Aqua­[N-(1-naphth­yl)acetamido-κN]bis­[2-(2-pyrid­yl)phenyl-κ2N,C1]iridium(III) ethyl­ene glycol hemisolvate

Fu, H.; Ding, Y.; Chen, G.

doi:10.1107/S1600536808010040

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page m731

doi:10.1107/S1600536808010040

Open

access

Aqua[N-(1-naphthyl)acetamido-κN]bis[2-(2-pyridyl)phenyl-κ²N,C¹]iridium(III) ethylene glycol hemisolvate

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

^aSchool of Chemical and Materials Engineering, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province, People's Republic of China, and ^bSchool of Science, Jiangnan University, 1800 Lihu Road, Wuxi, Jiangsu Province, People's Republic of China
^*Correspondence e-mail: yding@jiangnan.edu.cn

(Received 31 March 2008; accepted 12 April 2008; online 30 April 2008)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.038
wR(F²) = 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

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)

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

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
Symmetry code: (i) -x, -y+2, -z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

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.)

Related literature top

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

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); 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).

Figures top

	Fig. 1. The structure of (1) showing the atomic numbering scheme and octahedral coordination of Ir(III). Non-H atoms are shown with the 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (1).The intermolecluar hydrogen bonds are shown as dashed lines.

Aqua[N-(1-naphthyl)acetamido-λN]bis[2-(2-pyridyl)phenyl-κ²N,C¹]iridium(III) ethylene glycol hemisolvate top

Crystal data top

[Ir(C₁₁H₈N)₂(C₁₂H₁₀NO)(H₂O)]·0.5C₂H₆O₂	Z = 2
M_r = 733.83	F(000) = 726
Triclinic, P1	D_x = 1.621 Mg m⁻³
a = 10.097 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.888 (4) Å	Cell parameters from 2801 reflections
c = 14.453 (5) Å	θ = 2.3–22.3°
α = 95.580 (7)°	µ = 4.48 mm⁻¹
β = 92.940 (7)°	T = 273 K
γ = 107.423 (6)°	Block, green
V = 1503.4 (10) Å³	0.12 × 0.10 × 0.06 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	5269 independent reflections
Radiation source: fine-focus sealed tube	4451 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.615, T_max = 0.775	k = −12→12
7940 measured reflections	l = −17→8

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.05P)² + 0.001P]
5269 reflections	(Δ/σ)_max = 0.004
381 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

[Ir(C₁₁H₈N)₂(C₁₂H₁₀NO)(H₂O)]·0.5C₂H₆O₂	γ = 107.423 (6)°
M_r = 733.83	V = 1503.4 (10) Å³
Triclinic, P1	Z = 2
a = 10.097 (4) Å	Mo Kα radiation
b = 10.888 (4) Å	µ = 4.48 mm⁻¹
c = 14.453 (5) Å	T = 273 K
α = 95.580 (7)°	0.12 × 0.10 × 0.06 mm
β = 92.940 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5269 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4451 reflections with I > 2σ(I)
T_min = 0.615, T_max = 0.775	R_int = 0.027
7940 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.00	Δρ_max = 0.74 e Å⁻³
5269 reflections	Δρ_min = −0.91 e Å⁻³
381 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ir1	0.13408 (3)	0.89887 (2)	0.175881 (18)	0.03749 (11)
O1	0.1828 (5)	1.1138 (5)	0.0220 (4)	0.0639 (15)
O2	−0.0027 (5)	1.0120 (4)	0.1312 (3)	0.0525 (12)
H37	0.0550	1.0351	0.0906	0.063*
H36	−0.0767	0.9641	0.0998	0.063*
O3	0.9250 (19)	0.519 (2)	0.6241 (11)	0.287 (10)
H3	0.9913	0.5173	0.6586	0.431*
N1	0.3081 (5)	1.0563 (5)	0.1332 (4)	0.0443 (14)
N2	0.1680 (6)	0.9878 (5)	0.3092 (4)	0.0425 (13)
N3	0.0900 (6)	0.7881 (5)	0.0484 (4)	0.0461 (14)
C1	0.4217 (8)	1.2363 (8)	0.0431 (6)	0.068 (2)
H1A	0.4089	1.2499	−0.0210	0.102*
H1B	0.5047	1.2118	0.0525	0.102*
H1C	0.4303	1.3149	0.0826	0.102*
C2	0.2964 (7)	1.1287 (6)	0.0672 (5)	0.0473 (17)
C3	0.4419 (8)	1.0810 (8)	0.1841 (6)	0.059 (2)
C4	0.5249 (8)	1.0024 (8)	0.1629 (6)	0.068 (2)
H4	0.4975	0.9413	0.1104	0.082*
C5	0.6484 (9)	1.0104 (12)	0.2166 (9)	0.096 (4)
H5	0.7011	0.9557	0.2010	0.116*
C6	0.6883 (11)	1.1041 (14)	0.2944 (9)	0.106 (5)
H6	0.7689	1.1116	0.3316	0.127*
C7	0.6075 (9)	1.1888 (10)	0.3179 (6)	0.073 (3)
C8	0.4834 (8)	1.1748 (8)	0.2611 (5)	0.059 (2)
C9	0.4042 (10)	1.2587 (8)	0.2848 (6)	0.068 (2)
H9	0.3225	1.2530	0.2496	0.081*
C10	0.4520 (13)	1.3486 (10)	0.3613 (7)	0.104 (4)
H10	0.4020	1.4052	0.3782	0.125*
C11	0.5746 (15)	1.3572 (13)	0.4147 (8)	0.115 (5)
H11	0.6039	1.4191	0.4667	0.138*
C12	0.6483 (12)	1.2812 (13)	0.3937 (8)	0.099 (4)
H12	0.7295	1.2894	0.4305	0.119*
C13	0.1079 (8)	1.0713 (7)	0.3443 (5)	0.0556 (19)
H13	0.0478	1.0968	0.3049	0.067*
C14	0.1302 (10)	1.1234 (8)	0.4373 (6)	0.071 (2)
H14	0.0854	1.1822	0.4595	0.085*
C15	0.2177 (10)	1.0875 (9)	0.4957 (6)	0.074 (3)
H15	0.2348	1.1218	0.5582	0.089*
C16	0.2797 (9)	1.0009 (9)	0.4610 (6)	0.069 (2)
H16	0.3401	0.9758	0.5003	0.082*
C17	0.2551 (7)	0.9484 (7)	0.3676 (5)	0.0512 (19)
C18	0.3088 (7)	0.8496 (7)	0.3221 (5)	0.0519 (19)
C19	0.4038 (8)	0.7965 (9)	0.3665 (6)	0.066 (2)
H19	0.4368	0.8249	0.4285	0.079*
C20	0.4466 (9)	0.7041 (9)	0.3180 (8)	0.081 (3)
H20	0.5100	0.6702	0.3469	0.097*
C21	0.3967 (9)	0.6599 (8)	0.2261 (7)	0.074 (3)
H21	0.4255	0.5954	0.1940	0.089*
C22	0.3047 (8)	0.7107 (7)	0.1820 (6)	0.0573 (19)
H22	0.2724	0.6794	0.1202	0.069*
C23	0.2586 (7)	0.8065 (6)	0.2264 (5)	0.0430 (16)
C24	0.1684 (8)	0.8064 (7)	−0.0248 (5)	0.0557 (19)
H24	0.2491	0.8768	−0.0192	0.067*
C25	0.1343 (11)	0.7259 (8)	−0.1069 (6)	0.073 (3)
H25	0.1924	0.7396	−0.1553	0.088*
C26	0.0123 (12)	0.6241 (8)	−0.1167 (7)	0.085 (3)
H26	−0.0140	0.5683	−0.1720	0.102*
C27	−0.0684 (10)	0.6070 (8)	−0.0442 (6)	0.074 (3)
H27	−0.1516	0.5393	−0.0508	0.089*
C28	−0.0306 (8)	0.6881 (7)	0.0407 (5)	0.0534 (19)
C29	−0.1027 (7)	0.6709 (6)	0.1252 (5)	0.0500 (18)
C30	−0.2245 (8)	0.5705 (7)	0.1320 (7)	0.062 (2)
H30	−0.2696	0.5151	0.0792	0.074*
C31	−0.2773 (8)	0.5542 (8)	0.2165 (7)	0.072 (3)
H31	−0.3583	0.4871	0.2212	0.087*
C32	−0.2111 (8)	0.6368 (8)	0.2951 (7)	0.070 (2)
H32	−0.2468	0.6240	0.3527	0.083*
C33	−0.0919 (8)	0.7385 (7)	0.2885 (6)	0.059 (2)
H33	−0.0501	0.7947	0.3418	0.071*
C34	−0.0326 (6)	0.7588 (6)	0.2036 (5)	0.0426 (16)
C35	0.9687 (19)	0.537 (2)	0.5300 (13)	0.197 (10)
H35A	0.8860	0.5390	0.4936	0.237*
H35B	1.0322	0.6249	0.5357	0.237*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.03596 (15)	0.03611 (15)	0.03817 (16)	0.00916 (10)	−0.00124 (10)	0.00195 (10)
O1	0.057 (3)	0.066 (3)	0.067 (4)	0.013 (3)	−0.012 (3)	0.025 (3)
O2	0.048 (3)	0.057 (3)	0.057 (3)	0.024 (2)	−0.001 (2)	0.004 (2)
O3	0.33 (2)	0.33 (2)	0.175 (13)	0.053 (18)	−0.046 (15)	0.122 (15)
N1	0.039 (3)	0.044 (3)	0.046 (3)	0.009 (2)	−0.004 (3)	0.004 (3)
N2	0.042 (3)	0.038 (3)	0.043 (3)	0.007 (2)	0.004 (3)	0.000 (3)
N3	0.048 (3)	0.039 (3)	0.048 (4)	0.012 (3)	−0.007 (3)	0.001 (3)
C1	0.068 (5)	0.064 (5)	0.062 (5)	0.001 (4)	0.003 (4)	0.018 (4)
C2	0.047 (4)	0.040 (4)	0.051 (4)	0.009 (3)	0.007 (3)	0.002 (3)
C3	0.048 (4)	0.060 (5)	0.058 (5)	−0.001 (4)	0.000 (4)	0.016 (4)
C4	0.056 (5)	0.071 (6)	0.084 (6)	0.021 (4)	0.022 (5)	0.023 (5)
C5	0.048 (5)	0.131 (10)	0.125 (10)	0.031 (6)	0.018 (6)	0.069 (8)
C6	0.057 (6)	0.158 (12)	0.088 (8)	−0.007 (7)	−0.003 (6)	0.069 (8)
C7	0.047 (5)	0.094 (7)	0.059 (6)	−0.013 (5)	−0.006 (4)	0.029 (5)
C8	0.051 (4)	0.068 (5)	0.044 (5)	−0.007 (4)	0.001 (4)	0.019 (4)
C9	0.075 (6)	0.055 (5)	0.057 (5)	−0.002 (4)	0.014 (4)	0.000 (4)
C10	0.129 (9)	0.087 (7)	0.056 (6)	−0.025 (7)	0.005 (6)	−0.001 (5)
C11	0.131 (12)	0.105 (10)	0.056 (7)	−0.035 (8)	−0.007 (7)	0.000 (6)
C12	0.086 (8)	0.115 (10)	0.067 (8)	−0.009 (7)	−0.010 (6)	0.015 (7)
C13	0.052 (4)	0.053 (4)	0.055 (5)	0.007 (4)	0.008 (4)	0.000 (4)
C14	0.082 (6)	0.064 (5)	0.059 (6)	0.014 (5)	0.022 (5)	−0.006 (4)
C15	0.086 (7)	0.073 (6)	0.051 (5)	0.009 (5)	0.011 (5)	−0.007 (5)
C16	0.070 (6)	0.081 (6)	0.041 (5)	0.003 (5)	−0.006 (4)	0.002 (4)
C17	0.045 (4)	0.055 (4)	0.045 (4)	0.000 (3)	0.000 (3)	0.012 (4)
C18	0.041 (4)	0.056 (4)	0.053 (5)	0.004 (3)	−0.003 (3)	0.013 (4)
C19	0.052 (5)	0.080 (6)	0.062 (5)	0.012 (4)	−0.009 (4)	0.030 (5)
C20	0.067 (6)	0.083 (7)	0.108 (8)	0.041 (5)	−0.004 (6)	0.034 (6)
C21	0.075 (6)	0.060 (5)	0.099 (8)	0.034 (5)	0.002 (5)	0.020 (5)
C22	0.058 (5)	0.056 (5)	0.061 (5)	0.022 (4)	0.005 (4)	0.006 (4)
C23	0.036 (3)	0.033 (3)	0.054 (4)	0.001 (3)	0.001 (3)	0.005 (3)
C24	0.069 (5)	0.055 (5)	0.042 (4)	0.017 (4)	0.009 (4)	0.004 (4)
C25	0.122 (8)	0.061 (5)	0.044 (5)	0.037 (5)	0.011 (5)	0.006 (4)
C26	0.140 (10)	0.052 (5)	0.058 (6)	0.028 (6)	−0.011 (6)	−0.008 (4)
C27	0.087 (6)	0.061 (5)	0.061 (6)	0.009 (5)	−0.015 (5)	−0.005 (4)
C28	0.062 (5)	0.044 (4)	0.050 (5)	0.015 (4)	−0.013 (4)	0.000 (3)
C29	0.043 (4)	0.040 (4)	0.063 (5)	0.008 (3)	0.000 (4)	0.000 (3)
C30	0.045 (4)	0.051 (5)	0.081 (6)	0.004 (4)	−0.004 (4)	0.003 (4)
C31	0.050 (5)	0.051 (5)	0.107 (8)	−0.002 (4)	0.019 (5)	0.021 (5)
C32	0.055 (5)	0.070 (6)	0.087 (7)	0.016 (4)	0.029 (5)	0.022 (5)
C33	0.049 (4)	0.052 (4)	0.074 (6)	0.012 (4)	0.016 (4)	0.000 (4)
C34	0.031 (3)	0.049 (4)	0.054 (4)	0.022 (3)	0.006 (3)	0.007 (3)
C35	0.17 (2)	0.18 (2)	0.23 (3)	0.073 (13)	−0.10 (2)	−0.035 (17)

Geometric parameters (Å, º) top

Ir1—C23	1.982 (7)	C13—H13	0.9300
Ir1—C34	1.993 (7)	C14—C15	1.356 (12)
Ir1—N1	2.217 (5)	C14—H14	0.9300
Ir1—N2	2.035 (6)	C15—C16	1.351 (12)
Ir1—N3	2.052 (6)	C15—H15	0.9300
Ir1—O2	2.219 (4)	C16—C17	1.393 (10)
O1—C2	1.249 (8)	C16—H16	0.9300
O2—H37	0.8500	C17—C18	1.459 (11)
O2—H36	0.8500	C18—C19	1.417 (10)
O3—C35	1.47 (2)	C18—C23	1.432 (10)
O3—H3	0.8200	C19—C20	1.358 (12)
N1—C2	1.318 (8)	C19—H19	0.9300
N1—C3	1.443 (9)	C20—C21	1.381 (13)
N2—C13	1.313 (9)	C20—H20	0.9300
N2—C17	1.374 (9)	C21—C22	1.375 (10)
N3—C24	1.348 (9)	C21—H21	0.9300
N3—C28	1.360 (9)	C22—C23	1.382 (10)
C1—C2	1.527 (10)	C22—H22	0.9300
C1—H1A	0.9600	C24—C25	1.368 (10)
C1—H1B	0.9600	C24—H24	0.9300
C1—H1C	0.9600	C25—C26	1.378 (13)
C3—C8	1.389 (11)	C25—H25	0.9300
C3—C4	1.390 (11)	C26—C27	1.354 (13)
C4—C5	1.411 (12)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.403 (11)
C5—C6	1.397 (16)	C27—H27	0.9300
C5—H5	0.9300	C28—C29	1.453 (11)
C6—C7	1.432 (16)	C29—C30	1.394 (10)
C6—H6	0.9300	C29—C34	1.415 (9)
C7—C12	1.368 (14)	C30—C31	1.363 (12)
C7—C8	1.423 (11)	C30—H30	0.9300
C8—C9	1.413 (12)	C31—C32	1.382 (12)
C9—C10	1.365 (12)	C31—H31	0.9300
C9—H9	0.9300	C32—C33	1.386 (10)
C10—C11	1.399 (16)	C32—H32	0.9300
C10—H10	0.9300	C33—C34	1.401 (10)
C11—C12	1.293 (16)	C33—H33	0.9300
C11—H11	0.9300	C35—C35ⁱ	1.426 (18)
C12—H12	0.9300	C35—H35A	0.9700
C13—C14	1.388 (11)	C35—H35B	0.9700

C23—Ir1—C34	90.5 (2)	C15—C14—C13	119.3 (9)
C23—Ir1—N2	81.7 (3)	C15—C14—H14	120.3
C34—Ir1—N2	93.3 (3)	C13—C14—H14	120.3
C23—Ir1—N3	94.7 (3)	C16—C15—C14	118.5 (8)
C34—Ir1—N3	80.7 (3)	C16—C15—H15	120.8
N2—Ir1—N3	172.9 (2)	C14—C15—H15	120.8
C23—Ir1—N1	93.8 (2)	C15—C16—C17	121.5 (8)
C34—Ir1—N1	174.7 (2)	C15—C16—H16	119.2
N2—Ir1—N1	90.5 (2)	C17—C16—H16	119.2
N3—Ir1—N1	95.8 (2)	N2—C17—C16	119.1 (8)
C23—Ir1—O2	175.1 (2)	N2—C17—C18	113.6 (6)
C34—Ir1—O2	89.9 (2)	C16—C17—C18	127.3 (7)
N2—Ir1—O2	93.5 (2)	C19—C18—C23	120.1 (8)
N3—Ir1—O2	90.2 (2)	C19—C18—C17	124.4 (7)
N1—Ir1—O2	86.04 (19)	C23—C18—C17	115.5 (6)
Ir1—O2—H37	85.0	C20—C19—C18	119.8 (8)
Ir1—O2—H36	112.0	C20—C19—H19	120.1
H37—O2—H36	104.4	C18—C19—H19	120.1
C35—O3—H3	109.5	C19—C20—C21	120.6 (8)
C2—N1—C3	118.9 (6)	C19—C20—H20	119.7
C2—N1—Ir1	124.8 (4)	C21—C20—H20	119.7
C3—N1—Ir1	116.3 (4)	C22—C21—C20	120.3 (9)
C13—N2—C17	118.6 (6)	C22—C21—H21	119.8
C13—N2—Ir1	125.8 (5)	C20—C21—H21	119.8
C17—N2—Ir1	115.4 (5)	C21—C22—C23	122.3 (8)
C24—N3—C28	119.5 (6)	C21—C22—H22	118.9
C24—N3—Ir1	126.1 (5)	C23—C22—H22	118.9
C28—N3—Ir1	114.3 (5)	C22—C23—C18	116.9 (6)
C2—C1—H1A	109.5	C22—C23—Ir1	129.3 (6)
C2—C1—H1B	109.5	C18—C23—Ir1	113.8 (5)
H1A—C1—H1B	109.5	N3—C24—C25	122.8 (8)
C2—C1—H1C	109.5	N3—C24—H24	118.6
H1A—C1—H1C	109.5	C25—C24—H24	118.6
H1B—C1—H1C	109.5	C24—C25—C26	118.8 (9)
O1—C2—N1	121.9 (6)	C24—C25—H25	120.6
O1—C2—C1	116.8 (6)	C26—C25—H25	120.6
N1—C2—C1	121.3 (6)	C27—C26—C25	118.6 (9)
C8—C3—C4	118.9 (8)	C27—C26—H26	120.7
C8—C3—N1	120.5 (8)	C25—C26—H26	120.7
C4—C3—N1	120.4 (7)	C26—C27—C28	122.1 (8)
C3—C4—C5	123.5 (10)	C26—C27—H27	118.9
C3—C4—H4	118.2	C28—C27—H27	118.9
C5—C4—H4	118.2	N3—C28—C27	118.1 (8)
C6—C5—C4	117.1 (11)	N3—C28—C29	115.4 (6)
C6—C5—H5	121.4	C27—C28—C29	126.3 (7)
C4—C5—H5	121.4	C30—C29—C34	121.9 (7)
C5—C6—C7	121.3 (10)	C30—C29—C28	123.7 (7)
C5—C6—H6	119.4	C34—C29—C28	114.2 (6)
C7—C6—H6	119.4	C31—C30—C29	119.7 (8)
C12—C7—C8	120.5 (11)	C31—C30—H30	120.2
C12—C7—C6	120.8 (10)	C29—C30—H30	120.2
C8—C7—C6	118.6 (10)	C30—C31—C32	120.4 (7)
C3—C8—C9	121.2 (7)	C30—C31—H31	119.8
C3—C8—C7	120.5 (9)	C32—C31—H31	119.8
C9—C8—C7	118.3 (9)	C31—C32—C33	120.2 (8)
C10—C9—C8	117.7 (10)	C31—C32—H32	119.9
C10—C9—H9	121.2	C33—C32—H32	119.9
C8—C9—H9	121.2	C32—C33—C34	121.6 (8)
C9—C10—C11	121.4 (13)	C32—C33—H33	119.2
C9—C10—H10	119.3	C34—C33—H33	119.2
C11—C10—H10	119.3	C33—C34—C29	116.2 (6)
C12—C11—C10	121.7 (12)	C33—C34—Ir1	129.1 (5)
C12—C11—H11	119.2	C29—C34—Ir1	114.7 (5)
C10—C11—H11	119.2	C35ⁱ—C35—O3	130 (3)
C11—C12—C7	120.5 (12)	C35ⁱ—C35—H35A	104.8
C11—C12—H12	119.8	O3—C35—H35A	104.8
C7—C12—H12	119.8	C35ⁱ—C35—H35B	104.8
N2—C13—C14	122.9 (8)	O3—C35—H35B	104.8
N2—C13—H13	118.5	H35A—C35—H35B	105.8
C14—C13—H13	118.5

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H36···O1ⁱⁱ	0.85	1.98	2.756 (7)	150
O2—H36···O1ⁱⁱ	0.85	1.98	2.756 (7)	150

Symmetry code: (ii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Ir(C₁₁H₈N)₂(C₁₂H₁₀NO)(H₂O)]·0.5C₂H₆O₂
M_r	733.83
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	10.097 (4), 10.888 (4), 14.453 (5)
α, β, γ (°)	95.580 (7), 92.940 (7), 107.423 (6)
V (Å³)	1503.4 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.48
Crystal size (mm)	0.12 × 0.10 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.615, 0.775
No. of measured, independent and observed [I > 2σ(I)] reflections	7940, 5269, 4451
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.093, 1.00
No. of reflections	5269
No. of parameters	381
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.91

Computer programs: APEX2 (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

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

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H36···O1ⁱ	0.85	1.98	2.756 (7)	150.4
O2—H36···O1ⁱ	0.85	1.98	2.756 (7)	150.4

Symmetry code: (i) −x, −y+2, −z.

Acknowledgements

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).

References

Adachi, C., Baldo, M. A., Forrest, S. R. & Thompson, M. E. (2000). Appl. Phys. Lett. 77, 904–906. Web of Science CrossRef CAS Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Baldo, M. A., O'Brien, D. F., You, Y., Shoustikov, A., Sibley, S., Thompson, M. E. & Forrest, S. R. (1998). Nature (London), 395, 151–154. CAS Google Scholar
Beeby, A., Bettington, S., Samuel, I. D. W. & Wang, Z. (2003). J. Mater. Chem. 13, 80–83. Web of Science CrossRef CAS Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Lamansky, S., Djurovich, P., Murphy, D. & Abdel-Razzaq, F. (2001). J. Am. Chem. Soc. 123, 4304–4312. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
You, Y. & Park, S. Y. (2005). J. Am. Chem. Soc. 127, 12438–12439. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.