Abstract
In the title compound, C16H12N2O2·0.5CH3OH, the H atom of the –OH group has been transfered to the N atom in the azo group, forming a zwitterion. Hence, there is an intramolecular N—H⋯O, rather than an O—H⋯N, hydrogen bond in the molecule. The molecule is almost planar, the dihedral angle between the benzene ring and the mean plane of the naphthalene ring system being 4.51 (6)°. In the crystal, molecules are linked to and bridged by O—H⋯O hydrogen bonds involving the methanol molecule, which is located about a twofold rotation axis, and hence half-occupied, forming zigzag chains along [001]. Molecules are also linked via C—H⋯π and π–π interactions, the latter involving adjacent benzene and naphthalene rings and having a centroid–centroid distance of 3.6616 (13) Å, forming a three-dimensional network.
Highlights
In the title compound, C16H12N2O20.5CH3OH, the H atom of the –OH group has been transfered to the N atom in the azo group, forming a zwitterion
Cg2 and Cg3 are the centroids of the C5–C10 and C11–C16 rings, respectively
Molecules are linked to and bridged by O—H O hydrogen bonds involving the methanol molecule, which is located about a twofold rotation axis, and half-occupied, forming zigzag chains along [001]
Summary
Cg2 and Cg3 are the centroids of the C5–C10 and C11–C16 rings, respectively. C16H12N2O20.5CH3OH, the H atom of the –OH group has been transfered to the N atom in the azo group, forming a zwitterion. N—H O, rather than an O—H N, hydrogen bond in the molecule. The molecule is almost planar, the dihedral angle between the benzene ring and the mean plane of the naphthalene ring system being 4.51 (6). Molecules are linked to and bridged by O—H O hydrogen bonds involving the methanol molecule, which is located about a twofold rotation axis, and half-occupied, forming zigzag chains along [001]. H and – interactions, the latter involving adjacent benzene and naphthalene rings and having a centroid–. Centroid distance of 3.6616 (13) Å, forming a three-dimensional network
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