Crystal structure of [3-amino-2-(phenyldiazenyl)pyridine]chlorido(η6-p-cymene)ruthenium(II) chloride

The title compound, [RuCl(C10H14)(C11H10N4)]Cl is an RuII complex in which an η6-p-cymene ligand, two N atoms of 3-amino-2-(phenylazo)pyridine and one Cl ion form a piano-stool coordination environment around the metal ion. In the crystal structure, N—H⋯Cl hydrogen bonds play an important role in the formation of the supramolecular zigzag chain along the a-axis direction. Disorder is observed for the isopropyl group with site-occupancy factors refined to 0.78 (5) and 0.22 (5).


S0.1. Synthesis and crystallization
3-amino-2-(phenylazo)pyridine (3aazpy) was prepared by condensation of 2,3-diamino-pyridine (14 mg, 2 mmol) with nitrosobenzene (217 mg, 2.1 mmol) in a mixture of 30 M NaOH (3 mL) and 35 mL of benzene solution. The reaction mixture was stirred and heated under reflux for 14 h. The product was extracted many times with benzene to obtain the brown solution. Then the volume was reduced to 3 mL. The residue was purified by column chromatography. The redorange band was collected and evaporated to dryness (yield : 37%).
The title compound was obtained by the following procedure: [(η 6 -p-cym)RuCl 2 ] 2 (0.05 mmol) was added to a THF solution of 3aazpy (0.1 mmol); the solution color change from red to purple. The solution was stirred at ambient temperature for 2 h. The precipitate was collected by filtration, washed with a small amount of THF. Monocrystals were obtained by diffusion of ether into a dichloromethane solution of the complex (yield: 82%).

S1. Results and discussion
Organometallic ruthenium complexes have gained much interest due to promising anticancer activity (Almodares et al., 2014;Stepanenko et al., 2011). These arene complexes consist of a chelating ligand and one chloride ion. In this work, a new ruthenium(II) complex of this type is reported.

Figure 1
The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
Crystal packing of the title compound showing the N-H···Cl hydrogen bonds along the a axis.