5,6-Dihydro-2H-1,3-dithiolo[4,5-b][1,4]dioxine-2-thione.

The title mol-ecule, C(5)H(4)O(2)S(3), consists of a planar [mean deviation = 0.020 (1) Å] 1,3-dithiole-2-thione unit with an ethyl-enedi-oxy group in the 4,5-positions. The dioxine ring is in a twist-chair conformation.

Related literature

For related structures, see: Kanchanadevi et al. (2010 ▶); Rizvi et al. (2010 ▶); Suzuki et al. (1989 ▶); Xu et al. (2009 ▶); Sugumar et al. (2008 ▶). For the synthesis of the title compound, see: Hartke & Lindenblatt (1990 ▶); Suzuki et al. (1989 ▶).

Experimental

Crystal data

C5H4O2S3

M = 192.26

Monoclinic,

a = 5.4645 (8) Å

b = 13.430 (2) Å

c = 9.8189 (16) Å

β = 91.294 (3)°

V = 720.41 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.96 mm−1

T = 223 K

0.55 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.605, T max = 0.826

3605 measured reflections

1332 independent reflections

1199 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.083

S = 1.17

1332 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2005 ▶); 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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017417/aa2007sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017417/aa2007Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811017417/aa2007Isup3.cml

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

C5H4O2S3	F(000) = 392
Mr = 192.26	Dx = 1.773 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 3311 reflections
a = 5.4645 (8) Å	θ = 3.0–27.5°
b = 13.430 (2) Å	µ = 0.96 mm−1
c = 9.8189 (16) Å	T = 223 K
β = 91.294 (3)°	Block, yellow
V = 720.41 (19) Å3	0.55 × 0.20 × 0.20 mm
Z = 4

Rigaku Saturn diffractometer	1332 independent reflections
Radiation source: fine-focus sealed tube	1199 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 14.63 pixels mm-1	θmax = 25.5°, θmin = 3.0°
ω scans	h = −6→6
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −14→16
Tmin = 0.605, Tmax = 0.826	l = −11→9
3605 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0486P)2 + 0.013P] where P = (Fo2 + 2Fc2)/3
1332 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	1.15131 (11)	0.20574 (4)	1.05803 (6)	0.0394 (2)
S2	0.77835 (10)	0.36220 (4)	0.99990 (5)	0.03292 (19)
S3	1.18427 (10)	0.33798 (4)	0.81841 (6)	0.03387 (19)
O1	0.6189 (3)	0.51707 (11)	0.85167 (16)	0.0381 (4)
O2	1.0238 (3)	0.49167 (11)	0.66988 (16)	0.0367 (4)
C1	1.0418 (4)	0.29782 (14)	0.9629 (2)	0.0282 (5)
C2	0.7954 (4)	0.44643 (15)	0.8651 (2)	0.0276 (4)
C3	0.9812 (4)	0.43492 (14)	0.7810 (2)	0.0280 (5)
C4	0.6183 (4)	0.55689 (18)	0.7147 (2)	0.0412 (6)
H4A	0.5199	0.6179	0.7115	0.049*
H4B	0.5419	0.5086	0.6523	0.049*
C5	0.8699 (5)	0.57960 (16)	0.6687 (2)	0.0413 (6)
H5A	0.8607	0.6069	0.5761	0.050*
H5B	0.9437	0.6303	0.7286	0.050*

	U11	U22	U33	U12	U13	U23
S1	0.0427 (4)	0.0365 (3)	0.0392 (4)	0.0112 (2)	0.0020 (3)	0.0078 (2)
S2	0.0318 (3)	0.0340 (3)	0.0333 (3)	0.0071 (2)	0.0086 (2)	0.0068 (2)
S3	0.0289 (3)	0.0393 (3)	0.0337 (3)	0.0073 (2)	0.0071 (2)	0.0031 (2)
O1	0.0372 (8)	0.0368 (8)	0.0406 (9)	0.0126 (7)	0.0095 (7)	0.0107 (7)
O2	0.0364 (8)	0.0400 (9)	0.0340 (9)	0.0041 (7)	0.0079 (7)	0.0105 (6)
C1	0.0288 (11)	0.0264 (11)	0.0295 (11)	0.0008 (8)	0.0001 (9)	−0.0033 (8)
C2	0.0276 (10)	0.0260 (10)	0.0293 (11)	0.0013 (8)	0.0010 (8)	0.0018 (8)
C3	0.0256 (10)	0.0289 (10)	0.0296 (11)	−0.0021 (8)	−0.0003 (9)	0.0015 (8)
C4	0.0417 (13)	0.0424 (12)	0.0394 (13)	0.0116 (11)	0.0019 (10)	0.0134 (10)
C5	0.0499 (14)	0.0354 (12)	0.0387 (13)	0.0029 (10)	0.0026 (11)	0.0091 (10)

S1—C1	1.654 (2)	O2—C5	1.450 (3)
S2—C1	1.725 (2)	C2—C3	1.332 (3)
S2—C2	1.746 (2)	C4—C5	1.488 (3)
S3—C1	1.720 (2)	C4—H4A	0.9800
S3—C3	1.744 (2)	C4—H4B	0.9800
O1—C2	1.357 (2)	C5—H5A	0.9800
O1—C4	1.447 (3)	C5—H5B	0.9800
O2—C3	1.356 (2)
C1—S2—C2	96.07 (10)	O1—C4—C5	112.07 (18)
C1—S3—C3	96.32 (9)	O1—C4—H4A	109.2
C2—O1—C4	109.56 (15)	C5—C4—H4A	109.2
C3—O2—C5	110.75 (15)	O1—C4—H4B	109.2
S1—C1—S3	122.39 (12)	C5—C4—H4B	109.2
S1—C1—S2	123.28 (13)	H4A—C4—H4B	107.9
S3—C1—S2	114.33 (12)	O2—C5—C4	111.73 (18)
C3—C2—O1	124.84 (18)	O2—C5—H5A	109.3
C3—C2—S2	116.70 (16)	C4—C5—H5A	109.3
O1—C2—S2	118.45 (14)	O2—C5—H5B	109.3
C2—C3—O2	125.52 (18)	C4—C5—H5B	109.3
C2—C3—S3	116.52 (16)	H5A—C5—H5B	107.9
O2—C3—S3	117.97 (14)
C3—S3—C1—S1	−177.35 (13)	O1—C2—C3—S3	−179.51 (15)
C3—S3—C1—S2	2.19 (13)	S2—C2—C3—S3	−0.7 (2)
C2—S2—C1—S1	177.05 (14)	C5—O2—C3—C2	11.6 (3)
C2—S2—C1—S3	−2.48 (13)	C5—O2—C3—S3	−168.64 (15)
C4—O1—C2—C3	17.2 (3)	C1—S3—C3—C2	−0.90 (19)
C4—O1—C2—S2	−161.53 (15)	C1—S3—C3—O2	179.31 (15)
C1—S2—C2—C3	1.93 (18)	C2—O1—C4—C5	−45.5 (3)
C1—S2—C2—O1	−179.19 (16)	C3—O2—C5—C4	−39.8 (2)
O1—C2—C3—O2	0.3 (3)	O1—C4—C5—O2	59.5 (3)
S2—C2—C3—O2	179.05 (15)