(Pyridine-2-aldoximato-κ(2) N,N')bis-[2-(pyridin-2-yl)phenyl-κ(2) C (1),N]iridium(III).

In the title complex, [Ir(C11H8N)2(C6H5N2O)], the octa-hedrally coordinated Ir(III) atom is bonded to two 2-(pyridin-2-yl)phenyl ligands, through two phenyl C and two pydidine N atoms, and to one pyridine-2-aldoxime ligand through a pyridine N and an oxime N atom. The oxime O atom of the aldoxime unit forms inter-molecular C-H⋯O hydrogen bonds, which result in a two-dimensional hydrogen-bonded polymeric network parallel to (100). C-H⋯π inter-actions are also observed.

Related literature

For the synthesis of the iridium phenyl­pyridine starting material, see: Nonoyama (1974 ▶). For preparation of phenyl pyridine-based Ir(III) complexes, see: Lamansky et al. (2001 ▶). For similar types of complexes, see: Neve et al. (1999 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen bonding, see: Desiraju (1991 ▶) and for C—H⋯π inter­actions, see: Ma & Dougherty (1997 ▶). For oxime ligands, see: Godycki & Rundle (1953 ▶).

Experimental

Crystal data

[Ir(C11H8N)2(C6H5N2O)]

M = 621.71

Monoclinic,

a = 9.414 (1) Å

b = 14.226 (2) Å

c = 9.551 (1) Å

β = 117.260 (7)°

V = 1137.0 (2) Å3

Z = 2

Mo Kα radiation

μ = 5.90 mm−1

T = 293 K

0.40 × 0.32 × 0.24 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.201, T max = 0.332

25091 measured reflections

6898 independent reflections

5718 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.063

S = 0.96

6898 reflections

308 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.34 e Å−3

Δρmin = −0.83 e Å−3

Absolute structure: Flack (1983 ▶), 3193 Friedel pairs

Flack parameter: 0.007 (10)

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SMART (Bruker, 2003 ▶); data reduction: SAINT (Bruker, 2003 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004297/bg2497sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004297/bg2497Isup2.hkl

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

[Ir(C11H8N)2(C6H5N2O)]	F(000) = 604
Mr = 621.71	Dx = 1.816 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4353 reflections
a = 9.414 (1) Å	θ = 2.4–22.5°
b = 14.226 (2) Å	µ = 5.90 mm−1
c = 9.551 (1) Å	T = 293 K
β = 117.260 (7)°	Rod, yellow
V = 1137.0 (2) Å3	0.40 × 0.32 × 0.24 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	6898 independent reflections
Radiation source: fine-focus sealed tube	5718 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 30.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −13→13
Tmin = 0.201, Tmax = 0.332	k = −20→19
25091 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.0158P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
6898 reflections	Δρmax = 1.34 e Å−3
308 parameters	Δρmin = −0.83 e Å−3
1 restraint	Absolute structure: Flack (1983), 3193 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.007 (10)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Ir1	0.247960 (19)	0.64537 (3)	0.109712 (19)	0.02879 (5)
C13	0.0866 (8)	0.3975 (4)	−0.1836 (8)	0.0513 (16)
H13	−0.0105	0.3729	−0.2575	0.062*
C11	0.2459 (6)	0.5892 (4)	0.3030 (7)	0.0342 (12)
C15	0.3653 (8)	0.3892 (4)	−0.0391 (8)	0.0468 (16)
H15	0.4604	0.3575	−0.0137	0.056*
C20	0.7684 (7)	0.6230 (6)	0.3712 (8)	0.056 (3)
H20	0.8552	0.6562	0.4458	0.068*
C23	−0.1127 (5)	0.6426 (8)	0.0322 (6)	0.0425 (11)
H23	−0.0789	0.6100	0.1264	0.051*
N2	0.2292 (5)	0.5204 (3)	−0.0044 (5)	0.0326 (10)
C17	0.5112 (7)	0.5240 (4)	0.1504 (7)	0.0371 (12)
C5	0.2946 (7)	0.7521 (5)	0.3865 (7)	0.0352 (13)
C27	−0.0502 (7)	0.7182 (4)	−0.1511 (7)	0.0371 (12)
C1	0.3174 (8)	0.8495 (4)	0.2026 (8)	0.0448 (14)
H1	0.3124	0.8572	0.1038	0.054*
C12	0.0920 (8)	0.4817 (4)	−0.1096 (8)	0.0447 (14)
H12	−0.0034	0.5127	−0.1337	0.054*
N4	0.2216 (6)	0.7195 (3)	−0.0929 (6)	0.0380 (11)
C24	−0.2732 (7)	0.6586 (7)	−0.0593 (8)	0.052 (2)
H24	−0.3469	0.6387	−0.0260	0.062*
C6	0.2659 (6)	0.6565 (8)	0.4195 (6)	0.0344 (19)
C14	0.2258 (9)	0.3512 (4)	−0.1465 (8)	0.0499 (16)
H14	0.2252	0.2941	−0.1943	0.060*
N1	0.2887 (5)	0.7645 (3)	0.2439 (5)	0.0327 (10)
C3	0.3588 (8)	0.9144 (4)	0.4456 (8)	0.0511 (16)
H3	0.3837	0.9650	0.5145	0.061*
C2	0.3544 (8)	0.9260 (4)	0.3018 (9)	0.0507 (16)
H2	0.3758	0.9842	0.2714	0.061*
C18	0.6659 (8)	0.4887 (5)	0.2082 (8)	0.0496 (16)
H18	0.6829	0.4312	0.1721	0.060*
C16	0.3700 (7)	0.4756 (4)	0.0350 (7)	0.0361 (12)
C4	0.3268 (9)	0.8286 (4)	0.4882 (7)	0.0453 (15)
H4	0.3264	0.8211	0.5848	0.054*
O1	0.3361 (5)	0.7455 (3)	−0.1226 (5)	0.0514 (11)
C28	0.0738 (8)	0.7441 (4)	−0.1892 (7)	0.0461 (14)
H28	0.0509	0.7779	−0.2805	0.055*
C10	0.2257 (8)	0.4959 (5)	0.3361 (8)	0.0429 (14)
H10	0.2129	0.4497	0.2624	0.052*
C9	0.2242 (9)	0.4701 (5)	0.4751 (9)	0.0549 (18)
H9	0.2108	0.4073	0.4935	0.066*
C25	−0.3231 (8)	0.7045 (5)	−0.2005 (9)	0.0605 (19)
H25	−0.4313	0.7153	−0.2646	0.073*
C22	0.4815 (6)	0.6111 (4)	0.2015 (6)	0.0359 (13)
C26	−0.2123 (8)	0.7343 (5)	−0.2466 (8)	0.0549 (17)
H26	−0.2456	0.7654	−0.3422	0.066*
C19	0.7923 (7)	0.5379 (5)	0.3172 (8)	0.0536 (17)
H19	0.8952	0.5139	0.3551	0.064*
C8	0.2420 (8)	0.5359 (5)	0.5848 (7)	0.0529 (17)
H8	0.2419	0.5178	0.6783	0.063*
N3	−0.0031 (5)	0.6730 (3)	−0.0110 (5)	0.0325 (10)
C7	0.2606 (7)	0.6308 (10)	0.5584 (7)	0.048 (2)
H7	0.2692	0.6762	0.6320	0.058*
C21	0.6150 (7)	0.6598 (6)	0.3147 (7)	0.043 (2)
H21	0.6004	0.7174	0.3524	0.052*

	U11	U22	U33	U12	U13	U23
Ir1	0.02708 (8)	0.03172 (8)	0.02746 (9)	−0.0001 (2)	0.01240 (6)	−0.0010 (2)
C13	0.047 (4)	0.049 (4)	0.053 (4)	−0.014 (3)	0.019 (3)	−0.014 (3)
C11	0.024 (3)	0.040 (3)	0.036 (3)	0.004 (2)	0.012 (2)	0.004 (3)
C15	0.059 (4)	0.036 (3)	0.053 (4)	0.013 (3)	0.032 (4)	0.002 (3)
C20	0.033 (3)	0.076 (9)	0.053 (4)	−0.012 (3)	0.013 (3)	0.007 (4)
C23	0.035 (3)	0.043 (2)	0.055 (3)	0.005 (6)	0.025 (2)	0.012 (7)
N2	0.031 (3)	0.033 (2)	0.036 (3)	0.000 (2)	0.017 (2)	−0.002 (2)
C17	0.034 (3)	0.044 (3)	0.035 (3)	0.002 (2)	0.018 (3)	0.002 (2)
C5	0.023 (3)	0.048 (4)	0.033 (3)	0.006 (3)	0.011 (3)	−0.006 (3)
C27	0.037 (3)	0.035 (3)	0.032 (3)	0.000 (2)	0.009 (3)	−0.003 (2)
C1	0.052 (4)	0.038 (3)	0.043 (4)	−0.006 (3)	0.021 (3)	−0.003 (3)
C12	0.047 (4)	0.041 (3)	0.052 (4)	−0.007 (3)	0.028 (3)	−0.009 (3)
N4	0.047 (3)	0.039 (3)	0.031 (3)	−0.011 (2)	0.021 (3)	−0.006 (2)
C24	0.040 (3)	0.052 (6)	0.061 (4)	−0.002 (3)	0.022 (3)	−0.009 (4)
C6	0.029 (2)	0.039 (6)	0.034 (3)	0.003 (3)	0.013 (2)	−0.002 (3)
C14	0.068 (5)	0.035 (3)	0.054 (4)	−0.003 (3)	0.034 (4)	−0.007 (3)
N1	0.024 (2)	0.038 (2)	0.031 (2)	−0.0002 (19)	0.008 (2)	−0.0053 (19)
C3	0.050 (4)	0.044 (3)	0.049 (4)	−0.003 (3)	0.013 (3)	−0.017 (3)
C2	0.043 (4)	0.038 (3)	0.064 (5)	−0.002 (3)	0.017 (3)	−0.004 (3)
C18	0.040 (4)	0.064 (4)	0.048 (4)	0.013 (3)	0.023 (3)	0.011 (3)
C16	0.041 (3)	0.038 (3)	0.033 (3)	0.010 (2)	0.020 (3)	0.012 (2)
C4	0.052 (4)	0.047 (4)	0.032 (3)	0.001 (3)	0.015 (3)	−0.012 (3)
O1	0.055 (3)	0.062 (3)	0.048 (3)	−0.021 (2)	0.032 (2)	−0.006 (2)
C28	0.049 (4)	0.051 (4)	0.032 (3)	0.003 (3)	0.012 (3)	0.008 (3)
C10	0.035 (4)	0.046 (4)	0.048 (4)	0.003 (3)	0.019 (3)	0.010 (3)
C9	0.050 (4)	0.057 (4)	0.064 (5)	0.009 (3)	0.032 (4)	0.025 (4)
C25	0.030 (4)	0.063 (4)	0.068 (5)	0.003 (3)	0.006 (3)	−0.005 (4)
C22	0.028 (3)	0.045 (3)	0.033 (3)	0.000 (2)	0.013 (2)	0.003 (2)
C26	0.045 (4)	0.058 (4)	0.048 (4)	0.003 (3)	0.010 (3)	0.011 (3)
C19	0.024 (3)	0.082 (5)	0.051 (4)	0.010 (3)	0.014 (3)	0.015 (4)
C8	0.052 (4)	0.073 (5)	0.036 (4)	−0.001 (3)	0.022 (3)	0.009 (3)
N3	0.030 (2)	0.034 (3)	0.030 (2)	0.0030 (16)	0.0109 (19)	−0.0012 (16)
C7	0.043 (3)	0.071 (7)	0.030 (3)	0.001 (4)	0.018 (2)	−0.005 (4)
C21	0.038 (3)	0.041 (6)	0.046 (3)	0.002 (3)	0.015 (3)	−0.003 (3)

Ir1—C22	2.018 (5)	C1—N1	1.337 (7)
Ir1—C11	2.020 (6)	C1—C2	1.379 (8)
Ir1—N2	2.051 (4)	C1—H1	0.9300
Ir1—N1	2.053 (4)	C12—H12	0.9300
Ir1—N4	2.116 (5)	N4—O1	1.289 (6)
Ir1—N3	2.139 (4)	N4—C28	1.316 (8)
C13—C14	1.362 (9)	C24—C25	1.374 (10)
C13—C12	1.379 (8)	C24—H24	0.9300
C13—H13	0.9300	C6—C7	1.399 (8)
C11—C10	1.397 (8)	C14—H14	0.9300
C11—C6	1.414 (10)	C3—C4	1.362 (9)
C15—C14	1.355 (9)	C3—C2	1.365 (9)
C15—C16	1.409 (8)	C3—H3	0.9300
C15—H15	0.9300	C2—H2	0.9300
C20—C19	1.374 (11)	C18—C19	1.362 (9)
C20—C21	1.392 (9)	C18—H18	0.9300
C20—H20	0.9300	C4—H4	0.9300
C23—N3	1.345 (7)	C28—H28	0.9300
C23—C24	1.374 (8)	C10—C9	1.384 (9)
C23—H23	0.9300	C10—H10	0.9300
N2—C12	1.339 (7)	C9—C8	1.357 (10)
N2—C16	1.360 (7)	C9—H9	0.9300
C17—C18	1.392 (8)	C25—C26	1.372 (10)
C17—C22	1.407 (7)	C25—H25	0.9300
C17—C16	1.454 (8)	C22—C21	1.408 (8)
C5—N1	1.348 (7)	C26—H26	0.9300
C5—C4	1.397 (8)	C19—H19	0.9300
C5—C6	1.449 (13)	C8—C7	1.399 (16)
C27—N3	1.363 (7)	C8—H8	0.9300
C27—C26	1.392 (9)	C7—H7	0.9300
C27—C28	1.420 (8)	C21—H21	0.9300
C22—Ir1—C11	88.4 (2)	C11—C6—C5	115.8 (5)
C22—Ir1—N2	80.4 (2)	C15—C14—C13	119.2 (6)
C11—Ir1—N2	96.2 (2)	C15—C14—H14	120.4
C22—Ir1—N1	94.21 (19)	C13—C14—H14	120.4
C11—Ir1—N1	80.4 (2)	C1—N1—C5	119.8 (5)
N2—Ir1—N1	173.75 (19)	C1—N1—Ir1	124.6 (4)
C22—Ir1—N4	99.6 (2)	C5—N1—Ir1	115.6 (4)
C11—Ir1—N4	170.6 (2)	C4—C3—C2	120.0 (6)
N2—Ir1—N4	90.0 (2)	C4—C3—H3	120.0
N1—Ir1—N4	93.99 (17)	C2—C3—H3	120.0
C22—Ir1—N3	173.47 (18)	C3—C2—C1	118.5 (6)
C11—Ir1—N3	95.41 (19)	C3—C2—H2	120.7
N2—Ir1—N3	93.90 (17)	C1—C2—H2	120.7
N1—Ir1—N3	91.65 (16)	C19—C18—C17	120.5 (6)
N4—Ir1—N3	77.15 (18)	C19—C18—H18	119.8
C14—C13—C12	118.8 (6)	C17—C18—H18	119.8
C14—C13—H13	120.6	N2—C16—C15	117.9 (6)
C12—C13—H13	120.6	N2—C16—C17	115.1 (5)
C10—C11—C6	116.6 (6)	C15—C16—C17	127.0 (5)
C10—C11—Ir1	129.9 (5)	C3—C4—C5	119.8 (6)
C6—C11—Ir1	113.4 (5)	C3—C4—H4	120.1
C14—C15—C16	121.7 (6)	C5—C4—H4	120.1
C14—C15—H15	119.2	N4—C28—C27	118.8 (5)
C16—C15—H15	119.2	N4—C28—H28	120.6
C19—C20—C21	120.4 (6)	C27—C28—H28	120.6
C19—C20—H20	119.8	C9—C10—C11	122.1 (7)
C21—C20—H20	119.8	C9—C10—H10	119.0
N3—C23—C24	121.8 (6)	C11—C10—H10	119.0
N3—C23—H23	119.1	C8—C9—C10	120.4 (6)
C24—C23—H23	119.1	C8—C9—H9	119.8
C12—N2—C16	119.9 (5)	C10—C9—H9	119.8
C12—N2—Ir1	125.0 (4)	C26—C25—C24	119.6 (6)
C16—N2—Ir1	115.1 (4)	C26—C25—H25	120.2
C18—C17—C22	121.2 (6)	C24—C25—H25	120.2
C18—C17—C16	123.8 (5)	C17—C22—C21	116.8 (5)
C22—C17—C16	115.0 (5)	C17—C22—Ir1	114.4 (4)
N1—C5—C4	119.7 (6)	C21—C22—Ir1	128.8 (4)
N1—C5—C6	114.7 (5)	C25—C26—C27	120.4 (6)
C4—C5—C6	125.6 (5)	C25—C26—H26	119.8
N3—C27—C26	119.1 (5)	C27—C26—H26	119.8
N3—C27—C28	116.0 (5)	C18—C19—C20	120.2 (6)
C26—C27—C28	124.9 (6)	C18—C19—H19	119.9
N1—C1—C2	122.1 (6)	C20—C19—H19	119.9
N1—C1—H1	118.9	C9—C8—C7	120.5 (6)
C2—C1—H1	118.9	C9—C8—H8	119.7
N2—C12—C13	122.6 (6)	C7—C8—H8	119.7
N2—C12—H12	118.7	C23—N3—C27	120.2 (5)
C13—C12—H12	118.7	C23—N3—Ir1	126.1 (4)
O1—N4—C28	119.5 (5)	C27—N3—Ir1	113.4 (3)
O1—N4—Ir1	125.8 (4)	C6—C7—C8	119.0 (10)
C28—N4—Ir1	114.6 (4)	C6—C7—H7	120.5
C25—C24—C23	119.0 (6)	C8—C7—H7	120.5
C25—C24—H24	120.5	C20—C21—C22	121.0 (7)
C23—C24—H24	120.5	C20—C21—H21	119.5
C7—C6—C11	121.3 (11)	C22—C21—H21	119.5
C7—C6—C5	122.9 (9)
C22—Ir1—C11—C10	−84.3 (6)	C12—N2—C16—C17	−179.9 (5)
N2—Ir1—C11—C10	−4.2 (6)	Ir1—N2—C16—C17	−0.6 (6)
N1—Ir1—C11—C10	−178.9 (6)	C14—C15—C16—N2	0.0 (8)
N3—Ir1—C11—C10	90.4 (6)	C14—C15—C16—C17	−179.4 (6)
C22—Ir1—C11—C6	96.7 (4)	C18—C17—C16—N2	178.7 (5)
N2—Ir1—C11—C6	176.8 (4)	C22—C17—C16—N2	−1.4 (7)
N1—Ir1—C11—C6	2.1 (4)	C18—C17—C16—C15	−1.9 (9)
N3—Ir1—C11—C6	−88.6 (4)	C22—C17—C16—C15	178.0 (5)
C22—Ir1—N2—C12	−179.1 (5)	C2—C3—C4—C5	2.1 (10)
C11—Ir1—N2—C12	93.6 (5)	N1—C5—C4—C3	−2.9 (10)
N4—Ir1—N2—C12	−79.4 (5)	C6—C5—C4—C3	177.1 (6)
N3—Ir1—N2—C12	−2.3 (5)	O1—N4—C28—C27	−177.4 (5)
C22—Ir1—N2—C16	1.6 (4)	Ir1—N4—C28—C27	−1.1 (7)
C11—Ir1—N2—C16	−85.7 (4)	N3—C27—C28—N4	3.2 (8)
N4—Ir1—N2—C16	101.3 (4)	C26—C27—C28—N4	−175.7 (6)
N3—Ir1—N2—C16	178.4 (4)	C6—C11—C10—C9	0.4 (9)
C16—N2—C12—C13	−1.2 (9)	Ir1—C11—C10—C9	−178.5 (5)
Ir1—N2—C12—C13	179.6 (5)	C11—C10—C9—C8	0.2 (11)
C14—C13—C12—N2	1.1 (10)	C23—C24—C25—C26	−0.8 (12)
C22—Ir1—N4—O1	−10.4 (5)	C18—C17—C22—C21	−0.8 (8)
N2—Ir1—N4—O1	−90.6 (4)	C16—C17—C22—C21	179.3 (5)
N1—Ir1—N4—O1	84.6 (4)	C18—C17—C22—Ir1	−177.3 (4)
N3—Ir1—N4—O1	175.4 (5)	C16—C17—C22—Ir1	2.7 (6)
C22—Ir1—N4—C28	173.6 (4)	C11—Ir1—C22—C17	94.2 (4)
N2—Ir1—N4—C28	93.4 (4)	N2—Ir1—C22—C17	−2.4 (4)
N1—Ir1—N4—C28	−91.4 (4)	N1—Ir1—C22—C17	174.5 (4)
N3—Ir1—N4—C28	−0.6 (4)	N4—Ir1—C22—C17	−90.8 (4)
N3—C23—C24—C25	1.9 (14)	C11—Ir1—C22—C21	−81.8 (5)
C10—C11—C6—C7	−2.0 (8)	N2—Ir1—C22—C21	−178.4 (5)
Ir1—C11—C6—C7	177.2 (4)	N1—Ir1—C22—C21	−1.6 (5)
C10—C11—C6—C5	177.0 (6)	N4—Ir1—C22—C21	93.2 (5)
Ir1—C11—C6—C5	−3.8 (6)	C24—C25—C26—C27	0.0 (11)
N1—C5—C6—C7	−177.2 (5)	N3—C27—C26—C25	−0.4 (9)
C4—C5—C6—C7	2.9 (9)	C28—C27—C26—C25	178.5 (6)
N1—C5—C6—C11	3.8 (7)	C17—C18—C19—C20	0.0 (9)
C4—C5—C6—C11	−176.1 (6)	C21—C20—C19—C18	−0.2 (10)
C16—C15—C14—C13	−0.1 (9)	C10—C9—C8—C7	0.7 (11)
C12—C13—C14—C15	−0.4 (9)	C24—C23—N3—C27	−2.3 (13)
C2—C1—N1—C5	0.3 (9)	C24—C23—N3—Ir1	−175.4 (7)
C2—C1—N1—Ir1	−175.7 (4)	C26—C27—N3—C23	1.5 (9)
C4—C5—N1—C1	1.7 (8)	C28—C27—N3—C23	−177.5 (7)
C6—C5—N1—C1	−178.3 (5)	C26—C27—N3—Ir1	175.4 (4)
C4—C5—N1—Ir1	178.0 (5)	C28—C27—N3—Ir1	−3.5 (6)
C6—C5—N1—Ir1	−2.0 (6)	C11—Ir1—N3—C23	−10.0 (6)
C22—Ir1—N1—C1	88.4 (5)	N2—Ir1—N3—C23	86.6 (6)
C11—Ir1—N1—C1	176.0 (5)	N1—Ir1—N3—C23	−90.5 (6)
N4—Ir1—N1—C1	−11.5 (5)	N4—Ir1—N3—C23	175.8 (6)
N3—Ir1—N1—C1	−88.7 (5)	C11—Ir1—N3—C27	176.5 (4)
C22—Ir1—N1—C5	−87.7 (4)	N2—Ir1—N3—C27	−86.9 (4)
C11—Ir1—N1—C5	−0.1 (4)	N1—Ir1—N3—C27	96.0 (4)
N4—Ir1—N1—C5	172.4 (4)	N4—Ir1—N3—C27	2.3 (3)
N3—Ir1—N1—C5	95.1 (4)	C11—C6—C7—C8	2.9 (8)
C4—C3—C2—C1	−0.2 (10)	C5—C6—C7—C8	−176.1 (6)
N1—C1—C2—C3	−1.1 (9)	C9—C8—C7—C6	−2.2 (10)
C22—C17—C18—C19	0.5 (9)	C19—C20—C21—C22	−0.1 (10)
C16—C17—C18—C19	−179.6 (6)	C17—C22—C21—C20	0.6 (8)
C12—N2—C16—C15	0.6 (7)	Ir1—C22—C21—C20	176.5 (5)
Ir1—N2—C16—C15	179.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.35	3.235 (10)	159
C15—H15···O1ii	0.93	2.37	3.239 (9)	155
C3—H3···Cg1iii	0.93	2.74	3.604 (7)	155
C8—H8···Cg2i	0.93	2.69	3.606 (7)	170
C13—H13···Cg3iv	0.93	2.71	3.538 (9)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C17–C22, N2/C12–C16 and N1/C1–C5 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.35	3.235 (10)	159
C15—H15⋯O1ii	0.93	2.37	3.239 (9)	155
C3—H3⋯Cg1iii	0.93	2.74	3.604 (7)	155
C8—H8⋯Cg2i	0.93	2.69	3.606 (7)	170
C13—H13⋯Cg3iv	0.93	2.71	3.538 (9)	148

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