cis-Di­chloro­bis(2,2′-bi­quinoline)­iridium(III) hexa­fluoro­phosphate

Yoshikawa, N.; Sakamoto, J.; Kanehisa, N.; Kai, Y.; Matsumura-Inoue, T.; Takashima, H.; Tsukahara, K.

doi:10.1107/S1600536803014235

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cis-Dichlorobis(2,2'-biquinoline)iridium(III) hexafluorophosphate

N. Yoshikawa, J. Sakamoto, N. Kanehisa, Y. Kai, T. Matsumura-Inoue, H. Takashima and K. Tsukahara

The crystal structure of the title compound, [IrCl₂(bqn)₂]PF₆, (bqn is 2,2'-biquinoline, C₁₈H₁₂N₂), contains a monomeric [IrCl₂(bqn)₂]⁺ cation and a hexafluorophosphate anion. The iridium(III) ion is coordinated by four N atoms from two bqn ligands [mean Ir-N distance 2.065 (5) Å] and two Cl atoms [Ir-Cl = 2.342 (2) and 2.353 (2) Å], forming a distorted octahedral environment. Each 2,2'-biquinoline ligand is planar, the mean deviations from the least-squares planes being 0.2431 (6) and 0.1665 (6) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014235/ww6089sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014235/ww6089Isup2.hkl Contains datablock I

CCDC reference: 217432

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.009 Å
R factor = 0.036
wR factor = 0.097
Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
          Tmin and Tmax reported:      0.419     0.644
          Tmin and Tmax expected:      0.359     0.644
          RR =      1.166
          Please check that your absorption correction is appropriate.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         23
                   CL1 -IR1 -N4  -C28    50.00  1.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         24
                   CL1 -IR1 -N4  -C36  -116.00  1.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         25
                   CL2 -IR1 -N1  -C1   -125.90  0.90   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         26
                   CL2 -IR1 -N1  -C9     42.00  1.00   1.555   1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 5 Alert Level C = Please check

Comment top

Extensive studies of the photophysics of octahedral [4 d⁶] and [5 d⁶] complexes have been attracting much attention to the photochemical applications of the complexes on account of their long-lived excited states and good photoluminescence efficiencies. The studies have been focused mainly on the photophysical properties of octahedral metal–diimine complexes of iridium(III) having such ligands as the 2,2'-bipyridine and 1,10-phenanthroline. To our knowledge, no structure of an iridium complex with the 2,2'-biquinoline ligand (bqn) has been reported previously. In this report, we prepared and investigated an iridium bis-polypyridine complex, (I).

The crystal structure of (I) consists of a discrete [IrCl₂(bqn)₂]⁺ cation and a hexafluorophosphate anion. As illustrated in Fig. 1, the Ir^III atom is located in a distorted octahedral environment by two bqn ligands and two chloride anions. The Ir—N bond lengths are in the range 2.056 (5)–2.071 (5) Å. Three trans angles are in the range 168.3 (2)–174.4 (1)°. It is coordinated by four N atoms from a pair of cis-related chelating bqn ligands and two Cl atoms [Ir–Cl1 = 2.342 (2) Å and Ir—Cl2 = 2.353 (2) Å]. The equatorial plane is formed by atoms Cl1, N1, N2 and N4, with the largest deviation from the mean plane being 0.023 (2) Å and the Ir atom being 0.126 (2) Å out of this plane. The axial positions are occupied by the fourth bqn N atom and another Cl atom. Each bqn ligand is planar, the maximum mean deviation from the best planes is 0.205 (6) Å. The dihedral angle between bqn planes is 26.90 (9)°. The two Cl ligands were coordinated in a cis fashion, but PF₆⁻ was not coordinated to iridium metal. The average Ir—N bond length of 2.065 (5) Å and the average N1—Ir—N2 and N3—Ir—N4 angles of 78.0 (2)° compare well with the values published for [IrCl₂(bpy)₂]PF₆ (Yoshikawa et al., 2003; bpy is 2,2'-bipyridine) of 2.026 Å and 79.1°, respectively. No hydrogen-bonding interactions exist in the crystal structure.

Experimental top

The desired complex was prepared by the procedure with a ligand replacement. (NH₄)₃[IrCl₆]·H₂O (0.5 mmol) and 2,2'-biquinoline (1.0 mmol) were mixed in ethylene glycol (15 ml). The suspended mixture was refluxed for 15 min in a microwave oven under a purging nitrogen atmosphere. The mixture was cooled to room temperature. A saturated aqueous solution of KPF₆ (20 ml) was added as a counter-ion, and a brown product began to precipitate and was collected by vacuum filtration. The residue was dissolved in a minimal amount of acetone and flash precipitated in diethyl ether. The product was separated by vacuum filtration and dried under a vacuum. Brown single crystals were obtained by recrystallization from acetonitrile.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: TEXSAN (Molecular Structure Corportation, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

Figures top

Fig. 1. The olecular structure of (I), showing 50% probability displacement ellipsoids.

(I) top

Crystal data top

[IrCl₂(C₁₈H₁₂N₂)₂]PF₆	F(000) = 1792
M_r = 920.70	D_x = 1.879 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 42000 reflections
a = 10.5127 (2) Å	θ = 1.8–27.4°
b = 23.6279 (5) Å	µ = 4.40 mm⁻¹
c = 13.7750 (2) Å	T = 223 K
β = 108.0188 (3)°	Prism, red
V = 3253.8 (1) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku R-AXIS-RAPID Imaging Plate diffractometer	6212 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.045
ω scan	θ_max = 27.4°, θ_min = 1.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −13→13
T_min = 0.419, T_max = 0.644	k = −30→30
27860 measured reflections	l = −17→17
7310 independent reflections

Refinement top

Refinement on F²	Only H-atom displacement parameters refined
R[F² > 2σ(F²)] = 0.036	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.097	(Δ/σ)_max = 0.003
S = 1.30	Δρ_max = 0.90 e Å⁻³
6212 reflections	Δρ_min = −1.17 e Å⁻³
475 parameters

Crystal data top

[IrCl₂(C₁₈H₁₂N₂)₂]PF₆	V = 3253.8 (1) Å³
M_r = 920.70	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5127 (2) Å	µ = 4.40 mm⁻¹
b = 23.6279 (5) Å	T = 223 K
c = 13.7750 (2) Å	0.30 × 0.20 × 0.10 mm
β = 108.0188 (3)°

Data collection top

Rigaku R-AXIS-RAPID Imaging Plate diffractometer	7310 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	6212 reflections with I > 2σ(I)
T_min = 0.419, T_max = 0.644	R_int = 0.045
27860 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	475 parameters
wR(F²) = 0.097	Only H-atom displacement parameters refined
S = 1.30	Δρ_max = 0.90 e Å⁻³
6212 reflections	Δρ_min = −1.17 e Å⁻³

Special details top

Refinement. Refinement using reflections with F² > −10.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ir1	0.26472 (2)	0.01449 (1)	0.73590 (1)	0.02903 (7)
Cl1	0.4962 (1)	0.02929 (6)	0.7918 (1)	0.0504 (3)
Cl2	0.2675 (1)	−0.06151 (5)	0.6262 (1)	0.0440 (3)
P1	−0.2786 (3)	0.21685 (8)	0.6983 (2)	0.0792 (6)
F1	−0.395 (1)	0.2529 (3)	0.6207 (5)	0.182 (4)
F2	−0.231 (1)	0.1985 (3)	0.6079 (6)	0.206 (5)
F3	−0.3707 (8)	0.1643 (2)	0.6803 (5)	0.155 (3)
F4	−0.1729 (7)	0.1807 (3)	0.7759 (5)	0.146 (3)
F5	−0.3406 (6)	0.2375 (2)	0.7837 (4)	0.109 (2)
F6	−0.1869 (9)	0.2697 (2)	0.7223 (8)	0.184 (4)
N1	0.2420 (4)	0.0776 (2)	0.8322 (3)	0.0327 (8)
N2	0.2916 (4)	−0.0294 (2)	0.8708 (3)	0.0350 (9)
N3	0.2071 (4)	0.0667 (2)	0.6094 (3)	0.0328 (8)
N4	0.0582 (4)	0.0090 (2)	0.6925 (3)	0.0329 (8)
C1	0.2474 (5)	0.1356 (2)	0.8206 (4)	0.038 (1)
C2	0.3209 (6)	0.1593 (2)	0.7614 (4)	0.046 (1)
C3	0.3246 (7)	0.2166 (3)	0.7501 (5)	0.059 (2)
C4	0.2561 (8)	0.2521 (3)	0.7985 (7)	0.073 (2)
C5	0.1847 (7)	0.2303 (3)	0.8580 (6)	0.068 (2)
C6	0.1811 (6)	0.1716 (2)	0.8722 (4)	0.050 (1)
C7	0.1186 (6)	0.1468 (3)	0.9380 (5)	0.060 (2)
C8	0.1281 (6)	0.0902 (3)	0.9571 (4)	0.055 (1)
C9	0.1946 (5)	0.0561 (2)	0.9046 (4)	0.039 (1)
C10	0.2255 (5)	−0.0035 (2)	0.9271 (4)	0.037 (1)
C11	0.2001 (6)	−0.0314 (3)	1.0104 (4)	0.049 (1)
C12	0.2470 (6)	−0.0848 (3)	1.0355 (4)	0.056 (2)
C13	0.3259 (6)	−0.1097 (3)	0.9832 (4)	0.050 (1)
C14	0.3881 (7)	−0.1634 (3)	1.0127 (5)	0.063 (2)
C15	0.4684 (8)	−0.1853 (3)	0.9655 (6)	0.073 (2)
C16	0.4940 (6)	−0.1567 (3)	0.8833 (5)	0.062 (2)
C17	0.4362 (5)	−0.1052 (2)	0.8517 (4)	0.047 (1)
C18	0.3501 (5)	−0.0814 (2)	0.9009 (4)	0.037 (1)
C19	0.2834 (5)	0.0872 (2)	0.5517 (3)	0.037 (1)
C20	0.4049 (5)	0.0603 (2)	0.5539 (4)	0.041 (1)
C21	0.4809 (5)	0.0829 (3)	0.4985 (4)	0.047 (1)
C22	0.4415 (7)	0.1331 (3)	0.4420 (4)	0.057 (2)
C23	0.3252 (7)	0.1587 (3)	0.4375 (4)	0.057 (2)
C24	0.2407 (6)	0.1366 (2)	0.4896 (4)	0.045 (1)
C25	0.1150 (6)	0.1593 (3)	0.4823 (4)	0.053 (1)
C26	0.0360 (6)	0.1344 (2)	0.5310 (4)	0.049 (1)
C27	0.0841 (5)	0.0878 (2)	0.5953 (4)	0.039 (1)
C28	0.0023 (5)	0.0550 (2)	0.6445 (4)	0.038 (1)
C29	−0.1300 (5)	0.0708 (3)	0.6394 (4)	0.048 (1)
C30	−0.2000 (5)	0.0368 (3)	0.6832 (4)	0.050 (1)
C31	−0.1489 (5)	−0.0160 (2)	0.7237 (4)	0.043 (1)
C32	−0.2223 (6)	−0.0560 (3)	0.7610 (4)	0.053 (1)
C33	−0.1708 (6)	−0.1067 (3)	0.7934 (5)	0.054 (1)
C34	−0.0432 (6)	−0.1220 (2)	0.7902 (4)	0.049 (1)
C35	0.0334 (5)	−0.0843 (2)	0.7575 (4)	0.040 (1)
C36	−0.0172 (5)	−0.0305 (2)	0.7251 (3)	0.0346 (10)
H(2)	0.3671	0.1354	0.7289	0.0415 (2)*
H(3)	0.3738	0.2325	0.7094	0.0659 (3)*
H(4)	0.2580	0.2922	0.7902	0.1105 (4)*
H(5)	0.1388	0.2552	0.8893	0.0802 (3)*
H(7)	0.0691	0.1695	0.9693	0.0951 (3)*
H(8)	0.0887	0.0738	1.0041	0.0890 (3)*
H(11)	0.1505	−0.0128	1.0486	0.0803 (3)*
H(12)	0.2255	−0.1047	1.0884	0.0330 (2)*
H(14)	0.3706	−0.1838	1.0667	0.0610 (2)*
H(15)	0.5089	−0.2207	0.9862	0.0775 (3)*
H(16)	0.5507	−0.1730	0.8507	0.0926 (3)*
H(17)	0.4533	−0.0862	0.7967	0.0481 (2)*
H(20)	0.4335	0.0270	0.5934	0.0594 (2)*
H(21)	0.5607	0.0643	0.4982	0.0623 (2)*
H(22)	0.4983	0.1491	0.4068	0.0655 (2)*
H(23)	0.2989	0.1920	0.3976	0.1153 (4)*
H(25)	0.0839	0.1922	0.4423	0.0777 (3)*
H(26)	−0.0516	0.1484	0.5222	0.0609 (2)*
H(29)	−0.1693	0.1045	0.6052	0.0654 (2)*
H(30)	−0.2849	0.0486	0.6864	0.0751 (3)*
H(32)	−0.3092	−0.0474	0.7622	0.0979 (3)*
H(33)	−0.2205	−0.1329	0.8192	0.0565 (2)*
H(34)	−0.0104	−0.1589	0.8102	0.1183 (4)*
H(35)	0.1199	−0.0947	0.7569	0.0320 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.0275 (1)	0.0318 (1)	0.0293 (1)	0.00077 (7)	0.01092 (7)	−0.00103 (7)
Cl1	0.0337 (6)	0.0603 (8)	0.0576 (8)	−0.0019 (6)	0.0148 (6)	−0.0008 (6)
Cl2	0.0507 (7)	0.0423 (7)	0.0461 (7)	−0.0016 (6)	0.0252 (5)	−0.0103 (5)
P1	0.143 (2)	0.0397 (9)	0.070 (1)	−0.002 (1)	0.054 (1)	−0.0039 (8)
F1	0.29 (1)	0.131 (5)	0.099 (4)	0.111 (6)	0.031 (5)	0.017 (4)
F2	0.42 (1)	0.107 (5)	0.174 (6)	0.101 (7)	0.214 (8)	0.029 (4)
F3	0.204 (7)	0.078 (4)	0.151 (5)	−0.054 (4)	0.009 (5)	−0.032 (4)
F4	0.137 (5)	0.126 (5)	0.140 (5)	0.020 (5)	−0.009 (4)	0.010 (4)
F5	0.133 (5)	0.103 (4)	0.113 (4)	−0.037 (3)	0.071 (4)	−0.031 (3)
F6	0.219 (8)	0.075 (4)	0.35 (1)	−0.055 (5)	0.228 (9)	−0.047 (5)
N1	0.027 (2)	0.037 (2)	0.034 (2)	0.002 (2)	0.009 (1)	−0.005 (2)
N2	0.032 (2)	0.043 (2)	0.029 (2)	0.002 (2)	0.006 (1)	0.003 (2)
N3	0.031 (2)	0.036 (2)	0.031 (2)	0.000 (2)	0.009 (1)	−0.001 (2)
N4	0.029 (2)	0.038 (2)	0.030 (2)	−0.001 (2)	0.006 (1)	−0.005 (2)
C1	0.033 (2)	0.039 (3)	0.038 (3)	0.001 (2)	0.005 (2)	−0.005 (2)
C2	0.049 (3)	0.039 (3)	0.046 (3)	0.000 (2)	0.010 (2)	−0.003 (2)
C3	0.062 (4)	0.044 (3)	0.062 (4)	−0.001 (3)	0.007 (3)	0.006 (3)
C4	0.081 (5)	0.046 (3)	0.082 (5)	0.006 (4)	0.010 (4)	0.002 (4)
C5	0.072 (4)	0.047 (4)	0.080 (5)	0.016 (3)	0.014 (4)	−0.014 (3)
C6	0.048 (3)	0.047 (3)	0.053 (3)	0.007 (3)	0.012 (2)	−0.012 (2)
C7	0.059 (4)	0.063 (4)	0.062 (4)	0.007 (3)	0.026 (3)	−0.019 (3)
C8	0.056 (3)	0.067 (4)	0.047 (3)	0.004 (3)	0.026 (3)	−0.011 (3)
C9	0.035 (3)	0.048 (3)	0.034 (2)	0.000 (2)	0.011 (2)	−0.003 (2)
C10	0.032 (2)	0.048 (3)	0.032 (2)	−0.005 (2)	0.010 (2)	−0.006 (2)
C11	0.046 (3)	0.068 (4)	0.038 (3)	−0.011 (3)	0.019 (2)	−0.004 (2)
C12	0.064 (4)	0.067 (4)	0.039 (3)	−0.013 (3)	0.017 (3)	0.012 (3)
C13	0.047 (3)	0.055 (3)	0.040 (3)	−0.005 (3)	0.003 (2)	0.008 (2)
C14	0.064 (4)	0.057 (4)	0.063 (4)	0.000 (3)	0.010 (3)	0.022 (3)
C15	0.070 (5)	0.051 (4)	0.089 (5)	0.010 (4)	0.012 (4)	0.029 (4)
C16	0.046 (3)	0.055 (4)	0.086 (5)	0.011 (3)	0.023 (3)	0.010 (3)
C17	0.039 (3)	0.048 (3)	0.054 (3)	0.008 (2)	0.014 (2)	0.013 (2)
C18	0.031 (2)	0.038 (3)	0.036 (2)	−0.002 (2)	0.002 (2)	0.001 (2)
C19	0.040 (3)	0.044 (3)	0.028 (2)	0.000 (2)	0.011 (2)	0.000 (2)
C20	0.044 (3)	0.048 (3)	0.037 (3)	−0.001 (2)	0.020 (2)	0.000 (2)
C21	0.045 (3)	0.062 (3)	0.038 (3)	−0.009 (3)	0.018 (2)	−0.001 (2)
C22	0.069 (4)	0.067 (4)	0.040 (3)	−0.020 (3)	0.025 (3)	0.002 (3)
C23	0.081 (4)	0.050 (3)	0.039 (3)	−0.009 (3)	0.019 (3)	0.009 (2)
C24	0.058 (3)	0.041 (3)	0.033 (3)	−0.003 (2)	0.009 (2)	0.002 (2)
C25	0.066 (4)	0.047 (3)	0.042 (3)	0.011 (3)	0.013 (3)	0.009 (2)
C26	0.047 (3)	0.046 (3)	0.049 (3)	0.010 (3)	0.008 (2)	0.006 (2)
C27	0.040 (3)	0.043 (3)	0.032 (2)	0.008 (2)	0.009 (2)	0.002 (2)
C28	0.033 (2)	0.046 (3)	0.034 (2)	0.004 (2)	0.006 (2)	−0.005 (2)
C29	0.037 (3)	0.058 (3)	0.048 (3)	0.013 (2)	0.009 (2)	−0.003 (3)
C30	0.029 (3)	0.072 (4)	0.052 (3)	0.004 (3)	0.016 (2)	−0.008 (3)
C31	0.031 (2)	0.058 (3)	0.038 (3)	0.000 (2)	0.010 (2)	−0.011 (2)
C32	0.040 (3)	0.070 (4)	0.055 (3)	−0.013 (3)	0.025 (2)	−0.014 (3)
C33	0.052 (3)	0.060 (4)	0.059 (3)	−0.020 (3)	0.031 (3)	−0.012 (3)
C34	0.053 (3)	0.047 (3)	0.050 (3)	−0.014 (3)	0.020 (2)	−0.008 (2)
C35	0.040 (3)	0.042 (3)	0.041 (3)	−0.004 (2)	0.014 (2)	−0.005 (2)
C36	0.030 (2)	0.044 (3)	0.031 (2)	−0.006 (2)	0.012 (2)	−0.007 (2)

Geometric parameters (Å, º) top

Ir1—Cl1	2.340 (1)	C13—C14	1.427 (9)
Ir1—Cl2	2.353 (1)	C13—C18	1.406 (8)
Ir1—N1	2.058 (4)	C14—C15	1.32 (1)
Ir1—N2	2.070 (4)	C14—H(14)	0.952
Ir1—N3	2.068 (4)	C15—C16	1.41 (1)
Ir1—N4	2.070 (4)	C15—H(15)	0.942
P1—F1	1.600 (8)	C16—C17	1.370 (9)
P1—F2	1.54 (1)	C16—H(16)	0.933
P1—F3	1.546 (7)	C17—C18	1.406 (8)
P1—F4	1.540 (7)	C17—H(17)	0.944
P1—F5	1.588 (7)	C19—C20	1.418 (8)
P1—F6	1.549 (7)	C19—C24	1.434 (7)
N1—C1	1.384 (6)	C20—C21	1.372 (9)
N1—C9	1.344 (7)	C20—H(20)	0.950
N2—C10	1.339 (7)	C21—C22	1.409 (8)
N2—C18	1.379 (6)	C21—H(21)	0.948
N3—C19	1.379 (7)	C22—C23	1.35 (1)
N3—C27	1.343 (7)	C22—H(22)	0.956
N4—C28	1.314 (6)	C23—C24	1.404 (10)
N4—C36	1.387 (7)	C23—H(23)	0.950
C1—C2	1.401 (8)	C24—C25	1.401 (9)
C1—C6	1.422 (8)	C25—C26	1.353 (10)
C2—C3	1.365 (8)	C25—H(25)	0.951
C2—H(2)	0.943	C26—C27	1.405 (7)
C3—C4	1.40 (1)	C26—H(26)	0.951
C3—H(3)	0.950	C27—C28	1.469 (8)
C4—C5	1.37 (1)	C28—C29	1.420 (8)
C4—H(4)	0.953	C29—C30	1.351 (9)
C5—C6	1.403 (9)	C29—H(29)	0.952
C5—H(5)	0.945	C30—C31	1.403 (8)
C6—C7	1.402 (10)	C30—H(30)	0.949
C7—C8	1.361 (10)	C31—C32	1.415 (9)
C7—H(7)	0.939	C31—C36	1.421 (8)
C8—C9	1.404 (9)	C32—C33	1.332 (9)
C8—H(8)	0.952	C32—H(32)	0.941
C9—C10	1.457 (8)	C33—C34	1.404 (9)
C10—C11	1.418 (8)	C33—H(33)	0.948
C11—C12	1.360 (9)	C34—C35	1.367 (8)
C11—H(11)	0.955	C34—H(34)	0.947
C12—C13	1.387 (10)	C35—C36	1.396 (7)
C12—H(12)	0.951	C35—H(35)	0.945

Cl1···C12ⁱ	3.270 (6)	F5···C3^v	3.441 (10)
Cl1···C11ⁱ	3.498 (5)	F5···C14^vii	3.471 (10)
Cl2···C29ⁱⁱ	3.501 (5)	F5···C34ⁱⁱⁱ	3.574 (8)
F1···C34ⁱⁱⁱ	3.340 (10)	F6···C33ⁱⁱⁱ	3.258 (9)
F1···C7^iv	3.49 (1)	F6···C16^viii	3.33 (1)
F1···C33ⁱⁱⁱ	3.519 (9)	F6···C23^vi	3.38 (1)
F3···C21^v	3.161 (8)	C8···C33^vii	3.348 (9)
F3···C22^v	3.349 (8)	C22···C32ⁱⁱ	3.528 (8)
F3···C20^v	3.478 (8)	C23···C33ⁱⁱ	3.328 (8)
F5···C23^vi	3.354 (8)	C23···C32ⁱⁱ	3.564 (9)

Cl1—Ir1—Cl2	96.15 (5)	C11—C12—C13	119.4 (6)
Cl1—Ir1—N1	89.8 (1)	C11—C12—H(12)	120.0
Cl1—Ir1—N2	86.6 (1)	C13—C12—H(12)	120.7
Cl1—Ir1—N3	101.1 (1)	C12—C13—C14	121.7 (6)
Cl1—Ir1—N4	174.4 (1)	C12—C13—C18	120.2 (5)
Cl2—Ir1—N1	173.6 (1)	C14—C13—C18	118.1 (6)
Cl2—Ir1—N2	99.7 (1)	C13—C14—C15	121.0 (7)
Cl2—Ir1—N3	88.5 (1)	C13—C14—H(14)	119.4
Cl2—Ir1—N4	89.3 (1)	C15—C14—H(14)	119.6
N1—Ir1—N2	78.2 (2)	C14—C15—C16	121.1 (6)
N1—Ir1—N3	92.8 (2)	C14—C15—H(15)	119.8
N1—Ir1—N4	84.9 (1)	C16—C15—H(15)	119.1
N2—Ir1—N3	168.2 (2)	C15—C16—C17	120.2 (7)
N2—Ir1—N4	93.9 (2)	C15—C16—H(16)	119.8
N3—Ir1—N4	77.7 (2)	C17—C16—H(16)	120.0
F1—P1—F2	88.9 (4)	C16—C17—C18	119.4 (6)
F1—P1—F3	90.4 (4)	C16—C17—H(17)	120.2
F1—P1—F4	176.4 (5)	C18—C17—H(17)	120.5
F1—P1—F5	85.8 (4)	N2—C18—C13	119.4 (5)
F1—P1—F6	90.6 (4)	N2—C18—C17	120.4 (5)
F2—P1—F3	89.2 (4)	C13—C18—C17	120.2 (5)
F2—P1—F4	93.5 (4)	N3—C19—C20	120.7 (4)
F2—P1—F5	174.4 (4)	N3—C19—C24	119.9 (5)
F2—P1—F6	93.7 (6)	C20—C19—C24	119.4 (5)
F3—P1—F4	87.0 (4)	C19—C20—C21	119.3 (5)
F3—P1—F5	89.2 (4)	C19—C20—H(20)	120.4
F3—P1—F6	176.9 (5)	C21—C20—H(20)	120.3
F4—P1—F5	91.7 (4)	C20—C21—C22	120.9 (6)
F4—P1—F6	91.8 (4)	C20—C21—H(21)	119.4
F5—P1—F6	88.0 (5)	C22—C21—H(21)	119.7
Ir1—N1—C1	128.7 (3)	C21—C22—C23	120.7 (6)
Ir1—N1—C9	110.4 (3)	C21—C22—H(22)	119.4
C1—N1—C9	119.8 (4)	C23—C22—H(22)	119.9
Ir1—N2—C10	109.8 (3)	C22—C23—C24	121.1 (6)
Ir1—N2—C18	129.8 (4)	C22—C23—H(23)	119.7
C10—N2—C18	119.8 (4)	C24—C23—H(23)	119.2
Ir1—N3—C19	128.6 (3)	C19—C24—C23	118.5 (5)
Ir1—N3—C27	111.1 (3)	C19—C24—C25	117.9 (5)
C19—N3—C27	119.5 (4)	C23—C24—C25	123.5 (5)
Ir1—N4—C28	111.1 (3)	C24—C25—C26	120.6 (5)
Ir1—N4—C36	127.1 (3)	C24—C25—H(25)	120.2
C28—N4—C36	120.6 (4)	C26—C25—H(25)	119.3
N1—C1—C2	120.9 (5)	C25—C26—C27	119.8 (5)
N1—C1—C6	119.3 (5)	C25—C26—H(26)	120.3
C2—C1—C6	119.7 (5)	C27—C26—H(26)	119.9
C1—C2—C3	120.2 (6)	N3—C27—C26	121.6 (5)
C1—C2—H(2)	119.6	N3—C27—C28	114.4 (4)
C3—C2—H(2)	120.2	C26—C27—C28	123.8 (5)
C2—C3—C4	120.2 (7)	N4—C28—C27	115.7 (4)
C2—C3—H(3)	120.0	N4—C28—C29	121.4 (5)
C4—C3—H(3)	119.8	C27—C28—C29	122.9 (5)
C3—C4—C5	121.0 (7)	C28—C29—C30	118.9 (5)
C3—C4—H(4)	120.3	C28—C29—H(29)	120.8
C5—C4—H(4)	118.7	C30—C29—H(29)	120.3
C4—C5—C6	119.9 (7)	C29—C30—C31	120.7 (5)
C4—C5—H(5)	119.3	C29—C30—H(30)	119.7
C6—C5—H(5)	120.7	C31—C30—H(30)	119.6
C1—C6—C5	118.8 (6)	C30—C31—C32	123.6 (5)
C1—C6—C7	118.3 (5)	C30—C31—C36	118.2 (5)
C5—C6—C7	122.8 (6)	C32—C31—C36	118.2 (5)
C6—C7—C8	121.0 (7)	C31—C32—C33	120.8 (6)
C6—C7—H(7)	119.6	C31—C32—H(32)	120.1
C8—C7—H(7)	119.4	C33—C32—H(32)	119.1
C7—C8—C9	118.8 (6)	C32—C33—C34	121.0 (6)
C7—C8—H(8)	120.7	C32—C33—H(33)	119.9
C9—C8—H(8)	120.5	C34—C33—H(33)	119.1
N1—C9—C8	121.6 (5)	C33—C34—C35	120.5 (5)
N1—C9—C10	114.4 (5)	C33—C34—H(34)	119.6
C8—C9—C10	123.9 (5)	C35—C34—H(34)	119.9
N2—C10—C9	116.1 (5)	C34—C35—C36	119.6 (5)
N2—C10—C11	121.1 (5)	C34—C35—H(35)	119.9
C9—C10—C11	122.4 (5)	C36—C35—H(35)	120.5
C10—C11—C12	119.5 (6)	N4—C36—C31	119.0 (4)
C10—C11—H(11)	120.3	N4—C36—C35	121.1 (5)
C12—C11—H(11)	120.2	C31—C36—C35	119.9 (5)

Ir1—N1—C1—C2	−26.0 (6)	N4—C28—C27—C26	172.4 (5)
Ir1—N1—C1—C6	156.1 (3)	N4—C28—C29—C30	−1.5 (8)
Ir1—N1—C9—C8	−157.9 (4)	N4—C36—C31—C30	4.0 (7)
Ir1—N1—C9—C10	25.6 (4)	N4—C36—C31—C32	−177.6 (4)
Ir1—N2—C10—C9	−21.7 (5)	N4—C36—C35—C34	179.3 (4)
Ir1—N2—C10—C11	164.6 (4)	C1—N1—C9—C8	11.6 (6)
Ir1—N2—C18—C13	−163.0 (3)	C1—N1—C9—C10	−164.9 (4)
Ir1—N2—C18—C17	18.8 (6)	C1—C2—C3—C4	0.6 (8)
Ir1—N3—C19—C20	20.0 (6)	C1—C6—C5—C4	−2.7 (8)
Ir1—N3—C19—C24	−159.2 (3)	C1—C6—C7—C8	4.0 (8)
Ir1—N3—C27—C26	164.2 (4)	C2—C1—N1—C9	166.6 (4)
Ir1—N3—C27—C28	−21.3 (5)	C2—C1—C6—C5	3.5 (7)
Ir1—N4—C28—C27	24.1 (5)	C2—C1—C6—C7	−174.4 (5)
Ir1—N4—C28—C29	−157.2 (4)	C2—C3—C4—C5	0.2 (10)
Ir1—N4—C36—C31	153.9 (4)	C3—C2—C1—C6	−2.5 (7)
Ir1—N4—C36—C35	−27.0 (6)	C3—C4—C5—C6	0.9 (10)
Cl1—Ir1—N1—C1	76.4 (4)	C4—C5—C6—C7	175.1 (6)
Cl1—Ir1—N1—C9	−115.2 (3)	C5—C6—C7—C8	−173.8 (5)
Cl1—Ir1—N2—C10	117.5 (3)	C6—C1—N1—C9	−11.3 (6)
Cl1—Ir1—N2—C18	−71.0 (4)	C6—C7—C8—C9	−4.0 (8)
Cl1—Ir1—N3—C19	21.6 (4)	C7—C8—C9—C10	172.2 (5)
Cl1—Ir1—N3—C27	−148.4 (3)	C8—C9—C10—C11	−5.3 (7)
Cl1—Ir1—N4—C28	50 (1)	C9—C10—N2—C18	165.9 (4)
Cl1—Ir1—N4—C36	−116 (1)	C9—C10—C11—C12	−171.3 (5)
Cl2—Ir1—N1—C1	−125.9 (9)	C10—N2—C18—C13	7.8 (6)
Cl2—Ir1—N1—C9	42 (1)	C10—N2—C18—C17	−170.5 (4)
Cl2—Ir1—N2—C10	−146.8 (3)	C10—C11—C12—C13	3.9 (8)
Cl2—Ir1—N2—C18	24.7 (4)	C11—C10—N2—C18	−7.9 (7)
Cl2—Ir1—N3—C19	−74.3 (4)	C11—C12—C13—C14	174.0 (5)
Cl2—Ir1—N3—C27	115.6 (3)	C11—C12—C13—C18	−3.9 (8)
Cl2—Ir1—N4—C28	−115.8 (3)	C12—C13—C14—C15	−176.5 (6)
Cl2—Ir1—N4—C36	77.2 (4)	C12—C13—C18—C17	176.3 (5)
N1—Ir1—N2—C10	27.1 (3)	C13—C14—C15—C16	−0.9 (10)
N1—Ir1—N2—C18	−161.5 (4)	C13—C18—C17—C16	1.3 (7)
N1—Ir1—N3—C19	112.0 (4)	C14—C13—C18—C17	−1.6 (7)
N1—Ir1—N3—C27	−58.1 (3)	C14—C15—C16—C17	0.6 (10)
N1—Ir1—N4—C28	66.8 (3)	C15—C14—C13—C18	1.4 (9)
N1—Ir1—N4—C36	−100.2 (4)	C15—C16—C17—C18	−0.8 (8)
N1—C1—C2—C3	179.6 (4)	C19—N3—C27—C26	−6.8 (7)
N1—C1—C6—C5	−178.5 (4)	C19—N3—C27—C28	167.7 (4)
N1—C1—C6—C7	3.6 (7)	C19—C20—C21—C22	1.7 (7)
N1—C9—C8—C7	−3.9 (7)	C19—C24—C23—C22	2.7 (8)
N1—C9—C10—N2	−2.5 (6)	C19—C24—C25—C26	−1.2 (7)
N1—C9—C10—C11	171.1 (4)	C20—C19—N3—C27	−170.7 (4)
N2—Ir1—N1—C1	162.9 (4)	C20—C19—C24—C23	−3.8 (7)
N2—Ir1—N1—C9	−28.7 (3)	C20—C19—C24—C25	174.6 (5)
N2—Ir1—N3—C19	151.4 (6)	C20—C21—C22—C23	−2.8 (8)
N2—Ir1—N3—C27	−18.6 (9)	C21—C20—C19—C24	1.6 (7)
N2—Ir1—N4—C28	144.5 (3)	C21—C22—C23—C24	0.5 (8)
N2—Ir1—N4—C36	−22.4 (4)	C22—C23—C24—C25	−175.6 (5)
N2—C10—C9—C8	−178.9 (4)	C23—C24—C25—C26	177.1 (5)
N2—C10—C11—C12	2.0 (7)	C24—C19—N3—C27	10.1 (6)
N2—C18—C13—C12	−1.9 (7)	C24—C25—C26—C27	4.6 (8)
N2—C18—C13—C14	−179.9 (4)	C25—C26—C27—C28	−174.6 (5)
N2—C18—C17—C16	179.5 (5)	C26—C27—C28—C29	−6.3 (8)
N3—Ir1—N1—C1	−24.7 (4)	C27—C28—N4—C36	−167.9 (4)
N3—Ir1—N1—C9	143.7 (3)	C27—C28—C29—C30	177.2 (5)
N3—Ir1—N2—C10	−13.4 (9)	C28—N4—C36—C31	−12.0 (7)
N3—Ir1—N2—C18	158.0 (6)	C28—N4—C36—C35	167.1 (4)
N3—Ir1—N4—C28	−27.2 (3)	C28—C29—C30—C31	−6.5 (8)
N3—Ir1—N4—C36	165.8 (4)	C29—C28—N4—C36	10.8 (7)
N3—C19—C20—C21	−177.6 (4)	C29—C30—C31—C32	−173.2 (5)
N3—C19—C24—C23	175.5 (4)	C29—C30—C31—C36	5.1 (8)
N3—C19—C24—C25	−6.1 (7)	C30—C31—C32—C33	176.3 (6)
N3—C27—C26—C25	−0.6 (8)	C30—C31—C36—C35	−175.1 (5)
N3—C27—C28—N4	−2.0 (6)	C31—C32—C33—C34	−1.0 (9)
N3—C27—C28—C29	179.3 (4)	C31—C36—C35—C34	−1.6 (7)
N4—Ir1—N1—C1	−102.0 (4)	C32—C31—C36—C35	3.3 (7)
N4—Ir1—N1—C9	66.4 (3)	C32—C33—C34—C35	2.8 (9)
N4—Ir1—N2—C10	−56.9 (3)	C33—C32—C31—C36	−2.0 (8)
N4—Ir1—N2—C18	114.6 (4)	C33—C34—C35—C36	−1.4 (8)
N4—Ir1—N3—C19	−163.9 (4)	C33—C34—C35—C36	−1.4 (8)
N4—Ir1—N3—C27	26.1 (3)

Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x, −y, −z+1; (iii) −x−1/2, y+1/2, −z+3/2; (iv) x−1/2, −y+1/2, z−1/2; (v) x−1, y, z; (vi) x−1/2, −y+1/2, z+1/2; (vii) −x, −y, −z+2; (viii) −x+1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[IrCl₂(C₁₈H₁₂N₂)₂]PF₆
M_r	920.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	223
a, b, c (Å)	10.5127 (2), 23.6279 (5), 13.7750 (2)
β (°)	108.0188 (3)
V (Å³)	3253.8 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.40
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS-RAPID Imaging Plate diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.419, 0.644
No. of measured, independent and observed [I > 2σ(I)] reflections	27860, 7310, 6212
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.30
No. of reflections	6212
No. of parameters	475
No. of restraints	?
H-atom treatment	Only H-atom displacement parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.90, −1.17

Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, TEXSAN (Molecular Structure Corportation, 2000), SIR92 (Altomare et al., 1992), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top

Ir1—Cl1	2.340 (1)	Ir1—N2	2.070 (4)
Ir1—Cl2	2.353 (1)	Ir1—N3	2.068 (4)
Ir1—N1	2.058 (4)	Ir1—N4	2.070 (4)

Cl1—Ir1—Cl2	96.15 (5)	Cl2—Ir1—N4	89.3 (1)
Cl1—Ir1—N1	89.8 (1)	N1—Ir1—N2	78.2 (2)
Cl1—Ir1—N2	86.6 (1)	N1—Ir1—N3	92.8 (2)
Cl1—Ir1—N3	101.1 (1)	N1—Ir1—N4	84.9 (1)
Cl1—Ir1—N4	174.4 (1)	N2—Ir1—N3	168.2 (2)
Cl2—Ir1—N1	173.6 (1)	N2—Ir1—N4	93.9 (2)
Cl2—Ir1—N2	99.7 (1)	N3—Ir1—N4	77.7 (2)
Cl2—Ir1—N3	88.5 (1)

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cis-Di­chloro­bis(2,2'-bi­quinoline)­iridium(III) hexa­fluoro­phosphate