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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 9| Part 6| June 2024| x240501
https://doi.org/10.1107/S2414314624005017

(4-Butyl-1-ethyl-1,2,4-triazol-5-yl­­idene)[(1,2,5,6-η)-cyclo­octa-1,5-diene](tri­phenyl­phosphane)iridium(I) tetra­fluorido­borate

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Timothy G. Lerch,a Michael Gau,b Daniel R. Alberta and Edward Rajaseelana*

aDepartment of Chemistry, Millersville University, Millersville, PA 17551, USA, and bDepartment of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, USA
*Correspondence e-mail: edward.rajaseelan@millersville.edu

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 24 May 2024; accepted 28 May 2024; online 7 June 2024)

The title compound, [Ir(C8H12)(C8H15N3)(C18H15P)]BF4, a new triazole-based N-heterocyclic carbene iridium(I) cationic complex with a tetra­fluorido­borate counter-anion, crystallizes with two cations and two anions in the asymmetric unit of space group Pc. The Ir centers of the cations have distorted square-planar conformations, formed by a bidentate (η2 + η2) cyclo­octa-1,5-diene (COD) ligand, an N-heterocyclic carbene and a tri­phenyl­phosphane ligand with the NHC carbon atom and P atom being cis. In the extended structure, non-classical C–H⋯F hydrogen bonds, one of which is notably short (H⋯F = 2.21 Å), link the cations and anions. The carbon atoms of one of the COD ligands are disordered over adjacent sites in a 0.62:0.38 ratio.

CCDC reference: 2358743

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[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

N-heterocyclic carbenes (NHCs) have emerged as excellent spectator ligands in homogeneous catalysis (Cazin, 2013[Cazin, C. S. J. (2013). Dalton Trans. 42, 7254.]; de Frémont et al., 2009[Frémont, P. de, Marion, N. & Nolan, S. P. (2009). Coord. Chem. Rev. 253, 862-892.]; Díez-Gonzáles et al., 2009[Díez-González, S., Marion, N. & Nolan, S. P. (2009). Chem. Rev. 109, 3612-3676.]; Rovis & Nolan, 2013[Rovis, T. & Nolan, S. (2013). Synlett, 24, 1188-1189.]; Ruff et al., 2016[Ruff, A., Kirby, C., Chan, B. C. & O'Connor, A. R. (2016). Organometallics, 35, 327-335.]; Zuo et al., 2014[Zuo, W., Tauer, S., Prokopchuk, D. E. & Morris, R. H. (2014). Organometallics, 33, 5791-5801.]). Their catalytic activity in the transfer hydrogenation of ketones and imines has also been studied and reported (Albrecht et al., 2002[Albrecht, M., Miecznikowski, J. R., Samuel, A., Faller, J. W. & Crabtree, R. H. (2002). Organometallics, 21, 3596-3604.]; Gnanamgari et al., 2007[Gnanamgari, D., Moores, A., Rajaseelan, E. & Crabtree, R. H. (2007). Organometallics, 26, 1226-1230.]). NHC ligands can be tuned sterically and electronically by having different substituents on the nitro­gen atoms (Gusev, 2009[Gusev, D. G. (2009). Organometallics, 28, 6458-6461.]). Many imidazole- and triazole-based NHC rhodium and iridium complexes have been synthesized and structurally characterized (Herrmann et al., 2006[Herrmann, W. A., Schütz, J., Frey, G. D. & Herdtweck, E. (2006). Organometallics, 25, 2437-2448.]; Wang & Lin 1998[Wang, H. M. J. & Lin, I. J. B. (1998). Organometallics, 17, 972-975.]; Chianese et al., 2004[Chianese, A. R., Kovacevic, A., Zeglis, B. M., Faller, J. W. & Crabtree, R. H. (2004). Organometallics, 23, 2461-2468.]). We continue to synthesize new imidazole- and triazole-based NHC complexes of rhodium and iridium, to study the effect of different substituents on the NHCs and the other ligands coordinated to the metal in transfer hydrogenation reactions (Nichol et al., 2009[Nichol, G. S., Rajaseelan, J., Anna, L. J. & Rajaseelan, E. (2009). Eur. J. Inorg. Chem. pp. 4320-4328.], 2010[Nichol, G. S., Stasiw, D., Anna, L. J. & Rajaseelan, E. (2010). Acta Cryst. E66, m1114.], 2011[Nichol, G. S., Rajaseelan, J., Walton, D. P. & Rajaseelan, E. (2011). Acta Cryst. E67, m1860-m1861.], 2012[Nichol, G. S., Walton, D. P., Anna, L. J. & Rajaseelan, E. (2012). Acta Cryst. E68, m158-m159.]; Idrees et al., 2017a[Idrees, K. B., Rutledge, W. J., Roberts, S. A. & Rajaseelan, E. (2017a). IUCrData, 2, x171411.],b[Idrees, K. B., Astashkin, A. V. & Rajaseelan, E. (2017b). IUCrData, 2, x171081.]; Rood et al., 2021[Rood, J., Subedi, C. B., Risell, J. P., Astashkin, A. V. & Rajaseelan, E. (2021). IUCrData, 6, x210597.]; Rushlow et al., 2021[Rushlow, J., Astashkin, A. V., Albert, D. R. & Rajaseelan, E. (2021). IUCrData, 6, x210811.]; Newman et al., 2021[Newman, E. B., Astashkin, A. V., Albert, D. R. & Rajaseelan, E. (2021). IUCrData, 6, x210836.]; Castaldi et al., 2021[Castaldi, K. T., Astashkin, A. V., Albert, D. R. & Rajaseelan, E. (2021). IUCrData, 6, x211142.]; Maynard et al., 2023[Maynard, A., Gau, M., Albert, D. R. & Rajaseelan, E. (2023). IUCrData, 8, x230903.]). The structure of the rhodium analogue of the title compound has been reported (Lerch et al., 2024[Lerch, T. G., Gau, M., Albert, D. R. & Rajaseelan, E. (2024). IUCrData, 9, x240060.]), and the title compound was synthesized to study the effect of the metal on catalytic properties.

The mol­ecular structure of the title complex, [Ir(C8H12)(C18H15P)(C8H15N3)][BF4] (3), comprises an IrI cation complex and a tetra­fluorido­borate counter-anion, as shown in Fig. 1[link]. No solvent mol­ecules are found in the structure. Two cations (A containing Ir1 and B containing Ir1′) and two anions are contained in the assymetric unit, which crystallizes in the monoclinic space group Pc. The distorted square-planar geometry around the iridium atoms is characterized by C1—Ir—P bond angles of 92.97 (14)° for cation A and 91.62 (15)° for cation B. The N—C—N bond angles of the NHC ligand are 102.8 (4) and 102.6 (4)° for cations A and B, respectively. The metal–phospho­rous and metal–carbene bond lengths of the title compound are similar to those of the previously published rhodium analogue (Lerch et al., 2024[Lerch, T. G., Gau, M., Albert, D. R. & Rajaseelan, E. (2024). IUCrData, 9, x240060.]) with Ir—CNHC bond lengths of 2.035 (5) Å (cation A) and 2.034 (5) Å (cation B) and Ir—P bond lengths of 2.3145 (13) Å (cation A) and 2.3154 (13) Å (cation B). Fig. 2[link] shows the packing viewed along the a axis with non-classical C—H⋯F hydrogen bonds (Table 1[link]) in the range of 2.21–2.49 Å for the H⋯F contacts shown as dotted red lines. The shortest C—H⋯F contacts arise from inter­actions from the CH moieties of the NHC (C2 and C2′) inter­acting with adjacent tetra­fluorido­borate anions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯F4′ 0.95 2.35 3.255 (7) 158
C4—H4B⋯F2i 0.98 2.49 3.352 (8) 147
C2′—H2′⋯F1ii 0.95 2.21 3.014 (6) 141
C11′—H11′⋯F4iii 0.95 2.46 3.363 (7) 160
C30′—H30D⋯F3′iii 0.99 2.49 3.355 (15) 146
Symmetry codes: (i) [x, -y+1, z+{\script{1\over 2}}]; (ii) [x-1, -y+1, z-{\script{1\over 2}}]; (iii) [x, -y+1, z-{\script{1\over 2}}].
[Figure 1]
Figure 1
The mol­ecular entities of the title compound (3) with displacement ellipsoids drawn at the 50% probability level.
[Figure 2]
Figure 2
Crystal packing diagram of the title compound (3), viewed along [100]. C—H⋯F hydrogen bonds are shown as dotted red lines.

Synthesis and crystallization

4-Butyl-1-ethyl-1,2,4-triazolium bromide (1) was synthesized by a previously published procedure (Lerch et al., 2024[Lerch, T. G., Gau, M., Albert, D. R. & Rajaseelan, E. (2024). IUCrData, 9, x240060.]). All other compounds used in the syntheses were obtained from Sigma-Aldrich and Strem and used as received; all syntheses were performed under a nitro­gen atmosphere. The reaction scheme is shown in Fig. 3[link]. NMR spectra were recorded at room temperature in CDCl3 on a 400 MHz (operating at 100 MHz for 13C and 162 MHz for 31P) Varian spectrometer and referenced to the residual solvent peak (δ in p.p.m.). The title compound (3) was crystallized by slow diffusion of pentane into a CH2Cl­2 solution.

[Figure 3]
Figure 3
Reaction scheme for the synthesis of (3).

[(1,2,5,6-η)-Cyclo­octa-1,5-diene](4-butyl-1-ethyl-1,2,4-triazol-5-yl­idene)chloro­iridium (2): triazolium bromide (1) (0.070 g, 0.298 mmol) and Ag2O (0.035 g, 0.149 mmol) were stirred at room temperature in the dark for 1 h in CH2Cl2 (10 ml). The mixture was then filtered through Celite into [Ir(cod)Cl]2 (0.100 g, 0.149 mmol), and stirred again in the dark for 1.5 h. The resulting solution was filtered through Celite and the solvent was removed under reduced pressure in a rotary evaporator. The yellow solid product (2) was dried under vacuum. Yield: 0.145 g (99%). 1H NMR: δ 7.86 (s, 1 H, N—C3H—N), 4.75 (q, 2 H, N—CH2 of eth­yl), 4.62 (t, 2 H, N—CH2 of but­yl), 4.50 (m, 2 H, CH of COD), 4.48 (m, 2 H, CH of COD), 3.36, 3.24 (m, 4 H, CH2 of COD), 2.38, 2.08 (m, 4 H, CH2 of COD), 1.89 (m, 2 H, CH2 of but­yl), 1.55 (m, 2H, CH2 of but­yl), 1.43 (m, 2 H, CH2 of but­yl), 1.50 (t, 3 H, CH3 of eth­yl) 1.05 (t, 3 H, CH3 of but­yl). 13C NMR: δ 182.31 (Ir—C), 141.66 (N—C3H—N), 86.29, 85.89 (CH of COD), 48.19 (N—CH2 of eth­yl), 47.67 (N—CH­2 of but­yl), 33.81, 33.21, 32.56, 29.82 (CH2 of COD), 29.11 (CH­2 of but­yl), 19.90 (CH­2 of but­yl), 15.37 (CH3 of eth­yl), 13.61 (CH­3 of but­yl).

[(1,2,5,6-η)-Cyclo­octa-1,5-diene](4-butyl-1-ethyl-1,2,4-triazol-5-yl­idene)(tri­phenyl­phosphane)iridium(I) tetra­fluorido­borate (3): tri­phenyl­phosphane (0.0804 g, 0.307 mmol) and AgBF4 (0.059 g, 0.307 mmol) were added to (2) (0.150 g, 0.307 mmol) in CH2Cl2 (15 ml). The solution was stirred in the dark for 1.5 h. The resulting mixture was filtered through Celite and the solvent was removed under reduced pressure. The bright red-orange solid product (3) was dried under vacuum. Red blocks suitable for data collection were crystallized from CH2Cl2/pentane solution. Yield: 0.243 g (99%). 1H NMR: δ 8.19 (s, 1 H, N—C3H—N), 7.52-7.25 (m, 15 H, Harom), 4.41 (q, 2 H, N—CH2 of eth­yl), 4.27 (t, 2 H, N—CH2 of but­yl), 4.18 (m, 2 H, CH of COD), 3.96 (m, 2 H, CH of COD), 3.82 (m, 2 H, CH2 of COD), 3.76 (m, 2 H, CH2 of COD), 2.36 (m, 2 H, CH2 of COD), 2.26 (m, 2 H, CH2 of COD), 2.05 (m, CH2 of but­yl), 1.68 (m, 2 H, CH2 of but­yl), 1.22 (t, 3 H, CH3 of eth­yl), 0.88 (t, 3 H, CH3 of but­yl). 13C NMR: δ 177.39 (In—C), 143.62 (N—C3H—N), 133.63–129.04 (Carom), 87.24, 87.12, 86.22, 86.11 (CH of COD), 48.49 (N—CH2 of eth­yl), 47.66 (N—CH­2 of but­yl), 31.63, 31.37, 30.88, 30.85 (CH2 of COD), 30.42 (CH2 of but­yl), 19.99 (CH2 of but­yl), 13.85 (CH3 of eth­yl), 13.66 (CH3 of but­yl). 31P NMR: δ 17.56.

Refinement

Hydrogen atoms were refined using a riding model. All carbon atoms of one of the COD ligands are disordered over adjacent sites in a 0.62:0.38 ratio. Refinement details are provided in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula [Ir(C8H12)(C8H15N3)(C18H15P)]BF4
Mr 802.68
Crystal system, space group Monoclinic, Pc
Temperature (K) 100
a, b, c (Å) 14.1426 (3), 12.3103 (3), 18.8707 (3)
β (°) 98.492 (2)
V (Å3) 3249.36 (12)
Z 4
Radiation type Mo Kα
μ (mm−1) 4.21
Crystal size (mm) 0.38 × 0.21 × 0.14 × 1.90 (radius)
 
Data collection
Diffractometer Rigaku XtaLAB Synergy-S
Absorption correction Multi-scan (CrysAlisPr; Rigaku OD, 2024[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.072, 0.097
No. of measured, independent and observed [I > 2σ(I)] reflections 65731, 15859, 14407
Rint 0.043
(sin θ/λ)max (Å−1) 0.668
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.027, 0.066, 1.08
No. of reflections 15859
No. of parameters 869
No. of restraints 251
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.99, −0.79
Absolute structure Flack x determined using 6483 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter −0.013 (4)
Computer programs: CrysAlis PRO (Rigaku OD, 2024[Rigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018/3 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 2358743

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624005017/hb4475sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624005017/hb4475Isup2.hkl

checkCIF report


Computing details top

(4-Butyl-1-ethyl-1,2,4-triazol-5-ylidene)[(1,2,5,6-η)-cycloocta-1,5-diene](triphenylphosphane)iridium(I) tetrafluoridoborate top
Crystal data top
[Ir(C8H12)(C8H15N3)(C18H15P)]BF4F(000) = 1600
Mr = 802.68Dx = 1.641 Mg m−3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
a = 14.1426 (3) ÅCell parameters from 31113 reflections
b = 12.3103 (3) Åθ = 2.4–28.3°
c = 18.8707 (3) ŵ = 4.21 mm−1
β = 98.492 (2)°T = 100 K
V = 3249.36 (12) Å3Block, red
Z = 40.38 × 0.21 × 0.14 × 1.90 (radius) mm
Data collection top
Rigaku XtaLAB Synergy-S
diffractometer		14407 reflections with I > 2σ(I)
Detector resolution: 10.0 pixels mm-1Rint = 0.043
ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(CrysAlisPr; Rigaku OD, 2024)		h = −18→18
Tmin = 0.072, Tmax = 0.097k = −16→16
65731 measured reflectionsl = −25→25
15859 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027 w = 1/[σ2(Fo2) + (0.0345P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.066(Δ/σ)max = 0.001
S = 1.08Δρmax = 0.99 e Å−3
15859 reflectionsΔρmin = −0.79 e Å−3
869 parametersAbsolute structure: Flack x determined using 6483 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
251 restraintsAbsolute structure parameter: −0.013 (4)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ir10.56035 (2)0.04309 (2)0.74486 (2)0.01394 (13)
P10.68145 (9)0.16063 (10)0.72500 (7)0.0144 (3)
N10.4235 (3)0.2315 (3)0.7352 (2)0.0178 (9)
N20.3501 (3)0.2883 (4)0.6949 (2)0.0237 (10)
N30.3982 (3)0.1484 (4)0.6357 (2)0.0195 (9)
C10.4559 (3)0.1465 (4)0.7003 (3)0.0181 (10)
C20.3374 (4)0.2347 (5)0.6347 (3)0.0251 (13)
H20.2911600.2534120.5947750.030*
C30.4567 (4)0.2662 (5)0.8086 (3)0.0226 (12)
H3A0.4748960.3438520.8087200.027*
H3B0.5142740.2238780.8281040.027*
C40.3799 (4)0.2502 (5)0.8565 (3)0.0309 (13)
H4A0.3241260.2950470.8387510.046*
H4B0.4051460.2716740.9056210.046*
H4C0.3609480.1735700.8557540.046*
C50.4008 (4)0.0747 (5)0.5747 (3)0.0217 (11)
H5A0.4548250.0233540.5860430.026*
H5B0.4113800.1173090.5320960.026*
C60.3068 (4)0.0105 (5)0.5578 (3)0.0237 (11)
H6A0.302609−0.0429340.5963770.028*
H6B0.2520500.0610100.5560840.028*
C70.3009 (6)−0.0488 (5)0.4862 (5)0.0285 (18)
H7A0.3085380.0042360.4480060.034*
H7B0.353908−0.1019110.4887450.034*
C80.2059 (4)−0.1080 (5)0.4671 (3)0.0327 (14)
H8A0.205018−0.1461440.4214480.049*
H8B0.153473−0.0552900.4628540.049*
H8C0.198233−0.1606140.5048260.049*
C90.6539 (4)0.3060 (4)0.7094 (3)0.0185 (11)
C100.6971 (4)0.3901 (4)0.7508 (3)0.0260 (12)
H100.7431370.3747560.7915640.031*
C110.6731 (5)0.4968 (5)0.7327 (4)0.0336 (14)
H110.7022240.5540640.7618370.040*
C120.6080 (5)0.5212 (5)0.6736 (4)0.0314 (14)
H120.5930950.5948100.6617050.038*
C130.5640 (4)0.4383 (5)0.6311 (3)0.0273 (13)
H130.5184760.4546820.5902410.033*
C140.5872 (4)0.3307 (4)0.6489 (3)0.0228 (11)
H140.5575050.2736410.6198410.027*
C150.7333 (3)0.1272 (4)0.6451 (3)0.0166 (10)
C160.7041 (4)0.0378 (4)0.6029 (3)0.0221 (12)
H160.654527−0.0076900.6147970.027*
C170.7474 (4)0.0143 (5)0.5428 (3)0.0243 (11)
H170.727030−0.0470140.5140520.029*
C180.8203 (4)0.0802 (6)0.5248 (3)0.0280 (13)
H180.8500130.0632400.4842220.034*
C190.8495 (4)0.1709 (5)0.5664 (3)0.0270 (12)
H190.8992010.2159090.5541150.032*
C200.8063 (4)0.1958 (4)0.6256 (3)0.0227 (11)
H200.8253710.2587080.6532190.027*
C210.7818 (3)0.1570 (4)0.7983 (3)0.0171 (10)
C220.8659 (4)0.0997 (4)0.7922 (3)0.0219 (11)
H220.8759690.0706560.7472480.026*
C230.9346 (4)0.0857 (5)0.8525 (3)0.0306 (13)
H230.9916030.0469880.8482080.037*
C240.9212 (4)0.1270 (5)0.9183 (3)0.0331 (14)
H240.9688440.1173530.9589200.040*
C250.8375 (4)0.1830 (5)0.9248 (3)0.0312 (14)
H250.8280360.2117660.9699330.037*
C260.7677 (4)0.1969 (5)0.8656 (3)0.0226 (11)
H260.7099710.2336010.8707060.027*
C270.4678 (5)−0.1004 (5)0.7291 (4)0.0213 (14)
H270.415887−0.0935700.6872030.026*
C280.4476 (5)−0.0460 (4)0.7894 (4)0.0249 (13)
H280.384238−0.0083610.7824770.030*
C290.4832 (4)−0.0762 (5)0.8664 (3)0.0286 (13)
H29E0.442895−0.1353570.8811040.034*
H29F0.476632−0.0126520.8974210.034*
C300.5881 (4)−0.1133 (5)0.8775 (3)0.0248 (12)
H30E0.615473−0.1037520.9284910.030*
H30F0.590902−0.1915750.8659300.030*
C310.6483 (4)−0.0496 (4)0.8308 (3)0.0216 (12)
H310.700609−0.0058890.8587900.026*
C320.6697 (4)−0.0858 (5)0.7652 (4)0.0178 (13)
H320.734469−0.0640910.7549080.021*
C330.6311 (4)−0.1877 (4)0.7278 (3)0.0220 (11)
H33E0.666546−0.2507830.7509780.026*
H33F0.642737−0.1851160.6774160.026*
C340.5240 (4)−0.2050 (4)0.7289 (3)0.0196 (11)
H34E0.497327−0.2482880.6864050.024*
H34F0.515634−0.2476660.7720530.024*
Ir1'0.06571 (2)0.45638 (2)0.25589 (2)0.01456 (14)
P1'0.19170 (9)0.34777 (10)0.23359 (7)0.0147 (3)
N1'−0.0612 (3)0.2590 (4)0.2479 (2)0.0202 (9)
N2'−0.1265 (3)0.1937 (4)0.2068 (3)0.0275 (11)
N3'−0.0829 (3)0.3325 (4)0.1449 (2)0.0235 (10)
C1'−0.0316 (4)0.3448 (4)0.2119 (3)0.0191 (11)
C2'−0.1377 (4)0.2405 (5)0.1444 (3)0.0267 (13)
H2'−0.1786740.2142630.1035470.032*
C3'−0.0364 (4)0.2351 (5)0.3238 (3)0.0229 (11)
H3'A0.0153160.2845420.3451730.027*
H3'B−0.0123760.1596380.3298810.027*
C4'−0.1231 (4)0.2488 (5)0.3627 (3)0.0274 (12)
H4'A−0.1489810.3222960.3544970.041*
H4'B−0.1037000.2372810.4141860.041*
H4'C−0.1721610.1955230.3443620.041*
C5'−0.0823 (4)0.4058 (5)0.0832 (3)0.0253 (12)
H5'A−0.0667550.3638750.0416700.030*
H5'B−0.0322430.4618690.0951920.030*
C6'−0.1796 (4)0.4609 (5)0.0633 (3)0.0296 (14)
H6'A−0.1917210.5088560.1031640.036*
H6'B−0.2302230.4047380.0568740.036*
C7'−0.1851 (5)0.5282 (6)−0.0054 (4)0.0348 (16)
H7'A−0.1357480.5858180.0012920.042*
H7'B−0.1717740.480858−0.0451870.042*
C8'−0.2834 (5)0.5799 (6)−0.0249 (4)0.0426 (17)
H8'A−0.3318220.522864−0.0346860.064*
H8'B−0.2839230.625312−0.0676580.064*
H8'C−0.2975150.6249560.0150420.064*
C9'0.2347 (3)0.3836 (4)0.1503 (3)0.0166 (10)
C10'0.3040 (4)0.3168 (4)0.1259 (3)0.0210 (11)
H10'0.3255630.2530920.1517650.025*
C11'0.3407 (4)0.3439 (5)0.0641 (3)0.0235 (11)
H11'0.3882810.2994320.0481610.028*
C12'0.3078 (5)0.4364 (6)0.0250 (4)0.0254 (15)
H12'0.3328720.454839−0.0174800.030*
C13'0.2384 (4)0.5013 (4)0.0486 (3)0.0229 (11)
H13'0.2155550.5637050.0217540.028*
C14'0.2018 (4)0.4757 (5)0.1112 (3)0.0221 (11)
H14'0.1547550.5208420.1271830.026*
C15'0.1671 (4)0.2016 (4)0.2207 (3)0.0175 (11)
C16'0.1112 (4)0.1715 (4)0.1558 (3)0.0232 (11)
H16'0.0916200.2250430.1203950.028*
C17'0.0846 (5)0.0642 (5)0.1430 (4)0.0301 (14)
H17'0.0471370.0442800.0989590.036*
C18'0.1126 (5)−0.0143 (5)0.1948 (4)0.0308 (14)
H18'0.093809−0.0877870.1862350.037*
C19'0.1675 (5)0.0144 (5)0.2583 (4)0.0357 (15)
H19'0.186661−0.0395040.2935200.043*
C20'0.1952 (4)0.1220 (5)0.2715 (3)0.0277 (12)
H20'0.2334720.1409850.3154520.033*
C21'0.2975 (3)0.3578 (4)0.3019 (3)0.0173 (10)
C22'0.2909 (4)0.3235 (4)0.3713 (3)0.0200 (11)
H22'0.2333960.2911540.3813570.024*
C23'0.3676 (4)0.3361 (5)0.4263 (3)0.0252 (12)
H23'0.3629110.3101300.4730500.030*
C24'0.4511 (4)0.3868 (5)0.4126 (3)0.0253 (12)
H24'0.5035940.3952950.4498380.030*
C25'0.4570 (4)0.4248 (5)0.3442 (3)0.0241 (12)
H25'0.5133780.4605940.3348760.029*
C26'0.3808 (4)0.4109 (4)0.2891 (3)0.0196 (10)
H26'0.3854260.4376490.2425040.023*
C27"−0.054 (2)0.5546 (19)0.2923 (15)0.0225 (17)0.38
H27"−0.1163510.5149800.2908770.027*0.38
C27'−0.0481 (13)0.5362 (10)0.3006 (8)0.0217 (16)0.62
H27'−0.1094330.4945330.2941320.026*0.62
C28"−0.034 (3)0.588 (3)0.2269 (16)0.0219 (18)0.38
H28"−0.0847930.5699680.1861160.026*0.38
C28'−0.0329 (16)0.5953 (14)0.2398 (9)0.0216 (17)0.62
H28'−0.0850300.5863810.1981750.026*0.62
C29"0.0205 (13)0.6881 (15)0.2153 (9)0.0220 (18)0.38
H29A0.0045510.7082840.1641190.026*0.38
H29B−0.0034980.7470490.2435350.026*0.38
C29'0.0196 (8)0.7046 (8)0.2404 (6)0.0212 (15)0.62
H29C−0.0029830.7424300.1947610.025*0.62
H29D0.0006960.7495140.2795320.025*0.62
C30"0.1251 (17)0.686 (2)0.2331 (11)0.0230 (18)0.38
H30A0.1451130.7508080.2623430.028*0.38
H30B0.1522840.6926910.1878640.028*0.38
C30'0.1255 (10)0.6997 (12)0.2498 (7)0.0252 (17)0.62
H30C0.1516520.7603850.2811580.030*0.62
H30D0.1467040.7103250.2025450.030*0.62
C31"0.169 (4)0.589 (3)0.2720 (18)0.0231 (18)0.38
H31"0.2352110.5707530.2628640.028*0.38
C31'0.167 (2)0.5931 (18)0.2821 (10)0.0227 (17)0.62
H31'0.2324950.5773340.2701170.027*0.62
C32"0.148 (3)0.560 (2)0.341 (2)0.0235 (18)0.38
H32"0.2006200.5205430.3721730.028*0.38
C32'0.1504 (17)0.5444 (13)0.3434 (12)0.0228 (16)0.62
H32'0.2060800.5023960.3684310.027*0.62
C33"0.0839 (15)0.6266 (14)0.3833 (12)0.0244 (17)0.38
H33A0.1009720.6092980.4348050.029*0.38
H33B0.0981760.7043930.3770440.029*0.38
C33'0.0888 (8)0.5962 (9)0.3936 (7)0.0285 (16)0.62
H33C0.1131970.5737720.4432750.034*0.62
H33D0.0951830.6761650.3909510.034*0.62
C34"−0.0181 (12)0.6105 (13)0.3634 (9)0.0252 (17)0.38
H34A−0.0490880.6826310.3627340.030*0.38
H34B−0.0409380.5677790.4019570.030*0.38
C34'−0.0131 (7)0.5677 (9)0.3776 (6)0.0246 (15)0.62
H34C−0.0511770.6304040.3901220.030*0.62
H34D−0.0255900.5064070.4088990.030*0.62
F10.6760 (3)0.7630 (3)0.5436 (3)0.0520 (11)
F20.5460 (3)0.6681 (3)0.4912 (3)0.0522 (11)
F30.5814 (3)0.8334 (3)0.4480 (2)0.0428 (9)
F40.5261 (3)0.8233 (3)0.5531 (2)0.0504 (10)
B10.5832 (5)0.7701 (6)0.5084 (4)0.0310 (15)
F1'0.0448 (3)0.3162 (3)0.4888 (3)0.0691 (16)
F2'0.0456 (3)0.1342 (3)0.4753 (2)0.0416 (9)
F3'0.1072 (3)0.2088 (4)0.5808 (2)0.0597 (12)
F4'0.1850 (3)0.2295 (3)0.4875 (2)0.0460 (10)
B1'0.0940 (5)0.2228 (6)0.5074 (4)0.0288 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.01192 (18)0.01183 (12)0.0180 (4)−0.00071 (9)0.0020 (2)0.00016 (10)
P10.0139 (6)0.0127 (6)0.0169 (7)−0.0010 (5)0.0028 (5)−0.0006 (5)
N10.015 (2)0.016 (2)0.021 (2)0.0039 (16)0.0011 (17)0.0001 (18)
N20.020 (2)0.026 (2)0.024 (2)0.0069 (18)0.0009 (18)−0.0012 (19)
N30.019 (2)0.020 (2)0.020 (2)0.0008 (17)0.0025 (17)−0.0019 (17)
C10.014 (2)0.017 (3)0.022 (3)−0.0033 (19)−0.0005 (19)0.001 (2)
C20.019 (3)0.032 (3)0.023 (3)0.011 (2)−0.001 (2)0.005 (3)
C30.025 (3)0.018 (3)0.024 (3)0.004 (2)0.001 (2)−0.005 (2)
C40.028 (3)0.041 (4)0.024 (3)0.013 (3)0.006 (2)0.002 (3)
C50.019 (3)0.027 (3)0.019 (3)−0.001 (2)0.002 (2)−0.005 (2)
C60.020 (3)0.028 (3)0.023 (3)0.000 (2)0.001 (2)−0.003 (2)
C70.025 (4)0.030 (4)0.030 (4)−0.003 (2)0.003 (3)−0.002 (3)
C80.034 (3)0.035 (3)0.028 (3)−0.006 (3)0.000 (2)−0.004 (3)
C90.019 (3)0.014 (3)0.024 (3)−0.001 (2)0.008 (2)0.001 (2)
C100.023 (3)0.020 (3)0.033 (3)0.000 (2)0.001 (2)−0.005 (2)
C110.038 (3)0.017 (3)0.045 (4)−0.003 (2)0.003 (3)−0.007 (3)
C120.033 (3)0.018 (3)0.044 (4)0.005 (2)0.008 (3)0.000 (3)
C130.027 (3)0.023 (3)0.031 (3)0.007 (2)0.003 (2)0.005 (2)
C140.024 (3)0.021 (3)0.024 (3)−0.003 (2)0.004 (2)−0.001 (2)
C150.016 (2)0.016 (2)0.017 (2)0.0013 (19)0.0024 (18)0.000 (2)
C160.023 (3)0.019 (3)0.023 (3)−0.002 (2)0.001 (2)−0.001 (2)
C170.028 (3)0.025 (3)0.021 (3)0.002 (2)0.005 (2)−0.005 (2)
C180.031 (3)0.031 (3)0.025 (3)0.000 (3)0.013 (2)−0.001 (3)
C190.030 (3)0.024 (3)0.030 (3)−0.004 (2)0.016 (2)0.000 (2)
C200.023 (3)0.020 (3)0.026 (3)−0.002 (2)0.008 (2)−0.002 (2)
C210.016 (2)0.014 (2)0.021 (2)−0.0045 (18)0.0010 (19)0.0007 (19)
C220.018 (2)0.017 (3)0.030 (3)−0.005 (2)0.003 (2)0.006 (2)
C230.022 (3)0.028 (3)0.038 (3)−0.003 (2)−0.008 (2)0.011 (3)
C240.032 (3)0.035 (3)0.028 (3)−0.013 (3)−0.007 (2)0.011 (3)
C250.037 (3)0.035 (3)0.020 (3)−0.019 (3)−0.002 (2)0.002 (2)
C260.023 (3)0.022 (3)0.024 (3)−0.011 (2)0.005 (2)−0.001 (2)
C270.018 (3)0.015 (3)0.031 (4)−0.009 (2)0.001 (3)0.002 (3)
C280.020 (3)0.020 (3)0.037 (3)−0.006 (2)0.012 (2)0.005 (2)
C290.033 (3)0.025 (3)0.030 (3)−0.004 (2)0.013 (3)0.006 (2)
C300.029 (3)0.021 (3)0.024 (3)−0.001 (2)0.003 (2)0.008 (2)
C310.022 (3)0.015 (3)0.025 (3)0.0009 (19)−0.005 (2)0.005 (2)
C320.015 (3)0.011 (3)0.026 (4)0.002 (2)−0.002 (2)0.002 (2)
C330.021 (3)0.012 (2)0.031 (3)0.0022 (19)−0.002 (2)0.000 (2)
C340.017 (2)0.016 (3)0.026 (3)−0.0027 (19)0.002 (2)−0.001 (2)
Ir1'0.0130 (2)0.01289 (12)0.0178 (4)0.00096 (9)0.0025 (2)0.00014 (10)
P1'0.0139 (6)0.0129 (6)0.0176 (7)0.0016 (5)0.0036 (5)0.0015 (5)
N1'0.021 (2)0.019 (2)0.021 (2)−0.0064 (17)0.0040 (18)−0.0006 (18)
N2'0.026 (2)0.031 (3)0.025 (2)−0.015 (2)0.0024 (19)−0.004 (2)
N3'0.022 (2)0.027 (2)0.020 (2)−0.0055 (19)0.0001 (18)0.0025 (19)
C1'0.016 (2)0.022 (3)0.020 (2)0.001 (2)0.004 (2)−0.001 (2)
C2'0.021 (3)0.036 (4)0.023 (3)−0.015 (2)0.002 (2)−0.004 (3)
C3'0.021 (3)0.023 (3)0.025 (3)−0.003 (2)0.002 (2)0.005 (2)
C4'0.024 (3)0.039 (3)0.019 (3)−0.005 (2)0.003 (2)−0.001 (2)
C5'0.022 (3)0.034 (3)0.020 (3)−0.005 (2)0.002 (2)0.006 (2)
C6'0.019 (3)0.046 (4)0.024 (3)−0.001 (2)0.004 (2)0.003 (3)
C7'0.025 (3)0.045 (4)0.035 (4)0.008 (3)0.007 (3)0.008 (3)
C8'0.029 (3)0.060 (5)0.040 (4)0.008 (3)0.006 (3)0.015 (3)
C9'0.016 (2)0.018 (2)0.016 (2)0.0016 (19)0.0038 (18)0.0006 (19)
C10'0.020 (3)0.019 (3)0.024 (3)0.001 (2)0.004 (2)0.002 (2)
C11'0.024 (3)0.024 (3)0.024 (3)0.000 (2)0.008 (2)−0.003 (2)
C12'0.029 (4)0.030 (3)0.018 (3)−0.007 (3)0.008 (3)0.002 (3)
C13'0.028 (3)0.019 (3)0.021 (3)−0.002 (2)0.004 (2)0.004 (2)
C14'0.023 (3)0.021 (3)0.022 (3)0.001 (2)0.000 (2)0.000 (2)
C15'0.018 (2)0.012 (3)0.024 (3)0.0008 (19)0.008 (2)0.001 (2)
C16'0.029 (3)0.017 (2)0.024 (3)−0.003 (2)0.006 (2)0.001 (2)
C17'0.036 (3)0.022 (3)0.033 (3)−0.006 (2)0.007 (3)−0.007 (2)
C18'0.035 (3)0.013 (3)0.045 (4)−0.004 (2)0.007 (3)−0.004 (3)
C19'0.042 (4)0.017 (3)0.046 (4)0.001 (3)0.002 (3)0.009 (3)
C20'0.027 (3)0.023 (3)0.031 (3)0.001 (2)−0.002 (2)0.001 (2)
C21'0.016 (2)0.013 (2)0.023 (2)0.0050 (18)0.0019 (19)−0.0011 (19)
C22'0.019 (3)0.019 (3)0.022 (3)0.005 (2)0.004 (2)0.002 (2)
C23'0.029 (3)0.023 (3)0.023 (3)0.012 (2)0.004 (2)0.002 (2)
C24'0.021 (3)0.027 (3)0.025 (3)0.007 (2)−0.005 (2)−0.008 (2)
C25'0.017 (3)0.024 (3)0.031 (3)−0.001 (2)0.004 (2)−0.007 (2)
C26'0.020 (3)0.018 (2)0.020 (2)0.002 (2)0.002 (2)−0.004 (2)
C27"0.021 (3)0.017 (4)0.032 (4)0.007 (3)0.009 (3)0.000 (3)
C27'0.020 (3)0.016 (3)0.031 (4)0.006 (3)0.009 (3)0.000 (3)
C28"0.019 (3)0.016 (3)0.031 (4)0.006 (3)0.006 (3)0.000 (3)
C28'0.018 (3)0.016 (3)0.031 (4)0.008 (2)0.006 (3)0.000 (3)
C29"0.019 (3)0.015 (3)0.032 (4)0.004 (3)0.003 (3)0.001 (3)
C29'0.019 (2)0.014 (3)0.030 (4)0.005 (2)0.003 (3)0.000 (3)
C30"0.023 (3)0.014 (3)0.030 (4)0.000 (3)−0.003 (3)−0.002 (3)
C30'0.026 (3)0.015 (3)0.032 (4)−0.001 (2)−0.006 (3)0.001 (3)
C31"0.023 (3)0.015 (3)0.029 (4)0.002 (3)−0.006 (3)−0.002 (3)
C31'0.022 (3)0.015 (3)0.029 (4)0.001 (2)−0.005 (3)−0.002 (3)
C32"0.024 (3)0.017 (4)0.027 (3)0.007 (3)−0.004 (3)−0.003 (3)
C32'0.024 (3)0.015 (4)0.026 (3)0.007 (3)−0.005 (2)−0.005 (3)
C33"0.029 (3)0.016 (4)0.027 (3)0.010 (3)0.001 (3)0.000 (3)
C33'0.031 (3)0.024 (4)0.030 (3)0.014 (3)0.000 (3)−0.004 (3)
C34"0.027 (3)0.019 (4)0.030 (4)0.009 (3)0.007 (3)−0.002 (3)
C34'0.028 (3)0.018 (3)0.029 (3)0.007 (3)0.009 (3)0.001 (3)
F10.0285 (19)0.048 (2)0.073 (3)−0.0005 (16)−0.0142 (19)0.012 (2)
F20.039 (2)0.036 (2)0.078 (3)−0.0018 (18)−0.003 (2)−0.002 (2)
F30.039 (2)0.059 (2)0.0292 (19)−0.0038 (17)0.0004 (16)0.0076 (17)
F40.044 (2)0.067 (3)0.042 (2)−0.005 (2)0.0125 (18)−0.003 (2)
B10.020 (3)0.040 (4)0.032 (4)−0.006 (3)0.000 (3)0.002 (3)
F1'0.047 (2)0.028 (2)0.117 (4)0.0085 (18)−0.038 (3)−0.007 (3)
F2'0.0337 (19)0.035 (2)0.053 (2)−0.0053 (16)−0.0059 (17)−0.0016 (18)
F3'0.055 (2)0.099 (3)0.027 (2)−0.010 (2)0.0137 (18)−0.002 (2)
F4'0.035 (2)0.064 (3)0.042 (2)−0.0096 (18)0.0121 (17)0.011 (2)
B1'0.023 (3)0.037 (4)0.025 (3)−0.003 (3)−0.001 (3)0.004 (3)
Geometric parameters (Å, º) top
Ir1—P12.3145 (13)N2'—C2'1.299 (8)
Ir1—C12.035 (5)N3'—C1'1.370 (7)
Ir1—C272.192 (6)N3'—C2'1.372 (7)
Ir1—C282.202 (6)N3'—C5'1.473 (7)
Ir1—C312.210 (5)C2'—H2'0.9500
Ir1—C322.209 (6)C3'—H3'A0.9900
P1—C91.846 (5)C3'—H3'B0.9900
P1—C151.817 (5)C3'—C4'1.529 (8)
P1—C211.830 (5)C4'—H4'A0.9800
N1—N21.381 (6)C4'—H4'B0.9800
N1—C11.352 (7)C4'—H4'C0.9800
N1—C31.460 (7)C5'—H5'A0.9900
N2—C21.304 (7)C5'—H5'B0.9900
N3—C11.364 (6)C5'—C6'1.531 (8)
N3—C21.365 (7)C6'—H6'A0.9900
N3—C51.470 (7)C6'—H6'B0.9900
C2—H20.9500C6'—C7'1.532 (9)
C3—H3A0.9900C7'—H7'A0.9900
C3—H3B0.9900C7'—H7'B0.9900
C3—C41.525 (8)C7'—C8'1.523 (9)
C4—H4A0.9800C8'—H8'A0.9800
C4—H4B0.9800C8'—H8'B0.9800
C4—H4C0.9800C8'—H8'C0.9800
C5—H5A0.9900C9'—C10'1.408 (7)
C5—H5B0.9900C9'—C14'1.395 (7)
C5—C61.539 (7)C10'—H10'0.9500
C6—H6A0.9900C10'—C11'1.385 (8)
C6—H6B0.9900C11'—H11'0.9500
C6—C71.527 (10)C11'—C12'1.399 (9)
C7—H7A0.9900C12'—H12'0.9500
C7—H7B0.9900C12'—C13'1.389 (9)
C7—C81.524 (9)C13'—H13'0.9500
C8—H8A0.9800C13'—C14'1.394 (8)
C8—H8B0.9800C14'—H14'0.9500
C8—H8C0.9800C15'—C16'1.406 (7)
C9—C101.384 (8)C15'—C20'1.387 (8)
C9—C141.403 (7)C16'—H16'0.9500
C10—H100.9500C16'—C17'1.384 (8)
C10—C111.387 (8)C17'—H17'0.9500
C11—H110.9500C17'—C18'1.389 (9)
C11—C121.370 (9)C18'—H18'0.9500
C12—H120.9500C18'—C19'1.376 (9)
C12—C131.388 (9)C19'—H19'0.9500
C13—H130.9500C19'—C20'1.393 (8)
C13—C141.393 (8)C20'—H20'0.9500
C14—H140.9500C21'—C22'1.393 (7)
C15—C161.386 (7)C21'—C26'1.398 (7)
C15—C201.424 (7)C22'—H22'0.9500
C16—H160.9500C22'—C23'1.394 (7)
C16—C171.395 (8)C23'—H23'0.9500
C17—H170.9500C23'—C24'1.393 (8)
C17—C181.392 (8)C24'—H24'0.9500
C18—H180.9500C24'—C25'1.387 (8)
C18—C191.392 (9)C25'—H25'0.9500
C19—H190.9500C25'—C26'1.393 (7)
C19—C201.385 (8)C26'—H26'0.9500
C20—H200.9500C27"—H27"1.0000
C21—C221.402 (7)C27"—C28"1.37 (4)
C21—C261.404 (8)C27"—C34"1.53 (3)
C22—H220.9500C27'—H27'1.0000
C22—C231.393 (8)C27'—C28'1.401 (18)
C23—H230.9500C27'—C34'1.515 (12)
C23—C241.382 (9)C28"—H28"1.0000
C24—H240.9500C28"—C29"1.48 (3)
C24—C251.390 (9)C28'—H28'1.0000
C25—H250.9500C28'—C29'1.536 (12)
C25—C261.388 (8)C29"—H29A0.9900
C26—H260.9500C29"—H29B0.9900
C27—H271.0000C29"—C30"1.47 (2)
C27—C281.386 (10)C29'—H29C0.9900
C27—C341.514 (8)C29'—H29D0.9900
C28—H281.0000C29'—C30'1.484 (12)
C28—C291.511 (9)C30"—H30A0.9900
C29—H29E0.9900C30"—H30B0.9900
C29—H29F0.9900C30"—C31"1.49 (3)
C29—C301.537 (8)C30'—H30C0.9900
C30—H30E0.9900C30'—H30D0.9900
C30—H30F0.9900C30'—C31'1.529 (13)
C30—C311.530 (8)C31"—H31"1.0000
C31—H311.0000C31"—C32"1.44 (4)
C31—C321.390 (9)C31'—H31'1.0000
C32—H321.0000C31'—C32'1.36 (2)
C32—C331.502 (8)C32"—H32"1.0000
C33—H33E0.9900C32"—C33"1.53 (3)
C33—H33F0.9900C32'—H32'1.0000
C33—C341.533 (8)C32'—C33'1.519 (13)
C34—H34E0.9900C33"—H33A0.9900
C34—H34F0.9900C33"—H33B0.9900
Ir1'—P1'2.3154 (13)C33"—C34"1.45 (2)
Ir1'—C1'2.034 (5)C33'—H33C0.9900
Ir1'—C27"2.27 (3)C33'—H33D0.9900
Ir1'—C27'2.160 (17)C33'—C34'1.470 (11)
Ir1'—C28"2.16 (4)C34"—H34A0.9900
Ir1'—C28'2.20 (2)C34"—H34B0.9900
Ir1'—C31"2.18 (5)C34'—H34C0.9900
Ir1'—C31'2.22 (3)C34'—H34D0.9900
Ir1'—C32"2.24 (4)F1—B11.384 (7)
Ir1'—C32'2.18 (3)F2—B11.382 (8)
P1'—C9'1.822 (5)F3—B11.377 (8)
P1'—C15'1.842 (5)F4—B11.412 (8)
P1'—C21'1.829 (5)F1'—B1'1.362 (8)
N1'—N2'1.375 (6)F2'—B1'1.380 (8)
N1'—C1'1.354 (7)F3'—B1'1.381 (7)
N1'—C3'1.453 (7)F4'—B1'1.394 (7)
C1—Ir1—P192.97 (14)C1'—N1'—C3'127.2 (4)
C1—Ir1—C2793.7 (2)C2'—N2'—N1'103.5 (4)
C1—Ir1—C2886.9 (2)C1'—N3'—C2'108.5 (5)
C1—Ir1—C31157.2 (2)C1'—N3'—C5'126.7 (5)
C1—Ir1—C32165.4 (2)C2'—N3'—C5'124.7 (5)
C27—Ir1—P1157.38 (19)N1'—C1'—Ir1'124.2 (4)
C27—Ir1—C2836.8 (2)N1'—C1'—N3'102.6 (4)
C27—Ir1—C3186.8 (2)N3'—C1'—Ir1'133.2 (4)
C27—Ir1—C3280.4 (2)N2'—C2'—N3'111.5 (5)
C28—Ir1—P1165.48 (17)N2'—C2'—H2'124.2
C28—Ir1—C3179.8 (2)N3'—C2'—H2'124.2
C28—Ir1—C3296.0 (2)N1'—C3'—H3'A109.5
C31—Ir1—P195.25 (15)N1'—C3'—H3'B109.5
C32—Ir1—P187.78 (16)N1'—C3'—C4'110.9 (4)
C32—Ir1—C3136.7 (2)H3'A—C3'—H3'B108.0
C9—P1—Ir1119.21 (17)C4'—C3'—H3'A109.5
C15—P1—Ir1113.04 (16)C4'—C3'—H3'B109.5
C15—P1—C9100.9 (2)C3'—C4'—H4'A109.5
C15—P1—C21105.0 (2)C3'—C4'—H4'B109.5
C21—P1—Ir1111.86 (17)C3'—C4'—H4'C109.5
C21—P1—C9105.5 (2)H4'A—C4'—H4'B109.5
N2—N1—C3119.0 (4)H4'A—C4'—H4'C109.5
C1—N1—N2113.9 (4)H4'B—C4'—H4'C109.5
C1—N1—C3127.1 (4)N3'—C5'—H5'A109.5
C2—N2—N1102.7 (4)N3'—C5'—H5'B109.5
C1—N3—C2108.5 (4)N3'—C5'—C6'110.8 (5)
C1—N3—C5127.5 (4)H5'A—C5'—H5'B108.1
C2—N3—C5123.9 (5)C6'—C5'—H5'A109.5
N1—C1—Ir1124.1 (4)C6'—C5'—H5'B109.5
N1—C1—N3102.8 (4)C5'—C6'—H6'A109.2
N3—C1—Ir1133.0 (4)C5'—C6'—H6'B109.2
N2—C2—N3112.1 (5)C5'—C6'—C7'112.2 (5)
N2—C2—H2123.9H6'A—C6'—H6'B107.9
N3—C2—H2123.9C7'—C6'—H6'A109.2
N1—C3—H3A109.3C7'—C6'—H6'B109.2
N1—C3—H3B109.3C6'—C7'—H7'A109.4
N1—C3—C4111.5 (5)C6'—C7'—H7'B109.4
H3A—C3—H3B108.0H7'A—C7'—H7'B108.0
C4—C3—H3A109.3C8'—C7'—C6'111.2 (6)
C4—C3—H3B109.3C8'—C7'—H7'A109.4
C3—C4—H4A109.5C8'—C7'—H7'B109.4
C3—C4—H4B109.5C7'—C8'—H8'A109.5
C3—C4—H4C109.5C7'—C8'—H8'B109.5
H4A—C4—H4B109.5C7'—C8'—H8'C109.5
H4A—C4—H4C109.5H8'A—C8'—H8'B109.5
H4B—C4—H4C109.5H8'A—C8'—H8'C109.5
N3—C5—H5A109.4H8'B—C8'—H8'C109.5
N3—C5—H5B109.4C10'—C9'—P1'118.6 (4)
N3—C5—C6111.0 (4)C14'—C9'—P1'121.7 (4)
H5A—C5—H5B108.0C14'—C9'—C10'119.7 (5)
C6—C5—H5A109.4C9'—C10'—H10'120.0
C6—C5—H5B109.4C11'—C10'—C9'120.0 (5)
C5—C6—H6A109.4C11'—C10'—H10'120.0
C5—C6—H6B109.4C10'—C11'—H11'119.9
H6A—C6—H6B108.0C10'—C11'—C12'120.2 (6)
C7—C6—C5111.2 (5)C12'—C11'—H11'119.9
C7—C6—H6A109.4C11'—C12'—H12'120.2
C7—C6—H6B109.4C13'—C12'—C11'119.6 (6)
C6—C7—H7A109.3C13'—C12'—H12'120.2
C6—C7—H7B109.3C12'—C13'—H13'119.7
H7A—C7—H7B108.0C12'—C13'—C14'120.7 (6)
C8—C7—C6111.6 (6)C14'—C13'—H13'119.7
C8—C7—H7A109.3C9'—C14'—H14'120.1
C8—C7—H7B109.3C13'—C14'—C9'119.7 (5)
C7—C8—H8A109.5C13'—C14'—H14'120.1
C7—C8—H8B109.5C16'—C15'—P1'116.3 (4)
C7—C8—H8C109.5C20'—C15'—P1'124.7 (4)
H8A—C8—H8B109.5C20'—C15'—C16'118.9 (5)
H8A—C8—H8C109.5C15'—C16'—H16'119.8
H8B—C8—H8C109.5C17'—C16'—C15'120.4 (5)
C10—C9—P1124.7 (4)C17'—C16'—H16'119.8
C10—C9—C14119.0 (5)C16'—C17'—H17'120.0
C14—C9—P1116.2 (4)C16'—C17'—C18'120.0 (6)
C9—C10—H10120.1C18'—C17'—H17'120.0
C9—C10—C11119.8 (5)C17'—C18'—H18'120.0
C11—C10—H10120.1C19'—C18'—C17'120.0 (6)
C10—C11—H11119.4C19'—C18'—H18'120.0
C12—C11—C10121.3 (6)C18'—C19'—H19'119.7
C12—C11—H11119.4C18'—C19'—C20'120.5 (6)
C11—C12—H12120.0C20'—C19'—H19'119.7
C11—C12—C13120.0 (6)C15'—C20'—C19'120.2 (6)
C13—C12—H12120.0C15'—C20'—H20'119.9
C12—C13—H13120.3C19'—C20'—H20'119.9
C12—C13—C14119.3 (6)C22'—C21'—P1'118.7 (4)
C14—C13—H13120.3C22'—C21'—C26'118.6 (5)
C9—C14—H14119.7C26'—C21'—P1'122.2 (4)
C13—C14—C9120.6 (5)C21'—C22'—H22'119.5
C13—C14—H14119.7C21'—C22'—C23'120.9 (5)
C16—C15—P1122.3 (4)C23'—C22'—H22'119.5
C16—C15—C20119.2 (5)C22'—C23'—H23'120.0
C20—C15—P1118.5 (4)C24'—C23'—C22'119.9 (5)
C15—C16—H16119.9C24'—C23'—H23'120.0
C15—C16—C17120.2 (5)C23'—C24'—H24'120.2
C17—C16—H16119.9C25'—C24'—C23'119.5 (5)
C16—C17—H17119.8C25'—C24'—H24'120.2
C18—C17—C16120.5 (5)C24'—C25'—H25'119.8
C18—C17—H17119.8C24'—C25'—C26'120.5 (5)
C17—C18—H18120.1C26'—C25'—H25'119.8
C17—C18—C19119.9 (5)C21'—C26'—H26'119.8
C19—C18—H18120.1C25'—C26'—C21'120.4 (5)
C18—C19—H19119.9C25'—C26'—H26'119.8
C20—C19—C18120.2 (5)Ir1'—C27"—H27"115.1
C20—C19—H19119.9C28"—C27"—Ir1'68 (2)
C15—C20—H20120.0C28"—C27"—H27"115.1
C19—C20—C15120.1 (5)C28"—C27"—C34"125 (2)
C19—C20—H20120.0C34"—C27"—Ir1'109.6 (15)
C22—C21—P1121.5 (4)C34"—C27"—H27"115.1
C22—C21—C26119.1 (5)Ir1'—C27'—H27'113.7
C26—C21—P1118.5 (4)C28'—C27'—Ir1'72.8 (13)
C21—C22—H22120.2C28'—C27'—H27'113.7
C23—C22—C21119.5 (6)C28'—C27'—C34'125.8 (13)
C23—C22—H22120.2C34'—C27'—Ir1'109.5 (9)
C22—C23—H23119.4C34'—C27'—H27'113.7
C24—C23—C22121.1 (6)Ir1'—C28"—H28"113.6
C24—C23—H23119.4C27"—C28"—Ir1'76 (2)
C23—C24—H24120.2C27"—C28"—H28"113.6
C23—C24—C25119.5 (5)C27"—C28"—C29"124 (2)
C25—C24—H24120.2C29"—C28"—Ir1'109 (2)
C24—C25—H25119.9C29"—C28"—H28"113.6
C26—C25—C24120.3 (6)Ir1'—C28'—H28'113.7
C26—C25—H25119.9C27'—C28'—Ir1'69.7 (12)
C21—C26—H26119.8C27'—C28'—H28'113.7
C25—C26—C21120.4 (5)C27'—C28'—C29'125.5 (13)
C25—C26—H26119.8C29'—C28'—Ir1'112.6 (12)
Ir1—C27—H27113.2C29'—C28'—H28'113.7
C28—C27—Ir172.0 (3)C28"—C29"—H29A107.7
C28—C27—H27113.2C28"—C29"—H29B107.7
C28—C27—C34125.8 (6)H29A—C29"—H29B107.1
C34—C27—Ir1112.5 (4)C30"—C29"—C28"118 (2)
C34—C27—H27113.2C30"—C29"—H29A107.7
Ir1—C28—H28113.9C30"—C29"—H29B107.7
C27—C28—Ir171.3 (4)C28'—C29'—H29C108.2
C27—C28—H28113.9C28'—C29'—H29D108.2
C27—C28—C29126.2 (6)H29C—C29'—H29D107.3
C29—C28—Ir1109.4 (4)C30'—C29'—C28'116.4 (12)
C29—C28—H28113.9C30'—C29'—H29C108.2
C28—C29—H29E109.1C30'—C29'—H29D108.2
C28—C29—H29F109.1C29"—C30"—H30A107.9
C28—C29—C30112.5 (5)C29"—C30"—H30B107.9
H29E—C29—H29F107.8C29"—C30"—C31"118 (2)
C30—C29—H29E109.1H30A—C30"—H30B107.2
C30—C29—H29F109.1C31"—C30"—H30A107.9
C29—C30—H30E109.2C31"—C30"—H30B107.9
C29—C30—H30F109.2C29'—C30'—H30C108.8
H30E—C30—H30F107.9C29'—C30'—H30D108.8
C31—C30—C29112.2 (4)C29'—C30'—C31'113.9 (14)
C31—C30—H30E109.2H30C—C30'—H30D107.7
C31—C30—H30F109.2C31'—C30'—H30C108.8
Ir1—C31—H31113.7C31'—C30'—H30D108.8
C30—C31—Ir1112.7 (4)Ir1'—C31"—H31"115.5
C30—C31—H31113.7C30"—C31"—Ir1'108 (2)
C32—C31—Ir171.6 (3)C30"—C31"—H31"115.5
C32—C31—C30124.2 (5)C32"—C31"—Ir1'73 (3)
C32—C31—H31113.7C32"—C31"—C30"122 (3)
Ir1—C32—H32114.4C32"—C31"—H31"115.5
C31—C32—Ir171.7 (3)Ir1'—C31'—H31'113.0
C31—C32—H32114.4C30'—C31'—Ir1'111.3 (15)
C31—C32—C33125.0 (6)C30'—C31'—H31'113.0
C33—C32—Ir1108.8 (4)C32'—C31'—Ir1'70.5 (17)
C33—C32—H32114.4C32'—C31'—C30'127.8 (18)
C32—C33—H33E108.8C32'—C31'—H31'113.0
C32—C33—H33F108.8Ir1'—C32"—H32"114.2
C32—C33—C34113.7 (5)C31"—C32"—Ir1'69 (3)
H33E—C33—H33F107.7C31"—C32"—H32"114.2
C34—C33—H33E108.8C31"—C32"—C33"124 (3)
C34—C33—H33F108.8C33"—C32"—Ir1'113 (2)
C27—C34—C33113.7 (5)C33"—C32"—H32"114.2
C27—C34—H34E108.8Ir1'—C32'—H32'114.0
C27—C34—H34F108.8C31'—C32'—Ir1'73.7 (17)
C33—C34—H34E108.8C31'—C32'—H32'114.0
C33—C34—H34F108.8C31'—C32'—C33'122.4 (15)
H34E—C34—H34F107.7C33'—C32'—Ir1'112.3 (13)
C1'—Ir1'—P1'91.62 (15)C33'—C32'—H32'114.0
C1'—Ir1'—C27"89.5 (8)C32"—C33"—H33A108.3
C1'—Ir1'—C27'88.2 (5)C32"—C33"—H33B108.3
C1'—Ir1'—C28"91.6 (8)H33A—C33"—H33B107.4
C1'—Ir1'—C28'95.3 (5)C34"—C33"—C32"116 (2)
C1'—Ir1'—C31"164.0 (9)C34"—C33"—H33A108.3
C1'—Ir1'—C31'168.4 (5)C34"—C33"—H33B108.3
C1'—Ir1'—C32"157.7 (9)C32'—C33'—H33C108.7
C1'—Ir1'—C32'155.3 (5)C32'—C33'—H33D108.7
C27"—Ir1'—P1'172.7 (6)H33C—C33'—H33D107.6
C27'—Ir1'—P1'166.2 (3)C34'—C33'—C32'114.0 (12)
C27'—Ir1'—C28'37.5 (5)C34'—C33'—H33C108.7
C27'—Ir1'—C31'93.6 (7)C34'—C33'—H33D108.7
C27'—Ir1'—C32'80.6 (6)C27"—C34"—H34A107.6
C28"—Ir1'—P1'151.1 (8)C27"—C34"—H34B107.6
C28"—Ir1'—C27"36.0 (9)C33"—C34"—C27"118.8 (17)
C28"—Ir1'—C31"82.6 (13)C33"—C34"—H34A107.6
C28"—Ir1'—C32"90.3 (11)C33"—C34"—H34B107.6
C28'—Ir1'—P1'156.0 (4)H34A—C34"—H34B107.0
C28'—Ir1'—C31'79.5 (7)C27'—C34'—H34C108.4
C31"—Ir1'—P1'86.5 (11)C27'—C34'—H34D108.4
C31"—Ir1'—C27"94.3 (12)C33'—C34'—C27'115.4 (10)
C31"—Ir1'—C32"37.8 (11)C33'—C34'—H34C108.4
C31'—Ir1'—P1'89.3 (6)C33'—C34'—H34D108.4
C32"—Ir1'—P1'97.4 (8)H34C—C34'—H34D107.5
C32"—Ir1'—C27"79.1 (11)F1—B1—F4109.2 (6)
C32'—Ir1'—P1'94.2 (5)F2—B1—F1110.9 (6)
C32'—Ir1'—C28'89.1 (6)F2—B1—F4109.2 (5)
C32'—Ir1'—C31'35.9 (5)F3—B1—F1109.5 (5)
C9'—P1'—Ir1'112.40 (16)F3—B1—F2111.1 (6)
C9'—P1'—C15'101.7 (2)F3—B1—F4106.9 (6)
C9'—P1'—C21'104.4 (2)F1'—B1'—F2'110.6 (5)
C15'—P1'—Ir1'116.94 (17)F1'—B1'—F3'110.6 (6)
C21'—P1'—Ir1'113.86 (17)F1'—B1'—F4'109.7 (6)
C21'—P1'—C15'106.1 (2)F2'—B1'—F3'109.1 (5)
N2'—N1'—C3'118.8 (4)F2'—B1'—F4'110.3 (6)
C1'—N1'—N2'113.8 (4)F3'—B1'—F4'106.5 (5)
Ir1—P1—C9—C10121.4 (5)Ir1'—C27'—C28'—C29'−103.8 (19)
Ir1—P1—C9—C14−61.6 (5)Ir1'—C27'—C34'—C33'32.5 (12)
Ir1—P1—C15—C16−2.1 (5)Ir1'—C28"—C29"—C30"−7 (2)
Ir1—P1—C15—C20177.8 (4)Ir1'—C28'—C29'—C30'1.4 (15)
Ir1—P1—C21—C22101.8 (4)Ir1'—C31"—C32"—C33"−105 (4)
Ir1—P1—C21—C26−67.4 (4)Ir1'—C31'—C32'—C33'−106 (2)
Ir1—C27—C28—C29−100.8 (6)Ir1'—C32"—C33"—C34"2 (2)
Ir1—C27—C34—C33−9.0 (7)Ir1'—C32'—C33'—C34'5.9 (13)
Ir1—C28—C29—C30−40.2 (6)P1'—C9'—C10'—C11'−177.7 (4)
Ir1—C31—C32—C33−100.5 (6)P1'—C9'—C14'—C13'178.5 (4)
Ir1—C32—C33—C34−36.7 (6)P1'—C15'—C16'—C17'−176.3 (5)
P1—C9—C10—C11177.9 (5)P1'—C15'—C20'—C19'175.6 (5)
P1—C9—C14—C13−177.8 (5)P1'—C21'—C22'—C23'−175.7 (4)
P1—C15—C16—C17−178.7 (4)P1'—C21'—C26'—C25'174.6 (4)
P1—C15—C20—C19177.9 (4)N1'—N2'—C2'—N3'−0.5 (7)
P1—C21—C22—C23−170.6 (4)N2'—N1'—C1'—Ir1'−179.2 (4)
P1—C21—C26—C25171.6 (4)N2'—N1'—C1'—N3'0.9 (6)
N1—N2—C2—N30.2 (6)N2'—N1'—C3'—C4'−64.2 (7)
N2—N1—C1—Ir1−178.0 (3)N3'—C5'—C6'—C7'−173.8 (5)
N2—N1—C1—N3−1.6 (6)C1'—N1'—N2'—C2'−0.3 (6)
N2—N1—C3—C466.1 (6)C1'—N1'—C3'—C4'111.1 (6)
N3—C5—C6—C7168.7 (5)C1'—N3'—C2'—N2'1.1 (7)
C1—N1—N2—C20.9 (6)C1'—N3'—C5'—C6'−113.5 (6)
C1—N1—C3—C4−113.0 (6)C2'—N3'—C1'—Ir1'179.0 (4)
C1—N3—C2—N2−1.2 (7)C2'—N3'—C1'—N1'−1.2 (6)
C1—N3—C5—C6117.5 (6)C2'—N3'—C5'—C6'65.0 (7)
C2—N3—C1—Ir1177.6 (4)C3'—N1'—N2'—C2'175.6 (5)
C2—N3—C1—N11.6 (6)C3'—N1'—C1'—Ir1'5.3 (7)
C2—N3—C5—C6−65.0 (7)C3'—N1'—C1'—N3'−174.6 (5)
C3—N1—N2—C2−178.3 (5)C5'—N3'—C1'—Ir1'−2.3 (8)
C3—N1—C1—Ir11.1 (7)C5'—N3'—C1'—N1'177.5 (5)
C3—N1—C1—N3177.5 (5)C5'—N3'—C2'—N2'−177.6 (5)
C5—N3—C1—Ir1−4.7 (8)C5'—C6'—C7'—C8'178.7 (6)
C5—N3—C1—N1179.4 (5)C9'—P1'—C15'—C16'−50.2 (5)
C5—N3—C2—N2−179.0 (5)C9'—P1'—C15'—C20'133.5 (5)
C5—C6—C7—C8−177.1 (5)C9'—P1'—C21'—C22'−173.0 (4)
C9—P1—C15—C16−130.6 (5)C9'—P1'—C21'—C26'15.2 (5)
C9—P1—C15—C2049.4 (5)C9'—C10'—C11'—C12'−1.2 (9)
C9—P1—C21—C22−127.2 (4)C10'—C9'—C14'—C13'−0.5 (8)
C9—P1—C21—C2663.6 (5)C10'—C11'—C12'—C13'0.2 (10)
C9—C10—C11—C12−1.0 (9)C11'—C12'—C13'—C14'0.7 (10)
C10—C9—C14—C13−0.6 (8)C12'—C13'—C14'—C9'−0.5 (9)
C10—C11—C12—C130.8 (10)C14'—C9'—C10'—C11'1.3 (8)
C11—C12—C13—C14−0.5 (10)C15'—P1'—C9'—C10'−47.2 (5)
C12—C13—C14—C90.4 (9)C15'—P1'—C9'—C14'133.8 (5)
C14—C9—C10—C110.9 (8)C15'—P1'—C21'—C22'−66.0 (5)
C15—P1—C9—C10−114.3 (5)C15'—P1'—C21'—C26'122.2 (4)
C15—P1—C9—C1462.8 (4)C15'—C16'—C17'—C18'0.4 (9)
C15—P1—C21—C22−21.2 (5)C16'—C15'—C20'—C19'−0.6 (9)
C15—P1—C21—C26169.6 (4)C16'—C17'—C18'—C19'−0.6 (10)
C15—C16—C17—C180.1 (9)C17'—C18'—C19'—C20'0.2 (10)
C16—C15—C20—C19−2.1 (8)C18'—C19'—C20'—C15'0.4 (10)
C16—C17—C18—C19−0.8 (9)C20'—C15'—C16'—C17'0.2 (8)
C17—C18—C19—C200.0 (9)C21'—P1'—C9'—C10'63.0 (5)
C18—C19—C20—C151.4 (9)C21'—P1'—C9'—C14'−116.0 (5)
C20—C15—C16—C171.3 (8)C21'—P1'—C15'—C16'−159.1 (4)
C21—P1—C9—C10−5.3 (6)C21'—P1'—C15'—C20'24.6 (6)
C21—P1—C9—C14171.8 (4)C21'—C22'—C23'—C24'2.2 (8)
C21—P1—C15—C16120.0 (4)C22'—C21'—C26'—C25'2.7 (8)
C21—P1—C15—C20−60.0 (4)C22'—C23'—C24'—C25'0.3 (8)
C21—C22—C23—C240.2 (8)C23'—C24'—C25'—C26'−1.1 (8)
C22—C21—C26—C252.2 (8)C24'—C25'—C26'—C21'−0.4 (8)
C22—C23—C24—C250.5 (9)C26'—C21'—C22'—C23'−3.6 (8)
C23—C24—C25—C260.2 (9)C27"—C28"—C29"—C30"79 (4)
C24—C25—C26—C21−1.6 (8)C27'—C28'—C29'—C30'82 (2)
C26—C21—C22—C23−1.5 (7)C28"—C27"—C34"—C33"−55 (3)
C27—C28—C29—C3040.3 (8)C28"—C29"—C30"—C31"−9 (3)
C28—C27—C34—C33−92.5 (7)C28'—C27'—C34'—C33'−50 (2)
C28—C29—C30—C3136.3 (7)C28'—C29'—C30'—C31'−19.6 (16)
C29—C30—C31—Ir1−14.4 (6)C29"—C30"—C31"—Ir1'20 (2)
C29—C30—C31—C32−97.0 (7)C29"—C30"—C31"—C32"−60 (5)
C30—C31—C32—Ir1105.5 (5)C29'—C30'—C31'—Ir1'28.0 (15)
C30—C31—C32—C335.0 (9)C29'—C30'—C31'—C32'−53 (3)
C31—C32—C33—C3443.7 (8)C30"—C31"—C32"—Ir1'101 (4)
C32—C33—C34—C2731.0 (7)C30"—C31"—C32"—C33"−4 (6)
C34—C27—C28—Ir1105.1 (6)C30'—C31'—C32'—Ir1'102 (3)
C34—C27—C28—C294.4 (10)C30'—C31'—C32'—C33'−4 (4)
Ir1'—P1'—C9'—C10'−173.1 (4)C31"—C32"—C33"—C34"82 (4)
Ir1'—P1'—C9'—C14'7.9 (5)C31'—C32'—C33'—C34'90 (3)
Ir1'—P1'—C15'—C16'72.6 (4)C32"—C33"—C34"—C27"−16 (2)
Ir1'—P1'—C15'—C20'−103.7 (5)C32'—C33'—C34'—C27'−25.7 (14)
Ir1'—P1'—C21'—C22'64.1 (4)C34"—C27"—C28"—Ir1'99 (2)
Ir1'—P1'—C21'—C26'−107.8 (4)C34"—C27"—C28"—C29"−5 (5)
Ir1'—C27"—C28"—C29"−104 (3)C34'—C27'—C28'—Ir1'102.0 (15)
Ir1'—C27"—C34"—C33"21 (2)C34'—C27'—C28'—C29'−2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···F4′0.952.353.255 (7)158
C4—H4B···F2i0.982.493.352 (8)147
C2′—H2′···F1ii0.952.213.014 (6)141
C11′—H11′···F4iii0.952.463.363 (7)160
C30′—H30D···F3′iii0.992.493.355 (15)146
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x−1, −y+1, z−1/2; (iii) x, −y+1, z−1/2.
 

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Volume 9| Part 6| June 2024| x240501
https://doi.org/10.1107/S2414314624005017