Crystal structure of (3 S*,4 R*)-4-fluoro-3-(4-meth-oxy-phen-yl)-1-oxo-2-phenyl-1,2,3,4-tetra-hydro-iso-quinoline-4-carb-oxy-lic acid

Anna Lehmann; Lisa Lechner; Krzysztof Radacki; Holger Braunschweig; Ulrike Holzgrabe

doi:10.1107/S2056989017007186

Crystal structure of (3 S,4 R)-4-fluoro-3-(4-meth-oxy-phen-yl)-1-oxo-2-phenyl-1,2,3,4-tetra-hydro-iso-quinoline-4-carb-oxy-lic acid

Acta Crystallogr E Crystallogr Commun. 2017 May 23;73(Pt 6):867-870. doi: 10.1107/S2056989017007186. eCollection 2017 Jun 1.

Authors

Anna Lehmann¹, Lisa Lechner¹, Krzysztof Radacki², Holger Braunschweig², Ulrike Holzgrabe¹

Affiliations

¹ Institute of Pharmacy and Food Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, Germany.
² Institute of Inorganic Chemistry, University of Wuerzburg, Am Hubland, 97074 Wuerzburg, Germany.

Abstract

The title compound, C₂₃H₁₈FNO₄, crystallized as a racemate. It exhibits a cis conformation with respect to the F atom and the methine H atom. The piperidine ring has a screw-boat conformation. The meth-oxy-phenyl ring and the phenyl ring are inclined to the mean plane of the iso-quinoline ring system by 89.85 (4) and 46.62 (5)°, respectively, and by 78.15 (5)° to one another. In the crystal, mol-ecules are linked by an O-H⋯O hydrogen bond forming chains propagating along the a-axis direction. The chains are linked by C-H⋯F hydrogen bonds, forming layers lying parallel to the ab plane.

Keywords: 1-oxotetrahydroisoquinolinon-4-carboxylic acid; cis conformation; crystal structure; fluorination; hydrogen bonding.