Crystal structures of three 6-substituted coumarin-3-carboxamide derivatives

Lígia R Gomes; John Nicolson Low; André Fonseca; Maria João Matos; Fernanda Borges

doi:10.1107/S2056989016008665

Crystal structures of three 6-substituted coumarin-3-carboxamide derivatives

Acta Crystallogr E Crystallogr Commun. 2016 Jun 10;72(Pt 7):926-32. doi: 10.1107/S2056989016008665. eCollection 2016 Jul 1.

Authors

Lígia R Gomes¹, John Nicolson Low², André Fonseca³, Maria João Matos³, Fernanda Borges³

Affiliations

¹ REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007, Porto, Portugal; FP-ENAS-Faculdade de Ciências de Saúde, Escola Superior de Saúde da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal.
² Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland.
³ CIQUP/Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade do Porto, 4169-007 Porto, Portugal.

Abstract

Three coumarin derivatives, viz. 6-methyl-N-(3-methyl-phen-yl)-2-oxo-2H-chromene-3-carboxamide, C18H15NO3 (1), N-(3-meth-oxy-phen-yl)-6-methyl-2-oxo-2H-chromene-3-carboxamide, C18H15NO4 (2), and 6-meth-oxy-N-(3-meth-oxy-phen-yl)-2-oxo-2H-chromene-3-carboxamide, C18H15NO5 (3), were synthesized and structurally characterized. The mol-ecules display intra-molecular N-H⋯O and weak C-H⋯O hydrogen bonds, which probably contribute to the approximate planarity of the mol-ecules. The supra-molecular structures feature C-H⋯O hydrogen bonds and π-π inter-actions, as confirmed by Hirshfeld surface analyses.

Keywords: carboxamide; coumarin; crystal structure.