metal-organic compounds
Aqua[N-(1-naphthyl)acetamido-κN]bis[2-(2-pyridyl)phenyl-κ2N,C1]iridium(III) ethylene glycol hemisolvate
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
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
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell 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
10.1107/S1600536808010040/sg2232sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010040/sg2232Isup2.hkl
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
on silica gel with dichloromethane as to give a yellow solid. Single crystals suitable for X-ray diffraction were grown by slow diffusion of ethylene glycol solution.All H atoms were placed in calculated positions with C—H = 0.93 (aromatic), 0.97 Å (methylene), and refined using a riding model with Uiso(H) = 1.2Ueq(C,N). Water H atoms were tentatively located in difference Fourier maps and were refined with distance restraints of O–H = 0.82 Å and H···H = 1.29 Å, each within a standard deviation of 0.01 Å; and with Uiso(H) = 1.5 Ueq(O).
Data collection: APEX2 (Bruker, 2005); cell
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).[Ir(C11H8N)2(C12H10NO)(H2O)]·0.5C2H6O2 | Z = 2 |
Mr = 733.83 | F(000) = 726 |
Triclinic, P1 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 5269 independent reflections |
Radiation source: fine-focus sealed tube | 4451 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scans | θmax = 25.1°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→12 |
Tmin = 0.615, Tmax = 0.775 | k = −12→12 |
7940 measured reflections | l = −17→8 |
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(Fo2) + (0.05P)2 + 0.001P] |
5269 reflections | (Δ/σ)max = 0.004 |
381 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −0.91 e Å−3 |
[Ir(C11H8N)2(C12H10NO)(H2O)]·0.5C2H6O2 | γ = 107.423 (6)° |
Mr = 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)° |
Bruker SMART CCD area-detector diffractometer | 5269 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4451 reflections with I > 2σ(I) |
Tmin = 0.615, Tmax = 0.775 | Rint = 0.027 |
7940 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.74 e Å−3 |
5269 reflections | Δρmin = −0.91 e Å−3 |
381 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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. |
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 |
Mr | 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) |
Tmin, Tmax | 0.615, 0.775 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7940, 5269, 4451 |
Rint | 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 |
Δρmax, Δρmin (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).
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) |
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
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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—Nav = 2.048Å and Ir—Cav = 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.)