mer-[3-Phenyl-5-(2-pyridyl-κN)-1,2,4-triazol-1-ido-κN 1]bis(2-quinolylphenyl-κ2 C 1,N)iridium(III) deuterochloroform disolvate

In the title compound, [Ir(C13H9N4)(C15H10N)2]·2CDCl3, the coordination at iridium is octahedral, but with narrow ligand bite angles ranging from 74.85 (8) to 83.99 (8)°. The bond lengths at iridium show the expected trans influence, with Ir—N trans to C being appreciably longer than trans to N. The chelate rings are mutually perpendicular to a reasonable approximation [interplanar angles ranging from 77.79 (6) to 83.93 (7)°]. All ligands are approximately planar; the maximum interplanar angles within ligands are ca 12°. One CDCl3 solvent molecule is severly disordered and was excluded from the refinement.

In the title compound, [Ir(C 13 H 9 N 4 )(C 15 H 10 N) 2 ]Á2CDCl 3 , the coordination at iridium is octahedral, but with narrow ligand bite angles ranging from 74.85 (8) to 83.99 (8) . The bond lengths at iridium show the expected trans influence, with Ir-N trans to C being appreciably longer than trans to N. The chelate rings are mutually perpendicular to a reasonable approximation [interplanar angles ranging from 77.79 (6) to 83.93 (7) ]. All ligands are approximately planar; the maximum interplanar angles within ligands are ca 12 . One CDCl 3 solvent molecule is severly disordered and was excluded from the refinement.

Experimental
Crystal data [Ir(C 13  OLEDs with theoretically 100% internal quantum efficiencies. Furthermore, iridium(III) complexes possess relatively short excited state lifetimes, high quantum efficiencies and remarkable colour tuning by modification of the ligand structures.
The simple method of tuning the emission colour is to vary the combination of cyclometallating and ancillary ligands (e.g. acetylacetonate, picolinate or triazolate derivatives) coordinated to the iridium core. These heteroleptic complexes are particularly interesting as emitters for OLED applications. Quinoline-based iridium(III) complexes have proved to be especially efficient materials for red OLEDs. In this regard, we have synthesized and characterized the title compound, a new iridium(III) complex with 2-phenylquinoline as chromophoric ligands and 3-phenyl-5-(2-pyridyl)-1,2,4-triazole as ancillary ligand, and report here its crystal structure.
The structure of the title complex is shown in Fig. 1. It crystallizes with two molecules of deuterochloroform, one of which is severely disordered (see refinement details). The general features of the complex are similar to those of our other recent related structures (Jones et al., 2010a,b). The coordination at iridium is octahedral, whereby the major deviations in angles arise from the restricted bite of the chelating ligands: N1-Ir-C12 79.82 (10), N17-Ir-C28 79.82 (12), N33-Ir-N39 74.85 (8)°. The bond lengths at iridium show the expected trans influence, with Ir-N33 and Ir-N39, 2.129 (2) and 2.196 (2) Å respectively, trans to C being appreciably longer than the mutually trans Ir-N1 2.084 (2) and Ir-N17 2.093 (2) Å. The interplanar angles between the chelate rings amount to 78.8 (1)° from the IrN 2 C 2 ring to both IrNC 3 rings, and 83.9 (1)°b etween the latter. Within the ligands, the interplanar angles between phenyl and quinoline are 11.8 (1) and 12.3 (1)°, whereas in the triazole ligand the pyridyl and phenyl rings subtend angles of 1.8 (1) and 11.0 (1)° respectively to the triazole ring.

Refinement
Hydrogen atoms were included at calculated positions using a riding model with aromatic C-H 0.95, sp 3 -C-H 1.00 Å.
The U(H) values were fixed at 1.2 × U eq (C) of the parent C atom. Anisotropic displacement parameters of the N and C atoms were restrained to have approximately equal components along mutual bonds (command DELU).
One deuterochloroform molecule is well ordered. However, a region of significant residual electron density could not be successfully interpreted in terms of the only possible solvent (CDCl 3 ). The program SQUEEZE (as implemented in the PLATON system; Spek, 2009) was therefore used to remove mathematically the effects of this solvent. Values for the formula mass etc. are based on an assumed solvent content per asymmetric unit of one ordered and one squeezed CDCl 3 .
There are several peaks of 0.7-1.1 e Å -3 either ca 1 Å from the Ir atom, which may reasonably be attributed to residual absorption errors, or in the solvent region, corresponding to slight extra disorder or irregular displacement features. Fig. 1. Structure of the title compound in the crystal. Ellipsoids represent 50% probability levels. Solvent molecules and hydrogen atoms are omitted for clarity.

Figures
Crystal data [Ir(C 13   Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.