trans-Bis[1,3-bis­(2-methoxy­phen­yl)triazenido]dimethano­lcadmium(II)

In the title compound, [Cd(C14H14N3O2)2(CH3OH)2], each cadmium(II) center is six-coordinated by an N atom and an O atom of two 1,3-bis­(2-methoxy­phen­yl)triazene ligands and by the O atoms of two methanol mol­ecules. The distorted octa­hedral coordination geometry of the Cd atom has two N and two O atoms in the equatorial plane, and two O atoms in axial positions. The complex is stabilized by intra­molecular O—H⋯O and O—H⋯N hydrogen bonds. In the crystal structure the complexes are linked into chains via inter­molecular C—H⋯π stacking inter­actions. One of the methanol C atoms is disordered with ouccupancies of 0.7:0.3

[1,3-Bis(2-ethoxy­phen­yl)triazenido]chloridomercury(II)

In the title compound, [Hg(C16H18N3O2)Cl], the HgII atom is four-coordinated in a tetra­hedral geometry by two N atoms from the 1,3-chelating and one O atom of a 1,3-bis­(2-ethoxy­phen­yl)triazenido ligand and one terminal chloride ion. The dihedral angle between the aromatic rings is 1.72 (14)°. In the crystal C—H⋯π stacking inter­actions occur

Chlorido[1-(2-eth­oxy­phen­yl)3-(4-nitro­phen­yl)triazenido]mercury(II)

In the title compound, [Hg(C14H13N4O3)Cl], the HgII atom is four-coordinated by one O atom and two N atoms from a tridentate 1-(2-eth­oxy­phen­yl)-3-(4-nitro­phen­yl)triazenide ligand and one terminal chloride ion in a distorted square-planar geometry. In the crystal structure, the mononuclear complexes are linked into pairs through C—H⋯O and C—H⋯Cl hydrogen bonds as well as π–π and C—H⋯π stacking inter­actions. In addition, weak Hg–μ6-arene π-inter­actions [mean distance of 3.667 (2) Å] are present between these dimers. The π–π stacking inter­actions are between aromatic rings with a centroid–centroid distance of 3.884 (2) Å. Moreover, edge-to-face inter­actions are present between eth­oxy CH groups and aromatic rings with H⋯π distances of 2.81 Å

[1,3-Bis(2-ethoxy­phen­yl)triazenido]bromidomercury(II)

To the central atom of the title compound, [HgBr(C16H18N3O2)], is attached one bromide ion and a 1,3-bis­(2-ethoxy­phen­yl)triazenide ligand through one O and two N atoms, forming a distorted square-planar geometry around the HgII atom. The mononuclear complexes are linked into centrosymmetric dimers by non-classical inter­molecular C—H⋯N hydrogen bonds and by weak Hg–η3-arene π-inter­actions [mean distance = 3.434 (3) Å]. The resulting dimeric units are assembled into zigzag chains by translation along the crystallographic c axis through secondary C—H⋯π edge-to-face benzene ring inter­actions

4-[(4-Bromo­phen­yl)diazen­yl]-2-eth­oxy­aniline

The title compound, C14H14BrN3O, exhibits a trans geometry about the –N=N– double bond. The dihedral angle between the benzene rings is 24.01 (5)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, inter­molecular N—H⋯N hydrogen bonds between the amine groups lead to the formation of a C(8) polymeric chain along [101]

Bis[1,3-bis­(2-cyano­phen­yl)triazenido]mercury(II)

In the title compound, [Hg(C14H8N5)2], the central atom is four-coordinated by two bidentate 1,3-bis­(2-cyano­phen­yl)triazenide ligands in a distorted square-planar geometry. The asymmteric unit is composed of one ligand molecule and one HgII ion, which is disordered over two sites, one lying on an inversion center and the other on a general position with site-occupancy factors of 0.2378 (7) and 0.3811 (7), respectively. The monomeric mol­ecules of the complex are linked into pairs through non-classical C—H⋯N hydrogen bonds. The resulting dimeric units are assembled by translation along the crystallographic c axis into chains linked through secondary π–π inter­actions [centroid–centroid distances = 3.685 (2) and 3.574 (2) Å], as well as C—H⋯π stacking inter­actions, resulting in a two-dimensional architecture

1,3-Bis(2-ethoxy­phen­yl)triazene

The title compound, C16H19N3O2, exhibits a trans geometry about the N=N double bond in the triazene unit in the solid state, and individual mol­ecules are close to planar with r.m.s. deviations from planarity of 0.065 Å and 0.242 Å for the two independent molecules in the asymmetric unit. Distinct inter­molecular N—H⋯N hydrogen bonds lead to the formation of dimers with an R 2 2(8) graph-set motif. The steric demands of the eth­oxy groups in the ortho position prevent a coplanar arrangement of the two mol­ecules in the dimers and these instead consist of two inter­locked mol­ecules that are related by a non-crystallographic pseudo-twofold rotation axis. Weak C—H⋯π inter­actions between the CH groups and the aromatic phenyl rings also occur

1-(3,5-Dichloro­phen­yl)-3-(2-meth­oxy­phen­yl)triaz-1-ene

The title mol­ecule, C13H11Cl2N3O, is almost planar and adopts a trans conformation with respect to the –N=N– bond; the dihedral angle between the rings is 3.47 (2)°. The N—N bond lengths indicate the presence of single- and double-bond characters and hence the –N=N—NH– moiety. In the crystal, inversion dimers linked by pairs of N—H⋯Cl hydrogen bonds occur, and C—H⋯π and π–π stacking interactions are also observed

Bis[1-(2-eth­oxy­phen­yl)-3-(4-nitro­phen­yl)triazenido]mercury(II)

In the title compound, [Hg(C14H13N4O3)2], the central Hg atom (site symmetry 2) is six-coordinated by two tridentate 1-(2-eth­oxy­phen­yl)-3-(4-nitro­phen­yl)triazenide ligands through two N and one O atoms. The mononuclear complex mol­ecules are connected into two parallel chains by inter­molecular C—H⋯O hydrogen-bonding inter­actions. These chains are connected to each other by face-to-edge C—H⋯π inter­actions between the CH of the ethoxy groups and the aromatic rings, resulting in a two-dimensional architecture in the ac plane

N-(2-Eth­oxy­phen­yl)formamide

The title compound, C9H11NO2, was obtained as an unexpected product in an attempt to synthesize a triazene ligand. The title mol­ecule is almost planar, with the formamide and eth­oxy groups oriented at 2.7 (3) and 12.9 (2)°, respectively, with respect to the mean plane of the benzene ring. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O hydrogen bonds, forming a chain along the a axis. Weak C—H⋯π inter­actions with an H⋯π distance of 2.78 Å reinforce the crystal packing, resulting in a three-dimensional network