5,6,7,5'-Tetra-meth-oxy-3',4'-methyl-ene-dioxy-flavone monohydrate.

THE TITLE COMPOUND [SYSTEMATIC NAME: 5,6,7-trimeth-oxy-2-(7-meth-oxy-1,3-dihydro-2-benzofuran-5-yl)-4H-chromen-4-one monohydrate], C(20)H(18)O(8)·H(2)O, was isolated from the popular Chinese medicinal plant Entada phaseoloides. In the crystal, inversion-related mol-ecules are joined by pairs of weak C-H⋯O hydrogen bonds. The dimers are further inter-connected by a bridging water mol-ecule 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 = 404.36

Triclinic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.117

S = 1.07

3181 reflections

270 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.32 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015139/bg2446sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812015139/bg2446Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Enhanced figure: interactive version of Fig. 1

C20H18O8·H2O	Z = 2
Mr = 404.36	F(000) = 424
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0641P)2 + 0.3125P] where P = (Fo2 + 2Fc2)/3
3181 reflections	(Δ/σ)max < 0.001
270 parameters	Δρmax = 0.49 e Å−3
4 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .