organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890
Volume 66| Part 3| March 2010| Pages o647-o648

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

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

(Received 11 February 2010; accepted 11 February 2010; online 17 February 2010)

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—H⋯O 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[Pelizzi, G., Michelon, G. & Bonivento, M. (1976). Cryst. Struct. Commun. 5, 617-620.]); Svinning et al. (1976[Svinning, T., Mo, F. & Bruun, T. (1976). Acta Cryst. B32, 759-764.]); Chu & Madden (1978[Chu, S. S. C. & Madden, J. (1978). Acta Cryst. B34, 841-845.]); Ternay et al. (1978[Ternay, A. L. Jr, Lin, J., Sutliff, T., Chu, S. S. C. & Chung, B. (1978). J. Org. Chem. 43, 3024-3031.]); Cattalini et al. (1979[Cattalini, L., Michelon, G., Marangoni, G. & Pelizzi, G. (1979). J. Chem. Soc. Dalton Trans. pp. 96-101.]); Li et al. (2002[Li, J.-R., Zhang, R.-H. & Bu, X.-H. (2002). Acta Cryst. E58, o911-o912.], 2004[Li, J.-R., Bu, X.-H. & Zhang, R.-H. (2004). Inorg. Chem. 43, 237-244.]). For the preparation and separation of the steroisomers of the title compound, see: Hull & Bargar (1975[Hull, C. M. & Bargar, T. W. (1975). J. Org. Chem. 40, 3152-3154.]); Li et al. (2005[Li, J.-R., Bu, X.-H., Zhang, R.-H. & Ribas, J. (2005). Cryst. Growth Des. 5, 1919-1932.]). For information on the use of bis-sulfoxides as a ligand, see: de Souza et al. (1995[Souza, G. F. de, Filgueiras, C. A. L., Abras, A., Carvalho, C. C., Francisco, R. H. P. & Gambardella, M. T. Do. P. (1995). An. Ass. Bras. Quim. 44, 42-46.], 1997[Souza, G. F. de, Filgueiras, C. A. L., Hitchcock, P. B. & Nixon, J. F. (1997). Inorg. Chim. Acta, 261, 221-225.]); Huang et al. (1986[Huang, Z., Zhang, R., Wang, J. & Zhang, Z. (1986). Wuji Huaxue Xuebaoe, 2, 54-59.]); Huang & Zhang (1986[Huang, Z. & Zhang, Z. (1986). Wuji Huaxu Xuebaoe, 2, 64-71.]); Filgueiras & Marques (1985[Filgueiras, C. A. L. & Marques, E. V. (1985). Transition Met. Chem. 10, 241-243.]); Filgueiras et al. (1982[Filgueiras, C. A. L., Celso, C., Marques, E. V. & Johnson, B. F. G. (1982). Inorg. Chim. Acta, 59, 71-74.]); Bu et al. (2002[Bu, X.-H., Weng, W., Li, J.-R., Chen, W. & Zhang, R.-H. (2002). Inorg. Chem. 41, 413-415.]); Li et al. (2005[Li, J.-R., Bu, X.-H., Zhang, R.-H. & Ribas, J. (2005). Cryst. Growth Des. 5, 1919-1932.]); Yapp et al. (1997[Yapp, D. T. T., Rettig, S. J., James, B. R. & Skov, K. A. (1997). Inorg. Chem. 36, 5635-5641.]).

[Scheme 1]

Experimental

Crystal data
  • C8H18O2S2

  • Mr = 210.34

  • Monoclinic, P 21 /c

  • a = 11.9794 (9) Å

  • b = 5.2190 (3) Å

  • c = 8.7618 (5) Å

  • β = 97.191 (5)°

  • V = 543.48 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 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[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.527, Tmax = 0.746

  • 5666 measured reflections

  • 1239 independent reflections

  • 1167 reflections with I > 2σ(I)

  • Rint = 0.042

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.080

  • S = 1.06

  • 1239 reflections

  • 56 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1b⋯O1i 0.99 2.41 3.3035 (19) 150
C4—H4a⋯O1i 0.99 2.40 3.2751 (19) 147
C4—H4b⋯O1ii 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[Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). publCIF. In preparation.]).

Supporting information


Comment top

Bis-sulfoxides such as the title compound, (I), have found use as ligands (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). Details on the preparation and the separation of steroisomers of (I) are available in the literature (Hull & Bargar 1975; Li et al. 2005). Crystallography shows the molecule of (I) is disposed about a centre of inversion, Fig. 1, and the n-propyl chain has an extended conformation as seen in the value of the S1–C1–C2–C3 torsion angle of S1–C1–C2–C3 of -179.93 (11) °. The anti-disposition of the sulfinyl-O atoms allow for the optimisation of C–H···O interactions in the crystal structure, Table 1. Thus, each sulfinyl-O1 associates with three methylene-H atoms to form a supramolecular array in the bc plane, Fig. 2, which stack along the a axis, Fig. 3.

The central core in (I), including its disposition about a centre of inversion, resembles that found in each of the reported meso-RS( O)CH2CH2S(O)R structures, where R = Me (Svinning et al., 1976), Et (Li et al., 2004), Ph (Pelizzi, et al. 1976; Ternay et al. 1978; Cattalini et al., 1979), benzyl (Li et al. 2002), and mesityl (Chu & Madden, 1978), but not in their homo chiral stereoisomers where R = Ph (Ternay et al. 1978; Cattalini et al., 1979) and mesityl (Chu & Madden, 1978).

Related literature top

For the structures of 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 top

Compound (I) was prepared by a published method (Li et al., 2005) and had spectral and other parameters in agreement with published values (Li et al., 2005; Yapp et al., 1997). M.pt. 434-435 K. Lit. value 434-435 K (Hull & Bargar, 1975; Li et al., 2005). The sample used in the crystallographic study was grown from an ethanol solution of (I).

Refinement top

The C-bound H atoms were geometrically placed (C–H = 0.98–0.99 Å) and refined as riding with Uiso(H) = 1.2-1.5Ueq(C).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
[Figure 2] Fig. 2. A view of a supramolecular array in (I) in the bc plane. The C–H···O interactions are shown as blue dashed lines. Colour code: S, yellow; O, red; C, grey; and H, green.
[Figure 3] Fig. 3. View in projection down the c axis of the unit cell contents in (I). Colour code: S, yellow; O, red; C, grey; and H, green.
meso-1-{[2-(Propyl-1-sulfinyl)ethyl]sulfinyl}propane top
Crystal data top
C8H18O2S2F(000) = 228
Mr = 210.34Dx = 1.285 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 19160 reflections
a = 11.9794 (9) Åθ = 2.9–27.5°
b = 5.2190 (3) ŵ = 0.45 mm1
c = 8.7618 (5) ÅT = 120 K
β = 97.191 (5)°Plate, colourless
V = 543.48 (6) Å31.1 × 0.6 × 0.12 mm
Z = 2
Data collection top
Nonius KappaCCD area-detector
diffractometer
1239 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode1167 reflections with I > 2σ(I)
10 cm confocal mirrors monochromatorRint = 0.042
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.4°
ϕ and ω scansh = 1215
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
k = 66
Tmin = 0.527, Tmax = 0.746l = 1111
5666 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0344P)2 + 0.4193P]
where P = (Fo2 + 2Fc2)/3
1239 reflections(Δ/σ)max = 0.001
56 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C8H18O2S2V = 543.48 (6) Å3
Mr = 210.34Z = 2
Monoclinic, P21/cMo Kα radiation
a = 11.9794 (9) ŵ = 0.45 mm1
b = 5.2190 (3) ÅT = 120 K
c = 8.7618 (5) Å1.1 × 0.6 × 0.12 mm
β = 97.191 (5)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
1239 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
1167 reflections with I > 2σ(I)
Tmin = 0.527, Tmax = 0.746Rint = 0.042
5666 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.080H-atom parameters constrained
S = 1.06Δρmax = 0.33 e Å3
1239 reflectionsΔρmin = 0.35 e Å3
56 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.66819 (3)0.09909 (6)0.45405 (4)0.01305 (14)
O10.64458 (10)0.37397 (19)0.40786 (13)0.0187 (3)
C10.72083 (12)0.0560 (3)0.29375 (16)0.0149 (3)
H1A0.67050.01920.19780.018*
H1B0.72280.24380.30970.018*
C20.83896 (12)0.0425 (3)0.27975 (17)0.0191 (3)
H2A0.83630.23050.26460.023*
H2B0.88850.00650.37650.023*
C30.88818 (14)0.0828 (3)0.14553 (19)0.0246 (4)
H3A0.83980.04550.04940.037*
H3B0.96380.01470.13970.037*
H3C0.89250.26860.16140.037*
C40.53341 (12)0.0583 (3)0.44006 (15)0.0144 (3)
H4A0.54380.24430.45890.017*
H4B0.49240.03430.33580.017*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0150 (2)0.0110 (2)0.0135 (2)0.00060 (11)0.00307 (13)0.00048 (11)
O10.0238 (6)0.0087 (5)0.0244 (6)0.0012 (4)0.0066 (4)0.0004 (4)
C10.0176 (7)0.0133 (6)0.0147 (6)0.0002 (5)0.0048 (5)0.0007 (5)
C20.0179 (7)0.0221 (7)0.0181 (7)0.0014 (6)0.0057 (5)0.0005 (6)
C30.0210 (8)0.0325 (9)0.0217 (7)0.0031 (6)0.0078 (6)0.0010 (6)
C40.0167 (7)0.0111 (6)0.0162 (6)0.0018 (5)0.0049 (5)0.0013 (5)
Geometric parameters (Å, º) top
S1—O11.5077 (10)C2—H2B0.9900
S1—C41.8018 (14)C3—H3A0.9800
S1—C11.8021 (14)C3—H3B0.9800
C1—C21.525 (2)C3—H3C0.9800
C1—H1A0.9900C4—C4i1.525 (3)
C1—H1B0.9900C4—H4A0.9900
C2—C31.527 (2)C4—H4B0.9900
C2—H2A0.9900
O1—S1—C4106.20 (7)H2A—C2—H2B107.9
O1—S1—C1106.88 (7)C2—C3—H3A109.5
C4—S1—C198.06 (6)C2—C3—H3B109.5
C2—C1—S1109.27 (10)H3A—C3—H3B109.5
C2—C1—H1A109.8C2—C3—H3C109.5
S1—C1—H1A109.8H3A—C3—H3C109.5
C2—C1—H1B109.8H3B—C3—H3C109.5
S1—C1—H1B109.8C4i—C4—S1108.34 (13)
H1A—C1—H1B108.3C4i—C4—H4A110.0
C1—C2—C3111.67 (13)S1—C4—H4A110.0
C1—C2—H2A109.3C4i—C4—H4B110.0
C3—C2—H2A109.3S1—C4—H4B110.0
C1—C2—H2B109.3H4A—C4—H4B108.4
C3—C2—H2B109.3
O1—S1—C1—C271.04 (11)O1—S1—C4—C4i65.40 (14)
C4—S1—C1—C2179.23 (10)C1—S1—C4—C4i175.68 (13)
S1—C1—C2—C3179.93 (11)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1b···O1ii0.992.413.3035 (19)150
C4—H4a···O1ii0.992.403.2751 (19)147
C4—H4b···O1iii0.992.573.5124 (18)159
Symmetry codes: (ii) x, y+1, z; (iii) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC8H18O2S2
Mr210.34
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)11.9794 (9), 5.2190 (3), 8.7618 (5)
β (°) 97.191 (5)
V3)543.48 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.45
Crystal size (mm)1.1 × 0.6 × 0.12
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.527, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
5666, 1239, 1167
Rint0.042
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.080, 1.06
No. of reflections1239
No. of parameters56
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.35

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1b···O1i0.992.413.3035 (19)150
C4—H4a···O1i0.992.403.2751 (19)147
C4—H4b···O1ii0.992.573.5124 (18)159
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+1/2.
 

Footnotes

Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

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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Volume 66| Part 3| March 2010| Pages o647-o648
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