Aqua­[N-(1-naphth­yl)acetamido-κN]bis­[2-(2-pyrid­yl)phenyl-κ2 N,C 1]iridium(III) ethyl­ene glycol hemisolvate

Hao Fu; Yuqiang Ding; Guoqing Chen

doi:10.1107/S1600536808010040

. 2008 Apr 30;64(Pt 5):m731. doi: 10.1107/S1600536808010040

Aqua[N-(1-naphthyl)acetamido-κN]bis[2-(2-pyridyl)phenyl-κ² N,C ¹]iridium(III) ethylene glycol hemisolvate

Hao Fu ^a, Yuqiang Ding ^a,^*, Guoqing Chen ^b

PMCID: PMC2961167 PMID: 21202254

Abstract

In the title compound, [Ir(C₁₁H₈N)₂(C₁₂H₁₀NO)(H₂O)]·0.5C₂H₆O₂, the iridium center is coordinated by two N atoms and two C atoms from two 2-(2-pyridyl)phenyl (ppy) ligands, one N atom from the N-(1-naphthyl)acetamide ligand and one water O atom, forming a distorted octahedral environment. Molecules are linked by intermolecular O—H⋯O hydrogen bonds formed by the coordinated water molecule and the amide O atom of the N-(1-naphthyl)acetamide ligands.

Related literature

For related literature, see: Adachi et al. (2000 ▶); Lamansky et al. (2001 ▶); Beeby et al. (2003 ▶); You & Park (2005 ▶); Baldo et al. (1998 ▶).

Experimental

Crystal data

[Ir(C₁₁H₈N)₂(C₁₂H₁₀NO)(H₂O)]·0.5C₂H₆O₂
M _r = 733.83
Triclinic,
a = 10.097 (4) Å
b = 10.888 (4) Å
c = 14.453 (5) Å
α = 95.580 (7)°
β = 92.940 (7)°
γ = 107.423 (6)°
V = 1503.4 (10) Å³
Z = 2
Mo Kα radiation
μ = 4.48 mm⁻¹
T = 273 (2) K
0.12 × 0.10 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.615, T _max = 0.775
7940 measured reflections
5269 independent reflections
4451 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.093
S = 1.00
5269 reflections
381 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010040/sg2232sup1.cif

e-64-0m731-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010040/sg2232Isup2.hkl

e-64-0m731-Isup2.hkl^{(258KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected geometric parameters (Å, °).

Ir1—C23	1.982 (7)
Ir1—C34	1.993 (7)
Ir1—N1	2.217 (5)
Ir1—N2	2.035 (6)
Ir1—N3	2.052 (6)
Ir1—O2	2.219 (4)

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C23—Ir1—C34	90.5 (2)
C23—Ir1—N2	81.7 (3)
C34—Ir1—N3	80.7 (3)
N1—Ir1—O2	86.04 (19)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H36⋯O1ⁱ	0.85	1.98	2.756 (7)	150
O2—H36⋯O1ⁱ	0.85	1.98	2.756 (7)	150

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20571033) and by the Program for New Century Excellent Talents in Universities (NCET-06–0483).

supplementary crystallographic information

Comment

Since the initial work by Thompson and Forrest (Baldo et al., 1998), there have been considerable attention focused on designing homoleptic Ir triscyclometalates (CÑ)₃Ir and heteroleptic Ir complexes (CÑ)₂Ir(LX) for their application in organic light emitting diodes (OLEDs), where CÑ is a general abbreviation used hereafter for a cyclometalating ligand and LX is an ancillary ligand. (CÑ)₂Ir(LX) complexes, containing cyclometalating ligands 2-pyridylphenyl, have already been incorporated with different kinds of ancillary ligands, such as β-diketonate, 2-picolinic acid, to exploit their potential application in OLEDs. (Adachi et al., 2000; Lamansky et al., 2001; Beeby et al., 2003; You & Park, 2005). However, among all the ancillary lignads used in (CÑ)₂Ir(LX) complexes, N-(1-naphthyl)acetamide has never been studied..

In this paper, we report the crystal structure of (CÑ)₂Ir(LX) with N-(1-naphthyl)acetamide as ancillary ligand, it is a solvated neutral mononuclear [Ir(ppy)₂(N-acetyl-1-naphthylamino)(H₂O)] (ppy=2-pyridylphenyl) complex. The Ir atom has a distorted octahedral geometry involving two ppy ligands, one N-(1-naphthyl)acetamide ligand and one water molecule.The average bond lengthes from two N atoms and two C atoms in two ppy ligands to iridium center are Ir—N_av = 2.048Å and Ir—C_av = 1.987Å respectively, the bond lengthes from N atom in the N-acetylnaphthylamine ligand and the O atom in aqua to Ir atom are Ir—N=2.217 (5)Å and Ir—O= 2.219 (4).(Table 1).

The molecules of the title complexes are linked by O—H···O intermolecule hydrogen bonds formed by the coordinated water molecules and amido O atom of the N-acetyl-1-naphthylamino ligands.(Fig. 2.)

Experimental

0.107 g [(ppy)₂IrCl]₂ (1 eq.) and 0.047 g (2.5 eq.) N-(1-naphthyl)acetamide were dissolved in dichlomethane, 0.054 g sodium methanol(10eq.) then added to the mixture to neutralize the hydrochloric acid that produced in the reaction. The reaction was stirred at room temperature for 24 h. After the reaction, the solvent was removed and the residua was washed with hot water and ether. The crude product was separated by chromatography on silica gel with dichloromethane as eluent to give a yellow solid. Single crystals suitable for X-ray diffraction were grown by slow diffusion of ethylene glycol solution.