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The title zwitterion,, C16H11ClN2O, is approximately planar, the dihedral angle between the benzene ring and naphthalene ring system is 1.55 (13)°; an intra­molecular N—H...O hydrogen bond stabilizes the planar conformation. In the crystal, π–π stacking between the benzene ring and the naphthalene ring system of adjacent mol­ecules links the mol­ecules into supra­molecular chains running along the b axis, the centroid–centroid distance being 3.765 (2) Å.

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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—H...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].

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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—H...O hydrogen bond in each molecule helps to establish their near planar conformation. In the crystal, mol­ecules are linked through O—H...O 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.

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In the title zwitterion, C17H12N2O2, the dihedral angle between the benzene ring and naphthalene ring system is 11.76 (7)° and an intra­molecular N—H...O hydrogen bond exists. In the crystal, molecules are linked via pairs of C—H...O hydrogen bonds, forming inversion dimers.
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