Crystal structure of [2-(triethylammonio)ethyl][(2,4,6-triisopropylphenyl)sulfonyl]amide tetrahydrate

Golz, Christopher; Strohmann, Carsten

doi:10.1107/s2056989015008105

Acta Cryst E

2015

DOI: 10.1107/s2056989015008105

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Crystal structure of [2-(triethylammonio)ethyl][(2,4,6-triisopropylphenyl)sulfonyl]amide tetrahydrate

Christopher Golz¹,

Carsten Strohmann²

Abstract: The zwitterionic title compound shows a major disorder of the triisopropylphenyl group over two equally occupied locations. An interesting feature is the uncommon hydrate structure, exhibiting a tape-like motif which can be classified as a transition of the one-dimensional T4(2)6(2) motif into the two-dimensional L4(6)5(7)6(8) motif.

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Cited by 2 publications

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High-resolution structural study on pyridin-3-yl ebselen and its N-methylated tosylate and iodide derivatives

Fellowes

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2023

Acta Crystallogr C Struct Chem

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The crystal structure of the pyridine-substituted benzisoselenazolinone 2-(pyridin-3-yl)-2,3-dihydro-1,2-benzoselenazol-3-one (C12H8N2OSe, 2), related to the antioxidant ebselen [systematic name: 2-phenyl-1,2-benzoselenazol-3(2H)-one, 1], is characterized by strong intermolecular N...Se(—N) chalcogen bonding, where the N...Se distance of 2.3831 (6) Å is well within the sum of the van der Waals radii for N and Se (3.34 Å). This strong interaction results in significant lengthening of the internal N—Se distance, consistent with significant population of the Se—N σ* antibonding orbital. Much weaker intermolecular O...Se chalcogen bonding occurs between the amide-like O atom in 2 and the less polarized C—Se bond in this structure. Charge density analysis of 2 using multipole refinement of high-resolution data allowed the electrostatic surface potential for 2 to be mapped, and clearly reveals the σ-hole at the extension of the Se—N bond as an area of positive electrostatic potential. Topological analysis of the electron-density distribution in 2 was carried out within the Quantum Theory of Atoms in Molecules (QTAIM) framework and revealed bond paths and (3,−1) bond critical points (BCPs) for the N...Se—N moiety consistent with a closed-shell interaction; however, the potential energy term is suggestive of electron sharing. Analysis of the electron localization function (ELF) for the strong N...Se and the weak O...Se chalcogen-bonding interactions in the structure of 2 suggest significant electron sharing in the former interaction, and a largely electrostatic interaction in the latter. Conversion of 2 to its N-methylated derivatives by reaction with methyl iodide [1-methyl-3-(3-oxo-2,3-dihydro-1,2-benzoselenazol-2-yl)pyridin-1-ium iodide, C13H11N2OSe+·I−] and methyl tosylate [1-methyl-3-(3-oxo-2,3-dihydro-1,2-benzoselenazol-2-yl)pyridin-1-ium toluenesulfonate trihydrate, C13H11N2OSe+·C7H7O3S−·3H2O] removes the possibility of N...Se chalcogen bonding and instead structures are obtained where the iodide and tosylate counter-ions fulfill the role of chalcogen-bond acceptors, with a strong I−...Se interaction in the iodide salt and a weaker p-Tol-SO3 −...Se interaction in the tosylate salt.

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High-resolution structural study on pyridin-3-yl ebselen and its N-methylated tosylate and iodide derivatives

Fellowes

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2023

Acta Crystallogr C Struct Chem

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Crystal structure of 1-[(2,4,6-triisopropylphenyl)sulfonyl]aziridine

2015

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The title compound, C17H27NO2S, exhibits a distorted geometry of the aromatic ring with elongated bonds at the ipso-C atom. The S atom deviates from the aromatic ring plane by 0.393 (4) Å. Similar to this, the adjacent isopropyl groups are bent out of the aromatic ring plane by −0.125 (4) and −0.154 (4) Å. Even the distant isopropyl group in para-position to the sulfonyl moiety shows a slight deviation from the ring plane of 0.111 (5) Å. These distortions, which are caused by the bulky substituents, can also be observed in related sulfonylaziridine structures.

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Crystal structure of [2-(triethylammonio)ethyl][(2,4,6-triisopropylphenyl)sulfonyl]amide tetrahydrate

Cited by 2 publications

References 16 publications

High-resolution structural study on pyridin-3-yl ebselen and its N-methylated tosylate and iodide derivatives

High-resolution structural study on pyridin-3-yl ebselen and its N-methylated tosylate and iodide derivatives

Crystal structure of 1-[(2,4,6-triisopropylphenyl)sulfonyl]aziridine

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