Bis(methyl­sulfon­yl)methane

Awad, R.; Mallah, E.; Abu Dayyih, W.; Sweidan, K.; Steimann, M.

doi:10.1107/S1600536814016201

organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o877

doi:10.1107/S1600536814016201

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Bis(methylsulfonyl)methane

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

^aFaculty of Pharmacy and Medical Science, University of Petra, Amman, Jordan, ^bDepartment of Chemistry, Faculty of Science, The University of Jordan, Amman, Jordan, and ^cUniversity of Tübingen, Inorganic Chemistry, Auf der Morgenstelle 18, 72076 Tübingen, Germany
^*Correspondence e-mail: eyad782002@yahoo.com

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 6 June 2014; accepted 11 July 2014; online 23 July 2014)

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.

CCDC reference: 1013637

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_r = 172.21
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.031
wR(F²) = 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

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)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x, y+1, z; (iii) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x, -y+2, -z; (vi) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

CCDC reference: 1013637

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814016201/cv5464sup1.cif

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

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

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

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 50% probability displacement ellipsoids.

Bis(methylsulfonyl)methane top

Crystal data top

C₃H₈O₄S₂	F(000) = 360
M_r = 172.21	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0285P)² + 0.429P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
1441 reflections	Δρ_max = 0.42 e Å⁻³
115 parameters	Δρ_min = −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)

Crystal data top

C₃H₈O₄S₂	V = 702.3 (3) Å³
M_r = 172.21	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.0496 (18) Å	µ = 0.70 mm⁻¹
b = 5.793 (3) Å	T = 173 K
c = 11.0496 (6) Å	0.25 × 0.05 × 0.05 mm
β = 96.77 (3)°

Data collection top

Stoe IPDS diffractometer	1274 reflections with I > 2σ(I)
9692 measured reflections	R_int = 0.074
1441 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.073	All H-atom parameters refined
S = 1.10	Δρ_max = 0.42 e Å⁻³
1441 reflections	Δρ_min = −0.28 e Å⁻³
115 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y+1, z; (iii) −x−1/2, y−1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x, −y+2, −z; (vi) −x+1/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) x, y+1, z; (iii) −x−1/2, y−1/2, −z+1/2; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x, −y+2, −z; (vi) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

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

References

Awaleh, M. O., Badia, A. & Brisse, F. (2007). Inorg. Chem. 46, 3185–3191. Web of Science CSD CrossRef PubMed CAS Google Scholar
Berthou, J., Jéminet, G. & Laurent, A. (1972). Acta Cryst. B28, 2480–2485. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Gereben, O. & Pusztai, L. (2012). J. Phys. Chem. B, 116, 9114–9121. Web of Science CrossRef CAS PubMed Google Scholar
Glidewell, C., Ferguson, G., Nikas, S. & Varvoglis, A. (1996). Acta Cryst. C52, 1488–1490. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Glidewell, C., Lightfoot, P. & Patterson, I. L. J. (1995). Acta Cryst. C51, 1648–1651. CSD CrossRef Web of Science IUCr Journals Google Scholar
Meehan, P. R., Gregson, R. M., Glidewell, C. & Ferguson, G. (1997). Acta Cryst. C53, 1975–1978. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2008). IPDS, X-AREA and X-RED32, Stoe & Cie, Darmstadt, Germany. Google Scholar
Zhang, B., Chen, X., Kang, H., Sun, F., Wang, Y., Liu, J. & Wang, D. (2009). Acta Cryst. E65, o3198. Web of Science CSD CrossRef IUCr Journals Google Scholar