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In the title compound, C13H8N2O2, prepared from furfuryl alcohol and 4-nitrophthalonitrile in the presence of potassium carbonate in dimethylformamide, the furan and benzene rings are oriented at a dihedral angle of 53.45 (9)°. In the crystal, weak C—H
O and C—HN hydrogen bonds link the molecules into a three-dimensional network.
O and C—HN hydrogen bonds link the molecules into a three-dimensional network.organic compoundsOpen access
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The asymmetric unit of the title compound, C21H13N3O2, contains two independent molecules with a similar structure. In one molecule, the central benzene ring is oriented with respect to the terminal benzene rings at 27.23 (7) and 67.96 (7)°; in the other molecule, the corresponding dihedral angles are 12.42 (7) and 64.55 (7)°. In both molecules, there is a short O—HN interaction involving the OH group and the adjacent N atom. In the crystal, there are O—HN hydrogen bonds, and C—HO and N—HO interactions linking the molecules to form a three-dimensional network. π–π stacking between the pyridine and benzene rings and between the benzene rings [centroid–centroid distances = 3.989 (2), 3.705 (2) and 3.607 (2) Å] may further stabilize the structure. A weak C—Hπ interaction is present in the crystal.
N interaction involving the OH group and the adjacent N atom. In the crystal, there are O—HN hydrogen bonds, and C—HO and N—HO interactions linking the molecules to form a three-dimensional network. π–π stacking between the pyridine and benzene rings and between the benzene rings [centroid–centroid distances = 3.989 (2), 3.705 (2) and 3.607 (2) Å] may further stabilize the structure. A weak C—Hπ interaction is present in the crystal.
