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

organic compounds

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ISSN: 2056-9890

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

doi:10.1107/S1600536810005799

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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

(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 ); 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
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 ) T_min = 0.527, T_max = 0.746
5666 measured reflections
1239 independent reflections
1167 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.06
1239 reflections
56 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); 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 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536810005799/ez2201sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810005799/ez2201Isup2.hkl

checkCIF report

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).

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

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.
	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.
	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

C₈H₁₈O₂S₂	F(000) = 228
M_r = 210.34	D_x = 1.285 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19160 reflections
a = 11.9794 (9) Å	θ = 2.9–27.5°
b = 5.2190 (3) Å	µ = 0.45 mm⁻¹
c = 8.7618 (5) Å	T = 120 K
β = 97.191 (5)°	Plate, colourless
V = 543.48 (6) Å³	1.1 × 0.6 × 0.12 mm
Z = 2

Data collection top

Nonius KappaCCD area-detector diffractometer	1239 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1167 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.042
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ϕ and ω scans	h = −12→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −6→6
T_min = 0.527, T_max = 0.746	l = −11→11
5666 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0344P)² + 0.4193P] where P = (F_o² + 2F_c²)/3
1239 reflections	(Δ/σ)_max = 0.001
56 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₈H₁₈O₂S₂	V = 543.48 (6) Å³
M_r = 210.34	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9794 (9) Å	µ = 0.45 mm⁻¹
b = 5.2190 (3) Å	T = 120 K
c = 8.7618 (5) Å	1.1 × 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)
T_min = 0.527, T_max = 0.746	R_int = 0.042
5666 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	Δρ_max = 0.33 e Å⁻³
1239 reflections	Δρ_min = −0.35 e Å⁻³
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

	x	y	z	U_iso*/U_eq
S1	0.66819 (3)	−0.09909 (6)	0.45405 (4)	0.01305 (14)
O1	0.64458 (10)	−0.37397 (19)	0.40786 (13)	0.0187 (3)
C1	0.72083 (12)	0.0560 (3)	0.29375 (16)	0.0149 (3)
H1A	0.6705	0.0192	0.1978	0.018*
H1B	0.7228	0.2438	0.3097	0.018*
C2	0.83896 (12)	−0.0425 (3)	0.27975 (17)	0.0191 (3)
H2A	0.8363	−0.2305	0.2646	0.023*
H2B	0.8885	−0.0065	0.3765	0.023*
C3	0.88818 (14)	0.0828 (3)	0.14553 (19)	0.0246 (4)
H3A	0.8398	0.0455	0.0494	0.037*
H3B	0.9638	0.0147	0.1397	0.037*
H3C	0.8925	0.2686	0.1614	0.037*
C4	0.53341 (12)	0.0583 (3)	0.44006 (15)	0.0144 (3)
H4A	0.5438	0.2443	0.4589	0.017*
H4B	0.4924	0.0343	0.3358	0.017*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0150 (2)	0.0110 (2)	0.0135 (2)	0.00060 (11)	0.00307 (13)	0.00048 (11)
O1	0.0238 (6)	0.0087 (5)	0.0244 (6)	0.0012 (4)	0.0066 (4)	0.0004 (4)
C1	0.0176 (7)	0.0133 (6)	0.0147 (6)	−0.0002 (5)	0.0048 (5)	0.0007 (5)
C2	0.0179 (7)	0.0221 (7)	0.0181 (7)	0.0014 (6)	0.0057 (5)	0.0005 (6)
C3	0.0210 (8)	0.0325 (9)	0.0217 (7)	−0.0031 (6)	0.0078 (6)	0.0010 (6)
C4	0.0167 (7)	0.0111 (6)	0.0162 (6)	0.0018 (5)	0.0049 (5)	0.0013 (5)

Geometric parameters (Å, º) top

S1—O1	1.5077 (10)	C2—H2B	0.9900
S1—C4	1.8018 (14)	C3—H3A	0.9800
S1—C1	1.8021 (14)	C3—H3B	0.9800
C1—C2	1.525 (2)	C3—H3C	0.9800
C1—H1A	0.9900	C4—C4ⁱ	1.525 (3)
C1—H1B	0.9900	C4—H4A	0.9900
C2—C3	1.527 (2)	C4—H4B	0.9900
C2—H2A	0.9900

O1—S1—C4	106.20 (7)	H2A—C2—H2B	107.9
O1—S1—C1	106.88 (7)	C2—C3—H3A	109.5
C4—S1—C1	98.06 (6)	C2—C3—H3B	109.5
C2—C1—S1	109.27 (10)	H3A—C3—H3B	109.5
C2—C1—H1A	109.8	C2—C3—H3C	109.5
S1—C1—H1A	109.8	H3A—C3—H3C	109.5
C2—C1—H1B	109.8	H3B—C3—H3C	109.5
S1—C1—H1B	109.8	C4ⁱ—C4—S1	108.34 (13)
H1A—C1—H1B	108.3	C4ⁱ—C4—H4A	110.0
C1—C2—C3	111.67 (13)	S1—C4—H4A	110.0
C1—C2—H2A	109.3	C4ⁱ—C4—H4B	110.0
C3—C2—H2A	109.3	S1—C4—H4B	110.0
C1—C2—H2B	109.3	H4A—C4—H4B	108.4
C3—C2—H2B	109.3

O1—S1—C1—C2	−71.04 (11)	O1—S1—C4—C4ⁱ	65.40 (14)
C4—S1—C1—C2	179.23 (10)	C1—S1—C4—C4ⁱ	175.68 (13)
S1—C1—C2—C3	−179.93 (11)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1b···O1ⁱⁱ	0.99	2.41	3.3035 (19)	150
C4—H4a···O1ⁱⁱ	0.99	2.40	3.2751 (19)	147
C4—H4b···O1ⁱⁱⁱ	0.99	2.57	3.5124 (18)	159

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

Experimental details

Crystal data
Chemical formula	C₈H₁₈O₂S₂
M_r	210.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	11.9794 (9), 5.2190 (3), 8.7618 (5)
β (°)	97.191 (5)
V (Å³)	543.48 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	1.1 × 0.6 × 0.12

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.527, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	5666, 1239, 1167
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.06
No. of reflections	1239
No. of parameters	56
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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+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).

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