Crystal structures of a copper(II) and the isotypic nickel(II) and palladium(II) complexes of the ligand (E)-1-[(2,4,6-tri­bromo­phen­yl)diazen­yl]naphthalen-2-ol

In the copper(II) complex, bis­{(E)-1-[(2,4,6-tri­bromo­phen­yl)diazen­yl]naph­thalen-2- olato}copper(II), [Cu(C₁₆H₈Br₃N₂O)₂], (I), the metal cation is coord­inated by two N atoms and two O atoms from two bidentate (E)-1-[(2,4,6-tri­bromo­phen­yl)diazen­yl]naphthalen-2-olate ligands, forming a slightly distorted square-planar environment. In one of the ligands, the tri­bromo­benzene ring is inclined to the naphthalene ring system by 37.4 (5)°, creating a weak intra­molecular Cu...Br inter­action [3.134 (2) Å], while in the other ligand, the tri­bromo­benzene ring is inclined to the naphthalene ring system by 72.1 (6)°. In the isotypic nickel(II) and palladium(II) complexes, namely bis­{(E)-1-[(2,4,6-tri­bromo­phen­yl)diazen­ yl]naphthalen-2-olato}nickel(II), [Ni(C₁₆H₈Br₃N₂O)₂], (II), and bis­{(E)-1- [(2,4,6-tri­bromo­phen­yl)diazen­yl]naphthalen-2-olato}palladium(II), [Pd(C₁₆H₈Br₃N₂O)₂], (III), respectively, the metal atoms are located on centres of inversion, hence the metal coordination spheres have perfect square-planar geometries. The tri­bromo­benzene rings are inclined to the naphthalene ring systems by 80.79 (18)° in (II) and by 80.8 (3)° in (III). In the crystal of (I), mol­ecules are linked by C-H...Br hydrogen bonds, forming chains along [010]. The chains are linked by C-H...Pi inter­actions, forming sheets parallel to (011). In the crystals of (II) and (III), mol­ecules are linked by C-H...Pi inter­actions, forming slabs parallel to (10-1). For the copper(II) complex (I), a region of disordered electron density was corrected for using the SQUEEZE routine in PLATON [Spek (2015). Acta Cryst. C71, 9-18]. The formula mass and unit-cell characteristics of the disordered solvent mol­ecules were not taken into account during refinement

1-(4-Hydroxyphenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium methanol hemisolvate

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

(E)-1-[2-(3,4-Dimethylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

The title zwitterion, C18H16N2O, features an intramolecular N—H...O hydrogen bond. The dimethylbenzene ring is rotationally disordered about the N—C bond over two adjacent orientations in a 0.75:0.25 ratio. The dihedral angle between the major orientation of the benzene ring and the naphthalene ring system is 6.06 (2)°. In the crystal, aromatic π–π stacking occurs [shortest centroid–centroid distance = 3.574 (3) Å] and C—H...O interactions are also observed

(E)-1-[(2,4,6-Tribromophenyl)diazenyl]naphthalen-2-ol

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]

Chlorido{(E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-olato}palladium(II)

In the title complex, [Pd(C17H13N2O2)Cl], the PdII atom is tetracoordinated by an N and two O atoms of an (E)-1-[(2-methoxyphenyl)diazenyl]naphthalen-2-olate ligand and by a Cl atom, and has a square-planar coordination. In the crystal, molecules are linked by pairs of C—H...Cl hydrogen bonds, forming inversion dimers. The dimers are linked via offset π–π interactions [intercentroid distance = 3.546 (3) Å], forming chains running parallel to [100]

(E)-1-(4-Fluorophenyl)-2-(2-oxidonaphthalen-1-yl)diazen-1-ium

In the title zwitterion, C16H11FN2O, which belongs to the family of azo dyes, the dihedral angle between the benzene ring and the naphthalene ring system is 15.33 (7)° and an intramolecular N—H...O hydrogen bond closes an S(6) ring. In the crystal, inversion dimers linked by weak C—H...O hydrogen bonds generate R22(16) loops. Aromatic π–π stacking [centroid–centroid distance = 3.585 (11) Å] is also observed

Crystal structure of bis{1-[(E)-(2-methoxyphenyl)diazenyl]naphthalen-2-olato-κ3O,N2,O′}copper(II) containing an unknown solvate

The title complex, [Cu(C17H13N2O2)2], crystallizes with two independent molecules in the asymmetric unit. Each CuII atom has a distorted ocahedral coordination environment defined by two N atoms and four O atoms from two tridentate 1-[(E)-(2-methoxyphenyl)diazenyl]naphthalen-2-olate ligands. In the crystal, the two molecules are linked via weak C—H...O hydrogen bonds which in turn stack parallel to [010]. A region of disordered electron density, most probably disordered methanol solvent molecules, was corrected for using the SQUEEZE routine in PLATON [Spek (2015). Acta Cryst. C71, 9–18]. Their formula mass and unit-cell characteristics were not taken into account during refinement

1-[(E)-2-(2-Hydroxy-5-methylphenyl)diazen-2-ium-1-yl]naphthalen-2-olate

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

(E)-1-(2-Phenyldiazen-2-ium-1-yl)naphthalen-2-olate

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

Tautomerization of diazene<=>hydrazine via single proton tautomerization, spectral, XRD/HSA-interactions, optical and DFT/TD-DFT of new hydrazine ligand

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