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The title coumarin derivative, C20H14N2O3, displays intramolecular N—H...O and weak C—H...O hydrogen bonds, which probably contribute to the approximate planarity of the molecule [dihedral angle between the coumarin and quinoline ring systems = 6.08 (6)°]. The supramolecular structures feature C—H...O hydrogen bonds and π–π interactions, as confirmed by Hirshfeld surface analyses.

Three coumarin derivatives, viz. 6-methyl-N-(3-methylphenyl)-2-oxo-2H-chromene-3-carboxamide, C18H15NO3 (1), N-(3-methoxyphenyl)-6-methyl-2-oxo-2H-chromene-3-carboxamide, C18H15NO4 (2), and 6-methoxy-N-(3-methoxyphenyl)-2-oxo-2H-chromene-3-carboxamide, C18H15NO5 (3), were synthesized and structurally characterized. The molecules display intramolecular N—H...O and weak C—H...O hydrogen bonds, which probably contribute to the approximate planarity of the molecules. The supramolecular structures feature C—H...O hydrogen bonds and π–π interactions, as confirmed by Hirshfeld surface analyses.

The crystal structures of five 6-mercaptopurine derivatives, viz. 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(3-methoxyphenyl)ethan-1-one (1), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-methoxyphenyl)ethan-1-one (2), C16H14N4O3S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-chlorophenyl)ethan-1-one (3), C15H11ClN4O2S, 2-[(9-acetyl-9H-purin-6-yl)sulfanyl]-1-(4-bromophenyl)ethan-1-one (4), C15H11BrN4O2S, and 1-(3-methoxyphenyl)-2-[(9H-purin-6-yl)sulfanyl]ethan-1-one (5), C14H12N4O2S. Compounds (2), (3) and (4) are isomorphous and accordingly their molecular and supramolecular structures are similar. An analysis of the dihedral angles between the purine and exocyclic phenyl rings show that the molecules of (1) and (5) are essentially planar but that in the case of the three isomorphous compounds (2), (3) and (4), these rings are twisted by a dihedral angle of approximately 38°. With the exception of (1) all molecules are linked by weak C—H...O hydrogen bonds in their crystals. There is π–π stacking in all compounds. A Cambridge Structural Database search revealed the existence of 11 deposited compounds containing the 1-phenyl-2-sulfanylethanone scaffold; of these, only eight have a cyclic ring as substituent, the majority of these being heterocycles.