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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—HN, 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—HO 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—Hπ 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.
O, rather than an O—HN, 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—HO 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—Hπ 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.organic compoundsOpen access
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The title azo molecule, C16H9Br3N2O, adopts a trans conformation with respect to the azo N=N double bond. An intramolecular O—HN hydrogen bond forms an S(6) ring motif. The dihedral angle between the naphthalene ring system and the benzene ring is 33.80 (16)°. In the crystal, molecules are stacked in columns along the a axis by π–π interactions [centroid–centroid distances = 3.815 (3) and 3.990 (3) Å].
N hydrogen bond forms an S(6) ring motif. The dihedral angle between the naphthalene ring system and the benzene ring is 33.80 (16)°. In the crystal, molecules are stacked in columns along the a axis by π–π interactions [centroid–centroid distances = 3.815 (3) and 3.990 (3) Å].organic compoundsOpen access
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The title zwitterion, C17H14N2O2, crystallizes with two independent molecules in the asymmetric unit, both of which are approximately planar, the dihedral angles between the benzene ring and the naphthalene ring system being 4.39 (12)° in one molecule and 5.83 (12)° in the other, and show an E conformation with respect to the azo double bond. An intramolecular N—HO hydrogen bond in each molecule helps to establish their near planar conformation. In the crystal, molecules are linked through O—HO hydrogen bonds into infinite chains running along the a-axis direction. In addition, the chains are stacked along the b axis via π–π interactions between the benzene and the naphthalene rings of adjacent molecules, the centroid–centroid distances being 3.722 (3) and 3.823 (4) Å.
O hydrogen bond in each molecule helps to establish their near planar conformation. In the crystal, molecules are linked through O—HO hydrogen bonds into infinite chains running along the a-axis direction. In addition, the chains are stacked along the b axis via π–π interactions between the benzene and the naphthalene rings of adjacent molecules, the centroid–centroid distances being 3.722 (3) and 3.823 (4) 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.
