Spectroscopic, crystallographic, and Hirshfeld surface characterization of nine-membered-ring-containing 9-meth-oxy-3,4,5,6-tetra-hydro-1 H-benzo[ b]azonine-2,7-dione and its parent tetra-hydro-car-ba-zole

Maritza J Flores; Brandon Mai; Joseph M Tanski

doi:10.1107/S2056989023007259

Spectroscopic, crystallographic, and Hirshfeld surface characterization of nine-membered-ring-containing 9-meth-oxy-3,4,5,6-tetra-hydro-1 H-benzo[ b]azonine-2,7-dione and its parent tetra-hydro-car-ba-zole

Acta Crystallogr E Crystallogr Commun. 2023 Aug 23;79(Pt 9):831-836. doi: 10.1107/S2056989023007259. eCollection 2023 Sep 1.

Authors

Maritza J Flores¹, Brandon Mai¹, Joseph M Tanski¹

Affiliation

¹ Department of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA.

Abstract

9-Meth-oxy-3,4,5,6-tetra-hydro-1H-benzo[b]azonine-2,7-dione, C₁₃H₁₅NO₃, (I), and 6-meth-oxy-1,2,3,4-tetra-hydro-car-ba-zole, C₁₃H₁₅NO, (II), represent the structures of a benzoazonine that contains a nine-membered ring and its parent tetra-hydro-car-ba-zole. The mol-ecules of (I) pack together via strong amide N-H⋯O hydrogen bonding and weak C-H⋯O inter-actions, whereas the parent tetra-hydro-car-ba-zole (II) packs with C/N-H⋯π inter-actions, as visualized by Hirshfeld surface characterization.

Keywords: benzo[b]azonine; crystal structure; hydrogen bond; nine-membered ring; tetrahydrocarbazole.

Grants and funding

Funding for this research was provided by: National Science Foundation (grant Nos. 0521237 and 0911324 to J. M. Tanski).