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. 2025 Jan 10;81(Pt 2):114-119.
doi: 10.1107/S2056989025000118. eCollection 2025 Feb 1.

Crystal structures of three salts of the tri-phenylsulfonium ion

Rylan Artis  1 , Waylan Callaway  1 , Elizabeth Heyward  1 , Naomi Reyes  1 , Gavin Roberts  1 , Kaitlyn Van Ostenbridge  1 , Clifford W Padgett  1 , Will E Lynch  1
Affiliations

Crystal structures of three salts of the tri-phenylsulfonium ion

Rylan Artis et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The reactions of tri-phenyl-sulfonium chloride ([TPS][Cl]) with various acids in methanol yield the corresponding salts tri-phenyl-sulfonium triiodide, C18H15S+·I3 - or [TPS][I3] (I), tri-phenyl-sulfonium perchlorate, C18H15S+·ClO4 - or [TPS][ClO4] (II), and tri-phenyl-sulfonium hexa-fluoro-phosphate, C18H15S+·PF6 - or [TPS][PF6] (III), as crystalline products. These crystals were structurally characterized by single-crystal X-ray diffraction. In all three compounds, the sulfur atom in the tri-phenyl-sulfonium cation adopts a distorted trigonal-pyramidal geometry. [TPS][I3] (I) and [TPS][PF6] (III) both crystallize in the space group P21/n, while [TPS][ClO4] (II) crystallizes in P21. The S-C bond lengths are comparable across the three salts, and the S-C-S bond angles are consistently between 102 and 106°. Hirshfeld surface analyses reveal that each structure is dominated by hydrogen-based inter-molecular contacts, supplemented by anion-specific inter-actions such as I⋯H in (I), O⋯H in (II), and F⋯H in (III). These contacts organize the ions into mono-periodic ribbon- or chain-like arrangements. No significant π-π stacking is observed.

Keywords: crystal structure; salts; tri­phenyl­sulfonium ion.

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Figures

Figure 1
Figure 1
The mol­ecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
Figure 2
Figure 2
The mol­ecular structure of (II) with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
Figure 3
Figure 3
The mol­ecular structure of (III) with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
Figure 4
Figure 4
A view along the b-axis direction of the crystal packing of (I) with close contacts shown as red dashed lines.
Figure 5
Figure 5
A view along the [101] direction of the crystal packing of (II) with close contacts shown as red dashed lines.
Figure 6
Figure 6
A view along the c-axis direction of the crystal packing of (III) with close contacts shown as red dashed lines.
See this image and copyright information in PMC

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