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Acta Cryst. (2007). E63, m1818    [ doi:10.1107/S1600536807026621 ]

Dibromido([eta]5-pentamethylcyclopentadienyl)(5-phenyldibenzophosphole-[kappa]P)iridium(III) dichloromethane solvate

M. Kotera and T. Suzuki

Abstract top

The title compound, [IrBr2([eta]5-C10H15)(C18H13P)]·CH2Cl2, is the first example of an iridium(III) phosphole complex to be characterized by X-ray crystallographic analysis. The Ir-P bond length is 2.2828 (15) Å, which is shorter by 0.04 Å than that of the analogous PPh3 complex. This is indicative of the steric compactness of 5-phenyldibenzophosphole compared with PPh3. The dibenzophosphole portion of the ligand is nearly planar, and the planes of the dibenzophosphole units of neighbouring molecules are stacked on top of each other to form a dimer in the crystal structure. The closest C...C distances between the planes are ~3.9 Å.

Comment top

A large number of iridium(III) phosphine complexes has been characterized by X-ray analysis, while the structural study of the analogous phosphole complexes is limited. In fact, there has been no reports on the crystal structures of iridum(III) phosphole complexes, and only one paper describing the phosphole complex of iridium(I) (Hayashi et al., 1983). Here, we report the crystal structure of iridium(III) complex containing 5-phenyldibenzophosphole, [Cp*IrBr2(PhPC12H8)]·CH2Cl2 (Cp* = η5-C5Me5), (I). A perspective drawing of (I) is shown in Fig. 1. The structural parameters of the 5-phenyldibenzophosphole moiety are comparable to those of free ligand (Meehan et al., 1997) and of the other metal complexes (Affandi et al., 1988; Attar et al., 1990; Matsuura et al., 1992; Kessler et al., 1993). The Ir—P bond is 2.2828 (15) Å, which is shorter by 0.04 Å than that of [Cp*IrCl2(PPh3)] (2.324 (3) Å; Le Bras et al., 1997). This would be due to the steric compactness of 5-phenyldibenzophosphole than PPh3. The dibenzophosphole moiety is nearly planar; the P atom is deviated by only 0.081 (7) Å from the least-square plane defined by biphenyl group. In the crystal, the dibenzophosphole planes in the neighboring molecules are stacked with each other (Fig. 2); the closest C···C distances between the planes are ~3.9 Å.

Related literature top

For related literature, see: Affandi et al. (1988); Attar et al. (1990); Farrugia (1997); Harder et al. (1991); Hayashi et al. (1983); Kessler et al. (1993); Le Bras et al. (1997); Matsuura et al. (1992); Meehan et al. (1997).

Experimental top

The title complex, (I), was obtained as a by-product from the reaction mixture of [Cp*IrCl2]2, Ph2PC6H4Br (Harder et al., 1991) and nBuLi in THF (which was aimed to prepare [Cp*IrCl(Ph2PC6H4)]), together with the corresponding (bromo)(chloro) and dicholoro complexes, [Cp*IrBrCl(PhPC12H8)]·CH2Cl2 (II) and [Cp*IrCl2(PhPC12H8)]·CH2Cl2 (III), respectively. The resulting red powdery product was recrystallized from a mixture of dichloromethane and methanol, affording red prismatic crystals. Although the crystal structure analyzed was consistent with the dibromo complex (I), the elemental analyses and the NMR spectra of the bulk sample fit well to the 4:4:1 mixture of the dibromo (I), (bromo)(chloro) (II) and dichloro (III) complexes. Anal. Found: C 43.59, H 3.79%. Calcd for C28H28(Br/Cl)2IrP·CH2Cl2: C 43.44, H 3.77%. 1H NMR (399.7 MHz, 303 K, CD2Cl2): δ 1.34 (d, J = 2.4 Hz, Cp*; I), 1.30 (d, J = 2.4 Hz, Cp*; II), 1.26 (d, J = 2.4 Hz, Cp*; III), 7.22–8.20 (m, Ph—PC12H8). 31P{1H} NMR (202.4 MHz, 303 K, CD2Cl2): δ −17.78 (s; I), −14.64 (s; II), −11.34 (s; III).

Refinement top

The H atoms were located geometrically and constrained to ride on their parent atoms with C—H = 0.95–0.99 Å with Uiso(H) = 1.2Ueq(C). The highest peak and deepest hole in the difference Fourier map are located 0.42 and 0.38 Å, respectively, from atoms Ir1 and Br1.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. An ORTEP-3 (Farrugia, 1997) view of the components of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A plot of the dimeric pair of (I). H atoms and the dichloromethane molecule have been omitted for clarity. The asterisk (*) corresponds to symmetry code (1 − x, 1 − y, 1 − z).
Dibromido(η5-pentamethylcyclopentadienyl)(5-\ phenyldibenzophosphole-κP)iridium(III) dichloromethane solvate top
Crystal data top
[IrBr2(C10H15)(C18H13P)]·CH2Cl2F000 = 1600
Mr = 832.42Dx = 1.882 Mg m−3
Monoclinic, P21/aMo Kα radiation
λ = 0.71075 Å
Hall symbol: -P 2yabCell parameters from 17738 reflections
a = 11.0793 (5) Åθ = 3.2–27.4º
b = 23.3836 (10) ŵ = 7.52 mm−1
c = 12.8133 (5) ÅT = 200 (2) K
β = 117.746 (1)ºBlock, red
V = 2937.9 (2) Å30.22 × 0.16 × 0.12 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		6708 independent reflections
Radiation source: fine-focus sealed tube6185 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
Detector resolution: 10.00 pixels mm-1θmax = 27.5º
T = 200(2) Kθmin = 3.2º
ω scansh = −14→14
Absorption correction: numerical
(ABSCOR; Higashi, 1999)		k = −30→30
Tmin = 0.294, Tmax = 0.406l = −16→16
28567 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040  w = 1/[σ2(Fo2) + (0.0587P)2 + 23.6384P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.126(Δ/σ)max = 0.001
S = 1.08Δρmax = 1.76 e Å−3
6708 reflectionsΔρmin = −2.74 e Å−3
317 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00141 (19)
Secondary atom site location: difference Fourier map
Crystal data top
[IrBr2(C10H15)(C18H13P)]·CH2Cl2V = 2937.9 (2) Å3
Mr = 832.42Z = 4
Monoclinic, P21/aMo Kα
a = 11.0793 (5) ŵ = 7.52 mm−1
b = 23.3836 (10) ÅT = 200 (2) K
c = 12.8133 (5) Å0.22 × 0.16 × 0.12 mm
β = 117.746 (1)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		6708 independent reflections
Absorption correction: numerical
(ABSCOR; Higashi, 1999)		6185 reflections with I > 2σ(I)
Tmin = 0.294, Tmax = 0.406Rint = 0.045
28567 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.126  w = 1/[σ2(Fo2) + (0.0587P)2 + 23.6384P]
where P = (Fo2 + 2Fc2)/3
S = 1.08Δρmax = 1.76 e Å−3
6708 reflectionsΔρmin = −2.74 e Å−3
317 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ir10.59098 (2)0.358232 (9)0.903861 (19)0.02182 (11)
Br10.67400 (9)0.43878 (4)1.04905 (7)0.0467 (2)
Br20.83164 (8)0.32885 (4)0.96032 (8)0.0465 (2)
Cl1−0.1229 (3)0.68037 (15)0.6740 (3)0.0792 (8)
Cl20.1036 (4)0.67924 (19)0.6196 (4)0.1039 (13)
P10.60296 (15)0.41650 (6)0.76603 (13)0.0222 (3)
C10.4956 (7)0.2768 (3)0.8362 (7)0.0324 (14)
C20.3938 (6)0.3206 (3)0.7905 (6)0.0275 (12)
C30.3896 (7)0.3487 (3)0.8888 (6)0.0272 (12)
C40.4822 (7)0.3181 (3)0.9943 (6)0.0318 (14)
C50.5475 (7)0.2743 (3)0.9627 (7)0.0360 (15)
C60.5320 (9)0.2348 (3)0.7667 (9)0.051 (2)
H6A0.49140.19750.76650.061*
H6B0.63140.23090.80280.061*
H6C0.49700.24840.68550.061*
C70.2987 (7)0.3322 (3)0.6636 (6)0.0383 (16)
H7A0.34510.32420.61610.046*
H7B0.27060.37250.65400.046*
H7C0.21810.30770.63740.046*
C80.2938 (8)0.3953 (3)0.8842 (7)0.0401 (16)
H8A0.25220.41300.80590.048*
H8B0.34450.42420.94400.048*
H8C0.22230.37900.89970.048*
C90.5046 (9)0.3308 (4)1.1176 (7)0.0470 (19)
H9A0.59430.31651.17510.056*
H9B0.43360.31201.13050.056*
H9C0.50050.37221.12740.056*
C100.6511 (9)0.2319 (4)1.0427 (9)0.054 (2)
H10A0.69360.24631.12380.065*
H10B0.72120.22631.01740.065*
H10C0.60600.19531.03910.065*
C110.7462 (6)0.4656 (3)0.8101 (5)0.0259 (12)
C120.7382 (8)0.5204 (3)0.8489 (6)0.0338 (14)
H120.65880.53200.85370.041*
C130.8465 (8)0.5581 (3)0.8804 (6)0.0392 (16)
H130.84080.59550.90700.047*
C140.9620 (8)0.5419 (3)0.8734 (6)0.0449 (19)
H141.03550.56800.89510.054*
C150.9707 (7)0.4882 (4)0.8351 (7)0.0423 (17)
H151.05070.47730.83040.051*
C160.8643 (7)0.4492 (3)0.8029 (6)0.0333 (14)
H160.87130.41210.77640.040*
C170.4560 (7)0.4607 (3)0.6799 (6)0.0280 (12)
C180.3897 (8)0.4989 (3)0.7191 (7)0.0367 (15)
H180.42140.50500.80100.044*
C190.2749 (9)0.5281 (4)0.6349 (8)0.051 (2)
H190.22880.55470.65990.061*
C200.2282 (9)0.5183 (4)0.5150 (8)0.054 (2)
H200.15080.53860.45890.065*
C210.2930 (8)0.4794 (3)0.4762 (7)0.0433 (17)
H210.25910.47270.39420.052*
C220.4073 (7)0.4502 (3)0.5573 (6)0.0310 (13)
C230.4847 (7)0.4055 (3)0.5328 (6)0.0320 (14)
C240.4606 (9)0.3845 (4)0.4231 (6)0.0458 (19)
H240.38960.40010.35280.055*
C250.5406 (11)0.3410 (4)0.4178 (7)0.053 (2)
H250.52410.32720.34260.064*
C260.6434 (10)0.3167 (4)0.5166 (7)0.049 (2)
H260.69600.28630.50930.059*
C270.6702 (8)0.3370 (3)0.6280 (6)0.0357 (15)
H270.74060.32050.69760.043*
C280.5904 (7)0.3823 (3)0.6347 (5)0.0275 (12)
C290.0387 (14)0.6521 (6)0.7106 (13)0.090 (4)
H29A0.10230.66150.79370.109*
H29B0.03230.61000.70310.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.02293 (15)0.02034 (14)0.02187 (15)0.00001 (8)0.01015 (10)0.00051 (8)
Br10.0534 (5)0.0449 (4)0.0441 (4)−0.0071 (3)0.0247 (4)−0.0091 (3)
Br20.0401 (4)0.0448 (4)0.0530 (5)0.0051 (3)0.0204 (4)0.0048 (3)
Cl10.0736 (18)0.100 (2)0.0667 (16)0.0096 (16)0.0346 (14)0.0189 (15)
Cl20.091 (2)0.131 (3)0.107 (3)0.032 (2)0.060 (2)0.052 (2)
P10.0242 (7)0.0215 (7)0.0199 (7)−0.0004 (5)0.0093 (6)0.0001 (5)
C10.032 (3)0.020 (3)0.047 (4)−0.005 (2)0.020 (3)−0.004 (3)
C20.025 (3)0.027 (3)0.029 (3)−0.008 (2)0.011 (2)−0.003 (2)
C30.026 (3)0.024 (3)0.032 (3)−0.003 (2)0.015 (3)−0.002 (2)
C40.032 (3)0.036 (3)0.031 (3)−0.009 (3)0.017 (3)0.003 (3)
C50.033 (3)0.026 (3)0.050 (4)−0.003 (3)0.020 (3)0.011 (3)
C60.048 (5)0.037 (4)0.075 (6)−0.009 (3)0.035 (4)−0.021 (4)
C70.033 (4)0.047 (4)0.026 (3)−0.016 (3)0.007 (3)−0.002 (3)
C80.037 (4)0.037 (4)0.057 (5)0.001 (3)0.030 (4)−0.004 (3)
C90.048 (4)0.065 (5)0.031 (4)−0.015 (4)0.021 (3)0.001 (4)
C100.040 (4)0.047 (5)0.068 (6)0.002 (4)0.020 (4)0.027 (4)
C110.028 (3)0.027 (3)0.020 (3)−0.004 (2)0.008 (2)0.003 (2)
C120.040 (4)0.029 (3)0.029 (3)−0.003 (3)0.013 (3)0.001 (3)
C130.050 (4)0.029 (3)0.031 (3)−0.013 (3)0.013 (3)−0.003 (3)
C140.046 (4)0.044 (4)0.030 (3)−0.020 (3)0.006 (3)0.008 (3)
C150.027 (3)0.057 (5)0.037 (4)−0.004 (3)0.010 (3)0.010 (3)
C160.032 (3)0.033 (3)0.032 (3)0.001 (3)0.012 (3)0.007 (3)
C170.029 (3)0.025 (3)0.031 (3)0.003 (2)0.014 (3)0.002 (2)
C180.038 (4)0.035 (3)0.039 (4)0.008 (3)0.019 (3)0.006 (3)
C190.046 (4)0.049 (5)0.060 (5)0.024 (4)0.026 (4)0.016 (4)
C200.043 (4)0.060 (5)0.052 (5)0.021 (4)0.016 (4)0.025 (4)
C210.040 (4)0.047 (4)0.032 (4)0.006 (3)0.008 (3)0.011 (3)
C220.034 (3)0.031 (3)0.026 (3)0.000 (3)0.012 (3)0.008 (3)
C230.037 (3)0.033 (3)0.025 (3)−0.007 (3)0.013 (3)0.001 (3)
C240.062 (5)0.050 (4)0.023 (3)−0.008 (4)0.017 (3)−0.001 (3)
C250.082 (7)0.052 (5)0.030 (4)0.001 (5)0.030 (4)−0.009 (4)
C260.072 (6)0.044 (4)0.041 (4)0.007 (4)0.034 (4)−0.007 (3)
C270.047 (4)0.036 (3)0.029 (3)0.003 (3)0.022 (3)−0.003 (3)
C280.035 (3)0.026 (3)0.021 (3)−0.003 (2)0.013 (2)−0.001 (2)
C290.081 (9)0.100 (9)0.087 (9)0.032 (7)0.037 (7)0.046 (8)
Geometric parameters (Å, °) top
Ir1—C12.155 (6)C10—H10B0.9800
Ir1—C32.160 (6)C10—H10C0.9800
Ir1—C22.169 (6)C11—C121.393 (9)
Ir1—C42.231 (6)C11—C161.406 (10)
Ir1—C52.233 (6)C12—C131.389 (10)
Ir1—P12.2829 (15)C12—H120.9500
Ir1—Br12.5022 (8)C13—C141.376 (12)
Ir1—Br22.5118 (8)C13—H130.9500
Cl1—C291.756 (13)C14—C151.369 (12)
Cl2—C291.748 (14)C14—H140.9500
P1—C171.807 (6)C15—C161.391 (10)
P1—C281.809 (6)C15—H150.9500
P1—C111.823 (6)C16—H160.9500
C1—C21.431 (9)C17—C181.389 (9)
C1—C51.447 (10)C17—C221.426 (9)
C1—C61.502 (10)C18—C191.405 (10)
C2—C31.440 (9)C18—H180.9500
C2—C71.495 (9)C19—C201.394 (13)
C3—C41.450 (9)C19—H190.9500
C3—C81.502 (9)C20—C211.387 (12)
C4—C51.416 (10)C20—H200.9500
C4—C91.510 (10)C21—C221.386 (10)
C5—C101.504 (10)C21—H210.9500
C6—H6A0.9800C22—C231.476 (10)
C6—H6B0.9800C23—C241.393 (10)
C6—H6C0.9800C23—C281.396 (9)
C7—H7A0.9800C24—C251.370 (13)
C7—H7B0.9800C24—H240.9500
C7—H7C0.9800C25—C261.371 (13)
C8—H8A0.9800C25—H250.9500
C8—H8B0.9800C26—C271.399 (10)
C8—H8C0.9800C26—H260.9500
C9—H9A0.9800C27—C281.408 (10)
C9—H9B0.9800C27—H270.9500
C9—H9C0.9800C29—H29A0.9900
C10—H10A0.9800C29—H29B0.9900
C1—Ir1—C365.2 (2)C3—C8—H8B109.5
C1—Ir1—C238.7 (2)H8A—C8—H8B109.5
C3—Ir1—C238.9 (2)C3—C8—H8C109.5
C1—Ir1—C463.6 (3)H8A—C8—H8C109.5
C3—Ir1—C438.5 (2)H8B—C8—H8C109.5
C2—Ir1—C463.7 (2)C4—C9—H9A109.5
C1—Ir1—C538.5 (3)C4—C9—H9B109.5
C3—Ir1—C564.1 (2)H9A—C9—H9B109.5
C2—Ir1—C563.9 (3)C4—C9—H9C109.5
C4—Ir1—C537.0 (3)H9A—C9—H9C109.5
C1—Ir1—P1114.2 (2)H9B—C9—H9C109.5
C3—Ir1—P1114.97 (18)C5—C10—H10A109.5
C2—Ir1—P197.34 (17)C5—C10—H10B109.5
C4—Ir1—P1153.27 (19)H10A—C10—H10B109.5
C5—Ir1—P1152.2 (2)C5—C10—H10C109.5
C1—Ir1—Br1154.99 (19)H10A—C10—H10C109.5
C3—Ir1—Br198.68 (17)H10B—C10—H10C109.5
C2—Ir1—Br1135.27 (18)C12—C11—C16119.3 (6)
C4—Ir1—Br191.78 (18)C12—C11—P1120.0 (5)
C5—Ir1—Br1118.2 (2)C16—C11—P1120.7 (5)
P1—Ir1—Br189.56 (4)C13—C12—C11119.9 (7)
C1—Ir1—Br297.47 (18)C13—C12—H12120.1
C3—Ir1—Br2155.72 (17)C11—C12—H12120.1
C2—Ir1—Br2133.26 (18)C14—C13—C12120.6 (7)
C4—Ir1—Br2119.53 (18)C14—C13—H13119.7
C5—Ir1—Br291.69 (18)C12—C13—H13119.7
P1—Ir1—Br287.13 (4)C15—C14—C13119.9 (7)
Br1—Ir1—Br291.05 (3)C15—C14—H14120.0
C17—P1—C2891.6 (3)C13—C14—H14120.0
C17—P1—C11103.6 (3)C14—C15—C16121.0 (8)
C28—P1—C11104.2 (3)C14—C15—H15119.5
C17—P1—Ir1117.0 (2)C16—C15—H15119.5
C28—P1—Ir1116.6 (2)C15—C16—C11119.2 (7)
C11—P1—Ir1119.48 (19)C15—C16—H16120.4
C2—C1—C5108.2 (6)C11—C16—H16120.4
C2—C1—C6127.2 (7)C18—C17—C22121.1 (6)
C5—C1—C6124.2 (7)C18—C17—P1128.6 (5)
C2—C1—Ir171.2 (3)C22—C17—P1110.3 (5)
C5—C1—Ir173.7 (4)C17—C18—C19118.5 (7)
C6—C1—Ir1126.9 (5)C17—C18—H18120.7
C1—C2—C3108.0 (6)C19—C18—H18120.7
C1—C2—C7126.7 (6)C20—C19—C18120.4 (8)
C3—C2—C7125.1 (6)C20—C19—H19119.8
C1—C2—Ir170.1 (4)C18—C19—H19119.8
C3—C2—Ir170.2 (3)C21—C20—C19120.9 (7)
C7—C2—Ir1129.4 (4)C21—C20—H20119.5
C2—C3—C4107.0 (6)C19—C20—H20119.5
C2—C3—C8127.3 (6)C22—C21—C20120.0 (7)
C4—C3—C8125.1 (6)C22—C21—H21120.0
C2—C3—Ir170.9 (4)C20—C21—H21120.0
C4—C3—Ir173.4 (4)C21—C22—C17119.1 (7)
C8—C3—Ir1127.6 (5)C21—C22—C23127.5 (7)
C5—C4—C3108.9 (6)C17—C22—C23113.3 (6)
C5—C4—C9125.8 (7)C24—C23—C28119.4 (7)
C3—C4—C9125.3 (7)C24—C23—C22127.3 (7)
C5—C4—Ir171.6 (4)C28—C23—C22113.3 (6)
C3—C4—Ir168.1 (3)C25—C24—C23119.1 (7)
C9—C4—Ir1126.5 (5)C25—C24—H24120.4
C4—C5—C1107.6 (6)C23—C24—H24120.4
C4—C5—C10127.7 (8)C24—C25—C26122.8 (7)
C1—C5—C10124.7 (7)C24—C25—H25118.6
C4—C5—Ir171.4 (4)C26—C25—H25118.6
C1—C5—Ir167.8 (3)C25—C26—C27119.4 (8)
C10—C5—Ir1126.5 (5)C25—C26—H26120.3
C1—C6—H6A109.5C27—C26—H26120.3
C1—C6—H6B109.5C26—C27—C28118.5 (7)
H6A—C6—H6B109.5C26—C27—H27120.8
C1—C6—H6C109.5C28—C27—H27120.8
H6A—C6—H6C109.5C23—C28—C27120.9 (6)
H6B—C6—H6C109.5C23—C28—P1111.4 (5)
C2—C7—H7A109.5C27—C28—P1127.7 (5)
C2—C7—H7B109.5Cl2—C29—Cl1111.7 (6)
H7A—C7—H7B109.5Cl2—C29—H29A109.3
C2—C7—H7C109.5Cl1—C29—H29A109.3
H7A—C7—H7C109.5Cl2—C29—H29B109.3
H7B—C7—H7C109.5Cl1—C29—H29B109.3
C3—C8—H8A109.5H29A—C29—H29B107.9
C1—Ir1—P1—C1785.8 (3)C2—Ir1—C4—C580.8 (4)
C3—Ir1—P1—C1713.1 (3)P1—Ir1—C4—C5129.3 (4)
C2—Ir1—P1—C1749.4 (3)Br1—Ir1—C4—C5−138.1 (4)
C4—Ir1—P1—C176.8 (5)Br2—Ir1—C4—C5−45.9 (4)
C5—Ir1—P1—C1794.5 (5)C1—Ir1—C4—C3−82.6 (4)
Br1—Ir1—P1—C17−86.2 (2)C2—Ir1—C4—C3−39.3 (4)
Br2—Ir1—P1—C17−177.3 (2)C5—Ir1—C4—C3−120.1 (6)
C1—Ir1—P1—C28−21.1 (3)P1—Ir1—C4—C39.2 (6)
C3—Ir1—P1—C28−93.8 (3)Br1—Ir1—C4—C3101.7 (4)
C2—Ir1—P1—C28−57.5 (3)Br2—Ir1—C4—C3−166.0 (3)
C4—Ir1—P1—C28−100.1 (5)C1—Ir1—C4—C9158.8 (8)
C5—Ir1—P1—C28−12.4 (5)C3—Ir1—C4—C9−118.5 (8)
Br1—Ir1—P1—C28166.9 (2)C2—Ir1—C4—C9−157.8 (8)
Br2—Ir1—P1—C2875.8 (2)C5—Ir1—C4—C9121.4 (9)
C1—Ir1—P1—C11−147.9 (3)P1—Ir1—C4—C9−109.3 (7)
C3—Ir1—P1—C11139.4 (3)Br1—Ir1—C4—C9−16.8 (7)
C2—Ir1—P1—C11175.7 (3)Br2—Ir1—C4—C975.4 (7)
C4—Ir1—P1—C11133.1 (5)C3—C4—C5—C1−0.4 (7)
C5—Ir1—P1—C11−139.2 (5)C9—C4—C5—C1179.4 (6)
Br1—Ir1—P1—C1140.0 (2)Ir1—C4—C5—C1−58.4 (4)
Br2—Ir1—P1—C11−51.0 (2)C3—C4—C5—C10−179.8 (7)
C3—Ir1—C1—C237.3 (4)C9—C4—C5—C100.0 (11)
C4—Ir1—C1—C280.2 (4)Ir1—C4—C5—C10122.2 (7)
C5—Ir1—C1—C2116.3 (6)C3—C4—C5—Ir158.0 (4)
P1—Ir1—C1—C2−70.2 (4)C9—C4—C5—Ir1−122.2 (7)
Br1—Ir1—C1—C290.6 (6)C2—C1—C5—C4−2.6 (7)
Br2—Ir1—C1—C2−160.4 (4)C6—C1—C5—C4−175.5 (6)
C3—Ir1—C1—C5−79.0 (4)Ir1—C1—C5—C460.6 (5)
C2—Ir1—C1—C5−116.3 (6)C2—C1—C5—C10176.8 (6)
C4—Ir1—C1—C5−36.1 (4)C6—C1—C5—C104.0 (11)
P1—Ir1—C1—C5173.5 (3)Ir1—C1—C5—C10−119.9 (7)
Br1—Ir1—C1—C5−25.7 (7)C2—C1—C5—Ir1−63.3 (4)
Br2—Ir1—C1—C583.3 (4)C6—C1—C5—Ir1123.9 (7)
C3—Ir1—C1—C6160.2 (8)C1—Ir1—C5—C4−118.8 (6)
C2—Ir1—C1—C6122.9 (9)C3—Ir1—C5—C4−36.8 (4)
C4—Ir1—C1—C6−156.9 (8)C2—Ir1—C5—C4−80.2 (4)
C5—Ir1—C1—C6−120.8 (9)P1—Ir1—C5—C4−131.7 (4)
P1—Ir1—C1—C652.6 (7)Br1—Ir1—C5—C449.2 (4)
Br1—Ir1—C1—C6−146.5 (6)Br2—Ir1—C5—C4141.3 (4)
Br2—Ir1—C1—C6−37.6 (7)C3—Ir1—C5—C182.0 (4)
C5—C1—C2—C34.7 (7)C2—Ir1—C5—C138.6 (4)
C6—C1—C2—C3177.2 (7)C4—Ir1—C5—C1118.8 (6)
Ir1—C1—C2—C3−60.3 (4)P1—Ir1—C5—C1−12.9 (7)
C5—C1—C2—C7−170.2 (6)Br1—Ir1—C5—C1168.0 (3)
C6—C1—C2—C72.3 (11)Br2—Ir1—C5—C1−99.9 (4)
Ir1—C1—C2—C7124.9 (6)C1—Ir1—C5—C10117.6 (9)
C5—C1—C2—Ir164.9 (4)C3—Ir1—C5—C10−160.4 (8)
C6—C1—C2—Ir1−122.5 (7)C2—Ir1—C5—C10156.2 (8)
C3—Ir1—C2—C1−118.7 (5)C4—Ir1—C5—C10−123.6 (9)
C4—Ir1—C2—C1−79.8 (4)P1—Ir1—C5—C10104.7 (8)
C5—Ir1—C2—C1−38.4 (4)Br1—Ir1—C5—C10−74.4 (8)
P1—Ir1—C2—C1120.1 (4)Br2—Ir1—C5—C1017.7 (8)
Br1—Ir1—C2—C1−143.1 (3)C17—P1—C11—C1243.0 (6)
Br2—Ir1—C2—C127.1 (5)C28—P1—C11—C12138.2 (5)
C1—Ir1—C2—C3118.7 (5)Ir1—P1—C11—C12−89.4 (5)
C4—Ir1—C2—C338.9 (4)C17—P1—C11—C16−135.5 (5)
C5—Ir1—C2—C380.3 (4)C28—P1—C11—C16−40.3 (6)
P1—Ir1—C2—C3−121.2 (3)Ir1—P1—C11—C1692.1 (5)
Br1—Ir1—C2—C3−24.4 (5)C16—C11—C12—C13−0.3 (9)
Br2—Ir1—C2—C3145.8 (3)P1—C11—C12—C13−178.8 (5)
C1—Ir1—C2—C7−121.6 (8)C11—C12—C13—C140.2 (10)
C3—Ir1—C2—C7119.7 (8)C12—C13—C14—C150.0 (11)
C4—Ir1—C2—C7158.6 (7)C13—C14—C15—C16−0.1 (11)
C5—Ir1—C2—C7−160.0 (7)C14—C15—C16—C110.0 (10)
P1—Ir1—C2—C7−1.5 (7)C12—C11—C16—C150.2 (9)
Br1—Ir1—C2—C795.3 (6)P1—C11—C16—C15178.7 (5)
Br2—Ir1—C2—C7−94.5 (6)C28—P1—C17—C18175.0 (7)
C1—C2—C3—C4−4.8 (7)C11—P1—C17—C18−79.9 (7)
C7—C2—C3—C4170.1 (6)Ir1—P1—C17—C1853.9 (7)
Ir1—C2—C3—C4−65.0 (4)C28—P1—C17—C22−2.6 (5)
C1—C2—C3—C8−176.6 (6)C11—P1—C17—C22102.4 (5)
C7—C2—C3—C8−1.6 (10)Ir1—P1—C17—C22−123.8 (4)
Ir1—C2—C3—C8123.2 (7)C22—C17—C18—C19−1.5 (11)
C1—C2—C3—Ir160.2 (4)P1—C17—C18—C19−178.9 (6)
C7—C2—C3—Ir1−124.8 (6)C17—C18—C19—C200.8 (13)
C1—Ir1—C3—C2−37.2 (4)C18—C19—C20—C210.5 (14)
C4—Ir1—C3—C2−115.2 (5)C19—C20—C21—C22−1.0 (14)
C5—Ir1—C3—C2−79.9 (4)C20—C21—C22—C170.3 (11)
P1—Ir1—C3—C269.3 (4)C20—C21—C22—C23176.6 (8)
Br1—Ir1—C3—C2162.9 (3)C18—C17—C22—C211.0 (10)
Br2—Ir1—C3—C2−84.6 (5)P1—C17—C22—C21178.8 (6)
C1—Ir1—C3—C478.1 (4)C18—C17—C22—C23−175.8 (6)
C2—Ir1—C3—C4115.2 (5)P1—C17—C22—C232.0 (7)
C5—Ir1—C3—C435.4 (4)C21—C22—C23—C241.8 (12)
P1—Ir1—C3—C4−175.5 (3)C17—C22—C23—C24178.3 (7)
Br1—Ir1—C3—C4−81.9 (4)C21—C22—C23—C28−176.5 (7)
Br2—Ir1—C3—C430.7 (6)C17—C22—C23—C280.0 (8)
C1—Ir1—C3—C8−160.1 (7)C28—C23—C24—C250.6 (12)
C2—Ir1—C3—C8−122.9 (8)C22—C23—C24—C25−177.6 (8)
C4—Ir1—C3—C8121.8 (8)C23—C24—C25—C260.6 (15)
C5—Ir1—C3—C8157.2 (7)C24—C25—C26—C27−0.8 (15)
P1—Ir1—C3—C8−53.6 (7)C25—C26—C27—C28−0.4 (13)
Br1—Ir1—C3—C840.0 (6)C24—C23—C28—C27−1.8 (10)
Br2—Ir1—C3—C8152.5 (5)C22—C23—C28—C27176.7 (6)
C2—C3—C4—C53.2 (7)C24—C23—C28—P1179.6 (6)
C8—C3—C4—C5175.2 (6)C22—C23—C28—P1−2.0 (7)
Ir1—C3—C4—C5−60.1 (5)C26—C27—C28—C231.7 (11)
C2—C3—C4—C9−176.6 (6)C26—C27—C28—P1−179.9 (6)
C8—C3—C4—C9−4.6 (10)C17—P1—C28—C232.6 (5)
Ir1—C3—C4—C9120.1 (7)C11—P1—C28—C23−101.9 (5)
C2—C3—C4—Ir163.4 (4)Ir1—P1—C28—C23124.1 (4)
C8—C3—C4—Ir1−124.7 (6)C17—P1—C28—C27−175.9 (7)
C1—Ir1—C4—C537.5 (4)C11—P1—C28—C2779.6 (7)
C3—Ir1—C4—C5120.1 (6)Ir1—P1—C28—C27−54.4 (7)
Table 1
Selected geometric parameters (Å, °) top
Ir1—C12.155 (6)Ir1—Br12.5022 (8)
Ir1—C32.160 (6)Ir1—Br22.5118 (8)
Ir1—C22.169 (6)P1—C171.807 (6)
Ir1—C42.231 (6)P1—C281.809 (6)
Ir1—C52.233 (6)P1—C111.823 (6)
Ir1—P12.2829 (15)
P1—Ir1—Br189.56 (4)C28—P1—C11104.2 (3)
P1—Ir1—Br287.13 (4)C17—P1—Ir1117.0 (2)
Br1—Ir1—Br291.05 (3)C28—P1—Ir1116.6 (2)
C17—P1—C2891.6 (3)C11—P1—Ir1119.48 (19)
C17—P1—C11103.6 (3)
Acknowledgements top

This work was supported by a Grant-in-Aid for Scientific Research (No. 16550055) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

references
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