Crystal structure of chlorido-(2-{[2-(4-chloro-phen-yl)hydrazin-1-yl-idene-κN (1)](phen-yl)meth-yl}pyridine-κN)(η(5)-penta-methyl-cyclo-penta-dien-yl)iridium(III) tetra-phenyl-borate.

The title compound, [Ir(η(5)-C5Me5)Cl(C18H14ClN3)]B(C6H5)4, is chiral at the metal center and crystallizes as a racemate. In the cation, the hydrazinyl-idene-pyridine ligand is N,N-coordinated through the N-pyridyl and N-hydrazinyl-idene groups forming a five-membered metallacycle. An intra-molecular C-H⋯Cl hydrogen bond is observed. In the crystal, centrosymmetrically-related cations are connected by C-Cl⋯π inter-actions, forming a dimeric structure. The crystal packing is further stabilized by weak inter-ionic C-H⋯π inter-actions.

Related literature

For the pharmacological and catalytic properties of penta­methyl­cyclo­penta­dienyl iridium complexes, see: Johnpeter et al. (2013 ▸); Liu & Sadler (2014 ▸); Raja & Therrien (2014 ▸). For background to the chemistry and properties of hydrazinyl­idene­pyridine derivatives, see: Liu et al. (2002 ▸); Ghedini et al. (2004 ▸); Marandi et al. (2015 ▸); Devika et al. (2015 ▸); Ghosh et al. (2011 ▸, 2012 ▸). For the structures of related compounds, see: Prasad et al. (2010 ▸); Payne et al. (2013 ▸).

Experimental

Crystal data

[Ir(C10H15)Cl(C18H14ClN3)](C24H20B)

M = 989.85

Triclinic,

a = 8.9597 (4) Å

b = 12.5586 (6) Å

c = 20.0796 (9) Å

α = 98.228 (4)°

β = 95.860 (4)°

γ = 97.183 (4)°

V = 2201.95 (17) Å3

Z = 2

Mo Kα radiation

μ = 3.19 mm−1

T = 173 K

0.23 × 0.19 × 0.18 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: empirical (using intensity measurements) (DIFABS; Walker & Stuart, 1983 ▸) T min = 0.261, T max = 0.715

43057 measured reflections

11895 independent reflections

10423 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.058

S = 0.95

11895 reflections

541 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.58 e Å−3

Δρmin = −1.54 e Å−3

Data collection: IPDS EXPOSE (Stoe & Cie, 2000 ▸); cell refinement: IPDS CELL (Stoe & Cie, 2000 ▸); data reduction: IPDS INTEGRATE (Stoe & Cie, 2000 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015003023/rz5149sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015003023/rz5149Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015003023/rz5149fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015003023/rz5149fig2.tif

Dimeric structure involving two centrosymmetrically related cations.

CCDC reference: 1048992

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ir(C10H15)Cl(C18H14ClN3)](C24H20B)	Z = 2
Mr = 989.85	F(000) = 996
Triclinic, P1	Dx = 1.493 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9597 (4) Å	Cell parameters from 8000 reflections
b = 12.5586 (6) Å	θ = 1.9–28.9°
c = 20.0796 (9) Å	µ = 3.19 mm−1
α = 98.228 (4)°	T = 173 K
β = 95.860 (4)°	Block, red
γ = 97.183 (4)°	0.23 × 0.19 × 0.18 mm
V = 2201.95 (17) Å3

Stoe IPDS diffractometer	11895 independent reflections
Radiation source: fine-focus sealed tube	10423 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
phi oscillation scans	θmax = 29.2°, θmin = 1.7°
Absorption correction: empirical (using intensity measurements) (DIFABS; Walker & Stuart, 1983)	h = −12→11
Tmin = 0.261, Tmax = 0.715	k = −17→17
43057 measured reflections	l = −27→27

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ2(Fo2) + (0.0305P)2] where P = (Fo2 + 2Fc2)/3
11895 reflections	(Δ/σ)max = 0.002
541 parameters	Δρmax = 1.58 e Å−3
0 restraints	Δρmin = −1.54 e Å−3

Experimental. A crystal was mounted at 173 K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using Mo Kα graphite monochromated radiation. Image plate distance 100 mm, φ oscillation scans 0 - 180°, step Δφ = 1.2°, 5 minutes per frame.

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
C29	0.3816 (3)	0.68256 (18)	0.26342 (12)	0.0194 (5)
C30	0.2854 (3)	0.6179 (2)	0.20884 (13)	0.0246 (5)
H30	0.1834	0.6003	0.2136	0.029*
C31	0.3370 (4)	0.5790 (2)	0.14788 (14)	0.0307 (6)
H31	0.2698	0.5359	0.1132	0.037*
C32	0.4876 (4)	0.6044 (2)	0.13898 (14)	0.0322 (6)
H32	0.5220	0.5792	0.0983	0.039*
C33	0.5866 (3)	0.6679 (2)	0.19136 (15)	0.0291 (6)
H33	0.6882	0.6854	0.1860	0.035*
C34	0.5338 (3)	0.7053 (2)	0.25201 (14)	0.0231 (5)
H34	0.6024	0.7474	0.2866	0.028*
C41	0.4432 (3)	0.75292 (19)	0.39947 (13)	0.0193 (4)
C46	0.5465 (3)	0.6782 (2)	0.40772 (14)	0.0246 (5)
H46	0.5484	0.6222	0.3723	0.030*
C45	0.6455 (3)	0.6851 (2)	0.46676 (15)	0.0301 (6)
H45	0.7123	0.6345	0.4700	0.036*
C44	0.6449 (3)	0.7672 (2)	0.52088 (14)	0.0288 (6)
H44	0.7106	0.7720	0.5605	0.035*
C43	0.5444 (3)	0.8422 (2)	0.51493 (14)	0.0273 (5)
H43	0.5420	0.8974	0.5509	0.033*
C42	0.4476 (3)	0.8346 (2)	0.45520 (13)	0.0221 (5)
H42	0.3826	0.8864	0.4521	0.027*
C47	0.1657 (3)	0.6579 (2)	0.34644 (13)	0.0222 (5)
C52	0.1789 (4)	0.5770 (3)	0.38702 (19)	0.0391 (7)
H52	0.2746	0.5698	0.4070	0.047*
C51	0.0544 (4)	0.5066 (3)	0.3987 (2)	0.0519 (10)
H51	0.0688	0.4537	0.4259	0.062*
C50	−0.0903 (4)	0.5147 (3)	0.3703 (2)	0.0420 (8)
H50	−0.1735	0.4681	0.3782	0.050*
C49	−0.1084 (3)	0.5934 (2)	0.32995 (17)	0.0337 (6)
H49	−0.2047	0.6004	0.3105	0.040*
C48	0.0174 (3)	0.6627 (2)	0.31811 (15)	0.0278 (5)
H48	0.0021	0.7144	0.2902	0.033*
C35	0.2753 (3)	0.85771 (19)	0.31755 (13)	0.0193 (4)
C40	0.3444 (3)	0.9160 (2)	0.27141 (14)	0.0230 (5)
H40	0.4086	0.8824	0.2443	0.028*
C39	0.3212 (3)	1.0221 (2)	0.26434 (14)	0.0267 (5)
H39	0.3694	1.0576	0.2331	0.032*
C38	0.2256 (3)	1.0743 (2)	0.30421 (14)	0.0259 (5)
H38	0.2120	1.1457	0.3010	0.031*
C37	0.1509 (3)	1.0188 (2)	0.34875 (14)	0.0248 (5)
H37	0.0847	1.0522	0.3748	0.030*
C36	0.1749 (3)	0.9126 (2)	0.35462 (13)	0.0216 (5)
H36	0.1222	0.8765	0.3843	0.026*
C16	0.8371 (3)	−0.2312 (2)	0.07097 (14)	0.0259 (5)
C15	0.7281 (3)	−0.1629 (2)	0.06614 (14)	0.0269 (5)
H15	0.6522	−0.1765	0.0296	0.032*
C14	0.7332 (3)	−0.0734 (2)	0.11670 (14)	0.0238 (5)
H14	0.6582	−0.0286	0.1150	0.029*
C13	0.8507 (3)	−0.05156 (18)	0.16955 (12)	0.0187 (4)
C18	0.9592 (3)	−0.1224 (2)	0.17430 (14)	0.0227 (5)
H18	1.0359	−0.1090	0.2106	0.027*
C17	0.9515 (3)	−0.2127 (2)	0.12477 (14)	0.0262 (5)
H17	1.0226	−0.2604	0.1277	0.031*
C7	0.7727 (3)	0.10914 (19)	0.34383 (12)	0.0196 (5)
C12	0.7334 (3)	−0.0017 (2)	0.34617 (14)	0.0238 (5)
H12	0.6857	−0.0485	0.3077	0.029*
C11	0.7662 (3)	−0.0412 (2)	0.40643 (15)	0.0271 (6)
H11	0.7405	−0.1147	0.4084	0.032*
C10	0.8370 (3)	0.0288 (2)	0.46348 (14)	0.0294 (6)
H10	0.8573	0.0020	0.5038	0.035*
C9	0.8781 (3)	0.1384 (2)	0.46135 (14)	0.0290 (6)
H9	0.9269	0.1846	0.4999	0.035*
C8	0.8460 (3)	0.1788 (2)	0.40143 (13)	0.0244 (5)
H8	0.8734	0.2522	0.3997	0.029*
C5	0.6489 (3)	0.24523 (18)	0.28198 (12)	0.0179 (4)
C4	0.5715 (3)	0.2802 (2)	0.33544 (13)	0.0230 (5)
H4	0.5746	0.2467	0.3739	0.028*
C3	0.4887 (3)	0.3664 (2)	0.33071 (14)	0.0259 (5)
H3	0.4375	0.3923	0.3663	0.031*
C2	0.4841 (3)	0.4128 (2)	0.27214 (15)	0.0262 (5)
H2	0.4300	0.4705	0.2679	0.031*
C1	0.5610 (3)	0.3723 (2)	0.22002 (14)	0.0242 (5)
H1	0.5550	0.4026	0.1804	0.029*
C6	0.7347 (3)	0.15343 (18)	0.28092 (12)	0.0176 (4)
C22	0.8732 (3)	0.36272 (19)	0.12008 (14)	0.0227 (5)
C23	0.9768 (3)	0.2910 (2)	0.14045 (15)	0.0256 (5)
C19	0.9463 (3)	0.1923 (2)	0.09100 (14)	0.0239 (5)
C20	0.8205 (3)	0.2007 (2)	0.04434 (14)	0.0255 (5)
C21	0.7727 (3)	0.3067 (2)	0.06293 (14)	0.0234 (5)
C25	0.7491 (4)	0.1177 (3)	−0.01532 (15)	0.0357 (7)
H25A	0.7881	0.1360	−0.0557	0.054*
H25B	0.6412	0.1167	−0.0202	0.054*
H25C	0.7724	0.0473	−0.0083	0.054*
C24	1.0441 (4)	0.1043 (2)	0.08814 (18)	0.0352 (7)
H24A	0.9867	0.0378	0.0641	0.053*
H24B	1.0788	0.0944	0.1334	0.053*
H24C	1.1297	0.1241	0.0651	0.053*
C28	1.1065 (4)	0.3190 (3)	0.19625 (18)	0.0380 (7)
H28A	1.1949	0.3500	0.1788	0.057*
H28B	1.1267	0.2544	0.2138	0.057*
H28C	1.0808	0.3705	0.2319	0.057*
C27	0.8724 (4)	0.4769 (2)	0.15301 (16)	0.0316 (6)
H27A	0.9419	0.5251	0.1339	0.047*
H27B	0.9025	0.4832	0.2009	0.047*
H27C	0.7722	0.4958	0.1454	0.047*
C26	0.6498 (4)	0.3519 (2)	0.02314 (16)	0.0341 (6)
H26A	0.5749	0.3708	0.0519	0.051*
H26B	0.6032	0.2981	−0.0145	0.051*
H26C	0.6932	0.4154	0.0067	0.051*
B1	0.3166 (3)	0.7375 (2)	0.33184 (14)	0.0192 (5)
Cl1	0.49270 (7)	0.12986 (5)	0.10753 (3)	0.02555 (12)
Cl2	0.82834 (11)	−0.34453 (6)	0.00791 (4)	0.04097 (18)
N3	0.8735 (2)	0.04187 (16)	0.21931 (11)	0.0206 (4)
H3N	0.912 (4)	0.033 (2)	0.2572 (18)	0.025 (8)*
N2	0.7748 (2)	0.11793 (15)	0.22150 (10)	0.0168 (4)
N1	0.6440 (2)	0.29113 (15)	0.22428 (11)	0.0186 (4)
Ir1	0.747445 (11)	0.217327 (7)	0.145260 (5)	0.01615 (3)

	U11	U22	U33	U12	U13	U23
C29	0.0232 (12)	0.0170 (10)	0.0192 (11)	0.0060 (9)	0.0034 (9)	0.0039 (9)
C30	0.0266 (13)	0.0256 (12)	0.0213 (12)	0.0063 (10)	0.0005 (10)	0.0023 (10)
C31	0.0413 (16)	0.0323 (14)	0.0171 (12)	0.0103 (12)	−0.0026 (11)	−0.0014 (10)
C32	0.0482 (18)	0.0359 (14)	0.0183 (12)	0.0205 (13)	0.0107 (12)	0.0059 (11)
C33	0.0310 (14)	0.0336 (14)	0.0288 (14)	0.0140 (11)	0.0116 (12)	0.0111 (11)
C34	0.0241 (12)	0.0220 (11)	0.0241 (12)	0.0055 (9)	0.0041 (10)	0.0040 (10)
C41	0.0188 (11)	0.0202 (10)	0.0187 (11)	0.0011 (9)	0.0035 (9)	0.0028 (9)
C46	0.0271 (13)	0.0225 (11)	0.0233 (12)	0.0063 (10)	0.0008 (10)	−0.0003 (10)
C45	0.0313 (14)	0.0325 (14)	0.0278 (14)	0.0126 (11)	−0.0011 (12)	0.0057 (11)
C44	0.0298 (14)	0.0351 (14)	0.0205 (12)	0.0027 (11)	−0.0013 (11)	0.0059 (11)
C43	0.0312 (14)	0.0288 (13)	0.0207 (12)	0.0014 (11)	0.0063 (11)	0.0005 (10)
C42	0.0231 (12)	0.0232 (11)	0.0208 (12)	0.0035 (9)	0.0065 (10)	0.0033 (9)
C47	0.0208 (12)	0.0240 (11)	0.0211 (12)	0.0023 (9)	0.0043 (10)	0.0003 (9)
C52	0.0274 (15)	0.0381 (16)	0.053 (2)	−0.0004 (12)	0.0012 (14)	0.0204 (15)
C51	0.0419 (19)	0.0440 (18)	0.072 (3)	−0.0071 (15)	0.0017 (18)	0.0325 (19)
C50	0.0298 (16)	0.0382 (16)	0.056 (2)	−0.0090 (13)	0.0102 (15)	0.0091 (15)
C49	0.0197 (13)	0.0391 (15)	0.0388 (17)	−0.0009 (11)	0.0035 (12)	−0.0006 (13)
C48	0.0235 (13)	0.0316 (13)	0.0274 (14)	0.0031 (10)	0.0028 (11)	0.0029 (11)
C35	0.0168 (11)	0.0197 (10)	0.0202 (11)	0.0031 (8)	−0.0006 (9)	0.0008 (9)
C40	0.0205 (12)	0.0226 (11)	0.0262 (13)	0.0037 (9)	0.0042 (10)	0.0031 (10)
C39	0.0255 (13)	0.0274 (12)	0.0277 (13)	0.0010 (10)	0.0022 (11)	0.0097 (11)
C38	0.0279 (13)	0.0197 (11)	0.0289 (14)	0.0052 (10)	−0.0042 (11)	0.0031 (10)
C37	0.0248 (13)	0.0246 (12)	0.0238 (12)	0.0099 (10)	−0.0021 (10)	−0.0021 (10)
C36	0.0233 (12)	0.0243 (11)	0.0174 (11)	0.0067 (9)	0.0008 (10)	0.0018 (9)
C16	0.0366 (15)	0.0171 (11)	0.0228 (12)	−0.0013 (10)	0.0105 (11)	−0.0007 (9)
C15	0.0329 (14)	0.0243 (12)	0.0206 (12)	−0.0012 (10)	0.0005 (11)	0.0003 (10)
C14	0.0254 (13)	0.0204 (11)	0.0245 (13)	0.0018 (9)	0.0005 (10)	0.0023 (9)
C13	0.0226 (12)	0.0179 (10)	0.0165 (11)	0.0034 (9)	0.0049 (9)	0.0031 (8)
C18	0.0238 (12)	0.0215 (11)	0.0232 (12)	0.0056 (9)	0.0028 (10)	0.0033 (9)
C17	0.0312 (14)	0.0194 (11)	0.0303 (14)	0.0071 (10)	0.0113 (11)	0.0035 (10)
C7	0.0193 (11)	0.0239 (11)	0.0174 (11)	0.0072 (9)	0.0035 (9)	0.0051 (9)
C12	0.0219 (12)	0.0242 (12)	0.0254 (13)	0.0017 (9)	0.0007 (10)	0.0070 (10)
C11	0.0236 (13)	0.0308 (13)	0.0325 (14)	0.0064 (10)	0.0088 (11)	0.0176 (11)
C10	0.0283 (14)	0.0468 (16)	0.0194 (12)	0.0157 (12)	0.0069 (11)	0.0145 (12)
C9	0.0313 (14)	0.0397 (15)	0.0161 (12)	0.0117 (12)	0.0009 (11)	0.0007 (11)
C8	0.0290 (13)	0.0250 (12)	0.0203 (12)	0.0088 (10)	0.0035 (10)	0.0026 (10)
C5	0.0197 (11)	0.0158 (10)	0.0177 (11)	0.0020 (8)	0.0007 (9)	0.0024 (8)
C4	0.0252 (12)	0.0237 (11)	0.0214 (12)	0.0058 (10)	0.0044 (10)	0.0048 (9)
C3	0.0250 (13)	0.0247 (12)	0.0289 (14)	0.0081 (10)	0.0069 (11)	0.0005 (10)
C2	0.0240 (13)	0.0188 (11)	0.0354 (15)	0.0074 (9)	−0.0012 (11)	0.0025 (10)
C1	0.0285 (13)	0.0196 (11)	0.0255 (13)	0.0072 (10)	0.0010 (11)	0.0052 (10)
C6	0.0183 (11)	0.0167 (10)	0.0176 (11)	0.0018 (8)	0.0007 (9)	0.0034 (8)
C22	0.0199 (12)	0.0202 (11)	0.0272 (13)	−0.0014 (9)	0.0018 (10)	0.0056 (10)
C23	0.0208 (12)	0.0266 (12)	0.0300 (14)	−0.0004 (10)	0.0021 (11)	0.0105 (11)
C19	0.0249 (13)	0.0247 (12)	0.0238 (12)	0.0016 (10)	0.0097 (10)	0.0065 (10)
C20	0.0296 (14)	0.0264 (12)	0.0211 (12)	0.0002 (10)	0.0090 (11)	0.0046 (10)
C21	0.0219 (12)	0.0241 (11)	0.0242 (13)	−0.0018 (9)	0.0008 (10)	0.0095 (10)
C25	0.0418 (17)	0.0386 (15)	0.0216 (13)	−0.0050 (13)	0.0076 (12)	−0.0059 (11)
C24	0.0314 (15)	0.0312 (14)	0.0488 (19)	0.0087 (12)	0.0196 (14)	0.0114 (13)
C28	0.0284 (15)	0.0431 (17)	0.0401 (18)	−0.0023 (13)	−0.0091 (13)	0.0144 (14)
C27	0.0345 (15)	0.0212 (12)	0.0368 (16)	−0.0015 (11)	0.0012 (13)	0.0036 (11)
C26	0.0354 (16)	0.0361 (15)	0.0307 (15)	0.0014 (12)	−0.0068 (13)	0.0159 (12)
B1	0.0178 (12)	0.0194 (12)	0.0203 (13)	0.0044 (9)	0.0028 (10)	0.0013 (10)
Cl1	0.0191 (3)	0.0295 (3)	0.0263 (3)	−0.0005 (2)	−0.0014 (2)	0.0054 (2)
Cl2	0.0640 (5)	0.0239 (3)	0.0319 (4)	0.0004 (3)	0.0143 (4)	−0.0073 (3)
N3	0.0238 (11)	0.0211 (9)	0.0166 (10)	0.0089 (8)	−0.0023 (8)	0.0004 (8)
N2	0.0175 (9)	0.0165 (9)	0.0163 (9)	0.0038 (7)	0.0015 (8)	0.0019 (7)
N1	0.0184 (10)	0.0169 (9)	0.0206 (10)	0.0042 (7)	−0.0003 (8)	0.0033 (7)
Ir1	0.01740 (5)	0.01629 (4)	0.01465 (4)	0.00196 (3)	0.00082 (3)	0.00322 (3)

C29—C30	1.408 (4)	C7—C8	1.395 (4)
C29—C34	1.408 (4)	C7—C12	1.401 (3)
C29—B1	1.642 (4)	C7—C6	1.477 (3)
C30—C31	1.397 (4)	C12—C11	1.390 (4)
C30—H30	0.9300	C12—H12	0.9300
C31—C32	1.383 (5)	C11—C10	1.382 (4)
C31—H31	0.9300	C11—H11	0.9300
C32—C33	1.386 (5)	C10—C9	1.389 (4)
C32—H32	0.9300	C10—H10	0.9300
C33—C34	1.392 (4)	C9—C8	1.388 (4)
C33—H33	0.9300	C9—H9	0.9300
C34—H34	0.9300	C8—H8	0.9300
C41—C42	1.399 (3)	C5—N1	1.365 (3)
C41—C46	1.413 (3)	C5—C4	1.385 (3)
C41—B1	1.650 (4)	C5—C6	1.462 (3)
C46—C45	1.392 (4)	C4—C3	1.396 (3)
C46—H46	0.9300	C4—H4	0.9300
C45—C44	1.388 (4)	C3—C2	1.384 (4)
C45—H45	0.9300	C3—H3	0.9300
C44—C43	1.390 (4)	C2—C1	1.382 (4)
C44—H44	0.9300	C2—H2	0.9300
C43—C42	1.391 (4)	C1—N1	1.342 (3)
C43—H43	0.9300	C1—H1	0.9300
C42—H42	0.9300	C6—N2	1.314 (3)
C47—C52	1.399 (4)	C22—C21	1.422 (4)
C47—C48	1.403 (4)	C22—C23	1.441 (3)
C47—B1	1.655 (4)	C22—C27	1.492 (4)
C52—C51	1.395 (4)	C22—Ir1	2.174 (2)
C52—H52	0.9300	C23—C19	1.451 (4)
C51—C50	1.384 (5)	C23—C28	1.499 (4)
C51—H51	0.9300	C23—Ir1	2.163 (3)
C50—C49	1.379 (5)	C19—C20	1.414 (4)
C50—H50	0.9300	C19—C24	1.492 (4)
C49—C48	1.397 (4)	C19—Ir1	2.213 (3)
C49—H49	0.9300	C20—C21	1.459 (4)
C48—H48	0.9300	C20—C25	1.500 (4)
C35—C40	1.405 (4)	C20—Ir1	2.182 (3)
C35—C36	1.408 (3)	C21—C26	1.510 (4)
C35—B1	1.655 (3)	C21—Ir1	2.142 (2)
C40—C39	1.399 (3)	C25—H25A	0.9600
C40—H40	0.9300	C25—H25B	0.9600
C39—C38	1.391 (4)	C25—H25C	0.9600
C39—H39	0.9300	C24—H24A	0.9600
C38—C37	1.385 (4)	C24—H24B	0.9600
C38—H38	0.9300	C24—H24C	0.9600
C37—C36	1.397 (3)	C28—H28A	0.9600
C37—H37	0.9300	C28—H28B	0.9600
C36—H36	0.9300	C28—H28C	0.9600
C16—C15	1.382 (4)	C27—H27A	0.9600
C16—C17	1.384 (4)	C27—H27B	0.9600
C16—Cl2	1.753 (3)	C27—H27C	0.9600
C15—C14	1.396 (4)	C26—H26A	0.9600
C15—H15	0.9300	C26—H26B	0.9600
C14—C13	1.388 (4)	C26—H26C	0.9600
C14—H14	0.9300	Cl1—Ir1	2.4024 (6)
C13—C18	1.402 (3)	N3—N2	1.380 (3)
C13—N3	1.407 (3)	N3—H3N	0.83 (3)
C18—C17	1.387 (4)	N2—Ir1	2.1233 (19)
C18—H18	0.9300	N1—Ir1	2.081 (2)
C17—H17	0.9300
C30—C29—C34	115.0 (2)	C2—C3—H3	120.6
C30—C29—B1	122.0 (2)	C4—C3—H3	120.6
C34—C29—B1	122.7 (2)	C1—C2—C3	119.2 (2)
C31—C30—C29	122.6 (3)	C1—C2—H2	120.4
C31—C30—H30	118.7	C3—C2—H2	120.4
C29—C30—H30	118.7	N1—C1—C2	122.7 (2)
C32—C31—C30	120.2 (3)	N1—C1—H1	118.6
C32—C31—H31	119.9	C2—C1—H1	118.6
C30—C31—H31	119.9	N2—C6—C5	114.8 (2)
C31—C32—C33	119.3 (3)	N2—C6—C7	124.9 (2)
C31—C32—H32	120.4	C5—C6—C7	120.2 (2)
C33—C32—H32	120.4	C21—C22—C23	108.5 (2)
C32—C33—C34	119.9 (3)	C21—C22—C27	125.7 (2)
C32—C33—H33	120.1	C23—C22—C27	125.8 (2)
C34—C33—H33	120.1	C21—C22—Ir1	69.55 (14)
C33—C34—C29	123.0 (3)	C23—C22—Ir1	70.19 (14)
C33—C34—H34	118.5	C27—C22—Ir1	126.5 (2)
C29—C34—H34	118.5	C22—C23—C19	107.2 (2)
C42—C41—C46	115.0 (2)	C22—C23—C28	126.3 (3)
C42—C41—B1	122.8 (2)	C19—C23—C28	125.9 (3)
C46—C41—B1	122.0 (2)	C22—C23—Ir1	70.99 (14)
C45—C46—C41	122.7 (2)	C19—C23—Ir1	72.50 (15)
C45—C46—H46	118.7	C28—C23—Ir1	128.4 (2)
C41—C46—H46	118.7	C20—C19—C23	108.3 (2)
C44—C45—C46	120.2 (2)	C20—C19—C24	127.6 (3)
C44—C45—H45	119.9	C23—C19—C24	123.8 (3)
C46—C45—H45	119.9	C20—C19—Ir1	70.06 (15)
C45—C44—C43	119.0 (3)	C23—C19—Ir1	68.80 (14)
C45—C44—H44	120.5	C24—C19—Ir1	131.44 (18)
C43—C44—H44	120.5	C19—C20—C21	108.1 (2)
C44—C43—C42	119.9 (2)	C19—C20—C25	126.9 (3)
C44—C43—H43	120.0	C21—C20—C25	125.0 (3)
C42—C43—H43	120.0	C19—C20—Ir1	72.40 (15)
C43—C42—C41	123.3 (2)	C21—C20—Ir1	68.80 (14)
C43—C42—H42	118.4	C25—C20—Ir1	125.59 (19)
C41—C42—H42	118.4	C22—C21—C20	107.6 (2)
C52—C47—C48	114.8 (2)	C22—C21—C26	126.8 (2)
C52—C47—B1	121.4 (2)	C20—C21—C26	125.3 (3)
C48—C47—B1	123.7 (2)	C22—C21—Ir1	71.98 (14)
C51—C52—C47	122.8 (3)	C20—C21—Ir1	71.79 (14)
C51—C52—H52	118.6	C26—C21—Ir1	126.9 (2)
C47—C52—H52	118.6	C20—C25—H25A	109.5
C50—C51—C52	120.6 (3)	C20—C25—H25B	109.5
C50—C51—H51	119.7	H25A—C25—H25B	109.5
C52—C51—H51	119.7	C20—C25—H25C	109.5
C49—C50—C51	118.5 (3)	H25A—C25—H25C	109.5
C49—C50—H50	120.7	H25B—C25—H25C	109.5
C51—C50—H50	120.7	C19—C24—H24A	109.5
C50—C49—C48	120.3 (3)	C19—C24—H24B	109.5
C50—C49—H49	119.9	H24A—C24—H24B	109.5
C48—C49—H49	119.9	C19—C24—H24C	109.5
C49—C48—C47	123.0 (3)	H24A—C24—H24C	109.5
C49—C48—H48	118.5	H24B—C24—H24C	109.5
C47—C48—H48	118.5	C23—C28—H28A	109.5
C40—C35—C36	114.9 (2)	C23—C28—H28B	109.5
C40—C35—B1	123.2 (2)	H28A—C28—H28B	109.5
C36—C35—B1	121.8 (2)	C23—C28—H28C	109.5
C39—C40—C35	123.2 (2)	H28A—C28—H28C	109.5
C39—C40—H40	118.4	H28B—C28—H28C	109.5
C35—C40—H40	118.4	C22—C27—H27A	109.5
C38—C39—C40	119.7 (2)	C22—C27—H27B	109.5
C38—C39—H39	120.2	H27A—C27—H27B	109.5
C40—C39—H39	120.2	C22—C27—H27C	109.5
C37—C38—C39	119.2 (2)	H27A—C27—H27C	109.5
C37—C38—H38	120.4	H27B—C27—H27C	109.5
C39—C38—H38	120.4	C21—C26—H26A	109.5
C38—C37—C36	120.1 (2)	C21—C26—H26B	109.5
C38—C37—H37	120.0	H26A—C26—H26B	109.5
C36—C37—H37	120.0	C21—C26—H26C	109.5
C37—C36—C35	122.9 (2)	H26A—C26—H26C	109.5
C37—C36—H36	118.6	H26B—C26—H26C	109.5
C35—C36—H36	118.6	C29—B1—C41	111.8 (2)
C15—C16—C17	121.5 (2)	C29—B1—C35	106.48 (19)
C15—C16—Cl2	119.1 (2)	C41—B1—C35	109.75 (19)
C17—C16—Cl2	119.4 (2)	C29—B1—C47	109.7 (2)
C16—C15—C14	119.4 (3)	C41—B1—C47	107.3 (2)
C16—C15—H15	120.3	C35—B1—C47	111.8 (2)
C14—C15—H15	120.3	N2—N3—C13	122.2 (2)
C13—C14—C15	119.7 (2)	N2—N3—H3N	114 (2)
C13—C14—H14	120.2	C13—N3—H3N	115 (2)
C15—C14—H14	120.2	C6—N2—N3	117.3 (2)
C14—C13—C18	120.2 (2)	C6—N2—Ir1	116.71 (15)
C14—C13—N3	123.9 (2)	N3—N2—Ir1	122.48 (15)
C18—C13—N3	115.9 (2)	C1—N1—C5	118.2 (2)
C17—C18—C13	119.8 (2)	C1—N1—Ir1	124.82 (17)
C17—C18—H18	120.1	C5—N1—Ir1	116.59 (15)
C13—C18—H18	120.1	N1—Ir1—N2	76.15 (7)
C16—C17—C18	119.3 (2)	N1—Ir1—C21	115.49 (9)
C16—C17—H17	120.3	N2—Ir1—C21	165.88 (9)
C18—C17—H17	120.3	N1—Ir1—C23	114.56 (10)
C8—C7—C12	120.1 (2)	N2—Ir1—C23	103.16 (9)
C8—C7—C6	119.5 (2)	C21—Ir1—C23	65.35 (10)
C12—C7—C6	120.4 (2)	N1—Ir1—C22	98.28 (9)
C11—C12—C7	119.5 (3)	N2—Ir1—C22	135.84 (9)
C11—C12—H12	120.3	C21—Ir1—C22	38.47 (10)
C7—C12—H12	120.3	C23—Ir1—C22	38.82 (9)
C10—C11—C12	120.0 (3)	N1—Ir1—C20	154.47 (9)
C10—C11—H11	120.0	N2—Ir1—C20	129.39 (9)
C12—C11—H11	120.0	C21—Ir1—C20	39.41 (10)
C11—C10—C9	120.8 (2)	C23—Ir1—C20	64.63 (11)
C11—C10—H10	119.6	C22—Ir1—C20	64.50 (10)
C9—C10—H10	119.6	N1—Ir1—C19	152.64 (10)
C8—C9—C10	119.7 (3)	N2—Ir1—C19	101.40 (8)
C8—C9—H9	120.2	C21—Ir1—C19	64.54 (10)
C10—C9—H9	120.2	C23—Ir1—C19	38.70 (10)
C9—C8—C7	119.9 (2)	C22—Ir1—C19	64.10 (9)
C9—C8—H8	120.0	C20—Ir1—C19	37.54 (10)
C7—C8—H8	120.0	N1—Ir1—Cl1	82.17 (6)
N1—C5—C4	122.0 (2)	N2—Ir1—Cl1	92.12 (6)
N1—C5—C6	114.7 (2)	C21—Ir1—Cl1	97.28 (7)
C4—C5—C6	123.3 (2)	C23—Ir1—Cl1	159.44 (8)
C5—C4—C3	119.0 (2)	C22—Ir1—Cl1	131.07 (7)
C5—C4—H4	120.5	C20—Ir1—Cl1	95.06 (8)
C3—C4—H4	120.5	C19—Ir1—Cl1	125.16 (7)
C2—C3—C4	118.9 (2)
C34—C29—C30—C31	0.0 (4)	C7—C6—N2—Ir1	−166.92 (19)
B1—C29—C30—C31	173.9 (2)	C13—N3—N2—C6	134.8 (2)
C29—C30—C31—C32	−0.6 (4)	C13—N3—N2—Ir1	−67.1 (3)
C30—C31—C32—C33	0.6 (4)	C2—C1—N1—C5	1.7 (4)
C31—C32—C33—C34	−0.1 (4)	C2—C1—N1—Ir1	174.5 (2)
C32—C33—C34—C29	−0.5 (4)	C4—C5—N1—C1	−0.1 (4)
C30—C29—C34—C33	0.5 (3)	C6—C5—N1—C1	176.7 (2)
B1—C29—C34—C33	−173.3 (2)	C4—C5—N1—Ir1	−173.49 (19)
C42—C41—C46—C45	0.0 (4)	C6—C5—N1—Ir1	3.3 (3)
B1—C41—C46—C45	−174.6 (3)	C1—N1—Ir1—N2	−170.9 (2)
C41—C46—C45—C44	0.5 (4)	C5—N1—Ir1—N2	1.97 (17)
C46—C45—C44—C43	−0.2 (4)	C1—N1—Ir1—C21	17.6 (2)
C45—C44—C43—C42	−0.5 (4)	C5—N1—Ir1—C21	−169.51 (17)
C44—C43—C42—C41	1.0 (4)	C1—N1—Ir1—C23	90.7 (2)
C46—C41—C42—C43	−0.8 (4)	C5—N1—Ir1—C23	−96.38 (19)
B1—C41—C42—C43	173.8 (2)	C1—N1—Ir1—C22	53.8 (2)
C48—C47—C52—C51	−0.2 (5)	C5—N1—Ir1—C22	−133.33 (18)
B1—C47—C52—C51	−178.2 (3)	C1—N1—Ir1—C20	8.6 (3)
C47—C52—C51—C50	−0.4 (6)	C5—N1—Ir1—C20	−178.5 (2)
C52—C51—C50—C49	0.3 (6)	C1—N1—Ir1—C19	101.0 (3)
C51—C50—C49—C48	0.3 (5)	C5—N1—Ir1—C19	−86.1 (2)
C50—C49—C48—C47	−0.9 (5)	C1—N1—Ir1—Cl1	−76.8 (2)
C52—C47—C48—C49	0.8 (4)	C5—N1—Ir1—Cl1	96.12 (17)
B1—C47—C48—C49	178.7 (3)	C6—N2—Ir1—N1	−7.72 (17)
C36—C35—C40—C39	2.6 (4)	N3—N2—Ir1—N1	−166.01 (19)
B1—C35—C40—C39	−173.3 (2)	C6—N2—Ir1—C21	139.0 (3)
C35—C40—C39—C38	−0.1 (4)	N3—N2—Ir1—C21	−19.2 (5)
C40—C39—C38—C37	−2.1 (4)	C6—N2—Ir1—C23	104.74 (19)
C39—C38—C37—C36	1.7 (4)	N3—N2—Ir1—C23	−53.55 (19)
C38—C37—C36—C35	1.0 (4)	C6—N2—Ir1—C22	79.9 (2)
C40—C35—C36—C37	−3.1 (4)	N3—N2—Ir1—C22	−78.4 (2)
B1—C35—C36—C37	172.8 (2)	C6—N2—Ir1—C20	172.56 (17)
C17—C16—C15—C14	−0.1 (4)	N3—N2—Ir1—C20	14.3 (2)
Cl2—C16—C15—C14	179.1 (2)	C6—N2—Ir1—C19	144.34 (18)
C16—C15—C14—C13	2.6 (4)	N3—N2—Ir1—C19	−13.94 (19)
C15—C14—C13—C18	−3.6 (4)	C6—N2—Ir1—Cl1	−89.12 (17)
C15—C14—C13—N3	173.9 (2)	N3—N2—Ir1—Cl1	112.59 (17)
C14—C13—C18—C17	2.1 (4)	C22—C21—Ir1—N1	69.91 (17)
N3—C13—C18—C17	−175.6 (2)	C20—C21—Ir1—N1	−173.88 (14)
C15—C16—C17—C18	−1.4 (4)	C26—C21—Ir1—N1	−53.0 (3)
Cl2—C16—C17—C18	179.4 (2)	C22—C21—Ir1—N2	−74.0 (4)
C13—C18—C17—C16	0.4 (4)	C20—C21—Ir1—N2	42.2 (4)
C8—C7—C12—C11	0.8 (4)	C26—C21—Ir1—N2	163.1 (3)
C6—C7—C12—C11	−178.1 (2)	C22—C21—Ir1—C23	−36.82 (15)
C7—C12—C11—C10	0.1 (4)	C20—C21—Ir1—C23	79.39 (17)
C12—C11—C10—C9	−0.9 (4)	C26—C21—Ir1—C23	−159.8 (3)
C11—C10—C9—C8	0.8 (4)	C20—C21—Ir1—C22	116.2 (2)
C10—C9—C8—C7	0.0 (4)	C26—C21—Ir1—C22	−122.9 (3)
C12—C7—C8—C9	−0.9 (4)	C22—C21—Ir1—C20	−116.2 (2)
C6—C7—C8—C9	178.0 (2)	C26—C21—Ir1—C20	120.9 (3)
N1—C5—C4—C3	−1.4 (4)	C22—C21—Ir1—C19	−79.72 (16)
C6—C5—C4—C3	−177.9 (2)	C20—C21—Ir1—C19	36.49 (16)
C5—C4—C3—C2	1.3 (4)	C26—C21—Ir1—C19	157.3 (3)
C4—C3—C2—C1	0.2 (4)	C22—C21—Ir1—Cl1	154.68 (14)
C3—C2—C1—N1	−1.8 (4)	C20—C21—Ir1—Cl1	−89.11 (15)
N1—C5—C6—N2	−9.9 (3)	C26—C21—Ir1—Cl1	31.7 (2)
C4—C5—C6—N2	166.9 (2)	C22—C23—Ir1—N1	−71.61 (17)
N1—C5—C6—C7	168.8 (2)	C19—C23—Ir1—N1	172.47 (13)
C4—C5—C6—C7	−14.4 (4)	C28—C23—Ir1—N1	50.1 (3)
C8—C7—C6—N2	125.5 (3)	C22—C23—Ir1—N2	−152.20 (15)
C12—C7—C6—N2	−55.6 (4)	C19—C23—Ir1—N2	91.88 (15)
C8—C7—C6—C5	−53.1 (3)	C28—C23—Ir1—N2	−30.5 (3)
C12—C7—C6—C5	125.8 (3)	C22—C23—Ir1—C21	36.50 (16)
C21—C22—C23—C19	4.7 (3)	C19—C23—Ir1—C21	−79.42 (16)
C27—C22—C23—C19	−174.8 (3)	C28—C23—Ir1—C21	158.2 (3)
Ir1—C22—C23—C19	63.91 (17)	C19—C23—Ir1—C22	−115.9 (2)
C21—C22—C23—C28	176.7 (3)	C28—C23—Ir1—C22	121.7 (3)
C27—C22—C23—C28	−2.8 (4)	C22—C23—Ir1—C20	80.18 (17)
Ir1—C22—C23—C28	−124.2 (3)	C19—C23—Ir1—C20	−35.74 (15)
C21—C22—C23—Ir1	−59.18 (18)	C28—C23—Ir1—C20	−158.1 (3)
C27—C22—C23—Ir1	121.3 (3)	C22—C23—Ir1—C19	115.9 (2)
C22—C23—C19—C20	−3.8 (3)	C28—C23—Ir1—C19	−122.4 (3)
C28—C23—C19—C20	−175.8 (3)	C22—C23—Ir1—Cl1	70.8 (3)
Ir1—C23—C19—C20	59.08 (18)	C19—C23—Ir1—Cl1	−45.1 (3)
C22—C23—C19—C24	170.6 (2)	C28—C23—Ir1—Cl1	−167.52 (18)
C28—C23—C19—C24	−1.4 (4)	C21—C22—Ir1—N1	−121.06 (15)
Ir1—C23—C19—C24	−126.5 (2)	C23—C22—Ir1—N1	119.29 (16)
C22—C23—C19—Ir1	−62.91 (17)	C27—C22—Ir1—N1	−1.1 (2)
C28—C23—C19—Ir1	125.1 (3)	C21—C22—Ir1—N2	160.33 (14)
C23—C19—C20—C21	1.5 (3)	C23—C22—Ir1—N2	40.7 (2)
C24—C19—C20—C21	−172.7 (2)	C27—C22—Ir1—N2	−79.7 (3)
Ir1—C19—C20—C21	59.81 (18)	C23—C22—Ir1—C21	−119.7 (2)
C23—C19—C20—C25	−180.0 (3)	C27—C22—Ir1—C21	119.9 (3)
C24—C19—C20—C25	5.8 (4)	C21—C22—Ir1—C23	119.7 (2)
Ir1—C19—C20—C25	−121.7 (3)	C27—C22—Ir1—C23	−120.4 (3)
C23—C19—C20—Ir1	−58.30 (18)	C21—C22—Ir1—C20	39.13 (16)
C24—C19—C20—Ir1	127.5 (3)	C23—C22—Ir1—C20	−80.53 (17)
C23—C22—C21—C20	−3.8 (3)	C27—C22—Ir1—C20	159.1 (3)
C27—C22—C21—C20	175.7 (3)	C21—C22—Ir1—C19	80.97 (17)
Ir1—C22—C21—C20	−63.39 (17)	C23—C22—Ir1—C19	−38.69 (16)
C23—C22—C21—C26	−177.4 (3)	C27—C22—Ir1—C19	−159.1 (3)
C27—C22—C21—C26	2.1 (5)	C21—C22—Ir1—Cl1	−34.25 (18)
Ir1—C22—C21—C26	123.0 (3)	C23—C22—Ir1—Cl1	−153.90 (13)
C23—C22—C21—Ir1	59.57 (18)	C27—C22—Ir1—Cl1	85.7 (2)
C27—C22—C21—Ir1	−120.9 (3)	C19—C20—Ir1—N1	131.1 (2)
C19—C20—C21—C22	1.4 (3)	C21—C20—Ir1—N1	12.9 (3)
C25—C20—C21—C22	−177.1 (3)	C25—C20—Ir1—N1	−105.7 (3)
Ir1—C20—C21—C22	63.51 (18)	C19—C20—Ir1—N2	−49.54 (19)
C19—C20—C21—C26	175.1 (3)	C21—C20—Ir1—N2	−167.75 (13)
C25—C20—C21—C26	−3.4 (4)	C25—C20—Ir1—N2	73.7 (3)
Ir1—C20—C21—C26	−122.8 (3)	C19—C20—Ir1—C21	118.2 (2)
C19—C20—C21—Ir1	−62.10 (18)	C25—C20—Ir1—C21	−118.6 (3)
C25—C20—C21—Ir1	119.4 (3)	C19—C20—Ir1—C23	36.83 (15)
C30—C29—B1—C41	150.7 (2)	C21—C20—Ir1—C23	−81.38 (16)
C34—C29—B1—C41	−35.9 (3)	C25—C20—Ir1—C23	160.0 (3)
C30—C29—B1—C35	−89.4 (3)	C19—C20—Ir1—C22	80.01 (16)
C34—C29—B1—C35	83.9 (3)	C21—C20—Ir1—C22	−38.20 (15)
C30—C29—B1—C47	31.8 (3)	C25—C20—Ir1—C22	−156.8 (3)
C34—C29—B1—C47	−154.8 (2)	C21—C20—Ir1—C19	−118.2 (2)
C42—C41—B1—C29	151.8 (2)	C25—C20—Ir1—C19	123.2 (3)
C46—C41—B1—C29	−34.0 (3)	C19—C20—Ir1—Cl1	−146.48 (14)
C42—C41—B1—C35	33.9 (3)	C21—C20—Ir1—Cl1	95.32 (14)
C46—C41—B1—C35	−151.9 (2)	C25—C20—Ir1—Cl1	−23.3 (3)
C42—C41—B1—C47	−87.8 (3)	C20—C19—Ir1—N1	−135.02 (19)
C46—C41—B1—C47	86.4 (3)	C23—C19—Ir1—N1	−15.0 (3)
C40—C35—B1—C29	−24.8 (3)	C24—C19—Ir1—N1	101.9 (3)
C36—C35—B1—C29	159.6 (2)	C20—C19—Ir1—N2	143.14 (14)
C40—C35—B1—C41	96.3 (3)	C23—C19—Ir1—N2	−96.88 (15)
C36—C35—B1—C41	−79.3 (3)	C24—C19—Ir1—N2	20.1 (3)
C40—C35—B1—C47	−144.7 (2)	C20—C19—Ir1—C21	−38.29 (15)
C36—C35—B1—C47	39.7 (3)	C23—C19—Ir1—C21	81.69 (16)
C52—C47—B1—C29	90.4 (3)	C24—C19—Ir1—C21	−161.3 (3)
C48—C47—B1—C29	−87.4 (3)	C20—C19—Ir1—C23	−120.0 (2)
C52—C47—B1—C41	−31.3 (3)	C24—C19—Ir1—C23	117.0 (3)
C48—C47—B1—C41	151.0 (2)	C20—C19—Ir1—C22	−81.17 (16)
C52—C47—B1—C35	−151.7 (3)	C23—C19—Ir1—C22	38.81 (15)
C48—C47—B1—C35	30.5 (3)	C24—C19—Ir1—C22	155.8 (3)
C14—C13—N3—N2	3.3 (4)	C23—C19—Ir1—C20	120.0 (2)
C18—C13—N3—N2	−179.1 (2)	C24—C19—Ir1—C20	−123.0 (3)
C5—C6—N2—N3	171.2 (2)	C20—C19—Ir1—Cl1	42.29 (16)
C7—C6—N2—N3	−7.5 (3)	C23—C19—Ir1—Cl1	162.27 (12)
C5—C6—N2—Ir1	11.8 (3)	C24—C19—Ir1—Cl1	−80.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Cl1	0.93	2.64	3.553 (3)	168
C2—H2···Cg1	0.93	2.71	3.463 (3)	139
C11—H11···Cg2i	0.93	2.61	3.365 (3)	139
C18—H18···Cg3ii	0.93	2.60	3.518 (3)	169
C37—H37···Cg4iii	0.93	2.65	3.489 (3)	150
C16—Cl2···Cg5iv	1.75 (1)	3.58 (1)	4.359 (3)	105 (1)

Table 1

Hydrogen-bond geometry (, )

Cg1, Cg2, Cg3, Cg4 and Cg5 are the centroids of the C29C34, C41C46, C35C40, C7C12 and C19C23 rings, respectively.

DHA	DH	HA	D A	DHA
C14H14Cl1	0.93	2.64	3.553(3)	168
C2H2Cg1	0.93	2.71	3.463(3)	139
C11H11Cg2i	0.93	2.61	3.365(3)	139
C18H18Cg3ii	0.93	2.60	3.518(3)	169
C37H37Cg4iii	0.93	2.65	3.489(3)	150
C16Cl2Cg5iv	1.75(1)	3.58(1)	4.359(3)	105(1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .