1,4-Bis(thio-phen-2-yl)butane-1,4-dione.

In the centrosymmetric title compound, C(12)H(10)O(2)S(2), the alkyl chains adopt a fully extended all-trans conformation with respect to the C(thio-phene)-C bond. The non-H atoms of the mol-ecule are nearly planar, with a maximum deviation of 0.063 (2) Å from the mean plane of the constituent atoms. In the crystal, symmetry-related mol-ecules are linked via pairs of C-H⋯π contacts [H-centroid distances of the thio-phene units = 2.79 (9) and 2.82 (4) Å], in turn inter-digitating with each other along the bc plane, thus leading to an inter-woven two-dimensional network.

Related literature

For related structures, see: Becerra et al. (2010 ▶); Liu et al. (2008 ▶); Nair, Devipriya & Eringathodi (2007 ▶); Nair, Vellalath et al. (2007 ▶); Bushueva et al. (2010 ▶). For background information on applications, see: Atalar et al. (2009 ▶); Chen et al. (2009 ▶); Charati et al. (2008 ▶); Cao et al. (2008 ▶); Wu et al. (2008 ▶). For the synthetic procedure, see: Schweiger et al. (2000 ▶). For bond lengths, see: Allen et al. (1987 ▶). For related C—H⋯π hydrogen bonds, see: Hu et al. (2008 ▶); Ishihara et al. (2007 ▶); Jennings et al. (2001 ▶).

Experimental

Crystal data

C12H10O2S2

M = 250.34

Monoclinic,

a = 5.6345 (3) Å

b = 6.2244 (3) Å

c = 16.3779 (9) Å

β = 92.902 (4)°

V = 573.66 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.44 mm−1

T = 296 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.957, T max = 0.978

2000 measured reflections

1023 independent reflections

838 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.200

S = 1.09

1023 reflections

73 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005338/zj2057sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005338/zj2057Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005338/zj2057Isup3.cml

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

C12H10O2S2	F(000) = 260
Mr = 250.34	Dx = 1.449 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1252 reflections
a = 5.6345 (3) Å	θ = 2.6–22.6°
b = 6.2244 (3) Å	µ = 0.44 mm−1
c = 16.3779 (9) Å	T = 296 K
β = 92.902 (4)°	Bolck, yellow
V = 573.66 (5) Å3	0.20 × 0.15 × 0.10 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	1023 independent reflections
Radiation source: fine-focus sealed tube	838 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.1°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
Tmin = 0.957, Tmax = 0.978	k = −7→6
2000 measured reflections	l = −19→19

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.200	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.105P)2 + 0.7893P] where P = (Fo2 + 2Fc2)/3
1023 reflections	(Δ/σ)max < 0.001
73 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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	1.1013 (2)	−0.0356 (2)	0.69663 (7)	0.0577 (5)
C4	0.9593 (6)	0.0981 (6)	0.6181 (2)	0.0376 (9)
C5	1.0715 (7)	0.2877 (6)	0.5837 (2)	0.0403 (9)
C3	0.7295 (7)	0.0004 (6)	0.5931 (2)	0.0368 (9)
H3	0.6239	0.0483	0.5516	0.044*
C2	0.6983 (7)	−0.1823 (8)	0.6446 (3)	0.0537 (12)
H2	0.5649	−0.2702	0.6398	0.064*
C1	0.8824 (8)	−0.2171 (8)	0.7017 (3)	0.0515 (11)
H1	0.8850	−0.3295	0.7392	0.062*
O1	1.2671 (5)	0.3465 (5)	0.6091 (2)	0.0592 (9)
C6	0.9351 (7)	0.4030 (7)	0.5154 (2)	0.0419 (10)
H6A	0.7830	0.4485	0.5346	0.050*
H6B	0.9043	0.3038	0.4705	0.050*

	U11	U22	U33	U12	U13	U23
S1	0.0511 (8)	0.0646 (9)	0.0569 (8)	0.0067 (5)	−0.0020 (5)	0.0135 (6)
C4	0.0371 (19)	0.040 (2)	0.0356 (19)	0.0092 (16)	0.0000 (15)	−0.0042 (17)
C5	0.041 (2)	0.040 (2)	0.040 (2)	0.0079 (17)	0.0006 (16)	−0.0056 (17)
C3	0.039 (2)	0.038 (2)	0.0348 (19)	0.0114 (16)	0.0097 (15)	0.0031 (16)
C2	0.042 (2)	0.058 (3)	0.062 (3)	−0.002 (2)	0.012 (2)	−0.005 (2)
C1	0.047 (2)	0.054 (3)	0.055 (2)	0.008 (2)	0.0129 (19)	0.016 (2)
O1	0.0523 (18)	0.057 (2)	0.067 (2)	−0.0076 (15)	−0.0175 (15)	0.0107 (17)
C6	0.045 (2)	0.039 (2)	0.041 (2)	0.0047 (18)	−0.0052 (16)	−0.0003 (18)

S1—C1	1.678 (5)	C3—H3	0.9300
S1—C4	1.697 (4)	C2—C1	1.379 (6)
C4—C5	1.466 (6)	C2—H2	0.9300
C4—C3	1.470 (6)	C1—H1	0.9300
C5—O1	1.215 (5)	C6—C6i	1.512 (8)
C5—C6	1.506 (5)	C6—H6A	0.9700
C3—C2	1.431 (6)	C6—H6B	0.9700
C1—S1—C4	92.8 (2)	C1—C2—H2	122.8
C5—C4—C3	128.1 (3)	C3—C2—H2	122.8
C5—C4—S1	119.4 (3)	C2—C1—S1	112.9 (3)
C3—C4—S1	112.5 (3)	C2—C1—H1	123.5
O1—C5—C4	120.8 (4)	S1—C1—H1	123.5
O1—C5—C6	122.1 (4)	C5—C6—C6i	113.0 (4)
C4—C5—C6	117.1 (3)	C5—C6—H6A	109.0
C2—C3—C4	107.3 (3)	C6i—C6—H6A	109.0
C2—C3—H3	126.4	C5—C6—H6B	109.0
C4—C3—H3	126.4	C6i—C6—H6B	109.0
C1—C2—C3	114.5 (4)	H6A—C6—H6B	107.8
C1—S1—C4—C5	−179.8 (3)	S1—C4—C3—C2	−0.1 (4)
C1—S1—C4—C3	−0.1 (3)	C4—C3—C2—C1	0.3 (5)
C3—C4—C5—O1	−177.6 (4)	C3—C2—C1—S1	−0.3 (5)
S1—C4—C5—O1	2.0 (5)	C4—S1—C1—C2	0.2 (4)
C3—C4—C5—C6	1.7 (6)	O1—C5—C6—C6i	−1.1 (7)
S1—C4—C5—C6	−178.6 (3)	C4—C5—C6—C6i	179.6 (4)
C5—C4—C3—C2	179.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1ii	0.93	2.79 (9)	3.610 (5)	146
C6—H6B···Cg1iii	0.97	2.82 (4)	3.637 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C4/S1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg1i	0.93	2.79 (9)	3.610 (5)	146
C6—H6B⋯Cg1ii	0.97	2.82 (4)	3.637 (4)	143

Symmetry codes: (i) ; (ii) .