[2-Butyl-4-(4-tert-butyl­benz­yl)-1,2,4-triazol-3-yl­idene]chlorido[(1,2,5,6-η)-cyclo­octa-1,5-diene]iridium(I)

Nichol, G.S.; Walton, D.P.; Anna, L.J.; Rajaseelan, E.

doi:10.1107/S1600536812000992

[2-Butyl-4-(4-tert-butylbenzyl)-1,2,4-triazol-3-ylidene]chlorido[(1,2,5,6-η)-cycloocta-1,5-diene]iridium(I)

G. S. Nichol, D. P. Walton, L. J. Anna and E. Rajaseelan

In the title compound, [IrCl(C₈H₁₂)(C₁₇H₂₅N₃)], the Ir^I ion has a distorted square-planar coordination geometry. The N-heterocyclic carbene ligand has an extended S-shaped conformation. The butyl group was refined using a two-part 1:1 disorder model. In the crystal, three unique weak C—H

Cl contacts are present. Two of these form a motif described as R₂¹(6) in graph-set notation, while a third forms an R₂²(8) motif about a crystallographic inversion center. The result is a chain structure which extends parallel to the crystallographic a axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812000992/fj2494sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812000992/fj2494Isup2.hkl Contains datablock I
	Chemdraw file https://doi.org/10.1107/S1600536812000992/fj2494Isup3.cdx Supplementary material

CCDC reference: 867975

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.025
wR factor = 0.059
Data-to-parameter ratio = 22.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C18    -   C19    ...       1.39 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  CL1     ..       2.84 Ang.
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained Atom Sites ....          8
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Deg.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ir1    --  Cl1     ..        5.0 su
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................         13 Perc.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          9
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        106

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The title compound, (I), was prepared as part of our ongoing research into complexes of rhodium and iridium with N-heterocyclic carbene (NHC) ligands derived from 1,2,3-triazole (Nichol et al., 2009, 2010, 2011). The Ir center has an expected square planar conformation (Figure 1). The butyl group of the NHC ligand was refined using a two part disorder model, and both disorder components adopt an extended conformation. Three weak C–H···Cl contacts are present (Figure 2, Table 1). Two of these, involving H2 and H7A, combine to form a motif described in graph-set notion as R¹₂(6), while the third involves H18 and a symmetry related molecule to form an R²₂(8) motif, about an inversion center. The combination of these two motifs is a chain structure, connected by weak C–H···Cl contacts, which extends parallel to the crystallographic a axis.

Related literature top

For steric and electronic effects in related N-heterocyclic carbene (NHC) ligands, see: Gusev (2009). For the synthesis, structures and dynamics of related NHC rhodium and iridium complexes, see: Köcher & Herrmann (1997); Wang & Lin (1998); Chianese et al. (2004); Herrmann et al. (2006); Nichol et al. (2009, 2010, 2011); Lu et al. (2011); Huttenstine et al. (2011). For the catalytic activity of related complexes, see: Hillier et al. (2001); Albrecht et al. (2002); Gnanamgari et al. (2007).

Experimental top

Unless otherwise stated, all chemicals were purchased from Sigma Aldrich and Strem and used without further purification, in the dark, and under a nitrogen atmosphere. 1-Butyl-1,2,4-triazole (2.0 g, 16 mmol) and 4-tert-butylbenzyl bromide (4.10 g, 18.0 mmol) were refluxed in toluene (15 ml) for 3 d. After cooling, ether (50 ml) was added and the white solid that formed was filtered, washed with ether and air dried (79%). Transmetalation in CH₂Cl1₂ (10 ml) with 1-butyl-4-(4-tert-butylbenzyl)-1,2,4-triazolium bromide (0.166 g, 0.471 mmol), Ag₂O (0.0565 g, 0.244 mmol), and [Ir(cod)Cl1]₂ (0.1585 g, 0.236 mmol), gave a bright yellow solid (95%). X-ray quality crystals were grown from CH₂Cl1₂/Pentanes by slow diffusion.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., (2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The structure of (I) with displacement ellipsoids at the 50% probability level. The minor disorder component is omitted.
	Fig. 2. C–H···Cl contacts in (I), shown by blue dotted lines.

[2-Butyl-4-(4-tert-butylbenzyl)-1,2,4-triazol-3- ylidene]chlorido[(1,2,5,6-η)-cycloocta-1,5-diene]iridium(I) top

Crystal data top

[IrCl(C₈H₁₂)(C₁₇H₂₅N₃)]	Z = 2
M_r = 607.23	F(000) = 604
Triclinic, P1	D_x = 1.686 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2485 (3) Å	Cell parameters from 9406 reflections
b = 11.2843 (3) Å	θ = 2.5–30.5°
c = 11.9237 (4) Å	µ = 5.71 mm⁻¹
α = 65.213 (2)°	T = 100 K
β = 75.170 (2)°	Blade, yellow
γ = 76.052 (2)°	0.30 × 0.10 × 0.06 mm
V = 1196.07 (6) Å³

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	6993 independent reflections
Radiation source: fine-focus sealed tube with Miracol optics	6168 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
thin–slice ω scans	θ_max = 30.0°, θ_min = 1.9°
Absorption correction: numerical (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.277, T_max = 0.744	k = −15→15
23768 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.059	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0323P)²] where P = (F_o² + 2F_c²)/3
6993 reflections	(Δ/σ)_max = 0.002
313 parameters	Δρ_max = 1.33 e Å⁻³
106 restraints	Δρ_min = −1.83 e Å⁻³

Crystal data top

[IrCl(C₈H₁₂)(C₁₇H₂₅N₃)]	γ = 76.052 (2)°
M_r = 607.23	V = 1196.07 (6) Å³
Triclinic, P1	Z = 2
a = 10.2485 (3) Å	Mo Kα radiation
b = 11.2843 (3) Å	µ = 5.71 mm⁻¹
c = 11.9237 (4) Å	T = 100 K
α = 65.213 (2)°	0.30 × 0.10 × 0.06 mm
β = 75.170 (2)°

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	6993 independent reflections
Absorption correction: numerical (SADABS; Sheldrick, 1996)	6168 reflections with I > 2σ(I)
T_min = 0.277, T_max = 0.744	R_int = 0.039
23768 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	106 restraints
wR(F²) = 0.059	H-atom parameters constrained
S = 1.03	Δρ_max = 1.33 e Å⁻³
6993 reflections	Δρ_min = −1.83 e Å⁻³
313 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ir1	0.761759 (10)	0.744995 (10)	0.533869 (10)	0.01659 (4)
Cl1	0.69986 (7)	0.94124 (7)	0.57356 (8)	0.02660 (16)
N1	1.0046 (2)	0.6417 (2)	0.6693 (2)	0.0195 (5)
N2	1.1331 (3)	0.6607 (3)	0.6683 (3)	0.0229 (5)
N3	1.0507 (2)	0.8038 (2)	0.4997 (2)	0.0175 (5)
C1	0.9505 (3)	0.7272 (3)	0.5684 (3)	0.0173 (5)
C2	1.1573 (3)	0.7598 (3)	0.5638 (3)	0.0217 (6)
H2	1.2391	0.7974	0.5349	0.026*
C3	0.939 (3)	0.547 (2)	0.792 (3)	0.022 (3)	0.496 (11)
H3A	1.0092	0.4931	0.8441	0.026*	0.496 (11)
H3B	0.8961	0.4873	0.7761	0.026*	0.496 (11)
C4	0.8313 (8)	0.6212 (7)	0.8622 (6)	0.0241 (17)	0.496 (11)
H4A	0.7892	0.5561	0.9414	0.029*	0.496 (11)
H4B	0.7589	0.6708	0.8112	0.029*	0.496 (11)
C5	0.8829 (10)	0.7172 (8)	0.8936 (8)	0.0272 (16)	0.496 (11)
H5A	0.9222	0.7847	0.8148	0.033*	0.496 (11)
H5B	0.9565	0.6687	0.9435	0.033*	0.496 (11)
C6	0.770 (2)	0.7856 (18)	0.9672 (19)	0.035 (4)	0.496 (11)
H6A	0.6938	0.8280	0.9212	0.053*	0.496 (11)
H6B	0.8056	0.8526	0.9781	0.053*	0.496 (11)
H6C	0.7383	0.7203	1.0496	0.053*	0.496 (11)
C3'	0.933 (3)	0.551 (3)	0.776 (3)	0.023 (4)	0.504 (11)
H3'1	0.9867	0.4612	0.7964	0.028*	0.504 (11)
H3'2	0.8447	0.5481	0.7580	0.028*	0.504 (11)
C4'	0.9051 (8)	0.5896 (7)	0.8904 (6)	0.0251 (17)	0.504 (11)
H4'1	0.8552	0.5239	0.9632	0.030*	0.504 (11)
H4'2	0.9936	0.5863	0.9115	0.030*	0.504 (11)
C5'	0.8240 (11)	0.7245 (8)	0.8698 (8)	0.0318 (18)	0.504 (11)
H5'1	0.7400	0.7317	0.8395	0.038*	0.504 (11)
H5'2	0.8784	0.7915	0.8040	0.038*	0.504 (11)
C6'	0.785 (2)	0.7534 (17)	0.9910 (18)	0.031 (3)	0.504 (11)
H6'1	0.7287	0.6887	1.0557	0.047*	0.504 (11)
H6'2	0.7324	0.8424	0.9734	0.047*	0.504 (11)
H6'3	0.8675	0.7476	1.0207	0.047*	0.504 (11)
C7	1.0412 (3)	0.9194 (3)	0.3815 (3)	0.0192 (5)
H7A	1.0807	0.9903	0.3833	0.023*
H7B	0.9437	0.9527	0.3748	0.023*
C8	1.1136 (3)	0.8893 (3)	0.2679 (3)	0.0187 (5)
C9	1.0406 (3)	0.8707 (3)	0.1949 (3)	0.0249 (6)
H9	0.9440	0.8773	0.2172	0.030*
C10	1.1065 (3)	0.8425 (3)	0.0896 (3)	0.0251 (6)
H10	1.0541	0.8295	0.0417	0.030*
C11	1.2472 (3)	0.8329 (3)	0.0530 (3)	0.0209 (6)
C12	1.3200 (3)	0.8524 (3)	0.1274 (3)	0.0224 (6)
H12	1.4167	0.8457	0.1055	0.027*
C13	1.2544 (3)	0.8812 (3)	0.2317 (3)	0.0219 (6)
H13	1.3063	0.8956	0.2792	0.026*
C14	1.3230 (4)	0.8040 (3)	−0.0626 (3)	0.0255 (6)
C15	1.4246 (4)	0.6764 (4)	−0.0236 (3)	0.0339 (8)
H15A	1.4865	0.6841	0.0226	0.051*
H15B	1.4776	0.6610	−0.0986	0.051*
H15C	1.3749	0.6022	0.0302	0.051*
C16	1.2278 (4)	0.7869 (4)	−0.1330 (4)	0.0402 (9)
H16A	1.1774	0.7139	−0.0769	0.060*
H16B	1.2819	0.7675	−0.2056	0.060*
H16C	1.1633	0.8685	−0.1616	0.060*
C17	1.3998 (5)	0.9196 (4)	−0.1525 (3)	0.0412 (10)
H17A	1.3346	1.0016	−0.1753	0.062*
H17B	1.4473	0.9032	−0.2284	0.062*
H17C	1.4666	0.9277	−0.1111	0.062*
C18	0.5782 (3)	0.7866 (3)	0.4531 (3)	0.0234 (6)
H18	0.5357	0.8816	0.4244	0.028*
C19	0.5492 (3)	0.7181 (3)	0.5821 (3)	0.0221 (6)
H19	0.4886	0.7727	0.6287	0.027*
C20	0.5410 (3)	0.5724 (3)	0.6472 (3)	0.0262 (6)
H20A	0.4537	0.5563	0.6389	0.031*
H20B	0.5410	0.5447	0.7377	0.031*
C21	0.6599 (3)	0.4876 (3)	0.5934 (3)	0.0255 (6)
H21A	0.6756	0.3981	0.6588	0.031*
H21B	0.6355	0.4788	0.5224	0.031*
C22	0.7903 (3)	0.5482 (3)	0.5485 (3)	0.0207 (6)
H22	0.8681	0.4900	0.5911	0.025*
C23	0.8308 (3)	0.6334 (3)	0.4216 (3)	0.0201 (6)
H23	0.9319	0.6235	0.3919	0.024*
C24	0.7486 (3)	0.6750 (3)	0.3190 (3)	0.0232 (6)
H24A	0.7545	0.5989	0.2960	0.028*
H24B	0.7887	0.7457	0.2437	0.028*
C25	0.5969 (3)	0.7254 (3)	0.3581 (3)	0.0242 (6)
H25A	0.5602	0.7918	0.2829	0.029*
H25B	0.5443	0.6508	0.3943	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.01197 (5)	0.01520 (5)	0.02372 (6)	−0.00339 (3)	0.00016 (4)	−0.00966 (4)
Cl1	0.0150 (3)	0.0200 (3)	0.0505 (5)	−0.0050 (2)	0.0037 (3)	−0.0230 (3)
N1	0.0157 (11)	0.0181 (11)	0.0243 (13)	−0.0058 (9)	0.0000 (9)	−0.0078 (10)
N2	0.0194 (12)	0.0250 (13)	0.0261 (13)	−0.0042 (10)	−0.0061 (10)	−0.0098 (11)
N3	0.0147 (11)	0.0171 (11)	0.0194 (12)	−0.0035 (9)	0.0006 (9)	−0.0072 (9)
C1	0.0164 (13)	0.0159 (12)	0.0191 (13)	−0.0011 (10)	−0.0006 (10)	−0.0085 (10)
C2	0.0171 (13)	0.0241 (14)	0.0262 (15)	−0.0048 (11)	−0.0042 (11)	−0.0107 (12)
C3	0.028 (6)	0.017 (5)	0.015 (7)	−0.014 (4)	−0.003 (4)	0.004 (4)
C4	0.024 (4)	0.022 (3)	0.022 (3)	−0.006 (3)	−0.004 (3)	−0.002 (2)
C5	0.026 (4)	0.024 (3)	0.029 (4)	−0.008 (3)	−0.004 (3)	−0.006 (3)
C6	0.045 (8)	0.030 (8)	0.019 (7)	−0.014 (6)	0.007 (5)	−0.002 (5)
C3'	0.031 (6)	0.020 (6)	0.017 (7)	−0.003 (4)	−0.006 (4)	−0.005 (5)
C4'	0.027 (4)	0.027 (3)	0.017 (3)	−0.007 (3)	−0.005 (3)	−0.001 (2)
C5'	0.039 (5)	0.028 (3)	0.024 (4)	−0.003 (3)	−0.002 (3)	−0.008 (3)
C6'	0.044 (6)	0.030 (8)	0.018 (7)	−0.006 (6)	−0.007 (5)	−0.008 (6)
C7	0.0166 (13)	0.0160 (12)	0.0207 (14)	−0.0037 (10)	0.0011 (10)	−0.0048 (10)
C8	0.0163 (13)	0.0170 (13)	0.0205 (13)	−0.0040 (10)	−0.0007 (10)	−0.0058 (11)
C9	0.0160 (13)	0.0308 (16)	0.0264 (15)	−0.0095 (12)	−0.0019 (11)	−0.0074 (13)
C10	0.0227 (15)	0.0305 (16)	0.0272 (16)	−0.0087 (12)	−0.0042 (12)	−0.0136 (13)
C11	0.0248 (15)	0.0174 (13)	0.0189 (13)	−0.0062 (11)	−0.0021 (11)	−0.0049 (11)
C12	0.0151 (13)	0.0266 (15)	0.0242 (15)	−0.0039 (11)	−0.0002 (11)	−0.0100 (12)
C13	0.0177 (13)	0.0264 (15)	0.0230 (14)	−0.0061 (11)	−0.0012 (11)	−0.0106 (12)
C14	0.0337 (17)	0.0228 (14)	0.0200 (14)	−0.0059 (13)	−0.0013 (12)	−0.0093 (12)
C15	0.039 (2)	0.0299 (17)	0.0320 (18)	−0.0018 (15)	−0.0023 (15)	−0.0154 (15)
C16	0.049 (2)	0.046 (2)	0.036 (2)	0.0002 (18)	−0.0140 (18)	−0.0261 (18)
C17	0.063 (3)	0.0307 (18)	0.0233 (17)	−0.0152 (18)	0.0110 (17)	−0.0101 (14)
C18	0.0156 (13)	0.0170 (13)	0.0337 (17)	−0.0020 (10)	−0.0051 (12)	−0.0058 (12)
C19	0.0112 (12)	0.0230 (14)	0.0330 (16)	−0.0047 (10)	0.0016 (11)	−0.0135 (12)
C20	0.0234 (15)	0.0273 (16)	0.0294 (16)	−0.0127 (12)	0.0016 (12)	−0.0112 (13)
C21	0.0300 (16)	0.0169 (13)	0.0290 (16)	−0.0079 (12)	−0.0072 (13)	−0.0047 (12)
C22	0.0202 (14)	0.0150 (12)	0.0293 (15)	0.0014 (10)	−0.0062 (11)	−0.0119 (11)
C23	0.0150 (13)	0.0207 (13)	0.0280 (15)	−0.0010 (10)	−0.0036 (11)	−0.0134 (12)
C24	0.0228 (15)	0.0251 (15)	0.0271 (15)	−0.0068 (12)	−0.0046 (12)	−0.0133 (12)
C25	0.0176 (14)	0.0244 (15)	0.0326 (17)	−0.0060 (11)	−0.0075 (12)	−0.0096 (13)

Geometric parameters (Å, º) top

Ir1—Cl1	2.3618 (7)	C8—C13	1.389 (4)
Ir1—C18	2.193 (3)	C9—H9	0.950
Ir1—C19	2.168 (3)	C9—C10	1.389 (5)
Ir1—C22	2.106 (3)	C10—H10	0.950
Ir1—C23	2.092 (3)	C10—C11	1.387 (4)
N1—N2	1.381 (3)	C11—C12	1.405 (4)
N1—C1	1.340 (4)	C11—C14	1.522 (4)
N1—C3	1.51 (3)	C12—H12	0.950
N1—C3'	1.42 (3)	C12—C13	1.382 (4)
N2—C2	1.293 (4)	C13—H13	0.950
N3—C1	1.369 (3)	C14—C15	1.529 (5)
N3—C2	1.367 (4)	C14—C16	1.529 (5)
N3—C7	1.471 (4)	C14—C17	1.536 (5)
C2—H2	0.950	C15—H15A	0.980
C3—H3A	0.990	C15—H15B	0.980
C3—H3B	0.990	C15—H15C	0.980
C3—C4	1.51 (3)	C16—H16A	0.980
C4—H4A	0.990	C16—H16B	0.980
C4—H4B	0.990	C16—H16C	0.980
C4—C5	1.519 (11)	C17—H17A	0.980
C5—H5A	0.990	C17—H17B	0.980
C5—H5B	0.990	C17—H17C	0.980
C5—C6	1.52 (3)	C18—H18	1.000
C6—H6A	0.980	C18—C19	1.390 (5)
C6—H6B	0.980	C18—C25	1.509 (5)
C6—H6C	0.980	C19—H19	1.000
C3'—H3'1	0.990	C19—C20	1.509 (4)
C3'—H3'2	0.990	C20—H20A	0.990
C3'—C4'	1.54 (3)	C20—H20B	0.990
C4'—H4'1	0.990	C20—C21	1.537 (5)
C4'—H4'2	0.990	C21—H21A	0.990
C4'—C5'	1.499 (12)	C21—H21B	0.990
C5'—H5'1	0.990	C21—C22	1.519 (4)
C5'—H5'2	0.990	C22—H22	1.000
C5'—C6'	1.55 (2)	C22—C23	1.426 (4)
C6'—H6'1	0.980	C23—H23	1.000
C6'—H6'2	0.980	C23—C24	1.512 (4)
C6'—H6'3	0.980	C24—H24A	0.990
C7—H7A	0.990	C24—H24B	0.990
C7—H7B	0.990	C24—C25	1.544 (4)
C7—C8	1.500 (4)	C25—H25A	0.990
C8—C9	1.387 (4)	C25—H25B	0.990

Cl1—Ir1—C1	88.85 (8)	C9—C10—H10	119.3
Cl1—Ir1—C18	91.89 (8)	C9—C10—C11	121.4 (3)
Cl1—Ir1—C19	90.20 (8)	H10—C10—C11	119.3
Cl1—Ir1—C22	164.65 (9)	C10—C11—C12	117.0 (3)
Cl1—Ir1—C23	155.34 (9)	C10—C11—C14	123.1 (3)
C1—Ir1—C18	167.26 (11)	C12—C11—C14	119.9 (3)
C1—Ir1—C19	155.58 (12)	C11—C12—H12	119.2
C1—Ir1—C22	93.31 (11)	C11—C12—C13	121.5 (3)
C1—Ir1—C23	93.28 (11)	H12—C12—C13	119.2
C18—Ir1—C19	37.16 (12)	C8—C13—C12	120.8 (3)
C18—Ir1—C22	89.33 (11)	C8—C13—H13	119.6
C18—Ir1—C23	80.82 (12)	C12—C13—H13	119.6
C19—Ir1—C22	81.58 (11)	C11—C14—C15	109.6 (3)
C19—Ir1—C23	97.63 (11)	C11—C14—C16	112.9 (3)
C22—Ir1—C23	39.73 (12)	C11—C14—C17	108.7 (3)
N2—N1—C1	113.8 (2)	C15—C14—C16	107.7 (3)
N2—N1—C3	114.9 (12)	C15—C14—C17	109.8 (3)
N2—N1—C3'	121.3 (13)	C16—C14—C17	108.3 (3)
C1—N1—C3	130.1 (12)	C14—C15—H15A	109.5
C1—N1—C3'	124.4 (13)	C14—C15—H15B	109.5
N1—N2—C2	103.3 (2)	C14—C15—H15C	109.5
C1—N3—C2	108.4 (2)	H15A—C15—H15B	109.5
C1—N3—C7	125.7 (2)	H15A—C15—H15C	109.5
C2—N3—C7	125.9 (2)	H15B—C15—H15C	109.5
Ir1—C1—N1	128.0 (2)	C14—C16—H16A	109.5
Ir1—C1—N3	129.1 (2)	C14—C16—H16B	109.5
N1—C1—N3	102.8 (2)	C14—C16—H16C	109.5
N2—C2—N3	111.7 (3)	H16A—C16—H16B	109.5
N2—C2—H2	124.1	H16A—C16—H16C	109.5
N3—C2—H2	124.1	H16B—C16—H16C	109.5
N1—C3—H3A	109.5	C14—C17—H17A	109.5
N1—C3—H3B	109.5	C14—C17—H17B	109.5
N1—C3—C4	110.9 (16)	C14—C17—H17C	109.5
H3A—C3—H3B	108.1	H17A—C17—H17B	109.5
H3A—C3—C4	109.5	H17A—C17—H17C	109.5
H3B—C3—C4	109.5	H17B—C17—H17C	109.5
C3—C4—H4A	108.5	Ir1—C18—H18	114.0
C3—C4—H4B	108.5	Ir1—C18—C19	70.47 (17)
C3—C4—C5	115.1 (12)	Ir1—C18—C25	113.0 (2)
H4A—C4—H4B	107.5	H18—C18—C19	114.0
H4A—C4—C5	108.5	H18—C18—C25	114.0
H4B—C4—C5	108.5	C19—C18—C25	123.8 (3)
C4—C5—H5A	109.1	Ir1—C19—C18	72.37 (17)
C4—C5—H5B	109.1	Ir1—C19—H19	114.0
C4—C5—C6	112.3 (11)	Ir1—C19—C20	108.9 (2)
H5A—C5—H5B	107.9	C18—C19—H19	114.0
H5A—C5—C6	109.1	C18—C19—C20	125.5 (3)
H5B—C5—C6	109.1	H19—C19—C20	114.0
N1—C3'—H3'1	109.4	C19—C20—H20A	109.0
N1—C3'—H3'2	109.4	C19—C20—H20B	109.0
N1—C3'—C4'	111.1 (17)	C19—C20—C21	112.7 (2)
H3'1—C3'—H3'2	108.0	H20A—C20—H20B	107.8
H3'1—C3'—C4'	109.4	H20A—C20—C21	109.0
H3'2—C3'—C4'	109.4	H20B—C20—C21	109.0
C3'—C4'—H4'1	108.8	C20—C21—H21A	109.3
C3'—C4'—H4'2	108.8	C20—C21—H21B	109.3
C3'—C4'—C5'	113.8 (12)	C20—C21—C22	111.5 (2)
H4'1—C4'—H4'2	107.7	H21A—C21—H21B	108.0
H4'1—C4'—C5'	108.8	H21A—C21—C22	109.3
H4'2—C4'—C5'	108.8	H21B—C21—C22	109.3
C4'—C5'—H5'1	109.2	Ir1—C22—C21	114.4 (2)
C4'—C5'—H5'2	109.2	Ir1—C22—H22	114.1
C4'—C5'—C6'	112.1 (10)	Ir1—C22—C23	69.62 (16)
H5'1—C5'—H5'2	107.9	C21—C22—H22	114.1
H5'1—C5'—C6'	109.2	C21—C22—C23	122.9 (3)
H5'2—C5'—C6'	109.2	H22—C22—C23	114.1
C5'—C6'—H6'1	109.5	Ir1—C23—C22	70.66 (16)
C5'—C6'—H6'2	109.5	Ir1—C23—H23	113.9
C5'—C6'—H6'3	109.5	Ir1—C23—C24	113.0 (2)
H6'1—C6'—H6'2	109.5	C22—C23—H23	113.9
H6'1—C6'—H6'3	109.5	C22—C23—C24	124.1 (3)
H6'2—C6'—H6'3	109.5	H23—C23—C24	113.9
N3—C7—H7A	109.0	C23—C24—H24A	109.1
N3—C7—H7B	109.0	C23—C24—H24B	109.1
N3—C7—C8	113.0 (2)	C23—C24—C25	112.7 (3)
H7A—C7—H7B	107.8	H24A—C24—H24B	107.8
H7A—C7—C8	109.0	H24A—C24—C25	109.1
H7B—C7—C8	109.0	H24B—C24—C25	109.1
C7—C8—C9	120.5 (3)	C18—C25—C24	111.8 (2)
C7—C8—C13	121.4 (3)	C18—C25—H25A	109.2
C9—C8—C13	118.1 (3)	C18—C25—H25B	109.2
C8—C9—H9	119.5	C24—C25—H25A	109.2
C8—C9—C10	121.1 (3)	C24—C25—H25B	109.2
H9—C9—C10	119.5	H25A—C25—H25B	107.9

C1—N1—N2—C2	−0.3 (3)	C12—C11—C14—C17	−59.3 (4)
C3—N1—N2—C2	−169.4 (11)	Cl1—Ir1—C18—C19	−87.83 (17)
C3'—N1—N2—C2	−172.6 (12)	Cl1—Ir1—C18—C25	152.7 (2)
N2—N1—C1—Ir1	−175.89 (19)	C1—Ir1—C18—C19	179.0 (4)
N2—N1—C1—N3	0.3 (3)	C1—Ir1—C18—C25	59.6 (6)
C3—N1—C1—Ir1	−8.8 (13)	C19—Ir1—C18—C25	−119.4 (3)
C3—N1—C1—N3	167.3 (13)	C22—Ir1—C18—C19	76.87 (19)
C3'—N1—C1—Ir1	−3.9 (13)	C22—Ir1—C18—C25	−42.6 (2)
C3'—N1—C1—N3	172.3 (12)	C23—Ir1—C18—C19	115.85 (19)
C2—N3—C1—Ir1	175.9 (2)	C23—Ir1—C18—C25	−3.6 (2)
C2—N3—C1—N1	−0.2 (3)	Ir1—C18—C19—C20	−100.9 (3)
C7—N3—C1—Ir1	−0.2 (4)	C25—C18—C19—Ir1	105.2 (3)
C7—N3—C1—N1	−176.3 (2)	C25—C18—C19—C20	4.3 (5)
Cl1—Ir1—C1—N1	106.7 (2)	Cl1—Ir1—C19—C18	92.87 (17)
Cl1—Ir1—C1—N3	−68.5 (2)	Cl1—Ir1—C19—C20	−144.7 (2)
C18—Ir1—C1—N1	−159.8 (4)	C1—Ir1—C19—C18	−179.5 (2)
C18—Ir1—C1—N3	25.0 (6)	C1—Ir1—C19—C20	−57.0 (4)
C19—Ir1—C1—N1	18.7 (4)	C18—Ir1—C19—C20	122.4 (3)
C19—Ir1—C1—N3	−156.5 (2)	C22—Ir1—C19—C18	−100.14 (19)
C22—Ir1—C1—N1	−58.1 (3)	C22—Ir1—C19—C20	22.3 (2)
C22—Ir1—C1—N3	126.7 (3)	C23—Ir1—C19—C18	−63.68 (19)
C23—Ir1—C1—N1	−97.9 (3)	C23—Ir1—C19—C20	58.7 (2)
C23—Ir1—C1—N3	86.9 (3)	Ir1—C19—C20—C21	−36.1 (3)
N1—N2—C2—N3	0.2 (3)	C18—C19—C20—C21	45.3 (4)
C1—N3—C2—N2	0.0 (3)	C19—C20—C21—C22	32.9 (4)
C7—N3—C2—N2	176.2 (3)	C20—C21—C22—Ir1	−13.2 (3)
N2—N1—C3—C4	103.3 (17)	C20—C21—C22—C23	−93.8 (3)
C1—N1—C3—C4	−64 (2)	Cl1—Ir1—C22—C21	53.2 (4)
N1—C3—C4—C5	−59 (2)	Cl1—Ir1—C22—C23	171.1 (2)
C3—C4—C5—C6	−178.5 (15)	C1—Ir1—C22—C21	151.0 (2)
N2—N1—C3'—C4'	62 (2)	C1—Ir1—C22—C23	−91.16 (18)
C1—N1—C3'—C4'	−109.9 (17)	C18—Ir1—C22—C21	−41.5 (2)
C3—N1—C3'—C4'	37 (16)	C18—Ir1—C22—C23	76.37 (18)
N1—C3'—C4'—C5'	59 (2)	C19—Ir1—C22—C21	−5.0 (2)
C3'—C4'—C5'—C6'	173.5 (16)	C19—Ir1—C22—C23	112.85 (18)
C1—N3—C7—C8	−101.1 (3)	C23—Ir1—C22—C21	−117.9 (3)
C2—N3—C7—C8	83.4 (3)	Ir1—C22—C23—C24	−105.2 (3)
N3—C7—C8—C9	101.8 (3)	C21—C22—C23—Ir1	106.5 (3)
N3—C7—C8—C13	−79.1 (3)	C21—C22—C23—C24	1.3 (4)
C7—C8—C9—C10	−179.9 (3)	Cl1—Ir1—C23—C22	−174.37 (15)
C13—C8—C9—C10	1.1 (5)	Cl1—Ir1—C23—C24	−54.6 (3)
C8—C9—C10—C11	−0.5 (5)	C1—Ir1—C23—C22	91.22 (18)
C9—C10—C11—C12	0.3 (5)	C1—Ir1—C23—C24	−149.0 (2)
C9—C10—C11—C14	−179.2 (3)	C18—Ir1—C23—C22	−100.14 (18)
C10—C11—C12—C13	−0.7 (5)	C18—Ir1—C23—C24	19.7 (2)
C14—C11—C12—C13	178.8 (3)	C19—Ir1—C23—C22	−66.89 (18)
C11—C12—C13—C8	1.3 (5)	C19—Ir1—C23—C24	52.9 (2)
C7—C8—C13—C12	179.5 (3)	C22—Ir1—C23—C24	119.8 (3)
C9—C8—C13—C12	−1.4 (5)	Ir1—C23—C24—C25	−32.7 (3)
C10—C11—C14—C15	−119.9 (3)	C22—C23—C24—C25	48.9 (4)
C10—C11—C14—C16	0.0 (4)	Ir1—C18—C25—C24	−12.7 (3)
C10—C11—C14—C17	120.1 (4)	C19—C18—C25—C24	−94.0 (3)
C12—C11—C14—C15	60.6 (4)	C23—C24—C25—C18	29.2 (4)
C12—C11—C14—C16	−179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1ⁱ	0.95	2.84	3.568 (3)	135
C7—H7A···Cl1ⁱ	0.99	2.77	3.641 (3)	147
C18—H18···Cl1ⁱⁱ	1.00	2.74	3.617 (3)	147

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	[IrCl(C₈H₁₂)(C₁₇H₂₅N₃)]
M_r	607.23
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	10.2485 (3), 11.2843 (3), 11.9237 (4)
α, β, γ (°)	65.213 (2), 75.170 (2), 76.052 (2)
V (Å³)	1196.07 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	5.71
Crystal size (mm)	0.30 × 0.10 × 0.06

Data collection
Diffractometer	Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction	Numerical (SADABS; Sheldrick, 1996)
T_min, T_max	0.277, 0.744
No. of measured, independent and observed [I > 2σ(I)] reflections	23768, 6993, 6168
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.059, 1.03
No. of reflections	6993
No. of parameters	313
No. of restraints	106
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.33, −1.83

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., (2006), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).