1,2-Bis(4-ethynylphen-yl)disulfane.

In the title compound, C(16)H(10)S(2), the S atoms are almost coplanar with the benzene rings to which they are bonded [deviations of 0.092 (1) and 0.022 (1) Å from their respective ring planes]. The benzene rings enclose a dihedral angle of 79.17 (3)°. An intra-molecular C-H⋯S hydrogen bond results in the formation of a five-membered ring. In the crystal structure, mol-ecules are stacked parallel to the a axis direction. π-π inter-actions between benzene rings are present, with a face-to-face stacking distance of 3.622 (10) Å.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For the synthetic procedure, see Yonezawa et al. (2008 ▶).

Experimental

Crystal data

C16H10S2

M = 266.36

Triclinic,

a = 5.981 (1) Å

b = 8.881 (2) Å

c = 13.269 (3) Å

α = 94.92 (3)°

β = 99.29 (3)°

γ = 104.45 (3)°

V = 667.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 293 K

0.40 × 0.40 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.864, T max = 0.896

2887 measured reflections

2620 independent reflections

1969 reflections with I > 2σ(I)

R int = 0.033

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.194

S = 1.01

2620 reflections

169 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, XQ. DOI: 10.1107/S1600536810004721/im2180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004721/im2180Isup2.hkl

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

C16H10S2	Z = 2
Mr = 266.36	F(000) = 276
Triclinic, P1	Dx = 1.325 Mg m−3
Hall symbol: -P 1	Melting point: 391 K
a = 5.981 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.881 (2) Å	Cell parameters from 25 reflections
c = 13.269 (3) Å	θ = 10–13°
α = 94.92 (3)°	µ = 0.38 mm−1
β = 99.29 (3)°	T = 293 K
γ = 104.45 (3)°	Block, colourless
V = 667.7 (2) Å3	0.40 × 0.40 × 0.30 mm

Enraf–Nonius CAD-4 diffractometer	1969 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 26.0°, θmin = 1.6°
ω/2θ scans	h = −7→7
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.864, Tmax = 0.896	l = 0→16
2887 measured reflections	3 standard reflections every 200 reflections
2620 independent reflections	intensity decay: none

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.060P)2 + 2.P] where P = (Fo2 + 2Fc2)/3
2620 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.50 e Å−3
2 restraints	Δρmin = −0.40 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
S1	0.0903 (2)	0.50232 (15)	0.20304 (9)	0.0594 (4)
C1	0.8307 (10)	0.2056 (7)	0.5708 (4)	0.0674 (13)
S2	−0.1535 (2)	0.31363 (17)	0.11850 (10)	0.0619 (4)
C2	0.7075 (8)	0.2523 (6)	0.5110 (4)	0.0561 (11)
C3	0.5594 (8)	0.3096 (5)	0.4359 (3)	0.0479 (10)
C4	0.3177 (9)	0.2406 (6)	0.4127 (4)	0.0606 (12)
H4A	0.2522	0.1573	0.4461	0.073*
C5	0.1745 (8)	0.2953 (6)	0.3402 (4)	0.0571 (11)
H5A	0.0137	0.2475	0.3242	0.069*
C6	0.2705 (8)	0.4209 (5)	0.2916 (3)	0.0476 (10)
C7	0.5073 (8)	0.4891 (6)	0.3143 (4)	0.0575 (11)
H7A	0.5722	0.5718	0.2803	0.069*
C8	0.6516 (8)	0.4362 (6)	0.3876 (4)	0.0578 (11)
H8A	0.8116	0.4863	0.4042	0.069*
C9	0.3291 (10)	0.0564 (7)	−0.3034 (4)	0.0686 (14)
C10	0.2502 (8)	0.0917 (6)	−0.2347 (4)	0.0561 (11)
C11	0.1571 (8)	0.1440 (5)	−0.1475 (3)	0.0503 (10)
C12	0.2959 (8)	0.2639 (5)	−0.0736 (3)	0.0522 (10)
H12A	0.4508	0.3089	−0.0791	0.063*
C13	0.2091 (8)	0.3179 (6)	0.0079 (4)	0.0567 (11)
H13A	0.3057	0.3986	0.0570	0.068*
C14	−0.0207 (8)	0.2532 (5)	0.0175 (3)	0.0490 (10)
C15	−0.1597 (8)	0.1311 (5)	−0.0558 (4)	0.0542 (11)
H15A	−0.3133	0.0845	−0.0493	0.065*
C16	−0.0744 (8)	0.0782 (6)	−0.1376 (3)	0.0542 (11)
H16A	−0.1714	−0.0022	−0.1869	0.065*
H9	0.385 (8)	0.019 (5)	−0.362 (2)	0.065*
H1	0.947 (6)	0.176 (6)	0.617 (3)	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0706 (8)	0.0593 (7)	0.0513 (7)	0.0280 (6)	0.0044 (5)	0.0062 (5)
C1	0.069 (3)	0.071 (3)	0.062 (3)	0.021 (3)	0.006 (3)	0.012 (3)
S2	0.0527 (7)	0.0807 (9)	0.0534 (7)	0.0229 (6)	0.0062 (5)	0.0069 (6)
C2	0.055 (3)	0.060 (3)	0.049 (3)	0.014 (2)	0.004 (2)	0.002 (2)
C3	0.051 (2)	0.055 (2)	0.042 (2)	0.023 (2)	0.0102 (18)	0.0059 (18)
C4	0.059 (3)	0.064 (3)	0.060 (3)	0.017 (2)	0.010 (2)	0.018 (2)
C5	0.044 (2)	0.062 (3)	0.059 (3)	0.011 (2)	0.001 (2)	0.006 (2)
C6	0.050 (2)	0.045 (2)	0.046 (2)	0.0144 (18)	0.0069 (18)	0.0012 (18)
C7	0.059 (3)	0.058 (3)	0.057 (3)	0.013 (2)	0.013 (2)	0.017 (2)
C8	0.047 (2)	0.063 (3)	0.057 (3)	0.006 (2)	0.004 (2)	0.010 (2)
C9	0.072 (3)	0.070 (3)	0.068 (3)	0.024 (3)	0.021 (3)	0.005 (3)
C10	0.059 (3)	0.056 (3)	0.053 (3)	0.017 (2)	0.004 (2)	0.009 (2)
C11	0.053 (3)	0.053 (2)	0.049 (2)	0.021 (2)	0.0062 (19)	0.0157 (19)
C12	0.046 (2)	0.058 (3)	0.050 (2)	0.014 (2)	0.0022 (19)	0.007 (2)
C13	0.043 (2)	0.067 (3)	0.053 (3)	0.010 (2)	−0.0027 (19)	0.005 (2)
C14	0.057 (3)	0.054 (2)	0.040 (2)	0.023 (2)	0.0075 (18)	0.0115 (18)
C15	0.040 (2)	0.060 (3)	0.057 (3)	0.010 (2)	−0.0013 (19)	0.010 (2)
C16	0.052 (3)	0.058 (3)	0.048 (2)	0.016 (2)	−0.0040 (19)	0.001 (2)

S1—C6	1.786 (4)	C8—H8A	0.9300
S1—S2	2.030 (2)	C9—C10	1.147 (7)
C1—C2	1.169 (7)	C9—H9	0.959 (10)
C1—H1	0.956 (10)	C10—C11	1.452 (7)
S2—C14	1.774 (4)	C11—C12	1.379 (6)
C2—C3	1.436 (6)	C11—C16	1.394 (6)
C3—C8	1.382 (6)	C12—C13	1.374 (6)
C3—C4	1.393 (6)	C12—H12A	0.9300
C4—C5	1.384 (6)	C13—C14	1.382 (6)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.383 (6)	C14—C15	1.386 (6)
C5—H5A	0.9300	C15—C16	1.368 (7)
C6—C7	1.366 (6)	C15—H15A	0.9300
C7—C8	1.386 (6)	C16—H16A	0.9300
C7—H7A	0.9300
C6—S1—S2	104.69 (15)	C7—C8—H8A	119.8
C2—C1—H1	173 (3)	C10—C9—H9	175 (3)
C14—S2—S1	105.55 (17)	C9—C10—C11	177.3 (6)
C1—C2—C3	178.8 (5)	C12—C11—C16	118.5 (4)
C8—C3—C4	118.7 (4)	C12—C11—C10	120.2 (4)
C8—C3—C2	121.0 (4)	C16—C11—C10	121.4 (4)
C4—C3—C2	120.3 (4)	C13—C12—C11	121.0 (4)
C5—C4—C3	120.4 (4)	C13—C12—H12A	119.5
C5—C4—H4A	119.8	C11—C12—H12A	119.5
C3—C4—H4A	119.8	C12—C13—C14	120.6 (4)
C6—C5—C4	120.0 (4)	C12—C13—H13A	119.7
C6—C5—H5A	120.0	C14—C13—H13A	119.7
C4—C5—H5A	120.0	C13—C14—C15	118.5 (4)
C7—C6—C5	119.7 (4)	C13—C14—S2	124.8 (4)
C7—C6—S1	118.7 (3)	C15—C14—S2	116.7 (4)
C5—C6—S1	121.5 (3)	C16—C15—C14	121.0 (4)
C6—C7—C8	120.6 (4)	C16—C15—H15A	119.5
C6—C7—H7A	119.7	C14—C15—H15A	119.5
C8—C7—H7A	119.7	C15—C16—C11	120.4 (4)
C3—C8—C7	120.5 (4)	C15—C16—H16A	119.8
C3—C8—H8A	119.8	C11—C16—H16A	119.8

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···S1	0.93	2.71	3.216 (5)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯S1	0.93	2.71	3.216 (5)	115