Synthesis and crystal structure of (1,8-naphth­yridine-κ²N,N′)[2-(1H-pyrazol-1-yl)phenyl-κ²N²,C¹]iridium(III) hexa­fluorido­phosphate di­chloro­methane monosolvate

The coordination environment of the Ir^III atom in the complex cation is pseudo-octa­hedral, with an N₄C₂ coordination set.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.024
• wR factor = 0.062
• Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C27 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       Cl1      0.265 Check
PLAT336_ALERT_2_C Long Bond Distance for ..... C27      -Cl2            1.880 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).         10 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          9 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          6 Note
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       8.53 Why ?
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT244_ALERT_4_G Low    'Solvent' Ueq as Compared to Neighbors of         P1 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   7 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

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

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

(1,8-Naphthyridine-κ²N,N')[2-(1H-pyrazol-1-yl)phenyl-κ²N²,C¹]iridium(III) hexafluoridophosphate dichloromethane monosolvate

Crystal data

[Ir(C9H7N2)2(C8H6N2)]PF6·CH2Cl2	F(000) = 1624
Mr = 838.57	Dx = 1.785 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1222 (3) Å	Cell parameters from 9905 reflections
b = 15.5510 (4) Å	θ = 2.9–26.4°
c = 17.1579 (5) Å	µ = 4.57 mm^−1
β = 105.313 (1)°	T = 293 K
V = 3119.64 (14) Å^3	Block, red
Z = 4	0.20 × 0.18 × 0.15 mm

Data collection

APEXII CCD area detector diffractometer	5528 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.032
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 26.4°, θmin = 2.9°
Tmin = 0.417, Tmax = 0.504	h = −15→15
36216 measured reflections	k = −19→19
6387 independent reflections	l = −21→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0254P)^2 + 8.5285P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
6387 reflections	Δρmax = 1.29 e Å^−3
388 parameters	Δρmin = −1.03 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ir1	0.69497 (2)	0.12122 (2)	0.36803 (2)	0.02071 (5)
N1	0.5244 (3)	0.11978 (17)	0.35308 (18)	0.0227 (6)
N2	0.4908 (3)	0.11594 (18)	0.42268 (19)	0.0279 (7)
N3	0.8666 (3)	0.12796 (19)	0.3960 (2)	0.0324 (7)
N4	0.9109 (3)	0.2077 (2)	0.4177 (3)	0.0446 (10)
N5	0.6867 (3)	−0.00707 (18)	0.30844 (17)	0.0231 (6)
N6	0.6822 (3)	0.11475 (18)	0.23884 (18)	0.0229 (6)
C1	0.6907 (3)	0.1083 (2)	0.4841 (2)	0.0272 (8)
C2	0.7798 (4)	0.1025 (3)	0.5545 (3)	0.0423 (11)
H2A	0.8550	0.1019	0.5508	0.051*
C3	0.7581 (6)	0.0977 (3)	0.6303 (3)	0.0552 (15)
H3A	0.8190	0.0936	0.6763	0.066*
C4	0.6483 (6)	0.0990 (3)	0.6380 (3)	0.0541 (15)
H4A	0.6355	0.0960	0.6891	0.065*
C5	0.5570 (5)	0.1046 (3)	0.5705 (3)	0.0435 (11)
H5A	0.4822	0.1053	0.5749	0.052*
C6	0.5806 (4)	0.1092 (2)	0.4952 (2)	0.0295 (8)
C7	0.3761 (4)	0.1172 (3)	0.4054 (3)	0.0379 (10)
H7A	0.3329	0.1153	0.4428	0.045*
C8	0.3336 (4)	0.1219 (3)	0.3234 (3)	0.0389 (10)
H8A	0.2572	0.1237	0.2943	0.047*
C9	0.4292 (3)	0.1233 (2)	0.2927 (2)	0.0301 (8)
H9A	0.4269	0.1262	0.2381	0.036*
C10	0.7152 (3)	0.2476 (2)	0.3880 (2)	0.0280 (8)
C11	0.6328 (4)	0.3117 (2)	0.3775 (2)	0.0296 (8)
H11A	0.5559	0.2964	0.3638	0.036*
C12	0.6627 (4)	0.3982 (3)	0.3869 (3)	0.0387 (10)
H12A	0.6058	0.4399	0.3784	0.046*
C13	0.7757 (5)	0.4221 (3)	0.4087 (3)	0.0512 (13)
H13A	0.7950	0.4800	0.4149	0.061*
C14	0.8604 (5)	0.3609 (3)	0.4213 (4)	0.0572 (14)
H14A	0.9371	0.3767	0.4369	0.069*
C15	0.8290 (4)	0.2753 (3)	0.4102 (3)	0.0383 (10)
C16	1.0249 (4)	0.2038 (3)	0.4437 (4)	0.0682 (18)
H16A	1.0740	0.2498	0.4615	0.082*
C17	1.0564 (4)	0.1195 (3)	0.4393 (4)	0.0653 (17)
H17A	1.1302	0.0973	0.4536	0.078*
C18	0.9556 (4)	0.0745 (3)	0.4092 (3)	0.0451 (11)
H18A	0.9506	0.0156	0.3996	0.054*
C19	0.6751 (3)	0.1585 (2)	0.1718 (2)	0.0290 (8)
H19A	0.6762	0.2183	0.1736	0.035*
C20	0.6659 (4)	0.1168 (3)	0.0978 (2)	0.0353 (9)
H20A	0.6611	0.1492	0.0515	0.042*
C21	0.6641 (4)	0.0293 (3)	0.0932 (2)	0.0369 (9)
H21A	0.6585	0.0019	0.0441	0.044*
C22	0.6709 (3)	−0.0195 (2)	0.1641 (2)	0.0292 (8)
C23	0.6710 (4)	−0.1098 (3)	0.1724 (3)	0.0398 (10)
H23A	0.6657	−0.1451	0.1278	0.048*
C24	0.6790 (4)	−0.1446 (3)	0.2465 (3)	0.0420 (11)
H24A	0.6796	−0.2041	0.2526	0.050*
C25	0.6864 (4)	−0.0915 (2)	0.3141 (2)	0.0303 (8)
H25A	0.6913	−0.1167	0.3640	0.036*
C26	0.6794 (3)	0.0278 (2)	0.2341 (2)	0.0231 (7)
P1	0.33055 (9)	0.18918 (6)	0.06223 (6)	0.0258 (2)
F1	0.42475 (18)	0.23551 (13)	0.13286 (12)	0.0291 (5)
F2	0.2498 (2)	0.17991 (17)	0.12174 (15)	0.0450 (6)
F3	0.4115 (2)	0.20007 (16)	0.00312 (14)	0.0392 (6)
F4	0.3873 (2)	0.09807 (14)	0.09090 (15)	0.0417 (6)
F5	0.2744 (2)	0.28140 (14)	0.03324 (14)	0.0372 (5)
F6	0.2350 (2)	0.14372 (16)	−0.00851 (15)	0.0435 (6)
Cl1	−0.0040 (4)	0.7352 (5)	0.2789 (3)	0.279 (3)
Cl2	0.0137 (4)	0.5589 (5)	0.3252 (4)	0.302 (3)
C27	0.0177 (11)	0.6755 (13)	0.3551 (10)	0.214 (8)
H27A	−0.0402	0.6863	0.3836	0.256*
H27B	0.0918	0.6888	0.3915	0.256*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.02483 (8)	0.01435 (7)	0.02045 (8)	−0.00010 (5)	0.00159 (5)	−0.00110 (5)
N1	0.0284 (16)	0.0174 (14)	0.0222 (15)	0.0003 (12)	0.0064 (12)	0.0015 (11)
N2	0.0368 (18)	0.0195 (15)	0.0300 (17)	0.0019 (13)	0.0133 (14)	0.0004 (12)
N3	0.0291 (17)	0.0183 (15)	0.046 (2)	−0.0023 (13)	0.0033 (15)	−0.0015 (14)
N4	0.0296 (19)	0.0245 (17)	0.070 (3)	−0.0053 (15)	−0.0045 (18)	−0.0040 (17)
N5	0.0264 (16)	0.0185 (14)	0.0221 (15)	−0.0024 (12)	0.0025 (12)	−0.0014 (11)
N6	0.0253 (15)	0.0186 (14)	0.0250 (15)	0.0012 (12)	0.0071 (12)	0.0016 (11)
C1	0.038 (2)	0.0158 (16)	0.0241 (18)	0.0026 (15)	0.0014 (16)	−0.0021 (13)
C2	0.059 (3)	0.028 (2)	0.030 (2)	0.0075 (19)	−0.007 (2)	−0.0012 (16)
C3	0.102 (5)	0.031 (2)	0.021 (2)	0.012 (3)	−0.004 (2)	0.0003 (17)
C4	0.110 (5)	0.028 (2)	0.026 (2)	0.012 (3)	0.021 (3)	0.0009 (17)
C5	0.078 (3)	0.027 (2)	0.033 (2)	0.008 (2)	0.026 (2)	0.0020 (17)
C6	0.049 (2)	0.0155 (17)	0.0236 (18)	0.0025 (16)	0.0089 (17)	−0.0006 (13)
C7	0.033 (2)	0.030 (2)	0.056 (3)	0.0010 (17)	0.021 (2)	0.0007 (18)
C8	0.027 (2)	0.029 (2)	0.058 (3)	0.0014 (17)	0.0057 (19)	0.0043 (19)
C9	0.029 (2)	0.0230 (18)	0.034 (2)	0.0001 (15)	0.0000 (16)	0.0030 (15)
C10	0.041 (2)	0.0170 (17)	0.0242 (18)	0.0010 (15)	0.0048 (16)	−0.0019 (13)
C11	0.043 (2)	0.0205 (18)	0.0253 (19)	0.0011 (16)	0.0093 (17)	−0.0020 (14)
C12	0.058 (3)	0.0200 (19)	0.038 (2)	0.0073 (18)	0.013 (2)	−0.0022 (16)
C13	0.062 (3)	0.018 (2)	0.071 (3)	−0.005 (2)	0.012 (3)	−0.007 (2)
C14	0.051 (3)	0.029 (2)	0.085 (4)	−0.013 (2)	0.008 (3)	−0.009 (2)
C15	0.035 (2)	0.0201 (19)	0.052 (3)	−0.0029 (17)	−0.002 (2)	−0.0036 (17)
C16	0.031 (3)	0.039 (3)	0.119 (5)	−0.008 (2)	−0.008 (3)	−0.006 (3)
C17	0.027 (2)	0.045 (3)	0.111 (5)	0.004 (2)	−0.005 (3)	−0.002 (3)
C18	0.033 (2)	0.028 (2)	0.068 (3)	0.0030 (18)	0.003 (2)	−0.001 (2)
C19	0.032 (2)	0.0225 (18)	0.033 (2)	0.0021 (15)	0.0094 (17)	0.0082 (15)
C20	0.044 (2)	0.038 (2)	0.0251 (19)	0.0044 (19)	0.0111 (18)	0.0101 (16)
C21	0.050 (3)	0.037 (2)	0.0234 (19)	−0.0016 (19)	0.0101 (18)	−0.0004 (16)
C22	0.036 (2)	0.0276 (19)	0.0232 (18)	−0.0051 (16)	0.0061 (16)	−0.0022 (15)
C23	0.066 (3)	0.028 (2)	0.028 (2)	−0.008 (2)	0.015 (2)	−0.0095 (16)
C24	0.074 (3)	0.0171 (18)	0.036 (2)	−0.008 (2)	0.018 (2)	−0.0052 (16)
C25	0.045 (2)	0.0189 (17)	0.0273 (19)	−0.0042 (16)	0.0102 (18)	0.0030 (14)
C26	0.0269 (19)	0.0199 (17)	0.0215 (17)	−0.0008 (14)	0.0046 (14)	0.0018 (13)
P1	0.0312 (5)	0.0184 (4)	0.0244 (5)	0.0010 (4)	0.0015 (4)	−0.0036 (3)
F1	0.0335 (12)	0.0243 (11)	0.0242 (11)	−0.0019 (9)	−0.0015 (9)	−0.0027 (8)
F2	0.0416 (14)	0.0511 (16)	0.0445 (15)	−0.0082 (12)	0.0155 (12)	−0.0054 (12)
F3	0.0461 (15)	0.0417 (14)	0.0311 (12)	0.0004 (11)	0.0122 (11)	−0.0046 (10)
F4	0.0535 (16)	0.0168 (11)	0.0486 (15)	0.0020 (10)	0.0023 (12)	0.0010 (10)
F5	0.0427 (14)	0.0249 (11)	0.0362 (13)	0.0089 (10)	−0.0035 (11)	−0.0021 (9)
F6	0.0433 (14)	0.0369 (13)	0.0396 (14)	−0.0039 (11)	−0.0077 (11)	−0.0148 (11)
Cl1	0.177 (4)	0.470 (9)	0.169 (4)	−0.139 (5)	0.008 (3)	0.032 (5)
Cl2	0.106 (3)	0.407 (9)	0.381 (8)	−0.022 (4)	0.043 (4)	0.061 (7)
C27	0.116 (10)	0.34 (2)	0.197 (15)	0.054 (13)	0.065 (10)	0.096 (17)

Geometric parameters (Å, º)

Ir1—C10	1.999 (4)	C11—H11A	0.9300
Ir1—N3	2.010 (3)	C12—C13	1.373 (7)
Ir1—N1	2.015 (3)	C12—H12A	0.9300
Ir1—C1	2.016 (4)	C13—C14	1.374 (7)
Ir1—N6	2.183 (3)	C13—H13A	0.9300
Ir1—N5	2.232 (3)	C14—C15	1.384 (6)
N1—C9	1.333 (5)	C14—H14A	0.9300
N1—N2	1.361 (4)	C16—C17	1.372 (7)
N2—C7	1.344 (5)	C16—H16A	0.9300
N2—C6	1.424 (5)	C17—C18	1.385 (6)
N3—C18	1.333 (5)	C17—H17A	0.9300
N3—N4	1.364 (4)	C18—H18A	0.9300
N4—C16	1.336 (6)	C19—C20	1.404 (6)
N4—C15	1.428 (5)	C19—H19A	0.9300
N5—C25	1.317 (5)	C20—C21	1.363 (6)
N5—C26	1.366 (4)	C20—H20A	0.9300
N6—C19	1.319 (5)	C21—C22	1.418 (5)
N6—C26	1.355 (4)	C21—H21A	0.9300
C1—C2	1.394 (6)	C22—C26	1.390 (5)
C1—C6	1.397 (6)	C22—C23	1.411 (5)
C2—C3	1.396 (7)	C23—C24	1.363 (6)
C2—H2A	0.9300	C23—H23A	0.9300
C3—C4	1.372 (8)	C24—C25	1.407 (5)
C3—H3A	0.9300	C24—H24A	0.9300
C4—C5	1.378 (7)	C25—H25A	0.9300
C4—H4A	0.9300	P1—F4	1.595 (2)
C5—C6	1.396 (6)	P1—F3	1.595 (3)
C5—H5A	0.9300	P1—F2	1.597 (3)
C7—C8	1.366 (7)	P1—F1	1.600 (2)
C7—H7A	0.9300	P1—F6	1.604 (2)
C8—C9	1.394 (6)	P1—F5	1.609 (2)
C8—H8A	0.9300	Cl1—C27	1.567 (14)
C9—H9A	0.9300	Cl2—C27	1.882 (19)
C10—C11	1.388 (5)	C27—H27A	0.9700
C10—C15	1.398 (6)	C27—H27B	0.9700
C11—C12	1.391 (5)
C10—Ir1—N3	80.52 (14)	C13—C12—C11	120.2 (4)
C10—Ir1—N1	96.21 (14)	C13—C12—H12A	119.9
N3—Ir1—N1	173.28 (13)	C11—C12—H12A	119.9
C10—Ir1—C1	87.88 (14)	C12—C13—C14	120.4 (4)
N3—Ir1—C1	93.67 (15)	C12—C13—H13A	119.8
N1—Ir1—C1	80.29 (14)	C14—C13—H13A	119.8
C10—Ir1—N6	101.05 (13)	C13—C14—C15	118.5 (5)
N3—Ir1—N6	92.10 (13)	C13—C14—H14A	120.7
N1—Ir1—N6	94.29 (11)	C15—C14—H14A	120.7
C1—Ir1—N6	170.06 (13)	C14—C15—C10	123.3 (4)
C10—Ir1—N5	161.07 (13)	C14—C15—N4	122.4 (4)
N3—Ir1—N5	94.28 (12)	C10—C15—N4	114.2 (3)
N1—Ir1—N5	90.63 (11)	N4—C16—C17	107.7 (4)
C1—Ir1—N5	110.71 (12)	N4—C16—H16A	126.1
N6—Ir1—N5	60.74 (10)	C17—C16—H16A	126.1
C9—N1—N2	106.6 (3)	C16—C17—C18	105.7 (4)
C9—N1—Ir1	138.3 (3)	C16—C17—H17A	127.1
N2—N1—Ir1	115.0 (2)	C18—C17—H17A	127.1
C7—N2—N1	109.7 (3)	N3—C18—C17	110.1 (4)
C7—N2—C6	134.6 (4)	N3—C18—H18A	125.0
N1—N2—C6	115.7 (3)	C17—C18—H18A	125.0
C18—N3—N4	106.1 (3)	N6—C19—C20	121.4 (3)
C18—N3—Ir1	138.4 (3)	N6—C19—H19A	119.3
N4—N3—Ir1	114.9 (2)	C20—C19—H19A	119.3
C16—N4—N3	110.3 (4)	C21—C20—C19	120.7 (4)
C16—N4—C15	134.2 (4)	C21—C20—H20A	119.7
N3—N4—C15	115.5 (3)	C19—C20—H20A	119.7
C25—N5—C26	117.6 (3)	C20—C21—C22	119.2 (4)
C25—N5—Ir1	149.1 (3)	C20—C21—H21A	120.4
C26—N5—Ir1	93.3 (2)	C22—C21—H21A	120.4
C19—N6—C26	117.9 (3)	C26—C22—C23	116.2 (3)
C19—N6—Ir1	146.3 (3)	C26—C22—C21	115.6 (3)
C26—N6—Ir1	95.8 (2)	C23—C22—C21	128.1 (4)
C2—C1—C6	115.7 (4)	C24—C23—C22	119.1 (4)
C2—C1—Ir1	130.2 (3)	C24—C23—H23A	120.4
C6—C1—Ir1	114.1 (3)	C22—C23—H23A	120.4
C1—C2—C3	121.1 (5)	C23—C24—C25	120.6 (4)
C1—C2—H2A	119.5	C23—C24—H24A	119.7
C3—C2—H2A	119.5	C25—C24—H24A	119.7
C4—C3—C2	121.1 (5)	N5—C25—C24	121.8 (4)
C4—C3—H3A	119.5	N5—C25—H25A	119.1
C2—C3—H3A	119.5	C24—C25—H25A	119.1
C3—C4—C5	120.2 (4)	N6—C26—N5	110.2 (3)
C3—C4—H4A	119.9	N6—C26—C22	125.1 (3)
C5—C4—H4A	119.9	N5—C26—C22	124.6 (3)
C4—C5—C6	117.8 (5)	F4—P1—F3	90.16 (14)
C4—C5—H5A	121.1	F4—P1—F2	90.57 (15)
C6—C5—H5A	121.1	F3—P1—F2	179.07 (15)
C5—C6—C1	124.1 (4)	F4—P1—F1	90.17 (12)
C5—C6—N2	121.1 (4)	F3—P1—F1	89.89 (13)
C1—C6—N2	114.8 (3)	F2—P1—F1	89.53 (13)
N2—C7—C8	108.4 (4)	F4—P1—F6	90.47 (13)
N2—C7—H7A	125.8	F3—P1—F6	90.46 (14)
C8—C7—H7A	125.8	F2—P1—F6	90.11 (14)
C7—C8—C9	105.4 (4)	F1—P1—F6	179.27 (14)
C7—C8—H8A	127.3	F4—P1—F5	179.49 (15)
C9—C8—H8A	127.3	F3—P1—F5	89.43 (14)
N1—C9—C8	109.9 (4)	F2—P1—F5	89.85 (14)
N1—C9—H9A	125.1	F1—P1—F5	89.54 (12)
C8—C9—H9A	125.1	F6—P1—F5	89.83 (13)
C11—C10—C15	116.0 (3)	Cl1—C27—Cl2	110.9 (11)
C11—C10—Ir1	129.2 (3)	Cl1—C27—H27A	109.5
C15—C10—Ir1	114.7 (3)	Cl2—C27—H27A	109.5
C10—C11—C12	121.5 (4)	Cl1—C27—H27B	109.5
C10—C11—H11A	119.2	Cl2—C27—H27B	109.5
C12—C11—H11A	119.2	H27A—C27—H27B	108.1
C9—N1—N2—C7	−0.1 (4)	Ir1—C10—C15—C14	175.5 (4)
Ir1—N1—N2—C7	178.7 (2)	C11—C10—C15—N4	−178.0 (4)
C9—N1—N2—C6	178.2 (3)	Ir1—C10—C15—N4	−2.2 (5)
Ir1—N1—N2—C6	−3.0 (4)	C16—N4—C15—C14	9.1 (9)
C18—N3—N4—C16	0.1 (6)	N3—N4—C15—C14	−172.8 (5)
Ir1—N3—N4—C16	173.1 (4)	C16—N4—C15—C10	−173.1 (6)
C18—N3—N4—C15	−178.5 (4)	N3—N4—C15—C10	5.0 (6)
Ir1—N3—N4—C15	−5.4 (5)	N3—N4—C16—C17	−0.2 (7)
C6—C1—C2—C3	0.2 (6)	C15—N4—C16—C17	177.9 (6)
Ir1—C1—C2—C3	177.0 (3)	N4—C16—C17—C18	0.3 (8)
C1—C2—C3—C4	−0.3 (7)	N4—N3—C18—C17	0.1 (6)
C2—C3—C4—C5	0.3 (7)	Ir1—N3—C18—C17	−170.4 (4)
C3—C4—C5—C6	−0.2 (6)	C16—C17—C18—N3	−0.3 (7)
C4—C5—C6—C1	0.1 (6)	C26—N6—C19—C20	−0.5 (6)
C4—C5—C6—N2	−179.4 (4)	Ir1—N6—C19—C20	−178.8 (3)
C2—C1—C6—C5	−0.1 (5)	N6—C19—C20—C21	0.0 (7)
Ir1—C1—C6—C5	−177.4 (3)	C19—C20—C21—C22	0.4 (7)
C2—C1—C6—N2	179.4 (3)	C20—C21—C22—C26	−0.2 (6)
Ir1—C1—C6—N2	2.2 (4)	C20—C21—C22—C23	−179.6 (5)
C7—N2—C6—C5	−2.1 (6)	C26—C22—C23—C24	0.1 (7)
N1—N2—C6—C5	−179.9 (3)	C21—C22—C23—C24	179.5 (5)
C7—N2—C6—C1	178.3 (4)	C22—C23—C24—C25	0.4 (7)
N1—N2—C6—C1	0.5 (4)	C26—N5—C25—C24	0.0 (6)
N1—N2—C7—C8	0.0 (4)	Ir1—N5—C25—C24	−179.4 (4)
C6—N2—C7—C8	−177.8 (4)	C23—C24—C25—N5	−0.5 (7)
N2—C7—C8—C9	0.0 (4)	C19—N6—C26—N5	−179.5 (3)
N2—N1—C9—C8	0.1 (4)	Ir1—N6—C26—N5	−0.5 (3)
Ir1—N1—C9—C8	−178.2 (3)	C19—N6—C26—C22	0.7 (6)
C7—C8—C9—N1	−0.1 (4)	Ir1—N6—C26—C22	179.7 (3)
C15—C10—C11—C12	1.4 (6)	C25—N5—C26—N6	−179.2 (3)
Ir1—C10—C11—C12	−173.6 (3)	Ir1—N5—C26—N6	0.5 (3)
C10—C11—C12—C13	−1.4 (6)	C25—N5—C26—C22	0.6 (6)
C11—C12—C13—C14	0.1 (8)	Ir1—N5—C26—C22	−179.7 (3)
C12—C13—C14—C15	1.1 (8)	C23—C22—C26—N6	179.1 (4)
C13—C14—C15—C10	−1.0 (8)	C21—C22—C26—N6	−0.3 (6)
C13—C14—C15—N4	176.6 (5)	C23—C22—C26—N5	−0.6 (6)
C11—C10—C15—C14	−0.3 (7)	C21—C22—C26—N5	179.9 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···F1	0.93	2.47	3.239 (4)	140
C9—H9A···F4	0.93	2.48	3.386 (5)	164
C16—H16A···F5^i	0.93	2.46	3.018 (5)	118
C16—H16A···F6^i	0.93	2.51	3.418 (6)	167
C7—H7A···F5^ii	0.93	2.46	3.201 (5)	136
C25—H25A···F5^iii	0.93	2.32	3.215 (4)	160
C27—H27A···F2^iv	0.97	2.52	3.370 (13)	146

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