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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1007.
Published online 2008 May 7. doi:  10.1107/S1600536808012695
PMCID: PMC2961574

3,3,4,4,5,5-Hexafluoro-1,2-bis­(5-formyl-2-methylsulfanyl-3-thienyl)cyclo­pent-1-ene

Abstract

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).

Related literature

See Liu et al. (2008 [triangle]) for background literature on this class of photochromic diaryl­ethene compounds.

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Object name is e-64-o1007-scheme1.jpg

Experimental

Crystal data

  • C17H10F6O2S4
  • M r = 488.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1007-efi1.jpg
  • a = 10.7640 (8) Å
  • b = 11.8807 (9) Å
  • c = 15.486 (1) Å
  • β = 93.407 (1)°
  • V = 1976.9 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.55 mm−1
  • T = 291 (2) K
  • 0.38 × 0.29 × 0.28 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.830, T max = 0.858
  • 12872 measured reflections
  • 4488 independent reflections
  • 3623 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.140
  • S = 1.03
  • 4488 reflections
  • 292 parameters
  • 32 restraints
  • H-atom parameters constrained
  • Δρmax = 1.28 e Å−3
  • Δρmin = −0.70 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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012695/xu2419sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012695/xu2419Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of Jiangxi, China (grant Nos. 0620012 and 050017), the Science Funds of the Education Office of Jiangxi, China (grant Nos. [2005]140 and [2007]279), and the Research Fund of Jiangxi Science and Technology Normal University, China.

supplementary crystallographic information

Comment

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.

Experimental

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%.

Refinement

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.

Figures

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.

Crystal data

C17H10F6O2S4F000 = 984
Mr = 488.49Dx = 1.641 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5293 reflections
a = 10.7640 (8) Åθ = 2.6–28.2º
b = 11.8807 (9) ŵ = 0.55 mm1
c = 15.486 (1) ÅT = 291 (2) K
β = 93.407 (1)ºBlock, yellow
V = 1976.9 (2) Å30.38 × 0.29 × 0.28 mm
Z = 4

Data collection

Bruker APEXII diffractometer4488 independent reflections
Radiation source: fine-focus sealed tube3623 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.017
T = 291(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 2.6º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.830, Tmax = 0.858k = −15→15
12872 measured reflectionsl = −20→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 1.28 e Å3
292 parametersΔρmin = −0.70 e Å3
32 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S10.85945 (7)0.33347 (7)0.64145 (5)0.0517 (2)
S20.88965 (7)−0.05788 (6)0.39840 (5)0.0492 (2)
S30.71640 (7)0.12007 (6)0.59914 (4)0.0464 (2)
S40.91715 (7)0.19624 (6)0.38742 (5)0.04583 (19)
F10.56368 (19)0.45268 (16)0.37042 (15)0.0697 (6)
F20.4537 (2)0.3805 (2)0.46758 (14)0.0746 (6)
F30.3300 (2)0.3052 (3)0.3266 (3)0.0812 (12)0.810 (5)
F40.4907 (3)0.3241 (2)0.25152 (15)0.0715 (10)0.810 (5)
F50.4988 (3)0.1142 (3)0.26891 (18)0.1259 (13)
F60.4066 (2)0.1119 (2)0.3863 (2)0.1093 (11)
O10.9727 (3)0.5672 (2)0.66318 (18)0.0827 (9)
O20.8080 (3)−0.3083 (2)0.4030 (3)0.0962 (10)
C10.8505 (3)0.4474 (2)0.5720 (2)0.0494 (7)
C20.7748 (3)0.4263 (2)0.49994 (19)0.0442 (6)
H20.75940.47840.45570.053*
C30.7220 (2)0.3165 (2)0.49939 (16)0.0371 (5)
C40.7605 (2)0.2565 (2)0.57284 (16)0.0377 (5)
C50.6309 (2)0.2760 (2)0.43218 (15)0.0356 (5)
C60.5253 (2)0.3536 (2)0.40199 (18)0.0431 (6)
C70.4524 (3)0.2905 (4)0.3281 (3)0.0486 (11)0.810 (5)
C80.4951 (3)0.1683 (2)0.3416 (2)0.0504 (7)
C90.6167 (2)0.1729 (2)0.39523 (16)0.0358 (5)
C100.6979 (2)0.0740 (2)0.39929 (16)0.0364 (5)
C110.8271 (2)0.0761 (2)0.39533 (16)0.0376 (5)
C120.7434 (3)−0.1179 (2)0.40298 (19)0.0461 (6)
C130.6523 (3)−0.0383 (2)0.40251 (17)0.0420 (6)
H130.5682−0.05570.40410.050*
C140.9139 (3)0.5520 (3)0.5951 (2)0.0642 (9)
H140.90910.61060.55520.077*
C150.7257 (4)−0.2395 (3)0.4026 (2)0.0620 (9)
H150.6444−0.26610.40200.074*
C160.7725 (3)0.1094 (3)0.71059 (18)0.0535 (7)
H16A0.86160.11570.71460.080*
H16B0.74850.03800.73340.080*
H16C0.73730.16890.74330.080*
C171.0583 (3)0.1414 (3)0.3464 (2)0.0593 (8)
H17A1.10260.09850.39080.089*
H17B1.10950.20260.32920.089*
H17C1.03800.09390.29750.089*
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)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0604 (5)0.0470 (4)0.0453 (4)−0.0169 (3)−0.0169 (3)−0.0005 (3)
S20.0508 (4)0.0352 (4)0.0612 (5)0.0014 (3)−0.0004 (3)0.0031 (3)
S30.0593 (4)0.0397 (4)0.0387 (3)−0.0147 (3)−0.0086 (3)0.0039 (3)
S40.0410 (4)0.0356 (3)0.0608 (4)−0.0068 (3)0.0023 (3)−0.0021 (3)
F10.0693 (12)0.0492 (10)0.0876 (14)−0.0059 (9)−0.0189 (10)0.0269 (10)
F20.0707 (13)0.0872 (16)0.0671 (12)0.0286 (11)0.0134 (10)−0.0040 (11)
F30.0335 (13)0.0724 (19)0.134 (3)0.0019 (12)−0.0234 (15)−0.0018 (19)
F40.086 (2)0.0789 (18)0.0469 (13)−0.0162 (15)−0.0187 (12)0.0168 (12)
F50.129 (2)0.140 (2)0.0991 (19)0.062 (2)−0.0753 (17)−0.0722 (19)
F60.0586 (13)0.0851 (17)0.180 (3)−0.0356 (12)−0.0303 (16)0.0536 (18)
O10.100 (2)0.0659 (16)0.0777 (17)−0.0379 (15)−0.0308 (15)−0.0051 (13)
O20.102 (2)0.0389 (13)0.147 (3)0.0066 (14)0.004 (2)0.0123 (16)
C10.0559 (17)0.0376 (14)0.0532 (16)−0.0134 (12)−0.0079 (13)−0.0022 (12)
C20.0512 (16)0.0328 (13)0.0474 (15)−0.0053 (11)−0.0067 (12)0.0013 (11)
C30.0411 (13)0.0315 (12)0.0381 (12)−0.0041 (10)−0.0035 (10)−0.0036 (10)
C40.0403 (13)0.0349 (12)0.0375 (12)−0.0070 (10)−0.0034 (10)−0.0034 (10)
C50.0357 (12)0.0345 (12)0.0361 (12)−0.0035 (10)−0.0019 (9)0.0020 (10)
C60.0421 (14)0.0399 (14)0.0469 (15)0.0008 (11)−0.0008 (11)0.0027 (11)
C70.0330 (18)0.057 (2)0.054 (3)−0.0033 (17)−0.007 (2)0.0045 (19)
C80.0456 (16)0.0448 (15)0.0584 (17)−0.0084 (12)−0.0162 (13)−0.0051 (13)
C90.0360 (12)0.0358 (12)0.0350 (12)−0.0067 (10)−0.0037 (9)0.0002 (10)
C100.0432 (14)0.0316 (12)0.0334 (12)−0.0063 (10)−0.0047 (10)−0.0013 (9)
C110.0428 (14)0.0331 (12)0.0364 (12)−0.0040 (10)−0.0038 (10)−0.0006 (10)
C120.0565 (17)0.0343 (13)0.0468 (15)−0.0083 (12)−0.0022 (12)0.0022 (11)
C130.0467 (15)0.0362 (13)0.0424 (14)−0.0100 (11)−0.0044 (11)−0.0010 (11)
C140.076 (2)0.0452 (17)0.069 (2)−0.0222 (16)−0.0169 (17)−0.0023 (15)
C150.080 (2)0.0343 (15)0.070 (2)−0.0059 (15)−0.0033 (17)0.0079 (14)
C160.0669 (19)0.0532 (17)0.0394 (14)−0.0042 (15)−0.0055 (13)0.0047 (13)
C170.0416 (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)

Geometric parameters (Å, °)

S1—C41.722 (2)C5—C61.516 (4)
S1—C11.728 (3)C6—C71.543 (4)
S2—C111.728 (3)C6—C7'1.554 (8)
S2—C121.734 (3)C7—C81.534 (5)
S3—C41.744 (3)C8—C91.509 (4)
S3—C161.799 (3)C8—C7'1.545 (8)
S4—C111.734 (3)C9—C101.463 (4)
S4—C171.803 (3)C10—C111.397 (4)
F1—C61.349 (3)C10—C131.424 (3)
F2—C61.349 (3)C12—C131.362 (4)
F3—C71.329 (4)C12—C151.456 (4)
F4—C71.339 (5)C13—H130.9300
F5—C81.298 (4)C14—H140.9300
F6—C81.384 (4)C15—H150.9300
O1—C141.211 (4)C16—H16A0.9600
O2—C151.205 (4)C16—H16B0.9600
C1—C21.364 (4)C16—H16C0.9600
C1—C141.453 (4)C17—H17A0.9600
C2—C31.423 (3)C17—H17B0.9600
C2—H20.9300C17—H17C0.9600
C3—C41.385 (4)F3'—C7'1.317 (8)
C3—C51.468 (3)F4'—C7'1.313 (8)
C5—C91.356 (3)
C4—S1—C191.26 (13)F6—C8—C7'90.5 (5)
C11—S2—C1291.55 (13)C9—C8—C7'108.8 (3)
C4—S3—C16102.05 (14)C5—C9—C10130.9 (2)
C11—S4—C17102.34 (14)C5—C9—C8109.7 (2)
C2—C1—C14127.4 (3)C10—C9—C8119.3 (2)
C2—C1—S1112.0 (2)C11—C10—C13111.4 (2)
C14—C1—S1120.6 (2)C11—C10—C9125.3 (2)
C1—C2—C3113.1 (2)C13—C10—C9123.3 (2)
C1—C2—H2123.5C10—C11—S2111.69 (19)
C3—C2—H2123.5C10—C11—S4125.5 (2)
C4—C3—C2111.5 (2)S2—C11—S4122.82 (16)
C4—C3—C5124.7 (2)C13—C12—C15126.5 (3)
C2—C3—C5123.7 (2)C13—C12—S2111.7 (2)
C3—C4—S1112.20 (19)C15—C12—S2121.8 (3)
C3—C4—S3126.69 (19)C12—C13—C10113.7 (2)
S1—C4—S3121.10 (15)C12—C13—H13123.2
C9—C5—C3130.4 (2)C10—C13—H13123.2
C9—C5—C6110.8 (2)O1—C14—C1123.8 (3)
C3—C5—C6118.5 (2)O1—C14—H14118.1
F1—C6—F2105.5 (2)C1—C14—H14118.1
F1—C6—C5113.7 (2)O2—C15—C12125.2 (4)
F2—C6—C5111.3 (2)O2—C15—H15117.4
F1—C6—C7107.9 (3)C12—C15—H15117.4
F2—C6—C7112.7 (3)S3—C16—H16A109.5
C5—C6—C7105.8 (2)S3—C16—H16B109.5
F1—C6—C7'121.9 (4)H16A—C16—H16B109.5
F2—C6—C7'95.4 (4)S3—C16—H16C109.5
C5—C6—C7'107.4 (3)H16A—C16—H16C109.5
F3—C7—F4107.7 (3)H16B—C16—H16C109.5
F3—C7—C8114.6 (3)S4—C17—H17A109.5
F4—C7—C8107.3 (3)S4—C17—H17B109.5
F3—C7—C6114.1 (4)H17A—C17—H17B109.5
F4—C7—C6110.1 (3)S4—C17—H17C109.5
C8—C7—C6102.9 (2)H17A—C17—H17C109.5
F5—C8—F6104.6 (3)H17B—C17—H17C109.5
F5—C8—C9115.2 (3)F4'—C7'—F3'116.1 (12)
F6—C8—C9110.0 (2)F4'—C7'—C8115.4 (10)
F5—C8—C7112.0 (3)F3'—C7'—C8100.0 (8)
F6—C8—C7108.5 (3)F4'—C7'—C6110.0 (9)
C9—C8—C7106.5 (2)F3'—C7'—C6112.1 (8)
F5—C8—C7'124.0 (4)C8—C7'—C6101.9 (4)
C4—S1—C1—C20.1 (3)F5—C8—C9—C5140.8 (3)
C4—S1—C1—C14177.1 (3)F6—C8—C9—C5−101.3 (3)
C14—C1—C2—C3−176.8 (3)C7—C8—C9—C516.0 (4)
S1—C1—C2—C30.0 (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—C5175.6 (3)F6—C8—C9—C1079.4 (3)
C2—C3—C4—S10.1 (3)C7—C8—C9—C10−163.3 (3)
C5—C3—C4—S1−175.5 (2)C7'—C8—C9—C10177.0 (5)
C2—C3—C4—S3178.9 (2)C5—C9—C10—C11−41.3 (4)
C5—C3—C4—S33.2 (4)C8—C9—C10—C11137.8 (3)
C1—S1—C4—C3−0.1 (2)C5—C9—C10—C13142.7 (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—S110.8 (2)C9—C10—C11—S2−177.9 (2)
C4—C3—C5—C9−41.9 (4)C13—C10—C11—S4178.00 (19)
C2—C3—C5—C9142.9 (3)C9—C10—C11—S41.6 (4)
C4—C3—C5—C6131.4 (3)C12—S2—C11—C101.0 (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—F158.0 (3)C17—S4—C11—S219.5 (2)
C9—C5—C6—F2113.5 (3)C11—S2—C12—C13−0.3 (2)
C3—C5—C6—F2−61.0 (3)C11—S2—C12—C15176.7 (3)
C9—C5—C6—C7−9.2 (3)C15—C12—C13—C10−177.4 (3)
C3—C5—C6—C7176.3 (3)S2—C12—C13—C10−0.6 (3)
C9—C5—C6—C7'10.3 (5)C11—C10—C13—C121.4 (3)
C3—C5—C6—C7'−164.2 (5)C9—C10—C13—C12177.8 (2)
F1—C6—C7—F3−95.2 (4)C2—C1—C14—O1174.5 (4)
F2—C6—C7—F320.9 (5)S1—C1—C14—O1−2.0 (6)
C5—C6—C7—F3142.8 (3)C13—C12—C15—O2180.0 (4)
C7'—C6—C7—F345.2 (10)S2—C12—C15—O23.4 (5)
F1—C6—C7—F425.9 (4)F5—C8—C7'—F4'−12.0 (12)
F2—C6—C7—F4142.0 (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—F4166.3 (11)C7—C8—C7'—F4'42.7 (11)
F1—C6—C7—C8140.1 (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—C818.0 (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—F588.4 (5)F5—C8—C7'—C6−131.2 (5)
F4—C7—C8—F5−31.1 (4)F6—C8—C7'—C6120.7 (5)
C6—C7—C8—F5−147.2 (3)C9—C8—C7'—C69.3 (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—F697.9 (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—C995.6 (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'—C8122.1 (5)
C6—C5—C9—C10175.0 (3)F2—C6—C7'—C8−125.8 (5)
C3—C5—C9—C8169.5 (3)C5—C6—C7'—C8−11.5 (7)
C6—C5—C9—C8−4.2 (3)C7—C6—C7'—C876.6 (10)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2419).

References

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