meso-1-{[2-(Propyl-1-sulfin-yl)eth-yl]sulfin-yl}propane.

The title mol-ecule, C(8)H(18)O(2)S(2), 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 inter-actions, which lead to the formation of supra-molecular 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 = 210.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 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

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H18O2S2	F(000) = 228
Mr = 210.34	Dx = 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

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	Rint = 0.042
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.4°
φ and ω scans	h = −12→15
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −6→6
Tmin = 0.527, Tmax = 0.746	l = −11→11
5666 measured reflections

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(Fo2) + (0.0344P)2 + 0.4193P] where P = (Fo2 + 2Fc2)/3
1239 reflections	(Δ/σ)max = 0.001
56 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .