(E)-1-[4-(Methyl-sulfan-yl)phen-yl]-2-(2,3,4-trimeth-oxy-phen-yl)ethene.

In the title compound, C(18)H(20)O(3)S, the rings are almost coplanar [inter-ring dihedral angle = 6.6 (2)°]. In the crystal, weak C-H⋯O hydrogen bonds between the meth-oxy groups connect adjacent mol-ecules, giving chains which extend along [001].

Related literature

For the synthesis, see: Cushman et al. (1991 ▶); Ulman et al. (1990 ▶). For the chemopreventive, cardioprotective and neuroprotective activity of the natural stilbene derivative trans-resveratrol (3,4′,5-trihy­droxy­stilbene), see: Goswami & Das (2009 ▶). For preclinical and clinical studies of its therapeutic action in cancer diseases, see: Bishayee et al. (2010 ▶); Kundu & Surh (2008) ▶; Rimando & Suh (2008 ▶). For the cancer prevention activity of other natural compounds with stilbene backbones, see: Saiko et al. (2008 ▶); Rimando & Suh (2008 ▶). For similar structures, see: Sopková-de Oliveira Santos et al. (2009 ▶). For bond-length data, see: Glusker et al. (1996 ▶).

Experimental

Crystal data

C18H20O3S

M = 316.40

Monoclinic,

a = 13.9633 (4) Å

b = 7.7094 (2) Å

c = 15.1518 (4) Å

β = 90.705 (3)°

V = 1630.95 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.55 × 0.5 × 0.01 mm

Data collection

Agilent Xcalibur Atlas CCD-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.900, T max = 1.000

8931 measured reflections

2862 independent reflections

2229 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.105

S = 1.12

2862 reflections

279 parameters

All H-atom parameters refined

Δρmax = 0.17 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036288/zs2220sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036288/zs2220Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812036288/zs2220Isup3.cml

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

C18H20O3S	F(000) = 672
Mr = 316.40	Dx = 1.289 Mg m−3
Monoclinic, P21/c	Melting point: 417 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.9633 (4) Å	Cell parameters from 6497 reflections
b = 7.7094 (2) Å	θ = 2.6–29.0°
c = 15.1518 (4) Å	µ = 0.21 mm−1
β = 90.705 (3)°	T = 293 K
V = 1630.95 (8) Å3	Plate, colourless
Z = 4	0.55 × 0.5 × 0.01 mm

Agilent Xcalibur Atlas CCD-detector diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	2229 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 10.3088 pixels mm-1	θmax = 25.0°, θmin = 2.7°
ω scans	h = −14→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→8
Tmin = 0.900, Tmax = 1.000	l = −18→18
8931 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)] = 0.050	Hydrogen site location: difference Fourier map
wR(F2) = 0.105	All H-atom parameters refined
S = 1.12	w = 1/[σ2(Fo2) + (0.0252P)2 + 1.2649P] where P = (Fo2 + 2Fc2)/3
2862 reflections	(Δ/σ)max = 0.001
279 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.25 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
C1	0.61061 (17)	0.0320 (3)	0.76027 (15)	0.0414 (6)
C2	0.55297 (19)	0.1096 (4)	0.69676 (16)	0.0473 (6)
H2	0.4970 (17)	0.165 (3)	0.7110 (14)	0.045 (7)*
C3	0.57983 (19)	0.1080 (4)	0.60942 (16)	0.0485 (7)
H3	0.5392 (18)	0.162 (4)	0.5676 (16)	0.055 (8)*
C4	0.66434 (17)	0.0313 (3)	0.58195 (15)	0.0414 (6)
C5	0.72238 (19)	−0.0446 (4)	0.64716 (17)	0.0476 (6)
H5	0.7822 (19)	−0.096 (3)	0.6326 (16)	0.054 (8)*
C6	0.69588 (19)	−0.0444 (4)	0.73424 (16)	0.0478 (6)
H6	0.7355 (19)	−0.101 (4)	0.7777 (17)	0.059 (8)*
S7	0.58562 (5)	0.02516 (10)	0.87413 (4)	0.0535 (2)
C8	0.4734 (3)	0.1316 (6)	0.8820 (2)	0.0704 (10)
H8C	0.482 (3)	0.258 (6)	0.863 (3)	0.120 (15)*
H8B	0.428 (2)	0.071 (4)	0.850 (2)	0.081 (11)*
H8A	0.456 (2)	0.131 (4)	0.942 (2)	0.086 (10)*
C9	0.68881 (19)	0.0317 (4)	0.48811 (16)	0.0467 (6)
H9	0.6450 (19)	0.091 (4)	0.4513 (17)	0.059 (8)*
C10	0.76519 (19)	−0.0373 (3)	0.45162 (16)	0.0431 (6)
H10	0.8099 (18)	−0.093 (3)	0.4862 (16)	0.050 (7)*
C11	0.78855 (16)	−0.0365 (3)	0.35739 (14)	0.0393 (5)
C12	0.73453 (18)	0.0533 (3)	0.29456 (16)	0.0445 (6)
H12	0.6803 (18)	0.120 (3)	0.3124 (16)	0.054 (7)*
C13	0.75702 (18)	0.0514 (4)	0.20615 (16)	0.0452 (6)
H13	0.7196 (17)	0.117 (3)	0.1650 (16)	0.049 (7)*
C14	0.83398 (17)	−0.0449 (3)	0.17705 (14)	0.0410 (6)
C15	0.89145 (16)	−0.1333 (3)	0.23833 (15)	0.0388 (6)
C16	0.86901 (17)	−0.1269 (3)	0.32758 (15)	0.0395 (6)
O17	0.92198 (13)	−0.2190 (3)	0.38833 (11)	0.0578 (5)
C18	1.0193 (3)	−0.1635 (6)	0.4006 (3)	0.0774 (11)
H18B	1.035 (3)	−0.201 (5)	0.457 (3)	0.116 (14)*
H18A	1.056 (3)	−0.217 (6)	0.356 (3)	0.139 (18)*
H18C	1.024 (4)	−0.033 (8)	0.399 (3)	0.19 (2)*
O19	0.96529 (12)	−0.2384 (2)	0.21239 (11)	0.0502 (5)
C20	1.0435 (2)	−0.1512 (5)	0.1699 (2)	0.0614 (8)
H20C	1.092 (3)	−0.230 (5)	0.166 (2)	0.105 (13)*
H20B	1.027 (2)	−0.119 (5)	0.109 (2)	0.104 (13)*
H20A	1.062 (3)	−0.048 (7)	0.200 (3)	0.15 (2)*
O21	0.85858 (12)	−0.0665 (2)	0.09066 (10)	0.0511 (5)
C22	0.7946 (2)	0.0007 (5)	0.02544 (19)	0.0604 (8)
H22C	0.790 (2)	0.128 (4)	0.0280 (17)	0.067 (9)*
H22B	0.820 (2)	−0.030 (4)	−0.0289 (19)	0.066 (9)*
H22A	0.729 (3)	−0.053 (4)	0.030 (2)	0.093 (11)*

	U11	U22	U33	U12	U13	U23
C1	0.0440 (14)	0.0393 (14)	0.0407 (12)	−0.0025 (12)	−0.0003 (10)	0.0012 (11)
C2	0.0412 (14)	0.0562 (17)	0.0445 (14)	0.0144 (13)	0.0042 (11)	0.0008 (12)
C3	0.0451 (15)	0.0568 (18)	0.0435 (14)	0.0140 (13)	−0.0012 (11)	0.0069 (12)
C4	0.0432 (13)	0.0376 (14)	0.0433 (12)	0.0018 (12)	0.0024 (10)	0.0016 (11)
C5	0.0430 (14)	0.0470 (16)	0.0527 (15)	0.0110 (13)	0.0044 (12)	0.0026 (12)
C6	0.0471 (15)	0.0502 (16)	0.0459 (14)	0.0097 (13)	−0.0036 (12)	0.0071 (12)
S7	0.0570 (4)	0.0646 (5)	0.0391 (3)	0.0026 (4)	0.0009 (3)	0.0045 (3)
C8	0.059 (2)	0.103 (3)	0.0489 (18)	0.006 (2)	0.0105 (15)	−0.0036 (19)
C9	0.0469 (15)	0.0486 (16)	0.0446 (13)	0.0087 (13)	0.0032 (11)	0.0044 (12)
C10	0.0463 (15)	0.0389 (14)	0.0441 (13)	0.0013 (12)	0.0035 (11)	0.0018 (11)
C11	0.0396 (13)	0.0352 (13)	0.0433 (12)	−0.0036 (11)	0.0030 (10)	−0.0026 (11)
C12	0.0392 (14)	0.0456 (16)	0.0487 (14)	0.0078 (12)	0.0029 (11)	−0.0028 (12)
C13	0.0415 (14)	0.0492 (16)	0.0447 (13)	0.0030 (13)	−0.0035 (11)	0.0027 (12)
C14	0.0412 (13)	0.0418 (14)	0.0401 (12)	−0.0064 (12)	0.0041 (10)	−0.0027 (11)
C15	0.0384 (13)	0.0288 (13)	0.0494 (13)	0.0004 (11)	0.0073 (10)	−0.0031 (10)
C16	0.0429 (13)	0.0305 (13)	0.0452 (13)	0.0010 (11)	0.0031 (10)	0.0035 (10)
O17	0.0595 (12)	0.0597 (13)	0.0545 (10)	0.0221 (10)	0.0079 (9)	0.0170 (9)
C18	0.070 (2)	0.090 (3)	0.072 (2)	0.023 (2)	−0.0233 (19)	−0.001 (2)
O19	0.0539 (11)	0.0388 (10)	0.0583 (10)	0.0096 (9)	0.0156 (8)	0.0020 (8)
C20	0.0468 (17)	0.064 (2)	0.074 (2)	0.0107 (17)	0.0185 (15)	0.0018 (18)
O21	0.0515 (10)	0.0631 (13)	0.0389 (9)	0.0022 (9)	0.0028 (8)	−0.0015 (8)
C22	0.065 (2)	0.073 (3)	0.0427 (15)	0.0063 (19)	−0.0016 (14)	0.0032 (15)

C1—C2	1.383 (3)	C12—C13	1.380 (3)
C1—C6	1.390 (3)	C12—H12	0.96 (3)
C1—S7	1.765 (2)	C13—C14	1.382 (3)
C2—C3	1.380 (3)	C13—H13	0.95 (2)
C2—H2	0.92 (2)	C14—O21	1.368 (3)
C3—C4	1.388 (3)	C14—C15	1.397 (3)
C3—H3	0.94 (3)	C15—O19	1.373 (3)
C4—C5	1.398 (3)	C15—C16	1.393 (3)
C4—C9	1.466 (3)	C16—O17	1.372 (3)
C5—C6	1.375 (3)	O17—C18	1.435 (4)
C5—H5	0.95 (3)	C18—H18B	0.92 (4)
C6—H6	0.96 (3)	C18—H18A	0.95 (4)
S7—C8	1.774 (3)	C18—H18C	1.00 (6)
C8—H8C	1.03 (4)	O19—C20	1.441 (3)
C8—H8B	0.93 (3)	C20—H20C	0.91 (4)
C8—H8A	0.94 (3)	C20—H20B	0.98 (4)
C9—C10	1.319 (3)	C20—H20A	0.95 (5)
C9—H9	0.94 (3)	O21—C22	1.422 (3)
C10—C11	1.469 (3)	C22—H22C	0.99 (3)
C10—H10	0.92 (2)	C22—H22B	0.93 (3)
C11—C12	1.392 (3)	C22—H22A	1.01 (3)
C11—C16	1.401 (3)
C2—C1—C6	118.6 (2)	C13—C12—H12	118.0 (15)
C2—C1—S7	124.92 (19)	C11—C12—H12	119.9 (15)
C6—C1—S7	116.43 (18)	C12—C13—C14	120.2 (2)
C3—C2—C1	120.0 (2)	C12—C13—H13	120.0 (15)
C3—C2—H2	118.2 (14)	C14—C13—H13	119.9 (15)
C1—C2—H2	121.8 (14)	O21—C14—C13	125.2 (2)
C2—C3—C4	122.2 (2)	O21—C14—C15	115.3 (2)
C2—C3—H3	118.2 (15)	C13—C14—C15	119.5 (2)
C4—C3—H3	119.6 (15)	O19—C15—C16	118.5 (2)
C3—C4—C5	117.0 (2)	O19—C15—C14	121.7 (2)
C3—C4—C9	119.9 (2)	C16—C15—C14	119.6 (2)
C5—C4—C9	123.1 (2)	O17—C16—C15	120.5 (2)
C6—C5—C4	121.2 (2)	O17—C16—C11	118.0 (2)
C6—C5—H5	117.9 (15)	C15—C16—C11	121.4 (2)
C4—C5—H5	120.9 (15)	C16—O17—C18	115.7 (2)
C5—C6—C1	121.0 (2)	O17—C18—H18B	104 (2)
C5—C6—H6	119.9 (16)	O17—C18—H18A	108 (3)
C1—C6—H6	119.1 (16)	H18B—C18—H18A	113 (4)
C1—S7—C8	103.76 (14)	O17—C18—H18C	111 (3)
S7—C8—H8C	108 (2)	H18B—C18—H18C	108 (4)
S7—C8—H8B	109 (2)	H18A—C18—H18C	113 (4)
H8C—C8—H8B	115 (3)	C15—O19—C20	115.4 (2)
S7—C8—H8A	108 (2)	O19—C20—H20C	107 (2)
H8C—C8—H8A	108 (3)	O19—C20—H20B	111 (2)
H8B—C8—H8A	109 (3)	H20C—C20—H20B	106 (3)
C10—C9—C4	127.2 (2)	O19—C20—H20A	112 (3)
C10—C9—H9	118.0 (16)	H20C—C20—H20A	112 (3)
C4—C9—H9	114.7 (16)	H20B—C20—H20A	108 (4)
C9—C10—C11	126.6 (2)	C14—O21—C22	117.2 (2)
C9—C10—H10	119.9 (15)	O21—C22—H22C	112.2 (17)
C11—C10—H10	113.5 (15)	O21—C22—H22B	106.2 (17)
C12—C11—C16	117.2 (2)	H22C—C22—H22B	108 (2)
C12—C11—C10	122.8 (2)	O21—C22—H22A	111.2 (19)
C16—C11—C10	120.0 (2)	H22C—C22—H22A	110 (3)
C13—C12—C11	122.1 (2)	H22B—C22—H22A	108 (3)
C6—C1—C2—C3	1.0 (4)	C12—C13—C14—O21	174.9 (2)
S7—C1—C2—C3	179.7 (2)	C12—C13—C14—C15	−3.1 (4)
C1—C2—C3—C4	−0.5 (4)	O21—C14—C15—O19	−2.0 (3)
C2—C3—C4—C5	−0.3 (4)	C13—C14—C15—O19	176.2 (2)
C2—C3—C4—C9	179.3 (3)	O21—C14—C15—C16	−176.6 (2)
C3—C4—C5—C6	0.7 (4)	C13—C14—C15—C16	1.6 (4)
C9—C4—C5—C6	−178.9 (3)	O19—C15—C16—O17	2.3 (3)
C4—C5—C6—C1	−0.3 (4)	C14—C15—C16—O17	177.1 (2)
C2—C1—C6—C5	−0.6 (4)	O19—C15—C16—C11	−173.4 (2)
S7—C1—C6—C5	−179.4 (2)	C14—C15—C16—C11	1.4 (4)
C2—C1—S7—C8	1.6 (3)	C12—C11—C16—O17	−178.7 (2)
C6—C1—S7—C8	−179.7 (2)	C10—C11—C16—O17	2.2 (3)
C3—C4—C9—C10	−179.0 (3)	C12—C11—C16—C15	−2.9 (4)
C5—C4—C9—C10	0.6 (4)	C10—C11—C16—C15	178.0 (2)
C4—C9—C10—C11	179.7 (2)	C15—C16—O17—C18	66.6 (3)
C9—C10—C11—C12	5.8 (4)	C11—C16—O17—C18	−117.6 (3)
C9—C10—C11—C16	−175.1 (3)	C16—C15—O19—C20	−119.7 (3)
C16—C11—C12—C13	1.5 (4)	C14—C15—O19—C20	65.6 (3)
C10—C11—C12—C13	−179.4 (2)	C13—C14—O21—C22	−6.6 (4)
C11—C12—C13—C14	1.5 (4)	C15—C14—O21—C22	171.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22B···O17i	0.93 (3)	2.72 (3)	3.505 (4)	143 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22B⋯O17i	0.93 (3)	2.72 (3)	3.505 (4)	143 (2)

Symmetry code: (i) .