1-(3,5-Dichloro-phen-yl)-3-(2-meth-oxy-phen-yl)triaz-1-ene.

The title mol-ecule, C(13)H(11)Cl(2)N(3)O, 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.

4-[(4-Bromo-phen-yl)diazen-yl]-2-eth-oxy-aniline.

The title compound, C(14)H(14)BrN(3)O, exhibits a trans geometry about the -N=N- double bond. The dihedral angle between the benzene rings is 24.01 (5)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, inter-molecular N-H⋯N hydrogen bonds between the amine groups lead to the formation of a C(8) polymeric chain along [101].

3-(2-Eth-oxy-phen-yl)-1-(3-nitro-phen-yl)triaz-1-ene.

The title compound, C(14)H(14)N(4)O(3), exhibits a trans geometry about the N=N double bond in the triazene unit. The mol-ecule is approximately planar (r.m.s. deviation = 0.044 Šfor all non-H atoms). An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, C-H⋯N hydrogen bonds lead to the formation of dimers which are, in turn, connected to each other by C-H⋯O hydrogen bonds, forming infinite chains of R(2) (2)(8) graph-set motif.

Chlorido[1-(2-eth-oxy-phen-yl)3-(4-nitro-phen-yl)triazenido]mercury(II).

In the title compound, [Hg(C(14)H(13)N(4)O(3))Cl], the Hg(II) atom is four-coordinated by one O atom and two N atoms from a tridentate 1-(2-eth-oxy-phen-yl)-3-(4-nitro-phen-yl)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 inter-actions. In addition, weak Hg-µ(6)-arene π-inter-actions [mean distance of 3.667 (2) Å] are present between these dimers. The π-π stacking inter-actions are between aromatic rings with a centroid-centroid distance of 3.884 (2) Å. Moreover, edge-to-face inter-actions are present between eth-oxy CH groups and aromatic rings with H⋯π distances of 2.81 Å.

1,3-Bis(2-ethoxy-phen-yl)triazene methanol 0.33-solvate.

There are three independent mol-ecules of 1,3-bis-(2-ethoxy-phen-yl)triazene and a mol-ecule of methanol in the asymmetric unit of the title compound, C(16)H(19)N(3)O(2)·0.33CH(3)OH. Two mol-ecules related by a non-crystallographic pseudo-twofold rotation axis are linked via distinct inter-molecular N-H⋯N hydrogen bonds, leading to the formation of a dimer with an R(2) (2)(8) graph set. The third mol-ecule is connected to the methanol mol-ecule by O-H⋯N and N-H⋯O hydrogen bonds. There are a number of weak C-H⋯π inter-actions, with H⋯π distances ranging from 2.74 to 2.89 Šbetween the C-H groups and the aromatic benzene rings.

[1,3-Bis(2-ethoxy-phen-yl)triazenido]chloridomercury(II).

In the title compound, [Hg(C(16)H(18)N(3)O(2))Cl], the Hg(II) atom is four-coordinated in a tetra-hedral geometry by two N atoms from the 1,3-chelating and one O atom of a 1,3-bis-(2-ethoxy-phen-yl)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 inter-actions occur.

trans-Bis[1,3-bis-(2-methoxy-phen-yl)triazenido]dimethano-lcadmium(II).

In the title compound, [Cd(C(14)H(14)N(3)O(2))(2)(CH(3)OH)(2)], each cadmium(II) center is six-coordinated by an N atom and an O atom of two 1,3-bis-(2-methoxy-phen-yl)triazene ligands and by the O atoms of two methanol mol-ecules. The distorted octa-hedral 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 intra-molecular O-H⋯O and O-H⋯N hydrogen bonds. In the crystal structure the complexes are linked into chains via inter-molecular C-H⋯π stacking inter-actions. One of the methanol C atoms is disordered with ouccupancies of 0.7:0.3.

1,3-Bis(2-ethoxy-phen-yl)triazene.

The title compound, C(16)H(19)N(3)O(2), exhibits a trans geometry about the N=N double bond in the triazene unit in the solid state, and individual mol-ecules are close to planar with r.m.s. deviations from planarity of 0.065 Šand 0.242 Šfor the two independent molecules in the asymmetric unit. Distinct inter-molecular 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 eth-oxy groups in the ortho position prevent a coplanar arrangement of the two mol-ecules in the dimers and these instead consist of two inter-locked mol-ecules that are related by a non-crystallographic pseudo-twofold rotation axis. Weak C-H⋯π inter-actions between the CH groups and the aromatic phenyl rings also occur.