S,S'-Butane-1,4-diyl bis-(benzene-carbo-thio-ate).

The title compound, C18H18O2S2, which lies on an inversion center, adopts a gauche (+)-trans-trans-trans-gauche (-) (g (+) tttg (-)) conformation in the S-CH2-CH2-CH2-CH2-S bond sequence. In the crystal, mol-ecules are packed in a herringbone arrangement through inter-molecular C-H⋯π inter-actions.

Related literature

For crystal structures and conformations of C6H5C(=O)S(CH2)SC(=O)C6H5 (n = 2, 3, 5, 7, 9), see: for example, Deguire & Brisse (1988 ▶); Leblanc & Brisse (1992 ▶); Abe & Sasanuma (2012 ▶).

Experimental

Crystal data

C18H18O2S2

M = 330.44

Monoclinic,

a = 13.2230 (14) Å

b = 4.8903 (5) Å

c = 13.2638 (15) Å

β = 106.897 (1)°

V = 820.67 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 173 K

0.30 × 0.30 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.908, T max = 0.984

4326 measured reflections

1845 independent reflections

1626 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.05

1845 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813026822/is5305sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026822/is5305Isup2.hkl

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

C18H18O2S2	F(000) = 348
Mr = 330.44	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Melting point: 323 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.2230 (14) Å	Cell parameters from 2016 reflections
b = 4.8903 (5) Å	θ = 3.2–26.8°
c = 13.2638 (15) Å	µ = 0.33 mm−1
β = 106.897 (1)°	T = 173 K
V = 820.67 (15) Å3	Plate, colourless
Z = 2	0.30 × 0.30 × 0.05 mm

Bruker APEXII CCD diffractometer	1845 independent reflections
Radiation source: fine-focus sealed tube	1626 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
Detector resolution: 8.333 pixels mm-1	θmax = 27.5°, θmin = 3.2°
φ and ω scans	h = −15→17
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −6→6
Tmin = 0.908, Tmax = 0.984	l = −13→17
4326 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0413P)2 + 0.1965P] where P = (Fo2 + 2Fc2)/3
1845 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.70285 (9)	0.4894 (3)	0.15671 (9)	0.0292 (3)
C2	0.62320 (10)	0.6555 (3)	0.09507 (10)	0.0350 (3)
H2	0.6032	0.6402	0.0205	0.042*
C3	0.57314 (11)	0.8429 (3)	0.14248 (12)	0.0422 (3)
H3	0.5188	0.9562	0.1003	0.051*
C4	0.60192 (12)	0.8656 (3)	0.25099 (12)	0.0414 (3)
H4	0.5688	0.9982	0.2832	0.050*
C5	0.67851 (12)	0.6964 (3)	0.31244 (11)	0.0427 (3)
H5	0.6968	0.7092	0.3870	0.051*
C6	0.72895 (11)	0.5077 (3)	0.26594 (10)	0.0376 (3)
H6	0.7814	0.3905	0.3087	0.045*
C7	0.75788 (10)	0.2993 (3)	0.10215 (10)	0.0311 (3)
C8	0.91038 (11)	−0.0700 (3)	0.08957 (11)	0.0377 (3)
H8A	0.9495	−0.2334	0.1244	0.045*
H8B	0.8470	−0.1342	0.0344	0.045*
C9	0.98021 (10)	0.0896 (3)	0.03740 (11)	0.0382 (3)
H9A	1.0415	0.1647	0.0924	0.046*
H9B	0.9397	0.2452	−0.0023	0.046*
O1	0.73074 (8)	0.2677 (2)	0.00745 (7)	0.0429 (3)
S1	0.86863 (3)	0.12549 (8)	0.18584 (3)	0.03886 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0297 (6)	0.0284 (6)	0.0294 (6)	−0.0041 (5)	0.0084 (5)	0.0010 (5)
C2	0.0353 (7)	0.0401 (7)	0.0308 (6)	0.0017 (5)	0.0115 (5)	0.0074 (5)
C3	0.0405 (7)	0.0437 (8)	0.0455 (8)	0.0097 (6)	0.0174 (6)	0.0129 (6)
C4	0.0428 (8)	0.0397 (7)	0.0477 (8)	0.0029 (6)	0.0224 (6)	−0.0016 (6)
C5	0.0469 (8)	0.0496 (9)	0.0322 (7)	0.0018 (7)	0.0123 (6)	−0.0050 (6)
C6	0.0392 (7)	0.0415 (8)	0.0294 (6)	0.0040 (6)	0.0057 (5)	0.0006 (6)
C7	0.0315 (6)	0.0308 (6)	0.0295 (6)	−0.0024 (5)	0.0063 (5)	0.0014 (5)
C8	0.0353 (7)	0.0341 (7)	0.0414 (7)	0.0042 (5)	0.0076 (6)	−0.0029 (6)
C9	0.0319 (7)	0.0347 (7)	0.0471 (8)	0.0018 (5)	0.0099 (6)	−0.0062 (6)
O1	0.0479 (6)	0.0495 (6)	0.0282 (5)	0.0103 (5)	0.0060 (4)	−0.0027 (4)
S1	0.0346 (2)	0.0456 (2)	0.0328 (2)	0.00686 (14)	0.00426 (14)	−0.00058 (14)

C1—C6	1.3913 (17)	C6—H6	0.9500
C1—C2	1.3916 (17)	C7—O1	1.2117 (15)
C1—C7	1.4912 (17)	C7—S1	1.7761 (13)
C2—C3	1.3841 (19)	C8—C9	1.5204 (19)
C2—H2	0.9500	C8—S1	1.8053 (14)
C3—C4	1.382 (2)	C8—H8A	0.9900
C3—H3	0.9500	C8—H8B	0.9900
C4—C5	1.377 (2)	C9—C9i	1.526 (3)
C4—H4	0.9500	C9—H9A	0.9900
C5—C6	1.384 (2)	C9—H9B	0.9900
C5—H5	0.9500
C6—C1—C2	119.39 (12)	C1—C6—H6	120.0
C6—C1—C7	122.48 (11)	O1—C7—C1	122.90 (12)
C2—C1—C7	118.13 (11)	O1—C7—S1	121.94 (10)
C3—C2—C1	119.98 (12)	C1—C7—S1	115.15 (9)
C3—C2—H2	120.0	C9—C8—S1	113.65 (10)
C1—C2—H2	120.0	C9—C8—H8A	108.8
C4—C3—C2	120.21 (13)	S1—C8—H8A	108.8
C4—C3—H3	119.9	C9—C8—H8B	108.8
C2—C3—H3	119.9	S1—C8—H8B	108.8
C5—C4—C3	120.04 (13)	H8A—C8—H8B	107.7
C5—C4—H4	120.0	C8—C9—C9i	111.70 (14)
C3—C4—H4	120.0	C8—C9—H9A	109.3
C4—C5—C6	120.26 (13)	C9i—C9—H9A	109.3
C4—C5—H5	119.9	C8—C9—H9B	109.3
C6—C5—H5	119.9	C9i—C9—H9B	109.3
C5—C6—C1	120.06 (13)	H9A—C9—H9B	107.9
C5—C6—H6	120.0	C7—S1—C8	100.22 (6)
C6—C1—C2—C3	2.1 (2)	C6—C1—C7—O1	174.55 (14)
C7—C1—C2—C3	−177.31 (13)	C2—C1—C7—O1	−6.1 (2)
C1—C2—C3—C4	−0.1 (2)	C6—C1—C7—S1	−6.66 (18)
C2—C3—C4—C5	−1.8 (2)	C2—C1—C7—S1	172.72 (11)
C3—C4—C5—C6	1.7 (2)	S1—C8—C9—C9i	175.95 (10)
C4—C5—C6—C1	0.4 (2)	O1—C7—S1—C8	−0.26 (14)
C2—C1—C6—C5	−2.3 (2)	C1—C7—S1—C8	−179.07 (11)
C7—C1—C6—C5	177.12 (14)	C9—C8—S1—C7	83.52 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg1ii	0.95	3.09	3.8810 (15)	141

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯Cg1i	0.95	3.09	3.8810 (15)	141

Symmetry code: (i) .