Bis[(methyl-sulfan-yl)carbon-yl]disulfane.

The title compound, C(4)H(6)O(2)S(4), was prepared by repeating, with subtle improvements, a multi-step route originally described by Mott & Barany [J. Chem. Soc. Perkin Trans. 1 (1984) ▶, pp. 2615-2621]. The title compound was obtained for the first time as a crystalline material. The two [(methyl-sulfan-yl)carbon-yl]sulfenyl moieties are essentially perpendic-ular to each other, each approximately planar (r.m.s. deviations of 0.02 and 0.01 Å) and with a C-S-S-C torsion angle = 90.99 (6)°, which compares well with the theoretical value of 90°.

Related literature

For the preparation of the title compound and for the preparation and structures of the corresponding trisulfane and tetrasulfane compounds, see: Mott & Barany (1984 ▶). For other related structures, see: Bereman et al. (1983 ▶); Rout et al. (1983 ▶); Paul & Srikrishnan (2004 ▶); Li et al. (2006 ▶); Schroll et al. (2012 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For optimum dihedral angles, see: Pauling (1960 ▶). For background to isomeric bis­(alk­oxy­thio­carbon­yl)­poly­sulfanes, see: Reid (1962 ▶).

Experimental

Crystal data

C4H6O2S4

M = 214.33

Triclinic,

a = 5.3300 (7) Å

b = 8.6935 (12) Å

c = 9.9166 (13) Å

α = 109.875 (2)°

β = 92.154 (2)°

γ = 101.481 (2)°

V = 420.71 (10) Å3

Z = 2

Mo Kα radiation

μ = 1.07 mm−1

T = 123 K

0.35 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008a ▶) T min = 0.707, T max = 0.776

5024 measured reflections

1894 independent reflections

1774 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.054

S = 1.07

1894 reflections

93 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1998 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024750/gw2119sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024750/gw2119Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024750/gw2119Isup3.cml

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

C4H6O2S4	Z = 2
Mr = 214.33	F(000) = 220
Triclinic, P1	Dx = 1.692 Mg m−3
a = 5.3300 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6935 (12) Å	Cell parameters from 2965 reflections
c = 9.9166 (13) Å	θ = 2.2–27.5°
α = 109.875 (2)°	µ = 1.07 mm−1
β = 92.154 (2)°	T = 123 K
γ = 101.481 (2)°	Block, colourless
V = 420.71 (10) Å3	0.35 × 0.30 × 0.25 mm

Bruker SMART CCD area-detector diffractometer	1894 independent reflections
Radiation source: sealed tube	1774 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	h = −6→6
Tmin = 0.707, Tmax = 0.776	k = −11→10
5024 measured reflections	l = 0→12

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0267P)2 + 0.1517P] where P = (Fo2 + 2Fc2)/3
1894 reflections	(Δ/σ)max = 0.001
93 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.24 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 > 2σ(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	0.14601 (6)	0.32879 (4)	0.88175 (3)	0.01738 (9)
S2	0.29712 (6)	0.29567 (4)	0.58244 (3)	0.01738 (9)
S3	0.59396 (6)	0.46586 (4)	0.72293 (4)	0.01720 (9)
S4	0.23910 (6)	0.67401 (4)	0.66158 (4)	0.01664 (9)
O1	−0.13318 (18)	0.13895 (12)	0.63241 (11)	0.0206 (2)
O2	0.68271 (19)	0.78866 (12)	0.83115 (12)	0.0242 (2)
C1	−0.1386 (3)	0.22275 (18)	0.93481 (15)	0.0203 (3)
H1A	−0.1228	0.2564	1.0402	0.030*
H1B	−0.1567	0.1011	0.8914	0.030*
H1C	−0.2906	0.2533	0.9016	0.030*
C2	0.0631 (2)	0.23846 (16)	0.69410 (14)	0.0151 (3)
C3	0.5248 (2)	0.66889 (17)	0.75182 (14)	0.0162 (3)
C4	0.2779 (3)	0.89933 (17)	0.72402 (17)	0.0224 (3)
H4A	0.1240	0.9264	0.6889	0.034*
H4B	0.4291	0.9490	0.6872	0.034*
H4C	0.3016	0.9447	0.8298	0.034*

	U11	U22	U33	U12	U13	U23
S1	0.01675 (17)	0.01802 (17)	0.01540 (17)	0.00122 (12)	0.00094 (12)	0.00507 (13)
S2	0.01809 (17)	0.01627 (17)	0.01596 (17)	0.00210 (12)	0.00280 (12)	0.00433 (13)
S3	0.01357 (16)	0.01617 (17)	0.02213 (18)	0.00337 (12)	0.00094 (13)	0.00725 (13)
S4	0.01479 (16)	0.01637 (17)	0.01887 (17)	0.00321 (12)	−0.00024 (12)	0.00678 (13)
O1	0.0178 (5)	0.0190 (5)	0.0212 (5)	0.0005 (4)	−0.0005 (4)	0.0048 (4)
O2	0.0210 (5)	0.0181 (5)	0.0297 (6)	0.0003 (4)	−0.0060 (4)	0.0070 (4)
C1	0.0189 (7)	0.0214 (7)	0.0213 (7)	0.0026 (5)	0.0049 (5)	0.0094 (6)
C2	0.0164 (6)	0.0130 (6)	0.0169 (6)	0.0058 (5)	0.0021 (5)	0.0050 (5)
C3	0.0151 (6)	0.0169 (6)	0.0184 (6)	0.0037 (5)	0.0031 (5)	0.0083 (5)
C4	0.0231 (7)	0.0162 (7)	0.0288 (8)	0.0053 (5)	0.0006 (6)	0.0090 (6)

S1—C2	1.7553 (14)	O2—C3	1.2067 (17)
S1—C1	1.8057 (14)	C1—H1A	0.9800
S2—C2	1.8057 (13)	C1—H1B	0.9800
S2—S3	2.0332 (5)	C1—H1C	0.9800
S3—C3	1.8047 (14)	C4—H4A	0.9800
S4—C3	1.7528 (14)	C4—H4B	0.9800
S4—C4	1.8077 (14)	C4—H4C	0.9800
O1—C2	1.2037 (16)
C2—S1—C1	98.04 (6)	O1—C2—S2	116.70 (10)
C2—S2—S3	105.23 (5)	S1—C2—S2	117.13 (7)
C3—S3—S2	105.85 (5)	O2—C3—S4	126.34 (11)
C3—S4—C4	97.96 (7)	O2—C3—S3	116.20 (10)
S1—C1—H1A	109.5	S4—C3—S3	117.46 (7)
S1—C1—H1B	109.5	S4—C4—H4A	109.5
H1A—C1—H1B	109.5	S4—C4—H4B	109.5
S1—C1—H1C	109.5	H4A—C4—H4B	109.5
H1A—C1—H1C	109.5	S4—C4—H4C	109.5
H1B—C1—H1C	109.5	H4A—C4—H4C	109.5
O1—C2—S1	126.15 (10)	H4B—C4—H4C	109.5
C2—S2—S3—C3	−90.99 (6)	C4—S4—C3—O2	1.13 (14)
C1—S1—C2—O1	1.09 (13)	C4—S4—C3—S3	−178.16 (8)
C1—S1—C2—S2	−177.21 (8)	S2—S3—C3—O2	−178.71 (10)
S3—S2—C2—O1	179.07 (9)	S2—S3—C3—S4	0.65 (8)
S3—S2—C2—S1	−2.46 (8)