(1E,4E)-1,5-Bis(thio-phen-3-yl)penta-1,4-dien-3-one.

The title compound, C(13)H(10)OS(2), exhibits twists between the central C(3)O and ethene residues [O-C-C-C torsion angles = -8.4 (3) and 11.8 (3)°], and between the ethene and adjacent thio-phenyl residues [C-C-C-C torsion angles = -4.2 (3) and 10.5 (3)°]. As a result, the mol-ecule is non-planar, the dihedral angle formed between the terminal thio-phenyl groups being 15.45 (10)°. The presence of C-H⋯O inter-actions involving the bifurcated carbonyl O atom leads to supra-molecular arrays in the ac plane. These are linked into a three-dimensional architecture by C-H⋯π inter-actions involving both thio-phenyl residues.

Related literature

For the use of chalcones in organic synthesis, see: Nehad et al. (2007 ▶); Xu et al. (2001 ▶). For the biological activity of chalcones, see: Lambert et al. (2009 ▶); Boumendjel et al. (2008 ▶). Semi-empirical quantum chemical calculations were performed using MOPAC2009, see: Stewart (2009 ▶).

Experimental

Crystal data

C13H10OS2

M = 246.33

Orthorhombic,

a = 11.8908 (3) Å

b = 7.1807 (1) Å

c = 28.3004 (6) Å

V = 2416.41 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.40 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

39245 measured reflections

2760 independent reflections

2187 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.121

S = 1.09

2760 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103248X/hg5079sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103248X/hg5079Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103248X/hg5079Isup3.cml

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

C13H10OS2	F(000) = 1024
Mr = 246.33	Dx = 1.354 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 50 reflections
a = 11.8908 (3) Å	θ = 5.0–30.0°
b = 7.1807 (1) Å	µ = 0.42 mm−1
c = 28.3004 (6) Å	T = 293 K
V = 2416.41 (9) Å3	Needle, colorless
Z = 8	0.40 × 0.20 × 0.10 mm

Bruker SMART APEX CCD diffractometer	2187 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 27.5°, θmin = 1.4°
ω and φ scans	h = −15→15
39245 measured reflections	k = −8→9
2760 independent reflections	l = −36→36

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) = 0.121	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0528P)2 + 0.9807P] where P = (Fo2 + 2Fc2)/3
2760 reflections	(Δ/σ)max = 0.002
145 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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 > 2σ(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	0.38360 (5)	0.12409 (9)	0.833684 (17)	0.0655 (2)
S2	0.38292 (5)	−0.15855 (9)	0.398067 (18)	0.0658 (2)
O1	0.17784 (11)	0.0181 (2)	0.61498 (4)	0.0581 (4)
C3	0.35238 (14)	0.0577 (2)	0.74599 (6)	0.0422 (4)
C5	0.29957 (15)	0.0511 (2)	0.69974 (6)	0.0441 (4)
H5	0.2294	0.1072	0.6971	0.053*
C8	0.33643 (16)	−0.0925 (3)	0.57374 (6)	0.0476 (4)
H8	0.4061	−0.1500	0.5770	0.057*
C2	0.45551 (15)	−0.0286 (3)	0.75867 (6)	0.0516 (4)
H2	0.5002	−0.0944	0.7375	0.062*
C10	0.34646 (15)	−0.1238 (2)	0.48658 (6)	0.0462 (4)
C6	0.34072 (15)	−0.0264 (3)	0.66085 (6)	0.0467 (4)
H6	0.4121	−0.0794	0.6617	0.056*
C11	0.30593 (18)	−0.0723 (3)	0.44352 (7)	0.0569 (5)
H11	0.2427	0.0024	0.4395	0.068*
C9	0.29452 (16)	−0.0692 (3)	0.53080 (6)	0.0472 (4)
H9	0.2246	−0.0118	0.5288	0.057*
C4	0.30471 (17)	0.1448 (3)	0.78394 (6)	0.0518 (4)
H4	0.2366	0.2084	0.7827	0.062*
C7	0.27673 (15)	−0.0308 (2)	0.61635 (6)	0.0447 (4)
C1	0.48190 (17)	−0.0050 (3)	0.80489 (7)	0.0616 (5)
H1	0.5460	−0.0536	0.8191	0.074*
C13	0.44370 (16)	−0.2385 (3)	0.48152 (7)	0.0550 (5)
H13	0.4836	−0.2873	0.5069	0.066*
C12	0.47191 (17)	−0.2690 (3)	0.43574 (8)	0.0616 (5)
H12	0.5326	−0.3415	0.4261	0.074*

	U11	U22	U33	U12	U13	U23
S1	0.0834 (4)	0.0759 (4)	0.0373 (3)	−0.0050 (3)	−0.0023 (2)	0.0014 (2)
S2	0.0802 (4)	0.0740 (4)	0.0433 (3)	0.0006 (3)	0.0076 (2)	−0.0057 (2)
O1	0.0456 (7)	0.0847 (10)	0.0442 (7)	0.0005 (7)	−0.0025 (5)	−0.0016 (7)
C3	0.0453 (9)	0.0400 (8)	0.0411 (8)	−0.0032 (7)	−0.0018 (7)	0.0029 (7)
C5	0.0441 (9)	0.0442 (9)	0.0440 (9)	−0.0013 (7)	−0.0045 (7)	0.0027 (7)
C8	0.0482 (10)	0.0500 (9)	0.0447 (9)	−0.0014 (8)	−0.0005 (8)	−0.0020 (8)
C2	0.0456 (10)	0.0615 (11)	0.0476 (10)	0.0033 (8)	−0.0019 (8)	0.0032 (8)
C10	0.0496 (10)	0.0457 (9)	0.0432 (9)	−0.0017 (8)	−0.0014 (7)	−0.0031 (7)
C6	0.0463 (9)	0.0509 (10)	0.0428 (9)	−0.0003 (8)	−0.0030 (7)	0.0022 (7)
C11	0.0659 (12)	0.0604 (11)	0.0445 (10)	0.0106 (10)	−0.0001 (9)	−0.0047 (8)
C9	0.0485 (9)	0.0485 (9)	0.0447 (9)	0.0013 (8)	0.0004 (7)	−0.0025 (7)
C4	0.0583 (11)	0.0530 (10)	0.0441 (9)	0.0040 (9)	−0.0001 (8)	0.0026 (8)
C7	0.0455 (10)	0.0478 (9)	0.0408 (9)	−0.0068 (8)	−0.0012 (7)	0.0023 (7)
C1	0.0542 (11)	0.0799 (14)	0.0507 (11)	−0.0015 (10)	−0.0095 (9)	0.0139 (10)
C13	0.0482 (10)	0.0634 (12)	0.0535 (11)	0.0015 (9)	−0.0024 (8)	−0.0028 (9)
C12	0.0508 (11)	0.0693 (13)	0.0648 (12)	0.0012 (10)	0.0094 (9)	−0.0111 (10)

S1—C4	1.6982 (19)	C2—H2	0.9300
S1—C1	1.700 (2)	C10—C11	1.362 (3)
S2—C11	1.6960 (19)	C10—C13	1.427 (3)
S2—C12	1.699 (2)	C10—C9	1.450 (2)
O1—C7	1.228 (2)	C6—C7	1.472 (2)
C3—C4	1.366 (2)	C6—H6	0.9300
C3—C2	1.420 (2)	C11—H11	0.9300
C3—C5	1.452 (2)	C9—H9	0.9300
C5—C6	1.327 (2)	C4—H4	0.9300
C5—H5	0.9300	C1—H1	0.9300
C8—C9	1.324 (2)	C13—C12	1.356 (3)
C8—C7	1.468 (2)	C13—H13	0.9300
C8—H8	0.9300	C12—H12	0.9300
C2—C1	1.356 (3)
C4—S1—C1	91.73 (9)	C10—C11—H11	123.6
C11—S2—C12	91.76 (10)	S2—C11—H11	123.6
C4—C3—C2	111.06 (16)	C8—C9—C10	126.70 (17)
C4—C3—C5	122.97 (16)	C8—C9—H9	116.7
C2—C3—C5	125.93 (16)	C10—C9—H9	116.7
C6—C5—C3	127.01 (17)	C3—C4—S1	112.49 (15)
C6—C5—H5	116.5	C3—C4—H4	123.8
C3—C5—H5	116.5	S1—C4—H4	123.8
C9—C8—C7	122.26 (17)	O1—C7—C8	121.58 (16)
C9—C8—H8	118.9	O1—C7—C6	121.05 (16)
C7—C8—H8	118.9	C8—C7—C6	117.36 (16)
C1—C2—C3	112.91 (18)	C2—C1—S1	111.80 (15)
C1—C2—H2	123.5	C2—C1—H1	124.1
C3—C2—H2	123.5	S1—C1—H1	124.1
C11—C10—C13	110.73 (17)	C12—C13—C10	112.92 (18)
C11—C10—C9	123.24 (17)	C12—C13—H13	123.5
C13—C10—C9	126.03 (17)	C10—C13—H13	123.5
C5—C6—C7	121.90 (17)	C13—C12—S2	111.74 (16)
C5—C6—H6	119.1	C13—C12—H12	124.1
C7—C6—H6	119.1	S2—C12—H12	124.1
C10—C11—S2	112.85 (15)
C4—C3—C5—C6	178.38 (18)	C5—C3—C4—S1	178.21 (13)
C2—C3—C5—C6	−4.2 (3)	C1—S1—C4—C3	−0.77 (16)
C4—C3—C2—C1	0.2 (2)	C9—C8—C7—O1	11.8 (3)
C5—C3—C2—C1	−177.47 (18)	C9—C8—C7—C6	−167.02 (17)
C3—C5—C6—C7	177.39 (16)	C5—C6—C7—O1	−8.4 (3)
C13—C10—C11—S2	−0.2 (2)	C5—C6—C7—C8	170.49 (17)
C9—C10—C11—S2	−179.36 (15)	C3—C2—C1—S1	−0.7 (2)
C12—S2—C11—C10	0.47 (17)	C4—S1—C1—C2	0.87 (17)
C7—C8—C9—C10	179.69 (17)	C11—C10—C13—C12	−0.2 (3)
C11—C10—C9—C8	−170.5 (2)	C9—C10—C13—C12	178.87 (18)
C13—C10—C9—C8	10.5 (3)	C10—C13—C12—S2	0.6 (2)
C2—C3—C4—S1	0.5 (2)	C11—S2—C12—C13	−0.61 (18)

Cg1 and Cg2 are the centroids of the S1,C1–C4 and S2,C10–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.93	2.49	3.256 (2)	140
C12—H12···O1ii	0.93	2.44	3.355 (2)	169
C2—H2···Cg1iii	0.93	2.86	3.671 (2)	147
C4—H4···Cg1iv	0.93	2.97	3.809 (2)	151
C11—H11···Cg2iv	0.93	2.83	3.702 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the S1,C1–C4 and S2,C10–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.49	3.256 (2)	140
C12—H12⋯O1ii	0.93	2.44	3.355 (2)	169
C2—H2⋯Cg1iii	0.93	2.86	3.671 (2)	147
C4—H4⋯Cg1iv	0.93	2.97	3.809 (2)	151
C11—H11⋯Cg2iv	0.93	2.83	3.702 (2)	156

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