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

In the first title compound, C₁₆H₁₀FNO₃ (<b>I</b>), the dihedral angle between the 2-oxo-2<i>H</i>-chromene ring system and the 2-fluoro-phenyl ring is 0.73 (16)°. In the second title compound, C₁₇H₁₃NO₅S (<b>II</b>), the corresponding angle is 12.44 (2)°. Compound (<b>I</b>) features a bifurcated intra-molecular N-H⋯(O,F) hydrogen bond, whereas (<b>II</b>) displays an N-H⋯O hydrogen bond. In the crystal of (<b>I</b>), the mol-ecules are connected through pairwise C-H⋯O hydrogen bonds forming an inversion dimer generating an <i>R</i> ₂ ²(14) motif, whereas in (<b>II</b>), C-H⋯O hydrogen bonds generate an <i>R</i> ₂ ²(8) motif. The packing for (<b>I</b>) also features a C-H⋯F contact, generating an <i>S</i>(6) chain along [001]. The major contributions to the Hirshfeld surface of (<b>I</b>) 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 (<b>II</b>) 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 (<b>II</b>) demonstrated moderate to good anti-bacterial activity with MIC values of 25 µg ml^-1 against <i>S. aureus</i> and 15 µg ml^-1 against <i>E. coli.</i>