trans-Ethyl-enedi-p-phenyl-ene diacetate.

The centrosymmetric title compound, C(18)H(26)O(4), was prepared in high yield from 4-acetoxy-styrene via Ru-catalysed homo-olefin metathesis. Exclusive formation of the E-configurated isomer was observed. In the crystal, a strong C-H⋯π inter-molecular inter-action links the mol-ecules together.

Related literature

For the preparation of differently substituted stilbenes using a Ru-catalysed metathesis strategy, see: Velder et al. (2006 ▶). For alternative methodologies for the synthesis of ­oxy-functionalized stilbenes using Wittig-type olefinations or Heck-couplings, see: Kim et al. (2002 ▶); Lion et al. (2005 ▶); Botella et al. (2004 ▶); Reetz et al. (1998 ▶). For the bioactivity of various stilbenes with a focus on their anti­cancer activity, see: Aggarwal et al. (2004 ▶); Wolter et al. (2002 ▶); Fremont (2000 ▶); Jang et al. (1997 ▶); Wieder et al. (2001 ▶). For related structures see: Malone et al. (1997 ▶). For a previous synthesis of the title compound see: Johnson et al. (1952 ▶).

Experimental

Crystal data

C18H16O4

M = 296.31

Monoclinic,

a = 9.7430 (4) Å

b = 7.2839 (4) Å

c = 11.2723 (6) Å

β = 113.649 (3)°

V = 732.78 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.52 × 0.36 × 0.34 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

3533 measured reflections

1595 independent reflections

1119 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.106

S = 1.03

1595 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SCHAKAL99 (Keller, 1999 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032620/hg2554sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032620/hg2554Isup2.hkl

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

C18H16O4	F(000) = 312
Mr = 296.31	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Melting point: 214 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.7430 (4) Å	Cell parameters from 3533 reflections
b = 7.2839 (4) Å	θ = 2.3–27.0°
c = 11.2723 (6) Å	µ = 0.10 mm−1
β = 113.649 (3)°	T = 100 K
V = 732.78 (7) Å3	Needle, colourless
Z = 2	0.52 × 0.36 × 0.34 mm

Nonius KappaCCD diffractometer	1119 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
graphite	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −12→12
3533 measured reflections	k = −8→9
1595 independent reflections	l = −14→14

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) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.0561P] where P = (Fo2 + 2Fc2)/3
1595 reflections	(Δ/σ)max = 0.002
101 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.21 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. The coordinates of the hydrogen atoms are constrained, and the U values of the H atoms are constrained relative to the Ueq of the atom the hydrogen binds to (1.2 for CH and CH2, 1.5 for CH3).

	x	y	z	Uiso*/Ueq
O1	0.26496 (12)	0.47976 (14)	0.58904 (9)	0.0210 (3)
O2	0.37476 (12)	0.75603 (15)	0.60504 (10)	0.0249 (3)
C1	0.06877 (16)	0.48067 (19)	0.04361 (14)	0.0165 (3)
H1	0.1412	0.4466	0.0111	0.020*
C2	0.11855 (16)	0.48580 (19)	0.18473 (14)	0.0151 (3)
C3	0.25433 (16)	0.4033 (2)	0.26319 (14)	0.0171 (3)
H3	0.3134	0.3468	0.2238	0.020*
C4	0.30488 (16)	0.4019 (2)	0.39715 (14)	0.0176 (3)
H4	0.3971	0.3446	0.4492	0.021*
C5	0.21842 (17)	0.4853 (2)	0.45310 (13)	0.0165 (4)
C6	0.08410 (17)	0.5691 (2)	0.37923 (14)	0.0189 (4)
H6	0.0261	0.6259	0.4195	0.023*
C7	0.03502 (17)	0.5694 (2)	0.24605 (14)	0.0179 (4)
H7	−0.0572	0.6274	0.1950	0.021*
C8	0.34023 (17)	0.6307 (2)	0.65644 (15)	0.0187 (4)
C9	0.37163 (18)	0.6128 (2)	0.79670 (14)	0.0245 (4)
H9A	0.4210	0.7245	0.8424	0.037*
H9B	0.4373	0.5070	0.8330	0.037*
H9C	0.2773	0.5951	0.8069	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0304 (7)	0.0177 (6)	0.0123 (6)	−0.0031 (5)	0.0058 (5)	−0.0012 (4)
O2	0.0264 (7)	0.0227 (6)	0.0258 (6)	−0.0058 (5)	0.0106 (5)	−0.0025 (5)
C1	0.0191 (8)	0.0139 (8)	0.0174 (8)	−0.0008 (6)	0.0083 (6)	−0.0011 (6)
C2	0.0168 (8)	0.0117 (7)	0.0154 (8)	−0.0031 (6)	0.0051 (6)	0.0008 (6)
C3	0.0184 (8)	0.0156 (8)	0.0175 (8)	−0.0012 (6)	0.0076 (7)	−0.0019 (6)
C4	0.0156 (8)	0.0154 (8)	0.0181 (8)	−0.0004 (6)	0.0027 (6)	0.0013 (6)
C5	0.0239 (9)	0.0132 (8)	0.0106 (8)	−0.0049 (6)	0.0049 (7)	−0.0005 (6)
C6	0.0245 (9)	0.0145 (8)	0.0192 (8)	0.0008 (6)	0.0102 (7)	−0.0023 (6)
C7	0.0198 (9)	0.0152 (8)	0.0169 (8)	0.0018 (6)	0.0055 (7)	0.0010 (6)
C8	0.0146 (8)	0.0187 (9)	0.0212 (8)	0.0035 (6)	0.0056 (7)	−0.0039 (7)
C9	0.0275 (9)	0.0245 (9)	0.0174 (9)	0.0029 (7)	0.0046 (7)	−0.0037 (7)

O1—C8	1.3700 (18)	C4—C5	1.380 (2)
O1—C5	1.4135 (16)	C4—H4	0.9500
O2—C8	1.1994 (17)	C5—C6	1.380 (2)
C1—C1i	1.336 (3)	C6—C7	1.381 (2)
C1—C2	1.466 (2)	C6—H6	0.9500
C1—H1	0.9500	C7—H7	0.9500
C2—C3	1.398 (2)	C8—C9	1.491 (2)
C2—C7	1.401 (2)	C9—H9A	0.9800
C3—C4	1.388 (2)	C9—H9B	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C8—O1—C5	116.48 (11)	C5—C6—C7	119.19 (14)
C1i—C1—C2	126.23 (17)	C5—C6—H6	120.4
C1i—C1—H1	116.9	C7—C6—H6	120.4
C2—C1—H1	116.9	C6—C7—C2	121.30 (14)
C3—C2—C7	117.66 (14)	C6—C7—H7	119.3
C3—C2—C1	119.52 (13)	C2—C7—H7	119.3
C7—C2—C1	122.81 (13)	O2—C8—O1	122.30 (14)
C4—C3—C2	121.62 (14)	O2—C8—C9	126.94 (14)
C4—C3—H3	119.2	O1—C8—C9	110.76 (13)
C2—C3—H3	119.2	C8—C9—H9A	109.5
C5—C4—C3	118.61 (14)	C8—C9—H9B	109.5
C5—C4—H4	120.7	H9A—C9—H9B	109.5
C3—C4—H4	120.7	C8—C9—H9C	109.5
C4—C5—C6	121.62 (13)	H9A—C9—H9C	109.5
C4—C5—O1	119.59 (13)	H9B—C9—H9C	109.5
C6—C5—O1	118.75 (13)
C1i—C1—C2—C3	165.70 (18)	C8—O1—C5—C6	−85.05 (16)
C1i—C1—C2—C7	−13.8 (3)	C4—C5—C6—C7	0.0 (2)
C7—C2—C3—C4	0.6 (2)	O1—C5—C6—C7	−177.66 (13)
C1—C2—C3—C4	−178.87 (13)	C5—C6—C7—C2	0.3 (2)
C2—C3—C4—C5	−0.4 (2)	C3—C2—C7—C6	−0.6 (2)
C3—C4—C5—C6	0.1 (2)	C1—C2—C7—C6	178.93 (13)
C3—C4—C5—O1	177.71 (12)	C5—O1—C8—O2	−5.1 (2)
C8—O1—C5—C4	97.22 (15)	C5—O1—C8—C9	175.46 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1ii	0.95	2.81	3.539 (2)	135

Table 1

Geometry the C—H⋯π interaction (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1i	0.95	2.81	3.539 (2)	135

Symmetry code: (i) . Cg1 is the centroid of the C2–C7 ring.