Acta Cryst. (2008). E64, o1007 [ doi:10.1107/S1600536808012695 ]
In the crystal structure of the title diarylethylene compound, C17H10F6O2S4, the two 3-thienyl substituents are aligned at 44.9 (1) and 40.2 (1)° with respect to the -C-C=C-C- fragment of the central cyclopentenyl ring. The five-membered cyclopentenyl ring adopts an envelope conformation. The flap atom of this ring and the two F atoms bonded to it are disordered over two positions with occupancies 0.810 (5)/0.190 (5).
5-(Methylthio)thiophene-2-carbaldehyde was brominated to 4-bromo-5-(methylthio)thiophene-2-carbaldehyde at 273 K. The carbonyl group was converted to an acetal group by the treatment of the aldehyde (3.2 g, 13.6 mmol) with glycol (4.2 g, 70 mmol) catalyzed by p-toluenesulfonic acid (0.07 g, 0.41 mmol) in benzene (150 ml). The resulting compound (3.82 g, 13.4 mmol) in THF (50 ml) was reacted with 2.5 M butyllithium (5.34 ml) at 195 K under a nitrogen atmosphere. Octafluorocyclopentene (0.91 ml, 6.68 mmol) was added, and the reaction was quenched by water. Column chromatography on silica gave 3,3,4,4,5,5-hexafluoro- 1,2-bis[5-(1,3-dioxolan-2-yl)-2-methylthio-3-thienyl]cyclopent-1-ene (1.2 g, 2.00 mmol). The compound was hydrolyzed to give the title compound in 90% yield. Yellow crystals were obtained by the vapor diffusion of chloroform and hexane (1:1). C and H elemental analysis, Calc. for C17H10F6O2S4 (%): C 41.80, H 2.06; found: C 41.73, H 2.07%.
The cyclopentenyl ring has a flat –C–C=C–C– fragment; the fifth member comprises the flap of the envelop, and is disordered. Restraints were imposed so that the ring adopts such a conformation; the 1,2-related atoms, C6/C7 and C7/C8 were restrained to 1.54±0.01 Å, and the 1,3-related C6/C8 atoms to 2.51±0.01 Å. The four C–F distances were restrained to within 0.01 Å of each other; the anisotropic temperature factors of the minor component atoms were restrained to be nearly isotropic. The disorder refined to a 81 (1):19 ratio. The final difference Fourier map had a large peak in the vicinity of the ordered fluorine atoms.
Hydrogen atoms were positioned geometrically (C–H 0.93 to 0.96 Å)] and constrained to ride on their parent atoms, with Uiso(H) = 1.2 to 1.5 times the Ueq of the parent atom.
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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
![[Figure 1]](./xu2419fig1thm.gif)
| Fig. 1. Thermal ellipsoid plot (Barbour) at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radii; the minor disorder component is not shown. |
| C17H10F6O2S4 | F000 = 984 |
| Mr = 488.49 | Dx = 1.641 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 5293 reflections |
| a = 10.7640 (8) Å | θ = 2.6–28.2º |
| b = 11.8807 (9) Å | µ = 0.55 mm−1 |
| c = 15.486 (1) Å | T = 291 (2) K |
| β = 93.407 (1)º | Block, yellow |
| V = 1976.9 (2) Å3 | 0.38 × 0.29 × 0.28 mm |
| Z = 4 |
| Bruker APEXII diffractometer | 4488 independent reflections |
| Radiation source: fine-focus sealed tube | 3623 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.017 |
| T = 291(2) K | θmax = 27.5º |
| φ and ω scans | θmin = 2.6º |
| Absorption correction: Multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
| Tmin = 0.830, Tmax = 0.858 | k = −15→15 |
| 12872 measured reflections | l = −20→19 |
| 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)] = 0.048 | H-atom parameters constrained |
| wR(F2) = 0.140 | w = 1/[σ2(Fo2) + (0.0719P)2 + 1.6843P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 4488 reflections | Δρmax = 1.28 e Å−3 |
| 292 parameters | Δρmin = −0.70 e Å−3 |
| 32 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C17H10F6O2S4 | V = 1976.9 (2) Å3 |
| Mr = 488.49 | Z = 4 |
| Monoclinic, P21/c | Mo Kα |
| a = 10.7640 (8) Å | µ = 0.55 mm−1 |
| b = 11.8807 (9) Å | T = 291 (2) K |
| c = 15.486 (1) Å | 0.38 × 0.29 × 0.28 mm |
| β = 93.407 (1)º |
| Bruker APEXII diffractometer | 4488 independent reflections |
| Absorption correction: Multi-scan (SADABS; Sheldrick, 1996) | 3623 reflections with I > 2σ(I) |
| Tmin = 0.830, Tmax = 0.858 | Rint = 0.017 |
| 12872 measured reflections |
| R[F2 > 2σ(F2)] = 0.048 | 32 restraints |
| wR(F2) = 0.140 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 1.28 e Å−3 |
| 4488 reflections | Δρmin = −0.70 e Å−3 |
| 292 parameters |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| S1 | 0.85945 (7) | 0.33347 (7) | 0.64145 (5) | 0.0517 (2) | |
| S2 | 0.88965 (7) | −0.05788 (6) | 0.39840 (5) | 0.0492 (2) | |
| S3 | 0.71640 (7) | 0.12007 (6) | 0.59914 (4) | 0.0464 (2) | |
| S4 | 0.91715 (7) | 0.19624 (6) | 0.38742 (5) | 0.04583 (19) | |
| F1 | 0.56368 (19) | 0.45268 (16) | 0.37042 (15) | 0.0697 (6) | |
| F2 | 0.4537 (2) | 0.3805 (2) | 0.46758 (14) | 0.0746 (6) | |
| F3 | 0.3300 (2) | 0.3052 (3) | 0.3266 (3) | 0.0812 (12) | 0.810 (5) |
| F4 | 0.4907 (3) | 0.3241 (2) | 0.25152 (15) | 0.0715 (10) | 0.810 (5) |
| F5 | 0.4988 (3) | 0.1142 (3) | 0.26891 (18) | 0.1259 (13) | |
| F6 | 0.4066 (2) | 0.1119 (2) | 0.3863 (2) | 0.1093 (11) | |
| O1 | 0.9727 (3) | 0.5672 (2) | 0.66318 (18) | 0.0827 (9) | |
| O2 | 0.8080 (3) | −0.3083 (2) | 0.4030 (3) | 0.0962 (10) | |
| C1 | 0.8505 (3) | 0.4474 (2) | 0.5720 (2) | 0.0494 (7) | |
| C2 | 0.7748 (3) | 0.4263 (2) | 0.49994 (19) | 0.0442 (6) | |
| H2 | 0.7594 | 0.4784 | 0.4557 | 0.053* | |
| C3 | 0.7220 (2) | 0.3165 (2) | 0.49939 (16) | 0.0371 (5) | |
| C4 | 0.7605 (2) | 0.2565 (2) | 0.57284 (16) | 0.0377 (5) | |
| C5 | 0.6309 (2) | 0.2760 (2) | 0.43218 (15) | 0.0356 (5) | |
| C6 | 0.5253 (2) | 0.3536 (2) | 0.40199 (18) | 0.0431 (6) | |
| C7 | 0.4524 (3) | 0.2905 (4) | 0.3281 (3) | 0.0486 (11) | 0.810 (5) |
| C8 | 0.4951 (3) | 0.1683 (2) | 0.3416 (2) | 0.0504 (7) | |
| C9 | 0.6167 (2) | 0.1729 (2) | 0.39523 (16) | 0.0358 (5) | |
| C10 | 0.6979 (2) | 0.0740 (2) | 0.39929 (16) | 0.0364 (5) | |
| C11 | 0.8271 (2) | 0.0761 (2) | 0.39533 (16) | 0.0376 (5) | |
| C12 | 0.7434 (3) | −0.1179 (2) | 0.40298 (19) | 0.0461 (6) | |
| C13 | 0.6523 (3) | −0.0383 (2) | 0.40251 (17) | 0.0420 (6) | |
| H13 | 0.5682 | −0.0557 | 0.4041 | 0.050* | |
| C14 | 0.9139 (3) | 0.5520 (3) | 0.5951 (2) | 0.0642 (9) | |
| H14 | 0.9091 | 0.6106 | 0.5552 | 0.077* | |
| C15 | 0.7257 (4) | −0.2395 (3) | 0.4026 (2) | 0.0620 (9) | |
| H15 | 0.6444 | −0.2661 | 0.4020 | 0.074* | |
| C16 | 0.7725 (3) | 0.1094 (3) | 0.71059 (18) | 0.0535 (7) | |
| H16A | 0.8616 | 0.1157 | 0.7146 | 0.080* | |
| H16B | 0.7485 | 0.0380 | 0.7334 | 0.080* | |
| H16C | 0.7373 | 0.1689 | 0.7433 | 0.080* | |
| C17 | 1.0583 (3) | 0.1414 (3) | 0.3464 (2) | 0.0593 (8) | |
| H17A | 1.1026 | 0.0985 | 0.3908 | 0.089* | |
| H17B | 1.1095 | 0.2026 | 0.3292 | 0.089* | |
| H17C | 1.0380 | 0.0939 | 0.2975 | 0.089* | |
| F3' | 0.3375 (10) | 0.2469 (12) | 0.4024 (8) | 0.081 (4) | 0.190 (5) |
| F4' | 0.3867 (17) | 0.3304 (12) | 0.2800 (9) | 0.090 (5) | 0.190 (5) |
| C7' | 0.4250 (7) | 0.2804 (7) | 0.3523 (7) | 0.050 (6) | 0.190 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0604 (5) | 0.0470 (4) | 0.0453 (4) | −0.0169 (3) | −0.0169 (3) | −0.0005 (3) |
| S2 | 0.0508 (4) | 0.0352 (4) | 0.0612 (5) | 0.0014 (3) | −0.0004 (3) | 0.0031 (3) |
| S3 | 0.0593 (4) | 0.0397 (4) | 0.0387 (3) | −0.0147 (3) | −0.0086 (3) | 0.0039 (3) |
| S4 | 0.0410 (4) | 0.0356 (3) | 0.0608 (4) | −0.0068 (3) | 0.0023 (3) | −0.0021 (3) |
| F1 | 0.0693 (12) | 0.0492 (10) | 0.0876 (14) | −0.0059 (9) | −0.0189 (10) | 0.0269 (10) |
| F2 | 0.0707 (13) | 0.0872 (16) | 0.0671 (12) | 0.0286 (11) | 0.0134 (10) | −0.0040 (11) |
| F3 | 0.0335 (13) | 0.0724 (19) | 0.134 (3) | 0.0019 (12) | −0.0234 (15) | −0.0018 (19) |
| F4 | 0.086 (2) | 0.0789 (18) | 0.0469 (13) | −0.0162 (15) | −0.0187 (12) | 0.0168 (12) |
| F5 | 0.129 (2) | 0.140 (2) | 0.0991 (19) | 0.062 (2) | −0.0753 (17) | −0.0722 (19) |
| F6 | 0.0586 (13) | 0.0851 (17) | 0.180 (3) | −0.0356 (12) | −0.0303 (16) | 0.0536 (18) |
| O1 | 0.100 (2) | 0.0659 (16) | 0.0777 (17) | −0.0379 (15) | −0.0308 (15) | −0.0051 (13) |
| O2 | 0.102 (2) | 0.0389 (13) | 0.147 (3) | 0.0066 (14) | 0.004 (2) | 0.0123 (16) |
| C1 | 0.0559 (17) | 0.0376 (14) | 0.0532 (16) | −0.0134 (12) | −0.0079 (13) | −0.0022 (12) |
| C2 | 0.0512 (16) | 0.0328 (13) | 0.0474 (15) | −0.0053 (11) | −0.0067 (12) | 0.0013 (11) |
| C3 | 0.0411 (13) | 0.0315 (12) | 0.0381 (12) | −0.0041 (10) | −0.0035 (10) | −0.0036 (10) |
| C4 | 0.0403 (13) | 0.0349 (12) | 0.0375 (12) | −0.0070 (10) | −0.0034 (10) | −0.0034 (10) |
| C5 | 0.0357 (12) | 0.0345 (12) | 0.0361 (12) | −0.0035 (10) | −0.0019 (9) | 0.0020 (10) |
| C6 | 0.0421 (14) | 0.0399 (14) | 0.0469 (15) | 0.0008 (11) | −0.0008 (11) | 0.0027 (11) |
| C7 | 0.0330 (18) | 0.057 (2) | 0.054 (3) | −0.0033 (17) | −0.007 (2) | 0.0045 (19) |
| C8 | 0.0456 (16) | 0.0448 (15) | 0.0584 (17) | −0.0084 (12) | −0.0162 (13) | −0.0051 (13) |
| C9 | 0.0360 (12) | 0.0358 (12) | 0.0350 (12) | −0.0067 (10) | −0.0037 (9) | 0.0002 (10) |
| C10 | 0.0432 (14) | 0.0316 (12) | 0.0334 (12) | −0.0063 (10) | −0.0047 (10) | −0.0013 (9) |
| C11 | 0.0428 (14) | 0.0331 (12) | 0.0364 (12) | −0.0040 (10) | −0.0038 (10) | −0.0006 (10) |
| C12 | 0.0565 (17) | 0.0343 (13) | 0.0468 (15) | −0.0083 (12) | −0.0022 (12) | 0.0022 (11) |
| C13 | 0.0467 (15) | 0.0362 (13) | 0.0424 (14) | −0.0100 (11) | −0.0044 (11) | −0.0010 (11) |
| C14 | 0.076 (2) | 0.0452 (17) | 0.069 (2) | −0.0222 (16) | −0.0169 (17) | −0.0023 (15) |
| C15 | 0.080 (2) | 0.0343 (15) | 0.070 (2) | −0.0059 (15) | −0.0033 (17) | 0.0079 (14) |
| C16 | 0.0669 (19) | 0.0532 (17) | 0.0394 (14) | −0.0042 (15) | −0.0055 (13) | 0.0047 (13) |
| C17 | 0.0416 (16) | 0.0531 (18) | 0.084 (2) | −0.0022 (13) | 0.0075 (15) | 0.0001 (16) |
| F3' | 0.048 (5) | 0.102 (8) | 0.093 (8) | −0.017 (5) | 0.007 (5) | −0.019 (6) |
| F4' | 0.083 (9) | 0.094 (8) | 0.086 (7) | 0.014 (7) | −0.043 (7) | 0.001 (6) |
| C7' | 0.057 (10) | 0.053 (8) | 0.038 (8) | −0.001 (7) | −0.002 (7) | 0.014 (6) |
| S1—C4 | 1.722 (2) | C5—C6 | 1.516 (4) |
| S1—C1 | 1.728 (3) | C6—C7 | 1.543 (4) |
| S2—C11 | 1.728 (3) | C6—C7' | 1.554 (8) |
| S2—C12 | 1.734 (3) | C7—C8 | 1.534 (5) |
| S3—C4 | 1.744 (3) | C8—C9 | 1.509 (4) |
| S3—C16 | 1.799 (3) | C8—C7' | 1.545 (8) |
| S4—C11 | 1.734 (3) | C9—C10 | 1.463 (4) |
| S4—C17 | 1.803 (3) | C10—C11 | 1.397 (4) |
| F1—C6 | 1.349 (3) | C10—C13 | 1.424 (3) |
| F2—C6 | 1.349 (3) | C12—C13 | 1.362 (4) |
| F3—C7 | 1.329 (4) | C12—C15 | 1.456 (4) |
| F4—C7 | 1.339 (5) | C13—H13 | 0.9300 |
| F5—C8 | 1.298 (4) | C14—H14 | 0.9300 |
| F6—C8 | 1.384 (4) | C15—H15 | 0.9300 |
| O1—C14 | 1.211 (4) | C16—H16A | 0.9600 |
| O2—C15 | 1.205 (4) | C16—H16B | 0.9600 |
| C1—C2 | 1.364 (4) | C16—H16C | 0.9600 |
| C1—C14 | 1.453 (4) | C17—H17A | 0.9600 |
| C2—C3 | 1.423 (3) | C17—H17B | 0.9600 |
| C2—H2 | 0.9300 | C17—H17C | 0.9600 |
| C3—C4 | 1.385 (4) | F3'—C7' | 1.317 (8) |
| C3—C5 | 1.468 (3) | F4'—C7' | 1.313 (8) |
| C5—C9 | 1.356 (3) | ||
| C4—S1—C1 | 91.26 (13) | F6—C8—C7' | 90.5 (5) |
| C11—S2—C12 | 91.55 (13) | C9—C8—C7' | 108.8 (3) |
| C4—S3—C16 | 102.05 (14) | C5—C9—C10 | 130.9 (2) |
| C11—S4—C17 | 102.34 (14) | C5—C9—C8 | 109.7 (2) |
| C2—C1—C14 | 127.4 (3) | C10—C9—C8 | 119.3 (2) |
| C2—C1—S1 | 112.0 (2) | C11—C10—C13 | 111.4 (2) |
| C14—C1—S1 | 120.6 (2) | C11—C10—C9 | 125.3 (2) |
| C1—C2—C3 | 113.1 (2) | C13—C10—C9 | 123.3 (2) |
| C1—C2—H2 | 123.5 | C10—C11—S2 | 111.69 (19) |
| C3—C2—H2 | 123.5 | C10—C11—S4 | 125.5 (2) |
| C4—C3—C2 | 111.5 (2) | S2—C11—S4 | 122.82 (16) |
| C4—C3—C5 | 124.7 (2) | C13—C12—C15 | 126.5 (3) |
| C2—C3—C5 | 123.7 (2) | C13—C12—S2 | 111.7 (2) |
| C3—C4—S1 | 112.20 (19) | C15—C12—S2 | 121.8 (3) |
| C3—C4—S3 | 126.69 (19) | C12—C13—C10 | 113.7 (2) |
| S1—C4—S3 | 121.10 (15) | C12—C13—H13 | 123.2 |
| C9—C5—C3 | 130.4 (2) | C10—C13—H13 | 123.2 |
| C9—C5—C6 | 110.8 (2) | O1—C14—C1 | 123.8 (3) |
| C3—C5—C6 | 118.5 (2) | O1—C14—H14 | 118.1 |
| F1—C6—F2 | 105.5 (2) | C1—C14—H14 | 118.1 |
| F1—C6—C5 | 113.7 (2) | O2—C15—C12 | 125.2 (4) |
| F2—C6—C5 | 111.3 (2) | O2—C15—H15 | 117.4 |
| F1—C6—C7 | 107.9 (3) | C12—C15—H15 | 117.4 |
| F2—C6—C7 | 112.7 (3) | S3—C16—H16A | 109.5 |
| C5—C6—C7 | 105.8 (2) | S3—C16—H16B | 109.5 |
| F1—C6—C7' | 121.9 (4) | H16A—C16—H16B | 109.5 |
| F2—C6—C7' | 95.4 (4) | S3—C16—H16C | 109.5 |
| C5—C6—C7' | 107.4 (3) | H16A—C16—H16C | 109.5 |
| F3—C7—F4 | 107.7 (3) | H16B—C16—H16C | 109.5 |
| F3—C7—C8 | 114.6 (3) | S4—C17—H17A | 109.5 |
| F4—C7—C8 | 107.3 (3) | S4—C17—H17B | 109.5 |
| F3—C7—C6 | 114.1 (4) | H17A—C17—H17B | 109.5 |
| F4—C7—C6 | 110.1 (3) | S4—C17—H17C | 109.5 |
| C8—C7—C6 | 102.9 (2) | H17A—C17—H17C | 109.5 |
| F5—C8—F6 | 104.6 (3) | H17B—C17—H17C | 109.5 |
| F5—C8—C9 | 115.2 (3) | F4'—C7'—F3' | 116.1 (12) |
| F6—C8—C9 | 110.0 (2) | F4'—C7'—C8 | 115.4 (10) |
| F5—C8—C7 | 112.0 (3) | F3'—C7'—C8 | 100.0 (8) |
| F6—C8—C7 | 108.5 (3) | F4'—C7'—C6 | 110.0 (9) |
| C9—C8—C7 | 106.5 (2) | F3'—C7'—C6 | 112.1 (8) |
| F5—C8—C7' | 124.0 (4) | C8—C7'—C6 | 101.9 (4) |
| C4—S1—C1—C2 | 0.1 (3) | F5—C8—C9—C5 | 140.8 (3) |
| C4—S1—C1—C14 | 177.1 (3) | F6—C8—C9—C5 | −101.3 (3) |
| C14—C1—C2—C3 | −176.8 (3) | C7—C8—C9—C5 | 16.0 (4) |
| S1—C1—C2—C3 | 0.0 (4) | C7'—C8—C9—C5 | −3.7 (5) |
| C1—C2—C3—C4 | −0.1 (4) | F5—C8—C9—C10 | −38.5 (4) |
| C1—C2—C3—C5 | 175.6 (3) | F6—C8—C9—C10 | 79.4 (3) |
| C2—C3—C4—S1 | 0.1 (3) | C7—C8—C9—C10 | −163.3 (3) |
| C5—C3—C4—S1 | −175.5 (2) | C7'—C8—C9—C10 | 177.0 (5) |
| C2—C3—C4—S3 | 178.9 (2) | C5—C9—C10—C11 | −41.3 (4) |
| C5—C3—C4—S3 | 3.2 (4) | C8—C9—C10—C11 | 137.8 (3) |
| C1—S1—C4—C3 | −0.1 (2) | C5—C9—C10—C13 | 142.7 (3) |
| C1—S1—C4—S3 | −178.93 (19) | C8—C9—C10—C13 | −38.2 (4) |
| C16—S3—C4—C3 | −167.9 (3) | C13—C10—C11—S2 | −1.5 (3) |
| C16—S3—C4—S1 | 10.8 (2) | C9—C10—C11—S2 | −177.9 (2) |
| C4—C3—C5—C9 | −41.9 (4) | C13—C10—C11—S4 | 178.00 (19) |
| C2—C3—C5—C9 | 142.9 (3) | C9—C10—C11—S4 | 1.6 (4) |
| C4—C3—C5—C6 | 131.4 (3) | C12—S2—C11—C10 | 1.0 (2) |
| C2—C3—C5—C6 | −43.8 (4) | C12—S2—C11—S4 | −178.51 (18) |
| C9—C5—C6—F1 | −127.5 (3) | C17—S4—C11—C10 | −160.0 (2) |
| C3—C5—C6—F1 | 58.0 (3) | C17—S4—C11—S2 | 19.5 (2) |
| C9—C5—C6—F2 | 113.5 (3) | C11—S2—C12—C13 | −0.3 (2) |
| C3—C5—C6—F2 | −61.0 (3) | C11—S2—C12—C15 | 176.7 (3) |
| C9—C5—C6—C7 | −9.2 (3) | C15—C12—C13—C10 | −177.4 (3) |
| C3—C5—C6—C7 | 176.3 (3) | S2—C12—C13—C10 | −0.6 (3) |
| C9—C5—C6—C7' | 10.3 (5) | C11—C10—C13—C12 | 1.4 (3) |
| C3—C5—C6—C7' | −164.2 (5) | C9—C10—C13—C12 | 177.8 (2) |
| F1—C6—C7—F3 | −95.2 (4) | C2—C1—C14—O1 | 174.5 (4) |
| F2—C6—C7—F3 | 20.9 (5) | S1—C1—C14—O1 | −2.0 (6) |
| C5—C6—C7—F3 | 142.8 (3) | C13—C12—C15—O2 | 180.0 (4) |
| C7'—C6—C7—F3 | 45.2 (10) | S2—C12—C15—O2 | 3.4 (5) |
| F1—C6—C7—F4 | 25.9 (4) | F5—C8—C7'—F4' | −12.0 (12) |
| F2—C6—C7—F4 | 142.0 (3) | F6—C8—C7'—F4' | −120.0 (10) |
| C5—C6—C7—F4 | −96.1 (3) | C9—C8—C7'—F4' | 128.6 (10) |
| C7'—C6—C7—F4 | 166.3 (11) | C7—C8—C7'—F4' | 42.7 (11) |
| F1—C6—C7—C8 | 140.1 (3) | F5—C8—C7'—F3' | 113.4 (7) |
| F2—C6—C7—C8 | −103.8 (3) | F6—C8—C7'—F3' | 5.4 (7) |
| C5—C6—C7—C8 | 18.0 (3) | C9—C8—C7'—F3' | −106.0 (7) |
| C7'—C6—C7—C8 | −79.5 (10) | C7—C8—C7'—F3' | 168.0 (14) |
| F3—C7—C8—F5 | 88.4 (5) | F5—C8—C7'—C6 | −131.2 (5) |
| F4—C7—C8—F5 | −31.1 (4) | F6—C8—C7'—C6 | 120.7 (5) |
| C6—C7—C8—F5 | −147.2 (3) | C9—C8—C7'—C6 | 9.3 (7) |
| F3—C7—C8—F6 | −26.5 (5) | C7—C8—C7'—C6 | −76.6 (10) |
| F4—C7—C8—F6 | −146.0 (3) | F1—C6—C7'—F4' | −0.8 (12) |
| C6—C7—C8—F6 | 97.9 (3) | F2—C6—C7'—F4' | 111.2 (10) |
| F3—C7—C8—C9 | −144.9 (4) | C5—C6—C7'—F4' | −134.5 (10) |
| F4—C7—C8—C9 | 95.6 (3) | C7—C6—C7'—F4' | −46.4 (12) |
| C6—C7—C8—C9 | −20.5 (4) | F1—C6—C7'—F3' | −131.7 (8) |
| F3—C7—C8—C7' | −44.8 (10) | F2—C6—C7'—F3' | −19.7 (9) |
| F4—C7—C8—C7' | −164.3 (11) | C5—C6—C7'—F3' | 94.7 (9) |
| C6—C7—C8—C7' | 79.6 (10) | C7—C6—C7'—F3' | −177.3 (15) |
| C3—C5—C9—C10 | −11.3 (5) | F1—C6—C7'—C8 | 122.1 (5) |
| C6—C5—C9—C10 | 175.0 (3) | F2—C6—C7'—C8 | −125.8 (5) |
| C3—C5—C9—C8 | 169.5 (3) | C5—C6—C7'—C8 | −11.5 (7) |
| C6—C5—C9—C8 | −4.2 (3) | C7—C6—C7'—C8 | 76.6 (10) |
This work was supported by the Natural Science Foundation of Jiangxi, China (0620012, 050017), the Science Funds of the Education Office of Jiangxi, China ([2005]140, [2007]279) and the Research Fund of Jiangxi S&T Normal University, China.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Liu, G., Tu, Q., Zhang, Q., Fan, C. & Yang, T. (2008). Acta Cryst. E64, o938.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2008). publCIF. In preparation.
A previous study describes the structure of a photochromic compound, 1,2-bis[5-(4-cyanophenyl)-2-methyl-3-thienyl]-3,3,4,4,5,5-\ hexafluorocyclopent-1-ene (Liu et al., 2008). The study is extended to the title compound (Scheme I, Fig. 1). The diarylethylene compound, C17H10F6O2S4, has its 3-thienyl substituents aligned at 41.4 (1) and 43.5 (1)° with respect to the central cyclopentenyl ring, which is almost flat.