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The title compound, [IrBr25-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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026621/is2170sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026621/is2170Isup2.hkl
Contains datablock I

CCDC reference: 654710

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.012 Å
  • R factor = 0.040
  • wR factor = 0.126
  • Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ir1 - Br1 .. 28.14 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ir1 - Br2 .. 30.00 su
Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 11
Alert level G ABSTM02_ALERT_3_G The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.294 0.406 Tmin and Tmax expected: 0.249 0.406 RR = 1.180 Please check that your absorption correction is appropriate.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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.

Structure description 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.

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).

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-πhenyldibenzophosphole-κP)iridium(III) dichloromethane solvate top
Crystal data top
[IrBr2(C10H15)(C18H13P)]·CH2Cl2F(000) = 1600
Mr = 832.42Dx = 1.882 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yabCell parameters from 17738 reflections
a = 11.0793 (5) Åθ = 3.2–27.4°
b = 23.3836 (10) ŵ = 7.52 mm1
c = 12.8133 (5) ÅT = 200 K
β = 117.746 (1)°Block, 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)
Graphite monochromatorRint = 0.045
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 3.2°
ω scansh = 1414
Absorption correction: numerical
(ABSCOR; Higashi, 1999)
k = 3030
Tmin = 0.294, Tmax = 0.406l = 1616
28567 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
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 = 1.08(Δ/σ)max = 0.001
6708 reflectionsΔρmax = 1.76 e Å3
317 parametersΔρmin = 2.74 e Å3
0 restraintsExtinction 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)
Crystal data top
[IrBr2(C10H15)(C18H13P)]·CH2Cl2V = 2937.9 (2) Å3
Mr = 832.42Z = 4
Monoclinic, P21/aMo Kα radiation
a = 11.0793 (5) ŵ = 7.52 mm1
b = 23.3836 (10) ÅT = 200 K
c = 12.8133 (5) Å0.22 × 0.16 × 0.12 mm
β = 117.746 (1)°
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)] = 0.0400 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0587P)2 + 23.6384P]
where P = (Fo2 + 2Fc2)/3
6708 reflectionsΔρmax = 1.76 e Å3
317 parametersΔρmin = 2.74 e Å3
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)
Cl10.1229 (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, º) 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—C5138.1 (4)
C4—Ir1—P1—C176.8 (5)Br2—Ir1—C4—C545.9 (4)
C5—Ir1—P1—C1794.5 (5)C1—Ir1—C4—C382.6 (4)
Br1—Ir1—P1—C1786.2 (2)C2—Ir1—C4—C339.3 (4)
Br2—Ir1—P1—C17177.3 (2)C5—Ir1—C4—C3120.1 (6)
C1—Ir1—P1—C2821.1 (3)P1—Ir1—C4—C39.2 (6)
C3—Ir1—P1—C2893.8 (3)Br1—Ir1—C4—C3101.7 (4)
C2—Ir1—P1—C2857.5 (3)Br2—Ir1—C4—C3166.0 (3)
C4—Ir1—P1—C28100.1 (5)C1—Ir1—C4—C9158.8 (8)
C5—Ir1—P1—C2812.4 (5)C3—Ir1—C4—C9118.5 (8)
Br1—Ir1—P1—C28166.9 (2)C2—Ir1—C4—C9157.8 (8)
Br2—Ir1—P1—C2875.8 (2)C5—Ir1—C4—C9121.4 (9)
C1—Ir1—P1—C11147.9 (3)P1—Ir1—C4—C9109.3 (7)
C3—Ir1—P1—C11139.4 (3)Br1—Ir1—C4—C916.8 (7)
C2—Ir1—P1—C11175.7 (3)Br2—Ir1—C4—C975.4 (7)
C4—Ir1—P1—C11133.1 (5)C3—C4—C5—C10.4 (7)
C5—Ir1—P1—C11139.2 (5)C9—C4—C5—C1179.4 (6)
Br1—Ir1—P1—C1140.0 (2)Ir1—C4—C5—C158.4 (4)
Br2—Ir1—P1—C1151.0 (2)C3—C4—C5—C10179.8 (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—C270.2 (4)C9—C4—C5—Ir1122.2 (7)
Br1—Ir1—C1—C290.6 (6)C2—C1—C5—C42.6 (7)
Br2—Ir1—C1—C2160.4 (4)C6—C1—C5—C4175.5 (6)
C3—Ir1—C1—C579.0 (4)Ir1—C1—C5—C460.6 (5)
C2—Ir1—C1—C5116.3 (6)C2—C1—C5—C10176.8 (6)
C4—Ir1—C1—C536.1 (4)C6—C1—C5—C104.0 (11)
P1—Ir1—C1—C5173.5 (3)Ir1—C1—C5—C10119.9 (7)
Br1—Ir1—C1—C525.7 (7)C2—C1—C5—Ir163.3 (4)
Br2—Ir1—C1—C583.3 (4)C6—C1—C5—Ir1123.9 (7)
C3—Ir1—C1—C6160.2 (8)C1—Ir1—C5—C4118.8 (6)
C2—Ir1—C1—C6122.9 (9)C3—Ir1—C5—C436.8 (4)
C4—Ir1—C1—C6156.9 (8)C2—Ir1—C5—C480.2 (4)
C5—Ir1—C1—C6120.8 (9)P1—Ir1—C5—C4131.7 (4)
P1—Ir1—C1—C652.6 (7)Br1—Ir1—C5—C449.2 (4)
Br1—Ir1—C1—C6146.5 (6)Br2—Ir1—C5—C4141.3 (4)
Br2—Ir1—C1—C637.6 (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—C360.3 (4)P1—Ir1—C5—C112.9 (7)
C5—C1—C2—C7170.2 (6)Br1—Ir1—C5—C1168.0 (3)
C6—C1—C2—C72.3 (11)Br2—Ir1—C5—C199.9 (4)
Ir1—C1—C2—C7124.9 (6)C1—Ir1—C5—C10117.6 (9)
C5—C1—C2—Ir164.9 (4)C3—Ir1—C5—C10160.4 (8)
C6—C1—C2—Ir1122.5 (7)C2—Ir1—C5—C10156.2 (8)
C3—Ir1—C2—C1118.7 (5)C4—Ir1—C5—C10123.6 (9)
C4—Ir1—C2—C179.8 (4)P1—Ir1—C5—C10104.7 (8)
C5—Ir1—C2—C138.4 (4)Br1—Ir1—C5—C1074.4 (8)
P1—Ir1—C2—C1120.1 (4)Br2—Ir1—C5—C1017.7 (8)
Br1—Ir1—C2—C1143.1 (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—C1289.4 (5)
C4—Ir1—C2—C338.9 (4)C17—P1—C11—C16135.5 (5)
C5—Ir1—C2—C380.3 (4)C28—P1—C11—C1640.3 (6)
P1—Ir1—C2—C3121.2 (3)Ir1—P1—C11—C1692.1 (5)
Br1—Ir1—C2—C324.4 (5)C16—C11—C12—C130.3 (9)
Br2—Ir1—C2—C3145.8 (3)P1—C11—C12—C13178.8 (5)
C1—Ir1—C2—C7121.6 (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—C160.1 (11)
C5—Ir1—C2—C7160.0 (7)C14—C15—C16—C110.0 (10)
P1—Ir1—C2—C71.5 (7)C12—C11—C16—C150.2 (9)
Br1—Ir1—C2—C795.3 (6)P1—C11—C16—C15178.7 (5)
Br2—Ir1—C2—C794.5 (6)C28—P1—C17—C18175.0 (7)
C1—C2—C3—C44.8 (7)C11—P1—C17—C1879.9 (7)
C7—C2—C3—C4170.1 (6)Ir1—P1—C17—C1853.9 (7)
Ir1—C2—C3—C465.0 (4)C28—P1—C17—C222.6 (5)
C1—C2—C3—C8176.6 (6)C11—P1—C17—C22102.4 (5)
C7—C2—C3—C81.6 (10)Ir1—P1—C17—C22123.8 (4)
Ir1—C2—C3—C8123.2 (7)C22—C17—C18—C191.5 (11)
C1—C2—C3—Ir160.2 (4)P1—C17—C18—C19178.9 (6)
C7—C2—C3—Ir1124.8 (6)C17—C18—C19—C200.8 (13)
C1—Ir1—C3—C237.2 (4)C18—C19—C20—C210.5 (14)
C4—Ir1—C3—C2115.2 (5)C19—C20—C21—C221.0 (14)
C5—Ir1—C3—C279.9 (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—C284.6 (5)P1—C17—C22—C21178.8 (6)
C1—Ir1—C3—C478.1 (4)C18—C17—C22—C23175.8 (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—C4175.5 (3)C17—C22—C23—C24178.3 (7)
Br1—Ir1—C3—C481.9 (4)C21—C22—C23—C28176.5 (7)
Br2—Ir1—C3—C430.7 (6)C17—C22—C23—C280.0 (8)
C1—Ir1—C3—C8160.1 (7)C28—C23—C24—C250.6 (12)
C2—Ir1—C3—C8122.9 (8)C22—C23—C24—C25177.6 (8)
C4—Ir1—C3—C8121.8 (8)C23—C24—C25—C260.6 (15)
C5—Ir1—C3—C8157.2 (7)C24—C25—C26—C270.8 (15)
P1—Ir1—C3—C853.6 (7)C25—C26—C27—C280.4 (13)
Br1—Ir1—C3—C840.0 (6)C24—C23—C28—C271.8 (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—P12.0 (7)
Ir1—C3—C4—C560.1 (5)C26—C27—C28—C231.7 (11)
C2—C3—C4—C9176.6 (6)C26—C27—C28—P1179.9 (6)
C8—C3—C4—C94.6 (10)C17—P1—C28—C232.6 (5)
Ir1—C3—C4—C9120.1 (7)C11—P1—C28—C23101.9 (5)
C2—C3—C4—Ir163.4 (4)Ir1—P1—C28—C23124.1 (4)
C8—C3—C4—Ir1124.7 (6)C17—P1—C28—C27175.9 (7)
C1—Ir1—C4—C537.5 (4)C11—P1—C28—C2779.6 (7)
C3—Ir1—C4—C5120.1 (6)Ir1—P1—C28—C2754.4 (7)

Experimental details

Crystal data
Chemical formula[IrBr2(C10H15)(C18H13P)]·CH2Cl2
Mr832.42
Crystal system, space groupMonoclinic, P21/a
Temperature (K)200
a, b, c (Å)11.0793 (5), 23.3836 (10), 12.8133 (5)
β (°) 117.746 (1)
V3)2937.9 (2)
Z4
Radiation typeMo Kα
µ (mm1)7.52
Crystal size (mm)0.22 × 0.16 × 0.12
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionNumerical
(ABSCOR; Higashi, 1999)
Tmin, Tmax0.294, 0.406
No. of measured, independent and
observed [I > 2σ(I)] reflections
28567, 6708, 6185
Rint0.045
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.126, 1.08
No. of reflections6708
No. of parameters317
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0587P)2 + 23.6384P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.76, 2.74

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) 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)
 

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