5-[2-(4-Acetyl­oxyphen­yl)ethen­yl]benzene-1,3-diyl diacetate

Tang, L.; Dai, D.; Gong, Y.; Zhong, J.

doi:10.1107/S1600536811044722

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o3129

doi:10.1107/S1600536811044722

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5-[2-(4-Acetyloxyphenyl)ethenyl]benzene-1,3-diyl diacetate

Lin Tang,^a Dongmei Dai,^b Yanqing Gong ^c ^* and Jialiang Zhong ^d

^aZhejiang Pharmaceutical College, Ningbo 315100, People's Republic of China, ^bKey Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315104, People's Republic of China, ^cState Key Laboratory of Bio-Organic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, People's Republic of China, and ^dShanghai Institute of Pharmaceutical Industry, 1320 Beijing Road (West), Shanghai 200040, People's Republic of China
^*Correspondence e-mail: gongyanqing@sioc.ac.cn

(Received 3 October 2011; accepted 26 October 2011; online 29 October 2011)

The title compound, C₂₀H₁₈O₆, was prepared from resveratrol {systematic name: 5-[(E)-2-(4-hydroxyphenyl)ethenyl]benzene-1,3-diol}, which can be isolated from grapes, through triacetylation with using acetic anhydride in pyridine. The two benzene rings are approximately coplanar, making a dihedral angle of 6.64 (14)°, and the three acetoxy group are located on the same side of the plane. The skeleton of the compound resembles a table with three legs. In the crystal, molecules 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_r = 354.34
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.191
S = 1.05
3181 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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⋯O6^iv	0.93	2.58	3.441 (4)	154
Symmetry codes: (i) $[-x, y-1, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811044722/rk2305sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811044722/rk2305Isup3.cml

checkCIF report

Comment top

The title molecule, 3,4',5-triacetoxy-trans-stilbene (Fig. 1), is the triacetylation product of resveratrol, which can be isolated from grapes (González-Barrio et al., 2006). In the molecular structure of the title compound, two benzene rings were substantially coplanar with dihedral angle 6.64 (14)°. Three acetoxy group located in the same side of the plane. As a result, the whole structure looks like an interesting long table with three legs.

In the crystal, molecules of title compound packed with formation an infinite Z form (Fig. 2). Molecules are linked by non-classical C–H···O hydrogen bonds, which played an important role for the stability of the crystal structure (Table 1).

Koide's study (Koide et al., 2011) showed that the title compound effectively protected the live cells after γ-irradiation and it may be a leading candidate for radioprotective drug development.

Related literature top

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 top

The title compound was prepared according to the procedure (Sarpierto et al., 2007) through triacetylation by using acetic anhydride in pyridine (1:1, v/v). Crystals appropriate for X-ray diffraction data collection were obtained from methanol solution, yielding colourless block-like crystals after a week at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule structure with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The packing diagram of the title compound, viewed down the b axis.

5-[2-(4-Acetyloxyphenyl)ethenyl]benzene-1,3-diyl diacetate top

Crystal data top

C₂₀H₁₈O₆	F(000) = 1488
M_r = 354.34	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1023P)² + 2.2789P] where P = (F_o² + 2F_c²)/3
3181 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₀H₁₈O₆	V = 3624.2 (14) Å³
M_r = 354.34	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 31.520 (6) Å	µ = 0.80 mm⁻¹
b = 6.1211 (12) Å	T = 296 K
c = 20.110 (4) Å	0.23 × 0.10 × 0.08 mm
β = 110.92 (3)°

Data collection top

Bruker APEXII CCD diffractometer	3181 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2532 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.939	R_int = 0.020
11742 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.05	Δρ_max = 0.57 e Å⁻³
3181 reflections	Δρ_min = −0.19 e Å⁻³
235 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O6^iv	0.93	2.58	3.441 (4)	154
C16—H16A···O3^v	0.96	2.70	3.185 (4)	112

Symmetry codes: (i) −x, y−1, −z+1/2; (ii) −x, y, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x, −y+1, −z; (v) −x+1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈O₆
M_r	354.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	31.520 (6), 6.1211 (12), 20.110 (4)
β (°)	110.92 (3)
V (Å³)	3624.2 (14)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.23 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.837, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	11742, 3181, 2532
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.191, 1.05
No. of reflections	3181
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.19

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···O1ⁱ	0.96	2.56	3.402 (4)	146.5
C16—H16B···O5ⁱⁱ	0.96	2.56	3.438 (4)	152.6
C18—H18A···O3ⁱⁱⁱ	0.96	2.60	3.494 (4)	155.6
C8—H8A···O6^iv	0.93	2.58	3.441 (4)	154.1
C16—H16A···O3^v	0.96	2.70	3.185 (4)	111.7

Symmetry codes: (i) −x, y−1, −z+1/2; (ii) −x, y, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x, −y+1, −z; (v) −x+1/2, −y+3/2, −z+1.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
González-Barrio, R., Beltrán, D., Cantos, E., Gil, M. I., Espín, J.-C. & Tomás-Barberan, F. (2006). J. Agric. Food Chem. 54, 4222–4228. PubMed Google Scholar
Koide, K., Osman, S., Garner, A. L., Song, F. L., Dixon, T., Greenberger, J. S. & Epperly, M. W. (2011). Am. Chem. Soc. Med. Chem. Lett. 2, 270–274. Web of Science CrossRef CAS Google Scholar
Sarpierto, M. G., Spatafora, C., Tringali, C., Micieli, D. & Castelli, F. (2007). J. Agric. Food Chem. 55, 3720–3728. PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o3129

doi:10.1107/S1600536811044722

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