(Butane-1,4-di-yl)(trimethyl-phosphane-κP)[tris-(3,5-dimethyl-pyrazol-1-yl-κN (2))hydro-borato]iridium(III).

In the mononuclear title iridium(III) complex, [Ir(C4H8)(C15H22BN6)(C3H9P)], which is based on the [tris-(3,5-dimethyl-pyrazol-1-yl)hydro-borato]iridium moiety, Ir[Tp(Me2)], the Ir(III) atom is coordinated by a chelating butane-1,4-diyl fragment and a trimethyl-phosphane ligand in a modestly distorted octa-hedral coordination environment formed by three facial N, two C and one P atom. The iridium-butane-1,4-diyl ring has an envelope conformation. This ring is disordered because alternately the second or the third C atom of the butane-1,4-diyl fragment function as an envelope flap atom (the occupancy ratio is 1:1). In the crystal, mol-ecules are organized into densely packed columns extending along [101]. Coherence between the mol-ecules is essentially based on van der Waals inter-actions.

Related literature

For general aspects of hydrogen tris­pyrazolylborate ligands, see: Pettinari & Trofimenko (2008 ▶). For general information on mechanistic aspects of organometallic reactions, involving oxidative addition and reductive elimination, see: Crabtree (2005 ▶). For information on σ-CAM mechanisms, see: Perutz & Sabo-Etienne (2007 ▶). For general information on the chemistry and potential of Ir[TpMe2] complexes, see: Conejero et al. (2010 ▶). For selected aspects of the synthesis and the crystal structure of the precursor of the title compound, see: Paneque et al. (2000 ▶). For aspects of the chemistry of a CO- instead of PMe3-containing analogue to the precursor of the title compound, see: Gómez et al. (2007 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[Ir(C4H8)(C15H22BN6)(C3H9P)]

M = 621.57

Monoclinic,

a = 11.1865 (5) Å

b = 18.1771 (8) Å

c = 13.4748 (6) Å

β = 112.883 (1)°

V = 2524.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 5.37 mm−1

T = 173 K

0.22 × 0.15 × 0.14 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.36, T max = 0.47

37102 measured reflections

7359 independent reflections

6892 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.040

S = 1.08

7359 reflections

298 parameters

25 restraints

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008040/gk2565sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008040/gk2565Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ir(C4H8)(C15H22BN6)(C3H9P)]	F(000) = 1240
Mr = 621.57	Dx = 1.636 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8250 reflections
a = 11.1865 (5) Å	θ = 2.3–30.0°
b = 18.1771 (8) Å	µ = 5.37 mm−1
c = 13.4748 (6) Å	T = 173 K
β = 112.883 (1)°	Oval, colourless
V = 2524.3 (2) Å3	0.22 × 0.15 × 0.14 mm
Z = 4

Bruker SMART APEX CCD diffractometer	7359 independent reflections
Radiation source: fine-focus sealed tube	6892 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 0.11 pixels mm-1	θmax = 30.0°, θmin = 2.0°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2003)	k = −25→25
Tmin = 0.36, Tmax = 0.47	l = −18→18
37102 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.040	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0188P)2 + 1.5354P] where P = (Fo2 + 2Fc2)/3
7359 reflections	(Δ/σ)max = 0.002
298 parameters	Δρmax = 0.86 e Å−3
25 restraints	Δρmin = −0.32 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ir1	0.330539 (6)	0.149427 (3)	0.140251 (5)	0.02163 (2)
P1	0.13156 (4)	0.17885 (3)	0.02261 (4)	0.02555 (9)
N1	0.41101 (15)	0.26249 (9)	0.13371 (12)	0.0279 (3)
N2	0.52542 (16)	0.26511 (9)	0.11853 (13)	0.0313 (3)
N3	0.39782 (14)	0.11256 (9)	0.01330 (12)	0.0271 (3)
N4	0.50615 (16)	0.14845 (9)	0.01311 (13)	0.0289 (3)
N5	0.52880 (14)	0.12008 (9)	0.24383 (12)	0.0258 (3)
N6	0.62443 (15)	0.14889 (9)	0.21463 (13)	0.0299 (3)
B1	0.5921 (2)	0.19391 (13)	0.11026 (17)	0.0312 (4)
H1	0.6748	0.2061	0.1017	0.037*
C1	0.2641 (3)	0.35688 (13)	0.1631 (3)	0.0507 (6)
H1A	0.2366	0.3178	0.1997	0.076*
H1B	0.1940	0.3674	0.0934	0.076*
H1C	0.2842	0.4014	0.2076	0.076*
C2	0.3816 (2)	0.33261 (11)	0.14579 (16)	0.0342 (4)
C3	0.4767 (2)	0.37982 (12)	0.13857 (17)	0.0402 (5)
H3	0.4791	0.4319	0.1446	0.048*
C4	0.5652 (2)	0.33560 (13)	0.12097 (17)	0.0406 (5)
C5	0.6899 (3)	0.35592 (16)	0.1088 (2)	0.0595 (8)
H5A	0.6973	0.4096	0.1075	0.089*
H5B	0.6894	0.3353	0.0415	0.089*
H5C	0.7639	0.3360	0.1697	0.089*
C6	0.2510 (2)	0.01374 (14)	−0.09982 (18)	0.0441 (5)
H6A	0.2293	0.0053	−0.0370	0.066*
H6B	0.2763	−0.0329	−0.1225	0.066*
H6C	0.1753	0.0339	−0.1589	0.066*
C7	0.36048 (18)	0.06676 (11)	−0.07123 (15)	0.0305 (4)
C8	0.4424 (2)	0.07415 (12)	−0.12664 (16)	0.0360 (4)
H8	0.4361	0.0486	−0.1900	0.043*
C9	0.5333 (2)	0.12547 (13)	−0.07166 (16)	0.0345 (4)
C10	0.6438 (3)	0.15446 (15)	−0.0960 (2)	0.0503 (6)
H10A	0.6357	0.2080	−0.1049	0.075*
H10B	0.6423	0.1320	−0.1626	0.075*
H10C	0.7258	0.1425	−0.0365	0.075*
C11	0.5281 (2)	0.04034 (13)	0.39711 (17)	0.0415 (5)
H11A	0.4682	0.0728	0.4134	0.062*
H11B	0.5949	0.0225	0.4645	0.062*
H11C	0.4801	−0.0016	0.3544	0.062*
C12	0.59054 (18)	0.08183 (11)	0.33483 (14)	0.0304 (4)
C13	0.72443 (19)	0.08640 (13)	0.36404 (16)	0.0375 (4)
H13	0.7898	0.0641	0.4247	0.045*
C14	0.74271 (19)	0.12949 (14)	0.28780 (16)	0.0370 (4)
C15	0.8676 (2)	0.15468 (18)	0.2836 (2)	0.0576 (8)
H15A	0.8712	0.2085	0.2857	0.086*
H15B	0.8734	0.1373	0.2168	0.086*
H15C	0.9403	0.1348	0.3455	0.086*
C16A	0.26125 (19)	0.04707 (11)	0.16388 (15)	0.0317 (4)	0.50
H16A	0.2210	0.0214	0.0938	0.038*	0.50
H16B	0.3346	0.0167	0.2114	0.038*	0.50
C17A	0.1607 (4)	0.0554 (2)	0.2149 (3)	0.0360 (8)	0.50
H17A	0.0758	0.0709	0.1603	0.043*	0.50
H17B	0.1492	0.0083	0.2471	0.043*	0.50
C18A	0.2157 (4)	0.11462 (19)	0.3022 (4)	0.0356 (10)	0.50
H18A	0.2755	0.0908	0.3692	0.043*	0.50
H18B	0.1433	0.1362	0.3174	0.043*	0.50
C19A	0.28856 (18)	0.17707 (11)	0.27285 (15)	0.0305 (3)	0.50
H19A	0.3703	0.1875	0.3351	0.037*	0.50
H19B	0.2348	0.2222	0.2567	0.037*	0.50
C16B	0.26125 (19)	0.04707 (11)	0.16388 (15)	0.0317 (4)	0.50
H16C	0.1903	0.0312	0.0963	0.038*	0.50
H16D	0.3319	0.0103	0.1821	0.038*	0.50
C17B	0.2106 (4)	0.0498 (2)	0.2547 (3)	0.0359 (8)	0.50
H17C	0.1297	0.0205	0.2327	0.043*	0.50
H17D	0.2753	0.0262	0.3197	0.043*	0.50
C18B	0.1831 (4)	0.12778 (18)	0.2842 (5)	0.0356 (10)	0.50
H18C	0.1874	0.1292	0.3590	0.043*	0.50
H18D	0.0958	0.1443	0.2349	0.043*	0.50
C19B	0.28856 (18)	0.17707 (11)	0.27285 (15)	0.0305 (3)	0.50
H19C	0.3686	0.1729	0.3389	0.037*	0.50
H19D	0.2594	0.2289	0.2660	0.037*	0.50
C20	0.0148 (2)	0.10666 (15)	−0.0424 (3)	0.0766 (11)
H20A	−0.0670	0.1289	−0.0908	0.115*
H20B	−0.0007	0.0773	0.0125	0.115*
H20C	0.0490	0.0749	−0.0839	0.115*
C21	0.0218 (2)	0.23610 (18)	0.0609 (2)	0.0561 (7)
H21A	−0.0599	0.2429	−0.0015	0.084*
H21B	0.0621	0.2841	0.0858	0.084*
H21C	0.0045	0.2120	0.1190	0.084*
C22	0.1375 (2)	0.22637 (14)	−0.09285 (17)	0.0415 (5)
H22A	0.0492	0.2385	−0.1427	0.062*
H22B	0.1786	0.1947	−0.1293	0.062*
H22C	0.1881	0.2717	−0.0693	0.062*

	U11	U22	U33	U12	U13	U23
Ir1	0.01893 (3)	0.02738 (4)	0.02017 (3)	0.00079 (2)	0.00933 (2)	0.00218 (2)
P1	0.01929 (19)	0.0272 (2)	0.0285 (2)	−0.00024 (16)	0.00746 (16)	0.00237 (17)
N1	0.0266 (7)	0.0315 (8)	0.0238 (7)	−0.0045 (6)	0.0080 (6)	0.0011 (6)
N2	0.0303 (8)	0.0394 (9)	0.0256 (7)	−0.0122 (6)	0.0122 (6)	−0.0033 (6)
N3	0.0234 (7)	0.0362 (8)	0.0225 (7)	−0.0001 (6)	0.0098 (6)	−0.0009 (6)
N4	0.0251 (7)	0.0427 (9)	0.0228 (7)	−0.0014 (6)	0.0137 (6)	−0.0009 (6)
N5	0.0214 (7)	0.0345 (8)	0.0225 (7)	0.0022 (6)	0.0096 (5)	−0.0004 (6)
N6	0.0198 (7)	0.0476 (10)	0.0235 (7)	−0.0001 (6)	0.0096 (6)	−0.0025 (6)
B1	0.0238 (9)	0.0479 (12)	0.0254 (9)	−0.0078 (8)	0.0134 (8)	−0.0018 (8)
C1	0.0451 (13)	0.0331 (11)	0.0691 (18)	0.0079 (9)	0.0169 (13)	0.0008 (10)
C2	0.0351 (10)	0.0329 (9)	0.0276 (9)	−0.0014 (8)	0.0047 (8)	0.0022 (7)
C3	0.0493 (12)	0.0316 (10)	0.0318 (10)	−0.0108 (9)	0.0073 (9)	0.0005 (8)
C4	0.0473 (12)	0.0437 (11)	0.0305 (10)	−0.0227 (10)	0.0148 (9)	−0.0029 (8)
C5	0.0594 (17)	0.0677 (18)	0.0575 (16)	−0.0358 (14)	0.0295 (14)	−0.0074 (13)
C6	0.0388 (11)	0.0524 (13)	0.0364 (11)	−0.0083 (10)	0.0094 (9)	−0.0112 (10)
C7	0.0289 (9)	0.0366 (10)	0.0236 (8)	0.0043 (7)	0.0076 (7)	−0.0016 (7)
C8	0.0378 (10)	0.0473 (11)	0.0249 (8)	0.0051 (9)	0.0144 (8)	−0.0057 (8)
C9	0.0358 (10)	0.0483 (11)	0.0259 (9)	0.0044 (9)	0.0190 (8)	0.0007 (8)
C10	0.0542 (15)	0.0689 (17)	0.0444 (13)	−0.0078 (12)	0.0371 (12)	−0.0049 (11)
C11	0.0430 (11)	0.0474 (12)	0.0287 (9)	0.0013 (9)	0.0080 (8)	0.0111 (9)
C12	0.0293 (9)	0.0364 (9)	0.0229 (8)	0.0066 (7)	0.0074 (7)	−0.0002 (7)
C13	0.0273 (9)	0.0522 (12)	0.0267 (9)	0.0113 (8)	0.0036 (7)	−0.0031 (8)
C14	0.0214 (8)	0.0593 (13)	0.0288 (9)	0.0030 (8)	0.0082 (7)	−0.0085 (9)
C15	0.0223 (10)	0.100 (2)	0.0496 (15)	−0.0031 (11)	0.0125 (10)	−0.0062 (13)
C16A	0.0358 (9)	0.0280 (8)	0.0341 (9)	0.0021 (7)	0.0167 (7)	0.0057 (7)
C17A	0.033 (2)	0.0384 (19)	0.040 (2)	−0.0027 (15)	0.0187 (18)	0.0128 (13)
C18A	0.017 (2)	0.0585 (14)	0.038 (2)	0.0027 (16)	0.018 (2)	0.0024 (14)
C19A	0.0327 (9)	0.0356 (8)	0.0287 (9)	0.0026 (7)	0.0180 (7)	0.0002 (7)
C16B	0.0358 (9)	0.0280 (8)	0.0341 (9)	0.0021 (7)	0.0167 (7)	0.0057 (7)
C17B	0.034 (2)	0.0433 (12)	0.032 (2)	−0.0098 (16)	0.0145 (17)	0.0081 (19)
C18B	0.017 (2)	0.0585 (14)	0.038 (2)	0.0027 (16)	0.018 (2)	0.0024 (14)
C19B	0.0327 (9)	0.0356 (8)	0.0287 (9)	0.0026 (7)	0.0180 (7)	0.0002 (7)
C20	0.0219 (10)	0.0399 (13)	0.136 (3)	−0.0061 (9)	−0.0040 (14)	−0.0021 (16)
C21	0.0346 (11)	0.087 (2)	0.0450 (13)	0.0244 (12)	0.0136 (10)	−0.0045 (13)
C22	0.0356 (10)	0.0567 (13)	0.0292 (9)	0.0088 (9)	0.0093 (8)	0.0135 (9)

Ir1—C19A	2.0780 (18)	C9—C10	1.492 (3)
Ir1—C16A	2.0871 (19)	C10—H10A	0.9800
Ir1—N5	2.1781 (14)	C10—H10B	0.9800
Ir1—N3	2.2233 (15)	C10—H10C	0.9800
Ir1—P1	2.2381 (5)	C11—C12	1.489 (3)
Ir1—N1	2.2590 (15)	C11—H11A	0.9800
P1—C22	1.803 (2)	C11—H11B	0.9800
P1—C20	1.818 (2)	C11—H11C	0.9800
P1—C21	1.830 (2)	C12—C13	1.395 (3)
N1—C2	1.342 (3)	C13—C14	1.369 (3)
N1—N2	1.373 (2)	C13—H13	0.9500
N2—C4	1.353 (3)	C14—C15	1.492 (3)
N2—B1	1.520 (3)	C15—H15A	0.9800
N3—C7	1.340 (2)	C15—H15B	0.9800
N3—N4	1.377 (2)	C15—H15C	0.9800
N4—C9	1.357 (2)	C16A—C17A	1.537 (2)
N4—B1	1.531 (3)	C16A—H16A	0.9900
N5—C12	1.344 (2)	C16A—H16B	0.9900
N5—N6	1.379 (2)	C17A—C18A	1.536 (2)
N6—C14	1.354 (2)	C17A—H17A	0.9900
N6—B1	1.544 (3)	C17A—H17B	0.9900
B1—H1	1.0000	C18A—C19A	1.536 (2)
C1—C2	1.489 (4)	C18A—H18A	0.9900
C1—H1A	0.9800	C18A—H18B	0.9900
C1—H1B	0.9800	C19A—H19A	0.9900
C1—H1C	0.9800	C19A—H19B	0.9900
C2—C3	1.399 (3)	C17B—C18B	1.536 (2)
C3—C4	1.366 (4)	C17B—H17C	0.9900
C3—H3	0.9500	C17B—H17D	0.9900
C4—C5	1.512 (3)	C18B—H18C	0.9900
C5—H5A	0.9800	C18B—H18D	0.9900
C5—H5B	0.9800	C20—H20A	0.9800
C5—H5C	0.9800	C20—H20B	0.9800
C6—C7	1.487 (3)	C20—H20C	0.9800
C6—H6A	0.9800	C21—H21A	0.9800
C6—H6B	0.9800	C21—H21B	0.9800
C6—H6C	0.9800	C21—H21C	0.9800
C7—C8	1.395 (3)	C22—H22A	0.9800
C8—C9	1.367 (3)	C22—H22B	0.9800
C8—H8	0.9500	C22—H22C	0.9800
C19A—Ir1—C16A	82.12 (8)	N4—C9—C8	107.64 (17)
C19A—Ir1—N5	91.29 (7)	N4—C9—C10	123.5 (2)
C16A—Ir1—N5	91.71 (7)	C8—C9—C10	128.87 (19)
C19A—Ir1—N3	172.64 (7)	C9—C10—H10A	109.5
C16A—Ir1—N3	96.06 (7)	C9—C10—H10B	109.5
N5—Ir1—N3	81.62 (5)	H10A—C10—H10B	109.5
C19A—Ir1—P1	93.22 (6)	C9—C10—H10C	109.5
C16A—Ir1—P1	89.71 (6)	H10A—C10—H10C	109.5
N5—Ir1—P1	175.42 (4)	H10B—C10—H10C	109.5
N3—Ir1—P1	93.90 (4)	C12—C11—H11A	109.5
C19A—Ir1—N1	92.31 (7)	C12—C11—H11B	109.5
C16A—Ir1—N1	173.83 (6)	H11A—C11—H11B	109.5
N5—Ir1—N1	85.75 (6)	C12—C11—H11C	109.5
N3—Ir1—N1	89.14 (6)	H11A—C11—H11C	109.5
P1—Ir1—N1	93.25 (4)	H11B—C11—H11C	109.5
C22—P1—C20	101.00 (15)	N5—C12—C13	109.95 (18)
C22—P1—C21	103.01 (12)	N5—C12—C11	126.10 (17)
C20—P1—C21	96.38 (14)	C13—C12—C11	123.96 (18)
C22—P1—Ir1	111.42 (7)	C14—C13—C12	106.23 (17)
C20—P1—Ir1	119.95 (9)	C14—C13—H13	126.9
C21—P1—Ir1	121.84 (8)	C12—C13—H13	126.9
C2—N1—N2	105.75 (16)	N6—C14—C13	107.86 (18)
C2—N1—Ir1	137.67 (14)	N6—C14—C15	123.8 (2)
N2—N1—Ir1	116.49 (12)	C13—C14—C15	128.3 (2)
C4—N2—N1	110.26 (18)	C14—C15—H15A	109.5
C4—N2—B1	129.95 (18)	C14—C15—H15B	109.5
N1—N2—B1	119.62 (15)	H15A—C15—H15B	109.5
C7—N3—N4	106.05 (15)	C14—C15—H15C	109.5
C7—N3—Ir1	138.98 (13)	H15A—C15—H15C	109.5
N4—N3—Ir1	114.84 (11)	H15B—C15—H15C	109.5
C9—N4—N3	109.95 (16)	C17A—C16A—Ir1	111.13 (19)
C9—N4—B1	127.88 (17)	C17A—C16A—H16A	109.4
N3—N4—B1	121.00 (14)	Ir1—C16A—H16A	109.4
C12—N5—N6	106.05 (15)	C17A—C16A—H16B	109.4
C12—N5—Ir1	138.20 (13)	Ir1—C16A—H16B	109.4
N6—N5—Ir1	115.71 (11)	H16A—C16A—H16B	108.0
C14—N6—N5	109.89 (16)	C18A—C17A—C16A	105.5 (3)
C14—N6—B1	128.16 (17)	C18A—C17A—H17A	110.6
N5—N6—B1	121.92 (15)	C16A—C17A—H17A	110.6
N2—B1—N4	111.05 (16)	C18A—C17A—H17B	110.6
N2—B1—N6	109.40 (15)	C16A—C17A—H17B	110.6
N4—B1—N6	109.86 (17)	H17A—C17A—H17B	108.8
N2—B1—H1	108.8	C17A—C18A—C19A	114.6 (3)
N4—B1—H1	108.8	C17A—C18A—H18A	108.6
N6—B1—H1	108.8	C19A—C18A—H18A	108.6
C2—C1—H1A	109.5	C17A—C18A—H18B	108.6
C2—C1—H1B	109.5	C19A—C18A—H18B	108.6
H1A—C1—H1B	109.5	H18A—C18A—H18B	107.6
C2—C1—H1C	109.5	C18A—C19A—Ir1	111.3 (2)
H1A—C1—H1C	109.5	C18A—C19A—H19A	109.4
H1B—C1—H1C	109.5	Ir1—C19A—H19A	109.4
N1—C2—C3	110.2 (2)	C18A—C19A—H19B	109.4
N1—C2—C1	124.98 (19)	Ir1—C19A—H19B	109.4
C3—C2—C1	124.8 (2)	H19A—C19A—H19B	108.0
C4—C3—C2	105.85 (19)	C18B—C17B—H17C	108.7
C4—C3—H3	127.1	C18B—C17B—H17D	108.7
C2—C3—H3	127.1	H17C—C17B—H17D	107.6
N2—C4—C3	107.92 (19)	C17B—C18B—H18C	110.6
N2—C4—C5	122.5 (2)	C17B—C18B—H18D	110.6
C3—C4—C5	129.5 (2)	H18C—C18B—H18D	108.7
C4—C5—H5A	109.5	P1—C20—H20A	109.5
C4—C5—H5B	109.5	P1—C20—H20B	109.5
H5A—C5—H5B	109.5	H20A—C20—H20B	109.5
C4—C5—H5C	109.5	P1—C20—H20C	109.5
H5A—C5—H5C	109.5	H20A—C20—H20C	109.5
H5B—C5—H5C	109.5	H20B—C20—H20C	109.5
C7—C6—H6A	109.5	P1—C21—H21A	109.5
C7—C6—H6B	109.5	P1—C21—H21B	109.5
H6A—C6—H6B	109.5	H21A—C21—H21B	109.5
C7—C6—H6C	109.5	P1—C21—H21C	109.5
H6A—C6—H6C	109.5	H21A—C21—H21C	109.5
H6B—C6—H6C	109.5	H21B—C21—H21C	109.5
N3—C7—C8	110.04 (17)	P1—C22—H22A	109.5
N3—C7—C6	125.19 (18)	P1—C22—H22B	109.5
C8—C7—C6	124.74 (18)	H22A—C22—H22B	109.5
C9—C8—C7	106.32 (17)	P1—C22—H22C	109.5
C9—C8—H8	126.8	H22A—C22—H22C	109.5
C7—C8—H8	126.8	H22B—C22—H22C	109.5
C19A—Ir1—P1—C22	139.06 (10)	C9—N4—B1—N6	−117.7 (2)
C16A—Ir1—P1—C22	−138.85 (10)	N3—N4—B1—N6	48.6 (2)
N3—Ir1—P1—C22	−42.79 (10)	C14—N6—B1—N2	−116.6 (2)
N1—Ir1—P1—C22	46.56 (10)	N5—N6—B1—N2	65.6 (2)
C19A—Ir1—P1—C20	−103.39 (16)	C14—N6—B1—N4	121.2 (2)
C16A—Ir1—P1—C20	−21.30 (16)	N5—N6—B1—N4	−56.6 (2)
N3—Ir1—P1—C20	74.76 (16)	N2—N1—C2—C3	−0.1 (2)
N1—Ir1—P1—C20	164.11 (16)	Ir1—N1—C2—C3	176.12 (14)
C19A—Ir1—P1—C21	17.18 (14)	N2—N1—C2—C1	179.2 (2)
C16A—Ir1—P1—C21	99.27 (14)	Ir1—N1—C2—C1	−4.5 (3)
N3—Ir1—P1—C21	−164.67 (13)	N1—C2—C3—C4	0.3 (2)
N1—Ir1—P1—C21	−75.32 (13)	C1—C2—C3—C4	−179.0 (2)
C19A—Ir1—N1—C2	−40.51 (19)	N1—N2—C4—C3	0.4 (2)
N5—Ir1—N1—C2	−131.63 (19)	B1—N2—C4—C3	−174.72 (18)
N3—Ir1—N1—C2	146.71 (19)	N1—N2—C4—C5	178.7 (2)
P1—Ir1—N1—C2	52.85 (19)	B1—N2—C4—C5	3.6 (3)
C19A—Ir1—N1—N2	135.43 (13)	C2—C3—C4—N2	−0.4 (2)
N5—Ir1—N1—N2	44.31 (12)	C2—C3—C4—C5	−178.6 (2)
N3—Ir1—N1—N2	−37.35 (12)	N4—N3—C7—C8	−1.2 (2)
P1—Ir1—N1—N2	−131.21 (11)	Ir1—N3—C7—C8	174.17 (15)
C2—N1—N2—C4	−0.2 (2)	N4—N3—C7—C6	176.69 (19)
Ir1—N1—N2—C4	−177.32 (13)	Ir1—N3—C7—C6	−7.9 (3)
C2—N1—N2—B1	175.50 (16)	N3—C7—C8—C9	1.1 (2)
Ir1—N1—N2—B1	−1.7 (2)	C6—C7—C8—C9	−176.8 (2)
C16A—Ir1—N3—C7	37.8 (2)	N3—N4—C9—C8	−0.2 (2)
N5—Ir1—N3—C7	128.7 (2)	B1—N4—C9—C8	167.3 (2)
P1—Ir1—N3—C7	−52.3 (2)	N3—N4—C9—C10	179.1 (2)
N1—Ir1—N3—C7	−145.5 (2)	B1—N4—C9—C10	−13.4 (3)
C16A—Ir1—N3—N4	−147.08 (13)	C7—C8—C9—N4	−0.5 (2)
N5—Ir1—N3—N4	−56.23 (12)	C7—C8—C9—C10	−179.7 (2)
P1—Ir1—N3—N4	122.79 (12)	N6—N5—C12—C13	0.3 (2)
N1—Ir1—N3—N4	29.60 (12)	Ir1—N5—C12—C13	−177.23 (15)
C7—N3—N4—C9	0.9 (2)	N6—N5—C12—C11	−179.78 (19)
Ir1—N3—N4—C9	−175.78 (13)	Ir1—N5—C12—C11	2.7 (3)
C7—N3—N4—B1	−167.66 (17)	N5—C12—C13—C14	0.5 (2)
Ir1—N3—N4—B1	15.7 (2)	C11—C12—C13—C14	−179.4 (2)
C19A—Ir1—N5—C12	45.3 (2)	N5—N6—C14—C13	1.3 (2)
C16A—Ir1—N5—C12	−36.8 (2)	B1—N6—C14—C13	−176.71 (19)
N3—Ir1—N5—C12	−132.7 (2)	N5—N6—C14—C15	−176.8 (2)
N1—Ir1—N5—C12	137.5 (2)	B1—N6—C14—C15	5.2 (3)
C19A—Ir1—N5—N6	−132.07 (13)	C12—C13—C14—N6	−1.1 (2)
C16A—Ir1—N5—N6	145.77 (13)	C12—C13—C14—C15	176.9 (2)
N3—Ir1—N5—N6	49.90 (12)	C19A—Ir1—C16A—C17A	29.0 (2)
N1—Ir1—N5—N6	−39.86 (12)	N5—Ir1—C16A—C17A	120.0 (2)
C12—N5—N6—C14	−1.0 (2)	N3—Ir1—C16A—C17A	−158.2 (2)
Ir1—N5—N6—C14	177.18 (13)	P1—Ir1—C16A—C17A	−64.3 (2)
C12—N5—N6—B1	177.15 (17)	Ir1—C16A—C17A—C18A	−42.2 (4)
Ir1—N5—N6—B1	−4.7 (2)	C16A—C17A—C18A—C19A	36.2 (5)
C4—N2—B1—N4	−123.3 (2)	C17A—C18A—C19A—Ir1	−14.3 (4)
N1—N2—B1—N4	62.0 (2)	C16A—Ir1—C19A—C18A	−8.1 (2)
C4—N2—B1—N6	115.2 (2)	N5—Ir1—C19A—C18A	−99.6 (2)
N1—N2—B1—N6	−59.4 (2)	P1—Ir1—C19A—C18A	81.2 (2)
C9—N4—B1—N2	121.1 (2)	N1—Ir1—C19A—C18A	174.6 (2)
N3—N4—B1—N2	−72.6 (2)

Table 1

Selected bond lengths (Å)

Ir1—C19A	2.0780 (18)
Ir1—C16A	2.0871 (19)
Ir1—N5	2.1781 (14)
Ir1—N3	2.2233 (15)
Ir1—P1	2.2381 (5)
Ir1—N1	2.2590 (15)