research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 75| Part 1| January 2019| Pages 75-80
https://doi.org/10.1107/S2056989018017644

Crystal structures of two PCN pincer iridium complexes and one PCP pincer carbodi­phospho­rane iridium inter­mediate: substitution of one phosphine moiety of a carbodi­phospho­rane by an organic azide

CROSSMARK_Color_square_no_text.svg
Gabriel Julian Partl,a* Felix Nussbaumer,a Walter Schuh,a Holger Kopacka,a Klaus Wursta and Paul Peringera

aInstitute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, A-6020 Innsbruck, Austria
*Correspondence e-mail: gabriel.partl@uibk.ac.at

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 21 November 2018; accepted 13 December 2018; online 1 January 2019)

The structure of [Ir{(4-Cl-C6H4N3)C(dppm)-κ3P,C,N}(dppm-κ2P,P′)]Cl·1.5CH2Cl2·0.5C7H8 (C57H48Cl2IrN3P4·1.5CH2Cl2·0.5C7H8) (2), dppm = bis­(di­phenyl­phosphino)methane {systematic name: [7-(4-chloro­phen­yl)-1,1,3,3-tetra­phenyl-5,6,7-tri­aza-κN7-1,3λ4-diphospha-κP1-hepta-4,6-dien-4-yl][methyl­ene­bis(di­phenyl­phosphine)-κ2P,P′]iridium(I) chloride–di­chloro­methane–toluene (2/3/1)}, resulting from the reaction of [IrClH{C(dppm)2-κ3P,C,P)(MeCN)]Cl (1a) with 1-azido-4-chloro­benzene, shows a monocationic five-coordinate IrI complex with a distorted trigonal–bipyramidal geometry. In 2, the iridium centre is coordinated by the neutral triazeneyl­idene­phospho­rane (4-Cl-C6H4N3)C(dppm) acting as a PCN pincer ligand, and a chelating dppm unit. The structure of the coordination compound [IrCl(CN)H(C(dppm)2-κ3P,C,P)]·CH3CN, (C52H45ClIrNP4·CH3CN) (1b) [systematic name: chlorido­cyanidohydrido(1,1,3,3,5,5,7,7-octa­phenyl-1,3λ5,5λ4,7-tetra­phospha-κ2P1,P7-hept-3-en-4-yl)iridium(III) aceto­nitrile monosolvate], prepared from 1a and KCN, reveals an octa­hedral IrIII central atom with a meridional PCP pincer carbodi­phospho­rane (CDP) ligand; the chloride ligand is located trans to the central carbon of the CDP functionality while the hydrido and cyanido ligands are situated trans to each other. The chiral coordination compound [Ir(CN)((4-Cl-C6H4N3)CH(CH(P(Ph)2)2)-κ3P,C,N)(dppm-κ2P,P′)]·2CH3OH, (C58H48ClIrN4P4·2CH3OH) (3) (systematic name: {4-[3-(4-chloro­phen­yl)triazenido-κN3]-1,1,3,3-tetra­phenyl-1,3λ5-diphospha-κP1-but-2-en-4-yl}cyanido[methyl­enebis(di­phenyl­phosphine)-κ2P,P′]iridium(III) methanol disolvate), formed via prolonged reaction of 1-azido-4-chloro­benzene with 1b, features a six-coordinate IrIII central atom. The iridium centre is coordinated by the dianionic facial PCN pincer ligand [(4-Cl-C6H4N3)CH(CH(P(Ph2)2)2)], a cyanido ligand trans to the central carbon of the PCN pincer ligand and a chelating dppm unit. Complex 2 exhibits a 2:1 positional disorder of the Cl− anion. The CH2Cl2 and C7H8 solvent mol­ecules show occupational disorder, with the toluene mol­ecule exhibiting additional 1:1 positional disorder with some nearly overlying carbon atoms.

CCDC references: 1880135; 1880134; 1880133

Similar articles

1. Chemical context

Carbodi­phospho­ranes (CDPs), also termed double ylides, consist of two tertiary phosphines connected to a central divalent carbon(0) atom. The P—C bonds are best described as donor–acceptor inter­actions (Petz & Frenking, 2010[Petz, W. & Frenking, G. (2010). Topics in Organometallic Chemistry, Vol. 30, edited by R. Chauvin and Y. Canac, pp. 49-92. Berlin, Heidelberg: Springer.]). Most of the chemistry associated with CDPs concerns compounds with Lewis acids. Since the central CDP carbon possesses two lone electron pairs, it is therefore able to inter­act with either one or two Lewis acids (Chauvin & Canac, 2010[Chauvin, R. & Canac, Y. (2010). Editors. Transition Metal Complexes of Neutral eta1-Carbon Ligands (Topics in Organometallic Chemistry , Vol. 30). Berlin, Heidelberg: Springer.]; Petz & Frenking, 2010[Petz, W. & Frenking, G. (2010). Topics in Organometallic Chemistry, Vol. 30, edited by R. Chauvin and Y. Canac, pp. 49-92. Berlin, Heidelberg: Springer.]). Reactions involving the cleavage of the P—C bonds of the CDP functionality are less common in contrast to phospho­rus ylides (Petz & Frenking, 2010[Petz, W. & Frenking, G. (2010). Topics in Organometallic Chemistry, Vol. 30, edited by R. Chauvin and Y. Canac, pp. 49-92. Berlin, Heidelberg: Springer.]; Kolodiazhnyi, 1999[Kolodiazhnyi, O. I. (1999). Phosphorus Ylides. Weinheim: Wiley-VCH.]). We hereby report the non-innocent reactivity (Poverenov & Milstein, 2013[Poverenov, E. & Milstein, D. (2013). Topics in Organometallic Chemistry, Vol. 40, edited by G. van Koten and D. Milstein, pp. 21-47. Berlin, Heidelberg: Springer.]) of a PCP pincer ligand, whose central carbon is part of a CDP functionality, with an organic azide in the coordination sphere of iridium.

Treatment of the IrIII PCP pincer CDP complex [Ir(Cl)(H)(C(dppm)2-κ3P,C,P)(MeCN)]Cl (1a) (Schlapp-Hackl et al., 2018[Schlapp-Hackl, I., Pauer, B., Falschlunger, C., Schuh, W., Kopacka, H., Wurst, K. & Peringer, P. (2018). Acta Cryst. E74, 1643-1647.]) with 1-azido-4-chloro­benzene affords the IrI complex [Ir((4-Cl-C6H4N3)C(dppm)-κ3P,C,N)(dppm-κ2P,P′)]Cl (2). The reaction implies the substitution of one phosphine moiety of the PCP pincer ligand C(dppm)2 for the organic azide, thus producing the triazeneyl­idene­phospho­rane (4-Cl-C6H4N3)C(dppm), which acts as a PCN pincer ligand in 2. The phosphine displaced from the CDP functionality ends up in the coordination sphere of iridium and becomes part of a four-membered dppm chelate ring (see scheme).

[Scheme 1]

We believe that the reaction is initiated by an inter­action of the electrophilic organic azide with the central CDP carbon of the PCP ligand, which disposes of one lone electron pair (Petz & Frenking, 2010[Petz, W. & Frenking, G. (2010). Topics in Organometallic Chemistry, Vol. 30, edited by R. Chauvin and Y. Canac, pp. 49-92. Berlin, Heidelberg: Springer.]). In a related reaction, N-heterocyclic carbenes (NHCs) have been reported to form end-on adducts with organic azides to form triazenes (Khramov & Bielawski, 2005[Khramov, D. M. & Bielawski, C. W. (2005). Chem. Commun. pp. 4958-4960.]). The inter­action of the CDP with the organic azide results in the formation of a double bond between the central carbon and the terminal nitro­gen of the organic azide and is associated with the cleavage of one P—C bond of the CDP functionality, while the carbon–iridium bond remains intact. At this stage, a deeply coloured and presumably five-coord­in­ate IrI inter­mediate was detected by monitoring the reaction via 31P-NMR spectroscopy. This inter­mediate features the triazenyl­idene­phospho­rane ligand (4-Cl-C6H4N3)C(dppm) and a monodentate dppm unit. The absence of a hydrido ligand is attributed to an antecedent reductive elimination of hydro­chloric acid, which, according to NMR spectroscopic results, is absorbed by the CDP carbon of the starting complex 1a. This carbon atom turns out to be the strongest base of the system, apparently more basic than the nitro­gen atoms and the central carbon of the PCN pincer ligand of 2. Consequently, only 50% of the educt is converted to 2. However, an almost qu­anti­tative and fast conversion into 2 was achieved upon addition of basic alumina. The formation of 2 is finalized via the dissociation of a chlorido ligand and the coordination of the displaced phosphine functionality to the Ir centre.

Treatment of 1a with KCN affords [Ir(Cl)(CN)(H)((C(dppm)2)-κ3P,C,P)] (1b), which reacts very slowly (over the course of weeks at room temperature) with 1-azido-4-chloro­benzene to the six-coordinate complex [Ir(CN)((4-Cl-C6H4N3)CH(CH(PPh2)2)-κ3P,C,N)(dppm-κ2P,P′)] (3). Related to the formation of 2, the organic azide substitutes one phosphine of the CDP functionality.

At first sight, the resulting PCN pincer ligand of 3 looks like a tautomer of the PCN pincer ligand of 2: while in the PCN pincer of 3, one proton is attached to C1 and C2 respectively, the PCN pincer of 2 carries two protons at C2 and none at C1. In contrast to the neutral ligand of 2, the PCN ligand in 3 carries a double negative charge, deduced as follows: first, in view of coordination number 6, 3 constitutes an IrIII complex. Second, the coordination compound 3 carries no charge. Third, the cyanido ligand contributes a −1 charge, and the iridium central atom a +3 charge. Since the dppm ligand is neutral, the charge of the PCN pincer ligand can be calculated to be −2. We suspect that the pathway of the reaction is similar to the formation of 2, except that the cyanido ligand permanently stays in the coordination sphere of iridium. The coordination of the displaced phosphine functionality to the IrI centre is thought to induce a two-electron transfer from iridium to the PCN ligand related to an oxidative addition reaction, and to be followed by the transfer of one proton from C2 to C1.

2. Structural commentary

The structures of compounds 2, 1b and 3 are given in Figs. 1[link], 2[link] and 3[link], respectively. Selected bond lengths and angles for all three compounds are given in Table 1[link].

Table 1
Selected bond lengths (Å) and angles (°) for 1b, 2 and 3

1b   2   3  
Ir1—C1 2.128 (4) Ir1—C1 1.996 (5) Ir1—C1 2.127 (3)
    Ir1—N1 1.999 (5) Ir1—N1 2.109 (2)
Ir1—P1 2.302 (1) Ir1—P1 2.2788 (14) Ir1—P1 2.3595 (6)
Ir1—P4 2.277 (1)        
Ir1—Cl1 2.445 (1) Ir1—P3 2.3748 (14) Ir1—P3 2.3584 (7)
Ir1—C4 2.0815 (5) Ir1—P4 2.2662 (14) Ir1—P4 2.3304 (6)
Ir1—H1 1.51 (4)     Ir1—C10 2.026 (2)
P2—C1 1.689 (4) P2—C1 1.776 (5) P2—C1 1.843 (2)
C1—P3 1.689 (4) C1—N3 1.346 (7) C1—N3 1.505 (3)
    N1—N2 1.354 (6) N1—N2 1.347 (3)
    N2—N3 1.308 (6) N2—N3 1.259 (3)
           
C4—Ir1—P1 94.22 (12) C1—Ir1—P1 85.35 (15) C1—Ir1—P1 87.23 (7)
C1—Ir1—P1 89.10 (12) N1—Ir1—P1 140.40 (13) N1—Ir1—P1 96.69 (6)
P4—Ir1—P1 173.16 (4) P4—Ir1—P1 95.59 (5) P4—Ir1—P1 98.11 (2)
C4—Ir1—P4 89.08 (12) C1—Ir1—P3 173.04 (16) P3—Ir1—P1 169.15 (2)
C1—Ir1—P4 84.94 (12) N1—Ir1—P3 100.49 (13) C10—Ir1—P1 92.84 (7)
C4—Ir1—Cl1 94.42 (13) P4—Ir1—P3 70.69 (5) C10—Ir1—P3 92.00 (7)
C1—Ir1—Cl1 175.28 (12) P1—Ir1—P3 101.62 (5) N1—Ir1—P3 92.64 (6)
P4—Ir1—Cl1 92.17 (4) C1—Ir1—P4 108.92 (16) C1—Ir1—P3 89.80 (7)
P1—Ir1—Cl1 93.55 (4) N1—Ir1—P4 122.71 (13) P4—Ir1—P3 72.19 (2)
C4—Ir1—C1 89.27 (17) C1—Ir1—N1 73.7 (2) C10—Ir1—P4 89.88 (7)
C4—Ir1—H1 176.6 (13)     N1—Ir1—P4 164.45 (6)
        C1—Ir1—P4 100.63 (7)
        C10—Ir1—N1 94.15 (9)
        C10—Ir1—C1 169.38 (9)
        N1—Ir1—C1 75.31 (9)
[Figure 1]
Figure 1
Structure of 2 with displacement ellipsoids drawn at the 30% probability level. For clarity, only the ipso carbon atoms of the phenyl groups are shown, and solvent mol­ecules have been omitted.
[Figure 2]
Figure 2
Structure of 1b with displacement ellipsoids drawn at the 30% probability level. Only the ipso carbon atoms of the phenyl groups are shown for clarity, and solvent mol­ecules have been omitted.
[Figure 3]
Figure 3
Structure of 3 with displacement ellipsoids drawn at the 30% probability level. Only the ipso carbon atoms of the phenyl groups are shown for clarity.

The structure of 2 (Fig. 1[link]) features a cationic five-coordinate iridium(I) complex with a chloride counter-ion. The asymmetric unit additionally contains 1.5 mol­ecules of di­chloro­methane and half a mol­ecule of toluene. The iridium centre is coordinated by a PCN pincer ligand and a chelating dppm; its coordination sphere displays a distorted trigonal–bipyramidal geometry, in which the PCN pincer occupies one axial (C1) and two equatorial (P1 and N1) positions. The donor atoms of the chelating dppm are found in the remaining axial (P3) and equatorial (P4) positions. Major distortions are apparent from the angles P4—Ir1—P3 [70.69 (5)°] and N1—Ir1—P1 [140.4 (1)°], which reflect the ring strain of both the four-membered dppm chelate ring and the PCN pincer ligand. The angles around the ylidic carbon C1 cover a range of 115.9 (4) to 124.5 (3)°, with a sum total of 359°. The C1=N3 bond exhibits an increased length [1.346 (7) Å] relative to typical C=N double bonds (1.29 Å), resulting in a formal bond order (BO) of 1.7. With a bond length of 1.308 (6) Å, the N2—N3 bond's BO is 1.7 as well; the N1—N2 distance amounts to 1.354 (6) Å (BO 1.5). In reported adducts of NHCs with organic azides, the C—N3 (numbering as in the free azides) bond lengths are similar to 2, whereas N1—N2 separations are shorter (ca 1.27 Å) and the N2—N3 distances are longer (ca 1.35 Å) compared to the corresponding bond lengths in 2 (Khramov & Bielawski, 2005[Khramov, D. M. & Bielawski, C. W. (2005). Chem. Commun. pp. 4958-4960.]). These differences are presumably due to the coordination of N3 to the Ir centre. Organic azides themselves exhibit a short N2—N3 bond [e.g. 1.1322 (2) Å, BO 2.5, for 2,4,6-trichlorphenyl­azide], whereas the N1—N2 bond is distinctly longer [1.252 (2) Å, BO 1.9; Takayama et al., 2010[Takayama, T., Mitsumori, T., Kawano, M., Sekine, A., Uekusa, H., Ohashi, Y. & Sugawara, T. (2010). Acta Cryst. B66, 639-646.]].

The structure of 1b (Fig. 2[link]) displays an octa­hedral irid­ium(III) coordination compound with a meridional C(dppm)2 PCP pincer ligand and one chlorido ligand situated trans to the central CDP carbon atom. The remaining sites are occupied by the hydrido and cyanido ligands positioned trans to each other. The structure is closely related to that of [Ir(Cl)2(H)(C(dppm)2)-κ3P,C,P)] (1c) (Partl et al., 2018[Partl, G. J., Nussbaumer, F., Schlapp-Hackl, I., Schuh, W., Kopacka, H., Wurst, K. & Peringer, P. (2018). Acta Cryst. E74, 846-852.]), which contains one chlorido ligand instead of the cyanido ligand trans to the hydrido ligand. The introduction of the cyanido ligand results in a markedly shorter Ir1—Cl1 bond trans to the CDP carbon [2.445 (1) Å compared to 2.5157 (14) Å for 1c], whereas the Ir1—C1 separation becomes longer [2.128 (4)Å compared to 2.101 (5) Å]. Ir—P distances are marginally affected (Table 1[link]).

The structure of 3 (Fig. 3[link]) shows a six-coordinate iridium(III) coordination compound with the PCN pincer ligand [(4-Cl-C6H4N3)CH(CH(PPh2)2)] in a facial mode, a bidentate dppm and a cyanido ligand trans to the central PCN carbon. Two mol­ecules of MeOH are connected to atoms N3 and N4 via hydrogen bonds. Distortions of the octa­hedral geometry are evident from the angles P3—Ir1—P4 and N1—Ir1—C1, amounting to 72.19 (2)° and 75.31 (9)°, respectively. The environment of the chiral carbon C1 is distorted tetra­hedral according to the angles N3—C1—Ir1 [109.8 (2)°], N3—C1—P2 [104.9 (2)°] and P2—C1—Ir1 [116.7 (1)°]. The deproton­ated dppm part of the PCN pincer ligand features delocal­ization over both P—C bonds [P1—C2 1.727 (3) and P2—C2 1.688 (3) Å, corresponding to a BO of ca 1.5 each). The C1—N3 bond is rather long [1.504 (3) Å, BO 0.8)] and appears to be in the range of protonated alkyl­amines, (Ishida, 2000[Ishida, H. (2000). Z. Naturforsch. Teil A, 55, 769-771.]) whereas the N2=N3 distance approximately corresponds to an N=N double bond [1.259 (3) Å, BO 1.9]. The N1—N2 separation is found to be in between a single and a double bond [1.347 (3) Å, BO 1.5].

3. Supra­molecular features

In the crystal of 2, supra­molecular features appear to revolve around the chloride anion (Table 2[link]): Cl1 interacts with the methyl­ene group of one dppm unit (C2—H2B⋯Cl1 = 2.62 Å) and to a proton of one di­chloro­methane mol­ecule (C11—H11B⋯Cl1i = 2.49 Å). It must be mentioned, however, that due to the positional disorder of both the chloride anion and the di­chloro­methane solvate units, these `bond' lengths are an estimation and may not necessarily reflect any actual inter­molecular inter­actions.

Table 2
Hydrogen-bond geometry (Å, °) for 2[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2B⋯Cl1 0.98 2.62 3.5215 (1) 153
C11—H11B⋯Cl1i 0.98 2.49 3.4594 (1) 170
C209—H209⋯N3ii 0.94 2.60 3.3722 (1) 140
C306—H306⋯Cl1Aiii 0.94 2.81 3.7037 (1) 159
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x+1, y, -z-{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

In the crystal of 1b, the nitro­gen atom of the aceto­nitrile solvate interacts with the methyl­ene group of one dppm unit in a hydrogen-bond like manner (C3—H3B⋯N2 = 2.58 Å; Table 3[link]). Inter­molecular halogen–hydrogen inter­actions are observed in two instances between phenyl protons and the chlorido ligand (C102—H102⋯Cl1 = 2.66 Å and C112—H112⋯Cl1i = 2.77 Å; Table 3[link]).

Table 3
Hydrogen-bond geometry (Å, °) for 1b[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3B⋯N2 0.98 2.58 3.4925 (1) 156
C102—H102⋯Cl1 0.94 2.66 3.5216 (1) 153
C112—H112⋯Cl1i 0.94 2.77 3.6470 (1) 155
C210—H210⋯N2ii 0.94 2.61 3.4554 (1) 150
C303—H303⋯N1iii 0.94 2.48 3.2064 (1) 134
Symmetry codes: (i) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) -x+2, -y+1, -z+1.

In the crystal of 3, inter­molecular features are restricted to solvate coordination (Table 4[link]): both methanol units are connected to the complex via hydrogen bonds, one to the triazenido group (O2—H2A⋯N3 = 2.16 Å) and the other to the cyanido ligand (O1—H1A⋯N4 = 2.02 Å).

Table 4
Hydrogen-bond geometry (Å, °) for 3[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯N4 0.83 2.02 2.8181 (1) 162
O2—H2A⋯N3 0.83 2.16 2.9486 (1) 158

4. Synthesis and crystallization

The syntheses of the title compounds are summarized in the general reaction scheme for the synthesis and crystallization of 2, 1b and 3, starting from 1a (1c is only mentioned for comparative purposes – see Structural commentary). All preparations were carried out under an inert atmosphere (N2) using standard Schlenk techniques. 1H, 13C and 31P NMR spectra were recorded on a Bruker DPX 300 NMR spectrometer (300 MHz) and were referenced against 13C/1H solvent peaks or an external 85% H3PO4 standard, respectively. The phospho­rus atoms in the NMR data are labelled in the same way as in the figures.

Synthesis of complex 2: 1a is formed upon stirring a mixture of [IrCl(cod)]2 (8.5 mg, 0.0125 mmol), [CH(dppm)2]Cl (20.5 mg, 0.025 mmol), (Reitsamer et al., 2012[Reitsamer, C., Stallinger, S., Schuh, W., Kopacka, H., Wurst, K., Obendorf, D. & Peringer, P. (2012). Dalton Trans. 41, 3503-3514.]), MeCN (0.1 ml) and MeOH (0.5 ml) for 25 min. After this, a solution of 1-azido-4-chloro­benzene (0.5 mol L−1 in methyl-tert-butyl ether, 0.1 ml, 0.050 mmol) and basic Al2O3 (30 mg) were subsequently added and the suspension was stirred for 5 min. The liquid part was separ­ated, and the volatiles evaporated in vacuo. The residue was then dissolved in CH2Cl2/toluene 1:2. Slow evaporation gave crystalline 2.

31P{1H}-NMR (MeCN/MeOH 1:5): δ = 16.1 (P1, ddd; JP1P2 = 30.6, JP1P3 = 6.1, JP1P4 = 33.7 Hz); 15.6 (P2, ddd; JP2P3 = 44.4, JP2P4 = 13.8 Hz); −37.4 (P3, ddd; JP3P4 = 52.0 Hz); −20.9 (P4, ddd) ppm. 13C{1H}-NMR (MeCN/MeOH 1:5): δ = 169.5 (C1, dddd; JC1P1 = 2.5, JC1P2 = 60.0, JC1P3 = 85.0, JC1P4 = 8.3 Hz) ppm.

Synthesis of coordination compounds 1b and 3: A mixture of [IrCl(cod)]2 (8.5 mg, 0.0125 mmol), [CH(dppm)2]Cl (20.5 mg, 0.025 mmol), MeCN (0.1 ml) and MeOH (0.4 ml) was stirred for 25 min. Then, a solution of KCN (2 mg, 0.03 mmol) in MeOH (0.2 ml) was added and the mixture stirred for 1 min. Thereafter, a solution of 1-azido-4-chloro­benzene in MTBE (0.1 ml, mol L−1 in MTBE, 0.05 mmol) was added. Yellow crystals of 1b formed within a few hours. Within 14 d, the orange crystals of 1b disappeared, and colourless crystals of 3 had developed.

1b 31P{1H}-NMR (MeCN/MeOH 1:6): δ = −0.3 (P1/P4, vt, NP1/P4P2/P3 = 67.3 Hz); 28.2 (P2/P3, vt) ppm. 13C{1H}-NMR (MeCN/MeOH 1:6): δ = −36.5 (C1, t, JC1P2/P3 = 100.1 Hz) ppm. 1H-NMR (MeCN/MeOH 1:6): δ = −12.2 (H1, s, 1H) ppm.

3 31P{1H}-NMR (CHCl3/MeOH 1:1): δ = 0.3 (P1, ddd, JP1P2 = 153.0, JP1P3 = 376.3, JP1P4 = 18.4 Hz); 55.2 (P2, dd, JP2P3 = 49.0 Hz); −57.0 (P3, ddd, JP3P4 = 27.5 Hz); −67.1 (P4, dd) ppm. 13C-NMR (CHCl3/MeOH 1:1): δ = 72.2 (C1, dd, JC1P2 = 38.7, JC1H1 = 142.1 Hz) ppm.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5[link]. Complex 2 involves a 2:1 positional disorder of the anion Cl1:Cl1A. The solvent mol­ecules CH2Cl2 and C7H8 show occupational disorder, with the toluene mol­ecule exhibiting additional 1:1 positional disorder with some nearly overlying carbon atoms. We propose a correlation between CH2Cl2 and C7H8, because of short inter­molecular Cl⋯C contacts. Therefore, the two solvent mol­ecules Cl3/C10–Cl4 and Cl5/C11–Cl6 have an occupancy of 0.75 and the `two' toluene mol­ecules, C12–C18 and C19–C25, an occupancy of 0.25. Several bond restraints were used to refine the toluene carbon atoms reasonably isotropically. The hydride hydrogen of 1b was localized and refined isotropically without restraints. The hydrogen atoms at C1 and C2 of 3 were localized and refined with isotropic displacement parameters. All other H atoms were positioned geometrically (C—H = 0.94–0.98 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C).

Table 5
Experimental details

  1b 2 3
Crystal data
Chemical formula [Ir(CN)ClH(C51H44P4)]·C2H3N [Ir(C25H22P2)(C32H26ClN3P2)]Cl·0.5C7H8·1.5CH2Cl2 [Ir(CN)(C23H22P2)(C34H26ClN3P2)]·2CH4O
Mr 1076.47 1335.42 1216.61
Crystal system, space group Monoclinic, P21/n Orthorhombic, Pbcn Triclinic, P[\overline{1}]
Temperature (K) 233 233 223
a, b, c (Å) 18.3264 (3), 13.6459 (2), 19.3010 (4) 28.1283 (3), 19.0989 (2), 23.6339 (2) 11.1683 (1), 12.7805 (2), 20.0591 (3)
α, β, γ (°) 90, 101.803 (1), 90 90, 90, 90 98.475 (1), 93.122 (1), 109.336 (1)
V (Å3) 4724.74 (14) 12696.6 (2) 2655.75 (6)
Z 4 8 2
Radiation type Mo Kα Mo Kα Mo Kα
μ (mm−1) 3.06 2.45 2.73
Crystal size (mm) 0.18 × 0.07 × 0.02 0.3 × 0.2 × 0.15 0.31 × 0.30 × 0.12
 
Data collection
Diffractometer Nonius KappaCCD Nonius KappaCCD Nonius KappaCCD
No. of measured, independent and observed [I > 2σ(I)] reflections 25915, 8317, 6345 73594, 11155, 9002 20072, 10396, 9895
Rint 0.086 0.039 0.034
(sin θ/λ)max (Å−1) 0.595 0.595 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.069, 1.03 0.042, 0.126, 1.05 0.023, 0.056, 1.05
No. of reflections 8317 11155 10396
No. of parameters 564 724 661
No. of restraints 0 30 0
H-atom treatment H atoms treated by a mixture of independent and constrained refinement H-atom parameters constrained H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.56, −1.04 1.66, −0.73 0.77, −1.11
Computer programs: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]), DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

CCDC references: 1880135; 1880134; 1880133

Crystal structure: contains datablocks global, 1b, 2, 3. DOI: https://doi.org/10.1107/S2056989018017644/su5464sup1.cif

Structure factors: contains datablock 1b. DOI: https://doi.org/10.1107/S2056989018017644/su54641bsup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989018017644/su54642sup3.hkl

Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2056989018017644/su54643sup4.hkl

checkCIF report


Computing details top

For all structures, data collection: COLLECT (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).

Chloridocyanidohydrido(1,1,3,3,5,5,7,7-octaphenyl-1,3λ5,5λ4,7-tetraphospha-κ2P1,P7-hept-3-en-4-yl)iridium(III) acetonitrile monosolvate (1b) top
Crystal data top
[Ir(CN)ClH(C51H44P4)]·C2H3NF(000) = 2160
Mr = 1076.47Dx = 1.513 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 18.3264 (3) ÅCell parameters from 52211 reflections
b = 13.6459 (2) Åθ = 1.0–25.0°
c = 19.3010 (4) ŵ = 3.06 mm−1
β = 101.803 (1)°T = 233 K
V = 4724.74 (14) Å3Prism, yellow
Z = 40.18 × 0.07 × 0.02 mm
Data collection top
Nonius KappaCCD
diffractometer		Rint = 0.086
phi– and ω–scansθmax = 25.0°, θmin = 1.4°
25915 measured reflectionsh = −21→20
8317 independent reflectionsk = −16→16
6345 reflections with I > 2σ(I)l = −22→22
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.021P)2 + 3.0711P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.003
8317 reflectionsΔρmax = 0.56 e Å−3
564 parametersΔρmin = −1.04 e Å−3
Special details top

Experimental. All data sets were measured with several scans to increase the number of redundant reflections. In our experience this method of averaging redundant reflections replaces in a good approximation semi-empirical absorptions methods (absorption correction programs like SORTAV lead to no better data sets).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Small crystal with low diffraction at higher 2 theta angles. Hydrogen at Ir were localized and refined isotropically without restraints.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ir11.08853 (2)0.20725 (2)0.71435 (2)0.02191 (7)
H11.1054 (19)0.172 (3)0.790 (2)0.020 (11)*
P11.20178 (6)0.28650 (9)0.73888 (6)0.0239 (3)
P21.10074 (7)0.40362 (9)0.80500 (6)0.0269 (3)
P30.94640 (6)0.35370 (9)0.72144 (6)0.0251 (3)
P40.97290 (6)0.13964 (9)0.70074 (6)0.0260 (3)
Cl11.14187 (7)0.05475 (9)0.68044 (7)0.0383 (3)
C41.0599 (2)0.2604 (3)0.6113 (3)0.0278 (11)
N11.0392 (2)0.2906 (3)0.5559 (2)0.0486 (12)
C11.0385 (2)0.3332 (3)0.7501 (2)0.0250 (11)
C21.1831 (2)0.4124 (3)0.7662 (3)0.0279 (11)
H2A1.22560.43750.80090.034*
H2B1.17380.45650.72520.034*
C30.9069 (2)0.2410 (3)0.6795 (3)0.0314 (12)
H3A0.89410.25020.62810.038*
H3B0.86100.22520.69580.038*
C1011.2526 (2)0.3058 (3)0.6676 (2)0.0268 (11)
C1021.2477 (3)0.2350 (4)0.6151 (3)0.0390 (13)
H1021.21890.17830.61670.047*
C1031.2852 (3)0.2482 (4)0.5605 (3)0.0518 (16)
H1031.28250.19960.52560.062*
C1041.3261 (3)0.3312 (4)0.5567 (3)0.0473 (15)
H1041.35090.33970.51910.057*
C1051.3309 (3)0.4013 (4)0.6076 (3)0.0468 (15)
H1051.35890.45830.60460.056*
C1061.2951 (3)0.3896 (4)0.6638 (3)0.0386 (13)
H1061.29940.43800.69910.046*
C1071.2722 (2)0.2390 (3)0.8118 (2)0.0260 (11)
C1081.2622 (3)0.1486 (4)0.8407 (3)0.0377 (13)
H1081.21990.11110.82100.045*
C1091.3127 (3)0.1120 (4)0.8979 (3)0.0500 (15)
H1091.30510.04990.91640.060*
C1101.3737 (3)0.1661 (4)0.9276 (3)0.0468 (15)
H1101.40710.14270.96780.056*
C1111.3864 (3)0.2544 (4)0.8988 (3)0.0451 (14)
H1111.42950.29020.91830.054*
C1121.3361 (2)0.2916 (4)0.8411 (3)0.0380 (12)
H1121.34520.35250.82170.046*
C2011.0711 (3)0.5264 (4)0.8215 (3)0.0333 (12)
C2021.0762 (3)0.6032 (4)0.7762 (3)0.0463 (14)
H2021.09880.59330.73720.056*
C2031.0482 (3)0.6950 (4)0.7877 (4)0.0652 (18)
H2031.05150.74680.75640.078*
C2041.0159 (3)0.7098 (5)0.8444 (4)0.0659 (19)
H2040.99630.77180.85150.079*
C2051.0116 (4)0.6357 (5)0.8910 (4)0.071 (2)
H2050.99000.64690.93050.085*
C2061.0394 (3)0.5437 (4)0.8798 (3)0.0479 (15)
H2061.03670.49270.91190.058*
C2071.1346 (3)0.3515 (4)0.8923 (3)0.0338 (12)
C2081.0916 (3)0.2794 (4)0.9159 (3)0.0468 (14)
H2081.04720.25810.88640.056*
C2091.1141 (4)0.2391 (5)0.9828 (3)0.0690 (19)
H2091.08400.19180.99870.083*
C2101.1788 (4)0.2670 (5)1.0253 (3)0.073 (2)
H2101.19420.23781.07000.088*
C2111.2217 (4)0.3377 (6)1.0034 (3)0.0672 (19)
H2111.26610.35771.03360.081*
C2121.2001 (3)0.3807 (4)0.9364 (3)0.0499 (15)
H2121.23000.42910.92150.060*
C3010.9145 (2)0.4436 (3)0.6526 (2)0.0277 (11)
C3020.9642 (3)0.4980 (4)0.6233 (3)0.0395 (13)
H3021.01570.49130.64080.047*
C3030.9379 (3)0.5629 (4)0.5678 (3)0.0450 (14)
H3030.97200.60040.54860.054*
C3040.8632 (3)0.5723 (4)0.5411 (3)0.0451 (14)
H3040.84580.61720.50450.054*
C3050.8135 (3)0.5153 (4)0.5686 (3)0.0518 (16)
H3050.76210.52050.54980.062*
C3060.8386 (3)0.4512 (4)0.6230 (3)0.0406 (14)
H3060.80440.41190.64060.049*
C3070.8966 (2)0.3862 (4)0.7904 (3)0.0309 (12)
C3080.8912 (3)0.3181 (4)0.8417 (3)0.0546 (17)
H3080.90990.25450.83820.066*
C3090.8585 (4)0.3418 (5)0.8983 (4)0.081 (2)
H3090.85510.29430.93280.097*
C3100.8316 (4)0.4334 (5)0.9041 (4)0.078 (2)
H3100.81020.44950.94290.094*
C3110.8354 (3)0.5022 (5)0.8537 (3)0.0642 (18)
H3110.81600.56530.85740.077*
C3120.8682 (3)0.4788 (4)0.7965 (3)0.0463 (14)
H3120.87100.52640.76200.056*
C4010.9435 (3)0.0522 (4)0.6292 (3)0.0346 (13)
C4020.9211 (3)0.0818 (4)0.5597 (3)0.0501 (15)
H4020.91820.14920.54940.060*
C4030.9029 (3)0.0156 (5)0.5046 (4)0.0666 (19)
H4030.88760.03810.45790.080*
C4040.9073 (3)−0.0821 (5)0.5184 (4)0.0650 (19)
H4040.8935−0.12730.48130.078*
C4050.9314 (4)−0.1145 (5)0.5855 (4)0.068 (2)
H4050.9358−0.18210.59450.082*
C4060.9502 (3)−0.0471 (4)0.6425 (3)0.0548 (16)
H4060.9671−0.07000.68890.066*
C4070.9433 (3)0.0784 (3)0.7744 (3)0.0332 (12)
C4080.9928 (3)0.0573 (4)0.8363 (3)0.0524 (16)
H4081.04330.07380.84070.063*
C4090.9695 (4)0.0124 (5)0.8918 (3)0.077 (2)
H4091.0043−0.00320.93330.092*
C4100.8955 (4)−0.0098 (5)0.8868 (4)0.083 (2)
H4100.8793−0.03850.92530.099*
C4110.8463 (4)0.0098 (5)0.8266 (5)0.084 (2)
H4110.7958−0.00600.82320.101*
C4120.8689 (3)0.0531 (4)0.7694 (3)0.0580 (17)
H4120.83400.06520.72730.070*
N20.7247 (3)0.2498 (6)0.7077 (4)0.103 (2)
C50.6995 (4)0.2484 (5)0.7548 (5)0.077 (2)
C60.6679 (6)0.2427 (8)0.8163 (5)0.158 (5)
H6A0.66290.17450.82870.237*
H6B0.61910.27350.80680.237*
H6C0.70000.27610.85530.237*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.02357 (11)0.02054 (11)0.02067 (10)0.00045 (9)0.00230 (7)−0.00009 (9)
P10.0248 (6)0.0235 (7)0.0224 (6)0.0009 (5)0.0023 (5)−0.0005 (6)
P20.0297 (7)0.0253 (7)0.0254 (7)0.0017 (5)0.0049 (5)−0.0042 (6)
P30.0262 (7)0.0263 (7)0.0235 (7)0.0017 (5)0.0062 (5)0.0006 (6)
P40.0261 (7)0.0241 (7)0.0268 (7)−0.0007 (5)0.0028 (5)0.0003 (6)
Cl10.0443 (8)0.0313 (7)0.0376 (8)0.0043 (6)0.0040 (6)−0.0016 (6)
C40.027 (3)0.023 (3)0.034 (3)−0.001 (2)0.008 (2)−0.002 (2)
N10.063 (3)0.050 (3)0.031 (3)0.001 (2)0.004 (2)0.013 (3)
C10.024 (3)0.030 (3)0.022 (3)−0.002 (2)0.007 (2)0.002 (2)
C20.027 (3)0.023 (3)0.034 (3)0.000 (2)0.006 (2)0.000 (2)
C30.032 (3)0.030 (3)0.032 (3)−0.002 (2)0.004 (2)0.001 (2)
C1010.025 (3)0.029 (3)0.027 (3)0.004 (2)0.007 (2)0.008 (2)
C1020.043 (3)0.035 (3)0.041 (3)−0.008 (2)0.014 (3)−0.013 (3)
C1030.068 (4)0.056 (4)0.039 (3)−0.008 (3)0.028 (3)−0.018 (3)
C1040.046 (4)0.061 (4)0.041 (4)0.002 (3)0.023 (3)0.005 (3)
C1050.048 (4)0.044 (4)0.056 (4)−0.007 (3)0.027 (3)0.007 (3)
C1060.039 (3)0.032 (3)0.046 (3)−0.002 (2)0.011 (3)−0.005 (3)
C1070.029 (3)0.022 (3)0.026 (3)0.004 (2)0.003 (2)−0.001 (2)
C1080.031 (3)0.038 (3)0.039 (3)−0.004 (2)−0.005 (2)0.006 (3)
C1090.049 (4)0.048 (4)0.045 (4)−0.002 (3)−0.010 (3)0.017 (3)
C1100.034 (3)0.063 (4)0.037 (3)0.008 (3)−0.008 (3)0.005 (3)
C1110.035 (3)0.050 (4)0.044 (3)−0.001 (3)−0.006 (3)−0.007 (3)
C1120.029 (3)0.033 (3)0.049 (3)−0.004 (2)0.001 (2)−0.003 (3)
C2010.031 (3)0.030 (3)0.038 (3)0.001 (2)0.005 (2)−0.007 (3)
C2020.045 (3)0.037 (4)0.057 (4)0.005 (3)0.012 (3)−0.007 (3)
C2030.073 (4)0.035 (4)0.087 (5)0.011 (3)0.017 (4)0.000 (4)
C2040.056 (4)0.040 (4)0.101 (6)0.011 (3)0.012 (4)−0.028 (4)
C2050.077 (5)0.060 (5)0.083 (5)0.012 (4)0.033 (4)−0.033 (4)
C2060.055 (4)0.039 (3)0.052 (4)0.005 (3)0.018 (3)−0.013 (3)
C2070.035 (3)0.037 (3)0.028 (3)0.007 (2)0.001 (2)−0.007 (3)
C2080.058 (4)0.048 (4)0.032 (3)0.003 (3)0.005 (3)−0.002 (3)
C2090.101 (6)0.068 (5)0.035 (4)0.012 (4)0.009 (4)0.019 (3)
C2100.099 (6)0.088 (6)0.029 (4)0.032 (5)0.003 (4)0.008 (4)
C2110.064 (4)0.097 (6)0.031 (4)0.015 (4)−0.012 (3)−0.009 (4)
C2120.049 (4)0.068 (4)0.031 (3)0.000 (3)0.004 (3)−0.008 (3)
C3010.027 (3)0.027 (3)0.028 (3)0.003 (2)0.005 (2)0.002 (2)
C3020.032 (3)0.043 (3)0.043 (3)−0.002 (2)0.005 (2)0.012 (3)
C3030.053 (4)0.042 (3)0.039 (3)−0.006 (3)0.009 (3)0.019 (3)
C3040.055 (4)0.042 (3)0.036 (3)0.009 (3)0.005 (3)0.017 (3)
C3050.038 (3)0.066 (4)0.049 (4)0.014 (3)0.003 (3)0.017 (3)
C3060.035 (3)0.045 (3)0.043 (3)0.008 (2)0.008 (3)0.015 (3)
C3070.028 (3)0.034 (3)0.031 (3)0.005 (2)0.005 (2)−0.001 (3)
C3080.070 (4)0.050 (4)0.055 (4)0.018 (3)0.037 (3)0.011 (3)
C3090.136 (7)0.060 (5)0.065 (5)0.022 (4)0.064 (5)0.022 (4)
C3100.118 (6)0.076 (5)0.056 (5)0.015 (5)0.057 (4)0.004 (4)
C3110.081 (5)0.058 (4)0.062 (4)0.022 (3)0.034 (4)−0.011 (4)
C3120.056 (4)0.045 (4)0.040 (3)0.013 (3)0.016 (3)0.007 (3)
C4010.025 (3)0.034 (3)0.045 (3)−0.007 (2)0.008 (2)−0.012 (3)
C4020.056 (4)0.055 (4)0.036 (3)−0.013 (3)0.002 (3)−0.017 (3)
C4030.059 (4)0.085 (6)0.054 (4)−0.014 (4)0.009 (3)−0.032 (4)
C4040.064 (4)0.063 (5)0.065 (5)−0.012 (4)0.007 (4)−0.035 (4)
C4050.070 (4)0.033 (4)0.104 (6)−0.009 (3)0.023 (4)−0.026 (4)
C4060.057 (4)0.039 (4)0.067 (4)−0.001 (3)0.009 (3)−0.002 (3)
C4070.035 (3)0.029 (3)0.037 (3)−0.002 (2)0.009 (2)0.007 (3)
C4080.044 (4)0.063 (4)0.052 (4)0.001 (3)0.015 (3)0.024 (3)
C4090.069 (5)0.109 (6)0.055 (4)0.004 (4)0.019 (3)0.047 (4)
C4100.077 (5)0.094 (6)0.090 (6)0.002 (4)0.048 (5)0.049 (5)
C4110.057 (5)0.092 (6)0.117 (7)−0.007 (4)0.048 (5)0.042 (5)
C4120.039 (4)0.063 (4)0.073 (5)−0.007 (3)0.013 (3)0.024 (4)
N20.065 (4)0.171 (7)0.072 (5)−0.012 (4)0.011 (4)−0.009 (5)
C50.088 (6)0.066 (5)0.082 (6)0.003 (4)0.029 (5)−0.008 (5)
C60.197 (11)0.182 (11)0.126 (9)−0.015 (9)0.104 (9)−0.010 (8)
Geometric parameters (Å, º) top
Ir1—P12.3020 (12)C207—C2081.395 (7)
Ir1—P42.2766 (12)C208—C2091.385 (7)
Ir1—C12.128 (4)C208—H2080.9400
Ir1—Cl12.4446 (12)C209—C2101.352 (9)
Ir1—C42.081 (5)C209—H2090.9400
Ir1—H11.51 (4)C210—C2111.365 (9)
P1—C1071.823 (5)C210—H2100.9400
P1—C1011.831 (4)C211—C2121.402 (8)
P1—C21.850 (4)C211—H2110.9400
P2—C11.690 (5)C212—H2120.9400
P2—C2011.810 (5)C301—C3021.382 (6)
P2—C2071.817 (5)C301—C3061.394 (6)
P2—C21.821 (4)C302—C3031.398 (7)
P3—C11.688 (4)C302—H3020.9400
P3—C3011.816 (5)C303—C3041.366 (7)
P3—C3071.817 (5)C303—H3030.9400
P3—C31.818 (5)C304—C3051.385 (7)
P4—C4011.822 (5)C304—H3040.9400
P4—C4071.826 (5)C305—C3061.372 (7)
P4—C31.828 (5)C305—H3050.9400
C4—N11.136 (6)C306—H3060.9400
C2—H2A0.9800C307—C3081.375 (7)
C2—H2B0.9800C307—C3121.380 (7)
C3—H3A0.9800C308—C3091.388 (7)
C3—H3B0.9800C308—H3080.9400
C101—C1021.391 (6)C309—C3101.357 (9)
C101—C1061.393 (6)C309—H3090.9400
C102—C1031.382 (7)C310—C3111.365 (8)
C102—H1020.9400C310—H3100.9400
C103—C1041.368 (7)C311—C3121.397 (7)
C103—H1030.9400C311—H3110.9400
C104—C1051.360 (7)C312—H3120.9400
C104—H1040.9400C401—C4061.379 (7)
C105—C1061.389 (7)C401—C4021.381 (7)
C105—H1050.9400C402—C4031.383 (7)
C106—H1060.9400C402—H4020.9400
C107—C1081.382 (6)C403—C4041.358 (9)
C107—C1121.391 (6)C403—H4030.9400
C108—C1091.381 (7)C404—C4051.355 (9)
C108—H1080.9400C404—H4040.9400
C109—C1101.365 (7)C405—C4061.420 (8)
C109—H1090.9400C405—H4050.9400
C110—C1111.366 (7)C406—H4060.9400
C110—H1100.9400C407—C4081.374 (7)
C111—C1121.390 (7)C407—C4121.389 (7)
C111—H1110.9400C408—C4091.376 (7)
C112—H1120.9400C408—H4080.9400
C201—C2021.381 (7)C409—C4101.374 (8)
C201—C2061.388 (7)C409—H4090.9400
C202—C2031.388 (7)C410—C4111.344 (9)
C202—H2020.9400C410—H4100.9400
C203—C2041.361 (9)C411—C4121.388 (8)
C203—H2030.9400C411—H4110.9400
C204—C2051.367 (9)C412—H4120.9400
C204—H2040.9400N2—C51.101 (8)
C205—C2061.388 (8)C5—C61.427 (10)
C205—H2050.9400C6—H6A0.9700
C206—H2060.9400C6—H6B0.9700
C207—C2121.380 (7)C6—H6C0.9700
C4—Ir1—C189.27 (17)C204—C205—C206119.6 (6)
C4—Ir1—P489.08 (12)C204—C205—H205120.2
C1—Ir1—P484.94 (12)C206—C205—H205120.2
C4—Ir1—P194.22 (12)C201—C206—C205120.5 (6)
C1—Ir1—P189.10 (12)C201—C206—H206119.7
P4—Ir1—P1173.16 (4)C205—C206—H206119.7
C4—Ir1—Cl194.42 (13)C212—C207—C208118.7 (5)
C1—Ir1—Cl1175.28 (12)C212—C207—P2123.2 (4)
P4—Ir1—Cl192.17 (4)C208—C207—P2118.1 (4)
P1—Ir1—Cl193.55 (4)C209—C208—C207120.3 (6)
C4—Ir1—H1176.6 (13)C209—C208—H208119.8
C1—Ir1—H187.8 (14)C207—C208—H208119.8
P4—Ir1—H189.0 (13)C210—C209—C208120.7 (7)
P1—Ir1—H187.4 (13)C210—C209—H209119.7
Cl1—Ir1—H188.4 (14)C208—C209—H209119.7
C107—P1—C101104.0 (2)C209—C210—C211120.0 (6)
C107—P1—C2104.7 (2)C209—C210—H210120.0
C101—P1—C2103.4 (2)C211—C210—H210120.0
C107—P1—Ir1117.25 (15)C210—C211—C212120.7 (6)
C101—P1—Ir1119.28 (16)C210—C211—H211119.7
C2—P1—Ir1106.46 (14)C212—C211—H211119.7
C1—P2—C201116.7 (2)C207—C212—C211119.6 (6)
C1—P2—C207114.7 (2)C207—C212—H212120.2
C201—P2—C207104.9 (2)C211—C212—H212120.2
C1—P2—C2106.8 (2)C302—C301—C306118.6 (4)
C201—P2—C2108.4 (2)C302—C301—P3121.4 (4)
C207—P2—C2104.6 (2)C306—C301—P3119.7 (4)
C1—P3—C301120.2 (2)C301—C302—C303120.0 (5)
C1—P3—C307114.8 (2)C301—C302—H302120.0
C301—P3—C307103.7 (2)C303—C302—H302120.0
C1—P3—C3106.6 (2)C304—C303—C302120.7 (5)
C301—P3—C3101.9 (2)C304—C303—H303119.7
C307—P3—C3108.6 (2)C302—C303—H303119.7
C401—P4—C407101.6 (2)C303—C304—C305119.4 (5)
C401—P4—C3104.2 (2)C303—C304—H304120.3
C407—P4—C3103.4 (2)C305—C304—H304120.3
C401—P4—Ir1118.52 (15)C306—C305—C304120.4 (5)
C407—P4—Ir1120.92 (17)C306—C305—H305119.8
C3—P4—Ir1106.10 (15)C304—C305—H305119.8
N1—C4—Ir1175.0 (4)C305—C306—C301120.8 (5)
P3—C1—P2127.8 (3)C305—C306—H306119.6
P3—C1—Ir1119.7 (2)C301—C306—H306119.6
P2—C1—Ir1112.5 (2)C308—C307—C312118.3 (5)
P2—C2—P1105.9 (2)C308—C307—P3118.9 (4)
P2—C2—H2A110.6C312—C307—P3122.7 (4)
P1—C2—H2A110.6C307—C308—C309121.0 (5)
P2—C2—H2B110.6C307—C308—H308119.5
P1—C2—H2B110.6C309—C308—H308119.5
H2A—C2—H2B108.7C310—C309—C308120.1 (6)
P3—C3—P4110.8 (2)C310—C309—H309119.9
P3—C3—H3A109.5C308—C309—H309119.9
P4—C3—H3A109.5C309—C310—C311120.2 (6)
P3—C3—H3B109.5C309—C310—H310119.9
P4—C3—H3B109.5C311—C310—H310119.9
H3A—C3—H3B108.1C310—C311—C312119.9 (6)
C102—C101—C106119.0 (4)C310—C311—H311120.1
C102—C101—P1118.7 (4)C312—C311—H311120.1
C106—C101—P1122.2 (4)C307—C312—C311120.5 (5)
C103—C102—C101119.8 (5)C307—C312—H312119.7
C103—C102—H102120.1C311—C312—H312119.7
C101—C102—H102120.1C406—C401—C402117.7 (5)
C104—C103—C102120.8 (5)C406—C401—P4120.1 (4)
C104—C103—H103119.6C402—C401—P4121.9 (4)
C102—C103—H103119.6C401—C402—C403122.2 (6)
C105—C104—C103119.9 (5)C401—C402—H402118.9
C105—C104—H104120.1C403—C402—H402118.9
C103—C104—H104120.1C404—C403—C402119.7 (7)
C104—C105—C106120.8 (5)C404—C403—H403120.1
C104—C105—H105119.6C402—C403—H403120.1
C106—C105—H105119.6C405—C404—C403120.1 (6)
C105—C106—C101119.6 (5)C405—C404—H404119.9
C105—C106—H106120.2C403—C404—H404119.9
C101—C106—H106120.2C404—C405—C406120.6 (6)
C108—C107—C112117.8 (4)C404—C405—H405119.7
C108—C107—P1119.9 (4)C406—C405—H405119.7
C112—C107—P1122.3 (4)C401—C406—C405119.6 (6)
C109—C108—C107121.5 (5)C401—C406—H406120.2
C109—C108—H108119.2C405—C406—H406120.2
C107—C108—H108119.2C408—C407—C412118.2 (5)
C110—C109—C108119.8 (5)C408—C407—P4121.6 (4)
C110—C109—H109120.1C412—C407—P4120.2 (4)
C108—C109—H109120.1C407—C408—C409121.0 (5)
C109—C110—C111120.0 (5)C407—C408—H408119.5
C109—C110—H110120.0C409—C408—H408119.5
C111—C110—H110120.0C410—C409—C408120.2 (6)
C110—C111—C112120.5 (5)C410—C409—H409119.9
C110—C111—H111119.7C408—C409—H409119.9
C112—C111—H111119.7C411—C410—C409119.6 (6)
C111—C112—C107120.2 (5)C411—C410—H410120.2
C111—C112—H112119.9C409—C410—H410120.2
C107—C112—H112119.9C410—C411—C412121.1 (6)
C202—C201—C206118.6 (5)C410—C411—H411119.4
C202—C201—P2122.0 (4)C412—C411—H411119.4
C206—C201—P2119.4 (4)C411—C412—C407119.8 (6)
C201—C202—C203120.5 (6)C411—C412—H412120.1
C201—C202—H202119.7C407—C412—H412120.1
C203—C202—H202119.7N2—C5—C6177.6 (10)
C204—C203—C202119.9 (6)C5—C6—H6A109.5
C204—C203—H203120.1C5—C6—H6B109.5
C202—C203—H203120.1H6A—C6—H6B109.5
C203—C204—C205120.8 (6)C5—C6—H6C109.5
C203—C204—H204119.6H6A—C6—H6C109.5
C205—C204—H204119.6H6B—C6—H6C109.5
C301—P3—C1—P276.6 (4)C2—P2—C207—C21242.9 (5)
C307—P3—C1—P2−48.1 (4)C1—P2—C207—C208−21.3 (5)
C3—P3—C1—P2−168.3 (3)C201—P2—C207—C208108.0 (4)
C301—P3—C1—Ir1−101.9 (3)C2—P2—C207—C208−138.0 (4)
C307—P3—C1—Ir1133.4 (2)C212—C207—C208—C2090.7 (8)
C3—P3—C1—Ir113.1 (3)P2—C207—C208—C209−178.4 (4)
C201—P2—C1—P3−13.5 (4)C207—C208—C209—C210−1.7 (9)
C207—P2—C1—P3109.7 (3)C208—C209—C210—C2111.9 (10)
C2—P2—C1—P3−134.9 (3)C209—C210—C211—C212−1.2 (10)
C201—P2—C1—Ir1165.1 (2)C208—C207—C212—C211−0.1 (8)
C207—P2—C1—Ir1−71.7 (3)P2—C207—C212—C211179.0 (4)
C2—P2—C1—Ir143.7 (3)C210—C211—C212—C2070.3 (9)
C1—P2—C2—P1−45.5 (3)C1—P3—C301—C302−1.3 (5)
C201—P2—C2—P1−172.0 (2)C307—P3—C301—C302128.6 (4)
C207—P2—C2—P176.5 (3)C3—P3—C301—C302−118.7 (4)
C107—P1—C2—P2−96.5 (2)C1—P3—C301—C306171.8 (4)
C101—P1—C2—P2154.8 (2)C307—P3—C301—C306−58.3 (4)
Ir1—P1—C2—P228.3 (2)C3—P3—C301—C30654.4 (4)
C1—P3—C3—P413.2 (3)C306—C301—C302—C3033.4 (8)
C301—P3—C3—P4140.1 (2)P3—C301—C302—C303176.6 (4)
C307—P3—C3—P4−110.9 (3)C301—C302—C303—C304−1.0 (8)
C401—P4—C3—P3−156.9 (2)C302—C303—C304—C305−1.4 (8)
C407—P4—C3—P397.2 (3)C303—C304—C305—C3061.3 (9)
Ir1—P4—C3—P3−31.1 (3)C304—C305—C306—C3011.2 (8)
C107—P1—C101—C10298.8 (4)C302—C301—C306—C305−3.6 (8)
C2—P1—C101—C102−152.1 (4)P3—C301—C306—C305−176.9 (4)
Ir1—P1—C101—C102−34.2 (4)C1—P3—C307—C308−65.0 (5)
C107—P1—C101—C106−82.2 (4)C301—P3—C307—C308161.9 (4)
C2—P1—C101—C10627.0 (4)C3—P3—C307—C30854.1 (5)
Ir1—P1—C101—C106144.9 (3)C1—P3—C307—C312110.4 (4)
C106—C101—C102—C1030.5 (7)C301—P3—C307—C312−22.6 (5)
P1—C101—C102—C103179.6 (4)C3—P3—C307—C312−130.4 (4)
C101—C102—C103—C104−1.2 (9)C312—C307—C308—C309−0.4 (9)
C102—C103—C104—C1050.8 (9)P3—C307—C308—C309175.2 (5)
C103—C104—C105—C1060.4 (9)C307—C308—C309—C310−0.3 (11)
C104—C105—C106—C101−1.1 (8)C308—C309—C310—C3111.0 (12)
C102—C101—C106—C1050.6 (7)C309—C310—C311—C312−1.0 (11)
P1—C101—C106—C105−178.5 (4)C308—C307—C312—C3110.4 (8)
C101—P1—C107—C108−121.7 (4)P3—C307—C312—C311−175.1 (5)
C2—P1—C107—C108130.1 (4)C310—C311—C312—C3070.3 (10)
Ir1—P1—C107—C10812.4 (4)C407—P4—C401—C406−38.3 (5)
C101—P1—C107—C11259.7 (4)C3—P4—C401—C406−145.5 (4)
C2—P1—C107—C112−48.5 (4)Ir1—P4—C401—C40696.9 (4)
Ir1—P1—C107—C112−166.2 (3)C407—P4—C401—C402148.4 (4)
C112—C107—C108—C1091.4 (7)C3—P4—C401—C40241.2 (5)
P1—C107—C108—C109−177.2 (4)Ir1—P4—C401—C402−76.4 (4)
C107—C108—C109—C1100.8 (8)C406—C401—C402—C4032.6 (8)
C108—C109—C110—C111−2.8 (9)P4—C401—C402—C403176.1 (4)
C109—C110—C111—C1122.5 (8)C401—C402—C403—C404−0.4 (9)
C110—C111—C112—C107−0.2 (8)C402—C403—C404—C405−2.0 (10)
C108—C107—C112—C111−1.7 (7)C403—C404—C405—C4062.0 (10)
P1—C107—C112—C111176.9 (4)C402—C401—C406—C405−2.5 (8)
C1—P2—C201—C202−84.0 (5)P4—C401—C406—C405−176.1 (4)
C207—P2—C201—C202147.9 (4)C404—C405—C406—C4010.3 (9)
C2—P2—C201—C20236.6 (5)C401—P4—C407—C408123.2 (5)
C1—P2—C201—C20693.2 (5)C3—P4—C407—C408−129.0 (5)
C207—P2—C201—C206−34.9 (5)Ir1—P4—C407—C408−10.6 (5)
C2—P2—C201—C206−146.2 (4)C401—P4—C407—C412−57.8 (5)
C206—C201—C202—C203−1.8 (8)C3—P4—C407—C41250.1 (5)
P2—C201—C202—C203175.4 (4)Ir1—P4—C407—C412168.5 (4)
C201—C202—C203—C2040.4 (9)C412—C407—C408—C409−0.1 (9)
C202—C203—C204—C2051.1 (10)P4—C407—C408—C409179.0 (5)
C203—C204—C205—C206−1.1 (10)C407—C408—C409—C410−1.7 (11)
C202—C201—C206—C2051.7 (8)C408—C409—C410—C4112.1 (12)
P2—C201—C206—C205−175.6 (5)C409—C410—C411—C412−0.6 (13)
C204—C205—C206—C201−0.2 (9)C410—C411—C412—C407−1.2 (11)
C1—P2—C207—C212159.6 (4)C408—C407—C412—C4111.5 (9)
C201—P2—C207—C212−71.0 (5)P4—C407—C412—C411−177.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3B···N20.982.583.4925 (1)156
C102—H102···Cl10.942.663.5216 (1)153
C112—H112···Cl1i0.942.773.6470 (1)155
C210—H210···N2ii0.942.613.4554 (1)150
C303—H303···N1iii0.942.483.2064 (1)134
Symmetry codes: (i) −x+5/2, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+2, −y+1, −z+1.
[7-(4-Chlorophenyl)-1,1,3,3-tetraphenyl-5,6,7-triaza-κN7-1,3λ4-diphospha-κP1-hepta-4,6-dien-4-yl][methylenebis(diphenylphosphine)-κ2P,P']iridium(I) chloride–dichloromethane–toluene (2/3/1) (2) top
Crystal data top
[Ir(C25H22P2)(C32H26ClN3P2)]Cl·0.5C7H8·1.5CH2Cl2Dx = 1.397 Mg m−3
Mr = 1335.42Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcnCell parameters from 221720 reflections
a = 28.1283 (3) Åθ = 1.0–26.0°
b = 19.0989 (2) ŵ = 2.45 mm−1
c = 23.6339 (2) ÅT = 233 K
V = 12696.6 (2) Å3Prism, red-brown
Z = 80.3 × 0.2 × 0.15 mm
F(000) = 5360
Data collection top
Nonius KappaCCD
diffractometer		Rint = 0.039
phi– and ω–scansθmax = 25.0°, θmin = 1.9°
73594 measured reflectionsh = −33→33
11155 independent reflectionsk = −22→22
9002 reflections with I > 2σ(I)l = −19→28
Refinement top
Refinement on F230 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0615P)2 + 44.6168P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
11155 reflectionsΔρmax = 1.66 e Å−3
724 parametersΔρmin = −0.73 e Å−3
Special details top

Experimental. All data sets were measured with several scans to increase the number of redundant reflections. In our experience this method of averaging redundant reflections replaces in a good approximation semi-empirical absorption methods (absorption correction programs like SORTAV lead to no better data sets).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. 2:1 positional disorder of the counter anion Cl1:Cl1A. The solvent molecules CH2Cl2 and C7H8 show occupational disorder, whereas the toluene shows additional positional disorder of ratio 1:1 with some nearly overlying carbon atoms. We think, because of short intermolecular Cl···C contacts between CH2Cl2 and C7H8, that there is a correlation between these molecules. Therefore, the two solvate molecules Cl3—C10–l4 and Cl5—C11—Cl6 have an occupancy of 0.75 and the `two' toluene molecules, C12–C18 and C19–C25, an occupancy of 0.25. Several bond restraints must be used to refine the toluene carbon atoms reasonably isotropically.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ir10.37466 (2)0.64909 (2)−0.05631 (2)0.03621 (9)
P10.32978 (5)0.71589 (7)−0.11572 (6)0.0422 (3)
P20.35994 (5)0.59865 (8)−0.19050 (6)0.0410 (3)
P30.36065 (6)0.70441 (8)0.03213 (6)0.0451 (3)
P40.31226 (5)0.59668 (8)−0.01288 (6)0.0437 (3)
Cl10.26332 (16)0.71646 (19)−0.30485 (14)0.0456 (8)0.65
Cl1A0.2678 (3)0.7368 (3)−0.3219 (2)0.0476 (18)0.35
Cl20.57143 (7)0.68950 (13)0.14255 (9)0.0891 (6)
N10.44176 (16)0.6172 (2)−0.04574 (17)0.0402 (10)
N20.46127 (17)0.5721 (3)−0.08336 (19)0.0470 (11)
N30.43390 (16)0.5618 (2)−0.12734 (19)0.0454 (11)
C10.3915 (2)0.5945 (3)−0.1255 (2)0.0405 (12)
C20.3129 (2)0.6596 (3)−0.1760 (2)0.0431 (12)
H2A0.28370.6341−0.16700.052*
H2B0.30700.6886−0.20950.052*
C30.3010 (2)0.6647 (3)0.0405 (3)0.0524 (14)
H3A0.29560.64560.07840.063*
H3B0.27520.69650.02990.063*
C40.47418 (19)0.6336 (3)−0.0010 (2)0.0421 (12)
C50.4929 (2)0.6995 (3)0.0022 (3)0.0575 (15)
H50.48460.7332−0.02500.069*
C60.5240 (2)0.7170 (4)0.0453 (3)0.0654 (18)
H60.53730.76220.04740.078*
C70.5352 (2)0.6665 (4)0.0852 (3)0.0607 (17)
C80.5178 (2)0.6007 (4)0.0822 (3)0.0576 (16)
H80.52660.56690.10910.069*
C90.4868 (2)0.5838 (3)0.0388 (3)0.0539 (15)
H90.47430.53830.03640.065*
C1010.2731 (2)0.7563 (3)−0.0966 (2)0.0506 (14)
C1020.2743 (3)0.8171 (4)−0.0636 (3)0.0679 (19)
H1020.30340.8384−0.05450.081*
C1030.2310 (4)0.8460 (5)−0.0439 (3)0.084 (3)
H1030.23120.8864−0.02110.101*
C1040.1885 (4)0.8149 (6)−0.0582 (4)0.094 (3)
H1040.15990.8339−0.04450.113*
C1050.1871 (3)0.7572 (5)−0.0918 (4)0.090 (3)
H1050.15780.7374−0.10240.108*
C1060.2295 (2)0.7277 (4)−0.1104 (3)0.0679 (18)
H1060.22840.6872−0.13300.081*
C1070.3610 (2)0.7881 (3)−0.1498 (2)0.0525 (15)
C1080.4091 (3)0.7953 (4)−0.1443 (3)0.073 (2)
H1080.42610.7643−0.12090.088*
C1090.4331 (4)0.8475 (5)−0.1729 (5)0.107 (3)
H1090.46610.8523−0.16850.129*
C1100.4091 (5)0.8922 (5)−0.2075 (5)0.113 (4)
H1100.42550.9278−0.22670.136*
C1110.3607 (4)0.8854 (4)−0.2143 (4)0.098 (3)
H1110.34420.9157−0.23880.117*
C1120.3369 (3)0.8348 (4)−0.1857 (3)0.070 (2)
H1120.30380.8309−0.19000.084*
C2010.3333 (2)0.5177 (3)−0.2137 (2)0.0485 (13)
C2020.3455 (2)0.4540 (3)−0.1901 (3)0.0620 (17)
H2020.36840.4521−0.16110.074*
C2030.3240 (3)0.3927 (4)−0.2092 (4)0.079 (2)
H2030.33260.3494−0.19320.095*
C2040.2907 (3)0.3951 (4)−0.2508 (3)0.076 (2)
H2040.27640.3535−0.26370.091*
C2050.2776 (3)0.4592 (5)−0.2743 (3)0.081 (2)
H2050.25430.4607−0.30270.097*
C2060.2988 (2)0.5206 (4)−0.2560 (3)0.0653 (17)
H2060.29000.5638−0.27200.078*
C2070.3977 (2)0.6277 (3)−0.2470 (2)0.0485 (13)
C2080.4304 (3)0.5804 (4)−0.2676 (3)0.0675 (18)
H2080.43140.5345−0.25310.081*
C2090.4618 (3)0.6005 (5)−0.3096 (3)0.084 (2)
H2090.48310.5674−0.32450.101*
C2100.4627 (3)0.6665 (5)−0.3295 (3)0.080 (2)
H2100.48550.6798−0.35650.096*
C2110.4296 (4)0.7149 (5)−0.3102 (3)0.090 (3)
H2110.42950.7608−0.32460.108*
C2120.3961 (3)0.6950 (4)−0.2688 (3)0.071 (2)
H2120.37300.7269−0.25610.085*
C3010.3552 (2)0.7980 (3)0.0390 (3)0.0555 (15)
C3020.3843 (3)0.8405 (4)0.0069 (4)0.073 (2)
H3020.40620.8204−0.01850.087*
C3030.3814 (4)0.9136 (5)0.0121 (5)0.108 (3)
H3030.40090.9430−0.00980.130*
C3040.3495 (5)0.9411 (5)0.0500 (6)0.119 (4)
H3040.34720.99000.05360.143*
C3050.3215 (4)0.9003 (5)0.0819 (4)0.099 (3)
H3050.30040.92110.10780.119*
C3060.3230 (3)0.8279 (4)0.0774 (3)0.072 (2)
H3060.30300.79950.09950.087*
C3070.3913 (2)0.6819 (4)0.0979 (2)0.0531 (15)
C3080.4215 (3)0.7297 (5)0.1240 (3)0.076 (2)
H3080.42720.77320.10680.092*
C3090.4432 (3)0.7140 (6)0.1749 (4)0.090 (3)
H3090.46270.74720.19280.108*
C3100.4358 (3)0.6490 (6)0.1991 (3)0.097 (3)
H3100.45110.63760.23330.116*
C3110.4066 (4)0.6015 (6)0.1741 (4)0.107 (3)
H3110.40130.55770.19120.129*
C3120.3845 (3)0.6181 (5)0.1232 (3)0.086 (2)
H3120.36460.58490.10580.103*
C4010.2564 (2)0.5722 (3)−0.0459 (2)0.0507 (14)
C4020.2583 (2)0.5251 (4)−0.0908 (3)0.0604 (16)
H4020.28790.5079−0.10320.072*
C4030.2169 (3)0.5034 (4)−0.1173 (3)0.077 (2)
H4030.21830.4712−0.14740.093*
C4040.1747 (3)0.5286 (5)−0.1000 (4)0.091 (3)
H4040.14680.5146−0.11890.109*
C4050.1716 (3)0.5739 (5)−0.0558 (4)0.091 (3)
H4050.14170.5903−0.04400.109*
C4060.2126 (2)0.5962 (4)−0.0277 (3)0.074 (2)
H4060.21050.62710.00320.089*
C4070.3282 (2)0.5166 (3)0.0241 (2)0.0494 (14)
C4080.3714 (2)0.4846 (3)0.0137 (3)0.0570 (16)
H4080.39170.5024−0.01450.068*
C4090.3848 (3)0.4258 (4)0.0449 (3)0.071 (2)
H4090.41430.40400.03830.085*
C4100.3547 (3)0.4002 (4)0.0855 (3)0.076 (2)
H4100.36420.36160.10730.091*
C4110.3110 (3)0.4297 (4)0.0948 (3)0.075 (2)
H4110.29040.41040.12190.089*
C4120.2976 (3)0.4877 (4)0.0645 (3)0.0638 (18)
H4120.26770.50800.07080.077*
C120.6027 (14)0.889 (2)−0.113 (2)0.150 (19)*0.25
C130.5711 (18)0.867 (2)−0.069 (2)0.18 (3)*0.25
H130.57860.8275−0.04690.216*0.25
C140.5296 (18)0.903 (3)−0.059 (2)0.19 (3)*0.25
H140.50800.8870−0.03140.227*0.25
C150.5195 (13)0.964 (2)−0.0888 (16)0.112 (13)*0.25
H150.49650.9958−0.07580.134*0.25
C160.5445 (13)0.9764 (19)−0.1389 (15)0.098 (11)*0.25
H160.53341.0100−0.16480.118*0.25
C170.585 (2)0.940 (4)−0.150 (2)0.27 (5)*0.25
H170.60180.9488−0.18390.330*0.25
C180.648 (2)0.844 (4)−0.127 (4)0.22 (5)*0.25
H18A0.65440.8116−0.09630.325*0.25
H18B0.64240.8172−0.16160.325*0.25
H18C0.67510.8743−0.13250.325*0.25
C190.5276 (16)0.991 (2)−0.1188 (19)0.141 (18)*0.25
C200.491 (2)1.019 (3)−0.0841 (19)0.22 (3)*0.25
H200.48460.9993−0.04870.262*0.25
C210.4658 (11)1.0766 (17)−0.1020 (14)0.092 (10)*0.25
H210.44231.0959−0.07840.111*0.25
C220.4743 (15)1.106 (2)−0.1540 (17)0.149 (18)*0.25
H220.45341.1396−0.16870.178*0.25
C230.5139 (16)1.085 (2)−0.1849 (15)0.152 (19)*0.25
H230.52111.1076−0.21940.183*0.25
C240.5423 (15)1.033 (3)−0.165 (2)0.18 (2)*0.25
H240.57201.0251−0.18200.215*0.25
C250.555 (2)0.922 (2)−0.103 (3)0.18 (2)*0.25
H25A0.53220.8853−0.09520.269*0.25
H25B0.57400.9307−0.06940.269*0.25
H25C0.57530.9087−0.13400.269*0.25
C100.6644 (7)0.7998 (10)−0.1009 (12)0.182 (11)0.75
H10A0.65730.7705−0.13390.218*0.75
H10B0.69250.7800−0.08240.218*0.75
Cl30.6794 (3)0.8884 (3)−0.1262 (2)0.194 (3)0.75
Cl40.6209 (3)0.7945 (4)−0.0581 (2)0.180 (2)0.75
C110.3470 (6)1.1480 (6)−0.2714 (6)0.105 (4)0.75
H11A0.36611.1584−0.30500.126*0.75
H11B0.31611.1707−0.27640.126*0.75
Cl50.3737 (2)1.1831 (3)−0.2153 (2)0.178 (2)0.75
Cl60.3386 (3)1.0614 (2)−0.2681 (2)0.180 (3)0.75
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.04080 (14)0.03873 (13)0.02908 (13)0.00223 (8)0.00040 (8)0.00056 (8)
P10.0501 (8)0.0421 (7)0.0342 (7)0.0083 (6)−0.0006 (6)0.0002 (6)
P20.0471 (8)0.0430 (7)0.0328 (7)0.0031 (6)0.0002 (6)−0.0040 (6)
P30.0513 (8)0.0505 (8)0.0336 (7)0.0017 (7)0.0012 (6)−0.0051 (6)
P40.0449 (8)0.0498 (8)0.0365 (7)−0.0025 (6)0.0018 (6)0.0023 (6)
Cl10.0656 (15)0.0489 (19)0.0225 (18)0.0087 (14)−0.0159 (15)0.0030 (12)
Cl1A0.080 (4)0.053 (4)0.010 (3)0.041 (3)−0.025 (3)−0.008 (2)
Cl20.0687 (12)0.1216 (18)0.0771 (12)−0.0142 (11)−0.0299 (10)−0.0132 (12)
N10.041 (2)0.045 (3)0.034 (2)0.000 (2)0.0021 (19)0.0033 (19)
N20.047 (3)0.054 (3)0.040 (3)0.008 (2)0.002 (2)0.001 (2)
N30.047 (3)0.049 (3)0.041 (3)0.004 (2)−0.001 (2)−0.001 (2)
C10.048 (3)0.038 (3)0.035 (3)0.002 (2)0.002 (2)0.000 (2)
C20.046 (3)0.049 (3)0.034 (3)0.005 (2)−0.003 (2)0.000 (2)
C30.055 (4)0.062 (4)0.040 (3)0.001 (3)0.005 (3)−0.003 (3)
C40.038 (3)0.049 (3)0.039 (3)−0.002 (2)0.002 (2)0.002 (2)
C50.060 (4)0.057 (4)0.056 (4)−0.004 (3)−0.004 (3)0.007 (3)
C60.064 (4)0.062 (4)0.070 (4)−0.022 (3)−0.011 (3)0.000 (3)
C70.042 (3)0.087 (5)0.053 (4)−0.002 (3)−0.008 (3)−0.013 (4)
C80.059 (4)0.064 (4)0.050 (3)0.006 (3)−0.013 (3)0.002 (3)
C90.065 (4)0.050 (3)0.046 (3)−0.003 (3)−0.009 (3)0.003 (3)
C1010.058 (4)0.054 (3)0.040 (3)0.019 (3)0.001 (3)0.001 (3)
C1020.080 (5)0.070 (5)0.054 (4)0.027 (4)−0.010 (3)−0.013 (3)
C1030.104 (7)0.088 (6)0.060 (4)0.049 (5)−0.001 (4)−0.020 (4)
C1040.084 (6)0.110 (7)0.089 (6)0.049 (6)0.015 (5)0.007 (5)
C1050.064 (5)0.091 (6)0.115 (7)0.021 (4)0.006 (5)−0.011 (5)
C1060.057 (4)0.075 (5)0.072 (4)0.016 (3)−0.001 (3)−0.009 (4)
C1070.070 (4)0.045 (3)0.043 (3)0.003 (3)−0.002 (3)0.003 (3)
C1080.081 (5)0.070 (5)0.069 (5)−0.010 (4)0.000 (4)0.023 (4)
C1090.100 (7)0.107 (7)0.114 (8)−0.035 (6)0.003 (6)0.034 (6)
C1100.146 (10)0.079 (6)0.115 (8)−0.025 (6)0.024 (7)0.044 (6)
C1110.160 (10)0.060 (5)0.073 (5)0.008 (6)0.021 (6)0.028 (4)
C1120.098 (6)0.053 (4)0.058 (4)0.013 (4)0.002 (4)0.005 (3)
C2010.052 (3)0.051 (3)0.042 (3)−0.001 (3)0.003 (3)−0.003 (3)
C2020.066 (4)0.053 (4)0.067 (4)0.003 (3)−0.009 (3)−0.007 (3)
C2030.090 (6)0.054 (4)0.093 (6)−0.005 (4)−0.008 (5)−0.012 (4)
C2040.078 (5)0.067 (5)0.082 (5)−0.017 (4)−0.004 (4)−0.015 (4)
C2050.076 (5)0.094 (6)0.072 (5)−0.017 (4)−0.021 (4)−0.013 (4)
C2060.070 (4)0.068 (4)0.057 (4)−0.009 (3)−0.013 (3)−0.004 (3)
C2070.055 (3)0.059 (3)0.032 (3)0.000 (3)−0.001 (3)−0.009 (3)
C2080.076 (5)0.070 (4)0.056 (4)0.013 (4)0.016 (3)0.001 (3)
C2090.072 (5)0.122 (7)0.058 (4)0.022 (5)0.026 (4)0.009 (5)
C2100.069 (5)0.113 (7)0.058 (4)−0.013 (5)0.019 (4)−0.004 (5)
C2110.127 (8)0.082 (5)0.061 (5)−0.026 (5)0.021 (5)0.012 (4)
C2120.094 (5)0.062 (4)0.057 (4)−0.003 (4)0.026 (4)−0.004 (3)
C3010.061 (4)0.057 (4)0.048 (3)0.005 (3)−0.004 (3)−0.010 (3)
C3020.086 (5)0.057 (4)0.075 (5)0.001 (4)−0.003 (4)−0.003 (4)
C3030.136 (9)0.051 (5)0.138 (9)−0.010 (5)−0.013 (7)−0.002 (6)
C3040.158 (11)0.053 (5)0.146 (10)0.027 (7)−0.038 (9)−0.025 (6)
C3050.120 (8)0.083 (6)0.096 (7)0.039 (6)−0.016 (6)−0.039 (6)
C3060.079 (5)0.074 (5)0.064 (4)0.021 (4)−0.009 (4)−0.022 (4)
C3070.056 (3)0.070 (4)0.034 (3)0.003 (3)−0.001 (3)−0.003 (3)
C3080.066 (4)0.096 (6)0.067 (5)0.000 (4)−0.012 (4)−0.003 (4)
C3090.067 (5)0.133 (8)0.070 (5)−0.004 (5)−0.023 (4)−0.021 (5)
C3100.084 (6)0.164 (10)0.042 (4)0.009 (6)−0.016 (4)0.007 (5)
C3110.130 (8)0.131 (8)0.060 (5)−0.017 (7)−0.026 (5)0.038 (5)
C3120.111 (7)0.095 (6)0.051 (4)−0.020 (5)−0.022 (4)0.019 (4)
C4010.047 (3)0.056 (4)0.049 (3)−0.007 (3)−0.003 (3)0.007 (3)
C4020.061 (4)0.064 (4)0.056 (4)−0.012 (3)0.000 (3)−0.006 (3)
C4030.073 (5)0.089 (5)0.070 (5)−0.020 (4)−0.011 (4)−0.011 (4)
C4040.074 (6)0.122 (7)0.076 (5)−0.024 (5)−0.021 (4)0.002 (5)
C4050.054 (5)0.121 (8)0.098 (7)−0.005 (5)−0.003 (4)−0.003 (6)
C4060.052 (4)0.097 (6)0.074 (5)0.003 (4)−0.004 (3)−0.007 (4)
C4070.059 (4)0.050 (3)0.039 (3)−0.012 (3)−0.005 (3)0.003 (3)
C4080.057 (4)0.055 (4)0.059 (4)−0.007 (3)−0.001 (3)0.011 (3)
C4090.079 (5)0.048 (4)0.085 (5)0.002 (3)−0.008 (4)0.016 (4)
C4100.109 (6)0.048 (4)0.070 (5)−0.011 (4)−0.021 (5)0.017 (4)
C4110.099 (6)0.075 (5)0.049 (4)−0.025 (4)0.000 (4)0.021 (4)
C4120.068 (4)0.071 (4)0.052 (4)−0.012 (4)0.004 (3)0.006 (3)
C100.143 (15)0.123 (15)0.28 (3)−0.022 (13)0.029 (19)−0.125 (18)
Cl30.282 (8)0.178 (5)0.121 (4)−0.029 (6)0.024 (4)−0.015 (4)
Cl40.224 (7)0.181 (6)0.135 (4)−0.024 (5)0.009 (4)−0.033 (4)
C110.120 (11)0.088 (9)0.106 (10)0.001 (7)−0.036 (9)−0.005 (7)
Cl50.249 (7)0.173 (5)0.112 (3)−0.071 (4)−0.039 (3)−0.028 (3)
Cl60.315 (8)0.076 (2)0.150 (4)−0.040 (3)−0.071 (4)0.026 (2)
Geometric parameters (Å, º) top
Ir1—P12.2788 (14)C301—C3021.380 (10)
Ir1—C11.998 (5)C301—C3061.402 (10)
Ir1—N11.999 (4)C302—C3031.405 (11)
Ir1—P32.3748 (14)C302—H3020.9400
Ir1—P42.2662 (14)C303—C3041.372 (16)
P1—C1071.821 (6)C303—H3030.9400
P1—C1011.827 (6)C304—C3051.341 (15)
P1—C21.846 (5)C304—H3040.9400
P2—C11.775 (5)C305—C3061.387 (12)
P2—C2071.794 (6)C305—H3050.9400
P2—C21.795 (5)C306—H3060.9400
P2—C2011.803 (6)C307—C3121.372 (11)
P3—C3011.802 (7)C307—C3081.391 (10)
P3—C3071.828 (6)C308—C3091.381 (11)
P3—C31.851 (6)C308—H3080.9400
P3—P42.686 (2)C309—C3101.384 (13)
P4—C4011.817 (6)C309—H3090.9400
P4—C4071.818 (6)C310—C3111.359 (13)
P4—C31.838 (6)C310—H3100.9400
Cl1—Cl1A0.574 (6)C311—C3121.392 (11)
Cl2—C71.751 (6)C311—H3110.9400
N1—N21.354 (6)C312—H3120.9400
N1—C41.431 (7)C401—C4061.382 (9)
N2—N31.308 (6)C401—C4021.392 (9)
N3—C11.346 (7)C402—C4031.387 (9)
C2—H2A0.9800C402—H4020.9400
C2—H2B0.9800C403—C4041.345 (12)
C3—H3A0.9800C403—H4030.9400
C3—H3B0.9800C404—C4051.361 (12)
C4—C51.367 (8)C404—H4040.9400
C4—C91.384 (8)C405—C4061.398 (11)
C5—C61.383 (9)C405—H4050.9400
C5—H50.9400C406—H4060.9400
C6—C71.387 (10)C407—C4081.383 (9)
C6—H60.9400C407—C4121.398 (9)
C7—C81.350 (9)C408—C4091.396 (9)
C8—C91.384 (8)C408—H4080.9400
C8—H80.9400C409—C4101.369 (11)
C9—H90.9400C409—H4090.9400
C101—C1061.384 (9)C410—C4111.369 (11)
C101—C1021.400 (9)C410—H4100.9400
C102—C1031.417 (11)C411—C4121.371 (10)
C102—H1020.9400C411—H4110.9400
C103—C1041.377 (13)C412—H4120.9400
C103—H1030.9400C12—C171.401 (17)
C104—C1051.359 (13)C12—C131.430 (17)
C104—H1040.9400C12—C181.575 (17)
C105—C1061.389 (10)C13—C141.381 (17)
C105—H1050.9400C13—H130.9400
C106—H1060.9400C14—C151.388 (17)
C107—C1081.368 (10)C14—H140.9400
C107—C1121.406 (9)C15—C161.397 (17)
C108—C1091.381 (11)C15—H150.9400
C108—H1080.9400C16—C171.369 (17)
C109—C1101.360 (14)C16—H160.9400
C109—H1090.9400C17—H170.9400
C110—C1111.375 (14)C18—H18A0.9700
C110—H1100.9400C18—H18B0.9700
C111—C1121.356 (11)C18—H18C0.9700
C111—H1110.9400C19—C241.421 (17)
C112—H1120.9400C19—C201.422 (17)
C201—C2021.382 (9)C19—C251.559 (16)
C201—C2061.395 (9)C20—C211.373 (16)
C202—C2031.394 (9)C20—H200.9400
C202—H2020.9400C21—C221.370 (17)
C203—C2041.361 (11)C21—H210.9400
C203—H2030.9400C22—C231.387 (17)
C204—C2051.392 (11)C22—H220.9400
C204—H2040.9400C23—C241.362 (17)
C205—C2061.385 (10)C23—H230.9400
C205—H2050.9400C24—H240.9400
C206—H2060.9400C25—H25A0.9700
C207—C2081.380 (9)C25—H25B0.9700
C207—C2121.384 (9)C25—H25C0.9700
C208—C2091.382 (10)C10—Cl41.59 (2)
C208—H2080.9400C10—Cl31.84 (2)
C209—C2101.347 (12)C10—H10A0.9800
C209—H2090.9400C10—H10B0.9800
C210—C2111.389 (12)C11—Cl51.665 (13)
C210—H2100.9400C11—Cl61.672 (12)
C211—C2121.411 (10)C11—H11A0.9800
C211—H2110.9400C11—H11B0.9800
C212—H2120.9400
C1—Ir1—N173.7 (2)C208—C209—H209119.2
C1—Ir1—P4108.92 (16)C209—C210—C211119.7 (7)
N1—Ir1—P4122.71 (13)C209—C210—H210120.1
C1—Ir1—P185.35 (15)C211—C210—H210120.1
N1—Ir1—P1140.40 (13)C210—C211—C212119.7 (8)
P4—Ir1—P195.59 (5)C210—C211—H211120.1
C1—Ir1—P3173.04 (16)C212—C211—H211120.1
N1—Ir1—P3100.49 (13)C207—C212—C211119.1 (7)
P4—Ir1—P370.69 (5)C207—C212—H212120.4
P1—Ir1—P3101.62 (5)C211—C212—H212120.4
C107—P1—C101102.1 (3)C302—C301—C306120.0 (7)
C107—P1—C2102.9 (3)C302—C301—P3118.8 (5)
C101—P1—C2102.3 (3)C306—C301—P3121.1 (6)
C107—P1—Ir1115.4 (2)C301—C302—C303120.0 (9)
C101—P1—Ir1124.54 (19)C301—C302—H302120.0
C2—P1—Ir1106.97 (18)C303—C302—H302120.0
C1—P2—C207111.2 (3)C304—C303—C302118.5 (10)
C1—P2—C2103.4 (2)C304—C303—H303120.8
C207—P2—C2112.2 (3)C302—C303—H303120.8
C1—P2—C201115.6 (3)C305—C304—C303121.9 (9)
C207—P2—C201106.5 (3)C305—C304—H304119.0
C2—P2—C201108.0 (3)C303—C304—H304119.0
C301—P3—C307101.4 (3)C304—C305—C306121.2 (9)
C301—P3—C3108.6 (3)C304—C305—H305119.4
C307—P3—C3103.9 (3)C306—C305—H305119.4
C301—P3—Ir1122.3 (2)C305—C306—C301118.4 (9)
C307—P3—Ir1124.5 (2)C305—C306—H306120.8
C3—P3—Ir193.54 (19)C301—C306—H306120.8
C301—P3—P4138.8 (2)C312—C307—C308118.3 (6)
C307—P3—P4113.3 (2)C312—C307—P3120.9 (5)
C3—P3—P443.06 (19)C308—C307—P3120.7 (5)
Ir1—P3—P452.76 (4)C309—C308—C307120.9 (8)
C401—P4—C407101.7 (3)C309—C308—H308119.5
C401—P4—C3109.2 (3)C307—C308—H308119.5
C407—P4—C3107.9 (3)C308—C309—C310119.3 (8)
C401—P4—Ir1126.1 (2)C308—C309—H309120.4
C407—P4—Ir1113.5 (2)C310—C309—H309120.4
C3—P4—Ir197.6 (2)C311—C310—C309120.6 (8)
C401—P4—P3143.7 (2)C311—C310—H310119.7
C407—P4—P3109.19 (19)C309—C310—H310119.7
C3—P4—P343.4 (2)C310—C311—C312119.6 (9)
Ir1—P4—P356.54 (5)C310—C311—H311120.2
N2—N1—C4111.5 (4)C312—C311—H311120.2
N2—N1—Ir1119.6 (3)C307—C312—C311121.1 (8)
C4—N1—Ir1128.9 (4)C307—C312—H312119.4
N3—N2—N1112.3 (4)C311—C312—H312119.4
N2—N3—C1115.2 (4)C406—C401—C402119.2 (6)
N3—C1—P2115.9 (4)C406—C401—P4123.4 (5)
N3—C1—Ir1118.5 (4)C402—C401—P4117.4 (5)
P2—C1—Ir1124.5 (3)C403—C402—C401120.3 (7)
P2—C2—P1109.6 (3)C403—C402—H402119.8
P2—C2—H2A109.7C401—C402—H402119.8
P1—C2—H2A109.7C404—C403—C402119.8 (8)
P2—C2—H2B109.7C404—C403—H403120.1
P1—C2—H2B109.7C402—C403—H403120.1
H2A—C2—H2B108.2C403—C404—C405121.2 (8)
P4—C3—P393.5 (3)C403—C404—H404119.4
P4—C3—H3A113.0C405—C404—H404119.4
P3—C3—H3A113.0C404—C405—C406120.4 (8)
P4—C3—H3B113.0C404—C405—H405119.8
P3—C3—H3B113.0C406—C405—H405119.8
H3A—C3—H3B110.4C401—C406—C405119.0 (8)
C5—C4—C9119.7 (5)C401—C406—H406120.5
C5—C4—N1119.2 (5)C405—C406—H406120.5
C9—C4—N1121.1 (5)C408—C407—C412119.2 (6)
C4—C5—C6120.5 (6)C408—C407—P4120.2 (4)
C4—C5—H5119.7C412—C407—P4120.6 (5)
C6—C5—H5119.7C407—C408—C409119.9 (6)
C5—C6—C7118.4 (6)C407—C408—H408120.1
C5—C6—H6120.8C409—C408—H408120.1
C7—C6—H6120.8C410—C409—C408119.4 (7)
C8—C7—C6122.0 (6)C410—C409—H409120.3
C8—C7—Cl2119.0 (6)C408—C409—H409120.3
C6—C7—Cl2118.9 (6)C409—C410—C411121.4 (7)
C7—C8—C9118.9 (6)C409—C410—H410119.3
C7—C8—H8120.5C411—C410—H410119.3
C9—C8—H8120.5C410—C411—C412119.6 (7)
C4—C9—C8120.4 (6)C410—C411—H411120.2
C4—C9—H9119.8C412—C411—H411120.2
C8—C9—H9119.8C411—C412—C407120.4 (7)
C106—C101—C102118.6 (6)C411—C412—H412119.8
C106—C101—P1123.3 (5)C407—C412—H412119.8
C102—C101—P1117.9 (5)C17—C12—C13116.2 (15)
C101—C102—C103119.2 (8)C17—C12—C18122.0 (18)
C101—C102—H102120.4C13—C12—C18119.9 (18)
C103—C102—H102120.4C14—C13—C12120.4 (15)
C104—C103—C102119.7 (7)C14—C13—H13119.8
C104—C103—H103120.1C12—C13—H13119.8
C102—C103—H103120.1C13—C14—C15120.2 (16)
C105—C104—C103121.4 (8)C13—C14—H14119.9
C105—C104—H104119.3C15—C14—H14119.9
C103—C104—H104119.3C14—C15—C16118.2 (16)
C104—C105—C106119.2 (9)C14—C15—H15120.9
C104—C105—H105120.4C16—C15—H15120.9
C106—C105—H105120.4C17—C16—C15120.0 (15)
C101—C106—C105121.8 (7)C17—C16—H16120.0
C101—C106—H106119.1C15—C16—H16120.0
C105—C106—H106119.1C16—C17—C12121.7 (15)
C108—C107—C112118.0 (6)C16—C17—H17119.1
C108—C107—P1120.8 (5)C12—C17—H17119.1
C112—C107—P1121.1 (6)C12—C18—H18A109.5
C107—C108—C109120.7 (8)C12—C18—H18B109.5
C107—C108—H108119.7H18A—C18—H18B109.5
C109—C108—H108119.7C12—C18—H18C109.5
C110—C109—C108120.3 (10)H18A—C18—H18C109.5
C110—C109—H109119.8H18B—C18—H18C109.5
C108—C109—H109119.8C24—C19—C20115.5 (14)
C109—C110—C111120.2 (8)C24—C19—C25121.4 (16)
C109—C110—H110119.9C20—C19—C25122.5 (16)
C111—C110—H110119.9C21—C20—C19120.4 (15)
C112—C111—C110119.8 (9)C21—C20—H20119.8
C112—C111—H111120.1C19—C20—H20119.8
C110—C111—H111120.1C22—C21—C20120.5 (15)
C111—C112—C107121.1 (9)C22—C21—H21119.7
C111—C112—H112119.5C20—C21—H21119.7
C107—C112—H112119.5C21—C22—C23119.9 (15)
C202—C201—C206119.9 (6)C21—C22—H22120.0
C202—C201—P2121.9 (5)C23—C22—H22120.0
C206—C201—P2118.3 (5)C24—C23—C22119.6 (15)
C201—C202—C203120.1 (7)C24—C23—H23120.2
C201—C202—H202120.0C22—C23—H23120.2
C203—C202—H202120.0C23—C24—C19120.9 (17)
C204—C203—C202120.3 (7)C23—C24—H24119.5
C204—C203—H203119.8C19—C24—H24119.5
C202—C203—H203119.8C19—C25—H25A109.5
C203—C204—C205119.9 (7)C19—C25—H25B109.5
C203—C204—H204120.0H25A—C25—H25B109.5
C205—C204—H204120.0C19—C25—H25C109.5
C206—C205—C204120.5 (7)H25A—C25—H25C109.5
C206—C205—H205119.7H25B—C25—H25C109.5
C204—C205—H205119.7Cl4—C10—Cl3116.1 (11)
C205—C206—C201119.2 (7)Cl4—C10—H10A108.3
C205—C206—H206120.4Cl3—C10—H10A108.3
C201—C206—H206120.4Cl4—C10—H10B108.3
C208—C207—C212119.9 (6)Cl3—C10—H10B108.3
C208—C207—P2117.1 (5)H10A—C10—H10B107.4
C212—C207—P2123.0 (5)Cl5—C11—Cl6115.1 (8)
C207—C208—C209119.8 (7)Cl5—C11—H11A108.5
C207—C208—H208120.1Cl6—C11—H11A108.5
C209—C208—H208120.1Cl5—C11—H11B108.5
C210—C209—C208121.6 (8)Cl6—C11—H11B108.5
C210—C209—H209119.2H11A—C11—H11B107.5
C4—N1—N2—N3−173.9 (4)C207—C208—C209—C2102.8 (12)
Ir1—N1—N2—N38.1 (6)C208—C209—C210—C211−3.8 (13)
N1—N2—N3—C1−3.1 (7)C209—C210—C211—C2121.5 (13)
N2—N3—C1—P2165.7 (4)C208—C207—C212—C211−2.7 (11)
N2—N3—C1—Ir1−3.0 (6)P2—C207—C212—C211175.1 (6)
C207—P2—C1—N3−47.9 (5)C210—C211—C212—C2071.7 (12)
C2—P2—C1—N3−168.5 (4)C307—P3—C301—C302105.5 (6)
C201—P2—C1—N373.7 (5)C3—P3—C301—C302−145.5 (6)
C207—P2—C1—Ir1120.0 (4)Ir1—P3—C301—C302−38.6 (7)
C2—P2—C1—Ir1−0.6 (4)P4—P3—C301—C302−107.2 (6)
C201—P2—C1—Ir1−118.4 (3)C307—P3—C301—C306−72.4 (6)
C1—P2—C2—P122.3 (4)C3—P3—C301—C30636.6 (6)
C207—P2—C2—P1−97.7 (3)Ir1—P3—C301—C306143.5 (5)
C201—P2—C2—P1145.3 (3)P4—P3—C301—C30674.9 (7)
C107—P1—C2—P288.6 (3)C306—C301—C302—C303−0.9 (12)
C101—P1—C2—P2−165.8 (3)P3—C301—C302—C303−178.8 (7)
Ir1—P1—C2—P2−33.4 (3)C301—C302—C303—C3040.7 (15)
C401—P4—C3—P3−150.9 (3)C302—C303—C304—C3050.3 (17)
C407—P4—C3—P399.3 (3)C303—C304—C305—C306−1.1 (17)
Ir1—P4—C3—P3−18.4 (3)C304—C305—C306—C3010.8 (14)
C301—P3—C3—P4143.3 (3)C302—C301—C306—C3050.1 (11)
C307—P3—C3—P4−109.4 (3)P3—C301—C306—C305178.1 (6)
Ir1—P3—C3—P417.4 (2)C301—P3—C307—C312150.3 (7)
N2—N1—C4—C5110.7 (6)C3—P3—C307—C31237.6 (7)
Ir1—N1—C4—C5−71.5 (7)Ir1—P3—C307—C312−66.7 (7)
N2—N1—C4—C9−69.1 (7)P4—P3—C307—C312−6.9 (7)
Ir1—N1—C4—C9108.6 (6)C301—P3—C307—C308−28.8 (6)
C9—C4—C5—C6−0.7 (10)C3—P3—C307—C308−141.4 (6)
N1—C4—C5—C6179.4 (6)Ir1—P3—C307—C308114.3 (5)
C4—C5—C6—C7−0.7 (10)P4—P3—C307—C308174.1 (5)
C5—C6—C7—C82.0 (11)C312—C307—C308—C309−1.7 (11)
C5—C6—C7—Cl2−175.9 (5)P3—C307—C308—C309177.4 (6)
C6—C7—C8—C9−1.9 (10)C307—C308—C309—C3102.0 (13)
Cl2—C7—C8—C9176.0 (5)C308—C309—C310—C311−1.6 (15)
C5—C4—C9—C80.8 (9)C309—C310—C311—C3121.0 (16)
N1—C4—C9—C8−179.3 (5)C308—C307—C312—C3111.0 (13)
C7—C8—C9—C40.5 (10)P3—C307—C312—C311−178.0 (8)
C107—P1—C101—C106128.3 (6)C310—C311—C312—C307−0.7 (16)
C2—P1—C101—C10622.1 (6)C407—P4—C401—C406106.9 (6)
Ir1—P1—C101—C106−98.8 (6)C3—P4—C401—C406−7.0 (7)
C107—P1—C101—C102−55.4 (5)Ir1—P4—C401—C406−122.2 (6)
C2—P1—C101—C102−161.7 (5)P3—P4—C401—C406−41.4 (8)
Ir1—P1—C101—C10277.5 (5)C407—P4—C401—C402−71.2 (5)
C106—C101—C102—C1032.0 (10)C3—P4—C401—C402175.0 (5)
P1—C101—C102—C103−174.4 (6)Ir1—P4—C401—C40259.8 (6)
C101—C102—C103—C104−1.1 (12)P3—P4—C401—C402140.6 (4)
C102—C103—C104—C105−1.0 (14)C406—C401—C402—C4030.9 (10)
C103—C104—C105—C1062.2 (14)P4—C401—C402—C403179.0 (6)
C102—C101—C106—C105−0.8 (11)C401—C402—C403—C4040.7 (12)
P1—C101—C106—C105175.4 (6)C402—C403—C404—C405−1.7 (14)
C104—C105—C106—C101−1.3 (13)C403—C404—C405—C4061.0 (15)
C101—P1—C107—C108145.3 (6)C402—C401—C406—C405−1.6 (11)
C2—P1—C107—C108−108.9 (6)P4—C401—C406—C405−179.6 (6)
Ir1—P1—C107—C1087.2 (6)C404—C405—C406—C4010.7 (13)
C101—P1—C107—C112−39.5 (6)C401—P4—C407—C408123.5 (5)
C2—P1—C107—C11266.3 (6)C3—P4—C407—C408−121.7 (5)
Ir1—P1—C107—C112−177.6 (5)Ir1—P4—C407—C408−14.8 (6)
C112—C107—C108—C1090.8 (11)P3—P4—C407—C408−75.7 (5)
P1—C107—C108—C109176.1 (7)C401—P4—C407—C412−58.2 (6)
C107—C108—C109—C110−0.8 (15)C3—P4—C407—C41256.7 (6)
C108—C109—C110—C111−0.2 (17)Ir1—P4—C407—C412163.6 (4)
C109—C110—C111—C1121.2 (16)P3—P4—C407—C412102.6 (5)
C110—C111—C112—C107−1.2 (13)C412—C407—C408—C409−2.7 (10)
C108—C107—C112—C1110.2 (11)P4—C407—C408—C409175.7 (5)
P1—C107—C112—C111−175.1 (6)C407—C408—C409—C4100.5 (11)
C1—P2—C201—C202−14.3 (6)C408—C409—C410—C4112.0 (12)
C207—P2—C201—C202109.8 (6)C409—C410—C411—C412−2.3 (12)
C2—P2—C201—C202−129.6 (5)C410—C411—C412—C4070.1 (11)
C1—P2—C201—C206164.5 (5)C408—C407—C412—C4112.4 (10)
C207—P2—C201—C206−71.4 (6)P4—C407—C412—C411−175.9 (5)
C2—P2—C201—C20649.2 (6)C17—C12—C13—C14−11 (10)
C206—C201—C202—C2031.1 (10)C18—C12—C13—C14−175 (7)
P2—C201—C202—C203179.8 (6)C12—C13—C14—C15−4 (10)
C201—C202—C203—C204−0.5 (12)C13—C14—C15—C1617 (9)
C202—C203—C204—C205−0.5 (13)C14—C15—C16—C17−16 (8)
C203—C204—C205—C2060.8 (13)C15—C16—C17—C121 (12)
C204—C205—C206—C201−0.2 (12)C13—C12—C17—C1613 (12)
C202—C201—C206—C205−0.8 (10)C18—C12—C17—C16177 (8)
P2—C201—C206—C205−179.6 (6)C24—C19—C20—C2114 (9)
C1—P2—C207—C20874.4 (6)C25—C19—C20—C21−175 (6)
C2—P2—C207—C208−170.3 (5)C19—C20—C21—C221 (9)
C201—P2—C207—C208−52.4 (6)C20—C21—C22—C23−11 (8)
C1—P2—C207—C212−103.4 (6)C21—C22—C23—C244 (9)
C2—P2—C207—C21211.9 (7)C22—C23—C24—C1912 (9)
C201—P2—C207—C212129.8 (6)C20—C19—C24—C23−20 (9)
C212—C207—C208—C2090.5 (11)C25—C19—C24—C23168 (6)
P2—C207—C208—C209−177.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2B···Cl10.982.623.5215 (1)153
C11—H11B···Cl1i0.982.493.4594 (1)170
C209—H209···N3ii0.942.603.3722 (1)140
C306—H306···Cl1Aiii0.942.813.7037 (1)159
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1, y, −z−1/2; (iii) −x+1/2, −y+3/2, z+1/2.
{4-[3-(4-Chlorophenyl)triazenido-κN3]-1,1,3,3-tetraphenyl-1,3λ5-diphospha-κP1-but-2-en-4-yl}cyanido[methylenebis(diphenylphosphine)-κ2P,P']iridium(III) methanol disolvate (3) top
Crystal data top
[Ir(CN)(C23H22P2)(C34H26ClN3P2)]·2CH4OZ = 2
Mr = 1216.61F(000) = 1228
Triclinic, P1Dx = 1.521 Mg m−3
a = 11.1683 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.7805 (2) ÅCell parameters from 31262 reflections
c = 20.0591 (3) Åθ = 1.0–27.5°
α = 98.475 (1)°µ = 2.73 mm−1
β = 93.122 (1)°T = 223 K
γ = 109.336 (1)°Prism, colourless
V = 2655.75 (6) Å30.31 × 0.30 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer		Rint = 0.034
phi– and ω–scansθmax = 26.0°, θmin = 1.7°
20072 measured reflectionsh = −13→13
10396 independent reflectionsk = −15→15
9895 reflections with I > 2σ(I)l = −24→24
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.023H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.056 w = 1/[σ2(Fo2) + (0.0184P)2 + 2.0572P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
10396 reflectionsΔρmax = 0.77 e Å−3
661 parametersΔρmin = −1.10 e Å−3
Special details top

Experimental. All data sets were measured with several scans to increase the number of redundant reflections. In our experience this method of averaging redundant reflections replaces in a good approximation semi-empirical absorption methods (absorption correction programs like SORTAV lead to no better data sets).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms at C1 and C2 were localized and refined with isotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ir10.35118 (2)0.22849 (2)0.74840 (2)0.01977 (4)
Cl1−0.33530 (7)−0.10915 (7)0.67497 (5)0.0557 (2)
P10.37841 (6)0.34073 (5)0.85641 (3)0.02148 (13)
P20.46189 (6)0.51310 (5)0.77072 (3)0.02315 (13)
P30.36652 (6)0.12853 (6)0.64246 (3)0.02637 (14)
P40.54330 (6)0.19402 (5)0.75590 (3)0.02464 (14)
N10.17849 (19)0.24596 (18)0.71335 (11)0.0256 (5)
N20.1886 (2)0.31929 (18)0.67036 (11)0.0294 (5)
N30.2975 (2)0.38693 (18)0.66488 (11)0.0298 (5)
C10.4080 (2)0.3808 (2)0.70859 (13)0.0238 (5)
H10.473 (3)0.388 (3)0.6813 (16)0.040 (8)*
C20.4452 (2)0.4807 (2)0.84909 (14)0.0280 (6)
H20.455 (3)0.539 (2)0.8856 (15)0.033 (8)*
C30.5057 (3)0.0974 (2)0.67372 (14)0.0319 (6)
H3A0.57500.11690.64480.038*
H3B0.48400.01850.67910.038*
C40.0537 (2)0.1642 (2)0.70456 (14)0.0273 (5)
C50.0021 (2)0.1141 (2)0.75831 (14)0.0310 (6)
H50.04870.13730.80150.037*
C6−0.1164 (3)0.0310 (2)0.74920 (16)0.0359 (6)
H6−0.1502−0.00220.78600.043*
C7−0.1853 (3)−0.0034 (2)0.68569 (17)0.0384 (7)
C8−0.1381 (3)0.0446 (3)0.63178 (16)0.0403 (7)
H8−0.18640.02120.58900.048*
C9−0.0181 (3)0.1284 (2)0.64053 (15)0.0359 (6)
H90.01490.16110.60340.043*
C1010.2366 (2)0.3316 (2)0.90152 (13)0.0260 (5)
C1020.1406 (2)0.3617 (2)0.87082 (14)0.0319 (6)
H1020.14580.37800.82670.038*
C1030.0374 (3)0.3679 (3)0.90492 (16)0.0404 (7)
H103−0.02650.38860.88380.048*
C1040.0282 (3)0.3438 (3)0.96972 (18)0.0487 (8)
H104−0.04130.34860.99280.058*
C1050.1213 (3)0.3129 (3)1.00026 (17)0.0511 (8)
H1050.11460.29561.04420.061*
C1060.2251 (3)0.3070 (3)0.96686 (15)0.0381 (7)
H1060.28830.28610.98850.046*
C1070.4795 (2)0.3081 (2)0.91953 (13)0.0261 (5)
C1080.5897 (3)0.3915 (2)0.95340 (14)0.0333 (6)
H1080.61250.46480.94350.040*
C1090.6661 (3)0.3677 (3)1.00168 (15)0.0425 (7)
H1090.74080.42451.02380.051*
C1100.6325 (3)0.2609 (3)1.01710 (16)0.0462 (8)
H1100.68390.24471.04990.055*
C1110.5228 (3)0.1775 (3)0.98416 (15)0.0405 (7)
H1110.49950.10480.99500.049*
C1120.4471 (3)0.2003 (2)0.93538 (14)0.0321 (6)
H1120.37340.14270.91280.038*
C2010.3767 (2)0.6072 (2)0.75281 (14)0.0266 (5)
C2020.2929 (3)0.6294 (2)0.79717 (16)0.0365 (6)
H2020.27730.59320.83500.044*
C2030.2323 (3)0.7053 (3)0.78555 (19)0.0472 (8)
H2030.17700.72130.81600.057*
C2040.2527 (3)0.7568 (3)0.7300 (2)0.0506 (9)
H2040.21040.80710.72220.061*
C2050.3354 (3)0.7352 (3)0.68530 (19)0.0482 (8)
H2050.34870.77030.64700.058*
C2060.3984 (3)0.6617 (2)0.69712 (16)0.0370 (7)
H2060.45610.64850.66740.044*
C2070.6230 (2)0.5994 (2)0.75804 (15)0.0315 (6)
C2080.6933 (3)0.6839 (2)0.81107 (18)0.0424 (7)
H2080.65840.69330.85220.051*
C2090.8150 (3)0.7547 (3)0.8039 (2)0.0545 (10)
H2090.86170.81200.84010.065*
C2100.8674 (3)0.7416 (3)0.7443 (2)0.0600 (11)
H2100.94980.78960.73970.072*
C2110.7991 (3)0.6580 (3)0.6913 (2)0.0559 (9)
H2110.83560.64850.65070.067*
C2120.6765 (3)0.5873 (3)0.69726 (17)0.0418 (7)
H2120.62960.53150.66040.050*
C3010.2520 (3)−0.0063 (2)0.59993 (14)0.0329 (6)
C3020.1351 (3)−0.0519 (2)0.62255 (16)0.0400 (7)
H3020.1138−0.01390.66130.048*
C3030.0481 (4)−0.1541 (3)0.58850 (19)0.0555 (9)
H303−0.0323−0.18360.60380.067*
C3040.0787 (4)−0.2118 (3)0.53297 (19)0.0611 (10)
H3040.0193−0.28020.50980.073*
C3050.1971 (4)−0.1687 (3)0.51126 (19)0.0647 (11)
H3050.2195−0.20940.47400.078*
C3060.2839 (4)−0.0658 (3)0.54393 (17)0.0510 (8)
H3060.3640−0.03640.52820.061*
C3070.4113 (3)0.2083 (2)0.57471 (14)0.0356 (6)
C3080.3161 (4)0.2147 (3)0.52929 (16)0.0523 (9)
H3080.23050.17030.53050.063*
C3090.3469 (5)0.2860 (4)0.48258 (19)0.0697 (12)
H3090.28200.29060.45250.084*
C3100.4706 (6)0.3496 (4)0.4798 (2)0.0771 (14)
H3100.49030.39790.44770.092*
C3110.5669 (5)0.3443 (4)0.5230 (2)0.0754 (13)
H3110.65220.38790.52040.091*
C3120.5367 (4)0.2732 (3)0.57100 (19)0.0544 (9)
H3120.60220.26940.60100.065*
C4010.5894 (2)0.1128 (2)0.81428 (13)0.0273 (5)
C4020.5127 (3)0.0026 (2)0.81453 (15)0.0346 (6)
H4020.4341−0.02820.78710.041*
C4030.5503 (3)−0.0625 (3)0.85466 (17)0.0419 (7)
H4030.4980−0.13740.85410.050*
C4040.6653 (3)−0.0170 (3)0.89567 (17)0.0447 (8)
H4040.6916−0.06120.92280.054*
C4050.7413 (3)0.0928 (3)0.89676 (16)0.0426 (7)
H4050.81860.12370.92530.051*
C4060.7048 (2)0.1581 (2)0.85609 (15)0.0335 (6)
H4060.75770.23290.85670.040*
C4070.6942 (2)0.3041 (2)0.75248 (15)0.0314 (6)
C4080.7255 (2)0.4061 (2)0.79592 (15)0.0335 (6)
H4080.66520.42080.82330.040*
C4090.8465 (3)0.4872 (3)0.79924 (19)0.0458 (8)
H4090.86890.55570.82970.055*
C4100.9334 (3)0.4660 (3)0.7573 (2)0.0532 (9)
H4101.01370.52170.75810.064*
C4110.9036 (3)0.3646 (3)0.7146 (2)0.0526 (9)
H4110.96360.35060.68670.063*
C4120.7852 (3)0.2833 (3)0.71273 (18)0.0429 (7)
H4120.76570.21310.68430.051*
N40.2110 (2)0.0011 (2)0.80197 (13)0.0404 (6)
C100.2640 (2)0.0841 (2)0.78323 (13)0.0263 (5)
O20.1944 (4)0.4619 (3)0.54949 (16)0.0904 (10)
H2A0.24290.45260.57910.136*
C120.1072 (5)0.5034 (4)0.5799 (3)0.0897 (16)
H12A0.13300.52600.62830.135*
H12B0.02340.44530.57190.135*
H12C0.10410.56800.56080.135*
O10.1200 (6)−0.1236 (4)0.9047 (3)0.1429 (19)
H1A0.1484−0.09990.87030.214*
C110.0930 (7)−0.0440 (5)0.9440 (3)0.120 (2)
H11A0.0488−0.07470.98080.180*
H11B0.0390−0.01570.91760.180*
H11C0.17160.01700.96240.180*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.02111 (5)0.01730 (6)0.02081 (6)0.00605 (4)0.00309 (4)0.00405 (4)
Cl10.0292 (4)0.0364 (4)0.0900 (7)0.0023 (3)−0.0012 (4)−0.0010 (4)
P10.0230 (3)0.0193 (3)0.0215 (3)0.0062 (2)0.0027 (2)0.0037 (2)
P20.0222 (3)0.0183 (3)0.0288 (3)0.0060 (2)0.0034 (2)0.0059 (3)
P30.0339 (3)0.0246 (3)0.0225 (3)0.0125 (3)0.0043 (3)0.0038 (3)
P40.0233 (3)0.0224 (3)0.0292 (4)0.0087 (3)0.0040 (3)0.0053 (3)
N10.0226 (10)0.0280 (11)0.0267 (11)0.0092 (9)−0.0002 (8)0.0058 (9)
N20.0331 (12)0.0272 (12)0.0285 (12)0.0120 (10)−0.0019 (9)0.0049 (9)
N30.0378 (12)0.0251 (12)0.0262 (12)0.0105 (10)0.0011 (9)0.0058 (9)
C10.0250 (12)0.0229 (13)0.0234 (13)0.0065 (10)0.0068 (10)0.0063 (10)
C20.0341 (14)0.0190 (13)0.0286 (14)0.0061 (10)0.0046 (11)0.0043 (11)
C30.0355 (14)0.0324 (15)0.0326 (15)0.0187 (12)0.0060 (11)0.0027 (12)
C40.0216 (12)0.0269 (14)0.0337 (14)0.0099 (10)0.0014 (10)0.0028 (11)
C50.0321 (13)0.0269 (14)0.0324 (15)0.0098 (11)0.0024 (11)0.0017 (11)
C60.0317 (14)0.0300 (15)0.0445 (17)0.0094 (12)0.0092 (12)0.0031 (13)
C70.0252 (13)0.0257 (14)0.058 (2)0.0056 (11)−0.0009 (13)−0.0025 (13)
C80.0339 (15)0.0384 (17)0.0422 (18)0.0112 (13)−0.0099 (13)−0.0044 (14)
C90.0319 (14)0.0399 (16)0.0306 (15)0.0079 (12)−0.0014 (11)0.0026 (12)
C1010.0264 (12)0.0198 (12)0.0292 (14)0.0051 (10)0.0062 (10)0.0016 (10)
C1020.0285 (13)0.0315 (15)0.0317 (15)0.0073 (11)0.0005 (11)0.0016 (12)
C1030.0251 (13)0.0425 (17)0.0504 (19)0.0096 (12)0.0041 (12)0.0036 (14)
C1040.0331 (16)0.057 (2)0.055 (2)0.0131 (14)0.0196 (14)0.0068 (17)
C1050.055 (2)0.066 (2)0.0386 (18)0.0221 (17)0.0223 (15)0.0181 (17)
C1060.0401 (15)0.0479 (18)0.0336 (16)0.0201 (14)0.0127 (12)0.0150 (13)
C1070.0291 (12)0.0287 (14)0.0215 (12)0.0121 (11)0.0015 (10)0.0028 (10)
C1080.0345 (14)0.0343 (15)0.0286 (14)0.0110 (12)−0.0006 (11)0.0015 (12)
C1090.0392 (16)0.0499 (19)0.0328 (16)0.0152 (14)−0.0096 (13)−0.0051 (14)
C1100.0558 (19)0.060 (2)0.0303 (16)0.0327 (17)−0.0058 (14)0.0049 (15)
C1110.0593 (19)0.0426 (18)0.0296 (15)0.0277 (15)0.0075 (14)0.0120 (13)
C1120.0391 (15)0.0305 (15)0.0287 (14)0.0136 (12)0.0054 (11)0.0073 (11)
C2010.0244 (12)0.0161 (12)0.0360 (15)0.0040 (9)−0.0020 (10)0.0030 (10)
C2020.0319 (14)0.0294 (15)0.0452 (17)0.0098 (12)0.0014 (12)0.0003 (13)
C2030.0357 (16)0.0344 (17)0.071 (2)0.0174 (13)−0.0012 (15)−0.0034 (16)
C2040.0395 (17)0.0250 (15)0.085 (3)0.0164 (13)−0.0196 (17)−0.0007 (16)
C2050.0517 (19)0.0301 (16)0.062 (2)0.0135 (14)−0.0126 (16)0.0145 (15)
C2060.0376 (15)0.0305 (15)0.0429 (17)0.0114 (12)−0.0004 (13)0.0090 (13)
C2070.0234 (12)0.0283 (14)0.0448 (17)0.0075 (11)0.0012 (11)0.0170 (12)
C2080.0326 (15)0.0324 (16)0.057 (2)0.0040 (12)−0.0038 (14)0.0126 (14)
C2090.0367 (17)0.0373 (18)0.078 (3)−0.0021 (14)−0.0114 (17)0.0171 (17)
C2100.0294 (16)0.057 (2)0.093 (3)0.0015 (15)0.0052 (18)0.043 (2)
C2110.0370 (17)0.064 (2)0.074 (3)0.0126 (16)0.0211 (17)0.040 (2)
C2120.0318 (15)0.0429 (18)0.0527 (19)0.0091 (13)0.0087 (13)0.0223 (15)
C3010.0474 (16)0.0239 (14)0.0274 (14)0.0144 (12)−0.0041 (12)0.0019 (11)
C3020.0468 (17)0.0289 (15)0.0388 (17)0.0082 (13)0.0025 (13)0.0008 (13)
C3030.061 (2)0.0341 (18)0.058 (2)0.0005 (15)−0.0018 (17)0.0047 (16)
C3040.088 (3)0.0293 (17)0.050 (2)0.0053 (18)−0.010 (2)−0.0013 (16)
C3050.104 (3)0.042 (2)0.042 (2)0.029 (2)0.000 (2)−0.0146 (16)
C3060.069 (2)0.0428 (19)0.0401 (18)0.0213 (17)0.0081 (16)−0.0024 (15)
C3070.0569 (18)0.0309 (15)0.0254 (14)0.0215 (13)0.0124 (13)0.0065 (12)
C3080.077 (2)0.056 (2)0.0317 (17)0.0309 (19)0.0040 (16)0.0107 (15)
C3090.118 (4)0.069 (3)0.038 (2)0.048 (3)0.010 (2)0.0218 (19)
C3100.151 (5)0.059 (3)0.040 (2)0.049 (3)0.037 (3)0.0278 (19)
C3110.106 (3)0.058 (3)0.064 (3)0.018 (2)0.047 (3)0.027 (2)
C3120.063 (2)0.052 (2)0.052 (2)0.0183 (17)0.0219 (17)0.0175 (17)
C4010.0283 (13)0.0273 (14)0.0289 (14)0.0123 (11)0.0049 (10)0.0059 (11)
C4020.0331 (14)0.0269 (14)0.0402 (16)0.0068 (11)−0.0016 (12)0.0053 (12)
C4030.0465 (17)0.0283 (15)0.0509 (19)0.0107 (13)0.0012 (14)0.0136 (14)
C4040.0505 (18)0.0455 (19)0.0488 (19)0.0249 (15)0.0039 (15)0.0219 (15)
C4050.0335 (15)0.0462 (18)0.0483 (19)0.0136 (13)−0.0067 (13)0.0134 (15)
C4060.0270 (13)0.0297 (15)0.0423 (16)0.0072 (11)0.0000 (11)0.0089 (12)
C4070.0239 (12)0.0308 (14)0.0452 (17)0.0118 (11)0.0074 (11)0.0171 (12)
C4080.0256 (13)0.0300 (15)0.0466 (17)0.0103 (11)0.0015 (12)0.0105 (13)
C4090.0302 (15)0.0337 (17)0.070 (2)0.0068 (12)−0.0053 (14)0.0124 (15)
C4100.0257 (15)0.0431 (19)0.094 (3)0.0092 (13)0.0066 (16)0.0294 (19)
C4110.0331 (16)0.053 (2)0.085 (3)0.0204 (15)0.0261 (16)0.0310 (19)
C4120.0344 (15)0.0371 (17)0.063 (2)0.0162 (13)0.0164 (14)0.0134 (15)
N40.0439 (14)0.0306 (13)0.0466 (15)0.0086 (11)0.0101 (12)0.0148 (12)
C100.0292 (13)0.0269 (14)0.0247 (13)0.0118 (11)0.0030 (10)0.0052 (11)
O20.118 (3)0.096 (2)0.069 (2)0.041 (2)0.011 (2)0.0424 (19)
C120.096 (4)0.070 (3)0.096 (4)0.029 (3)−0.034 (3)0.009 (3)
O10.227 (5)0.106 (3)0.138 (4)0.076 (3)0.103 (4)0.078 (3)
C110.146 (6)0.107 (5)0.080 (4)0.004 (4)0.039 (4)0.018 (3)
Geometric parameters (Å, º) top
Ir1—P12.3595 (6)C205—H2050.9400
Ir1—P32.3584 (7)C206—H2060.9400
Ir1—P42.3304 (6)C207—C2081.387 (4)
Ir1—N12.1090 (19)C207—C2121.397 (4)
Ir1—C12.127 (3)C208—C2091.390 (4)
Ir1—C102.027 (3)C208—H2080.9400
Cl1—C71.747 (3)C209—C2101.373 (5)
P1—C21.727 (3)C209—H2090.9400
P1—C1071.834 (2)C210—C2111.374 (5)
P1—C1011.846 (3)C210—H2100.9400
P2—C21.688 (3)C211—C2121.392 (4)
P2—C2011.824 (3)C211—H2110.9400
P2—C2071.827 (3)C212—H2120.9400
P2—C11.843 (3)C301—C3021.374 (4)
P3—C3071.811 (3)C301—C3061.392 (4)
P3—C3011.823 (3)C302—C3031.393 (4)
P3—C31.829 (3)C302—H3020.9400
P4—C4071.815 (3)C303—C3041.366 (5)
P4—C4011.833 (3)C303—H3030.9400
P4—C31.844 (3)C304—C3051.376 (6)
N1—N21.347 (3)C304—H3040.9400
N1—C41.421 (3)C305—C3061.390 (5)
N2—N31.259 (3)C305—H3050.9400
N3—C11.504 (3)C306—H3060.9400
C1—H10.92 (3)C307—C3121.384 (5)
C2—H20.93 (3)C307—C3081.393 (4)
C3—H3A0.9800C308—C3091.381 (5)
C3—H3B0.9800C308—H3080.9400
C4—C51.390 (4)C309—C3101.360 (7)
C4—C91.405 (4)C309—H3090.9400
C5—C61.378 (4)C310—C3111.370 (7)
C5—H50.9400C310—H3100.9400
C6—C71.383 (4)C311—C3121.399 (5)
C6—H60.9400C311—H3110.9400
C7—C81.366 (5)C312—H3120.9400
C8—C91.394 (4)C401—C4021.387 (4)
C8—H80.9400C401—C4061.394 (4)
C9—H90.9400C402—C4031.382 (4)
C101—C1061.395 (4)C402—H4020.9400
C101—C1021.395 (4)C403—C4041.384 (4)
C102—C1031.390 (4)C403—H4030.9400
C102—H1020.9400C404—C4051.374 (4)
C103—C1041.381 (5)C404—H4040.9400
C103—H1030.9400C405—C4061.386 (4)
C104—C1051.373 (5)C405—H4050.9400
C104—H1040.9400C406—H4060.9400
C105—C1061.388 (4)C407—C4081.382 (4)
C105—H1050.9400C407—C4121.395 (4)
C106—H1060.9400C408—C4091.395 (4)
C107—C1081.393 (4)C408—H4080.9400
C107—C1121.394 (4)C409—C4101.386 (5)
C108—C1091.389 (4)C409—H4090.9400
C108—H1080.9400C410—C4111.370 (5)
C109—C1101.378 (5)C410—H4100.9400
C109—H1090.9400C411—C4121.379 (4)
C110—C1111.383 (5)C411—H4110.9400
C110—H1100.9400C412—H4120.9400
C111—C1121.383 (4)N4—C101.158 (3)
C111—H1110.9400O2—C121.383 (6)
C112—H1120.9400O2—H2A0.8300
C201—C2061.392 (4)C12—H12A0.9700
C201—C2021.393 (4)C12—H12B0.9700
C202—C2031.392 (4)C12—H12C0.9700
C202—H2020.9400O1—C111.318 (7)
C203—C2041.367 (5)O1—H1A0.8300
C203—H2030.9400C11—H11A0.9700
C204—C2051.387 (5)C11—H11B0.9700
C204—H2040.9400C11—H11C0.9700
C205—C2061.385 (4)
C10—Ir1—N194.15 (9)C201—C202—H202120.0
C10—Ir1—C1169.38 (9)C204—C203—C202120.4 (3)
N1—Ir1—C175.31 (9)C204—C203—H203119.8
C10—Ir1—P489.88 (7)C202—C203—H203119.8
N1—Ir1—P4164.45 (6)C203—C204—C205120.3 (3)
C1—Ir1—P4100.63 (7)C203—C204—H204119.9
C10—Ir1—P392.00 (7)C205—C204—H204119.9
N1—Ir1—P392.64 (6)C206—C205—C204119.9 (3)
C1—Ir1—P389.80 (7)C206—C205—H205120.1
P4—Ir1—P372.19 (2)C204—C205—H205120.1
C10—Ir1—P192.84 (7)C205—C206—C201120.3 (3)
N1—Ir1—P196.69 (6)C205—C206—H206119.8
C1—Ir1—P187.23 (7)C201—C206—H206119.8
P4—Ir1—P198.11 (2)C208—C207—C212118.8 (3)
P3—Ir1—P1169.15 (2)C208—C207—P2117.7 (2)
C2—P1—C107109.18 (12)C212—C207—P2123.5 (2)
C2—P1—C101105.42 (12)C207—C208—C209120.5 (3)
C107—P1—C101100.87 (12)C207—C208—H208119.7
C2—P1—Ir1108.81 (10)C209—C208—H208119.7
C107—P1—Ir1113.21 (8)C210—C209—C208120.4 (3)
C101—P1—Ir1118.72 (8)C210—C209—H209119.8
C2—P2—C201112.23 (13)C208—C209—H209119.8
C2—P2—C207115.04 (13)C209—C210—C211119.8 (3)
C201—P2—C20799.28 (12)C209—C210—H210120.1
C2—P2—C1108.32 (13)C211—C210—H210120.1
C201—P2—C1111.83 (11)C210—C211—C212120.6 (4)
C207—P2—C1110.00 (13)C210—C211—H211119.7
C307—P3—C301104.16 (13)C212—C211—H211119.7
C307—P3—C3107.86 (14)C211—C212—C207119.9 (3)
C301—P3—C3105.55 (12)C211—C212—H212120.1
C307—P3—Ir1117.31 (9)C207—C212—H212120.1
C301—P3—Ir1125.75 (10)C302—C301—C306118.9 (3)
C3—P3—Ir193.86 (9)C302—C301—P3121.5 (2)
C407—P4—C401102.00 (12)C306—C301—P3119.5 (2)
C407—P4—C3106.82 (14)C301—C302—C303120.5 (3)
C401—P4—C3103.06 (12)C301—C302—H302119.7
C407—P4—Ir1121.19 (9)C303—C302—H302119.7
C401—P4—Ir1125.97 (9)C304—C303—C302120.5 (4)
C3—P4—Ir194.38 (8)C304—C303—H303119.7
N2—N1—C4111.0 (2)C302—C303—H303119.7
N2—N1—Ir1115.61 (15)C303—C304—C305119.4 (3)
C4—N1—Ir1127.86 (17)C303—C304—H304120.3
N3—N2—N1118.7 (2)C305—C304—H304120.3
N2—N3—C1116.7 (2)C304—C305—C306120.6 (3)
N3—C1—P2104.86 (16)C304—C305—H305119.7
N3—C1—Ir1109.85 (16)C306—C305—H305119.7
P2—C1—Ir1116.66 (13)C305—C306—C301119.9 (4)
N3—C1—H1105.7 (19)C305—C306—H306120.1
P2—C1—H1104.7 (19)C301—C306—H306120.1
Ir1—C1—H1114.1 (19)C312—C307—C308118.6 (3)
P2—C2—P1118.42 (16)C312—C307—P3121.8 (2)
P2—C2—H2118.6 (18)C308—C307—P3119.3 (3)
P1—C2—H2121.5 (19)C309—C308—C307120.3 (4)
P3—C3—P497.54 (12)C309—C308—H308119.9
P3—C3—H3A112.3C307—C308—H308119.9
P4—C3—H3A112.3C310—C309—C308120.5 (4)
P3—C3—H3B112.3C310—C309—H309119.8
P4—C3—H3B112.3C308—C309—H309119.8
H3A—C3—H3B109.9C309—C310—C311120.9 (4)
C5—C4—C9118.4 (2)C309—C310—H310119.6
C5—C4—N1120.9 (2)C311—C310—H310119.6
C9—C4—N1120.7 (2)C310—C311—C312119.2 (4)
C6—C5—C4121.0 (3)C310—C311—H311120.4
C6—C5—H5119.5C312—C311—H311120.4
C4—C5—H5119.5C307—C312—C311120.6 (4)
C5—C6—C7119.7 (3)C307—C312—H312119.7
C5—C6—H6120.1C311—C312—H312119.7
C7—C6—H6120.1C402—C401—C406119.1 (2)
C8—C7—C6120.9 (3)C402—C401—P4119.99 (19)
C8—C7—Cl1120.0 (2)C406—C401—P4120.9 (2)
C6—C7—Cl1119.1 (3)C403—C402—C401120.8 (3)
C7—C8—C9119.7 (3)C403—C402—H402119.6
C7—C8—H8120.1C401—C402—H402119.6
C9—C8—H8120.1C402—C403—C404119.7 (3)
C8—C9—C4120.2 (3)C402—C403—H403120.1
C8—C9—H9119.9C404—C403—H403120.1
C4—C9—H9119.9C405—C404—C403120.0 (3)
C106—C101—C102118.1 (2)C405—C404—H404120.0
C106—C101—P1124.0 (2)C403—C404—H404120.0
C102—C101—P1117.6 (2)C404—C405—C406120.6 (3)
C103—C102—C101120.6 (3)C404—C405—H405119.7
C103—C102—H102119.7C406—C405—H405119.7
C101—C102—H102119.7C405—C406—C401119.8 (3)
C104—C103—C102120.3 (3)C405—C406—H406120.1
C104—C103—H103119.8C401—C406—H406120.1
C102—C103—H103119.8C408—C407—C412119.1 (3)
C105—C104—C103119.6 (3)C408—C407—P4119.3 (2)
C105—C104—H104120.2C412—C407—P4121.1 (2)
C103—C104—H104120.2C407—C408—C409120.1 (3)
C104—C105—C106120.6 (3)C407—C408—H408119.9
C104—C105—H105119.7C409—C408—H408119.9
C106—C105—H105119.7C410—C409—C408119.5 (3)
C105—C106—C101120.7 (3)C410—C409—H409120.3
C105—C106—H106119.6C408—C409—H409120.3
C101—C106—H106119.6C411—C410—C409120.8 (3)
C108—C107—C112118.6 (2)C411—C410—H410119.6
C108—C107—P1120.4 (2)C409—C410—H410119.6
C112—C107—P1120.99 (19)C410—C411—C412119.7 (3)
C109—C108—C107120.7 (3)C410—C411—H411120.2
C109—C108—H108119.6C412—C411—H411120.2
C107—C108—H108119.6C411—C412—C407120.8 (3)
C110—C109—C108120.0 (3)C411—C412—H412119.6
C110—C109—H109120.0C407—C412—H412119.6
C108—C109—H109120.0N4—C10—Ir1178.1 (2)
C109—C110—C111119.8 (3)C12—O2—H2A109.5
C109—C110—H110120.1O2—C12—H12A109.5
C111—C110—H110120.1O2—C12—H12B109.5
C110—C111—C112120.5 (3)H12A—C12—H12B109.5
C110—C111—H111119.8O2—C12—H12C109.5
C112—C111—H111119.8H12A—C12—H12C109.5
C111—C112—C107120.4 (3)H12B—C12—H12C109.5
C111—C112—H112119.8C11—O1—H1A109.5
C107—C112—H112119.8O1—C11—H11A109.5
C206—C201—C202119.1 (3)O1—C11—H11B109.5
C206—C201—P2121.1 (2)H11A—C11—H11B109.5
C202—C201—P2119.7 (2)O1—C11—H11C109.5
C203—C202—C201120.0 (3)H11A—C11—H11C109.5
C203—C202—H202120.0H11B—C11—H11C109.5
C4—N1—N2—N3−169.9 (2)C203—C204—C205—C206−0.5 (5)
Ir1—N1—N2—N3−14.0 (3)C204—C205—C206—C2011.6 (4)
N1—N2—N3—C1−1.1 (3)C202—C201—C206—C205−1.3 (4)
N2—N3—C1—P2−111.2 (2)P2—C201—C206—C205−178.3 (2)
N2—N3—C1—Ir114.9 (3)C2—P2—C207—C208−38.4 (3)
C2—P2—C1—N3118.60 (17)C201—P2—C207—C20881.5 (2)
C201—P2—C1—N3−5.6 (2)C1—P2—C207—C208−161.0 (2)
C207—P2—C1—N3−114.89 (17)C2—P2—C207—C212144.0 (2)
C2—P2—C1—Ir1−3.16 (17)C201—P2—C207—C212−96.0 (2)
C201—P2—C1—Ir1−127.35 (14)C1—P2—C207—C21221.4 (3)
C207—P2—C1—Ir1123.34 (13)C212—C207—C208—C209−0.4 (4)
C201—P2—C2—P1120.99 (16)P2—C207—C208—C209−178.0 (2)
C207—P2—C2—P1−126.49 (16)C207—C208—C209—C210−0.3 (5)
C1—P2—C2—P1−3.0 (2)C208—C209—C210—C2110.1 (5)
C107—P1—C2—P2131.02 (16)C209—C210—C211—C2120.8 (5)
C101—P1—C2—P2−121.34 (17)C210—C211—C212—C207−1.5 (5)
Ir1—P1—C2—P27.02 (18)C208—C207—C212—C2111.2 (4)
C307—P3—C3—P4108.45 (14)P2—C207—C212—C211178.8 (2)
C301—P3—C3—P4−140.67 (13)C307—P3—C301—C302−129.3 (2)
Ir1—P3—C3—P4−11.87 (12)C3—P3—C301—C302117.2 (2)
C407—P4—C3—P3−112.44 (13)Ir1—P3—C301—C30210.6 (3)
C401—P4—C3—P3140.52 (13)C307—P3—C301—C30651.9 (3)
Ir1—P4—C3—P312.02 (12)C3—P3—C301—C306−61.6 (3)
N2—N1—C4—C5−151.0 (2)Ir1—P3—C301—C306−168.3 (2)
Ir1—N1—C4—C556.8 (3)C306—C301—C302—C303−2.4 (5)
N2—N1—C4—C931.9 (3)P3—C301—C302—C303178.8 (3)
Ir1—N1—C4—C9−120.4 (2)C301—C302—C303—C3041.5 (5)
C9—C4—C5—C60.3 (4)C302—C303—C304—C3050.8 (6)
N1—C4—C5—C6−176.9 (2)C303—C304—C305—C306−2.1 (6)
C4—C5—C6—C70.0 (4)C304—C305—C306—C3011.2 (6)
C5—C6—C7—C8−0.6 (4)C302—C301—C306—C3051.0 (5)
C5—C6—C7—Cl1179.9 (2)P3—C301—C306—C305179.9 (3)
C6—C7—C8—C90.8 (5)C301—P3—C307—C312−137.7 (3)
Cl1—C7—C8—C9−179.6 (2)C3—P3—C307—C312−25.8 (3)
C7—C8—C9—C4−0.5 (4)Ir1—P3—C307—C31278.4 (3)
C5—C4—C9—C80.0 (4)C301—P3—C307—C30849.5 (3)
N1—C4—C9—C8177.2 (3)C3—P3—C307—C308161.3 (2)
C2—P1—C101—C106−112.8 (2)Ir1—P3—C307—C308−94.4 (2)
C107—P1—C101—C1060.8 (3)C312—C307—C308—C309−1.1 (5)
Ir1—P1—C101—C106125.1 (2)P3—C307—C308—C309171.9 (3)
C2—P1—C101—C10260.8 (2)C307—C308—C309—C3100.8 (6)
C107—P1—C101—C102174.4 (2)C308—C309—C310—C3110.1 (6)
Ir1—P1—C101—C102−61.4 (2)C309—C310—C311—C312−0.7 (6)
C106—C101—C102—C1030.6 (4)C308—C307—C312—C3110.5 (5)
P1—C101—C102—C103−173.4 (2)P3—C307—C312—C311−172.4 (3)
C101—C102—C103—C104−0.2 (4)C310—C311—C312—C3070.4 (6)
C102—C103—C104—C105−0.5 (5)C407—P4—C401—C402−159.6 (2)
C103—C104—C105—C1060.8 (5)C3—P4—C401—C402−49.0 (3)
C104—C105—C106—C101−0.4 (5)Ir1—P4—C401—C40256.4 (3)
C102—C101—C106—C105−0.3 (4)C407—P4—C401—C40616.7 (3)
P1—C101—C106—C105173.3 (3)C3—P4—C401—C406127.4 (2)
C2—P1—C107—C1080.8 (3)Ir1—P4—C401—C406−127.2 (2)
C101—P1—C107—C108−109.9 (2)C406—C401—C402—C403−1.1 (4)
Ir1—P1—C107—C108122.2 (2)P4—C401—C402—C403175.3 (2)
C2—P1—C107—C112179.9 (2)C401—C402—C403—C4040.7 (5)
C101—P1—C107—C11269.2 (2)C402—C403—C404—C4050.5 (5)
Ir1—P1—C107—C112−58.7 (2)C403—C404—C405—C406−1.2 (5)
C112—C107—C108—C1090.4 (4)C404—C405—C406—C4010.8 (5)
P1—C107—C108—C109179.4 (2)C402—C401—C406—C4050.3 (4)
C107—C108—C109—C110−0.8 (5)P4—C401—C406—C405−176.1 (2)
C108—C109—C110—C1110.3 (5)C401—P4—C407—C408−93.6 (2)
C109—C110—C111—C1120.6 (5)C3—P4—C407—C408158.6 (2)
C110—C111—C112—C107−1.0 (5)Ir1—P4—C407—C40852.6 (3)
C108—C107—C112—C1110.5 (4)C401—P4—C407—C41278.8 (3)
P1—C107—C112—C111−178.6 (2)C3—P4—C407—C412−29.0 (3)
C2—P2—C201—C206167.1 (2)Ir1—P4—C407—C412−135.1 (2)
C207—P2—C201—C20645.1 (2)C412—C407—C408—C4090.6 (4)
C1—P2—C201—C206−71.0 (2)P4—C407—C408—C409173.1 (2)
C2—P2—C201—C202−9.8 (2)C407—C408—C409—C4101.9 (5)
C207—P2—C201—C202−131.8 (2)C408—C409—C410—C411−2.6 (5)
C1—P2—C201—C202112.1 (2)C409—C410—C411—C4120.8 (5)
C206—C201—C202—C203−0.1 (4)C410—C411—C412—C4071.7 (5)
P2—C201—C202—C203176.9 (2)C408—C407—C412—C411−2.4 (5)
C201—C202—C203—C2041.2 (4)P4—C407—C412—C411−174.8 (3)
C202—C203—C204—C205−0.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N40.832.022.8181 (1)162
O2—H2A···N30.832.162.9486 (1)158
Selected bond lengths (Å) and angles (°) for 1b, 2 and 3 top
1b23
Ir1—C12.128 (4)Ir1—C11.996 (5)Ir1—C12.127 (3)
Ir1—N11.999 (5)Ir1—N12.109 (2)
Ir1—P12.302 (1)Ir1—P12.2788 (14)Ir1—P12.3595 (6)
Ir1—P42.277 (1)
Ir1—Cl12.445 (1)Ir1—P32.3748 (14)Ir1—P32.3584 (7)
Ir1—C42.0815 (5)Ir1—P42.2662 (14)Ir1—P42.3304 (6)
Ir1—H11.51 (4)Ir1—C102.026 (2)
P2—C11.689 (4)P2—C11.776 (5)P2—C11.843 (2)
C1—P31.689 (4)C1—N31.346 (7)C1—N31.505 (3)
N1—N21.354 (6)N1—N21.347 (3)
N2—N31.308 (6)N2—N31.259 (3)
C4—Ir1—P194.22 (12)C1—Ir1—P185.35 (15)C1—Ir1—P187.23 (7)
C1—Ir1—P189.10 (12)N1—Ir1—P1140.40 (13)N1—Ir1—P196.69 (6)
P4—Ir1—P1173.16 (4)P4—Ir1—P195.59 (5)P4—Ir1—P198.11 (2)
C4—Ir1—P489.08 (12)C1—Ir1—P3173.04 (16)P3—Ir1—P1169.15 (2)
C1—Ir1—P484.94 (12)N1—Ir1—P3100.49 (13)C10—Ir1—P192.84 (7)
C4—Ir1—Cl194.42 (13)P4—Ir1—P370.69 (5)C10—Ir1—P392.00 (7)
C1—Ir1—Cl1175.28 (12)P1—Ir1—P3101.62 (5)N1—Ir1—P392.64 (6)
P4—Ir1—Cl192.17 (4)C1—Ir1—P4108.92 (16)C1—Ir1—P389.80 (7)
P1—Ir1—Cl193.55 (4)N1—Ir1—P4122.71 (13)P4—Ir1—P372.19 (2)
C4—Ir1—C189.27 (17)C1—Ir1—N173.7 (2)C10—Ir1—P489.88 (7)
C4—Ir1—H1176.6 (13)N1—Ir1—P4164.45 (6)
C1—Ir1—P4100.63 (7)
C10—Ir1—N194.15 (9)
C10—Ir1—C1169.38 (9)
N1—Ir1—C175.31 (9)
 

References

First citationChauvin, R. & Canac, Y. (2010). Editors. Transition Metal Complexes of Neutral eta1–Carbon Ligands (Topics in Organometallic Chemistry , Vol. 30). Berlin, Heidelberg: Springer.  Google Scholar
 First citationIshida, H. (2000). Z. Naturforsch. Teil A, 55, 769–771.  Google Scholar
 First citationKhramov, D. M. & Bielawski, C. W. (2005). Chem. Commun. pp. 4958–4960.  Web of Science CrossRef Google Scholar
 First citationKolodiazhnyi, O. I. (1999). Phosphorus Ylides. Weinheim: Wiley-VCH.  Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationPartl, G. J., Nussbaumer, F., Schlapp-Hackl, I., Schuh, W., Kopacka, H., Wurst, K. & Peringer, P. (2018). Acta Cryst. E74, 846–852.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationPetz, W. & Frenking, G. (2010). Topics in Organometallic Chemistry, Vol. 30, edited by R. Chauvin and Y. Canac, pp. 49–92. Berlin, Heidelberg: Springer.  Google Scholar
 First citationPoverenov, E. & Milstein, D. (2013). Topics in Organometallic Chemistry, Vol. 40, edited by G. van Koten and D. Milstein, pp. 21–47. Berlin, Heidelberg: Springer.  Google Scholar
 First citationReitsamer, C., Stallinger, S., Schuh, W., Kopacka, H., Wurst, K., Obendorf, D. & Peringer, P. (2012). Dalton Trans. 41, 3503–3514.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationSchlapp-Hackl, I., Pauer, B., Falschlunger, C., Schuh, W., Kopacka, H., Wurst, K. & Peringer, P. (2018). Acta Cryst. E74, 1643–1647.  CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationTakayama, T., Mitsumori, T., Kawano, M., Sekine, A., Uekusa, H., Ohashi, Y. & Sugawara, T. (2010). Acta Cryst. B66, 639–646.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 75| Part 1| January 2019| Pages 75-80
https://doi.org/10.1107/S2056989018017644
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS