5-[2-(4-Acetyl-oxyphen-yl)ethen-yl]benzene-1,3-diyl diacetate.

The title compound, C(20)H(18)O(6), was prepared from resveratrol {systematic name: 5-[(E)-2-(4-hy-droxy-phen-yl)ethen-yl]ben-z-ene-1,3-diol}, which can be isolated from grapes, through triacetyl-ation with using acetic anhydride in pyridine. The two benzene rings are approximately coplanar, making a dihedral angle of 6.64 (14)°, and the three acet-oxy group are located on the same side of the plane. The skeleton of the compound resembles a table with three legs. In the crystal, mol-ecules are linked via C-H⋯O interactions, forming inversion dimers. These dimers are further linked via C-H⋯O interactions, forming a three-dimensional structure.

Related literature

For background to this class of compound, see: González-Barrio et al. (2006 ▶). For the preparation of the title compound, see: Sarpierto et al. (2007 ▶). For a study of its potential use in radioprotective drug development, see: Koide et al. (2011 ▶).

Experimental

Crystal data

C20H18O6

M = 354.34

Monoclinic,

a = 31.520 (6) Å

b = 6.1211 (12) Å

c = 20.110 (4) Å

β = 110.92 (3)°

V = 3624.2 (14) Å3

Z = 8

Cu Kα radiation

μ = 0.80 mm−1

T = 296 K

0.23 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.837, T max = 0.939

11742 measured reflections

3181 independent reflections

2532 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.191

S = 1.05

3181 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811044722/rk2305sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044722/rk2305Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044722/rk2305Isup3.cml

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

C20H18O6	F(000) = 1488
Mr = 354.34	Dx = 1.299 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 3228 reflections
a = 31.520 (6) Å	θ = 4.7–67.0°
b = 6.1211 (12) Å	µ = 0.80 mm−1
c = 20.110 (4) Å	T = 296 K
β = 110.92 (3)°	Block, colourless
V = 3624.2 (14) Å3	0.23 × 0.10 × 0.08 mm
Z = 8

Bruker APEXII CCD diffractometer	3181 independent reflections
Radiation source: fine-focus sealed tube	2532 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 67.0°, θmin = 4.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −37→36
Tmin = 0.837, Tmax = 0.939	k = −7→7
11742 measured reflections	l = −19→24

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1023P)2 + 2.2789P] where P = (Fo2 + 2Fc2)/3
3181 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.19 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 > 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	0.16481 (6)	0.7332 (3)	0.46756 (9)	0.0754 (5)
O2	0.21472 (8)	0.5358 (4)	0.43718 (12)	0.0992 (7)
O3	0.21702 (7)	1.1732 (4)	0.29763 (12)	0.0906 (6)
O4	0.14826 (6)	1.2873 (3)	0.29000 (10)	0.0714 (5)
O5	−0.11728 (7)	0.1955 (4)	−0.02189 (12)	0.1001 (7)
O6	−0.07902 (11)	0.0003 (4)	−0.07410 (13)	0.1110 (8)
C1	0.08924 (7)	0.7665 (4)	0.28105 (13)	0.0645 (6)
C2	0.10294 (7)	0.9669 (4)	0.26198 (12)	0.0646 (6)
H2A	0.0887	1.0215	0.2162	0.077*
C3	0.13752 (7)	1.0835 (4)	0.31104 (12)	0.0600 (5)
C4	0.15881 (7)	1.0105 (4)	0.37985 (12)	0.0620 (6)
H4A	0.1815	1.0918	0.4130	0.074*
C5	0.14503 (8)	0.8119 (4)	0.39738 (12)	0.0617 (6)
C6	0.11048 (8)	0.6919 (4)	0.34968 (13)	0.0642 (6)
H6A	0.1015	0.5605	0.3638	0.077*
C7	0.05373 (8)	0.6257 (5)	0.23138 (15)	0.0767 (7)
H7A	0.0469	0.4975	0.2502	0.092*
C8	0.03135 (9)	0.6616 (5)	0.16494 (15)	0.0761 (7)
H8A	0.0389	0.7872	0.1456	0.091*
C9	−0.00525 (8)	0.5237 (5)	0.11593 (16)	0.0741 (7)
C10	−0.01673 (9)	0.3156 (5)	0.13435 (16)	0.0803 (8)
H10A	0.0004	0.2548	0.1781	0.096*
C11	−0.05336 (9)	0.2001 (5)	0.08785 (16)	0.0792 (7)
H11A	−0.0613	0.0633	0.1000	0.095*
C12	−0.07737 (9)	0.2943 (5)	0.02379 (16)	0.0772 (7)
C13	−0.06570 (10)	0.4942 (5)	0.00422 (17)	0.0835 (8)
H13A	−0.0823	0.5524	−0.0402	0.100*
C14	−0.02968 (10)	0.6077 (5)	0.05012 (16)	0.0808 (7)
H14A	−0.0217	0.7424	0.0366	0.097*
C15	0.19909 (8)	0.5858 (4)	0.48039 (14)	0.0699 (6)
C16	0.21382 (11)	0.5035 (6)	0.55443 (17)	0.0948 (9)
H16A	0.2381	0.4006	0.5623	0.142*
H16B	0.1887	0.4330	0.5621	0.142*
H16C	0.2242	0.6235	0.5870	0.142*
C17	0.18971 (9)	1.3158 (4)	0.28572 (12)	0.0668 (6)
C18	0.19501 (12)	1.5425 (5)	0.26272 (19)	0.0925 (9)
H18A	0.2247	1.5590	0.2602	0.139*
H18B	0.1914	1.6449	0.2965	0.139*
H18C	0.1724	1.5698	0.2167	0.139*
C19	−0.11458 (13)	0.0548 (5)	−0.07061 (14)	0.0847 (8)
C20	−0.16046 (14)	−0.0225 (7)	−0.11694 (17)	0.1184 (14)
H20A	−0.1575	−0.1227	−0.1518	0.178*
H20B	−0.1785	0.1002	−0.1406	0.178*
H20C	−0.1749	−0.0949	−0.0883	0.178*

	U11	U22	U33	U12	U13	U23
O1	0.0720 (10)	0.0922 (12)	0.0612 (10)	0.0095 (9)	0.0228 (8)	0.0065 (8)
O2	0.0966 (14)	0.1150 (17)	0.0855 (14)	0.0354 (13)	0.0319 (12)	0.0047 (12)
O3	0.0806 (12)	0.1032 (15)	0.1010 (15)	0.0186 (11)	0.0483 (11)	0.0178 (11)
O4	0.0629 (9)	0.0650 (10)	0.0877 (12)	0.0039 (7)	0.0287 (8)	0.0061 (8)
O5	0.0743 (12)	0.1182 (17)	0.0978 (15)	−0.0211 (11)	0.0186 (11)	−0.0451 (13)
O6	0.141 (2)	0.1095 (18)	0.0868 (15)	−0.0075 (16)	0.0461 (15)	−0.0264 (12)
C1	0.0513 (11)	0.0761 (15)	0.0679 (14)	−0.0055 (10)	0.0235 (10)	−0.0116 (11)
C2	0.0519 (11)	0.0831 (16)	0.0554 (12)	0.0072 (11)	0.0150 (10)	−0.0011 (11)
C3	0.0544 (11)	0.0611 (12)	0.0664 (13)	0.0046 (10)	0.0239 (10)	−0.0005 (10)
C4	0.0534 (11)	0.0670 (14)	0.0632 (13)	−0.0008 (10)	0.0178 (10)	−0.0098 (10)
C5	0.0565 (12)	0.0715 (14)	0.0577 (12)	0.0044 (10)	0.0212 (10)	−0.0025 (10)
C6	0.0607 (13)	0.0670 (14)	0.0685 (14)	−0.0035 (10)	0.0275 (11)	−0.0031 (11)
C7	0.0627 (14)	0.0930 (18)	0.0749 (16)	−0.0060 (13)	0.0252 (12)	−0.0037 (14)
C8	0.0691 (15)	0.0825 (17)	0.0778 (17)	−0.0064 (13)	0.0277 (13)	−0.0042 (13)
C9	0.0584 (13)	0.0822 (17)	0.0881 (18)	−0.0114 (12)	0.0338 (13)	−0.0290 (14)
C10	0.0642 (14)	0.097 (2)	0.0773 (16)	0.0033 (13)	0.0220 (12)	−0.0157 (14)
C11	0.0681 (15)	0.0801 (17)	0.0874 (19)	−0.0074 (12)	0.0255 (14)	−0.0200 (14)
C12	0.0637 (14)	0.0838 (18)	0.0844 (18)	−0.0133 (13)	0.0266 (13)	−0.0318 (14)
C13	0.0751 (16)	0.096 (2)	0.0774 (17)	−0.0051 (14)	0.0248 (14)	−0.0176 (14)
C14	0.0764 (16)	0.0869 (18)	0.0805 (18)	−0.0104 (14)	0.0299 (14)	−0.0170 (14)
C15	0.0592 (13)	0.0694 (14)	0.0734 (15)	−0.0003 (11)	0.0143 (11)	0.0024 (12)
C16	0.0807 (18)	0.110 (2)	0.085 (2)	0.0081 (17)	0.0194 (15)	0.0267 (17)
C17	0.0672 (14)	0.0792 (16)	0.0565 (12)	0.0017 (12)	0.0253 (11)	−0.0013 (11)
C18	0.104 (2)	0.088 (2)	0.102 (2)	−0.0070 (17)	0.0569 (19)	0.0091 (16)
C19	0.114 (2)	0.0813 (18)	0.0563 (14)	−0.0215 (17)	0.0277 (15)	−0.0038 (13)
C20	0.147 (3)	0.118 (3)	0.0649 (17)	−0.054 (2)	0.0076 (19)	−0.0127 (17)

O1—C15	1.360 (3)	C9—C14	1.372 (4)
O1—C5	1.409 (3)	C9—C10	1.409 (4)
O2—C15	1.182 (3)	C10—C11	1.392 (4)
O3—C17	1.188 (3)	C10—H10A	0.9300
O4—C17	1.351 (3)	C11—C12	1.367 (4)
O4—C3	1.397 (3)	C11—H11A	0.9300
O5—C19	1.330 (4)	C12—C13	1.375 (4)
O5—C12	1.403 (3)	C13—C14	1.369 (4)
O6—C19	1.195 (4)	C13—H13A	0.9300
C1—C6	1.379 (3)	C14—H14A	0.9300
C1—C2	1.399 (4)	C15—C16	1.481 (4)
C1—C7	1.481 (4)	C16—H16A	0.9600
C2—C3	1.380 (3)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C3—C4	1.379 (3)	C17—C18	1.491 (4)
C4—C5	1.378 (3)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.378 (3)	C18—H18C	0.9600
C6—H6A	0.9300	C19—C20	1.490 (5)
C7—C8	1.288 (4)	C20—H20A	0.9600
C7—H7A	0.9300	C20—H20B	0.9600
C8—C9	1.484 (4)	C20—H20C	0.9600
C8—H8A	0.9300
C15—O1—C5	117.03 (19)	C11—C12—C13	122.0 (3)
C17—O4—C3	118.62 (19)	C11—C12—O5	120.0 (3)
C19—O5—C12	118.9 (2)	C13—C12—O5	117.7 (3)
C6—C1—C2	118.5 (2)	C14—C13—C12	120.0 (3)
C6—C1—C7	117.5 (2)	C14—C13—H13A	120.0
C2—C1—C7	123.9 (2)	C12—C13—H13A	120.0
C3—C2—C1	120.0 (2)	C13—C14—C9	120.3 (3)
C3—C2—H2A	120.0	C13—C14—H14A	119.8
C1—C2—H2A	120.0	C9—C14—H14A	119.8
C4—C3—C2	121.8 (2)	O2—C15—O1	123.0 (2)
C4—C3—O4	120.6 (2)	O2—C15—C16	126.0 (3)
C2—C3—O4	117.4 (2)	O1—C15—C16	111.0 (2)
C5—C4—C3	117.2 (2)	C15—C16—H16A	109.5
C5—C4—H4A	121.4	C15—C16—H16B	109.5
C3—C4—H4A	121.4	H16A—C16—H16B	109.5
C4—C5—C6	122.3 (2)	C15—C16—H16C	109.5
C4—C5—O1	119.4 (2)	H16A—C16—H16C	109.5
C6—C5—O1	118.2 (2)	H16B—C16—H16C	109.5
C5—C6—C1	120.0 (2)	O3—C17—O4	122.7 (2)
C5—C6—H6A	120.0	O3—C17—C18	126.3 (3)
C1—C6—H6A	120.0	O4—C17—C18	111.0 (2)
C8—C7—C1	127.1 (3)	C17—C18—H18A	109.5
C8—C7—H7A	116.5	C17—C18—H18B	109.5
C1—C7—H7A	116.5	H18A—C18—H18B	109.5
C7—C8—C9	126.9 (3)	C17—C18—H18C	109.5
C7—C8—H8A	116.6	H18A—C18—H18C	109.5
C9—C8—H8A	116.6	H18B—C18—H18C	109.5
C14—C9—C10	118.9 (2)	O6—C19—O5	122.2 (3)
C14—C9—C8	117.6 (3)	O6—C19—C20	126.5 (3)
C10—C9—C8	123.4 (3)	O5—C19—C20	111.3 (3)
C11—C10—C9	120.8 (3)	C19—C20—H20A	109.5
C11—C10—H10A	119.6	C19—C20—H20B	109.5
C9—C10—H10A	119.6	H20A—C20—H20B	109.5
C12—C11—C10	117.8 (3)	C19—C20—H20C	109.5
C12—C11—H11A	121.1	H20A—C20—H20C	109.5
C10—C11—H11A	121.1	H20B—C20—H20C	109.5
C6—C1—C2—C3	1.1 (3)	C7—C8—C9—C10	−8.3 (4)
C7—C1—C2—C3	−177.6 (2)	C14—C9—C10—C11	−2.5 (4)
C1—C2—C3—C4	−1.4 (3)	C8—C9—C10—C11	175.7 (2)
C1—C2—C3—O4	−177.03 (19)	C9—C10—C11—C12	0.6 (4)
C17—O4—C3—C4	68.8 (3)	C10—C11—C12—C13	1.4 (4)
C17—O4—C3—C2	−115.5 (2)	C10—C11—C12—O5	−173.5 (2)
C2—C3—C4—C5	1.8 (3)	C19—O5—C12—C11	−91.5 (3)
O4—C3—C4—C5	177.33 (19)	C19—O5—C12—C13	93.4 (3)
C3—C4—C5—C6	−2.1 (3)	C11—C12—C13—C14	−1.6 (4)
C3—C4—C5—O1	−178.2 (2)	O5—C12—C13—C14	173.4 (3)
C15—O1—C5—C4	−98.1 (3)	C12—C13—C14—C9	−0.4 (4)
C15—O1—C5—C6	85.7 (3)	C10—C9—C14—C13	2.4 (4)
C4—C5—C6—C1	1.9 (3)	C8—C9—C14—C13	−175.9 (2)
O1—C5—C6—C1	178.0 (2)	C5—O1—C15—O2	5.8 (4)
C2—C1—C6—C5	−1.3 (3)	C5—O1—C15—C16	−175.1 (2)
C7—C1—C6—C5	177.4 (2)	C3—O4—C17—O3	1.7 (4)
C6—C1—C7—C8	−177.1 (3)	C3—O4—C17—C18	−179.9 (2)
C2—C1—C7—C8	1.5 (4)	C12—O5—C19—O6	4.4 (5)
C1—C7—C8—C9	−177.9 (2)	C12—O5—C19—C20	−176.5 (3)
C7—C8—C9—C14	170.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···O1i	0.96	2.56	3.402 (4)	147.
C16—H16B···O5ii	0.96	2.56	3.438 (4)	153.
C18—H18A···O3iii	0.96	2.60	3.494 (4)	156.
C8—H8A···O6iv	0.93	2.58	3.441 (4)	154.
C16—H16A···O3v	0.96	2.70	3.185 (4)	112.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20C⋯O1i	0.96	2.56	3.402 (4)	147
C16—H16B⋯O5ii	0.96	2.56	3.438 (4)	153
C18—H18A⋯O3iii	0.96	2.60	3.494 (4)	156
C8—H8A⋯O6iv	0.93	2.58	3.441 (4)	154

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