title: Three derivatives of 4-fluoro-5-sulfonylisoquinoline.
abstract: In 4-fluoroisoquinoline-5-sulfonyl chloride, C(9)H(5)ClFNO(2)S, (I), one of the two sulfonyl O atoms lies approximately on the isoquinoline plane as a result of minimizing the steric repulsion between the chlorosulfonyl group and the neighbouring F atom. In (S)-(-)-4-fluoro-N-(1-hydroxypropan-2-yl)isoquinoline-5-sulfonamide, C(12)H(13)FN(2)O(3)S, (II), there are two crystallographically independent molecules (Z' = 2). The molecular conformations of these two molecules differ in that the amine group of one forms an intramolecular bifurcated hydrogen bond with the F and OH groups, whilst the other forms only a single intramolecular N-H···F hydrogen bond. The N-H···F hydrogen bonds correspond to weak coupling between the N(H) and (19)F nuclei, observed in the (1)H NMR solution-state spectra. In (S)-(-)-4-[(4-fluoroisoquinolin-5-yl)sulfonyl]-3-methyl-1,4-diazepan-1-ium chloride, C(15)H(19)FN(3)O(2)S(+)·Cl(-), (III), the isoquinoline plane is slightly deformed, suggestive of a steric effect induced by the bulky substituent on the sulfonyl group.
authors.affiliation: Research and Education Center for Natural Sciences, Keio University, Hiyoshi, Kohoku-ku, Yokohama, Japan. ohba@a3.keio.jp
authors.forename: Shigeru
authors.initials: S
authors.lastname: Ohba
authors.forename: Noriaki
authors.initials: N
authors.lastname: Gomi
authors.forename: Tadaaki
authors.initials: T
authors.lastname: Ohgiya
authors.forename: Kimiyuki
authors.initials: K
authors.lastname: Shibuya
mesh_terms: D001381:Azepines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D007546:Isoquinolines / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: C577027:(S)-(-)-4-((4-fluoroisoquinolin-5-yl)sulfonyl)-3-methyl-1,4-diazepan-1-ium chloride; C577026:4-fluoro-5-sulfonylisoquinoline; D001381:Azepines; D007546:Isoquinolines