2,5-Dichloro-thio-phene 1,1-dioxide.

The complete mol-ecule of the title compound, C(4)H(2)Cl(2)O(2)S, is generated by crystallographic twofold symmetry, with the S atom lying on the rotation axis. In the crystal, the molecules are linked by C-H⋯O hydrogen bonds..

Related literature

For a related thio­phene-1,1-dioxide structure, see: Douglas et al. (1993 ▶). For the synthetic utility and related applications of thio­phene-1,1-dioxides, see: Moiseev et al. (2006 ▶); Nakayama & Sugihara (1999 ▶); Shul’ts et al. (2003 ▶); Lou et al. (2002 ▶).

Experimental

Crystal data

C4H2Cl2O2S

M = 185.02

Monoclinic,

a = 7.588 (2) Å

b = 10.584 (3) Å

c = 8.745 (3) Å

β = 90.275 (9)°

V = 702.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.14 mm−1

T = 296 K

0.50 × 0.40 × 0.30 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.590, T max = 0.726

3352 measured reflections

622 independent reflections

549 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.12

622 reflections

42 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.31 e Å−3

Data collection: GIS (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT (Bruker, 2007 ▶); 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/S1600536809050776/fl2274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050776/fl2274Isup2.hkl

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

C4H2Cl2O2S	F(000) = 368
Mr = 185.02	Dx = 1.750 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1863 reflections
a = 7.588 (2) Å	θ = 3.3–24.8°
b = 10.584 (3) Å	µ = 1.14 mm−1
c = 8.745 (3) Å	T = 296 K
β = 90.275 (9)°	Block, colourless
V = 702.4 (3) Å3	0.50 × 0.40 × 0.30 mm
Z = 4

Bruker SMART X2S diffractometer	622 independent reflections
Radiation source: micro-focus sealed tube	549 reflections with I > 2σ(I)
doubly curved silicon crystal	Rint = 0.028
ω scans	θmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→8
Tmin = 0.590, Tmax = 0.726	k = −12→12
3352 measured reflections	l = −10→10

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.6008P] where P = (Fo2 + 2Fc2)/3
622 reflections	(Δ/σ)max = 0.013
42 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.31 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
Cl1	0.32276 (10)	0.08665 (9)	0.07774 (10)	0.0906 (4)
S1	0.0000	0.15554 (8)	0.2500	0.0529 (3)
O1	−0.0844 (3)	0.2242 (2)	0.1299 (2)	0.0779 (6)
C1	0.1415 (3)	0.0379 (3)	0.1743 (3)	0.0582 (6)
C2	0.0827 (4)	−0.0754 (3)	0.2059 (3)	0.0677 (8)
H2	0.1398	−0.1490	0.1757	0.081*

	U11	U22	U33	U12	U13	U23
Cl1	0.0634 (5)	0.1157 (8)	0.0932 (6)	0.0154 (4)	0.0365 (4)	0.0078 (5)
S1	0.0513 (5)	0.0506 (5)	0.0570 (5)	0.000	0.0174 (4)	0.000
O1	0.0812 (13)	0.0728 (12)	0.0799 (13)	0.0258 (11)	0.0188 (10)	0.0181 (10)
C1	0.0518 (14)	0.0674 (15)	0.0553 (14)	0.0134 (12)	0.0115 (11)	0.0005 (12)
C2	0.0788 (19)	0.0587 (15)	0.0657 (17)	0.0167 (14)	0.0042 (14)	−0.0020 (13)

Cl1—C1	1.698 (3)	S1—C1i	1.774 (2)
S1—O1i	1.427 (2)	C1—C2	1.310 (4)
S1—O1	1.427 (2)	C2—C2i	1.476 (6)
S1—C1	1.774 (2)	C2—H2	0.9300
O1i—S1—O1	118.8 (2)	C2—C1—Cl1	131.4 (2)
O1i—S1—C1	111.19 (13)	C2—C1—S1	110.9 (2)
O1—S1—C1	110.68 (12)	Cl1—C1—S1	117.74 (16)
O1i—S1—C1i	110.68 (12)	C1—C2—C2i	113.68 (16)
O1—S1—C1i	111.19 (13)	C1—C2—H2	123.2
C1—S1—C1i	90.87 (18)	C2i—C2—H2	123.2

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ii	0.93	2.52	3.367 (4)	152

X···Y	π···π
C1···C2	4.137 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.52	3.367 (4)	152

Symmetry code: (i) .