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

• Type: Article in International Scientific Journal
• Date: 2015

Authors

Gomes, LR (Author) Other; Low, JN (Author) Other; Fernando Cagide (Author) FCUP; Fernanda Borges (Author) FCUP; Lough, AJ (Author) Other

Journal

Title: Acta Crystallographica Section E: Crystallographic Communications

Vol. 71

Pages: 88-+

Publisher: International Union of Crystallography

Indexing

ISI Web of Knowledge - 9 Citations

Scopus - 9 Citations

Other information

Authenticus ID: P-00A-C3F

DOI: 10.1107/s2056989014027054

Abstract (EN): 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-iodopheny1)-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 C-arom-C-arom 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 center dot center dot center dot O hydrogen bond between the amide N atom and the 0 atom of the carbonyl group of the pyrone ring, forming an S(6) ring, and a weak C-arom-H center dot center dot center dot 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 supra molecular structure, consisting of R-2(2)(13) rings that are propagated along the a axis direction by unit translation. There is pi-pi stacking involving inversion related molecules in each structure.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 22