meso-1-{[2-(Propyl-1-sulfin­yl)eth­yl]sulfin­yl}propane

Wardell, S.M.S.V.; Wardell, J.L.; Lima, G.M. de; Tiekink, E.R.T.

doi:10.1107/S1600536810005799

Volume 66
Part 3
Pages o647-o648
March 2010

Received 11 February 2010
Accepted 11 February 2010
Online 17 February 2010

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.080
Data-to-parameter ratio = 22.1
Details

meso-1-{[2-(Propyl-1-sulfinyl)ethyl]sulfinyl}propane

Solange M. S. V. Wardell,^a James L. Wardell,^b ⁺ Geraldo M. de Lima ^c and Edward R. T. Tiekink ^d ^*

^aCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland,^bCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil,^cDepartamento de Quimica, ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, MG, Brazil, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: Edward.Tiekink@gmail.com

The title molecule, C₈H₁₈O₂S₂, is disposed about a centre of inversion implying an anti-disposition of the sulfinyl-O atoms; the terminal n-propyl group has an extended conformation. The crystal packing is dominated by C-HO interactions, which lead to the formation of supramolecular arrays in the bc plane.

Related literature

For the structures of the stereoisomers of RS(=O)CH₂CH₂S(=O)R, see: Pelizzi et al. (1976); Svinning et al. (1976); Chu & Madden (1978); Ternay et al. (1978); Cattalini et al. (1979); Li et al. (2002, 2004). For the preparation and separation of the steroisomers of the title compound, see: Hull & Bargar (1975); Li et al. (2005). For information on the use of bis-sulfoxides as a ligand, see: de Souza et al. (1995, 1997); Huang et al. (1986); Huang & Zhang (1986); Filgueiras & Marques (1985); Filgueiras et al. (1982); Bu et al. (2002); Li et al. (2005); Yapp et al. (1997).

Experimental

Crystal data

C₈H₁₈O₂S₂
M_r = 210.34
Monoclinic, P 2₁ /c
a = 11.9794 (9) Å
b = 5.2190 (3) Å
c = 8.7618 (5) Å
= 97.191 (5)°
V = 543.48 (6) Å³
Z = 2
Mo K radiation
= 0.45 mm^-1
T = 120 K
1.1 × 0.6 × 0.12 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T_min = 0.527, T_max = 0.746
5666 measured reflections
1239 independent reflections
1167 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.080
S = 1.06
1239 reflections
56 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1bO1ⁱ	0.99	2.41	3.3035 (19)	150
C4-H4aO1ⁱ	0.99	2.40	3.2751 (19)	147
C4-H4bO1ⁱⁱ	0.99	2.57	3.5124 (18)	159
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2201 ).

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from CAPES and FAPEMIG (Brazil).

References

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organic compounds