Ethane-1,2-diyl bis-(benzene-dithio-ate).

In the crystal structure, the title compound, C(16)H(14)S(4), is located on an inversion center and exhibits a gauche(+)-trans-gauche(-) conformation in the S-CH(2)-CH(2)-S bond sequence. The S-C=S plane makes a dihedral angle of 30.63 (17)° with the phenyl ring. An inter-molecular C-H⋯π inter-action is observed.

Related literature

For crystal structures and conformations of related compounds with S—CH2—CH2—S bond sequences, see: for example, Takahashi et al. (1968 ▶); Deguire & Brisse (1988 ▶); Sasanuma & Watanabe (2006 ▶).

Experimental

Crystal data

C16H14S4

M = 334.53

Monoclinic,

a = 11.5431 (7) Å

b = 8.74071 (16) Å

c = 8.93720 (16) Å

β = 122.3772 (7)°

V = 761.54 (5) Å3

Z = 2

Cu Kα radiation

μ = 5.60 mm−1

T = 93 K

0.32 × 0.27 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.195, T max = 0.639

8415 measured reflections

1389 independent reflections

1292 reflections with F 2 > 2σ(F 2)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.079

S = 1.14

1389 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.39 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku Americas & Rigaku, 2007 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010245/is2686sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010245/is2686Isup2.hkl

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

C16H14S4	F(000) = 348.00
Mr = 334.53	Dx = 1.459 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 7723 reflections
a = 11.5431 (7) Å	θ = 4.5–68.2°
b = 8.74071 (16) Å	µ = 5.60 mm−1
c = 8.93720 (16) Å	T = 93 K
β = 122.3772 (7)°	Prism, orange
V = 761.54 (5) Å3	0.32 × 0.27 × 0.08 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	1292 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.054
ω scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
Tmin = 0.195, Tmax = 0.639	k = −10→10
8415 measured reflections	l = −10→10
1389 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.0329P)2 + 0.4332P] where P = (Fo2 + 2Fc2)/3
1389 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.39 e Å−3
Primary atom site location: structure-invariant direct methods

Geometry. All e.s.d.'s (except that 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 was performed with all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2, while the R-factor on F. The threshold expression of F2 > 2.0 σ(F2) was used only for calculating R-factor.

	x	y	z	Uiso*/Ueq
S1	0.27738 (4)	0.43962 (5)	0.38957 (6)	0.01677 (15)
S2	0.03137 (4)	0.26716 (5)	0.11103 (6)	0.01529 (15)
C1	0.26047 (17)	0.1259 (2)	0.3631 (2)	0.0107 (3)
C2	0.35523 (17)	0.1069 (2)	0.5448 (2)	0.0132 (4)
C3	0.41019 (18)	−0.0366 (2)	0.6127 (2)	0.0154 (4)
C4	0.37290 (18)	−0.1615 (2)	0.4996 (2)	0.0174 (4)
C5	0.28006 (18)	−0.1431 (2)	0.3188 (2)	0.0157 (4)
C6	0.22359 (18)	−0.0005 (2)	0.2505 (2)	0.0134 (3)
C7	0.19836 (18)	0.2793 (2)	0.2954 (2)	0.0116 (3)
C8	−0.02347 (18)	0.4635 (2)	0.0565 (2)	0.0143 (4)
H2	0.3821	0.1924	0.6221	0.016*
H3	0.4733	−0.0493	0.7363	0.019*
H4	0.4109	−0.2594	0.5460	0.021*
H5	0.2552	−0.2285	0.2417	0.019*
H6	0.1596	0.0112	0.1269	0.016*
H8A	−0.1248	0.4677	−0.0080	0.017*
H8B	0.0137	0.5229	0.1674	0.017*

	U11	U22	U33	U12	U13	U23
S1	0.0199 (2)	0.0102 (2)	0.0133 (2)	−0.00211 (16)	0.0043 (2)	−0.00110 (17)
S2	0.0121 (2)	0.0111 (2)	0.0152 (3)	0.00043 (15)	0.0024 (2)	0.00257 (17)
C1	0.0106 (7)	0.0115 (8)	0.0113 (9)	0.0003 (6)	0.0068 (7)	0.0013 (7)
C2	0.0112 (7)	0.0137 (9)	0.0129 (10)	−0.0019 (6)	0.0053 (7)	0.0001 (7)
C3	0.0113 (8)	0.0176 (9)	0.0123 (10)	−0.0007 (6)	0.0029 (7)	0.0027 (7)
C4	0.0150 (8)	0.0120 (9)	0.0236 (11)	0.0024 (6)	0.0092 (8)	0.0045 (8)
C5	0.0162 (8)	0.0118 (8)	0.0168 (10)	−0.0003 (6)	0.0072 (8)	−0.0021 (7)
C6	0.0127 (8)	0.0156 (9)	0.0098 (9)	−0.0005 (6)	0.0045 (7)	0.0005 (7)
C7	0.0134 (8)	0.0137 (9)	0.0089 (9)	0.0001 (6)	0.0067 (7)	0.0002 (7)
C8	0.0143 (8)	0.0119 (8)	0.0153 (10)	0.0050 (6)	0.0070 (8)	0.0039 (7)

S1—C7	1.6376 (17)	C5—C6	1.387 (2)
S2—C7	1.7436 (15)	C8—C8i	1.519 (3)
S2—C8	1.8033 (17)	C2—H2	0.950
C1—C2	1.400 (2)	C3—H3	0.950
C1—C6	1.399 (2)	C4—H4	0.950
C1—C7	1.488 (2)	C5—H5	0.950
C2—C3	1.390 (2)	C6—H6	0.950
C3—C4	1.389 (2)	C8—H8A	0.990
C4—C5	1.390 (2)	C8—H8B	0.990
S1···H4ii	2.990	H4···S1vi	2.990
C1···H8Aiii	2.866	H4···H2v	2.664
C2···H8Aiii	2.779	H5···H8Avii	2.763
C3···H8Aiii	2.903	H8A···C1viii	2.866
H2···H3iv	2.687	H8A···C2viii	2.779
H2···H4iv	2.664	H8A···C3viii	2.903
H3···H2v	2.687	H8A···H5vii	2.763
C7—S2—C8	104.35 (7)	C3—C2—H2	119.9
C2—C1—C6	119.24 (15)	C2—C3—H3	120.0
C2—C1—C7	119.06 (16)	C4—C3—H3	120.0
C6—C1—C7	121.67 (14)	C3—C4—H4	120.0
C1—C2—C3	120.25 (17)	C5—C4—H4	120.0
C2—C3—C4	120.03 (16)	C4—C5—H5	119.9
C3—C4—C5	120.03 (16)	C6—C5—H5	119.9
C4—C5—C6	120.22 (17)	C1—C6—H6	119.9
C1—C6—C5	120.22 (16)	C5—C6—H6	119.9
S1—C7—S2	124.57 (10)	S2—C8—H8A	109.1
S1—C7—C1	123.21 (11)	S2—C8—H8B	109.1
S2—C7—C1	112.18 (11)	C8i—C8—H8A	109.1
S2—C8—C8i	112.39 (16)	C8i—C8—H8B	109.1
C1—C2—H2	119.9	H8A—C8—H8B	107.9
C7—S2—C8—C8i	83.65 (14)	C6—C1—C7—S1	−152.1 (2)
C8—S2—C7—S1	0.8 (2)	C6—C1—C7—S2	30.0 (3)
C8—S2—C7—C1	178.65 (18)	C7—C1—C6—C5	−177.9 (2)
C2—C1—C6—C5	0.3 (3)	C1—C2—C3—C4	1.1 (3)
C6—C1—C2—C3	−1.0 (3)	C2—C3—C4—C5	−0.3 (3)
C2—C1—C7—S1	29.7 (3)	C3—C4—C5—C6	−0.4 (3)
C2—C1—C7—S2	−148.13 (18)	C4—C5—C6—C1	0.5 (3)
C7—C1—C2—C3	177.1 (2)

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

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cg1viii	0.99	2.65	3.451 (1)	138

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
C8—H8A⋯Cg1i	0.99	2.65	3.451 (1)	138

Symmetry code: (i) .