(E)-1-(2,5-Dimethyl-3-thien-yl)-3-(2,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C(18)H(20)O(4)S, the thio-phene and benzene rings are oriented at a dihedral angle of 10.83 (11)°. The central chain makes dihedral angles of 1.86 (13) and 9.25 (12)° with the benzene and thio-phene rings, respectively. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O inter-actions. π-π inter-actions are also observed between the benzene rings with a centroid-centroid distance of 3.6832 (12) Å. The slippage between the benzene rings is 0.956 Å.

Related literature

For the biological activity of 1,3-diphenyl-2-propene-1-ones, see: Gökhan-Kelekçi et al. (2007 ▶); Ducki et al. (2009 ▶); dos Santos et al. (2008 ▶); Hussain et al. (2009 ▶); Dandia et al. (2006 ▶); Valla et al. (2006 ▶); Ye et al. (2004 ▶). For related structures, see: Asiri et al. (2009 ▶): Hussain et al. (2010 ▶): Fun et al. (2010 ▶).

Experimental

Crystal data

C18H20O4S

M = 332.40

Tetragonal,

a = 19.5263 (5) Å

c = 17.9952 (4) Å

V = 6861.2 (3) Å3

Z = 16

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.26 × 0.18 × 0.16 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.966, T max = 0.975

25995 measured reflections

3106 independent reflections

2225 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.113

S = 1.05

3106 reflections

213 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028709/si2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028709/si2278Isup2.hkl

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

C18H20O4S	Dx = 1.287 Mg m−3
Mr = 332.40	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 2225 reflections
Hall symbol: -I 4ad	θ = 2.1–25.2°
a = 19.5263 (5) Å	µ = 0.21 mm−1
c = 17.9952 (4) Å	T = 296 K
V = 6861.2 (3) Å3	Prism, yellow
Z = 16	0.26 × 0.18 × 0.16 mm
F(000) = 2816

Bruker KAPPA APEXII CCD diffractometer	3106 independent reflections
Radiation source: fine-focus sealed tube	2225 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 8.10 pixels mm-1	θmax = 25.2°, θmin = 2.1°
ω scans	h = −20→23
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −23→23
Tmin = 0.966, Tmax = 0.975	l = −21→21
25995 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0466P)2 + 4.0141P] where P = (Fo2 + 2Fc2)/3
3106 reflections	(Δ/σ)max = 0.001
213 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S1	0.35094 (3)	0.20431 (3)	0.27680 (3)	0.0714 (2)
O1	0.12845 (9)	0.01126 (9)	0.64860 (7)	0.0807 (6)
O2	−0.03254 (9)	−0.15317 (9)	0.54859 (9)	0.0813 (6)
O3	0.00824 (9)	−0.12701 (10)	0.41648 (8)	0.0862 (7)
O4	0.27754 (9)	0.14060 (9)	0.50556 (8)	0.0818 (6)
C1	0.12078 (10)	−0.00807 (10)	0.52048 (10)	0.0514 (7)
C2	0.09748 (11)	−0.02371 (11)	0.59198 (10)	0.0556 (7)
C3	0.04661 (11)	−0.07194 (11)	0.60327 (11)	0.0600 (7)
C4	0.01787 (11)	−0.10560 (11)	0.54363 (12)	0.0600 (8)
C5	0.04047 (11)	−0.09097 (12)	0.47106 (11)	0.0604 (8)
C6	0.09028 (11)	−0.04341 (11)	0.46095 (11)	0.0569 (7)
C7	0.10721 (14)	−0.00049 (14)	0.72270 (11)	0.0754 (9)
C8	−0.05983 (14)	−0.16834 (16)	0.61946 (14)	0.0904 (11)
C9	0.03306 (14)	−0.12099 (15)	0.34337 (12)	0.0829 (10)
C10	0.17351 (10)	0.04257 (11)	0.51010 (10)	0.0553 (7)
C11	0.20201 (11)	0.06423 (11)	0.44711 (11)	0.0581 (7)
C12	0.25438 (11)	0.11732 (11)	0.44709 (11)	0.0579 (7)
C13	0.28009 (11)	0.14298 (11)	0.37456 (10)	0.0536 (7)
C14	0.25098 (12)	0.12648 (12)	0.30381 (11)	0.0622 (8)
C15	0.28342 (12)	0.15590 (12)	0.24581 (11)	0.0636 (8)
C16	0.26802 (14)	0.14998 (15)	0.16401 (12)	0.0857 (10)
C17	0.33529 (11)	0.18552 (11)	0.36833 (11)	0.0577 (7)
C18	0.38074 (14)	0.21495 (14)	0.42741 (13)	0.0810 (10)
H3	0.03178	−0.08165	0.65123	0.0720*
H6	0.10480	−0.03382	0.41285	0.0683*
H7A	0.05890	0.00783	0.72682	0.1132*
H7B	0.13148	0.02983	0.75542	0.1132*
H7C	0.11684	−0.04708	0.73613	0.1132*
H8A	−0.02460	−0.18752	0.65031	0.1355*
H8B	−0.09654	−0.20070	0.61437	0.1355*
H8C	−0.07688	−0.12709	0.64183	0.1355*
H9A	0.02961	−0.07418	0.32751	0.1242*
H9B	0.00640	−0.14950	0.31093	0.1242*
H9C	0.08010	−0.13520	0.34178	0.1242*
H10	0.18992	0.06293	0.55329	0.0664*
H11	0.18819	0.04507	0.40224	0.0697*
H14	0.21311	0.09805	0.29830	0.0747*
H16A	0.30512	0.12692	0.13955	0.1286*
H16B	0.26257	0.19491	0.14319	0.1286*
H16C	0.22655	0.12433	0.15719	0.1286*
H18A	0.35531	0.24738	0.45650	0.1215*
H18B	0.41902	0.23751	0.40458	0.1215*
H18C	0.39698	0.17880	0.45898	0.1215*

	U11	U22	U33	U12	U13	U23
S1	0.0843 (4)	0.0798 (4)	0.0502 (3)	−0.0019 (3)	0.0108 (3)	0.0054 (3)
O1	0.1053 (13)	0.0996 (12)	0.0372 (7)	−0.0388 (10)	−0.0040 (8)	−0.0007 (8)
O2	0.0825 (11)	0.0952 (12)	0.0662 (10)	−0.0260 (10)	0.0093 (8)	−0.0140 (9)
O3	0.0853 (12)	0.1182 (14)	0.0552 (9)	−0.0282 (10)	0.0079 (8)	−0.0337 (9)
O4	0.0953 (12)	0.1074 (13)	0.0426 (8)	−0.0294 (10)	−0.0032 (8)	−0.0034 (8)
C1	0.0545 (12)	0.0567 (12)	0.0430 (10)	0.0055 (10)	−0.0006 (8)	−0.0037 (9)
C2	0.0648 (13)	0.0599 (12)	0.0421 (10)	−0.0002 (11)	−0.0039 (9)	−0.0020 (9)
C3	0.0685 (14)	0.0697 (14)	0.0417 (10)	−0.0026 (12)	0.0018 (9)	0.0004 (10)
C4	0.0582 (13)	0.0642 (14)	0.0575 (12)	−0.0024 (11)	0.0040 (10)	−0.0072 (10)
C5	0.0594 (13)	0.0720 (14)	0.0497 (12)	0.0016 (12)	0.0015 (10)	−0.0171 (10)
C6	0.0582 (12)	0.0691 (14)	0.0434 (10)	0.0050 (11)	0.0060 (9)	−0.0084 (9)
C7	0.0982 (18)	0.0905 (17)	0.0376 (11)	−0.0146 (14)	−0.0026 (11)	0.0011 (10)
C8	0.093 (2)	0.104 (2)	0.0743 (16)	−0.0267 (17)	0.0136 (14)	0.0047 (14)
C9	0.0979 (19)	0.100 (2)	0.0507 (13)	−0.0002 (16)	−0.0021 (12)	−0.0240 (12)
C10	0.0624 (13)	0.0620 (13)	0.0416 (10)	0.0028 (10)	−0.0034 (9)	−0.0044 (9)
C11	0.0659 (13)	0.0673 (14)	0.0411 (10)	−0.0020 (11)	−0.0016 (9)	−0.0048 (9)
C12	0.0644 (13)	0.0685 (14)	0.0408 (10)	0.0026 (11)	−0.0012 (9)	−0.0016 (9)
C13	0.0584 (12)	0.0586 (12)	0.0439 (10)	0.0069 (10)	0.0009 (9)	0.0003 (9)
C14	0.0656 (14)	0.0786 (15)	0.0425 (11)	0.0027 (11)	−0.0005 (10)	−0.0003 (10)
C15	0.0700 (14)	0.0767 (15)	0.0440 (11)	0.0121 (12)	0.0002 (10)	−0.0011 (10)
C16	0.0957 (19)	0.120 (2)	0.0414 (12)	0.0123 (16)	−0.0012 (12)	0.0040 (12)
C17	0.0666 (14)	0.0611 (13)	0.0454 (11)	0.0065 (11)	0.0041 (9)	−0.0021 (9)
C18	0.0866 (18)	0.0967 (19)	0.0597 (14)	−0.0225 (15)	0.0038 (12)	−0.0086 (13)

S1—C15	1.715 (2)	C15—C16	1.507 (3)
S1—C17	1.715 (2)	C17—C18	1.499 (3)
O1—C2	1.368 (2)	C3—H3	0.9300
O1—C7	1.415 (2)	C6—H6	0.9300
O2—C4	1.356 (3)	C7—H7A	0.9600
O2—C8	1.414 (3)	C7—H7B	0.9600
O3—C5	1.362 (3)	C7—H7C	0.9600
O3—C9	1.407 (3)	C8—H8A	0.9600
O4—C12	1.232 (3)	C8—H8B	0.9600
C1—C2	1.399 (3)	C8—H8C	0.9600
C1—C6	1.407 (3)	C9—H9A	0.9600
C1—C10	1.440 (3)	C9—H9B	0.9600
C2—C3	1.384 (3)	C9—H9C	0.9600
C3—C4	1.378 (3)	C10—H10	0.9300
C4—C5	1.408 (3)	C11—H11	0.9300
C5—C6	1.357 (3)	C14—H14	0.9300
C10—C11	1.332 (3)	C16—H16A	0.9600
C11—C12	1.456 (3)	C16—H16B	0.9600
C12—C13	1.486 (3)	C16—H16C	0.9600
C13—C14	1.431 (3)	C18—H18A	0.9600
C13—C17	1.365 (3)	C18—H18B	0.9600
C14—C15	1.349 (3)	C18—H18C	0.9600
O2···O3	2.559 (2)	H6···C9	2.5300
O2···C9i	3.410 (3)	H6···C11	2.7700
O3···O2	2.559 (2)	H6···H9A	2.2700
O3···C9i	3.209 (3)	H6···H9C	2.4100
O4···C18	2.854 (3)	H6···H11	2.2500
O1···H10	2.3200	H6···H10viii	2.5900
O3···H9Ci	2.5500	H7A···C3	2.7300
O4···H10	2.4400	H7A···H3	2.2800
O4···H18A	2.7300	H7A···H9Aiv	2.3700
O4···H18C	2.5900	H7B···C16v	2.9300
O4···H8Cii	2.7600	H7B···H16Av	2.4700
O4···H9Aiii	2.8400	H7B···C1iii	2.9100
O4···H14iii	2.5700	H7B···C6iii	3.0400
C4···C6iv	3.596 (3)	H7C···C3	2.8000
C6···C4iv	3.596 (3)	H7C···H3	2.3600
C7···C16v	3.464 (3)	H7C···C15ix	2.8900
C9···O3vi	3.209 (3)	H8A···C3	2.7800
C9···O2vi	3.410 (3)	H8A···H3	2.3400
C16···C7vii	3.464 (3)	H8C···C3	2.7300
C18···O4	2.854 (3)	H8C···H3	2.3100
C1···H7Bviii	2.9100	H8C···O4xiii	2.7600
C2···H16Aix	2.9000	H9A···C6	2.7400
C3···H8C	2.7300	H9A···H6	2.2700
C3···H8A	2.7800	H9A···H7Aiv	2.3700
C3···H7A	2.7300	H9A···O4viii	2.8400
C3···H7C	2.8000	H9C···C6	2.8000
C6···H7Bviii	3.0400	H9C···H6	2.4100
C6···H9C	2.8000	H9C···O3vi	2.5500
C6···H11	2.7800	H10···O1	2.3200
C6···H9A	2.7400	H10···O4	2.4400
C7···H3	2.5200	H10···H6iii	2.5900
C8···H3	2.5300	H11···C6	2.7800
C9···H6	2.5300	H11···C14	2.6800
C11···H6	2.7700	H11···H6	2.2500
C11···H14	2.7700	H11···H14	2.1900
C12···H14iii	3.0200	H14···C11	2.7700
C12···H18C	3.0400	H14···H11	2.1900
C12···H16Ciii	3.0600	H14···O4viii	2.5700
C13···H16Ciii	3.0300	H14···C12viii	3.0200
C14···H11	2.6800	H16A···C2x	2.9000
C15···H7Cx	2.8900	H16A···H7Bvii	2.4700
C16···H7Bvii	2.9300	H16B···C17xi	3.0200
C17···H16Bxi	3.0200	H16C···C12viii	3.0600
C18···H18Bxii	3.1000	H16C···C13viii	3.0300
H3···C7	2.5200	H18A···O4	2.7300
H3···C8	2.5300	H18B···C18xiv	3.1000
H3···H7A	2.2800	H18B···H18Bxiv	2.5000
H3···H7C	2.3600	H18B···H18Bxii	2.5000
H3···H8A	2.3400	H18C···O4	2.5900
H3···H8C	2.3100	H18C···C12	3.0400
C15—S1—C17	93.29 (10)	O1—C7—H7A	109.00
C2—O1—C7	119.44 (18)	O1—C7—H7B	109.00
C4—O2—C8	118.45 (19)	O1—C7—H7C	109.00
C5—O3—C9	118.16 (19)	H7A—C7—H7B	109.00
C2—C1—C6	117.12 (18)	H7A—C7—H7C	109.00
C2—C1—C10	120.13 (17)	H7B—C7—H7C	109.00
C6—C1—C10	122.75 (17)	O2—C8—H8A	109.00
O1—C2—C1	115.63 (18)	O2—C8—H8B	109.00
O1—C2—C3	123.22 (17)	O2—C8—H8C	109.00
C1—C2—C3	121.15 (18)	H8A—C8—H8B	109.00
C2—C3—C4	120.17 (19)	H8A—C8—H8C	109.00
O2—C4—C3	124.82 (19)	H8B—C8—H8C	109.00
O2—C4—C5	115.31 (19)	O3—C9—H9A	109.00
C3—C4—C5	119.9 (2)	O3—C9—H9B	109.00
O3—C5—C4	114.78 (19)	O3—C9—H9C	109.00
O3—C5—C6	126.01 (19)	H9A—C9—H9B	109.00
C4—C5—C6	119.20 (19)	H9A—C9—H9C	109.00
C1—C6—C5	122.49 (18)	H9B—C9—H9C	109.00
C1—C10—C11	128.86 (18)	C1—C10—H10	116.00
C10—C11—C12	121.32 (19)	C11—C10—H10	116.00
O4—C12—C11	121.34 (19)	C10—C11—H11	119.00
O4—C12—C13	120.12 (19)	C12—C11—H11	119.00
C11—C12—C13	118.53 (18)	C13—C14—H14	123.00
C12—C13—C14	124.86 (19)	C15—C14—H14	123.00
C12—C13—C17	122.97 (18)	C15—C16—H16A	109.00
C14—C13—C17	112.18 (18)	C15—C16—H16B	109.00
C13—C14—C15	114.0 (2)	C15—C16—H16C	109.00
S1—C15—C14	110.12 (16)	H16A—C16—H16B	109.00
S1—C15—C16	120.88 (17)	H16A—C16—H16C	109.00
C14—C15—C16	129.0 (2)	H16B—C16—H16C	109.00
S1—C17—C13	110.47 (15)	C17—C18—H18A	109.00
S1—C17—C18	119.58 (17)	C17—C18—H18B	109.00
C13—C17—C18	129.96 (19)	C17—C18—H18C	109.00
C2—C3—H3	120.00	H18A—C18—H18B	109.00
C4—C3—H3	120.00	H18A—C18—H18C	109.00
C1—C6—H6	119.00	H18B—C18—H18C	109.00
C5—C6—H6	119.00
C17—S1—C15—C14	−0.40 (19)	O2—C4—C5—O3	−0.1 (3)
C17—S1—C15—C16	−179.6 (2)	O2—C4—C5—C6	179.3 (2)
C15—S1—C17—C13	0.38 (18)	C3—C4—C5—O3	−179.7 (2)
C15—S1—C17—C18	179.9 (2)	C3—C4—C5—C6	−0.3 (3)
C7—O1—C2—C1	178.9 (2)	O3—C5—C6—C1	179.6 (2)
C7—O1—C2—C3	−1.5 (3)	C4—C5—C6—C1	0.3 (3)
C8—O2—C4—C3	2.2 (3)	C1—C10—C11—C12	178.9 (2)
C8—O2—C4—C5	−177.3 (2)	C10—C11—C12—O4	5.2 (3)
C9—O3—C5—C4	−173.0 (2)	C10—C11—C12—C13	−175.2 (2)
C9—O3—C5—C6	7.6 (3)	O4—C12—C13—C14	−171.4 (2)
C6—C1—C2—O1	179.65 (19)	O4—C12—C13—C17	8.8 (3)
C6—C1—C2—C3	0.0 (3)	C11—C12—C13—C14	9.0 (3)
C10—C1—C2—O1	−0.7 (3)	C11—C12—C13—C17	−170.8 (2)
C10—C1—C2—C3	179.7 (2)	C12—C13—C14—C15	−179.9 (2)
C2—C1—C6—C5	−0.2 (3)	C17—C13—C14—C15	0.0 (3)
C10—C1—C6—C5	−179.8 (2)	C12—C13—C17—S1	179.55 (17)
C2—C1—C10—C11	−180.0 (2)	C12—C13—C17—C18	0.2 (4)
C6—C1—C10—C11	−0.3 (3)	C14—C13—C17—S1	−0.3 (2)
O1—C2—C3—C4	−179.6 (2)	C14—C13—C17—C18	−179.7 (2)
C1—C2—C3—C4	0.0 (3)	C13—C14—C15—S1	0.3 (3)
C2—C3—C4—O2	−179.4 (2)	C13—C14—C15—C16	179.4 (2)
C2—C3—C4—C5	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9C···O3vi	0.96	2.55	3.209 (3)	126
C14—H14···O4viii	0.93	2.57	3.483 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9C⋯O3i	0.96	2.55	3.209 (3)	126
C14—H14⋯O4ii	0.93	2.57	3.483 (3)	168

Symmetry codes: (i) ; (ii) .