Butane-1,4-diyl bis-(benzene-carbodi-thio-ate).

The title compound, C18H18S4, which lies on an inversion center, adopts a trans-gauche (+)-trans-gauche (-)-trans (tg (+) tg (-) t) conformation of the S-CH2-CH2-CH2-CH2-S bond sequence. In the crystal, a π-π inter-action with a centroid-centroid distance of 3.8797 (16) Å is observed.

Related literature

For crystal structures and conformations of C6H5C(=S)S(CH2)2SC(=S)C6H5 and C6H5C(=O)S(CH2)4SC(=O)C6H5, see: Abe et al. (2011 ▶, 2013 ▶). For related compounds, see: Sawanobori et al. (2001 ▶); Sasanuma et al. (2002 ▶). For the synthesis of piperidinium di­thio­benzoate, see: Kato et al. (1973 ▶).

Experimental

Crystal data

C18H18S4

M = 362.56

Monoclinic,

a = 11.0205 (6) Å

b = 7.2535 (5) Å

c = 11.3090 (7) Å

β = 110.805 (2)°

V = 845.06 (9) Å3

Z = 2

Cu Kα radiation

μ = 5.09 mm−1

T = 173 K

0.40 × 0.20 × 0.01 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.235, T max = 0.951

4872 measured reflections

1480 independent reflections

1468 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.13

1480 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.31 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813027529/is5312sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027529/is5312Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027529/is5312Isup3.cml

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

C18H18S4	F(000) = 380
Mr = 362.56	Dx = 1.425 Mg m−3
Monoclinic, P21/n	Melting point: 341 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 11.0205 (6) Å	Cell parameters from 5003 reflections
b = 7.2535 (5) Å	θ = 4.8–67.8°
c = 11.3090 (7) Å	µ = 5.09 mm−1
β = 110.805 (2)°	T = 173 K
V = 845.06 (9) Å3	Plate, pink
Z = 2	0.40 × 0.20 × 0.01 mm

Bruker APEXII CCD area-detector diffractometer	1480 independent reflections
Radiation source: Bruker TXS fine-focus rotating anode	1468 reflections with I > 2σ(I)
Bruker Helios multilayer confocal mirror monochromator	Rint = 0.028
Detector resolution: 8.333 pixels mm-1	θmax = 68.1°, θmin = 4.8°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −8→7
Tmin = 0.235, Tmax = 0.951	l = −13→13
4872 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0393P)2 + 1.0478P] where P = (Fo2 + 2Fc2)/3
1480 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.31 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	−0.0082 (2)	0.2157 (3)	0.3798 (2)	0.0226 (5)
C2	0.0225 (2)	0.2350 (4)	0.5097 (2)	0.0271 (5)
H2	0.1068	0.2029	0.5658	0.033*
C3	−0.0686 (2)	0.3004 (4)	0.5579 (2)	0.0309 (5)
H3	−0.0463	0.3138	0.6467	0.037*
C4	−0.1921 (2)	0.3461 (4)	0.4770 (3)	0.0314 (6)
H4	−0.2547	0.3904	0.5100	0.038*
C5	−0.2237 (2)	0.3270 (4)	0.3480 (3)	0.0347 (6)
H5	−0.3085	0.3581	0.2923	0.042*
C6	−0.1329 (2)	0.2628 (4)	0.2992 (2)	0.0300 (5)
H6	−0.1556	0.2508	0.2103	0.036*
C7	0.0885 (2)	0.1450 (3)	0.3270 (2)	0.0222 (5)
C8	0.3424 (2)	0.0498 (4)	0.3534 (2)	0.0288 (5)
H8A	0.3123	−0.0796	0.3375	0.035*
H8B	0.3313	0.1080	0.2710	0.035*
C9	0.4854 (2)	0.0543 (4)	0.4385 (2)	0.0270 (5)
H9A	0.5121	0.1841	0.4594	0.032*
H9B	0.5381	0.0031	0.3913	0.032*
S1	0.04887 (5)	0.05242 (9)	0.18505 (5)	0.0286 (2)
S2	0.24732 (5)	0.17228 (9)	0.42927 (5)	0.0278 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0177 (10)	0.0217 (12)	0.0276 (11)	−0.0011 (9)	0.0072 (9)	0.0005 (9)
C2	0.0197 (11)	0.0330 (13)	0.0271 (11)	0.0003 (10)	0.0064 (9)	0.0023 (10)
C3	0.0304 (12)	0.0364 (14)	0.0286 (12)	−0.0004 (11)	0.0136 (10)	−0.0013 (11)
C4	0.0255 (12)	0.0310 (14)	0.0429 (14)	0.0014 (10)	0.0186 (11)	−0.0034 (11)
C5	0.0189 (11)	0.0430 (16)	0.0389 (14)	0.0067 (11)	0.0063 (10)	−0.0015 (12)
C6	0.0210 (11)	0.0391 (15)	0.0269 (11)	0.0026 (10)	0.0047 (9)	−0.0026 (10)
C7	0.0169 (10)	0.0228 (12)	0.0255 (11)	0.0010 (8)	0.0058 (8)	0.0044 (9)
C8	0.0178 (11)	0.0406 (15)	0.0283 (11)	0.0071 (10)	0.0087 (9)	−0.0003 (10)
C9	0.0172 (11)	0.0335 (14)	0.0312 (12)	0.0040 (9)	0.0097 (9)	0.0022 (10)
S1	0.0211 (3)	0.0387 (4)	0.0246 (3)	−0.0006 (2)	0.0062 (2)	−0.0052 (2)
S2	0.0143 (3)	0.0394 (4)	0.0271 (3)	0.0035 (2)	0.0040 (2)	−0.0065 (2)

C1—C2	1.392 (3)	C6—H6	0.9500
C1—C6	1.395 (3)	C7—S1	1.649 (2)
C1—C7	1.487 (3)	C7—S2	1.732 (2)
C2—C3	1.386 (4)	C8—C9	1.527 (3)
C2—H2	0.9500	C8—S2	1.807 (2)
C3—C4	1.383 (4)	C8—H8A	0.9900
C3—H3	0.9500	C8—H8B	0.9900
C4—C5	1.381 (4)	C9—C9i	1.530 (5)
C4—H4	0.9500	C9—H9A	0.9900
C5—C6	1.384 (3)	C9—H9B	0.9900
C5—H5	0.9500
C2—C1—C6	118.6 (2)	C1—C6—H6	119.8
C2—C1—C7	121.2 (2)	C1—C7—S1	123.48 (16)
C6—C1—C7	120.2 (2)	C1—C7—S2	113.01 (16)
C3—C2—C1	120.7 (2)	S1—C7—S2	123.51 (13)
C3—C2—H2	119.6	C9—C8—S2	109.43 (16)
C1—C2—H2	119.6	C9—C8—H8A	109.8
C4—C3—C2	120.1 (2)	S2—C8—H8A	109.8
C4—C3—H3	120.0	C9—C8—H8B	109.8
C2—C3—H3	120.0	S2—C8—H8B	109.8
C5—C4—C3	119.6 (2)	H8A—C8—H8B	108.2
C5—C4—H4	120.2	C8—C9—C9i	113.5 (2)
C3—C4—H4	120.2	C8—C9—H9A	108.9
C4—C5—C6	120.5 (2)	C9i—C9—H9A	108.9
C4—C5—H5	119.7	C8—C9—H9B	108.9
C6—C5—H5	119.7	C9i—C9—H9B	108.9
C5—C6—C1	120.4 (2)	H9A—C9—H9B	107.7
C5—C6—H6	119.8	C7—S2—C8	104.20 (11)
C6—C1—C2—C3	−0.3 (4)	C2—C1—C7—S1	158.30 (19)
C7—C1—C2—C3	−179.8 (2)	C6—C1—C7—S1	−21.2 (3)
C1—C2—C3—C4	0.5 (4)	C2—C1—C7—S2	−22.3 (3)
C2—C3—C4—C5	−0.3 (4)	C6—C1—C7—S2	158.2 (2)
C3—C4—C5—C6	−0.1 (4)	S2—C8—C9—C9i	66.7 (3)
C4—C5—C6—C1	0.3 (4)	C1—C7—S2—C8	172.54 (17)
C2—C1—C6—C5	−0.1 (4)	S1—C7—S2—C8	−8.11 (19)
C7—C1—C6—C5	179.4 (2)	C9—C8—S2—C7	−176.88 (17)