4-Bromo-5-[(2-bromo-ethyl)-sulfanyl]-1,3-dithiole-2-thione.

The title compound, C(5)H(4)Br(2)S(4), consists of a statistically planar, 4-bromo-1,3-dithiole-2-thione unit [maximum deviation from the ring plane 0.001 (2) Å], with a bromo-ethyl-sulfanyl substituent in the 5-position. In the crystal structure, weak inter-molecular S⋯S [3.438 (15) and 3.522 (15) Å] and S⋯Br [3.422 (14) and 3.498 (14) Å] inter-actions generate a three-dimensional supra-molecular architecture.

Related literature

For general background to the applications of halogenated 1,3-dithiole-2-thio­nes, see: Alberola et al. 2006 ▶; Batsanov et al. (2001 ▶); Jeppesen et al. (2004 ▶); Segura & Martin (2001 ▶); Wang et al. (1995 ▶). For a related structure, see: Zhao et al. (2008 ▶).

Experimental

Crystal data

C5H4Br2S4

M = 352.14

Monoclinic,

a = 4.7892 (12) Å

b = 20.381 (5) Å

c = 10.809 (3) Å

β = 96.922 (3)°

V = 1047.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 8.47 mm−1

T = 294 K

0.44 × 0.17 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.117, T max = 0.613

9101 measured reflections

2391 independent reflections

1845 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.081

S = 1.05

2391 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.81 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 I, global. DOI: 10.1107/S1600536809036770/sj2640sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036770/sj2640Isup2.hkl

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

C5H4Br2S4	F(000) = 672
Mr = 352.14	Dx = 2.233 Mg m−3
Monoclinic, P21/c	Melting point: 331 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 4.7892 (12) Å	Cell parameters from 3116 reflections
b = 20.381 (5) Å	θ = 3.6–26.1°
c = 10.809 (3) Å	µ = 8.47 mm−1
β = 96.922 (3)°	T = 294 K
V = 1047.3 (5) Å3	Block, yellow
Z = 4	0.44 × 0.17 × 0.06 mm

Bruker SMART CCD area-detector diffractometer	2391 independent reflections
Radiation source: fine-focus sealed tube	1845 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −6→6
Tmin = 0.117, Tmax = 0.613	k = −26→26
9101 measured reflections	l = −13→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.5713P] where P = (Fo2 + 2Fc2)/3
2391 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.81 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
Br1	0.33646 (9)	0.39616 (2)	−0.03831 (4)	0.05782 (14)
Br2	−0.12031 (10)	0.252098 (19)	0.33275 (4)	0.06158 (15)
S1	0.6869 (2)	0.39508 (5)	0.69591 (9)	0.0506 (2)
S2	0.25370 (18)	0.43827 (4)	0.49022 (8)	0.0406 (2)
S3	0.3149 (2)	0.30064 (4)	0.54490 (10)	0.0517 (3)
S4	−0.20103 (18)	0.42118 (5)	0.27552 (9)	0.0481 (2)
C1	0.4319 (7)	0.37956 (16)	0.5834 (3)	0.0379 (7)
C2	0.0385 (7)	0.38613 (16)	0.3924 (3)	0.0379 (7)
C3	0.0692 (8)	0.32205 (17)	0.4204 (3)	0.0439 (8)
C4	0.0261 (7)	0.43820 (17)	0.1567 (3)	0.0432 (8)
H4A	−0.0737	0.4654	0.0923	0.052*
H4B	0.1900	0.4623	0.1935	0.052*
C5	0.1193 (8)	0.37586 (17)	0.0993 (4)	0.0458 (8)
H5A	−0.0441	0.3498	0.0686	0.055*
H5B	0.2340	0.3503	0.1620	0.055*

	U11	U22	U33	U12	U13	U23
Br1	0.0521 (2)	0.0758 (3)	0.0462 (3)	0.00042 (19)	0.00845 (17)	0.00156 (19)
Br2	0.0753 (3)	0.0501 (2)	0.0572 (3)	−0.01945 (19)	−0.0007 (2)	−0.00821 (18)
S1	0.0503 (5)	0.0586 (6)	0.0406 (5)	−0.0006 (4)	−0.0045 (4)	0.0014 (4)
S2	0.0410 (5)	0.0369 (4)	0.0424 (5)	−0.0004 (3)	−0.0003 (4)	−0.0019 (3)
S3	0.0659 (6)	0.0388 (4)	0.0483 (6)	−0.0032 (4)	−0.0021 (5)	0.0048 (4)
S4	0.0341 (5)	0.0628 (5)	0.0462 (5)	0.0083 (4)	0.0001 (4)	−0.0038 (4)
C1	0.0390 (18)	0.0420 (17)	0.0342 (19)	0.0010 (14)	0.0098 (14)	0.0002 (14)
C2	0.0346 (17)	0.0441 (17)	0.0349 (19)	−0.0009 (14)	0.0039 (13)	−0.0031 (14)
C3	0.048 (2)	0.0448 (18)	0.039 (2)	−0.0081 (16)	0.0068 (16)	−0.0056 (15)
C4	0.0414 (19)	0.0425 (18)	0.043 (2)	0.0030 (15)	−0.0038 (15)	0.0016 (15)
C5	0.045 (2)	0.0448 (18)	0.048 (2)	−0.0022 (15)	0.0083 (16)	−0.0004 (16)

Br1—C5	1.959 (4)	S4—C4	1.814 (4)
Br2—C3	1.883 (3)	C2—C3	1.345 (5)
S1—C1	1.647 (4)	C4—C5	1.505 (5)
S2—C1	1.723 (3)	C4—H4A	0.9700
S2—C2	1.746 (3)	C4—H4B	0.9700
S3—C3	1.734 (4)	C5—H5A	0.9700
S3—C1	1.737 (3)	C5—H5B	0.9700
S4—C2	1.753 (4)
C1—S2—C2	98.40 (16)	C5—C4—S4	111.3 (2)
C3—S3—C1	97.02 (17)	C5—C4—H4A	109.4
C2—S4—C4	101.05 (16)	S4—C4—H4A	109.4
S1—C1—S2	124.7 (2)	C5—C4—H4B	109.4
S1—C1—S3	122.9 (2)	S4—C4—H4B	109.4
S2—C1—S3	112.34 (19)	H4A—C4—H4B	108.0
C3—C2—S2	114.5 (3)	C4—C5—Br1	110.2 (2)
C3—C2—S4	127.0 (3)	C4—C5—H5A	109.6
S2—C2—S4	118.41 (19)	Br1—C5—H5A	109.6
C2—C3—S3	117.7 (3)	C4—C5—H5B	109.6
C2—C3—Br2	126.1 (3)	Br1—C5—H5B	109.6
S3—C3—Br2	116.2 (2)	H5A—C5—H5B	108.1
C2—S2—C1—S1	177.1 (2)	S2—C2—C3—S3	−0.9 (4)
C2—S2—C1—S3	−2.4 (2)	S4—C2—C3—S3	−177.7 (2)
C3—S3—C1—S1	−177.5 (2)	S2—C2—C3—Br2	−178.3 (2)
C3—S3—C1—S2	2.0 (2)	S4—C2—C3—Br2	4.9 (5)
C1—S2—C2—C3	2.0 (3)	C1—S3—C3—C2	−0.7 (3)
C1—S2—C2—S4	179.1 (2)	C1—S3—C3—Br2	176.9 (2)
C4—S4—C2—C3	−102.6 (3)	C2—S4—C4—C5	69.7 (3)
C4—S4—C2—S2	80.7 (2)	S4—C4—C5—Br1	175.02 (17)