(4-Butyl-1-methyl-1,2,4-triazol-5-yl­idene)[(1,2,5,6-η)-cyclo­octa-1,5-diene](tri­phenyl­phosphane)iridium(I) tetra­fluorido­borate

A new triazole-based N-heterocyclic cationic carbene iridium(I) complex with a tetra­fluorido­borate counter-anion, [Ir(C₈H₁₂)(C₇H₁₃N₃)(C₁₈H₁₅P)]BF₄, has been synthesized and structurally characterized. The Ir^I atom of the cationic complex has an expected square-planar coordination environment with unexceptional bond lengths. There are several close F...H contacts between the cations and the anions in the range 2.36–2.58 Å, stabilizing the orientation of the out-sphere [BF₄⁻] counter-anion. In the crystal, C—H...π(ring) inter­actions are observed that orient the phenyl rings of the tri­phenyl­phosphane ligands.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.017
• wR factor = 0.039
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of         B1 Check

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

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

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Computing details

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

(4-Butyl-1-methyl-1,2,4-triazol-5-ylidene)[(1,2,5,6-η)-cycloocta-1,5-diene](triphenylphosphane)iridium(I) tetrafluoridoborate

Crystal data

[Ir(C8H12)(C7H13N3)(C18H15P)]BF4	F(000) = 1568
Mr = 788.66	Dx = 1.655 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8966 (9) Å	Cell parameters from 9226 reflections
b = 16.3247 (17) Å	θ = 2.4–26.4°
c = 20.0560 (19) Å	µ = 4.32 mm^−1
β = 102.285 (4)°	T = 100 K
V = 3166.0 (5) Å^3	Irregular, clear light pink
Z = 4	0.31 × 0.21 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer	5986 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.028
Absorption correction: multi-scan (SADABS; Bruker, 2015)	θmax = 26.4°, θmin = 1.6°
Tmin = 0.668, Tmax = 0.745	h = −9→12
34219 measured reflections	k = −20→20
6457 independent reflections	l = −25→25

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.017	H-atom parameters constrained
wR(F^2) = 0.039	w = 1/[σ^2(Fo^2) + (0.0154P)^2 + 3.1892P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.002
6457 reflections	Δρmax = 0.88 e Å^−3
390 parameters	Δρmin = −0.46 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	0.65716 (2)	0.26151 (2)	0.45405 (2)	0.01160 (3)
P1	0.89650 (6)	0.26064 (3)	0.46457 (3)	0.01218 (11)
F3	0.71162 (17)	0.08389 (9)	0.20651 (8)	0.0358 (4)
F4	0.55953 (16)	0.17666 (10)	0.14868 (7)	0.0353 (4)
F1	0.5266 (2)	0.12606 (12)	0.24796 (9)	0.0503 (5)
F2	0.70664 (17)	0.21312 (10)	0.24647 (9)	0.0433 (4)
N1	0.65074 (19)	0.44904 (11)	0.47394 (9)	0.0162 (4)
N3	0.63018 (19)	0.41838 (11)	0.36915 (9)	0.0161 (4)
N2	0.6419 (2)	0.52330 (12)	0.44004 (10)	0.0211 (4)
C19	0.6459 (2)	0.38401 (13)	0.43264 (11)	0.0133 (4)
C14	1.1314 (2)	0.29788 (13)	0.56684 (11)	0.0173 (5)
H14	1.179953	0.300731	0.530836	0.021*
C1	0.9725 (2)	0.16434 (13)	0.44288 (11)	0.0142 (4)
C7	0.9666 (2)	0.33788 (14)	0.41425 (11)	0.0153 (4)
C30	0.6753 (2)	0.14351 (13)	0.50736 (11)	0.0164 (4)
H30	0.772530	0.124875	0.525058	0.020*
C13	0.9890 (2)	0.28236 (13)	0.55206 (10)	0.0140 (4)
C27	0.4612 (2)	0.26324 (14)	0.49000 (12)	0.0165 (4)
H27	0.439383	0.317551	0.508224	0.020*
C18	0.9175 (2)	0.28029 (14)	0.60557 (11)	0.0169 (4)
H18	0.820762	0.270299	0.596020	0.020*
C6	1.0729 (2)	0.12075 (13)	0.48883 (11)	0.0166 (4)
H6	1.102300	0.139853	0.534351	0.020*
C2	0.9277 (2)	0.13410 (14)	0.37611 (11)	0.0189 (5)
H2	0.856611	0.161719	0.344911	0.023*
C29	0.5865 (2)	0.14483 (14)	0.56032 (11)	0.0191 (5)
H29A	0.639649	0.170571	0.602525	0.023*
H29B	0.565779	0.087741	0.571466	0.023*
C31	0.6252 (2)	0.12923 (13)	0.43760 (11)	0.0173 (5)
H31	0.694465	0.102954	0.414647	0.021*
C33	0.3877 (2)	0.18133 (15)	0.37746 (12)	0.0208 (5)
H33A	0.396562	0.191149	0.329864	0.025*
H33B	0.289372	0.169226	0.376674	0.025*
C26	0.4292 (2)	0.25843 (14)	0.41893 (12)	0.0175 (5)
H26	0.388874	0.309840	0.395824	0.021*
C10	1.0450 (3)	0.46222 (16)	0.33383 (12)	0.0271 (6)
H10	1.070139	0.504338	0.306101	0.033*
C8	0.9513 (2)	0.42037 (14)	0.42979 (11)	0.0174 (5)
H8	0.914969	0.434381	0.468486	0.021*
C28	0.4490 (2)	0.19174 (14)	0.53677 (11)	0.0190 (5)
H28A	0.377662	0.153371	0.512567	0.023*
H28B	0.417828	0.212455	0.577402	0.023*
C20	0.6288 (2)	0.50151 (14)	0.37636 (12)	0.0209 (5)
H20	0.619314	0.539019	0.339443	0.025*
C21	0.6380 (2)	0.37261 (15)	0.30676 (11)	0.0211 (5)
H21A	0.619985	0.313956	0.313919	0.025*
H21B	0.733011	0.377231	0.298694	0.025*
C12	1.0261 (2)	0.31863 (15)	0.35861 (12)	0.0215 (5)
H12	1.040077	0.262983	0.347945	0.026*
C11	1.0647 (3)	0.38084 (17)	0.31903 (12)	0.0275 (6)
H11	1.105034	0.367323	0.281487	0.033*
C9	0.9881 (2)	0.48205 (15)	0.38964 (12)	0.0220 (5)
H9	0.974646	0.537806	0.400139	0.026*
C4	1.0889 (2)	0.02184 (14)	0.40176 (13)	0.0224 (5)
H4	1.130025	−0.025843	0.387538	0.027*
C3	0.9873 (2)	0.06395 (14)	0.35580 (12)	0.0214 (5)
H3	0.958607	0.044591	0.310313	0.026*
C25	0.6757 (2)	0.44862 (14)	0.54844 (11)	0.0201 (5)
H25A	0.770805	0.430993	0.567206	0.030*
H25B	0.611083	0.410699	0.563228	0.030*
H25C	0.661787	0.503904	0.564823	0.030*
C5	1.1299 (2)	0.04971 (14)	0.46846 (12)	0.0208 (5)
H5	1.197231	0.020093	0.500216	0.025*
C22	0.5356 (2)	0.40274 (16)	0.24331 (11)	0.0227 (5)
H22A	0.550364	0.462150	0.237934	0.027*
H22B	0.556200	0.374777	0.202807	0.027*
C24	0.2888 (3)	0.41824 (17)	0.17845 (12)	0.0273 (6)
H24A	0.312914	0.390240	0.139350	0.041*
H24B	0.299661	0.477499	0.173758	0.041*
H24C	0.192680	0.405874	0.180060	0.041*
C15	1.2020 (2)	0.30915 (14)	0.63392 (12)	0.0213 (5)
H15	1.299068	0.318279	0.643787	0.026*
C23	0.3847 (2)	0.38868 (16)	0.24451 (12)	0.0246 (5)
H23A	0.361964	0.418257	0.283794	0.029*
H23B	0.369070	0.329525	0.250673	0.029*
C16	1.1305 (3)	0.30704 (15)	0.68664 (12)	0.0242 (5)
H16	1.178888	0.315308	0.732387	0.029*
C32	0.4761 (2)	0.10623 (14)	0.40586 (12)	0.0200 (5)
H32A	0.434297	0.079092	0.440757	0.024*
H32B	0.475337	0.066578	0.368436	0.024*
B1	0.6273 (3)	0.15018 (17)	0.21277 (13)	0.0199 (5)
C17	0.9887 (3)	0.29291 (15)	0.67276 (11)	0.0224 (5)
H17	0.940288	0.291852	0.708901	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.01031 (5)	0.01204 (5)	0.01236 (4)	0.00107 (3)	0.00225 (3)	0.00077 (3)
P1	0.0116 (3)	0.0132 (3)	0.0115 (2)	0.0014 (2)	0.0020 (2)	0.00072 (19)
F3	0.0445 (10)	0.0277 (8)	0.0356 (9)	0.0155 (7)	0.0094 (7)	0.0015 (7)
F4	0.0410 (9)	0.0387 (9)	0.0223 (8)	0.0116 (7)	−0.0024 (6)	0.0008 (6)
F1	0.0625 (12)	0.0533 (12)	0.0466 (11)	−0.0028 (9)	0.0373 (9)	−0.0002 (8)
F2	0.0370 (9)	0.0358 (9)	0.0489 (10)	0.0014 (8)	−0.0092 (8)	−0.0191 (8)
N1	0.0179 (10)	0.0126 (9)	0.0182 (9)	0.0020 (7)	0.0040 (7)	0.0012 (7)
N3	0.0155 (9)	0.0157 (10)	0.0168 (9)	0.0030 (7)	0.0025 (7)	0.0034 (7)
N2	0.0226 (11)	0.0141 (10)	0.0263 (11)	0.0025 (8)	0.0046 (8)	0.0044 (8)
C19	0.0094 (10)	0.0155 (11)	0.0155 (10)	0.0022 (8)	0.0038 (8)	0.0015 (8)
C14	0.0164 (11)	0.0128 (11)	0.0228 (11)	0.0017 (9)	0.0044 (9)	−0.0002 (9)
C1	0.0118 (10)	0.0141 (11)	0.0176 (11)	−0.0007 (8)	0.0050 (8)	−0.0002 (8)
C7	0.0096 (10)	0.0203 (12)	0.0157 (10)	−0.0006 (9)	0.0017 (8)	0.0036 (8)
C30	0.0156 (11)	0.0113 (11)	0.0223 (11)	0.0026 (9)	0.0042 (9)	0.0024 (8)
C13	0.0154 (11)	0.0108 (10)	0.0145 (10)	0.0013 (8)	0.0005 (8)	0.0008 (8)
C27	0.0100 (10)	0.0167 (11)	0.0237 (11)	0.0015 (9)	0.0053 (9)	−0.0009 (9)
C18	0.0158 (11)	0.0165 (11)	0.0180 (11)	0.0022 (9)	0.0023 (9)	0.0014 (8)
C6	0.0151 (11)	0.0153 (11)	0.0190 (11)	−0.0028 (9)	0.0032 (9)	−0.0004 (8)
C2	0.0159 (11)	0.0210 (12)	0.0191 (11)	−0.0009 (9)	0.0023 (9)	0.0002 (9)
C29	0.0213 (12)	0.0177 (12)	0.0190 (11)	−0.0022 (9)	0.0060 (9)	0.0031 (9)
C31	0.0177 (12)	0.0125 (11)	0.0232 (12)	0.0009 (9)	0.0075 (9)	−0.0003 (8)
C33	0.0164 (12)	0.0255 (13)	0.0192 (11)	−0.0038 (10)	0.0009 (9)	−0.0027 (9)
C26	0.0076 (10)	0.0182 (11)	0.0251 (12)	0.0016 (8)	0.0000 (9)	0.0020 (9)
C10	0.0295 (14)	0.0295 (14)	0.0220 (12)	−0.0114 (11)	0.0045 (10)	0.0085 (10)
C8	0.0130 (11)	0.0202 (12)	0.0182 (11)	0.0002 (9)	0.0015 (8)	0.0011 (9)
C28	0.0172 (12)	0.0213 (12)	0.0201 (11)	−0.0028 (9)	0.0078 (9)	−0.0019 (9)
C20	0.0211 (12)	0.0162 (12)	0.0254 (12)	0.0031 (9)	0.0051 (10)	0.0070 (9)
C21	0.0222 (12)	0.0264 (13)	0.0151 (11)	0.0065 (10)	0.0046 (9)	0.0004 (9)
C12	0.0212 (12)	0.0238 (12)	0.0207 (12)	−0.0019 (10)	0.0073 (9)	−0.0010 (9)
C11	0.0288 (14)	0.0375 (15)	0.0188 (12)	−0.0090 (12)	0.0109 (10)	−0.0013 (10)
C9	0.0203 (12)	0.0191 (12)	0.0244 (12)	−0.0036 (10)	−0.0002 (9)	0.0038 (9)
C4	0.0231 (13)	0.0139 (11)	0.0333 (13)	0.0004 (9)	0.0131 (10)	−0.0039 (9)
C3	0.0228 (12)	0.0207 (12)	0.0222 (12)	−0.0034 (10)	0.0082 (10)	−0.0063 (9)
C25	0.0235 (12)	0.0193 (12)	0.0176 (11)	0.0017 (10)	0.0048 (9)	−0.0024 (9)
C5	0.0154 (11)	0.0166 (12)	0.0295 (13)	0.0019 (9)	0.0028 (9)	0.0016 (9)
C22	0.0255 (13)	0.0276 (13)	0.0152 (11)	0.0055 (10)	0.0051 (9)	0.0029 (9)
C24	0.0248 (13)	0.0332 (15)	0.0214 (12)	0.0077 (11)	−0.0006 (10)	−0.0011 (10)
C15	0.0176 (12)	0.0147 (11)	0.0274 (12)	0.0014 (9)	−0.0048 (9)	−0.0019 (9)
C23	0.0234 (13)	0.0278 (14)	0.0211 (12)	−0.0003 (10)	0.0016 (10)	0.0019 (10)
C16	0.0282 (13)	0.0193 (12)	0.0196 (11)	0.0029 (10)	−0.0067 (10)	−0.0008 (9)
C32	0.0208 (12)	0.0185 (12)	0.0214 (12)	−0.0039 (9)	0.0064 (9)	−0.0053 (9)
B1	0.0218 (14)	0.0206 (13)	0.0173 (12)	0.0026 (11)	0.0043 (10)	−0.0017 (10)
C17	0.0282 (13)	0.0232 (12)	0.0154 (11)	0.0021 (10)	0.0040 (9)	0.0006 (9)

Geometric parameters (Å, º)

Ir1—P1	2.3330 (6)	C33—H33A	0.9900
Ir1—C19	2.043 (2)	C33—H33B	0.9900
Ir1—C30	2.192 (2)	C33—C26	1.516 (3)
Ir1—C27	2.208 (2)	C33—C32	1.543 (3)
Ir1—C31	2.197 (2)	C26—H26	1.0000
Ir1—C26	2.216 (2)	C10—H10	0.9500
P1—C1	1.834 (2)	C10—C11	1.384 (4)
P1—C7	1.841 (2)	C10—C9	1.394 (4)
P1—C13	1.833 (2)	C8—H8	0.9500
F3—B1	1.389 (3)	C8—C9	1.386 (3)
F4—B1	1.386 (3)	C28—H28A	0.9900
F1—B1	1.394 (3)	C28—H28B	0.9900
F2—B1	1.380 (3)	C20—H20	0.9500
N1—N2	1.384 (3)	C21—H21A	0.9900
N1—C19	1.341 (3)	C21—H21B	0.9900
N1—C25	1.462 (3)	C21—C22	1.530 (3)
N3—C19	1.370 (3)	C12—H12	0.9500
N3—C20	1.365 (3)	C12—C11	1.392 (3)
N3—C21	1.474 (3)	C11—H11	0.9500
N2—C20	1.305 (3)	C9—H9	0.9500
C14—H14	0.9500	C4—H4	0.9500
C14—C13	1.400 (3)	C4—C3	1.392 (3)
C14—C15	1.390 (3)	C4—C5	1.389 (3)
C1—C6	1.398 (3)	C3—H3	0.9500
C1—C2	1.407 (3)	C25—H25A	0.9800
C7—C8	1.398 (3)	C25—H25B	0.9800
C7—C12	1.404 (3)	C25—H25C	0.9800
C30—H30	1.0000	C5—H5	0.9500
C30—C29	1.515 (3)	C22—H22A	0.9900
C30—C31	1.401 (3)	C22—H22B	0.9900
C13—C18	1.406 (3)	C22—C23	1.516 (3)
C27—H27	1.0000	C24—H24A	0.9800
C27—C26	1.395 (3)	C24—H24B	0.9800
C27—C28	1.518 (3)	C24—H24C	0.9800
C18—H18	0.9500	C24—C23	1.534 (3)
C18—C17	1.396 (3)	C15—H15	0.9500
C6—H6	0.9500	C15—C16	1.392 (4)
C6—C5	1.389 (3)	C23—H23A	0.9900
C2—H2	0.9500	C23—H23B	0.9900
C2—C3	1.388 (3)	C16—H16	0.9500
C29—H29A	0.9900	C16—C17	1.391 (3)
C29—H29B	0.9900	C32—H32A	0.9900
C29—C28	1.546 (3)	C32—H32B	0.9900
C31—H31	1.0000	C17—H17	0.9500
C31—C32	1.525 (3)
C19—Ir1—P1	91.94 (6)	C33—C26—Ir1	109.39 (15)
C19—Ir1—C30	163.28 (8)	C33—C26—H26	114.1
C19—Ir1—C27	92.51 (8)	C11—C10—H10	120.2
C19—Ir1—C31	158.53 (9)	C11—C10—C9	119.6 (2)
C19—Ir1—C26	87.09 (8)	C9—C10—H10	120.2
C30—Ir1—P1	88.54 (6)	C7—C8—H8	119.5
C30—Ir1—C27	80.69 (8)	C9—C8—C7	121.1 (2)
C30—Ir1—C31	37.22 (8)	C9—C8—H8	119.5
C30—Ir1—C26	96.15 (8)	C27—C28—C29	112.87 (18)
C27—Ir1—P1	156.32 (6)	C27—C28—H28A	109.0
C27—Ir1—C26	36.76 (8)	C27—C28—H28B	109.0
C31—Ir1—P1	96.80 (6)	C29—C28—H28A	109.0
C31—Ir1—C27	87.32 (8)	C29—C28—H28B	109.0
C31—Ir1—C26	79.96 (8)	H28A—C28—H28B	107.8
C26—Ir1—P1	166.86 (6)	N3—C20—H20	124.0
C1—P1—Ir1	116.32 (7)	N2—C20—N3	111.9 (2)
C1—P1—C7	103.62 (10)	N2—C20—H20	124.0
C7—P1—Ir1	116.12 (7)	N3—C21—H21A	108.9
C13—P1—Ir1	112.09 (7)	N3—C21—H21B	108.9
C13—P1—C1	104.27 (10)	N3—C21—C22	113.45 (19)
C13—P1—C7	102.86 (10)	H21A—C21—H21B	107.7
N2—N1—C25	119.05 (18)	C22—C21—H21A	108.9
C19—N1—N2	113.57 (18)	C22—C21—H21B	108.9
C19—N1—C25	127.14 (19)	C7—C12—H12	119.9
C19—N3—C21	124.44 (19)	C11—C12—C7	120.2 (2)
C20—N3—C19	108.08 (18)	C11—C12—H12	119.9
C20—N3—C21	126.70 (19)	C10—C11—C12	120.7 (2)
C20—N2—N1	102.98 (18)	C10—C11—H11	119.7
N1—C19—Ir1	130.67 (16)	C12—C11—H11	119.7
N1—C19—N3	103.41 (18)	C10—C9—H9	120.0
N3—C19—Ir1	125.92 (16)	C8—C9—C10	119.9 (2)
C13—C14—H14	119.8	C8—C9—H9	120.0
C15—C14—H14	119.8	C3—C4—H4	120.1
C15—C14—C13	120.4 (2)	C5—C4—H4	120.1
C6—C1—P1	123.34 (16)	C5—C4—C3	119.9 (2)
C6—C1—C2	119.0 (2)	C2—C3—C4	120.3 (2)
C2—C1—P1	117.67 (16)	C2—C3—H3	119.8
C8—C7—P1	117.78 (17)	C4—C3—H3	119.8
C8—C7—C12	118.5 (2)	N1—C25—H25A	109.5
C12—C7—P1	123.60 (18)	N1—C25—H25B	109.5
Ir1—C30—H30	114.4	N1—C25—H25C	109.5
C29—C30—Ir1	109.27 (14)	H25A—C25—H25B	109.5
C29—C30—H30	114.4	H25A—C25—H25C	109.5
C31—C30—Ir1	71.60 (12)	H25B—C25—H25C	109.5
C31—C30—H30	114.4	C6—C5—C4	120.2 (2)
C31—C30—C29	124.6 (2)	C6—C5—H5	119.9
C14—C13—P1	120.85 (16)	C4—C5—H5	119.9
C14—C13—C18	119.33 (19)	C21—C22—H22A	108.6
C18—C13—P1	119.76 (16)	C21—C22—H22B	108.6
Ir1—C27—H27	113.8	H22A—C22—H22B	107.6
C26—C27—Ir1	71.92 (13)	C23—C22—C21	114.7 (2)
C26—C27—H27	113.8	C23—C22—H22A	108.6
C26—C27—C28	123.9 (2)	C23—C22—H22B	108.6
C28—C27—Ir1	112.53 (14)	H24A—C24—H24B	109.5
C28—C27—H27	113.8	H24A—C24—H24C	109.5
C13—C18—H18	120.0	H24B—C24—H24C	109.5
C17—C18—C13	120.1 (2)	C23—C24—H24A	109.5
C17—C18—H18	120.0	C23—C24—H24B	109.5
C1—C6—H6	119.7	C23—C24—H24C	109.5
C5—C6—C1	120.5 (2)	C14—C15—H15	120.0
C5—C6—H6	119.7	C14—C15—C16	119.9 (2)
C1—C2—H2	120.0	C16—C15—H15	120.0
C3—C2—C1	120.1 (2)	C22—C23—C24	111.7 (2)
C3—C2—H2	120.0	C22—C23—H23A	109.3
C30—C29—H29A	108.9	C22—C23—H23B	109.3
C30—C29—H29B	108.9	C24—C23—H23A	109.3
C30—C29—C28	113.38 (18)	C24—C23—H23B	109.3
H29A—C29—H29B	107.7	H23A—C23—H23B	108.0
C28—C29—H29A	108.9	C15—C16—H16	119.8
C28—C29—H29B	108.9	C17—C16—C15	120.4 (2)
Ir1—C31—H31	113.6	C17—C16—H16	119.8
C30—C31—Ir1	71.18 (12)	C31—C32—C33	112.38 (19)
C30—C31—H31	113.6	C31—C32—H32A	109.1
C30—C31—C32	124.3 (2)	C31—C32—H32B	109.1
C32—C31—Ir1	113.60 (15)	C33—C32—H32A	109.1
C32—C31—H31	113.6	C33—C32—H32B	109.1
H33A—C33—H33B	107.8	H32A—C32—H32B	107.9
C26—C33—H33A	109.0	F3—B1—F1	109.5 (2)
C26—C33—H33B	109.0	F4—B1—F3	109.9 (2)
C26—C33—C32	113.01 (18)	F4—B1—F1	107.5 (2)
C32—C33—H33A	109.0	F2—B1—F3	109.5 (2)
C32—C33—H33B	109.0	F2—B1—F4	109.5 (2)
Ir1—C26—H26	114.1	F2—B1—F1	110.8 (2)
C27—C26—Ir1	71.32 (12)	C18—C17—H17	120.1
C27—C26—C33	125.7 (2)	C16—C17—C18	119.8 (2)
C27—C26—H26	114.1	C16—C17—H17	120.1
Ir1—P1—C1—C6	−120.92 (17)	C30—C31—C32—C33	95.6 (3)
Ir1—P1—C1—C2	59.92 (19)	C13—P1—C1—C6	3.0 (2)
Ir1—P1—C7—C8	64.05 (18)	C13—P1—C1—C2	−176.11 (17)
Ir1—P1—C7—C12	−111.60 (18)	C13—P1—C7—C8	−58.73 (19)
Ir1—P1—C13—C14	−169.45 (15)	C13—P1—C7—C12	125.61 (19)
Ir1—P1—C13—C18	13.1 (2)	C13—C14—C15—C16	−1.6 (3)
Ir1—C30—C29—C28	37.1 (2)	C13—C18—C17—C16	−0.4 (4)
Ir1—C30—C31—C32	−106.2 (2)	C6—C1—C2—C3	−2.8 (3)
Ir1—C27—C26—C33	100.9 (2)	C2—C1—C6—C5	1.5 (3)
Ir1—C27—C28—C29	11.8 (2)	C29—C30—C31—Ir1	101.1 (2)
Ir1—C31—C32—C33	13.0 (2)	C29—C30—C31—C32	−5.1 (3)
P1—C1—C6—C5	−177.65 (17)	C31—C30—C29—C28	−43.4 (3)
P1—C1—C2—C3	176.41 (18)	C26—C27—C28—C29	94.6 (3)
P1—C7—C8—C9	−173.12 (17)	C26—C33—C32—C31	−33.8 (3)
P1—C7—C12—C11	173.78 (18)	C8—C7—C12—C11	−1.8 (3)
P1—C13—C18—C17	176.94 (17)	C28—C27—C26—Ir1	−105.4 (2)
N1—N2—C20—N3	−0.5 (2)	C28—C27—C26—C33	−4.6 (3)
N3—C21—C22—C23	−66.4 (3)	C20—N3—C19—Ir1	−179.37 (16)
N2—N1—C19—Ir1	178.98 (15)	C20—N3—C19—N1	1.0 (2)
N2—N1—C19—N3	−1.4 (2)	C20—N3—C21—C22	−48.3 (3)
C19—N1—N2—C20	1.2 (2)	C21—N3—C19—Ir1	−8.9 (3)
C19—N3—C20—N2	−0.3 (3)	C21—N3—C19—N1	171.45 (19)
C19—N3—C21—C22	143.0 (2)	C21—N3—C20—N2	−170.5 (2)
C14—C13—C18—C17	−0.6 (3)	C21—C22—C23—C24	−178.4 (2)
C14—C15—C16—C17	0.6 (4)	C12—C7—C8—C9	2.8 (3)
C1—P1—C7—C8	−167.13 (17)	C11—C10—C9—C8	−0.2 (4)
C1—P1—C7—C12	17.2 (2)	C9—C10—C11—C12	1.1 (4)
C1—P1—C13—C14	63.90 (19)	C3—C4—C5—C6	−1.9 (4)
C1—P1—C13—C18	−113.56 (18)	C25—N1—N2—C20	176.05 (19)
C1—C6—C5—C4	0.8 (3)	C25—N1—C19—Ir1	4.7 (3)
C1—C2—C3—C4	1.8 (3)	C25—N1—C19—N3	−175.69 (19)
C7—P1—C1—C6	110.38 (19)	C5—C4—C3—C2	0.6 (4)
C7—P1—C1—C2	−68.78 (19)	C15—C14—C13—P1	−175.91 (17)
C7—P1—C13—C14	−44.0 (2)	C15—C14—C13—C18	1.6 (3)
C7—P1—C13—C18	138.53 (18)	C15—C16—C17—C18	0.4 (4)
C7—C8—C9—C10	−1.8 (3)	C32—C33—C26—Ir1	37.6 (2)
C7—C12—C11—C10	−0.1 (4)	C32—C33—C26—C27	−42.9 (3)
C30—C29—C28—C27	−32.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F2	0.95	2.36	3.285 (3)	165
C20—H20···F1^i	0.95	2.47	3.329 (3)	150
C25—H25B···F4^ii	0.98	2.37	3.245 (3)	149

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