Bis(η2-ethyl­ene)[aza­nidediylbis(diiso­propyl­phosphine selenide)-κ2Se,Se′]iridium(III)

Wu, F.-H.; Lu, L.; Duan, T.; Zhang, Q.-F.

doi:10.1107/S1600536809050156

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1696

doi:10.1107/S1600536809050156

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Bis(η²-ethylene)[azanidediylbis(diisopropylphosphine selenide)-κ²Se,Se′]iridium(III)

Fang-Hui Wu,^a Lude Lu,^a Taike Duan ^b ^* and Qian-Feng Zhang ^b

^aMaterial Chemistry Laboratory, Nanjing University of Science and Technology, Nanjing 210094, People's Republic of China, and ^bInstitute of Molecular Engineering and Applied Chemsitry, Anhui University of Technology, Ma'anshan, Anhui 243002, People's Republic of China
^*Correspondence e-mail: imc@ahut.edu.cn

(Received 2 November 2009; accepted 22 November 2009; online 28 November 2009)

In the title compound, [Ir(η²-C₂H₄)₂(C₁₂H₂₈NP₂Se₂)], the central Ir atom is chelated by the [N(ⁱPr₂PSe)₂]⁻ ligand via two Se atoms and is coordinated by two η²-ethylene molecules via four C atoms in an octahedral coordination geometry.

Related literature

For studies of complexes containing [N(R₂PQ)₂]⁻ (Q = S, Se, Te) ligands, see: Ly & Woollins (1998 ); Rudler et al. (1997 ). For metal complexes with [N(R₂PQ)₂]⁻ (Q = S, Se, Te) as NMR shift reagents, see: Barkaoui et al. (1997 ). For related structures, see: Cheung et al. (2006 ); Kirchmann et al. (2008 ); Lundquist et al. (1990 ); Parr et al. (1999 ). For the C—C bond length in free ethylene, see: Stoicheff (1962 ).

Experimental

Crystal data

[Ir(C₂H₄)₂(C₁₂H₂₈NP₂Se₂)]
M_r = 654.52
Triclinic, $[P \overline 1]$
a = 9.6965 (1) Å
b = 10.3962 (1) Å
c = 12.0620 (1) Å
α = 98.511 (1)°
β = 96.055 (1)°
γ = 107.273 (1)°
V = 1133.84 (2) Å³
Z = 2
Mo Kα radiation
μ = 9.24 mm⁻¹
T = 296 K
0.30 × 0.21 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.168, T_max = 0.320
15331 measured reflections
5170 independent reflections
4505 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.067
S = 1.03
5170 reflections
207 parameters
H-atom parameters constrained
Δρ_max = 1.39 e Å⁻³
Δρ_min = −1.03 e Å⁻³

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050156/ng2681sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050156/ng2681Isup2.hkl

checkCIF report

Comment top

Imidotetraaryldichalcogenodiphosphinates of general formula [N(R₂PQ)₂]^- (Q = S, Se, Te) have a well defined coordination chemistry, with examples of simple complexes known for elements from each block of the periodic table (Ly & Woollins, 1998). Metal complexes with [N(R₂PQ)₂]^- have been used as catalysts for organic reactions (Rudler et al., 1997) and NMR shift reagents (Barkaoui et al., 1997). Despite the high affinity of [N(R₂PQ)₂]^- for late transition metal ions, their complexes with iridium have not been well explored. The only structurally characterized iridium imidotetraaryldichalcogenodiphosphinates are the half-sandwich complexes [Cp*Ir{N(R₂PQ)₂}X] (X = Cl, SCN, SeCN) (Parr et al., 1999). To explore the organometallic chemistry of imidotetraaryldichalcogenodiphosphinates, we are interested to synthesize organoiridium compounds with [N(R₂PQ)₂]^- ligands. We have previously reported the syntheses and crystal structures of iridium imidotetraaryldithiodiphosphinates compounds containing carbonyl, 1,5-cyclooctadiene, and olefin co-ligands (Cheung et al., 2006). We herein describe molecular structure of an organoiridium compound [Ir{N(ⁱPr₂PSe)₂}(η²-C₂H₄)₂] with imido-tetra-iso-propyldiselenodiphosphinate and ethylene ligands in this paper.

The title compound crystallizes in the triclinic space group P-1. The molecular structure with atomic numbering is depicted in Fig. 1. The central iridium atom is hexacoordinated by one chelating [N(ⁱPr₂PSe)₂]^- ligand via two selenium atoms and two η²-ethylene molecules via four carbon atoms, thereby forming a distorded octahedral environment. The [N(ⁱPr₂PSe)₂]^- acts as a chelating ligand through its two selenium atoms to bond the iridium center in a cis geometry. Similar to analogue complexes [Ir{N(ⁱPr₂PS)₂}(η²-C₂H₄)₂] and [Ir{N(Ph₂PS)₂}(η²-COE)₂] (COE = cyclooctene) with imido-tetra-iso-propyldiselenodiphosphinate ligands (Cheung et al., 2006), the conformation of the six-membered IrSe₂P₂N ring in the title compound is described as a twisted-boat imposed by the non-parallel orientation of the two P—Se bonds. The bite angle of Se(1)—Ir(1)—Se(2) is 99.332 (16)°, the other angles in the chelate ring are Ir(1)—Se(1)—P(1) 109.29 (3)°, Ir(1)—Se(2)—P(2) 110.38 (3)°, Se(1)—P(1)—N(1) 116.89 (14)°, Se(2)—P(2)—N(1) 116.88 (13)°, and P(1)—N(1)—P(2) 127.3 (2)°. The average Ir—Se bond length (av. 2.4601 (5) Å) in the title compound is slightly longer than those in [Cp^*Ir{N(Ph₂PSe)₂}Cl] (av. 2.5139 (5) Å) (Parr et al., 1999) and [Cp^*Ir{N(Ph₂PSe)₂}(SCN)] (av. 2.5159 (8) Å) (Parr et al., 1999). The ethylene molecules bind to the central iridium atom in an η²-coordination mode with the small bite angles C(1)—Ir(1)—C(2) and C(1)—Ir(1)—C(2) of 38.1 (2) and 38.4 (2)°, respectively. The average C—C bond length in the title compound (av. 1.398 (9) Å) is longer than that in free ethylene (1.339 Å) (Stoicheff, 1962), but compares with corresponding bond lengths in [Ir{N(ⁱPr₂PS)₂}(η²-C₂H₄)₂] (av. 1.400 (6) Å) (Cheung et al., 2006), [Ir(PMe₂Ph)₃(η²-C₂H₄)₂][BF₄] (av. 1.42 (2) Å) (Lundquist et al., 1990) and [Me₄N][Ir(SnB₁₁H₁₁)(CO)(η²-C₂H₄)(PPh₃)₂] (av. 1.44 (3) Å) (Kirchmann et al., 2008). The average Ir—C bond length in the title compound (av. 2.133 (5) Å) compares well with those in [Ir{N(ⁱPr₂PS)₂}(η²-C₂H₄)₂] (av. 2.124 (5) Å) (Cheung et al., 2006), [Ir(PMe₂Ph)₃(η²-C₂H₄)₂][BF₄] (av. 2.20 (3) Å) (Lundquist et al., 1990) and [Me₄N][Ir(SnB₁₁H₁₁)(CO)(η²-C₂H₄)(PPh₃)₂] (av. 2.22 (2) Å) (Kirchmann et al., 2008).

Related literature top

For studies of complexes containing [N(R₂PQ)₂]^- (Q = S, Se, Te) ligands, see: Ly & Woollins (1998); Rudler et al. (1997). For metal complexes with [N(R₂PQ)₂]^- (Q = S, Se, Te) as NMR shift reagents, see: Barkaoui et al. (1997). For related structures, see: Cheung et al. (2006); Kirchmann et al. (2008); Lundquist et al. (1990); Parr et al. (1999). For the C—C bond length in free ethylene, see: Stoicheff (1962).

Experimental top

The title compound was prepared according to the literature method (Cheung et al., 2006) and similarly as for [Ir{N(ⁱPr₂PS)₂}(η²-C₂H₄)₂] using K[N(ⁱPr₂PSe)₂] instead of K[N(ⁱPr₂PS)₂]. Orange single crystals of the title compound were obtained from the hexane solution at -40 °C.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level.

Bis(η²-ethylene)[azanidediylbis(diisopropylphosphine selenide)- κ²Se,Se']iridium(III) top

Crystal data top

[Ir(C₂H₄)₂(C₁₂H₂₈NP₂Se₂)]	Z = 2
M_r = 654.52	F(000) = 628
Triclinic, P1	D_x = 1.917 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6965 (1) Å	Cell parameters from 6523 reflections
b = 10.3962 (1) Å	θ = 2.5–26.8°
c = 12.0620 (1) Å	µ = 9.24 mm⁻¹
α = 98.511 (1)°	T = 296 K
β = 96.055 (1)°	Prism, orange
γ = 107.273 (1)°	0.30 × 0.21 × 0.16 mm
V = 1133.84 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5170 independent reflections
Radiation source: fine-focus sealed tube	4505 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
phi and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.168, T_max = 0.320	k = −12→13
15331 measured reflections	l = −15→15

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0339P)² + 0.943P] where P = (F_o² + 2F_c²)/3
5170 reflections	(Δ/σ)_max < 0.001
207 parameters	Δρ_max = 1.39 e Å⁻³
0 restraints	Δρ_min = −1.03 e Å⁻³

Crystal data top

[Ir(C₂H₄)₂(C₁₂H₂₈NP₂Se₂)]	γ = 107.273 (1)°
M_r = 654.52	V = 1133.84 (2) Å³
Triclinic, P1	Z = 2
a = 9.6965 (1) Å	Mo Kα radiation
b = 10.3962 (1) Å	µ = 9.24 mm⁻¹
c = 12.0620 (1) Å	T = 296 K
α = 98.511 (1)°	0.30 × 0.21 × 0.16 mm
β = 96.055 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5170 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4505 reflections with I > 2σ(I)
T_min = 0.168, T_max = 0.320	R_int = 0.024
15331 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.067	H-atom parameters constrained
S = 1.03	Δρ_max = 1.39 e Å⁻³
5170 reflections	Δρ_min = −1.03 e Å⁻³
207 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
Ir1	0.183001 (17)	0.291467 (16)	0.217100 (14)	0.03765 (6)
Se1	0.07448 (5)	0.45184 (4)	0.31713 (4)	0.04549 (12)
Se2	0.39296 (5)	0.45760 (5)	0.16421 (5)	0.04878 (12)
P1	0.24433 (11)	0.65130 (11)	0.37985 (9)	0.0347 (2)
P2	0.35610 (11)	0.65739 (11)	0.16970 (9)	0.0356 (2)
N1	0.3238 (4)	0.7270 (3)	0.2873 (3)	0.0398 (8)
C1	0.3029 (7)	0.1529 (6)	0.1735 (6)	0.0703 (16)
H1A	0.3089	0.2106	0.2419	0.084*
H1B	0.3632	0.0982	0.1679	0.084*
C2	0.2036 (7)	0.1485 (6)	0.0795 (5)	0.0737 (18)
H2A	0.1433	0.2033	0.0852	0.088*
H2B	0.1976	0.0909	0.0112	0.088*
C3	0.0789 (7)	0.1508 (6)	0.3164 (6)	0.0790 (19)
H3A	0.1740	0.2104	0.3255	0.095*
H3B	0.0517	0.0953	0.3694	0.095*
C4	−0.0233 (6)	0.1446 (6)	0.2229 (6)	0.0764 (19)
H4A	0.0039	0.2000	0.1699	0.092*
H4B	−0.1184	0.0850	0.2138	0.092*
C11	0.1481 (5)	0.7590 (5)	0.4494 (4)	0.0475 (11)
H11A	0.1057	0.7149	0.5098	0.057*
C12	0.0227 (6)	0.7685 (6)	0.3672 (5)	0.0652 (15)
H12A	−0.0331	0.8161	0.4079	0.098*
H12B	−0.0393	0.6778	0.3319	0.098*
H12C	0.0613	0.8175	0.3100	0.098*
C13	0.2494 (7)	0.9012 (6)	0.5043 (6)	0.086 (2)
H13A	0.3119	0.9376	0.4521	0.129*
H13B	0.3080	0.8959	0.5717	0.129*
H13C	0.1924	0.9601	0.5237	0.129*
C14	0.3761 (5)	0.6209 (5)	0.4850 (4)	0.0490 (11)
H14A	0.4022	0.5431	0.4475	0.059*
C15	0.5195 (6)	0.7394 (7)	0.5211 (6)	0.080 (2)
H15A	0.5045	0.8113	0.5733	0.121*
H15B	0.5513	0.7739	0.4554	0.121*
H15C	0.5927	0.7074	0.5571	0.121*
C16	0.3095 (7)	0.5757 (8)	0.5874 (5)	0.084 (2)
H16A	0.3764	0.5451	0.6329	0.126*
H16B	0.2194	0.5020	0.5619	0.126*
H16C	0.2909	0.6515	0.6319	0.126*
C21	0.5261 (5)	0.7694 (5)	0.1388 (4)	0.0465 (11)
H21A	0.5384	0.7316	0.0624	0.056*
C22	0.6584 (5)	0.7730 (6)	0.2205 (5)	0.0679 (16)
H22A	0.7462	0.8198	0.1941	0.102*
H22B	0.6563	0.6809	0.2245	0.102*
H22C	0.6560	0.8204	0.2946	0.102*
C23	0.5204 (7)	0.9147 (6)	0.1376 (7)	0.085 (2)
H23A	0.4863	0.9469	0.2049	0.128*
H23B	0.4548	0.9139	0.0719	0.128*
H23C	0.6164	0.9746	0.1354	0.128*
C24	0.2058 (5)	0.6298 (5)	0.0541 (4)	0.0510 (12)
H24A	0.1274	0.5496	0.0641	0.061*
C25	0.1402 (7)	0.7457 (7)	0.0570 (6)	0.0793 (18)
H25A	0.2084	0.8238	0.0375	0.119*
H25B	0.1196	0.7703	0.1319	0.119*
H25C	0.0513	0.7164	0.0035	0.119*
C26	0.2453 (7)	0.5916 (9)	−0.0620 (5)	0.092 (2)
H26A	0.1588	0.5617	−0.1182	0.138*
H26B	0.2874	0.5190	−0.0616	0.138*
H26C	0.3148	0.6702	−0.0798	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ir1	0.03986 (10)	0.03282 (9)	0.03745 (10)	0.00918 (7)	0.00462 (7)	0.00396 (6)
Se1	0.0369 (2)	0.0379 (2)	0.0589 (3)	0.00759 (18)	0.0148 (2)	0.0044 (2)
Se2	0.0454 (2)	0.0417 (2)	0.0647 (3)	0.01693 (19)	0.0215 (2)	0.0117 (2)
P1	0.0354 (5)	0.0349 (5)	0.0337 (6)	0.0103 (4)	0.0063 (4)	0.0076 (4)
P2	0.0335 (5)	0.0390 (6)	0.0348 (6)	0.0110 (4)	0.0058 (4)	0.0090 (4)
N1	0.046 (2)	0.0352 (19)	0.037 (2)	0.0096 (16)	0.0086 (16)	0.0081 (15)
C1	0.087 (4)	0.050 (3)	0.081 (4)	0.038 (3)	0.023 (4)	−0.007 (3)
C2	0.083 (4)	0.057 (3)	0.069 (4)	0.017 (3)	0.021 (3)	−0.025 (3)
C3	0.090 (4)	0.057 (3)	0.100 (5)	0.015 (3)	0.043 (4)	0.045 (4)
C4	0.067 (4)	0.049 (3)	0.091 (5)	−0.019 (3)	0.030 (3)	0.007 (3)
C11	0.059 (3)	0.043 (2)	0.046 (3)	0.019 (2)	0.020 (2)	0.010 (2)
C12	0.071 (3)	0.060 (3)	0.080 (4)	0.039 (3)	0.021 (3)	0.018 (3)
C13	0.097 (5)	0.054 (3)	0.092 (5)	0.016 (3)	0.021 (4)	−0.019 (3)
C14	0.042 (2)	0.064 (3)	0.042 (3)	0.018 (2)	0.002 (2)	0.015 (2)
C15	0.055 (3)	0.096 (5)	0.066 (4)	−0.004 (3)	−0.014 (3)	0.018 (3)
C16	0.074 (4)	0.129 (6)	0.064 (4)	0.035 (4)	0.015 (3)	0.056 (4)
C21	0.044 (2)	0.051 (3)	0.047 (3)	0.012 (2)	0.018 (2)	0.015 (2)
C22	0.041 (3)	0.068 (4)	0.082 (4)	−0.002 (2)	0.009 (3)	0.015 (3)
C23	0.074 (4)	0.055 (4)	0.135 (6)	0.013 (3)	0.039 (4)	0.042 (4)
C24	0.045 (2)	0.067 (3)	0.040 (3)	0.020 (2)	0.000 (2)	0.006 (2)
C25	0.082 (4)	0.095 (5)	0.072 (4)	0.051 (4)	−0.006 (3)	0.013 (4)
C26	0.077 (4)	0.157 (7)	0.042 (3)	0.056 (5)	−0.006 (3)	−0.005 (4)

Geometric parameters (Å, º) top

Ir1—C3	2.119 (5)	C13—H13A	0.9600
Ir1—C2	2.125 (5)	C13—H13B	0.9600
Ir1—C4	2.141 (5)	C13—H13C	0.9600
Ir1—C1	2.145 (5)	C14—C16	1.524 (7)
Ir1—Se2	2.4590 (5)	C14—C15	1.529 (7)
Ir1—Se1	2.4611 (5)	C14—H14A	0.9800
Se1—P1	2.1975 (11)	C15—H15A	0.9600
Se2—P2	2.2026 (12)	C15—H15B	0.9600
P1—N1	1.595 (3)	C15—H15C	0.9600
P1—C11	1.826 (5)	C16—H16A	0.9600
P1—C14	1.832 (5)	C16—H16B	0.9600
P2—N1	1.599 (4)	C16—H16C	0.9600
P2—C21	1.825 (4)	C21—C22	1.521 (7)
P2—C24	1.832 (5)	C21—C23	1.530 (7)
C1—C2	1.394 (9)	C21—H21A	0.9800
C1—H1A	0.9300	C22—H22A	0.9600
C1—H1B	0.9300	C22—H22B	0.9600
C2—H2A	0.9300	C22—H22C	0.9600
C2—H2B	0.9300	C23—H23A	0.9600
C3—C4	1.401 (9)	C23—H23B	0.9600
C3—H3A	0.9300	C23—H23C	0.9600
C3—H3B	0.9300	C24—C26	1.518 (7)
C4—H4A	0.9300	C24—C25	1.519 (8)
C4—H4B	0.9300	C24—H24A	0.9800
C11—C13	1.517 (7)	C25—H25A	0.9600
C11—C12	1.522 (7)	C25—H25B	0.9600
C11—H11A	0.9800	C25—H25C	0.9600
C12—H12A	0.9600	C26—H26A	0.9600
C12—H12B	0.9600	C26—H26B	0.9600
C12—H12C	0.9600	C26—H26C	0.9600

C3—Ir1—C2	98.6 (3)	C11—C12—H12C	109.5
C3—Ir1—C4	38.4 (2)	H12A—C12—H12C	109.5
C2—Ir1—C4	86.8 (2)	H12B—C12—H12C	109.5
C3—Ir1—C1	86.0 (2)	C11—C13—H13A	109.5
C2—Ir1—C1	38.1 (2)	C11—C13—H13B	109.5
C4—Ir1—C1	98.9 (2)	H13A—C13—H13B	109.5
C3—Ir1—Se2	154.8 (2)	C11—C13—H13C	109.5
C2—Ir1—Se2	86.18 (16)	H13A—C13—H13C	109.5
C4—Ir1—Se2	166.4 (2)	H13B—C13—H13C	109.5
C1—Ir1—Se2	82.61 (16)	C16—C14—C15	111.5 (5)
C3—Ir1—Se1	86.27 (17)	C16—C14—P1	112.6 (4)
C2—Ir1—Se1	156.23 (19)	C15—C14—P1	114.1 (4)
C4—Ir1—Se1	82.66 (17)	C16—C14—H14A	105.9
C1—Ir1—Se1	165.18 (18)	C15—C14—H14A	105.9
Se2—Ir1—Se1	99.332 (16)	P1—C14—H14A	105.9
P1—Se1—Ir1	109.29 (3)	C14—C15—H15A	109.5
P2—Se2—Ir1	110.38 (3)	C14—C15—H15B	109.5
N1—P1—C11	108.1 (2)	H15A—C15—H15B	109.5
N1—P1—C14	111.3 (2)	C14—C15—H15C	109.5
C11—P1—C14	110.2 (2)	H15A—C15—H15C	109.5
N1—P1—Se1	116.89 (14)	H15B—C15—H15C	109.5
C11—P1—Se1	104.32 (16)	C14—C16—H16A	109.5
C14—P1—Se1	105.85 (17)	C14—C16—H16B	109.5
N1—P2—C21	108.2 (2)	H16A—C16—H16B	109.5
N1—P2—C24	111.2 (2)	C14—C16—H16C	109.5
C21—P2—C24	110.3 (2)	H16A—C16—H16C	109.5
N1—P2—Se2	116.88 (13)	H16B—C16—H16C	109.5
C21—P2—Se2	104.26 (16)	C22—C21—C23	110.5 (5)
C24—P2—Se2	105.67 (17)	C22—C21—P2	112.0 (3)
P1—N1—P2	127.3 (2)	C23—C21—P2	111.8 (3)
C2—C1—Ir1	70.2 (3)	C22—C21—H21A	107.4
C2—C1—H1A	120.0	C23—C21—H21A	107.4
Ir1—C1—H1A	49.8	P2—C21—H21A	107.4
C2—C1—H1B	120.0	C21—C22—H22A	109.5
Ir1—C1—H1B	169.8	C21—C22—H22B	109.5
H1A—C1—H1B	120.0	H22A—C22—H22B	109.5
C1—C2—Ir1	71.7 (3)	C21—C22—H22C	109.5
C1—C2—H2A	120.0	H22A—C22—H22C	109.5
Ir1—C2—H2A	48.3	H22B—C22—H22C	109.5
C1—C2—H2B	120.0	C21—C23—H23A	109.5
Ir1—C2—H2B	168.3	C21—C23—H23B	109.5
H2A—C2—H2B	120.0	H23A—C23—H23B	109.5
C4—C3—Ir1	71.7 (3)	C21—C23—H23C	109.5
C4—C3—H3A	120.0	H23A—C23—H23C	109.5
Ir1—C3—H3A	48.3	H23B—C23—H23C	109.5
C4—C3—H3B	120.0	C26—C24—C25	111.0 (5)
Ir1—C3—H3B	168.3	C26—C24—P2	112.6 (4)
H3A—C3—H3B	120.0	C25—C24—P2	114.7 (4)
C3—C4—Ir1	69.9 (3)	C26—C24—H24A	105.9
C3—C4—H4A	120.0	C25—C24—H24A	105.9
Ir1—C4—H4A	50.1	P2—C24—H24A	105.9
C3—C4—H4B	120.0	C24—C25—H25A	109.5
Ir1—C4—H4B	170.1	C24—C25—H25B	109.5
H4A—C4—H4B	120.0	H25A—C25—H25B	109.5
C13—C11—C12	110.4 (5)	C24—C25—H25C	109.5
C13—C11—P1	112.6 (4)	H25A—C25—H25C	109.5
C12—C11—P1	111.3 (3)	H25B—C25—H25C	109.5
C13—C11—H11A	107.5	C24—C26—H26A	109.5
C12—C11—H11A	107.5	C24—C26—H26B	109.5
P1—C11—H11A	107.5	H26A—C26—H26B	109.5
C11—C12—H12A	109.5	C24—C26—H26C	109.5
C11—C12—H12B	109.5	H26A—C26—H26C	109.5
H12A—C12—H12B	109.5	H26B—C26—H26C	109.5

C3—Ir1—Se1—P1	131.1 (2)	C1—Ir1—C3—C4	−109.8 (4)
C2—Ir1—Se1—P1	−126.0 (4)	Se2—Ir1—C3—C4	−173.1 (3)
C4—Ir1—Se1—P1	169.5 (2)	Se1—Ir1—C3—C4	82.9 (4)
C1—Ir1—Se1—P1	72.3 (6)	C2—Ir1—C4—C3	108.1 (4)
Se2—Ir1—Se1—P1	−24.11 (4)	C1—Ir1—C4—C3	71.8 (4)
C3—Ir1—Se2—P2	−121.0 (4)	Se2—Ir1—C4—C3	167.4 (6)
C2—Ir1—Se2—P2	136.9 (2)	Se1—Ir1—C4—C3	−93.3 (4)
C4—Ir1—Se2—P2	77.5 (7)	N1—P1—C11—C13	−57.8 (5)
C1—Ir1—Se2—P2	175.02 (19)	C14—P1—C11—C13	63.9 (5)
Se1—Ir1—Se2—P2	−19.84 (4)	Se1—P1—C11—C13	177.1 (4)
Ir1—Se1—P1—N1	59.94 (15)	N1—P1—C11—C12	66.7 (4)
Ir1—Se1—P1—C11	179.16 (16)	C14—P1—C11—C12	−171.6 (3)
Ir1—Se1—P1—C14	−64.58 (17)	Se1—P1—C11—C12	−58.3 (4)
Ir1—Se2—P2—N1	56.66 (15)	N1—P1—C14—C16	168.3 (4)
Ir1—Se2—P2—C21	175.99 (16)	C11—P1—C14—C16	48.5 (5)
Ir1—Se2—P2—C24	−67.67 (17)	Se1—P1—C14—C16	−63.7 (5)
C11—P1—N1—P2	−148.8 (3)	N1—P1—C14—C15	39.8 (5)
C14—P1—N1—P2	90.1 (3)	C11—P1—C14—C15	−80.0 (5)
Se1—P1—N1—P2	−31.6 (3)	Se1—P1—C14—C15	167.8 (4)
C21—P2—N1—P1	−147.9 (3)	N1—P2—C21—C22	69.1 (4)
C24—P2—N1—P1	90.8 (3)	C24—P2—C21—C22	−169.0 (4)
Se2—P2—N1—P1	−30.7 (3)	Se2—P2—C21—C22	−55.9 (4)
C3—Ir1—C1—C2	109.3 (4)	N1—P2—C21—C23	−55.5 (5)
C4—Ir1—C1—C2	73.1 (4)	C24—P2—C21—C23	66.4 (5)
Se2—Ir1—C1—C2	−93.2 (3)	Se2—P2—C21—C23	179.4 (4)
Se1—Ir1—C1—C2	168.2 (5)	N1—P2—C24—C26	168.1 (5)
C3—Ir1—C2—C1	−72.2 (4)	C21—P2—C24—C26	48.1 (5)
C4—Ir1—C2—C1	−108.8 (4)	Se2—P2—C24—C26	−64.1 (5)
Se2—Ir1—C2—C1	82.9 (3)	N1—P2—C24—C25	39.9 (5)
Se1—Ir1—C2—C1	−172.5 (3)	C21—P2—C24—C25	−80.2 (5)
C2—Ir1—C3—C4	−73.7 (4)	Se2—P2—C24—C25	167.7 (4)

Experimental details

Crystal data
Chemical formula	[Ir(C₂H₄)₂(C₁₂H₂₈NP₂Se₂)]
M_r	654.52
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.6965 (1), 10.3962 (1), 12.0620 (1)
α, β, γ (°)	98.511 (1), 96.055 (1), 107.273 (1)
V (Å³)	1133.84 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	9.24
Crystal size (mm)	0.30 × 0.21 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.168, 0.320
No. of measured, independent and observed [I > 2σ(I)] reflections	15331, 5170, 4505
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.067, 1.03
No. of reflections	5170
No. of parameters	207
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.39, −1.03

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This project was supported by the Program for New Century Excellent Talents in Universities of China (NCET-06–0556 and NCET-08–0618).

References

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