Oxyresveratrol from Mulberry as a dihydrate.

The title compound {systematic name: 4-[(E)-2-(3,5-dihy-droxy-phen-yl)ethen-yl]benzene-1,3-diol dihydrate}, C(14)H(12)O(4)·2H(2)O, a derivative of resveratrol, was isolated from mulberry. The linking C=C double bond has a trans conformation and allows the formation of a conjugated system throughout the mol-ecule. The dihedral angle between the benzene rings is 9.39 (9)°. In the crystal, mol-ecules are connected into a three-dimensional architecture through O-H⋯O hydrogen bonds between hy-droxy groups of oxyresveratrol and solvent water mol-ecules.

Related literature

For medicinal properties and the biological activity of oxyresveratrol, see: Mongolsuk et al. (1957 ▶); Charoenlarp et al. (1981 ▶, 1989 ▶); Zheng et al. (2010 ▶, 2011 ▶); Kim et al. (2002 ▶, 2004 ▶); Shin et al. (1998 ▶); Lipipun et al. (2011 ▶); Galindo et al. (2011 ▶); Sasivimolphan et al. (2009 ▶); Chuanasa et al. (2008 ▶); Likhitwitayawuid (2008 ▶); Likhitwitayawuid et al. (2005 ▶, 2006 ▶); Liu et al. (2009 ▶); Breuer et al. (2006 ▶); Chung et al. (2003 ▶); Chao et al. (2008 ▶); Ban et al. (2006 ▶, 2008 ▶); Breuer et al. (2006 ▶); Andrabi et al. (2004 ▶). For related structures, see: Piao et al. (2009 ▶); Qiu et al.(1996 ▶); Hano et al. (1986 ▶).

Experimental

Crystal data

C14H12O4·2H2O

M = 280.27

Triclinic,

a = 6.6523 (5) Å

b = 9.2005 (9) Å

c = 11.5294 (8) Å

α = 72.533 (7)°

β = 78.686 (6)°

γ = 79.651 (7)°

V = 654.51 (9) Å3

Z = 2

Cu Kα radiation

μ = 0.95 mm−1

T = 293 K

0.40 × 0.30 × 0.20 mm

Data collection

Agilent Xcalibur Onyx Nova diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.704, T max = 0.834

4145 measured reflections

2297 independent reflections

2002 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.141

S = 1.13

2297 reflections

197 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014018/tk5080sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812014018/tk5080Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014018/tk5080Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812014018/tk5080Isup4.cml

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

C14H12O4·2H2O	Z = 2
Mr = 280.27	F(000) = 296
Triclinic, P1	Dx = 1.422 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 6.6523 (5) Å	Cell parameters from 2627 reflections
b = 9.2005 (9) Å	θ = 4.1–71.3°
c = 11.5294 (8) Å	µ = 0.95 mm−1
α = 72.533 (7)°	T = 293 K
β = 78.686 (6)°	Block, colourless
γ = 79.651 (7)°	0.40 × 0.30 × 0.20 mm
V = 654.51 (9) Å3

Agilent Xcalibur Onyx Nova diffractometer	2297 independent reflections
Radiation source: Nova (Cu) X-ray Source	2002 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.022
Detector resolution: 8.2417 pixels mm-1	θmax = 66.6°, θmin = 4.1°
ω scans	h = −7→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −10→8
Tmin = 0.704, Tmax = 0.834	l = −13→13
4145 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.081P)2 + 0.176P] where P = (Fo2 + 2Fc2)/3
2297 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.50 e Å−3
5 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	−0.1126 (3)	0.9054 (2)	0.76812 (16)	0.0253 (4)
C2	−0.2896 (3)	0.8772 (2)	0.85658 (16)	0.0251 (4)
C3	−0.4773 (3)	0.9699 (2)	0.84350 (16)	0.0260 (4)
H3	−0.5945	0.9490	0.9051	0.031*
C4	−0.4925 (3)	1.0933 (2)	0.73988 (17)	0.0270 (4)
C5	−0.3191 (3)	1.1277 (2)	0.65217 (18)	0.0304 (4)
H5	−0.3286	1.2143	0.5825	0.036*
C6	−0.1329 (3)	1.0347 (2)	0.66730 (17)	0.0291 (4)
H6	−0.0149	1.0594	0.6073	0.035*
C7	0.0785 (3)	0.7976 (2)	0.78124 (16)	0.0265 (4)
H7	0.0724	0.7073	0.8482	0.032*
C8	0.2599 (3)	0.8143 (2)	0.70802 (17)	0.0266 (4)
H8	0.2682	0.9072	0.6438	0.032*
C9	0.4478 (3)	0.7025 (2)	0.71754 (16)	0.0241 (4)
C10	0.6184 (3)	0.7319 (2)	0.62552 (16)	0.0258 (4)
H10	0.6122	0.8242	0.5605	0.031*
C11	0.7979 (3)	0.6264 (2)	0.62855 (16)	0.0257 (4)
C12	0.8084 (3)	0.4895 (2)	0.72244 (17)	0.0273 (4)
H12	0.9292	0.4163	0.7238	0.033*
C13	0.6385 (3)	0.4623 (2)	0.81404 (16)	0.0260 (4)
C14	0.4594 (3)	0.5662 (2)	0.81327 (16)	0.0257 (4)
H14	0.3454	0.5451	0.8771	0.031*
O1	−0.27079 (18)	0.75380 (14)	0.95877 (12)	0.0298 (3)
H1	−0.3888	0.7321	0.9944	0.045*
O2	−0.68101 (19)	1.17941 (15)	0.72308 (13)	0.0352 (4)
H2	−0.6634	1.2691	0.6802	0.053*
O3	0.95691 (19)	0.66150 (15)	0.53537 (12)	0.0316 (3)
H3A	1.0617	0.5971	0.5509	0.047*
O4	0.64072 (19)	0.32934 (15)	0.90904 (12)	0.0330 (4)
H4	0.7589	0.2786	0.9044	0.049*
O5	0.01297 (19)	0.14910 (15)	0.92354 (12)	0.0318 (3)
H5A	0.085 (3)	0.187 (3)	0.963 (2)	0.048*
H5B	0.095 (3)	0.148 (3)	0.8524 (14)	0.048*
O6	0.67051 (19)	0.52209 (15)	0.40983 (12)	0.0300 (3)
H6A	0.637 (4)	0.490 (3)	0.3506 (17)	0.045*
H6B	0.701 (7)	0.618 (2)	0.394 (4)	0.045*	0.50
H6C	0.565 (6)	0.513 (6)	0.472 (3)	0.045*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0192 (9)	0.0256 (9)	0.0278 (9)	−0.0011 (7)	−0.0025 (7)	−0.0043 (7)
C2	0.0202 (8)	0.0243 (9)	0.0270 (9)	−0.0018 (6)	−0.0028 (7)	−0.0025 (7)
C3	0.0182 (8)	0.0268 (9)	0.0285 (9)	−0.0011 (7)	0.0012 (7)	−0.0051 (7)
C4	0.0187 (8)	0.0261 (9)	0.0322 (9)	0.0029 (7)	−0.0031 (7)	−0.0057 (7)
C5	0.0249 (9)	0.0280 (9)	0.0300 (9)	0.0003 (7)	−0.0011 (7)	0.0003 (7)
C6	0.0190 (8)	0.0307 (10)	0.0301 (9)	−0.0006 (7)	0.0017 (7)	−0.0023 (8)
C7	0.0220 (9)	0.0234 (9)	0.0295 (9)	0.0010 (7)	−0.0047 (7)	−0.0023 (7)
C8	0.0217 (9)	0.0224 (9)	0.0314 (9)	0.0006 (7)	−0.0037 (7)	−0.0034 (7)
C9	0.0204 (8)	0.0234 (9)	0.0280 (9)	−0.0009 (6)	−0.0029 (7)	−0.0080 (7)
C10	0.0211 (9)	0.0239 (9)	0.0290 (9)	−0.0010 (7)	−0.0025 (7)	−0.0042 (7)
C11	0.0195 (8)	0.0280 (9)	0.0273 (9)	−0.0042 (7)	−0.0002 (7)	−0.0056 (7)
C12	0.0182 (8)	0.0271 (9)	0.0318 (10)	0.0018 (7)	−0.0029 (7)	−0.0043 (7)
C13	0.0205 (8)	0.0266 (9)	0.0269 (9)	−0.0025 (7)	−0.0021 (7)	−0.0029 (7)
C14	0.0175 (8)	0.0303 (9)	0.0261 (9)	−0.0009 (7)	0.0003 (7)	−0.0066 (7)
O1	0.0184 (6)	0.0289 (7)	0.0309 (7)	−0.0003 (5)	−0.0007 (5)	0.0049 (5)
O2	0.0210 (7)	0.0280 (7)	0.0427 (8)	0.0060 (5)	−0.0017 (6)	0.0036 (6)
O3	0.0180 (6)	0.0314 (7)	0.0341 (7)	0.0013 (5)	0.0036 (5)	0.0003 (5)
O4	0.0189 (6)	0.0316 (7)	0.0333 (7)	0.0035 (5)	0.0022 (5)	0.0059 (6)
O5	0.0238 (7)	0.0339 (7)	0.0329 (7)	0.0019 (5)	−0.0046 (5)	−0.0050 (6)
O6	0.0239 (7)	0.0299 (7)	0.0343 (8)	−0.0026 (5)	−0.0023 (5)	−0.0078 (6)

C1—C6	1.399 (3)	C10—C11	1.396 (2)
C1—C2	1.405 (2)	C10—H10	0.9500
C1—C7	1.468 (2)	C11—O3	1.359 (2)
C2—O1	1.377 (2)	C11—C12	1.394 (3)
C2—C3	1.387 (2)	C12—C13	1.389 (2)
C3—C4	1.385 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—O4	1.376 (2)
C4—O2	1.373 (2)	C13—C14	1.387 (2)
C4—C5	1.391 (3)	C14—H14	0.9500
C5—C6	1.382 (3)	O1—H1	0.8400
C5—H5	0.9500	O2—H2	0.8400
C6—H6	0.9500	O3—H3A	0.8400
C7—C8	1.335 (3)	O4—H4	0.8400
C7—H7	0.9500	O5—H5A	0.890 (10)
C8—C9	1.469 (2)	O5—H5B	0.893 (10)
C8—H8	0.9500	O6—H6A	0.897 (10)
C9—C10	1.397 (2)	O6—H6B	0.894 (10)
C9—C14	1.402 (2)	O6—H6C	0.896 (10)
C6—C1—C2	116.74 (16)	C10—C9—C8	118.39 (16)
C6—C1—C7	123.22 (15)	C14—C9—C8	122.38 (15)
C2—C1—C7	119.97 (16)	C11—C10—C9	120.38 (16)
O1—C2—C3	120.45 (15)	C11—C10—H10	119.8
O1—C2—C1	117.62 (15)	C9—C10—H10	119.8
C3—C2—C1	121.93 (16)	O3—C11—C12	122.21 (15)
C4—C3—C2	119.39 (16)	O3—C11—C10	117.25 (16)
C4—C3—H3	120.3	C12—C11—C10	120.51 (16)
C2—C3—H3	120.3	C13—C12—C11	118.52 (16)
O2—C4—C3	119.43 (15)	C13—C12—H12	120.7
O2—C4—C5	120.23 (16)	C11—C12—H12	120.7
C3—C4—C5	120.32 (16)	O4—C13—C14	117.15 (15)
C6—C5—C4	119.44 (17)	O4—C13—C12	120.98 (15)
C6—C5—H5	120.3	C14—C13—C12	121.86 (16)
C4—C5—H5	120.3	C13—C14—C9	119.49 (15)
C5—C6—C1	122.11 (16)	C13—C14—H14	120.3
C5—C6—H6	118.9	C9—C14—H14	120.3
C1—C6—H6	118.9	C2—O1—H1	109.5
C8—C7—C1	126.20 (16)	C4—O2—H2	109.5
C8—C7—H7	116.9	C11—O3—H3A	109.5
C1—C7—H7	116.9	C13—O4—H4	109.5
C7—C8—C9	126.05 (17)	H5A—O5—H5B	104 (2)
C7—C8—H8	117.0	H6A—O6—H6B	119 (4)
C9—C8—H8	117.0	H6A—O6—H6C	109 (4)
C10—C9—C14	119.21 (15)	H6B—O6—H6C	106 (5)
C6—C1—C2—O1	−177.63 (15)	C1—C7—C8—C9	−176.59 (16)
C7—C1—C2—O1	5.2 (3)	C7—C8—C9—C10	173.61 (18)
C6—C1—C2—C3	1.8 (3)	C7—C8—C9—C14	−4.5 (3)
C7—C1—C2—C3	−175.39 (16)	C14—C9—C10—C11	0.3 (3)
O1—C2—C3—C4	−179.97 (16)	C8—C9—C10—C11	−177.84 (16)
C1—C2—C3—C4	0.7 (3)	C9—C10—C11—O3	179.27 (15)
C2—C3—C4—O2	175.96 (16)	C9—C10—C11—C12	0.9 (3)
C2—C3—C4—C5	−2.6 (3)	O3—C11—C12—C13	−179.80 (16)
O2—C4—C5—C6	−176.49 (17)	C10—C11—C12—C13	−1.5 (3)
C3—C4—C5—C6	2.1 (3)	C11—C12—C13—O4	−179.83 (16)
C4—C5—C6—C1	0.5 (3)	C11—C12—C13—C14	1.0 (3)
C2—C1—C6—C5	−2.3 (3)	O4—C13—C14—C9	−179.06 (15)
C7—C1—C6—C5	174.73 (18)	C12—C13—C14—C9	0.2 (3)
C6—C1—C7—C8	6.8 (3)	C10—C9—C14—C13	−0.8 (3)
C2—C1—C7—C8	−176.28 (18)	C8—C9—C14—C13	177.25 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.84	1.90	2.7329 (18)	173
O2—H2···O6ii	0.84	1.89	2.720 (2)	171
O3—H3A···O6iii	0.84	1.97	2.8045 (19)	169
O4—H4···O5iv	0.84	1.89	2.7259 (19)	170
O5—H5A···O1i	0.89 (2)	1.90 (2)	2.7879 (19)	172 (2)
O5—H5B···O2v	0.89 (2)	1.88 (2)	2.7449 (19)	161 (2)
O6—H6B···O2ii	0.90 (3)	1.95 (3)	2.720 (2)	143 (4)
O6—H6C···O6vi	0.90 (4)	1.87 (4)	2.7583 (19)	172 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.84	1.90	2.7329 (18)	173
O2—H2⋯O6ii	0.84	1.89	2.720 (2)	171
O3—H3A⋯O6iii	0.84	1.97	2.8045 (19)	169
O4—H4⋯O5iv	0.84	1.89	2.7259 (19)	170
O5—H5A⋯O1i	0.89 (2)	1.90 (2)	2.7879 (19)	172 (2)
O5—H5B⋯O2v	0.89 (2)	1.88 (2)	2.7449 (19)	161 (2)
O6—H6B⋯O2ii	0.90 (3)	1.95 (3)	2.720 (2)	143 (4)
O6—H6C⋯O6vi	0.90 (4)	1.87 (4)	2.7583 (19)	172 (5)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .