(E,E)-1,5-Di-2-thienylpenta-1,4-dien-3-one.

In the title compound, C(13)H(10)OS(2), the dihedral angle between the thio-phene rings is 14.3 (1)°. The mol-ecular structure is stabilized by C-H⋯π inter-actions between a thio-phene H atom and an adjacent thio-phene ring, and by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the bioactivity of chalcones, see: Go et al. (2005 ▶). For uses in organic solid-state photochemistry, see: Gould et al. (1995 ▶); For a related structure, see: Arshad et al. (2008 ▶). For the non-linear optical properties of bis-chalcones, see: Uchida et al. (1998 ▶).

Experimental

Crystal data

C13H10OS2

M = 246.35

Orthorhombic,

a = 12.1141 (4) Å

b = 7.4449 (3) Å

c = 27.246 (1) Å

V = 2457.27 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.41 mm−1

T = 293 (2) K

0.26 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.987

13976 measured reflections

2373 independent reflections

1719 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.210

S = 1.01

2373 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.36 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 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026603/lx2066sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026603/lx2066Isup2.hkl

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

C13H10OS2	F000 = 1024
Mr = 246.35	Dx = 1.332 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10259 reflections
a = 12.1141 (4) Å	θ = 2.3–30.3º
b = 7.4449 (3) Å	µ = 0.41 mm−1
c = 27.246 (1) Å	T = 293 (2) K
V = 2457.27 (16) Å3	Block, colourless
Z = 8	0.26 × 0.15 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	2373 independent reflections
Radiation source: fine-focus sealed tube	1719 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
Detector resolution: 10 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 1.5º
ω scans	h = −11→14
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	k = −7→9
Tmin = 0.984, Tmax = 0.987	l = −32→31
13976 measured reflections

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.211	w = 1/[σ2(Fo2) + (0.1295P)2 + 1.4091P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2373 reflections	Δρmax = 0.49 e Å−3
145 parameters	Δρmin = −0.36 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.52710 (7)	0.54328 (13)	0.23889 (4)	0.0733 (4)
S2	0.53529 (8)	0.23805 (14)	0.51370 (4)	0.0801 (4)
O1	0.82061 (18)	0.5548 (4)	0.38920 (9)	0.0734 (7)
C1	0.5312 (3)	0.2113 (6)	0.57495 (18)	0.0876 (13)
H1	0.4768	0.1455	0.5910	0.105*
C2	0.6135 (4)	0.2934 (6)	0.59817 (16)	0.0907 (12)
H2	0.6209	0.2904	0.6321	0.109*
C3	0.6903 (3)	0.3874 (5)	0.56716 (12)	0.0667 (9)
H3	0.7525	0.4507	0.5773	0.080*
C4	0.6519 (3)	0.3642 (4)	0.51665 (13)	0.0612 (8)
C5	0.7055 (3)	0.4350 (4)	0.47339 (13)	0.0610 (8)
H5	0.7755	0.4843	0.4774	0.073*
C6	0.6638 (3)	0.4359 (4)	0.42854 (13)	0.0612 (8)
H6	0.5938	0.3881	0.4236	0.073*
C7	0.7236 (2)	0.5093 (4)	0.38617 (12)	0.0573 (8)
C8	0.6611 (2)	0.5283 (4)	0.34019 (12)	0.0594 (8)
H8	0.5901	0.4810	0.3384	0.071*
C9	0.7027 (2)	0.6109 (4)	0.30106 (12)	0.0565 (7)
H9	0.7733	0.6583	0.3045	0.068*
C10	0.6513 (2)	0.6354 (4)	0.25413 (12)	0.0536 (7)
C11	0.6974 (2)	0.7299 (4)	0.21337 (11)	0.0541 (7)
H11	0.7653	0.7882	0.2132	0.065*
C12	0.6228 (3)	0.7207 (6)	0.17301 (14)	0.0794 (10)
H12	0.6364	0.7764	0.1431	0.095*
C13	0.5322 (3)	0.6260 (6)	0.18183 (15)	0.0774 (11)
H13	0.4771	0.6074	0.1586	0.093*

	U11	U22	U33	U12	U13	U23
S1	0.0542 (6)	0.0750 (6)	0.0909 (8)	−0.0090 (4)	−0.0089 (4)	−0.0068 (5)
S2	0.0619 (6)	0.0821 (7)	0.0962 (9)	−0.0065 (4)	0.0047 (4)	0.0076 (5)
O1	0.0483 (13)	0.1008 (18)	0.0710 (16)	−0.0067 (11)	0.0009 (10)	−0.0029 (12)
C1	0.069 (2)	0.090 (3)	0.103 (3)	0.0109 (19)	0.018 (2)	0.033 (2)
C2	0.091 (3)	0.113 (3)	0.068 (2)	0.012 (3)	0.000 (2)	0.013 (2)
C3	0.071 (2)	0.073 (2)	0.056 (2)	−0.0057 (16)	−0.0001 (15)	0.0110 (15)
C4	0.0558 (17)	0.0542 (15)	0.074 (2)	0.0020 (13)	0.0024 (14)	0.0003 (14)
C5	0.0527 (16)	0.0593 (17)	0.071 (2)	−0.0027 (13)	−0.0005 (15)	−0.0028 (14)
C6	0.0510 (16)	0.0621 (17)	0.071 (2)	−0.0018 (13)	0.0012 (14)	−0.0036 (15)
C7	0.0497 (17)	0.0576 (16)	0.065 (2)	0.0021 (13)	0.0033 (13)	−0.0081 (14)
C8	0.0467 (15)	0.0646 (17)	0.067 (2)	−0.0029 (13)	0.0012 (14)	−0.0081 (15)
C9	0.0435 (14)	0.0592 (16)	0.067 (2)	−0.0007 (12)	−0.0031 (13)	−0.0097 (14)
C10	0.0457 (15)	0.0511 (14)	0.0641 (19)	0.0013 (12)	−0.0020 (13)	−0.0103 (13)
C11	0.0442 (14)	0.0624 (17)	0.0558 (18)	−0.0046 (12)	−0.0030 (12)	−0.0082 (13)
C12	0.081 (2)	0.096 (3)	0.062 (2)	0.013 (2)	0.0044 (18)	−0.0026 (18)
C13	0.063 (2)	0.091 (3)	0.078 (3)	0.0085 (18)	−0.0146 (17)	−0.022 (2)

S1—C13	1.673 (5)	C6—C7	1.468 (5)
S1—C10	1.704 (3)	C6—H6	0.9300
S2—C1	1.682 (5)	C7—C8	1.471 (5)
S2—C4	1.699 (3)	C8—C9	1.330 (5)
O1—C7	1.225 (4)	C8—H8	0.9300
C1—C2	1.330 (6)	C9—C10	1.434 (4)
C1—H1	0.9300	C9—H9	0.9300
C2—C3	1.438 (5)	C10—C11	1.429 (4)
C2—H2	0.9300	C11—C12	1.425 (5)
C3—C4	1.463 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.326 (5)
C4—C5	1.445 (5)	C12—H12	0.9300
C5—C6	1.322 (5)	C13—H13	0.9300
C5—H5	0.9300
C13—S1—C10	92.62 (17)	O1—C7—C8	121.6 (3)
C1—S2—C4	92.5 (2)	C6—C7—C8	116.8 (3)
C2—C1—S2	113.3 (3)	C9—C8—C7	122.1 (3)
C2—C1—H1	123.3	C9—C8—H8	118.9
S2—C1—H1	123.3	C7—C8—H8	118.9
C1—C2—C3	115.4 (4)	C8—C9—C10	127.5 (3)
C1—C2—H2	122.3	C8—C9—H9	116.3
C3—C2—H2	122.3	C10—C9—H9	116.3
C2—C3—C4	106.8 (3)	C9—C10—C11	125.9 (3)
C2—C3—H3	126.6	C9—C10—S1	123.3 (2)
C4—C3—H3	126.6	C11—C10—S1	110.7 (2)
C5—C4—C3	125.6 (3)	C12—C11—C10	109.1 (3)
C5—C4—S2	122.5 (3)	C12—C11—H11	125.4
C3—C4—S2	112.0 (2)	C10—C11—H11	125.4
C6—C5—C4	125.7 (3)	C13—C12—C11	114.2 (4)
C6—C5—H5	117.1	C13—C12—H12	122.9
C4—C5—H5	117.1	C11—C12—H12	122.9
C5—C6—C7	122.7 (3)	C12—C13—S1	113.3 (3)
C5—C6—H6	118.7	C12—C13—H13	123.4
C7—C6—H6	118.7	S1—C13—H13	123.4
O1—C7—C6	121.5 (3)
C4—S2—C1—C2	0.3 (4)	O1—C7—C8—C9	−6.5 (5)
S2—C1—C2—C3	−0.5 (5)	C6—C7—C8—C9	172.5 (3)
C1—C2—C3—C4	0.5 (5)	C7—C8—C9—C10	178.8 (3)
C2—C3—C4—C5	−179.2 (3)	C8—C9—C10—C11	177.9 (3)
C2—C3—C4—S2	−0.3 (4)	C8—C9—C10—S1	−5.4 (4)
C1—S2—C4—C5	179.0 (3)	C13—S1—C10—C9	−177.9 (3)
C1—S2—C4—C3	0.1 (3)	C13—S1—C10—C11	−0.8 (2)
C3—C4—C5—C6	−170.2 (3)	C9—C10—C11—C12	178.5 (3)
S2—C4—C5—C6	11.1 (5)	S1—C10—C11—C12	1.5 (3)
C4—C5—C6—C7	−179.5 (3)	C10—C11—C12—C13	−1.6 (4)
C5—C6—C7—O1	8.6 (5)	C11—C12—C13—S1	1.0 (4)
C5—C6—C7—C8	−170.4 (3)	C10—S1—C13—C12	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1i	0.93	2.47	3.374 (5)	165
C13—H13···O1ii	0.93	2.33	3.255 (4)	171
C11—H11···Cgiii	0.93	3.12	3.936 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.47	3.374 (5)	165
C13—H13⋯O1ii	0.93	2.33	3.255 (4)	171
C11—H11⋯Cgiii	0.93	3.12	3.936 (5)	148

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the C10/C11/C12/C13/S1 thio­phene ring.