Bis(methyl-sulfon-yl)methane.

In the title compound, C3H8O4S2, the two central S-C(H2) bond lengths are almost identical [1.781 (2) and 1.789 (2) Å]. In the crystal, each mol-ecule utilizes CH2 and CH3 bonds to form weak C-H⋯O hydrogen bonds to six other mol-ecules, thus linking mol-ecules into a three-dimensional network.

Related literature

For the structures of similar compounds, see: Berthou et al. (1972 ▶); Glidewell et al. (1995 ▶, 1996 ▶); Meehan et al. (1997 ▶); Zhang et al. (2009 ▶). For information of the use of the title compound in the food industry, see: Awaleh et al. (2007 ▶); Gereben & Pusztai (2012 ▶).

Experimental

Crystal data

C3H8O4S2

M = 172.21

Monoclinic,

a = 11.0496 (18) Å

b = 5.793 (3) Å

c = 11.0496 (6) Å

β = 96.77 (3)°

V = 702.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 173 K

0.25 × 0.05 × 0.05 mm

Data collection

Stoe IPDS diffractometer

9692 measured reflections

1441 independent reflections

1274 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.073

S = 1.10

1441 reflections

115 parameters

All H-atom parameters refined

Δρmax = 0.42 e Å−3

Δρmin = −0.28 e Å−3

Data collection: IPDS (Stoe & Cie, 2008 ▶); cell refinement: X-AREA (Stoe & Cie, 2008 ▶); data reduction: IPDS; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814016201/cv5464sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814016201/cv5464Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814016201/cv5464Isup3.cml

CCDC reference: 1013637

Additional supporting information: crystallographic information; 3D view; checkCIF report

C3H8O4S2	F(000) = 360
Mr = 172.21	Dx = 1.629 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.0496 (18) Å	θ = 5.7–16.2°
b = 5.793 (3) Å	µ = 0.70 mm−1
c = 11.0496 (6) Å	T = 173 K
β = 96.77 (3)°	Needle, colourless
V = 702.3 (3) Å3	0.25 × 0.05 × 0.05 mm
Z = 4

Stoe IPDS diffractometer	1274 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
Graphite monochromator	θmax = 26.3°, θmin = 3.7°
πhi scans	h = −13→13
9692 measured reflections	k = −6→7
1441 independent reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	All H-atom parameters refined
wR(F2) = 0.073	w = 1/[σ2(Fo2) + (0.0285P)2 + 0.429P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
1441 reflections	Δρmax = 0.42 e Å−3
115 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0073 (18)

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
S1	0.16353 (4)	1.01190 (7)	0.35533 (4)	0.01773 (15)
S2	−0.07227 (4)	1.00358 (8)	0.18190 (4)	0.02323 (16)
C1	0.11691 (19)	1.2396 (3)	0.44401 (18)	0.0233 (4)
H1A	0.033 (2)	1.226 (4)	0.448 (2)	0.034 (6)*
H1B	0.137 (2)	1.376 (4)	0.409 (2)	0.030 (6)*
H1C	0.160 (2)	1.220 (4)	0.524 (2)	0.037 (6)*
C2	−0.0862 (2)	0.7028 (4)	0.1665 (2)	0.0349 (5)
H2A	−0.052 (2)	0.634 (5)	0.239 (2)	0.041 (7)*
H2B	−0.046 (3)	0.657 (5)	0.099 (3)	0.048 (7)*
H2C	−0.166 (3)	0.673 (5)	0.158 (2)	0.049 (8)*
C3	0.08763 (16)	1.0559 (3)	0.20496 (16)	0.0210 (4)
H3A	0.127 (2)	0.955 (4)	0.153 (2)	0.028 (6)*
H3B	0.103 (2)	1.214 (4)	0.1858 (19)	0.027 (6)*
O4	0.12487 (12)	0.7950 (2)	0.40149 (12)	0.0254 (3)
O5	−0.12516 (12)	1.0780 (3)	0.28823 (13)	0.0325 (4)
O6	0.29086 (11)	1.0408 (2)	0.34274 (12)	0.0248 (3)
O7	−0.11405 (14)	1.1120 (3)	0.06711 (13)	0.0360 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0156 (2)	0.0170 (2)	0.0206 (2)	0.00100 (16)	0.00237 (15)	0.00051 (16)
S2	0.0151 (2)	0.0293 (3)	0.0248 (3)	0.00225 (17)	0.00043 (17)	−0.00117 (18)
C1	0.0216 (9)	0.0220 (9)	0.0267 (9)	0.0008 (7)	0.0044 (7)	−0.0055 (8)
C2	0.0240 (11)	0.0325 (12)	0.0479 (14)	−0.0070 (9)	0.0031 (10)	−0.0062 (10)
C3	0.0170 (8)	0.0243 (9)	0.0218 (9)	−0.0013 (7)	0.0024 (7)	0.0023 (7)
O4	0.0295 (7)	0.0196 (6)	0.0273 (7)	−0.0003 (5)	0.0047 (5)	0.0038 (5)
O5	0.0189 (7)	0.0465 (9)	0.0327 (8)	0.0046 (6)	0.0053 (5)	−0.0066 (7)
O6	0.0145 (6)	0.0274 (7)	0.0325 (7)	0.0017 (5)	0.0019 (5)	−0.0021 (6)
O7	0.0273 (7)	0.0492 (10)	0.0292 (7)	0.0091 (7)	−0.0061 (6)	0.0039 (7)

S1—O6	1.4398 (13)	S2—O5	1.4386 (14)
S1—O4	1.4397 (14)	S2—O7	1.4416 (15)
S1—C1	1.7563 (19)	S2—C2	1.756 (2)
S1—C3	1.7889 (18)	S2—C3	1.7811 (19)
O6—S1—O4	118.02 (8)	O5—S2—C2	109.70 (11)
O6—S1—C1	108.72 (9)	O7—S2—C2	109.39 (11)
O4—S1—C1	109.82 (10)	O5—S2—C3	108.90 (9)
O6—S1—C3	104.48 (8)	O7—S2—C3	105.13 (9)
O4—S1—C3	109.10 (8)	C2—S2—C3	104.87 (10)
C1—S1—C3	105.96 (10)	S2—C3—S1	117.20 (10)
O5—S2—O7	117.99 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O4i	0.94 (2)	2.55 (2)	3.342 (3)	142.3 (18)
C1—H1B···O4ii	0.92 (2)	2.43 (2)	3.254 (3)	149.1 (19)
C2—H2C···O5iii	0.89 (3)	2.51 (3)	3.365 (3)	160.3 (19)
C3—H3A···O6iv	0.96 (2)	2.56 (2)	3.339 (3)	138.1 (18)
C3—H3A···O7v	0.96 (2)	2.45 (2)	3.206 (3)	135.5 (18)
C3—H3B···O6vi	0.96 (2)	2.27 (2)	3.184 (3)	159.2 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O4i	0.94 (2)	2.55 (2)	3.342 (3)	142.3 (18)
C1—H1B⋯O4ii	0.92 (2)	2.43 (2)	3.254 (3)	149.1 (19)
C2—H2C⋯O5iii	0.89 (3)	2.51 (3)	3.365 (3)	160.3 (19)
C3—H3A⋯O6iv	0.96 (2)	2.56 (2)	3.339 (3)	138.1 (18)
C3—H3A⋯O7v	0.96 (2)	2.45 (2)	3.206 (3)	135.5 (18)
C3—H3B⋯O6vi	0.96 (2)	2.27 (2)	3.184 (3)	159.2 (19)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .