Crystal structure of tri­chlorido­(4′-ferrocenyl-2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)iridium(III) aceto­nitrile disolvate

Davaasuren, B.; Padhy, H.; Rothenberger, A.

doi:10.1107/S2056989015003473

metal-organic compounds

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Volume 71| Part 3| March 2015| Pages m69-m70

doi:10.1107/S2056989015003473

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Crystal structure of trichlorido(4′-ferrocenyl-2,2′:6′,2′′-terpyridine-κ³N,N′,N′′)iridium(III) acetonitrile disolvate

Bambar Davaasuren,^a Harihara Padhy ^a and Alexander Rothenberger ^a ^*

^aPhysical Sciences and Engineering Division, King Abdullah University of Science and Technology, KAUST, Thuwal 23955-6900, Kingdom of , Saudi Arabia
^*Correspondence e-mail: alexander.rothenberger@kaust.edu.sa

Edited by M. Weil, Vienna University of Technology, Austria (Received 9 February 2015; accepted 19 February 2015; online 25 February 2015)

In the title compound, [FeIr(C₅H₅)(C₂₀H₁₄N₃)Cl₃]·2CH₃CN, the central Ir^III atom is sixfold coordinated by three chloride ligands and three terpyridine N atoms in a slightly distorted octahedral fashion. The terpyridine ligand is functionalized at the 4′-position with a ferrocenyl group, the latter being in an eclipsed conformation. In the crystal, molecules are stacked in rows parallel to [001], with the acetonitrile solvent molecules situated between the rows. An extensive network of intra- and intermolecular C—H⋯Cl interactions is present, stabilizing the three-dimensional structure.

Keywords: crystal structure; iridium; 4′-ferrocenyl-2,2′:6′,2′′-terpyridine.

CCDC reference: 1050374

1. Related literature

Complexes of metal ions with ferrocene-substituted terpyridine ligands show interesting electron transport dynamics (Sakamoto et al., 2015 ), DNA cleavage and anticancer activity (Maity et al., 2010 ) and enhanced electro-optical properties (Wu et al., 2011 ). For the preparation of the ferrocenylterpyridine ligand, see: Constable et al. (1994 ).

2. Experimental

2.1. Crystal data

[FeIr(C₅H₅)(C₂₀H₁₄N₃)Cl₃]·2C₂H₃N
M_r = 797.94
Monoclinic, P 2₁ /a
a = 11.557 (5) Å
b = 21.663 (5) Å
c = 11.579 (5) Å
β = 105.974 (5)°
V = 2787.0 (18) Å³
Z = 4
Mo Kα radiation
μ = 5.61 mm⁻¹
T = 150 K
0.30 × 0.23 × 0.20 mm

2.2. Data collection

Stoe IPDS 2 diffractometer
Absorption correction: numerical (X-AREA and X-RED32; Stoe & Cie, 2013 ) T_min = 0.348, T_max = 0.390
26757 measured reflections
7374 independent reflections
5312 reflections with I > 2σ(I)
R_int = 0.069

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.076
S = 1.02
7374 reflections
354 parameters
H-atom parameters constrained
Δρ_max = 1.11 e Å⁻³
Δρ_min = −1.10 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cl3ⁱ	0.98	2.83	3.771 (5)	162
C24—H24A⋯Cl1ⁱⁱ	0.95	2.75	3.701 (9)	174
C6—H6⋯Cl3ⁱ	0.95	2.83	3.731 (6)	159
C9—H9B⋯Cl3	0.98	2.99	3.875 (10)	151
C11—H11⋯Cl3ⁱ	0.95	2.82	3.711 (5)	157
C17—H17⋯Cl1	0.95	2.90	3.486 (6)	121
C20—H20⋯Cl1	0.95	2.89	3.484 (5)	122
C24—H24A⋯Cl1ⁱⁱ	0.98	2.73	3.701 (8)	174
C19—H19⋯Cl2ⁱⁱⁱ	0.95	2.82	3.716 (6)	158
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) x, y, z-1; (iii) -x+1, -y, -z.

Data collection: X-AREA (Stoe & Cie, 2013); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL.

Supporting information

CCDC reference: 1050374

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015003473/wm5126sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015003473/wm5126Isup2.hkl

checkCIF report

Synthesis and crystallization top

IrCl₃ (1 mmol) was suspended in 50 ml of methanol and stirred for 20 minutes. 4'-Ferrocenyl-2,2':6',2''-terpyridine (1.2 mmol), dissolved in 3 ml THF, was dropwise added to the IrCl₃ suspension and refluxed at 368 K overnight. The reaction mixture was cooled down to room temperature and filtered. The dark blue residue was subsequently washed with methanol and diethyl ether. The yield was around 80%. Rhombic dark-violet crystals were grown by diffusion from an acetonitrile/diethyl ether mixture.

Refinement top

The H atoms were treated as riding and U_iso(H) values set at 1.2 (aromatic) or 1.5 (methyl) U_eq(C).

Related literature top

Complexes of metal ions with ferrocene-substituted terpyridine ligands show interesting electron transport dynamics (Sakamoto et al. (2015), DNA cleavage and anticancer activity (Maity et al., 2010) and enhanced electro-optical properties (Wu et al., 2011). For the preparation of the ferrocenylterpyridine ligand, see: Constable et al. (1994).

Computing details top

Data collection: X-AREA (Stoe, 2013); cell refinement: X-AREA (Stoe, 2013); data reduction: X-AREA (Stoe, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL (Sheldrick, b).

Figures top

	Fig. 1. The molecular components of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Intra- and intermolecular C—H···Cl interactions in the crystal packing, indicated by dashed-red lines.
	Fig. 3. Packing diagram of the title compound viewed along [010].

Trichlorido(4'-ferrocenyl-2,2':6',2''-terpyridine-κ³N,N',N'')iridium(III) acetonitrile disolvate top

Crystal data top

[FeIr(C₅H₅)(C₂₀H₁₄N₃)Cl₃]·2C₂H₃N	F(000) = 1552
M_r = 797.94	D_x = 1.902 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
a = 11.557 (5) Å	Cell parameters from 9378 reflections
b = 21.663 (5) Å	θ = 1.8–29.3°
c = 11.579 (5) Å	µ = 5.61 mm⁻¹
β = 105.974 (5)°	T = 150 K
V = 2787.0 (18) Å³	Block, dark-violet
Z = 4	0.30 × 0.23 × 0.20 mm

Data collection top

STOE IPDS 2 diffractometer	7374 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	5312 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.069
rotation method scans	θ_max = 29.2°, θ_min = 1.8°
Absorption correction: numerical (X-AREA and X-RED32; Stoe, 2013)	h = −15→15
T_min = 0.348, T_max = 0.390	k = −28→29
26757 measured reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.0322P)² + 2.6254P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
7374 reflections	Δρ_max = 1.11 e Å⁻³
354 parameters	Δρ_min = −1.10 e Å⁻³

Crystal data top

[FeIr(C₅H₅)(C₂₀H₁₄N₃)Cl₃]·2C₂H₃N	V = 2787.0 (18) Å³
M_r = 797.94	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 11.557 (5) Å	µ = 5.61 mm⁻¹
b = 21.663 (5) Å	T = 150 K
c = 11.579 (5) Å	0.30 × 0.23 × 0.20 mm
β = 105.974 (5)°

Data collection top

STOE IPDS 2 diffractometer	7374 independent reflections
Absorption correction: numerical (X-AREA and X-RED32; Stoe, 2013)	5312 reflections with I > 2σ(I)
T_min = 0.348, T_max = 0.390	R_int = 0.069
26757 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.076	H-atom parameters constrained
S = 1.02	Δρ_max = 1.11 e Å⁻³
7374 reflections	Δρ_min = −1.10 e Å⁻³
354 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.

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

	x	y	z	U_iso*/U_eq
Ir1	0.26476 (2)	0.10206 (2)	0.12149 (2)	0.02014 (5)
Fe1	0.62436 (7)	0.19070 (3)	−0.31981 (7)	0.02452 (15)
Cl1	0.13455 (12)	0.07759 (6)	0.24188 (13)	0.0293 (3)
Cl2	0.42892 (11)	0.05633 (6)	0.26314 (11)	0.0261 (2)
Cl3	0.10318 (12)	0.14691 (6)	−0.02370 (12)	0.0277 (3)
N1	0.2392 (8)	0.1022 (4)	−0.3477 (7)	0.083 (3)
N2	0.3740 (4)	0.12151 (18)	0.0261 (4)	0.0213 (8)
N3	0.2439 (4)	0.02408 (18)	0.0187 (4)	0.0229 (8)
N4	0.3233 (4)	0.18687 (18)	0.1925 (4)	0.0217 (8)
N5	0.1880 (7)	−0.0828 (3)	−0.4257 (6)	0.0595 (17)
C1	0.6807 (5)	0.1118 (2)	−0.2268 (5)	0.0264 (10)
H1	0.6479	0.0695	−0.2495	0.032*
C2	0.3395 (5)	0.2744 (2)	0.3209 (5)	0.0282 (11)
H2	0.3156	0.2952	0.3828	0.034*
C3	0.3169 (4)	0.0234 (2)	−0.0569 (5)	0.0219 (9)
C4	0.6388 (5)	0.1554 (2)	−0.1528 (5)	0.0235 (10)
C5	0.4361 (4)	0.1751 (2)	0.0470 (5)	0.0221 (10)
C6	0.4562 (5)	0.2697 (2)	0.1801 (5)	0.0253 (10)
H6	0.5133	0.2875	0.1446	0.030*
C7	0.3932 (5)	0.0789 (2)	−0.0515 (5)	0.0224 (10)
C8	0.4053 (5)	0.2128 (2)	0.1420 (5)	0.0222 (10)
C9	0.0512 (8)	0.0476 (4)	−0.3117 (9)	0.064 (2)
H9A	−0.0203	0.0576	−0.3772	0.095*
H9B	0.0399	0.0620	−0.2354	0.095*
H9C	0.0634	0.0028	−0.3083	0.095*
C10	0.4768 (5)	0.0895 (2)	−0.1144 (5)	0.0234 (10)
H10	0.4892	0.0599	−0.1703	0.028*
C11	0.5210 (5)	0.1880 (2)	−0.0131 (5)	0.0236 (10)
H11	0.5639	0.2259	0.0006	0.028*
C12	0.7121 (5)	0.2094 (2)	−0.1450 (5)	0.0275 (11)
H12	0.7035	0.2482	−0.1012	0.033*
C13	0.5157 (6)	0.2642 (2)	−0.3859 (6)	0.0341 (13)
H13	0.5050	0.3018	−0.3399	0.041*
C14	0.1662 (5)	−0.0745 (2)	−0.0555 (5)	0.0313 (12)
H14	0.1132	−0.1079	−0.0543	0.038*
C15	0.5438 (5)	0.1451 (2)	−0.0944 (5)	0.0228 (10)
C16	0.7782 (5)	0.1396 (3)	−0.2599 (5)	0.0320 (12)
H16	0.8245	0.1203	−0.3119	0.038*
C17	0.1695 (5)	−0.0228 (2)	0.0186 (5)	0.0253 (10)
H17	0.1177	−0.0213	0.0696	0.030*
C18	0.4226 (5)	0.3002 (2)	0.2706 (5)	0.0277 (11)
H18	0.4571	0.3392	0.2980	0.033*
C19	0.3176 (5)	−0.0262 (2)	−0.1311 (5)	0.0252 (10)
H19	0.3692	−0.0265	−0.1824	0.030*
C20	0.2910 (5)	0.2170 (2)	0.2793 (5)	0.0267 (10)
H20	0.2334	0.1988	0.3137	0.032*
C21	0.7980 (5)	0.1994 (3)	−0.2092 (5)	0.0332 (12)
H21	0.8599	0.2297	−0.2192	0.040*
C22	0.4898 (6)	0.1674 (3)	−0.4711 (5)	0.0347 (13)
H22	0.4583	0.1249	−0.4947	0.042*
C23	0.6027 (6)	0.2562 (3)	−0.4513 (6)	0.0365 (13)
H23	0.6641	0.2872	−0.4594	0.044*
C24	0.3273 (8)	−0.0102 (4)	−0.5027 (7)	0.058 (2)
H24A	0.2789	0.0110	−0.5746	0.088*
H24B	0.3902	−0.0346	−0.5233	0.088*
H24C	0.3646	0.0204	−0.4414	0.088*
C25	0.4470 (5)	0.2092 (3)	−0.3980 (6)	0.0348 (13)
H25	0.3794	0.2013	−0.3614	0.042*
C26	0.2412 (5)	−0.0762 (2)	−0.1299 (6)	0.0291 (11)
H26	0.2409	−0.1110	−0.1799	0.035*
C27	0.5857 (6)	0.1966 (3)	−0.5037 (5)	0.0358 (13)
H27	0.6343	0.1780	−0.5542	0.043*
C28	0.2512 (7)	−0.0504 (3)	−0.4568 (6)	0.0462 (16)
C29	0.1552 (8)	0.0774 (4)	−0.3329 (8)	0.057 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.02160 (8)	0.01507 (7)	0.02675 (8)	0.00012 (8)	0.01168 (6)	0.00098 (8)
Fe1	0.0263 (4)	0.0222 (3)	0.0289 (4)	0.0001 (3)	0.0140 (3)	0.0010 (3)
Cl1	0.0290 (6)	0.0285 (6)	0.0366 (7)	0.0003 (5)	0.0193 (6)	0.0053 (5)
Cl2	0.0270 (6)	0.0230 (5)	0.0295 (6)	0.0024 (4)	0.0099 (5)	0.0016 (4)
Cl3	0.0282 (6)	0.0231 (5)	0.0330 (6)	0.0048 (5)	0.0102 (5)	0.0033 (5)
N1	0.089 (6)	0.081 (5)	0.073 (5)	−0.031 (5)	0.013 (4)	0.022 (5)
N2	0.022 (2)	0.0174 (17)	0.026 (2)	0.0003 (14)	0.0098 (17)	0.0027 (15)
N3	0.026 (2)	0.0193 (18)	0.026 (2)	−0.0014 (16)	0.0117 (18)	−0.0014 (16)
N4	0.025 (2)	0.0174 (18)	0.026 (2)	−0.0037 (15)	0.0130 (17)	−0.0025 (15)
N5	0.074 (5)	0.048 (3)	0.060 (4)	−0.007 (3)	0.026 (4)	0.010 (3)
C1	0.028 (2)	0.025 (3)	0.030 (2)	0.0002 (19)	0.013 (2)	−0.0027 (19)
C2	0.039 (3)	0.019 (2)	0.028 (3)	0.007 (2)	0.013 (2)	0.0005 (19)
C3	0.022 (2)	0.017 (2)	0.028 (2)	0.0016 (17)	0.010 (2)	0.0019 (18)
C4	0.028 (2)	0.020 (2)	0.026 (2)	0.0006 (19)	0.014 (2)	−0.0013 (18)
C5	0.024 (2)	0.0145 (19)	0.029 (2)	−0.0016 (17)	0.010 (2)	0.0037 (17)
C6	0.029 (3)	0.016 (2)	0.032 (3)	0.0013 (18)	0.012 (2)	0.0012 (19)
C7	0.024 (2)	0.019 (2)	0.027 (2)	0.0020 (18)	0.012 (2)	0.0027 (18)
C8	0.026 (2)	0.0145 (19)	0.027 (2)	−0.0001 (17)	0.009 (2)	0.0007 (17)
C9	0.051 (4)	0.057 (5)	0.082 (6)	0.009 (4)	0.016 (4)	0.002 (4)
C10	0.027 (2)	0.019 (2)	0.028 (2)	0.0011 (17)	0.012 (2)	−0.0010 (17)
C11	0.023 (2)	0.018 (2)	0.031 (3)	−0.0020 (18)	0.009 (2)	0.0004 (19)
C12	0.027 (3)	0.026 (2)	0.031 (3)	−0.0046 (19)	0.010 (2)	−0.004 (2)
C13	0.042 (3)	0.019 (2)	0.042 (3)	0.007 (2)	0.013 (3)	0.005 (2)
C14	0.036 (3)	0.019 (2)	0.038 (3)	−0.014 (2)	0.008 (3)	−0.004 (2)
C15	0.026 (2)	0.020 (2)	0.025 (2)	0.0009 (18)	0.011 (2)	0.0032 (18)
C16	0.029 (3)	0.037 (3)	0.036 (3)	0.006 (2)	0.018 (2)	0.002 (2)
C17	0.023 (2)	0.022 (2)	0.033 (3)	−0.0022 (19)	0.012 (2)	0.005 (2)
C18	0.031 (3)	0.021 (2)	0.031 (3)	0.0035 (19)	0.009 (2)	0.0012 (19)
C19	0.028 (3)	0.020 (2)	0.030 (3)	−0.0042 (19)	0.010 (2)	−0.0033 (19)
C20	0.029 (3)	0.024 (2)	0.032 (3)	0.000 (2)	0.016 (2)	0.000 (2)
C21	0.027 (3)	0.042 (3)	0.033 (3)	−0.003 (2)	0.012 (2)	−0.002 (2)
C22	0.038 (3)	0.031 (3)	0.034 (3)	0.001 (2)	0.006 (3)	0.000 (2)
C23	0.037 (3)	0.034 (3)	0.039 (3)	−0.002 (2)	0.011 (3)	0.015 (2)
C24	0.058 (5)	0.067 (5)	0.054 (4)	0.008 (4)	0.023 (4)	0.025 (4)
C25	0.030 (3)	0.036 (3)	0.041 (3)	0.001 (2)	0.015 (3)	0.006 (2)
C26	0.032 (3)	0.020 (2)	0.034 (3)	−0.004 (2)	0.007 (2)	−0.005 (2)
C27	0.043 (3)	0.044 (3)	0.024 (3)	0.010 (3)	0.014 (3)	0.005 (2)
C28	0.055 (4)	0.049 (4)	0.036 (3)	0.007 (3)	0.013 (3)	0.004 (3)
C29	0.060 (5)	0.042 (4)	0.069 (5)	0.009 (4)	0.018 (4)	0.005 (4)

Geometric parameters (Å, º) top

Ir1—N2	1.939 (4)	C6—H6	0.9500
Ir1—N3	2.042 (4)	C7—C10	1.379 (7)
Ir1—N4	2.050 (4)	C9—C29	1.444 (12)
Ir1—Cl3	2.3516 (14)	C9—H9A	0.9800
Ir1—Cl2	2.3575 (14)	C9—H9B	0.9800
Ir1—Cl1	2.3756 (15)	C9—H9C	0.9800
Fe1—C1	2.029 (5)	C10—C15	1.416 (7)
Fe1—C12	2.040 (5)	C10—H10	0.9500
Fe1—C25	2.040 (6)	C11—C15	1.398 (7)
Fe1—C13	2.041 (5)	C11—H11	0.9500
Fe1—C4	2.044 (5)	C12—C21	1.411 (8)
Fe1—C23	2.046 (6)	C12—H12	1.0000
Fe1—C16	2.047 (6)	C13—C25	1.416 (8)
Fe1—C27	2.056 (6)	C13—C23	1.426 (9)
Fe1—C22	2.059 (6)	C13—H13	1.0000
Fe1—C21	2.071 (6)	C14—C26	1.380 (9)
N1—C29	1.163 (11)	C14—C17	1.405 (7)
N2—C7	1.349 (6)	C14—H14	0.9500
N2—C5	1.351 (6)	C16—C21	1.416 (8)
N3—C17	1.331 (6)	C16—H16	1.0000
N3—C3	1.372 (7)	C17—H17	0.9500
N4—C20	1.334 (7)	C18—H18	0.9500
N4—C8	1.364 (6)	C19—C26	1.400 (7)
N5—C28	1.142 (10)	C19—H19	0.9500
C1—C16	1.420 (8)	C20—H20	0.9500
C1—C4	1.445 (7)	C21—H21	1.0000
C1—H1	1.0000	C22—C27	1.415 (9)
C2—C18	1.372 (8)	C22—C25	1.419 (8)
C2—C20	1.395 (7)	C22—H22	1.0000
C2—H2	0.9500	C23—C27	1.417 (9)
C3—C19	1.377 (7)	C23—H23	1.0000
C3—C7	1.483 (7)	C24—C28	1.438 (11)
C4—C12	1.433 (7)	C24—H24A	0.9800
C4—C15	1.457 (7)	C24—H24B	0.9800
C5—C11	1.379 (7)	C24—H24C	0.9800
C5—C8	1.489 (7)	C25—H25	1.0000
C6—C18	1.382 (8)	C26—H26	0.9500
C6—C8	1.386 (7)	C27—H27	1.0000

N2—Ir1—N3	80.72 (17)	N2—C7—C3	112.2 (4)
N2—Ir1—N4	80.75 (17)	C10—C7—C3	127.4 (5)
N3—Ir1—N4	161.46 (17)	N4—C8—C6	120.9 (5)
N2—Ir1—Cl3	90.93 (13)	N4—C8—C5	115.3 (4)
N3—Ir1—Cl3	88.97 (13)	C6—C8—C5	123.8 (5)
N4—Ir1—Cl3	91.49 (12)	C29—C9—H9A	109.5
N2—Ir1—Cl2	87.84 (13)	C29—C9—H9B	109.5
N3—Ir1—Cl2	90.07 (13)	H9A—C9—H9B	109.5
N4—Ir1—Cl2	89.08 (12)	C29—C9—H9C	109.5
Cl3—Ir1—Cl2	178.55 (5)	H9A—C9—H9C	109.5
N2—Ir1—Cl1	178.77 (13)	H9B—C9—H9C	109.5
N3—Ir1—Cl1	99.50 (13)	C7—C10—C15	119.1 (5)
N4—Ir1—Cl1	99.03 (12)	C7—C10—H10	120.5
Cl3—Ir1—Cl1	90.29 (6)	C15—C10—H10	120.5
Cl2—Ir1—Cl1	90.94 (6)	C5—C11—C15	119.8 (4)
C1—Fe1—C12	69.0 (2)	C5—C11—H11	120.1
C1—Fe1—C25	122.5 (2)	C15—C11—H11	120.1
C12—Fe1—C25	124.4 (2)	C21—C12—C4	109.3 (5)
C1—Fe1—C13	158.4 (2)	C21—C12—Fe1	71.1 (3)
C12—Fe1—C13	107.7 (2)	C4—C12—Fe1	69.6 (3)
C25—Fe1—C13	40.6 (2)	C21—C12—H12	125.3
C1—Fe1—C4	41.56 (19)	C4—C12—H12	125.3
C12—Fe1—C4	41.1 (2)	Fe1—C12—H12	125.3
C25—Fe1—C4	107.7 (2)	C25—C13—C23	107.7 (5)
C13—Fe1—C4	121.9 (2)	C25—C13—Fe1	69.7 (3)
C1—Fe1—C23	159.2 (2)	C23—C13—Fe1	69.8 (3)
C12—Fe1—C23	121.7 (2)	C25—C13—H13	126.1
C25—Fe1—C23	68.3 (2)	C23—C13—H13	126.1
C13—Fe1—C23	40.8 (3)	Fe1—C13—H13	126.1
C4—Fe1—C23	157.7 (2)	C26—C14—C17	119.1 (5)
C1—Fe1—C16	40.8 (2)	C26—C14—H14	120.5
C12—Fe1—C16	67.9 (2)	C17—C14—H14	120.5
C25—Fe1—C16	158.4 (2)	C11—C15—C10	118.7 (5)
C13—Fe1—C16	159.4 (2)	C11—C15—C4	121.1 (4)
C4—Fe1—C16	68.9 (2)	C10—C15—C4	120.2 (4)
C23—Fe1—C16	123.0 (3)	C21—C16—C1	109.0 (5)
C1—Fe1—C27	123.3 (2)	C21—C16—Fe1	70.8 (3)
C12—Fe1—C27	157.3 (2)	C1—C16—Fe1	68.9 (3)
C25—Fe1—C27	67.8 (3)	C21—C16—H16	125.5
C13—Fe1—C27	68.1 (2)	C1—C16—H16	125.5
C4—Fe1—C27	160.3 (2)	Fe1—C16—H16	125.5
C23—Fe1—C27	40.4 (3)	N3—C17—C14	121.2 (5)
C16—Fe1—C27	107.8 (2)	N3—C17—H17	119.4
C1—Fe1—C22	107.6 (2)	C14—C17—H17	119.4
C12—Fe1—C22	161.0 (2)	C2—C18—C6	120.2 (5)
C25—Fe1—C22	40.5 (2)	C2—C18—H18	119.9
C13—Fe1—C22	68.2 (2)	C6—C18—H18	119.9
C4—Fe1—C22	124.0 (2)	C3—C19—C26	119.0 (5)
C23—Fe1—C22	68.1 (2)	C3—C19—H19	120.5
C16—Fe1—C22	122.6 (2)	C26—C19—H19	120.5
C27—Fe1—C22	40.2 (3)	N4—C20—C2	121.8 (5)
C1—Fe1—C21	68.5 (2)	N4—C20—H20	119.1
C12—Fe1—C21	40.1 (2)	C2—C20—H20	119.1
C25—Fe1—C21	160.2 (2)	C12—C21—C16	107.6 (5)
C13—Fe1—C21	123.5 (2)	C12—C21—Fe1	68.7 (3)
C4—Fe1—C21	68.6 (2)	C16—C21—Fe1	69.0 (3)
C23—Fe1—C21	107.2 (2)	C12—C21—H21	126.2
C16—Fe1—C21	40.2 (2)	C16—C21—H21	126.2
C27—Fe1—C21	122.2 (3)	Fe1—C21—H21	126.2
C22—Fe1—C21	157.6 (2)	C27—C22—C25	107.6 (5)
C7—N2—C5	122.1 (4)	C27—C22—Fe1	69.8 (3)
C7—N2—Ir1	118.9 (3)	C25—C22—Fe1	69.0 (3)
C5—N2—Ir1	118.8 (3)	C27—C22—H22	126.2
C17—N3—C3	120.0 (4)	C25—C22—H22	126.2
C17—N3—Ir1	127.2 (4)	Fe1—C22—H22	126.2
C3—N3—Ir1	112.7 (3)	C27—C23—C13	107.6 (5)
C20—N4—C8	119.6 (4)	C27—C23—Fe1	70.2 (3)
C20—N4—Ir1	127.6 (3)	C13—C23—Fe1	69.4 (3)
C8—N4—Ir1	112.8 (3)	C27—C23—H23	126.2
C16—C1—C4	107.7 (5)	C13—C23—H23	126.2
C16—C1—Fe1	70.3 (3)	Fe1—C23—H23	126.2
C4—C1—Fe1	69.8 (3)	C28—C24—H24A	109.5
C16—C1—H1	126.1	C28—C24—H24B	109.5
C4—C1—H1	126.1	H24A—C24—H24B	109.5
Fe1—C1—H1	126.1	C28—C24—H24C	109.5
C18—C2—C20	118.6 (5)	H24A—C24—H24C	109.5
C18—C2—H2	120.7	H24B—C24—H24C	109.5
C20—C2—H2	120.7	C13—C25—C22	108.5 (5)
N3—C3—C19	121.2 (4)	C13—C25—Fe1	69.7 (3)
N3—C3—C7	115.3 (4)	C22—C25—Fe1	70.5 (3)
C19—C3—C7	123.5 (5)	C13—C25—H25	125.8
C12—C4—C1	106.4 (5)	C22—C25—H25	125.8
C12—C4—C15	127.2 (5)	Fe1—C25—H25	125.8
C1—C4—C15	126.4 (4)	C14—C26—C19	119.5 (5)
C12—C4—Fe1	69.3 (3)	C14—C26—H26	120.3
C1—C4—Fe1	68.7 (3)	C19—C26—H26	120.3
C15—C4—Fe1	128.4 (4)	C22—C27—C23	108.6 (5)
N2—C5—C11	120.0 (5)	C22—C27—Fe1	70.0 (3)
N2—C5—C8	112.3 (4)	C23—C27—Fe1	69.4 (3)
C11—C5—C8	127.6 (4)	C22—C27—H27	125.7
C18—C6—C8	119.0 (5)	C23—C27—H27	125.7
C18—C6—H6	120.5	Fe1—C27—H27	125.7
C8—C6—H6	120.5	N5—C28—C24	176.8 (8)
N2—C7—C10	120.4 (4)	N1—C29—C9	178.6 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl3ⁱ	0.98	2.83	3.771 (5)	162
C24—H24A···Cl1ⁱⁱ	0.95	2.75	3.701 (9)	174
C6—H6···Cl3ⁱ	0.95	2.83	3.731 (6)	159
C9—H9B···Cl3	0.98	2.99	3.875 (10)	151
C11—H11···Cl3ⁱ	0.95	2.82	3.711 (5)	157
C17—H17···Cl1	0.95	2.90	3.486 (6)	121
C20—H20···Cl1	0.95	2.89	3.484 (5)	122
C24—H24A···Cl1ⁱⁱ	0.98	2.73	3.701 (8)	174
C19—H19···Cl2ⁱⁱⁱ	0.95	2.82	3.716 (6)	158

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

Experimental details

Crystal data
Chemical formula	[FeIr(C₅H₅)(C₂₀H₁₄N₃)Cl₃]·2C₂H₃N
M_r	797.94
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	150
a, b, c (Å)	11.557 (5), 21.663 (5), 11.579 (5)
β (°)	105.974 (5)
V (Å³)	2787.0 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.61
Crystal size (mm)	0.30 × 0.23 × 0.20

Data collection
Diffractometer	STOE IPDS 2 diffractometer
Absorption correction	Numerical (X-AREA and X-RED32; Stoe, 2013)
T_min, T_max	0.348, 0.390
No. of measured, independent and observed [I > 2σ(I)] reflections	26757, 7374, 5312
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.076, 1.02
No. of reflections	7374
No. of parameters	354
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −1.10

Computer programs: X-AREA (Stoe, 2013), SHELXT (Sheldrick, 2015a), SHELXL (Sheldrick, 2015b), DIAMOND (Brandenburg, 2006), SHELXL (Sheldrick, b).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cl3ⁱ	0.98	2.83	3.771 (5)	162
C24—H24A···Cl1ⁱⁱ	0.95	2.75	3.701 (9)	174
C6—H6···Cl3ⁱ	0.95	2.83	3.731 (6)	158.8
C9—H9B···Cl3	0.98	2.99	3.875 (10)	150.8
C11—H11···Cl3ⁱ	0.95	2.82	3.711 (5)	156.8
C17—H17···Cl1	0.95	2.90	3.486 (6)	121.2
C20—H20···Cl1	0.95	2.89	3.484 (5)	121.5
C24—H24A···Cl1ⁱⁱ	0.98	2.73	3.701 (8)	173.7
C19—H19···Cl2ⁱⁱⁱ	0.95	2.82	3.716 (6)	158.1

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

Acknowledgements

This work was supported by the King Abdullah University of Science and Technology (KAUST) baseline fund BAS/1/1302-01-01.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Constable, E. C., Edwards, A. J., Martinez-Manez, R., Raithby, P. R. & Cargill Thompson, A. M. W. (1994). Dalton Trans. 5, 645–650. CSD CrossRef Google Scholar
Maity, B., Roy, M., Banik, B., Majumdar, R., Dighe, R. R. & Chakravarty, A. R. (2010). Organometallics, 29, 3632–3641. Web of Science CSD CrossRef CAS Google Scholar
Sakamoto, R., Katagiri, S., Maeda, H., Nishimori, Y., Miyashita, S. & Nishihara, H. (2015). J. Am. Chem. Soc. 137, 734–741. CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
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Wu, K.-Q., Guo, J., Yan, J.-F., Xie, L.-L., Xu, F.-B., Bai, S., Nockemann, P. & Yuan, Y.-F. (2011). Organometallics, 30, 3504–3511. CSD CrossRef CAS Google Scholar

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Volume 71| Part 3| March 2015| Pages m69-m70

doi:10.1107/S2056989015003473

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