The title compound, C
31H
18F
6S
2, 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
CCDC reference: 295405
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
C31H18F6S2 | F(000) = 1160 |
Mr = 568.57 | Dx = 1.467 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 18629 reflections |
a = 26.7998 (17) Å | θ = 1.6–25.6° |
b = 9.0730 (5) Å | µ = 0.27 mm−1 |
c = 10.7628 (6) Å | T = 173 K |
β = 100.337 (5)° | Block, pale blue |
V = 2574.5 (3) Å3 | 0.40 × 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 tube | Rint = 0.107 |
Graphite monochromator | θmax = 25.1°, θmin = 1.5° |
ω and φ scans | h = −31→32 |
18574 measured reflections | k = −10→10 |
4577 independent reflections | l = −12→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-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 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.34895 (2) | 0.76528 (7) | 0.45326 (5) | 0.0379 (2) | |
S2 | 0.12231 (2) | 0.80828 (7) | 0.41051 (6) | 0.0398 (2) | |
F1 | 0.32795 (6) | 1.30758 (18) | 0.52818 (18) | 0.0581 (6) | |
F2 | 0.31196 (7) | 1.31709 (17) | 0.32463 (17) | 0.0577 (6) | |
F3 | 0.26073 (7) | 1.51004 (18) | 0.50694 (18) | 0.0599 (6) | |
F4 | 0.22731 (7) | 1.44263 (19) | 0.31683 (16) | 0.0579 (6) | |
F5 | 0.21202 (6) | 1.31613 (16) | 0.60861 (13) | 0.0440 (5) | |
F6 | 0.16018 (5) | 1.33706 (16) | 0.43064 (15) | 0.0459 (5) | |
C1 | 0.26856 (9) | 1.1350 (3) | 0.4265 (2) | 0.0320 (7) | |
C2 | 0.29071 (9) | 1.2874 (3) | 0.4264 (2) | 0.0389 (8) | |
C3 | 0.24712 (10) | 1.3924 (3) | 0.4336 (2) | 0.0414 (8) | |
C4 | 0.20798 (9) | 1.2963 (3) | 0.4802 (2) | 0.0350 (7) | |
C5 | 0.22081 (9) | 1.1409 (3) | 0.4503 (2) | 0.0307 (7) | |
C6 | 0.30109 (9) | 1.0085 (3) | 0.4139 (2) | 0.0328 (7) | |
C7 | 0.33498 (9) | 1.0014 (3) | 0.3260 (2) | 0.0344 (7) | |
C8 | 0.36350 (8) | 0.8771 (3) | 0.3350 (2) | 0.0331 (7) | |
C9 | 0.30490 (9) | 0.8863 (3) | 0.4910 (2) | 0.0352 (7) | |
C10 | 0.27898 (10) | 0.8530 (3) | 0.5989 (2) | 0.0426 (8) | |
C11 | 0.40284 (9) | 0.8354 (3) | 0.2627 (2) | 0.0355 (7) | |
C12 | 0.42398 (9) | 0.9408 (3) | 0.1947 (2) | 0.0401 (8) | |
C13 | 0.46085 (9) | 0.9048 (3) | 0.1265 (2) | 0.0442 (8) | |
C14 | 0.47852 (9) | 0.7611 (3) | 0.1248 (2) | 0.0447 (8) | |
C15 | 0.45725 (10) | 0.6532 (3) | 0.1919 (2) | 0.0459 (8) | |
C16 | 0.42004 (10) | 0.6907 (3) | 0.2599 (2) | 0.0426 (8) | |
C17 | 0.51853 (11) | 0.7244 (4) | 0.0575 (3) | 0.0534 (10) | |
C18 | 0.55257 (12) | 0.6946 (4) | 0.0055 (3) | 0.0673 (13) | |
C19 | 0.18264 (9) | 1.0271 (3) | 0.4556 (2) | 0.0326 (7) | |
C20 | 0.14783 (8) | 1.0373 (3) | 0.5407 (2) | 0.0333 (7) | |
C21 | 0.11279 (9) | 0.9273 (3) | 0.5291 (2) | 0.0345 (7) | |
C22 | 0.17305 (9) | 0.9062 (3) | 0.3770 (2) | 0.0357 (7) | |
C23 | 0.19812 (10) | 0.8564 (3) | 0.2713 (2) | 0.0421 (8) | |
C24 | 0.07078 (9) | 0.9107 (3) | 0.5977 (2) | 0.0349 (7) | |
C25 | 0.07284 (9) | 0.9788 (3) | 0.7143 (2) | 0.0394 (8) | |
C26 | 0.03244 (10) | 0.9718 (3) | 0.7769 (2) | 0.0406 (8) | |
C27 | −0.01161 (9) | 0.8977 (3) | 0.7246 (2) | 0.0395 (8) | |
C28 | −0.01360 (10) | 0.8272 (3) | 0.6089 (3) | 0.0431 (8) | |
C29 | 0.02686 (9) | 0.8326 (3) | 0.5468 (2) | 0.0406 (8) | |
C30 | −0.05386 (10) | 0.8964 (3) | 0.7901 (3) | 0.0483 (9) | |
C31 | −0.08845 (11) | 0.8980 (4) | 0.8444 (3) | 0.0599 (11) | |
H7A | 0.33740 | 1.07710 | 0.26640 | 0.0410* | |
H10A | 0.24640 | 0.80490 | 0.56750 | 0.0640* | |
H10B | 0.30030 | 0.78720 | 0.65830 | 0.0640* | |
H10C | 0.27310 | 0.94480 | 0.64200 | 0.0640* | |
H12A | 0.41270 | 1.04000 | 0.19530 | 0.0480* | |
H13A | 0.47440 | 0.97900 | 0.07990 | 0.0530* | |
H15A | 0.46840 | 0.55390 | 0.19070 | 0.0550* | |
H16A | 0.40590 | 0.61660 | 0.30560 | 0.0510* | |
H18A | 0.57990 | 0.67060 | −0.03620 | 0.0810* | |
H20A | 0.14900 | 1.11460 | 0.60070 | 0.0400* | |
H23A | 0.17330 | 0.80540 | 0.20780 | 0.0630* | |
H23B | 0.22590 | 0.78890 | 0.30400 | 0.0630* | |
H23C | 0.21160 | 0.94200 | 0.23270 | 0.0630* | |
H25A | 0.10260 | 1.03090 | 0.75120 | 0.0470* | |
H26A | 0.03470 | 1.01820 | 0.85690 | 0.0490* | |
H28A | −0.04330 | 0.77480 | 0.57240 | 0.0520* | |
H29A | 0.02500 | 0.78270 | 0.46850 | 0.0490* | |
H31A | −0.11630 | 0.89930 | 0.88800 | 0.0720* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0398 (3) | 0.0410 (4) | 0.0338 (3) | 0.0087 (3) | 0.0090 (2) | 0.0045 (3) |
S2 | 0.0421 (4) | 0.0360 (4) | 0.0417 (3) | −0.0069 (3) | 0.0085 (3) | −0.0049 (3) |
F1 | 0.0432 (9) | 0.0515 (10) | 0.0749 (11) | −0.0086 (7) | −0.0017 (8) | −0.0155 (9) |
F2 | 0.0724 (11) | 0.0404 (9) | 0.0720 (11) | −0.0028 (8) | 0.0447 (9) | 0.0034 (8) |
F3 | 0.0665 (11) | 0.0372 (9) | 0.0833 (12) | −0.0139 (8) | 0.0328 (9) | −0.0201 (9) |
F4 | 0.0682 (11) | 0.0540 (10) | 0.0554 (9) | 0.0095 (8) | 0.0215 (8) | 0.0219 (8) |
F5 | 0.0586 (9) | 0.0393 (8) | 0.0373 (7) | −0.0041 (7) | 0.0169 (7) | −0.0085 (6) |
F6 | 0.0397 (8) | 0.0393 (8) | 0.0588 (9) | 0.0075 (6) | 0.0089 (7) | 0.0045 (7) |
C1 | 0.0363 (12) | 0.0310 (12) | 0.0292 (11) | −0.0005 (9) | 0.0076 (9) | 0.0004 (9) |
C2 | 0.0386 (13) | 0.0357 (13) | 0.0451 (13) | −0.0056 (11) | 0.0149 (11) | −0.0029 (11) |
C3 | 0.0500 (14) | 0.0304 (13) | 0.0454 (14) | −0.0011 (11) | 0.0132 (11) | −0.0014 (11) |
C4 | 0.0370 (12) | 0.0338 (13) | 0.0350 (12) | 0.0025 (10) | 0.0089 (10) | −0.0012 (10) |
C5 | 0.0353 (12) | 0.0295 (12) | 0.0267 (10) | 0.0010 (9) | 0.0043 (9) | 0.0004 (9) |
C6 | 0.0326 (12) | 0.0332 (12) | 0.0318 (11) | −0.0005 (9) | 0.0034 (9) | −0.0029 (10) |
C7 | 0.0350 (12) | 0.0354 (13) | 0.0332 (12) | −0.0020 (10) | 0.0071 (9) | 0.0002 (10) |
C8 | 0.0302 (11) | 0.0393 (13) | 0.0290 (11) | −0.0004 (10) | 0.0029 (9) | −0.0024 (10) |
C9 | 0.0356 (12) | 0.0383 (13) | 0.0310 (11) | 0.0020 (10) | 0.0040 (9) | 0.0007 (10) |
C10 | 0.0466 (14) | 0.0459 (15) | 0.0382 (13) | 0.0113 (12) | 0.0153 (11) | 0.0087 (11) |
C11 | 0.0308 (11) | 0.0438 (14) | 0.0307 (11) | 0.0021 (10) | 0.0022 (9) | −0.0039 (10) |
C12 | 0.0400 (13) | 0.0388 (14) | 0.0436 (13) | −0.0028 (11) | 0.0129 (11) | −0.0069 (11) |
C13 | 0.0399 (14) | 0.0506 (16) | 0.0439 (14) | −0.0057 (12) | 0.0127 (11) | −0.0065 (12) |
C14 | 0.0334 (13) | 0.0638 (18) | 0.0365 (12) | 0.0042 (12) | 0.0052 (10) | −0.0060 (13) |
C15 | 0.0440 (14) | 0.0521 (16) | 0.0416 (14) | 0.0159 (12) | 0.0076 (11) | 0.0005 (12) |
C16 | 0.0424 (14) | 0.0476 (16) | 0.0383 (13) | 0.0094 (12) | 0.0089 (11) | 0.0052 (12) |
C17 | 0.0429 (15) | 0.066 (2) | 0.0516 (16) | 0.0078 (14) | 0.0096 (12) | −0.0036 (15) |
C18 | 0.0514 (18) | 0.089 (3) | 0.068 (2) | 0.0113 (17) | 0.0285 (16) | −0.0038 (19) |
C19 | 0.0334 (12) | 0.0296 (12) | 0.0340 (11) | 0.0003 (9) | 0.0039 (9) | 0.0008 (10) |
C20 | 0.0343 (12) | 0.0321 (12) | 0.0332 (11) | 0.0012 (10) | 0.0050 (9) | −0.0003 (10) |
C21 | 0.0355 (12) | 0.0332 (13) | 0.0343 (12) | 0.0004 (10) | 0.0049 (9) | 0.0035 (10) |
C22 | 0.0378 (12) | 0.0345 (13) | 0.0340 (12) | 0.0016 (10) | 0.0042 (9) | 0.0007 (10) |
C23 | 0.0440 (14) | 0.0433 (15) | 0.0399 (13) | −0.0037 (11) | 0.0098 (11) | −0.0062 (11) |
C24 | 0.0342 (12) | 0.0310 (12) | 0.0390 (12) | 0.0016 (10) | 0.0051 (10) | 0.0054 (10) |
C25 | 0.0378 (13) | 0.0373 (14) | 0.0422 (13) | −0.0068 (10) | 0.0045 (10) | −0.0004 (11) |
C26 | 0.0458 (14) | 0.0358 (14) | 0.0419 (13) | −0.0016 (11) | 0.0123 (11) | 0.0016 (11) |
C27 | 0.0367 (13) | 0.0351 (13) | 0.0473 (14) | 0.0025 (10) | 0.0095 (11) | 0.0122 (11) |
C28 | 0.0368 (13) | 0.0405 (15) | 0.0501 (15) | −0.0074 (11) | 0.0030 (11) | 0.0056 (12) |
C29 | 0.0405 (13) | 0.0378 (14) | 0.0424 (13) | −0.0045 (11) | 0.0042 (11) | 0.0028 (11) |
C30 | 0.0431 (15) | 0.0450 (16) | 0.0572 (16) | 0.0017 (12) | 0.0105 (13) | 0.0130 (13) |
C31 | 0.0476 (16) | 0.067 (2) | 0.070 (2) | 0.0046 (15) | 0.0235 (15) | 0.0195 (17) |
Geometric parameters (Å, º) top
S1—C8 | 1.726 (2) | C19—C22 | 1.381 (4) |
S1—C9 | 1.714 (3) | C20—C21 | 1.361 (4) |
S2—C21 | 1.725 (2) | C21—C24 | 1.461 (3) |
S2—C22 | 1.716 (3) | C22—C23 | 1.491 (3) |
F1—C2 | 1.355 (3) | C24—C25 | 1.391 (3) |
F2—C2 | 1.349 (3) | C24—C29 | 1.399 (3) |
F3—C3 | 1.339 (3) | C25—C26 | 1.376 (4) |
F4—C3 | 1.353 (3) | C26—C27 | 1.387 (4) |
F5—C4 | 1.379 (3) | C27—C28 | 1.392 (4) |
F6—C4 | 1.348 (3) | C27—C30 | 1.437 (4) |
C1—C2 | 1.505 (4) | C28—C29 | 1.373 (4) |
C1—C5 | 1.351 (3) | C30—C31 | 1.181 (4) |
C1—C6 | 1.462 (4) | C7—H7A | 0.9500 |
C2—C3 | 1.520 (4) | C10—H10A | 0.9800 |
C3—C4 | 1.517 (4) | C10—H10B | 0.9800 |
C4—C5 | 1.500 (4) | C10—H10C | 0.9800 |
C5—C19 | 1.462 (4) | C12—H12A | 0.9500 |
C6—C7 | 1.426 (3) | C13—H13A | 0.9500 |
C6—C9 | 1.378 (4) | C15—H15A | 0.9500 |
C7—C8 | 1.356 (4) | C16—H16A | 0.9500 |
C8—C11 | 1.468 (3) | C18—H18A | 0.9500 |
C9—C10 | 1.487 (3) | C20—H20A | 0.9500 |
C11—C12 | 1.386 (4) | C23—H23A | 0.9800 |
C11—C16 | 1.394 (4) | C23—H23B | 0.9800 |
C12—C13 | 1.372 (3) | C23—H23C | 0.9800 |
C13—C14 | 1.388 (4) | C25—H25A | 0.9500 |
C14—C15 | 1.397 (4) | C26—H26A | 0.9500 |
C14—C17 | 1.437 (4) | C28—H28A | 0.9500 |
C15—C16 | 1.381 (4) | C29—H29A | 0.9500 |
C17—C18 | 1.184 (4) | C31—H31A | 0.9500 |
C19—C20 | 1.423 (3) | | |
| | | |
S1···F3i | 3.4317 (19) | C28···C24x | 3.424 (4) |
S1···C13ii | 3.584 (2) | C28···C29x | 3.500 (4) |
S1···C11ii | 3.505 (2) | C28···C21x | 3.580 (4) |
S1···C12ii | 3.524 (2) | C28···C26xi | 3.519 (4) |
S1···C16ii | 3.525 (2) | C29···C29x | 3.434 (4) |
S1···C14ii | 3.636 (2) | C29···C28x | 3.500 (4) |
S1···C15ii | 3.591 (3) | C31···C22x | 3.469 (4) |
S2···C26iii | 3.617 (3) | C1···H10C | 2.8800 |
S2···C25iii | 3.464 (3) | C1···H23C | 2.9300 |
S1···H16A | 2.7500 | C2···H7A | 2.9900 |
S2···H29A | 2.8000 | C4···H20A | 2.7600 |
F1···F3 | 2.554 (2) | C5···H23C | 2.9300 |
F2···F4 | 2.526 (3) | C5···H10C | 2.8900 |
F2···C7 | 2.929 (3) | C6···H23C | 2.8700 |
F2···F3 | 3.125 (3) | C6···H23B | 2.9300 |
F3···F1 | 2.554 (2) | C7···H12A | 2.7400 |
F3···F2 | 3.125 (3) | C8···H10Biii | 2.7500 |
F3···C10iv | 3.275 (3) | C9···H23B | 2.7900 |
F3···S1iv | 3.4317 (19) | C11···H10Biii | 2.9900 |
F3···F6 | 3.099 (2) | C12···H7A | 2.8600 |
F3···F5 | 2.551 (2) | C13···H15Avii | 2.8200 |
F4···F6 | 2.539 (2) | C17···H13Axii | 3.0900 |
F4···C20v | 3.336 (3) | C18···H15Axiii | 3.0700 |
F4···F2 | 2.526 (3) | C19···H10A | 2.7700 |
F5···F3 | 2.551 (2) | C19···H10C | 2.9500 |
F5···C20 | 3.073 (3) | C20···H25A | 2.7600 |
F6···F3 | 3.099 (2) | C22···H10A | 2.7300 |
F6···C20 | 3.008 (3) | C25···H20A | 2.8400 |
F6···F4 | 2.539 (2) | C27···H29Aii | 3.1000 |
F1···H7Avi | 2.7400 | C28···H26Axi | 2.9000 |
F1···H18Avii | 2.7500 | C30···H29Aii | 3.0600 |
F2···H7A | 2.4000 | C31···H28Aii | 2.9800 |
F3···H10Aiv | 2.8000 | H7A···F2 | 2.4000 |
F4···H10Cv | 2.6300 | H7A···C2 | 2.9900 |
F5···H20A | 2.4800 | H7A···C12 | 2.8600 |
F5···H31Aviii | 2.6800 | H7A···H12A | 2.3100 |
F5···H23Cvi | 2.5700 | H7A···F1v | 2.7400 |
F6···H20A | 2.7800 | H10A···F3i | 2.8000 |
F6···H31Aviii | 2.5200 | H10A···C19 | 2.7700 |
F6···H25Av | 2.5400 | H10A···C22 | 2.7300 |
C1···C23 | 3.408 (4) | H10B···C8ii | 2.7500 |
C5···C10 | 3.304 (4) | H10B···C11ii | 2.9900 |
C6···C22 | 3.508 (3) | H10C···C1 | 2.8800 |
C6···C23 | 3.218 (4) | H10C···C5 | 2.8900 |
C7···F2 | 2.929 (3) | H10C···C19 | 2.9500 |
C9···C23 | 3.380 (3) | H10C···F4vi | 2.6300 |
C9···C22 | 3.531 (3) | H12A···C7 | 2.7400 |
C9···C19 | 3.473 (4) | H12A···H7A | 2.3100 |
C10···F3i | 3.275 (3) | H13A···C17xii | 3.0900 |
C10···C22 | 3.400 (3) | H13A···H13Axii | 2.4200 |
C10···C5 | 3.304 (4) | H15A···C13ix | 2.8200 |
C10···C19 | 3.180 (4) | H15A···C18xiii | 3.0700 |
C11···S1iii | 3.505 (2) | H16A···S1 | 2.7500 |
C12···S1iii | 3.524 (2) | H18A···F1ix | 2.7500 |
C13···S1iii | 3.584 (2) | H20A···F5 | 2.4800 |
C13···C15vii | 3.490 (4) | H20A···F6 | 2.7800 |
C14···S1iii | 3.636 (2) | H20A···C4 | 2.7600 |
C15···C13ix | 3.490 (4) | H20A···C25 | 2.8400 |
C15···S1iii | 3.591 (3) | H20A···H25A | 2.3400 |
C16···S1iii | 3.525 (2) | H23B···C6 | 2.9300 |
C19···C9 | 3.473 (4) | H23B···C9 | 2.7900 |
C19···C10 | 3.180 (4) | H23C···C1 | 2.9300 |
C20···F6 | 3.008 (3) | H23C···C5 | 2.9300 |
C20···F5 | 3.073 (3) | H23C···C6 | 2.8700 |
C20···F4vi | 3.336 (3) | H23C···F5v | 2.5700 |
C21···C28x | 3.580 (4) | H25A···C20 | 2.7600 |
C22···C10 | 3.400 (3) | H25A···H20A | 2.3400 |
C22···C6 | 3.508 (3) | H25A···F6vi | 2.5400 |
C22···C9 | 3.531 (3) | H26A···C28viii | 2.9000 |
C22···C31x | 3.469 (4) | H26A···H28Aviii | 2.4500 |
C23···C6 | 3.218 (4) | H28A···H26Axi | 2.4500 |
C23···C1 | 3.408 (4) | H28A···C31iii | 2.9800 |
C23···C9 | 3.380 (3) | H29A···S2 | 2.8000 |
C24···C28x | 3.424 (4) | H29A···C27iii | 3.1000 |
C25···S2ii | 3.464 (3) | H29A···C30iii | 3.0600 |
C26···C28viii | 3.519 (4) | H31A···F5xi | 2.6800 |
C26···S2ii | 3.617 (3) | H31A···F6xi | 2.5200 |
| | | |
C8—S1—C9 | 93.13 (12) | S2—C21—C20 | 109.62 (17) |
C21—S2—C22 | 93.41 (12) | S2—C21—C24 | 122.62 (19) |
C2—C1—C5 | 110.6 (2) | C20—C21—C24 | 127.7 (2) |
C2—C1—C6 | 118.6 (2) | S2—C22—C19 | 110.48 (17) |
C5—C1—C6 | 130.5 (2) | S2—C22—C23 | 119.08 (19) |
F1—C2—F2 | 105.8 (2) | C19—C22—C23 | 130.4 (2) |
F1—C2—C1 | 110.9 (2) | C21—C24—C25 | 120.1 (2) |
F1—C2—C3 | 109.59 (19) | C21—C24—C29 | 121.7 (2) |
F2—C2—C1 | 114.1 (2) | C25—C24—C29 | 118.2 (2) |
F2—C2—C3 | 110.9 (2) | C24—C25—C26 | 120.9 (2) |
C1—C2—C3 | 105.6 (2) | C25—C26—C27 | 120.7 (2) |
F3—C3—F4 | 107.4 (2) | C26—C27—C28 | 118.6 (2) |
F3—C3—C2 | 113.5 (2) | C26—C27—C30 | 119.5 (2) |
F3—C3—C4 | 113.3 (2) | C28—C27—C30 | 121.9 (2) |
F4—C3—C2 | 109.93 (19) | C27—C28—C29 | 120.8 (2) |
F4—C3—C4 | 108.8 (2) | C24—C29—C28 | 120.7 (2) |
C2—C3—C4 | 103.9 (2) | C27—C30—C31 | 178.8 (3) |
F5—C4—F6 | 105.01 (19) | C6—C7—H7A | 123.00 |
F5—C4—C3 | 108.78 (19) | C8—C7—H7A | 123.00 |
F5—C4—C5 | 110.98 (19) | C9—C10—H10A | 109.00 |
F6—C4—C3 | 112.1 (2) | C9—C10—H10B | 109.00 |
F6—C4—C5 | 114.3 (2) | C9—C10—H10C | 110.00 |
C3—C4—C5 | 105.7 (2) | H10A—C10—H10B | 109.00 |
C1—C5—C4 | 109.9 (2) | H10A—C10—H10C | 109.00 |
C1—C5—C19 | 132.3 (3) | H10B—C10—H10C | 109.00 |
C4—C5—C19 | 117.8 (2) | C11—C12—H12A | 119.00 |
C1—C6—C7 | 124.0 (2) | C13—C12—H12A | 119.00 |
C1—C6—C9 | 123.8 (2) | C12—C13—H13A | 120.00 |
C7—C6—C9 | 112.1 (2) | C14—C13—H13A | 120.00 |
C6—C7—C8 | 114.1 (2) | C14—C15—H15A | 120.00 |
S1—C8—C7 | 110.03 (17) | C16—C15—H15A | 120.00 |
S1—C8—C11 | 121.21 (19) | C11—C16—H16A | 119.00 |
C7—C8—C11 | 128.7 (2) | C15—C16—H16A | 120.00 |
S1—C9—C6 | 110.65 (17) | C17—C18—H18A | 180.00 |
S1—C9—C10 | 119.54 (19) | C19—C20—H20A | 123.00 |
C6—C9—C10 | 129.7 (2) | C21—C20—H20A | 123.00 |
C8—C11—C12 | 120.2 (2) | C22—C23—H23A | 109.00 |
C8—C11—C16 | 121.7 (2) | C22—C23—H23B | 109.00 |
C12—C11—C16 | 118.1 (2) | C22—C23—H23C | 110.00 |
C11—C12—C13 | 121.4 (2) | H23A—C23—H23B | 109.00 |
C12—C13—C14 | 120.7 (2) | H23A—C23—H23C | 110.00 |
C13—C14—C15 | 118.6 (2) | H23B—C23—H23C | 109.00 |
C13—C14—C17 | 120.8 (2) | C24—C25—H25A | 119.00 |
C15—C14—C17 | 120.6 (3) | C26—C25—H25A | 120.00 |
C14—C15—C16 | 120.1 (2) | C25—C26—H26A | 120.00 |
C11—C16—C15 | 121.1 (2) | C27—C26—H26A | 120.00 |
C14—C17—C18 | 177.9 (3) | C27—C28—H28A | 120.00 |
C5—C19—C20 | 121.6 (2) | C29—C28—H28A | 120.00 |
C5—C19—C22 | 126.3 (2) | C24—C29—H29A | 120.00 |
C20—C19—C22 | 112.0 (2) | C28—C29—H29A | 120.00 |
C19—C20—C21 | 114.5 (2) | C30—C31—H31A | 180.00 |
| | | |
C9—S1—C8—C7 | −0.37 (19) | C1—C5—C19—C22 | −38.4 (4) |
C9—S1—C8—C11 | 178.0 (2) | C4—C5—C19—C20 | −31.1 (3) |
C8—S1—C9—C6 | 0.65 (19) | C4—C5—C19—C22 | 144.1 (2) |
C8—S1—C9—C10 | −176.7 (2) | C1—C6—C7—C8 | 176.6 (2) |
C22—S2—C21—C20 | 0.0 (2) | C9—C6—C7—C8 | 0.5 (3) |
C22—S2—C21—C24 | 176.7 (2) | C1—C6—C9—S1 | −176.90 (19) |
C21—S2—C22—C19 | 0.3 (2) | C1—C6—C9—C10 | 0.1 (4) |
C21—S2—C22—C23 | −177.6 (2) | C7—C6—C9—S1 | −0.8 (3) |
C5—C1—C2—F1 | 110.2 (2) | C7—C6—C9—C10 | 176.2 (2) |
C5—C1—C2—F2 | −130.5 (2) | C6—C7—C8—S1 | 0.0 (3) |
C5—C1—C2—C3 | −8.5 (2) | C6—C7—C8—C11 | −178.2 (2) |
C6—C1—C2—F1 | −64.4 (3) | S1—C8—C11—C12 | −161.84 (18) |
C6—C1—C2—F2 | 55.0 (3) | S1—C8—C11—C16 | 18.2 (3) |
C6—C1—C2—C3 | 177.01 (18) | C7—C8—C11—C12 | 16.2 (4) |
C2—C1—C5—C4 | −5.2 (2) | C7—C8—C11—C16 | −163.8 (2) |
C2—C1—C5—C19 | 177.2 (2) | C8—C11—C12—C13 | 179.9 (2) |
C6—C1—C5—C4 | 168.5 (2) | C16—C11—C12—C13 | −0.1 (3) |
C6—C1—C5—C19 | −9.2 (4) | C8—C11—C16—C15 | −179.7 (2) |
C2—C1—C6—C7 | −43.9 (3) | C12—C11—C16—C15 | 0.3 (3) |
C2—C1—C6—C9 | 131.9 (2) | C11—C12—C13—C14 | −0.7 (3) |
C5—C1—C6—C7 | 142.9 (3) | C12—C13—C14—C15 | 1.3 (3) |
C5—C1—C6—C9 | −41.4 (4) | C12—C13—C14—C17 | −177.5 (2) |
F1—C2—C3—F3 | 21.9 (3) | C13—C14—C15—C16 | −1.1 (3) |
F1—C2—C3—F4 | 142.3 (2) | C17—C14—C15—C16 | 177.7 (2) |
F1—C2—C3—C4 | −101.5 (2) | C14—C15—C16—C11 | 0.3 (4) |
F2—C2—C3—F3 | −94.5 (2) | C5—C19—C20—C21 | 176.3 (2) |
F2—C2—C3—F4 | 25.8 (3) | C22—C19—C20—C21 | 0.6 (3) |
F2—C2—C3—C4 | 142.06 (19) | C5—C19—C22—S2 | −176.1 (2) |
C1—C2—C3—F3 | 141.5 (2) | C5—C19—C22—C23 | 1.6 (4) |
C1—C2—C3—F4 | −98.2 (2) | C20—C19—C22—S2 | −0.5 (3) |
C1—C2—C3—C4 | 18.0 (2) | C20—C19—C22—C23 | 177.1 (2) |
F3—C3—C4—F5 | −25.3 (3) | C19—C20—C21—S2 | −0.3 (3) |
F3—C3—C4—F6 | 90.4 (2) | C19—C20—C21—C24 | −176.8 (2) |
F3—C3—C4—C5 | −144.6 (2) | S2—C21—C24—C25 | 160.7 (2) |
F4—C3—C4—F5 | −144.6 (2) | S2—C21—C24—C29 | −22.1 (3) |
F4—C3—C4—F6 | −29.0 (3) | C20—C21—C24—C25 | −23.2 (4) |
F4—C3—C4—C5 | 96.1 (2) | C20—C21—C24—C29 | 153.9 (3) |
C2—C3—C4—F5 | 98.3 (2) | C21—C24—C25—C26 | 176.1 (2) |
C2—C3—C4—F6 | −146.02 (19) | C29—C24—C25—C26 | −1.1 (4) |
C2—C3—C4—C5 | −20.9 (2) | C21—C24—C29—C28 | −175.4 (3) |
F5—C4—C5—C1 | −101.0 (2) | C25—C24—C29—C28 | 1.9 (4) |
F5—C4—C5—C19 | 77.1 (3) | C24—C25—C26—C27 | −0.6 (4) |
F6—C4—C5—C1 | 140.5 (2) | C25—C26—C27—C28 | 1.7 (4) |
F6—C4—C5—C19 | −41.4 (3) | C25—C26—C27—C30 | −177.9 (3) |
C3—C4—C5—C1 | 16.8 (2) | C26—C27—C28—C29 | −1.0 (4) |
C3—C4—C5—C19 | −165.13 (19) | C30—C27—C28—C29 | 178.6 (3) |
C1—C5—C19—C20 | 146.5 (3) | C27—C28—C29—C24 | −0.8 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x, y+1, z; (v) x, −y+5/2, z−1/2; (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, y−1/2, −z+1/2; (x) −x, −y+2, −z+1; (xi) −x, y−1/2, −z+3/2; (xii) −x+1, −y+2, −z; (xiii) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···F2 | 0.95 | 2.40 | 2.929 (3) | 115 |
C16—H16A···S1 | 0.95 | 2.75 | 3.137 (3) | 105 |
C20—H20A···F5 | 0.95 | 2.48 | 3.073 (3) | 120 |
C25—H25A···F6vi | 0.95 | 2.54 | 3.426 (3) | 154 |
C29—H29A···S2 | 0.95 | 2.80 | 3.177 (2) | 105 |
C31—H31A···F6xi | 0.95 | 2.52 | 3.396 (3) | 154 |
Symmetry codes: (vi) x, −y+5/2, z+1/2; (xi) −x, y−1/2, −z+3/2. |