organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1,2-Bis(4-ethynylphen­yl)disulfane

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: zhuhjnjut@hotmail.com

(Received 24 January 2010; accepted 6 February 2010; online 13 February 2010)

In the title compound, C16H10S2, 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 intra­molecular C—H⋯S hydrogen bond results in the formation of a five-membered ring. In the crystal structure, mol­ecules are stacked parallel to the a axis direction. ππ inter­actions 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[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the synthetic procedure, see Yonezawa et al. (2008[Yonezawa, T., Uchida, K., Yamanoi, Y., Horinouchi, S., Terasaki, N. & Nishihara, H. (2008). Phys. Chem. Chem. Phys. 10, 6925-6927.]).

[Scheme 1]

Experimental

Crystal data
  • C16H10S2

  • Mr = 266.36

  • Triclinic, [P \overline 1]

  • 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[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.864, Tmax = 0.896

  • 2887 measured reflections

  • 2620 independent reflections

  • 1969 reflections with I > 2σ(I)

  • Rint = 0.033

  • 3 standard reflections every 200 reflections intensity decay: none

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: CAD-4 Software (Enraf–Nonius, 1985[Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, (I), is a kind of aromatic acetylide organic intermediate which can be used for many fields such as molecular electronic materials, organometallic chemistry etc. (Yonezawa et al., 2008). We herein report its crystal structure.

In the molecule of (I), (Fig.1), the bond lengths and angles are within normal ranges (Allen et al., 1987). S atoms are situated in the same plane as the benzene rings they are bonded to. Rings A (C3—C8) and B (C11—C16) are, of course, planar and they enclose a dihedral angle of 79.17 (3) °. An intramolecular C—H···S hydrogen bond (Table 1) results in the formation of a five-membered ring C (S1/S2/C14/C13/H13A). The distance between atoms S2 and H5A is 2.91 Å, which is significantly longer than the hydrogen bond between atoms S1 and H13A.

As can be seen from the packing diagram, (Fig. 2), the molecules are stacked along the a axis. There are also the π-π interactions of benzene rings with a face-to-face stacking distance of 3.622 Å.

Related literature top

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

Experimental top

The title compound, (I) was prepared by a literature method (Yonezawa et al., 2008). Crystals suitable for X-ray analysis were obtained by dissolving (I) (0.5 g) in hexane (20 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H and 0.95 Å for acetylide H. In the refinement all hydrogens were constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), with x = 1.2 for aromatic H, and x = 1.5 for other H.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of (I). Hydrogen bonds are shown as dashed lines.
1,2-bis(4-ethynylphenyl)disulfane top
Crystal data top
C16H10S2Z = 2
Mr = 266.36F(000) = 276
Triclinic, P1Dx = 1.325 Mg m3
Hall symbol: -P 1Melting point: 391 K
a = 5.981 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.881 (2) ÅCell parameters from 25 reflections
c = 13.269 (3) Åθ = 10–13°
α = 94.92 (3)°µ = 0.38 mm1
β = 99.29 (3)°T = 293 K
γ = 104.45 (3)°Block, colourless
V = 667.7 (2) Å30.40 × 0.40 × 0.30 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1969 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
Graphite monochromatorθmax = 26.0°, θmin = 1.6°
ω/2θ scansh = 77
Absorption correction: ψ scan
(North et al., 1968)
k = 1010
Tmin = 0.864, Tmax = 0.896l = 016
2887 measured reflections3 standard reflections every 200 reflections
2620 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H 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 parametersΔρmax = 0.50 e Å3
2 restraintsΔρmin = 0.40 e Å3
Crystal data top
C16H10S2γ = 104.45 (3)°
Mr = 266.36V = 667.7 (2) Å3
Triclinic, P1Z = 2
a = 5.981 (1) ÅMo Kα radiation
b = 8.881 (2) ŵ = 0.38 mm1
c = 13.269 (3) ÅT = 293 K
α = 94.92 (3)°0.40 × 0.40 × 0.30 mm
β = 99.29 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1969 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.033
Tmin = 0.864, Tmax = 0.8963 standard reflections every 200 reflections
2887 measured reflections intensity decay: none
2620 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0602 restraints
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.50 e Å3
2620 reflectionsΔρmin = 0.40 e Å3
169 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.0903 (2)0.50232 (15)0.20304 (9)0.0594 (4)
C10.8307 (10)0.2056 (7)0.5708 (4)0.0674 (13)
S20.1535 (2)0.31363 (17)0.11850 (10)0.0619 (4)
C20.7075 (8)0.2523 (6)0.5110 (4)0.0561 (11)
C30.5594 (8)0.3096 (5)0.4359 (3)0.0479 (10)
C40.3177 (9)0.2406 (6)0.4127 (4)0.0606 (12)
H4A0.25220.15730.44610.073*
C50.1745 (8)0.2953 (6)0.3402 (4)0.0571 (11)
H5A0.01370.24750.32420.069*
C60.2705 (8)0.4209 (5)0.2916 (3)0.0476 (10)
C70.5073 (8)0.4891 (6)0.3143 (4)0.0575 (11)
H7A0.57220.57180.28030.069*
C80.6516 (8)0.4362 (6)0.3876 (4)0.0578 (11)
H8A0.81160.48630.40420.069*
C90.3291 (10)0.0564 (7)0.3034 (4)0.0686 (14)
C100.2502 (8)0.0917 (6)0.2347 (4)0.0561 (11)
C110.1571 (8)0.1440 (5)0.1475 (3)0.0503 (10)
C120.2959 (8)0.2639 (5)0.0736 (3)0.0522 (10)
H12A0.45080.30890.07910.063*
C130.2091 (8)0.3179 (6)0.0079 (4)0.0567 (11)
H13A0.30570.39860.05700.068*
C140.0207 (8)0.2532 (5)0.0175 (3)0.0490 (10)
C150.1597 (8)0.1311 (5)0.0558 (4)0.0542 (11)
H15A0.31330.08450.04930.065*
C160.0744 (8)0.0782 (6)0.1376 (3)0.0542 (11)
H16A0.17140.00220.18690.065*
H90.385 (8)0.019 (5)0.362 (2)0.065*
H10.947 (6)0.176 (6)0.617 (3)0.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0706 (8)0.0593 (7)0.0513 (7)0.0280 (6)0.0044 (5)0.0062 (5)
C10.069 (3)0.071 (3)0.062 (3)0.021 (3)0.006 (3)0.012 (3)
S20.0527 (7)0.0807 (9)0.0534 (7)0.0229 (6)0.0062 (5)0.0069 (6)
C20.055 (3)0.060 (3)0.049 (3)0.014 (2)0.004 (2)0.002 (2)
C30.051 (2)0.055 (2)0.042 (2)0.023 (2)0.0102 (18)0.0059 (18)
C40.059 (3)0.064 (3)0.060 (3)0.017 (2)0.010 (2)0.018 (2)
C50.044 (2)0.062 (3)0.059 (3)0.011 (2)0.001 (2)0.006 (2)
C60.050 (2)0.045 (2)0.046 (2)0.0144 (18)0.0069 (18)0.0012 (18)
C70.059 (3)0.058 (3)0.057 (3)0.013 (2)0.013 (2)0.017 (2)
C80.047 (2)0.063 (3)0.057 (3)0.006 (2)0.004 (2)0.010 (2)
C90.072 (3)0.070 (3)0.068 (3)0.024 (3)0.021 (3)0.005 (3)
C100.059 (3)0.056 (3)0.053 (3)0.017 (2)0.004 (2)0.009 (2)
C110.053 (3)0.053 (2)0.049 (2)0.021 (2)0.0062 (19)0.0157 (19)
C120.046 (2)0.058 (3)0.050 (2)0.014 (2)0.0022 (19)0.007 (2)
C130.043 (2)0.067 (3)0.053 (3)0.010 (2)0.0027 (19)0.005 (2)
C140.057 (3)0.054 (2)0.040 (2)0.023 (2)0.0075 (18)0.0115 (18)
C150.040 (2)0.060 (3)0.057 (3)0.010 (2)0.0013 (19)0.010 (2)
C160.052 (3)0.058 (3)0.048 (2)0.016 (2)0.0040 (19)0.001 (2)
Geometric parameters (Å, º) top
S1—C61.786 (4)C8—H8A0.9300
S1—S22.030 (2)C9—C101.147 (7)
C1—C21.169 (7)C9—H90.959 (10)
C1—H10.956 (10)C10—C111.452 (7)
S2—C141.774 (4)C11—C121.379 (6)
C2—C31.436 (6)C11—C161.394 (6)
C3—C81.382 (6)C12—C131.374 (6)
C3—C41.393 (6)C12—H12A0.9300
C4—C51.384 (6)C13—C141.382 (6)
C4—H4A0.9300C13—H13A0.9300
C5—C61.383 (6)C14—C151.386 (6)
C5—H5A0.9300C15—C161.368 (7)
C6—C71.366 (6)C15—H15A0.9300
C7—C81.386 (6)C16—H16A0.9300
C7—H7A0.9300
C6—S1—S2104.69 (15)C7—C8—H8A119.8
C2—C1—H1173 (3)C10—C9—H9175 (3)
C14—S2—S1105.55 (17)C9—C10—C11177.3 (6)
C1—C2—C3178.8 (5)C12—C11—C16118.5 (4)
C8—C3—C4118.7 (4)C12—C11—C10120.2 (4)
C8—C3—C2121.0 (4)C16—C11—C10121.4 (4)
C4—C3—C2120.3 (4)C13—C12—C11121.0 (4)
C5—C4—C3120.4 (4)C13—C12—H12A119.5
C5—C4—H4A119.8C11—C12—H12A119.5
C3—C4—H4A119.8C12—C13—C14120.6 (4)
C6—C5—C4120.0 (4)C12—C13—H13A119.7
C6—C5—H5A120.0C14—C13—H13A119.7
C4—C5—H5A120.0C13—C14—C15118.5 (4)
C7—C6—C5119.7 (4)C13—C14—S2124.8 (4)
C7—C6—S1118.7 (3)C15—C14—S2116.7 (4)
C5—C6—S1121.5 (3)C16—C15—C14121.0 (4)
C6—C7—C8120.6 (4)C16—C15—H15A119.5
C6—C7—H7A119.7C14—C15—H15A119.5
C8—C7—H7A119.7C15—C16—C11120.4 (4)
C3—C8—C7120.5 (4)C15—C16—H16A119.8
C3—C8—H8A119.8C11—C16—H16A119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···S10.932.713.216 (5)115

Experimental details

Crystal data
Chemical formulaC16H10S2
Mr266.36
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.981 (1), 8.881 (2), 13.269 (3)
α, β, γ (°)94.92 (3), 99.29 (3), 104.45 (3)
V3)667.7 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.38
Crystal size (mm)0.40 × 0.40 × 0.30
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.864, 0.896
No. of measured, independent and
observed [I > 2σ(I)] reflections
2887, 2620, 1969
Rint0.033
(sin θ/λ)max1)0.616
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.194, 1.01
No. of reflections2620
No. of parameters169
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.50, 0.40

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···S10.93002.71003.216 (5)115.00
 

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationEnraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYonezawa, T., Uchida, K., Yamanoi, Y., Horinouchi, S., Terasaki, N. & Nishihara, H. (2008). Phys. Chem. Chem. Phys. 10, 6925–6927.  Web of Science CrossRef PubMed CAS Google Scholar

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