3,3',5,5'-Tetra-bromo-2,2'-bithio-phene.

The title compound, C(8)H(2)Br(4)S(2), was prepared by bromination of 2,2'-bithio-phene with bromine. The mol-ecule is located on a crystallographic twofold rotation axis, thereby imposing equal geometry of the two thio-phene rings. Each five-membered ring is planar [maximum deviation 0.011 (9) Å] and the dihedral angle between the planes through the rings is 47.2 (4)°. The mol-ecules are arranged to minimize intramolecular contacts between the 3-3' and 5-5'-bromine atoms.

Related literature

For use of the title compound as an intermediate in the synthesis of oligothiophenes and polythiophenes, see: Roncali (1997 ▶); Funahashi et al. (2005 ▶). For synthetic methods, see: Takahashi et al. (2006 ▶); Lin et al. (2005 ▶).

Experimental

Crystal data

C8H2Br4S2

M = 481.86

Monoclinic,

a = 17.164 (3) Å

b = 4.0153 (7) Å

c = 18.655 (3) Å

β = 115.395 (3)°

V = 1161.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 14.18 mm−1

T = 293 K

0.40 × 0.17 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.258, T max = 1.000 (expected range = 0.122–0.472)

2792 measured reflections

1077 independent reflections

886 reflections with I > 2σ(I)

R int = 0.146

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.208

S = 1.00

1077 reflections

64 parameters

H-atom parameters constrained

Δρmax = 1.15 e Å−3

Δρmin = −1.06 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809011647/kj2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011647/kj2109Isup2.hkl

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

C8H2Br4S2	Dx = 2.756 Mg m−3
Mr = 481.86	Melting point = 413–414 K
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.164 (3) Å	Cell parameters from 1249 reflections
b = 4.0153 (7) Å	θ = 4.8–55.3°
c = 18.655 (3) Å	µ = 14.18 mm−1
β = 115.395 (3)°	T = 293 K
V = 1161.4 (4) Å3	Prismatic, yellow
Z = 4	0.40 × 0.17 × 0.05 mm
F(000) = 888

Bruker SMART CCD area-detector diffractometer	1077 independent reflections
Radiation source: fine-focus sealed tube	886 reflections with I > 2σ(I)
graphite	Rint = 0.146
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −20→18
Tmin = 0.258, Tmax = 1.000	k = −4→4
2792 measured reflections	l = −22→21

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1428P)2] where P = (Fo2 + 2Fc2)/3
1077 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 1.15 e Å−3
0 restraints	Δρmin = −1.06 e Å−3

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
Br1	0.17755 (6)	0.2991 (3)	0.27753 (6)	0.0443 (5)
Br2	0.11718 (8)	0.7463 (3)	0.54198 (6)	0.0562 (5)
S1	−0.00225 (17)	0.7354 (6)	0.36201 (13)	0.0393 (7)
C1	0.0301 (5)	0.581 (2)	0.2918 (4)	0.0331 (17)
C2	0.1140 (5)	0.480 (2)	0.3291 (4)	0.0354 (17)
C4	0.0973 (6)	0.650 (2)	0.4373 (5)	0.041 (2)
C3	0.1540 (5)	0.521 (2)	0.4129 (4)	0.0411 (19)
H3	0.2109	0.4669	0.4459	0.049*

	U11	U22	U33	U12	U13	U23
Br1	0.0524 (7)	0.0457 (7)	0.0483 (7)	0.0023 (4)	0.0344 (6)	−0.0050 (4)
Br2	0.0735 (9)	0.0718 (9)	0.0312 (7)	−0.0072 (5)	0.0298 (6)	−0.0063 (4)
S1	0.0508 (15)	0.0482 (13)	0.0306 (12)	0.0043 (9)	0.0286 (11)	−0.0007 (8)
C1	0.050 (5)	0.030 (4)	0.034 (4)	0.000 (4)	0.032 (4)	0.000 (3)
C2	0.052 (5)	0.030 (4)	0.034 (4)	−0.006 (3)	0.028 (4)	0.001 (3)
C4	0.059 (6)	0.042 (5)	0.028 (4)	0.003 (4)	0.025 (4)	0.006 (3)
C3	0.050 (5)	0.046 (5)	0.035 (4)	−0.003 (4)	0.025 (4)	0.005 (4)

Br1—C2	1.882 (8)	C1—C1i	1.455 (15)
Br2—C4	1.873 (8)	C2—C3	1.422 (11)
S1—C4	1.719 (9)	C4—C3	1.342 (11)
S1—C1	1.741 (7)	C3—H3	0.9300
C1—C2	1.365 (11)
C4—S1—C1	91.0 (4)	C3—C4—S1	114.3 (6)
C2—C1—C1i	131.0 (8)	C3—C4—Br2	126.8 (7)
C2—C1—S1	109.2 (6)	S1—C4—Br2	118.9 (5)
C1i—C1—S1	119.8 (7)	C4—C3—C2	109.8 (8)
C1—C2—C3	115.6 (7)	C4—C3—H3	125.1
C1—C2—Br1	124.7 (6)	C2—C3—H3	125.1
C3—C2—Br1	119.6 (6)
C4—S1—C1—C2	−0.9 (6)	C1—S1—C4—C3	1.7 (7)
C4—S1—C1—C1i	179.8 (5)	C1—S1—C4—Br2	−179.2 (5)
C1i—C1—C2—C3	179.2 (5)	S1—C4—C3—C2	−1.9 (10)
S1—C1—C2—C3	0.1 (9)	Br2—C4—C3—C2	179.1 (6)
C1i—C1—C2—Br1	−0.2 (11)	C1—C2—C3—C4	1.2 (11)
S1—C1—C2—Br1	−179.4 (4)	Br1—C2—C3—C4	−179.4 (6)