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The title compound, C18H14N2O2, crystallized with two independent zwitterion molecules (A and B) in the asymmetric unit. They are both close to planar, the dihedral angle between the benzene ring and naphthalene ring system being 4.30 (9)° in A and 4.69 (9)° in B. Each molecule has an E conformation with respect to the azo double bond. In each of the independent molecules, an intramolecular N—H
O hydrogen bond forms an S(6) ring motif. In the crystal, molecules are linked via C—HO hydrogen bonds, forming –A—A—A– and –B—B—B– chains parallel to one another and propagating along the a-axis direction. There are also π–π interactions between adjacent molecules involving benzene and naphthalene rings [centroid–centroid distance of 3.626 (3) Å for adjacent A molecules and 3.652 (3) Å for adjacent B molecules].
O hydrogen bond forms an S(6) ring motif. In the crystal, molecules are linked via C—HO hydrogen bonds, forming –A—A—A– and –B—B—B– chains parallel to one another and propagating along the a-axis direction. There are also π–π interactions between adjacent molecules involving benzene and naphthalene rings [centroid–centroid distance of 3.626 (3) Å for adjacent A molecules and 3.652 (3) Å for adjacent B molecules].organic compoundsOpen access
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There are two independent zwitterion molecules (A and B) in the asymmetric unit of the title compound, C17H11N3O, which belongs to the family of azo dyes. The dihedral angle between the benzene ring and the naphthalene ring system is 6.99 (6)° in molecule A and 4.38 (6)° in molecule B. The azo group adopts an E conformation with respect to the –N=N– bond and each of the independent molecules has an intramolecular N—HO hydrogen bond. In the crystal, molecules are linked by C—HO and C—HN hydrogen bonds, forming ribbons propagating along [-110]. The ribbons are linked via π–π interactions involving the benzene and naphthalene rings of inversion-related A and inversion-related B molecules, forming a three-dimensional structure. The most significant centroid–centroid distances vary from 3.6599 (6) to 3.7538 (9) Å.
O hydrogen bond. In the crystal, molecules are linked by C—HO and C—HN hydrogen bonds, forming ribbons propagating along [-110]. The ribbons are linked via π–π interactions involving the benzene and naphthalene rings of inversion-related A and inversion-related B molecules, forming a three-dimensional structure. The most significant centroid–centroid distances vary from 3.6599 (6) to 3.7538 (9) Å.organic compoundsOpen access
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In the title zwitterionic compound, C16H12N2O, the dihedral angle between the phenyl ring and the naphthalene ring system is 17.85 (8)°; an intramolecular N—HO hydrogen bond occurs. In the crystal, π–π stacking is observed between naphthalene ring systems of adjacent molecules, the centroid–centroid distance being 3.6486 (11) Å.
O hydrogen bond occurs. In the crystal, π–π stacking is observed between naphthalene ring systems of adjacent molecules, the centroid–centroid distance being 3.6486 (11) Å.
