organic compounds
λ4,3-ditelluratetracyclo[5.5.2.04,13.010,14]tetradeca-1(12),4,6,10,13-pentaen-2-ylium trifluoromethanesulfonate
of 2-phenyl-2aEaStCHEM School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland
*Correspondence e-mail: jdw3@st-and.ac.uk
In the title compound, C18H13Te2+·CF3O3S−, the TeII atom of the cation and one O atom of the trifluoromethanesulfonate counter-ion form a close-to-linear Te—Te—O system, with a Te—Te—O angle of 172.3 (1)° and a Te—O distance of 2.816 (5) Å, which may suggest the presence of a three-centre–four-electron (3c–4e) bond. Secondary Te⋯O interactions [3.003 (4) and 3.016 (4) Å], involving the second TeII atom of the binuclear molecule, are also noted, resulting in a supramolecular layer in the bc plane.
Keywords: crystal structure; acenaphthene; triflate; tellurium.
CCDC reference: 1018417
1. Related literature
For studies on related interactions with halogen counter-ions, see: Knight et al. (2010, 2012). For discussions of 3c–4e bonding in this type of system, see: Aschenbach et al. (2012). For a general review of peri-substituted naphthalenes and acenaphthenes, see: Kilian et al. (2011).
2. Experimental
2.1. Crystal data
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2.1.3. Refinement
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Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2014); software used to prepare material for publication: CrystalStructure.
Supporting information
CCDC reference: 1018417
10.1107/S1600536814018170/tk5334sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018170/tk5334Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018170/tk5334Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536814018170/tk5334Isup4.cml
5,6-Bis(phenyltelluro)acenaphthene (0.22 g, 0.39 mmol) was added to a solution of copper triflate (0.15 g, 0.40 mmol) in dichloromethane (20 ml) at 263 K. The resulting dark-purple solution was left to stir at this temperature for 3 h, then at room temperature for a further 12 h. The solution was filtered to give a grey solid and a dark-orange filtrate. The filtrate was evaporated under reduced pressure to yield an orange oil. The oil was redissolved in the minimum amount of dichloromethane, hexane was layered on top and the solution was left at 243 K. After 24 h the solution had yielded red needle-like crystals (0.03 g, 9%).
Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell
CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2014); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).Fig. 1. The molecular structure of I with displacement ellipsoids drawn at the 50% probability level, hydrogen atoms omitted for clarity. |
C18H13Te2+·CF3O3S− | F(000) = 1192.00 |
Mr = 633.57 | Dx = 2.161 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 6711 reflections |
a = 10.687 (2) Å | θ = 2.2–25.4° |
b = 15.264 (3) Å | µ = 3.15 mm−1 |
c = 12.242 (3) Å | T = 93 K |
β = 102.808 (6)° | Prism, red |
V = 1947.4 (7) Å3 | 0.06 × 0.03 × 0.03 mm |
Z = 4 |
Rigaku Mercury70 diffractometer | 2926 reflections with F2 > 2σ(F2) |
Detector resolution: 14.629 pixels mm-1 | Rint = 0.053 |
ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (REQAB; Rigaku, 1998) | h = −12→9 |
Tmin = 0.619, Tmax = 0.910 | k = −18→16 |
11783 measured reflections | l = −13→14 |
3407 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0442P)2 + 0.2589P] where P = (Fo2 + 2Fc2)/3 |
3407 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 1.19 e Å−3 |
0 restraints | Δρmin = −1.03 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C18H13Te2+·CF3O3S− | V = 1947.4 (7) Å3 |
Mr = 633.57 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.687 (2) Å | µ = 3.15 mm−1 |
b = 15.264 (3) Å | T = 93 K |
c = 12.242 (3) Å | 0.06 × 0.03 × 0.03 mm |
β = 102.808 (6)° |
Rigaku Mercury70 diffractometer | 3407 independent reflections |
Absorption correction: multi-scan (REQAB; Rigaku, 1998) | 2926 reflections with F2 > 2σ(F2) |
Tmin = 0.619, Tmax = 0.910 | Rint = 0.053 |
11783 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.19 e Å−3 |
3407 reflections | Δρmin = −1.03 e Å−3 |
253 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Te1 | 0.92263 (3) | 0.03268 (2) | 0.27873 (3) | 0.03050 (15) | |
Te2 | 1.06486 (3) | 0.15215 (2) | 0.19281 (3) | 0.03058 (15) | |
S1 | 1.22291 (14) | 0.36194 (10) | 0.05449 (12) | 0.0343 (3) | |
F1 | 1.3368 (4) | 0.2922 (3) | −0.0924 (3) | 0.0736 (12) | |
F2 | 1.4264 (3) | 0.4088 (3) | −0.0175 (3) | 0.0663 (11) | |
F3 | 1.4490 (3) | 0.2900 (3) | 0.0760 (3) | 0.0580 (10) | |
O1 | 1.1412 (4) | 0.4067 (3) | −0.0381 (3) | 0.0504 (11) | |
O2 | 1.1831 (5) | 0.2769 (3) | 0.0794 (4) | 0.0708 (15) | |
O3 | 1.2729 (4) | 0.4160 (3) | 0.1503 (3) | 0.0561 (12) | |
C1 | 0.8098 (5) | 0.0140 (3) | 0.1162 (4) | 0.0306 (12) | |
C2 | 0.7081 (5) | −0.0459 (4) | 0.0972 (4) | 0.0336 (13) | |
C3 | 0.6348 (5) | −0.0581 (4) | −0.0142 (5) | 0.0369 (13) | |
C4 | 0.6668 (5) | −0.0150 (3) | −0.1026 (5) | 0.0339 (13) | |
C5 | 0.7726 (5) | 0.0419 (3) | −0.0806 (4) | 0.0254 (12) | |
C6 | 0.7958 (5) | 0.0781 (3) | −0.1800 (4) | 0.0323 (12) | |
C7 | 0.8986 (6) | 0.1343 (4) | −0.1715 (5) | 0.0348 (13) | |
C8 | 0.9751 (6) | 0.1531 (3) | −0.0650 (5) | 0.0323 (13) | |
C9 | 0.9514 (5) | 0.1190 (3) | 0.0320 (4) | 0.0311 (12) | |
C10 | 0.8473 (5) | 0.0597 (3) | 0.0259 (4) | 0.0272 (11) | |
C11 | 0.6098 (6) | −0.0171 (4) | −0.2265 (5) | 0.0393 (14) | |
C12 | 0.6954 (6) | 0.0459 (4) | −0.2789 (5) | 0.0398 (14) | |
C13 | 0.8004 (5) | 0.1217 (3) | 0.3394 (5) | 0.0321 (12) | |
C14 | 0.8276 (6) | 0.1392 (4) | 0.4527 (5) | 0.0383 (14) | |
C15 | 0.7547 (5) | 0.1992 (4) | 0.4949 (5) | 0.0378 (13) | |
C16 | 0.6548 (5) | 0.2397 (4) | 0.4255 (5) | 0.0374 (13) | |
C17 | 0.6254 (5) | 0.2217 (4) | 0.3126 (5) | 0.0405 (14) | |
C18 | 0.6985 (5) | 0.1620 (3) | 0.2671 (5) | 0.0341 (13) | |
C19 | 1.3656 (6) | 0.3386 (4) | 0.0029 (5) | 0.0411 (15) | |
H2 | 0.68829 | −0.07808 | 0.15763 | 0.0403* | |
H3 | 0.56297 | −0.09649 | −0.02735 | 0.0443* | |
H7 | 0.91742 | 0.15997 | −0.23669 | 0.0417* | |
H8 | 1.04654 | 0.19114 | −0.06005 | 0.0387* | |
H11A | 0.51973 | 0.00346 | −0.24279 | 0.0472* | |
H11B | 0.61218 | −0.07721 | −0.25642 | 0.0472* | |
H12A | 0.73565 | 0.01444 | −0.33292 | 0.0478* | |
H12B | 0.64423 | 0.09538 | −0.31778 | 0.0478* | |
H14 | 0.89646 | 0.10994 | 0.50143 | 0.0460* | |
H15 | 0.77437 | 0.21228 | 0.57267 | 0.0453* | |
H16 | 0.60456 | 0.28089 | 0.45527 | 0.0449* | |
H17 | 0.55472 | 0.25015 | 0.26522 | 0.0486* | |
H18 | 0.67911 | 0.14935 | 0.18917 | 0.0409* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Te1 | 0.0320 (2) | 0.0332 (3) | 0.0270 (2) | 0.00187 (14) | 0.00796 (17) | 0.00255 (15) |
Te2 | 0.0295 (3) | 0.0324 (3) | 0.0307 (2) | −0.00155 (14) | 0.00854 (18) | −0.00344 (15) |
S1 | 0.0339 (8) | 0.0419 (8) | 0.0283 (8) | −0.0023 (6) | 0.0093 (6) | −0.0031 (6) |
F1 | 0.073 (3) | 0.106 (3) | 0.040 (2) | 0.035 (3) | 0.009 (2) | −0.018 (2) |
F2 | 0.043 (2) | 0.092 (3) | 0.066 (3) | −0.004 (2) | 0.0170 (19) | 0.030 (2) |
F3 | 0.055 (2) | 0.080 (3) | 0.038 (2) | 0.022 (2) | 0.0064 (17) | 0.0081 (19) |
O1 | 0.033 (2) | 0.075 (3) | 0.043 (2) | 0.015 (2) | 0.0056 (19) | 0.005 (2) |
O2 | 0.075 (3) | 0.069 (3) | 0.069 (3) | −0.039 (3) | 0.019 (3) | 0.007 (3) |
O3 | 0.056 (3) | 0.068 (3) | 0.041 (2) | 0.011 (2) | 0.004 (2) | −0.026 (2) |
C1 | 0.035 (3) | 0.033 (3) | 0.024 (3) | 0.006 (2) | 0.007 (2) | −0.001 (2) |
C2 | 0.025 (3) | 0.049 (3) | 0.028 (3) | −0.003 (2) | 0.008 (2) | −0.015 (3) |
C3 | 0.034 (3) | 0.038 (3) | 0.043 (3) | −0.009 (2) | 0.015 (3) | −0.008 (3) |
C4 | 0.032 (3) | 0.040 (3) | 0.030 (3) | 0.001 (2) | 0.008 (3) | −0.008 (3) |
C5 | 0.029 (3) | 0.022 (3) | 0.029 (3) | 0.004 (2) | 0.012 (2) | −0.002 (2) |
C6 | 0.038 (3) | 0.031 (3) | 0.028 (3) | 0.003 (2) | 0.007 (2) | −0.003 (2) |
C7 | 0.047 (4) | 0.032 (3) | 0.029 (3) | 0.005 (3) | 0.016 (3) | 0.006 (2) |
C8 | 0.038 (3) | 0.025 (3) | 0.037 (3) | −0.002 (2) | 0.015 (3) | 0.002 (2) |
C9 | 0.036 (3) | 0.029 (3) | 0.027 (3) | 0.005 (2) | 0.005 (2) | −0.002 (2) |
C10 | 0.029 (3) | 0.028 (3) | 0.028 (3) | 0.003 (2) | 0.014 (2) | −0.003 (2) |
C11 | 0.041 (3) | 0.044 (3) | 0.032 (3) | −0.008 (3) | 0.007 (3) | −0.006 (3) |
C12 | 0.048 (4) | 0.039 (3) | 0.033 (3) | −0.001 (3) | 0.010 (3) | −0.001 (3) |
C13 | 0.030 (3) | 0.035 (3) | 0.032 (3) | −0.004 (2) | 0.011 (2) | 0.006 (3) |
C14 | 0.037 (3) | 0.043 (3) | 0.035 (3) | −0.003 (3) | 0.008 (3) | −0.002 (3) |
C15 | 0.038 (3) | 0.043 (3) | 0.033 (3) | −0.006 (3) | 0.009 (3) | −0.003 (3) |
C16 | 0.033 (3) | 0.038 (3) | 0.043 (3) | −0.003 (3) | 0.012 (3) | −0.004 (3) |
C17 | 0.035 (3) | 0.039 (3) | 0.048 (4) | 0.008 (3) | 0.009 (3) | 0.011 (3) |
C18 | 0.035 (3) | 0.038 (3) | 0.029 (3) | 0.001 (2) | 0.006 (3) | 0.004 (2) |
C19 | 0.047 (4) | 0.053 (4) | 0.023 (3) | 0.010 (3) | 0.008 (3) | 0.008 (3) |
Te1—Te2 | 2.7297 (6) | C8—C9 | 1.370 (8) |
Te1—C1 | 2.104 (5) | C9—C10 | 1.424 (7) |
Te1—C13 | 2.130 (6) | C11—C12 | 1.560 (9) |
Te2—C9 | 2.131 (5) | C13—C14 | 1.379 (8) |
S1—O1 | 1.441 (4) | C13—C18 | 1.385 (7) |
S1—O2 | 1.420 (5) | C14—C15 | 1.374 (8) |
S1—O3 | 1.437 (4) | C15—C16 | 1.357 (7) |
S1—C19 | 1.810 (7) | C16—C17 | 1.376 (8) |
F1—C19 | 1.341 (7) | C17—C18 | 1.394 (8) |
F2—C19 | 1.307 (7) | C2—H2 | 0.950 |
F3—C19 | 1.339 (6) | C3—H3 | 0.950 |
C1—C2 | 1.401 (7) | C7—H7 | 0.950 |
C1—C10 | 1.437 (8) | C8—H8 | 0.950 |
C2—C3 | 1.426 (7) | C11—H11A | 0.990 |
C3—C4 | 1.373 (8) | C11—H11B | 0.990 |
C4—C5 | 1.403 (7) | C12—H12A | 0.990 |
C4—C11 | 1.505 (7) | C12—H12B | 0.990 |
C5—C6 | 1.408 (8) | C14—H14 | 0.950 |
C5—C10 | 1.396 (7) | C15—H15 | 0.950 |
C6—C7 | 1.379 (8) | C16—H16 | 0.950 |
C6—C12 | 1.510 (7) | C17—H17 | 0.950 |
C7—C8 | 1.407 (7) | C18—H18 | 0.950 |
F1···O1 | 2.913 (6) | F2···H11Axiv | 3.5516 |
F1···O2 | 2.951 (7) | F2···H11Bvi | 2.7142 |
F2···O1 | 3.003 (5) | F2···H12Avi | 2.7467 |
F2···O3 | 2.902 (6) | F2···H12Bvi | 3.4740 |
F3···O2 | 2.859 (6) | F2···H12Bxiv | 2.9799 |
F3···O3 | 2.972 (6) | F2···H16iv | 3.5216 |
C1···C4 | 2.810 (7) | F3···H3ix | 3.0105 |
C1···C18 | 3.302 (8) | F3···H12Bxiv | 2.8107 |
C2···C5 | 2.770 (8) | F3···H15iv | 3.4861 |
C3···C6 | 3.600 (8) | F3···H16iv | 2.6844 |
C3···C10 | 2.853 (7) | F3···H17vii | 2.4194 |
C5···C8 | 2.724 (7) | F3···H18vii | 3.3265 |
C6···C9 | 2.825 (7) | O1···H8 | 3.4347 |
C7···C10 | 2.832 (8) | O1···H12Avi | 2.8026 |
C13···C16 | 2.739 (8) | O1···H14viii | 3.1733 |
C14···C17 | 2.748 (7) | O1···H14iii | 2.7746 |
C15···C18 | 2.778 (8) | O2···H8 | 2.3778 |
Te1···O1i | 3.003 (4) | O2···H14iii | 3.4610 |
Te1···O3ii | 3.016 (5) | O3···H2viii | 2.2975 |
Te2···F1i | 3.563 (4) | O3···H11Axiv | 2.9415 |
Te2···O1i | 3.336 (4) | C2···H3x | 3.5714 |
Te2···O2 | 2.816 (5) | C2···H8ix | 3.5384 |
F1···Te2iii | 3.563 (4) | C2···H11Ax | 3.3843 |
F1···C16iv | 3.391 (7) | C3···H3x | 3.2820 |
F1···C17iv | 3.536 (8) | C5···H16iii | 3.3296 |
F2···F2v | 3.179 (6) | C7···H15xv | 3.3385 |
F2···C11vi | 3.272 (7) | C9···H15iii | 3.2977 |
F2···C12vi | 3.294 (7) | C10···H16iii | 3.5217 |
F2···C16iv | 3.512 (7) | C12···H15xv | 3.3381 |
F3···C16iv | 3.198 (7) | C12···H17iii | 3.5496 |
F3···C17vii | 3.258 (6) | C14···H8i | 3.5166 |
O1···Te1iii | 3.003 (4) | C14···H12Axvi | 3.5530 |
O1···Te2iii | 3.336 (4) | C15···H7xvi | 3.4127 |
O1···C14iii | 3.401 (7) | C15···H12Axvi | 3.5535 |
O2···Te2 | 2.816 (5) | C15···H12Bxvi | 3.2196 |
O2···C8 | 3.145 (7) | C15···H18i | 3.5368 |
O2···C9 | 3.411 (7) | C17···H11Bx | 3.3179 |
O3···Te1viii | 3.016 (5) | C17···H12Bi | 3.2449 |
O3···C1viii | 3.509 (7) | C18···H7i | 3.5931 |
O3···C2viii | 3.108 (7) | C18···H11Ax | 3.4055 |
O3···C13viii | 3.245 (7) | C18···H11Bx | 3.5389 |
C1···O3ii | 3.509 (7) | C18···H15iii | 3.2957 |
C1···C8ix | 3.581 (8) | C19···H11Bvi | 3.3364 |
C2···O3ii | 3.108 (7) | C19···H12Avi | 3.4216 |
C3···C3x | 3.466 (8) | C19···H12Bxiv | 3.4361 |
C5···C16iii | 3.571 (7) | C19···H16iv | 3.2939 |
C6···C16iii | 3.542 (8) | H2···S1ii | 3.5604 |
C6···C17iii | 3.549 (8) | H2···F1ix | 3.3609 |
C8···O2 | 3.145 (7) | H2···O3ii | 2.2975 |
C8···C1ix | 3.581 (8) | H2···H11Ax | 2.8904 |
C8···C14iii | 3.568 (8) | H3···F1ix | 3.3946 |
C8···C15iii | 3.455 (8) | H3···F3ix | 3.0105 |
C9···O2 | 3.411 (7) | H3···C2x | 3.5714 |
C9···C15iii | 3.450 (7) | H3···C3x | 3.2820 |
C11···F2xi | 3.272 (7) | H3···H3x | 3.3670 |
C12···F2xi | 3.294 (7) | H3···H16xvii | 2.8615 |
C13···O3ii | 3.245 (7) | H3···H18x | 2.9994 |
C14···O1i | 3.401 (7) | H7···Te1ix | 3.4963 |
C14···C8i | 3.568 (8) | H7···Te2iii | 3.4720 |
C15···C8i | 3.455 (8) | H7···C15xv | 3.4127 |
C15···C9i | 3.450 (7) | H7···C18iii | 3.5931 |
C16···F1xii | 3.391 (7) | H7···H14xv | 3.2547 |
C16···F2xii | 3.512 (7) | H7···H15xv | 2.6153 |
C16···F3xii | 3.198 (7) | H8···S1 | 3.3383 |
C16···C5i | 3.571 (7) | H8···F1 | 3.5644 |
C16···C6i | 3.542 (8) | H8···O1 | 3.4347 |
C17···F1xii | 3.536 (8) | H8···O2 | 2.3778 |
C17···F3xiii | 3.258 (6) | H8···C2ix | 3.5384 |
C17···C6i | 3.549 (8) | H8···C14iii | 3.5166 |
Te1···H2 | 3.1116 | H8···H14iii | 3.5907 |
Te1···H14 | 3.0397 | H11A···F2xi | 3.4316 |
Te1···H18 | 3.1435 | H11A···F2xviii | 3.5516 |
Te2···H8 | 3.1155 | H11A···O3xviii | 2.9415 |
C1···H3 | 3.2925 | H11A···C2x | 3.3843 |
C1···H18 | 2.7511 | H11A···C18x | 3.4055 |
C2···H18 | 3.2258 | H11A···H2x | 2.8904 |
C3···H11A | 2.9500 | H11A···H18x | 3.3175 |
C3···H11B | 2.9360 | H11B···Te2ix | 3.5548 |
C4···H2 | 3.2867 | H11B···F1xi | 2.8537 |
C4···H12A | 3.1007 | H11B···F2xi | 2.7142 |
C4···H12B | 3.0915 | H11B···C17x | 3.3179 |
C5···H3 | 3.2482 | H11B···C18x | 3.5389 |
C5···H7 | 3.2570 | H11B···C19xi | 3.3364 |
C5···H11A | 3.0345 | H11B···H17x | 3.1743 |
C5···H11B | 3.0394 | H11B···H18x | 3.5662 |
C5···H12A | 3.0546 | H12A···Te2ix | 3.5117 |
C5···H12B | 3.0352 | H12A···F1xi | 3.5539 |
C6···H8 | 3.2511 | H12A···F2xi | 2.7467 |
C6···H11A | 3.0967 | H12A···O1xi | 2.8026 |
C6···H11B | 3.0874 | H12A···C14xv | 3.5530 |
C7···H12A | 2.9595 | H12A···C15xv | 3.5535 |
C7···H12B | 2.9649 | H12A···C19xi | 3.4216 |
C9···H7 | 3.2884 | H12A···H14xv | 3.2766 |
C10···H2 | 3.3355 | H12A···H15xv | 3.2922 |
C10···H8 | 3.2652 | H12B···F2xi | 3.4740 |
C10···H18 | 3.2698 | H12B···F2xviii | 2.9799 |
C11···H3 | 2.8646 | H12B···F3xviii | 2.8107 |
C12···H7 | 2.8954 | H12B···C15xv | 3.2196 |
C13···H15 | 3.2397 | H12B···C17iii | 3.2449 |
C13···H17 | 3.2406 | H12B···C19xviii | 3.4361 |
C14···H16 | 3.2237 | H12B···H15xv | 2.7828 |
C14···H18 | 3.2682 | H12B···H17iii | 2.8174 |
C15···H17 | 3.2273 | H14···S1i | 3.4313 |
C16···H14 | 3.2238 | H14···O1ii | 3.1733 |
C16···H18 | 3.2674 | H14···O1i | 2.7746 |
C17···H15 | 3.2316 | H14···O2i | 3.4610 |
C18···H14 | 3.2628 | H14···H7xvi | 3.2547 |
C18···H16 | 3.2611 | H14···H8i | 3.5907 |
H2···H3 | 2.3783 | H14···H12Axvi | 3.2766 |
H2···H18 | 3.4967 | H15···F3xii | 3.4861 |
H3···H11A | 2.9928 | H15···C7xvi | 3.3385 |
H3···H11B | 2.9802 | H15···C9i | 3.2977 |
H7···H8 | 2.3418 | H15···C12xvi | 3.3381 |
H7···H12A | 3.0135 | H15···C18i | 3.2957 |
H7···H12B | 3.0326 | H15···H7xvi | 2.6153 |
H11A···H12A | 2.7748 | H15···H12Axvi | 3.2922 |
H11A···H12B | 2.2635 | H15···H12Bxvi | 2.7828 |
H11B···H12A | 2.2635 | H15···H18i | 2.8592 |
H11B···H12B | 2.7813 | H16···F1xii | 3.0054 |
H14···H15 | 2.3255 | H16···F2xii | 3.5216 |
H15···H16 | 2.3021 | H16···F3xii | 2.6844 |
H16···H17 | 2.3168 | H16···C5i | 3.3296 |
H17···H18 | 2.3559 | H16···C10i | 3.5217 |
Te1···H7ix | 3.4963 | H16···C19xii | 3.2939 |
Te2···H7i | 3.4720 | H16···H3xix | 2.8615 |
Te2···H11Bix | 3.5548 | H16···H18i | 2.9927 |
Te2···H12Aix | 3.5117 | H17···F1xii | 3.2678 |
S1···H2viii | 3.5604 | H17···F3xiii | 2.4194 |
S1···H8 | 3.3383 | H17···C12i | 3.5496 |
S1···H14iii | 3.4313 | H17···H11Bx | 3.1743 |
F1···H2ix | 3.3609 | H17···H12Bi | 2.8174 |
F1···H3ix | 3.3946 | H18···F3xiii | 3.3265 |
F1···H8 | 3.5644 | H18···C15iii | 3.5368 |
F1···H11Bvi | 2.8537 | H18···H3x | 2.9994 |
F1···H12Avi | 3.5539 | H18···H11Ax | 3.3175 |
F1···H16iv | 3.0054 | H18···H11Bx | 3.5662 |
F1···H17iv | 3.2678 | H18···H15iii | 2.8592 |
F2···H11Avi | 3.4316 | H18···H16iii | 2.9927 |
Te2—Te1—C1 | 88.70 (15) | C14—C15—C16 | 120.1 (5) |
Te2—Te1—C13 | 98.34 (15) | C15—C16—C17 | 120.7 (5) |
C1—Te1—C13 | 98.6 (2) | C16—C17—C18 | 120.6 (5) |
Te1—Te2—C9 | 86.91 (15) | C13—C18—C17 | 117.7 (5) |
O1—S1—O2 | 116.3 (3) | S1—C19—F1 | 111.1 (4) |
O1—S1—O3 | 114.9 (3) | S1—C19—F2 | 113.5 (4) |
O1—S1—C19 | 103.3 (3) | S1—C19—F3 | 111.3 (4) |
O2—S1—O3 | 115.1 (3) | F1—C19—F2 | 107.1 (5) |
O2—S1—C19 | 102.2 (3) | F1—C19—F3 | 106.2 (5) |
O3—S1—C19 | 102.0 (3) | F2—C19—F3 | 107.2 (5) |
Te1—C1—C2 | 120.4 (4) | C1—C2—H2 | 120.450 |
Te1—C1—C10 | 117.6 (3) | C3—C2—H2 | 120.449 |
C2—C1—C10 | 121.8 (4) | C2—C3—H3 | 119.656 |
C1—C2—C3 | 119.1 (5) | C4—C3—H3 | 119.651 |
C2—C3—C4 | 120.7 (5) | C6—C7—H7 | 120.424 |
C3—C4—C5 | 118.5 (5) | C8—C7—H7 | 120.429 |
C3—C4—C11 | 131.9 (5) | C7—C8—H8 | 118.517 |
C5—C4—C11 | 109.6 (5) | C9—C8—H8 | 118.501 |
C4—C5—C6 | 111.5 (4) | C4—C11—H11A | 110.757 |
C4—C5—C10 | 124.7 (5) | C4—C11—H11B | 110.756 |
C6—C5—C10 | 123.8 (5) | C12—C11—H11A | 110.759 |
C5—C6—C7 | 118.0 (4) | C12—C11—H11B | 110.756 |
C5—C6—C12 | 109.5 (5) | H11A—C11—H11B | 108.843 |
C7—C6—C12 | 132.5 (5) | C6—C12—H12A | 110.873 |
C6—C7—C8 | 119.1 (5) | C6—C12—H12B | 110.872 |
C7—C8—C9 | 123.0 (5) | C11—C12—H12A | 110.874 |
Te2—C9—C8 | 122.3 (4) | C11—C12—H12B | 110.871 |
Te2—C9—C10 | 118.5 (4) | H12A—C12—H12B | 108.910 |
C8—C9—C10 | 119.2 (4) | C13—C14—H14 | 120.132 |
C1—C10—C5 | 115.2 (4) | C15—C14—H14 | 120.134 |
C1—C10—C9 | 128.0 (4) | C14—C15—H15 | 119.953 |
C5—C10—C9 | 116.9 (5) | C16—C15—H15 | 119.953 |
C4—C11—C12 | 104.9 (4) | C15—C16—H16 | 119.680 |
C6—C12—C11 | 104.4 (4) | C17—C16—H16 | 119.670 |
Te1—C13—C14 | 117.7 (4) | C16—C17—H17 | 119.695 |
Te1—C13—C18 | 121.1 (4) | C18—C17—H17 | 119.691 |
C14—C13—C18 | 121.2 (5) | C13—C18—H18 | 121.144 |
C13—C14—C15 | 119.7 (5) | C17—C18—H18 | 121.146 |
Te2—Te1—C1—C2 | 179.4 (3) | C3—C4—C11—C12 | −178.6 (5) |
Te2—Te1—C1—C10 | 4.1 (3) | C5—C4—C11—C12 | 0.4 (6) |
C1—Te1—Te2—C9 | −4.04 (15) | C11—C4—C5—C6 | −1.5 (6) |
Te2—Te1—C13—C14 | −101.8 (3) | C11—C4—C5—C10 | 179.5 (4) |
Te2—Te1—C13—C18 | 76.9 (4) | C4—C5—C6—C7 | −178.9 (4) |
C13—Te1—Te2—C9 | −102.50 (13) | C4—C5—C6—C12 | 2.0 (6) |
C1—Te1—C13—C14 | 168.2 (3) | C4—C5—C10—C1 | 0.7 (7) |
C1—Te1—C13—C18 | −13.0 (4) | C4—C5—C10—C9 | 179.7 (4) |
C13—Te1—C1—C2 | −82.3 (4) | C6—C5—C10—C1 | −178.2 (4) |
C13—Te1—C1—C10 | 102.3 (3) | C6—C5—C10—C9 | 0.8 (7) |
Te1—Te2—C9—C8 | −175.5 (4) | C10—C5—C6—C7 | 0.1 (7) |
Te1—Te2—C9—C10 | 4.7 (3) | C10—C5—C6—C12 | −179.0 (4) |
O1—S1—C19—F1 | −56.7 (4) | C5—C6—C7—C8 | −0.1 (8) |
O1—S1—C19—F2 | 64.1 (4) | C5—C6—C12—C11 | −1.6 (5) |
O1—S1—C19—F3 | −174.8 (3) | C7—C6—C12—C11 | 179.4 (5) |
O2—S1—C19—F1 | 64.5 (4) | C12—C6—C7—C8 | 178.8 (5) |
O2—S1—C19—F2 | −174.8 (3) | C6—C7—C8—C9 | −1.0 (8) |
O2—S1—C19—F3 | −53.7 (4) | C7—C8—C9—Te2 | −177.8 (4) |
O3—S1—C19—F1 | −176.2 (3) | C7—C8—C9—C10 | 2.0 (8) |
O3—S1—C19—F2 | −55.4 (4) | Te2—C9—C10—C1 | −3.2 (7) |
O3—S1—C19—F3 | 65.7 (4) | Te2—C9—C10—C5 | 177.9 (3) |
Te1—C1—C2—C3 | −179.0 (3) | C8—C9—C10—C1 | 177.0 (4) |
Te1—C1—C10—C5 | 177.2 (3) | C8—C9—C10—C5 | −1.8 (7) |
Te1—C1—C10—C9 | −1.7 (7) | C4—C11—C12—C6 | 0.7 (5) |
C2—C1—C10—C5 | 2.0 (7) | Te1—C13—C14—C15 | 177.1 (3) |
C2—C1—C10—C9 | −176.9 (5) | Te1—C13—C18—C17 | −177.9 (3) |
C10—C1—C2—C3 | −3.9 (8) | C14—C13—C18—C17 | 0.8 (8) |
C1—C2—C3—C4 | 3.1 (8) | C18—C13—C14—C15 | −1.6 (8) |
C2—C3—C4—C5 | −0.6 (8) | C13—C14—C15—C16 | 1.3 (8) |
C2—C3—C4—C11 | 178.3 (5) | C14—C15—C16—C17 | −0.3 (8) |
C3—C4—C5—C6 | 177.6 (4) | C15—C16—C17—C18 | −0.5 (8) |
C3—C4—C5—C10 | −1.4 (8) | C16—C17—C18—C13 | 0.3 (8) |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z−1/2; (v) −x+3, −y+1, −z; (vi) −x+2, y+1/2, −z−1/2; (vii) x+1, y, z; (viii) −x+2, y+1/2, −z+1/2; (ix) −x+2, −y, −z; (x) −x+1, −y, −z; (xi) −x+2, y−1/2, −z−1/2; (xii) x−1, −y+1/2, z+1/2; (xiii) x−1, y, z; (xiv) x+1, −y+1/2, z+1/2; (xv) x, y, z−1; (xvi) x, y, z+1; (xvii) −x+1, y−1/2, −z+1/2; (xviii) x−1, −y+1/2, z−1/2; (xix) −x+1, y+1/2, −z+1/2. |
Acknowledgements
We are grateful to the University of St Andrews and the EPSRC for support.
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