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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1105.
Published online 2009 April 25. doi:  10.1107/S1600536809013993
PMCID: PMC2977783

1-[5-(3-Chloro­phen­yl)-2-methyl-3-thi­en­yl]-3,3,4,4,5,5-hexa­fluoro-2-(2-methoxy­phen­yl)­cyclo­pent-1-ene

Abstract

The title compound, C23H15ClF6OS, has thienyl and phenyl­ene substituents on the double-bond C atoms of the envelope-shaped cyclo­pentenyl ring. The aromatic systems are aligned at 55.3 (4) (thien­yl) and 60.8 (7)° (phenyl­ene) with respect to the planar C—C=C—C portion of the main central cyclo­pentenyl ring.

Related literature

For the synthesis of the precursors and related compounds, see: Fan et al. (2008 [triangle], 2009 [triangle]); Pu et al. (2008 [triangle]).

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Object name is e-65-o1105-scheme1.jpg

Experimental

Crystal data

  • C23H15ClF6OS
  • M r = 488.86
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1105-efi1.jpg
  • a = 9.4057 (10) Å
  • b = 10.2900 (11) Å
  • c = 11.9548 (13) Å
  • α = 83.529 (1)°
  • β = 71.564 (1)°
  • γ = 80.639 (1)°
  • V = 1080.7 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.34 mm−1
  • T = 291 K
  • 0.49 × 0.45 × 0.33 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.851, T max = 0.896
  • 8254 measured reflections
  • 3997 independent reflections
  • 3358 reflections with I > 2σ(I)
  • R int = 0.011

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.111
  • S = 1.03
  • 3997 reflections
  • 321 parameters
  • 553 restraints
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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: ORTEPIII (Burnett & Johnson, 1996 [triangle]) and ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013993/ng2571sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013993/ng2571Isup2.hkl

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

Acknowledgments

This work was supported by the Science Fund of the Education Office of Jiangxi (grant Nos. GJJ09306 and GJJ09302) and the Youth Science Fund of the Education Office of Jiangxi (grant Nos. GJJ09567 and GJJ09572).

supplementary crystallographic information

Comment

Crystal of the compound when dissolved in hexane can show photochromism. Upon irradiation with 365 nm light, the colorless crystals hexane solution turns blue rapidly. The blue compound displays an absorption maximum at 584 nm. Upon irradiation with visible light with a wavelength greater than 510 nm, the blue crystals hexane solution revert to their initial colorless state; a hexane solution has an absorption maximum at 291 nm. In a polymethylmethacylate amorphous film, the title diarylethene also demonstrates photochromism as similar as that in hexane.

Experimental

The title compound was synthesized from the reaction of (2-methoxylpheny)perfluorocyclopent-1-ene (1.43 g, 4.75 mmol) (Fan et al., 2009) and 3-bromo-2-methyl-5-(3-chlorophenyl)thiophene (1.44 g, 5 mmol) (Fan et al., 2008) with n-butyllithium (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 eluent to give the title compound 1.58 g (3.23 mmol) in 68% yield. C&H elemental analysis. Calc. for C23H15ClF6OS: C 56.51, H, 3.09%. Found C 55.92, H 3.15%.

Refinement

All H atoms attached to C were fixed geometrically and treated as riding with C—H = 0.96 Å (methyl) or 0.93 Å (aromatic) with Uiso(H) = 1.2Ueq(aromatic) or Uiso(H) = 1.5Ueq(methyl). The cyclopent-1-ene ring in C9, C10, C11-envelope conformation is disorder, the C8—C9, C8—C9', C12—C11 and C12—C11' distance was strained to 1.50 (1) Å, respectively. The distance of C9—F1, C9—F2, F9'—F1', C9'—F2', C10—F3, C10—F4, C10'—F3', C10'—F4', C11—F5, C11—F6, C11'—F5'and C11—F6' was restrained to 1.34 (1) Å, respectively. The occupancies of the disorder components refined to a 0.784 (3):0.216 (3) ratio for C9:C9', F1:F1' and F2:F2'. The occupances of the disorder components refined to a 0.834 (5):0.166 (5) ratio for C11:C11', F5:F5', F6:F6' and 0.826 (2):0.174 (2) ratio for C10:C10', F3:F3', F4:F4'.

Figures

Fig. 1.
Molecular view the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
Fig. 2.
The diorder in cyclopent-1-ene ring.

Crystal data

C23H15ClF6OSZ = 2
Mr = 488.86F(000) = 496
Triclinic, P1Dx = 1.502 Mg m3
a = 9.4057 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2900 (11) ÅCell parameters from 4346 reflections
c = 11.9548 (13) Åθ = 2.5–28.1°
α = 83.529 (1)°µ = 0.34 mm1
β = 71.564 (1)°T = 291 K
γ = 80.639 (1)°Block, colourless
V = 1080.7 (2) Å30.49 × 0.45 × 0.33 mm

Data collection

Bruker SMART CCD area-detector diffractometer3997 independent reflections
Radiation source: fine-focus sealed tube3358 reflections with I > 2σ(I)
graphiteRint = 0.011
[var phi] and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.851, Tmax = 0.896k = −12→12
8254 measured reflectionsl = −14→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0497P)2 + 0.4496P] where P = (Fo2 + 2Fc2)/3
3997 reflections(Δ/σ)max = 0.001
321 parametersΔρmax = 0.28 e Å3
553 restraintsΔρmin = −0.36 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
C90.7086 (3)0.7630 (3)0.5031 (3)0.0560 (8)0.784 (3)
F10.5898 (3)0.8609 (2)0.5303 (2)0.0930 (9)0.784 (3)
F20.7750 (3)0.7584 (2)0.58991 (15)0.0854 (7)0.784 (3)
C9'0.6784 (10)0.7854 (12)0.4846 (8)0.0560 (8)0.216 (3)
F1'0.5498 (9)0.8402 (8)0.4640 (8)0.0930 (9)0.216 (3)
F2'0.6890 (12)0.8415 (10)0.5755 (6)0.0854 (7)0.216 (3)
C100.6576 (3)0.6302 (3)0.5013 (3)0.0566 (7)0.826 (2)
F30.52853 (19)0.6483 (2)0.4715 (2)0.0893 (6)0.826 (2)
F40.6283 (3)0.56317 (19)0.60649 (15)0.0877 (6)0.826 (2)
C10'0.6811 (14)0.6391 (15)0.5180 (12)0.0566 (7)0.174 (2)
F3'0.5428 (9)0.6053 (11)0.5606 (12)0.0893 (6)0.174 (2)
F4'0.7538 (10)0.5982 (9)0.5974 (7)0.0877 (6)0.174 (2)
C110.7876 (3)0.5608 (3)0.4040 (3)0.0504 (6)0.834 (5)
F50.7345 (3)0.4861 (3)0.34450 (17)0.0778 (7)0.834 (5)
F60.8815 (3)0.4760 (2)0.4529 (2)0.0771 (7)0.834 (5)
C11'0.7621 (15)0.5759 (12)0.4012 (12)0.0504 (6)0.166 (5)
F5'0.6680 (14)0.5518 (13)0.3457 (9)0.0778 (7)0.166 (5)
F6'0.8458 (15)0.4630 (13)0.4176 (13)0.0771 (7)0.166 (5)
Cl11.52883 (10)0.09741 (8)0.13406 (7)0.1001 (3)
S11.10823 (7)0.64743 (6)−0.01005 (5)0.05725 (18)
O11.11475 (18)0.81945 (15)0.35023 (17)0.0710 (5)
C11.0232 (2)0.9304 (2)0.32810 (19)0.0521 (5)
C21.0714 (3)1.0534 (2)0.2928 (2)0.0672 (6)
H21.17151.06340.28190.081*
C30.9705 (3)1.1608 (2)0.2740 (2)0.0705 (7)
H31.00391.24270.25000.085*
C40.8232 (3)1.1490 (2)0.2899 (2)0.0650 (6)
H40.75621.22220.27770.078*
C50.7744 (3)1.0270 (2)0.32442 (19)0.0539 (5)
H50.67381.01880.33560.065*
C60.8730 (2)0.91614 (18)0.34282 (16)0.0444 (4)
C71.2362 (3)0.8347 (3)0.3900 (2)0.0758 (7)
H7A1.31430.86890.32560.114*
H7B1.27550.75060.41980.114*
H7C1.20170.89490.45180.114*
C80.8185 (2)0.78631 (19)0.38147 (17)0.0442 (4)
C120.8636 (2)0.67244 (18)0.32766 (16)0.0413 (4)
C130.9725 (2)0.64498 (17)0.21130 (16)0.0419 (4)
C141.0915 (2)0.53693 (18)0.19382 (17)0.0440 (4)
H141.10960.47980.25540.053*
C151.1763 (2)0.52489 (19)0.07887 (17)0.0461 (4)
C160.9669 (2)0.71461 (19)0.10727 (18)0.0488 (5)
C170.8561 (3)0.8294 (2)0.0852 (2)0.0666 (6)
H17A0.76030.82630.14510.100*
H17B0.84390.82480.00900.100*
H17C0.89320.91040.08730.100*
C181.3086 (2)0.4285 (2)0.02687 (17)0.0480 (4)
C191.3943 (3)0.4423 (2)−0.0917 (2)0.0658 (6)
H191.36660.5128−0.13990.079*
C201.5198 (3)0.3523 (3)−0.1381 (2)0.0772 (7)
H201.57630.3638−0.21700.093*
C211.5622 (3)0.2472 (3)−0.0706 (2)0.0681 (6)
H211.64670.1868−0.10250.082*
C221.4773 (3)0.2320 (2)0.0462 (2)0.0594 (5)
C231.3525 (2)0.3205 (2)0.09609 (19)0.0531 (5)
H231.29770.30840.17540.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C90.0574 (15)0.0530 (16)0.0522 (14)−0.0082 (12)−0.0075 (11)−0.0065 (12)
F10.0854 (14)0.0621 (11)0.0886 (17)0.0065 (10)0.0275 (13)−0.0103 (11)
F20.1147 (17)0.1028 (17)0.0470 (9)−0.0445 (13)−0.0213 (10)−0.0054 (10)
C9'0.0574 (15)0.0530 (16)0.0522 (14)−0.0082 (12)−0.0075 (11)−0.0065 (12)
F1'0.0854 (14)0.0621 (11)0.0886 (17)0.0065 (10)0.0275 (13)−0.0103 (11)
F2'0.1147 (17)0.1028 (17)0.0470 (9)−0.0445 (13)−0.0213 (10)−0.0054 (10)
C100.0539 (14)0.0575 (13)0.0548 (14)−0.0176 (11)−0.0095 (10)0.0055 (11)
F30.0540 (9)0.0936 (14)0.1218 (17)−0.0148 (9)−0.0273 (11)−0.0044 (12)
F40.1098 (16)0.0752 (11)0.0590 (10)−0.0282 (11)0.0021 (10)0.0153 (8)
C10'0.0539 (14)0.0575 (13)0.0548 (14)−0.0176 (11)−0.0095 (10)0.0055 (11)
F3'0.0540 (9)0.0936 (14)0.1218 (17)−0.0148 (9)−0.0273 (11)−0.0044 (12)
F4'0.1098 (16)0.0752 (11)0.0590 (10)−0.0282 (11)0.0021 (10)0.0153 (8)
C110.0549 (14)0.0419 (12)0.0553 (11)−0.0108 (11)−0.0182 (10)0.0030 (9)
F50.0961 (16)0.0636 (15)0.0790 (10)−0.0429 (13)−0.0152 (10)−0.0131 (10)
F60.0748 (13)0.0608 (10)0.0836 (16)0.0013 (9)−0.0233 (9)0.0277 (10)
C11'0.0549 (14)0.0419 (12)0.0553 (11)−0.0108 (11)−0.0182 (10)0.0030 (9)
F5'0.0961 (16)0.0636 (15)0.0790 (10)−0.0429 (13)−0.0152 (10)−0.0131 (10)
F6'0.0748 (13)0.0608 (10)0.0836 (16)0.0013 (9)−0.0233 (9)0.0277 (10)
Cl10.0996 (6)0.0937 (5)0.0895 (5)0.0389 (4)−0.0325 (4)0.0023 (4)
S10.0699 (4)0.0557 (3)0.0415 (3)0.0014 (3)−0.0171 (2)0.0026 (2)
O10.0581 (9)0.0508 (9)0.1132 (14)−0.0043 (7)−0.0380 (9)−0.0118 (9)
C10.0571 (12)0.0424 (10)0.0589 (12)−0.0093 (9)−0.0176 (10)−0.0084 (9)
C20.0677 (14)0.0549 (13)0.0837 (16)−0.0232 (11)−0.0220 (12)−0.0052 (12)
C30.0964 (19)0.0432 (12)0.0748 (16)−0.0224 (12)−0.0259 (14)0.0020 (11)
C40.0873 (17)0.0440 (12)0.0642 (14)−0.0038 (11)−0.0281 (12)0.0024 (10)
C50.0603 (12)0.0479 (11)0.0533 (12)−0.0045 (9)−0.0188 (10)−0.0024 (9)
C60.0521 (11)0.0388 (10)0.0421 (10)−0.0067 (8)−0.0127 (8)−0.0059 (8)
C70.0712 (16)0.0849 (18)0.0764 (17)−0.0021 (14)−0.0305 (13)−0.0147 (14)
C80.0458 (10)0.0430 (10)0.0450 (10)−0.0086 (8)−0.0144 (8)−0.0029 (8)
C120.0436 (10)0.0388 (9)0.0451 (10)−0.0074 (8)−0.0181 (8)−0.0002 (8)
C130.0484 (10)0.0366 (9)0.0436 (10)−0.0088 (8)−0.0171 (8)−0.0016 (7)
C140.0510 (11)0.0389 (9)0.0429 (10)−0.0050 (8)−0.0171 (8)0.0006 (8)
C150.0516 (11)0.0424 (10)0.0457 (10)−0.0070 (8)−0.0169 (9)−0.0019 (8)
C160.0577 (12)0.0431 (10)0.0471 (11)−0.0033 (9)−0.0203 (9)−0.0015 (8)
C170.0837 (17)0.0573 (13)0.0593 (13)0.0119 (12)−0.0337 (12)−0.0014 (11)
C180.0510 (11)0.0471 (11)0.0461 (10)−0.0060 (8)−0.0142 (9)−0.0067 (8)
C190.0787 (16)0.0590 (13)0.0490 (12)−0.0009 (11)−0.0087 (11)−0.0029 (10)
C200.0825 (17)0.0754 (17)0.0548 (14)−0.0005 (14)0.0032 (12)−0.0114 (12)
C210.0601 (14)0.0703 (15)0.0658 (15)0.0051 (11)−0.0086 (11)−0.0218 (12)
C220.0572 (13)0.0586 (13)0.0627 (13)0.0036 (10)−0.0226 (11)−0.0089 (10)
C230.0513 (11)0.0568 (12)0.0477 (11)−0.0030 (9)−0.0115 (9)−0.0058 (9)

Geometric parameters (Å, °)

C9—F11.359 (3)C3—H30.9300
C9—F21.363 (4)C4—C51.381 (3)
C9—C81.514 (3)C4—H40.9300
C9—C101.525 (4)C5—C61.392 (3)
C9'—F2'1.324 (9)C5—H50.9300
C9'—F1'1.332 (9)C6—C81.481 (3)
C9'—C81.493 (8)C7—H7A0.9600
C9'—C10'1.512 (9)C7—H7B0.9600
C10—F41.334 (3)C7—H7C0.9600
C10—F31.349 (3)C8—C121.342 (3)
C10—C111.536 (4)C12—C131.469 (3)
C10'—F3'1.327 (10)C13—C161.375 (3)
C10'—F4'1.332 (10)C13—C141.426 (3)
C10'—C11'1.524 (9)C14—C151.361 (3)
C11—F51.348 (3)C14—H140.9300
C11—F61.358 (3)C15—C181.472 (3)
C11—C121.510 (3)C16—C171.502 (3)
C11'—F6'1.326 (10)C17—H17A0.9600
C11'—F5'1.328 (10)C17—H17B0.9600
C11'—C121.500 (9)C17—H17C0.9600
Cl1—C221.741 (2)C18—C191.396 (3)
S1—C161.718 (2)C18—C231.396 (3)
S1—C151.731 (2)C19—C201.380 (3)
O1—C11.368 (3)C19—H190.9300
O1—C71.405 (3)C20—C211.359 (4)
C1—C21.389 (3)C20—H200.9300
C1—C61.398 (3)C21—C221.377 (3)
C2—C31.383 (4)C21—H210.9300
C2—H20.9300C22—C231.376 (3)
C3—C41.361 (4)C23—H230.9300
F1—C9—F2105.1 (3)C5—C6—C8120.66 (18)
F1—C9—C8112.8 (2)C1—C6—C8120.53 (17)
F2—C9—C8111.9 (2)O1—C7—H7A109.5
F1—C9—C10111.9 (3)O1—C7—H7B109.5
F2—C9—C10110.1 (2)H7A—C7—H7B109.5
C8—C9—C10105.2 (2)O1—C7—H7C109.5
F2'—C9'—F1'107.7 (8)H7A—C7—H7C109.5
F2'—C9'—C8112.1 (8)H7B—C7—H7C109.5
F1'—C9'—C8116.1 (8)C12—C8—C6129.26 (18)
F2'—C9'—C10'107.2 (10)C12—C8—C9'114.1 (5)
F1'—C9'—C10'112.4 (9)C6—C8—C9'115.9 (5)
C8—C9'—C10'100.9 (7)C12—C8—C9109.6 (2)
F4—C10—F3106.5 (2)C6—C8—C9120.8 (2)
F4—C10—C9112.6 (3)C8—C12—C13129.51 (17)
F3—C10—C9110.1 (3)C8—C12—C11'106.6 (6)
F4—C10—C11114.1 (3)C13—C12—C11'123.3 (6)
F3—C10—C11110.1 (2)C8—C12—C11111.5 (2)
C9—C10—C11103.5 (2)C13—C12—C11118.97 (19)
F3'—C10'—F4'108.1 (9)C16—C13—C14112.60 (17)
F3'—C10'—C9'111.9 (11)C16—C13—C12124.45 (17)
F4'—C10'—C9'112.7 (11)C14—C13—C12122.85 (16)
F3'—C10'—C11'109.3 (11)C15—C14—C13113.91 (17)
F4'—C10'—C11'111.1 (11)C15—C14—H14123.0
C9'—C10'—C11'103.7 (9)C13—C14—H14123.0
F5—C11—F6105.7 (2)C14—C15—C18129.71 (18)
F5—C11—C12113.2 (2)C14—C15—S1109.86 (15)
F6—C11—C12112.9 (2)C18—C15—S1120.42 (15)
F5—C11—C10110.8 (2)C13—C16—C17129.94 (19)
F6—C11—C10110.0 (3)C13—C16—S1110.41 (15)
C12—C11—C10104.2 (2)C17—C16—S1119.58 (16)
F6'—C11'—F5'107.9 (9)C16—C17—H17A109.5
F6'—C11'—C12109.1 (11)C16—C17—H17B109.5
F5'—C11'—C12110.4 (9)H17A—C17—H17B109.5
F6'—C11'—C10'110.9 (12)C16—C17—H17C109.5
F5'—C11'—C10'113.1 (11)H17A—C17—H17C109.5
C12—C11'—C10'105.4 (8)H17B—C17—H17C109.5
C16—S1—C1593.21 (9)C19—C18—C23118.1 (2)
C1—O1—C7118.22 (18)C19—C18—C15121.50 (19)
O1—C1—C2123.8 (2)C23—C18—C15120.39 (18)
O1—C1—C6116.66 (17)C20—C19—C18120.6 (2)
C2—C1—C6119.5 (2)C20—C19—H19119.7
C3—C2—C1120.0 (2)C18—C19—H19119.7
C3—C2—H2120.0C21—C20—C19121.2 (2)
C1—C2—H2120.0C21—C20—H20119.4
C4—C3—C2121.2 (2)C19—C20—H20119.4
C4—C3—H3119.4C20—C21—C22118.6 (2)
C2—C3—H3119.4C20—C21—H21120.7
C3—C4—C5119.2 (2)C22—C21—H21120.7
C3—C4—H4120.4C23—C22—C21122.0 (2)
C5—C4—H4120.4C23—C22—Cl1118.70 (18)
C4—C5—C6121.3 (2)C21—C22—Cl1119.34 (18)
C4—C5—H5119.4C22—C23—C18119.6 (2)
C6—C5—H5119.4C22—C23—H23120.2
C5—C6—C1118.77 (18)C18—C23—H23120.2
F1—C9—C10—F4−89.8 (3)C10—C9—C8—C12−16.4 (3)
F2—C9—C10—F426.7 (4)F1—C9—C8—C647.6 (4)
C8—C9—C10—F4147.5 (3)F2—C9—C8—C6−70.7 (3)
F1—C9—C10—F328.9 (4)C10—C9—C8—C6169.7 (2)
F2—C9—C10—F3145.4 (3)F1—C9—C8—C9'−29.7 (18)
C8—C9—C10—F3−93.8 (3)F2—C9—C8—C9'−148 (2)
F1—C9—C10—C11146.6 (3)C10—C9—C8—C9'92 (2)
F2—C9—C10—C11−96.9 (3)C6—C8—C12—C13−4.6 (3)
C8—C9—C10—C1123.8 (3)C9'—C8—C12—C13165.0 (5)
F2'—C9'—C10'—F3'95.5 (11)C9—C8—C12—C13−177.7 (2)
F1'—C9'—C10'—F3'−22.6 (13)C6—C8—C12—C11'−175.7 (6)
C8—C9'—C10'—F3'−147.0 (10)C9'—C8—C12—C11'−6.1 (7)
F2'—C9'—C10'—F4'−26.6 (13)C9—C8—C12—C11'11.2 (6)
F1'—C9'—C10'—F4'−144.7 (9)C6—C8—C12—C11174.6 (2)
C8—C9'—C10'—F4'90.9 (11)C9'—C8—C12—C11−15.8 (5)
F2'—C9'—C10'—C11'−146.8 (9)C9—C8—C12—C111.5 (3)
F1'—C9'—C10'—C11'95.0 (10)F6'—C11'—C12—C8−132.9 (9)
C8—C9'—C10'—C11'−29.3 (10)F5'—C11'—C12—C8108.7 (10)
F4—C10—C11—F592.5 (3)C10'—C11'—C12—C8−13.7 (10)
F3—C10—C11—F5−27.2 (3)F6'—C11'—C12—C1355.3 (12)
C9—C10—C11—F5−144.9 (2)F5'—C11'—C12—C13−63.1 (12)
F4—C10—C11—F6−24.1 (3)C10'—C11'—C12—C13174.5 (6)
F3—C10—C11—F6−143.8 (3)F6'—C11'—C12—C11−13 (3)
C9—C10—C11—F698.5 (3)F5'—C11'—C12—C11−131 (4)
F4—C10—C11—C12−145.4 (2)C10'—C11'—C12—C11106 (4)
F3—C10—C11—C1294.9 (3)F5—C11—C12—C8134.4 (2)
C9—C10—C11—C12−22.8 (3)F6—C11—C12—C8−105.5 (3)
F3'—C10'—C11'—F6'−95.1 (13)C10—C11—C12—C813.9 (3)
F4'—C10'—C11'—F6'24.1 (13)F5—C11—C12—C13−46.3 (3)
C9'—C10'—C11'—F6'145.4 (10)F6—C11—C12—C1373.8 (3)
F3'—C10'—C11'—F5'26.3 (13)C10—C11—C12—C13−166.80 (19)
F4'—C10'—C11'—F5'145.5 (10)F5—C11—C12—C11'71 (4)
C9'—C10'—C11'—F5'−93.2 (10)F6—C11—C12—C11'−169 (4)
F3'—C10'—C11'—C12146.9 (10)C10—C11—C12—C11'−49 (4)
F4'—C10'—C11'—C12−93.8 (11)C8—C12—C13—C16−52.8 (3)
C9'—C10'—C11'—C1227.4 (12)C11'—C12—C13—C16117.0 (7)
C7—O1—C1—C228.8 (3)C11—C12—C13—C16128.1 (2)
C7—O1—C1—C6−151.1 (2)C8—C12—C13—C14131.0 (2)
O1—C1—C2—C3−179.1 (2)C11'—C12—C13—C14−59.2 (7)
C6—C1—C2—C30.8 (4)C11—C12—C13—C14−48.2 (3)
C1—C2—C3—C40.3 (4)C16—C13—C14—C150.6 (2)
C2—C3—C4—C5−0.6 (4)C12—C13—C14—C15177.27 (17)
C3—C4—C5—C6−0.2 (3)C13—C14—C15—C18178.83 (18)
C4—C5—C6—C11.3 (3)C13—C14—C15—S1−0.5 (2)
C4—C5—C6—C8179.1 (2)C16—S1—C15—C140.21 (16)
O1—C1—C6—C5178.30 (19)C16—S1—C15—C18−179.19 (16)
C2—C1—C6—C5−1.6 (3)C14—C13—C16—C17176.5 (2)
O1—C1—C6—C80.5 (3)C12—C13—C16—C17−0.1 (3)
C2—C1—C6—C8−179.4 (2)C14—C13—C16—S1−0.4 (2)
C5—C6—C8—C12120.1 (2)C12—C13—C16—S1−177.03 (14)
C1—C6—C8—C12−62.1 (3)C15—S1—C16—C130.14 (16)
C5—C6—C8—C9'−49.3 (5)C15—S1—C16—C17−177.15 (18)
C1—C6—C8—C9'128.5 (5)C14—C15—C18—C19−171.0 (2)
C5—C6—C8—C9−67.4 (3)S1—C15—C18—C198.3 (3)
C1—C6—C8—C9110.4 (2)C14—C15—C18—C238.5 (3)
F2'—C9'—C8—C12137.0 (8)S1—C15—C18—C23−172.26 (16)
F1'—C9'—C8—C12−98.6 (9)C23—C18—C19—C20−0.8 (4)
C10'—C9'—C8—C1223.2 (8)C15—C18—C19—C20178.7 (2)
F2'—C9'—C8—C6−52.0 (10)C18—C19—C20—C210.9 (4)
F1'—C9'—C8—C672.5 (10)C19—C20—C21—C22−0.2 (4)
C10'—C9'—C8—C6−165.8 (6)C20—C21—C22—C23−0.6 (4)
F2'—C9'—C8—C959.4 (16)C20—C21—C22—Cl1179.5 (2)
F1'—C9'—C8—C9−176 (3)C21—C22—C23—C180.6 (3)
C10'—C9'—C8—C9−54.4 (18)Cl1—C22—C23—C18−179.50 (17)
F1—C9—C8—C12−138.6 (3)C19—C18—C23—C220.1 (3)
F2—C9—C8—C12103.1 (3)C15—C18—C23—C22−179.40 (19)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2571).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Fan, C., Liu, G., Liu, W., Yang, T. & Ng, S. W. (2009). Acta Cryst. C65, o243–o244. [PubMed]
  • Fan, C.-B., Pu, S.-Z., Liu, G. & Yang, T.-S. (2008). J. Photochem. Photobiol. A, 194, 333–343.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Pu, S.-Z., Fan, C.-B., Miao, W.-J. & Liu, G. (2008). Tetrahedron, 64, 9464–9470.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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