Bis(acetyl­acetonato-κ2O,O′)­aqua­(diacetyl­methanido-κC)iridium(III)

Chang, Q.-W.; Xie, M.-J.; Liu, W.-P.; Chen, X.-Z.; Ye, Q.-S.

doi:10.1107/S160053680903760X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page m1264

doi:10.1107/S160053680903760X

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Bis(acetylacetonato-κ²O,O′)aqua(diacetylmethanido-κC)iridium(III)

Qiao-Wen Chang,^a Ming-Jin Xie,^b Wei-Ping Liu,^a ^* Xi-Zhu Chen ^a and Qing-Song Ye ^a

^aChemistry Laboratory, Kunming Institute of Precious Metals, Kunming, People's Republic of China, and ^bDepartment of Chemistry, Yunnan University, Kunming, People's Republic of China
^*Correspondence e-mail: liuweiping0917@126.com

(Received 8 May 2009; accepted 17 September 2009; online 30 September 2009)

In the crystal structure of the title compound, [Ir(C₅H₇O₂)₃(H₂O)], the Ir^III atom is six-coordinated and situated in a slightly distorted octahedral environment. The complex contains both Ir—O and Ir—C bonds and was isolated from a reaction mixture of IrCl₃(H₂O)_x, pentane-2,5-dione and NaHCO₃. O—H⋯O hydrogen bonding between the water molecules and the carbonyl O atoms of adjacent molecules leads to a layered motif extending parallel to (010).

Related literature

For background to the title compound, see: Bennett & Mitchell (1976 ); Bhalla et al. (2005 ); Gibson (1969 ); Matsumoto et al. (2000 ); Periana et al. (2002 ); Wong-Foy et al. (2003 ). For a related structure, see: Isakova et al. (1999 ); For background on hydrogen bonding, see: Desiraju (1996 ).

Experimental

Crystal data

[Ir(C₅H₇O₂)₃(H₂O)]
M_r = 507.54
Triclinic, $[P \overline 1]$
a = 7.7853 (13) Å
b = 7.9461 (13) Å
c = 16.362 (3) Å
α = 77.295 (2)°
β = 77.927 (2)°
γ = 60.918 (1)°
V = 856.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 7.82 mm⁻¹
T = 293 K
0.15 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.387, T_max = 0.539
7435 measured reflections
3900 independent reflections
2885 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.127
S = 1.03
3900 reflections
215 parameters
H-atom parameters constrained
Δρ_max = 2.37 e Å⁻³
Δρ_min = −1.88 e Å⁻³

Table 1
Selected bond lengths (Å)

Ir1—O1	2.015 (8)
Ir1—O4	2.017 (7)
Ir1—O3	2.026 (7)
Ir1—O2	2.029 (7)
Ir1—C11	2.131 (11)
Ir1—O5	2.155 (7)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5D⋯O7ⁱ	0.82	2.24	2.706 (11)	116
O5—H5E⋯O6ⁱⁱ	0.89	2.11	2.715 (11)	125
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903760X/er2069sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903760X/er2069Isup2.hkl

checkCIF report

Comment top

[Ir(acac-O, O)₂(acac-C³)(H₂O)], as a novel, themally stable, homogeneous bis-acac-O, O—Ir(III) complex catalyst for the anti-Markovnikov, hydroarylation of olefins, has attracted considerable attention (Periana et al., 2002, Wong-Foy et al. 2003, Bhalla et al., 2005). Bennett et al. obtained [Ir(µ-acac-O,O,C³)(acac-O, O)(acac-C³)] and an unknown yellow solid as byproducts in the course of an attempt to improve the synthesis of Ir(acac)₃ (Bennett & Mitchell, 1976). However, they were unable to purify the yellow solid or characterize its structure. Recently Periana et al. successfully isolated this yellow product in pure form and proved it to be [Ir(acac-O, O)₂(acac-C³)(H₂O)] by spectroscopic data(Periana et al., 2002). Despite the thermal and oxidative stability of octahedral iridium (III)-carbon σ -bonded complexes, there are little well characterized γ-C-bonded β-diketone complexes of iridium (III) except [Ir(µ-acac-O,O,C³)(acac-O, O)(acac-C³)] (Gibson, 1969, Matsumoto et al., 2000).

Recently the single-crystal of the compound was obtained in our laboratory and we report its crystallographic structure. In the complex, the central Ir atom is coordinated by a octahedron of four oxygen atoms of two acetylacetone ligands, one carbon atom of one acetylacetone ligand and one oxygen atom of water molcule. The average Ir—O bond length of two acetylacetone ligands is 2.02 Å, which agree with the literature data of Ir(acac)₃ (Isakova et al., 1999), however, Ir—O bond length of coordinated water is 2.15 Å, which is longer than the former, whereas Ir—C bond length is found to be 2.13 Å. Intermolecular C—H···O hydrogen bond (Desiraju, 1996) and C—H···C hydrogen bond are present in the structure; while the C···O distances are within the range of 3.039 (9)–3.486 (10) Å, C—H···O are found to be within the range of 110–168°. The compound forms a hydrogen-bonded chain in which the O5 water uses two H atom to serve as a donor to the O atoms of adjacent molecules, these weaker interactions giving rise to a three-dimensional framework structure.

Related literature top

For background on the title compound, see: Bennett & Mitchell (1976); Bhalla et al. (2005); Gibson (1969); Matsumoto et al. (2000); Periana et al. (2002); Wong-Foy et al. (2003). For a related structure, see: Isakova et al. (1999); For background on hydrogen bonding, see: Desiraju (1996). Please check added text.t

Experimental top

The complex was synthesized according literature (see Periana et al., 2002). In a round-bottom flask equipped with a reflux condenser vented to an oil bubble, 5 g of IrCl₃ (H₂O)_x (54.34% of Ir, 14.13 mmol), 50 ml of 2, 5-pentadione (48.75 mmol) and 5 g of NaHCO₃(59.5 mmol) were added. The mixture was heated to gentle reflux with stirring for 48 h. During this time, a yellow solid precipitated. The reaction mixture was cooled to room temperature and the solid was collected as crude product. The yellow solid was dissolved in 200 ml H2O at room temperature under vigorous stirring and was filtered. Solution was concentrated under vacuo to give 3.15 g (43.6%) complex as yellow microcrystalline. The compound was crystallized from water to obtain crystals suitable for X-ray structure analysis. 1HNMR (CD3OD,p.p.m.):5.54(s, 2H, CH), 5.49(s, 1H, CH), 1.96(s, 12H, CH3), 1.83(s, 6H, CH3). 13CNMR (dmso,p.p.m.): 208.4(s, C-acac, C=O), 186.1(s, O-acac, C=O), 102.6(s, O-acac, CH), 48.6(s, C-acac, CH), 31.6(s, C-acac, CH3, 26.6(s, O-acac, CH3). Anal. Calcd: Ir, 37.95; C, 35.54; H, 4.93. Found: Ir, 37.90; C, 35.48; H, 4.87.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of the complex, with the atomic labeling scheme. Displacement ellipsoids are shown at the 30% probability level.
	Fig. 2. Packing view, showing the C—H···O hydrogen-bond network between the complexes. Only the H atoms involved in H bonding are drawn. Hydrogen bonds are shown as dashed lines.

Bis(acetylacetonato-κ²O,O')aqua(diacetylmethanido- κC)iridium(III) top

Crystal data top

[Ir(C₅H₇O₂)₃(H₂O)]	Z = 2
M_r = 507.54	F(000) = 492
Triclinic, P1	D_x = 1.968 Mg m⁻³
a = 7.7853 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9461 (13) Å	Cell parameters from 1164 reflections
c = 16.362 (3) Å	θ = 1.3–28.4°
α = 77.295 (2)°	µ = 7.82 mm⁻¹
β = 77.927 (2)°	T = 293 K
γ = 60.918 (1)°	Block, orange
V = 856.7 (3) Å³	0.15 × 0.13 × 0.09 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3900 independent reflections
Radiation source: fine-focus sealed tube	2885 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.387, T_max = 0.539	k = −10→10
7435 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0469P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3900 reflections	Δρ_max = 2.37 e Å⁻³
215 parameters	Δρ_min = −1.88 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (5)

Crystal data top

[Ir(C₅H₇O₂)₃(H₂O)]	γ = 60.918 (1)°
M_r = 507.54	V = 856.7 (3) Å³
Triclinic, P1	Z = 2
a = 7.7853 (13) Å	Mo Kα radiation
b = 7.9461 (13) Å	µ = 7.82 mm⁻¹
c = 16.362 (3) Å	T = 293 K
α = 77.295 (2)°	0.15 × 0.13 × 0.09 mm
β = 77.927 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3900 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2885 reflections with I > 2σ(I)
T_min = 0.387, T_max = 0.539	R_int = 0.061
7435 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.03	Δρ_max = 2.37 e Å⁻³
3900 reflections	Δρ_min = −1.88 e Å⁻³
215 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	0.36783 (6)	0.62096 (6)	0.25137 (3)	0.02612 (17)
O1	0.3350 (11)	0.7800 (11)	0.1361 (5)	0.0327 (18)
O2	0.6421 (11)	0.4122 (11)	0.2154 (5)	0.0355 (19)
O3	0.1042 (10)	0.8433 (10)	0.2871 (5)	0.0315 (17)
O4	0.4064 (11)	0.4697 (11)	0.3682 (5)	0.0334 (18)
O5	0.5066 (10)	0.7689 (10)	0.2858 (5)	0.0337 (18)
H5D	0.5577	0.8115	0.2430	0.050*
H5E	0.5997	0.6857	0.3187	0.050*
O6	−0.0934 (12)	0.5794 (12)	0.2823 (6)	0.046 (2)
O7	0.4419 (13)	0.1349 (12)	0.2185 (5)	0.048 (2)
C1	0.4627 (18)	0.7249 (17)	0.0700 (7)	0.035 (3)
C2	0.402 (2)	0.8478 (19)	−0.0103 (7)	0.047 (3)
H2A	0.3312	0.8038	−0.0347	0.070*
H2B	0.5167	0.8398	−0.0483	0.070*
H2C	0.3172	0.9801	−0.0006	0.070*
C3	0.6452 (19)	0.5594 (18)	0.0726 (8)	0.046 (3)
H3	0.7256	0.5384	0.0212	0.055*
C4	0.7252 (17)	0.4194 (15)	0.1418 (8)	0.034 (3)
C5	0.9347 (19)	0.256 (2)	0.1293 (9)	0.055 (4)
H5A	0.9385	0.1353	0.1578	0.083*
H5B	1.0224	0.2819	0.1519	0.083*
H5C	0.9756	0.2480	0.0701	0.083*
C6	0.2844 (19)	0.5342 (18)	0.4321 (7)	0.040 (3)
C7	0.334 (2)	0.402 (2)	0.5146 (8)	0.055 (4)
H7A	0.2550	0.3352	0.5289	0.083*
H7B	0.3074	0.4781	0.5582	0.083*
H7C	0.4718	0.3091	0.5092	0.083*
C8	0.1094 (19)	0.7063 (19)	0.4332 (8)	0.044 (3)
H8	0.0380	0.7318	0.4860	0.052*
C9	0.0265 (18)	0.8459 (17)	0.3658 (7)	0.036 (3)
C10	−0.1719 (19)	1.0193 (19)	0.3801 (8)	0.054 (4)
H10A	−0.1759	1.1296	0.3405	0.080*
H10B	−0.1923	1.0475	0.4365	0.080*
H10C	−0.2742	0.9916	0.3725	0.080*
C11	0.2348 (16)	0.4738 (15)	0.2148 (8)	0.034 (3)
H11	0.2784	0.4669	0.1544	0.041*
C12	0.0184 (17)	0.5990 (16)	0.2220 (8)	0.033 (3)
C13	−0.0656 (19)	0.7536 (19)	0.1483 (8)	0.051 (3)
H13A	−0.0591	0.6933	0.1022	0.076*
H13B	0.0101	0.8241	0.1309	0.076*
H13C	−0.2009	0.8417	0.1649	0.076*
C14	0.3079 (17)	0.2716 (16)	0.2559 (7)	0.030 (2)
C15	0.226 (2)	0.2179 (18)	0.3450 (8)	0.046 (3)
H15A	0.3341	0.1330	0.3776	0.070*
H15B	0.1511	0.1529	0.3428	0.070*
H15C	0.1427	0.3337	0.3707	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.0211 (2)	0.0223 (2)	0.0273 (2)	−0.00479 (17)	−0.00288 (16)	−0.00175 (15)
O1	0.028 (4)	0.031 (4)	0.035 (4)	−0.012 (4)	0.001 (4)	−0.007 (4)
O2	0.030 (4)	0.030 (4)	0.039 (5)	−0.008 (4)	0.000 (4)	−0.006 (4)
O3	0.025 (4)	0.027 (4)	0.032 (4)	−0.002 (3)	−0.007 (3)	−0.007 (3)
O4	0.033 (4)	0.041 (5)	0.024 (4)	−0.017 (4)	−0.004 (3)	0.003 (3)
O5	0.021 (4)	0.032 (4)	0.038 (4)	−0.008 (3)	−0.006 (3)	0.003 (4)
O6	0.026 (5)	0.044 (5)	0.058 (6)	−0.010 (4)	−0.005 (4)	0.000 (4)
O7	0.056 (6)	0.028 (4)	0.048 (5)	−0.011 (4)	0.009 (4)	−0.016 (4)
C1	0.045 (7)	0.039 (7)	0.024 (6)	−0.021 (6)	−0.007 (5)	−0.003 (5)
C2	0.059 (9)	0.051 (8)	0.030 (7)	−0.028 (7)	−0.018 (6)	0.011 (6)
C3	0.052 (8)	0.043 (8)	0.029 (7)	−0.012 (7)	−0.003 (6)	−0.004 (6)
C4	0.030 (6)	0.020 (5)	0.049 (7)	−0.009 (5)	0.004 (6)	−0.015 (5)
C5	0.039 (8)	0.054 (9)	0.060 (9)	−0.010 (7)	0.011 (7)	−0.029 (7)
C6	0.046 (8)	0.048 (8)	0.029 (6)	−0.029 (7)	0.002 (6)	0.002 (6)
C7	0.054 (9)	0.078 (11)	0.039 (7)	−0.036 (8)	−0.011 (7)	0.002 (7)
C8	0.044 (8)	0.055 (8)	0.031 (7)	−0.023 (7)	0.009 (6)	−0.016 (6)
C9	0.039 (7)	0.033 (7)	0.036 (7)	−0.017 (6)	0.003 (6)	−0.012 (5)
C10	0.038 (8)	0.049 (8)	0.043 (8)	0.001 (7)	−0.001 (6)	−0.005 (7)
C11	0.021 (6)	0.022 (6)	0.050 (7)	−0.002 (5)	−0.005 (5)	−0.003 (5)
C12	0.030 (6)	0.026 (6)	0.043 (7)	−0.010 (5)	−0.011 (6)	−0.009 (5)
C13	0.043 (8)	0.047 (8)	0.049 (8)	−0.015 (7)	−0.006 (6)	0.003 (6)
C14	0.038 (7)	0.030 (6)	0.032 (6)	−0.021 (5)	−0.009 (5)	−0.006 (5)
C15	0.058 (9)	0.041 (7)	0.042 (7)	−0.024 (7)	−0.003 (6)	−0.005 (6)

Geometric parameters (Å, º) top

Ir1—O1	2.015 (8)	C5—H5C	0.9600
Ir1—O4	2.017 (7)	C6—C8	1.384 (17)
Ir1—O3	2.026 (7)	C6—C7	1.508 (16)
Ir1—O2	2.029 (7)	C7—H7A	0.9600
Ir1—C11	2.131 (11)	C7—H7B	0.9600
Ir1—O5	2.155 (7)	C7—H7C	0.9600
O1—C1	1.297 (13)	C8—C9	1.388 (17)
O2—C4	1.245 (13)	C8—H8	0.9300
O3—C9	1.302 (13)	C9—C10	1.504 (16)
O4—C6	1.266 (13)	C10—H10A	0.9600
O5—H5D	0.8200	C10—H10B	0.9600
O5—H5E	0.8900	C10—H10C	0.9600
O6—C12	1.208 (13)	C11—C14	1.468 (14)
O7—C14	1.252 (13)	C11—C12	1.477 (15)
C1—C3	1.391 (16)	C11—H11	0.9800
C1—C2	1.468 (15)	C12—C13	1.513 (16)
C2—H2A	0.9600	C13—H13A	0.9600
C2—H2B	0.9600	C13—H13B	0.9600
C2—H2C	0.9600	C13—H13C	0.9600
C3—C4	1.406 (16)	C14—C15	1.520 (15)
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.518 (16)	C15—H15B	0.9600
C5—H5A	0.9600	C15—H15C	0.9600
C5—H5B	0.9600

O1—Ir1—O4	177.1 (3)	O4—C6—C7	115.2 (11)
O1—Ir1—O3	84.6 (3)	C8—C6—C7	117.6 (11)
O4—Ir1—O3	95.1 (3)	C6—C7—H7A	109.5
O1—Ir1—O2	94.2 (3)	C6—C7—H7B	109.5
O4—Ir1—O2	85.9 (3)	H7A—C7—H7B	109.5
O3—Ir1—O2	175.4 (3)	C6—C7—H7C	109.5
O1—Ir1—C11	87.6 (4)	H7A—C7—H7C	109.5
O4—Ir1—C11	95.3 (4)	H7B—C7—H7C	109.5
O3—Ir1—C11	93.5 (4)	C6—C8—C9	128.5 (11)
O2—Ir1—C11	90.9 (4)	C6—C8—H8	115.7
O1—Ir1—O5	91.6 (3)	C9—C8—H8	115.7
O4—Ir1—O5	85.5 (3)	O3—C9—C8	126.0 (11)
O3—Ir1—O5	87.3 (3)	O3—C9—C10	113.8 (10)
O2—Ir1—O5	88.2 (3)	C8—C9—C10	120.2 (11)
C11—Ir1—O5	178.8 (4)	C9—C10—H10A	109.5
C1—O1—Ir1	123.5 (7)	C9—C10—H10B	109.5
C4—O2—Ir1	122.2 (7)	H10A—C10—H10B	109.5
C9—O3—Ir1	121.2 (7)	C9—C10—H10C	109.5
C6—O4—Ir1	121.9 (8)	H10A—C10—H10C	109.5
Ir1—O5—H5D	109.5	H10B—C10—H10C	109.5
Ir1—O5—H5E	109.5	C14—C11—C12	117.6 (10)
H5D—O5—H5E	109.2	C14—C11—Ir1	112.4 (8)
O1—C1—C3	123.7 (10)	C12—C11—Ir1	108.4 (7)
O1—C1—C2	115.6 (11)	C14—C11—H11	105.8
C3—C1—C2	120.7 (11)	C12—C11—H11	105.8
C1—C2—H2A	109.5	Ir1—C11—H11	105.8
C1—C2—H2B	109.5	O6—C12—C11	123.2 (11)
H2A—C2—H2B	109.5	O6—C12—C13	119.2 (11)
C1—C2—H2C	109.5	C11—C12—C13	117.6 (11)
H2A—C2—H2C	109.5	C12—C13—H13A	109.5
H2B—C2—H2C	109.5	C12—C13—H13B	109.5
C1—C3—C4	129.1 (11)	H13A—C13—H13B	109.5
C1—C3—H3	115.5	C12—C13—H13C	109.5
C4—C3—H3	115.5	H13A—C13—H13C	109.5
O2—C4—C3	126.9 (11)	H13B—C13—H13C	109.5
O2—C4—C5	114.0 (11)	O7—C14—C11	120.8 (10)
C3—C4—C5	119.1 (11)	O7—C14—C15	117.0 (10)
C4—C5—H5A	109.5	C11—C14—C15	122.2 (10)
C4—C5—H5B	109.5	C14—C15—H15A	109.5
H5A—C5—H5B	109.5	C14—C15—H15B	109.5
C4—C5—H5C	109.5	H15A—C15—H15B	109.5
H5A—C5—H5C	109.5	C14—C15—H15C	109.5
H5B—C5—H5C	109.5	H15A—C15—H15C	109.5
O4—C6—C8	127.1 (11)	H15B—C15—H15C	109.5

O4—Ir1—O1—C1	96 (6)	C1—C3—C4—C5	−176.5 (12)
O3—Ir1—O1—C1	−179.7 (9)	Ir1—O4—C6—C8	2.3 (17)
O2—Ir1—O1—C1	4.8 (9)	Ir1—O4—C6—C7	179.4 (8)
C11—Ir1—O1—C1	−85.9 (9)	O4—C6—C8—C9	1 (2)
O5—Ir1—O1—C1	93.2 (9)	C7—C6—C8—C9	−176.4 (13)
O1—Ir1—O2—C4	0.1 (9)	Ir1—O3—C9—C8	1.1 (16)
O4—Ir1—O2—C4	−177.0 (9)	Ir1—O3—C9—C10	−178.4 (8)
O3—Ir1—O2—C4	−76 (4)	C6—C8—C9—O3	−3 (2)
C11—Ir1—O2—C4	87.7 (9)	C6—C8—C9—C10	176.9 (13)
O5—Ir1—O2—C4	−91.4 (9)	O1—Ir1—C11—C14	149.4 (8)
O1—Ir1—O3—C9	−176.0 (8)	O4—Ir1—C11—C14	−30.7 (8)
O4—Ir1—O3—C9	1.1 (8)	O3—Ir1—C11—C14	−126.1 (8)
O2—Ir1—O3—C9	−100 (4)	O2—Ir1—C11—C14	55.2 (8)
C11—Ir1—O3—C9	96.8 (9)	O5—Ir1—C11—C14	101 (17)
O5—Ir1—O3—C9	−84.1 (8)	O1—Ir1—C11—C12	−78.8 (8)
O1—Ir1—O4—C6	81 (6)	O4—Ir1—C11—C12	101.0 (8)
O3—Ir1—O4—C6	−2.7 (9)	O3—Ir1—C11—C12	5.6 (8)
O2—Ir1—O4—C6	172.7 (9)	O2—Ir1—C11—C12	−173.0 (8)
C11—Ir1—O4—C6	−96.8 (9)	O5—Ir1—C11—C12	−127 (16)
O5—Ir1—O4—C6	84.2 (9)	C14—C11—C12—O6	30.9 (17)
Ir1—O1—C1—C3	−6.4 (16)	Ir1—C11—C12—O6	−98.0 (11)
Ir1—O1—C1—C2	172.5 (8)	C14—C11—C12—C13	−146.7 (11)
O1—C1—C3—C4	2 (2)	Ir1—C11—C12—C13	84.4 (11)
C2—C1—C3—C4	−176.5 (13)	C12—C11—C14—O7	135.2 (12)
Ir1—O2—C4—C3	−3.7 (17)	Ir1—C11—C14—O7	−97.9 (11)
Ir1—O2—C4—C5	176.3 (7)	C12—C11—C14—C15	−45.0 (16)
C1—C3—C4—O2	3 (2)	Ir1—C11—C14—C15	82.0 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5D···O7ⁱ	0.82	2.24	2.706 (11)	116
O5—H5E···O6ⁱⁱ	0.89	2.11	2.715 (11)	125

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Ir(C₅H₇O₂)₃(H₂O)]
M_r	507.54
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7853 (13), 7.9461 (13), 16.362 (3)
α, β, γ (°)	77.295 (2), 77.927 (2), 60.918 (1)
V (Å³)	856.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.82
Crystal size (mm)	0.15 × 0.13 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.387, 0.539
No. of measured, independent and observed [I > 2σ(I)] reflections	7435, 3900, 2885
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.127, 1.03
No. of reflections	3900
No. of parameters	215
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.37, −1.88

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ir1—O1	2.015 (8)	Ir1—O2	2.029 (7)
Ir1—O4	2.017 (7)	Ir1—C11	2.131 (11)
Ir1—O3	2.026 (7)	Ir1—O5	2.155 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5D···O7ⁱ	0.82	2.24	2.706 (11)	116.3
O5—H5E···O6ⁱⁱ	0.89	2.11	2.715 (11)	124.8

Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z.

Acknowledgements

This work was financially supported by Yunnan Provincial Science and Technology Department of the People's Republic of China (grant Nos. 2008IA008 and 2008CF002)

References

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