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The photochromic title compound, C24H18F6O2S, has thienyl and aryl substituents on the C=C double bond of the shallow half-chair-shaped cyclo­pentene ring. The planes of the two substituent rings are inclined to that of the cyclopentene ring, with dihedral angles between the mean plane of the cyclopentene ring and those of the phenyl­ene and thienyl rings of 51.2 (1) and 51.3 (1)°, respectively. The mol­ecule adopts an anti­parallel conformation, with a distance between the two photoreactive C atoms of 3.717 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270109013468/sf3103sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270109013468/sf3103Isup2.hkl
Contains datablock I

CCDC reference: 729601

Comment top

Photochromic diarylethenes find possible applications in optical memory-storage devices and as optical switches (Irie, 2000; Tian & Yang, 2004). In our own studies, we have found that central to photochromic activity of the class of perfluorocyclopentenes is a pendant five-membered heterocyclic ring (Fan et al., 2008), a feature that is displayed by the title compound, (I).

The envelope-shaped cyclopentenyl ring [the r.m.s.deviation of the constituent C atoms is 0.08 Å] has a substituent thienyl group and an anisyl group on opposing ends of the CC double bond (Fig. 1). Steric hindrance is avoided by twisting of these rings [the dihedral angles being 51.2 (1)° for the phenylene ring and 51.3 (1)° for the thienyl ring], but the avoidance of crowding places the aliphatic ring substituents on opposites sides of the mean cyclopentenyl plane. This configuration is crucial for the manifestation of photochromism and other photo-induced properties (Woodward & Hoffmann, 1970). More importantly, the CC double bond of the cyclopentenyl ring can, theoretically, change to a C—C single bond. Such a reduction in bond order would accompany the formation of a new C—C bond between the C atom of the phenylene group bearing the methoxy unit and the C atom of the thienyl group bearing the methyl substituent (Fig. 2).

As the distance between these two C atoms is 3.717 (2) Å, the compound can be expected to exhibit photochromism (Fig. 2). It is known that photochromic activity in similar compounds is usually present when this distance is less than 4.2 Å (Kobatake & Irie, 2004; Ramamurthy & Venkatesan, 1987). We have been able to verify this experimentally. Upon irradiation with 365 nm radiation, the colorless crystals turned blue rapidly, but if the UV light is removed, the blue color returns to colorless immediately. In hexane, the irradiated compound showed an absorption maximum at 592 nm. Upon irradiation using a wavelength of more than 510 nm, the blue hexane solution was rendered colorless and showed an absorption maximum at 287 nm. In a poly(methyl methacylate) amorphous film, the title diarylethene also demonstrates photochromism. Yamamoto et al. (2003) have tested photocyclization of a photochromic diarylethene derivative in single crystals. The result showed a photogenerated closed-ring diarylethene whose occupancy was estimated to be roughly 9%. In order to prove that the diarylethene crystals structure is change by UV light, we hope to design an experiment where a continually irradiated crystal can be subjected to X-ray crystallographic analysis to see if changes in the intensities and the unit cell can be observed and interpreted.

Related literature top

For related literature, see: Fan et al. (2008); Irie (2000); Kobatake & Irie (2004); Perters et al. (2003); Ramamurthy & Venkatesan (1987); Tian & Yang (2004); Woodward & Hoffmann (1970); Yamamoto et al. (2003).

Experimental top

To a THF solution of 2-bromomethoxylbenzene (0.94 g, 5 mmol) was added a hexane solution of n-butyl lithium (2.0 ml, 5 mmol) at 195 K under a nitrogen atmosphere. The mixture was stirred for half an hour. An excess of octafluorocyclopentene (1.5 ml, 10 mmol) was added and stirring was continued for another two hours at this temperature. The reaction was then quenched by the addition of water. The product, 3,3,4,4,5,5-heptafluoro-(2-methoxylpheny)cyclopent-1-ene (1.43 g, 4.75 mmol), was collected and dried (yield 90%). This compound (1.43 g, 4.75 mmol) was reacted with 3-bromo-2-methyl-5-(4-methoxylphenyl)thiophene (0.94 g, 5 mmol; Perters et al., 2003) in the presence of n-butyl lithium (2.0 ml, 5 mmol) at 195 K under a nitrogen atmosphere. After an hour, the reaction was quenced by the addition of water. The solid product was purified by column chromatography on silica with petroleum ether as the eluant to give the title compound (1.50 g, 3.10 mmol, 65% yield; m.p. 384–390 K). Analysis calculated for C24H18F6O2S: C 59.50, H 3.75%; found: C 59.22, H 3.80%. 1H NMR (400 MHz, CDCl3, TMS): δ 1.87 (s, 3H, –CH3), 3.50 (s, 3H, –OCH3), 3.84 (s, 3H, –OCH3), 6.83, 6.85 (d, J = 8.0 Hz, 1H, aromatic H), 6.90, 6.92 (d, J = 8.0 Hz, 2H, aromatic H), 6.99 (t, J = 8.0 Hz, 1H, aromatic H), 7.11 (s, 1H, thienyl H), 7.37 (t, J = 8.0 Hz, 2H, aromatic H), 7.44, 7.46 (d, J = 8.0 Hz, 2H, aromatic H) p.p.m. 13C NMR (100 MHz, CDCl3): δ 14.03, 55.22, 55.39, 111.48, 114.36, 117.50, 120.80, 121.92, 126.79, 129.97, 131.73, 138.76, 141.07, 157.13, 159.32 p.p.m.

Refinement top

All H atoms were positioned geometrically and treated as riding [C—H = 0.96 Å (methyl) or 0.93 Å (aromatic), and Uiso(H) = 1.2Ueq(Caromatic) or 1.5Ueq(Cmethyl).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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, 2009).

Figures top
[Figure 1] Fig. 1. A displacement ellipsoid plot (Barbour, 2001) of (I). Ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Photochromic interconvertion of (I).
3,3,4,4,5,5-Hexafluoro-1-(2-methoxyphenyl)-2-[5-(4-methoxyphenyl)- 2-methyl-3-thienyl]cyclopent-1-ene top
Crystal data top
C24H18F6O2SZ = 2
Mr = 484.44F(000) = 496
Triclinic, P1Dx = 1.458 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.477 (1) ÅCell parameters from 4266 reflections
b = 10.398 (1) Åθ = 2.6–28.1°
c = 11.4573 (1) ŵ = 0.22 mm1
α = 90.259 (1)°T = 291 K
β = 101.436 (1)°Block, colorless
γ = 94.055 (1)°0.43 × 0.35 × 0.27 mm
V = 1103.7 (2) Å3
Data collection top
Bruker SMART area-detector
diffractometer
4979 independent reflections
Radiation source: fine-focus sealed tube4028 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
ϕ and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1112
Tmin = 0.913, Tmax = 0.944k = 1313
9784 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0706P)2 + 0.2768P]
where P = (Fo2 + 2Fc2)/3
4979 reflections(Δ/σ)max = 0.001
301 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C24H18F6O2Sγ = 94.055 (1)°
Mr = 484.44V = 1103.7 (2) Å3
Triclinic, P1Z = 2
a = 9.477 (1) ÅMo Kα radiation
b = 10.398 (1) ŵ = 0.22 mm1
c = 11.4573 (1) ÅT = 291 K
α = 90.259 (1)°0.43 × 0.35 × 0.27 mm
β = 101.436 (1)°
Data collection top
Bruker SMART area-detector
diffractometer
4979 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4028 reflections with I > 2σ(I)
Tmin = 0.913, Tmax = 0.944Rint = 0.012
9784 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.06Δρmax = 0.42 e Å3
4979 reflectionsΔρmin = 0.27 e Å3
301 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.35767 (5)0.62175 (4)0.50957 (4)0.04695 (15)
F10.84196 (17)0.83930 (15)1.03918 (12)0.0849 (5)
F20.96010 (13)0.88468 (13)0.90055 (16)0.0858 (5)
F30.95213 (17)0.62311 (14)1.03354 (13)0.0862 (5)
F40.99110 (15)0.65263 (15)0.85574 (16)0.0847 (5)
F50.69068 (16)0.53213 (15)0.95267 (14)0.0867 (5)
F60.77693 (16)0.49067 (12)0.79713 (13)0.0813 (5)
O10.44100 (15)0.82927 (15)0.87811 (15)0.0646 (4)
O20.11648 (17)0.11781 (15)0.54858 (14)0.0669 (4)
C10.5029 (2)0.93844 (19)0.83981 (16)0.0500 (4)
C20.4398 (3)1.0558 (3)0.8238 (2)0.0704 (7)
H20.34731.06280.83780.084*
C30.5152 (4)1.1620 (2)0.7870 (2)0.0808 (8)
H30.47221.23990.77640.097*
C40.6514 (3)1.1550 (2)0.7658 (2)0.0746 (7)
H40.70031.22720.74090.089*
C50.7158 (2)1.03886 (18)0.78183 (18)0.0551 (5)
H50.80871.03380.76790.066*
C60.64338 (19)0.92958 (16)0.81847 (15)0.0417 (4)
C70.2991 (2)0.8299 (4)0.9020 (2)0.0876 (9)
H7A0.29780.89400.96230.131*
H7B0.27090.74660.92920.131*
H7C0.23290.84950.83050.131*
C80.71278 (17)0.80721 (16)0.84067 (14)0.0376 (3)
C90.8542 (2)0.80428 (18)0.92724 (17)0.0487 (4)
C100.8935 (2)0.66381 (19)0.92636 (18)0.0507 (4)
C110.7535 (2)0.58817 (17)0.86666 (17)0.0490 (4)
C120.66143 (17)0.68728 (16)0.80123 (14)0.0383 (3)
C130.50794 (18)0.70038 (16)0.59793 (15)0.0405 (4)
C140.53461 (18)0.64722 (15)0.70866 (15)0.0382 (3)
C150.43241 (18)0.54275 (16)0.72156 (16)0.0424 (4)
H150.43640.49630.79120.051*
C160.32821 (18)0.51795 (16)0.62128 (15)0.0407 (4)
C170.5883 (2)0.80790 (19)0.54656 (17)0.0519 (5)
H17A0.54560.88740.55580.078*
H17B0.58360.79040.46350.078*
H17C0.68740.81490.58750.078*
C180.20679 (18)0.41865 (16)0.60024 (15)0.0414 (4)
C190.1658 (2)0.3508 (2)0.69379 (18)0.0584 (5)
H190.21190.37240.77150.070*
C200.0578 (2)0.2520 (2)0.67377 (19)0.0662 (6)
H200.03280.20740.73780.079*
C210.0134 (2)0.21922 (19)0.55872 (17)0.0491 (4)
C220.0214 (2)0.28777 (19)0.46465 (17)0.0510 (4)
H220.02810.26830.38740.061*
C230.1308 (2)0.38607 (19)0.48563 (17)0.0505 (4)
H230.15400.43150.42140.061*
C240.1867 (3)0.0760 (2)0.4314 (2)0.0674 (6)
H24A0.24090.14390.39270.101*
H24B0.25080.00140.43600.101*
H24C0.11570.05480.38660.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0456 (3)0.0474 (3)0.0423 (2)0.00456 (19)0.00182 (18)0.00416 (18)
F10.0981 (11)0.0933 (10)0.0543 (8)0.0385 (9)0.0173 (7)0.0272 (7)
F20.0436 (7)0.0618 (8)0.1404 (14)0.0125 (6)0.0047 (8)0.0113 (8)
F30.0996 (11)0.0693 (8)0.0707 (9)0.0207 (8)0.0343 (8)0.0006 (7)
F40.0596 (8)0.0831 (10)0.1170 (13)0.0075 (7)0.0305 (8)0.0217 (9)
F50.0775 (9)0.0878 (10)0.0871 (10)0.0098 (8)0.0022 (8)0.0478 (8)
F60.0921 (10)0.0483 (7)0.0893 (10)0.0241 (7)0.0223 (8)0.0198 (6)
O10.0442 (7)0.0713 (10)0.0815 (11)0.0034 (7)0.0236 (7)0.0145 (8)
O20.0623 (9)0.0681 (9)0.0609 (9)0.0297 (7)0.0018 (7)0.0053 (7)
C10.0460 (10)0.0564 (11)0.0445 (10)0.0085 (8)0.0001 (7)0.0135 (8)
C20.0656 (14)0.0808 (16)0.0607 (13)0.0338 (12)0.0066 (11)0.0190 (12)
C30.112 (2)0.0588 (14)0.0659 (15)0.0401 (15)0.0073 (14)0.0043 (11)
C40.116 (2)0.0439 (11)0.0608 (14)0.0116 (12)0.0081 (14)0.0066 (9)
C50.0694 (13)0.0426 (10)0.0529 (11)0.0027 (9)0.0117 (9)0.0035 (8)
C60.0457 (9)0.0388 (8)0.0385 (8)0.0040 (7)0.0032 (7)0.0040 (6)
C70.0405 (11)0.151 (3)0.0719 (16)0.0008 (14)0.0158 (11)0.0157 (17)
C80.0355 (8)0.0387 (8)0.0380 (8)0.0002 (6)0.0068 (6)0.0002 (6)
C90.0419 (9)0.0468 (10)0.0524 (10)0.0009 (8)0.0019 (8)0.0072 (8)
C100.0438 (10)0.0508 (10)0.0533 (11)0.0105 (8)0.0025 (8)0.0011 (8)
C110.0552 (11)0.0377 (9)0.0495 (10)0.0014 (8)0.0002 (8)0.0030 (7)
C120.0367 (8)0.0383 (8)0.0384 (8)0.0008 (6)0.0051 (6)0.0020 (6)
C130.0392 (8)0.0369 (8)0.0432 (9)0.0005 (7)0.0038 (7)0.0001 (7)
C140.0378 (8)0.0336 (8)0.0408 (8)0.0004 (6)0.0031 (6)0.0016 (6)
C150.0435 (9)0.0383 (8)0.0426 (9)0.0020 (7)0.0033 (7)0.0022 (7)
C160.0389 (8)0.0373 (8)0.0445 (9)0.0001 (7)0.0061 (7)0.0006 (7)
C170.0555 (11)0.0509 (10)0.0463 (10)0.0072 (9)0.0070 (8)0.0074 (8)
C180.0376 (8)0.0394 (9)0.0452 (9)0.0008 (7)0.0050 (7)0.0013 (7)
C190.0554 (11)0.0721 (13)0.0411 (10)0.0191 (10)0.0025 (8)0.0000 (9)
C200.0651 (13)0.0805 (15)0.0461 (11)0.0271 (11)0.0052 (9)0.0104 (10)
C210.0418 (9)0.0494 (10)0.0523 (10)0.0091 (8)0.0044 (8)0.0010 (8)
C220.0496 (10)0.0541 (11)0.0441 (10)0.0097 (8)0.0015 (8)0.0030 (8)
C230.0514 (10)0.0525 (11)0.0434 (10)0.0106 (8)0.0043 (8)0.0024 (8)
C240.0639 (13)0.0611 (13)0.0681 (14)0.0232 (11)0.0011 (10)0.0055 (10)
Geometric parameters (Å, º) top
S1—C131.726 (2)C8—C91.503 (2)
S1—C161.730 (2)C9—C101.533 (3)
F1—C91.361 (2)C10—C111.528 (3)
F2—C91.344 (2)C11—C121.504 (2)
F3—C101.328 (2)C12—C141.471 (2)
F4—C101.355 (2)C13—C141.370 (2)
F5—C111.362 (2)C13—C171.497 (2)
F6—C111.344 (2)C14—C151.432 (2)
O1—C11.356 (3)C15—C161.369 (2)
O1—C71.425 (3)C15—H150.9300
O2—C211.374 (2)C16—C181.472 (2)
O2—C241.426 (3)C17—H17A0.9600
C1—C21.393 (3)C17—H17B0.9600
C1—C61.409 (3)C17—H17C0.9600
C2—C31.386 (4)C18—C191.390 (3)
C2—H20.9300C18—C231.394 (2)
C3—C41.366 (4)C19—C201.383 (3)
C3—H30.9300C19—H190.9300
C4—C51.388 (3)C20—C211.386 (3)
C4—H40.9300C20—H200.9300
C5—C61.395 (3)C21—C221.376 (3)
C5—H50.9300C22—C231.388 (3)
C6—C81.474 (2)C22—H220.9300
C7—H7A0.9600C23—H230.9300
C7—H7B0.9600C24—H24A0.9600
C7—H7C0.9600C24—H24B0.9600
C8—C121.348 (2)C24—H24C0.9600
C13—S1—C1693.16 (8)C12—C11—C10105.0 (1)
C1—O1—C7119.3 (2)C8—C12—C14129.0 (2)
C21—O2—C24117.4 (2)C8—C12—C11110.7 (2)
O1—C1—C2125.0 (2)C14—C12—C11120.4 (1)
O1—C1—C6115.6 (2)C14—C13—C17130.5 (2)
C2—C1—C6119.3 (2)C14—C13—S1110.4 (1)
C3—C2—C1119.9 (2)C17—C13—S1119.1 (1)
C3—C2—H2120.1C13—C14—C15113.0 (2)
C1—C2—H2120.1C13—C14—C12123.2 (2)
C4—C3—C2121.5 (2)C15—C14—C12123.6 (2)
C4—C3—H3119.2C16—C15—C14113.3 (2)
C2—C3—H3119.2C16—C15—H15123.3
C3—C4—C5119.2 (2)C14—C15—H15123.3
C3—C4—H4120.4C15—C16—C18129.1 (2)
C5—C4—H4120.4C15—C16—S1110.1 (1)
C4—C5—C6121.0 (2)C18—C16—S1120.8 (1)
C4—C5—H5119.5C13—C17—H17A109.5
C6—C5—H5119.5C13—C17—H17B109.5
C5—C6—C1119.0 (2)H17A—C17—H17B109.5
C5—C6—C8121.6 (2)C13—C17—H17C109.5
C1—C6—C8119.4 (2)H17A—C17—H17C109.5
O1—C7—H7A109.5H17B—C17—H17C109.5
O1—C7—H7B109.5C19—C18—C23117.2 (2)
H7A—C7—H7B109.5C19—C18—C16121.3 (2)
O1—C7—H7C109.5C23—C18—C16121.6 (2)
H7A—C7—H7C109.5C20—C19—C18121.4 (2)
H7B—C7—H7C109.5C20—C19—H19119.3
C12—C8—C6128.9 (2)C18—C19—H19119.3
C12—C8—C9110.9 (2)C19—C20—C21120.3 (2)
C6—C8—C9119.9 (2)C19—C20—H20119.9
F2—C9—F1105.5 (2)C21—C20—H20119.9
F2—C9—C8113.9 (2)O2—C21—C22124.9 (2)
F1—C9—C8111.6 (2)O2—C21—C20115.5 (2)
F2—C9—C10111.1 (2)C22—C21—C20119.6 (2)
F1—C9—C10109.5 (2)C21—C22—C23119.7 (2)
C8—C9—C10105.3 (1)C21—C22—H22120.2
F3—C10—F4107.3 (2)C23—C22—H22120.2
F3—C10—C9113.1 (2)C22—C23—C18121.9 (2)
F4—C10—C9109.0 (2)C22—C23—H23119.1
F3—C10—C11114.8 (2)C18—C23—H23119.1
F4—C10—C11107.8 (2)O2—C24—H24A109.5
C9—C10—C11104.6 (1)O2—C24—H24B109.5
F6—C11—F5105.7 (2)H24A—C24—H24B109.5
F6—C11—C12114.1 (2)O2—C24—H24C109.5
F5—C11—C12111.1 (2)H24A—C24—H24C109.5
F6—C11—C10112.3 (2)H24B—C24—H24C109.5
F5—C11—C10108.7 (2)
C7—O1—C1—C21.6 (3)C9—C8—C12—C14173.9 (2)
C7—O1—C1—C6179.9 (2)C6—C8—C12—C11167.6 (2)
O1—C1—C2—C3178.4 (2)C9—C8—C12—C116.3 (2)
C6—C1—C2—C30.2 (3)F6—C11—C12—C8139.5 (2)
C1—C2—C3—C40.1 (4)F5—C11—C12—C8101.2 (2)
C2—C3—C4—C50.2 (4)C10—C11—C12—C816.1 (2)
C3—C4—C5—C60.4 (3)F6—C11—C12—C1440.7 (2)
C4—C5—C6—C10.3 (3)F5—C11—C12—C1478.6 (2)
C4—C5—C6—C8177.4 (2)C10—C11—C12—C14164.1 (2)
O1—C1—C6—C5178.4 (2)C16—S1—C13—C140.7 (1)
C2—C1—C6—C50.0 (3)C16—S1—C13—C17179.3 (2)
O1—C1—C6—C81.2 (2)C17—C13—C14—C15178.7 (2)
C2—C1—C6—C8177.2 (2)S1—C13—C14—C150.2 (2)
C5—C6—C8—C12131.2 (2)C17—C13—C14—C123.0 (3)
C1—C6—C8—C1251.7 (3)S1—C13—C14—C12175.5 (1)
C5—C6—C8—C955.4 (2)C8—C12—C14—C1349.3 (3)
C1—C6—C8—C9121.7 (2)C11—C12—C14—C13130.9 (2)
C12—C8—C9—F2128.0 (2)C8—C12—C14—C15135.4 (2)
C6—C8—C9—F257.5 (2)C11—C12—C14—C1544.3 (2)
C12—C8—C9—F1112.6 (2)C13—C14—C15—C160.6 (2)
C6—C8—C9—F161.9 (2)C12—C14—C15—C16176.2 (2)
C12—C8—C9—C106.1 (2)C14—C15—C16—C18179.5 (2)
C6—C8—C9—C10179.4 (2)C14—C15—C16—S11.0 (2)
F2—C9—C10—F395.2 (2)C13—S1—C16—C151.0 (1)
F1—C9—C10—F321.0 (2)C13—S1—C16—C18179.6 (1)
C8—C9—C10—F3141.0 (2)C15—C16—C18—C1913.6 (3)
F2—C9—C10—F424.1 (2)S1—C16—C18—C19168.0 (1)
F1—C9—C10—F4140.3 (2)C15—C16—C18—C23164.5 (2)
C8—C9—C10—F499.7 (2)S1—C16—C18—C2313.8 (2)
F2—C9—C10—C11139.2 (2)C23—C18—C19—C202.4 (3)
F1—C9—C10—C11104.7 (2)C16—C18—C19—C20175.9 (2)
C8—C9—C10—C1115.4 (2)C18—C19—C20—C210.7 (4)
F3—C10—C11—F692.2 (2)C24—O2—C21—C223.7 (3)
F4—C10—C11—F627.3 (2)C24—O2—C21—C20176.5 (2)
C9—C10—C11—F6143.3 (2)C19—C20—C21—O2178.6 (2)
F3—C10—C11—F524.4 (2)C19—C20—C21—C221.6 (4)
F4—C10—C11—F5143.9 (2)O2—C21—C22—C23178.1 (2)
C9—C10—C11—F5100.2 (2)C20—C21—C22—C232.2 (3)
F3—C10—C11—C12143.3 (2)C21—C22—C23—C180.4 (3)
F4—C10—C11—C1297.2 (2)C19—C18—C23—C221.8 (3)
C9—C10—C11—C1218.8 (2)C16—C18—C23—C22176.4 (2)
C6—C8—C12—C1412.2 (3)

Experimental details

Crystal data
Chemical formulaC24H18F6O2S
Mr484.44
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)9.477 (1), 10.398 (1), 11.4573 (1)
α, β, γ (°)90.259 (1), 101.436 (1), 94.055 (1)
V3)1103.7 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.43 × 0.35 × 0.27
Data collection
DiffractometerBruker SMART area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.913, 0.944
No. of measured, independent and
observed [I > 2σ(I)] reflections
9784, 4979, 4028
Rint0.012
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.135, 1.06
No. of reflections4979
No. of parameters301
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.42, 0.27

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

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