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Acta Cryst. (2007). E63, m1469-m1470    [ doi:10.1107/S1600536807019575 ]

Chlorido(ethylenediamine-[kappa]2N)([eta]5-pentamethylcyclopentadienyl)iridium(III) trifluoromethanesulfonate

M. Scharwitz, T. van Almsick and W. S. Sheldrick

Abstract top

The title compound, [Ir([eta]5-C5Me5)Cl(en-[kappa]2N)](CF3SO3) (en is ethylenediamine) or [Ir(C10H15)Cl(C2H8N2)](CF3SO3), contains a half-sandwich ([eta]5-C5Me5)IrIII fragment coordinated in a bidentate manner by the N atoms of an en ligand. N-H...O hydrogen bonds between the en amino groups and O atoms of the trifluoromethanesulfonate anions generate polymeric chains. The cation and anion both have Cs symmetry. The C atoms of the en ligand are disordered about a mirror plane. The crystal structure involves N-H...O, C-H...O and N-H...Cl hydrogen bonds.

Comment top

Although many (pentamethylcyclopentadienyl)iridium(III) complexes with bidentate aromatic N-donor ligands such as 2,2-bipyridine (Dadci et al., 1995; Youinou & Ziessel, 1989) or 1,10-phenanthroline (Gencaslan & Sheldrick, 2005) have been structurally characterized, few examples are known for ligands containing two or three amino or alkylamino N-donor functions. The Cambridge Structural Database (Version 5.27, December 2006; Allen, 2002) contain two entries [(η5-C5Me5)Ir(1,2-diaminocyclohexane-κ2N)](ClO4)2*2H2O (Poth et al., 2001) and [(η5-C5Me5)IrCl(2-amino-3-dimethylaminopropionate-κ2N)] *H2O (Bergs et al., 1997) for bidentate ligands of this type. Crystal structures have also been reported for [(η5-C5Me5)Ir(1,4,7-triazacyclononane-κ3N)](PF6)2 *CH3NO2 (Grant et al., 2005) and [(η5-C5Me5)Ir(dien-κ3N)](CF3SO3)2 (dien is diethylenetriamine) (Scharwitz et al., 2007c), both of which contain κ3N amino ligands. As part of our continuing studies on organoruthenium(II) and organoiridium(III) half-sandwhich complexes with N and S donor ligands (Gleichmann et al., 1995, Korn & Sheldrick, 1997; Schäfer & Sheldrick, 2007; Scharwitz et al., 2007a,b,c, Scharwitz et al., 2007) we have now determined the structure of the title compound [(η5-C5Me5)IrCl(en-κ2N)](CF3SO3), (I).

The molecular structure of (I) is depicted in Fig. 1. Both the cation and anion exhibit crystallographic Cs symmetry with the ethylenediamine carbon atoms C2 and C3 being disordered (s.o.f.s = 1/2) with symmetry-equivalent sites (i) [(i) = x, 0.5 - y, z] generated by the mirror plane. A twist δ conformation is observed for the five-membered chelate ring containing C2 and C3 with a λ conformation for the alternative disordered ring with C2i and C3i. Carbon atoms C2 and C3 are displaced respectively 0.258 (9) and -0.292 (19) Å from the best plane through the ring atoms. The Ir1—C13 distance of 2.127 (10) Å is somewhat shorter than the Ir1—C11 and Ir1—C12 distances of respectively 2.156 (7) and 2.162 (7) Å. Participation of the N1 atoms in N1—H1···O2 hydrogen bonds of length 2.954 (9) Å (H1···O2 = 2.09 Å, N1—H1···O2 = 161.8°) to symmetry-related trifluoromethanesulfonate counter-anions is observed (Fig. 1). Hydrogen bonding interactions of the type N1—H2···Cl1i [(i) = 1 - x, -y, -z] (Table 1) link the cations and anions of (I) (Fig. 2).

Related literature top

For related literature, see: Allen (2002); Bergs et al. (1997); Dadci et al. (1995); Gencaslan & Sheldrick (2005); Gleichmann et al. (1995); Grant et al. (2005); Korn & Sheldrick (1997); Poth et al. (2001); Schäfer & Sheldrick (2007); Scharwitz et al. (2007, 2007a,b,c); Youinou & Ziessel (1989).

Experimental top

Ag(CF3SO3) (25.7 mg, 0.1 mmol) was added to a solution of [(η5-C5Me5)IrCl2]2 (39.8 mg, 0.05 mmol) in acetone (10 ml) and stirred at room temperature for 30 min. After centrifugation of the precipitated AgCl and solvent removal from the resulting solution, the yellow residue was redissolved in CH3OH/CH2Cl2 (10 ml, 1:1) and treated with 6.1 µl ethylendiamine (0.1 mmol). The reaction solution was heated for 2 h at 348 K and the solvent subsequently removed to afford (I), which was dissolved in methanol (3 ml) and reprecipitated with diethyl ether prior to drying in vacuum (yield 89%). Suitable crystals for X-ray analysis were grown by slow evaporation of a solution of (I) in CH3OH/H2O (1:). Elemental analysis found: C 27.4, H 4.5, N 5.2%; calculated for C13H23ClF3IrN2O3S: C 27.3, H 4.1, N 4.9%. FAB-MS on a VG Autospec instrument (m/z): 537 (30) [M—Cl]+, 423 (100) [M—CF3SO3]+, 387 (60) [M—CF3SO3—Cl]+.

Refinement top

H atoms were constrained to idealized positions and refined using a riding model, with C—H distances of 0.97 Å for the methylene C atoms and 0.96 Å for the methyl groups; Uiso(H) = 1.2 Uiso(C) for methylene and 1.5 Uiso(C) for methyl groups. The methyl groups were allowed to rotate but not tip.

Computing details top

Data collection: R3m/V (Siemens, 1989); cell refinement: R3m/V; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1995); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Structure of the cation and counter anion of (I). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen bonding interactions in the crystal structure of (I) in a projection along [100].
Chlorido(ethylenediamine-κ2N)(η5-pentamethylcyclopentadienyl)iridium(III) trifluoromethanesulfonate top
Crystal data top
[Ir(C10H15)Cl(C2H8N2)](CF3O3S)F(000) = 1104
Mr = 572.04Dx = 2.027 Mg m−3
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 14 reflections
a = 15.400 (5) Åθ = 3.5–12.7°
b = 8.5728 (16) ŵ = 7.42 mm−1
c = 14.202 (5) ÅT = 292 K
V = 1874.9 (10) Å3Block, colourless
Z = 40.22 × 0.20 × 0.16 mm
Data collection top
Siemens P4 four-circle
diffractometer		1308 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
graphiteθmax = 25.0°, θmin = 2.7°
ω scansh = −1→18
Absorption correction: ψ scan
(XPREP; Sheldrick, 1995)		k = −1→10
Tmin = 0.211, Tmax = 0.308l = −1→16
2309 measured reflections3 standard reflections every 97 reflections
1743 independent reflections intensity decay: 0.00%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0415P)2]
where P = (Fo2 + 2Fc2)/3
1743 reflections(Δ/σ)max < 0.001
133 parametersΔρmax = 0.77 e Å−3
3 restraintsΔρmin = −0.93 e Å−3
Crystal data top
[Ir(C10H15)Cl(C2H8N2)](CF3O3S)V = 1874.9 (10) Å3
Mr = 572.04Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 15.400 (5) ŵ = 7.42 mm−1
b = 8.5728 (16) ÅT = 292 K
c = 14.202 (5) Å0.22 × 0.20 × 0.16 mm
Data collection top
Siemens P4 four-circle
diffractometer		1308 reflections with I > 2σ(I)
Absorption correction: ψ scan
(XPREP; Sheldrick, 1995)		Rint = 0.037
Tmin = 0.211, Tmax = 0.308θmax = 25.0°
2309 measured reflections3 standard reflections every 97 reflections
1743 independent reflections intensity decay: 0.00%
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.079Δρmax = 0.77 e Å−3
S = 0.99Δρmin = −0.93 e Å−3
1743 reflectionsAbsolute structure: ?
133 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Ir10.40783 (2)0.25000.10854 (3)0.03035 (15)
Cl10.4968 (2)0.2500−0.0318 (2)0.0512 (8)
N10.5019 (3)0.0926 (8)0.1612 (4)0.0391 (16)0.50
H10.48080.04640.21330.047*0.50
H20.51120.01770.11790.047*0.50
C20.5844 (9)0.166 (3)0.1841 (14)0.054 (5)0.50
H210.61930.18050.12790.065*0.50
H220.61680.10340.22870.065*0.50
C30.5607 (14)0.321 (3)0.2265 (13)0.068 (8)0.50
H310.53180.30510.28640.081*0.50
H320.61280.38180.23770.081*0.50
N1'0.5019 (3)0.0926 (8)0.1612 (4)0.0391 (16)0.50
H1'0.47560.01390.19200.047*0.50
H2'0.53280.05200.11330.047*0.50
C110.2866 (5)0.1665 (10)0.0516 (5)0.053 (2)
C1110.2773 (7)0.0629 (15)−0.0350 (6)0.106 (4)
H1110.21700.0526−0.05090.159*
H1120.3012−0.0382−0.02190.159*
H1130.30800.1090−0.08690.159*
C120.2946 (5)0.1144 (9)0.1460 (6)0.0400 (19)
C1210.2943 (6)−0.0504 (9)0.1767 (7)0.070 (3)
H1210.3197−0.05810.23830.105*
H1220.3274−0.11190.13310.105*
H1230.2356−0.08810.17870.105*
C130.3020 (7)0.25000.2048 (7)0.036 (3)
C1310.3134 (8)0.25000.3093 (8)0.063 (4)
H13A0.36500.19320.32540.095*0.50
H13B0.26400.20130.33830.095*0.50
H13C0.31840.35550.33130.095*0.50
S10.5106 (2)−0.25000.3332 (2)0.0544 (9)
O10.5902 (7)−0.25000.2830 (8)0.105 (4)
O20.4614 (5)−0.1126 (9)0.3224 (5)0.099 (3)
C100.5384 (16)−0.25000.4557 (12)0.096 (6)
F10.4739 (11)−0.25000.5110 (7)0.149 (6)
F20.5861 (6)−0.1274 (14)0.4760 (7)0.192 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ir10.0303 (2)0.0298 (2)0.0309 (2)0.0000.0003 (2)0.000
Cl10.0616 (19)0.0525 (19)0.0396 (15)0.0000.0153 (14)0.000
N10.038 (3)0.042 (4)0.038 (4)0.003 (3)0.008 (3)0.002 (3)
C20.039 (10)0.065 (12)0.059 (13)0.006 (11)0.002 (10)0.003 (14)
C30.056 (13)0.093 (19)0.054 (14)−0.017 (13)−0.008 (10)−0.018 (14)
N1'0.038 (3)0.042 (4)0.038 (4)0.003 (3)0.008 (3)0.002 (3)
C110.032 (4)0.074 (6)0.053 (4)−0.005 (5)−0.008 (4)−0.006 (5)
C1110.084 (8)0.154 (12)0.079 (7)−0.010 (9)−0.024 (7)−0.070 (8)
C120.026 (4)0.031 (4)0.063 (5)−0.003 (4)−0.001 (4)0.005 (4)
C1210.056 (6)0.032 (5)0.122 (8)−0.011 (5)0.010 (6)0.015 (6)
C130.032 (6)0.036 (6)0.039 (6)0.0000.007 (5)0.000
C1310.040 (7)0.106 (12)0.044 (7)0.0000.005 (6)0.000
S10.059 (2)0.059 (2)0.0449 (18)0.000−0.0136 (17)0.000
O10.080 (8)0.139 (11)0.098 (9)0.0000.011 (7)0.000
O20.122 (6)0.093 (6)0.081 (5)0.046 (5)−0.004 (5)0.030 (5)
C100.142 (18)0.093 (15)0.052 (10)0.000−0.033 (12)0.000
F10.217 (15)0.173 (13)0.057 (6)0.0000.017 (8)0.000
F20.206 (9)0.233 (12)0.137 (7)−0.095 (8)−0.065 (7)−0.045 (8)
Geometric parameters (Å, °) top
Ir1—N1'i2.116 (6)C111—H1120.9600
Ir1—N1i2.116 (6)C111—H1130.9600
Ir1—N12.116 (6)C12—C131.436 (9)
Ir1—C132.127 (10)C12—C1211.479 (10)
Ir1—C112.156 (7)C121—H1210.9600
Ir1—C11i2.156 (7)C121—H1220.9600
Ir1—C122.162 (7)C121—H1230.9600
Ir1—C12i2.162 (7)C13—C12i1.436 (9)
Ir1—Cl12.419 (3)C13—C1311.494 (14)
N1—C21.455 (10)C131—H13A0.9600
N1—H10.9000C131—H13B0.9600
N1—H20.9000C131—H13C0.9600
C2—C31.503 (13)S1—O2ii1.409 (7)
C2—H210.9700S1—O21.409 (7)
C2—H220.9700S1—O21.409 (7)
C3—N1i1.49 (2)S1—O11.417 (11)
C3—H310.9700S1—C101.791 (16)
C3—H320.9700O2—O20.00 (2)
C11—C121.417 (10)C10—F11.27 (2)
C11—C11i1.431 (18)C10—F21.315 (15)
C11—C1111.525 (11)C10—F2ii1.315 (15)
C111—H1110.9600
N1'i—Ir1—N1i0.0 (5)C12—C11—C11i108.4 (5)
N1'i—Ir1—N179.2 (3)C12—C11—C111126.0 (8)
N1i—Ir1—N179.2 (3)C11i—C11—C111125.6 (6)
N1'i—Ir1—C13107.3 (3)C12—C11—Ir171.1 (4)
N1i—Ir1—C13107.3 (3)C11i—C11—Ir170.6 (2)
N1—Ir1—C13107.3 (3)C111—C11—Ir1125.2 (6)
N1'i—Ir1—C11159.5 (3)C11—C111—H111109.5
N1i—Ir1—C11159.5 (3)C11—C111—H112109.5
N1—Ir1—C11120.9 (3)H111—C111—H112109.5
C13—Ir1—C1165.0 (3)C11—C111—H113109.5
N1'i—Ir1—C11i120.9 (3)H111—C111—H113109.5
N1i—Ir1—C11i120.9 (3)H112—C111—H113109.5
N1—Ir1—C11i159.5 (3)C11—C12—C13107.6 (7)
C13—Ir1—C11i65.0 (3)C11—C12—C121125.4 (8)
C11—Ir1—C11i38.8 (5)C13—C12—C121127.0 (8)
N1'i—Ir1—C12143.9 (3)C11—C12—Ir170.6 (4)
N1i—Ir1—C12143.9 (3)C13—C12—Ir169.1 (5)
N1—Ir1—C1297.0 (3)C121—C12—Ir1126.0 (6)
C13—Ir1—C1239.1 (2)C12—C121—H121109.5
C11—Ir1—C1238.3 (3)C12—C121—H122109.5
C11i—Ir1—C1264.7 (3)H121—C121—H122109.5
N1'i—Ir1—C12i97.0 (3)C12—C121—H123109.5
N1i—Ir1—C12i97.0 (3)H121—C121—H123109.5
N1—Ir1—C12i143.9 (3)H122—C121—H123109.5
C13—Ir1—C12i39.1 (2)C12—C13—C12i108.1 (9)
C11—Ir1—C12i64.7 (3)C12—C13—C131126.0 (4)
C11i—Ir1—C12i38.3 (3)C12i—C13—C131126.0 (4)
C12—Ir1—C12i65.0 (4)C12—C13—Ir171.8 (5)
N1'i—Ir1—Cl184.45 (17)C12i—C13—Ir171.8 (5)
N1i—Ir1—Cl184.45 (17)C131—C13—Ir1123.3 (8)
N1—Ir1—Cl184.45 (17)C13—C131—H13A109.5
C13—Ir1—Cl1164.5 (3)C13—C131—H13B109.5
C11—Ir1—Cl1100.5 (2)H13A—C131—H13B109.5
C11i—Ir1—Cl1100.5 (2)C13—C131—H13C109.5
C12—Ir1—Cl1131.3 (2)H13A—C131—H13C109.5
C12i—Ir1—Cl1131.3 (2)H13B—C131—H13C109.5
C2—N1—Ir1113.6 (12)O2ii—S1—O2113.4 (7)
C2—N1—H1108.9O2ii—S1—O2113.4 (7)
Ir1—N1—H1108.9O2—S1—O20.0 (8)
C2—N1—H2108.9O2ii—S1—O1114.2 (4)
Ir1—N1—H2108.9O2—S1—O1114.2 (4)
H1—N1—H2107.7O2—S1—O1114.2 (4)
N1—C2—C3105.1 (18)O2ii—S1—C10103.5 (5)
N1—C2—H21110.7O2—S1—C10103.5 (5)
C3—C2—H21110.7O2—S1—C10103.5 (5)
N1—C2—H22110.7O1—S1—C10106.4 (10)
C3—C2—H22110.7O2—O2—S10(10)
H21—C2—H22108.8F1—C10—F2107.6 (12)
N1i—C3—C2109.6 (18)F1—C10—F2ii107.6 (12)
N1i—C3—H31109.7F2—C10—F2ii106.1 (19)
C2—C3—H31109.7F1—C10—S1114.6 (16)
N1i—C3—H32109.7F2—C10—S1110.3 (11)
C2—C3—H32109.7F2ii—C10—S1110.3 (11)
H31—C3—H32108.2
N1'i—Ir1—N1—C2−12.7 (10)N1'i—Ir1—C12—C121−93.8 (9)
N1i—Ir1—N1—C2−12.7 (10)N1i—Ir1—C12—C121−93.8 (9)
C13—Ir1—N1—C2−117.7 (9)N1—Ir1—C12—C121−12.4 (8)
C11—Ir1—N1—C2171.6 (9)C13—Ir1—C12—C121−121.3 (10)
C11i—Ir1—N1—C2177.8 (9)C11—Ir1—C12—C121120.3 (10)
C12—Ir1—N1—C2−156.4 (9)C11i—Ir1—C12—C121157.9 (9)
C12i—Ir1—N1—C2−99.9 (9)C12i—Ir1—C12—C121−159.6 (7)
Cl1—Ir1—N1—C272.7 (9)Cl1—Ir1—C12—C12176.4 (8)
Ir1—N1—C2—C338.5 (15)C11—C12—C13—C12i2.6 (12)
N1—C2—C3—N1i−53.5 (14)C121—C12—C13—C12i−176.9 (6)
N1'i—Ir1—C11—C12−109.7 (8)Ir1—C12—C13—C12i63.0 (7)
N1i—Ir1—C11—C12−109.7 (8)C11—C12—C13—C131−178.7 (9)
N1—Ir1—C11—C1258.2 (5)C121—C12—C13—C1311.8 (16)
C13—Ir1—C11—C12−37.7 (4)Ir1—C12—C13—C131−118.3 (11)
C11i—Ir1—C11—C12−118.3 (4)C11—C12—C13—Ir1−60.4 (6)
C12i—Ir1—C11—C12−81.1 (6)C121—C12—C13—Ir1120.1 (8)
Cl1—Ir1—C11—C12148.0 (4)N1'i—Ir1—C13—C12−163.5 (4)
N1'i—Ir1—C11—C11i8.6 (7)N1i—Ir1—C13—C12−163.5 (4)
N1i—Ir1—C11—C11i8.6 (7)N1—Ir1—C13—C12−79.7 (5)
N1—Ir1—C11—C11i176.5 (3)C11—Ir1—C13—C1237.0 (5)
C13—Ir1—C11—C11i80.56 (18)C11i—Ir1—C13—C1279.9 (6)
C12—Ir1—C11—C11i118.3 (4)C12i—Ir1—C13—C12116.9 (9)
C12i—Ir1—C11—C11i37.2 (3)Cl1—Ir1—C13—C1258.4 (4)
Cl1—Ir1—C11—C11i−93.72 (9)N1'i—Ir1—C13—C12i79.7 (5)
N1'i—Ir1—C11—C111129.1 (9)N1i—Ir1—C13—C12i79.7 (5)
N1i—Ir1—C11—C111129.1 (9)N1—Ir1—C13—C12i163.5 (4)
N1—Ir1—C11—C111−63.0 (9)C11—Ir1—C13—C12i−79.9 (6)
C13—Ir1—C11—C111−158.9 (9)C11i—Ir1—C13—C12i−37.0 (5)
C11i—Ir1—C11—C111120.5 (8)C12—Ir1—C13—C12i−116.9 (9)
C12—Ir1—C11—C111−121.2 (10)Cl1—Ir1—C13—C12i−58.4 (4)
C12i—Ir1—C11—C111157.7 (9)N1'i—Ir1—C13—C131−41.90 (19)
Cl1—Ir1—C11—C11126.8 (8)N1i—Ir1—C13—C131−41.90 (19)
C11i—C11—C12—C13−1.6 (7)N1—Ir1—C13—C13141.90 (19)
C111—C11—C12—C13179.8 (8)C11—Ir1—C13—C131158.5 (3)
Ir1—C11—C12—C1359.5 (6)C11i—Ir1—C13—C131−158.5 (3)
C11i—C11—C12—C121177.9 (7)C12—Ir1—C13—C131121.6 (4)
C111—C11—C12—C121−0.7 (13)C12i—Ir1—C13—C131−121.6 (4)
Ir1—C11—C12—C121−121.0 (8)Cl1—Ir1—C13—C131180.000 (1)
C11i—C11—C12—Ir1−61.1 (2)O2ii—S1—O2—O20.00 (12)
C111—C11—C12—Ir1120.3 (8)O1—S1—O2—O20.0 (3)
N1'i—Ir1—C12—C11146.0 (5)C10—S1—O2—O20.0 (2)
N1i—Ir1—C12—C11146.0 (5)O2ii—S1—C10—F1−59.3 (4)
N1—Ir1—C12—C11−132.7 (5)O2—S1—C10—F159.3 (4)
C13—Ir1—C12—C11118.5 (7)O2—S1—C10—F159.3 (4)
C11i—Ir1—C12—C1137.6 (5)O1—S1—C10—F1180.000 (2)
C12i—Ir1—C12—C1180.1 (5)O2ii—S1—C10—F2179.2 (14)
Cl1—Ir1—C12—C11−43.9 (5)O2—S1—C10—F2−62.3 (17)
N1'i—Ir1—C12—C1327.5 (7)O2—S1—C10—F2−62.3 (17)
N1i—Ir1—C12—C1327.5 (7)O1—S1—C10—F258.4 (15)
N1—Ir1—C12—C13108.9 (5)O2ii—S1—C10—F2ii62.3 (17)
C11—Ir1—C12—C13−118.5 (7)O2—S1—C10—F2ii−179.2 (14)
C11i—Ir1—C12—C13−80.9 (5)O2—S1—C10—F2ii−179.2 (14)
C12i—Ir1—C12—C13−38.4 (5)O1—S1—C10—F2ii−58.4 (15)
Cl1—Ir1—C12—C13−162.3 (4)
Symmetry codes: (i) x, −y+1/2, z; (ii) x, −y−1/2, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.902.092.954 (9)162
C121—H121···O20.962.533.345 (12)143
N1—H2···Cl1iii0.902.603.464 (7)160
N1'—H1'···O20.902.162.954 (9)147
Symmetry codes: (iii) −x+1, −y, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.902.092.954 (9)162
C121—H121···O20.962.533.345 (12)143
N1—H2···Cl1i0.902.603.464 (7)160
N1'—H1'···O20.902.162.954 (9)147
Symmetry codes: (i) −x+1, −y, −z.
references
References top

Allen, F. H. (2002). Acta Cryst. B58, 380–388.

Bergs, R., Sünkel, K., Robl, C. & Beck, W. (1997). J. Organomet. Chem. 533, 247–255.

Dadci, L., Elias, H., Frey, V., Horning, A., Koelle, U., Merbach, A. E., Paulus, H. & Schneider, J. S. (1995). Inorg. Chem. 34, 306–315.

Gencaslan, S. & Sheldrick, W. S. (2005). Eur. J. Inorg. Chem. pp. 3840–3849.

Gleichmann, A. J., Wolff, J. M. & Sheldrick, W. S. (1995). J. Chem. Soc. Dalton Trans. pp. 1549–1554.

Grant, G. J., Lee, J. P., Helm, M. L., VanDerveer, D. G., Pennington, W. T., Harris, J. L., Mehne, L. F. & Klinger, D. W. (2005). J. Organomet. Chem. 690, 629–639.

Korn, S. & Sheldrick, W. S. (1997). Inorg. Chim. Acta, 254, 85–91.

Poth, T., Paulus, H., Elias, H., Ducker-Benfer, C. & van Eldik, R. (2001). Eur. J. Inorg. Chem. pp. 1361–1369.

Schäfer, S. & Sheldrick, W. S. (2007). J. Organomet. Chem. 692, 1300–1309.

Scharwitz, M., Schäfer, S., van Almsick, T. & Sheldrick, W. S. (2007). Acta Cryst. E63, m1111–m1113.

Scharwitz, M., van Almsick, T. & Sheldrick, W. S. (2007a). Acta Cryst. E63, m105–m107.

Scharwitz, M., van Almsick, T. & Sheldrick, W. S. (2007b). Acta Cryst. E63, m230–m232.

Scharwitz, M., van Almsick, T. & Sheldrick, W. S. (2007c). Acta Cryst. E63, m537–m539.

Sheldrick, G. M. (1995). SHELXTL, Release 5.03. Siemens Analytical X-Ray Instruments, Inc., Madison, USA.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Siemens (1989). R3m/V User's Guide. Version 3.2. Siemens Analytical X-ray Instruments, Inc., Madison, Wisconsin, USA.

Youinou, M.-T. & Ziessel, R. (1989). J. Organomet. Chem. 363, 197–208.