Bis(methyl­sulfon­yl)methane

Riad Awad; Eyad Mallah; Wael Abu Dayyih; Kamal Sweidan; Manfred Steimann

doi:10.1107/S1600536814016201

. 2014 Jul 23;70(Pt 8):o877. doi: 10.1107/S1600536814016201

Bis(methylsulfonyl)methane

Riad Awad ^a, Eyad Mallah ^a,^*, Wael Abu Dayyih ^a, Kamal Sweidan ^b, Manfred Steimann ^c

PMCID: PMC4158514 PMID: 25249921

Abstract

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 molecule utilizes CH₂ and CH₃ bonds to form weak C—H⋯O hydrogen bonds to six other molecules, thus linking molecules into a three-dimensional network.

Keywords: crystal structure

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 ▶). graphic file with name e-70-0o877-scheme1.jpg

Experimental

Crystal data

C₃H₈O₄S₂
M _r = 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
Δρ_max = 0.42 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-70-0o877-sup1.cif^{(12.7KB, cif)}

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

e-70-0o877-Isup2.hkl^{(71.1KB, hkl)}

Click here for additional data file.^{(2.6KB, cml)}

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

CCDC reference: 1013637

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

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⋯O6^iv	0.96 (2)	2.56 (2)	3.339 (3)	138.1 (18)
C3—H3A⋯O7^v	0.96 (2)	2.45 (2)	3.206 (3)	135.5 (18)
C3—H3B⋯O6^vi	0.96 (2)	2.27 (2)	3.184 (3)	159.2 (19)

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

Acknowledgments

The authors are grateful to the University of Petra for financial support and the University of Tübingen for technical assistance.

supplementary crystallographic information

S1. Comment

The title compound, bis (methylthio) methane (I), is an odorous constituent of truffle which considered as an essential food and industrial flavor used as a primary aromatic ingredient in the truffle oil when combined in an olive oil base (Gereben & Pusztai, 2012; Awaleh et al., 2007).

In (I) (Fig. 1), the two central C—S bond distances [1.781 (2) Å and 1.789 (2) Å] are very close to those reported by Glidewell et al. (1995) for (PhSO₂)₂CH₂ [1.786 Å], but smaller than the corresponding distances in the (PhSO₂)₂CBr₂ [1.863 Å] and (PhSO₂)₂CI)₂ [1.854 Å], respectively. This fact could be attributed due to the large size of halogen atoms Br and I relative to the hydrogen atom in the prepared molecule. The S2—C3—S1 angle of 117.20 (10)° and the two O—S—O angles of 118.02 (8)° and 108.72 (9)° entirely consistent with those reported previously by Lucchi et al. (1985). The overall conformation is close to the corresponding conformations reported for similar compounds (Berthou et al., 1972; Glidewell et al., 1995).

S2. Experimental

The title compound was prepared by addition of Bis (methylthio) methane (2.00 ml, 19.58 mmol) to a solution containing acetic acid (16.00 ml, 279.76 mmol) with stirring at 0°C for 15 min. After that (17.00 ml, 720 mmol) of hydrogen peroxide was added drop wise at room temperature, and then the mixture was heated for 3 h at 55°C, the whit precipitate was formed, washed with methanol and dried in vacuo. Yield after recystallization from dichloromethane / diethyl ether 2.72 g (82%), as colorless plate crystals.