Bis[μ-2-(aminosulfanyl)pyridine(1-)]bis-[(η-penta-methyl-cyclo-penta-dien-yl)iridium(III)] diiodide.

In the title dinuclear iridium(III) complex, [Ir(2)(C(10)H(15))(2)(C(5)H(5)N(2)S)(2)]I(2), the iridium(III) atoms are bridged by 2-(aminosulfanyl)pyridine(1-) [(2-py)SNH] ligands in a μ-(2-py)SNH-κ(2)N(py),N(NH):κN(NH) mode. The dinuclear complex cation lies on a crystallographic inversion center, resulting in a planar Ir(2)N(2) ring with an Ir-N(py) bond length of 2.085 (9) Å and bridging Ir-N(NH) bonds of 2.110 (9) and 2.113 (9) Å. The two (2-py)S units have mutually anti configurations with respect to the Ir(2)N(2) ring.

Related literature

For nitro­gen-atom transfer, see: Du Bois et al. (1997 ▶); Birk & Bendix (2003 ▶). For photolysis of iridium(III) azido complexes, see: Kotera et al. (2008 ▶); Sekioka et al. (2005 ▶); Suzuki et al. (2003 ▶). For related organic compounds, see: Robinson & Hurley (1965 ▶); Brito et al. (2002 ▶); Miura et al. (2003 ▶). For related coordination compounds, see: Nakayama et al. (1999 ▶); Esquivias et al. (2007 ▶); Nanthakumar et al. (1999 ▶); Ishiwata et al. (2006 ▶); Arita et al. (2008 ▶). For 2-pyridylmethyl­amido complexes showing the μ-κ2 N(py),N(NH):κN(NH) bridging mode, see: Westerhausen et al. (2002 ▶); Wong & Wong(2002 ▶).

Experimental

Crystal data

[Ir2(C10H15)2(C5H5N2S)2]I2

M = 1158.98

Monoclinic,

a = 12.839 (3) Å

b = 12.169 (3) Å

c = 11.299 (4) Å

β = 102.754 (19)°

V = 1721.8 (8) Å3

Z = 2

Mo Kα radiation

μ = 9.66 mm−1

T = 296 K

0.20 × 0.10 × 0.08 mm

Data collection

Rigaku AFC7R diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.248, T max = 0.512

5294 measured reflections

5006 independent reflections

3621 reflections with I > 2σ(I)

R int = 0.080

3 standard reflections every 150 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.212

S = 1.02

5006 reflections

182 parameters

H-atom parameters constrained

Δρmax = 3.47 e Å−3

Δρmin = −3.49 e Å−3

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999 ▶); cell refinement: WinAFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037167/zs2007sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037167/zs2007Isup2.hkl

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

[Ir2(C10H15)2(C5H5N2S)2]I2	F(000) = 1080
Mr = 1158.98	Dx = 2.235 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 12.839 (3) Å	θ = 15.1–17.0°
b = 12.169 (3) Å	µ = 9.66 mm−1
c = 11.299 (4) Å	T = 296 K
β = 102.754 (19)°	Plate, yellow
V = 1721.8 (8) Å3	0.20 × 0.10 × 0.08 mm
Z = 2

Rigaku AFC7R diffractometer	3621 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.080
graphite	θmax = 30.0°, θmin = 2.7°
ω–2θ scans	h = −17→18
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
Tmin = 0.248, Tmax = 0.512	l = −15→6
5294 measured reflections	3 standard reflections every 150 reflections
5006 independent reflections	intensity decay: none

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1625P)2] where P = (Fo2 + 2Fc2)/3
5006 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 3.47 e Å−3
0 restraints	Δρmin = −3.49 e Å−3

	x	y	z	Uiso*/Ueq
Ir1	0.44162 (3)	0.04859 (3)	0.10915 (3)	0.03051 (16)
I1	0.43226 (8)	−0.33173 (7)	0.19002 (9)	0.0577 (3)
S1	0.6607 (2)	0.1519 (2)	0.0834 (3)	0.0444 (6)
N1	0.5900 (6)	−0.0006 (7)	0.2111 (8)	0.0347 (17)
N2	0.5455 (7)	0.0923 (7)	−0.0044 (8)	0.0360 (17)
C2	0.6748 (8)	0.0563 (8)	0.1992 (11)	0.037 (2)
C3	0.7773 (9)	0.0412 (11)	0.2784 (13)	0.053 (3)
C4	0.7850 (9)	−0.0313 (12)	0.3700 (13)	0.054 (3)
C5	0.7009 (11)	−0.0948 (10)	0.3812 (11)	0.049 (3)
C6	0.6016 (10)	−0.0797 (10)	0.3026 (10)	0.046 (2)
H2	0.5119	0.1449	−0.0563	0.043*
H3	0.8367	0.0801	0.2670	0.064*
H4	0.8493	−0.0379	0.4267	0.064*
H5	0.7093	−0.1484	0.4412	0.059*
H6	0.5435	−0.1222	0.3110	0.055*
C11	0.3852 (11)	0.2107 (12)	0.1475 (14)	0.058 (3)
C12	0.4010 (9)	0.1434 (11)	0.2566 (11)	0.046 (3)
C13	0.3359 (9)	0.0464 (9)	0.2330 (12)	0.044 (3)
C14	0.2687 (12)	0.0600 (12)	0.1115 (14)	0.061 (4)
C15	0.3039 (13)	0.1527 (13)	0.0590 (12)	0.062 (4)
C16	0.4361 (18)	0.3130 (13)	0.133 (2)	0.103 (9)
C17	0.4780 (12)	0.1724 (16)	0.3763 (15)	0.082 (6)
C18	0.3265 (16)	−0.0390 (11)	0.3278 (17)	0.067 (4)
C19	0.1763 (11)	−0.016 (2)	0.059 (2)	0.092 (7)
C20	0.2544 (17)	0.2022 (18)	−0.0683 (16)	0.102 (8)
H16A	0.4104	0.3393	0.0513	0.123*
H16B	0.5119	0.3024	0.1474	0.123*
H16C	0.4199	0.3658	0.1890	0.123*
H17A	0.5124	0.2411	0.3677	0.098*
H17B	0.5309	0.1157	0.3970	0.098*
H17C	0.4390	0.1787	0.4394	0.098*
H18A	0.2779	−0.0956	0.2912	0.080*
H18B	0.3002	−0.0048	0.3920	0.080*
H18C	0.3954	−0.0705	0.3602	0.080*
H19A	0.1715	−0.0727	0.1177	0.111*
H19B	0.1881	−0.0498	−0.0135	0.111*
H19C	0.1110	0.0247	0.0413	0.111*
H20A	0.2943	0.2659	−0.0816	0.122*
H20B	0.1815	0.2226	−0.0718	0.122*
H20C	0.2568	0.1484	−0.1298	0.122*

	U11	U22	U33	U12	U13	U23
Ir1	0.0272 (2)	0.0357 (2)	0.0303 (2)	0.00425 (13)	0.00992 (14)	0.00336 (13)
I1	0.0620 (5)	0.0496 (5)	0.0624 (6)	−0.0088 (4)	0.0159 (4)	0.0109 (4)
S1	0.0439 (14)	0.0407 (13)	0.0502 (15)	−0.0105 (11)	0.0143 (11)	−0.0015 (11)
N1	0.031 (4)	0.033 (4)	0.043 (5)	0.005 (3)	0.015 (3)	−0.003 (3)
N2	0.036 (4)	0.032 (4)	0.040 (4)	0.007 (3)	0.008 (3)	0.006 (3)
C2	0.030 (5)	0.035 (5)	0.049 (6)	−0.001 (3)	0.012 (4)	0.000 (4)
C3	0.025 (5)	0.074 (9)	0.059 (8)	−0.002 (5)	0.007 (5)	−0.023 (6)
C4	0.027 (5)	0.076 (9)	0.051 (7)	0.002 (5)	−0.007 (5)	−0.010 (6)
C5	0.058 (7)	0.044 (6)	0.040 (6)	0.006 (5)	0.000 (5)	0.001 (5)
C6	0.054 (7)	0.046 (6)	0.039 (5)	0.012 (5)	0.014 (5)	0.004 (5)
C11	0.051 (7)	0.059 (8)	0.067 (8)	0.016 (6)	0.024 (6)	0.012 (6)
C12	0.034 (5)	0.056 (6)	0.053 (6)	0.004 (5)	0.020 (5)	−0.012 (5)
C13	0.032 (5)	0.048 (6)	0.052 (7)	0.002 (4)	0.011 (5)	−0.011 (5)
C14	0.047 (7)	0.081 (10)	0.055 (8)	0.009 (6)	0.007 (6)	−0.018 (7)
C15	0.068 (9)	0.081 (10)	0.045 (7)	0.015 (7)	0.028 (6)	−0.008 (7)
C16	0.14 (2)	0.045 (8)	0.16 (2)	0.032 (10)	0.095 (18)	0.038 (10)
C17	0.048 (8)	0.128 (16)	0.066 (9)	−0.007 (8)	0.007 (7)	−0.059 (10)
C18	0.086 (12)	0.045 (7)	0.083 (11)	−0.004 (7)	0.052 (10)	0.012 (7)
C19	0.030 (6)	0.138 (17)	0.112 (16)	−0.018 (9)	0.021 (8)	−0.055 (14)
C20	0.104 (15)	0.132 (17)	0.070 (11)	0.086 (14)	0.022 (10)	0.045 (11)

Ir1—N1	2.085 (9)	C14—C15	1.40 (2)
Ir1—N2	2.113 (9)	C14—C19	1.52 (2)
Ir1—N2i	2.110 (9)	C15—C20	1.56 (2)
Ir1—C11	2.177 (14)	N2—H2	0.9100
Ir1—C12	2.182 (11)	C3—H3	0.9300
Ir1—C13	2.154 (13)	C4—H4	0.9300
Ir1—C14	2.231 (15)	C5—H5	0.9300
Ir1—C15	2.147 (15)	C6—H6	0.9300
S1—C2	1.730 (11)	C16—H16A	0.9600
S1—N2	1.747 (9)	C16—H16B	0.9600
N1—C2	1.322 (13)	C16—H16C	0.9600
N1—C6	1.396 (15)	C17—H17A	0.9600
C2—C3	1.431 (16)	C17—H17B	0.9600
C3—C4	1.35 (2)	C17—H17C	0.9600
C4—C5	1.357 (19)	C18—H18A	0.9600
C5—C6	1.395 (17)	C18—H18B	0.9600
C11—C12	1.457 (19)	C18—H18C	0.9600
C11—C15	1.46 (2)	C19—H19A	0.9600
C11—C16	1.43 (2)	C19—H19B	0.9600
C12—C13	1.437 (16)	C19—H19C	0.9600
C12—C17	1.531 (18)	C20—H20A	0.9600
C13—C14	1.46 (2)	C20—H20B	0.9600
C13—C18	1.515 (18)	C20—H20C	0.9600
N1—Ir1—N2i	84.3 (3)	C12—C13—Ir1	71.7 (7)
N1—Ir1—N2	77.6 (3)	C14—C13—Ir1	73.4 (8)
N2i—Ir1—N2	74.1 (4)	C18—C13—Ir1	128.9 (9)
N1—Ir1—C11	117.0 (5)	C12—C13—C14	106.3 (12)
N2—Ir1—C11	100.1 (4)	C12—C13—C18	124.4 (13)
N2i—Ir1—C11	156.7 (5)	C14—C13—C18	128.2 (13)
N1—Ir1—C12	94.2 (4)	C13—C14—Ir1	67.7 (7)
N2—Ir1—C12	128.3 (4)	C15—C14—Ir1	68.2 (9)
N2i—Ir1—C12	156.8 (4)	C19—C14—Ir1	130.6 (10)
N1—Ir1—C13	105.5 (4)	C13—C14—C15	108.2 (13)
N2—Ir1—C13	166.1 (4)	C13—C14—C19	122.9 (16)
N2i—Ir1—C13	119.5 (4)	C15—C14—C19	129.0 (17)
N1—Ir1—C14	143.3 (5)	C11—C15—Ir1	71.4 (8)
N2—Ir1—C14	139.0 (5)	C14—C15—Ir1	74.7 (9)
N2i—Ir1—C14	105.0 (4)	C20—C15—Ir1	128.0 (9)
N1—Ir1—C15	156.1 (5)	C11—C15—C14	110.5 (13)
N2—Ir1—C15	106.5 (4)	C11—C15—C20	122.0 (17)
N2i—Ir1—C15	119.6 (5)	C14—C15—C20	126.8 (17)
C11—Ir1—C12	39.1 (5)	C2—C3—H3	121.1
C11—Ir1—C13	66.2 (5)	C4—C3—H3	121.1
C11—Ir1—C14	64.3 (5)	C3—C4—H4	119.3
C11—Ir1—C15	39.4 (6)	C5—C4—H4	119.3
C12—Ir1—C13	38.7 (4)	C4—C5—H5	120.0
C12—Ir1—C14	63.4 (5)	C6—C5—H5	120.0
C12—Ir1—C15	64.4 (5)	C5—C6—H6	120.1
C13—Ir1—C14	38.9 (5)	N1—C6—H6	120.1
C13—Ir1—C15	65.1 (5)	C11—C16—H16A	109.5
C14—Ir1—C15	37.1 (6)	C11—C16—H16B	109.5
C2—S1—N2	94.9 (5)	C11—C16—H16C	109.5
C2—N1—C6	118.7 (10)	H16A—C16—H16B	109.5
C2—N1—Ir1	117.8 (7)	H16A—C16—H16C	109.5
C6—N1—Ir1	122.8 (7)	H16B—C16—H16C	109.5
Ir1i—N2—Ir1	105.9 (4)	C12—C17—H17A	109.5
S1—N2—Ir1	109.2 (4)	C12—C17—H17B	109.5
S1—N2—Ir1i	119.6 (4)	C12—C17—H17C	109.5
S1—N2—H2	107.2	H17A—C17—H17B	109.5
Ir1i—N2—H2	107.2	H17A—C17—H17C	109.5
Ir1—N2—H2	107.2	H17B—C17—H17C	109.5
N1—C2—S1	118.6 (8)	C13—C18—H18A	109.5
C3—C2—S1	119.2 (9)	C13—C18—H18B	109.5
N1—C2—C3	122.2 (11)	C13—C18—H18C	109.5
C2—C3—C4	117.8 (11)	H18A—C18—H18B	109.5
C3—C4—C5	121.4 (11)	H18A—C18—H18C	109.5
C4—C5—C6	119.9 (12)	H18B—C18—H18C	109.5
C5—C6—N1	119.7 (12)	C14—C19—H19A	109.5
C12—C11—Ir1	70.7 (7)	C14—C19—H19B	109.5
C15—C11—Ir1	69.2 (8)	C14—C19—H19C	109.5
C16—C11—Ir1	125.7 (11)	H19A—C19—H19B	109.5
C12—C11—C15	104.6 (13)	H19A—C19—H19C	109.5
C12—C11—C16	127.3 (16)	H19B—C19—H19C	109.5
C15—C11—C16	128.0 (17)	C15—C20—H20A	109.5
C11—C12—Ir1	70.3 (7)	C15—C20—H20B	109.5
C13—C12—Ir1	69.6 (7)	C15—C20—H20C	109.5
C17—C12—Ir1	125.5 (8)	H20A—C20—H20B	109.5
C11—C12—C13	109.8 (12)	H20A—C20—H20C	109.5
C11—C12—C17	124.1 (14)	H20B—C20—H20C	109.5
C13—C12—C17	126.2 (14)
N2i—Ir1—N1—C2	106.2 (8)	C11—C12—C13—C14	−6.9 (13)
N2—Ir1—N1—C2	31.3 (8)	C17—C12—C13—C14	174.6 (12)
C15—Ir1—N1—C2	−71.6 (14)	Ir1—C12—C13—C14	−65.8 (8)
C13—Ir1—N1—C2	−134.7 (8)	C11—C12—C13—C18	−176.0 (12)
C11—Ir1—N1—C2	−63.8 (9)	C17—C12—C13—C18	5.4 (19)
C12—Ir1—N1—C2	−97.1 (8)	Ir1—C12—C13—C18	125.1 (12)
C14—Ir1—N1—C2	−146.2 (9)	C11—C12—C13—Ir1	58.9 (8)
N2i—Ir1—N1—C6	−83.1 (9)	C17—C12—C13—Ir1	−119.7 (12)
N2—Ir1—N1—C6	−158.0 (9)	N1—Ir1—C13—C12	77.0 (7)
C15—Ir1—N1—C6	99.1 (14)	N2i—Ir1—C13—C12	169.3 (6)
C13—Ir1—N1—C6	36.0 (9)	N2—Ir1—C13—C12	−24 (2)
C11—Ir1—N1—C6	106.9 (9)	C15—Ir1—C13—C12	−79.5 (8)
C12—Ir1—N1—C6	73.6 (9)	C11—Ir1—C13—C12	−36.1 (8)
C14—Ir1—N1—C6	24.5 (12)	C14—Ir1—C13—C12	−114.0 (11)
C2—S1—N2—Ir1i	−78.5 (6)	N1—Ir1—C13—C14	−169.0 (7)
C2—S1—N2—Ir1	43.6 (5)	N2i—Ir1—C13—C14	−76.8 (8)
N1—Ir1—N2—S1	−42.5 (4)	N2—Ir1—C13—C14	89.8 (17)
N2i—Ir1—N2—S1	−130.0 (6)	C15—Ir1—C13—C14	34.5 (8)
C15—Ir1—N2—S1	113.2 (6)	C11—Ir1—C13—C14	77.9 (9)
C13—Ir1—N2—S1	62.1 (17)	C12—Ir1—C13—C14	114.0 (11)
C11—Ir1—N2—S1	73.2 (6)	N1—Ir1—C13—C18	−42.9 (14)
C12—Ir1—N2—S1	43.1 (7)	N2i—Ir1—C13—C18	49.4 (15)
C14—Ir1—N2—S1	135.3 (6)	N2—Ir1—C13—C18	−144.1 (15)
N1—Ir1—N2—Ir1i	87.6 (4)	C15—Ir1—C13—C18	160.6 (15)
N2i—Ir1—N2—Ir1i	0.0	C11—Ir1—C13—C18	−156.0 (15)
C15—Ir1—N2—Ir1i	−116.8 (5)	C12—Ir1—C13—C18	−119.9 (16)
C13—Ir1—N2—Ir1i	−167.8 (15)	C14—Ir1—C13—C18	126.1 (16)
C11—Ir1—N2—Ir1i	−156.8 (5)	C12—C13—C14—C15	8.5 (14)
C12—Ir1—N2—Ir1i	173.1 (4)	C18—C13—C14—C15	177.1 (13)
C14—Ir1—N2—Ir1i	−94.7 (7)	Ir1—C13—C14—C15	−56.1 (10)
C6—N1—C2—C3	−1.4 (16)	C12—C13—C14—C19	−170.4 (13)
Ir1—N1—C2—C3	169.7 (8)	C18—C13—C14—C19	−2(2)
C6—N1—C2—S1	178.4 (8)	Ir1—C13—C14—C19	125.0 (13)
Ir1—N1—C2—S1	−10.5 (11)	C12—C13—C14—Ir1	64.7 (8)
N2—S1—C2—N1	−21.7 (9)	C18—C13—C14—Ir1	−126.8 (13)
N2—S1—C2—C3	158.2 (9)	N1—Ir1—C14—C15	139.6 (8)
N1—C2—C3—C4	−2.2 (18)	N2i—Ir1—C14—C15	−119.5 (8)
S1—C2—C3—C4	177.9 (9)	N2—Ir1—C14—C15	−36.7 (11)
C2—C3—C4—C5	5(2)	C13—Ir1—C14—C15	121.8 (11)
C3—C4—C5—C6	−5(2)	C11—Ir1—C14—C15	38.3 (8)
C4—C5—C6—N1	1.3 (19)	C12—Ir1—C14—C15	82.1 (9)
C2—N1—C6—C5	1.9 (16)	N1—Ir1—C14—C13	17.9 (11)
Ir1—N1—C6—C5	−168.7 (8)	N2i—Ir1—C14—C13	118.7 (7)
N1—Ir1—C11—C16	62.4 (18)	N2—Ir1—C14—C13	−158.4 (6)
N2i—Ir1—C11—C16	−92 (2)	C15—Ir1—C14—C13	−121.8 (11)
N2—Ir1—C11—C16	−18.7 (18)	C11—Ir1—C14—C13	−83.4 (8)
C15—Ir1—C11—C16	−123 (2)	C12—Ir1—C14—C13	−39.7 (7)
C13—Ir1—C11—C16	158.4 (18)	N1—Ir1—C14—C19	−97.1 (19)
C12—Ir1—C11—C16	123 (2)	N2i—Ir1—C14—C19	3.8 (19)
C14—Ir1—C11—C16	−158.7 (19)	N2—Ir1—C14—C19	86.6 (19)
N1—Ir1—C11—C12	−60.2 (8)	C15—Ir1—C14—C19	123 (2)
N2i—Ir1—C11—C12	145.6 (9)	C13—Ir1—C14—C19	−115 (2)
N2—Ir1—C11—C12	−141.3 (7)	C11—Ir1—C14—C19	162 (2)
C15—Ir1—C11—C12	114.8 (11)	C12—Ir1—C14—C19	−155 (2)
C13—Ir1—C11—C12	35.8 (7)	C13—C14—C15—C11	−7.1 (15)
C14—Ir1—C11—C12	78.7 (8)	C19—C14—C15—C11	171.7 (14)
N1—Ir1—C11—C15	−175.0 (7)	Ir1—C14—C15—C11	−63.0 (10)
N2i—Ir1—C11—C15	30.7 (15)	C13—C14—C15—C20	−177.7 (13)
N2—Ir1—C11—C15	103.8 (8)	C19—C14—C15—C20	1(2)
C13—Ir1—C11—C15	−79.1 (9)	Ir1—C14—C15—C20	126.4 (14)
C12—Ir1—C11—C15	−114.8 (11)	C13—C14—C15—Ir1	55.9 (9)
C14—Ir1—C11—C15	−36.1 (8)	C19—C14—C15—Ir1	−125.3 (15)
C16—C11—C12—C13	−179.2 (14)	C16—C11—C15—C14	−175.3 (15)
C15—C11—C12—C13	2.7 (13)	C12—C11—C15—C14	2.8 (15)
Ir1—C11—C12—C13	−58.5 (8)	Ir1—C11—C15—C14	65.0 (10)
C16—C11—C12—C17	−1(2)	C16—C11—C15—C20	−4(2)
C15—C11—C12—C17	−178.7 (11)	C12—C11—C15—C20	174.0 (12)
Ir1—C11—C12—C17	120.1 (11)	Ir1—C11—C15—C20	−123.8 (13)
C16—C11—C12—Ir1	−120.7 (15)	C16—C11—C15—Ir1	119.7 (16)
C15—C11—C12—Ir1	61.2 (9)	C12—C11—C15—Ir1	−62.2 (8)
N1—Ir1—C12—C13	−109.7 (7)	N1—Ir1—C15—C14	−107.4 (13)
N2i—Ir1—C12—C13	−24.3 (14)	N2i—Ir1—C15—C14	75.1 (9)
N2—Ir1—C12—C13	172.8 (6)	N2—Ir1—C15—C14	155.9 (8)
C15—Ir1—C12—C13	81.4 (8)	C13—Ir1—C15—C14	−36.0 (8)
C11—Ir1—C12—C13	121.1 (11)	C11—Ir1—C15—C14	−118.3 (12)
C14—Ir1—C12—C13	39.9 (8)	C12—Ir1—C15—C14	−79.0 (9)
N1—Ir1—C12—C11	129.2 (8)	N1—Ir1—C15—C11	10.9 (16)
N2i—Ir1—C12—C11	−145.4 (10)	N2i—Ir1—C15—C11	−166.5 (7)
N2—Ir1—C12—C11	51.7 (9)	N2—Ir1—C15—C11	−85.8 (8)
C15—Ir1—C12—C11	−39.7 (9)	C13—Ir1—C15—C11	82.3 (8)
C13—Ir1—C12—C11	−121.1 (11)	C12—Ir1—C15—C11	39.3 (8)
C14—Ir1—C12—C11	−81.2 (9)	C14—Ir1—C15—C11	118.3 (12)
N1—Ir1—C12—C17	10.8 (14)	N1—Ir1—C15—C20	127.5 (16)
N2i—Ir1—C12—C17	96.2 (15)	N2i—Ir1—C15—C20	−50.0 (19)
N2—Ir1—C12—C17	−66.7 (15)	N2—Ir1—C15—C20	30.8 (19)
C15—Ir1—C12—C17	−158.1 (15)	C13—Ir1—C15—C20	−161 (2)
C13—Ir1—C12—C17	120.5 (16)	C11—Ir1—C15—C20	117 (2)
C11—Ir1—C12—C17	−118.4 (16)	C12—Ir1—C15—C20	156 (2)
C14—Ir1—C12—C17	160.4 (15)	C14—Ir1—C15—C20	−125 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···I1i	0.91	2.91	3.64 (1)	139

Table 1

Selected bond angles (°)

N1—Ir1—N2i	84.3 (3)
N1—Ir1—N2	77.6 (3)
N2i—Ir1—N2	74.1 (4)
Ir1i—N2—Ir1	105.9 (4)

Symmetry code: (i) .