[(1,2,5,6-η)-Cyclo­octa-1,5-diene](1-ethyl-3-isopropyl-1,3-imidazol-2-yl­idene-κC²)(tri­phenylphosphane-κP)iridium(I) tetra­fluorido­borate

In the title compound, [Ir(C₈H₁₂)(C₈H₁₄N₂)(C₁₈H₁₅P)]BF₄, the cationic complex has the anti­cipated square-planar geometry. The asymmetric unit comprises the iridium complex and one tetra­fluorido­borate anion. The space group is non-centrosymmetric, with the Flack parameter of 0.007 (3) well determined, and confirms the hand for the complex cation. This compound shows promising catalytic activity in transfer hydrogenation reactions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.015
• wR factor = 0.033
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H28    ..  F3      ..       2.58 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11B   ..  F4      ..       2.60 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19    ..  F3      ..       2.60 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16    ..  F2      ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16    ..  F2      ..       2.66 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  F4      ..       2.56 Ang.
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         66 %

Alert level G
PLAT244_ALERT_4_G Low    'Solvent' Ueq as Compared to Neighbors of         B1 Check
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
   7 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
   1 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: Olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

[(1,2,5,6-η)-Cycloocta-1,5-diene](1-ethyl-3-isopropyl-1,3-imidazol-2-ylidene-κC²)(triphenylphosphane-κP)iridium(I) tetrafluoridoborate

Crystal data

C34H41IrN2P^+·BF4^−	F(000) = 1568
Mr = 787.67	Dx = 1.659 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 17.4915 (13) Å	Cell parameters from 9729 reflections
b = 10.2653 (8) Å	θ = 2.3–28.3°
c = 18.644 (2) Å	µ = 4.34 mm^−1
β = 109.6047 (16)°	T = 150 K
V = 3153.5 (5) Å^3	Plate, clear orange
Z = 4	0.3 × 0.2 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	6410 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.026
Absorption correction: multi-scan (SADABS; Bruker, 2012)	θmax = 28.3°, θmin = 2.3°
Tmin = 0.576, Tmax = 0.746	h = −23→13
25634 measured reflections	k = −13→13
6517 independent reflections	l = −24→24

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.015	w = 1/[σ^2(Fo^2)] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.033	(Δ/σ)max = 0.001
S = 1.01	Δρmax = 0.81 e Å^−3
6517 reflections	Δρmin = −0.57 e Å^−3
391 parameters	Absolute structure: Flack x determined using 2467 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al, 2013)
2 restraints	Absolute structure parameter: 0.007 (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	0.38107 (2)	0.82129 (2)	0.58767 (2)	0.01181 (3)
C1	0.2700 (4)	0.8408 (4)	0.6009 (3)	0.0148 (11)
C13	0.4968 (4)	0.8485 (6)	0.5689 (4)	0.0219 (11)
H13	0.4929	0.8445	0.5142	0.026*
C14	0.5403 (3)	0.9684 (4)	0.6107 (2)	0.0275 (10)
H14A	0.5199	1.0462	0.5786	0.033*
H14B	0.5990	0.9603	0.6190	0.033*
N1	0.2213 (2)	0.9453 (3)	0.59388 (18)	0.0161 (7)
N2	0.22893 (16)	0.7402 (3)	0.61841 (16)	0.0164 (5)
C4	0.2575 (2)	0.6041 (3)	0.6270 (2)	0.0220 (7)
H4A	0.3089	0.5989	0.6157	0.026*
H4B	0.2169	0.5491	0.5894	0.026*
C3	0.1544 (2)	0.7809 (3)	0.6207 (2)	0.0204 (7)
H3	0.1146	0.7286	0.6312	0.024*
C12	0.49705 (19)	0.7269 (3)	0.60237 (19)	0.0193 (7)
H12	0.4931	0.6521	0.5669	0.023*
C6	0.2415 (2)	1.0805 (3)	0.57994 (19)	0.0189 (7)
H6	0.2945	1.0796	0.5706	0.023*
P1	0.31715 (7)	0.77862 (11)	0.45900 (6)	0.0133 (2)
C9	0.4315 (3)	0.8179 (3)	0.7132 (3)	0.0198 (11)
H9	0.3896	0.8169	0.7388	0.024*
C10	0.4914 (3)	0.7073 (4)	0.7358 (2)	0.0232 (8)
H10A	0.4615	0.6247	0.7335	0.028*
H10B	0.5271	0.7203	0.7892	0.028*
C29	0.2240 (3)	0.6807 (3)	0.4333 (2)	0.0163 (7)
C23	0.3788 (2)	0.7051 (3)	0.40747 (19)	0.0171 (6)
C22	0.2172 (2)	0.9413 (3)	0.34318 (18)	0.0194 (7)
H22	0.1847	0.8664	0.3245	0.023*
C34	0.1553 (2)	0.7331 (3)	0.44541 (18)	0.0184 (7)
H34	0.1563	0.8210	0.4617	0.022*
C18	0.3319 (2)	1.0435 (3)	0.43574 (19)	0.0200 (7)
H18	0.3779	1.0383	0.4809	0.024*
C19	0.3123 (3)	1.1609 (3)	0.3976 (2)	0.0270 (8)
H19	0.3449	1.2357	0.4161	0.032*
C28	0.4147 (2)	0.5825 (3)	0.43037 (19)	0.0215 (7)
H28	0.4041	0.5363	0.4702	0.026*
C17	0.28505 (19)	0.9328 (3)	0.40866 (18)	0.0166 (6)
C21	0.1968 (2)	1.0597 (3)	0.3051 (2)	0.0262 (8)
H21	0.1502	1.0656	0.2606	0.031*
C16	0.4456 (2)	0.9395 (3)	0.68829 (18)	0.0193 (7)
H16	0.4113	1.0097	0.6990	0.023*
C30	0.2198 (2)	0.5519 (3)	0.40753 (19)	0.0237 (7)
H30	0.2651	0.5144	0.3980	0.028*
C2	0.1494 (2)	0.9095 (3)	0.6053 (2)	0.0200 (7)
H2	0.1052	0.9653	0.6027	0.024*
C33	0.0858 (2)	0.6591 (3)	0.4341 (2)	0.0247 (8)
H33	0.0401	0.6959	0.4432	0.030*
C32	0.0835 (2)	0.5312 (4)	0.4095 (2)	0.0275 (8)
H32	0.0363	0.4799	0.4021	0.033*
C24	0.3962 (2)	0.7705 (3)	0.3494 (2)	0.0215 (7)
H24	0.3727	0.8536	0.3335	0.026*
C11	0.5439 (2)	0.6955 (3)	0.6852 (2)	0.0249 (8)
H11A	0.5907	0.7555	0.7040	0.030*
H11B	0.5654	0.6056	0.6886	0.030*
C20	0.2444 (3)	1.1690 (3)	0.3321 (2)	0.0282 (9)
H20	0.2307	1.2496	0.3057	0.034*
C26	0.4826 (2)	0.5959 (4)	0.3378 (2)	0.0290 (8)
H26	0.5183	0.5593	0.3145	0.035*
C5	0.2714 (2)	0.5513 (3)	0.7060 (2)	0.0276 (8)
H5A	0.2924	0.4622	0.7094	0.041*
H5B	0.2201	0.5512	0.7163	0.041*
H5C	0.3109	0.6064	0.7435	0.041*
C27	0.4655 (2)	0.5290 (4)	0.3950 (2)	0.0265 (8)
H27	0.4890	0.4457	0.4103	0.032*
C8	0.2512 (3)	1.1643 (3)	0.6500 (3)	0.0315 (9)
H8A	0.1988	1.1719	0.6580	0.047*
H8B	0.2704	1.2512	0.6424	0.047*
H8C	0.2907	1.1237	0.6948	0.047*
C31	0.1498 (2)	0.4784 (3)	0.3958 (2)	0.0295 (8)
H31	0.1476	0.3912	0.3783	0.035*
C15	0.5280 (2)	0.9876 (4)	0.6880 (2)	0.0247 (8)
H15A	0.5713	0.9404	0.7277	0.030*
H15B	0.5334	1.0814	0.7012	0.030*
C25	0.4471 (2)	0.7169 (4)	0.3144 (2)	0.0296 (8)
H25	0.4579	0.7625	0.2745	0.036*
C7	0.1775 (2)	1.1369 (4)	0.5098 (2)	0.0303 (8)
H7A	0.1716	1.0805	0.4659	0.045*
H7B	0.1941	1.2242	0.4997	0.045*
H7C	0.1255	1.1424	0.5188	0.045*
F3	0.46323 (17)	0.3183 (2)	0.53320 (17)	0.0442 (7)
F4	0.4980 (2)	0.3779 (4)	0.6562 (2)	0.0893 (14)
B1	0.4349 (3)	0.3333 (4)	0.5942 (3)	0.0272 (9)
F1	0.3696 (3)	0.4149 (3)	0.5731 (3)	0.0969 (17)
F2	0.41140 (18)	0.2160 (3)	0.61307 (19)	0.0560 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.01033 (5)	0.01332 (5)	0.01119 (5)	−0.00084 (8)	0.00286 (3)	−0.00066 (7)
C1	0.016 (3)	0.0157 (18)	0.010 (2)	−0.0001 (16)	0.0005 (18)	−0.0021 (15)
C13	0.009 (2)	0.036 (2)	0.022 (3)	0.000 (2)	0.0065 (19)	−0.004 (2)
C14	0.0154 (18)	0.033 (2)	0.032 (2)	−0.0116 (16)	0.0040 (18)	−0.0027 (18)
N1	0.0129 (14)	0.0152 (13)	0.0190 (16)	−0.0006 (11)	0.0036 (13)	−0.0018 (12)
N2	0.0157 (13)	0.0160 (13)	0.0184 (14)	−0.0017 (11)	0.0070 (11)	−0.0029 (10)
C4	0.0278 (18)	0.0119 (14)	0.0289 (18)	−0.0015 (13)	0.0131 (15)	−0.0013 (13)
C3	0.0181 (16)	0.0232 (16)	0.0236 (17)	−0.0061 (14)	0.0120 (14)	−0.0045 (14)
C12	0.0126 (15)	0.0258 (16)	0.0183 (16)	0.0042 (13)	0.0036 (13)	−0.0049 (14)
C6	0.0192 (16)	0.0154 (15)	0.0235 (17)	0.0005 (12)	0.0088 (14)	−0.0011 (12)
P1	0.0140 (5)	0.0135 (5)	0.0117 (4)	0.0006 (4)	0.0033 (4)	0.0000 (4)
C9	0.019 (2)	0.027 (3)	0.0121 (18)	0.0011 (16)	0.0029 (16)	−0.0018 (15)
C10	0.024 (2)	0.0253 (17)	0.0158 (17)	0.0038 (17)	0.0011 (16)	0.0042 (14)
C29	0.0156 (18)	0.0178 (16)	0.0142 (16)	−0.0023 (12)	0.0034 (14)	0.0018 (12)
C23	0.0153 (16)	0.0201 (15)	0.0148 (15)	−0.0015 (12)	0.0035 (13)	−0.0043 (12)
C22	0.0212 (16)	0.0210 (16)	0.0139 (15)	0.0003 (13)	0.0031 (13)	−0.0007 (12)
C34	0.0162 (16)	0.0190 (15)	0.0177 (16)	−0.0016 (13)	0.0028 (13)	−0.0009 (12)
C18	0.0201 (16)	0.0208 (15)	0.0171 (15)	−0.0021 (13)	0.0036 (13)	0.0011 (13)
C19	0.031 (2)	0.0208 (17)	0.030 (2)	−0.0049 (14)	0.0110 (17)	0.0008 (14)
C28	0.0204 (17)	0.0221 (16)	0.0202 (17)	−0.0004 (13)	0.0043 (14)	−0.0037 (13)
C17	0.0186 (15)	0.0178 (15)	0.0145 (15)	0.0017 (12)	0.0070 (13)	0.0021 (12)
C21	0.0293 (19)	0.0294 (18)	0.0173 (16)	0.0044 (15)	0.0041 (14)	0.0074 (14)
C16	0.0179 (15)	0.0213 (16)	0.0162 (15)	−0.0030 (13)	0.0022 (13)	−0.0064 (12)
C30	0.0227 (17)	0.0225 (16)	0.0245 (17)	−0.0029 (14)	0.0061 (15)	−0.0048 (14)
C2	0.0133 (14)	0.0246 (16)	0.0239 (17)	−0.0006 (13)	0.0087 (13)	−0.0053 (13)
C33	0.0170 (17)	0.0339 (19)	0.0218 (18)	−0.0033 (14)	0.0045 (15)	−0.0009 (14)
C32	0.0233 (18)	0.0285 (18)	0.0285 (19)	−0.0127 (15)	0.0059 (15)	0.0004 (15)
C24	0.0227 (17)	0.0229 (17)	0.0194 (17)	−0.0026 (14)	0.0077 (14)	−0.0016 (13)
C11	0.0190 (18)	0.0278 (18)	0.0234 (19)	0.0072 (14)	0.0013 (15)	0.0001 (14)
C20	0.036 (2)	0.0231 (18)	0.025 (2)	0.0043 (15)	0.0107 (18)	0.0105 (14)
C26	0.0237 (18)	0.036 (2)	0.031 (2)	−0.0038 (16)	0.0133 (16)	−0.0181 (16)
C5	0.033 (2)	0.0200 (16)	0.0297 (19)	−0.0013 (15)	0.0107 (16)	0.0023 (14)
C27	0.0246 (18)	0.0244 (17)	0.0292 (19)	0.0036 (15)	0.0073 (15)	−0.0075 (15)
C8	0.036 (2)	0.0240 (18)	0.039 (2)	−0.0057 (15)	0.018 (2)	−0.0114 (15)
C31	0.0302 (19)	0.0208 (17)	0.034 (2)	−0.0077 (15)	0.0057 (16)	−0.0062 (15)
C15	0.0182 (16)	0.0266 (18)	0.0251 (18)	−0.0053 (14)	0.0017 (14)	−0.0041 (14)
C25	0.032 (2)	0.036 (2)	0.0244 (19)	−0.0092 (17)	0.0146 (17)	−0.0064 (16)
C7	0.029 (2)	0.0283 (18)	0.034 (2)	0.0080 (16)	0.0104 (17)	0.0092 (16)
F3	0.0328 (15)	0.0667 (19)	0.0371 (15)	0.0054 (11)	0.0172 (12)	0.0015 (11)
F4	0.077 (2)	0.137 (3)	0.074 (2)	−0.074 (2)	0.053 (2)	−0.067 (2)
B1	0.028 (2)	0.0185 (19)	0.040 (3)	−0.0021 (16)	0.017 (2)	−0.0008 (16)
F1	0.110 (3)	0.083 (2)	0.134 (4)	0.073 (3)	0.087 (3)	0.062 (3)
F2	0.059 (2)	0.0327 (13)	0.079 (2)	−0.0114 (13)	0.0269 (17)	0.0123 (14)

Geometric parameters (Å, º)

Ir1—C1	2.049 (7)	C34—H34	0.9500
Ir1—C12	2.181 (3)	C18—C19	1.382 (5)
Ir1—C13	2.185 (7)	C18—C17	1.394 (4)
Ir1—C16	2.201 (3)	C18—H18	0.9500
Ir1—C9	2.207 (5)	C19—C20	1.391 (6)
Ir1—P1	2.3232 (11)	C19—H19	0.9500
C1—N1	1.349 (6)	C28—C27	1.385 (5)
C1—N2	1.359 (6)	C28—H28	0.9500
C13—C12	1.395 (7)	C21—C20	1.388 (5)
C13—C14	1.517 (7)	C21—H21	0.9500
C13—H13	1.0000	C16—C15	1.526 (5)
C14—C15	1.540 (6)	C16—H16	1.0000
C14—H14A	0.9900	C30—C31	1.392 (5)
C14—H14B	0.9900	C30—H30	0.9500
N1—C2	1.393 (5)	C2—H2	0.9500
N1—C6	1.477 (4)	C33—C32	1.387 (5)
N2—C3	1.384 (4)	C33—H33	0.9500
N2—C4	1.474 (4)	C32—C31	1.378 (5)
C4—C5	1.511 (5)	C32—H32	0.9500
C4—H4A	0.9900	C24—C25	1.382 (5)
C4—H4B	0.9900	C24—H24	0.9500
C3—C2	1.348 (5)	C11—H11A	0.9900
C3—H3	0.9500	C11—H11B	0.9900
C12—C11	1.520 (5)	C20—H20	0.9500
C12—H12	1.0000	C26—C27	1.383 (5)
C6—C7	1.521 (5)	C26—C25	1.391 (6)
C6—C8	1.526 (5)	C26—H26	0.9500
C6—H6	1.0000	C5—H5A	0.9800
P1—C17	1.829 (3)	C5—H5B	0.9800
P1—C23	1.830 (4)	C5—H5C	0.9800
P1—C29	1.837 (4)	C27—H27	0.9500
C9—C16	1.383 (5)	C8—H8A	0.9800
C9—C10	1.507 (6)	C8—H8B	0.9800
C9—H9	1.0000	C8—H8C	0.9800
C10—C11	1.526 (6)	C31—H31	0.9500
C10—H10A	0.9900	C15—H15A	0.9900
C10—H10B	0.9900	C15—H15B	0.9900
C29—C30	1.400 (4)	C25—H25	0.9500
C29—C34	1.402 (5)	C7—H7A	0.9800
C23—C24	1.392 (5)	C7—H7B	0.9800
C23—C28	1.408 (4)	C7—H7C	0.9800
C22—C17	1.391 (4)	F3—B1	1.393 (6)
C22—C21	1.392 (5)	F4—B1	1.381 (6)
C22—H22	0.9500	B1—F2	1.356 (5)
C34—C33	1.387 (5)	B1—F1	1.363 (6)
C1—Ir1—C12	155.25 (16)	C19—C18—C17	120.7 (3)
C1—Ir1—C13	166.86 (13)	C19—C18—H18	119.7
C12—Ir1—C13	37.26 (17)	C17—C18—H18	119.7
C1—Ir1—C16	94.56 (17)	C18—C19—C20	119.7 (3)
C12—Ir1—C16	87.05 (13)	C18—C19—H19	120.1
C13—Ir1—C16	80.12 (19)	C20—C19—H19	120.1
C1—Ir1—C9	86.1 (2)	C27—C28—C23	120.2 (3)
C12—Ir1—C9	80.55 (17)	C27—C28—H28	119.9
C13—Ir1—C9	96.3 (2)	C23—C28—H28	119.9
C16—Ir1—C9	36.56 (13)	C22—C17—C18	119.5 (3)
C1—Ir1—P1	89.72 (16)	C22—C17—P1	122.0 (2)
C12—Ir1—P1	98.70 (9)	C18—C17—P1	118.5 (2)
C13—Ir1—P1	90.55 (17)	C20—C21—C22	120.1 (3)
C16—Ir1—P1	156.29 (9)	C20—C21—H21	120.0
C9—Ir1—P1	167.06 (11)	C22—C21—H21	120.0
N1—C1—N2	105.1 (5)	C9—C16—C15	124.7 (4)
N1—C1—Ir1	131.3 (4)	C9—C16—Ir1	72.0 (2)
N2—C1—Ir1	123.6 (3)	C15—C16—Ir1	113.0 (2)
C12—C13—C14	124.8 (5)	C9—C16—H16	113.4
C12—C13—Ir1	71.2 (3)	C15—C16—H16	113.4
C14—C13—Ir1	110.7 (4)	Ir1—C16—H16	113.4
C12—C13—H13	114.1	C31—C30—C29	120.5 (3)
C14—C13—H13	114.1	C31—C30—H30	119.8
Ir1—C13—H13	114.1	C29—C30—H30	119.8
C13—C14—C15	112.4 (4)	C3—C2—N1	107.1 (3)
C13—C14—H14A	109.1	C3—C2—H2	126.5
C15—C14—H14A	109.1	N1—C2—H2	126.5
C13—C14—H14B	109.1	C32—C33—C34	119.7 (4)
C15—C14—H14B	109.1	C32—C33—H33	120.2
H14A—C14—H14B	107.9	C34—C33—H33	120.2
C1—N1—C2	110.4 (3)	C31—C32—C33	120.0 (3)
C1—N1—C6	125.7 (4)	C31—C32—H32	120.0
C2—N1—C6	123.8 (3)	C33—C32—H32	120.0
C1—N2—C3	110.9 (3)	C25—C24—C23	121.3 (3)
C1—N2—C4	124.0 (3)	C25—C24—H24	119.4
C3—N2—C4	124.9 (3)	C23—C24—H24	119.4
N2—C4—C5	112.5 (3)	C12—C11—C10	112.3 (3)
N2—C4—H4A	109.1	C12—C11—H11A	109.1
C5—C4—H4A	109.1	C10—C11—H11A	109.1
N2—C4—H4B	109.1	C12—C11—H11B	109.1
C5—C4—H4B	109.1	C10—C11—H11B	109.1
H4A—C4—H4B	107.8	H11A—C11—H11B	107.9
C2—C3—N2	106.5 (3)	C21—C20—C19	120.1 (3)
C2—C3—H3	126.8	C21—C20—H20	120.0
N2—C3—H3	126.8	C19—C20—H20	120.0
C13—C12—C11	124.3 (4)	C27—C26—C25	119.7 (3)
C13—C12—Ir1	71.5 (3)	C27—C26—H26	120.1
C11—C12—Ir1	112.6 (2)	C25—C26—H26	120.1
C13—C12—H12	113.7	C4—C5—H5A	109.5
C11—C12—H12	113.7	C4—C5—H5B	109.5
Ir1—C12—H12	113.7	H5A—C5—H5B	109.5
N1—C6—C7	111.0 (3)	C4—C5—H5C	109.5
N1—C6—C8	110.1 (3)	H5A—C5—H5C	109.5
C7—C6—C8	111.1 (3)	H5B—C5—H5C	109.5
N1—C6—H6	108.2	C26—C27—C28	120.6 (3)
C7—C6—H6	108.2	C26—C27—H27	119.7
C8—C6—H6	108.2	C28—C27—H27	119.7
C17—P1—C23	102.75 (16)	C6—C8—H8A	109.5
C17—P1—C29	104.30 (16)	C6—C8—H8B	109.5
C23—P1—C29	105.38 (16)	H8A—C8—H8B	109.5
C17—P1—Ir1	108.98 (11)	C6—C8—H8C	109.5
C23—P1—Ir1	117.10 (12)	H8A—C8—H8C	109.5
C29—P1—Ir1	116.74 (13)	H8B—C8—H8C	109.5
C16—C9—C10	126.1 (5)	C32—C31—C30	120.6 (3)
C16—C9—Ir1	71.5 (2)	C32—C31—H31	119.7
C10—C9—Ir1	107.6 (3)	C30—C31—H31	119.7
C16—C9—H9	114.3	C16—C15—C14	113.0 (3)
C10—C9—H9	114.3	C16—C15—H15A	109.0
Ir1—C9—H9	114.3	C14—C15—H15A	109.0
C9—C10—C11	113.2 (3)	C16—C15—H15B	109.0
C9—C10—H10A	108.9	C14—C15—H15B	109.0
C11—C10—H10A	108.9	H15A—C15—H15B	107.8
C9—C10—H10B	108.9	C24—C25—C26	119.8 (4)
C11—C10—H10B	108.9	C24—C25—H25	120.1
H10A—C10—H10B	107.8	C26—C25—H25	120.1
C30—C29—C34	118.0 (3)	C6—C7—H7A	109.5
C30—C29—P1	123.1 (3)	C6—C7—H7B	109.5
C34—C29—P1	118.8 (2)	H7A—C7—H7B	109.5
C24—C23—C28	118.3 (3)	C6—C7—H7C	109.5
C24—C23—P1	122.1 (3)	H7A—C7—H7C	109.5
C28—C23—P1	119.4 (3)	H7B—C7—H7C	109.5
C17—C22—C21	120.0 (3)	F2—B1—F1	108.8 (4)
C17—C22—H22	120.0	F2—B1—F4	107.6 (4)
C21—C22—H22	120.0	F1—B1—F4	113.2 (4)
C33—C34—C29	121.3 (3)	F2—B1—F3	109.6 (3)
C33—C34—H34	119.4	F1—B1—F3	109.0 (4)
C29—C34—H34	119.4	F4—B1—F3	108.5 (4)
C12—C13—C14—C15	−44.5 (7)	P1—C23—C28—C27	−176.1 (3)
Ir1—C13—C14—C15	36.4 (5)	C21—C22—C17—C18	0.3 (5)
N2—C1—N1—C2	−1.4 (5)	C21—C22—C17—P1	−177.5 (3)
Ir1—C1—N1—C2	177.5 (4)	C19—C18—C17—C22	−0.9 (5)
N2—C1—N1—C6	175.8 (3)	C19—C18—C17—P1	177.0 (3)
Ir1—C1—N1—C6	−5.4 (7)	C23—P1—C17—C22	85.0 (3)
N1—C1—N2—C3	1.3 (5)	C29—P1—C17—C22	−24.8 (3)
Ir1—C1—N2—C3	−177.6 (3)	Ir1—P1—C17—C22	−150.1 (3)
N1—C1—N2—C4	176.3 (3)	C23—P1—C17—C18	−92.8 (3)
Ir1—C1—N2—C4	−2.7 (6)	C29—P1—C17—C18	157.4 (3)
C1—N2—C4—C5	118.7 (4)	Ir1—P1—C17—C18	32.0 (3)
C3—N2—C4—C5	−67.0 (4)	C17—C22—C21—C20	0.4 (5)
C1—N2—C3—C2	−0.8 (4)	C10—C9—C16—C15	−7.2 (7)
C4—N2—C3—C2	−175.7 (3)	Ir1—C9—C16—C15	−105.9 (3)
C14—C13—C12—C11	−2.6 (8)	C10—C9—C16—Ir1	98.6 (4)
Ir1—C13—C12—C11	−105.2 (4)	C34—C29—C30—C31	−1.2 (5)
C14—C13—C12—Ir1	102.6 (6)	P1—C29—C30—C31	173.9 (3)
C1—N1—C6—C7	125.0 (4)	N2—C3—C2—N1	−0.1 (4)
C2—N1—C6—C7	−58.1 (4)	C1—N1—C2—C3	0.9 (4)
C1—N1—C6—C8	−111.6 (4)	C6—N1—C2—C3	−176.3 (3)
C2—N1—C6—C8	65.2 (4)	C29—C34—C33—C32	−0.8 (5)
C16—C9—C10—C11	−38.8 (6)	C34—C33—C32—C31	−0.5 (6)
Ir1—C9—C10—C11	40.8 (4)	C28—C23—C24—C25	0.4 (5)
C17—P1—C29—C30	131.1 (3)	P1—C23—C24—C25	175.8 (3)
C23—P1—C29—C30	23.3 (3)	C13—C12—C11—C10	95.9 (5)
Ir1—P1—C29—C30	−108.6 (3)	Ir1—C12—C11—C10	13.5 (4)
C17—P1—C29—C34	−53.9 (3)	C9—C10—C11—C12	−36.7 (5)
C23—P1—C29—C34	−161.7 (3)	C22—C21—C20—C19	−0.6 (6)
Ir1—P1—C29—C34	66.4 (3)	C18—C19—C20—C21	0.0 (6)
C17—P1—C23—C24	4.7 (3)	C25—C26—C27—C28	−1.2 (5)
C29—P1—C23—C24	113.6 (3)	C23—C28—C27—C26	0.9 (5)
Ir1—P1—C23—C24	−114.7 (3)	C33—C32—C31—C30	0.9 (6)
C17—P1—C23—C28	−179.9 (3)	C29—C30—C31—C32	−0.1 (6)
C29—P1—C23—C28	−71.0 (3)	C9—C16—C15—C14	95.5 (4)
Ir1—P1—C23—C28	60.7 (3)	Ir1—C16—C15—C14	12.2 (4)
C30—C29—C34—C33	1.6 (5)	C13—C14—C15—C16	−32.1 (5)
P1—C29—C34—C33	−173.6 (3)	C23—C24—C25—C26	−0.7 (6)
C17—C18—C19—C20	0.8 (6)	C27—C26—C25—C24	1.1 (6)
C24—C23—C28—C27	−0.5 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···F1	0.99	2.43	3.153 (5)	130
C28—H28···F3	0.95	2.58	3.265 (4)	130
C28—H28···F1	0.95	2.52	3.474 (6)	178
C11—H11B···F4	0.99	2.60	3.357 (5)	134
C19—H19···F3^i	0.95	2.60	3.390 (5)	141
C16—H16···F2^i	1.00	2.66	3.134 (4)	109
C16—H16···F2^i	1.00	2.66	3.134 (4)	109
C2—H2···F4^ii	0.95	2.56	3.116 (5)	117

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