Acta Cryst. (2010). E66, o916 [ doi:10.1107/S1600536810010342 ]
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
![[pi]](/logos/entities/pi_rmgif.gif)
interaction.
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.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./om2327fig1thm.gif)
| 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. |
| C8H6S2 | Dx = 1.465 Mg m−3 |
| Mr = 166.25 | Melting point: 406 K |
| Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.5187 (7) Å | Cell parameters from 124 reflections |
| b = 18.2181 (17) Å | θ = 2.8–30.5° |
| c = 5.5029 (5) Å | µ = 0.62 mm−1 |
| V = 753.77 (12) Å3 | T = 150 K |
| Z = 4 | Plate, yellow |
| F(000) = 344 | 0.60 × 0.40 × 0.04 mm |
| Bruker SMART APEXII diffractometer | 1151 independent reflections |
| Radiation source: fine-focus sealed tube | 987 reflections with I > 2σ(I) |
| graphite | Rint = 0.039 |
| ω scans | θmax = 30.6°, θmin = 4.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→10 |
| Tmin = 0.709, Tmax = 0.976 | k = −23→26 |
| 11635 measured reflections | l = −7→7 |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.101 | H-atom parameters constrained |
| S = 1.10 | w = 1/[σ2(Fo2) + (0.0478P)2 + 0.3736P] where P = (Fo2 + 2Fc2)/3 |
| 1151 reflections | (Δ/σ)max = 0.001 |
| 59 parameters | Δρmax = 0.48 e Å−3 |
| 6 restraints | Δρmin = −0.33 e Å−3 |
| C8H6S2 | V = 753.77 (12) Å3 |
| Mr = 166.25 | Z = 4 |
| Orthorhombic, Pccn | Mo Kα radiation |
| a = 7.5187 (7) Å | µ = 0.62 mm−1 |
| b = 18.2181 (17) Å | T = 150 K |
| c = 5.5029 (5) Å | 0.60 × 0.40 × 0.04 mm |
| Bruker SMART APEXII diffractometer | 1151 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | 987 reflections with I > 2σ(I) |
| Tmin = 0.709, Tmax = 0.976 | Rint = 0.039 |
| 11635 measured reflections | θmax = 30.6° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.101 | Δρmax = 0.48 e Å−3 |
| S = 1.10 | Δρmin = −0.33 e Å−3 |
| 1151 reflections | Absolute structure: ? |
| 59 parameters | Flack parameter: ? |
| 6 restraints | Rogers parameter: ? |
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 | Occ. (<1) | |
| S1 | 0.44974 (10) | 0.67774 (2) | 0.55925 (11) | 0.03155 (18) | 0.839 (2) |
| C5A | 0.446 (2) | 0.6612 (2) | 0.5331 (18) | 0.0246 (5) | 0.161 (2) |
| H5A | 0.4003 | 0.7061 | 0.4718 | 0.030* | 0.161 (2) |
| C2 | 0.4207 (2) | 0.59508 (6) | 0.4154 (2) | 0.0255 (3) | |
| H2 | 0.3574 | 0.5891 | 0.2673 | 0.031* | |
| C3 | 0.50025 (17) | 0.53842 (7) | 0.5407 (2) | 0.0199 (3) | |
| C4 | 0.58337 (19) | 0.56308 (7) | 0.7572 (3) | 0.0262 (3) | |
| H4 | 0.6439 | 0.5314 | 0.8666 | 0.031* | |
| C5 | 0.5674 (8) | 0.63775 (10) | 0.7926 (7) | 0.0246 (5) | 0.839 (2) |
| H5 | 0.6150 | 0.6636 | 0.9277 | 0.030* | 0.839 (2) |
| S1A | 0.5658 (13) | 0.65626 (13) | 0.7988 (13) | 0.0391 (12) | 0.161 (2) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0353 (3) | 0.0217 (2) | 0.0377 (3) | 0.0028 (2) | 0.0068 (2) | 0.00256 (18) |
| C5A | 0.0243 (10) | 0.0215 (10) | 0.0279 (10) | −0.0028 (13) | 0.0000 (8) | −0.0033 (10) |
| C2 | 0.0264 (7) | 0.0274 (6) | 0.0227 (6) | 0.0032 (5) | 0.0010 (5) | 0.0039 (5) |
| C3 | 0.0152 (6) | 0.0247 (6) | 0.0198 (6) | 0.0022 (5) | 0.0025 (5) | 0.0022 (5) |
| C4 | 0.0234 (7) | 0.0303 (7) | 0.0249 (6) | 0.0026 (5) | −0.0034 (5) | −0.0015 (5) |
| C5 | 0.0243 (10) | 0.0215 (10) | 0.0279 (10) | −0.0028 (13) | 0.0000 (8) | −0.0033 (10) |
| S1A | 0.040 (2) | 0.0276 (17) | 0.049 (2) | −0.001 (2) | 0.0038 (15) | −0.0074 (17) |
| S1—C2 | 1.7152 (9) | C3—C4 | 1.4181 (19) |
| S1—C5 | 1.7215 (10) | C3—C3i | 1.470 (3) |
| C5A—C2 | 1.3802 (10) | C4—C5 | 1.3794 (10) |
| C5A—S1A | 1.7203 (10) | C4—S1A | 1.7180 (10) |
| C5A—H5A | 0.9500 | C4—H4 | 0.9500 |
| C2—C3 | 1.3778 (19) | C5—H5 | 0.9500 |
| C2—H2 | 0.9500 | ||
| C2—S1—C5 | 92.19 (8) | C4—C3—C3i | 123.98 (15) |
| C2—C5A—S1A | 115.2 (3) | C5—C4—C3 | 113.15 (13) |
| C2—C5A—H5A | 122.4 | C3—C4—S1A | 113.04 (17) |
| S1A—C5A—H5A | 122.4 | C5—C4—H4 | 123.4 |
| C3—C2—C5A | 111.1 (2) | C3—C4—H4 | 123.4 |
| C3—C2—S1 | 111.81 (10) | S1A—C4—H4 | 123.5 |
| C3—C2—H2 | 124.1 | C4—C5—S1 | 110.87 (12) |
| C5A—C2—H2 | 124.9 | C4—C5—H5 | 124.6 |
| S1—C2—H2 | 124.1 | S1—C5—H5 | 124.6 |
| C2—C3—C4 | 111.98 (11) | C4—S1A—C5A | 88.8 (2) |
| C2—C3—C3i | 124.05 (15) | ||
| S1A—C5A—C2—C3 | −0.2 (15) | C3i—C3—C4—C5 | 179.3 (3) |
| C5—S1—C2—C3 | −0.6 (3) | C2—C3—C4—S1A | −1.3 (5) |
| C5A—C2—C3—C4 | 1.0 (8) | C3i—C3—C4—S1A | 178.5 (4) |
| S1—C2—C3—C4 | 0.73 (16) | C3—C4—C5—S1 | 0.1 (5) |
| C5A—C2—C3—C3i | −178.8 (8) | C2—S1—C5—C4 | 0.3 (4) |
| S1—C2—C3—C3i | −179.03 (14) | C3—C4—S1A—C5A | 1.0 (10) |
| C2—C3—C4—C5 | −0.5 (3) | C2—C5A—S1A—C4 | −0.4 (14) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
| Cg and Cg' are the centroids of the thiophene ring in the major and minor occupancy disorder components, respectively. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···Cgii | 0.95 | 2.86 | 3.6039 (17) | 136 |
| C2—H2···Cg'ii | 0.95 | 2.86 | 3.607 (5) | 136 |
| Symmetry codes: (ii) −x+1/2, y, z−1/2. |
| Cg and Cg' are the centroids of the thiophene ring in the major and minor occupancy disorder components, respectively. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C2—H2···Cgi | 0.95 | 2.86 | 3.6039 (17) | 136 |
| C2—H2···Cg'i | 0.95 | 2.86 | 3.607 (5) | 136 |
| Symmetry codes: (i) −x+1/2, y, z−1/2. |
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.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
Visser, G. J., Heeres, G. J., Wolters, J. & Vos, A. (1968). Acta Cryst. B24, 467–473.
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.