Home Physical Sciences Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
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Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe

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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 239 Issue 1

Abstract

C16H25F3O5STe, monoclinic, P21/c (no. 14), a = 5.8214(2) Å, b = 16.0059(5) Å, c = 21.9311(7) Å, β = 94.760(3)°, V = 2036.42(12) Å3, Z = 4, R gt(F) = 0.0282, wR ref(F 2) = 0.0598, T = 293 K.

CCDC no.: 2314079

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colourless prism
Size: 0.40 × 0.20 × 0.10 mm
Wavelength: MoKα radiation (0.71073 Å)
μ: 1.61 mm−1
Diffractometer, scan mode: XtaLAB Pro, ω
θ max, completeness: 29.4°, >99 %
N(hkl)measured, N(hkl)unique, R int: 29,146, 5013, 0.045
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 4203
N(param)refined: 247
Programs: CrysAlis Pro [1], Shelx [2, 3], Olex2 [4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
Te1 −0.04480 (3) 0.63825 (2) 0.44080 (2) 0.01553 (5)
O1 −0.3278 (3) 0.64277 (11) 0.38472 (8) 0.0195 (4)
H1 −0.409407 0.603844 0.397991 0.029*
O2 0.1371 (4) 0.57150 (11) 0.39152 (8) 0.0244 (4)
H2 0.163239 0.524126 0.408242 0.037*
C1 0.0752 (4) 0.75297 (14) 0.40908 (10) 0.0123 (4)
C2 0.1286 (4) 0.76408 (14) 0.34813 (10) 0.0126 (4)
C3 0.2454 (4) 0.83757 (15) 0.33513 (11) 0.0136 (5)
H3 0.286249 0.846110 0.295496 0.016*
C4 0.3029 (4) 0.89836 (15) 0.37915 (11) 0.0136 (5)
C5 0.2299 (4) 0.88745 (14) 0.43773 (11) 0.0126 (4)
H5 0.258289 0.929503 0.466638 0.015*
C6 0.1161 (4) 0.81545 (14) 0.45402 (10) 0.0116 (4)
C7 0.0545 (4) 0.70568 (15) 0.29544 (10) 0.0144 (5)
H7 −0.022336 0.657393 0.312235 0.017*
C8 0.2586 (5) 0.67339 (17) 0.26213 (12) 0.0220 (5)
H8A 0.333167 0.719520 0.243930 0.033*
H8B 0.203768 0.634701 0.230780 0.033*
H8C 0.366564 0.645748 0.290848 0.033*
C9 −0.1215 (4) 0.75073 (17) 0.25080 (12) 0.0206 (5)
H9A −0.250596 0.768218 0.272168 0.031*
H9B −0.173365 0.713394 0.218270 0.031*
H9C −0.050342 0.798736 0.234064 0.031*
C10 0.4404 (4) 0.97502 (15) 0.36397 (12) 0.0181 (5)
H10 0.474577 1.006491 0.401968 0.022*
C11 0.3059 (5) 1.03217 (17) 0.31881 (16) 0.0305 (7)
H11A 0.273310 1.003370 0.280672 0.046*
H11B 0.395538 1.081226 0.312270 0.046*
H11C 0.163889 1.048065 0.334899 0.046*
C12 0.6711 (4) 0.95028 (16) 0.33997 (13) 0.0203 (5)
H12A 0.753061 0.913587 0.368777 0.030*
H12B 0.761572 0.999520 0.334741 0.030*
H12C 0.643070 0.922245 0.301368 0.030*
C13 0.0226 (4) 0.80798 (15) 0.51678 (10) 0.0135 (5)
H13 0.041550 0.749671 0.529886 0.016*
C14 −0.2363 (4) 0.82733 (19) 0.51168 (13) 0.0246 (6)
H14A −0.260547 0.884408 0.499334 0.037*
H14B −0.296236 0.818629 0.550662 0.037*
H14C −0.314191 0.791052 0.481841 0.037*
C15 0.1467 (4) 0.86231 (18) 0.56626 (11) 0.0212 (5)
H15A 0.310037 0.854169 0.566275 0.032*
H15B 0.097601 0.847001 0.605464 0.032*
H15C 0.110385 0.919979 0.558191 0.032*
S1 0.54239 (11) 0.40927 (4) 0.44132 (3) 0.01662 (12)
O3 0.2948 (3) 0.41948 (13) 0.43240 (9) 0.0274 (4)
O4 0.6718 (4) 0.48501 (12) 0.44131 (10) 0.0328 (5)
O5 0.6168 (3) 0.35064 (11) 0.48920 (8) 0.0206 (4)
C16 0.6107 (5) 0.35701 (19) 0.37101 (12) 0.0258 (6)
F1 0.5475 (4) 0.40322 (14) 0.32249 (8) 0.0473 (5)
F2 0.8352 (3) 0.34227 (13) 0.37165 (8) 0.0397 (5)
F3 0.5018 (3) 0.28402 (12) 0.36496 (8) 0.0414 (5)

1 Source of material

A mixture of 2,4,6-tripropylbenzenetellurinic anhydride (0.7097 g, 0.9997 mmol) and trifluoromethanesulfonic anhydride (0.3103 g, 1.100 mmol) in dichloromethane (10 ml) was stirred at room temperature for 18 h under an argon atmosphere. After removing the solvent under reduced pressure, the resulting highly viscous residue was left at room temperature in the presence of air for three days. The precipitated crystals were then washed with hexane to obtain the final compound (0.4504 g, 0.8762 mmol, 44 %).

2 Experimental details

Hydrogen atoms were placed at predetermined positions and refined using a riding model. In this model, the C–H bond distances were set to 0.96 Å for methyl groups, 0.98 Å for methane groups, and 0.93 Å for aromatic groups. For methyl H atoms, the uncertainty displacement parameter (U iso(H)) was constrained to 1.5 times the equivalent isotropic displacement parameter (U eq(C)), and for all other H atoms, it was constrained to 1.2 times U eq(C).

3 Comment

Tellurinic acid is a fundamental organotellurium oxoacid that usually exists as complex aggregates because of highly polarized Te–O bonds that form intermolecular interactions. In 2008, the first well-defined tellurinic acid was isolated as a kinetically stabilized dimer by introducing bulky substituents onto the tellurium atom [5]. Recently, the isolation of a monomeric 2-(2-pyridyl)phenyltellurinic acid [ppyTe(O)OH], stabilized via intramolecular chalcogen bonding, has been reported [6]. Conversely, the sodium salt of tellurinic acid exists as a monomer without bulky substituents or stabilizing intramolecular bonds [7]. In this study, we report the crystal structure of a structurally rare dihydroxytelluronium compound, which can be considered to be a protonated form of tellurinic acid.

The asymmetric unit of the compound contains one ion pair associated with a medium-strength hydrogen bond (O2⋯O3 2.726 (3) Å) [8]. The donor–acceptor (O⋯O) distance is slightly shorter than that observed in the structurally related hydroxydiaryltelluronium trifluoromethanesulfonate [(8-Me2NC10H6)2TeOH]OTf (O⋯O 2.814 (6) Å) [9]. For the molecular structure, the geometry around the Te center in the dihydroxy(2,4,6-triisopropylphenyl)telluronium moiety is best described as a distorted tetrahedral with a CO2 donor set, considering the lone pair. The angles C1–Te1–O1, C1–Te1–O2, and O11–Te1–O2 are 92.57 (8)°, 94.97 (9)° and 98.15 (8)°, respectively. The two Te–OH bond lengths are not the same. The bond distance of Te1–O1 (1.974 (2) Å) is comparable to those observed in ppyTe(O)OH (Te–OH 1.966 (2) Å) and [(8-Me2NC10H6)2TeOH]OTf (Te–OH 1.957 (4) Å), whereas the Te1–O2 distance (1.903 (2) Å) is intermediate between those and Te=O (1.834 (2) Å in ppyTe(O)OH), indicating that the title compound was formed by the protonation of tellurinic acid. In the crystal lattice, O1 is hydrogen bonded to another TfO− (O1⋯O4 i 2.814 (3) Å, i = −1 + x, y, z), although it is slightly weaker than the O2⋯O3 hydrogen bond described above. As a result, hydrogen bonds alternately bind telluronium cations and trifluoromethanesulfonate anions, forming a column structure along the a-axis.

Corresponding author: Makoto Oba, Department of Bioengineering, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa 259-1292, Japan, E-mail:

Funding source: Tokai University

Acknowledgments

The authors wish to thank Enago (www.enago.jp) for the English language review.

  1. Author contributions: All authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: This research was supported in part by a doctoral dissertation grant from Tokai University.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2023-11-10
Accepted: 2023-12-13
Published Online: 2023-12-29
Published in Print: 2024-02-26

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
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  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
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  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
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  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
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  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
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https://doi.org/10.1515/ncrs-2023-0496
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of poly[diaqua-(μ4-3,3′-di(1H-1,2,4-triazol-1-yl)-[1,1′-biphenyl]-4,4′-dicarboxylate-N:N′:O:O′)cadmium(II)], C18H14N6O6Cd
  4. Crystal structure of (8R,8′S,13S,13′R)-8,8′-bis(hydroxymethyl)-9,9′,10,10′-tetramethoxy-5,5′,6,6′,8,8′,13,13′-octahydro-[13,13′-bi[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline]-7,7′-diium chloride-methanol (1/2), C46H58N2O14Cl2
  5. The crystal structure of 8-methoxy-2,2-diphenyl-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C29H25BN2O3S
  6. Crystal structure of aqua-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N″,N‴)copper(II) 5-carboxyisophthalate tetrahydrate, C25H50N4CuO11
  7. The crystal structure of 1-(naphthalen-2-ylsulfonyl)-2,2-diphenyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ij]quinoline, C31H23BN2O2S
  8. Crystal structure of iodido-(η6-benzene) (1-(pyridin-2-yl)-N-(p-fluoro-methanamine)-κ2N,Nʹ)ruthenium(II) hexaflourophosphate, (C18H15F7IN2RuP)
  9. The crystal structure of 1-(3-oxo-1-phenyl-3-(p-tolyl) propylidene)-1,3-dihydro-2H-inden-2-one, C25H20O2
  10. Crystal structure of tricyclohexyl[4-(4H-1,2,4-triazol-4-yl)-benzoato-κO]tin(IV), C27H39N3O2Sn
  11. Crystal structure of [triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ4N,O,O,O)cadmium(II)]monohydrate, C12H15NO9Cd
  12. Crystal structure of ethyl 2-((4-(3,5-dimethylisoxazol-4-yl)-2,6-difluorophenyl)amino)benzoate, C20H18F2N2O3
  13. The crystal structure of 2-(hydroxymethyl)-2-(4H-1,2,4-triazol-4-yl)propane-1,3-diol, C6H11N3O3
  14. The crystal structure of 1,2-bis(2,4-dinitrophenyl) hydrazine, C12H8N6O8
  15. Crystal structure of 1-(2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-one, C19H14Cl2N2O3
  16. The crystal structure of 5-amino-5-oxo-4-(1-oxo-4-(2-oxopyrrolidin-1-yl)isoindolin-2-yl)pentanoic acid, C17H19N3O5
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  18. The crystal structure of (E)-2-methoxy-6-(((5-methyl-1,3,4-thiadiazol-2-yl)imino)methyl)phenol, C11H11N3O2S
  19. The crystal structure of 3-((tert-butyldiphenylsilyl)methyl)-5,5-diphenyl-6-(p-tolyl) tetrahydro-2H-pyran-2-one, C41H42O2Si
  20. Crystal structure of 9-fluoro-4-(6-methoxypyridin-3-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  21. The crystal structure of 2-bromo-5-(4-cyanophenoxy)benzyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate, C21H19BrN2O3
  22. Crystal structure of 3,3′-(1,4-phenylenebis(methylene))bis(1-isopropyl-1H-imidazol-3-ium) bis(hexafluorophosphate(V)), C10H14F6N2P
  23. The crystal structure of 2,2-di(thiophen-3-yl)-1-tosyl-1,2-dihydro-2λ4,3λ4-[1,3,2]diazaborolo[4,5,1-ig]quinoline, C24H19BN2O2S3
  24. Crystal structure of 5-bromo-1-(2-iodobenzoyl)-1H-indole-3-carbaldehyde, C16H9BrINO2
  25. The crystal structure of monocarbonyl-2-carboxypyridinato-κ2N,O-triphenylphosphine-rhodium(I) acetonitrile solvate, C26H20.50N1.50O3PRh
  26. Crystal structure of dichlorido-tetrakis(1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ1N)manganese(II), C60H68O4N12Cl10Mn
  27. Crystal structure of 3-(tert-butyldiphenylsilyl)-1-(2,6-dichlorophenyl)-2,2-diphenylpropan-1-ol, C37H36Cl2OSi
  28. Crystal structure of langite from Mine du Pradet (France)
  29. The crystal structure of 5′-(furan-2-yl)-3′-((4-methylphenyl)sulfonamido)-3′,4′,5′,6′-tetrahydro-[1,1′:3′,1″-terphenyl]-4′-carboxylic acid, C30H27NO5S
  30. Synthesis and crystal structure of bis{2-(((4-acetophenone)imino)methyl)-4-fluorophenolato-κ2N,O}zinc(II), C30H22F2N2O4Zn
  31. The crystal structure of poly[(tripyridine-κ3N,N′,N″) μ3-(pyridine-3,4-dicarboxylate-κ3N:O:O′) manganese(II)], C22H22N4O8Mn
  32. The crystal structure of (E)-4-chloro-N′-(1-(4-hydroxyphenyl)propylidene)benzohydrazide, C16H15ClN2O2
  33. Synthesis and crystal structure of bis{2-(tert-butyl)-6-((E)-((4-((E)-1-(methoxyimino) ethyl)phenyl)imino)methyl)phenolato-κ2N,O}cobalt(II), C40H46CoN4O4
  34. Crystal structure of tetraaqua-[(1-(carboxymethyl)-1H-pyrazole-3-carboxylato-κ2N,O)cobalt(II)], C6H12CoN2O8
  35. (6R,7S)-2,3,13-trimethoxy-6,7-dimethyl-5,6,7,8-tetrahydrobenzo[3′,4′]cycloocta [1′,2′:4,5]benzo[1,2-d][1,3]dioxol-1-ol, C22H26O6
  36. Crystal structure of 2-((2,6-dichloro-4-(3,5-dimethylisoxazol-4-yl)phenyl)amino)benzoic acid, C18H14Cl2N2O3
  37. Crystal structure of (5aS,6aS,8aR,9R,11aS, 11bS,13R,13aS)-1,1,8a,11a-tetramethyl-9-((S)-1-((S)-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl)-3-oxo-1,7,8,8a,9,10,11,11a,11b,12,13,13a-dodecahydro-3H,6H-cyclopenta[5,6]cyclopropa[1,8a]naphtho[2,1-c]oxepin-13-yl acetate, C32H44O6
  38. Crystal structure of catena-poly[triaqua-(μ2-1-(4-carboxylatophenyl)-4-oxo-1,4-dihydropyridazine-3-carboxylato-O,O′:O″)cobalt(II)], C12H12N2O8Co
  39. Crystal structure of 3-[(furan-2-ylmethyl)-amino]-2-(2,3,4,5-tetrafluoro-benzoyl)-acrylic acid ethyl ester, C17H13F4NO4
  40. Crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3-methoxybenzoate, C13H16O6
  41. Crystal structure of 4-bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, C13H7BrClF3N2
  42. The crystal structure of triaqua-(8-carboxymethoxy-quinoline-2-carboxylate-κ3N,O,O)nickel(II) monohydrate, C12H15NO9Ni
  43. Crystal structure of dihydroxy(2,4,6-triisopro-pylphenyl)telluronium trifluoromethanesulfonate, C16H25F3O5STe
  44. The crystal structure of 1-(carboxymethyl)-1H-imidazole 3-oxide
  45. The crystal structure of 1,3,5-tris(dibromomethyl)benzene, C9H6Br6
  46. Crystal structure of (Z)-3-(4-methoxyphenyl)-4-(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)-N-phenylthiazol-2(3H)-imine, C25H21N5OS
  47. Crystal structure of (Z)-3-(3-(4-hydroxyphenyl)-2-(phenylimino)-2,3-dihydrothiazol-4-yl)-2H-chromen-2-one, C24H16N2O3S
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