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access2-(9H-Fluoren-9-ylidenemethyl)thiophene
aInstitute of Physical Chemistry and Chemical Physics, Slovak University of Technology, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and bInstitute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical Technology, Slovak Technical University, Radlinskeho 9, Bratislava 81237, Slovak Republic
*Correspondence e-mail: lucia.perasinova@stuba.sk
The title compound, C18H12S, contains a thiophene ring which is disordered by rotation of 180° about the linking C—C bond. The site occupancies of the major and minor components of the disordered ring are 0.900 (3) and 0.100 (3), respectively. In one of these disordered components, the molecule is stabilized by an intramolecular C—H⋯S hydrogen bond. The compound was synthesized in good yield (80%) by a modified phase-transfer-catalysed condensation of fluorene with thiophene-2-carbaldehyde.
Related literature
For a related structure, see: Fave et al., 2004![[Fave, C., Hissler, M., Karpati, T., Rault-Berthelot, J., Deborde, V., Toupet, L., Nyulaszi, L. & Reau, R. (2004). J. Am. Chem. Soc. 126, 6058-6059.]](../../../../../../logos/arrows/e_arr.gif "Fave, C., Hissler, M., Karpati, T., Rault-Berthelot, J., Deborde, V., Toupet, L., Nyulaszi, L. & Reau, R. (2004). J. Am. Chem. Soc. 126, 6058-6059.")
. For related literature, see: Allen (2002); Lukeš et al. (2003); Mullen & Wegner (1998).
![[Scheme 1]](fj2086scheme1.gif)
Experimental
Crystal data
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Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004).
Supporting information
contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807065099/fj2086sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065099/fj2086Isup2.hkl
8.3 g (0.05 mol) of fluorene and 5.6 g (0.05 mol) of thiophene-2-carbaldehyde were dissolved in 70 ml of toluene. Then 70 ml 40% NaOH and 2.9 g (0.009 mol) (n-Bu)4N+Br- were added. The resulting heterogenous mixture was vigorously stirred at room temperature for 12 h. After completion of the reaction (TLC control), the water layer was separated, and the organic layer was washed with 100 ml 10% HCl, 300 ml water, 300 ml of brine and dried over Na2SO4. After evaporation of the solvent under reduced pressure, a dark oil was obtained, which was further dissolved in boiling MeOH, decolorized with Norit, filtered and left to cool to room temperature to obtain 10.4 g (80%) of yellow needles m.p.: 75°C (lit. 73–75°C) (Lukeš et al., 2003). The crude product could be purified by using silica gel Merck 60 in toluene as an Rf = 0.71 (toluene).
1H NMR (300 MHz, CDCl3 p.p.m.): δ = 8.11 (d, J=7.79 Hz, 1 H), 7.68 – 7.74 (m, 3 H), 7.60 (s, 1 H), 7.42 – 7.45 (m, 2 H), 7.27 – 7.38 (m, 3 H), 7.12 – 7.23 (m, 2 H).
13C-NMR (75 MHz, CDCl3, p.p.m.) δ = 141.19, 139.48, 139.06, 138.91, 136.51, 136.12, 129.25, 128.72, 128.22, 127.57, 127.32, 126.97, 126.82, 124.34, 120.14, 119.74, 119.58, 118.98.
H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.95 Å and Uiso(H) = 1.2 Ueq(C).
Our synthetic efforts have been focused on a set of multi-ring monomer systems based on thiophene and fluorene ring system. In this respect, the relationship between the charge transport properties in OFET devices (Mullen & Wegner, 1998) and molecular properties such as redox reversibility and have been investigated. As active layers, we used oligomers based on molecules consisting of alternating thiophene and fluorene moieties.
In the title compound (1) the S1—C15 and S1—C18 bond lengths of 1.725 (3) Å and 1.692 (3) Å are in a quite good agreement with similar thiophene compounds in the Cambridge Structural Database (CSD; Version 5.27, 2006 release; Allen, 2002); for example, 2,2',5,5'-tetrakis(2-Thienyl)-3,4:3',4'- bis(tetramethylene)-1,1'-biphosphole (Fave et. al., 2004; CDS refcode BERCIL). The thiophene ring is disordered by rotation about the inter-ring C—C bond. There is one intramolecular C–H···S hydrogen bond.
For a related structure, see: Fave et al., 2004.
For related literature, see: Allen (2002); Lukeš et al. (2003); Mullen & Wegner (1998).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004).
![[Figure 1]](./fj2086fig1thm.gif) | Fig. 1. The atomic numbering scheme of 2-(9H-fluoren-9-ylidenemethyl)thiophene. Only the major component of the disordered thiophene ring is shown. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen-bond interactions are indicated by dashed lines. |
| C18H12S | F(000) = 2176 |
| Mr = 260.34 | Dx = 1.333 Mg m−3 |
| Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: F 2 -2d | Cell parameters from 4617 reflections |
| a = 20.757 (4) Å | θ = 3.7–29.1° |
| b = 44.434 (9) Å | µ = 0.23 mm−1 |
| c = 5.6260 (11) Å | T = 100 K |
| V = 5189.0 (18) Å3 | Block, yellow |
| Z = 16 | 0.57 × 0.13 × 0.08 mm |
| Oxford Diffraction Gemini R CCD diffractometer | 3018 independent reflections |
| Radiation source: fine-focus sealed tube | 1903 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.029 |
| Rotation method data acquisition using ω and φ scans | θmax = 29.1°, θmin = 3.8° |
| Absorption correction: analytical (Clark & Reid, 1995) | h = −27→25 |
| Tmin = 0.938, Tmax = 0.985 | k = −59→58 |
| 11725 measured reflections | l = −7→7 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0485P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.99 | (Δ/σ)max < 0.001 |
| 3018 reflections | Δρmax = 0.15 e Å−3 |
| 180 parameters | Δρmin = −0.17 e Å−3 |
| 4 restraints | Absolute structure: Flack (1983), 1110 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.07 (8) |
| C18H12S | V = 5189.0 (18) Å3 |
| Mr = 260.34 | Z = 16 |
| Orthorhombic, Fdd2 | Mo Kα radiation |
| a = 20.757 (4) Å | µ = 0.23 mm−1 |
| b = 44.434 (9) Å | T = 100 K |
| c = 5.6260 (11) Å | 0.57 × 0.13 × 0.08 mm |
| Oxford Diffraction Gemini R CCD diffractometer | 3018 independent reflections |
| Absorption correction: analytical (Clark & Reid, 1995) | 1903 reflections with I > 2σ(I) |
| Tmin = 0.938, Tmax = 0.985 | Rint = 0.029 |
| 11725 measured reflections |
| R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
| wR(F2) = 0.090 | Δρmax = 0.15 e Å−3 |
| S = 0.99 | Δρmin = −0.17 e Å−3 |
| 3018 reflections | Absolute structure: Flack (1983), 1110 Friedel pairs |
| 180 parameters | Absolute structure parameter: −0.07 (8) |
| 4 restraints |
Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006) |
Geometry. All e.s.d.'s (except the 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 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) | |
| C1 | 0.35040 (9) | 0.03543 (4) | −0.1480 (3) | 0.0504 (5) | |
| C2 | 0.40287 (10) | 0.01668 (4) | −0.1107 (4) | 0.0605 (6) | |
| H2A | 0.4298 | 0.0194 | 0.0241 | 0.073* | |
| C3 | 0.41552 (10) | −0.00616 (5) | −0.2727 (4) | 0.0656 (6) | |
| H3A | 0.4516 | −0.0189 | −0.2475 | 0.079* | |
| C4 | 0.37726 (11) | −0.01069 (5) | −0.4680 (4) | 0.0640 (6) | |
| H4A | 0.3876 | −0.0262 | −0.5781 | 0.077* | |
| C5 | 0.32362 (10) | 0.00724 (4) | −0.5052 (4) | 0.0594 (5) | |
| H5A | 0.2965 | 0.0040 | −0.6387 | 0.071* | |
| C6 | 0.31044 (9) | 0.02985 (4) | −0.3442 (3) | 0.0490 (5) | |
| C7 | 0.25624 (9) | 0.05093 (4) | −0.3394 (3) | 0.0493 (5) | |
| C8 | 0.20399 (10) | 0.05396 (5) | −0.4884 (4) | 0.0607 (5) | |
| H8A | 0.1994 | 0.0413 | −0.6237 | 0.073* | |
| C9 | 0.15827 (11) | 0.07574 (5) | −0.4373 (4) | 0.0670 (6) | |
| H9A | 0.1219 | 0.0780 | −0.5380 | 0.080* | |
| C10 | 0.16522 (10) | 0.09415 (5) | −0.2405 (4) | 0.0658 (6) | |
| H10A | 0.1334 | 0.1090 | −0.2079 | 0.079* | |
| C11 | 0.21746 (10) | 0.09134 (5) | −0.0913 (4) | 0.0608 (5) | |
| H11A | 0.2221 | 0.1043 | 0.0419 | 0.073* | |
| C12 | 0.26339 (9) | 0.06932 (4) | −0.1380 (3) | 0.0490 (5) | |
| C13 | 0.32372 (9) | 0.06148 (4) | −0.0145 (3) | 0.0490 (5) | |
| C14 | 0.34399 (9) | 0.07789 (4) | 0.1761 (3) | 0.0518 (5) | |
| H14A | 0.3125 | 0.0921 | 0.2256 | 0.062* | |
| C15A | 0.40114 (9) | 0.07913 (4) | 0.3214 (3) | 0.0513 (5) | 0.900 (3) |
| C18A | 0.50774 (12) | 0.07874 (5) | 0.5125 (5) | 0.0731 (7) | 0.900 (3) |
| H18A | 0.5513 | 0.0759 | 0.5592 | 0.088* | 0.900 (3) |
| C17A | 0.46607 (12) | 0.09565 (5) | 0.6332 (4) | 0.0670 (6) | 0.900 (3) |
| H17A | 0.4767 | 0.1058 | 0.7767 | 0.080* | 0.900 (3) |
| C16A | 0.4056 (4) | 0.0970 (4) | 0.529 (3) | 0.0747 (14) | 0.900 (3) |
| H16A | 0.3710 | 0.1087 | 0.5900 | 0.090* | 0.900 (3) |
| S1A | 0.47511 (8) | 0.06280 (3) | 0.26734 (16) | 0.0755 (3) | 0.900 (3) |
| C15B | 0.40114 (9) | 0.07913 (4) | 0.3214 (3) | 0.0513 (5) | 0.100 (3) |
| C17B | 0.46607 (12) | 0.09565 (5) | 0.6332 (4) | 0.0670 (6) | 0.100 (3) |
| H17B | 0.4781 | 0.1058 | 0.7750 | 0.080* | 0.100 (3) |
| C18B | 0.50774 (12) | 0.07874 (5) | 0.5125 (5) | 0.0731 (7) | 0.100 (3) |
| H18B | 0.5512 | 0.0758 | 0.5602 | 0.088* | 0.100 (3) |
| C16B | 0.481 (3) | 0.0659 (10) | 0.311 (4) | 0.0755 (3) | 0.100 (3) |
| H16B | 0.5013 | 0.0532 | 0.1960 | 0.091* | 0.100 (3) |
| S1B | 0.3980 (11) | 0.0978 (10) | 0.532 (7) | 0.0747 (14) | 0.100 (3) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0532 (11) | 0.0451 (11) | 0.0528 (11) | −0.0072 (9) | 0.0047 (9) | −0.0017 (9) |
| C2 | 0.0557 (12) | 0.0503 (12) | 0.0754 (13) | −0.0021 (10) | −0.0032 (11) | −0.0117 (11) |
| C3 | 0.0575 (12) | 0.0517 (12) | 0.0874 (16) | 0.0001 (10) | 0.0055 (12) | −0.0126 (12) |
| C4 | 0.0699 (14) | 0.0503 (13) | 0.0717 (13) | −0.0051 (11) | 0.0093 (13) | −0.0153 (12) |
| C5 | 0.0684 (13) | 0.0544 (12) | 0.0555 (11) | −0.0128 (10) | 0.0014 (11) | −0.0072 (11) |
| C6 | 0.0570 (11) | 0.0428 (11) | 0.0473 (10) | −0.0082 (9) | 0.0039 (10) | −0.0004 (9) |
| C7 | 0.0542 (11) | 0.0438 (11) | 0.0500 (11) | −0.0054 (9) | 0.0035 (9) | 0.0041 (10) |
| C8 | 0.0657 (13) | 0.0608 (13) | 0.0557 (10) | −0.0042 (11) | −0.0049 (12) | 0.0017 (11) |
| C9 | 0.0649 (14) | 0.0688 (15) | 0.0673 (15) | −0.0031 (11) | −0.0130 (11) | 0.0128 (12) |
| C10 | 0.0643 (13) | 0.0580 (13) | 0.0750 (14) | 0.0076 (10) | −0.0009 (12) | 0.0077 (13) |
| C11 | 0.0671 (13) | 0.0519 (12) | 0.0634 (12) | 0.0033 (10) | 0.0028 (12) | −0.0026 (11) |
| C12 | 0.0520 (11) | 0.0468 (10) | 0.0483 (11) | −0.0047 (9) | 0.0057 (8) | 0.0018 (9) |
| C13 | 0.0528 (10) | 0.0461 (10) | 0.0482 (11) | −0.0072 (9) | 0.0042 (9) | 0.0000 (9) |
| C14 | 0.0555 (11) | 0.0487 (11) | 0.0513 (11) | −0.0028 (9) | 0.0087 (9) | −0.0005 (9) |
| C15A | 0.0598 (12) | 0.0461 (11) | 0.0480 (11) | −0.0100 (9) | −0.0005 (9) | 0.0023 (9) |
| C18A | 0.0757 (15) | 0.0666 (15) | 0.0771 (14) | −0.0061 (12) | −0.0193 (14) | 0.0019 (14) |
| C17A | 0.0865 (16) | 0.0614 (14) | 0.0531 (12) | −0.0118 (13) | −0.0108 (12) | −0.0052 (12) |
| C16A | 0.082 (3) | 0.0744 (16) | 0.0680 (12) | −0.022 (2) | −0.005 (2) | 0.0022 (11) |
| S1A | 0.0667 (6) | 0.0868 (6) | 0.0731 (5) | 0.0098 (4) | −0.0143 (4) | −0.0252 (5) |
| C15B | 0.0598 (12) | 0.0461 (11) | 0.0480 (11) | −0.0100 (9) | −0.0005 (9) | 0.0023 (9) |
| C17B | 0.0865 (16) | 0.0614 (14) | 0.0531 (12) | −0.0118 (13) | −0.0108 (12) | −0.0052 (12) |
| C18B | 0.0757 (15) | 0.0666 (15) | 0.0771 (14) | −0.0061 (12) | −0.0193 (14) | 0.0019 (14) |
| C16B | 0.0667 (6) | 0.0868 (6) | 0.0731 (5) | 0.0098 (4) | −0.0143 (4) | −0.0252 (5) |
| S1B | 0.082 (3) | 0.0744 (16) | 0.0680 (12) | −0.022 (2) | −0.005 (2) | 0.0022 (11) |
| C1—C2 | 1.387 (3) | C10—C11 | 1.377 (3) |
| C1—C6 | 1.403 (3) | C10—H10A | 0.9500 |
| C1—C13 | 1.487 (3) | C11—C12 | 1.391 (3) |
| C2—C3 | 1.389 (3) | C11—H11A | 0.9500 |
| C2—H2A | 0.9500 | C12—C13 | 1.474 (3) |
| C3—C4 | 1.371 (3) | C13—C14 | 1.363 (3) |
| C3—H3A | 0.9500 | C14—C15A | 1.442 (3) |
| C4—C5 | 1.385 (3) | C14—H14A | 0.9500 |
| C4—H4A | 0.9500 | C15A—C16A | 1.416 (19) |
| C5—C6 | 1.380 (3) | C15A—S1A | 1.725 (3) |
| C5—H5A | 0.9500 | C18A—C17A | 1.332 (3) |
| C6—C7 | 1.464 (3) | C18A—S1A | 1.692 (3) |
| C7—C8 | 1.377 (3) | C18A—H18A | 0.9500 |
| C7—C12 | 1.405 (3) | C17A—C16A | 1.388 (3) |
| C8—C9 | 1.386 (3) | C17A—H17A | 0.9500 |
| C8—H8A | 0.9500 | C16A—H16A | 0.9500 |
| C9—C10 | 1.384 (3) | C16B—H16B | 0.9500 |
| C9—H9A | 0.9500 | ||
| C2—C1—C6 | 118.53 (18) | C11—C10—H10A | 119.5 |
| C2—C1—C13 | 133.10 (18) | C9—C10—H10A | 119.5 |
| C6—C1—C13 | 108.35 (17) | C10—C11—C12 | 119.2 (2) |
| C1—C2—C3 | 119.2 (2) | C10—C11—H11A | 120.4 |
| C1—C2—H2A | 120.4 | C12—C11—H11A | 120.4 |
| C3—C2—H2A | 120.4 | C11—C12—C7 | 119.26 (19) |
| C4—C3—C2 | 121.6 (2) | C11—C12—C13 | 131.25 (18) |
| C4—C3—H3A | 119.2 | C7—C12—C13 | 109.45 (17) |
| C2—C3—H3A | 119.2 | C14—C13—C12 | 120.45 (17) |
| C3—C4—C5 | 120.2 (2) | C14—C13—C1 | 134.33 (19) |
| C3—C4—H4A | 119.9 | C12—C13—C1 | 105.19 (16) |
| C5—C4—H4A | 119.9 | C13—C14—C15A | 136.09 (18) |
| C6—C5—C4 | 118.6 (2) | C13—C14—H14A | 112.0 |
| C6—C5—H5A | 120.7 | C15A—C14—H14A | 112.0 |
| C4—C5—H5A | 120.7 | C16A—C15A—C14 | 122.8 (4) |
| C5—C6—C1 | 121.84 (18) | C16A—C15A—S1A | 108.9 (4) |
| C5—C6—C7 | 129.06 (17) | C14—C15A—S1A | 128.03 (14) |
| C1—C6—C7 | 109.09 (16) | C17A—C18A—S1A | 113.1 (2) |
| C8—C7—C12 | 121.16 (18) | C17A—C18A—H18A | 123.5 |
| C8—C7—C6 | 131.03 (19) | S1A—C18A—H18A | 123.5 |
| C12—C7—C6 | 107.78 (17) | C18A—C17A—C16A | 113.4 (9) |
| C7—C8—C9 | 118.8 (2) | C18A—C17A—H17A | 123.3 |
| C7—C8—H8A | 120.6 | C16A—C17A—H17A | 123.3 |
| C9—C8—H8A | 120.6 | C17A—C16A—C15A | 112.5 (12) |
| C10—C9—C8 | 120.5 (2) | C17A—C16A—H16A | 123.8 |
| C10—C9—H9A | 119.8 | C15A—C16A—H16A | 123.8 |
| C8—C9—H9A | 119.8 | C18A—S1A—C15A | 92.08 (13) |
| C11—C10—C9 | 121.1 (2) |
Experimental details
| Crystal data | |
| Chemical formula | C18H12S |
| Mr | 260.34 |
| Crystal system, space group | Orthorhombic, Fdd2 |
| Temperature (K) | 100 |
| a, b, c (Å) | 20.757 (4), 44.434 (9), 5.6260 (11) |
| V (Å3) | 5189.0 (18) |
| Z | 16 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.23 |
| Crystal size (mm) | 0.57 × 0.13 × 0.08 |
| Data collection | |
| Diffractometer | Oxford Diffraction Gemini R CCD |
| Absorption correction | Analytical (Clark & Reid, 1995) |
| Tmin, Tmax | 0.938, 0.985 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 11725, 3018, 1903 |
| Rint | 0.029 |
| (sin θ/λ)max (Å−1) | 0.683 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.090, 0.99 |
| No. of reflections | 3018 |
| No. of parameters | 180 |
| No. of restraints | 4 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.15, −0.17 |
| Absolute structure | Flack (1983), 1110 Friedel pairs |
| Absolute structure parameter | −0.07 (8) |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 1998), enCIFer (Allen et al., 2004).
Acknowledgements
The authors thank the Grant Agency of Slovak Republic (grant Nos. 1/2449/05, 1/4453/07 and APVT-20–007304) as well as the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.
References
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Our synthetic efforts have been focused on a set of multi-ring monomer systems based on thiophene and fluorene ring system. In this respect, the relationship between the charge transport properties in OFET devices (Mullen & Wegner, 1998) and molecular properties such as redox reversibility and crystal structure have been investigated. As active layers, we used oligomers based on molecules consisting of alternating thiophene and fluorene moieties.
In the title compound (1) the S1—C15 and S1—C18 bond lengths of 1.725 (3) Å and 1.692 (3) Å are in a quite good agreement with similar thiophene compounds in the Cambridge Structural Database (CSD; Version 5.27, 2006 release; Allen, 2002); for example, 2,2',5,5'-tetrakis(2-Thienyl)-3,4:3',4'- bis(tetramethylene)-1,1'-biphosphole (Fave et. al., 2004; CDS refcode BERCIL). The thiophene ring is disordered by rotation about the inter-ring C—C bond. There is one intramolecular C–H···S hydrogen bond.