(4-Chloro-acetanilido-κ(2)N,O)bis-[2-(pyridin-2-yl)phenyl-κ(2)C(1),N]iridium(III).

In the neutral mononuclear iridium(III) title compound, [Ir(C(8)H(7)ClNO)(C(11)H(8)N)(2)], the Ir(III) atom adopts an octa-hedral geometry, and is coordinated by two 2-phenyl-pyridyl ligands and one anionic 4-chloro-acetanilide ligand. The 2-phenyl-pyridyl ligands are arranged in a cis-C,C' and cis-N,N' fashion. Each 2-phenyl-pyridyl ligand forms a five-membered ring with the Ir(III) atom. The 2-phenyl-pyridyl planes are perpendicular to each other [dihedral angle = 89.9 (1)°]. The Ir-C and Ir-N bond lengths are comparable to those reported for related iridium(III) 2-phenyl-pyridyl complexes. The remaining two coordination sites are occupied by the amidate N and O atoms, which form a four-membered ring with the iridium atom (Ir-N-C-O). The amidate plane is nearly perpendicular to both 2-phenyl-pyridyl ligands [dihedral angles = 87.8 (2) and 88.3 (2)°].

Related literature

For related iridium(III) complexes containing 2-phenyl­pyridyl derivatives as cyclo­metalating ligands, see: Lamansky et al. (2001 ▶); Tamayo et al. (2003 ▶); Yang et al. (2011 ▶); You & Park (2005 ▶); Zhang et al. (2011 ▶). For the coordination geometry of some heteroleptic iridium(III) complexes containing amidate ancillary ligands, see: Yang et al. (2011 ▶); Zhang et al. (2011 ▶). For a general procedure for the preparation of a chloride-bridged iridium(III) dimer, see: Nonoyama (1974 ▶).

Experimental

Crystal data

[Ir(C8H7ClNO)(C11H8N)2]

M = 669.16

Orthorhombic,

a = 12.8391 (15) Å

b = 11.0697 (13) Å

c = 35.897 (4) Å

V = 5101.8 (11) Å3

Z = 8

Mo Kα radiation

μ = 5.37 mm−1

T = 293 K

0.58 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.073, T max = 0.584

41875 measured reflections

4668 independent reflections

4140 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.099

S = 1.11

4668 reflections

326 parameters

H-atom parameters constrained

Δρmax = 1.56 e Å−3

Δρmin = −0.76 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000433/pk2461sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000433/pk2461Isup2.hkl

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

[Ir(C8H7ClNO)(C11H8N)2]	F(000) = 2608
Mr = 669.16	Dx = 1.742 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15543 reflections
a = 12.8391 (15) Å	θ = 3.2–25.3°
b = 11.0697 (13) Å	µ = 5.37 mm−1
c = 35.897 (4) Å	T = 293 K
V = 5101.8 (11) Å3	Block, yellow
Z = 8	0.58 × 0.20 × 0.20 mm

Rigaku Mercury diffractometer	4668 independent reflections
Radiation source: fine-focus sealed tube	4140 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 7.31 pixels mm-1	θmax = 25.4°, θmin = 3.2°
ω scans	h = −15→15
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→13
Tmin = 0.073, Tmax = 0.584	l = −39→43
41875 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0063P)2 + 60.1899P] where P = (Fo2 + 2Fc2)/3
4668 reflections	(Δ/σ)max = 0.002
326 parameters	Δρmax = 1.56 e Å−3
0 restraints	Δρmin = −0.76 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
Ir1	0.52201 (3)	0.20795 (3)	0.647807 (9)	0.03746 (11)
Cl1	0.3095 (3)	0.6436 (3)	0.50134 (10)	0.1069 (13)
O1	0.5741 (5)	0.3599 (5)	0.68362 (16)	0.0476 (15)
N1	0.6555 (5)	0.2045 (6)	0.61709 (18)	0.0394 (16)
N2	0.5537 (7)	0.0664 (7)	0.6804 (2)	0.061 (2)
N3	0.4950 (5)	0.3970 (6)	0.63019 (19)	0.0417 (18)
C1	0.4800 (7)	0.0911 (7)	0.6084 (2)	0.039 (2)
C2	0.3862 (8)	0.0282 (9)	0.6052 (3)	0.055 (3)
H2	0.3350	0.0393	0.6231	0.066*
C3	0.3673 (9)	−0.0505 (9)	0.5759 (3)	0.064 (3)
H3	0.3040	−0.0910	0.5741	0.076*
C4	0.4440 (10)	−0.0680 (10)	0.5492 (3)	0.067 (3)
H4	0.4316	−0.1196	0.5293	0.081*
C5	0.5373 (9)	−0.0104 (9)	0.5519 (3)	0.059 (3)
H5	0.5885	−0.0240	0.5340	0.070*
C6	0.5566 (8)	0.0689 (8)	0.5813 (2)	0.045 (2)
C7	0.6552 (7)	0.1308 (8)	0.5868 (2)	0.044 (2)
C8	0.7431 (9)	0.1250 (10)	0.5643 (3)	0.062 (3)
H8	0.7437	0.0739	0.5438	0.075*
C9	0.8285 (9)	0.1937 (11)	0.5722 (3)	0.067 (3)
H9	0.8873	0.1894	0.5571	0.080*
C10	0.8271 (8)	0.2694 (10)	0.6026 (3)	0.061 (3)
H10	0.8841	0.3180	0.6083	0.074*
C11	0.7394 (7)	0.2712 (8)	0.6244 (3)	0.048 (2)
H11	0.7384	0.3212	0.6452	0.057*
C12	0.3849 (5)	0.2006 (7)	0.6768 (2)	0.0288 (16)
C13	0.3043 (8)	0.2713 (9)	0.6708 (3)	0.056 (3)
H13	0.3085	0.3286	0.6519	0.067*
C14	0.2129 (8)	0.2639 (11)	0.6915 (3)	0.066 (3)
H14	0.1575	0.3160	0.6869	0.079*
C15	0.2069 (9)	0.1791 (11)	0.7185 (4)	0.073 (3)
H15	0.1470	0.1727	0.7329	0.088*
C16	0.2895 (8)	0.1019 (10)	0.7247 (3)	0.064 (3)
H16	0.2853	0.0423	0.7429	0.077*
C17	0.3792 (7)	0.1150 (9)	0.7032 (3)	0.049 (2)
C18	0.4726 (8)	0.0400 (8)	0.7067 (2)	0.046 (2)
C19	0.4866 (8)	−0.0518 (9)	0.7327 (2)	0.055 (3)
H19	0.4337	−0.0694	0.7495	0.066*
C20	0.5770 (9)	−0.1162 (10)	0.7337 (3)	0.063 (3)
H20	0.5858	−0.1765	0.7515	0.076*
C21	0.6547 (9)	−0.0930 (9)	0.7087 (3)	0.059 (3)
H21	0.7158	−0.1378	0.7096	0.071*
C22	0.6436 (7)	−0.0036 (8)	0.6822 (3)	0.047 (2)
H22	0.6970	0.0099	0.6652	0.056*
C23	0.5404 (7)	0.4395 (8)	0.6608 (2)	0.042 (2)
C24	0.5570 (8)	0.5710 (8)	0.6703 (3)	0.060 (3)
H24A	0.4970	0.6015	0.6832	0.091*
H24B	0.5673	0.6163	0.6478	0.091*
H24C	0.6173	0.5789	0.6859	0.091*
C25	0.4504 (7)	0.4570 (9)	0.6010 (3)	0.050 (2)
C26	0.4552 (10)	0.4051 (10)	0.5657 (3)	0.069 (3)
H26	0.4883	0.3310	0.5626	0.083*
C27	0.4117 (9)	0.4619 (11)	0.5354 (3)	0.071 (3)
H27	0.4153	0.4259	0.5121	0.085*
C28	0.3634 (10)	0.5700 (11)	0.5395 (3)	0.071 (3)
C29	0.3555 (10)	0.6215 (10)	0.5731 (4)	0.076 (4)
H29	0.3217	0.6954	0.5754	0.091*
C30	0.3972 (9)	0.5661 (9)	0.6046 (3)	0.067 (3)
H30	0.3896	0.6018	0.6279	0.081*

	U11	U22	U33	U12	U13	U23
Ir1	0.04144 (19)	0.03439 (18)	0.03655 (19)	0.00003 (16)	0.00421 (15)	−0.00038 (16)
Cl1	0.142 (3)	0.083 (2)	0.095 (3)	−0.004 (2)	−0.052 (2)	0.027 (2)
O1	0.058 (4)	0.045 (4)	0.040 (3)	−0.003 (3)	0.001 (3)	−0.008 (3)
N1	0.043 (4)	0.041 (4)	0.034 (4)	−0.001 (4)	0.006 (3)	0.009 (3)
N2	0.076 (6)	0.054 (5)	0.052 (5)	−0.013 (5)	0.000 (5)	−0.005 (4)
N3	0.044 (4)	0.042 (4)	0.039 (4)	0.010 (3)	−0.006 (3)	0.010 (3)
C1	0.045 (5)	0.034 (5)	0.039 (5)	0.003 (4)	−0.006 (4)	0.011 (4)
C2	0.059 (6)	0.057 (6)	0.049 (6)	−0.003 (5)	−0.006 (5)	0.001 (5)
C3	0.070 (7)	0.051 (6)	0.069 (7)	−0.017 (6)	−0.018 (6)	−0.003 (6)
C4	0.092 (9)	0.057 (7)	0.053 (7)	0.004 (7)	−0.021 (6)	−0.006 (5)
C5	0.072 (8)	0.058 (6)	0.045 (6)	0.012 (6)	0.000 (5)	−0.004 (5)
C6	0.058 (6)	0.039 (5)	0.039 (5)	0.008 (5)	−0.004 (4)	0.004 (4)
C7	0.053 (6)	0.046 (5)	0.032 (5)	0.005 (5)	0.004 (4)	0.000 (4)
C8	0.069 (7)	0.064 (7)	0.054 (6)	0.007 (6)	0.019 (6)	0.006 (6)
C9	0.063 (7)	0.083 (8)	0.054 (6)	0.011 (7)	0.025 (5)	−0.004 (6)
C10	0.048 (6)	0.066 (7)	0.070 (7)	−0.012 (5)	0.007 (5)	0.011 (6)
C11	0.051 (5)	0.041 (5)	0.051 (5)	−0.008 (5)	0.008 (5)	0.006 (4)
C12	0.024 (4)	0.030 (4)	0.033 (4)	0.002 (4)	0.004 (3)	−0.006 (4)
C13	0.060 (6)	0.044 (6)	0.063 (6)	−0.006 (5)	0.009 (5)	−0.006 (5)
C14	0.042 (6)	0.075 (8)	0.082 (8)	0.007 (6)	0.011 (6)	−0.019 (7)
C15	0.048 (6)	0.085 (9)	0.086 (9)	−0.017 (6)	0.025 (6)	−0.011 (7)
C16	0.054 (6)	0.073 (7)	0.066 (7)	−0.019 (6)	0.028 (5)	−0.009 (6)
C17	0.050 (6)	0.051 (6)	0.046 (5)	−0.016 (5)	0.003 (4)	−0.021 (5)
C18	0.055 (6)	0.049 (5)	0.033 (5)	−0.015 (5)	0.004 (4)	−0.003 (4)
C19	0.066 (7)	0.061 (6)	0.037 (5)	−0.018 (6)	0.000 (5)	0.006 (5)
C20	0.083 (8)	0.058 (6)	0.048 (6)	0.004 (6)	−0.013 (6)	0.014 (5)
C21	0.072 (7)	0.057 (6)	0.048 (6)	0.012 (6)	−0.010 (5)	0.004 (5)
C22	0.048 (5)	0.041 (5)	0.051 (6)	0.007 (4)	0.000 (4)	0.002 (4)
C23	0.052 (6)	0.031 (5)	0.043 (5)	−0.007 (4)	0.006 (4)	−0.009 (4)
C24	0.070 (7)	0.043 (6)	0.068 (7)	−0.009 (5)	−0.012 (6)	−0.007 (5)
C25	0.044 (6)	0.050 (6)	0.055 (6)	−0.012 (5)	0.001 (5)	0.003 (5)
C26	0.104 (9)	0.050 (6)	0.055 (7)	0.013 (6)	−0.006 (6)	0.001 (5)
C27	0.092 (9)	0.076 (8)	0.045 (6)	0.008 (7)	−0.009 (6)	0.002 (6)
C28	0.087 (9)	0.065 (8)	0.060 (7)	−0.009 (7)	−0.023 (6)	0.015 (6)
C29	0.083 (9)	0.043 (6)	0.103 (10)	−0.002 (6)	−0.019 (8)	0.014 (7)
C30	0.084 (8)	0.047 (6)	0.072 (8)	0.005 (6)	−0.001 (6)	−0.004 (6)

Ir1—C1	1.990 (9)	C12—C13	1.315 (12)
Ir1—N2	1.998 (9)	C12—C17	1.344 (12)
Ir1—N1	2.039 (7)	C13—C14	1.392 (13)
Ir1—C12	2.045 (7)	C13—H13	0.9300
Ir1—N3	2.213 (7)	C14—C15	1.350 (15)
Ir1—O1	2.220 (6)	C14—H14	0.9300
Ir1—C23	2.616 (8)	C15—C16	1.380 (15)
Cl1—C28	1.738 (11)	C15—H15	0.9300
O1—C23	1.279 (10)	C16—C17	1.395 (12)
N1—C11	1.331 (11)	C16—H16	0.9300
N1—C7	1.359 (11)	C17—C18	1.463 (13)
N2—C22	1.391 (12)	C18—C19	1.390 (12)
N2—C18	1.436 (12)	C19—C20	1.363 (14)
N3—C23	1.330 (10)	C19—H19	0.9300
N3—C25	1.367 (11)	C20—C21	1.365 (14)
C1—C2	1.396 (13)	C20—H20	0.9300
C1—C6	1.407 (12)	C21—C22	1.380 (12)
C2—C3	1.387 (13)	C21—H21	0.9300
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.387 (15)	C23—C24	1.510 (12)
C3—H3	0.9300	C24—H24A	0.9600
C4—C5	1.360 (15)	C24—H24B	0.9600
C4—H4	0.9300	C24—H24C	0.9600
C5—C6	1.394 (13)	C25—C26	1.391 (13)
C5—H5	0.9300	C25—C30	1.394 (14)
C6—C7	1.453 (13)	C26—C27	1.375 (14)
C7—C8	1.388 (13)	C26—H26	0.9300
C8—C9	1.364 (15)	C27—C28	1.356 (15)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.376 (14)	C28—C29	1.336 (16)
C9—H9	0.9300	C29—C30	1.394 (15)
C10—C11	1.371 (13)	C29—H29	0.9300
C10—H10	0.9300	C30—H30	0.9300
C11—H11	0.9300
C1—Ir1—N2	87.8 (3)	C13—C12—C17	119.5 (8)
C1—Ir1—N1	80.3 (3)	C13—C12—Ir1	124.8 (7)
N2—Ir1—N1	97.5 (3)	C17—C12—Ir1	115.7 (6)
C1—Ir1—C12	95.8 (3)	C12—C13—C14	122.8 (10)
N2—Ir1—C12	81.2 (3)	C12—C13—H13	118.6
N1—Ir1—C12	176.0 (3)	C14—C13—H13	118.6
C1—Ir1—N3	111.7 (3)	C15—C14—C13	118.2 (10)
N2—Ir1—N3	160.2 (3)	C15—C14—H14	120.9
N1—Ir1—N3	89.7 (3)	C13—C14—H14	120.9
C12—Ir1—N3	92.7 (3)	C14—C15—C16	120.2 (10)
C1—Ir1—O1	170.1 (3)	C14—C15—H15	119.9
N2—Ir1—O1	101.2 (3)	C16—C15—H15	119.9
N1—Ir1—O1	94.3 (3)	C15—C16—C17	118.7 (11)
C12—Ir1—O1	89.7 (3)	C15—C16—H16	120.7
N3—Ir1—O1	59.8 (2)	C17—C16—H16	120.7
C1—Ir1—C23	142.0 (3)	C12—C17—C16	120.6 (10)
N2—Ir1—C23	130.2 (3)	C12—C17—C18	114.6 (8)
N1—Ir1—C23	92.2 (3)	C16—C17—C18	124.8 (10)
C12—Ir1—C23	91.5 (3)	C19—C18—N2	119.7 (9)
N3—Ir1—C23	30.5 (3)	C19—C18—C17	125.3 (9)
O1—Ir1—C23	29.2 (2)	N2—C18—C17	115.0 (8)
C23—O1—Ir1	92.8 (5)	C20—C19—C18	120.7 (10)
C11—N1—C7	119.5 (8)	C20—C19—H19	119.7
C11—N1—Ir1	124.2 (6)	C18—C19—H19	119.7
C7—N1—Ir1	116.2 (6)	C19—C20—C21	120.4 (10)
C22—N2—C18	117.2 (8)	C19—C20—H20	119.8
C22—N2—Ir1	129.3 (7)	C21—C20—H20	119.8
C18—N2—Ir1	113.4 (7)	C20—C21—C22	120.8 (10)
C23—N3—C25	130.2 (8)	C20—C21—H21	119.6
C23—N3—Ir1	91.7 (5)	C22—C21—H21	119.6
C25—N3—Ir1	138.1 (6)	C21—C22—N2	121.1 (9)
C2—C1—C6	117.2 (8)	C21—C22—H22	119.4
C2—C1—Ir1	128.2 (7)	N2—C22—H22	119.4
C6—C1—Ir1	114.6 (7)	O1—C23—N3	115.7 (7)
C3—C2—C1	121.9 (10)	O1—C23—C24	118.2 (8)
C3—C2—H2	119.1	N3—C23—C24	126.1 (9)
C1—C2—H2	119.1	O1—C23—Ir1	57.9 (4)
C2—C3—C4	119.1 (10)	N3—C23—Ir1	57.7 (4)
C2—C3—H3	120.5	C24—C23—Ir1	175.9 (7)
C4—C3—H3	120.5	C23—C24—H24A	109.5
C5—C4—C3	120.8 (10)	C23—C24—H24B	109.5
C5—C4—H4	119.6	H24A—C24—H24B	109.5
C3—C4—H4	119.6	C23—C24—H24C	109.5
C4—C5—C6	120.3 (10)	H24A—C24—H24C	109.5
C4—C5—H5	119.8	H24B—C24—H24C	109.5
C6—C5—H5	119.8	N3—C25—C26	118.6 (9)
C5—C6—C1	120.7 (9)	N3—C25—C30	123.7 (9)
C5—C6—C7	123.8 (9)	C26—C25—C30	117.7 (10)
C1—C6—C7	115.6 (8)	C27—C26—C25	120.8 (10)
N1—C7—C8	119.3 (9)	C27—C26—H26	119.6
N1—C7—C6	113.3 (8)	C25—C26—H26	119.6
C8—C7—C6	127.3 (9)	C28—C27—C26	120.3 (11)
C9—C8—C7	120.5 (10)	C28—C27—H27	119.9
C9—C8—H8	119.8	C26—C27—H27	119.9
C7—C8—H8	119.8	C29—C28—C27	120.6 (11)
C8—C9—C10	119.6 (10)	C29—C28—Cl1	118.7 (10)
C8—C9—H9	120.2	C27—C28—Cl1	120.7 (10)
C10—C9—H9	120.2	C28—C29—C30	121.0 (11)
C11—C10—C9	118.1 (10)	C28—C29—H29	119.5
C11—C10—H10	120.9	C30—C29—H29	119.5
C9—C10—H10	120.9	C25—C30—C29	119.5 (11)
N1—C11—C10	123.0 (9)	C25—C30—H30	120.2
N1—C11—H11	118.5	C29—C30—H30	120.2
C10—C11—H11	118.5
C1—Ir1—O1—C23	31 (2)	C9—C10—C11—N1	−1.0 (15)
N2—Ir1—O1—C23	−174.5 (6)	C1—Ir1—C12—C13	−90.0 (8)
N1—Ir1—O1—C23	87.0 (5)	N2—Ir1—C12—C13	−176.8 (8)
C12—Ir1—O1—C23	−93.5 (5)	N1—Ir1—C12—C13	−106 (4)
N3—Ir1—O1—C23	−0.2 (5)	N3—Ir1—C12—C13	22.2 (8)
C1—Ir1—N1—C11	177.9 (7)	O1—Ir1—C12—C13	81.9 (8)
N2—Ir1—N1—C11	−95.7 (7)	C23—Ir1—C12—C13	52.7 (8)
C12—Ir1—N1—C11	−166 (4)	C1—Ir1—C12—C17	89.0 (6)
N3—Ir1—N1—C11	65.8 (7)	N2—Ir1—C12—C17	2.1 (6)
O1—Ir1—N1—C11	6.2 (7)	N1—Ir1—C12—C17	73 (4)
C23—Ir1—N1—C11	35.4 (7)	N3—Ir1—C12—C17	−158.9 (6)
C1—Ir1—N1—C7	−0.2 (6)	O1—Ir1—C12—C17	−99.2 (6)
N2—Ir1—N1—C7	86.2 (6)	C23—Ir1—C12—C17	−128.4 (6)
C12—Ir1—N1—C7	16 (4)	C17—C12—C13—C14	1.9 (14)
N3—Ir1—N1—C7	−112.3 (6)	Ir1—C12—C13—C14	−179.2 (7)
O1—Ir1—N1—C7	−171.9 (6)	C12—C13—C14—C15	−1.1 (16)
C23—Ir1—N1—C7	−142.7 (6)	C13—C14—C15—C16	−0.5 (17)
C1—Ir1—N2—C22	84.0 (8)	C14—C15—C16—C17	1.2 (17)
N1—Ir1—N2—C22	4.1 (8)	C13—C12—C17—C16	−1.1 (13)
C12—Ir1—N2—C22	−179.7 (8)	Ir1—C12—C17—C16	179.9 (7)
N3—Ir1—N2—C22	−106.4 (11)	C13—C12—C17—C18	178.5 (8)
O1—Ir1—N2—C22	−91.8 (8)	Ir1—C12—C17—C18	−0.5 (9)
C23—Ir1—N2—C22	−95.3 (8)	C15—C16—C17—C12	−0.4 (15)
C1—Ir1—N2—C18	−99.6 (6)	C15—C16—C17—C18	180.0 (9)
N1—Ir1—N2—C18	−179.5 (6)	C22—N2—C18—C19	0.6 (12)
C12—Ir1—N2—C18	−3.3 (6)	Ir1—N2—C18—C19	−176.3 (7)
N3—Ir1—N2—C18	69.9 (12)	C22—N2—C18—C17	−179.0 (8)
O1—Ir1—N2—C18	84.6 (6)	Ir1—N2—C18—C17	4.1 (10)
C23—Ir1—N2—C18	81.1 (7)	C12—C17—C18—C19	178.0 (8)
C1—Ir1—N3—C23	−174.4 (5)	C16—C17—C18—C19	−2.3 (15)
N2—Ir1—N3—C23	16.9 (12)	C12—C17—C18—N2	−2.4 (11)
N1—Ir1—N3—C23	−94.9 (5)	C16—C17—C18—N2	177.3 (9)
C12—Ir1—N3—C23	88.2 (5)	N2—C18—C19—C20	0.6 (14)
O1—Ir1—N3—C23	0.2 (5)	C17—C18—C19—C20	−179.8 (9)
C1—Ir1—N3—C25	6.3 (10)	C18—C19—C20—C21	−1.1 (16)
N2—Ir1—N3—C25	−162.4 (10)	C19—C20—C21—C22	0.3 (16)
N1—Ir1—N3—C25	85.8 (9)	C20—C21—C22—N2	1.0 (15)
C12—Ir1—N3—C25	−91.1 (9)	C18—N2—C22—C21	−1.4 (13)
O1—Ir1—N3—C25	−179.1 (10)	Ir1—N2—C22—C21	174.9 (7)
C23—Ir1—N3—C25	−179.3 (12)	Ir1—O1—C23—N3	0.3 (8)
N2—Ir1—C1—C2	79.6 (8)	Ir1—O1—C23—C24	−178.4 (8)
N1—Ir1—C1—C2	177.6 (8)	C25—N3—C23—O1	179.1 (8)
C12—Ir1—C1—C2	−1.3 (8)	Ir1—N3—C23—O1	−0.3 (8)
N3—Ir1—C1—C2	−96.6 (8)	C25—N3—C23—C24	−2.3 (15)
O1—Ir1—C1—C2	−125.3 (17)	Ir1—N3—C23—C24	178.3 (9)
C23—Ir1—C1—C2	−101.3 (9)	C25—N3—C23—Ir1	179.4 (11)
N2—Ir1—C1—C6	−99.0 (6)	C1—Ir1—C23—O1	−171.8 (6)
N1—Ir1—C1—C6	−1.0 (6)	N2—Ir1—C23—O1	7.1 (7)
C12—Ir1—C1—C6	−179.9 (6)	N1—Ir1—C23—O1	−94.7 (5)
N3—Ir1—C1—C6	84.8 (6)	C12—Ir1—C23—O1	86.8 (5)
O1—Ir1—C1—C6	56 (2)	N3—Ir1—C23—O1	179.7 (9)
C23—Ir1—C1—C6	80.1 (8)	C1—Ir1—C23—N3	8.5 (8)
C6—C1—C2—C3	−1.9 (14)	N2—Ir1—C23—N3	−172.6 (5)
Ir1—C1—C2—C3	179.6 (7)	N1—Ir1—C23—N3	85.6 (5)
C1—C2—C3—C4	0.5 (16)	C12—Ir1—C23—N3	−92.9 (5)
C2—C3—C4—C5	1.0 (16)	O1—Ir1—C23—N3	−179.7 (9)
C3—C4—C5—C6	−1.1 (16)	C1—Ir1—C23—C24	−152 (10)
C4—C5—C6—C1	−0.3 (14)	N2—Ir1—C23—C24	27 (10)
C4—C5—C6—C7	178.0 (9)	N1—Ir1—C23—C24	−75 (10)
C2—C1—C6—C5	1.7 (13)	C12—Ir1—C23—C24	106 (10)
Ir1—C1—C6—C5	−179.5 (7)	N3—Ir1—C23—C24	−161 (10)
C2—C1—C6—C7	−176.7 (8)	O1—Ir1—C23—C24	20 (10)
Ir1—C1—C6—C7	2.1 (10)	C23—N3—C25—C26	148.1 (10)
C11—N1—C7—C8	1.0 (13)	Ir1—N3—C25—C26	−32.7 (14)
Ir1—N1—C7—C8	179.3 (7)	C23—N3—C25—C30	−33.9 (15)
C11—N1—C7—C6	−176.8 (8)	Ir1—N3—C25—C30	145.3 (9)
Ir1—N1—C7—C6	1.4 (10)	N3—C25—C26—C27	−179.9 (10)
C5—C6—C7—N1	179.4 (8)	C30—C25—C26—C27	2.0 (17)
C1—C6—C7—N1	−2.3 (11)	C25—C26—C27—C28	0.2 (19)
C5—C6—C7—C8	1.7 (15)	C26—C27—C28—C29	−1 (2)
C1—C6—C7—C8	−179.9 (9)	C26—C27—C28—Cl1	179.2 (10)
N1—C7—C8—C9	−1.0 (15)	C27—C28—C29—C30	1 (2)
C6—C7—C8—C9	176.6 (10)	Cl1—C28—C29—C30	179.9 (9)
C7—C8—C9—C10	−0.1 (17)	N3—C25—C30—C29	179.1 (10)
C8—C9—C10—C11	1.1 (16)	C26—C25—C30—C29	−2.9 (16)
C7—N1—C11—C10	−0.1 (14)	C28—C29—C30—C25	1.7 (18)
Ir1—N1—C11—C10	−178.1 (7)