Crystal structure of mer-tris­{2,6-di­fluoro-3-[5-(2-fluoro­phen­yl)pyridin-2-yl-κN]pyridin-4-yl-κC⁴}iridium(III) di­chloro­methane hemisolvate n-hexane hemisolvate

Iridium(III) complexes based on 2,3′-bi­pyridine ligands are known to exhibit strong emission from blue to green that makes them of inter­est for organic light-emitting diodes and organic lighting uses. In the title compound, the Ir^III ion adopts a distorted octa­hedral coordination environment defined by three C,N-chelating 2,6-di­fluoro-3-[5-(2-fluoro­phen­yl)pyridin-2-yl]pyridin-4-yl ligands in a meridional manner. In the crystal, inter­molecular C—H...F and C—H...π hydrogen bonds, as well as inter­molecular C—F...π inter­actions, are present, leading to a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in solvent or counterion
• R factor = 0.030
• wR factor = 0.080
• Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C53      - C54      .       1.40 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C54      - C54_b    .       1.36 Ang.
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  <I>CG</I> Check
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  <I>CG</I> Check
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  <I>CG</I> Check
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  <I>CG</I> Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          8 Report
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.46A   From Cl1             2.22 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  0.56A   From Cl1            -1.99 eA-3
PLAT972_ALERT_2_C Check Calcd Resid. Dens.  0.63A   From Cl1            -1.59 eA-3

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          2 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by a Factor ...       0.50 Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT300_ALERT_4_G Atom Site Occupancy of C55        Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H55A       Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of H55B       Constrained at        0.5 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )        33% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         16 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

mer-Tris{2,6-difluoro-3-[5-(2-fluorophenyl)pyridin-2-yl-κN]pyridin-4-yl-κC⁴}iridium(III) dichloromethane hemisolvate n-hexane hemisolvate

Crystal data

[Ir(C17H11F2N2)3]·0.5C6H14·0.5CH2Cl2	Z = 2
Mr = 1121.58	F(000) = 1116
Triclinic, P1	Dx = 1.640 Mg m^−3
a = 12.5753 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.4054 (3) Å	Cell parameters from 9893 reflections
c = 14.8668 (3) Å	θ = 2.3–28.2°
α = 117.0678 (5)°	µ = 3.07 mm^−1
β = 101.9336 (6)°	T = 173 K
γ = 97.2102 (6)°	Block, yellow
V = 2270.58 (8) Å^3	0.42 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer	10233 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.035
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 28.3°, θmin = 1.6°
Tmin = 0.532, Tmax = 0.746	h = −16→16
40374 measured reflections	k = −19→19
11187 independent reflections	l = −18→19

Refinement

Refinement on F^2	16 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 1.7767P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.003
11187 reflections	Δρmax = 2.38 e Å^−3
625 parameters	Δρmin = −2.06 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	Occ. (<1)
Ir1	0.80627 (2)	0.75047 (2)	0.53831 (2)	0.01827 (4)
F1	0.8673 (2)	0.6415 (2)	0.8511 (2)	0.0543 (7)
F2	1.12093 (19)	0.59363 (19)	0.6739 (2)	0.0429 (6)
N1	0.9274 (2)	0.6888 (2)	0.4727 (2)	0.0208 (5)
N2	0.9932 (3)	0.6203 (2)	0.7616 (3)	0.0340 (7)
C1	0.8725 (2)	0.6929 (2)	0.6358 (3)	0.0212 (6)
C2	0.8363 (3)	0.6866 (3)	0.7161 (3)	0.0276 (7)
H2	0.7702	0.7072	0.7304	0.033*
C3	0.8993 (3)	0.6498 (3)	0.7734 (3)	0.0341 (8)
C4	1.0248 (3)	0.6251 (3)	0.6851 (3)	0.0298 (7)
C5	0.9706 (3)	0.6581 (2)	0.6176 (3)	0.0232 (6)
C6	1.0025 (2)	0.6582 (2)	0.5291 (3)	0.0229 (6)
C7	1.0955 (3)	0.6311 (3)	0.4960 (3)	0.0303 (7)
H7	1.1495	0.6127	0.5356	0.036*
C8	1.1101 (3)	0.6307 (3)	0.4064 (3)	0.0330 (8)
H8	1.1749	0.6136	0.3859	0.040*
C9	1.0306 (3)	0.6551 (3)	0.3459 (3)	0.0300 (7)
C10	0.9416 (3)	0.6851 (2)	0.3839 (3)	0.0252 (7)
H10	0.8873	0.7041	0.3450	0.030*
C11	1.0395 (3)	0.6562 (3)	0.2480 (3)	0.0339 (8)
C12	1.1385 (4)	0.7141 (4)	0.2506 (4)	0.0489 (11)
H12	1.2007	0.7477	0.3130	0.059*
C13	1.1479 (5)	0.7235 (4)	0.1634 (5)	0.0611 (14)
H13	1.2159	0.7634	0.1662	0.073*
C14	1.0573 (5)	0.6742 (4)	0.0724 (4)	0.0597 (14)
H14	1.0625	0.6816	0.0131	0.072*
C15	0.9605 (5)	0.6148 (4)	0.0677 (4)	0.0510 (11)
H15	0.8996	0.5801	0.0042	0.061*
C16	0.9490 (4)	0.6041 (3)	0.1545 (3)	0.0388 (9)
C17	0.8413 (4)	0.5336 (4)	0.1405 (4)	0.0510 (11)
H17A	0.8564	0.4994	0.1840	0.077*
H17B	0.8090	0.4780	0.0659	0.077*
H17C	0.7882	0.5775	0.1625	0.077*
F3	0.5772 (3)	0.7962 (2)	0.2111 (2)	0.0757 (10)
F4	0.8327 (2)	1.08740 (18)	0.4761 (2)	0.0466 (6)
N3	0.9257 (2)	0.9044 (2)	0.6254 (2)	0.0202 (5)
N4	0.7040 (3)	0.9417 (3)	0.3469 (3)	0.0402 (8)
C18	0.7582 (3)	0.8195 (3)	0.4460 (3)	0.0242 (6)
C19	0.6756 (3)	0.7747 (3)	0.3490 (3)	0.0350 (8)
H19	0.6349	0.7013	0.3136	0.042*
C20	0.6547 (4)	0.8392 (4)	0.3060 (3)	0.0440 (10)
C21	0.7826 (3)	0.9830 (3)	0.4368 (3)	0.0321 (8)
C22	0.8172 (3)	0.9295 (3)	0.4913 (3)	0.0236 (6)
C23	0.9103 (3)	0.9743 (2)	0.5882 (3)	0.0229 (6)
C24	0.9824 (3)	1.0773 (3)	0.6421 (3)	0.0299 (7)
H24	0.9710	1.1270	0.6179	0.036*
C25	1.0702 (3)	1.1068 (3)	0.7304 (3)	0.0307 (7)
H25	1.1189	1.1771	0.7667	0.037*
C26	1.0887 (3)	1.0351 (3)	0.7673 (3)	0.0241 (6)
C27	1.0117 (2)	0.9351 (2)	0.7118 (3)	0.0212 (6)
H27	1.0204	0.8854	0.7365	0.025*
C28	1.1851 (3)	1.0651 (3)	0.8603 (3)	0.0259 (7)
C29	1.2073 (3)	1.1663 (3)	0.9495 (3)	0.0377 (8)
H29	1.1586	1.2118	0.9500	0.045*
C30	1.2990 (4)	1.2017 (3)	1.0375 (3)	0.0457 (10)
H30	1.3132	1.2709	1.0976	0.055*
C31	1.3691 (3)	1.1359 (4)	1.0369 (3)	0.0459 (11)
H31	1.4327	1.1599	1.0964	0.055*
C32	1.3476 (3)	1.0351 (3)	0.9502 (3)	0.0380 (9)
H32	1.3965	0.9903	0.9516	0.046*
C33	1.2560 (3)	0.9967 (3)	0.8603 (3)	0.0293 (7)
C34	1.2406 (3)	0.8875 (3)	0.7682 (3)	0.0349 (8)
H34A	1.2296	0.8922	0.7033	0.052*
H34B	1.1748	0.8377	0.7613	0.052*
H34C	1.3075	0.8611	0.7796	0.052*
F5	0.5676 (2)	0.34823 (18)	0.2318 (2)	0.0532 (7)
F6	0.38409 (17)	0.55554 (19)	0.4386 (2)	0.0466 (6)
N5	0.6894 (2)	0.8035 (2)	0.6117 (2)	0.0210 (5)
N6	0.4774 (3)	0.4534 (3)	0.3367 (3)	0.0386 (8)
C35	0.6786 (3)	0.6197 (3)	0.4518 (3)	0.0232 (6)
C36	0.6739 (3)	0.5210 (3)	0.3648 (3)	0.0298 (7)
H36	0.7383	0.5075	0.3418	0.036*
C37	0.5732 (3)	0.4448 (3)	0.3142 (3)	0.0356 (8)
C38	0.4829 (3)	0.5465 (3)	0.4172 (3)	0.0324 (8)
C39	0.5777 (3)	0.6319 (3)	0.4795 (3)	0.0255 (7)
C40	0.5854 (3)	0.7342 (3)	0.5712 (3)	0.0246 (6)
C41	0.5035 (3)	0.7659 (3)	0.6217 (3)	0.0325 (8)
H41	0.4299	0.7199	0.5929	0.039*
C42	0.5293 (3)	0.8633 (3)	0.7127 (3)	0.0339 (8)
H42	0.4734	0.8836	0.7469	0.041*
C43	0.6366 (3)	0.9335 (3)	0.7561 (3)	0.0256 (7)
C44	0.7122 (3)	0.8998 (3)	0.6997 (3)	0.0243 (6)
H44	0.7842	0.9473	0.7245	0.029*
C45	0.6669 (3)	1.0390 (3)	0.8546 (3)	0.0288 (7)
C46	0.5870 (3)	1.0993 (3)	0.8704 (3)	0.0356 (8)
H46	0.5167	1.0726	0.8173	0.043*
C47	0.6081 (4)	1.1971 (3)	0.9618 (3)	0.0428 (9)
H47	0.5525	1.2367	0.9713	0.051*
C48	0.7093 (4)	1.2364 (3)	1.0383 (3)	0.0456 (10)
H48	0.7247	1.3038	1.1009	0.055*
C49	0.7893 (3)	1.1773 (3)	1.0239 (3)	0.0385 (9)
H49	0.8592	1.2055	1.0778	0.046*
C50	0.7712 (3)	1.0787 (3)	0.9339 (3)	0.0311 (7)
C51	0.8620 (3)	1.0185 (4)	0.9291 (3)	0.0417 (9)
H51A	0.8275	0.9409	0.8916	0.063*
H51B	0.9071	1.0410	1.0011	0.063*
H51C	0.9104	1.0347	0.8915	0.063*
C52	0.3642 (9)	0.5534 (10)	0.1629 (11)	0.164 (5)
H52A	0.3244	0.5125	0.1889	0.246*
H52B	0.4233	0.6141	0.2223	0.246*
H52C	0.3111	0.5806	0.1289	0.246*
C53	0.4179 (10)	0.4784 (9)	0.0806 (10)	0.143 (4)
H53A	0.4697	0.4498	0.1153	0.171*
H53B	0.3576	0.4164	0.0220	0.171*
C54	0.4771 (10)	0.5289 (7)	0.0381 (9)	0.140 (4)
H54A	0.4255	0.5619	0.0091	0.168*
H54C	0.5386	0.5887	0.0977	0.168*
C55	0.4858 (8)	1.0429 (5)	0.4679 (6)	0.070 (3)	0.5
H55A	0.5258	1.0535	0.4212	0.084*	0.5
H55B	0.4281	1.0844	0.4747	0.084*	0.5
Cl1	0.4193 (4)	0.9067 (4)	0.4086 (4)	0.245 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.01779 (6)	0.01590 (6)	0.02123 (7)	0.00411 (4)	0.00436 (4)	0.00994 (5)
F1	0.0766 (18)	0.0687 (17)	0.0456 (15)	0.0301 (14)	0.0258 (14)	0.0449 (14)
F2	0.0406 (12)	0.0478 (13)	0.0472 (14)	0.0263 (10)	0.0083 (10)	0.0272 (12)
N1	0.0205 (12)	0.0147 (12)	0.0255 (14)	0.0042 (9)	0.0059 (10)	0.0090 (11)
N2	0.0455 (17)	0.0254 (15)	0.0286 (16)	0.0110 (13)	0.0018 (14)	0.0147 (13)
C1	0.0210 (13)	0.0137 (13)	0.0243 (16)	−0.0001 (11)	0.0012 (12)	0.0092 (12)
C2	0.0326 (17)	0.0247 (16)	0.0260 (17)	0.0048 (13)	0.0065 (14)	0.0144 (15)
C3	0.049 (2)	0.0285 (18)	0.0264 (18)	0.0083 (16)	0.0070 (16)	0.0173 (16)
C4	0.0316 (17)	0.0196 (15)	0.0303 (18)	0.0082 (13)	−0.0005 (14)	0.0096 (14)
C5	0.0233 (14)	0.0149 (14)	0.0267 (16)	0.0040 (11)	0.0009 (12)	0.0096 (13)
C6	0.0216 (14)	0.0151 (14)	0.0260 (16)	0.0038 (11)	0.0032 (12)	0.0071 (13)
C7	0.0259 (15)	0.0233 (16)	0.036 (2)	0.0095 (13)	0.0059 (14)	0.0102 (15)
C8	0.0266 (16)	0.0265 (17)	0.041 (2)	0.0090 (13)	0.0154 (15)	0.0103 (16)
C9	0.0368 (18)	0.0184 (15)	0.0346 (19)	0.0066 (13)	0.0173 (15)	0.0103 (15)
C10	0.0331 (16)	0.0166 (14)	0.0278 (17)	0.0061 (12)	0.0122 (14)	0.0114 (13)
C11	0.050 (2)	0.0235 (16)	0.040 (2)	0.0162 (15)	0.0278 (18)	0.0172 (16)
C12	0.057 (3)	0.042 (2)	0.053 (3)	0.009 (2)	0.032 (2)	0.022 (2)
C13	0.071 (3)	0.057 (3)	0.083 (4)	0.018 (3)	0.053 (3)	0.044 (3)
C14	0.092 (4)	0.056 (3)	0.061 (3)	0.035 (3)	0.051 (3)	0.038 (3)
C15	0.079 (3)	0.048 (3)	0.047 (3)	0.029 (2)	0.034 (2)	0.030 (2)
C16	0.057 (2)	0.0300 (19)	0.040 (2)	0.0194 (17)	0.0244 (19)	0.0198 (18)
C17	0.062 (3)	0.052 (3)	0.040 (2)	0.010 (2)	0.013 (2)	0.026 (2)
F3	0.092 (2)	0.0570 (17)	0.0537 (18)	0.0057 (16)	−0.0304 (16)	0.0328 (15)
F4	0.0643 (15)	0.0293 (11)	0.0506 (15)	0.0084 (10)	0.0053 (12)	0.0290 (11)
N3	0.0202 (11)	0.0174 (12)	0.0256 (14)	0.0064 (9)	0.0090 (10)	0.0115 (11)
N4	0.0490 (19)	0.0394 (18)	0.0415 (19)	0.0159 (15)	0.0069 (16)	0.0291 (17)
C18	0.0242 (15)	0.0263 (16)	0.0272 (17)	0.0100 (12)	0.0090 (13)	0.0159 (14)
C19	0.0382 (19)	0.0275 (18)	0.0309 (19)	0.0045 (14)	−0.0030 (15)	0.0142 (16)
C20	0.051 (2)	0.044 (2)	0.034 (2)	0.0133 (18)	−0.0040 (18)	0.0230 (19)
C21	0.0415 (19)	0.0271 (17)	0.036 (2)	0.0128 (15)	0.0114 (16)	0.0215 (16)
C22	0.0267 (15)	0.0240 (15)	0.0264 (17)	0.0110 (12)	0.0096 (13)	0.0156 (14)
C23	0.0246 (14)	0.0194 (14)	0.0286 (17)	0.0084 (12)	0.0109 (13)	0.0132 (14)
C24	0.0330 (17)	0.0217 (16)	0.039 (2)	0.0084 (13)	0.0110 (15)	0.0181 (16)
C25	0.0341 (17)	0.0158 (15)	0.035 (2)	0.0017 (13)	0.0069 (15)	0.0095 (15)
C26	0.0235 (14)	0.0197 (15)	0.0266 (17)	0.0031 (12)	0.0092 (13)	0.0093 (14)
C27	0.0184 (13)	0.0195 (14)	0.0249 (16)	0.0033 (11)	0.0063 (12)	0.0108 (13)
C28	0.0231 (14)	0.0242 (16)	0.0265 (17)	−0.0021 (12)	0.0050 (13)	0.0125 (14)
C29	0.041 (2)	0.0283 (18)	0.033 (2)	−0.0028 (15)	0.0063 (16)	0.0110 (17)
C30	0.049 (2)	0.037 (2)	0.030 (2)	−0.0120 (18)	0.0022 (18)	0.0100 (18)
C31	0.037 (2)	0.052 (3)	0.038 (2)	−0.0142 (18)	−0.0050 (17)	0.027 (2)
C32	0.0257 (16)	0.044 (2)	0.042 (2)	−0.0016 (15)	0.0002 (16)	0.027 (2)
C33	0.0223 (15)	0.0310 (18)	0.0323 (19)	−0.0002 (13)	0.0052 (14)	0.0167 (16)
C34	0.0271 (16)	0.0335 (19)	0.041 (2)	0.0092 (14)	0.0068 (15)	0.0174 (18)
F5	0.0495 (14)	0.0276 (12)	0.0478 (15)	−0.0026 (10)	0.0112 (12)	−0.0048 (11)
F6	0.0240 (10)	0.0421 (13)	0.0539 (15)	−0.0029 (9)	0.0100 (10)	0.0113 (12)
N5	0.0172 (11)	0.0211 (13)	0.0258 (14)	0.0053 (9)	0.0044 (10)	0.0131 (11)
N6	0.0332 (16)	0.0273 (16)	0.0378 (18)	−0.0041 (12)	0.0028 (14)	0.0082 (14)
C35	0.0220 (14)	0.0212 (15)	0.0263 (16)	0.0028 (11)	0.0032 (12)	0.0139 (14)
C36	0.0281 (16)	0.0230 (16)	0.0315 (18)	0.0040 (13)	0.0058 (14)	0.0098 (15)
C37	0.0369 (19)	0.0219 (17)	0.034 (2)	0.0007 (14)	0.0062 (16)	0.0063 (16)
C38	0.0230 (15)	0.0324 (18)	0.038 (2)	0.0016 (13)	0.0072 (14)	0.0162 (17)
C39	0.0247 (15)	0.0232 (16)	0.0270 (17)	0.0042 (12)	0.0065 (13)	0.0120 (14)
C40	0.0197 (14)	0.0234 (15)	0.0288 (17)	0.0038 (12)	0.0054 (13)	0.0124 (14)
C41	0.0215 (15)	0.0345 (19)	0.036 (2)	0.0012 (13)	0.0090 (14)	0.0140 (17)
C42	0.0262 (16)	0.038 (2)	0.038 (2)	0.0101 (14)	0.0149 (15)	0.0172 (18)
C43	0.0255 (15)	0.0276 (16)	0.0273 (17)	0.0091 (13)	0.0081 (13)	0.0157 (15)
C44	0.0226 (14)	0.0244 (16)	0.0284 (17)	0.0069 (12)	0.0090 (13)	0.0143 (14)
C45	0.0320 (16)	0.0278 (17)	0.0304 (18)	0.0093 (13)	0.0150 (14)	0.0146 (15)
C46	0.0383 (19)	0.037 (2)	0.036 (2)	0.0157 (16)	0.0150 (16)	0.0181 (17)
C47	0.054 (2)	0.039 (2)	0.042 (2)	0.0218 (19)	0.026 (2)	0.0185 (19)
C48	0.066 (3)	0.030 (2)	0.034 (2)	0.0056 (19)	0.024 (2)	0.0084 (18)
C49	0.040 (2)	0.037 (2)	0.0301 (19)	−0.0029 (16)	0.0104 (16)	0.0135 (17)
C50	0.0311 (17)	0.0330 (18)	0.0300 (18)	0.0037 (14)	0.0116 (15)	0.0164 (16)
C51	0.0281 (18)	0.056 (3)	0.036 (2)	0.0114 (17)	0.0069 (16)	0.019 (2)
C52	0.114 (8)	0.181 (12)	0.207 (14)	0.014 (8)	0.007 (8)	0.126 (11)
C53	0.183 (11)	0.123 (8)	0.161 (11)	0.051 (8)	0.048 (9)	0.100 (8)
C54	0.172 (10)	0.068 (6)	0.172 (12)	0.019 (6)	0.064 (8)	0.050 (7)
C55	0.070 (3)	0.071 (3)	0.071 (3)	0.020 (2)	0.023 (2)	0.035 (2)
Cl1	0.210 (2)	0.257 (3)	0.244 (3)	0.0489 (18)	0.0950 (19)	0.0951 (18)

Geometric parameters (Å, º)

Ir1—C35	1.991 (3)	C29—C30	1.387 (6)
Ir1—N5	2.030 (3)	C29—H29	0.9500
Ir1—N1	2.056 (3)	C30—C31	1.372 (7)
Ir1—C1	2.061 (3)	C30—H30	0.9500
Ir1—C18	2.070 (3)	C31—C32	1.378 (6)
Ir1—N3	2.143 (3)	C31—H31	0.9500
F1—C3	1.349 (4)	C32—C33	1.396 (5)
F2—C4	1.359 (4)	C32—H32	0.9500
N1—C10	1.346 (4)	C33—C34	1.496 (5)
N1—C6	1.378 (4)	C34—H34A	0.9800
N2—C4	1.307 (5)	C34—H34B	0.9800
N2—C3	1.323 (5)	C34—H34C	0.9800
C1—C2	1.397 (5)	F5—C37	1.352 (4)
C1—C5	1.421 (4)	F6—C38	1.352 (4)
C2—C3	1.369 (5)	N5—C44	1.346 (4)
C2—H2	0.9500	N5—C40	1.367 (4)
C4—C5	1.389 (5)	N6—C38	1.310 (5)
C5—C6	1.453 (5)	N6—C37	1.322 (5)
C6—C7	1.393 (5)	C35—C36	1.405 (5)
C7—C8	1.378 (5)	C35—C39	1.420 (4)
C7—H7	0.9500	C36—C37	1.371 (5)
C8—C9	1.392 (5)	C36—H36	0.9500
C8—H8	0.9500	C38—C39	1.389 (5)
C9—C10	1.386 (5)	C39—C40	1.456 (5)
C9—C11	1.490 (5)	C40—C41	1.400 (5)
C10—H10	0.9500	C41—C42	1.372 (5)
C11—C12	1.392 (5)	C41—H41	0.9500
C11—C16	1.404 (6)	C42—C43	1.401 (5)
C12—C13	1.390 (7)	C42—H42	0.9500
C12—H12	0.9500	C43—C44	1.384 (5)
C13—C14	1.385 (8)	C43—C45	1.483 (5)
C13—H13	0.9500	C44—H44	0.9500
C14—C15	1.366 (7)	C45—C46	1.396 (5)
C14—H14	0.9500	C45—C50	1.413 (5)
C15—C16	1.401 (6)	C46—C47	1.384 (6)
C15—H15	0.9500	C46—H46	0.9500
C16—C17	1.502 (6)	C47—C48	1.367 (6)
C17—H17A	0.9800	C47—H47	0.9500
C17—H17B	0.9800	C48—C49	1.385 (6)
C17—H17C	0.9800	C48—H48	0.9500
F3—C20	1.345 (5)	C49—C50	1.386 (5)
F4—C21	1.346 (4)	C49—H49	0.9500
N3—C27	1.343 (4)	C50—C51	1.513 (5)
N3—C23	1.367 (4)	C51—H51A	0.9800
N4—C21	1.305 (5)	C51—H51B	0.9800
N4—C20	1.316 (5)	C51—H51C	0.9800
C18—C19	1.392 (5)	C52—C53	1.562 (14)
C18—C22	1.429 (4)	C52—H52A	0.9800
C19—C20	1.369 (5)	C52—H52B	0.9800
C19—H19	0.9500	C52—H52C	0.9800
C21—C22	1.394 (5)	C53—C54	1.400 (13)
C22—C23	1.460 (5)	C53—H53A	0.9900
C23—C24	1.395 (4)	C53—H53B	0.9900
C24—C25	1.377 (5)	C54—C54^i	1.358 (18)
C24—H24	0.9500	C54—H54A	0.9900
C25—C26	1.396 (5)	C54—H54C	0.9900
C25—H25	0.9500	C55—Cl1^ii	1.727 (3)
C26—C27	1.389 (4)	C55—Cl1	1.741 (3)
C26—C28	1.483 (5)	C55—H55A	0.9900
C27—H27	0.9500	C55—H55B	0.9900
C28—C29	1.395 (5)	Cl1—C55^ii	1.727 (4)
C28—C33	1.410 (5)
C35—Ir1—N5	80.32 (12)	C29—C28—C33	119.4 (3)
C35—Ir1—N1	98.62 (12)	C29—C28—C26	118.1 (3)
N5—Ir1—N1	174.15 (10)	C33—C28—C26	122.4 (3)
C35—Ir1—C1	92.12 (12)	C30—C29—C28	121.3 (4)
N5—Ir1—C1	94.75 (12)	C30—C29—H29	119.4
N1—Ir1—C1	79.51 (12)	C28—C29—H29	119.4
C35—Ir1—C18	94.00 (13)	C31—C30—C29	119.3 (4)
N5—Ir1—C18	88.72 (11)	C31—C30—H30	120.3
N1—Ir1—C18	97.10 (12)	C29—C30—H30	120.3
C1—Ir1—C18	173.39 (11)	C30—C31—C32	120.2 (4)
C35—Ir1—N3	170.98 (11)	C30—C31—H31	119.9
N5—Ir1—N3	94.39 (10)	C32—C31—H31	119.9
N1—Ir1—N3	87.37 (10)	C31—C32—C33	122.0 (4)
C1—Ir1—N3	95.61 (11)	C31—C32—H32	119.0
C18—Ir1—N3	78.49 (12)	C33—C32—H32	119.0
C10—N1—C6	119.6 (3)	C32—C33—C28	117.7 (3)
C10—N1—Ir1	123.6 (2)	C32—C33—C34	118.6 (3)
C6—N1—Ir1	116.6 (2)	C28—C33—C34	123.6 (3)
C4—N2—C3	114.9 (3)	C33—C34—H34A	109.5
C2—C1—C5	117.7 (3)	C33—C34—H34B	109.5
C2—C1—Ir1	129.4 (2)	H34A—C34—H34B	109.5
C5—C1—Ir1	112.8 (2)	C33—C34—H34C	109.5
C3—C2—C1	117.8 (3)	H34A—C34—H34C	109.5
C3—C2—H2	121.1	H34B—C34—H34C	109.5
C1—C2—H2	121.1	C44—N5—C40	120.0 (3)
N2—C3—F1	113.6 (3)	C44—N5—Ir1	122.9 (2)
N2—C3—C2	126.4 (4)	C40—N5—Ir1	117.0 (2)
F1—C3—C2	120.0 (4)	C38—N6—C37	114.1 (3)
N2—C4—F2	113.9 (3)	C36—C35—C39	116.7 (3)
N2—C4—C5	126.7 (3)	C36—C35—Ir1	128.7 (2)
F2—C4—C5	119.4 (3)	C39—C35—Ir1	114.4 (2)
C4—C5—C1	116.4 (3)	C37—C36—C35	117.6 (3)
C4—C5—C6	126.8 (3)	C37—C36—H36	121.2
C1—C5—C6	116.8 (3)	C35—C36—H36	121.2
N1—C6—C7	118.6 (3)	N6—C37—F5	113.9 (3)
N1—C6—C5	112.9 (3)	N6—C37—C36	127.4 (4)
C7—C6—C5	128.5 (3)	F5—C37—C36	118.6 (3)
C8—C7—C6	120.9 (3)	N6—C38—F6	113.8 (3)
C8—C7—H7	119.6	N6—C38—C39	126.6 (3)
C6—C7—H7	119.6	F6—C38—C39	119.5 (3)
C7—C8—C9	120.5 (3)	C38—C39—C35	117.4 (3)
C7—C8—H8	119.8	C38—C39—C40	127.0 (3)
C9—C8—H8	119.8	C35—C39—C40	115.6 (3)
C10—C9—C8	116.5 (3)	N5—C40—C41	118.9 (3)
C10—C9—C11	119.3 (3)	N5—C40—C39	112.5 (3)
C8—C9—C11	124.1 (3)	C41—C40—C39	128.6 (3)
N1—C10—C9	123.8 (3)	C42—C41—C40	120.1 (3)
N1—C10—H10	118.1	C42—C41—H41	120.0
C9—C10—H10	118.1	C40—C41—H41	120.0
C12—C11—C16	119.2 (4)	C41—C42—C43	121.2 (3)
C12—C11—C9	119.0 (4)	C41—C42—H42	119.4
C16—C11—C9	121.7 (3)	C43—C42—H42	119.4
C13—C12—C11	121.1 (5)	C44—C43—C42	115.9 (3)
C13—C12—H12	119.5	C44—C43—C45	121.8 (3)
C11—C12—H12	119.5	C42—C43—C45	122.3 (3)
C14—C13—C12	119.4 (4)	N5—C44—C43	123.7 (3)
C14—C13—H13	120.3	N5—C44—H44	118.1
C12—C13—H13	120.3	C43—C44—H44	118.1
C15—C14—C13	120.3 (5)	C46—C45—C50	119.1 (3)
C15—C14—H14	119.9	C46—C45—C43	118.1 (3)
C13—C14—H14	119.9	C50—C45—C43	122.7 (3)
C14—C15—C16	121.4 (5)	C47—C46—C45	121.4 (4)
C14—C15—H15	119.3	C47—C46—H46	119.3
C16—C15—H15	119.3	C45—C46—H46	119.3
C15—C16—C11	118.7 (4)	C48—C47—C46	119.7 (4)
C15—C16—C17	117.6 (4)	C48—C47—H47	120.2
C11—C16—C17	123.6 (4)	C46—C47—H47	120.2
C16—C17—H17A	109.5	C47—C48—C49	119.6 (4)
C16—C17—H17B	109.5	C47—C48—H48	120.2
H17A—C17—H17B	109.5	C49—C48—H48	120.2
C16—C17—H17C	109.5	C48—C49—C50	122.5 (4)
H17A—C17—H17C	109.5	C48—C49—H49	118.8
H17B—C17—H17C	109.5	C50—C49—H49	118.8
C27—N3—C23	119.4 (3)	C49—C50—C45	117.7 (3)
C27—N3—Ir1	124.7 (2)	C49—C50—C51	118.0 (3)
C23—N3—Ir1	115.9 (2)	C45—C50—C51	124.3 (3)
C21—N4—C20	114.6 (3)	C50—C51—H51A	109.5
C19—C18—C22	116.7 (3)	C50—C51—H51B	109.5
C19—C18—Ir1	129.1 (3)	H51A—C51—H51B	109.5
C22—C18—Ir1	114.1 (2)	C50—C51—H51C	109.5
C20—C19—C18	118.2 (3)	H51A—C51—H51C	109.5
C20—C19—H19	120.9	H51B—C51—H51C	109.5
C18—C19—H19	120.9	C53—C52—H52A	109.5
N4—C20—F3	114.1 (3)	C53—C52—H52B	109.5
N4—C20—C19	127.1 (4)	H52A—C52—H52B	109.5
F3—C20—C19	118.8 (4)	C53—C52—H52C	109.5
N4—C21—F4	113.4 (3)	H52A—C52—H52C	109.5
N4—C21—C22	126.5 (3)	H52B—C52—H52C	109.5
F4—C21—C22	120.1 (3)	C54—C53—C52	114.3 (9)
C21—C22—C18	116.9 (3)	C54—C53—H53A	108.7
C21—C22—C23	126.1 (3)	C52—C53—H53A	108.7
C18—C22—C23	117.0 (3)	C54—C53—H53B	108.7
N3—C23—C24	119.5 (3)	C52—C53—H53B	108.7
N3—C23—C22	114.0 (3)	H53A—C53—H53B	107.6
C24—C23—C22	126.4 (3)	C54^i—C54—C53	120.0 (12)
C25—C24—C23	119.9 (3)	C54^i—C54—H54A	107.3
C25—C24—H24	120.0	C53—C54—H54A	107.3
C23—C24—H24	120.0	C54^i—C54—H54C	107.3
C24—C25—C26	121.1 (3)	C53—C54—H54C	107.3
C24—C25—H25	119.5	H54A—C54—H54C	106.9
C26—C25—H25	119.5	Cl1^ii—C55—Cl1	113.6 (6)
C27—C26—C25	115.9 (3)	Cl1^ii—C55—H55A	108.8
C27—C26—C28	122.8 (3)	Cl1—C55—H55A	108.8
C25—C26—C28	121.4 (3)	Cl1^ii—C55—H55B	108.8
N3—C27—C26	124.1 (3)	Cl1—C55—H55B	108.8
N3—C27—H27	117.9	H55A—C55—H55B	107.7
C26—C27—H27	117.9	C55^ii—Cl1—C55	66.4 (6)
C5—C1—C2—C3	1.5 (5)	C22—C23—C24—C25	−177.0 (3)
Ir1—C1—C2—C3	−176.6 (3)	C23—C24—C25—C26	0.1 (5)
C4—N2—C3—F1	178.4 (3)	C24—C25—C26—C27	−2.0 (5)
C4—N2—C3—C2	−1.9 (6)	C24—C25—C26—C28	178.1 (3)
C1—C2—C3—N2	0.9 (6)	C23—N3—C27—C26	−0.5 (5)
C1—C2—C3—F1	−179.5 (3)	Ir1—N3—C27—C26	179.8 (2)
C3—N2—C4—F2	−179.5 (3)	C25—C26—C27—N3	2.2 (5)
C3—N2—C4—C5	0.4 (5)	C28—C26—C27—N3	−177.8 (3)
N2—C4—C5—C1	1.9 (5)	C27—C26—C28—C29	−134.7 (4)
F2—C4—C5—C1	−178.2 (3)	C25—C26—C28—C29	45.2 (5)
N2—C4—C5—C6	−176.6 (3)	C27—C26—C28—C33	47.1 (5)
F2—C4—C5—C6	3.4 (5)	C25—C26—C28—C33	−133.0 (4)
C2—C1—C5—C4	−2.7 (4)	C33—C28—C29—C30	1.2 (6)
Ir1—C1—C5—C4	175.7 (2)	C26—C28—C29—C30	−177.0 (3)
C2—C1—C5—C6	175.8 (3)	C28—C29—C30—C31	−0.2 (6)
Ir1—C1—C5—C6	−5.7 (3)	C29—C30—C31—C32	−0.8 (6)
C10—N1—C6—C7	4.3 (4)	C30—C31—C32—C33	0.8 (6)
Ir1—N1—C6—C7	−170.7 (2)	C31—C32—C33—C28	0.2 (6)
C10—N1—C6—C5	−175.1 (3)	C31—C32—C33—C34	178.2 (4)
Ir1—N1—C6—C5	9.9 (3)	C29—C28—C33—C32	−1.2 (5)
C4—C5—C6—N1	175.8 (3)	C26—C28—C33—C32	176.9 (3)
C1—C5—C6—N1	−2.6 (4)	C29—C28—C33—C34	−179.0 (3)
C4—C5—C6—C7	−3.5 (5)	C26—C28—C33—C34	−0.9 (5)
C1—C5—C6—C7	178.1 (3)	C39—C35—C36—C37	−0.2 (5)
N1—C6—C7—C8	−2.5 (5)	Ir1—C35—C36—C37	−176.3 (3)
C5—C6—C7—C8	176.8 (3)	C38—N6—C37—F5	179.3 (3)
C6—C7—C8—C9	−1.4 (5)	C38—N6—C37—C36	−0.3 (6)
C7—C8—C9—C10	3.5 (5)	C35—C36—C37—N6	1.1 (6)
C7—C8—C9—C11	−179.8 (3)	C35—C36—C37—F5	−178.5 (3)
C6—N1—C10—C9	−2.2 (5)	C37—N6—C38—F6	178.9 (3)
Ir1—N1—C10—C9	172.4 (2)	C37—N6—C38—C39	−1.6 (6)
C8—C9—C10—N1	−1.7 (5)	N6—C38—C39—C35	2.4 (6)
C11—C9—C10—N1	−178.6 (3)	F6—C38—C39—C35	−178.1 (3)
C10—C9—C11—C12	126.0 (4)	N6—C38—C39—C40	−177.8 (4)
C8—C9—C11—C12	−50.7 (5)	F6—C38—C39—C40	1.8 (6)
C10—C9—C11—C16	−51.4 (5)	C36—C35—C39—C38	−1.3 (5)
C8—C9—C11—C16	131.9 (4)	Ir1—C35—C39—C38	175.4 (3)
C16—C11—C12—C13	1.8 (6)	C36—C35—C39—C40	178.8 (3)
C9—C11—C12—C13	−175.6 (4)	Ir1—C35—C39—C40	−4.5 (4)
C11—C12—C13—C14	−0.2 (7)	C44—N5—C40—C41	1.0 (5)
C12—C13—C14—C15	−1.5 (7)	Ir1—N5—C40—C41	177.7 (3)
C13—C14—C15—C16	1.5 (7)	C44—N5—C40—C39	−177.0 (3)
C14—C15—C16—C11	0.2 (6)	Ir1—N5—C40—C39	−0.3 (4)
C14—C15—C16—C17	−177.5 (4)	C38—C39—C40—N5	−176.8 (3)
C12—C11—C16—C15	−1.8 (5)	C35—C39—C40—N5	3.1 (4)
C9—C11—C16—C15	175.5 (3)	C38—C39—C40—C41	5.5 (6)
C12—C11—C16—C17	175.8 (4)	C35—C39—C40—C41	−174.6 (3)
C9—C11—C16—C17	−6.9 (6)	N5—C40—C41—C42	−2.6 (5)
C22—C18—C19—C20	−1.9 (5)	C39—C40—C41—C42	175.0 (4)
Ir1—C18—C19—C20	176.1 (3)	C40—C41—C42—C43	1.0 (6)
C21—N4—C20—F3	−177.2 (4)	C41—C42—C43—C44	2.1 (5)
C21—N4—C20—C19	1.7 (7)	C41—C42—C43—C45	−179.7 (3)
C18—C19—C20—N4	−0.6 (7)	C40—N5—C44—C43	2.3 (5)
C18—C19—C20—F3	178.3 (4)	Ir1—N5—C44—C43	−174.2 (2)
C20—N4—C21—F4	179.1 (4)	C42—C43—C44—N5	−3.8 (5)
C20—N4—C21—C22	−0.2 (6)	C45—C43—C44—N5	178.0 (3)
N4—C21—C22—C18	−2.2 (6)	C44—C43—C45—C46	139.1 (4)
F4—C21—C22—C18	178.5 (3)	C42—C43—C45—C46	−39.0 (5)
N4—C21—C22—C23	175.5 (4)	C44—C43—C45—C50	−43.0 (5)
F4—C21—C22—C23	−3.7 (6)	C42—C43—C45—C50	138.8 (4)
C19—C18—C22—C21	3.2 (5)	C50—C45—C46—C47	0.2 (6)
Ir1—C18—C22—C21	−175.2 (3)	C43—C45—C46—C47	178.2 (4)
C19—C18—C22—C23	−174.8 (3)	C45—C46—C47—C48	0.4 (6)
Ir1—C18—C22—C23	6.8 (4)	C46—C47—C48—C49	−0.6 (6)
C27—N3—C23—C24	−1.6 (5)	C47—C48—C49—C50	0.2 (6)
Ir1—N3—C23—C24	178.2 (2)	C48—C49—C50—C45	0.5 (6)
C27—N3—C23—C22	177.4 (3)	C48—C49—C50—C51	−176.9 (4)
Ir1—N3—C23—C22	−2.9 (3)	C46—C45—C50—C49	−0.7 (5)
C21—C22—C23—N3	179.7 (3)	C43—C45—C50—C49	−178.5 (3)
C18—C22—C23—N3	−2.5 (4)	C46—C45—C50—C51	176.5 (4)
C21—C22—C23—C24	−1.5 (6)	C43—C45—C50—C51	−1.3 (6)
C18—C22—C23—C24	176.3 (3)	C52—C53—C54—C54^i	−176.7 (15)
N3—C23—C24—C25	1.8 (5)	Cl1^ii—C55—Cl1—C55^ii	0.000 (1)

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

Hydrogen-bond geometry (Å, º)

Cg3, Cg4 and Cg6 are the centroids of the N4/C18–C21, N5/C40–C44, and C45–C50 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···F2	0.95	2.29	2.895 (5)	121
C24—H24···F4	0.95	2.22	2.851 (4)	123
C36—H36···F2^iii	0.95	2.41	3.245 (4)	146
C41—H41···F6	0.95	2.32	2.917 (4)	121
C44—H44···N3	0.95	2.50	3.112 (4)	122
C46—H46···F3^ii	0.95	2.50	3.067 (5)	119
C13—H13···Cg6^iv	0.95	2.98	3.777 (7)	142
C55—H55A···Cg4^ii	0.99	2.96	3.326 (9)	103
C55—H55B···Cg3^ii	0.99	3.00	3.718 (10)	131
C55—H55B···Cg4^ii	0.99	2.78	3.326 (10)	116

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