A commonly used spin label: S-(2,2,5,5-tetra-methyl-1-oxyl- Δ3-pyrrolin-3-ylmeth-yl) methane-thio-sulfonate

Vitali Zielke, Henning Eickmeier, K. Hideg, Hans Reuter, Heinz Jürgen Steinhoff

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The title compound, C10H18NO3S2, which finds application as a spin label, has triclinic (P ) symmetry at 100 (2) K with two independent mol-ecules in the asymmetric unit. Both mol-ecules are very similar with respect to bond lengths and angles, but mol-ecule 2 shows disordering of its side chain. The pyrroline rings differ slightly with respect to the position of the NO group, which in both cases are sterically shielded by the surrounding methyl groups. The crystal structure of the title compound represents the first example of a 2,2,5,5-tetra-methyl-1-oxyl-Δ3-pyrroline derivative with a side chain at the double bond which is linked to it through an sp 3-hybridized C atom. In the solid state, the side chain adopts a conformation with the methyl group above/below the pyrroline ring and a H atom directed towards a C atom of the double bond. The disordered side chain of mol-ecule 2 represents a second conformation with low potential energy. Both mol-ecules exhibit planar chirality, but in the solid state both pairs of stereoisomers are present. These four stereoisomers are stacked one behind the other in four different columns, denoted A, A′, B and B′, the angle between the vectors of the N - O bonds in columns A and B being 80.38 (8)°.

Original languageEnglish
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume64
Issue number11
DOIs
Publication statusPublished - 2008

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Spin Labels
Methane
Stereoisomerism
Atoms
Conformations
Chirality
Bond length
Potential energy
Crystal structure
Derivatives
pyrroline

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

A commonly used spin label : S-(2,2,5,5-tetra-methyl-1-oxyl- Δ3-pyrrolin-3-ylmeth-yl) methane-thio-sulfonate. / Zielke, Vitali; Eickmeier, Henning; Hideg, K.; Reuter, Hans; Steinhoff, Heinz Jürgen.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 64, No. 11, 2008.

Research output: Contribution to journalArticle

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abstract = "The title compound, C10H18NO3S2, which finds application as a spin label, has triclinic (P ) symmetry at 100 (2) K with two independent mol-ecules in the asymmetric unit. Both mol-ecules are very similar with respect to bond lengths and angles, but mol-ecule 2 shows disordering of its side chain. The pyrroline rings differ slightly with respect to the position of the NO group, which in both cases are sterically shielded by the surrounding methyl groups. The crystal structure of the title compound represents the first example of a 2,2,5,5-tetra-methyl-1-oxyl-Δ3-pyrroline derivative with a side chain at the double bond which is linked to it through an sp 3-hybridized C atom. In the solid state, the side chain adopts a conformation with the methyl group above/below the pyrroline ring and a H atom directed towards a C atom of the double bond. The disordered side chain of mol-ecule 2 represents a second conformation with low potential energy. Both mol-ecules exhibit planar chirality, but in the solid state both pairs of stereoisomers are present. These four stereoisomers are stacked one behind the other in four different columns, denoted A, A′, B and B′, the angle between the vectors of the N - O bonds in columns A and B being 80.38 (8)°.",
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