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The title compound, C31H18F6S2, is a mol­ecular switch based on dithienylperfluoro­cyclo­pentene. The mol­ecule possesses pseudo-C2 symmetry and has the open form of the switch. There are a number of intra­molecular C—H...F hydrogen bonds, but in the crystal structure there are no inter­actions between symmetry-related mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032545/ez2021sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032545/ez2021Isup2.hkl
Contains datablock I

CCDC reference: 295405

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.048
  • wR factor = 0.129
  • Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.107 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C14 - C17 ... 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C27 - C30 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2004); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

1,2-bis[5-(4-ethynylphenyl)-2-methylthiophen-3-yl]-3,3,4,4,5,5-hexacyclopentene top
Crystal data top
C31H18F6S2F(000) = 1160
Mr = 568.57Dx = 1.467 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 18629 reflections
a = 26.7998 (17) Åθ = 1.6–25.6°
b = 9.0730 (5) ŵ = 0.27 mm1
c = 10.7628 (6) ÅT = 173 K
β = 100.337 (5)°Block, pale blue
V = 2574.5 (3) Å30.40 × 0.37 × 0.30 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
3722 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.107
Graphite monochromatorθmax = 25.1°, θmin = 1.5°
ω and φ scansh = 3132
18574 measured reflectionsk = 1010
4577 independent reflectionsl = 1212
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0628P)2 + 0.7289P]
where P = (Fo2 + 2Fc2)/3
4577 reflections(Δ/σ)max = 0.001
354 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.39 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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*/Ueq
S10.34895 (2)0.76528 (7)0.45326 (5)0.0379 (2)
S20.12231 (2)0.80828 (7)0.41051 (6)0.0398 (2)
F10.32795 (6)1.30758 (18)0.52818 (18)0.0581 (6)
F20.31196 (7)1.31709 (17)0.32463 (17)0.0577 (6)
F30.26073 (7)1.51004 (18)0.50694 (18)0.0599 (6)
F40.22731 (7)1.44263 (19)0.31683 (16)0.0579 (6)
F50.21202 (6)1.31613 (16)0.60861 (13)0.0440 (5)
F60.16018 (5)1.33706 (16)0.43064 (15)0.0459 (5)
C10.26856 (9)1.1350 (3)0.4265 (2)0.0320 (7)
C20.29071 (9)1.2874 (3)0.4264 (2)0.0389 (8)
C30.24712 (10)1.3924 (3)0.4336 (2)0.0414 (8)
C40.20798 (9)1.2963 (3)0.4802 (2)0.0350 (7)
C50.22081 (9)1.1409 (3)0.4503 (2)0.0307 (7)
C60.30109 (9)1.0085 (3)0.4139 (2)0.0328 (7)
C70.33498 (9)1.0014 (3)0.3260 (2)0.0344 (7)
C80.36350 (8)0.8771 (3)0.3350 (2)0.0331 (7)
C90.30490 (9)0.8863 (3)0.4910 (2)0.0352 (7)
C100.27898 (10)0.8530 (3)0.5989 (2)0.0426 (8)
C110.40284 (9)0.8354 (3)0.2627 (2)0.0355 (7)
C120.42398 (9)0.9408 (3)0.1947 (2)0.0401 (8)
C130.46085 (9)0.9048 (3)0.1265 (2)0.0442 (8)
C140.47852 (9)0.7611 (3)0.1248 (2)0.0447 (8)
C150.45725 (10)0.6532 (3)0.1919 (2)0.0459 (8)
C160.42004 (10)0.6907 (3)0.2599 (2)0.0426 (8)
C170.51853 (11)0.7244 (4)0.0575 (3)0.0534 (10)
C180.55257 (12)0.6946 (4)0.0055 (3)0.0673 (13)
C190.18264 (9)1.0271 (3)0.4556 (2)0.0326 (7)
C200.14783 (8)1.0373 (3)0.5407 (2)0.0333 (7)
C210.11279 (9)0.9273 (3)0.5291 (2)0.0345 (7)
C220.17305 (9)0.9062 (3)0.3770 (2)0.0357 (7)
C230.19812 (10)0.8564 (3)0.2713 (2)0.0421 (8)
C240.07078 (9)0.9107 (3)0.5977 (2)0.0349 (7)
C250.07284 (9)0.9788 (3)0.7143 (2)0.0394 (8)
C260.03244 (10)0.9718 (3)0.7769 (2)0.0406 (8)
C270.01161 (9)0.8977 (3)0.7246 (2)0.0395 (8)
C280.01360 (10)0.8272 (3)0.6089 (3)0.0431 (8)
C290.02686 (9)0.8326 (3)0.5468 (2)0.0406 (8)
C300.05386 (10)0.8964 (3)0.7901 (3)0.0483 (9)
C310.08845 (11)0.8980 (4)0.8444 (3)0.0599 (11)
H7A0.337401.077100.266400.0410*
H10A0.246400.804900.567500.0640*
H10B0.300300.787200.658300.0640*
H10C0.273100.944800.642000.0640*
H12A0.412701.040000.195300.0480*
H13A0.474400.979000.079900.0530*
H15A0.468400.553900.190700.0550*
H16A0.405900.616600.305600.0510*
H18A0.579900.670600.036200.0810*
H20A0.149001.114600.600700.0400*
H23A0.173300.805400.207800.0630*
H23B0.225900.788900.304000.0630*
H23C0.211600.942000.232700.0630*
H25A0.102601.030900.751200.0470*
H26A0.034701.018200.856900.0490*
H28A0.043300.774800.572400.0520*
H29A0.025000.782700.468500.0490*
H31A0.116300.899300.888000.0720*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0398 (3)0.0410 (4)0.0338 (3)0.0087 (3)0.0090 (2)0.0045 (3)
S20.0421 (4)0.0360 (4)0.0417 (3)0.0069 (3)0.0085 (3)0.0049 (3)
F10.0432 (9)0.0515 (10)0.0749 (11)0.0086 (7)0.0017 (8)0.0155 (9)
F20.0724 (11)0.0404 (9)0.0720 (11)0.0028 (8)0.0447 (9)0.0034 (8)
F30.0665 (11)0.0372 (9)0.0833 (12)0.0139 (8)0.0328 (9)0.0201 (9)
F40.0682 (11)0.0540 (10)0.0554 (9)0.0095 (8)0.0215 (8)0.0219 (8)
F50.0586 (9)0.0393 (8)0.0373 (7)0.0041 (7)0.0169 (7)0.0085 (6)
F60.0397 (8)0.0393 (8)0.0588 (9)0.0075 (6)0.0089 (7)0.0045 (7)
C10.0363 (12)0.0310 (12)0.0292 (11)0.0005 (9)0.0076 (9)0.0004 (9)
C20.0386 (13)0.0357 (13)0.0451 (13)0.0056 (11)0.0149 (11)0.0029 (11)
C30.0500 (14)0.0304 (13)0.0454 (14)0.0011 (11)0.0132 (11)0.0014 (11)
C40.0370 (12)0.0338 (13)0.0350 (12)0.0025 (10)0.0089 (10)0.0012 (10)
C50.0353 (12)0.0295 (12)0.0267 (10)0.0010 (9)0.0043 (9)0.0004 (9)
C60.0326 (12)0.0332 (12)0.0318 (11)0.0005 (9)0.0034 (9)0.0029 (10)
C70.0350 (12)0.0354 (13)0.0332 (12)0.0020 (10)0.0071 (9)0.0002 (10)
C80.0302 (11)0.0393 (13)0.0290 (11)0.0004 (10)0.0029 (9)0.0024 (10)
C90.0356 (12)0.0383 (13)0.0310 (11)0.0020 (10)0.0040 (9)0.0007 (10)
C100.0466 (14)0.0459 (15)0.0382 (13)0.0113 (12)0.0153 (11)0.0087 (11)
C110.0308 (11)0.0438 (14)0.0307 (11)0.0021 (10)0.0022 (9)0.0039 (10)
C120.0400 (13)0.0388 (14)0.0436 (13)0.0028 (11)0.0129 (11)0.0069 (11)
C130.0399 (14)0.0506 (16)0.0439 (14)0.0057 (12)0.0127 (11)0.0065 (12)
C140.0334 (13)0.0638 (18)0.0365 (12)0.0042 (12)0.0052 (10)0.0060 (13)
C150.0440 (14)0.0521 (16)0.0416 (14)0.0159 (12)0.0076 (11)0.0005 (12)
C160.0424 (14)0.0476 (16)0.0383 (13)0.0094 (12)0.0089 (11)0.0052 (12)
C170.0429 (15)0.066 (2)0.0516 (16)0.0078 (14)0.0096 (12)0.0036 (15)
C180.0514 (18)0.089 (3)0.068 (2)0.0113 (17)0.0285 (16)0.0038 (19)
C190.0334 (12)0.0296 (12)0.0340 (11)0.0003 (9)0.0039 (9)0.0008 (10)
C200.0343 (12)0.0321 (12)0.0332 (11)0.0012 (10)0.0050 (9)0.0003 (10)
C210.0355 (12)0.0332 (13)0.0343 (12)0.0004 (10)0.0049 (9)0.0035 (10)
C220.0378 (12)0.0345 (13)0.0340 (12)0.0016 (10)0.0042 (9)0.0007 (10)
C230.0440 (14)0.0433 (15)0.0399 (13)0.0037 (11)0.0098 (11)0.0062 (11)
C240.0342 (12)0.0310 (12)0.0390 (12)0.0016 (10)0.0051 (10)0.0054 (10)
C250.0378 (13)0.0373 (14)0.0422 (13)0.0068 (10)0.0045 (10)0.0004 (11)
C260.0458 (14)0.0358 (14)0.0419 (13)0.0016 (11)0.0123 (11)0.0016 (11)
C270.0367 (13)0.0351 (13)0.0473 (14)0.0025 (10)0.0095 (11)0.0122 (11)
C280.0368 (13)0.0405 (15)0.0501 (15)0.0074 (11)0.0030 (11)0.0056 (12)
C290.0405 (13)0.0378 (14)0.0424 (13)0.0045 (11)0.0042 (11)0.0028 (11)
C300.0431 (15)0.0450 (16)0.0572 (16)0.0017 (12)0.0105 (13)0.0130 (13)
C310.0476 (16)0.067 (2)0.070 (2)0.0046 (15)0.0235 (15)0.0195 (17)
Geometric parameters (Å, º) top
S1—C81.726 (2)C19—C221.381 (4)
S1—C91.714 (3)C20—C211.361 (4)
S2—C211.725 (2)C21—C241.461 (3)
S2—C221.716 (3)C22—C231.491 (3)
F1—C21.355 (3)C24—C251.391 (3)
F2—C21.349 (3)C24—C291.399 (3)
F3—C31.339 (3)C25—C261.376 (4)
F4—C31.353 (3)C26—C271.387 (4)
F5—C41.379 (3)C27—C281.392 (4)
F6—C41.348 (3)C27—C301.437 (4)
C1—C21.505 (4)C28—C291.373 (4)
C1—C51.351 (3)C30—C311.181 (4)
C1—C61.462 (4)C7—H7A0.9500
C2—C31.520 (4)C10—H10A0.9800
C3—C41.517 (4)C10—H10B0.9800
C4—C51.500 (4)C10—H10C0.9800
C5—C191.462 (4)C12—H12A0.9500
C6—C71.426 (3)C13—H13A0.9500
C6—C91.378 (4)C15—H15A0.9500
C7—C81.356 (4)C16—H16A0.9500
C8—C111.468 (3)C18—H18A0.9500
C9—C101.487 (3)C20—H20A0.9500
C11—C121.386 (4)C23—H23A0.9800
C11—C161.394 (4)C23—H23B0.9800
C12—C131.372 (3)C23—H23C0.9800
C13—C141.388 (4)C25—H25A0.9500
C14—C151.397 (4)C26—H26A0.9500
C14—C171.437 (4)C28—H28A0.9500
C15—C161.381 (4)C29—H29A0.9500
C17—C181.184 (4)C31—H31A0.9500
C19—C201.423 (3)
S1···F3i3.4317 (19)C28···C24x3.424 (4)
S1···C13ii3.584 (2)C28···C29x3.500 (4)
S1···C11ii3.505 (2)C28···C21x3.580 (4)
S1···C12ii3.524 (2)C28···C26xi3.519 (4)
S1···C16ii3.525 (2)C29···C29x3.434 (4)
S1···C14ii3.636 (2)C29···C28x3.500 (4)
S1···C15ii3.591 (3)C31···C22x3.469 (4)
S2···C26iii3.617 (3)C1···H10C2.8800
S2···C25iii3.464 (3)C1···H23C2.9300
S1···H16A2.7500C2···H7A2.9900
S2···H29A2.8000C4···H20A2.7600
F1···F32.554 (2)C5···H23C2.9300
F2···F42.526 (3)C5···H10C2.8900
F2···C72.929 (3)C6···H23C2.8700
F2···F33.125 (3)C6···H23B2.9300
F3···F12.554 (2)C7···H12A2.7400
F3···F23.125 (3)C8···H10Biii2.7500
F3···C10iv3.275 (3)C9···H23B2.7900
F3···S1iv3.4317 (19)C11···H10Biii2.9900
F3···F63.099 (2)C12···H7A2.8600
F3···F52.551 (2)C13···H15Avii2.8200
F4···F62.539 (2)C17···H13Axii3.0900
F4···C20v3.336 (3)C18···H15Axiii3.0700
F4···F22.526 (3)C19···H10A2.7700
F5···F32.551 (2)C19···H10C2.9500
F5···C203.073 (3)C20···H25A2.7600
F6···F33.099 (2)C22···H10A2.7300
F6···C203.008 (3)C25···H20A2.8400
F6···F42.539 (2)C27···H29Aii3.1000
F1···H7Avi2.7400C28···H26Axi2.9000
F1···H18Avii2.7500C30···H29Aii3.0600
F2···H7A2.4000C31···H28Aii2.9800
F3···H10Aiv2.8000H7A···F22.4000
F4···H10Cv2.6300H7A···C22.9900
F5···H20A2.4800H7A···C122.8600
F5···H31Aviii2.6800H7A···H12A2.3100
F5···H23Cvi2.5700H7A···F1v2.7400
F6···H20A2.7800H10A···F3i2.8000
F6···H31Aviii2.5200H10A···C192.7700
F6···H25Av2.5400H10A···C222.7300
C1···C233.408 (4)H10B···C8ii2.7500
C5···C103.304 (4)H10B···C11ii2.9900
C6···C223.508 (3)H10C···C12.8800
C6···C233.218 (4)H10C···C52.8900
C7···F22.929 (3)H10C···C192.9500
C9···C233.380 (3)H10C···F4vi2.6300
C9···C223.531 (3)H12A···C72.7400
C9···C193.473 (4)H12A···H7A2.3100
C10···F3i3.275 (3)H13A···C17xii3.0900
C10···C223.400 (3)H13A···H13Axii2.4200
C10···C53.304 (4)H15A···C13ix2.8200
C10···C193.180 (4)H15A···C18xiii3.0700
C11···S1iii3.505 (2)H16A···S12.7500
C12···S1iii3.524 (2)H18A···F1ix2.7500
C13···S1iii3.584 (2)H20A···F52.4800
C13···C15vii3.490 (4)H20A···F62.7800
C14···S1iii3.636 (2)H20A···C42.7600
C15···C13ix3.490 (4)H20A···C252.8400
C15···S1iii3.591 (3)H20A···H25A2.3400
C16···S1iii3.525 (2)H23B···C62.9300
C19···C93.473 (4)H23B···C92.7900
C19···C103.180 (4)H23C···C12.9300
C20···F63.008 (3)H23C···C52.9300
C20···F53.073 (3)H23C···C62.8700
C20···F4vi3.336 (3)H23C···F5v2.5700
C21···C28x3.580 (4)H25A···C202.7600
C22···C103.400 (3)H25A···H20A2.3400
C22···C63.508 (3)H25A···F6vi2.5400
C22···C93.531 (3)H26A···C28viii2.9000
C22···C31x3.469 (4)H26A···H28Aviii2.4500
C23···C63.218 (4)H28A···H26Axi2.4500
C23···C13.408 (4)H28A···C31iii2.9800
C23···C93.380 (3)H29A···S22.8000
C24···C28x3.424 (4)H29A···C27iii3.1000
C25···S2ii3.464 (3)H29A···C30iii3.0600
C26···C28viii3.519 (4)H31A···F5xi2.6800
C26···S2ii3.617 (3)H31A···F6xi2.5200
C8—S1—C993.13 (12)S2—C21—C20109.62 (17)
C21—S2—C2293.41 (12)S2—C21—C24122.62 (19)
C2—C1—C5110.6 (2)C20—C21—C24127.7 (2)
C2—C1—C6118.6 (2)S2—C22—C19110.48 (17)
C5—C1—C6130.5 (2)S2—C22—C23119.08 (19)
F1—C2—F2105.8 (2)C19—C22—C23130.4 (2)
F1—C2—C1110.9 (2)C21—C24—C25120.1 (2)
F1—C2—C3109.59 (19)C21—C24—C29121.7 (2)
F2—C2—C1114.1 (2)C25—C24—C29118.2 (2)
F2—C2—C3110.9 (2)C24—C25—C26120.9 (2)
C1—C2—C3105.6 (2)C25—C26—C27120.7 (2)
F3—C3—F4107.4 (2)C26—C27—C28118.6 (2)
F3—C3—C2113.5 (2)C26—C27—C30119.5 (2)
F3—C3—C4113.3 (2)C28—C27—C30121.9 (2)
F4—C3—C2109.93 (19)C27—C28—C29120.8 (2)
F4—C3—C4108.8 (2)C24—C29—C28120.7 (2)
C2—C3—C4103.9 (2)C27—C30—C31178.8 (3)
F5—C4—F6105.01 (19)C6—C7—H7A123.00
F5—C4—C3108.78 (19)C8—C7—H7A123.00
F5—C4—C5110.98 (19)C9—C10—H10A109.00
F6—C4—C3112.1 (2)C9—C10—H10B109.00
F6—C4—C5114.3 (2)C9—C10—H10C110.00
C3—C4—C5105.7 (2)H10A—C10—H10B109.00
C1—C5—C4109.9 (2)H10A—C10—H10C109.00
C1—C5—C19132.3 (3)H10B—C10—H10C109.00
C4—C5—C19117.8 (2)C11—C12—H12A119.00
C1—C6—C7124.0 (2)C13—C12—H12A119.00
C1—C6—C9123.8 (2)C12—C13—H13A120.00
C7—C6—C9112.1 (2)C14—C13—H13A120.00
C6—C7—C8114.1 (2)C14—C15—H15A120.00
S1—C8—C7110.03 (17)C16—C15—H15A120.00
S1—C8—C11121.21 (19)C11—C16—H16A119.00
C7—C8—C11128.7 (2)C15—C16—H16A120.00
S1—C9—C6110.65 (17)C17—C18—H18A180.00
S1—C9—C10119.54 (19)C19—C20—H20A123.00
C6—C9—C10129.7 (2)C21—C20—H20A123.00
C8—C11—C12120.2 (2)C22—C23—H23A109.00
C8—C11—C16121.7 (2)C22—C23—H23B109.00
C12—C11—C16118.1 (2)C22—C23—H23C110.00
C11—C12—C13121.4 (2)H23A—C23—H23B109.00
C12—C13—C14120.7 (2)H23A—C23—H23C110.00
C13—C14—C15118.6 (2)H23B—C23—H23C109.00
C13—C14—C17120.8 (2)C24—C25—H25A119.00
C15—C14—C17120.6 (3)C26—C25—H25A120.00
C14—C15—C16120.1 (2)C25—C26—H26A120.00
C11—C16—C15121.1 (2)C27—C26—H26A120.00
C14—C17—C18177.9 (3)C27—C28—H28A120.00
C5—C19—C20121.6 (2)C29—C28—H28A120.00
C5—C19—C22126.3 (2)C24—C29—H29A120.00
C20—C19—C22112.0 (2)C28—C29—H29A120.00
C19—C20—C21114.5 (2)C30—C31—H31A180.00
C9—S1—C8—C70.37 (19)C1—C5—C19—C2238.4 (4)
C9—S1—C8—C11178.0 (2)C4—C5—C19—C2031.1 (3)
C8—S1—C9—C60.65 (19)C4—C5—C19—C22144.1 (2)
C8—S1—C9—C10176.7 (2)C1—C6—C7—C8176.6 (2)
C22—S2—C21—C200.0 (2)C9—C6—C7—C80.5 (3)
C22—S2—C21—C24176.7 (2)C1—C6—C9—S1176.90 (19)
C21—S2—C22—C190.3 (2)C1—C6—C9—C100.1 (4)
C21—S2—C22—C23177.6 (2)C7—C6—C9—S10.8 (3)
C5—C1—C2—F1110.2 (2)C7—C6—C9—C10176.2 (2)
C5—C1—C2—F2130.5 (2)C6—C7—C8—S10.0 (3)
C5—C1—C2—C38.5 (2)C6—C7—C8—C11178.2 (2)
C6—C1—C2—F164.4 (3)S1—C8—C11—C12161.84 (18)
C6—C1—C2—F255.0 (3)S1—C8—C11—C1618.2 (3)
C6—C1—C2—C3177.01 (18)C7—C8—C11—C1216.2 (4)
C2—C1—C5—C45.2 (2)C7—C8—C11—C16163.8 (2)
C2—C1—C5—C19177.2 (2)C8—C11—C12—C13179.9 (2)
C6—C1—C5—C4168.5 (2)C16—C11—C12—C130.1 (3)
C6—C1—C5—C199.2 (4)C8—C11—C16—C15179.7 (2)
C2—C1—C6—C743.9 (3)C12—C11—C16—C150.3 (3)
C2—C1—C6—C9131.9 (2)C11—C12—C13—C140.7 (3)
C5—C1—C6—C7142.9 (3)C12—C13—C14—C151.3 (3)
C5—C1—C6—C941.4 (4)C12—C13—C14—C17177.5 (2)
F1—C2—C3—F321.9 (3)C13—C14—C15—C161.1 (3)
F1—C2—C3—F4142.3 (2)C17—C14—C15—C16177.7 (2)
F1—C2—C3—C4101.5 (2)C14—C15—C16—C110.3 (4)
F2—C2—C3—F394.5 (2)C5—C19—C20—C21176.3 (2)
F2—C2—C3—F425.8 (3)C22—C19—C20—C210.6 (3)
F2—C2—C3—C4142.06 (19)C5—C19—C22—S2176.1 (2)
C1—C2—C3—F3141.5 (2)C5—C19—C22—C231.6 (4)
C1—C2—C3—F498.2 (2)C20—C19—C22—S20.5 (3)
C1—C2—C3—C418.0 (2)C20—C19—C22—C23177.1 (2)
F3—C3—C4—F525.3 (3)C19—C20—C21—S20.3 (3)
F3—C3—C4—F690.4 (2)C19—C20—C21—C24176.8 (2)
F3—C3—C4—C5144.6 (2)S2—C21—C24—C25160.7 (2)
F4—C3—C4—F5144.6 (2)S2—C21—C24—C2922.1 (3)
F4—C3—C4—F629.0 (3)C20—C21—C24—C2523.2 (4)
F4—C3—C4—C596.1 (2)C20—C21—C24—C29153.9 (3)
C2—C3—C4—F598.3 (2)C21—C24—C25—C26176.1 (2)
C2—C3—C4—F6146.02 (19)C29—C24—C25—C261.1 (4)
C2—C3—C4—C520.9 (2)C21—C24—C29—C28175.4 (3)
F5—C4—C5—C1101.0 (2)C25—C24—C29—C281.9 (4)
F5—C4—C5—C1977.1 (3)C24—C25—C26—C270.6 (4)
F6—C4—C5—C1140.5 (2)C25—C26—C27—C281.7 (4)
F6—C4—C5—C1941.4 (3)C25—C26—C27—C30177.9 (3)
C3—C4—C5—C116.8 (2)C26—C27—C28—C291.0 (4)
C3—C4—C5—C19165.13 (19)C30—C27—C28—C29178.6 (3)
C1—C5—C19—C20146.5 (3)C27—C28—C29—C240.8 (4)
Symmetry codes: (i) x, y1, z; (ii) x, y+3/2, z+1/2; (iii) x, y+3/2, z1/2; (iv) x, y+1, z; (v) x, y+5/2, z1/2; (vi) x, y+5/2, z+1/2; (vii) x+1, y+1/2, z+1/2; (viii) x, y+1/2, z+3/2; (ix) x+1, y1/2, z+1/2; (x) x, y+2, z+1; (xi) x, y1/2, z+3/2; (xii) x+1, y+2, z; (xiii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···F20.952.402.929 (3)115
C16—H16A···S10.952.753.137 (3)105
C20—H20A···F50.952.483.073 (3)120
C25—H25A···F6vi0.952.543.426 (3)154
C29—H29A···S20.952.803.177 (2)105
C31—H31A···F6xi0.952.523.396 (3)154
Symmetry codes: (vi) x, y+5/2, z+1/2; (xi) x, y1/2, z+3/2.
 

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