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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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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 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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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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