(E)-1-(3,4-Dimeth-oxy-phen-yl)-3-[4-(methyl-sulfan-yl)phen-yl]prop-2-en-1-one.

In the title compound, C(18)H(18)O(3)S, the C=C double bond exists in an E configuration and the dihedral angle between the two benzene rings is 11.74 (8)°. In the crystal, mol-ecules are linked into a three-dimensional network by C-H⋯O hydrogen bonds. The crystal structure is also stabilized by weak C-H⋯π inter-actions.

Related literature

For the biological activity of chalcone derivatives, see: Rajendra Prasad et al. (2008 ▶); Won et al. (2005) ▶; Sivakumar et al. (2007 ▶); Churkin et al. (1982 ▶). For related structures, see: Narayana et al. (2007 ▶); Fun et al. (2011 ▶).

Experimental

Crystal data

C18H18O3S

M = 314.38

Tetragonal,

a = 19.0863 (7) Å

c = 8.9633 (4) Å

V = 3265.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.60 × 0.27 × 0.21 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.886, T max = 0.957

65941 measured reflections

4760 independent reflections

3944 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.03

4760 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 2109 Friedel pairs

Flack parameter: −0.01 (7)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103323X/wn2447sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103323X/wn2447Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103323X/wn2447Isup3.cml

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

C18H18O3S	Dx = 1.279 Mg m−3
Mr = 314.38	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421c	Cell parameters from 9341 reflections
Hall symbol: P -4 2n	θ = 2.4–26.5°
a = 19.0863 (7) Å	µ = 0.21 mm−1
c = 8.9633 (4) Å	T = 296 K
V = 3265.2 (2) Å3	Block, colourless
Z = 8	0.60 × 0.27 × 0.21 mm
F(000) = 1328

Bruker APEX DUO CCD area-detector diffractometer	4760 independent reflections
Radiation source: fine-focus sealed tube	3944 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.886, Tmax = 0.957	k = −26→26
65941 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0476P)2 + 0.3471P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4760 reflections	Δρmax = 0.13 e Å−3
202 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack (1983), 2109 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (7)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
S1	−0.04907 (3)	0.61987 (3)	0.96772 (6)	0.08374 (17)
O1	0.20901 (6)	0.80886 (8)	0.25811 (15)	0.0801 (4)
O2	0.18232 (6)	0.88384 (6)	−0.28422 (13)	0.0638 (3)
O3	0.04997 (6)	0.89660 (7)	−0.32673 (13)	0.0682 (3)
C1	0.16475 (7)	0.84377 (7)	−0.02843 (18)	0.0498 (3)
H1A	0.2126	0.8392	−0.0120	0.060*
C2	0.14116 (7)	0.86658 (7)	−0.16444 (16)	0.0496 (3)
C3	0.06866 (8)	0.87441 (8)	−0.18887 (17)	0.0533 (3)
C4	0.02241 (8)	0.85920 (9)	−0.07543 (19)	0.0613 (4)
H4A	−0.0255	0.8649	−0.0906	0.074*
C5	0.04682 (8)	0.83541 (8)	0.06130 (17)	0.0558 (3)
H5A	0.0151	0.8249	0.1368	0.067*
C6	0.11757 (7)	0.82725 (7)	0.08653 (16)	0.0482 (3)
C7	0.14607 (8)	0.80464 (8)	0.23353 (18)	0.0535 (3)
C8	0.09822 (8)	0.77645 (8)	0.34700 (17)	0.0554 (3)
H8A	0.0505	0.7747	0.3263	0.067*
C9	0.12086 (8)	0.75347 (8)	0.47766 (17)	0.0550 (3)
H9A	0.1687	0.7578	0.4951	0.066*
C10	0.07975 (8)	0.72221 (8)	0.59750 (16)	0.0513 (3)
C11	0.00713 (9)	0.71448 (11)	0.59020 (18)	0.0697 (5)
H11A	−0.0166	0.7301	0.5058	0.084*
C12	−0.03014 (9)	0.68459 (12)	0.7040 (2)	0.0727 (5)
H12A	−0.0786	0.6807	0.6963	0.087*
C13	0.00383 (9)	0.65988 (9)	0.83166 (17)	0.0570 (3)
C14	0.07588 (8)	0.66729 (8)	0.84138 (17)	0.0574 (3)
H14A	0.0996	0.6513	0.9254	0.069*
C15	0.11254 (8)	0.69847 (8)	0.72617 (17)	0.0551 (3)
H15A	0.1608	0.7037	0.7352	0.066*
C16	0.25489 (9)	0.86904 (11)	−0.2721 (3)	0.0832 (6)
H16A	0.2770	0.8761	−0.3671	0.125*
H16B	0.2612	0.8213	−0.2413	0.125*
H16C	0.2756	0.8997	−0.1996	0.125*
C17	−0.02357 (10)	0.89919 (13)	−0.3594 (2)	0.0833 (6)
H17A	−0.0302	0.9087	−0.4636	0.125*
H17B	−0.0451	0.9356	−0.3015	0.125*
H17C	−0.0447	0.8550	−0.3348	0.125*
C18	0.01027 (13)	0.59980 (14)	1.1152 (2)	0.0967 (7)
H18A	−0.0149	0.5788	1.1964	0.145*
H18B	0.0324	0.6421	1.1490	0.145*
H18C	0.0453	0.5677	1.0797	0.145*

	U11	U22	U33	U12	U13	U23
S1	0.0711 (3)	0.1198 (4)	0.0603 (2)	−0.0176 (3)	0.0045 (2)	0.0147 (3)
O1	0.0511 (6)	0.1106 (10)	0.0786 (8)	0.0013 (6)	−0.0057 (6)	0.0289 (8)
O2	0.0579 (6)	0.0706 (7)	0.0629 (6)	0.0057 (5)	0.0190 (5)	0.0133 (6)
O3	0.0606 (6)	0.0881 (8)	0.0560 (6)	0.0054 (6)	0.0033 (5)	0.0256 (6)
C1	0.0445 (6)	0.0461 (7)	0.0588 (7)	0.0023 (5)	0.0042 (6)	0.0027 (6)
C2	0.0507 (7)	0.0441 (6)	0.0540 (7)	0.0009 (5)	0.0118 (6)	0.0046 (6)
C3	0.0545 (7)	0.0541 (7)	0.0512 (7)	0.0038 (6)	0.0042 (6)	0.0101 (6)
C4	0.0445 (7)	0.0786 (10)	0.0608 (9)	0.0041 (7)	0.0025 (6)	0.0185 (8)
C5	0.0479 (7)	0.0671 (9)	0.0523 (8)	0.0016 (6)	0.0072 (6)	0.0145 (7)
C6	0.0486 (7)	0.0442 (6)	0.0519 (7)	0.0023 (5)	0.0040 (6)	0.0042 (5)
C7	0.0513 (7)	0.0519 (7)	0.0573 (8)	0.0048 (6)	−0.0002 (6)	0.0067 (6)
C8	0.0526 (7)	0.0619 (8)	0.0518 (8)	0.0014 (6)	−0.0029 (6)	0.0063 (6)
C9	0.0527 (7)	0.0604 (8)	0.0519 (7)	0.0007 (6)	−0.0046 (6)	0.0019 (6)
C10	0.0525 (7)	0.0559 (8)	0.0456 (7)	0.0004 (6)	−0.0051 (6)	0.0001 (6)
C11	0.0569 (9)	0.1012 (13)	0.0509 (8)	−0.0060 (9)	−0.0156 (7)	0.0129 (9)
C12	0.0497 (8)	0.1083 (14)	0.0602 (10)	−0.0101 (9)	−0.0099 (7)	0.0117 (10)
C13	0.0588 (8)	0.0664 (9)	0.0456 (7)	−0.0050 (7)	−0.0008 (6)	−0.0015 (6)
C14	0.0574 (8)	0.0661 (9)	0.0486 (7)	0.0021 (7)	−0.0092 (6)	0.0064 (7)
C15	0.0486 (7)	0.0635 (8)	0.0532 (7)	0.0004 (6)	−0.0072 (6)	0.0053 (6)
C16	0.0605 (9)	0.0824 (12)	0.1066 (15)	0.0140 (9)	0.0337 (10)	0.0321 (12)
C17	0.0682 (11)	0.1129 (16)	0.0687 (11)	0.0062 (10)	−0.0067 (9)	0.0341 (11)
C18	0.0957 (16)	0.1238 (19)	0.0706 (12)	−0.0081 (14)	0.0019 (11)	0.0352 (13)

S1—C13	1.7579 (16)	C9—H9A	0.9300
S1—C18	1.783 (2)	C10—C15	1.388 (2)
O1—C7	1.2239 (19)	C10—C11	1.396 (2)
O2—C2	1.3705 (16)	C11—C12	1.368 (2)
O2—C16	1.418 (2)	C11—H11A	0.9300
O3—C3	1.3541 (18)	C12—C13	1.397 (2)
O3—C17	1.435 (2)	C12—H12A	0.9300
C1—C2	1.371 (2)	C13—C14	1.385 (2)
C1—C6	1.4042 (19)	C14—C15	1.382 (2)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.409 (2)	C15—H15A	0.9300
C3—C4	1.378 (2)	C16—H16A	0.9600
C4—C5	1.387 (2)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.378 (2)	C17—H17A	0.9600
C5—H5A	0.9300	C17—H17B	0.9600
C6—C7	1.489 (2)	C17—H17C	0.9600
C7—C8	1.469 (2)	C18—H18A	0.9600
C8—C9	1.323 (2)	C18—H18B	0.9600
C8—H8A	0.9300	C18—H18C	0.9600
C9—C10	1.458 (2)
C13—S1—C18	104.06 (9)	C12—C11—C10	121.70 (15)
C2—O2—C16	116.87 (13)	C12—C11—H11A	119.1
C3—O3—C17	117.05 (13)	C10—C11—H11A	119.1
C2—C1—C6	120.90 (13)	C11—C12—C13	120.67 (15)
C2—C1—H1A	119.6	C11—C12—H12A	119.7
C6—C1—H1A	119.6	C13—C12—H12A	119.7
O2—C2—C1	125.80 (13)	C14—C13—C12	118.54 (15)
O2—C2—C3	114.56 (13)	C14—C13—S1	124.81 (12)
C1—C2—C3	119.63 (12)	C12—C13—S1	116.64 (12)
O3—C3—C4	124.80 (13)	C15—C14—C13	119.97 (14)
O3—C3—C2	115.71 (13)	C15—C14—H14A	120.0
C4—C3—C2	119.49 (13)	C13—C14—H14A	120.0
C3—C4—C5	120.39 (14)	C14—C15—C10	122.21 (14)
C3—C4—H4A	119.8	C14—C15—H15A	118.9
C5—C4—H4A	119.8	C10—C15—H15A	118.9
C6—C5—C4	120.73 (14)	O2—C16—H16A	109.5
C6—C5—H5A	119.6	O2—C16—H16B	109.5
C4—C5—H5A	119.6	H16A—C16—H16B	109.5
C5—C6—C1	118.85 (13)	O2—C16—H16C	109.5
C5—C6—C7	122.40 (13)	H16A—C16—H16C	109.5
C1—C6—C7	118.69 (12)	H16B—C16—H16C	109.5
O1—C7—C8	120.64 (15)	O3—C17—H17A	109.5
O1—C7—C6	119.91 (14)	O3—C17—H17B	109.5
C8—C7—C6	119.44 (13)	H17A—C17—H17B	109.5
C9—C8—C7	122.08 (14)	O3—C17—H17C	109.5
C9—C8—H8A	119.0	H17A—C17—H17C	109.5
C7—C8—H8A	119.0	H17B—C17—H17C	109.5
C8—C9—C10	127.74 (14)	S1—C18—H18A	109.5
C8—C9—H9A	116.1	S1—C18—H18B	109.5
C10—C9—H9A	116.1	H18A—C18—H18B	109.5
C15—C10—C11	116.89 (14)	S1—C18—H18C	109.5
C15—C10—C9	120.21 (13)	H18A—C18—H18C	109.5
C11—C10—C9	122.91 (14)	H18B—C18—H18C	109.5
C16—O2—C2—C1	7.8 (2)	C5—C6—C7—C8	12.6 (2)
C16—O2—C2—C3	−172.66 (15)	C1—C6—C7—C8	−170.27 (13)
C6—C1—C2—O2	−179.74 (13)	O1—C7—C8—C9	−1.3 (3)
C6—C1—C2—C3	0.8 (2)	C6—C7—C8—C9	177.77 (14)
C17—O3—C3—C4	−4.9 (2)	C7—C8—C9—C10	−177.71 (15)
C17—O3—C3—C2	174.67 (17)	C8—C9—C10—C15	177.66 (16)
O2—C2—C3—O3	1.0 (2)	C8—C9—C10—C11	−2.3 (3)
C1—C2—C3—O3	−179.45 (14)	C15—C10—C11—C12	−0.3 (3)
O2—C2—C3—C4	−179.36 (15)	C9—C10—C11—C12	179.63 (18)
C1—C2—C3—C4	0.2 (2)	C10—C11—C12—C13	−0.8 (3)
O3—C3—C4—C5	178.71 (16)	C11—C12—C13—C14	1.0 (3)
C2—C3—C4—C5	−0.9 (3)	C11—C12—C13—S1	−177.93 (16)
C3—C4—C5—C6	0.6 (3)	C18—S1—C13—C14	4.20 (19)
C4—C5—C6—C1	0.3 (2)	C18—S1—C13—C12	−176.97 (16)
C4—C5—C6—C7	177.46 (15)	C12—C13—C14—C15	−0.1 (2)
C2—C1—C6—C5	−1.0 (2)	S1—C13—C14—C15	178.71 (13)
C2—C1—C6—C7	−178.28 (13)	C13—C14—C15—C10	−1.0 (2)
C5—C6—C7—O1	−168.32 (16)	C11—C10—C15—C14	1.2 (2)
C1—C6—C7—O1	8.8 (2)	C9—C10—C15—C14	−178.74 (15)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16B···O1i	0.96	2.33	3.235 (2)	157
C17—H17A···O3ii	0.96	2.47	3.344 (2)	151
C4—H4A···Cg1iii	0.93	2.79	3.5776 (17)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16B⋯O1i	0.96	2.33	3.235 (2)	157
C17—H17A⋯O3ii	0.96	2.47	3.344 (2)	151
C4—H4A⋯Cg1iii	0.93	2.79	3.5776 (17)	143

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