5,7-Dihy-droxy-3,6-dimeth-oxy-2-(4-meth-oxy-phen-yl)-4H-chromen-4-one monohydrate.

The title compound, C(18)H(16)O(7)·H(2)O, is a flavonoid isolated from Dodonaea viscosa-. The benzopyran ring system of the flavonoid is essentially planar [maximum deviation = 0.025 (2) Å] and inclined at 5.83 (2)° to the attached benzene ring. The water of hydration is involved in extensive hydrogen bonding, assembling the mol-ecules into a supra-molecular network via classical inter-molecular O-H⋯O hydrogen bonding. The crystal structure is further stabilized by π-π stacking inter-actions [centroid-centroid distance between benzene rings = 3.564 (3) Å].

Related literature

For the anti-oxidant activity of flavonoids, see: Pedrielli et al. (2001 ▶, for their anti-protozoal activity, see: Calzada et al. (1999 ▶) and for their anti-viral activity, see: Lin et al. (1999 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶). For related structures, see: Arfan et al. (2010 ▶); Azhar ul et al. (2004 ▶); Ferheen et al. (2005 ▶); Hussain et al. (2008 ▶, 2009 ▶); Jan et al. (2009 ▶); Khan et al. (2005a ▶,b ▶); Nisar et al. (2010 ▶); Riaz et al. (2002 ▶); Sharif et al. (2005 ▶).

Experimental

Crystal data

C18H16O7·H2O

M = 362.32

Monoclinic,

a = 19.869 (4) Å

b = 6.8126 (15) Å

c = 24.424 (5) Å

β = 91.298 (4)°

V = 3305.2 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 150 K

0.19 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.978, T max = 0.990

14127 measured reflections

3400 independent reflections

2072 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.142

S = 1.05

3400 reflections

243 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b ▶); molecular graphics: SHELXTL (Sheldrick, 2008b ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039012/rk2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039012/rk2231Isup2.hkl

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

C18H16O7·H2O	F(000) = 1520
Mr = 362.32	Dx = 1.456 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1391 reflections
a = 19.869 (4) Å	θ = 2.6–22.0°
b = 6.8126 (15) Å	µ = 0.12 mm−1
c = 24.424 (5) Å	T = 150 K
β = 91.298 (4)°	Block, yellow
V = 3305.2 (12) Å3	0.19 × 0.18 × 0.09 mm
Z = 8

Bruker APEXII CCD diffractometer	3400 independent reflections
Radiation source: fine–focus sealed tube	2072 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −24→24
Tmin = 0.978, Tmax = 0.990	k = −8→8
14127 measured reflections	l = −30→30

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0597P)2 + 1.2286P] where P = (Fo2 + 2Fc2)/3
3400 reflections	(Δ/σ)max < 0.001
243 parameters	Δρmax = 0.28 e Å−3
3 restraints	Δρmin = −0.28 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.69131 (8)	0.1125 (2)	0.73867 (6)	0.0233 (4)
C1	0.65171 (12)	0.1096 (4)	0.69190 (10)	0.0229 (6)
C2	0.58358 (12)	0.0898 (4)	0.69845 (10)	0.0258 (6)
H2	0.5651	0.0824	0.7339	0.031*
C3	0.54256 (13)	0.0807 (4)	0.65176 (10)	0.0263 (6)
O2	0.47576 (9)	0.0548 (3)	0.65803 (8)	0.0367 (5)
H2A	0.4573	0.0329	0.6274	0.063 (11)*
C4	0.56984 (13)	0.0955 (4)	0.59938 (10)	0.0268 (6)
O3	0.52807 (9)	0.0810 (2)	0.55366 (7)	0.0313 (5)
C5	0.50843 (15)	0.2684 (4)	0.53157 (11)	0.0381 (7)
H5A	0.4789	0.2488	0.4993	0.057*
H5B	0.5486	0.3413	0.5210	0.057*
H5C	0.4844	0.3429	0.5593	0.057*
C6	0.63836 (13)	0.1158 (4)	0.59382 (10)	0.0248 (6)
O4	0.66442 (10)	0.1283 (3)	0.54307 (7)	0.0326 (5)
H4A	0.7066	0.1279	0.5456	0.079 (13)*
C7	0.68135 (12)	0.1217 (4)	0.64058 (9)	0.0223 (5)
C8	0.75264 (12)	0.1433 (4)	0.63673 (10)	0.0236 (6)
O5	0.78120 (9)	0.1632 (3)	0.59130 (7)	0.0314 (5)
C9	0.79061 (12)	0.1419 (4)	0.68777 (10)	0.0230 (6)
O6	0.85888 (8)	0.1730 (3)	0.68523 (7)	0.0308 (5)
C10	0.89618 (14)	0.0038 (5)	0.66731 (12)	0.0463 (8)
H10A	0.9442	0.0360	0.6666	0.069*
H10B	0.8805	−0.0341	0.6305	0.069*
H10C	0.8892	−0.1054	0.6927	0.069*
C11	0.75982 (12)	0.1256 (4)	0.73687 (10)	0.0227 (6)
C12	0.79011 (12)	0.1236 (3)	0.79246 (10)	0.0216 (5)
C13	0.85991 (12)	0.1219 (4)	0.80250 (10)	0.0264 (6)
H13	0.8895	0.1229	0.7725	0.032*
C14	0.88602 (13)	0.1188 (4)	0.85496 (10)	0.0253 (6)
H14	0.9334	0.1153	0.8609	0.030*
C15	0.84399 (12)	0.1208 (4)	0.89942 (10)	0.0225 (5)
O7	0.87539 (8)	0.1210 (3)	0.94962 (7)	0.0300 (4)
C16	0.83423 (14)	0.1220 (5)	0.99661 (10)	0.0407 (7)
H16A	0.8629	0.1224	1.0298	0.061*
H16B	0.8057	0.0047	0.9963	0.061*
H16C	0.8058	0.2396	0.9960	0.061*
C17	0.77463 (12)	0.1225 (4)	0.89071 (10)	0.0252 (6)
H17	0.7453	0.1239	0.9209	0.030*
C18	0.74882 (12)	0.1220 (4)	0.83780 (10)	0.0232 (6)
H18	0.7014	0.1206	0.8321	0.028*
O1W	0.88745 (11)	0.4465 (4)	0.57732 (8)	0.0492 (6)
H1A	0.8602 (15)	0.357 (4)	0.5866 (12)	0.074*
H1B	0.8908 (17)	0.435 (5)	0.5425 (7)	0.074*

	U11	U22	U33	U12	U13	U23
O1	0.0190 (9)	0.0306 (10)	0.0200 (9)	−0.0011 (7)	−0.0033 (7)	−0.0012 (8)
C1	0.0253 (13)	0.0201 (13)	0.0230 (13)	0.0015 (10)	−0.0049 (11)	−0.0001 (11)
C2	0.0245 (14)	0.0287 (15)	0.0243 (13)	0.0006 (11)	0.0005 (11)	−0.0022 (11)
C3	0.0240 (14)	0.0253 (15)	0.0294 (14)	−0.0005 (11)	−0.0028 (11)	−0.0007 (11)
O2	0.0221 (10)	0.0538 (14)	0.0340 (11)	−0.0035 (9)	−0.0051 (8)	−0.0030 (9)
C4	0.0340 (15)	0.0214 (14)	0.0246 (14)	0.0005 (11)	−0.0076 (11)	−0.0029 (11)
O3	0.0352 (11)	0.0284 (10)	0.0297 (10)	−0.0006 (8)	−0.0143 (8)	−0.0011 (8)
C5	0.0397 (17)	0.0334 (17)	0.0405 (17)	0.0053 (13)	−0.0154 (13)	0.0020 (13)
C6	0.0314 (15)	0.0206 (13)	0.0223 (13)	0.0029 (11)	−0.0003 (11)	−0.0013 (11)
O4	0.0339 (12)	0.0423 (12)	0.0217 (10)	0.0024 (9)	−0.0011 (8)	−0.0005 (8)
C7	0.0260 (13)	0.0190 (13)	0.0219 (13)	0.0025 (11)	−0.0018 (10)	−0.0010 (10)
C8	0.0277 (14)	0.0206 (13)	0.0226 (13)	0.0014 (11)	0.0029 (11)	−0.0005 (10)
O5	0.0288 (10)	0.0439 (12)	0.0217 (10)	0.0000 (9)	0.0026 (8)	0.0000 (8)
C9	0.0191 (13)	0.0246 (14)	0.0253 (13)	−0.0010 (10)	0.0012 (10)	−0.0005 (11)
O6	0.0211 (9)	0.0428 (12)	0.0285 (10)	−0.0036 (8)	0.0024 (8)	0.0014 (8)
C10	0.0263 (16)	0.072 (2)	0.0404 (17)	0.0160 (15)	0.0009 (13)	−0.0118 (16)
C11	0.0189 (13)	0.0216 (13)	0.0276 (14)	0.0014 (10)	−0.0004 (11)	−0.0009 (11)
C12	0.0229 (13)	0.0181 (13)	0.0238 (13)	−0.0001 (10)	−0.0028 (10)	−0.0014 (10)
C13	0.0236 (13)	0.0291 (14)	0.0267 (14)	−0.0003 (11)	0.0013 (11)	−0.0012 (12)
C14	0.0216 (13)	0.0264 (14)	0.0278 (14)	0.0005 (11)	−0.0027 (11)	0.0016 (11)
C15	0.0245 (13)	0.0189 (13)	0.0239 (13)	−0.0004 (10)	−0.0027 (11)	−0.0003 (10)
O7	0.0262 (10)	0.0426 (11)	0.0211 (9)	0.0009 (8)	−0.0041 (7)	0.0002 (8)
C16	0.0323 (16)	0.068 (2)	0.0211 (14)	−0.0006 (15)	−0.0012 (12)	0.0013 (14)
C17	0.0249 (14)	0.0281 (14)	0.0228 (13)	0.0010 (11)	0.0016 (11)	−0.0008 (11)
C18	0.0207 (13)	0.0242 (13)	0.0246 (13)	−0.0001 (11)	−0.0005 (10)	−0.0011 (11)
O1W	0.0424 (13)	0.0714 (17)	0.0334 (12)	−0.0225 (11)	−0.0046 (10)	0.0037 (11)

O1—C11	1.366 (3)	O6—C10	1.444 (3)
O1—C1	1.372 (3)	C10—H10A	0.9800
C1—C2	1.373 (3)	C10—H10B	0.9800
C1—C7	1.399 (3)	C10—H10C	0.9800
C2—C3	1.388 (3)	C11—C12	1.473 (3)
C2—H2	0.9500	C12—C18	1.393 (3)
C3—O2	1.351 (3)	C12—C13	1.403 (3)
C3—C4	1.404 (4)	C13—C14	1.372 (3)
O2—H2A	0.8400	C13—H13	0.9500
C4—C6	1.378 (4)	C14—C15	1.385 (3)
C4—O3	1.380 (3)	C14—H14	0.9500
O3—C5	1.436 (3)	C15—O7	1.363 (3)
C5—H5A	0.9800	C15—C17	1.390 (3)
C5—H5B	0.9800	O7—C16	1.424 (3)
C5—H5C	0.9800	C16—H16A	0.9800
C6—O4	1.357 (3)	C16—H16B	0.9800
C6—C7	1.411 (3)	C16—H16C	0.9800
O4—H4A	0.8400	C17—C18	1.379 (3)
C7—C8	1.429 (3)	C17—H17	0.9500
C8—O5	1.265 (3)	C18—H18	0.9500
C8—C9	1.442 (3)	O1W—H1A	0.852 (17)
C9—C11	1.363 (3)	O1W—H1B	0.859 (17)
C9—O6	1.376 (3)
C11—O1—C1	121.81 (19)	O6—C10—H10A	109.5
O1—C1—C2	116.9 (2)	O6—C10—H10B	109.5
O1—C1—C7	120.0 (2)	H10A—C10—H10B	109.5
C2—C1—C7	123.1 (2)	O6—C10—H10C	109.5
C1—C2—C3	118.1 (2)	H10A—C10—H10C	109.5
C1—C2—H2	121.0	H10B—C10—H10C	109.5
C3—C2—H2	121.0	C9—C11—O1	120.1 (2)
O2—C3—C2	118.2 (2)	C9—C11—C12	129.0 (2)
O2—C3—C4	120.9 (2)	O1—C11—C12	110.9 (2)
C2—C3—C4	120.9 (2)	C18—C12—C13	117.3 (2)
C3—O2—H2A	109.5	C18—C12—C11	119.8 (2)
C6—C4—O3	120.3 (2)	C13—C12—C11	122.9 (2)
C6—C4—C3	120.0 (2)	C14—C13—C12	121.0 (2)
O3—C4—C3	119.7 (2)	C14—C13—H13	119.5
C4—O3—C5	113.20 (19)	C12—C13—H13	119.5
O3—C5—H5A	109.5	C13—C14—C15	120.7 (2)
O3—C5—H5B	109.5	C13—C14—H14	119.7
H5A—C5—H5B	109.5	C15—C14—H14	119.7
O3—C5—H5C	109.5	O7—C15—C14	115.7 (2)
H5A—C5—H5C	109.5	O7—C15—C17	124.7 (2)
H5B—C5—H5C	109.5	C14—C15—C17	119.6 (2)
O4—C6—C4	119.6 (2)	C15—O7—C16	117.7 (2)
O4—C6—C7	120.1 (2)	O7—C16—H16A	109.5
C4—C6—C7	120.3 (2)	O7—C16—H16B	109.5
C6—O4—H4A	109.5	H16A—C16—H16B	109.5
C1—C7—C6	117.6 (2)	O7—C16—H16C	109.5
C1—C7—C8	120.2 (2)	H16A—C16—H16C	109.5
C6—C7—C8	122.2 (2)	H16B—C16—H16C	109.5
O5—C8—C7	122.3 (2)	C18—C17—C15	119.3 (2)
O5—C8—C9	121.5 (2)	C18—C17—H17	120.3
C7—C8—C9	116.2 (2)	C15—C17—H17	120.3
C11—C9—O6	121.0 (2)	C17—C18—C12	122.1 (2)
C11—C9—C8	121.6 (2)	C17—C18—H18	118.9
O6—C9—C8	117.2 (2)	C12—C18—H18	118.9
C9—O6—C10	113.8 (2)	H1A—O1W—H1B	105 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1Wi	0.84	1.92	2.712 (3)	157
O2—H2A···O3	0.84	2.33	2.780 (3)	114
O4—H4A···O5	0.84	1.85	2.589 (3)	146
O1W—H1A···O5	0.85 (2)	2.05 (2)	2.886 (3)	165 (3)
O1W—H1A···O6	0.85 (2)	2.71 (3)	3.288 (3)	126 (3)
O1W—H1B···O4ii	0.86 (2)	2.38 (2)	3.135 (3)	148 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1Wi	0.84	1.92	2.712 (3)	157
O2—H2A⋯O3	0.84	2.33	2.780 (3)	114
O4—H4A⋯O5	0.84	1.85	2.589 (3)	146
O1W—H1A⋯O5	0.85 (2)	2.05 (2)	2.886 (3)	165 (3)
O1W—H1A⋯O6	0.85 (2)	2.71 (3)	3.288 (3)	126 (3)
O1W—H1B⋯O4ii	0.86 (2)	2.38 (2)	3.135 (3)	148 (3)

Symmetry codes: (i) ; (ii) .