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ISSN: 2056-9890

cis-Di­iodido(N,N,N′,N′-tetra­methyl­ethylenedi­amine-κ2N,N′)palladium(II)

aGrupo de Química Organometálica, Departamento de Química Inorgánica, Universidad de Murcia, Murcia 30071, Spain, and bSAI, Universidad de Murcia, Murcia 30071, Spain
*Correspondence e-mail: dbc@um.es

(Received 29 June 2012; accepted 20 July 2012; online 28 July 2012)

In the title complex, cis-[PdI2(C6H16N2)], the PdII atom lies on a crystallographic twofold rotation axis and is four-coordinated by the two N atoms of a chelating N,N,N′,N′-tetra­methyl­ethylenediamine ligand [Pd—N = 2.125 (3) Å] and two I atoms [Pd—I = 2.5833 (4) Å], displaying a distorted square-planar geometry (r.m.s. deviation = 0.005 Å), imposed by the small bite of the chelating ligand [N—Pd—N angle = 84.68 (18)°].

Related literature

For related diiodido complexes, see: Jones et al. (2007[Jones, P. G., Fernández-Rodríguez, M. J. & Martínez-Martínez, A. J. (2007). Acta Cryst. E63, m2758.]); Wursche et al. (1999[Wursche, R., Klinga, M. & Rieger, B. (1999). Private communication (deposition number 136187). CCDC, Cambridge, England.]); Dodd et al. (2006[Dodd, D. W., Toews, H. E., Carneiro, F. S., Jennings, M. C. & Jones, N. D. (2006). Inorg. Chim. Acta, 359 2850-2858.]); Alsters et al. (1993[Alsters, P. L., Engel, P. F., Hogerheide, M. P., Copijn, M., Spek, A. L. & van Koten, G. (1993). Organometallics, 12, 1831-1844.]); Bhattacharyya et al. (2009[Bhattacharyya, S., Clark, A. E. & Pink, M. M. Z. J. (2009). Inorg. Chem. 48, 3916-3925.]); Ha (2009[Ha, K. (2009). Acta Cryst. E65, m1588.], 2010[Ha, K. (2010). Z. Kristallogr. New Cryst. Struct. 225, 317-318.]). For mol­ecular parameters in related dichlorido complexes, see: Boyle et al. (2004[Boyle, R. C., Mague, J. T. & Fink, M. J. (2004). Acta Cryst. E60, m40-m41.]); Iball et al. (1975[Iball, J., MacDougall, M. & Scrimgeour, S. (1975). Acta Cryst. B31, 1672-1674.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [PdI2(C6H16N2)]

  • Mr = 476.41

  • Monoclinic, C 2/c

  • a = 7.9266 (4) Å

  • b = 14.6911 (7) Å

  • c = 10.5309 (5) Å

  • β = 107.262 (2)°

  • V = 1171.09 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 6.81 mm−1

  • T = 100 K

  • 0.22 × 0.15 × 0.03 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.581, Tmax = 0.822

  • 6502 measured reflections

  • 1351 independent reflections

  • 1326 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.023

  • wR(F2) = 0.060

  • S = 1.14

  • 1351 reflections

  • 53 parameters

  • H-atom parameters constrained

  • Δρmax = 1.23 e Å−3

  • Δρmin = −0.73 e Å−3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

A small amount of the title compound (1) formed when the complex [PdI(C6H4{NHC(Me)=C{C(O)Me}C(C(CO2Me)C=CHCO2Me}-2(tmeda)] was heated in toluene with the aim to isomerize it. The insoluble complex 1 was separated by filtration and, single crystals, obtained by the liquid diffusion method using dichloromethane and diethyl ether, were used for struture determintation. The pure compound 1 was prepared as stated in the Experimental section, and crystals grown using the same method and solvents as above were used to confirm the cell dimensions.

Only a few complexes of the type [PdI2(N^N)] (N^N = chelating nitrongen donor ligand) have been characterized by their X ray crystal structures, namely those with N^N = 4,4'-di-tert-butyl-2,2'-bipyridine (Jones et al. 2007); 2-((4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)pyridine (Dodd et al. 2006); 1,2-bis(1-pyrrolidino)ethane (Wursche et al., 1999); N-2-iodobenzyl-N,N',N'-trimethylethane-1,2-diamine (Alsters et al. 1993); 2,2'-bipyridine (Ha 2009); 1,4-dibenzyl-1,4-diazacyclododec-8-ene-6,10-diyne-N1,N4 (Bhattacharyya et al. 2009) and 1,10-phenanthroline (Ha 2010). This contrasts with the nearly five hundred crystal structures of dichloro homologous complexes (CCDC, November 2010).

The molecular structure of complex 1 is shown in Fig. 1. The asymmetric unit comprises a half of the molecule as the Pd atom lies on a crystallographic twofold axis. The coordinated ligand atoms and Pd(II) are coplanar within the limits of experimental errors: I1 and N1 are displaced from the least square plane defined by the five atoms by +0.0050 (15) and +0.0062 (19) Å, respectively. The bite of the chelating tmeda ligand displays a N(1)–C(1)–C(1 A)–N(1 A) torsion angle of -56.37(0.60)°. The planes of the two NMe2 fragments substend an angle of 12.10(0.08)°.

The Pd–N bonds in the diiodo complex 1 (2.125 (3) Å) are slightly longer than in the homologous dichloro complex [2.053 (3) and 2.073 (3) Å] reflecting the greater trans influence of the iodo ligands. The I(1)—Pd(1)—I(1 A) bond angle in 1 (87.907 (18)°) is narrower than the Cl(1)—Pd—Cl(2) one in [PdCl2(tmeda)] (Boyle et al. 2004) (90.72 (5)°) although the opposite was expected in view of the smaller electronegativity and the bigger size of the iodo ligand compared to chloro. We attribute this fact to the steric hyndrance caused on the iodo ligands by the NMe2 groups in the chelating ligand, imposed by the short Pd—N bonds. This is supported by both, the larger Cl—Pd—Cl angle in [PdCl2(en)] (Iball et al. 1975) (95.3 (3)°) than that in [PdCl2(tmeda)] (90.72 (5)°) and on a search at the Cambridge Crystallographic Database (version 5.32, November 2010, updated November 2011) for [PdX2(P^P)] (X = Cl, I, P^P = phorphorus donor chelating ligands) showing that the I—Pd—I angles are, as expected, wider than the Cl—Pd—Cl ones in homologous complexes, probably because, in this case, the longer Pd—P bond distances keep the phosphorus substituents away enough from the halogen ligands.

Related literature top

For related diiodo complexes, see: Jones et al. (2007); Wursche et al. (1999); Dodd et al. (2006); Alsters et al. (1993); Bhattacharyya et al. (2009); Ha (2009, 2010). For molecular parameters in related dichlorido complexes, see: Boyle et al. (2004); Iball et al. (1975). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Synthesis. The pure compound (1) was prepared in 88% yield from [PdCl2(tmeda)] and NaI (1:5, in acetone, 3 h at room temperature). The complex was extracted into dichloromethane and precipitated with diethyl ether. M.p. 194 °C (decomposition). 1H NMR (200 MHz, CDCl3): d 2.68 (s, 2 H, CH2), 2.96 (s, 6 H, Me). Analysis calcd for C6H16I2N2Pd: C, 15.13; H, 3.39; N, 5.88. Found: C, 15.62; H, 3.43; N, 6.03.

Refinement top

Methyl H atoms were identified in difference syntheses, idealized and refined using rigid groups allowed to rotate but not tip, with C—H 0.98 Å, H—C—H 109.5°. Other H atoms were introduced at the calculated positions and refined using a riding model, with methylene C—H 0.99 Å. The Uiso(H) values were set equal to mUeq(C) of the parent carbons, with m = 1.5 for methyls and 1.2 for all other H.

Structure description top

A small amount of the title compound (1) formed when the complex [PdI(C6H4{NHC(Me)=C{C(O)Me}C(C(CO2Me)C=CHCO2Me}-2(tmeda)] was heated in toluene with the aim to isomerize it. The insoluble complex 1 was separated by filtration and, single crystals, obtained by the liquid diffusion method using dichloromethane and diethyl ether, were used for struture determintation. The pure compound 1 was prepared as stated in the Experimental section, and crystals grown using the same method and solvents as above were used to confirm the cell dimensions.

Only a few complexes of the type [PdI2(N^N)] (N^N = chelating nitrongen donor ligand) have been characterized by their X ray crystal structures, namely those with N^N = 4,4'-di-tert-butyl-2,2'-bipyridine (Jones et al. 2007); 2-((4S)-4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)pyridine (Dodd et al. 2006); 1,2-bis(1-pyrrolidino)ethane (Wursche et al., 1999); N-2-iodobenzyl-N,N',N'-trimethylethane-1,2-diamine (Alsters et al. 1993); 2,2'-bipyridine (Ha 2009); 1,4-dibenzyl-1,4-diazacyclododec-8-ene-6,10-diyne-N1,N4 (Bhattacharyya et al. 2009) and 1,10-phenanthroline (Ha 2010). This contrasts with the nearly five hundred crystal structures of dichloro homologous complexes (CCDC, November 2010).

The molecular structure of complex 1 is shown in Fig. 1. The asymmetric unit comprises a half of the molecule as the Pd atom lies on a crystallographic twofold axis. The coordinated ligand atoms and Pd(II) are coplanar within the limits of experimental errors: I1 and N1 are displaced from the least square plane defined by the five atoms by +0.0050 (15) and +0.0062 (19) Å, respectively. The bite of the chelating tmeda ligand displays a N(1)–C(1)–C(1 A)–N(1 A) torsion angle of -56.37(0.60)°. The planes of the two NMe2 fragments substend an angle of 12.10(0.08)°.

The Pd–N bonds in the diiodo complex 1 (2.125 (3) Å) are slightly longer than in the homologous dichloro complex [2.053 (3) and 2.073 (3) Å] reflecting the greater trans influence of the iodo ligands. The I(1)—Pd(1)—I(1 A) bond angle in 1 (87.907 (18)°) is narrower than the Cl(1)—Pd—Cl(2) one in [PdCl2(tmeda)] (Boyle et al. 2004) (90.72 (5)°) although the opposite was expected in view of the smaller electronegativity and the bigger size of the iodo ligand compared to chloro. We attribute this fact to the steric hyndrance caused on the iodo ligands by the NMe2 groups in the chelating ligand, imposed by the short Pd—N bonds. This is supported by both, the larger Cl—Pd—Cl angle in [PdCl2(en)] (Iball et al. 1975) (95.3 (3)°) than that in [PdCl2(tmeda)] (90.72 (5)°) and on a search at the Cambridge Crystallographic Database (version 5.32, November 2010, updated November 2011) for [PdX2(P^P)] (X = Cl, I, P^P = phorphorus donor chelating ligands) showing that the I—Pd—I angles are, as expected, wider than the Cl—Pd—Cl ones in homologous complexes, probably because, in this case, the longer Pd—P bond distances keep the phosphorus substituents away enough from the halogen ligands.

For related diiodo complexes, see: Jones et al. (2007); Wursche et al. (1999); Dodd et al. (2006); Alsters et al. (1993); Bhattacharyya et al. (2009); Ha (2009, 2010). For molecular parameters in related dichlorido complexes, see: Boyle et al. (2004); Iball et al. (1975). For a description of the Cambridge Structural Database, see: Allen (2002).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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
[Figure 1] Fig. 1. The molecular structure of the title compound. Ellipsoids represent 50% probability levels.
[Figure 2] Fig. 2. Packing diagram of the title compound view down b axis Hydrogen atoms are omitted.
cis-Diiodido(N,N,N',N'-\ tetramethylethylenediamine-κ2N,N')palladium(II) top
Crystal data top
[PdI2(C6H16N2)]F(000) = 872
Mr = 476.41Dx = 2.702 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4971 reflections
a = 7.9266 (4) Åθ = 2.8–28.1°
b = 14.6911 (7) ŵ = 6.81 mm1
c = 10.5309 (5) ÅT = 100 K
β = 107.262 (2)°Needle, red
V = 1171.09 (10) Å30.22 × 0.15 × 0.03 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
1351 independent reflections
Radiation source: fine-focus sealed tube1326 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 8.26 pixels mm-1θmax = 28.1°, θmin = 2.8°
ω scanh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
k = 1818
Tmin = 0.581, Tmax = 0.822l = 1313
6502 measured reflections
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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.025P)2 + 10.9315P]
where P = (Fo2 + 2Fc2)/3
1351 reflections(Δ/σ)max = 0.001
53 parametersΔρmax = 1.23 e Å3
0 restraintsΔρmin = 0.73 e Å3
Crystal data top
[PdI2(C6H16N2)]V = 1171.09 (10) Å3
Mr = 476.41Z = 4
Monoclinic, C2/cMo Kα radiation
a = 7.9266 (4) ŵ = 6.81 mm1
b = 14.6911 (7) ÅT = 100 K
c = 10.5309 (5) Å0.22 × 0.15 × 0.03 mm
β = 107.262 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
1351 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
1326 reflections with I > 2σ(I)
Tmin = 0.581, Tmax = 0.822Rint = 0.020
6502 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.060H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.025P)2 + 10.9315P]
where P = (Fo2 + 2Fc2)/3
1351 reflectionsΔρmax = 1.23 e Å3
53 parametersΔρmin = 0.73 e Å3
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 0.3294 (0.0368) x + 14.6093 (0.0042) y + 1.1036 (0.0293) z = 6.0620 (0.0112)

* 0.0000 (0.0000) N1 * 0.0000 (0.0000) C2 * 0.0000 (0.0000) C3

Rms deviation of fitted atoms = 0.0000

0.3294 (0.0369) x + 14.6093 (0.0042) y - 1.1036 (0.0293) z = 5.8396 (0.0312)

Angle to previous plane (with approximate e.s.d.) = 12.10 (0.08)

* 0.0000 (0.0000) N1_$1 * 0.0000 (0.0000) C2_$1 * 0.0000 (0.0000) C3_$1

Rms deviation of fitted atoms = 0.0000

5.5219 (0.0048) x - 0.0000 (0.0000) y - 9.3919 (0.0040) z = 0.4130 (0.0034)

Angle to previous plane (with approximate e.s.d.) = 84.35 (0.22)

* 0.0000 (0.0000) Pd1 * 0.0062 (0.0019) N1 * 0.0050 (0.0015) I1 * -0.0062 (0.0019) N1_$1 * -0.0050 (0.0015) I1_$1

Rms deviation of fitted atoms = 0.0050

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*/Ueq
Pd10.50000.51798 (3)0.25000.01073 (10)
I10.71154 (4)0.644568 (18)0.37384 (3)0.02349 (10)
N10.3317 (4)0.4111 (2)0.1504 (3)0.0136 (6)
C10.4427 (5)0.3275 (3)0.1794 (4)0.0191 (8)
H1A0.51750.32460.11920.023*
H1B0.36560.27310.16320.023*
C20.1807 (5)0.4035 (3)0.2057 (4)0.0209 (8)
H2A0.11290.46030.18960.031*
H2B0.22510.39220.30160.031*
H2C0.10450.35290.16250.031*
C30.2605 (6)0.4205 (3)0.0038 (4)0.0216 (8)
H3A0.19470.36540.03360.032*
H3B0.35840.42910.03410.032*
H3C0.18160.47330.01760.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.01163 (18)0.01133 (18)0.00958 (18)0.0000.00366 (13)0.000
I10.02803 (17)0.02164 (16)0.01984 (16)0.01018 (10)0.00561 (11)0.00239 (10)
N10.0124 (14)0.0169 (15)0.0119 (14)0.0017 (12)0.0040 (11)0.0028 (12)
C10.0214 (19)0.0140 (17)0.022 (2)0.0004 (15)0.0073 (16)0.0038 (15)
C20.0145 (18)0.029 (2)0.022 (2)0.0052 (15)0.0090 (15)0.0034 (17)
C30.024 (2)0.025 (2)0.0134 (18)0.0046 (16)0.0033 (15)0.0043 (16)
Geometric parameters (Å, º) top
Pd1—N12.125 (3)C1—H1A0.9900
Pd1—N1i2.125 (3)C1—H1B0.9900
Pd1—I12.5833 (4)C2—H2A0.9800
Pd1—I1i2.5833 (4)C2—H2B0.9800
N1—C21.483 (5)C2—H2C0.9800
N1—C31.484 (5)C3—H3A0.9800
N1—C11.488 (5)C3—H3B0.9800
C1—C1i1.494 (8)C3—H3C0.9800
N1—Pd1—N1i84.68 (18)N1—C1—H1B109.5
N1—Pd1—I1178.36 (9)C1i—C1—H1B109.5
N1i—Pd1—I193.71 (9)H1A—C1—H1B108.1
N1—Pd1—I1i93.71 (9)N1—C2—H2A109.5
N1i—Pd1—I1i178.36 (9)N1—C2—H2B109.5
I1—Pd1—I1i87.906 (18)H2A—C2—H2B109.5
C2—N1—C3108.3 (3)N1—C2—H2C109.5
C2—N1—C1110.7 (3)H2A—C2—H2C109.5
C3—N1—C1108.1 (3)H2B—C2—H2C109.5
C2—N1—Pd1108.9 (2)N1—C3—H3A109.5
C3—N1—Pd1115.7 (2)N1—C3—H3B109.5
C1—N1—Pd1105.2 (2)H3A—C3—H3B109.5
N1—C1—C1i110.6 (3)N1—C3—H3C109.5
N1—C1—H1A109.5H3A—C3—H3C109.5
C1i—C1—H1A109.5H3B—C3—H3C109.5
N1i—Pd1—N1—C2104.9 (3)I1i—Pd1—N1—C1166.5 (2)
I1i—Pd1—N1—C274.8 (2)C2—N1—C1—C1i77.3 (4)
N1i—Pd1—N1—C3133.0 (3)C3—N1—C1—C1i164.2 (4)
I1i—Pd1—N1—C347.3 (3)Pd1—N1—C1—C1i40.1 (4)
N1i—Pd1—N1—C113.83 (18)N1—C1—C1i—N1i56.4 (6)
Symmetry code: (i) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formula[PdI2(C6H16N2)]
Mr476.41
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)7.9266 (4), 14.6911 (7), 10.5309 (5)
β (°) 107.262 (2)
V3)1171.09 (10)
Z4
Radiation typeMo Kα
µ (mm1)6.81
Crystal size (mm)0.22 × 0.15 × 0.03
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.581, 0.822
No. of measured, independent and
observed [I > 2σ(I)] reflections
6502, 1351, 1326
Rint0.020
(sin θ/λ)max1)0.662
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.060, 1.14
No. of reflections1351
No. of parameters53
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.025P)2 + 10.9315P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)1.23, 0.73

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors acknowledge financial support from the Ministerio de Educación y Ciencia (Spain), FEDER (CTQ2007–60808/BQU) and the Fundación Séneca (04539/GERM/06 and 03059/PI/05) and thank Professor Vicente (Universidad de Murcia) for his continuing support and encouragement.

References

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