Chlorido(pyridine-κN)bis­[2-(quinolin-2-yl)phenyl-κ2C1,N]iridium(III) mono­hydrate

Li, C.; Dong, X.-Q.; Wang, Q.; Ren, C.-X.; Ding, Y.-Q.

doi:10.1107/S1600536808025452

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page m1205

doi:10.1107/S1600536808025452

Open

access

Chlorido(pyridine-κN)bis[2-(quinolin-2-yl)phenyl-κ²C¹,N]iridium(III) monohydrate

Cheng Li,^a Xiao-Qing Dong,^a Quan Wang,^a Chun-Xia Ren ^a and Yu-Qiang Ding ^a ^*

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

(Received 11 July 2008; accepted 7 August 2008; online 30 August 2008)

In the neutral mononuclear iridium(III) title complex, [Ir(C₁₅H₁₀N)₂Cl(C₅H₅N)]·H₂O, the Ir atom is coordinated by two N atoms and two C atoms from two 2-(quinolin-2-yl)phenyl ligands, one N atom from a pyridine ligand and one Cl atom in an octahedral geometry.

Related literature

For related literature, see: Adachi et al. (2000 ); Baldo et al. (1998 ); Gao et al. (2002 ); Lamansky et al. (2001a ,b ); Liu et al. (2007 ).

Experimental

Crystal data

[Ir(C₁₅H₁₀N)₂Cl(C₅H₅N)]·H₂O
M_r = 733.25
Monoclinic, P 2₁ /n
a = 9.8949 (15) Å
b = 17.653 (3) Å
c = 16.424 (3) Å
β = 98.545 (3)°
V = 2837.0 (8) Å³
Z = 4
Mo Kα radiation
μ = 4.83 mm⁻¹
T = 273 (2) K
0.16 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.511, T_max = 0.684
14857 measured reflections
5027 independent reflections
3702 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.075
S = 1.02
5027 reflections
370 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ir1—C11	1.990 (6)
Ir1—C26	1.992 (6)
Ir1—N1	2.090 (5)
Ir1—N2	2.092 (5)
Ir1—N3	2.221 (5)
Ir1—Cl1	2.5182 (16)

C11—Ir1—C26	87.3 (2)
C11—Ir1—N1	80.0 (2)
C26—Ir1—N1	93.3 (2)
C11—Ir1—N2	94.9 (2)
C26—Ir1—N2	80.0 (2)
N1—Ir1—N2	171.7 (2)
C11—Ir1—N3	173.07 (19)
C26—Ir1—N3	87.8 (2)
N1—Ir1—N3	105.16 (18)
N2—Ir1—N3	79.48 (17)
C11—Ir1—Cl1	96.67 (17)
C26—Ir1—Cl1	174.02 (16)
N1—Ir1—Cl1	83.02 (14)
N2—Ir1—Cl1	104.10 (14)
N3—Ir1—Cl1	88.68 (13)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025452/hy2145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808025452/hy2145Isup2.hkl

checkCIF report

Comment top

Since the significant work by Thompson and Forrest (Adachi et al., 2000; Baldo et al., 1998), the chemistry of cyclometalated Ir^III complexes has received a great deal of attention. These homoleptic complexes, (CÑ)₂Ir(LX), have proven to be very efficient when used in organic light emitting diodes (OLEDs), where CÑ is a general abbreviation used hereafter for a cyclometalating ligand and LX stands for other ligands. (CÑ)₂Ir(LX) complexes with different ligands have various emissions (Gao et al., 2002; Lamansky et al., 2001a, b; Liu et al., 2007).

In this paper, we report the crystal structure of the title compound, which is a neutral mononuclear complex. The Ir^III atom is coordinated by two N atoms and two C atoms from two 2-phenylquinoline (pq) ligands, one N atom from a pyridine ligand and one Cl atom in an octahedral geometry (Fig. 1). The Ir1—N1 and Ir1—N2 bond lengths are 2.090 (5) and 2.092 (5)Å (Table 1) and agree well with those observed in the related (CÑ)₂Ir(LX) complexes (Gao et al., 2002; Lamansky et al., 2001a). The Ir—C bond lengths of 1.990 (6) and 1.992 (6)Å are slightly shorter than the Ir—C bond length [2.003 (9) Å] in the complex [Ir(ppy)₂(acac)] (ppy = 2-pyridylphenyl; acac = acetylacetone) (Lamansky et al., 2001a). The N—Ir—C angles of 80.0 (2)° are comparable to that [81.7 (4)°] in [Ir(ppy)₂(acac)].

Related literature top

For related literature, see: Adachi et al. (2000); Baldo et al. (1998); Gao et al. (2002); Lamansky et al. (2001a,b); Liu et al. (2007).

Experimental top

A mixture of (pq)₂IrCl (0.126 g, 0.2 mmol) and sodium bicarbonate (0.04 g, 0.5 mmol) dissolved in pyridine (12 ml) and dichloromethane (10 ml) was refluxed for 24 h and then cooled to room temperature. The solvent was removed in vacuum. The residue was washed with hexane and hot water. The crude product was separated by chromatography on silica gel with dichloromethane as eluent to give a red solid. Single crystals suitable for X-ray diffraction were obtained by slow diffusion of hexane into the dichloromethane solution.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.

Chlorido(pyridine-κN)bis[2-(quinolin-2-yl)phenyl- κ²C¹,N]iridium(III) monohydrate top

Crystal data top

[Ir(C₁₅H₁₀N)₂Cl(C₅H₅N)]·H₂O	F(000) = 1440
M_r = 733.25	D_x = 1.717 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3064 reflections
a = 9.8949 (15) Å	θ = 2.5–23.5°
b = 17.653 (3) Å	µ = 4.83 mm⁻¹
c = 16.424 (3) Å	T = 273 K
β = 98.545 (3)°	Block, red
V = 2837.0 (8) Å³	0.16 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5027 independent reflections
Radiation source: fine-focus sealed tube	3702 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.511, T_max = 0.684	k = −20→21
14857 measured reflections	l = −16→19

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0276P)² + 1.7551P] where P = (F_o² + 2F_c²)/3
5027 reflections	(Δ/σ)_max = 0.001
370 parameters	Δρ_max = 0.78 e Å⁻³
9 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Ir(C₁₅H₁₀N)₂Cl(C₅H₅N)]·H₂O	V = 2837.0 (8) Å³
M_r = 733.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.8949 (15) Å	µ = 4.83 mm⁻¹
b = 17.653 (3) Å	T = 273 K
c = 16.424 (3) Å	0.16 × 0.12 × 0.08 mm
β = 98.545 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5027 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3702 reflections with I > 2σ(I)
T_min = 0.511, T_max = 0.684	R_int = 0.049
14857 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	9 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.02	Δρ_max = 0.78 e Å⁻³
5027 reflections	Δρ_min = −0.72 e Å⁻³
370 parameters

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

	x	y	z	U_iso*/U_eq
Ir1	0.09759 (3)	0.240147 (11)	0.005833 (14)	0.03528 (9)
Cl1	0.20494 (18)	0.31961 (8)	−0.09466 (10)	0.0514 (4)
N1	0.0132 (5)	0.3437 (2)	0.0339 (3)	0.0410 (13)
N2	0.1566 (5)	0.1294 (3)	−0.0176 (3)	0.0394 (12)
N3	0.2997 (5)	0.2349 (2)	0.0852 (3)	0.0382 (11)
O1	0.4549 (12)	0.4379 (6)	0.9584 (8)	0.245 (5)
C1	0.0782 (7)	0.4038 (3)	0.0794 (4)	0.0442 (17)
C2	0.2205 (8)	0.4034 (3)	0.1040 (4)	0.056 (2)
H2	0.2725	0.3631	0.0893	0.067*
C3	0.2822 (8)	0.4615 (4)	0.1490 (5)	0.066 (2)
H3	0.3764	0.4605	0.1648	0.080*
C4	0.2069 (9)	0.5232 (4)	0.1724 (5)	0.067 (2)
H4	0.2501	0.5617	0.2051	0.081*
C5	0.0719 (9)	0.5258 (4)	0.1467 (4)	0.062 (2)
H5	0.0226	0.5678	0.1598	0.074*
C6	0.0025 (7)	0.4663 (3)	0.1002 (4)	0.0464 (17)
C7	−0.1381 (8)	0.4686 (3)	0.0732 (4)	0.0566 (19)
H7	−0.1897	0.5093	0.0874	0.068*
C8	−0.1989 (8)	0.4119 (3)	0.0268 (4)	0.0541 (18)
H8	−0.2924	0.4135	0.0084	0.065*
C9	−0.1209 (7)	0.3500 (3)	0.0060 (4)	0.0432 (16)
C10	−0.1786 (7)	0.2886 (3)	−0.0478 (4)	0.0425 (16)
C11	−0.0862 (6)	0.2318 (3)	−0.0616 (3)	0.0396 (14)
C12	−0.1354 (7)	0.1741 (3)	−0.1161 (4)	0.0469 (17)
H12	−0.0758	0.1362	−0.1279	0.056*
C13	−0.2704 (8)	0.1716 (4)	−0.1532 (4)	0.0553 (19)
H13	−0.3008	0.1324	−0.1893	0.066*
C14	−0.3594 (8)	0.2273 (4)	−0.1365 (4)	0.065 (2)
H14	−0.4507	0.2250	−0.1602	0.078*
C15	−0.3145 (7)	0.2865 (4)	−0.0848 (4)	0.0568 (19)
H15	−0.3745	0.3248	−0.0748	0.068*
C16	0.2238 (7)	0.1046 (3)	−0.0807 (4)	0.0475 (17)
C17	0.2191 (8)	0.1467 (4)	−0.1529 (4)	0.064 (2)
H17	0.1692	0.1915	−0.1591	0.077*
C18	0.2872 (10)	0.1225 (5)	−0.2148 (5)	0.086 (3)
H18	0.2808	0.1499	−0.2636	0.103*
C19	0.3657 (10)	0.0572 (6)	−0.2046 (7)	0.098 (3)
H19	0.4180	0.0436	−0.2449	0.118*
C20	0.3677 (10)	0.0138 (5)	−0.1382 (6)	0.093 (3)
H20	0.4175	−0.0311	−0.1342	0.111*
C21	0.2959 (8)	0.0346 (4)	−0.0741 (5)	0.062 (2)
C22	0.2865 (9)	−0.0103 (4)	−0.0068 (6)	0.084 (3)
H22	0.3361	−0.0551	0.0004	0.100*
C23	0.2056 (8)	0.0103 (4)	0.0493 (5)	0.070 (2)
H23	0.1929	−0.0226	0.0916	0.084*
C24	0.1409 (7)	0.0813 (3)	0.0435 (4)	0.0439 (16)
C25	0.0577 (7)	0.1094 (3)	0.1027 (4)	0.0447 (17)
C26	0.0204 (6)	0.1851 (3)	0.0943 (4)	0.0383 (15)
C27	−0.0564 (6)	0.2134 (4)	0.1515 (4)	0.0507 (17)
H27	−0.0838	0.2638	0.1477	0.061*
C28	−0.0932 (7)	0.1694 (5)	0.2134 (4)	0.060 (2)
H28	−0.1419	0.1908	0.2519	0.072*
C29	−0.0586 (8)	0.0943 (5)	0.2190 (5)	0.065 (2)
H29	−0.0866	0.0643	0.2600	0.078*
C30	0.0164 (8)	0.0637 (4)	0.1646 (4)	0.061 (2)
H30	0.0404	0.0127	0.1682	0.073*
C31	0.4148 (7)	0.2258 (3)	0.0510 (4)	0.0507 (17)
H31	0.4105	0.2314	−0.0056	0.061*
C32	0.5380 (7)	0.2085 (4)	0.0979 (5)	0.062 (2)
H32	0.6156	0.2022	0.0729	0.075*
C33	0.5461 (8)	0.2007 (4)	0.1814 (5)	0.068 (2)
H33	0.6291	0.1894	0.2136	0.082*
C34	0.4306 (7)	0.2098 (4)	0.2167 (4)	0.0548 (18)
H34	0.4329	0.2039	0.2732	0.066*
C35	0.3112 (6)	0.2276 (3)	0.1669 (4)	0.0439 (15)
H35	0.2335	0.2352	0.1915	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.04334 (15)	0.03234 (13)	0.02941 (13)	−0.00102 (12)	0.00295 (9)	0.00188 (11)
Cl1	0.0700 (12)	0.0461 (9)	0.0389 (9)	−0.0098 (8)	0.0114 (8)	0.0051 (7)
N1	0.055 (4)	0.035 (3)	0.031 (3)	0.003 (2)	0.002 (3)	0.005 (2)
N2	0.045 (3)	0.037 (3)	0.035 (3)	0.000 (2)	0.004 (2)	−0.001 (2)
N3	0.038 (3)	0.039 (3)	0.036 (3)	0.002 (2)	0.002 (2)	−0.001 (2)
O1	0.244 (5)	0.245 (5)	0.245 (5)	0.0004 (10)	0.0366 (13)	−0.0004 (10)
C1	0.063 (5)	0.034 (3)	0.034 (4)	−0.001 (3)	0.004 (3)	0.008 (3)
C2	0.073 (6)	0.038 (4)	0.053 (5)	−0.002 (3)	−0.006 (4)	0.001 (3)
C3	0.082 (6)	0.040 (4)	0.069 (5)	−0.008 (4)	−0.016 (4)	0.000 (4)
C4	0.093 (7)	0.044 (4)	0.059 (5)	−0.015 (4)	−0.010 (5)	−0.011 (4)
C5	0.106 (7)	0.037 (4)	0.044 (4)	−0.002 (4)	0.015 (4)	0.001 (3)
C6	0.068 (5)	0.038 (4)	0.035 (4)	0.001 (3)	0.012 (3)	0.004 (3)
C7	0.079 (6)	0.038 (4)	0.054 (5)	0.013 (4)	0.015 (4)	0.000 (3)
C8	0.059 (5)	0.051 (4)	0.052 (4)	0.008 (4)	0.005 (4)	0.004 (3)
C9	0.058 (5)	0.036 (3)	0.035 (4)	0.004 (3)	0.008 (3)	0.007 (3)
C10	0.053 (4)	0.038 (3)	0.033 (4)	0.000 (3)	−0.004 (3)	0.008 (3)
C11	0.049 (4)	0.038 (3)	0.030 (3)	0.001 (3)	0.000 (3)	0.009 (3)
C12	0.057 (5)	0.038 (3)	0.043 (4)	−0.004 (3)	−0.003 (3)	0.001 (3)
C13	0.073 (6)	0.048 (4)	0.041 (4)	−0.011 (4)	−0.005 (4)	−0.001 (3)
C14	0.060 (5)	0.066 (5)	0.061 (5)	−0.007 (4)	−0.017 (4)	0.004 (4)
C15	0.054 (5)	0.058 (4)	0.055 (5)	0.006 (3)	−0.004 (4)	0.004 (4)
C16	0.054 (5)	0.042 (4)	0.049 (4)	−0.004 (3)	0.013 (3)	−0.015 (3)
C17	0.095 (6)	0.049 (4)	0.053 (5)	−0.016 (4)	0.026 (4)	−0.013 (4)
C18	0.118 (8)	0.082 (6)	0.068 (6)	−0.019 (6)	0.049 (6)	−0.021 (5)
C19	0.107 (8)	0.101 (8)	0.100 (8)	−0.004 (6)	0.059 (7)	−0.029 (6)
C20	0.111 (8)	0.079 (6)	0.091 (8)	0.023 (6)	0.025 (6)	−0.034 (6)
C21	0.067 (5)	0.054 (4)	0.064 (5)	0.005 (4)	0.009 (4)	−0.017 (4)
C22	0.105 (8)	0.062 (5)	0.081 (7)	0.036 (5)	0.002 (6)	−0.007 (5)
C23	0.092 (7)	0.046 (4)	0.072 (6)	0.014 (4)	0.011 (5)	0.014 (4)
C24	0.054 (4)	0.032 (3)	0.042 (4)	−0.002 (3)	−0.003 (3)	0.002 (3)
C25	0.052 (4)	0.046 (4)	0.034 (4)	−0.008 (3)	−0.001 (3)	0.011 (3)
C26	0.035 (4)	0.048 (4)	0.030 (3)	−0.005 (3)	−0.002 (3)	0.003 (3)
C27	0.044 (4)	0.067 (4)	0.041 (4)	0.007 (3)	0.005 (3)	0.015 (3)
C28	0.035 (4)	0.101 (6)	0.043 (4)	−0.010 (4)	0.008 (3)	0.013 (4)
C29	0.058 (5)	0.087 (6)	0.050 (5)	−0.018 (4)	0.007 (4)	0.020 (4)
C30	0.076 (6)	0.056 (4)	0.048 (5)	−0.001 (4)	0.003 (4)	0.016 (4)
C31	0.053 (5)	0.052 (4)	0.047 (4)	−0.003 (3)	0.007 (3)	−0.004 (3)
C32	0.042 (5)	0.075 (5)	0.071 (6)	0.007 (4)	0.011 (4)	−0.011 (4)
C33	0.050 (5)	0.087 (6)	0.062 (5)	0.009 (4)	−0.009 (4)	−0.002 (4)
C34	0.058 (5)	0.065 (4)	0.038 (4)	−0.001 (4)	−0.003 (4)	0.003 (3)
C35	0.047 (4)	0.046 (4)	0.038 (4)	−0.002 (3)	0.005 (3)	−0.007 (3)

Geometric parameters (Å, º) top

Ir1—C11	1.990 (6)	C15—H15	0.9300
Ir1—C26	1.992 (6)	C16—C17	1.395 (9)
Ir1—N1	2.090 (5)	C16—C21	1.423 (9)
Ir1—N2	2.092 (5)	C17—C18	1.368 (10)
Ir1—N3	2.221 (5)	C17—H17	0.9300
Ir1—Cl1	2.5182 (16)	C18—C19	1.387 (12)
N1—C9	1.342 (7)	C18—H18	0.9300
N1—C1	1.398 (7)	C19—C20	1.331 (12)
N2—C24	1.340 (7)	C19—H19	0.9300
N2—C16	1.382 (8)	C20—C21	1.404 (11)
N3—C35	1.337 (7)	C20—H20	0.9300
N3—C31	1.351 (8)	C21—C22	1.374 (10)
C1—C6	1.404 (9)	C22—C23	1.357 (10)
C1—C2	1.406 (9)	C22—H22	0.9300
C2—C3	1.357 (8)	C23—C24	1.404 (8)
C2—H2	0.9300	C23—H23	0.9300
C3—C4	1.404 (10)	C24—C25	1.452 (9)
C3—H3	0.9300	C25—C26	1.389 (8)
C4—C5	1.341 (9)	C25—C30	1.405 (9)
C4—H4	0.9300	C26—C27	1.386 (8)
C5—C6	1.415 (9)	C27—C28	1.371 (8)
C5—H5	0.9300	C27—H27	0.9300
C6—C7	1.397 (9)	C28—C29	1.370 (9)
C7—C8	1.345 (9)	C28—H28	0.9300
C7—H7	0.9300	C29—C30	1.356 (10)
C8—C9	1.408 (8)	C29—H29	0.9300
C8—H8	0.9300	C30—H30	0.9300
C9—C10	1.460 (8)	C31—C32	1.376 (9)
C10—C15	1.392 (8)	C31—H31	0.9300
C10—C11	1.398 (8)	C32—C33	1.369 (9)
C11—C12	1.395 (8)	C32—H32	0.9300
C12—C13	1.384 (8)	C33—C34	1.366 (9)
C12—H12	0.9300	C33—H33	0.9300
C13—C14	1.375 (9)	C34—C35	1.370 (8)
C13—H13	0.9300	C34—H34	0.9300
C14—C15	1.378 (9)	C35—H35	0.9300
C14—H14	0.9300

C11—Ir1—C26	87.3 (2)	C15—C14—H14	119.7
C11—Ir1—N1	80.0 (2)	C14—C15—C10	119.4 (7)
C26—Ir1—N1	93.3 (2)	C14—C15—H15	120.3
C11—Ir1—N2	94.9 (2)	C10—C15—H15	120.3
C26—Ir1—N2	80.0 (2)	N2—C16—C17	120.7 (6)
N1—Ir1—N2	171.7 (2)	N2—C16—C21	120.6 (6)
C11—Ir1—N3	173.07 (19)	C17—C16—C21	118.7 (7)
C26—Ir1—N3	87.8 (2)	C18—C17—C16	120.6 (8)
N1—Ir1—N3	105.16 (18)	C18—C17—H17	119.7
N2—Ir1—N3	79.48 (17)	C16—C17—H17	119.7
C11—Ir1—Cl1	96.67 (17)	C17—C18—C19	119.9 (9)
C26—Ir1—Cl1	174.02 (16)	C17—C18—H18	120.0
N1—Ir1—Cl1	83.02 (14)	C19—C18—H18	120.0
N2—Ir1—Cl1	104.10 (14)	C20—C19—C18	121.2 (9)
N3—Ir1—Cl1	88.68 (13)	C20—C19—H19	119.4
C9—N1—C1	118.3 (5)	C18—C19—H19	119.4
C9—N1—Ir1	113.8 (4)	C19—C20—C21	121.0 (9)
C1—N1—Ir1	127.9 (4)	C19—C20—H20	119.5
C24—N2—C16	118.8 (5)	C21—C20—H20	119.5
C24—N2—Ir1	112.8 (4)	C22—C21—C20	123.7 (8)
C16—N2—Ir1	127.7 (4)	C22—C21—C16	117.9 (7)
C35—N3—C31	117.0 (5)	C20—C21—C16	118.3 (8)
C35—N3—Ir1	121.9 (4)	C23—C22—C21	120.6 (7)
C31—N3—Ir1	120.1 (4)	C23—C22—H22	119.7
N1—C1—C6	120.4 (6)	C21—C22—H22	119.7
N1—C1—C2	120.8 (6)	C22—C23—C24	120.2 (7)
C6—C1—C2	118.8 (6)	C22—C23—H23	119.9
C3—C2—C1	120.2 (7)	C24—C23—H23	119.9
C3—C2—H2	119.9	N2—C24—C23	120.9 (7)
C1—C2—H2	119.9	N2—C24—C25	115.2 (5)
C2—C3—C4	121.5 (7)	C23—C24—C25	123.8 (6)
C2—C3—H3	119.3	C26—C25—C30	121.6 (7)
C4—C3—H3	119.3	C26—C25—C24	115.5 (6)
C5—C4—C3	119.0 (6)	C30—C25—C24	123.0 (6)
C5—C4—H4	120.5	C27—C26—C25	116.3 (6)
C3—C4—H4	120.5	C27—C26—Ir1	128.8 (5)
C4—C5—C6	121.7 (7)	C25—C26—Ir1	114.7 (5)
C4—C5—H5	119.1	C28—C27—C26	122.1 (7)
C6—C5—H5	119.1	C28—C27—H27	118.9
C7—C6—C1	119.2 (6)	C26—C27—H27	118.9
C7—C6—C5	122.0 (6)	C29—C28—C27	120.4 (7)
C1—C6—C5	118.8 (7)	C29—C28—H28	119.8
C8—C7—C6	119.9 (6)	C27—C28—H28	119.8
C8—C7—H7	120.1	C30—C29—C28	119.9 (7)
C6—C7—H7	120.1	C30—C29—H29	120.1
C7—C8—C9	120.0 (7)	C28—C29—H29	120.1
C7—C8—H8	120.0	C29—C30—C25	119.6 (7)
C9—C8—H8	120.0	C29—C30—H30	120.2
N1—C9—C8	122.1 (6)	C25—C30—H30	120.2
N1—C9—C10	115.0 (5)	N3—C31—C32	121.7 (6)
C8—C9—C10	122.9 (6)	N3—C31—H31	119.2
C15—C10—C11	121.5 (6)	C32—C31—H31	119.2
C15—C10—C9	123.3 (6)	C33—C32—C31	119.9 (7)
C11—C10—C9	115.2 (5)	C33—C32—H32	120.1
C12—C11—C10	117.0 (6)	C31—C32—H32	120.1
C12—C11—Ir1	127.9 (5)	C34—C33—C32	119.0 (7)
C10—C11—Ir1	114.9 (4)	C34—C33—H33	120.5
C13—C12—C11	121.9 (6)	C32—C33—H33	120.5
C13—C12—H12	119.1	C33—C34—C35	118.4 (7)
C11—C12—H12	119.1	C33—C34—H34	120.8
C14—C13—C12	119.6 (6)	C35—C34—H34	120.8
C14—C13—H13	120.2	N3—C35—C34	124.0 (6)
C12—C13—H13	120.2	N3—C35—H35	118.0
C13—C14—C15	120.6 (7)	C34—C35—H35	118.0
C13—C14—H14	119.7

C11—Ir1—N1—C9	9.3 (4)	Cl1—Ir1—C11—C10	−90.5 (4)
C26—Ir1—N1—C9	−77.3 (4)	C10—C11—C12—C13	−1.9 (9)
N3—Ir1—N1—C9	−165.9 (4)	Ir1—C11—C12—C13	173.5 (5)
Cl1—Ir1—N1—C9	107.4 (4)	C11—C12—C13—C14	0.1 (10)
C11—Ir1—N1—C1	−173.1 (5)	C12—C13—C14—C15	1.7 (10)
C26—Ir1—N1—C1	100.3 (5)	C13—C14—C15—C10	−1.7 (11)
N3—Ir1—N1—C1	11.7 (5)	C11—C10—C15—C14	−0.1 (10)
Cl1—Ir1—N1—C1	−75.0 (5)	C9—C10—C15—C14	178.4 (6)
C11—Ir1—N2—C24	−98.7 (4)	C24—N2—C16—C17	167.2 (6)
C26—Ir1—N2—C24	−12.3 (4)	Ir1—N2—C16—C17	−22.6 (9)
N3—Ir1—N2—C24	77.2 (4)	C24—N2—C16—C21	−11.0 (9)
Cl1—Ir1—N2—C24	163.2 (4)	Ir1—N2—C16—C21	159.2 (5)
C11—Ir1—N2—C16	90.6 (5)	N2—C16—C17—C18	179.1 (7)
C26—Ir1—N2—C16	176.9 (5)	C21—C16—C17—C18	−2.6 (11)
N3—Ir1—N2—C16	−93.5 (5)	C16—C17—C18—C19	−2.4 (12)
Cl1—Ir1—N2—C16	−7.5 (5)	C17—C18—C19—C20	5.5 (15)
C26—Ir1—N3—C35	−24.1 (4)	C18—C19—C20—C21	−3.4 (16)
N1—Ir1—N3—C35	68.6 (4)	C19—C20—C21—C22	175.4 (9)
N2—Ir1—N3—C35	−104.4 (4)	C19—C20—C21—C16	−1.8 (13)
Cl1—Ir1—N3—C35	151.0 (4)	N2—C16—C21—C22	5.6 (10)
C26—Ir1—N3—C31	144.4 (5)	C17—C16—C21—C22	−172.7 (7)
N1—Ir1—N3—C31	−122.9 (4)	N2—C16—C21—C20	−177.0 (7)
N2—Ir1—N3—C31	64.1 (4)	C17—C16—C21—C20	4.7 (10)
Cl1—Ir1—N3—C31	−40.5 (4)	C20—C21—C22—C23	−174.1 (8)
C9—N1—C1—C6	4.5 (8)	C16—C21—C22—C23	3.1 (12)
Ir1—N1—C1—C6	−173.0 (4)	C21—C22—C23—C24	−6.3 (13)
C9—N1—C1—C2	−174.3 (6)	C16—N2—C24—C23	7.9 (9)
Ir1—N1—C1—C2	8.1 (8)	Ir1—N2—C24—C23	−163.8 (5)
N1—C1—C2—C3	−179.2 (6)	C16—N2—C24—C25	−174.1 (5)
C6—C1—C2—C3	1.9 (10)	Ir1—N2—C24—C25	14.2 (6)
C1—C2—C3—C4	0.0 (11)	C22—C23—C24—N2	0.7 (11)
C2—C3—C4—C5	−2.6 (11)	C22—C23—C24—C25	−177.1 (7)
C3—C4—C5—C6	3.1 (11)	N2—C24—C25—C26	−7.9 (8)
N1—C1—C6—C7	−1.4 (9)	C23—C24—C25—C26	170.0 (6)
C2—C1—C6—C7	177.5 (6)	N2—C24—C25—C30	171.9 (6)
N1—C1—C6—C5	179.7 (6)	C23—C24—C25—C30	−10.2 (10)
C2—C1—C6—C5	−1.4 (9)	C30—C25—C26—C27	1.7 (9)
C4—C5—C6—C7	−180.0 (7)	C24—C25—C26—C27	−178.5 (5)
C4—C5—C6—C1	−1.1 (10)	C30—C25—C26—Ir1	177.2 (5)
C1—C6—C7—C8	−1.1 (10)	C24—C25—C26—Ir1	−3.0 (7)
C5—C6—C7—C8	177.7 (6)	C11—Ir1—C26—C27	−81.6 (6)
C6—C7—C8—C9	0.6 (10)	N1—Ir1—C26—C27	−1.8 (6)
C1—N1—C9—C8	−5.2 (9)	N2—Ir1—C26—C27	−177.1 (6)
Ir1—N1—C9—C8	172.7 (5)	N3—Ir1—C26—C27	103.2 (5)
C1—N1—C9—C10	174.1 (5)	N1—Ir1—C26—C25	−176.8 (4)
Ir1—N1—C9—C10	−8.0 (6)	N2—Ir1—C26—C25	8.0 (4)
C7—C8—C9—N1	2.7 (10)	N3—Ir1—C26—C25	−71.7 (4)
C7—C8—C9—C10	−176.5 (6)	C25—C26—C27—C28	0.4 (9)
N1—C9—C10—C15	−177.8 (6)	Ir1—C26—C27—C28	−174.5 (5)
C8—C9—C10—C15	1.5 (10)	C26—C27—C28—C29	−2.3 (10)
N1—C9—C10—C11	0.8 (8)	C27—C28—C29—C30	2.2 (11)
C8—C9—C10—C11	−179.9 (6)	C28—C29—C30—C25	−0.2 (11)
C15—C10—C11—C12	1.9 (9)	C26—C25—C30—C29	−1.8 (10)
C9—C10—C11—C12	−176.7 (5)	C24—C25—C30—C29	178.5 (6)
C15—C10—C11—Ir1	−174.1 (5)	C35—N3—C31—C32	1.1 (9)
C9—C10—C11—Ir1	7.3 (7)	Ir1—N3—C31—C32	−167.9 (5)
C26—Ir1—C11—C12	−90.5 (6)	N3—C31—C32—C33	−0.5 (10)
N1—Ir1—C11—C12	175.7 (6)	C31—C32—C33—C34	0.5 (11)
N2—Ir1—C11—C12	−10.8 (6)	C32—C33—C34—C35	−1.1 (11)
Cl1—Ir1—C11—C12	94.1 (5)	C31—N3—C35—C34	−1.8 (9)
C26—Ir1—C11—C10	85.0 (5)	Ir1—N3—C35—C34	167.0 (5)
N1—Ir1—C11—C10	−8.8 (4)	C33—C34—C35—N3	1.9 (10)
N2—Ir1—C11—C10	164.7 (4)

Experimental details

Crystal data
Chemical formula	[Ir(C₁₅H₁₀N)₂Cl(C₅H₅N)]·H₂O
M_r	733.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	9.8949 (15), 17.653 (3), 16.424 (3)
β (°)	98.545 (3)
V (Å³)	2837.0 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.83
Crystal size (mm)	0.16 × 0.12 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.511, 0.684
No. of measured, independent and observed [I > 2σ(I)] reflections	14857, 5027, 3702
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.075, 1.02
No. of reflections	5027
No. of parameters	370
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.72

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Ir1—C11	1.990 (6)	Ir1—N2	2.092 (5)
Ir1—C26	1.992 (6)	Ir1—N3	2.221 (5)
Ir1—N1	2.090 (5)	Ir1—Cl1	2.5182 (16)

C11—Ir1—C26	87.3 (2)	N1—Ir1—N3	105.16 (18)
C11—Ir1—N1	80.0 (2)	N2—Ir1—N3	79.48 (17)
C26—Ir1—N1	93.3 (2)	C11—Ir1—Cl1	96.67 (17)
C11—Ir1—N2	94.9 (2)	C26—Ir1—Cl1	174.02 (16)
C26—Ir1—N2	80.0 (2)	N1—Ir1—Cl1	83.02 (14)
N1—Ir1—N2	171.7 (2)	N2—Ir1—Cl1	104.10 (14)
C11—Ir1—N3	173.07 (19)	N3—Ir1—Cl1	88.68 (13)
C26—Ir1—N3	87.8 (2)

Acknowledgements

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

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
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gao, R., Ho, D. G., Hernandez, B., Selke, M., Murphy, D., Djurovich, P. & Thompson, M. E. (2002). J. Am. Chem. Soc. 124, 14828–14829. Web of Science CrossRef PubMed CAS Google Scholar
Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Kwong, R., Tsyba, I., Bortz, M., Mui, B., Bau, R. & Thompson, M. E. (2001a). Inorg. Chem. 40, 1704–1711. Web of Science CSD CrossRef PubMed CAS Google Scholar
Lamansky, S., Djurovich, P., Murphy, D., Abdel-Razzaq, F., Lee, H.-E., Adachi, C., Burrows, P. E., Forrest, S. R. & Thompson, M. E. (2001b). J. Am. Chem. Soc. 123, 4304–4312. Web of Science CrossRef PubMed CAS Google Scholar
Liu, T., Xia, B.-H., Zhou, X., Zhang, H.-X., Pan, Q.-J. & Gao, J.-S. (2007). Organometallics, 26, 143–149. Web of Science CrossRef 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals 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.