cis-Di­chloro­bis(4,4′-di­methyl-2,2′-bi­pyridine)­iridium(III) hexa­fluoro­phosphate

Yoshikawa, N.; Sakamoto, J.; Kanehisa, N.; Kai, Y.; Matsumura-Inoue, T.

doi:10.1107/S160053680300429X

cis-Dichlorobis(4,4'-dimethyl-2,2'-bipyridine)iridium(III) hexafluorophosphate

N. Yoshikawa, J. Sakamoto, N. Kanehisa, Y. Kai and T. Matsumura-Inoue

The crystal structure of the title compound, [IrCl₂(C₂₄H₂₄N₄)₂]PF₆, contains a monomeric [IrCl₂(dmbpy)₂]⁺ cation (dmbpy is 4,4'-dimethyl-2,2'-bipyridine) and a hexafluorophosphate anion. The iridium(III) ion is coordinated by four N atoms from two dmbpy ligands [mean Ir-N distance = 2.052 (5) Å] and two Cl atoms [Ir-Cl = 2.360 (9) and 2.356 (2) Å], forming a distorted octahedral environment. Each 4,4'-dimethyl-2,2'-bipyridine ligand is planar, the mean deviations from the least-squares planes being 0.035 (4) and 0.013 (3) Å.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300429X/na6193sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680300429X/na6193Isup2.hkl Contains datablock I

CCDC reference: 209884

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.009 Å
R factor = 0.053
wR factor = 0.126
Data-to-parameter ratio = 18.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     17
                   CL1 -IR1 -N1  -C1     93.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     18
                   CL1 -IR1 -N1  -C5    -79.00  3.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     29
                   CL2 -IR1 -N3  -C13   171.00  1.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     30
                   CL2 -IR1 -N3  -C17    -9.00  2.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     49
                   N2  -IR1 -N4  -C18   -63.00  2.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     50
                   N2  -IR1 -N4  -C22   118.00  2.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     70
                   N4  -IR1 -N2  -C6    -40.00  2.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     71
                   N4  -IR1 -N2  -C10   142.00  2.00   1.555   1.555   1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 8 Alert Level C = Please check

Comment top

Transition metals in particular iridium polypyridine complexes have received much interest on account of their intense emission properties. Theses iridium complexes exhibit a very intense emission at around 532 nm, originating from ³LC (ligand-centered charge transfer) state in acetonitrile solution even at room temperature. Recent research in this area has been focused on trials to replace bipyridine ligands with other polypyridine ligands. However, the difficulties of the synthesis precluded further work along these lines. To our knowledge, no structure of an iridium complex with the 4,4'-dimethyl-2,2'-bipyridine ligand (dmbpy) has been reported previously.

In this paper, we report the synthesis and crystal structure of a mononuclear iridium compound, viz. [IrCl₂(dmbpy)₂]PF₆, (I),whose crystal structure consists of a discrete [IrCl₂(dmbpy)₂]⁺ cation and a hexafluorophosphate anion. As illustrated in Fig. 1, the Ir^III atom is located in a distorted octahedral environment by two dmbpy ligands and two chloride anions. The Ir—N bond lengths are in the range 2.015 (5)–2.131 (5) Å. Three trans angles are in the range 175.1 (2)–175.9 (3) Å. It is coordinated by four N atoms from a pair of cis-related chelating dmbpy ligands and two Cl atoms [Ir—Cl1 2.360 (9) Å and Ir—Cl2 2.356 (2) Å]. The equatorial plane is formed by atoms Cl1, N1, N2 and N4, with the largest deviation from the mean plane being 0.035 (4) Å and the Ir atom being 0.013 (3) Å out of this plane. The axial positions are occupied by the fourth dmbpy N atom and another Cl atom. Atom Cl1 has a particularly high anisotropic displacement coefficients, probably indicative of some disorder. Each dmbpy ligand is planar, the mean deviation from the best planes is 0.024 (6) Å. The dihedral angle between dmbpy planes is 79.7 (1) Å. The two Cl ligands were coordinated in a cis fasion, but PF₆^- was not coordinated to the iridium metal atom. The average length of the Ir—N bonds is 2.052 (5) Å and the average of the N1—Ir—N2 and N3—Ir—N4 ligand angles is 78.9 (2)°, which compare well with the values published for Ir(bpy)₃(ClO₄)₃ (bpy = 2,2'-bipyridine; Hazell & Gronbaek Hazell, 1984) of 2.026 Å and 79.1°. No hydrogen-bond interactions exist in the crystal packing.

Experimental top

The precursor (NH₄)₃[IrCl₆]H₂O and two equivalents of 4,4'-dimethyl-2,2'-bipyridine were suspended in ethylene glycol. Under a purging nitrogen atmosphere, the suspension was subjected to reflux for 15 min under microwave irradiation with a frequency of 2450 MHz to activate the OH group of ethylene glycol, and then cooled to room temperature. The saturated aqueous solution of KPF₆ was added to the brown solution. Air-stable yellow single crystals were obtained by recrystallization from acetonitrile (Yoshikawa et al., 2000).

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); 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 molecular structure of (I), showing ellipsoids at the 50% probability level.

(I) top

Crystal data top

[IrCl₂(C₂₄H₂₄N₄)₂]PF₆	D_x = 1.835 Mg m⁻³
M_r = 776.57	Mo Kα radiation, λ = 0.7107 Å
Monoclinic, P2₁/n	Cell parameters from 25815 reflections
a = 7.8114 (2) Å	θ = 1.5–30.5°
b = 21.6075 (7) Å	µ = 5.07 mm⁻¹
c = 16.6606 (5) Å	T = 296 K
β = 91.4634 (7)°	Platelet, yellow
V = 2811.1 (1) Å³	0.80 × 0.10 × 0.02 mm
Z = 4

Data collection top

Rigaku RAXIS-RAPID imaging plate diffractometer	6274 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.068
ω scans	θ_max = 30.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→11
T_min = 0.552, T_max = 0.904	k = −30→30
32401 measured reflections	l = −23→23
8462 independent reflections

Refinement top

Refinement on F²	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.053	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.126	(Δ/σ)_max = −0.003
S = 1.41	Δρ_max = 2.81 e Å⁻³
6274 reflections	Δρ_min = −2.53 e Å⁻³
343 parameters

Crystal data top

[IrCl₂(C₂₄H₂₄N₄)₂]PF₆	V = 2811.1 (1) Å³
M_r = 776.57	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.8114 (2) Å	µ = 5.07 mm⁻¹
b = 21.6075 (7) Å	T = 296 K
c = 16.6606 (5) Å	0.80 × 0.10 × 0.02 mm
β = 91.4634 (7)°

Data collection top

Rigaku RAXIS-RAPID imaging plate diffractometer	8462 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	6274 reflections with I > 2σ(I)
T_min = 0.552, T_max = 0.904	R_int = 0.068
32401 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	343 parameters
wR(F²) = 0.126	H-atom parameters not refined
S = 1.41	Δρ_max = 2.81 e Å⁻³
6274 reflections	Δρ_min = −2.53 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	0.75103 (2)	0.09645 (1)	0.68643 (1)	0.03194 (8)
Cl1	0.927 (2)	0.1849 (3)	0.6777 (5)	0.326 (5)
Cl2	0.8864 (2)	0.05412 (9)	0.57419 (9)	0.0502 (4)
P1	0.9986 (3)	−0.14521 (8)	0.8504 (1)	0.0510 (4)
F1	0.8195 (9)	−0.1717 (4)	0.8311 (5)	0.132 (3)
F2	0.9897 (7)	−0.1778 (2)	0.9370 (3)	0.081 (1)
F3	1.1789 (9)	−0.1184 (4)	0.8734 (5)	0.144 (3)
F4	1.0012 (8)	−0.1116 (3)	0.7664 (3)	0.083 (2)
F5	0.917 (1)	−0.0856 (3)	0.8853 (4)	0.133 (3)
F6	1.081 (1)	−0.2044 (3)	0.8160 (4)	0.123 (3)
N1	0.6018 (6)	0.0139 (2)	0.6873 (3)	0.037 (1)
N2	0.5546 (6)	0.1182 (2)	0.6089 (3)	0.037 (1)
N3	0.6511 (6)	0.1313 (2)	0.7872 (3)	0.038 (1)
N4	0.9320 (5)	0.0702 (2)	0.7687 (3)	0.0332 (10)
C1	0.6333 (7)	−0.0368 (3)	0.7319 (4)	0.041 (1)
C2	0.5429 (9)	−0.0898 (3)	0.7226 (5)	0.050 (2)
C3	0.4145 (8)	−0.0939 (3)	0.6625 (4)	0.043 (1)
C4	0.3798 (7)	−0.0409 (3)	0.6179 (4)	0.040 (1)
C5	0.4745 (7)	0.0124 (3)	0.6317 (3)	0.033 (1)
C6	0.4458 (7)	0.0709 (3)	0.5875 (3)	0.033 (1)
C7	0.3169 (8)	0.0789 (3)	0.5300 (4)	0.040 (1)
C8	0.2917 (8)	0.1355 (3)	0.4930 (4)	0.045 (1)
C9	0.3964 (9)	0.1836 (3)	0.5179 (4)	0.051 (2)
C10	0.5244 (9)	0.1736 (3)	0.5737 (4)	0.048 (2)
C11	0.3162 (10)	−0.1533 (3)	0.6481 (5)	0.061 (2)
C12	0.1496 (9)	0.1438 (4)	0.4313 (5)	0.058 (2)
C13	0.5026 (7)	0.1622 (3)	0.7926 (4)	0.047 (2)
C14	0.4442 (9)	0.1843 (4)	0.8639 (5)	0.061 (2)
C15	0.5330 (8)	0.1750 (3)	0.9339 (4)	0.049 (2)
C16	0.6897 (8)	0.1425 (3)	0.9291 (4)	0.047 (1)
C17	0.7441 (7)	0.1218 (3)	0.8554 (4)	0.034 (1)
C18	0.9062 (7)	0.0876 (3)	0.8449 (4)	0.034 (1)
C19	1.0224 (7)	0.0738 (3)	0.9065 (4)	0.040 (1)
C20	1.1728 (7)	0.0420 (3)	0.8898 (4)	0.044 (1)
C21	1.1951 (7)	0.0243 (3)	0.8114 (4)	0.042 (1)
C22	1.0769 (8)	0.0389 (3)	0.7529 (4)	0.042 (1)
C23	0.472 (1)	0.1964 (5)	1.0131 (6)	0.078 (3)
C24	1.2991 (9)	0.0245 (4)	0.9547 (5)	0.060 (2)
H1	0.7216	−0.0347	0.7736	0.0412*
H2	0.5665	−0.1259	0.7558	0.0503*
H3	0.2903	−0.0412	0.5773	0.0403*
H4	0.2424	0.0449	0.5182	0.0401*
H5	0.3809	0.2245	0.4949	0.0506*
H6	0.5960	0.2075	0.5900	0.0482*
H7	0.3927	−0.1858	0.6338	0.0608*
H8	0.2344	−0.1477	0.6050	0.0608*
H9	0.2578	−0.1650	0.6950	0.0608*
H10	0.1644	0.1165	0.3868	0.0585*
H11	0.0413	0.1371	0.4533	0.0585*
H12	0.1524	0.1858	0.4103	0.0585*
H13	0.4421	0.1714	0.7416	0.0473*
H14	0.3364	0.2060	0.8643	0.0611*
H15	0.7586	0.1373	0.9764	0.0470*
H16	1.0015	0.0874	0.9596	0.0400*
H17	1.2977	0.0007	0.7989	0.0424*
H18	1.0964	0.0271	0.6977	0.0424*
H19	0.3730	0.2164	1.0069	0.0782*
H20	0.5607	0.2221	1.0387	0.0782*
H21	0.4628	0.1601	1.0475	0.0782*
H22	1.2612	0.0406	1.0061	0.0604*
H23	1.4070	0.0422	0.9446	0.0604*
H24	1.3085	−0.0189	0.9593	0.0604*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.0286 (1)	0.0367 (1)	0.0303 (1)	−0.00082 (9)	−0.00345 (7)	−0.0027 (1)
Cl1	0.59 (2)	0.148 (5)	0.253 (8)	0.008 (7)	0.168 (9)	0.067 (5)
Cl2	0.0390 (7)	0.077 (1)	0.0342 (7)	−0.0007 (8)	0.0019 (6)	−0.0120 (7)
P1	0.062 (1)	0.0464 (10)	0.0441 (10)	0.0031 (8)	−0.0082 (8)	0.0011 (8)
F1	0.095 (4)	0.182 (7)	0.116 (5)	−0.053 (5)	−0.043 (4)	0.036 (5)
F2	0.121 (4)	0.067 (3)	0.054 (3)	−0.005 (3)	−0.013 (3)	0.014 (2)
F3	0.109 (5)	0.149 (6)	0.169 (8)	−0.067 (5)	−0.076 (5)	0.075 (6)
F4	0.110 (4)	0.087 (3)	0.053 (3)	0.019 (3)	0.005 (3)	0.013 (2)
F5	0.246 (10)	0.076 (4)	0.078 (4)	0.066 (5)	0.042 (5)	0.007 (3)
F6	0.194 (7)	0.068 (4)	0.110 (5)	0.045 (4)	0.057 (5)	0.009 (3)
N1	0.033 (2)	0.045 (3)	0.034 (2)	0.000 (2)	0.000 (2)	−0.001 (2)
N2	0.036 (2)	0.041 (2)	0.034 (2)	0.003 (2)	−0.005 (2)	−0.002 (2)
N3	0.036 (2)	0.039 (3)	0.038 (3)	0.001 (2)	−0.003 (2)	−0.003 (2)
N4	0.023 (2)	0.042 (3)	0.034 (2)	0.000 (2)	−0.002 (2)	−0.006 (2)
C1	0.034 (3)	0.047 (3)	0.042 (3)	0.001 (3)	−0.007 (2)	0.004 (3)
C2	0.051 (4)	0.040 (3)	0.060 (4)	0.001 (3)	−0.001 (3)	0.008 (3)
C3	0.042 (3)	0.040 (3)	0.048 (4)	0.000 (3)	0.004 (3)	−0.006 (3)
C4	0.036 (3)	0.048 (3)	0.036 (3)	0.002 (3)	−0.002 (2)	−0.002 (3)
C5	0.029 (2)	0.040 (3)	0.031 (3)	0.007 (2)	0.006 (2)	−0.002 (2)
C6	0.029 (2)	0.041 (3)	0.031 (3)	0.003 (2)	0.000 (2)	−0.004 (2)
C7	0.037 (3)	0.047 (3)	0.036 (3)	0.002 (3)	−0.004 (2)	−0.007 (3)
C8	0.038 (3)	0.062 (4)	0.033 (3)	0.011 (3)	−0.007 (2)	−0.004 (3)
C9	0.050 (3)	0.053 (4)	0.047 (4)	0.010 (3)	−0.011 (3)	0.010 (3)
C10	0.058 (4)	0.039 (3)	0.046 (4)	−0.002 (3)	−0.016 (3)	0.001 (3)
C11	0.061 (4)	0.045 (4)	0.078 (5)	−0.014 (3)	0.006 (4)	−0.004 (4)
C12	0.049 (4)	0.080 (5)	0.046 (4)	0.012 (4)	−0.014 (3)	0.008 (4)
C13	0.032 (3)	0.050 (4)	0.059 (4)	0.010 (3)	−0.005 (3)	−0.010 (3)
C14	0.046 (4)	0.062 (5)	0.076 (5)	0.013 (3)	0.012 (4)	−0.018 (4)
C15	0.045 (3)	0.045 (4)	0.058 (4)	0.008 (3)	0.006 (3)	−0.013 (3)
C16	0.046 (3)	0.056 (4)	0.039 (3)	0.001 (3)	−0.002 (3)	−0.006 (3)
C17	0.029 (2)	0.035 (3)	0.038 (3)	0.001 (2)	0.000 (2)	−0.005 (2)
C18	0.036 (3)	0.035 (3)	0.032 (3)	0.001 (2)	−0.001 (2)	−0.006 (2)
C19	0.034 (3)	0.051 (3)	0.035 (3)	0.000 (3)	−0.006 (2)	−0.002 (3)
C20	0.034 (3)	0.047 (3)	0.050 (4)	0.001 (3)	−0.010 (3)	0.005 (3)
C21	0.030 (2)	0.052 (4)	0.045 (3)	0.008 (3)	−0.004 (2)	−0.002 (3)
C22	0.037 (3)	0.048 (3)	0.042 (3)	0.005 (3)	−0.002 (3)	−0.009 (3)
C23	0.075 (5)	0.099 (7)	0.061 (5)	0.016 (5)	0.013 (4)	−0.024 (5)
C24	0.049 (4)	0.070 (5)	0.062 (5)	0.010 (4)	−0.022 (3)	0.005 (4)

Geometric parameters (Å, º) top

Ir1—Cl1	2.360 (9)	C8—C12	1.505 (9)
Ir1—Cl2	2.356 (2)	C9—C10	1.365 (10)
Ir1—N1	2.131 (5)	C9—H5	0.970
Ir1—N2	2.036 (5)	C10—H6	0.956
Ir1—N3	2.015 (5)	C11—H7	0.956
Ir1—N4	2.024 (4)	C11—H8	0.957
P1—F1	1.538 (7)	C11—H9	0.949
P1—F2	1.610 (5)	C12—H10	0.957
P1—F3	1.561 (8)	C12—H11	0.943
P1—F4	1.577 (5)	C12—H12	0.973
P1—F5	1.558 (7)	C13—C14	1.37 (1)
P1—F6	1.548 (7)	C13—H13	0.983
N1—C1	1.344 (8)	C14—C15	1.36 (1)
N1—C5	1.341 (7)	C14—H14	0.964
N2—C6	1.371 (7)	C15—C16	1.416 (9)
N2—C10	1.350 (8)	C15—C23	1.49 (1)
N3—C13	1.344 (8)	C16—C17	1.385 (9)
N3—C17	1.349 (8)	C16—H15	0.948
N4—C18	1.345 (8)	C17—C18	1.480 (8)
N4—C22	1.351 (8)	C18—C19	1.385 (8)
C1—C2	1.352 (9)	C19—C20	1.395 (9)
C1—H1	0.967	C19—H16	0.951
C2—C3	1.40 (1)	C20—C21	1.376 (9)
C2—H2	0.971	C20—C24	1.493 (10)
C3—C4	1.387 (9)	C21—C22	1.363 (9)
C3—C11	1.513 (10)	C21—H17	0.977
C4—C5	1.385 (8)	C22—H18	0.969
C4—H3	0.961	C23—H19	0.893
C5—C6	1.479 (8)	C23—H20	0.974
C6—C7	1.383 (8)	C23—H21	0.976
C7—C8	1.382 (10)	C24—H22	0.976
C7—H4	0.954	C24—H23	0.945
C8—C9	1.380 (10)	C24—H24	0.943

Cl2···C7ⁱ	3.502 (6)	F4···C12^v	3.539 (9)
F1···C23ⁱⁱ	3.54 (1)	F5···C24^iv	3.45 (1)
F2···C9ⁱⁱⁱ	3.208 (9)	F5···C19^iv	3.498 (9)
F2···C10ⁱⁱⁱ	3.217 (8)	F6···C10ⁱⁱⁱ	3.327 (9)
F2···C16^iv	3.397 (8)	F6···C13ⁱⁱⁱ	3.457 (9)
F2···C19^iv	3.445 (8)	F6···C11ⁱ	3.56 (1)
F3···C16^iv	3.46 (1)	C4···C7^v	3.557 (9)
F4···C11ⁱ	3.32 (1)

Cl1—Ir1—Cl2	89.5 (2)	C7—C8—C9	117.2 (6)
Cl1—Ir1—N1	175.9 (3)	C7—C8—C12	120.3 (6)
Cl1—Ir1—N2	101.7 (3)	C9—C8—C12	122.5 (6)
Cl1—Ir1—N3	89.3 (3)	C8—C9—C10	120.3 (6)
Cl1—Ir1—N4	82.6 (3)	C8—C9—H5	120.0
Cl2—Ir1—N1	86.4 (1)	C10—C9—H5	119.7
Cl2—Ir1—N2	86.1 (1)	N2—C10—C9	123.5 (6)
Cl2—Ir1—N3	175.8 (1)	N2—C10—H6	117.5
Cl2—Ir1—N4	96.2 (1)	C9—C10—H6	119.0
N1—Ir1—N2	78.1 (2)	C3—C11—H7	110.2
N1—Ir1—N3	94.8 (2)	C3—C11—H8	109.8
N1—Ir1—N4	97.7 (2)	C3—C11—H9	110.4
N2—Ir1—N3	98.1 (2)	H7—C11—H8	108.4
N2—Ir1—N4	175.1 (2)	H7—C11—H9	109.1
N3—Ir1—N4	79.6 (2)	H8—C11—H9	109.0
F1—P1—F2	87.9 (4)	C8—C12—H10	110.7
F1—P1—F3	177.8 (5)	C8—C12—H11	111.7
F1—P1—F4	91.1 (4)	C8—C12—H12	109.5
F1—P1—F5	90.3 (5)	H10—C12—H11	109.5
F1—P1—F6	90.0 (4)	H10—C12—H12	107.1
F2—P1—F3	90.1 (4)	H11—C12—H12	108.2
F2—P1—F4	177.7 (3)	N3—C13—C14	122.7 (6)
F2—P1—F5	89.9 (3)	N3—C13—H13	116.1
F2—P1—F6	89.9 (3)	C14—C13—H13	121.1
F3—P1—F4	90.8 (4)	C13—C14—C15	121.3 (7)
F3—P1—F5	88.7 (5)	C13—C14—H14	119.1
F3—P1—F6	91.0 (4)	C15—C14—H14	119.6
F4—P1—F5	88.0 (3)	C14—C15—C16	116.7 (7)
F4—P1—F6	92.2 (3)	C14—C15—C23	123.4 (7)
F5—P1—F6	179.6 (4)	C16—C15—C23	119.9 (7)
Ir1—N1—C1	126.4 (4)	C15—C16—C17	119.7 (6)
Ir1—N1—C5	114.3 (4)	C15—C16—H15	119.1
C1—N1—C5	118.9 (5)	C17—C16—H15	121.2
Ir1—N2—C6	116.4 (4)	N3—C17—C16	121.9 (5)
Ir1—N2—C10	126.9 (4)	N3—C17—C18	114.9 (5)
C6—N2—C10	116.6 (5)	C16—C17—C18	123.2 (5)
Ir1—N3—C13	126.6 (4)	N4—C18—C17	113.5 (5)
Ir1—N3—C17	115.7 (4)	N4—C18—C19	121.9 (5)
C13—N3—C17	117.8 (5)	C17—C18—C19	124.6 (5)
Ir1—N4—C18	116.3 (4)	C18—C19—C20	119.9 (6)
Ir1—N4—C22	125.6 (4)	C18—C19—H16	119.9
C18—N4—C22	118.1 (5)	C20—C19—H16	120.2
N1—C1—C2	122.6 (6)	C19—C20—C21	116.9 (6)
N1—C1—H1	118.5	C19—C20—C24	121.6 (6)
C2—C1—H1	118.9	C21—C20—C24	121.3 (6)
C1—C2—C3	119.8 (6)	C20—C21—C22	121.0 (6)
C1—C2—H2	121.6	C20—C21—H17	118.1
C3—C2—H2	118.6	C22—C21—H17	120.8
C2—C3—C4	117.3 (6)	N4—C22—C21	122.2 (6)
C2—C3—C11	121.1 (6)	N4—C22—H18	118.0
C4—C3—C11	121.6 (6)	C21—C22—H18	119.8
C3—C4—C5	120.0 (5)	C15—C23—H19	110.0
C3—C4—H3	120.2	C15—C23—H20	109.2
C5—C4—H3	119.8	C15—C23—H21	107.6
N1—C5—C4	121.3 (5)	H19—C23—H20	112.3
N1—C5—C6	115.0 (5)	H19—C23—H21	112.2
C4—C5—C6	123.7 (5)	H20—C23—H21	105.4
N2—C6—C5	115.1 (5)	C20—C24—H22	109.6
N2—C6—C7	121.5 (5)	C20—C24—H23	110.1
C5—C6—C7	123.4 (5)	C20—C24—H24	111.0
C6—C7—C8	120.8 (6)	H22—C24—H23	107.7
C6—C7—H4	118.4	H22—C24—H24	107.8
C8—C7—H4	120.7	H23—C24—H24	110.5

Ir1—N1—C1—C2	−172.6 (5)	C2—C3—C11—H7	−60.5
Ir1—N1—C1—H1	9.7	C2—C3—C11—H8	−179.8
Ir1—N1—C5—C4	171.8 (4)	C2—C3—C11—H9	60.1
Ir1—N1—C5—C6	−7.8 (6)	C3—C2—C1—H1	−180.0
Ir1—N2—C6—C5	7.2 (6)	C3—C4—C5—C6	−179.7 (6)
Ir1—N2—C6—C7	−174.3 (4)	C4—C3—C2—H2	177.8
Ir1—N2—C10—C9	175.3 (5)	C4—C3—C11—H7	120.5
Ir1—N2—C10—H6	−5.8	C4—C3—C11—H8	1.2
Ir1—N3—C13—C14	180.0 (5)	C4—C3—C11—H9	−118.9
Ir1—N3—C13—H13	−5.4	C4—C5—C6—C7	2.6 (9)
Ir1—N3—C17—C16	−179.1 (5)	C5—N1—C1—H1	−177.0
Ir1—N3—C17—C18	0.5 (6)	C5—C4—C3—C11	−178.8 (6)
Ir1—N4—C18—C17	1.7 (6)	C5—C6—N2—C10	−175.4 (5)
Ir1—N4—C18—C19	−178.5 (4)	C5—C6—C7—C8	177.2 (6)
Ir1—N4—C22—C21	178.2 (5)	C5—C6—C7—H4	0.1
Ir1—N4—C22—H18	−1.1	C6—N2—C10—C9	−1.7 (9)
Cl1—Ir1—N1—C1	93 (3)	C6—N2—C10—H6	177.1
Cl1—Ir1—N1—C5	−79 (3)	C6—C5—C4—H3	0.5
Cl1—Ir1—N2—C6	167.2 (4)	C6—C7—C8—C9	−2.0 (9)
Cl1—Ir1—N2—C10	−9.8 (6)	C6—C7—C8—C12	−179.2 (6)
Cl1—Ir1—N3—C13	98.2 (6)	C7—C6—N2—C10	3.1 (8)
Cl1—Ir1—N3—C17	−82.3 (5)	C7—C8—C9—C10	3.4 (10)
Cl1—Ir1—N4—C18	89.4 (5)	C7—C8—C9—H5	−178.1
Cl1—Ir1—N4—C22	−88.4 (5)	C7—C8—C12—H10	−60.3
Cl2—Ir1—N1—C1	95.7 (5)	C7—C8—C12—H11	62.0
Cl2—Ir1—N1—C5	−77.9 (4)	C7—C8—C12—H12	−178.2
Cl2—Ir1—N2—C6	78.5 (4)	C8—C9—C10—H6	179.6
Cl2—Ir1—N2—C10	−98.5 (5)	C9—C8—C7—H4	175.0
Cl2—Ir1—N3—C13	171 (1)	C9—C8—C12—H10	122.6
Cl2—Ir1—N3—C17	−9 (2)	C9—C8—C12—H11	−115.0
Cl2—Ir1—N4—C18	178.1 (4)	C9—C8—C12—H12	4.8
Cl2—Ir1—N4—C22	0.3 (5)	C10—C9—C8—C12	−179.5 (6)
N1—Ir1—N2—C6	−8.6 (4)	C11—C3—C2—H2	−1.2
N1—Ir1—N2—C10	174.4 (6)	C11—C3—C4—H3	1.0
N1—Ir1—N3—C13	−82.2 (5)	C12—C8—C7—H4	−2.2
N1—Ir1—N3—C17	97.3 (4)	C12—C8—C9—H5	−0.9
N1—Ir1—N4—C18	−94.7 (4)	C13—N3—C17—C16	0.4 (9)
N1—Ir1—N4—C22	87.5 (5)	C13—N3—C17—C18	−180.0 (5)
N1—C1—C2—C3	2 (1)	C13—C14—C15—C16	1 (1)
N1—C1—C2—H2	−179.2	C13—C14—C15—C23	−178.1 (7)
N1—C5—C4—C3	0.8 (9)	C14—C13—N3—C17	0.5 (9)
N1—C5—C4—H3	−179.0	C14—C15—C16—C17	−0.2 (10)
N1—C5—C6—N2	0.7 (7)	C14—C15—C16—H15	176.3
N1—C5—C6—C7	−177.8 (5)	C14—C15—C23—H19	−1.3
N2—Ir1—N1—C1	−177.5 (5)	C14—C15—C23—H20	−125.0
N2—Ir1—N1—C5	8.9 (4)	C14—C15—C23—H21	121.1
N2—Ir1—N3—C13	−3.5 (5)	C15—C14—C13—H13	−175.7
N2—Ir1—N3—C17	176.0 (4)	C15—C16—C17—C18	179.9 (6)
N2—Ir1—N4—C18	−63 (2)	C16—C15—C14—H14	179.6
N2—Ir1—N4—C22	118 (2)	C16—C15—C23—H19	179.5
N2—C6—C5—C4	−178.9 (5)	C16—C15—C23—H20	55.8
N2—C6—C7—C8	−1.2 (9)	C16—C15—C23—H21	−58.0
N2—C6—C7—H4	−178.3	C16—C17—C18—C19	−1.6 (9)
N2—C10—C9—C8	−1 (1)	C17—N3—C13—H13	175.2
N2—C10—C9—H5	179.9	C17—C16—C15—C23	179.0 (7)
N3—Ir1—N1—C1	−80.2 (5)	C17—C18—N4—C22	179.7 (5)
N3—Ir1—N1—C5	106.2 (4)	C17—C18—C19—C20	−179.0 (6)
N3—Ir1—N2—C6	−101.8 (4)	C17—C18—C19—H16	−1.5
N3—Ir1—N2—C10	81.1 (5)	C18—N4—C22—C21	0.4 (9)
N3—Ir1—N4—C18	−1.2 (4)	C18—N4—C22—H18	−178.9
N3—Ir1—N4—C22	−179.0 (5)	C18—C17—C16—H15	3.4
N3—C13—C14—C15	−1 (1)	C18—C19—C20—C21	−1.7 (9)
N3—C13—C14—H14	−179.8	C18—C19—C20—C24	−178.1 (6)
N3—C17—C16—C15	−0.5 (10)	C19—C18—N4—C22	−0.5 (8)
N3—C17—C16—H15	−177.0	C19—C20—C21—C22	1.6 (10)
N3—C17—C18—N4	−1.4 (7)	C19—C20—C21—H17	−177.9
N3—C17—C18—C19	178.8 (6)	C19—C20—C24—H22	−3.0
N4—Ir1—N1—C1	−0.1 (5)	C19—C20—C24—H23	−121.2
N4—Ir1—N1—C5	−173.7 (4)	C19—C20—C24—H24	116.0
N4—Ir1—N2—C6	−40 (2)	C20—C21—C22—H18	178.3
N4—Ir1—N2—C10	142 (2)	C21—C20—C19—H16	−179.3
N4—Ir1—N3—C13	−179.2 (5)	C21—C20—C24—H22	−179.3
N4—Ir1—N3—C17	0.3 (4)	C21—C20—C24—H23	62.5
N4—C18—C17—C16	178.2 (6)	C21—C20—C24—H24	−60.3
N4—C18—C19—C20	1.2 (9)	C22—C21—C20—C24	178.1 (6)
N4—C18—C19—H16	178.8	C23—C15—C14—H14	0.4
N4—C22—C21—C20	−1.1 (10)	C23—C15—C16—H15	−4.5
N4—C22—C21—H17	178.5	C24—C20—C19—H16	4.3
C1—N1—C5—C4	−2.2 (8)	C24—C20—C21—H17	−1.4
C1—N1—C5—C6	178.1 (5)	H1—C1—C2—H2	−1.5
C1—C2—C3—C4	−3 (1)	H5—C9—C10—H6	1.0
C1—C2—C3—C11	177.3 (7)	H13—C13—C14—H14	5.8
C2—C1—N1—C5	0.7 (9)	H17—C21—C22—H18	−2.2
C2—C3—C4—C5	2.2 (9)	H17—C21—C22—H18	−2.2
C2—C3—C4—H3	−178.0

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

Experimental details

Crystal data
Chemical formula	[IrCl₂(C₂₄H₂₄N₄)₂]PF₆
M_r	776.57
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.8114 (2), 21.6075 (7), 16.6606 (5)
β (°)	91.4634 (7)
V (Å³)	2811.1 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.07
Crystal size (mm)	0.80 × 0.10 × 0.02

Data collection
Diffractometer	Rigaku RAXIS-RAPID imaging plate diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.552, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	32401, 8462, 6274
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.126, 1.41
No. of reflections	6274
No. of parameters	343
No. of restraints	?
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	2.81, −2.53

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1996), MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), TEXSAN.

Selected geometric parameters (Å, º) top

Ir1—Cl1	2.360 (9)	Ir1—N2	2.036 (5)
Ir1—Cl2	2.356 (2)	Ir1—N3	2.015 (5)
Ir1—N1	2.131 (5)	Ir1—N4	2.024 (4)

Cl1—Ir1—Cl2	89.5 (2)	Cl2—Ir1—N4	96.2 (1)
Cl1—Ir1—N1	175.9 (3)	N1—Ir1—N2	78.1 (2)
Cl1—Ir1—N2	101.7 (3)	N1—Ir1—N3	94.8 (2)
Cl1—Ir1—N3	89.3 (3)	N1—Ir1—N4	97.7 (2)
Cl1—Ir1—N4	82.6 (3)	N2—Ir1—N3	98.1 (2)
Cl2—Ir1—N1	86.4 (1)	N2—Ir1—N4	175.1 (2)
Cl2—Ir1—N2	86.1 (1)	N3—Ir1—N4	79.6 (2)
Cl2—Ir1—N3	175.8 (1)

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cis-Di­chloro­bis(4,4'-di­methyl-2,2'-bi­pyridine)­iridium(III) hexa­fluoro­phosphate

Supporting information

Key indicators

checkCIF results

cis-Dichlorobis(4,4'-dimethyl-2,2'-bipyridine)iridium(III) hexafluorophosphate