) |
| C4''' | 0.0177 (12) | 0.0156 (17) | 0.0152 (12) | −0.0002 (11) | −0.0028 (9) | 0.0046 (11) |
| C5''' | 0.0149 (12) | 0.0163 (16) | 0.0178 (12) | −0.0005 (11) | −0.0001 (9) | 0.0009 (12) |
| C6''' | 0.0255 (14) | 0.025 (2) | 0.0250 (14) | 0.0081 (13) | 0.0017 (11) | −0.0009 (13) |
| C1' | 0.0202 (13) | 0.0202 (18) | 0.0142 (12) | 0.0015 (12) | −0.0005 (9) | 0.0013 (12) |
| C2' | 0.0243 (14) | 0.0163 (17) | 0.0172 (13) | 0.0023 (12) | −0.0004 (10) | −0.0006 (12) |
| C3' | 0.0264 (14) | 0.0153 (17) | 0.0153 (12) | 0.0019 (12) | 0.0007 (10) | −0.0023 (11) |
| C4' | 0.0192 (12) | 0.0196 (17) | 0.0149 (12) | −0.0013 (12) | 0.0005 (9) | 0.0018 (12) |
| C5' | 0.0306 (15) | 0.0114 (17) | 0.0186 (13) | 0.0010 (12) | 0.0000 (11) | −0.0017 (12) |
| C6' | 0.0328 (15) | 0.0180 (18) | 0.0159 (13) | 0.0025 (13) | 0.0010 (11) | −0.0031 (12) |
Geometric parameters (Å, °) top
| O1—C2 | 1.352 (4) | C8—C9 | 1.379 (5) |
| O1—C9 | 1.373 (3) | C8—H8A | 0.9500 |
| O2—C4 | 1.269 (3) | C9—C13 | 1.414 (4) |
| O3—C7 | 1.347 (4) | C1''—C2'' | 1.522 (4) |
| O3—H3 | 0.89 (2) | C1''—H1'' | 1.0000 |
| O4—C5 | 1.384 (3) | C2''—C3'' | 1.528 (4) |
| O4—C1'' | 1.409 (3) | C2''—H2'' | 1.0000 |
| O5—C1'' | 1.420 (3) | C3''—C4'' | 1.532 (4) |
| O5—C5'' | 1.436 (3) | C3''—H3'' | 1.0000 |
| O6—C3'' | 1.423 (3) | C4''—C5'' | 1.524 (3) |
| O6—H6 | 0.82 (2) | C4''—H4'' | 1.0000 |
| O7—C4'' | 1.424 (4) | C5''—C6'' | 1.505 (4) |
| O7—H7 | 0.85 (2) | C5''—H5'' | 1.0000 |
| O8—C6'' | 1.439 (3) | C6''—H6''1 | 0.9900 |
| O8—H8 | 0.82 (2) | C6''—H6''2 | 0.9900 |
| O9—C1''' | 1.423 (3) | C1'''—C2''' | 1.534 (4) |
| O9—C2'' | 1.432 (3) | C1'''—H1''' | 1.0000 |
| O10—C1''' | 1.412 (3) | C2'''—C3''' | 1.539 (4) |
| O10—C5''' | 1.457 (3) | C2'''—H2''' | 1.0000 |
| O11—C2''' | 1.431 (3) | C3'''—C4''' | 1.514 (4) |
| O11—H11 | 0.86 (2) | C3'''—H3''' | 1.0000 |
| O12—C3''' | 1.425 (3) | C4'''—C5''' | 1.529 (4) |
| O12—H12 | 0.85 (3) | C4'''—H4''' | 1.0000 |
| O13—C4''' | 1.432 (3) | C5'''—C6''' | 1.511 (4) |
| O13—H13 | 0.87 (2) | C5'''—H5''' | 1.0000 |
| O14—C4' | 1.360 (3) | C6'''—H6''3 | 0.9800 |
| O14—H14 | 0.87 (3) | C6'''—H6''4 | 0.9800 |
| O15—H15A | 0.80 (3) | C6'''—H6''5 | 0.9800 |
| O15—H15B | 0.84 (3) | C1'—C6' | 1.393 (5) |
| C2—C3 | 1.361 (4) | C1'—C2' | 1.400 (4) |
| C2—C1' | 1.472 (4) | C2'—C3' | 1.379 (4) |
| C3—C4 | 1.437 (4) | C2'—H2' | 0.9500 |
| C3—H3A | 0.9500 | C3'—C4' | 1.386 (4) |
| C4—C13 | 1.440 (4) | C3'—H3' | 0.9500 |
| C5—C6 | 1.371 (4) | C4'—C5' | 1.403 (4) |
| C5—C13 | 1.424 (4) | C5'—C6' | 1.381 (4) |
| C6—C7 | 1.406 (4) | C5'—H5' | 0.9500 |
| C6—H6A | 0.9500 | C6'—H6' | 0.9500 |
| C7—C8 | 1.381 (4) | | |
| | | |
| C2—O1—C9 | 120.8 (2) | O5—C5''—C4'' | 108.0 (2) |
| C7—O3—H3 | 111 (2) | C6''—C5''—C4'' | 115.2 (2) |
| C5—O4—C1'' | 115.7 (2) | O5—C5''—H5'' | 108.8 |
| C1''—O5—C5'' | 111.37 (19) | C6''—C5''—H5'' | 108.8 |
| C3''—O6—H6 | 108 (3) | C4''—C5''—H5'' | 108.8 |
| C4''—O7—H7 | 112 (3) | O8—C6''—C5'' | 110.5 (2) |
| C6''—O8—H8 | 109 (3) | O8—C6''—H6''1 | 109.6 |
| C1'''—O9—C2'' | 120.72 (19) | C5''—C6''—H6''1 | 109.6 |
| C1'''—O10—C5''' | 115.13 (19) | O8—C6''—H6''2 | 109.6 |
| C2'''—O11—H11 | 104 (2) | C5''—C6''—H6''2 | 109.6 |
| C3'''—O12—H12 | 105 (3) | H6''1—C6''—H6''2 | 108.1 |
| C4'''—O13—H13 | 107 (2) | O10—C1'''—O9 | 113.9 (2) |
| C4'—O14—H14 | 116 (2) | O10—C1'''—C2''' | 112.6 (2) |
| H15A—O15—H15B | 110 (4) | O9—C1'''—C2''' | 102.6 (2) |
| O1—C2—C3 | 121.1 (3) | O10—C1'''—H1''' | 109.2 |
| O1—C2—C1' | 112.4 (2) | O9—C1'''—H1''' | 109.2 |
| C3—C2—C1' | 126.5 (3) | C2'''—C1'''—H1''' | 109.2 |
| C2—C3—C4 | 121.8 (3) | O11—C2'''—C1''' | 108.4 (2) |
| C2—C3—H3A | 119.1 | O11—C2'''—C3''' | 110.7 (2) |
| C4—C3—H3A | 119.1 | C1'''—C2'''—C3''' | 108.2 (2) |
| O2—C4—C3 | 120.0 (3) | O11—C2'''—H2''' | 109.8 |
| O2—C4—C13 | 123.7 (2) | C1'''—C2'''—H2''' | 109.8 |
| C3—C4—C13 | 116.4 (2) | C3'''—C2'''—H2''' | 109.8 |
| C6—C5—O4 | 122.3 (2) | O12—C3'''—C4''' | 112.2 (2) |
| C6—C5—C13 | 121.4 (2) | O12—C3'''—C2''' | 109.6 (2) |
| O4—C5—C13 | 116.3 (2) | C4'''—C3'''—C2''' | 109.0 (2) |
| C5—C6—C7 | 120.0 (3) | O12—C3'''—H3''' | 108.7 |
| C5—C6—H6A | 120.0 | C4'''—C3'''—H3''' | 108.7 |
| C7—C6—H6A | 120.0 | C2'''—C3'''—H3''' | 108.7 |
| O3—C7—C8 | 118.7 (2) | O13—C4'''—C3''' | 110.2 (2) |
| O3—C7—C6 | 120.3 (3) | O13—C4'''—C5''' | 111.0 (2) |
| C8—C7—C6 | 121.0 (3) | C3'''—C4'''—C5''' | 109.0 (2) |
| C9—C8—C7 | 117.8 (3) | O13—C4'''—H4''' | 108.9 |
| C9—C8—H8A | 121.1 | C3'''—C4'''—H4''' | 108.9 |
| C7—C8—H8A | 121.1 | C5'''—C4'''—H4''' | 108.9 |
| O1—C9—C8 | 114.7 (2) | O10—C5'''—C6''' | 107.3 (2) |
| O1—C9—C13 | 121.2 (3) | O10—C5'''—C4''' | 109.2 (2) |
| C8—C9—C13 | 124.1 (3) | C6'''—C5'''—C4''' | 112.7 (3) |
| C9—C13—C5 | 115.4 (3) | O10—C5'''—H5''' | 109.2 |
| C9—C13—C4 | 118.7 (2) | C6'''—C5'''—H5''' | 109.2 |
| C5—C13—C4 | 125.8 (2) | C4'''—C5'''—H5''' | 109.2 |
| O4—C1''—O5 | 106.9 (2) | C5'''—C6'''—H6''3 | 109.5 |
| O4—C1''—C2'' | 110.6 (2) | C5'''—C6'''—H6''4 | 109.5 |
| O5—C1''—C2'' | 110.8 (2) | H6''3—C6'''—H6''4 | 109.5 |
| O4—C1''—H1'' | 109.5 | C5'''—C6'''—H6''5 | 109.5 |
| O5—C1''—H1'' | 109.5 | H6''3—C6'''—H6''5 | 109.5 |
| C2''—C1''—H1'' | 109.5 | H6''4—C6'''—H6''5 | 109.5 |
| O9—C2''—C1'' | 103.53 (19) | C6'—C1'—C2' | 119.1 (3) |
| O9—C2''—C3'' | 112.7 (2) | C6'—C1'—C2 | 121.0 (2) |
| C1''—C2''—C3'' | 107.5 (2) | C2'—C1'—C2 | 119.9 (3) |
| O9—C2''—H2'' | 110.9 | C3'—C2'—C1' | 119.9 (3) |
| C1''—C2''—H2'' | 110.9 | C3'—C2'—H2' | 120.0 |
| C3''—C2''—H2'' | 110.9 | C1'—C2'—H2' | 120.0 |
| O6—C3''—C2'' | 107.5 (2) | C2'—C3'—C4' | 120.7 (3) |
| O6—C3''—C4'' | 111.7 (2) | C2'—C3'—H3' | 119.6 |
| C2''—C3''—C4'' | 110.7 (2) | C4'—C3'—H3' | 119.6 |
| O6—C3''—H3'' | 109.0 | O14—C4'—C3' | 117.2 (2) |
| C2''—C3''—H3'' | 109.0 | O14—C4'—C5' | 122.9 (3) |
| C4''—C3''—H3'' | 109.0 | C3'—C4'—C5' | 119.9 (3) |
| O7—C4''—C5'' | 107.7 (2) | C6'—C5'—C4' | 119.2 (3) |
| O7—C4''—C3'' | 110.9 (2) | C6'—C5'—H5' | 120.4 |
| C5''—C4''—C3'' | 109.3 (2) | C4'—C5'—H5' | 120.4 |
| O7—C4''—H4'' | 109.6 | C5'—C6'—C1' | 121.2 (3) |
| C5''—C4''—H4'' | 109.6 | C5'—C6'—H6' | 119.4 |
| C3''—C4''—H4'' | 109.6 | C1'—C6'—H6' | 119.4 |
| O5—C5''—C6'' | 107.1 (2) | | |
| | | |
| C9—O1—C2—C3 | 0.7 (4) | O6—C3''—C4''—C5'' | 175.5 (2) |
| C9—O1—C2—C1' | −179.5 (2) | C2''—C3''—C4''—C5'' | 55.7 (3) |
| O1—C2—C3—C4 | −2.6 (4) | C1''—O5—C5''—C6'' | −170.6 (2) |
| C1'—C2—C3—C4 | 177.6 (2) | C1''—O5—C5''—C4'' | 64.7 (3) |
| C2—C3—C4—O2 | −175.6 (3) | O7—C4''—C5''—O5 | −179.4 (2) |
| C2—C3—C4—C13 | 3.5 (4) | C3''—C4''—C5''—O5 | −58.9 (3) |
| C1''—O4—C5—C6 | 9.7 (3) | O7—C4''—C5''—C6'' | 60.8 (3) |
| C1''—O4—C5—C13 | −169.0 (2) | C3''—C4''—C5''—C6'' | −178.6 (3) |
| O4—C5—C6—C7 | −174.0 (2) | O5—C5''—C6''—O8 | 70.4 (3) |
| C13—C5—C6—C7 | 4.6 (4) | C4''—C5''—C6''—O8 | −169.4 (2) |
| C5—C6—C7—O3 | 179.2 (3) | C5'''—O10—C1'''—O9 | −61.0 (3) |
| C5—C6—C7—C8 | −1.0 (4) | C5'''—O10—C1'''—C2''' | 55.4 (3) |
| O3—C7—C8—C9 | 177.3 (3) | C2''—O9—C1'''—O10 | −43.8 (3) |
| C6—C7—C8—C9 | −2.5 (4) | C2''—O9—C1'''—C2''' | −165.8 (2) |
| C2—O1—C9—C8 | 179.2 (2) | O10—C1'''—C2'''—O11 | 66.0 (3) |
| C2—O1—C9—C13 | 0.2 (4) | O9—C1'''—C2'''—O11 | −171.1 (2) |
| C7—C8—C9—O1 | −176.4 (2) | O10—C1'''—C2'''—C3''' | −54.2 (3) |
| C7—C8—C9—C13 | 2.5 (4) | O9—C1'''—C2'''—C3''' | 68.7 (3) |
| O1—C9—C13—C5 | 179.7 (2) | O11—C2'''—C3'''—O12 | 62.0 (3) |
| C8—C9—C13—C5 | 0.9 (4) | C1'''—C2'''—C3'''—O12 | −179.3 (2) |
| O1—C9—C13—C4 | 0.8 (4) | O11—C2'''—C3'''—C4''' | −61.2 (3) |
| C8—C9—C13—C4 | −178.1 (3) | C1'''—C2'''—C3'''—C4''' | 57.5 (3) |
| C6—C5—C13—C9 | −4.5 (4) | O12—C3'''—C4'''—O13 | 55.4 (3) |
| O4—C5—C13—C9 | 174.2 (2) | C2'''—C3'''—C4'''—O13 | 176.9 (2) |
| C6—C5—C13—C4 | 174.4 (3) | O12—C3'''—C4'''—C5''' | 177.5 (2) |
| O4—C5—C13—C4 | −6.9 (4) | C2'''—C3'''—C4'''—C5''' | −61.0 (3) |
| O2—C4—C13—C9 | 176.5 (2) | C1'''—O10—C5'''—C6''' | −179.1 (2) |
| C3—C4—C13—C9 | −2.5 (4) | C1'''—O10—C5'''—C4''' | −56.6 (3) |
| O2—C4—C13—C5 | −2.3 (4) | O13—C4'''—C5'''—O10 | −179.9 (2) |
| C3—C4—C13—C5 | 178.7 (2) | C3'''—C4'''—C5'''—O10 | 58.5 (3) |
| C5—O4—C1''—O5 | −80.2 (3) | O13—C4'''—C5'''—C6''' | −60.8 (3) |
| C5—O4—C1''—C2'' | 159.1 (2) | C3'''—C4'''—C5'''—C6''' | 177.7 (2) |
| C5''—O5—C1''—O4 | 173.8 (2) | O1—C2—C1'—C6' | 160.3 (3) |
| C5''—O5—C1''—C2'' | −65.7 (3) | C3—C2—C1'—C6' | −19.9 (4) |
| C1'''—O9—C2''—C1'' | 158.0 (2) | O1—C2—C1'—C2' | −19.2 (3) |
| C1'''—O9—C2''—C3'' | −86.2 (3) | C3—C2—C1'—C2' | 160.6 (3) |
| O4—C1''—C2''—O9 | −64.0 (3) | C6'—C1'—C2'—C3' | 0.9 (4) |
| O5—C1''—C2''—O9 | 177.7 (2) | C2—C1'—C2'—C3' | −179.6 (3) |
| O4—C1''—C2''—C3'' | 176.6 (2) | C1'—C2'—C3'—C4' | −1.1 (4) |
| O5—C1''—C2''—C3'' | 58.3 (3) | C2'—C3'—C4'—O14 | −178.2 (2) |
| O9—C2''—C3''—O6 | 70.4 (3) | C2'—C3'—C4'—C5' | 0.7 (4) |
| C1''—C2''—C3''—O6 | −176.2 (2) | O14—C4'—C5'—C6' | 178.8 (3) |
| O9—C2''—C3''—C4'' | −167.4 (2) | C3'—C4'—C5'—C6' | 0.0 (4) |
| C1''—C2''—C3''—C4'' | −53.9 (3) | C4'—C5'—C6'—C1' | −0.2 (4) |
| O6—C3''—C4''—O7 | −66.0 (3) | C2'—C1'—C6'—C5' | −0.3 (4) |
| C2''—C3''—C4''—O7 | 174.2 (2) | C2—C1'—C6'—C5' | −179.7 (3) |
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O15 | 0.89 (3) | 1.80 (3) | 2.684 (3) | 177 (5) |
| O6—H6···O10i | 0.82 (3) | 2.08 (3) | 2.881 (3) | 166 (3) |
| O7—H7···O11i | 0.85 (3) | 1.99 (3) | 2.817 (3) | 164 (4) |
| O8—H8···O14ii | 0.82 (4) | 2.17 (3) | 2.821 (3) | 136 (3) |
| O11—H11···O2iii | 0.87 (3) | 2.19 (3) | 3.006 (3) | 158 (3) |
| O13—H13···O2 | 0.87 (3) | 1.79 (3) | 2.653 (3) | 172 (3) |
| O14—H14···O13iv | 0.87 (3) | 1.76 (3) | 2.617 (3) | 170 (3) |
| O15—H15A···O8 | 0.80 (3) | 2.06 (4) | 2.829 (3) | 161 (4) |
| O15—H15B···O2v | 0.84 (3) | 2.00 (3) | 2.820 (4) | 168 (4) |
| Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z; (iii) x+1, y, z; (iv) x−1/2, −y+5/2, −z; (v) x, y−1, z. |
Table 1
Hydrogen-bond geometry (Å, °) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O15 | 0.89 (3) | 1.80 (3) | 2.684 (3) | 177 (5) |
| O6—H6···O10i | 0.82 (3) | 2.08 (3) | 2.881 (3) | 166 (3) |
| O7—H7···O11i | 0.85 (3) | 1.99 (3) | 2.817 (3) | 164 (4) |
| O8—H8···O14ii | 0.82 (4) | 2.17 (3) | 2.821 (3) | 136 (3) |
| O11—H11···O2iii | 0.87 (3) | 2.19 (3) | 3.006 (3) | 158 (3) |
| O13—H13···O2 | 0.87 (3) | 1.79 (3) | 2.653 (3) | 172 (3) |
| O14—H14···O13iv | 0.87 (3) | 1.76 (3) | 2.617 (3) | 170 (3) |
| O15—H15A···O8 | 0.80 (3) | 2.06 (4) | 2.829 (3) | 161 (4) |
| O15—H15B···O2v | 0.84 (3) | 2.00 (3) | 2.820 (4) | 168 (4) |
| Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1/2, −y+3/2, −z; (iii) x+1, y, z; (iv) x−1/2, −y+5/2, −z; (v) x, y−1, z. |
Li, W., Deng, Y. L., Dai, R. J., Yu, Y. H., Saeed, M. K., Li, L., Meng, W. W. & &Zhang, X. S. (2007). J. Pharm. Biomed. Anal. 45, 38–46.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corp., Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
![[Figure 1]](./bt2776fig1thm.gif)
The title compound was prepared from compound (II) by hydrolysis (scheme 2).
The hydroxyphenyl ring makes a dihedral angle of 20.05 (11)° with the benzopyranone ring. The two saturated rings adopt chair configurations. The crystal structure is stabilized by intra- and intermolecular O—H···O hydrogen bonds (Table 1), with O···O distances in the range 2.617 (3)–3.006 (3) Å.