5,6,7,5′-Tetra­meth­oxy-3′,4′-methyl­ene­dioxy­flavone monohydrate

Li, H.-J.; Zhou, D.-L.; Xu, T.-J.; Lam, C.-K.; Lan, W.-J.

doi:10.1107/S1600536812015139

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1390

doi:10.1107/S1600536812015139

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5,6,7,5′-Tetramethoxy-3′,4′-methylenedioxyflavone monohydrate

Hou-Jin Li,^a Da-Lang Zhou,^a Ting-Juan Xu,^a Chi-Keung Lam ^a and Wen-Jian Lan ^b ^*

^aSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, People's Republic of China, and ^bSchool of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: lanwj@mail.sysu.edu.cn

(Received 21 February 2012; accepted 5 April 2012; online 13 April 2012)

The title compound [systematic name: 5,6,7-trimethoxy-2-(7-methoxy-1,3-dihydro-2-benzofuran-5-yl)-4H-chromen-4-one monohydrate], C₂₀H₁₈O₈·H₂O, was isolated from the popular Chinese medicinal plant Entada phaseoloides. In the crystal, inversion-related molecules are joined by pairs of weak C—H⋯O hydrogen bonds. The dimers are further interconnected by a bridging water molecule via weak C—H⋯O_water and pairs of (O—H)_water⋯O hydrogen bonds into a linear tape running parallel to the b axis.

Related literature

For the isolation of 5,6,7,5′-tetramethoxy-3′,4′-methylenedioxyflavone, see: Chen et al. (1984 ); Vyas et al. (1986a ); Souza et al. (1995 ); Tomazela et al. (2000 ). For the NMR spectroscopic studies, see Vyas et al. (1986b ). For the biological activity of flavonoids, see: Genoux et al. (2011 ); Bodewes et al. (2011 ); Jacob et al. (2011 ); Veitch & Grayer (2011 ).

Experimental

Crystal data

C₂₀H₁₈O₈·H₂O
M_r = 404.36
Triclinic, $[P \overline 1]$
a = 9.3014 (17) Å
b = 9.3146 (17) Å
c = 11.009 (2) Å
α = 105.413 (3)°
β = 91.798 (3)°
γ = 100.985 (3)°
V = 899.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 173 K
0.41 × 0.35 × 0.32 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.772, T_max = 1.000
6560 measured reflections
3181 independent reflections
2608 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.117
S = 1.07
3181 reflections
270 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H11⋯O5	0.83 (2)	2.03 (2)	2.823 (2)	160 (3)
O1W—H12⋯O4	0.83 (2)	2.33 (3)	2.987 (2)	137 (3)
C3—H3A⋯O5ⁱ	0.95	2.41	3.255 (2)	147
C8—H8A⋯O1Wⁱⁱ	0.95	2.42	3.372 (2)	175
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812015139/bg2446sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015139/bg2446Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015139/bg2446Isup3.cml

checkCIF report

Comment top

Flavonoids are an important secondary metabolites produced in some medicinal or dietary plants. They are reported to show diverse biological activities, including antioxidant, anti-inflammatory, anti-cancer activities, as well as slowing down the progression of cardiovascular and neurodegenerative diseases (Genoux et al., 2011; Bodewes et al., 2011; Jacob et al., 2011; Veitch et al., 2011).

Entada phaseoloides (L.) Merr., a popular Chinese medicinal plant, is distributed widely in the South China and the trunk has been used clinically for a long time to treat rheumatism. The title compound, 5,6,7,5'-tetramethoxy-3',4'-methylenedioxyflavone was isolated from the ethanol extract of Entada phaseoloides. In the crystals, the methoxy oxygen atom and the adjacent carbonyl oxygen atom are bridged by a water molecule via O1w—H11···O5 and O1w—H12···O4 hydrogen bonds. Neighboring molecules related by an inversion centre are joined together via a pair of weak C3—H···O5═C4 hydrogen bonds. The molecules are further cross linked by a weak C8'-H···O5═C and C8—H8A···O1w intermolecular interactions.

Related literature top

For the isolation of 5,6,7,5'-tetramethoxy-3',4'-methylenedioxyflavone, see: Chen et al. (1984); Vyas et al. (1986a); Souza et al. (1995); Tomazela et al. (2000). For the NMR spectroscopic studies, see Vyas et al. (1986b). For the biological activity of flavonoids, see: Genoux et al. (2011); Bodewes et al. (2011); Jacob et al. (2011); Veitch & Grayer (2011). Scheme: please revise to show solvent molecule

Experimental top

The trunk of Entada phaseoloides (L.) Merr. was successively extracted three times with ethanol. The extract was concentrated by low-temperature rotary evaporation and chromatographed on a silica gel column with a petroleum ether–EtOAc–MeOH gradient as the eluent to afford 20 fractions (Fr. 1–Fr. 20). Fr. 8–10 were further purified by RP-HPLC eluted with H₂O–MeCN (60:40, v/v) to yield 5,6,7,5'-tetramethoxy-3',4'-methylenedioxyflavone. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the compound in EtOAc.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of the title compound showing displacement ellipsoids at the 50% probability level.

5,6,7-trimethoxy-2-(7-methoxy-1,3-dihydro-2-benzofuran-5-yl)- 4H-chromen-4-one monohydrate top

Crystal data top

C₂₀H₁₈O₈·H₂O	Z = 2
M_r = 404.36	F(000) = 424
Triclinic, P1	D_x = 1.493 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3014 (17) Å	Cell parameters from 4354 reflections
b = 9.3146 (17) Å	θ = 2.2–27.0°
c = 11.009 (2) Å	µ = 0.12 mm⁻¹
α = 105.413 (3)°	T = 173 K
β = 91.798 (3)°	Block, colourless
γ = 100.985 (3)°	0.41 × 0.35 × 0.32 mm
V = 899.3 (3) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	3181 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scan	θ_max = 25.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
T_min = 0.772, T_max = 1.000	k = −11→11
6560 measured reflections	l = −13→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0641P)² + 0.3125P] where P = (F_o² + 2F_c²)/3
3181 reflections	(Δ/σ)_max < 0.001
270 parameters	Δρ_max = 0.49 e Å⁻³
4 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₀H₁₈O₈·H₂O	γ = 100.985 (3)°
M_r = 404.36	V = 899.3 (3) Å³
Triclinic, P1	Z = 2
a = 9.3014 (17) Å	Mo Kα radiation
b = 9.3146 (17) Å	µ = 0.12 mm⁻¹
c = 11.009 (2) Å	T = 173 K
α = 105.413 (3)°	0.41 × 0.35 × 0.32 mm
β = 91.798 (3)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3181 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2608 reflections with I > 2σ(I)
T_min = 0.772, T_max = 1.000	R_int = 0.018
6560 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	4 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.49 e Å⁻³
3181 reflections	Δρ_min = −0.32 e Å⁻³
270 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	U_iso*/U_eq
O1	0.53779 (12)	0.48854 (12)	0.20513 (10)	0.0240 (3)
O1W	0.4889 (2)	−0.09163 (18)	0.36332 (16)	0.0525 (4)
H11	0.487 (3)	−0.071 (4)	0.295 (2)	0.093 (11)*
H12	0.422 (2)	−0.055 (5)	0.3978 (15)	0.23 (3)*
O2	0.22755 (13)	0.59084 (13)	0.53871 (11)	0.0311 (3)
O3	0.14023 (13)	0.30245 (14)	0.51890 (12)	0.0341 (3)
O4	0.25387 (13)	0.08319 (13)	0.34924 (11)	0.0286 (3)
O5	0.44095 (14)	0.03101 (13)	0.16068 (11)	0.0317 (3)
O6	0.93016 (15)	0.40373 (14)	−0.22376 (12)	0.0388 (3)
O7	0.97888 (14)	0.66696 (14)	−0.17464 (12)	0.0363 (3)
O8	0.85089 (14)	0.85819 (13)	0.01787 (12)	0.0356 (3)
C2	0.59340 (17)	0.39067 (18)	0.11252 (14)	0.0218 (3)
C3	0.56048 (18)	0.23941 (18)	0.09729 (15)	0.0241 (4)
H3A	0.6018	0.1753	0.0316	0.029*
C4	0.46578 (18)	0.17052 (18)	0.17582 (15)	0.0237 (4)
C5	0.30091 (18)	0.23401 (18)	0.35496 (15)	0.0234 (4)
C6	0.24590 (17)	0.34069 (19)	0.44266 (15)	0.0244 (4)
C7	0.29046 (17)	0.49663 (19)	0.45016 (15)	0.0243 (4)
C8	0.38842 (17)	0.54320 (18)	0.36968 (15)	0.0229 (4)
H8A	0.4182	0.6479	0.3738	0.027*
C9	0.44252 (17)	0.43264 (18)	0.28223 (14)	0.0214 (3)
C10	0.40336 (17)	0.27721 (18)	0.27200 (15)	0.0215 (3)
C11	0.1301 (2)	0.0098 (2)	0.2581 (2)	0.0422 (5)
H11A	0.1008	−0.0971	0.2579	0.063*
H11B	0.1571	0.0153	0.1739	0.063*
H11C	0.0479	0.0610	0.2804	0.063*
C12	0.1733 (2)	0.2124 (2)	0.59780 (18)	0.0384 (5)
H12A	0.0901	0.1921	0.6476	0.058*
H12B	0.2611	0.2671	0.6549	0.058*
H12C	0.1916	0.1158	0.5453	0.058*
C13	0.2578 (2)	0.7486 (2)	0.54402 (18)	0.0372 (4)
H13A	0.2063	0.8038	0.6116	0.056*
H13B	0.2240	0.7610	0.4629	0.056*
H13C	0.3638	0.7893	0.5612	0.056*
C16	1.01507 (19)	0.5318 (2)	−0.25493 (16)	0.0295 (4)
H16A	0.9920	0.5253	−0.3449	0.035*
H16B	1.1213	0.5340	−0.2413	0.035*
C1'	0.69092 (17)	0.46871 (18)	0.03700 (15)	0.0222 (3)
C2'	0.75922 (19)	0.38195 (19)	−0.06075 (16)	0.0270 (4)
H2'A	0.7408	0.2740	−0.0814	0.032*
C3'	0.85314 (18)	0.46137 (19)	−0.12415 (15)	0.0261 (4)
C4'	0.88199 (18)	0.61765 (19)	−0.09635 (15)	0.0257 (4)
C5'	0.81543 (18)	0.70520 (18)	−0.00182 (15)	0.0247 (4)
C6'	0.71763 (17)	0.62730 (18)	0.06452 (15)	0.0231 (4)
H6'A	0.6686	0.6832	0.1294	0.028*
C8'	0.7778 (2)	0.95003 (19)	0.11035 (17)	0.0326 (4)
H8'A	0.8132	1.0575	0.1148	0.049*
H8'B	0.7982	0.9339	0.1931	0.049*
H8'C	0.6716	0.9218	0.0868	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0278 (6)	0.0202 (6)	0.0242 (6)	0.0049 (5)	0.0109 (5)	0.0057 (5)
O1W	0.0677 (11)	0.0415 (8)	0.0526 (10)	0.0061 (8)	−0.0019 (8)	0.0246 (7)
O2	0.0364 (7)	0.0241 (6)	0.0331 (7)	0.0078 (5)	0.0176 (5)	0.0059 (5)
O3	0.0319 (7)	0.0366 (7)	0.0437 (7)	0.0131 (5)	0.0209 (6)	0.0218 (6)
O4	0.0325 (6)	0.0218 (6)	0.0335 (7)	0.0043 (5)	0.0092 (5)	0.0113 (5)
O5	0.0449 (7)	0.0193 (6)	0.0331 (7)	0.0082 (5)	0.0145 (6)	0.0087 (5)
O6	0.0485 (8)	0.0321 (7)	0.0413 (7)	0.0131 (6)	0.0296 (6)	0.0134 (6)
O7	0.0420 (7)	0.0320 (7)	0.0404 (7)	0.0088 (6)	0.0233 (6)	0.0162 (6)
O8	0.0439 (8)	0.0223 (6)	0.0413 (7)	0.0049 (5)	0.0173 (6)	0.0097 (5)
C2	0.0217 (8)	0.0242 (8)	0.0195 (8)	0.0070 (6)	0.0031 (6)	0.0041 (6)
C3	0.0261 (8)	0.0234 (8)	0.0235 (8)	0.0075 (7)	0.0064 (7)	0.0057 (7)
C4	0.0254 (8)	0.0226 (8)	0.0236 (8)	0.0055 (7)	0.0018 (7)	0.0067 (7)
C5	0.0227 (8)	0.0223 (8)	0.0266 (8)	0.0039 (6)	0.0024 (7)	0.0098 (7)
C6	0.0217 (8)	0.0279 (9)	0.0265 (8)	0.0058 (7)	0.0074 (7)	0.0114 (7)
C7	0.0228 (8)	0.0264 (9)	0.0234 (8)	0.0071 (7)	0.0038 (7)	0.0047 (7)
C8	0.0237 (8)	0.0203 (8)	0.0238 (8)	0.0034 (6)	0.0036 (6)	0.0053 (6)
C9	0.0206 (8)	0.0237 (8)	0.0206 (8)	0.0031 (6)	0.0041 (6)	0.0081 (6)
C10	0.0213 (8)	0.0228 (8)	0.0214 (8)	0.0056 (6)	0.0027 (6)	0.0069 (6)
C11	0.0330 (10)	0.0297 (10)	0.0580 (13)	−0.0048 (8)	0.0017 (9)	0.0104 (9)
C12	0.0452 (11)	0.0461 (11)	0.0305 (9)	0.0121 (9)	0.0147 (8)	0.0186 (9)
C13	0.0461 (11)	0.0255 (9)	0.0400 (10)	0.0096 (8)	0.0178 (9)	0.0057 (8)
C16	0.0284 (9)	0.0347 (10)	0.0293 (9)	0.0097 (7)	0.0120 (7)	0.0125 (7)
C1'	0.0206 (8)	0.0251 (8)	0.0213 (8)	0.0045 (6)	0.0027 (6)	0.0072 (7)
C2'	0.0310 (9)	0.0239 (8)	0.0284 (9)	0.0079 (7)	0.0092 (7)	0.0086 (7)
C3'	0.0273 (9)	0.0299 (9)	0.0239 (8)	0.0108 (7)	0.0083 (7)	0.0083 (7)
C4'	0.0240 (8)	0.0314 (9)	0.0250 (8)	0.0058 (7)	0.0052 (7)	0.0134 (7)
C5'	0.0267 (8)	0.0231 (8)	0.0253 (8)	0.0047 (7)	0.0024 (7)	0.0085 (7)
C6'	0.0232 (8)	0.0258 (8)	0.0213 (8)	0.0076 (7)	0.0042 (6)	0.0063 (7)
C8'	0.0386 (10)	0.0241 (9)	0.0339 (9)	0.0072 (7)	0.0044 (8)	0.0056 (7)

Geometric parameters (Å, º) top

O1—C2	1.3627 (18)	C8—C9	1.393 (2)
O1—C9	1.3723 (19)	C8—H8A	0.9500
O1W—H11	0.829 (17)	C9—C10	1.397 (2)
O1W—H12	0.826 (19)	C11—H11A	0.9800
O2—C7	1.3564 (19)	C11—H11B	0.9800
O2—C13	1.427 (2)	C11—H11C	0.9800
O3—C6	1.369 (2)	C12—H12A	0.9800
O3—C12	1.422 (2)	C12—H12B	0.9800
O4—C5	1.3732 (19)	C12—H12C	0.9800
O4—C11	1.436 (2)	C13—H13A	0.9800
O5—C4	1.240 (2)	C13—H13B	0.9800
O6—C3'	1.374 (2)	C13—H13C	0.9800
O6—C16	1.428 (2)	C16—H16A	0.9900
O7—C4'	1.367 (2)	C16—H16B	0.9900
O7—C16	1.438 (2)	C1'—C6'	1.398 (2)
O8—C5'	1.356 (2)	C1'—C2'	1.411 (2)
O8—C8'	1.426 (2)	C2'—C3'	1.365 (2)
C2—C3	1.347 (2)	C2'—H2'A	0.9500
C2—C1'	1.470 (2)	C3'—C4'	1.376 (2)
C3—C4	1.436 (2)	C4'—C5'	1.383 (2)
C3—H3A	0.9500	C5'—C6'	1.400 (2)
C4—C10	1.465 (2)	C6'—H6'A	0.9500
C5—C6	1.377 (2)	C8'—H8'A	0.9800
C5—C10	1.417 (2)	C8'—H8'B	0.9800
C6—C7	1.412 (2)	C8'—H8'C	0.9800
C7—C8	1.381 (2)

C2—O1—C9	119.79 (12)	O3—C12—H12B	109.5
H11—O1W—H12	103 (3)	H12A—C12—H12B	109.5
C7—O2—C13	117.60 (13)	O3—C12—H12C	109.5
C6—O3—C12	116.78 (13)	H12A—C12—H12C	109.5
C5—O4—C11	112.69 (13)	H12B—C12—H12C	109.5
C3'—O6—C16	106.39 (13)	O2—C13—H13A	109.5
C4'—O7—C16	105.55 (13)	O2—C13—H13B	109.5
C5'—O8—C8'	117.93 (13)	H13A—C13—H13B	109.5
C3—C2—O1	121.29 (14)	O2—C13—H13C	109.5
C3—C2—C1'	125.84 (14)	H13A—C13—H13C	109.5
O1—C2—C1'	112.86 (13)	H13B—C13—H13C	109.5
C2—C3—C4	123.01 (15)	O6—C16—O7	107.82 (13)
C2—C3—H3A	118.5	O6—C16—H16A	110.1
C4—C3—H3A	118.5	O7—C16—H16A	110.1
O5—C4—C3	121.05 (15)	O6—C16—H16B	110.1
O5—C4—C10	124.15 (15)	O7—C16—H16B	110.1
C3—C4—C10	114.80 (14)	H16A—C16—H16B	108.5
O4—C5—C6	118.34 (14)	C6'—C1'—C2'	120.90 (15)
O4—C5—C10	120.27 (14)	C6'—C1'—C2	119.88 (14)
C6—C5—C10	121.39 (14)	C2'—C1'—C2	119.20 (14)
O3—C6—C5	122.89 (14)	C3'—C2'—C1'	116.46 (15)
O3—C6—C7	117.07 (14)	C3'—C2'—H2'A	121.8
C5—C6—C7	119.88 (15)	C1'—C2'—H2'A	121.8
O2—C7—C8	124.83 (15)	C2'—C3'—O6	127.60 (15)
O2—C7—C6	114.65 (14)	C2'—C3'—C4'	123.06 (15)
C8—C7—C6	120.50 (15)	O6—C3'—C4'	109.34 (14)
C7—C8—C9	118.29 (15)	O7—C4'—C3'	110.80 (14)
C7—C8—H8A	120.9	O7—C4'—C5'	127.57 (15)
C9—C8—H8A	120.9	C3'—C4'—C5'	121.61 (15)
O1—C9—C8	114.47 (14)	O8—C5'—C4'	117.04 (15)
O1—C9—C10	122.08 (14)	O8—C5'—C6'	126.13 (15)
C8—C9—C10	123.45 (14)	C4'—C5'—C6'	116.82 (15)
C9—C10—C5	116.48 (14)	C1'—C6'—C5'	121.13 (15)
C9—C10—C4	118.96 (14)	C1'—C6'—H6'A	119.4
C5—C10—C4	124.54 (14)	C5'—C6'—H6'A	119.4
O4—C11—H11A	109.5	O8—C8'—H8'A	109.5
O4—C11—H11B	109.5	O8—C8'—H8'B	109.5
H11A—C11—H11B	109.5	H8'A—C8'—H8'B	109.5
O4—C11—H11C	109.5	O8—C8'—H8'C	109.5
H11A—C11—H11C	109.5	H8'A—C8'—H8'C	109.5
H11B—C11—H11C	109.5	H8'B—C8'—H8'C	109.5
O3—C12—H12A	109.5

C9—O1—C2—C3	−2.1 (2)	C6—C5—C10—C4	−179.51 (14)
C9—O1—C2—C1'	178.78 (12)	O5—C4—C10—C9	178.31 (15)
O1—C2—C3—C4	0.1 (2)	C3—C4—C10—C9	−1.8 (2)
C1'—C2—C3—C4	179.04 (14)	O5—C4—C10—C5	−3.6 (3)
C2—C3—C4—O5	−178.26 (15)	C3—C4—C10—C5	176.28 (14)
C2—C3—C4—C10	1.8 (2)	C3'—O6—C16—O7	−3.22 (18)
C11—O4—C5—C6	93.10 (18)	C4'—O7—C16—O6	2.76 (18)
C11—O4—C5—C10	−86.81 (18)	C3—C2—C1'—C6'	−178.88 (15)
C12—O3—C6—C5	57.9 (2)	O1—C2—C1'—C6'	0.2 (2)
C12—O3—C6—C7	−126.79 (17)	C3—C2—C1'—C2'	−0.4 (2)
O4—C5—C6—O3	−4.0 (2)	O1—C2—C1'—C2'	178.63 (13)
C10—C5—C6—O3	175.91 (14)	C6'—C1'—C2'—C3'	1.0 (2)
O4—C5—C6—C7	−179.23 (14)	C2—C1'—C2'—C3'	−177.43 (14)
C10—C5—C6—C7	0.7 (2)	C1'—C2'—C3'—O6	−178.60 (16)
C13—O2—C7—C8	4.0 (2)	C1'—C2'—C3'—C4'	0.0 (2)
C13—O2—C7—C6	−174.70 (15)	C16—O6—C3'—C2'	−178.74 (17)
O3—C6—C7—O2	3.6 (2)	C16—O6—C3'—C4'	2.46 (18)
C5—C6—C7—O2	179.09 (14)	C16—O7—C4'—C3'	−1.28 (19)
O3—C6—C7—C8	−175.18 (14)	C16—O7—C4'—C5'	179.85 (16)
C5—C6—C7—C8	0.3 (2)	C2'—C3'—C4'—O7	−179.62 (15)
O2—C7—C8—C9	−179.16 (14)	O6—C3'—C4'—O7	−0.7 (2)
C6—C7—C8—C9	−0.5 (2)	C2'—C3'—C4'—C5'	−0.7 (3)
C2—O1—C9—C8	−177.44 (13)	O6—C3'—C4'—C5'	178.20 (15)
C2—O1—C9—C10	2.1 (2)	C8'—O8—C5'—C4'	176.80 (14)
C7—C8—C9—O1	179.29 (13)	C8'—O8—C5'—C6'	−3.2 (2)
C7—C8—C9—C10	−0.3 (2)	O7—C4'—C5'—O8	−1.0 (3)
O1—C9—C10—C5	−178.32 (13)	C3'—C4'—C5'—O8	−179.78 (15)
C8—C9—C10—C5	1.2 (2)	O7—C4'—C5'—C6'	178.95 (15)
O1—C9—C10—C4	−0.1 (2)	C3'—C4'—C5'—C6'	0.2 (2)
C8—C9—C10—C4	179.43 (14)	C2'—C1'—C6'—C5'	−1.5 (2)
O4—C5—C10—C9	178.51 (13)	C2—C1'—C6'—C5'	176.92 (14)
C6—C5—C10—C9	−1.4 (2)	O8—C5'—C6'—C1'	−179.14 (15)
O4—C5—C10—C4	0.4 (2)	C4'—C5'—C6'—C1'	0.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O5	0.83 (2)	2.03 (2)	2.823 (2)	160 (3)
O1W—H12···O4	0.83 (2)	2.33 (3)	2.987 (2)	137 (3)
C3—H3A···O5ⁱ	0.95	2.41	3.255 (2)	147
C8—H8A···O1Wⁱⁱ	0.95	2.42	3.372 (2)	175

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈O₈·H₂O
M_r	404.36
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.3014 (17), 9.3146 (17), 11.009 (2)
α, β, γ (°)	105.413 (3), 91.798 (3), 100.985 (3)
V (Å³)	899.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.41 × 0.35 × 0.32

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.772, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6560, 3181, 2608
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.117, 1.07
No. of reflections	3181
No. of parameters	270
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.32

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H11···O5	0.829 (17)	2.03 (2)	2.823 (2)	160 (3)
O1W—H12···O4	0.826 (19)	2.33 (3)	2.987 (2)	137 (3)
C3—H3A···O5ⁱ	0.95	2.41	3.255 (2)	147
C8—H8A···O1Wⁱⁱ	0.95	2.42	3.372 (2)	175

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 30973633), the Guangdong Provincial Science and Technology Research Program (Nos. 2009B030801199, 2010B030800002 and 2010B030600011), the Research Program from the Administration of Traditional Chinese Medicine of Guangdong Province (No. 20111164) and the Fund for Undergraduate Innovative Experiment and Research of Guangdong Province (No.1055811012).

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