Synthesis, crystal structure and Hirshfeld surface analysis of phenyl­methanaminium 2-oxo-2H-chromene-3-carboxyl­ate

Abstract

The title salt, C7H10N+·C10H4O−, formed between 2-oxo-2H-chromene-3-carb­oxy­lic acid and benzyl­amine crystallizes in the triclinic space group P1. Proton transfer from 2-oxo-2H-chromene-3-carb­oxy­lic acid to the NH2 group of benzyl­amine results in a N—H⋯(O,O) hydrogen bond between cation and the carboxylate group of the anion. The 2-oxo-2H-chromene moiety is almost planar with a dihedral angle between the two fused rings of 1.48 (11)°. The dihedral angle between the rings of the anion and cation is 29.49 (10)°. In the crystal, N—H⋯O hydrogen-bonding inter­actions generate an R44(12) synthon parallel to the ac plane. The mol­ecules are linked by further C—H⋯π inter­actions, which consolidate the packing. In addition, π–π stacking inter­actions are observed with centroid-to-centroid distances of 3.5832 (14) and 3.8167 (15) Å. The two-dimensional fingerprint plots indicates that the most important contributions to the crystal packing are from H⋯H (39.7%), H⋯O/O⋯H (30.6%) and H⋯C/C⋯H (20.9%) contacts. The anti­bacterial activity, with MIC values of 30 µg ml−1 against S. aureus and 25 µg ml−1 against E. coli. The lower MIC against E. coli suggests that the compound is more effective against Gram-negative bacteria than Gram-positive bacteria.