4',5-Dihy-droxy-7-meth-oxy-flavanone dihydrate.

The title compound, C(16)H(14)O(5)·2H(2)O [systematic name: 5-hy-droxy-2-(4-hy-droxy-phen-yl)-7-meth-oxy-chroman-4-one dihydrate], is a natural phytoalexin flavone isolated from the native chilean species Heliotropium taltalense and crystallizes with an organic mol-ecule and two water mol-ecules in the asymmetric unit. The 5-hy-droxy group forms a strong intra-molecular hydrogen bond with the carbonyl group, resulting in a six-membered ring. In the crystal, the components are linked by O-H⋯O hydrogen bonds, forming a three-dimensional network. The 4-hy-droxy-phenyl benzene ring is bonded equatorially to the pyrone ring, which adopts a slightly distorted sofa conformation. The title compound is the hydrated form of a previously reported structure [Shoja (1990 ▶). Acta Cryst. C46, 1969-1971]. There are only slight variations in the mol-ecular geometry between the two compounds.

Related literature

For the first study of the title compound, see: Narasimhachari & Seshadri (1949 ▶); Atkinson & Blakeman (1982 ▶). For its biological properties, see: Plowright et al. (1996 ▶); Atkinson & Blakeman (1982 ▶), Saito et al. (2008 ▶). For its spectroscopic properties, see: Agrawal (1989 ▶); Ogawa et al. (2007 ▶). For the structure of the unsolvated compound, see: Shoja (1990 ▶). For similar compounds, see: Modak et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For mol­ecular geometry calculations, see: Macrae et al. (2008 ▶).

Experimental

Crystal data

C16H14O5·2H2O

M = 322.30

Orthorhombic,

a = 5.0869 (10) Å

b = 9.4622 (19) Å

c = 32.318 (7) Å

V = 1555.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.20 × 0.15 × 0.03 mm

Data collection

Nonius KappaCCD area-detector diffractometer

9743 measured reflections

2021 independent reflections

1623 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.180

S = 1.17

2021 reflections

224 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶; cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811051221/kj2193sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051221/kj2193Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051221/kj2193Isup3.cml

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

C16H14O5·2H2O	F(000) = 680
Mr = 322.30	Dx = 1.376 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2419 reflections
a = 5.0869 (10) Å	θ = 3.3–28.4°
b = 9.4622 (19) Å	µ = 0.11 mm−1
c = 32.318 (7) Å	T = 293 K
V = 1555.6 (5) Å3	Block, yellow
Z = 4	0.20 × 0.15 × 0.03 mm

Nonius KappaCCD area-detector diffractometer	1623 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
graphite	θmax = 28.4°, θmin = 3.3°
φ and ω scans with κ offsets	h = 0→6
9743 measured reflections	k = 0→12
2021 independent reflections	l = −40→42

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0649P)2 + 1.4205P] where P = (Fo2 + 2Fc2)/3
2021 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.29 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	0.1698 (7)	0.3272 (3)	0.39766 (8)	0.0317 (8)
O2	−0.3650 (7)	0.5120 (4)	0.31855 (10)	0.0370 (9)
O3	−0.1585 (7)	0.3656 (4)	0.25747 (9)	0.0350 (8)
H3	−0.2576	0.4224	0.2686	0.053*
O4	0.5380 (7)	0.0576 (4)	0.28692 (9)	0.0341 (8)
O5	0.1305 (11)	0.5341 (6)	0.58135 (12)	0.0610 (15)
H5	0.247 (18)	0.564 (8)	0.593 (2)	0.07 (3)*
C2	0.0708 (9)	0.4690 (5)	0.40716 (13)	0.0266 (10)
H2	0.1893	0.5381	0.3945	0.032*
C3	−0.2023 (9)	0.4877 (6)	0.38806 (13)	0.0345 (12)
H3A	−0.3254	0.4250	0.4018	0.041*
H3B	−0.2613	0.5840	0.3924	0.041*
C4	−0.2002 (9)	0.4562 (5)	0.34223 (13)	0.0265 (10)
C10	−0.0071 (9)	0.3561 (5)	0.32828 (12)	0.0247 (9)
C5	0.0125 (9)	0.3128 (5)	0.28607 (12)	0.0248 (10)
C6	0.1952 (10)	0.2153 (5)	0.27344 (13)	0.0278 (10)
H6	0.2063	0.1899	0.2457	0.033*
C7	0.3658 (9)	0.1537 (5)	0.30263 (13)	0.0251 (9)
C8	0.3505 (9)	0.1902 (5)	0.34455 (13)	0.0267 (9)
H8	0.4586	0.1465	0.3639	0.032*
C9	0.1720 (8)	0.2925 (5)	0.35667 (12)	0.0221 (9)
C1'	0.0839 (9)	0.4870 (5)	0.45324 (13)	0.0265 (10)
C2'	−0.0739 (11)	0.4059 (6)	0.48002 (14)	0.0379 (12)
H2'	−0.1923	0.3410	0.4691	0.046*
C3'	−0.0542 (12)	0.4220 (6)	0.52256 (15)	0.0439 (14)
H3'	−0.1581	0.3673	0.5400	0.053*
C4'	0.1203 (10)	0.5197 (6)	0.53925 (13)	0.0367 (12)
C5'	0.2769 (12)	0.6004 (6)	0.51347 (15)	0.0441 (14)
H5'	0.3940	0.6656	0.5246	0.053*
C6'	0.2585 (11)	0.5837 (6)	0.47061 (14)	0.0361 (12)
H6'	0.3645	0.6381	0.4534	0.043*
C11	0.7076 (11)	−0.0153 (6)	0.31527 (15)	0.0364 (12)
H11A	0.6039	−0.0734	0.3334	0.055*
H11B	0.8043	0.0523	0.3314	0.055*
H11C	0.8280	−0.0737	0.3001	0.055*
O6	0.2193 (9)	0.7134 (5)	0.32036 (13)	0.0500 (11)
H6A	0.354 (18)	0.659 (8)	0.316 (2)	0.07 (2)*
H6B	0.209 (15)	0.761 (6)	0.2996 (19)	0.06 (2)*
O7	0.5931 (9)	0.6486 (6)	0.60698 (12)	0.0586 (13)
H7A	0.7450	0.6441	0.5961	0.088*
H7B	0.6306	0.6736	0.6315	0.088*

	U11	U22	U33	U12	U13	U23
O1	0.0332 (19)	0.0370 (19)	0.0248 (15)	0.0105 (18)	−0.0035 (13)	−0.0066 (13)
O2	0.0244 (17)	0.046 (2)	0.0406 (18)	0.0133 (18)	−0.0064 (14)	0.0006 (16)
O3	0.0334 (19)	0.039 (2)	0.0324 (16)	0.0081 (19)	−0.0069 (14)	0.0014 (14)
O4	0.0292 (18)	0.041 (2)	0.0324 (16)	0.0126 (17)	−0.0009 (14)	−0.0085 (14)
O5	0.061 (3)	0.096 (4)	0.0258 (18)	−0.028 (3)	0.0028 (19)	−0.006 (2)
C2	0.018 (2)	0.032 (2)	0.030 (2)	0.001 (2)	0.0035 (17)	−0.0057 (18)
C3	0.022 (2)	0.044 (3)	0.038 (2)	0.012 (3)	0.0049 (19)	−0.006 (2)
C4	0.018 (2)	0.029 (2)	0.032 (2)	0.000 (2)	−0.0033 (18)	0.0001 (18)
C10	0.018 (2)	0.028 (2)	0.028 (2)	−0.001 (2)	0.0005 (17)	−0.0006 (17)
C5	0.023 (2)	0.027 (2)	0.025 (2)	−0.005 (2)	−0.0066 (17)	0.0041 (17)
C6	0.032 (2)	0.031 (2)	0.0204 (19)	0.002 (2)	0.0008 (18)	−0.0029 (17)
C7	0.017 (2)	0.026 (2)	0.032 (2)	0.002 (2)	0.0021 (17)	−0.0008 (18)
C8	0.023 (2)	0.031 (2)	0.026 (2)	0.002 (2)	−0.0012 (17)	0.0009 (18)
C9	0.0115 (18)	0.029 (2)	0.0259 (19)	−0.0042 (19)	−0.0017 (15)	−0.0002 (17)
C1'	0.022 (2)	0.029 (2)	0.028 (2)	−0.001 (2)	−0.0004 (17)	−0.0030 (18)
C2'	0.032 (3)	0.048 (3)	0.033 (2)	−0.008 (3)	−0.002 (2)	−0.006 (2)
C3'	0.039 (3)	0.054 (4)	0.039 (3)	−0.012 (3)	0.012 (2)	0.003 (2)
C4'	0.034 (3)	0.050 (3)	0.027 (2)	−0.001 (3)	0.005 (2)	0.000 (2)
C5'	0.039 (3)	0.057 (4)	0.036 (3)	−0.008 (3)	−0.003 (2)	−0.009 (2)
C6'	0.029 (3)	0.047 (3)	0.031 (2)	−0.012 (2)	0.0050 (19)	−0.001 (2)
C11	0.027 (3)	0.040 (3)	0.042 (3)	0.014 (3)	0.000 (2)	−0.001 (2)
O6	0.048 (3)	0.058 (3)	0.044 (2)	0.020 (2)	0.007 (2)	0.001 (2)
O7	0.049 (3)	0.084 (3)	0.042 (2)	−0.008 (3)	−0.0053 (19)	−0.007 (2)

O1—C9	1.365 (5)	C7—C8	1.400 (6)
O1—C2	1.465 (5)	C8—C9	1.383 (6)
O2—C4	1.252 (5)	C8—H8	0.9300
O3—C5	1.364 (5)	C1'—C6'	1.393 (6)
O3—H3	0.8200	C1'—C2'	1.408 (7)
O4—C7	1.361 (5)	C2'—C3'	1.387 (7)
O4—C11	1.435 (6)	C2'—H2'	0.9300
O5—C4'	1.369 (6)	C3'—C4'	1.391 (7)
O5—H5	0.75 (8)	C3'—H3'	0.9300
C2—C1'	1.501 (6)	C4'—C5'	1.382 (7)
C2—C3	1.530 (6)	C5'—C6'	1.397 (6)
C2—H2	0.9800	C5'—H5'	0.9300
C3—C4	1.511 (6)	C6'—H6'	0.9300
C3—H3A	0.9700	C11—H11A	0.9600
C3—H3B	0.9700	C11—H11B	0.9600
C4—C10	1.437 (6)	C11—H11C	0.9600
C10—C9	1.426 (6)	O6—H6A	0.87 (9)
C10—C5	1.427 (6)	O6—H6B	0.81 (6)
C5—C6	1.372 (6)	O7—H7A	0.8500
C6—C7	1.408 (6)	O7—H7B	0.8501
C6—H6	0.9300
C9—O1—C2	115.3 (3)	C9—C8—H8	120.6
C5—O3—H3	109.5	C7—C8—H8	120.6
C7—O4—C11	118.0 (4)	O1—C9—C8	116.7 (4)
C4'—O5—H5	123 (6)	O1—C9—C10	121.2 (4)
O1—C2—C1'	107.3 (4)	C8—C9—C10	122.2 (4)
O1—C2—C3	109.5 (4)	C6'—C1'—C2'	118.3 (4)
C1'—C2—C3	115.3 (4)	C6'—C1'—C2	120.2 (4)
O1—C2—H2	108.2	C2'—C1'—C2	121.5 (4)
C1'—C2—H2	108.2	C3'—C2'—C1'	120.6 (5)
C3—C2—H2	108.2	C3'—C2'—H2'	119.7
C4—C3—C2	111.5 (4)	C1'—C2'—H2'	119.7
C4—C3—H3A	109.3	C2'—C3'—C4'	120.2 (5)
C2—C3—H3A	109.3	C2'—C3'—H3'	119.9
C4—C3—H3B	109.3	C4'—C3'—H3'	119.9
C2—C3—H3B	109.3	O5—C4'—C5'	121.5 (5)
H3A—C3—H3B	108.0	O5—C4'—C3'	118.4 (5)
O2—C4—C10	123.0 (4)	C5'—C4'—C3'	120.1 (5)
O2—C4—C3	120.7 (4)	C4'—C5'—C6'	119.8 (5)
C10—C4—C3	116.3 (4)	C4'—C5'—H5'	120.1
C9—C10—C5	116.7 (4)	C6'—C5'—H5'	120.1
C9—C10—C4	120.9 (4)	C1'—C6'—C5'	121.1 (4)
C5—C10—C4	122.4 (4)	C1'—C6'—H6'	119.5
O3—C5—C6	118.5 (4)	C5'—C6'—H6'	119.5
O3—C5—C10	119.9 (4)	O4—C11—H11A	109.5
C6—C5—C10	121.6 (4)	O4—C11—H11B	109.5
C5—C6—C7	119.8 (4)	H11A—C11—H11B	109.5
C5—C6—H6	120.1	O4—C11—H11C	109.5
C7—C6—H6	120.1	H11A—C11—H11C	109.5
O4—C7—C8	124.2 (4)	H11B—C11—H11C	109.5
O4—C7—C6	115.0 (4)	H6A—O6—H6B	105 (6)
C8—C7—C6	120.8 (4)	H7A—O7—H7B	101.2
C9—C8—C7	118.9 (4)
C9—O1—C2—C1'	−180.0 (4)	C2—O1—C9—C8	155.2 (4)
C9—O1—C2—C3	54.2 (5)	C2—O1—C9—C10	−26.6 (6)
O1—C2—C3—C4	−54.4 (5)	C7—C8—C9—O1	−178.2 (4)
C1'—C2—C3—C4	−175.4 (4)	C7—C8—C9—C10	3.6 (6)
C2—C3—C4—O2	−153.5 (5)	C5—C10—C9—O1	179.7 (4)
C2—C3—C4—C10	28.6 (6)	C4—C10—C9—O1	−1.7 (6)
O2—C4—C10—C9	−178.3 (4)	C5—C10—C9—C8	−2.2 (6)
C3—C4—C10—C9	−0.5 (6)	C4—C10—C9—C8	176.4 (4)
O2—C4—C10—C5	0.3 (7)	O1—C2—C1'—C6'	112.6 (5)
C3—C4—C10—C5	178.0 (4)	C3—C2—C1'—C6'	−125.2 (5)
C9—C10—C5—O3	177.7 (4)	O1—C2—C1'—C2'	−66.1 (6)
C4—C10—C5—O3	−0.9 (7)	C3—C2—C1'—C2'	56.1 (6)
C9—C10—C5—C6	−0.2 (6)	C6'—C1'—C2'—C3'	−0.3 (8)
C4—C10—C5—C6	−178.8 (4)	C2—C1'—C2'—C3'	178.5 (5)
O3—C5—C6—C7	−176.9 (4)	C1'—C2'—C3'—C4'	0.6 (8)
C10—C5—C6—C7	1.1 (7)	C2'—C3'—C4'—O5	178.9 (5)
C11—O4—C7—C8	2.6 (7)	C2'—C3'—C4'—C5'	−0.6 (9)
C11—O4—C7—C6	−176.5 (4)	O5—C4'—C5'—C6'	−179.3 (5)
C5—C6—C7—O4	179.5 (4)	C3'—C4'—C5'—C6'	0.2 (9)
C5—C6—C7—C8	0.4 (7)	C2'—C1'—C6'—C5'	−0.1 (8)
O4—C7—C8—C9	178.2 (4)	C2—C1'—C6'—C5'	−178.9 (5)
C6—C7—C8—C9	−2.7 (7)	C4'—C5'—C6'—C1'	0.2 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.90	2.630 (5)	147
O5—H5···O7	0.76 (9)	1.99 (9)	2.720 (7)	163 (7)
O6—H6A···O2i	0.87 (9)	2.00 (8)	2.847 (6)	166 (7)
O6—H6B···O3ii	0.81 (6)	2.11 (6)	2.915 (5)	174 (8)
O7—H7A···O5i	0.85	2.27	3.055 (7)	153
O7—H7B···O6iii	0.85	1.94	2.763 (6)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.90	2.630 (5)	147
O5—H5⋯O7	0.76 (9)	1.99 (9)	2.720 (7)	163 (7)
O6—H6A⋯O2i	0.87 (9)	2.00 (8)	2.847 (6)	166 (7)
O6—H6B⋯O3ii	0.81 (6)	2.11 (6)	2.915 (5)	174 (8)
O7—H7A⋯O5i	0.85	2.27	3.055 (7)	153
O7—H7B⋯O6iii	0.85	1.94	2.763 (6)	163

Symmetry codes: (i) ; (ii) ; (iii) .