Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Di-l-benzenethiolato-l-chlorido-bis{hydrido-[(
S
)-(
)-2,2
000-bis(di-
p
-tolylphosphanyl)-1,1
000-binaphthyl]iridium(III)} chloride 1,2-dichloroethane
disolvate
Tsuneaki Yamagata,a* Kazunori Hoshida,aAika Isekiaand Kazuhide Tanib
aDepartment of Chemistry, Graduate School of
Engineering Science, Osaka University, Machikaneyama 1-3, Toyonaka, Osaka 560-8531, Japan, andbHigashiosaka College,
Nishitutumi Gakuen-chou 3-1-1, Higashiosaka, Osaka 577-8567, Japan
Correspondence e-mail: tyama@chem.es.osaka-u.ac.jp
Key indicators
Single-crystal X-ray study
T= 100 K
Mean(C–C) = 0.010 A˚
Rfactor = 0.040
wRfactor = 0.098
Data-to-parameter ratio = 20.1
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 16 January 2007 Accepted 21 February 2007
The cation of the title compound, [Ir2ClH2(C6H5S)2
-(C48H40P2)2]Cl2C2H4Cl2, exists as a bridged bifacial
octa-hedral dinuclear iridium structure withC2symmetry (Cl lies
on the rotation axis). The coordination environment of the Ir atom can be described as highly distorted octahedral with two P atoms, two bridging phenyl thiolato S atoms, a bridging chloride ligand, and a terminal hydride ligand.
Comment
Recently, we have found highly diastereoselective oxidative
addition of carboxylic acids to an IrI chiral diphosphane
complex, [IrCl(diphosphane)]2 (diphosphane: BINAP [2,20
-bis(diphenylphosphanyl)-1,10-binaphthyl], tolBINAP {2,20
-bis-[di(p-tolyl)phosphanyl]-1,10-binaphthyl}) to give mononuclear
hydrido(2-carboxylato)complexes (Yamagata et al., 2006).
[IrCl(binap)]2reacted with excess amounts of MeOH at room
temperature gives a hydrido(methoxo)iridium complex,
[{IrH(binap)}2(-Cl)(-OMe)2]Cl, (II) (Tani et al., 1998),
which is an efficient catalyst precursor for transfer hydro-genation of alkynes using methanol as a hydrogen source
(Tani et al., 1999). During our studies on the reactivity of
[IrCl(diphosphane)]2, we have found that a series of thiolato
complexes, [{IrH(diphosphane)]2(-Cl)(-SAr)2]Cl, could be
prepared quantitatively, by reaction of [IrCl(diphosphane)]2
with excess amounts of ArSH (Ar: C6H5, C6H4CH3-p).
The title compound, [{IrH{(S)-tolBINAP}]2(-Cl)(
-S-C6H5)2]Cl2C2H4Cl2, (I), crystallizing as a 1,2-dichloroethane disolvate, has a dinuclear structure (Fig. 1) and the coordin-ation geometry of each Ir atom can be described as highly distorted octahedral with two P atoms, two bridging phenyl thiolate S atoms, one bridging chloride, and a terminal hydride ligand (Table 1). The complete cation is generated by twofold symmetry, with the Cl atom lying on the crystallographic rotation axis.
SPh)2]ClO4, (III) (Roberts & Ferguson, 1976). A terminal hydride ligand is present at the positiontransto the-chlorido
ligand andcisto the two phenyl thiolate ligands. The phenyl
groups of the thiolate and the p-tolyl rings of
di(p-tol-yl)phosphanyl units of the tolBINAP ligands are arranged in a stack [dihedral angle 28.5 (2)]. The Ir Iri
[symmetry code: (i) x, 1 y, 1 z] distance [3.3558 (4) A˚ ] in (I) is slightly
shorter than that in (III) (3.377 A˚ ) and longer than that
observed in (II) [3.1461 (7) A˚ ].
The Ir—S distances in (I) are comparable to the equivalent ones in (III) [2.399 (5)–2.416 (5) A˚ ] and longer than the Ir—O
distances in (III) [2.106 (4) and 2.138 (4) A˚ ]. The Ir—Cl
distance in (I) is similar to those in (III) [2.556 (4) and 2.559 (5) A˚ ], but longer than that in (II) [2.534 (2) A˚]. The bridging Ir—Cl—Ir angle in (I) [82.16 (5)] is similar to that in
(III) (82.6) but larger than that in (II) [76.75 (5)]. The
dihedral angle [74.9 (1)] between the pair of naphthyl ring
systems in (I) is smaller than that in (II) [81.4 (1)]. These
structural differences between the
hydrido(phenylthiol-ato)iridium cations in (I) and (III) and the hydrido(methox-o)iridium cation in (II) reflect the different coordination radii for O (0.730 A˚ ) and S (1.020 A˚) atoms.
Experimental
All manipulations of air-sensitive materials were performed under an argon atmosphere using standard Schlenk and vacuum techniques (8
10 2 Torr). For the preparation of [{IrH{(S)-tolBINAP}}2(
-Cl)(-SC6H5)2]Cl: a mixture of [IrCl(coe)2]2 (coe = cycloethene)
(115 mg, 1.33104mol) and (S)-tolBINAP (177 mg, 2.61104 mol) in toluene (10 ml) was stirred under argon for 6 h at ambient temperature. The colour of the reaction mixture changed from yellow to deep red. Benzenethiol (100ml, 9.74104mol) was added to the toluene solution. The colour of the solution immediately changed
from deep-red to dark-yellow. After a few hours, the solution became a suspension. The suspension was stirred for 15 h. Removal of the volatile materials in vacuo and washing with hexanes (5 ml 6) afforded a pale-yellow powder (308 mg, quantitative yield). Recrys-tallization from chloroform–hexanes (1:10v/v) afforded an analyti-cally pure product [m.p. > 459 K (decomposition in a capillary under argon)]. Single crystals of (I) suitable for X-ray analysis were grown from a solution in a 1,2-dichloroethane–hexanes mixture (1:1v/v). Analysis calculated for C108H92Cl2Ir2P4S22C2H4Cl2: C 60.29, H
4.52%; found: C 60.00, H 4.47%.
[{IrH{(S)-BINAP}}2(-Cl)(-SPh)2]Cl [96% yield, m.p. > 397 K
(decomposition in a capillary under argon)].
[{IrH{(S)-BINAP}}2(-Cl)(-SC6H4CH3-p)2]Cl [quantitative
yield, m.p. > 404 K (decomposition in a capillary under argon). [{IrH{(S)-tolBINAP}}2(-Cl)(-SC6H4CH3-p)2]Cl [quantitative
yield, m.p. > 465 K (decomposition in a capillary under argon). Analysis calculated for C110H96Cl2Ir2P4S2C2H4Cl2: C 60.61, H 4.64%;
found: C 60.00, H 4.47%.
Crystal data
[Ir2ClH2(C6H5S)2(C48H40P2)2]Cl
-2C2H4Cl2
Mr= 2231.02
Orthorhombic,C2221
a= 16.8773 (3) A˚ b= 21.1322 (4) A˚ c= 27.4623 (4) A˚
V= 9794.5 (3) A˚3 Z= 4
MoKradiation
= 3.04 mm1
T= 100 (1) K 0.290.090.08 mm
Data collection
Rigaku RAXIS-RAPID Imaging Plate diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1998) Tmin= 0.839,Tmax= 0.957
103545 measured reflections 11258 independent reflections 10700 reflections withI> 2(I) Rint= 0.085
Refinement
R[F2> 2(F2)] = 0.040 wR(F2) = 0.098
S= 1.10 11258 reflections 559 parameters
H-atom parameters constrained
max= 1.62 e A˚
3 min=1.24 e A˚
3
Absolute structure: Flack (1983), 5178 Friedel pairs
Flack parameter: 0.007 (6)
Table 1
Selected geometric parameters (A˚ ,).
Ir—P1 2.2885 (15)
Ir—P2 2.2937 (14)
Ir—S 2.4094 (14)
Ir—Si
2.4190 (13)
Ir—Cl1 2.5534 (14)
Ir—Iri
3.3558 (4)
Ir—H0 1.603
P1—Ir—P2 93.78 (6)
P1—Ir—S 92.72 (5)
P2—Ir—S 172.91 (5)
P1—Ir—Si
173.00 (5)
P2—Ir—Si 91.58 (5)
S—Ir—Si
82.17 (5)
P1—Ir—Cl1 97.99 (4)
P2—Ir—Cl1 105.48 (4)
S—Ir—Cl1 76.38 (4)
Si
—Ir—Cl1 76.22 (4)
Ir—S—Iri 88.06 (4)
Ir—Cl1—Iri
82.16 (5)
Symmetry code: (i)x;yþ1;zþ1.
The hydrido (H0) ligand was found in a difference Fourier map and calculated at the minimum of the potential energy by the programHYDEX(Orpen, 1980) and was included as a riding atom (Ir—H = 1.603 A˚ ). Spectroscopic data show the presence of this terminal hydride ligand. All other H atoms were positioned geome-trically (C—H = 0.95–0.99 A˚ ) and refined as riding, withUiso(H) =
1.2Ueq(C) or 1.5Ueq(methyl C). The atoms of the dichloroethane solvent molecule showed very large displacement parameters and
Acta Cryst.(2007). E63, m918–m920 Yamagataet al. [Ir
[image:2.610.46.295.77.276.2]2ClH2(C6H5S)2(C48H40P2)2]Cl2C2H4Cl2
m919
Figure 1
distance restraints were used to stabilize the refinement: C—Cl, C— C, C Cl (non-bonding) and Cl Cl (non-bonding) distances were restrained to 1.78 (2), 1.52 (2), 2.71 (2) and 4.33 (2) A˚ , respectively. The two Cl atoms and the two C atoms of the solvent molecule were refined anisotropically and isotropically, respectively.
Data collection: RAPID-AUTO(Rigaku, 1998); cell refinement:
RAPID-AUTO; data reduction: PROCESS in TEXSAN (Rigaku/ MSC, 2004); program(s) used to solve structure:DIRDIF99 (Beurs-kens et al., 1999); program(s) used to refine structure:SHELXL97
(Sheldrick, 1997); molecular graphics: ORTEP-3(Farrugia, 1999); software used to prepare material for publication: modified
SHELXL97.
This research was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.
References
Beurskens, P. T., Beurskens, G., de Gelder, R., Garcı´a-Granda, S., Israel, R., Gould, R. O. & Smits, J. M. M. (1999).The DIRDIF99 Program System. Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands.
Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838. Flack, H. D. (1983).Acta Cryst.A39, 876–881.
Higashi, H. (1998).NUMABS. Rigaku Corporation, Tokyo, Japan. Orpen, A. G. (1980).J. Chem. Soc. Dalton Trans.pp. 2509–2516. Rigaku (1998).RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Rigaku/MSC (2004).TEXSAN. Version 2.0. Rigaku/MSC, The Woodlands,
Texas, USA.
Roberts, P. J. & Ferguson, G. (1976).Acta Cryst.B32, 1513–1517. Sheldrick, G. M. (1997).SHELXL97. University of Go¨ttingen, Germany. Tani, K., Iseki, A. & Yamagata, T. (1998).Angew. Chem. Int. Ed.37, 3381–
3383.
Tani, K., Iseki, A. & Yamagata, T. (1999).Chem. Commun.pp. 1821–1822. Yamagata, T., Tadaoka, H., Nagata, M., Hirao, T., Kataoka, Y.,
sup-1 Acta Cryst. (2007). E63, m918–m920
supporting information
Acta Cryst. (2007). E63, m918–m920 [https://doi.org/10.1107/S1600536807008665]
Di-
µ
-benzenethiolato-
µ
-chlorido-bis{hydrido[(
S
)-(
−
)-2,2
′
-bis(di-
p
-tolyl-phosphanyl)-1,1
′
-binaphthyl]iridium(III)} chloride 1,2-dichloroethane disolvate
Tsuneaki Yamagata, Kazunori Hoshida, Aika Iseki and Kazuhide Tani
Di-µ-benzenethiolato-µ-chlorido-bis{hydrido[(S)-(-)-2,2′-bis(di-p- tolylphosphanyl)-1,1′-binaphthyl]iridium(III)} chloride 1,2-dichloroethane disolvate
Crystal data
[Ir2ClH2(C6H5S)2(C48H40P2)2]Cl·2C2H4Cl2
Mr = 2231.02
Orthorhombic, C2221 Hall symbol: C 2c 2
a = 16.8773 (3) Å
b = 21.1322 (4) Å
c = 27.4623 (4) Å
V = 9794.5 (3) Å3
Z = 4
F(000) = 4480
Dx = 1.513 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 253402 reflections
θ = 1.5–32.6°
µ = 3.04 mm−1
T = 100 K
Prism, pale yellow 0.29 × 0.09 × 0.08 mm
Data collection
Rigaku RAXIS-RAPID Imaging Plate diffractometer
Radiation source: normal-focus sealed tube Graphite monochromator
Detector resolution: 10.00 pixels mm-1
ω scans
Absorption correction: numerical (NUMABS; Higashi, 1998)
Tmin = 0.839, Tmax = 0.957
103545 measured reflections 11258 independent reflections 10700 reflections with I > 2σ(I)
Rint = 0.085
θmax = 27.5°, θmin = 2.5°
h = −21→21
k = −27→27
l = −34→35
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.040
wR(F2) = 0.098
S = 1.10
11258 reflections 559 parameters 6 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0487P)2 + 60.5557P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.002 Δρmax = 1.62 e Å−3 Δρmin = −1.24 e Å−3
Absolute structure: Flack (1983), 5178 Friedel pairs
Special details
Experimental. Indexing was performed from 2 oscillations which were exposed for 6.8 minunites. The camera radiuswas
127.40 mm. Readout performed in the 0.100 mm pixel mode. #1 Phi=0.0, chi=55.0, omega=60.0 to 240.0 with 2.0deg step #2 Phi=180.0, chi=45.0, omega=0.0 to 180.0 with 2.0deg step #4 Phi=180.0, chi=410.0, omega=0.0 to 180.0 with 2.0deg step A total of 270 images, corresponding to 540.0 °. osillation angles, were collected with 3 different goniometer setting. Exposure time was 130 s per degree. The camera radiuswas 127.40 mm. Readout performed in the 0.100 mm pixel mode.
1H NMR (CD2Cl2, 300 MHz, 303 K): δ 5.97–8.20 (m, 66H, Ph + naphthyl + SPh), 2.12 (s, 6H, CH3), 2.10 (s, 6H, CH3), 1.95 (s, 6H, CH3), 1.78 (s, 6H, CH3), -23.00 (dd, 2JH–P = 13.5, 19.2 Hz, 2H, Ir—H), 31P{1H} NMR (CD2Cl2, 121.49 MHz, 303 K): δ 5.7 (m), -8.8 (m). The simulated 31P{1H} NMR spectrum showed a four spin system of AA′BB′ pattern. The simulated chemical shifts and the coupling constants were as follows: δ P1: -8.771, P2: -8.763, P3: 5.698, P4: 5.696; 3J12 = 20.78, 2J13 = 9.74, 3J14 = 16.22, 3J23 = 16.08, 2J24 = -0.49, 3J34 = 20.38 Hz. IR (KBr tablet, cm-1): 2265 (br, m, νIr—H). Λ0 = 102.7 S cm2 mol-1 (CH2Cl2, 298 K). Single crystals of (I) suitable for X-ray analysis were grown from a solution in a 1,2-dichloroethane–hexanes mixture (1:1 v/v). Analysis calculated for C108H92Cl2Ir2P4S2·2C2H4Cl2: C 60.29, H 4.52%; found: C 60.00, H 4.47%.
[{IrH{(S)-binap}}2(µ-Cl)(µ-SPh)2]Cl [96% yield, m.p. > 397 K (decomposition in a capillary under argon)]. 1H NMR (CD2Cl2, 300 MHz, 303 K): δ 6.05–8.25 (m, 74H, Ph + naphthyl + SPh), -22.75 (dd, 2JH–P = 12.9, 18.7 Hz, 2H, Ir—H), 31P{1H} NMR (CD2Cl2, 121 MHz, 303 K): δ 6.8 (m), -6.5 (m). IR (KBr tablet, cm-1): 2261 (br, m, νIr—H). Λ0 = 62.9 S cm2 mol-1 (CH2Cl2, 298 K).
[{IrH{(S)-binap}}2(µ-Cl)(µ-SC6H4CH3-p)2]Cl [quantitative yield, m.p. > 404 K (decomposition in a capillary under argon). 1H NMR (CD2Cl2, 300 MHz, 303 K): δ 6.08–8.24 (m, 72H, Ph + naphthyl + SC6H4CH3-p), 2.24 (s, 6H, CH3), -22.75 (dd, 2JH–P = 13.2, 19.2 Hz, 2H, Ir—H), 31P {1H} NMR (CD2Cl2, 121 MHz, 303 K): δ 6.9 (m), -6.7 (m). IR (KBr tablet, cm-1): 2265 (br, m, νIr—H). Λ0 = S cm2 mol-1 (CH2Cl2, 298 K).
[{IrH{(S)-tolbinap}}2(µ-Cl)(µ-SC6H4CH3-p)2]Cl [quantitative yield, m.p. > 465 K (decompition in a capillary under argon). 1H NMR (CD2Cl2, 300 MHz, 308 K: δ 5.96–8.20 (m, 64H, Ph + naphthyl + SC6H4CH3-p), 2.23 (s, 6H,
sup-3 Acta Cryst. (2007). E63, m918–m920
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)
15.5622 (0.0046) x + 6.3759 (0.0115) y - 6.6556 (0.0129) z = 8.8090 (0.0059) * 0.0000 (0.0000) Ir * 0.0000 (0.0000) S * 0.0000 (0.0000) S_$1
Rms deviation of fitted atoms = 0.0000
15.5622 (0.0045) x - 6.3760 (0.0114) y + 6.6556 (0.0130) z = 9.0886 (0.0058) Angle to previous plane (with approximate e.s.d.) = 45.54 (0.03)
* 0.0000 (0.0000) Ir_$1 * 0.0000 (0.0000) S * 0.0000 (0.0000) S_$1 Rms deviation of fitted atoms = 0.0000
15.4851 (0.0030) x + 7.1768 (0.0082) y - 5.6837 (0.0105) z = 9.6512 (0.0061) Angle to previous plane (with approximate e.s.d.) = 46.10 (0.03)
* -0.0770 (0.0006) P1 * 0.0775 (0.0005) P2 * 0.0812 (0.0006) S * -0.0817 (0.0006) S_$1 0.0157 (0.0008) Ir -2.4123 (0.0019) Cl1
Rms deviation of fitted atoms = 0.0793
15.4851 (0.0030) x - 7.1768 (0.0082) y + 5.6837 (0.0105) z = 8.1582 (0.0063) Angle to previous plane (with approximate e.s.d.) = 46.87 (0.02)
* -0.0770 (0.0006) P1_$1 * 0.0775 (0.0005) P2_$1 * -0.0817 (0.0006) S * 0.0812 (0.0006) S_$1 Rms deviation of fitted atoms = 0.0793
- 0.3873(0.0300)x + 21.0254(0.0035)y + 2.6846(0.0402)z = 15.3266(0.0133) Angle to previous plane (with approximate e.s.d.) = 70.20 (0.10)
* -0.0443 (0.0047) C1 * -0.0052 (0.0049) C2 * 0.0212 (0.0052) C3 * 0.0197 (0.0057) C4 * -0.0080 (0.0058) C5 * -0.0191 (0.0063) C6 * -0.0163 (0.0059) C7 * 0.0153 (0.0055) C8 * 0.0227 (0.0052) C9 * 0.0140 (0.0045) C10 Rms deviation of fitted atoms = 0.0211
8.7714(0.0290)x + 4.0530(0.0256)y + 22.8633(0.0309)z = 15.2551(0.0178) Angle to previous plane (with approximate e.s.d.) = 74.91 (0.12)
* 0.0230 (0.0048) C11 * -0.0066 (0.0054) C12 * -0.0203 (0.0055) C13 * -0.0206 (0.0058) C14 * 0.0126 (0.0059) C15 * 0.0280 (0.0059) C16 * 0.0132 (0.0059) C17 * -0.0266 (0.0058) C18 * -0.0257 (0.0052) C19 * 0.0230 (0.0046) C20 Rms deviation of fitted atoms = 0.0210
- 3.1346(0.0443)x + 20.7488(0.0109)y + 1.0509(0.0789)z = 10.4480(0.0325) Angle to previous plane (with approximate e.s.d.) = 82.90 (0.18)
* -0.0012 (0.0044) C35 * 0.0063 (0.0050) C36 * -0.0048 (0.0054) C37 * -0.0021 (0.0051) C38 * 0.0073 (0.0048) C39 * -0.0056 (0.0045) C40
Rms deviation of fitted atoms = 0.0050
8.7714(0.0290)x + 4.0530(0.0256)y + 22.8633(0.0309)z = 15.2551(0.0178) Angle to previous plane (with approximate e.s.d.) = 82.90 (0.18)
* 0.0230 (0.0048) C11 * -0.0066 (0.0054) C12 * -0.0203 (0.0055) C13 * -0.0206 (0.0058) C14 * 0.0126 (0.0059) C15 * 0.0280 (0.0059) C16 * 0.0132 (0.0059) C17 * -0.0266 (0.0058) C18 * -0.0257 (0.0052) C19 * 0.0230 (0.0046) C20 Rms deviation of fitted atoms = 0.0210
12.6244(0.0324)x - 13.2160(0.0485)y + 6.1010(0.0734)z = 0.2536(0.0659) Angle to previous plane (with approximate e.s.d.) = 63.01 (0.18)
* -0.0182 (0.0044) C28 * 0.0011 (0.0050) C29 * 0.0126 (0.0053) C30 * -0.0093 (0.0051) C31 * -0.0080 (0.0048) C32 * 0.0219 (0.0045) C33
Rms deviation of fitted atoms = 0.0137
5.6299 (0.0455) x + 1.3171 (0.0612) y + 25.8327 (0.0266) z = 15.9828 (0.0469) Angle to previous plane (with approximate e.s.d.) = 65.20 (0.24)
* -0.0096 (0.0044) C21 * 0.0014 (0.0051) C22 * 0.0059 (0.0056) C23 * -0.0049 (0.0054) C24 * -0.0034 (0.0049) C25 * 0.0105 (0.0044) C26
Rms deviation of fitted atoms = 0.0067
8.7714 (0.0290) x + 4.0530 (0.0256) y + 22.8633 (0.0309) z = 15.2551 (0.0178) Angle to previous plane (with approximate e.s.d.) = 14.43 (0.26)
* 0.0230 (0.0048) C11 * -0.0066 (0.0054) C12 * -0.0203 (0.0055) C13 * -0.0206 (0.0058) C14 * 0.0126 (0.0059) C15 * 0.0280 (0.0059) C16 * 0.0132 (0.0059) C17 * -0.0266 (0.0058) C18 * -0.0257 (0.0052) C19 * 0.0230 (0.0046) C20 Rms deviation of fitted atoms = 0.0210
5.6299 (0.0455) x + 1.3171 (0.0612) y + 25.8327 (0.0266) z = 15.9828 (0.0469) Angle to previous plane (with approximate e.s.d.) = 14.43 (0.26)
* -0.0096 (0.0044) C21 * 0.0014 (0.0051) C22 * 0.0059 (0.0056) C23 * -0.0049 (0.0054) C24 * -0.0034 (0.0049) C25 * 0.0105 (0.0044) C26
Rms deviation of fitted atoms = 0.0067
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. The Friedel pairs reflections were included in the refinements. Six restraints were applied to the solvate molecules (CH2CH2Cl).
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
Ir 0.533307 (12) 0.562118 (10) 0.461944 (7) 0.01859 (6)
H0 0.6262 0.5644 0.4501 0.022*
S 0.57503 (8) 0.54702 (6) 0.54504 (5) 0.0207 (3)
Cl1 0.41927 (11) 0.5000 0.5000 0.0207 (4)
Cl2 1.0000 0.6482 (2) 0.2500 0.0898 (14)
P1 0.48675 (8) 0.66185 (7) 0.47733 (5) 0.0193 (3)
P2 0.50500 (9) 0.56718 (8) 0.38035 (5) 0.0223 (3)
C1 0.3942 (3) 0.6774 (3) 0.4444 (2) 0.0207 (11)
C2 0.3209 (3) 0.6747 (3) 0.4697 (2) 0.0252 (12)
H2 0.3209 0.6706 0.5041 0.030*
C3 0.2506 (3) 0.6777 (3) 0.4456 (2) 0.0277 (13)
H3 0.2025 0.6754 0.4636 0.033*
C4 0.2477 (3) 0.6841 (3) 0.3946 (2) 0.0244 (12)
C5 0.1741 (4) 0.6847 (3) 0.3685 (2) 0.0310 (14)
H5 0.1257 0.6811 0.3859 0.037*
C6 0.1727 (4) 0.6905 (4) 0.3187 (3) 0.0371 (15)
H6 0.1235 0.6913 0.3018 0.045*
C7 0.2441 (4) 0.6953 (4) 0.2929 (2) 0.0341 (15)
H7 0.2428 0.6987 0.2584 0.041*
C8 0.3161 (4) 0.6951 (3) 0.3165 (2) 0.0287 (13)
H8 0.3637 0.6991 0.2983 0.034*
C9 0.3192 (4) 0.6889 (3) 0.3685 (2) 0.0223 (11)
C10 0.3948 (3) 0.6866 (2) 0.3938 (2) 0.0174 (10)
C11 0.4685 (4) 0.6962 (3) 0.36509 (19) 0.0223 (10)
C12 0.4841 (4) 0.7583 (3) 0.3468 (2) 0.0261 (13)
C13 0.4338 (4) 0.8101 (3) 0.3563 (3) 0.0310 (14)
H13 0.3870 0.8038 0.3750 0.037*
C14 0.4511 (4) 0.8689 (3) 0.3392 (3) 0.0405 (17)
H14 0.4156 0.9027 0.3458 0.049*
C15 0.5202 (5) 0.8811 (4) 0.3120 (3) 0.045 (2)
H15 0.5320 0.9225 0.3007 0.055*
C16 0.5700 (5) 0.8312 (4) 0.3024 (3) 0.0415 (18)
H16 0.6168 0.8386 0.2841 0.050*
C17 0.5534 (4) 0.7692 (3) 0.3191 (2) 0.0304 (14)
C18 0.6030 (4) 0.7178 (4) 0.3075 (3) 0.0366 (16)
H18 0.6483 0.7247 0.2877 0.044*
C19 0.5874 (4) 0.6580 (3) 0.3241 (2) 0.0284 (13)
sup-5 Acta Cryst. (2007). E63, m918–m920
C20 0.5207 (4) 0.6456 (3) 0.35404 (19) 0.0245 (12)
C21 0.5483 (3) 0.7301 (3) 0.4616 (2) 0.0234 (11)
C22 0.5159 (3) 0.7907 (3) 0.4660 (3) 0.0329 (14)
H22 0.4631 0.7954 0.4774 0.039*
C23 0.5590 (4) 0.8434 (3) 0.4541 (3) 0.0402 (17)
H23 0.5356 0.8840 0.4575 0.048*
C24 0.6357 (4) 0.8386 (4) 0.4372 (3) 0.0387 (17)
C25 0.6688 (4) 0.7782 (3) 0.4331 (2) 0.0325 (15)
H25 0.7215 0.7739 0.4215 0.039*
C26 0.6262 (3) 0.7243 (3) 0.4457 (2) 0.0254 (12)
H26 0.6502 0.6838 0.4434 0.031*
C27 0.6809 (5) 0.8958 (4) 0.4230 (4) 0.059 (3)
H27A 0.7333 0.8833 0.4111 0.089*
H27B 0.6868 0.9236 0.4513 0.089*
H27C 0.6523 0.9183 0.3972 0.089*
C28 0.4637 (4) 0.6754 (2) 0.5420 (2) 0.0240 (10)
C29 0.5009 (4) 0.7220 (3) 0.5694 (2) 0.0301 (13)
H29 0.5376 0.7496 0.5540 0.036*
C30 0.4853 (4) 0.7293 (4) 0.6192 (3) 0.0376 (16)
H30 0.5120 0.7613 0.6371 0.045*
C31 0.4315 (4) 0.6904 (4) 0.6425 (2) 0.0311 (14)
C32 0.3953 (4) 0.6433 (3) 0.6158 (2) 0.0301 (13)
H32 0.3579 0.6161 0.6311 0.036*
C33 0.4130 (4) 0.6351 (3) 0.5664 (2) 0.0263 (13)
H33 0.3895 0.6010 0.5491 0.032*
C34 0.4112 (5) 0.6996 (5) 0.6955 (3) 0.050 (2)
H34A 0.4427 0.7345 0.7089 0.075*
H34B 0.4229 0.6607 0.7136 0.075*
H34C 0.3547 0.7096 0.6986 0.075*
C35 0.4081 (4) 0.5471 (3) 0.3566 (2) 0.0239 (12)
C36 0.3966 (4) 0.5483 (3) 0.3056 (2) 0.0337 (15)
H36 0.4399 0.5565 0.2844 0.040*
C37 0.3216 (5) 0.5374 (4) 0.2870 (3) 0.0408 (17)
H37 0.3143 0.5375 0.2527 0.049*
C38 0.2580 (4) 0.5264 (3) 0.3163 (3) 0.0357 (16)
C39 0.2692 (4) 0.5260 (3) 0.3666 (3) 0.0319 (15)
H39 0.2250 0.5190 0.3874 0.038*
C40 0.3429 (4) 0.5355 (3) 0.3867 (2) 0.0268 (12)
H40 0.3495 0.5342 0.4210 0.032*
C41 0.1743 (5) 0.5188 (4) 0.2960 (4) 0.055 (2)
H41A 0.1761 0.5191 0.2604 0.083*
H41B 0.1411 0.5539 0.3074 0.083*
H41C 0.1518 0.4787 0.3073 0.083*
C42 0.5717 (4) 0.5132 (3) 0.3482 (2) 0.0263 (12)
C43 0.5442 (4) 0.4581 (3) 0.3272 (2) 0.0308 (14)
H43 0.4886 0.4518 0.3245 0.037*
C44 0.5951 (5) 0.4117 (4) 0.3099 (3) 0.0394 (17)
C45 0.6764 (5) 0.4208 (4) 0.3119 (3) 0.0397 (17)
C46 0.7038 (4) 0.4760 (4) 0.3325 (3) 0.0380 (16)
H46 0.7593 0.4833 0.3341 0.046*
C47 0.6531 (4) 0.5209 (3) 0.3510 (3) 0.0332 (15)
H47 0.6742 0.5578 0.3659 0.040*
C48 0.7323 (6) 0.3706 (5) 0.2924 (4) 0.061 (3)
H48A 0.7014 0.3356 0.2786 0.092*
H48B 0.7654 0.3546 0.3190 0.092*
H48C 0.7660 0.3890 0.2671 0.092*
C49 0.6787 (3) 0.5619 (3) 0.5476 (2) 0.0292 (12)
C50 0.7371 (4) 0.5161 (3) 0.5515 (3) 0.0339 (15)
H50 0.7227 0.4726 0.5514 0.041*
C51 0.8151 (4) 0.5327 (4) 0.5556 (3) 0.0389 (16)
H51 0.8542 0.5007 0.5592 0.047*
C52 0.8374 (5) 0.5951 (4) 0.5546 (3) 0.051 (2)
H52 0.8918 0.6062 0.5566 0.061*
C53 0.7797 (5) 0.6423 (4) 0.5507 (4) 0.053 (2)
H53 0.7953 0.6855 0.5498 0.064*
C54 0.7010 (5) 0.6268 (3) 0.5481 (3) 0.0417 (18)
H54 0.6618 0.6590 0.5467 0.050*
Cl3 0.4932 (4) 0.9211 (4) 0.5859 (4) 0.280 (6)
Cl4 0.2866 (4) 0.8362 (4) 0.6344 (4) 0.340 (8)
C55 0.4013 (13) 0.8769 (14) 0.5843 (8) 0.228 (13)*
H55A 0.3617 0.8977 0.5630 0.274*
H55B 0.4099 0.8330 0.5730 0.274*
C56 0.3742 (11) 0.8788 (11) 0.6409 (7) 0.174 (9)*
H56A 0.3648 0.9224 0.6526 0.209*
H56B 0.4126 0.8572 0.6625 0.209*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Ir 0.01902 (9) 0.02020 (9) 0.01654 (8) 0.00008 (9) 0.00126 (8) 0.00000 (8) S 0.0217 (6) 0.0208 (7) 0.0197 (7) −0.0011 (5) −0.0003 (5) −0.0006 (5)
Cl1 0.0193 (8) 0.0225 (9) 0.0202 (9) 0.000 0.000 0.0019 (7)
Cl2 0.067 (2) 0.080 (3) 0.123 (4) 0.000 −0.056 (2) 0.000
P1 0.0187 (7) 0.0211 (7) 0.0182 (6) −0.0018 (5) 0.0020 (5) 0.0011 (5) P2 0.0235 (6) 0.0245 (7) 0.0190 (6) −0.0010 (6) 0.0028 (5) −0.0014 (6)
C1 0.018 (2) 0.018 (3) 0.027 (3) 0.003 (2) 0.002 (2) −0.001 (2)
C2 0.026 (3) 0.026 (3) 0.023 (3) −0.003 (2) 0.006 (2) 0.001 (2) C3 0.017 (3) 0.033 (3) 0.033 (3) −0.001 (2) 0.007 (2) 0.003 (3)
C4 0.019 (3) 0.023 (3) 0.031 (3) 0.002 (2) 0.004 (2) −0.001 (2)
C5 0.024 (3) 0.035 (3) 0.034 (3) 0.006 (3) 0.008 (3) 0.004 (3)
C6 0.028 (3) 0.050 (4) 0.034 (4) 0.004 (3) −0.007 (3) 0.000 (3) C7 0.032 (3) 0.046 (4) 0.024 (3) −0.004 (3) −0.002 (3) 0.000 (3) C8 0.028 (3) 0.032 (3) 0.026 (3) −0.003 (3) 0.003 (2) 0.003 (3)
C9 0.032 (3) 0.013 (2) 0.021 (3) 0.006 (2) 0.007 (2) 0.002 (2)
sup-7 Acta Cryst. (2007). E63, m918–m920
Geometric parameters (Å, º)
Ir—P1 2.2885 (15) C27—H27B 0.9800
Ir—P2 2.2937 (14) C27—H27C 0.9800
Ir—S 2.4094 (14) C28—C33 1.380 (8)
Ir—Si 2.4190 (13) C28—C29 1.389 (9)
Ir—Cl1 2.5534 (14) C29—C30 1.400 (9)
Ir—Iri 3.3558 (4) C29—H29 0.9500
Ir—H0 1.603 C30—C31 1.382 (10)
S—C49 1.779 (6) C30—H30 0.9500
S—Iri 2.4190 (13) C31—C32 1.380 (10)
Cl1—Iri 2.5534 (14) C31—C34 1.508 (9)
P1—C21 1.829 (6) C32—C33 1.401 (9)
P1—C1 1.834 (6) C32—H32 0.9500
P1—C28 1.841 (6) C33—H33 0.9500
P2—C35 1.811 (6) C34—H34A 0.9800
P2—C20 1.827 (6) C34—H34B 0.9800
P2—C42 1.830 (6) C34—H34C 0.9800
C1—C10 1.404 (8) C35—C40 1.398 (9)
C1—C2 1.421 (8) C35—C36 1.413 (8)
C2—C3 1.359 (9) C36—C37 1.386 (10)
C2—H2 0.9500 C36—H36 0.9500
C3—C4 1.409 (9) C37—C38 1.361 (11)
C3—H3 0.9500 C37—H37 0.9500
C4—C9 1.408 (8) C38—C39 1.394 (10)
C4—C5 1.434 (9) C38—C41 1.528 (10)
C5—C6 1.375 (10) C39—C40 1.376 (9)
C5—H5 0.9500 C39—H39 0.9500
C6—C7 1.402 (10) C40—H40 0.9500
C6—H6 0.9500 C41—H41A 0.9800
C7—C8 1.377 (9) C41—H41B 0.9800
C7—H7 0.9500 C41—H41C 0.9800
C8—C9 1.436 (8) C42—C43 1.378 (9)
C8—H8 0.9500 C42—C47 1.386 (10)
C9—C10 1.453 (8) C43—C44 1.388 (9)
C10—C11 1.486 (8) C43—H43 0.9500
C11—C20 1.417 (8) C44—C45 1.387 (11)
C11—C12 1.430 (8) C44—H44 0.9500
C12—C13 1.410 (9) C45—C46 1.377 (11)
C12—C17 1.414 (9) C45—C48 1.517 (10)
C13—C14 1.360 (10) C46—C47 1.375 (10)
C13—H13 0.9500 C46—H46 0.9500
C14—C15 1.408 (11) C47—H47 0.9500
C14—H14 0.9500 C48—H48A 0.9800
C15—C16 1.372 (12) C48—H48B 0.9800
C15—H15 0.9500 C48—H48C 0.9800
C16—C17 1.416 (9) C49—C50 1.385 (9)
sup-9 Acta Cryst. (2007). E63, m918–m920
C17—C18 1.409 (11) C50—C51 1.367 (10)
C18—C19 1.367 (10) C50—H50 0.9500
C18—H18 0.9500 C51—C52 1.372 (11)
C19—C20 1.419 (8) C51—H51 0.9500
C19—H19 0.9500 C52—C53 1.397 (12)
C21—C26 1.391 (8) C52—H52 0.9500
C21—C22 1.397 (8) C53—C54 1.371 (11)
C22—C23 1.371 (9) C53—H53 0.9500
C22—H22 0.9500 C54—H54 0.9500
C23—C24 1.379 (10) Cl3—C55 1.811 (16)
C23—H23 0.9500 Cl4—C56 1.740 (15)
C24—C25 1.398 (11) C55—C56 1.621 (17)
C24—C27 1.480 (10) C55—H55A 0.9900
C25—C26 1.390 (9) C55—H55B 0.9900
C25—H25 0.9500 C56—H56A 0.9900
C26—H26 0.9500 C56—H56B 0.9900
C27—H27A 0.9800
P1—Ir—P2 93.78 (6) C25—C26—C21 119.7 (6)
P1—Ir—S 92.72 (5) C25—C26—H26 120.2
P2—Ir—S 172.91 (5) C21—C26—H26 120.2
P1—Ir—Si 173.00 (5) C24—C27—H27A 109.5
P2—Ir—Si 91.58 (5) C24—C27—H27B 109.5
S—Ir—Si 82.17 (5) H27A—C27—H27B 109.5
P1—Ir—Cl1 97.99 (4) C24—C27—H27C 109.5
P2—Ir—Cl1 105.48 (4) H27A—C27—H27C 109.5
S—Ir—Cl1 76.38 (4) H27B—C27—H27C 109.5
Si—Ir—Cl1 76.22 (4) C33—C28—C29 117.1 (6)
P1—Ir—Iri 127.26 (4) C33—C28—P1 120.1 (4)
P2—Ir—Iri 130.16 (4) C29—C28—P1 122.5 (5)
S—Ir—Iri 46.09 (3) C28—C29—C30 121.5 (6)
Si—Ir—Iri 45.85 (3) C28—C29—H29 119.3
Cl1—Ir—Iri 48.92 (3) C30—C29—H29 119.3
P1—Ir—H0 110.2 C31—C30—C29 120.7 (6)
P2—Ir—H0 90.2 C31—C30—H30 119.7
S—Ir—H0 84.9 C29—C30—H30 119.7
Si—Ir—H0 74.2 C32—C31—C30 118.3 (6)
Cl1—Ir—H0 146.8 C32—C31—C34 120.4 (7)
Iri—Ir—H0 98.7 C30—C31—C34 121.3 (7)
C49—S—Ir 107.5 (2) C31—C32—C33 120.7 (6)
C49—S—Iri 117.3 (2) C31—C32—H32 119.7
Ir—S—Iri 88.06 (4) C33—C32—H32 119.7
Ir—Cl1—Iri 82.16 (5) C28—C33—C32 121.7 (6)
C21—P1—C1 103.1 (3) C28—C33—H33 119.2
C21—P1—C28 103.0 (3) C32—C33—H33 119.2
C1—P1—C28 105.6 (3) C31—C34—H34A 109.5
C21—P1—Ir 119.18 (19) C31—C34—H34B 109.5
C28—P1—Ir 113.20 (18) C31—C34—H34C 109.5
C35—P2—C20 101.6 (3) H34A—C34—H34C 109.5
C35—P2—C42 103.6 (3) H34B—C34—H34C 109.5
C20—P2—C42 106.6 (3) C40—C35—C36 118.7 (6)
C35—P2—Ir 122.0 (2) C40—C35—P2 122.6 (5)
C20—P2—Ir 113.48 (19) C36—C35—P2 118.5 (5)
C42—P2—Ir 108.4 (2) C37—C36—C35 119.3 (6)
C10—C1—C2 119.7 (5) C37—C36—H36 120.4
C10—C1—P1 120.5 (4) C35—C36—H36 120.4
C2—C1—P1 119.6 (4) C38—C37—C36 122.0 (7)
C3—C2—C1 121.4 (6) C38—C37—H37 119.0
C3—C2—H2 119.3 C36—C37—H37 119.0
C1—C2—H2 119.3 C37—C38—C39 118.8 (6)
C2—C3—C4 121.2 (5) C37—C38—C41 122.1 (7)
C2—C3—H3 119.4 C39—C38—C41 119.0 (7)
C4—C3—H3 119.4 C40—C39—C38 121.2 (7)
C9—C4—C3 118.9 (5) C40—C39—H39 119.4
C9—C4—C5 119.2 (6) C38—C39—H39 119.4
C3—C4—C5 121.9 (5) C39—C40—C35 120.1 (6)
C6—C5—C4 120.9 (6) C39—C40—H40 120.0
C6—C5—H5 119.5 C35—C40—H40 120.0
C4—C5—H5 119.5 C38—C41—H41A 109.5
C5—C6—C7 119.6 (6) C38—C41—H41B 109.5
C5—C6—H6 120.2 H41A—C41—H41B 109.5
C7—C6—H6 120.2 C38—C41—H41C 109.5
C8—C7—C6 121.4 (6) H41A—C41—H41C 109.5
C8—C7—H7 119.3 H41B—C41—H41C 109.5
C6—C7—H7 119.3 C43—C42—C47 117.1 (6)
C7—C8—C9 120.1 (6) C43—C42—P2 121.4 (5)
C7—C8—H8 119.9 C47—C42—P2 120.6 (5)
C9—C8—H8 119.9 C42—C43—C44 122.0 (7)
C4—C9—C8 118.8 (6) C42—C43—H43 119.0
C4—C9—C10 120.5 (5) C44—C43—H43 119.0
C8—C9—C10 120.7 (5) C45—C44—C43 120.1 (7)
C1—C10—C9 118.1 (5) C45—C44—H44 119.9
C1—C10—C11 123.3 (5) C43—C44—H44 119.9
C9—C10—C11 118.5 (5) C46—C45—C44 117.7 (7)
C20—C11—C12 120.2 (6) C46—C45—C48 122.0 (8)
C20—C11—C10 122.1 (5) C44—C45—C48 120.3 (8)
C12—C11—C10 117.7 (5) C47—C46—C45 121.8 (7)
C13—C12—C17 118.1 (6) C47—C46—H46 119.1
C13—C12—C11 122.5 (6) C45—C46—H46 119.1
C17—C12—C11 119.4 (6) C46—C47—C42 121.1 (7)
C14—C13—C12 121.1 (7) C46—C47—H47 119.5
C14—C13—H13 119.5 C42—C47—H47 119.5
C12—C13—H13 119.5 C45—C48—H48A 109.5
C13—C14—C15 121.9 (7) C45—C48—H48B 109.5
sup-11 Acta Cryst. (2007). E63, m918–m920
C15—C14—H14 119.1 C45—C48—H48C 109.5
C16—C15—C14 117.9 (6) H48A—C48—H48C 109.5
C16—C15—H15 121.0 H48B—C48—H48C 109.5
C14—C15—H15 121.0 C50—C49—C54 119.0 (6)
C15—C16—C17 121.8 (7) C50—C49—S 125.4 (5)
C15—C16—H16 119.1 C54—C49—S 115.5 (5)
C17—C16—H16 119.1 C51—C50—C49 120.8 (7)
C18—C17—C12 119.1 (6) C51—C50—H50 119.6
C18—C17—C16 121.6 (6) C49—C50—H50 119.6
C12—C17—C16 119.3 (7) C50—C51—C52 120.6 (7)
C19—C18—C17 121.5 (6) C50—C51—H51 119.7
C19—C18—H18 119.2 C52—C51—H51 119.7
C17—C18—H18 119.2 C51—C52—C53 119.8 (7)
C18—C19—C20 121.1 (6) C51—C52—H52 120.1
C18—C19—H19 119.4 C53—C52—H52 120.1
C20—C19—H19 119.4 C54—C53—C52 120.5 (7)
C11—C20—C19 118.5 (6) C54—C53—H53 119.7
C11—C20—P2 120.6 (4) C52—C53—H53 119.7
C19—C20—P2 120.8 (5) C53—C54—C49 119.2 (7)
C26—C21—C22 118.5 (5) C53—C54—H54 120.4
C26—C21—P1 122.8 (5) C49—C54—H54 120.4
C22—C21—P1 118.7 (4) C56—C55—Cl3 101.9 (12)
C23—C22—C21 121.1 (6) C56—C55—H55A 111.4
C23—C22—H22 119.4 Cl3—C55—H55A 111.4
C21—C22—H22 119.4 C56—C55—H55B 111.4
C22—C23—C24 121.3 (7) Cl3—C55—H55B 111.4
C22—C23—H23 119.3 H55A—C55—H55B 109.3
C24—C23—H23 119.3 C55—C56—Cl4 97.4 (11)
C23—C24—C25 117.9 (6) C55—C56—H56A 112.3
C23—C24—C27 120.8 (8) Cl4—C56—H56A 112.3
C25—C24—C27 121.3 (7) C55—C56—H56B 112.3
C26—C25—C24 121.5 (6) Cl4—C56—H56B 112.3
C26—C25—H25 119.3 H56A—C56—H56B 109.9
C24—C25—H25 119.3
P1—Ir—S—C49 −99.3 (3) C10—C11—C20—C19 176.4 (5)
Si—Ir—S—C49 85.5 (2) C12—C11—C20—P2 176.0 (4)
Cl1—Ir—S—C49 163.2 (3) C10—C11—C20—P2 −6.7 (8)
Iri—Ir—S—C49 118.0 (3) C18—C19—C20—C11 2.2 (9)
P1—Ir—S—Iri 142.71 (4) C18—C19—C20—P2 −174.7 (5)
Si—Ir—S—Iri −32.49 (6) C35—P2—C20—C11 61.0 (5)
Cl1—Ir—S—Iri 45.14 (3) C42—P2—C20—C11 169.1 (5)
P1—Ir—Cl1—Iri −133.52 (4) Ir—P2—C20—C11 −71.7 (5)
P2—Ir—Cl1—Iri 130.28 (4) C35—P2—C20—C19 −122.2 (5)
S—Ir—Cl1—Iri −42.65 (3) C42—P2—C20—C19 −14.1 (6)
Si—Ir—Cl1—Iri 42.48 (3) Ir—P2—C20—C19 105.1 (5)
P2—Ir—P1—C21 −78.0 (2) C1—P1—C21—C26 −131.6 (5)
Cl1—Ir—P1—C21 175.8 (2) Ir—P1—C21—C26 −7.5 (6)
Iri—Ir—P1—C21 132.4 (2) C1—P1—C21—C22 48.8 (6)
P2—Ir—P1—C1 41.9 (2) C28—P1—C21—C22 −60.9 (6)
S—Ir—P1—C1 −141.0 (2) Ir—P1—C21—C22 172.9 (4)
Cl1—Ir—P1—C1 −64.4 (2) C26—C21—C22—C23 1.2 (10)
Iri—Ir—P1—C1 −107.7 (2) P1—C21—C22—C23 −179.1 (6)
P2—Ir—P1—C28 160.7 (2) C21—C22—C23—C24 0.2 (12)
S—Ir—P1—C28 −22.1 (2) C22—C23—C24—C25 −0.8 (12)
Cl1—Ir—P1—C28 54.5 (2) C22—C23—C24—C27 178.1 (8)
Iri—Ir—P1—C28 11.1 (2) C23—C24—C25—C26 −0.1 (11)
P1—Ir—P2—C35 −85.8 (2) C27—C24—C25—C26 −179.0 (7)
Si—Ir—P2—C35 89.7 (2) C24—C25—C26—C21 1.6 (10)
Cl1—Ir—P2—C35 13.6 (2) C22—C21—C26—C25 −2.1 (9)
Iri—Ir—P2—C35 62.4 (2) P1—C21—C26—C25 178.3 (5)
P1—Ir—P2—C20 36.2 (2) C21—P1—C28—C33 175.6 (5)
Si—Ir—P2—C20 −148.3 (2) C1—P1—C28—C33 67.8 (5)
Cl1—Ir—P2—C20 135.5 (2) Ir—P1—C28—C33 −54.4 (5)
Iri—Ir—P2—C20 −175.7 (2) C21—P1—C28—C29 −10.1 (6)
P1—Ir—P2—C42 154.3 (2) C1—P1—C28—C29 −117.9 (6)
Si—Ir—P2—C42 −30.2 (2) Ir—P1—C28—C29 119.9 (5)
Cl1—Ir—P2—C42 −106.3 (2) C33—C28—C29—C30 −2.2 (10)
Iri—Ir—P2—C42 −57.5 (2) P1—C28—C29—C30 −176.7 (6)
C21—P1—C1—C10 56.6 (5) C28—C29—C30—C31 −0.7 (11)
C28—P1—C1—C10 164.3 (4) C29—C30—C31—C32 1.6 (11)
Ir—P1—C1—C10 −72.4 (5) C29—C30—C31—C34 −177.0 (7)
C21—P1—C1—C2 −128.8 (5) C30—C31—C32—C33 0.3 (11)
C28—P1—C1—C2 −21.1 (5) C34—C31—C32—C33 179.0 (7)
Ir—P1—C1—C2 102.2 (4) C29—C28—C33—C32 4.2 (9)
C10—C1—C2—C3 3.3 (9) P1—C28—C33—C32 178.8 (5)
P1—C1—C2—C3 −171.4 (5) C31—C32—C33—C28 −3.4 (10)
C1—C2—C3—C4 −0.4 (9) C20—P2—C35—C40 −118.8 (5)
C2—C3—C4—C9 −1.5 (9) C42—P2—C35—C40 130.7 (5)
C2—C3—C4—C5 177.4 (6) Ir—P2—C35—C40 8.5 (6)
C9—C4—C5—C6 −0.6 (10) C20—P2—C35—C36 55.8 (5)
C3—C4—C5—C6 −179.5 (7) C42—P2—C35—C36 −54.6 (5)
C4—C5—C6—C7 0.6 (11) Ir—P2—C35—C36 −176.8 (4)
C5—C6—C7—C8 −0.9 (12) C40—C35—C36—C37 −0.7 (10)
C6—C7—C8—C9 1.1 (11) P2—C35—C36—C37 −175.5 (6)
C3—C4—C9—C8 179.7 (6) C35—C36—C37—C38 1.0 (11)
C5—C4—C9—C8 0.8 (9) C36—C37—C38—C39 −0.2 (11)
C3—C4—C9—C10 0.6 (9) C36—C37—C38—C41 175.7 (7)
C5—C4—C9—C10 −178.3 (6) C37—C38—C39—C40 −0.9 (11)
C7—C8—C9—C4 −1.1 (10) C41—C38—C39—C40 −177.0 (7)
C7—C8—C9—C10 178.1 (6) C38—C39—C40—C35 1.3 (10)
C2—C1—C10—C9 −4.1 (8) C36—C35—C40—C39 −0.5 (9)
P1—C1—C10—C9 170.5 (4) P2—C35—C40—C39 174.2 (5)
C2—C1—C10—C11 174.0 (5) C35—P2—C42—C43 −21.0 (6)
sup-13 Acta Cryst. (2007). E63, m918–m920
C4—C9—C10—C1 2.2 (8) Ir—P2—C42—C43 109.8 (5)
C8—C9—C10—C1 −176.9 (5) C35—P2—C42—C47 169.8 (6)
C4—C9—C10—C11 −176.0 (5) C20—P2—C42—C47 63.1 (6)
C8—C9—C10—C11 4.9 (8) Ir—P2—C42—C47 −59.4 (6)
C1—C10—C11—C20 75.2 (7) C47—C42—C43—C44 0.6 (10)
C9—C10—C11—C20 −106.7 (6) P2—C42—C43—C44 −169.0 (5)
C1—C10—C11—C12 −107.4 (6) C42—C43—C44—C45 −2.3 (11)
C9—C10—C11—C12 70.6 (7) C43—C44—C45—C46 1.8 (11)
C20—C11—C12—C13 179.4 (6) C43—C44—C45—C48 −179.2 (8)
C10—C11—C12—C13 2.0 (9) C44—C45—C46—C47 0.3 (11)
C20—C11—C12—C17 −2.3 (8) C48—C45—C46—C47 −178.7 (8)
C10—C11—C12—C17 −179.7 (5) C45—C46—C47—C42 −2.0 (11)
C17—C12—C13—C14 0.3 (10) C43—C42—C47—C46 1.5 (10)
C11—C12—C13—C14 178.6 (6) P2—C42—C47—C46 171.1 (6)
C12—C13—C14—C15 −1.0 (11) Ir—S—C49—C50 −104.9 (5)
C13—C14—C15—C16 0.8 (11) Iri—S—C49—C50 −7.9 (6)
C14—C15—C16—C17 −0.1 (11) Ir—S—C49—C54 78.6 (5)
C13—C12—C17—C18 −177.5 (6) Iri—S—C49—C54 175.6 (5)
C11—C12—C17—C18 4.1 (9) C54—C49—C50—C51 −0.4 (10)
C13—C12—C17—C16 0.4 (9) S—C49—C50—C51 −176.8 (6)
C11—C12—C17—C16 −177.9 (6) C49—C50—C51—C52 −1.7 (12)
C15—C16—C17—C18 177.3 (7) C50—C51—C52—C53 1.7 (14)
C15—C16—C17—C12 −0.6 (10) C51—C52—C53—C54 0.4 (15)
C12—C17—C18—C19 −2.9 (10) C52—C53—C54—C49 −2.4 (14)
C16—C17—C18—C19 179.2 (7) C50—C49—C54—C53 2.5 (11)
C17—C18—C19—C20 −0.3 (10) S—C49—C54—C53 179.2 (7)
C12—C11—C20—C19 −0.9 (8) Cl3—C55—C56—Cl4 179.6 (14)