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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o916.
Published online 2010 March 24. doi:  10.1107/S1600536810010342
PMCID: PMC2983999

3,3′-Bithio­phene

Abstract

The title compound, C8H6S2, is disordered [occupancy ratio = 0.839 (2):0.161 (2)] and sits across a centre of symmetry. In the crystal, the mol­ecules are linked by a weak C—H(...)π inter­action.

Related literature

For a discussion of the disorder in this compound, see: Visser et al. (1968 [triangle]). For thio­phene C–S bond distances, see: Allen et al. (1987 [triangle]).

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Object name is e-66-0o916-scheme1.jpg

Experimental

Crystal data

  • C8H6S2
  • M r = 166.25
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o916-efi1.jpg
  • a = 7.5187 (7) Å
  • b = 18.2181 (17) Å
  • c = 5.5029 (5) Å
  • V = 753.77 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.62 mm−1
  • T = 150 K
  • 0.60 × 0.40 × 0.04 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.709, T max = 0.976
  • 11635 measured reflections
  • 1151 independent reflections
  • 987 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.101
  • S = 1.10
  • 1151 reflections
  • 59 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 0.48 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010342/om2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010342/om2327Isup2.hkl

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

Acknowledgments

LRG thanks the Fundação para o Ensino e Cultura Fernando Pessoa for support.

supplementary crystallographic information

Comment

The disorder in the title compound was discussed briefly by Visser et al. (1968). However, this paper gives no coordinates and the structure determination was at room temperature. This is a low temerature determination. A view of the major, 0.839 (2), site occupancy, and minor, 0.161 (2), site occupancy, components are shown in Fig. 1. There is a weak C–H···π interaction, C2–H2···Cg(thiophene) (0.5-x, y, z-0.5) in which H2···Cg is 2.86Å and C2···Cg is 3.6039 (17) Å. The angle at H2 ia 136° for the major component. The C2···Cg2 distance for the minor component is 3.607 (5) Å. The H2···Cg distance and angle at H2 are the same.

Experimental

The compound was obtained commercially and re-crystallised from dichloromethane.

Refinement

H atoms were treated as riding atoms with C—H(aromatic), 0.95Å. The S atom was disordered by rotation of 180° around the bond connecting the 2 thiophene rings. The C—S distances were restrained the average value quoted in Allen, et al., 1987 using tight restraints. Specifically, the C2-C5a and C4-C5 bonds were restrained in SHELXL97 refinements using DFIX 1.380 0.001 and the C5-S1, C2-S1, C4-S1A and C5A-S1A bonds were restrained using DFIX 1.72 0.001. The anisotropic thermal parameters for atom C5A (minor component) were constrained to be the same as those those of atom C5 (major component) using the EADP instruction.

Figures

Fig. 1.
A view of the title compound with our numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The molecule sits across the centre-of-symmetry at (0.5,0.5,0.5). The bonds in the minor component are marked as dotted lines.

Crystal data

C8H6S2Dx = 1.465 Mg m3
Mr = 166.25Melting point: 406 K
Orthorhombic, PccnMo Kα radiation, λ = 0.71073 Å
a = 7.5187 (7) ÅCell parameters from 124 reflections
b = 18.2181 (17) Åθ = 2.8–30.5°
c = 5.5029 (5) ŵ = 0.62 mm1
V = 753.77 (12) Å3T = 150 K
Z = 4Plate, yellow
F(000) = 3440.60 × 0.40 × 0.04 mm

Data collection

Bruker SMART APEXII diffractometer1151 independent reflections
Radiation source: fine-focus sealed tube987 reflections with I > 2σ(I)
graphiteRint = 0.039
ω scansθmax = 30.6°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −10→10
Tmin = 0.709, Tmax = 0.976k = −23→26
11635 measured reflectionsl = −7→7

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.0478P)2 + 0.3736P] where P = (Fo2 + 2Fc2)/3
1151 reflections(Δ/σ)max = 0.001
59 parametersΔρmax = 0.48 e Å3
6 restraintsΔρmin = −0.33 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
S10.44974 (10)0.67774 (2)0.55925 (11)0.03155 (18)0.839 (2)
C5A0.446 (2)0.6612 (2)0.5331 (18)0.0246 (5)0.161 (2)
H5A0.40030.70610.47180.030*0.161 (2)
C20.4207 (2)0.59508 (6)0.4154 (2)0.0255 (3)
H20.35740.58910.26730.031*
C30.50025 (17)0.53842 (7)0.5407 (2)0.0199 (3)
C40.58337 (19)0.56308 (7)0.7572 (3)0.0262 (3)
H40.64390.53140.86660.031*
C50.5674 (8)0.63775 (10)0.7926 (7)0.0246 (5)0.839 (2)
H50.61500.66360.92770.030*0.839 (2)
S1A0.5658 (13)0.65626 (13)0.7988 (13)0.0391 (12)0.161 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0353 (3)0.0217 (2)0.0377 (3)0.0028 (2)0.0068 (2)0.00256 (18)
C5A0.0243 (10)0.0215 (10)0.0279 (10)−0.0028 (13)0.0000 (8)−0.0033 (10)
C20.0264 (7)0.0274 (6)0.0227 (6)0.0032 (5)0.0010 (5)0.0039 (5)
C30.0152 (6)0.0247 (6)0.0198 (6)0.0022 (5)0.0025 (5)0.0022 (5)
C40.0234 (7)0.0303 (7)0.0249 (6)0.0026 (5)−0.0034 (5)−0.0015 (5)
C50.0243 (10)0.0215 (10)0.0279 (10)−0.0028 (13)0.0000 (8)−0.0033 (10)
S1A0.040 (2)0.0276 (17)0.049 (2)−0.001 (2)0.0038 (15)−0.0074 (17)

Geometric parameters (Å, °)

S1—C21.7152 (9)C3—C41.4181 (19)
S1—C51.7215 (10)C3—C3i1.470 (3)
C5A—C21.3802 (10)C4—C51.3794 (10)
C5A—S1A1.7203 (10)C4—S1A1.7180 (10)
C5A—H5A0.9500C4—H40.9500
C2—C31.3778 (19)C5—H50.9500
C2—H20.9500
C2—S1—C592.19 (8)C4—C3—C3i123.98 (15)
C2—C5A—S1A115.2 (3)C5—C4—C3113.15 (13)
C2—C5A—H5A122.4C3—C4—S1A113.04 (17)
S1A—C5A—H5A122.4C5—C4—H4123.4
C3—C2—C5A111.1 (2)C3—C4—H4123.4
C3—C2—S1111.81 (10)S1A—C4—H4123.5
C3—C2—H2124.1C4—C5—S1110.87 (12)
C5A—C2—H2124.9C4—C5—H5124.6
S1—C2—H2124.1S1—C5—H5124.6
C2—C3—C4111.98 (11)C4—S1A—C5A88.8 (2)
C2—C3—C3i124.05 (15)
S1A—C5A—C2—C3−0.2 (15)C3i—C3—C4—C5179.3 (3)
C5—S1—C2—C3−0.6 (3)C2—C3—C4—S1A−1.3 (5)
C5A—C2—C3—C41.0 (8)C3i—C3—C4—S1A178.5 (4)
S1—C2—C3—C40.73 (16)C3—C4—C5—S10.1 (5)
C5A—C2—C3—C3i−178.8 (8)C2—S1—C5—C40.3 (4)
S1—C2—C3—C3i−179.03 (14)C3—C4—S1A—C5A1.0 (10)
C2—C3—C4—C5−0.5 (3)C2—C5A—S1A—C4−0.4 (14)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

Cg and Cg' are the centroids of the thiophene ring in the major and minor occupancy disorder components, respectively.
D—H···AD—HH···AD···AD—H···A
C2—H2···Cgii0.952.863.6039 (17)136
C2—H2···Cg'ii0.952.863.607 (5)136

Symmetry codes: (ii) −x+1/2, y, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2327).

References

  • 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.
  • Bruker (2004). APEXII, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Johnson, C. K. (1976). ORTEPII Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Visser, G. J., Heeres, G. J., Wolters, J. & Vos, A. (1968). Acta Cryst. B24, 467–473.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography