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The CuII atom in the title compound, [Cu(C16H10ClN2O)2], is located on an inversion center and is tetra­coordinated by two N and two O atoms from two bidentate 1-[(E)-(2-chloro­phen­yl)diazen­yl]naphthalen-2-olate ligands, forming a square-planar complex. In the crystal, mol­ecules are linked via weak C—H...O and C—H...Cl hydrogen bonds, forming chains propagating along [010]. There are also π–π inter­actions present involving adjacent naphthalene rings [centroid–centroid distance = 3.661 (13) Å].

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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—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.

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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—H...O hydrogen bonds, forming –AAA– and –BBB– 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].

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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 zwitterionic compound, C16H12N2O, the dihedral angle between the phenyl ring and the naphthalene ring system is 17.85 (8)°; an intra­molecular N—H...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.

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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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