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

In the first title compound, C 16 H 10 FNO 3 ( I ), the dihedral angle between the 2-oxo-2 H -chromene ring system and the 2-fluorophenyl ring is 0.73 (16)°. In the second title compound, C 17 H 13 NO 5 S ( 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 R 2 2 (14) motif, whereas in ( II ), C—H...O hydrogen bonds generate an R 2 2 (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.