Syntheses and structures of N-(2-fluoro­phen­yl)-2-oxo-2H-chromene-3-carboxamide and N-[4-(methyl­sulfon­yl)phen­yl]-2-oxo-2H-chromene-3-carboxamide

Abstract

In the first title compound, C16H10FNO3 (I), the dihedral angle between the 2-oxo-2H-chromene ring system and the 2-fluoro­phenyl ring is 0.73 (16)°. In the second title compound, C17H13NO5S (II), the corresponding angle is 12.44 (2)°. Compound (I) features a bifurcated intra­molecular N—H⋯(O,F) hydrogen bond, whereas (II) displays an N—H⋯O hydrogen bond. In the crystal of (I), the mol­ecules are connected through pairwise C—H⋯O hydrogen bonds forming an inversion dimer generating an R22(14) motif, whereas in (II), C—H⋯O hydrogen bonds generate an R22(8) motif. The packing for (I) also features a C—H⋯F contact, generating an S(6) chain along [001]. The major contributions to the Hirshfeld surface of (I) are from H⋯H (30.0%), O⋯H/H⋯O (21.0%), C⋯H/H⋯C (15.9%), C⋯C (12.5%), F⋯H/H⋯F (10.8%) and O⋯C/C⋯O (5.0%) contacts while those in (II) are from H⋯H (28.0%), O⋯H/H⋯O (36.7%), C⋯H/H⋯C (19.8%), C⋯C (5.6%), and O⋯C/C⋯O (6.9%) contacts. Compound (II) demonstrated moderate to good anti-bacterial activity with MIC values of 25 µg ml−1 against S. aureus and 15 µg ml−1 against E. coli.