2,3,4-Tribromo-thio-phene.

In the title compound, C(4)HBr(3)S, there are two essentially planar mol-ecules in the asymmetric unit. In the crystal structure, bifurcated C-H⋯Br hydrogen bonds link the mol-ecules into chains. Weak Br⋯Br inter-actions [Br⋯Br = 3.634 (4)-3.691 (4) Å] then lead to undulating sheets in the bc plane.

Related literature

For related polybromo­thio­phene structures, see: Helmholdt et al. (2007 ▶); Murakami et al. (2002 ▶); Xie et al. (1997 ▶, 1998 ▶). For information on halogen⋯halogen contacts, see: Pedireddi et al. (1994 ▶). For details of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C4HBr3S

M = 320.84

Orthorhombic,

a = 12.4529 (11) Å

b = 3.9724 (4) Å

c = 28.846 (3) Å

V = 1426.9 (2) Å3

Z = 8

Mo Kα radiation

μ = 17.14 mm−1

T = 91 (2) K

0.17 × 0.06 × 0.02 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.434, T max = 0.710

12082 measured reflections

2163 independent reflections

1852 reflections with I > 2σ(I)

R int = 0.092

θmax = 23.7°

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.172

S = 0.86

2163 reflections

109 parameters

1 restraint

H-atom parameters constrained

Δρmax = 3.39 e Å−3

Δρmin = −1.30 e Å−3

Absolute structure: Flack (1983 ▶), 1050 Friedel pairs

Flack parameter: 0.11 (6)

Data collection: APEX2 (Bruker 2006 ▶); cell refinement: APEX2 and SAINT (Bruker 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and TITAN (Hunter & Simpson, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006600/hb2706sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006600/hb2706Isup2.hkl

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

C4HBr3S	F000 = 1168
Mr = 320.84	Dx = 2.987 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1448 reflections
a = 12.4529 (11) Å	θ = 3.4–21.9º
b = 3.9724 (4) Å	µ = 17.14 mm−1
c = 28.846 (3) Å	T = 91 (2) K
V = 1426.9 (2) Å3	Plate, colourless
Z = 8	0.17 × 0.06 × 0.02 mm

Bruker APEXII CCD area-detector diffractometer	2163 independent reflections
Radiation source: fine-focus sealed tube	1852 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.092
T = 91(2) K	θmax = 23.7º
ω scans	θmin = 1.4º
Absorption correction: multi-scan(SADABS; Bruker, 2006)	h = −14→14
Tmin = 0.434, Tmax = 0.710	k = −4→4
12082 measured reflections	l = −32→32

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.061	w = 1/[σ2(Fo2) + (0.1079P)2 + 95.665P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.172	(Δ/σ)max = 0.001
S = 0.86	Δρmax = 3.39 e Å−3
2163 reflections	Δρmin = −1.30 e Å−3
109 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1050 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.11 (6)
Secondary atom site location: difference Fourier map

Experimental. As the crystals were small and very weakly diffracting, data were collected using 55 sec exposures per frame.

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
S1A	0.6553 (5)	0.6506 (19)	0.2528 (2)	0.0307 (15)
C1A	0.723 (2)	0.726 (7)	0.2042 (10)	0.0307 (15)
H1A	0.7916	0.8311	0.2015	0.037*
C2A	0.6527 (19)	0.592 (6)	0.1649 (8)	0.0229 (6)
Br2A	0.69172 (17)	0.6009 (6)	0.10260 (10)	0.0229 (6)
C3A	0.5527 (17)	0.441 (7)	0.1819 (9)	0.021 (5)
Br3A	0.44805 (17)	0.2573 (6)	0.14378 (10)	0.0183 (7)
C4A	0.5485 (18)	0.455 (6)	0.2298 (8)	0.0197 (6)
Br4A	0.43447 (16)	0.3131 (7)	0.26658 (9)	0.0197 (6)
S1B	0.6092 (5)	0.3531 (17)	0.3764 (2)	0.0268 (14)
C1B	0.542 (2)	0.270 (6)	0.4273 (10)	0.0268 (14)
H1B	0.4743	0.1617	0.4311	0.032*
C2B	0.6136 (18)	0.407 (7)	0.4637 (8)	0.0227 (6)
Br2B	0.57498 (17)	0.4088 (6)	0.52692 (10)	0.0227 (6)
C3B	0.7118 (17)	0.544 (6)	0.4479 (8)	0.016 (5)
Br3B	0.82097 (17)	0.7329 (6)	0.48587 (10)	0.0193 (7)
C4B	0.7212 (17)	0.523 (6)	0.4001 (8)	0.0206 (6)
Br4B	0.83237 (18)	0.6820 (7)	0.36312 (9)	0.0206 (6)

	U11	U22	U33	U12	U13	U23
S1A	0.017 (3)	0.039 (4)	0.037 (4)	0.000 (3)	−0.004 (3)	0.002 (3)
C1A	0.017 (3)	0.039 (4)	0.037 (4)	0.000 (3)	−0.004 (3)	0.002 (3)
C2A	0.0147 (12)	0.0294 (16)	0.0246 (13)	−0.0022 (10)	0.0041 (10)	0.0019 (12)
Br2A	0.0147 (12)	0.0294 (16)	0.0246 (13)	−0.0022 (10)	0.0041 (10)	0.0019 (12)
C3A	0.005 (10)	0.035 (14)	0.024 (13)	0.008 (10)	−0.002 (9)	−0.006 (12)
Br3A	0.0104 (11)	0.0209 (16)	0.0237 (16)	−0.0040 (9)	−0.0040 (10)	−0.0015 (9)
C4A	0.0138 (12)	0.0212 (11)	0.0243 (14)	−0.0028 (9)	0.0055 (9)	−0.0012 (14)
Br4A	0.0138 (12)	0.0212 (11)	0.0243 (14)	−0.0028 (9)	0.0055 (9)	−0.0012 (14)
S1B	0.023 (3)	0.023 (3)	0.034 (4)	0.004 (3)	0.001 (3)	−0.005 (3)
C1B	0.023 (3)	0.023 (3)	0.034 (4)	0.004 (3)	0.001 (3)	−0.005 (3)
C2B	0.0142 (11)	0.0305 (15)	0.0235 (13)	−0.0007 (10)	0.0037 (10)	0.0040 (12)
Br2B	0.0142 (11)	0.0305 (15)	0.0235 (13)	−0.0007 (10)	0.0037 (10)	0.0040 (12)
C3B	0.016 (11)	0.015 (11)	0.017 (12)	0.000 (9)	0.000 (9)	0.002 (10)
Br3B	0.0090 (11)	0.0200 (16)	0.0290 (17)	0.0022 (10)	−0.0020 (10)	−0.0028 (10)
C4B	0.0125 (11)	0.0198 (10)	0.0295 (15)	0.0030 (10)	0.0056 (10)	0.0023 (14)
Br4B	0.0125 (11)	0.0198 (10)	0.0295 (15)	0.0030 (10)	0.0056 (10)	0.0023 (14)

S1A—C4A	1.68 (2)	S1B—C4B	1.69 (2)
S1A—C1A	1.66 (3)	S1B—C1B	1.72 (3)
C1A—C2A	1.53 (4)	C1B—C2B	1.48 (4)
C1A—H1A	0.9500	C1B—H1B	0.9500
C2A—C3A	1.47 (3)	C2B—C3B	1.41 (3)
C2A—Br2A	1.86 (2)	C2B—Br2B	1.89 (2)
C3A—C4A	1.38 (3)	C3B—C4B	1.39 (3)
C3A—Br3A	1.86 (2)	C3B—Br3B	1.90 (2)
C4A—Br4A	1.86 (2)	C4B—Br4B	1.86 (2)
C4A—S1A—C1A	98.9 (13)	C4B—S1B—C1B	97.7 (12)
C2A—C1A—S1A	105.5 (17)	C2B—C1B—S1B	103.8 (17)
C2A—C1A—H1A	127.2	C2B—C1B—H1B	128.1
S1A—C1A—H1A	127.2	S1B—C1B—H1B	128.1
C3A—C2A—C1A	112 (2)	C3B—C2B—C1B	116 (2)
C3A—C2A—Br2A	123.5 (18)	C3B—C2B—Br2B	122.1 (17)
C1A—C2A—Br2A	123.9 (18)	C1B—C2B—Br2B	122.1 (18)
C4A—C3A—C2A	110 (2)	C4B—C3B—C2B	112 (2)
C4A—C3A—Br3A	125.6 (19)	C4B—C3B—Br3B	122.4 (17)
C2A—C3A—Br3A	124.0 (19)	C2B—C3B—Br3B	125.8 (17)
C3A—C4A—S1A	112.5 (18)	C3B—C4B—S1B	110.9 (17)
C3A—C4A—Br4A	125.9 (18)	C3B—C4B—Br4B	127.9 (18)
S1A—C4A—Br4A	121.4 (14)	S1B—C4B—Br4B	121.1 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···Br3Ai	0.95	3.04	3.89 (3)	149
C1A—H1A···Br4Ai	0.95	2.96	3.68 (3)	134
C1B—H1B···Br3Bii	0.95	2.93	3.79 (3)	151
C1B—H1B···Br4Bii	0.95	2.97	3.66 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1A⋯Br3Ai	0.95	3.04	3.89 (3)	149
C1A—H1A⋯Br4Ai	0.95	2.96	3.68 (3)	134
C1B—H1B⋯Br3Bii	0.95	2.93	3.79 (3)	151
C1B—H1B⋯Br4Bii	0.95	2.97	3.66 (2)	131

Symmetry codes: (i) ; (ii) .