The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides

Acta Crystallographica Section E: Crystallographic Communications

Gomes, L.R.³  Borges, F.⁴  Cagide, F.⁵  Low, J.N.⁸ 

[1]CIQ/Departamento de Quι

[2]Department of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen, AB24 3UE, Scotland

[3]FP-ENAS-Faculdade de Ciê

[4]de da UFP, Universidade Fernando Pessoa, Rua Carlos da Maia, 296, P-4200-150 Porto, Portugal

[5]de, Escola Superior de Saú

[6]mica e Bioquι

[7]mica, Faculdade de Ciê

[8]ncias de Saú

[9]ncias, Universidade do Porto, 4169-007 Porto, Portugal

关键词: CRYSTAL STRUCTURE;    DRUG DESIGN;    CHROMONES;    CONFORMATION;    SUPRAMOLECULAR STRUCTURE;   

DOI  :  10.1107/S2056989014027054

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

Four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides (halo = F, Cl, Br and I), N-(4-fluoro­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C16H10FNO3, N-(4-chloro­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C16H10ClNO3, N-(4-bromo­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C16H10BrNO3, N-(4-iodo­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C16H10INO3, have been structurally characterized. The mol­ecules are essentially planar and each exhibits an anti conformation with respect to the C—N rotamer of the amide and a cis geometry with respect to the relative positions of the Carom—Carom bond of the chromone ring and the carbonyl group of the amide. The structures each exhibit an intra­molecular hydrogen-bonding network comprising an N—H⋯O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an S(6) ring, and a weak Carom—H⋯O inter­action with the O atom of the carbonyl group of the amide as acceptor, which forms another S(6) ring. All four compounds have the same supra­molecular structure, consisting of R22(13) rings that are propagated along the a-axis direction by unit translation. There is π–π stacking involving inversion-related mol­ecules in each structure.

【 授权许可】

CC BY