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A series of azo-metal chelate dyes have been synthesized by coupling substituted o-nitroaniline and p-t-/s-butylphenol. The spectral characterization of the azo dyes containing o-hydroxy group and azo-metal(II) chelate [metal(II): Cu, Ni, Co] dyes by IR spectra, UV-VIS spectra, NMR spectra, elemental analysis and magnetic susceptibility techniques are reported. The stoichiometry of the azo-metal chelates was determined by the spectroscopic titration method to be 1:2 (ML 2 ).

The crystal structure of the title compound, C14H13ClN2O, determined at 213 K, shows that the mol­ecule is approx­imately planar in the solid state, having a trans configuration with respect to the azo double bond, as found for other diazene (azo­benzene) derivatives. The dihedral angle between the planes of the two aromatic rings is 5.48 (10)°. Hydro­xyl groups are linked to each other by intermolecular hydrogen bonds along the b axis.

Key indicators: single-crystal X-ray study; T = 297 K; mean (C-C) = 0.006 Å; R factor = 0.067; wR factor = 0.190; data-to-parameter ratio = 17.0.In the title compound, C 34 H 28 O 6 Á0.5C 7 H 8 , the calix[4]arene molecule forms a cone-like conformation, stabilized by intramolecular O-HÁ Á ÁO hydrogen bonds. In the crystal structure, the calixarene molecules form centrosymmetric dimers via aromaticinteractions [centroid separation = 3.633 (3) Å ]. The toluene solvent molecule is disordered about an inversion centre.