Bis(2-thien-yl)acetyl-ene.

The planar [maximum deviation 0.0066 (4) Å] symmetrical mol-ecule of the title compound, C(10)H(6)S(2), lies across a crystallographic inversion centre. The thio-phene rings are rotationally disordered about the acetyl-ene bond, with the two pseudo inversion-related S atoms in 0.80:0.20 occupancy sites. The C C bond distance is 1.195 (9) Å.

Related literature

For the preparation of the title compound, related diaryl­acetyl­enes and cobalt-containing metallocenes derived from these materials, see: Harrison et al. (1997 ▶); Harcourt et al. (2008 ▶). For recent synthetic organic uses, see: Yu & Rovis (2006 ▶); Geyer et al. (2008 ▶). The metal center employed in an acetyl­ene cyclo­oligomerization may also remain as an integral component of the product, or products, see: Rausch & Genetti (1970 ▶). For spectroscopic data, see: Mio et al. (2002 ▶).

Experimental

Crystal data

C10H6S2

M = 190.29

Orthorhombic,

a = 10.6325 (15) Å

b = 10.8713 (15) Å

c = 7.5600 (5) Å

V = 873.85 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.54 mm−1

T = 120 K

0.55 × 0.05 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.755, T max = 0.984

3812 measured reflections

849 independent reflections

493 reflections with I > 2σ(I)

R int = 0.129

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.173

S = 1.08

849 reflections

58 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.41 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036812/zs2008sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036812/zs2008Isup2.hkl

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

C10H6S2	F(000) = 392
Mr = 190.29	Dx = 1.446 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1041 reflections
a = 10.6325 (15) Å	θ = 1.0–27.5°
b = 10.8713 (15) Å	µ = 0.54 mm−1
c = 7.5600 (5) Å	T = 120 K
V = 873.85 (18) Å3	Needle, colourless
Z = 4	0.55 × 0.05 × 0.03 mm

Nonius KappaCCD diffractometer	849 independent reflections
Radiation source: Bruker Nonius FR591 rotating anode	493 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.129
Detector resolution: 9.091 pixels mm-1	θmax = 26.0°, θmin = 2.7°
φ and ω scans	h = −13→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −13→12
Tmin = 0.755, Tmax = 0.984	l = −9→8
3812 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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.050P)2 + 3.1085P] where P = (Fo2 + 2Fc2)/3
849 reflections	(Δ/σ)max < 0.001
58 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. The minimum and maximum absorption values stated above are those calculated in SHELXL97 from the given crystal dimensions. The ratio of minimum to maximum apparent transmission was determined experimentally as 0.675726.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.17278 (13)	0.28773 (15)	0.17139 (19)	0.0303 (6)	0.80
C1	0.17278 (13)	0.28773 (15)	0.17139 (19)	0.0303 (6)	0.20
H1	0.1105	0.2380	0.2263	0.038*	0.20
C2	0.1671 (4)	0.4188 (5)	0.0513 (6)	0.0220 (12)
C3	0.2949 (3)	0.4642 (3)	−0.0126 (4)	0.0291 (9)	0.80
H3	0.3142	0.5342	−0.0827	0.036*	0.80
S3	0.2949 (3)	0.4642 (3)	−0.0126 (4)	0.0291 (9)	0.20
C4	0.3820 (5)	0.3703 (5)	0.0635 (6)	0.0295 (15)
H4	0.4705	0.3749	0.0468	0.037*
C5	0.3285 (4)	0.2786 (5)	0.1572 (6)	0.0271 (13)
H5	0.3757	0.2144	0.2105	0.034*
C6	0.0498 (4)	0.4768 (5)	0.0149 (6)	0.0235 (14)

	U11	U22	U33	U12	U13	U23
S1	0.0283 (8)	0.0314 (11)	0.0311 (8)	0.0002 (8)	−0.0017 (6)	0.0030 (7)
C1	0.0283 (8)	0.0314 (11)	0.0311 (8)	0.0002 (8)	−0.0017 (6)	0.0030 (7)
C2	0.022 (2)	0.023 (3)	0.021 (2)	−0.001 (2)	−0.0019 (19)	0.000 (2)
C3	0.0264 (16)	0.029 (2)	0.0322 (16)	0.0028 (17)	−0.0049 (13)	−0.0064 (15)
S3	0.0264 (16)	0.029 (2)	0.0322 (16)	0.0028 (17)	−0.0049 (13)	−0.0064 (15)
C4	0.021 (2)	0.035 (4)	0.032 (3)	−0.002 (3)	0.003 (2)	−0.008 (3)
C5	0.030 (3)	0.027 (3)	0.025 (2)	0.012 (3)	−0.007 (2)	−0.006 (2)
C6	0.025 (2)	0.021 (4)	0.025 (2)	−0.002 (2)	−0.001 (2)	−0.001 (2)

S1—C2	1.691 (5)	C4—C5	1.349 (7)
C2—C6	1.424 (6)	C4—H4	0.95
C2—C3	1.525 (5)	C5—H5	0.95
C3—C4	1.493 (6)	C6—C6i	1.195 (9)
C3—H3	0.95
C6—C2—C3	125.2 (4)	C5—C4—C3	116.4 (4)
C6—C2—S1	120.5 (4)	C5—C4—H4	121.8
C3—C2—S1	114.2 (3)	C3—C4—H4	121.8
C4—C3—C2	102.1 (3)	C4—C5—H5	122.9
C4—C3—H3	128.9	C6i—C6—C2	178.7 (7)
C2—C3—H3	128.9
C6—C2—C3—C4	179.9 (4)	C2—C3—C4—C5	0.8 (5)
S1—C2—C3—C4	−1.1 (4)