Dichlorido(9-methyl­adenine-κN7)(η5-penta­methyl­cyclo­penta­dien­yl)iridium(III) dichloromethane solvate

Bruhn, C.; Küger, T.; Steinborn, D.

doi:10.1107/S1600536808003760

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages m455-m456

doi:10.1107/S1600536808003760

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Dichlorido(9-methyladenine-κN⁷)(η⁵-pentamethylcyclopentadienyl)iridium(III) dichloromethane solvate

Clemens Bruhn,^a Thomas Küger ^b and Dirk Steinborn ^b ^*

^aUniversität Kassel, FB 18, Naturwissenschaften, Abt. Metallorganische Chemie, Heinrich-Plett-Strasse 40, 34132 Kassel, Germany, and ^bMartin-Luther-Universität Halle-Wittenberg, Institut für Chemie–Anorganische Chemie, Kurt-Mothes-Strasse 2, 06120 Halle, Germany
^*Correspondence e-mail: dirk.steinborn@chemie.uni-halle.de

(Received 9 January 2008; accepted 4 February 2008; online 6 February 2008)

In the title complex, [Ir(C₁₀H₁₅)Cl₂(C₆H₇N₅)]·CH₂Cl₂ or [Ir(η⁵-C₅Me₅)Cl₂(9-MeAde-κN⁷)]·CH₂Cl₂ (9-MeAde = 9-methyladenine), the coordination geometry of the Ir^III atom approximates to a three-legged piano stool. The 9-methyladenine ligand is coordinated in a monodentate fashion to the Ir centre through its N-7 atom. The crystal structure contains centrosymmetric pairs of molecules, interacting through two N—H⋯N hydrogen bonds. An intramolecular N—H⋯Cl hydrogen bond is formed between the H atom of an NH₂ group and a chlorido ligand. Further short intra- and intermolecular C—H⋯Cl contacts are observed.

Related literature

For background information, see: Lippert (2000 ); Houlton (2002 ). For related literature, see: Zhu et al. (2002 ); Gaballa et al. (2004 , 2008 ); Aakeröy et al. (1999 ); Baldovino-Pantaleon et al. (2007 ); Davies et al. (2003 ); Huang et al. (1998 ); Jeffrey & Saenger (1994 ); Kistenmacher & Rossi (1977 ); McMullan et al. (1980 ).

Experimental

Crystal data

[Ir(C₁₀H₁₅)Cl₂(C₆H₇N₅)]·CH₂Cl₂
M_r = 632.41
Triclinic, $[P \overline 1]$
a = 7.294 (2) Å
b = 11.8698 (14) Å
c = 13.649 (3) Å
α = 71.338 (15)°
β = 83.83 (3)°
γ = 78.003 (14)°
V = 1094.0 (4) Å³
Z = 2
Mo Kα radiation
μ = 6.60 mm⁻¹
T = 200 (2) K
0.19 × 0.15 × 0.13 mm

Data collection

Stoe STADI-4 diffractometer
Absorption correction: multi-scan (X-RED; Stoe & Cie, 2002 ) T_min = 0.32, T_max = 0.43
4132 measured reflections
3807 independent reflections
3246 reflections with I > 2σ(I)
R_int = 0.068
1 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.125
S = 1.13
3807 reflections
250 parameters
H-atom parameters constrained
Δρ_max = 2.87 e Å⁻³
Δρ_min = −3.41 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

C10—Ir	2.127 (10)
C11—Ir	2.165 (10)
C12—Ir	2.164 (10)
C13—Ir	2.159 (11)
C14—Ir	2.153 (10)
Cl1—Ir	2.402 (3)
Cl2—Ir	2.423 (3)
N7—Ir	2.152 (8)

N7—Ir—Cl1	86.0 (2)
N7—Ir—Cl2	91.0 (2)
Cl1—Ir—Cl2	85.72 (9)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯N1ⁱ	0.88	2.14	3.007 (13)	170
N6—H6B⋯Cl2	0.88	2.35	3.168 (10)	155
C8—H8⋯Cl1	0.95	2.77	3.237 (11)	111
C8—H8⋯Cl1ⁱⁱ	0.95	2.65	3.537 (11)	156
C9—H9B⋯Cl3ⁱⁱⁱ	0.98	2.75	3.697 (13)	163
C20—H20B⋯Cl1ⁱⁱ	0.99	2.75	3.519 (15)	135
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1.

Data collection: STADI4 (Stoe & Cie, 2002); cell refinement: STADI4 (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003760/fj2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003760/fj2096Isup2.hkl

checkCIF report

Comment top

Due to their importance in chemotherapy, nucleobase complexes of platinum and other transition metals attract attention. We are interested in syntheses and characterization of such complexes having, especially, metals in higher oxidation states (Zhu et al., 2002; Gaballa et al., 2004; Gaballa et al., 2007). The iridium(III) title complex [IrCl₂(η⁵-C₅Me₅)(9-MeAde-κN⁷)].CH₂Cl₂ (see Figure 1) crystallizes in the triclinic space group P1. Crystals contain centrosymmetric dinuclear molecules (see Figure 2). The coordination geometry of the iridium center approximates a three-legged piano stool, the irdium atom being directly bound to two chloro ligands, to a N7 coordinated 9-methyladenine ligand and to a η⁵-pentamethylcyclopentadienyl ligand. The 9-MeAde ligand is planar in good approximation, the greatest deviation from the mean plane was found for the exocyclic N6 atom (0.06 (1) Å). The Ir–N7 and Ir–Cl1/Ir–Cl2 bonds are as long as those in the complex [IrCl₂(η⁵-C₅Me₅)(NH₂Ph-κN)] (2.152 (8) versus. 2.152 Å and 2.402 (3)/2.423 (3) versus. 2.394/2.419 Å) (Davies et al., 2003).

The dimers are formed through two N6–H6A···N1' hydrogen bonds (N6···N1' 3.01 (1) Å; H6A···N1' 2.14 Å; N6–H6A···N1' 170°). Furthermore, the other hydrogen atom of the exocyclic amino group acts as hydrogen donor in a N6–H6B···Cl2 hydrogen bond (N6···Cl2 3.17 (1) Å; H6B···Cl2 2.35 Å; N6–H6B···Cl2 155°). The structural parameters of these two hydrogen bonds are in accord with analogous hydrogen bonds in nucleobases and in chloro metal complexes, respectively (Jeffrey & Saenger, 1994; Baldovino-Pantaleon et al., 2007). Noteworthy, in crystals of 9-methyladenine two N6–H6A···N1' and N6–H6B···N7' hydrogen bonds link molecules in ribbons (Kistenmacher & Rossi, 1977; McMullan et al., 1980). Furthermore, short intra- and intermolecular C–H···Cl contacts (see Table) indicate stabilizing interactions (Huang et al., 1998; Aakeröy et al., 1999).

Related literature top

For background information, see: Lippert (2000); Houlton (2002). For related literature, see: Zhu et al. (2002); Gaballa et al. (2004); Aakeröy et al. (1999); Baldovino-Pantaleon, Morales-Morales, Hernandez-Ortega, Toscano & Valdes-Martinez (2007); Davies et al. (2003); Gaballa et al. (2007); Huang et al. (1998); Jeffrey & Saenger (1994); Kistenmacher & Rossi (1977); McMullan et al. (1980).

Experimental top

Reaction of [{IrCl₂(η⁵-C₅Me₅)}₂] with 9-methyladenine (9-MeAde) in 1: 2 ratio in methylene chloride resulted in the formation of yellow crystals of the title complex in 67% yield. ¹H NMR (CD₂Cl₂, 200 MHz): δ 1.49 (s, 15H, C₅(CH₃)₅), 3.88 (s, 3H, NCH₃), 8.41 (s, br, 1H, H8), 8.64 (s, br, 1H, H2).

Computing details top

Data collection: STADI4 (Stoe & Cie, 2002); cell refinement: STADI4 (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Structure of the asymmetric unit of the title complex [IrCl₂(η⁵-C₅Me₅)(9-MeAde-κN⁷)].CH₂Cl₂. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Structure of the dinuclear complex [{IrCl₂(η⁵-C₅Me₅)(9-MeAde-κN⁷)}₂] in crystals of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. The numbering scheme of the C atoms is as shown in Figure 1. Symmetry codes: (i) –x + 2, –y, –z + 2.

Dichlorido(9-methyladenine-κN⁷)(η⁵– pentamethylcyclopentadienyl)iridium(III) dichloromethane solvate top

Crystal data top

[Ir(C₁₀H₁₅)Cl₂(C₆H₇N₅)]·CH₂Cl₂	Z = 2
M_r = 632.41	F(000) = 612
Triclinic, P1	D_x = 1.920 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.294 (2) Å	Cell parameters from 32 reflections
b = 11.8698 (14) Å	θ = 6.5–18.9°
c = 13.649 (3) Å	µ = 6.60 mm⁻¹
α = 71.338 (15)°	T = 200 K
β = 83.83 (3)°	Block, colourless
γ = 78.003 (14)°	0.19 × 0.15 × 0.13 mm
V = 1094.0 (4) Å³

Data collection top

Stoe STADI-4 diffractometer	3246 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.068
Graphite monochromator	θ_max = 25.0°, θ_min = 1.6°
profile data from ω/2θ scans	h = −8→8
Absorption correction: multi-scan (X-RED; Stoe & Cie, 2002)	k = −13→14
T_min = 0.32, T_max = 0.43	l = −8→16
4132 measured reflections	1 standard reflections every 60 min
3807 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.0666P)²] where P = (F_o² + 2F_c²)/3
3807 reflections	(Δ/σ)_max < 0.001
250 parameters	Δρ_max = 2.87 e Å⁻³
0 restraints	Δρ_min = −3.41 e Å⁻³
0 constraints

Crystal data top

[Ir(C₁₀H₁₅)Cl₂(C₆H₇N₅)]·CH₂Cl₂	γ = 78.003 (14)°
M_r = 632.41	V = 1094.0 (4) Å³
Triclinic, P1	Z = 2
a = 7.294 (2) Å	Mo Kα radiation
b = 11.8698 (14) Å	µ = 6.60 mm⁻¹
c = 13.649 (3) Å	T = 200 K
α = 71.338 (15)°	0.19 × 0.15 × 0.13 mm
β = 83.83 (3)°

Data collection top

Stoe STADI-4 diffractometer	3246 reflections with I > 2σ(I)
Absorption correction: multi-scan (X-RED; Stoe & Cie, 2002)	R_int = 0.068
T_min = 0.32, T_max = 0.43	1 standard reflections every 60 min
4132 measured reflections	intensity decay: none
3807 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.13	Δρ_max = 2.87 e Å⁻³
3807 reflections	Δρ_min = −3.41 e Å⁻³
250 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C2	0.9961 (15)	−0.0640 (10)	0.7978 (9)	0.030 (2)
H2	1.0628	−0.1450	0.8165	0.036*
C4	0.8452 (14)	0.0945 (9)	0.6832 (8)	0.023 (2)
C5	0.7931 (13)	0.1571 (8)	0.7549 (7)	0.019 (2)
C6	0.8617 (15)	0.0991 (9)	0.8549 (8)	0.026 (2)
C8	0.6814 (13)	0.2726 (9)	0.6092 (8)	0.020 (2)
H8	0.6198	0.3402	0.5573	0.024*
C9	0.7869 (16)	0.1435 (10)	0.4929 (8)	0.029 (2)
H9A	0.7137	0.2109	0.4416	0.035*
H9B	0.7375	0.0696	0.5034	0.035*
H9C	0.9185	0.1318	0.4682	0.035*
C10	0.2376 (14)	0.3257 (10)	0.7454 (8)	0.028 (2)
C11	0.3065 (16)	0.2573 (10)	0.8485 (9)	0.030 (3)
C12	0.2955 (15)	0.3417 (11)	0.9036 (8)	0.031 (3)
C13	0.2174 (16)	0.4615 (11)	0.8368 (10)	0.037 (3)
C14	0.1805 (14)	0.4482 (10)	0.7419 (9)	0.030 (3)
C15	0.213 (2)	0.2713 (14)	0.6624 (11)	0.053 (4)
H15A	0.2482	0.3242	0.5945	0.064*
H15B	0.0821	0.2632	0.6635	0.064*
H15C	0.2941	0.1914	0.6754	0.064*
C16	0.3688 (18)	0.1234 (10)	0.8885 (11)	0.045 (3)
H16A	0.4789	0.1048	0.9301	0.054*
H16B	0.4014	0.0907	0.8301	0.054*
H16C	0.2671	0.0869	0.9315	0.054*
C17	0.3513 (19)	0.3108 (14)	1.0118 (9)	0.050 (4)
H17A	0.4030	0.3772	1.0197	0.060*
H17B	0.4465	0.2366	1.0282	0.060*
H17C	0.2412	0.2982	1.0591	0.060*
C18	0.180 (2)	0.5756 (12)	0.8658 (13)	0.060 (4)
H18A	0.2126	0.6420	0.8067	0.072*
H18B	0.2555	0.5651	0.9243	0.072*
H18C	0.0464	0.5946	0.8855	0.072*
C19	0.0889 (17)	0.5477 (13)	0.6515 (12)	0.056 (4)
H19A	0.0830	0.6263	0.6621	0.068*
H19B	−0.0383	0.5361	0.6462	0.068*
H19C	0.1627	0.5454	0.5876	0.068*
C20	0.331 (2)	0.2130 (12)	0.3148 (10)	0.045 (3)
H20A	0.2167	0.2111	0.2826	0.053*
H20B	0.3533	0.2972	0.2903	0.053*
Cl1	0.5584 (4)	0.5480 (2)	0.6167 (2)	0.0268 (5)
Cl2	0.7133 (4)	0.4366 (2)	0.8520 (2)	0.0289 (6)
Cl3	0.2938 (5)	0.1691 (3)	0.4491 (3)	0.0505 (8)
Cl4	0.5213 (6)	0.1194 (4)	0.2750 (4)	0.0745 (12)
N1	0.9631 (12)	−0.0139 (8)	0.8738 (7)	0.027 (2)
N3	0.9494 (13)	−0.0174 (7)	0.6998 (7)	0.029 (2)
N6	0.8322 (13)	0.1512 (8)	0.9311 (7)	0.031 (2)
H6A	0.8789	0.1115	0.9921	0.037*
H6B	0.7663	0.2249	0.9199	0.037*
N7	0.6850 (11)	0.2692 (7)	0.7069 (6)	0.0188 (17)
N9	0.7732 (12)	0.1709 (8)	0.5912 (6)	0.0233 (18)
Ir	0.47641 (5)	0.39087 (3)	0.76639 (3)	0.01833 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.030 (6)	0.026 (6)	0.033 (6)	0.002 (5)	−0.006 (5)	−0.011 (5)
C4	0.025 (5)	0.024 (5)	0.026 (5)	−0.008 (4)	−0.003 (4)	−0.011 (4)
C5	0.022 (5)	0.017 (5)	0.017 (5)	−0.004 (4)	0.001 (4)	−0.006 (4)
C6	0.028 (6)	0.023 (5)	0.021 (5)	0.002 (4)	−0.003 (4)	−0.003 (4)
C8	0.014 (5)	0.017 (5)	0.025 (5)	0.002 (4)	−0.004 (4)	−0.004 (4)
C9	0.043 (7)	0.025 (6)	0.022 (5)	−0.009 (5)	0.006 (5)	−0.011 (4)
C10	0.018 (5)	0.040 (7)	0.029 (6)	−0.016 (5)	0.005 (4)	−0.011 (5)
C11	0.033 (6)	0.025 (6)	0.035 (6)	−0.017 (5)	0.016 (5)	−0.009 (5)
C12	0.026 (6)	0.043 (7)	0.025 (6)	−0.013 (5)	0.010 (4)	−0.012 (5)
C13	0.023 (6)	0.030 (6)	0.053 (8)	0.005 (5)	0.012 (5)	−0.015 (6)
C14	0.018 (5)	0.028 (6)	0.037 (6)	0.006 (4)	−0.002 (4)	−0.004 (5)
C15	0.055 (9)	0.069 (10)	0.053 (9)	−0.046 (8)	0.006 (7)	−0.026 (8)
C16	0.048 (8)	0.015 (6)	0.064 (9)	−0.014 (5)	0.005 (6)	0.001 (6)
C17	0.041 (7)	0.074 (10)	0.029 (7)	−0.006 (7)	0.006 (6)	−0.013 (7)
C18	0.054 (9)	0.041 (8)	0.092 (12)	0.003 (7)	0.027 (8)	−0.047 (8)
C19	0.019 (6)	0.057 (9)	0.068 (10)	−0.001 (6)	0.000 (6)	0.012 (7)
C20	0.054 (8)	0.037 (7)	0.047 (8)	−0.007 (6)	−0.001 (6)	−0.020 (6)
Cl1	0.0323 (14)	0.0227 (13)	0.0256 (13)	−0.0081 (10)	−0.0010 (10)	−0.0057 (10)
Cl2	0.0349 (14)	0.0274 (13)	0.0295 (14)	−0.0074 (11)	−0.0051 (11)	−0.0136 (11)
Cl3	0.055 (2)	0.0467 (19)	0.058 (2)	−0.0206 (16)	0.0060 (16)	−0.0227 (16)
Cl4	0.071 (3)	0.081 (3)	0.072 (3)	0.008 (2)	0.009 (2)	−0.042 (2)
N1	0.028 (5)	0.018 (4)	0.033 (5)	0.000 (4)	−0.002 (4)	−0.008 (4)
N3	0.032 (5)	0.015 (4)	0.040 (6)	0.001 (4)	0.000 (4)	−0.013 (4)
N6	0.043 (6)	0.023 (5)	0.023 (5)	0.011 (4)	−0.009 (4)	−0.011 (4)
N7	0.021 (4)	0.010 (4)	0.020 (4)	0.004 (3)	−0.002 (3)	−0.001 (3)
N9	0.029 (5)	0.022 (4)	0.019 (4)	−0.006 (4)	0.005 (3)	−0.008 (4)
Ir	0.0201 (2)	0.0154 (2)	0.0201 (2)	−0.00199 (14)	0.00201 (14)	−0.00814 (15)

Geometric parameters (Å, º) top

C2—N3	1.325 (14)	C13—C18	1.494 (17)
C2—N1	1.331 (14)	C13—Ir	2.159 (11)
C2—H2	0.9500	C14—C19	1.510 (16)
C4—N3	1.348 (13)	C14—Ir	2.153 (10)
C4—N9	1.375 (13)	C15—H15A	0.9800
C4—C5	1.386 (14)	C15—H15B	0.9800
C5—N7	1.392 (12)	C15—H15C	0.9800
C5—C6	1.410 (14)	C16—H16A	0.9800
C6—N1	1.349 (13)	C16—H16B	0.9800
C6—N6	1.349 (14)	C16—H16C	0.9800
C8—N7	1.325 (13)	C17—H17A	0.9800
C8—N9	1.335 (13)	C17—H17B	0.9800
C8—H8	0.9500	C17—H17C	0.9800
C9—N9	1.467 (13)	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800
C9—H9C	0.9800	C19—H19A	0.9800
C10—C14	1.414 (16)	C19—H19B	0.9800
C10—C11	1.463 (16)	C19—H19C	0.9800
C10—C15	1.514 (17)	C20—Cl4	1.743 (13)
C10—Ir	2.127 (10)	C20—Cl3	1.745 (13)
C11—C12	1.419 (16)	C20—H20A	0.9900
C11—C16	1.493 (15)	C20—H20B	0.9900
C11—Ir	2.165 (10)	Cl1—Ir	2.402 (3)
C12—C13	1.458 (16)	Cl2—Ir	2.423 (3)
C12—C17	1.484 (16)	N6—H6A	0.8800
C12—Ir	2.164 (10)	N6—H6B	0.8800
C13—C14	1.413 (17)	N7—Ir	2.152 (8)

N3—C2—N1	129.5 (10)	C12—C17—H17A	109.5
N3—C2—H2	115.3	C12—C17—H17B	109.5
N1—C2—H2	115.3	H17A—C17—H17B	109.5
N3—C4—N9	127.0 (9)	C12—C17—H17C	109.5
N3—C4—C5	127.0 (10)	H17A—C17—H17C	109.5
N9—C4—C5	106.0 (9)	H17B—C17—H17C	109.5
C4—C5—N7	108.9 (8)	C13—C18—H18A	109.5
C4—C5—C6	116.4 (9)	C13—C18—H18B	109.5
N7—C5—C6	134.6 (9)	H18A—C18—H18B	109.5
N1—C6—N6	119.0 (9)	C13—C18—H18C	109.5
N1—C6—C5	117.6 (9)	H18A—C18—H18C	109.5
N6—C6—C5	123.4 (9)	H18B—C18—H18C	109.5
N7—C8—N9	112.9 (8)	C14—C19—H19A	109.5
N7—C8—H8	123.5	C14—C19—H19B	109.5
N9—C8—H8	123.5	H19A—C19—H19B	109.5
N9—C9—H9A	109.5	C14—C19—H19C	109.5
N9—C9—H9B	109.5	H19A—C19—H19C	109.5
H9A—C9—H9B	109.5	H19B—C19—H19C	109.5
N9—C9—H9C	109.5	Cl4—C20—Cl3	112.3 (8)
H9A—C9—H9C	109.5	Cl4—C20—H20A	109.2
H9B—C9—H9C	109.5	Cl3—C20—H20A	109.2
C14—C10—C11	107.9 (10)	Cl4—C20—H20B	109.2
C14—C10—C15	126.5 (11)	Cl3—C20—H20B	109.2
C11—C10—C15	125.3 (11)	H20A—C20—H20B	107.9
C14—C10—Ir	71.7 (6)	C2—N1—C6	119.0 (9)
C11—C10—Ir	71.5 (6)	C2—N3—C4	110.4 (9)
C15—C10—Ir	127.3 (8)	C6—N6—H6A	120.0
C12—C11—C10	107.0 (10)	C6—N6—H6B	120.0
C12—C11—C16	126.9 (11)	H6A—N6—H6B	120.0
C10—C11—C16	126.1 (11)	C8—N7—C5	104.9 (8)
C12—C11—Ir	70.8 (6)	C8—N7—Ir	119.3 (6)
C10—C11—Ir	68.7 (5)	C5—N7—Ir	132.2 (6)
C16—C11—Ir	127.4 (8)	C8—N9—C4	107.2 (8)
C11—C12—C13	108.4 (10)	C8—N9—C9	126.4 (9)
C11—C12—C17	125.0 (12)	C4—N9—C9	126.3 (9)
C13—C12—C17	126.6 (12)	C10—Ir—N7	97.3 (4)
C11—C12—Ir	70.9 (6)	C10—Ir—C14	38.6 (4)
C13—C12—Ir	70.1 (6)	N7—Ir—C14	130.7 (4)
C17—C12—Ir	125.7 (8)	C10—Ir—C13	65.1 (5)
C14—C13—C12	107.3 (10)	N7—Ir—C13	160.2 (4)
C14—C13—C18	127.1 (12)	C14—Ir—C13	38.3 (5)
C12—C13—C18	125.6 (13)	C10—Ir—C12	65.4 (4)
C14—C13—Ir	70.6 (6)	N7—Ir—C12	126.5 (4)
C12—C13—Ir	70.4 (6)	C14—Ir—C12	64.8 (4)
C18—C13—Ir	125.4 (9)	C13—Ir—C12	39.4 (4)
C13—C14—C10	109.4 (10)	C10—Ir—C11	39.9 (4)
C13—C14—C19	125.8 (12)	N7—Ir—C11	95.5 (4)
C10—C14—C19	124.7 (12)	C14—Ir—C11	65.2 (4)
C13—C14—Ir	71.1 (6)	C13—Ir—C11	65.3 (4)
C10—C14—Ir	69.7 (6)	C12—Ir—C11	38.3 (4)
C19—C14—Ir	126.8 (8)	C10—Ir—Cl1	112.7 (3)
C10—C15—H15A	109.5	N7—Ir—Cl1	86.0 (2)
C10—C15—H15B	109.5	C14—Ir—Cl1	93.1 (3)
H15A—C15—H15B	109.5	C13—Ir—Cl1	108.6 (3)
C10—C15—H15C	109.5	C12—Ir—Cl1	147.4 (3)
H15A—C15—H15C	109.5	C11—Ir—Cl1	152.5 (3)
H15B—C15—H15C	109.5	C10—Ir—Cl2	160.2 (3)
C11—C16—H16A	109.5	N7—Ir—Cl2	91.0 (2)
C11—C16—H16B	109.5	C14—Ir—Cl2	138.2 (3)
H16A—C16—H16B	109.5	C13—Ir—Cl2	103.0 (4)
C11—C16—H16C	109.5	C12—Ir—Cl2	95.2 (3)
H16A—C16—H16C	109.5	C11—Ir—Cl2	121.6 (3)
H16B—C16—H16C	109.5	Cl1—Ir—Cl2	85.72 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N1ⁱ	0.88	2.14	3.007 (13)	170
N6—H6B···Cl2	0.88	2.35	3.168 (10)	155
C8—H8···Cl1	0.95	2.77	3.237 (11)	111
C8—H8···Cl1ⁱⁱ	0.95	2.65	3.537 (11)	156
C9—H9B···Cl3ⁱⁱⁱ	0.98	2.75	3.697 (13)	163
C20—H20B···Cl1ⁱⁱ	0.99	2.75	3.519 (15)	135

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

Experimental details

Crystal data
Chemical formula	[Ir(C₁₀H₁₅)Cl₂(C₆H₇N₅)]·CH₂Cl₂
M_r	632.41
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	7.294 (2), 11.8698 (14), 13.649 (3)
α, β, γ (°)	71.338 (15), 83.83 (3), 78.003 (14)
V (Å³)	1094.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	6.60
Crystal size (mm)	0.19 × 0.15 × 0.13

Data collection
Diffractometer	Stoe STADI-4 diffractometer
Absorption correction	Multi-scan (X-RED; Stoe & Cie, 2002)
T_min, T_max	0.32, 0.43
No. of measured, independent and observed [I > 2σ(I)] reflections	4132, 3807, 3246
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.125, 1.13
No. of reflections	3807
No. of parameters	250
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.87, −3.41

Computer programs: STADI4 (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Selected geometric parameters (Å, º) top

C10—Ir	2.127 (10)	C14—Ir	2.153 (10)
C11—Ir	2.165 (10)	Cl1—Ir	2.402 (3)
C12—Ir	2.164 (10)	Cl2—Ir	2.423 (3)
C13—Ir	2.159 (11)	N7—Ir	2.152 (8)

N7—Ir—Cl1	86.0 (2)	Cl1—Ir—Cl2	85.72 (9)
N7—Ir—Cl2	91.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N1ⁱ	0.8800	2.1400	3.007 (13)	170.00
N6—H6B···Cl2	0.8800	2.3500	3.168 (10)	155.00
C8—H8···Cl1	0.9500	2.7700	3.237 (11)	111.00
C8—H8···Cl1ⁱⁱ	0.9500	2.6500	3.537 (11)	156.00
C9—H9B···Cl3ⁱⁱⁱ	0.9800	2.7500	3.697 (13)	163.00
C20—H20B···Cl1ⁱⁱ	0.9900	2.7500	3.519 (15)	135.00

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

Acknowledgements

We thank the Deutsche Forschungsgemeinschaft for financial support.

References

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