Three derivatives of 4-fluoro-5-sulfonyl-isoquinoline

Shigeru Ohba, Noriaki Gomi, Tadaaki Ohgiya, Kimiyuki Shibuya

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

In 4-fluoro-isoquinoline-5-sulfonyl chloride, C9H 5ClFNO2S, (I), one of the two sulfonyl O atoms lies approximately on the isoquinoline plane as a result of minimizing the steric repulsion between the chloro-sulfonyl group and the neighbouring F atom. In (S)-(-)-4-fluoro-N-(1-hy-droxy-propan-2-yl)isoquinoline-5-sulfonamide, C 12H13FN2O3S, (II), there are two crystallographically independent molecules (Z′ = 2). The mol-ecular conformations of these two molecules differ in that the amine group of one forms an intra-molecular bifurcated hydrogen bond with the F and OH groups, whilst the other forms only a single intra-molecular N - H⋯F hydrogen bond. The N - H⋯F hydrogen bonds correspond to weak coupling between the N(H) and 19F nuclei, observed in the 1H NMR solution-state spectra. In (S)-(-)-4-[(4-fluoro-isoquinolin-5-yl)sulfon-yl]-3-methyl-1,4-diazepan-1-ium chloride, C15H19FN3O2S +·Cl-, (III), the isoquinoline plane is slightly deformed, suggestive of a steric effect induced by the bulky substituent on the sulfonyl group.

Original languageEnglish
JournalActa Crystallographica Section C: Crystal Structure Communications
Volume68
Issue number10
DOIs
Publication statusPublished - 2012 Oct

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Hydrogen
Hydrogen bonds
Derivatives
Atoms
Molecules
Amines
Conformations
Chlorides
Nuclear magnetic resonance
isoquinoline
isoquinoline-5-sulfonamide
sulfonyl chloride
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

Three derivatives of 4-fluoro-5-sulfonyl-isoquinoline. / Ohba, Shigeru; Gomi, Noriaki; Ohgiya, Tadaaki; Shibuya, Kimiyuki.

In: Acta Crystallographica Section C: Crystal Structure Communications, Vol. 68, No. 10, 10.2012.

Research output: Contribution to journalArticle

Ohba, Shigeru ; Gomi, Noriaki ; Ohgiya, Tadaaki ; Shibuya, Kimiyuki. / Three derivatives of 4-fluoro-5-sulfonyl-isoquinoline. In: Acta Crystallographica Section C: Crystal Structure Communications. 2012 ; Vol. 68, No. 10.
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AB - In 4-fluoro-isoquinoline-5-sulfonyl chloride, C9H 5ClFNO2S, (I), one of the two sulfonyl O atoms lies approximately on the isoquinoline plane as a result of minimizing the steric repulsion between the chloro-sulfonyl group and the neighbouring F atom. In (S)-(-)-4-fluoro-N-(1-hy-droxy-propan-2-yl)isoquinoline-5-sulfonamide, C 12H13FN2O3S, (II), there are two crystallographically independent molecules (Z′ = 2). The mol-ecular conformations of these two molecules differ in that the amine group of one forms an intra-molecular bifurcated hydrogen bond with the F and OH groups, whilst the other forms only a single intra-molecular N - H⋯F hydrogen bond. The N - H⋯F hydrogen bonds correspond to weak coupling between the N(H) and 19F nuclei, observed in the 1H NMR solution-state spectra. In (S)-(-)-4-[(4-fluoro-isoquinolin-5-yl)sulfon-yl]-3-methyl-1,4-diazepan-1-ium chloride, C15H19FN3O2S +·Cl-, (III), the isoquinoline plane is slightly deformed, suggestive of a steric effect induced by the bulky substituent on the sulfonyl group.

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