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The title compound, C19H16F6S4, is a new asymmetric photochromic diaryl­ethene which contains 3-thienyl substituents. The distance between the two reactive C atoms in the mol­ecule is 3.548 (3) Å. The dihedral angles between the central cyclo­pentene ring and two thio­phene rings are 45.7 (1) and 44.5 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015054/bt2060sup1.cif
Contains datablocks global, Ia

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015054/bt2060Iasup2.hkl
Contains datablock Ia

CCDC reference: 610703

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.054
  • wR factor = 0.111
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

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Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C12
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.49 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Bruker, 1997); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-(2,5-Dimethyl-3-thienyl)-2-[5-(1,3-dithiolan-2-yl)-2-methyl-3-thienyl]- 3,3,4,4,5,5-hexafluoro-cyclopent-1-ene top
Crystal data top
C19H16F6S4Z = 2
Mr = 486.56F(000) = 496
Triclinic, P1Dx = 1.549 Mg m3
Hall symbol: -P 1Melting point: 387.7 K
a = 8.954 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.305 (3) ÅCell parameters from 25 reflections
c = 13.329 (3) Åθ = 5.1–12.6°
α = 100.471 (14)°µ = 0.51 mm1
β = 106.617 (16)°T = 295 K
γ = 111.010 (17)°Prism, colourless
V = 1043.1 (6) Å30.5 × 0.4 × 0.3 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.2°
Graphite monochromatorh = 101
ω scansk = 1111
4403 measured reflectionsl = 1515
3638 independent reflections3 standard reflections every 97 reflections
3109 reflections with I > 2σ(I) intensity decay: none
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.001P)2 + 2P]
where P = (Fo2 + 2Fc2)/3
3638 reflections(Δ/σ)max = 0.006
269 parametersΔρmax = 1.14 e Å3
4 restraintsΔρmin = 0.46 e Å3
Special details top

Experimental. 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 1.818 (s, 3H, –CH3), 1.861 (s, 3H, –CH3), 2.422 (s, 3H, –CH3), 3.343–3.357 (t, 2H, J = 2.8 Hz, –CH2–), 3.439–3.464 (t, 2H, J = 5.0 Hz, –CH2–), 5.809 (s, 1H, –CH), 6.712 (s, 1H, thiophene-H), 6.979 (s, 1H, thiophene-H); 19F NMR (376 MHz, CDCl3, δ, p.p.m.): 109.92 (2 F), 110.23 (2 F), 131.90 (2 F); 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 14.15–15.06, 39.95, 50.52, 116.13, 1236.36–124.60, 125.19, 127.22, 131.10, 137.73, 139.71, 142.07, 145.15.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S11.01847 (7)0.76934 (7)0.49747 (5)0.05634 (17)
S21.27327 (11)0.58176 (8)0.45668 (7)0.0832 (3)
S31.45941 (9)0.88807 (8)0.60356 (7)0.0790 (3)
S40.34589 (8)0.42826 (7)0.14151 (6)0.06198 (19)
F10.5752 (3)0.83867 (18)0.00798 (13)0.1073 (8)
F20.5240 (2)0.96406 (17)0.11254 (16)0.0955 (6)
F30.8162 (3)1.1671 (2)0.1958 (2)0.1205 (9)
F40.8440 (3)1.0860 (2)0.04884 (16)0.1305 (8)
F51.0284 (2)0.9623 (2)0.14039 (14)0.0955 (5)
F61.0714 (2)1.12416 (18)0.28393 (14)0.0937 (7)
C10.8448 (3)0.8844 (2)0.23455 (18)0.0489 (6)
C20.6749 (3)0.8273 (2)0.17270 (18)0.0490 (6)
C30.6401 (3)0.9164 (3)0.0990 (2)0.0581 (7)
C40.8123 (4)1.0440 (3)0.1278 (2)0.0775 (9)
C50.9462 (3)1.0061 (3)0.1999 (2)0.0607 (7)
C60.8782 (3)0.8120 (2)0.40667 (18)0.0476 (6)
C70.9348 (3)0.8423 (2)0.32407 (17)0.0458 (6)
C81.0932 (3)0.8320 (2)0.33697 (19)0.0497 (6)
H8A1.15010.85140.28910.060*
C91.1533 (3)0.7913 (2)0.42565 (19)0.0512 (6)
C101.3144 (3)0.7709 (3)0.4635 (2)0.0601 (7)
H10A1.37550.79760.41460.072*
C11A1.4175 (9)0.6089 (6)0.5887 (4)0.0882 (19)0.423 (6)
H11A1.50310.57310.59020.106*0.423 (6)
H11B1.33760.54910.61510.106*0.423 (6)
C11B1.3224 (8)0.6101 (5)0.6000 (4)0.0882 (19)0.577 (6)
H11C1.34630.53350.62170.106*0.577 (6)
H11D1.22540.61100.61680.106*0.577 (6)
C121.4710 (5)0.7537 (3)0.6657 (3)0.1178 (16)
H12A1.58940.78810.71670.141*
H12B1.39870.74280.70860.141*
C130.7252 (3)0.8168 (3)0.4278 (2)0.0577 (7)
H13A0.69550.88630.39800.087*
H13B0.75260.84570.50590.087*
H13C0.62900.72150.39300.087*
C140.5396 (3)0.5614 (2)0.15406 (18)0.0509 (6)
C150.5313 (3)0.6930 (2)0.16426 (18)0.0476 (6)
C160.3668 (3)0.6830 (3)0.16073 (19)0.0549 (7)
H16A0.34000.76260.16540.066*
C170.2533 (3)0.5479 (3)0.1500 (2)0.0581 (7)
C180.6826 (3)0.5221 (3)0.1477 (2)0.0633 (8)
H18A0.74820.58370.11470.095*
H18B0.63450.42140.10350.095*
H18C0.75710.53610.22070.095*
C190.0714 (3)0.4962 (3)0.1450 (3)0.0777 (10)
H19A0.03500.57270.14000.117*
H19B0.06650.47170.21050.117*
H19C0.00380.41120.08130.117*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0487 (3)0.0690 (3)0.0553 (3)0.0254 (2)0.0193 (2)0.0301 (2)
S20.0921 (4)0.0663 (3)0.0863 (5)0.0430 (3)0.0162 (4)0.0250 (3)
S30.0552 (3)0.0620 (4)0.0922 (5)0.0173 (3)0.0008 (3)0.0273 (3)
S40.0548 (3)0.0512 (3)0.0682 (4)0.0168 (2)0.0150 (3)0.0200 (3)
F10.1589 (16)0.0734 (9)0.0533 (9)0.0412 (10)0.0013 (10)0.0231 (7)
F20.0924 (8)0.0964 (8)0.1459 (13)0.0657 (7)0.0571 (8)0.0759 (8)
F30.1100 (13)0.0665 (10)0.1620 (19)0.0364 (9)0.0282 (13)0.0283 (11)
F40.0940 (12)0.1936 (15)0.1206 (11)0.0473 (11)0.0403 (9)0.1197 (10)
F50.1024 (8)0.1280 (11)0.1095 (9)0.0652 (8)0.0739 (7)0.0713 (8)
F60.0852 (11)0.0721 (10)0.0811 (10)0.0017 (9)0.0162 (9)0.0302 (8)
C10.0459 (9)0.0517 (11)0.0496 (11)0.0207 (8)0.0183 (8)0.0182 (9)
C20.0491 (10)0.0512 (10)0.0470 (11)0.0236 (8)0.0145 (9)0.0183 (8)
C30.0586 (12)0.0574 (12)0.0565 (13)0.0273 (10)0.0137 (10)0.0231 (10)
C40.0778 (15)0.0777 (15)0.0872 (16)0.0333 (12)0.0319 (13)0.0494 (12)
C50.0519 (11)0.0654 (13)0.0598 (13)0.0183 (10)0.0202 (10)0.0256 (10)
C60.0393 (9)0.0458 (10)0.0478 (11)0.0136 (8)0.0104 (8)0.0131 (9)
C70.0393 (9)0.0449 (10)0.0463 (11)0.0143 (8)0.0124 (8)0.0141 (8)
C80.0436 (9)0.0518 (11)0.0522 (11)0.0180 (8)0.0187 (8)0.0184 (9)
C90.0431 (10)0.0491 (11)0.0578 (12)0.0169 (8)0.0162 (9)0.0202 (9)
C100.0503 (11)0.0658 (12)0.0722 (14)0.0283 (9)0.0226 (10)0.0346 (10)
C11A0.111 (4)0.0785 (19)0.086 (2)0.052 (3)0.026 (3)0.0463 (17)
C11B0.111 (4)0.0785 (19)0.086 (2)0.052 (3)0.026 (3)0.0463 (17)
C120.135 (3)0.0876 (19)0.094 (2)0.033 (2)0.002 (2)0.0469 (17)
C130.0497 (10)0.0665 (13)0.0562 (12)0.0244 (10)0.0209 (9)0.0190 (10)
C140.0474 (10)0.0527 (11)0.0444 (11)0.0206 (9)0.0087 (9)0.0144 (9)
C150.0429 (10)0.0487 (10)0.0441 (10)0.0179 (8)0.0089 (8)0.0156 (8)
C160.0475 (10)0.0560 (11)0.0571 (12)0.0240 (9)0.0129 (9)0.0174 (10)
C170.0465 (11)0.0612 (13)0.0556 (13)0.0177 (10)0.0138 (10)0.0154 (10)
C180.0559 (11)0.0596 (13)0.0661 (15)0.0283 (10)0.0132 (11)0.0114 (11)
C190.0525 (13)0.0846 (18)0.0845 (18)0.0205 (13)0.0253 (12)0.0227 (15)
Geometric parameters (Å, º) top
S1—C61.719 (2)C8—H8A0.9300
S1—C91.723 (3)C9—C101.490 (3)
S2—C11A1.762 (5)C10—H10A0.9800
S2—C11B1.775 (5)C11A—C121.469 (6)
S2—C101.829 (3)C11A—H11A0.9600
S3—C121.757 (4)C11A—H11B0.9600
S3—C101.817 (3)C11B—C121.476 (5)
S4—C171.720 (3)C11B—H11C0.9600
S4—C141.722 (2)C11B—H11D0.9600
F1—C31.338 (3)C12—H12A0.9700
F2—C31.340 (3)C12—H12B0.9700
F3—C41.401 (4)C13—H13A0.9600
F4—C41.274 (4)C13—H13B0.9600
F5—C51.348 (3)C13—H13C0.9600
F6—C51.342 (3)C14—C151.369 (3)
C1—C21.343 (3)C14—C181.494 (4)
C1—C71.467 (3)C15—C161.426 (3)
C1—C51.498 (3)C16—C171.349 (3)
C2—C151.471 (3)C16—H16A0.9300
C2—C31.504 (4)C17—C191.497 (4)
C3—C41.509 (4)C18—H18A0.9600
C4—C51.526 (4)C18—H18B0.9600
C6—C71.377 (3)C18—H18C0.9600
C6—C131.491 (3)C19—H19A0.9600
C7—C81.424 (3)C19—H19B0.9600
C8—C91.357 (3)C19—H19C0.9600
C6—S1—C992.82 (12)S2—C11A—H11A116.0
C11A—S2—C10100.8 (2)C12—C11A—H11B99.5
C11B—S2—C1095.93 (19)S2—C11A—H11B99.9
C12—S3—C1099.64 (14)H11A—C11A—H11B108.0
C17—S4—C1493.27 (12)C12—C11B—S2110.6 (4)
C2—C1—C7129.4 (2)C12—C11B—H11C109.9
C2—C1—C5110.7 (2)S2—C11B—H11C111.5
C7—C1—C5119.92 (18)C12—C11B—H11D107.2
C1—C2—C15129.8 (2)S2—C11B—H11D109.5
C1—C2—C3110.6 (2)H11C—C11B—H11D108.0
C15—C2—C3119.50 (18)C11A—C12—S3115.1 (3)
F1—C3—F2105.6 (2)C11B—C12—S3110.8 (3)
F1—C3—C2112.0 (2)C11A—C12—H12A108.5
F2—C3—C2112.7 (2)C11B—C12—H12A136.3
F1—C3—C4110.0 (2)S3—C12—H12A108.5
F2—C3—C4110.6 (2)C11A—C12—H12B108.5
C2—C3—C4106.0 (2)C11B—C12—H12B77.1
F4—C4—F3103.6 (3)S3—C12—H12B108.5
F4—C4—C3117.4 (2)H12A—C12—H12B107.5
F3—C4—C3107.7 (3)C6—C13—H13A109.5
F4—C4—C5116.1 (3)C6—C13—H13B109.5
F3—C4—C5106.3 (2)H13A—C13—H13B109.5
C3—C4—C5105.0 (2)C6—C13—H13C109.5
F6—C5—F5104.9 (2)H13A—C13—H13C109.5
F6—C5—C1114.4 (2)H13B—C13—H13C109.5
F5—C5—C1111.2 (2)C15—C14—C18129.8 (2)
F6—C5—C4111.6 (2)C15—C14—S4110.07 (19)
F5—C5—C4109.5 (2)C18—C14—S4120.06 (18)
C1—C5—C4105.2 (2)C15—C14—C673.37 (12)
C7—C6—C13130.1 (2)C18—C14—C679.86 (12)
C7—C6—S1110.55 (18)S4—C14—C6125.37 (12)
C13—C6—S1119.32 (19)C14—C15—C16112.5 (2)
C7—C6—C1473.58 (12)C14—C15—C2123.0 (2)
C13—C6—C1479.63 (12)C16—C15—C2124.4 (2)
S1—C6—C14125.07 (11)C17—C16—C15114.1 (2)
C6—C7—C8112.4 (2)C17—C16—H16A122.9
C6—C7—C1123.9 (2)C15—C16—H16A122.9
C8—C7—C1123.7 (2)C16—C17—C19129.4 (3)
C9—C8—C7113.6 (2)C16—C17—S4110.0 (2)
C9—C8—H8A123.2C19—C17—S4120.6 (2)
C7—C8—H8A123.2C14—C18—H18A109.5
C8—C9—C10127.7 (2)C14—C18—H18B109.5
C8—C9—S1110.57 (19)H18A—C18—H18B109.5
C10—C9—S1121.68 (19)C14—C18—H18C109.5
C9—C10—S3112.52 (19)H18A—C18—H18C109.5
C9—C10—S2113.36 (16)H18B—C18—H18C109.5
S3—C10—S2107.93 (14)C17—C19—H19A109.5
C9—C10—H10A107.6C17—C19—H19B109.5
S3—C10—H10A107.6H19A—C19—H19B109.5
S2—C10—H10A107.6C17—C19—H19C109.5
C12—C11A—S2111.7 (4)H19A—C19—H19C109.5
C12—C11A—H11A118.5H19B—C19—H19C109.5
C7—C1—C2—C1510.1 (5)C7—C8—C9—C10179.7 (2)
C5—C1—C2—C15168.9 (2)C7—C8—C9—S11.6 (2)
C7—C1—C2—C3173.8 (2)C6—S1—C9—C80.95 (17)
C5—C1—C2—C37.2 (3)C6—S1—C9—C10179.21 (18)
C1—C2—C3—F1116.9 (2)C8—C9—C10—S3121.5 (2)
C15—C2—C3—F159.7 (3)S1—C9—C10—S356.5 (2)
C1—C2—C3—F2124.2 (2)C8—C9—C10—S2115.7 (2)
C15—C2—C3—F259.3 (3)S1—C9—C10—S266.4 (2)
C1—C2—C3—C43.1 (3)C12—S3—C10—C9120.7 (2)
C15—C2—C3—C4179.6 (2)C12—S3—C10—S25.1 (2)
F1—C3—C4—F421.0 (4)C11A—S2—C10—C9131.8 (3)
F2—C3—C4—F495.3 (3)C11B—S2—C10—C9102.1 (3)
C2—C3—C4—F4142.2 (3)C11A—S2—C10—S36.5 (3)
F1—C3—C4—F3137.3 (2)C11B—S2—C10—S323.3 (3)
F2—C3—C4—F321.0 (3)C10—S2—C11A—C1218.7 (5)
C2—C3—C4—F3101.4 (3)C10—S2—C11B—C1238.6 (4)
F1—C3—C4—C5109.7 (3)S2—C11A—C12—S325.0 (6)
F2—C3—C4—C5134.0 (2)S2—C11B—C12—S339.7 (5)
C2—C3—C4—C511.6 (3)C10—S3—C12—C11A18.6 (5)
C2—C1—C5—F6137.3 (2)C10—S3—C12—C11B20.4 (4)
C7—C1—C5—F643.6 (4)C17—S4—C14—C150.05 (19)
C2—C1—C5—F5104.0 (2)C17—S4—C14—C18177.3 (2)
C7—C1—C5—F575.1 (3)C17—S4—C14—C683.39 (15)
C2—C1—C5—C414.4 (3)C7—C6—C14—C1577.6 (2)
C7—C1—C5—C4166.5 (2)C13—C6—C14—C1559.8 (2)
F4—C4—C5—F688.5 (3)S1—C6—C14—C15178.46 (19)
F3—C4—C5—F626.1 (3)C7—C6—C14—C1859.4 (2)
C3—C4—C5—F6140.1 (2)C13—C6—C14—C18163.1 (2)
F4—C4—C5—F527.2 (3)S1—C6—C14—C1844.5 (2)
F3—C4—C5—F5141.8 (2)C7—C6—C14—S4179.2 (2)
C3—C4—C5—F5104.2 (3)C13—C6—C14—S443.3 (2)
F4—C4—C5—C1146.8 (2)S1—C6—C14—S475.3 (2)
F3—C4—C5—C198.6 (2)C18—C14—C15—C16176.4 (2)
C3—C4—C5—C115.4 (3)S4—C14—C15—C160.5 (3)
C9—S1—C6—C70.09 (17)C6—C14—C15—C16122.8 (2)
C9—S1—C6—C13177.99 (17)C18—C14—C15—C20.9 (4)
C9—S1—C6—C1483.84 (14)S4—C14—C15—C2177.88 (17)
C13—C6—C7—C8176.8 (2)C6—C14—C15—C259.84 (19)
S1—C6—C7—C80.8 (2)C1—C2—C15—C1445.6 (4)
C14—C6—C7—C8122.71 (18)C3—C2—C15—C14130.1 (3)
C13—C6—C7—C11.6 (3)C1—C2—C15—C16137.3 (3)
S1—C6—C7—C1179.16 (16)C3—C2—C15—C1646.9 (3)
C14—C6—C7—C158.89 (18)C14—C15—C16—C171.0 (3)
C2—C1—C7—C644.0 (4)C2—C15—C16—C17178.3 (2)
C5—C1—C7—C6137.0 (2)C15—C16—C17—C19179.0 (3)
C2—C1—C7—C8137.8 (3)C15—C16—C17—S41.0 (3)
C5—C1—C7—C841.2 (3)C14—S4—C17—C160.6 (2)
C6—C7—C8—C91.5 (3)C14—S4—C17—C19179.4 (2)
C1—C7—C8—C9179.93 (19)
 

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