2,2'-Bithio-phene-3,3'-dicarbonitrile.

The complete mol-ecule of the title compound, C(10)H(4)N(2)S(2), is generated by an inversion center situated at the mid-point of the bridging C-C bond. The bithio-phene ring system is planar [maximum deviation = 0.003 (2) Å] and the central C-C bond length is 1.450 (2) Å. There are no significant inter-molecular inter-actions in the crystal structure, which is stabilized by van der Waals inter-actions.

Related literature

For the importance of bithio­phene derivatives, see: Katz et al. (1995 ▶). For their applications, see: Deng et al. (2011 ▶); Thomas et al. (2008 ▶). For background to the title compound, see: Demanze et al. (1996 ▶); Pletnev et al. (2002 ▶); For related structures, see: Benedict et al. (2004 ▶); Huang & Li (2011 ▶); Pelletier et al. (1995 ▶); Li & Li (2009 ▶); Teh et al. (2012 ▶). For thio­phene C—S bond lengths, see: Howie & Wardell (2006 ▶). For the normal bonding picture for bithio­phene, see: Khan et al. (2004 ▶).

Experimental

Crystal data

C10H4N2S2

M = 216.27

Monoclinic,

a = 3.9084 (1) Å

b = 9.8832 (4) Å

c = 12.0091 (5) Å

β = 93.900 (2)°

V = 462.81 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.881, T max = 0.900

6689 measured reflections

1802 independent reflections

1409 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.105

S = 1.05

1802 reflections

64 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.20 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032503/su2475sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032503/su2475Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032503/su2475Isup3.cml

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

C10H4N2S2	Z = 2
Mr = 216.27	F(000) = 220
Monoclinic, P21/c	Dx = 1.552 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 3.9084 (1) Å	θ = 2.7–33.5°
b = 9.8832 (4) Å	µ = 0.53 mm−1
c = 12.0091 (5) Å	T = 293 K
β = 93.900 (2)°	Block, yellow
V = 462.81 (3) Å3	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	1802 independent reflections
Radiation source: fine-focus sealed tube	1409 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω and φ scan	θmax = 33.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −5→5
Tmin = 0.881, Tmax = 0.900	k = −15→14
6689 measured reflections	l = −18→18

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.0819P] where P = (Fo2 + 2Fc2)/3
1802 reflections	(Δ/σ)max = 0.001
64 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

Experimental. Spectroscopic data for the title compund:IR (KBr, cm-1) 2221.0 (ν C≡N); 1H NMR (CDCl3, 500.13 MHz) δ 7.37 (d, J = 5.36 Hz, 2H),7.53 (d, J = 5.36 Hz, 2H); 13C NMR (CDCl3, 125.75 MHz); δ 110.0, 114.5, 128.3, 130.4, 141.0 p.p.m.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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	0.28852 (8)	0.68019 (3)	0.41382 (2)	0.04106 (12)
C1	0.4855 (3)	0.57190 (12)	0.51077 (9)	0.0320 (2)
C2	0.6002 (3)	0.64524 (13)	0.60413 (9)	0.0367 (2)
C5	0.7804 (4)	0.59005 (15)	0.70133 (10)	0.0439 (3)
C4	0.3580 (4)	0.81738 (13)	0.49772 (12)	0.0475 (3)
H4	0.2877	0.9046	0.4781	0.057*
C3	0.5265 (4)	0.78545 (14)	0.59594 (11)	0.0458 (3)
H3	0.5872	0.8480	0.6517	0.055*
N1	0.9252 (4)	0.55103 (16)	0.77997 (11)	0.0630 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0472 (2)	0.03822 (18)	0.03623 (18)	0.00130 (11)	−0.00859 (12)	0.00367 (11)
C1	0.0314 (4)	0.0354 (5)	0.0287 (5)	−0.0021 (4)	−0.0009 (3)	0.0025 (4)
C2	0.0394 (6)	0.0387 (6)	0.0313 (5)	−0.0030 (5)	−0.0020 (4)	−0.0006 (4)
C5	0.0518 (7)	0.0431 (6)	0.0354 (6)	−0.0063 (5)	−0.0073 (5)	−0.0029 (5)
C4	0.0567 (8)	0.0339 (6)	0.0507 (7)	0.0022 (5)	−0.0053 (6)	0.0005 (5)
C3	0.0554 (8)	0.0380 (6)	0.0429 (7)	−0.0015 (5)	−0.0044 (5)	−0.0048 (5)
N1	0.0802 (10)	0.0599 (8)	0.0454 (6)	−0.0049 (7)	−0.0218 (6)	0.0021 (6)

S1—C4	1.7000 (14)	C2—C5	1.4298 (16)
S1—C1	1.7240 (11)	C5—N1	1.1351 (17)
C1—C2	1.3838 (16)	C4—C3	1.3487 (19)
C1—C1i	1.450 (2)	C4—H4	0.9300
C2—C3	1.4173 (19)	C3—H3	0.9300
C4—S1—C1	92.80 (6)	N1—C5—C2	177.43 (15)
C2—C1—C1i	129.27 (13)	C3—C4—S1	112.37 (10)
C2—C1—S1	109.09 (9)	C3—C4—H4	123.8
C1i—C1—S1	121.63 (11)	S1—C4—H4	123.8
C1—C2—C3	113.76 (11)	C4—C3—C2	111.98 (12)
C1—C2—C5	125.17 (12)	C4—C3—H3	124.0
C3—C2—C5	121.07 (11)	C2—C3—H3	124.0