metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 10| October 2014| Pages m343-m344

Crystal structure of bis­­{μ-2-[(di­methyl­amino)­meth­yl]ferrocene­seleno­lato}bis­[chlorido­palladium(II)]

aDepartment of Chemistry, P.O. Box 3000, FI-90014 University of Oulu, Finland
*Correspondence e-mail: risto.laitinen@oulu.fi

Edited by M. Zeller, Youngstown State University, USA (Received 8 August 2014; accepted 28 August 2014; online 3 September 2014)

The dinuclear title compound, [PdCl{Se[(C5H5)Fe(C5H3)2CH2N(CH3)2]}]2 was obtained by the reaction of [PdCl2(NCPh)2] with 2-[(N,N′-di­methyl­amino)­meth­yl]ferro­cene­seleno­late and the crystals for the structure determination were grown from a mixture of THF and n-hexane. Both PdII atoms are coordinated by the bridging Se atoms and by the amino N atoms of the bidentate 2-[(N,N′-di­methyl­amino)­meth­yl]ferrocene­seleno­late ligand, as well as by Cl atoms, and show a distorted square-planar coordination. The angle between the Pd—Se—Se planes of the two Pd atoms is 149.31 (3)°. Weak Cl⋯H hydrogen bonds link the binuclear complexes into a three-dimensional network.

1. Related literature

The structural data for mononuclear [PdCl(C9H12NSe)PPh3] containing a chelating 2-[(N,N′-di­methyl­amino)­meth­yl]benzene­seleno­late ligand have been reported by Takaluoma et al. (2014[Takaluoma, E. M., Oilunkaniemi, R. & Laitinen, R. S. (2014). Acta Cryst. E70, m215.]). For the synthesis of a related dinuclear palladium complex containing a chiral 2-[(N,N′-di­methyl­amino)­eth­yl]ferrocene­seleno­late ligand, see: Kaur et al. (2009[Kaur, R., Menon, S. C., Panda, S., Singh, H. B., Patel, R. P. & Butcher, R. J. (2009). Organometallics, 28, 2363-2371.]). For the structure of the dinuclear palladium complex [PdCl(C9H12NSe)]2, see: Chakravorty et al. (2012[Chakravorty, T., Singh, H. B. & Butcher, R. J. (2012). Acta Cryst. E68, m113-m114.]); Pop et al. (2013[Pop, A., Rosca, D., Mitea, R. & Silvestru, A. (2013). Inorg. Chim. Acta, 405, 235-242.]). For the synthesis of lithium [2-(N,N′-di­methyl­amino)­meth­yl]ferrocene­seleno­late, see: Gornitzka et al. (1992[Gornitzka, H., Besser, S., Herbst-Irmer, R., Kilimann, U. & Edelmann, F. T. (1992). Angew. Chem. Int. Ed. Engl. 31, 1260-1261.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Fe2Pd2(C5H5)2Cl2(C8H11NSe)2]

  • Mr = 925.85

  • Monoclinic, P 21 /n

  • a = 13.030 (3) Å

  • b = 10.985 (2) Å

  • c = 19.925 (4) Å

  • β = 93.25 (3)°

  • V = 2847.4 (10) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 5.01 mm−1

  • T = 120 K

  • 0.40 × 0.05 × 0.05 mm

2.2. Data collection

  • Bruker–Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (XPREP in SHELXTL; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.655, Tmax = 0.938

  • 19836 measured reflections

  • 4847 independent reflections

  • 3937 reflections with I > 2σ(I)

  • Rint = 0.078

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.088

  • S = 1.07

  • 4847 reflections

  • 330 parameters

  • H-atom parameters constrained

  • Δρmax = 0.69 e Å−3

  • Δρmin = −0.62 e Å−3

Table 1
Selected geometric parameters (Å, °)

Pd1—N1 2.182 (5)
Pd1—Cl1 2.3585 (17)
Pd1—Se2 2.3898 (8)
Pd1—Se1 2.4051 (9)
Pd2—N2 2.152 (5)
Pd2—Cl2 2.3540 (17)
Pd2—Se2 2.3716 (8)
Pd2—Se1 2.4166 (8)
N1—Pd1—Cl1 92.99 (15)
N1—Pd1—Se2 93.62 (14)
Cl1—Pd1—Se2 173.39 (5)
N1—Pd1—Se1 172.87 (15)
Cl1—Pd1—Se1 93.59 (5)
Se2—Pd1—Se1 79.80 (3)
N2—Pd2—Cl2 92.05 (15)
N2—Pd2—Se2 175.53 (15)
Cl2—Pd2—Se2 91.22 (5)
N2—Pd2—Se1 96.84 (14)
Cl2—Pd2—Se1 171.10 (5)
Se2—Pd2—Se1 79.92 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C113—H11F⋯Cl1 0.98 2.70 3.347 (8) 124
C212—H21D⋯Cl2 0.98 2.75 3.394 (8) 124
C213—H21H⋯Cl2 0.98 2.74 3.384 (8) 124
C22—H22⋯Cl1 0.95 2.82 3.537 (7) 133

Data collection: COLLECT (Bruker, 2008[Bruker (2008). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol 276. Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]; molecular graphics: DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GmbH, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Synthesis and crystallization top

Lithium [2-(N,'N-di­methyl­amino)­methyl]­ferrocene­seleno­late was obtained, as described by Gornitzka et al. (1992). Li­thia­ted N,'N-di­methyl­amino­methyl­ferrocene (0.100 g, 0.40 mmol) was dissolved in 30 ml of THF and cooled to -78 °C. Selenium (0.030 g 0.38 mmol) was added into the solution and the reaction solution was warmed to room temperature. The light yellow solution was added to 0.144 g (0.38 mmol) of [PdCl2(NCPh)2] in 30 ml THF. The solution turned dark red and was stirred over night and was subsequently evaporated to 5 ml. A dark red powder was obtained by precipitation with n-hexane. It was washed twice with n-hexane and dried. Both mass spectrometry and elemental analysis indicated that the powder was a mixture. A small amount of dark red crystals of the title compound, which were suitable for crystal structure determination, were grown from a mixture of THF and n-hexane.

Refinement top

Crystal data, data collection and structure refinement details are summarized below. H atoms were positioned geometrically and refined using a riding model. The C—H fixed bond lengths are 0.98, 0.99, and 0.95 Å for methyl, methyl­ene, and aromatic hydrogens, respectively. Uiso(H) was constrained to be 1.5 times Ueq(C) for methyl hydrogens and 1.2 times Ueq(C) for methyl­ene and aromatic hydrogens.

Related literature top

The structural data for mononuclear [PdCl(C9H12NSe)PPh3] containing a chelating 2-[(N,N'-dimethylamino)methyl]benzeneselenolate ligand had been reported by Takaluoma et al. (2014). For the synthesis of a related dinuclear palladium complex containing a chiral 2-[(N,N'-dimethylamino)ethyl]ferroceneselenolate ligand, see: Kaur et al.(2009). For the structure of the dinuclear palladium complex [PdCl(C9H12NSe)]2, see: Chakravorty et al. (2012); Pop et al. (2013). For the synthesis of lithium [2-(N,N'-dimethylamino)methyl]ferroceneselenolate, see: Gornitzka et al. (1992).

Computing details top

Data collection: COLLECT (Bruker, 2008); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound indicating the numbering of the atoms. The thermal ellipsoids have been drawn at 50% probability. Hydrogen atoms have been omitted for clarity.
Bis{µ-2-[(dimethylamino)methyl]ferroceneselenolato}bis[chloridopalladium(II)] top
Crystal data top
[Fe2Pd2(C5H5)2Cl2(C8H11NSe)2]F(000) = 1792
Mr = 925.85Dx = 2.160 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.030 (3) ÅCell parameters from 3937 reflections
b = 10.985 (2) Åθ = 3.1–25.0°
c = 19.925 (4) ŵ = 5.01 mm1
β = 93.25 (3)°T = 120 K
V = 2847.4 (10) Å3Needle, red
Z = 40.40 × 0.05 × 0.05 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
3937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.078
ϕ scans, and ω scans with κ offsetsθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan
(XPREP in SHELXTL; Sheldrick, 2008)
h = 1515
Tmin = 0.655, Tmax = 0.938k = 1313
19836 measured reflectionsl = 2321
4847 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0248P)2 + 17.5058P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4847 reflectionsΔρmax = 0.69 e Å3
330 parametersΔρmin = 0.62 e Å3
0 restraintsExtinction correction: SHELXL2013 (Sheldrick, 2013), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00086 (12)
Crystal data top
[Fe2Pd2(C5H5)2Cl2(C8H11NSe)2]V = 2847.4 (10) Å3
Mr = 925.85Z = 4
Monoclinic, P21/nMo Kα radiation
a = 13.030 (3) ŵ = 5.01 mm1
b = 10.985 (2) ÅT = 120 K
c = 19.925 (4) Å0.40 × 0.05 × 0.05 mm
β = 93.25 (3)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
4847 independent reflections
Absorption correction: multi-scan
(XPREP in SHELXTL; Sheldrick, 2008)
3937 reflections with I > 2σ(I)
Tmin = 0.655, Tmax = 0.938Rint = 0.078
19836 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0248P)2 + 17.5058P]
where P = (Fo2 + 2Fc2)/3
4847 reflectionsΔρmax = 0.69 e Å3
330 parametersΔρmin = 0.62 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pd10.22704 (4)0.80997 (4)0.50395 (2)0.01626 (14)
Pd20.15556 (4)1.11994 (4)0.48597 (2)0.01682 (14)
Se10.10993 (5)0.94796 (5)0.55379 (3)0.01595 (16)
Se20.20573 (5)0.95790 (5)0.41633 (3)0.01657 (16)
Cl10.23531 (16)0.67804 (16)0.59748 (8)0.0326 (4)
Cl20.20566 (14)1.26486 (15)0.40718 (9)0.0304 (4)
N10.3262 (4)0.6940 (5)0.4467 (3)0.0218 (12)
N20.1156 (4)1.2594 (5)0.5557 (3)0.0214 (12)
Fe10.41999 (7)1.00911 (9)0.32407 (5)0.0206 (2)
Fe20.11295 (7)1.00558 (8)0.72807 (4)0.0182 (2)
C100.4069 (5)0.8686 (6)0.3912 (3)0.0210 (14)
C110.3504 (5)0.9741 (6)0.4102 (3)0.0165 (13)
C120.4197 (5)1.0724 (6)0.4203 (3)0.0238 (15)
H120.40281.15270.43340.029*
C130.5182 (5)1.0295 (7)0.4073 (3)0.0275 (16)
H130.57921.07700.41030.033*
C140.5132 (5)0.9046 (6)0.3891 (3)0.0229 (15)
H140.56900.85440.37770.028*
C150.3522 (6)0.9628 (7)0.2323 (4)0.0349 (18)
H150.31640.88940.22160.042*
C160.3081 (6)1.0701 (7)0.2564 (4)0.0304 (17)
H160.23761.08130.26440.037*
C170.3859 (6)1.1578 (7)0.2667 (4)0.0354 (18)
H170.37751.23820.28300.042*
C180.4799 (6)1.1041 (8)0.2481 (4)0.041 (2)
H180.54521.14270.24980.050*
C190.4585 (6)0.9825 (8)0.2265 (4)0.039 (2)
H190.50670.92550.21110.047*
C200.1446 (5)1.1310 (6)0.6565 (3)0.0186 (14)
C210.1723 (5)1.0104 (6)0.6354 (3)0.0175 (13)
C220.2458 (5)0.9604 (6)0.6829 (3)0.0199 (14)
H220.27610.88190.68100.024*
C230.2657 (5)1.0499 (6)0.7341 (3)0.0228 (15)
H230.31161.04120.77260.027*
C240.2051 (5)1.1540 (6)0.7174 (3)0.0256 (16)
H240.20461.22730.74270.031*
C250.0403 (5)1.0176 (6)0.7444 (3)0.0252 (16)
H250.08861.07050.72190.030*
C260.0156 (5)0.8971 (6)0.7233 (3)0.0269 (16)
H260.04350.85590.68460.032*
C270.0596 (5)0.8507 (6)0.7720 (4)0.0271 (16)
H270.09000.77220.77140.033*
C280.0807 (5)0.9414 (7)0.8208 (3)0.0261 (16)
H280.12830.93440.85850.031*
C290.0190 (5)1.0452 (7)0.8045 (3)0.0287 (16)
H290.01771.11920.82920.034*
C1110.3567 (5)0.7471 (6)0.3814 (3)0.0190 (14)
H11A0.40480.69090.36040.023*
H11B0.29490.75570.35050.023*
C1120.2682 (7)0.5809 (6)0.4316 (4)0.0354 (19)
H11C0.31310.52170.41100.053*
H11D0.20920.59890.40050.053*
H11E0.24380.54710.47330.053*
C1130.4211 (6)0.6654 (7)0.4884 (4)0.0310 (17)
H11F0.40290.62350.52950.047*
H11G0.45750.74110.50030.047*
H11H0.46550.61280.46290.047*
C2110.0708 (5)1.2127 (6)0.6178 (3)0.0222 (14)
H21A0.00691.16710.60540.027*
H21B0.05271.28220.64650.027*
C2120.2097 (6)1.3284 (6)0.5740 (4)0.0293 (16)
H21C0.19401.39350.60540.044*
H21D0.23651.36400.53340.044*
H21E0.26131.27380.59530.044*
C2130.0381 (6)1.3448 (6)0.5232 (4)0.0305 (17)
H21F0.02351.41030.55470.046*
H21G0.02551.30020.51100.046*
H21H0.06551.37960.48260.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0243 (3)0.0136 (2)0.0112 (2)0.0008 (2)0.0030 (2)0.00145 (18)
Pd20.0220 (3)0.0142 (2)0.0143 (3)0.0003 (2)0.0020 (2)0.00292 (19)
Se10.0195 (3)0.0157 (3)0.0128 (3)0.0016 (3)0.0025 (3)0.0013 (2)
Se20.0211 (3)0.0171 (3)0.0116 (3)0.0020 (3)0.0013 (3)0.0021 (2)
Cl10.0598 (12)0.0218 (8)0.0169 (8)0.0077 (8)0.0083 (8)0.0085 (7)
Cl20.0450 (11)0.0212 (8)0.0257 (9)0.0012 (8)0.0085 (8)0.0115 (7)
N10.031 (3)0.016 (3)0.019 (3)0.002 (2)0.006 (2)0.000 (2)
N20.026 (3)0.015 (3)0.023 (3)0.001 (2)0.001 (2)0.004 (2)
Fe10.0224 (5)0.0249 (5)0.0147 (5)0.0055 (4)0.0033 (4)0.0018 (4)
Fe20.0183 (5)0.0224 (5)0.0141 (5)0.0009 (4)0.0029 (4)0.0001 (4)
C100.025 (4)0.026 (4)0.012 (3)0.003 (3)0.002 (3)0.002 (3)
C110.017 (3)0.020 (3)0.012 (3)0.002 (3)0.006 (3)0.002 (3)
C120.030 (4)0.026 (4)0.016 (3)0.004 (3)0.005 (3)0.001 (3)
C130.028 (4)0.039 (4)0.015 (3)0.012 (3)0.002 (3)0.006 (3)
C140.023 (4)0.028 (4)0.019 (3)0.005 (3)0.005 (3)0.001 (3)
C150.045 (5)0.040 (5)0.019 (4)0.011 (4)0.003 (3)0.005 (3)
C160.028 (4)0.041 (4)0.023 (4)0.000 (3)0.004 (3)0.006 (3)
C170.042 (5)0.034 (4)0.030 (4)0.004 (4)0.003 (4)0.011 (3)
C180.032 (4)0.057 (6)0.035 (5)0.016 (4)0.003 (4)0.023 (4)
C190.040 (5)0.062 (6)0.015 (4)0.005 (4)0.004 (3)0.002 (4)
C200.019 (3)0.017 (3)0.020 (3)0.003 (3)0.009 (3)0.000 (3)
C210.019 (3)0.022 (3)0.012 (3)0.002 (3)0.002 (3)0.003 (3)
C220.021 (3)0.024 (3)0.015 (3)0.000 (3)0.002 (3)0.003 (3)
C230.021 (4)0.033 (4)0.014 (3)0.004 (3)0.000 (3)0.001 (3)
C240.025 (4)0.029 (4)0.023 (4)0.002 (3)0.002 (3)0.006 (3)
C250.016 (3)0.035 (4)0.024 (4)0.007 (3)0.001 (3)0.006 (3)
C260.031 (4)0.030 (4)0.019 (4)0.004 (3)0.007 (3)0.002 (3)
C270.027 (4)0.027 (4)0.029 (4)0.003 (3)0.014 (3)0.009 (3)
C280.019 (3)0.044 (4)0.014 (3)0.003 (3)0.003 (3)0.009 (3)
C290.026 (4)0.040 (4)0.021 (4)0.004 (3)0.007 (3)0.000 (3)
C1110.023 (3)0.021 (3)0.013 (3)0.003 (3)0.004 (3)0.001 (3)
C1120.061 (5)0.019 (4)0.028 (4)0.007 (3)0.014 (4)0.006 (3)
C1130.033 (4)0.034 (4)0.026 (4)0.012 (3)0.003 (3)0.003 (3)
C2110.027 (4)0.021 (3)0.018 (3)0.005 (3)0.002 (3)0.000 (3)
C2120.035 (4)0.022 (4)0.031 (4)0.005 (3)0.001 (3)0.001 (3)
C2130.037 (4)0.021 (4)0.034 (4)0.003 (3)0.003 (4)0.001 (3)
Geometric parameters (Å, º) top
Pd1—N12.182 (5)C15—C161.407 (11)
Pd1—Cl12.3585 (17)C15—C191.414 (11)
Pd1—Se22.3898 (8)C15—H150.9500
Pd1—Se12.4051 (9)C16—C171.405 (11)
Pd2—N22.152 (5)C16—H160.9500
Pd2—Cl22.3540 (17)C17—C181.427 (11)
Pd2—Se22.3716 (8)C17—H170.9500
Pd2—Se12.4166 (8)C18—C191.426 (12)
Se1—C211.904 (6)C18—H180.9500
Se2—C111.904 (6)C19—H190.9500
N1—C1121.475 (9)C20—C241.431 (10)
N1—C1131.483 (9)C20—C211.442 (9)
N1—C1111.500 (8)C20—C2111.497 (9)
N2—C2121.470 (9)C21—C221.417 (9)
N2—C2111.488 (8)C22—C231.431 (9)
N2—C2131.499 (9)C22—H220.9500
Fe1—C112.022 (6)C23—C241.419 (10)
Fe1—C172.029 (7)C23—H230.9500
Fe1—C182.031 (7)C24—H240.9500
Fe1—C122.039 (7)C25—C291.421 (10)
Fe1—C162.042 (7)C25—C261.431 (10)
Fe1—C152.050 (7)C25—H250.9500
Fe1—C132.049 (7)C26—C271.432 (10)
Fe1—C102.055 (6)C26—H260.9500
Fe1—C192.056 (7)C27—C281.409 (10)
Fe1—C142.072 (7)C27—H270.9500
Fe2—C202.042 (6)C28—C291.422 (10)
Fe2—C212.043 (6)C28—H280.9500
Fe2—C242.042 (7)C29—H290.9500
Fe2—C282.043 (7)C111—H11A0.9900
Fe2—C252.046 (7)C111—H11B0.9900
Fe2—C232.046 (7)C112—H11C0.9800
Fe2—C272.052 (7)C112—H11D0.9800
Fe2—C262.053 (7)C112—H11E0.9800
Fe2—C292.054 (7)C113—H11F0.9800
Fe2—C222.056 (6)C113—H11G0.9800
C10—C111.436 (9)C113—H11H0.9800
C10—C141.443 (9)C211—H21A0.9900
C10—C1111.494 (9)C211—H21B0.9900
C11—C121.415 (9)C212—H21C0.9800
C12—C131.404 (10)C212—H21D0.9800
C12—H120.9500C212—H21E0.9800
C13—C141.420 (10)C213—H21F0.9800
C13—H130.9500C213—H21G0.9800
C14—H140.9500C213—H21H0.9800
N1—Pd1—Cl192.99 (15)C12—C13—C14110.0 (6)
N1—Pd1—Se293.62 (14)C12—C13—Fe169.5 (4)
Cl1—Pd1—Se2173.39 (5)C14—C13—Fe170.7 (4)
N1—Pd1—Se1172.87 (15)C12—C13—H13125.0
Cl1—Pd1—Se193.59 (5)C14—C13—H13125.0
Se2—Pd1—Se179.80 (3)Fe1—C13—H13126.4
N2—Pd2—Cl292.05 (15)C13—C14—C10106.7 (6)
N2—Pd2—Se2175.53 (15)C13—C14—Fe169.0 (4)
Cl2—Pd2—Se291.22 (5)C10—C14—Fe168.9 (4)
N2—Pd2—Se196.84 (14)C13—C14—H14126.7
Cl2—Pd2—Se1171.10 (5)C10—C14—H14126.7
Se2—Pd2—Se179.92 (3)Fe1—C14—H14127.0
C21—Se1—Pd1109.23 (19)C16—C15—C19108.7 (7)
C21—Se1—Pd295.12 (19)C16—C15—Fe169.6 (4)
Pd1—Se1—Pd294.58 (3)C19—C15—Fe170.1 (4)
C11—Se2—Pd2105.90 (18)C16—C15—H15125.7
C11—Se2—Pd192.08 (19)C19—C15—H15125.7
Pd2—Se2—Pd196.17 (3)Fe1—C15—H15126.2
C112—N1—C113109.7 (6)C17—C16—C15108.6 (7)
C112—N1—C111108.0 (5)C17—C16—Fe169.3 (4)
C113—N1—C111108.3 (5)C15—C16—Fe170.2 (4)
C112—N1—Pd1106.7 (4)C17—C16—H16125.7
C113—N1—Pd1109.3 (4)C15—C16—H16125.7
C111—N1—Pd1114.8 (4)Fe1—C16—H16126.4
C212—N2—C211109.4 (5)C16—C17—C18107.5 (7)
C212—N2—C213108.4 (5)C16—C17—Fe170.3 (4)
C211—N2—C213106.8 (5)C18—C17—Fe169.5 (4)
C212—N2—Pd2107.3 (4)C16—C17—H17126.2
C211—N2—Pd2114.3 (4)C18—C17—H17126.2
C213—N2—Pd2110.4 (4)Fe1—C17—H17125.5
C11—Fe1—C17122.5 (3)C17—C18—C19108.1 (7)
C11—Fe1—C18160.0 (3)C17—C18—Fe169.3 (4)
C17—Fe1—C1841.1 (3)C19—C18—Fe170.5 (4)
C11—Fe1—C1240.8 (2)C17—C18—H18126.0
C17—Fe1—C12104.1 (3)C19—C18—H18126.0
C18—Fe1—C12123.1 (3)Fe1—C18—H18125.7
C11—Fe1—C16106.5 (3)C15—C19—C18107.1 (7)
C17—Fe1—C1640.4 (3)C15—C19—Fe169.6 (4)
C18—Fe1—C1668.2 (3)C18—C19—Fe168.6 (4)
C12—Fe1—C16118.0 (3)C15—C19—H19126.4
C11—Fe1—C15121.2 (3)C18—C19—H19126.4
C17—Fe1—C1568.1 (3)Fe1—C19—H19126.9
C18—Fe1—C1568.1 (3)C24—C20—C21105.9 (6)
C12—Fe1—C15154.1 (3)C24—C20—C211129.6 (6)
C16—Fe1—C1540.2 (3)C21—C20—C211124.4 (6)
C11—Fe1—C1367.9 (3)C24—C20—Fe269.5 (4)
C17—Fe1—C13118.4 (3)C21—C20—Fe269.3 (3)
C18—Fe1—C13107.4 (3)C211—C20—Fe2127.9 (4)
C12—Fe1—C1340.2 (3)C22—C21—C20109.4 (6)
C16—Fe1—C13152.7 (3)C22—C21—Se1132.1 (5)
C15—Fe1—C13165.3 (3)C20—C21—Se1118.5 (5)
C11—Fe1—C1041.2 (2)C22—C21—Fe270.3 (4)
C17—Fe1—C10161.4 (3)C20—C21—Fe269.3 (3)
C18—Fe1—C10157.0 (3)Se1—C21—Fe2126.7 (3)
C12—Fe1—C1068.9 (3)C21—C22—C23107.4 (6)
C16—Fe1—C10126.4 (3)C21—C22—Fe269.3 (4)
C15—Fe1—C10110.3 (3)C23—C22—Fe269.2 (4)
C13—Fe1—C1068.1 (3)C21—C22—H22126.3
C11—Fe1—C19157.0 (3)C23—C22—H22126.3
C17—Fe1—C1968.8 (3)Fe2—C22—H22126.8
C18—Fe1—C1940.8 (3)C24—C23—C22108.0 (6)
C12—Fe1—C19161.9 (3)C24—C23—Fe269.5 (4)
C16—Fe1—C1968.0 (3)C22—C23—Fe270.0 (4)
C15—Fe1—C1940.3 (3)C24—C23—H23126.0
C13—Fe1—C19127.3 (3)C22—C23—H23126.0
C10—Fe1—C19122.8 (3)Fe2—C23—H23126.1
C11—Fe1—C1468.9 (2)C23—C24—C20109.2 (6)
C17—Fe1—C14154.2 (3)C23—C24—Fe269.8 (4)
C18—Fe1—C14121.0 (3)C20—C24—Fe269.5 (4)
C12—Fe1—C1468.5 (3)C23—C24—H24125.4
C16—Fe1—C14165.0 (3)C20—C24—H24125.4
C15—Fe1—C14128.9 (3)Fe2—C24—H24126.9
C13—Fe1—C1440.3 (3)C29—C25—C26108.9 (6)
C10—Fe1—C1440.9 (3)C29—C25—Fe270.0 (4)
C19—Fe1—C14110.3 (3)C26—C25—Fe269.8 (4)
C20—Fe2—C2141.3 (2)C29—C25—H25125.5
C20—Fe2—C2441.0 (3)C26—C25—H25125.5
C21—Fe2—C2468.3 (3)Fe2—C25—H25126.2
C20—Fe2—C28157.6 (3)C27—C26—C25106.7 (6)
C21—Fe2—C28159.1 (3)C27—C26—Fe269.6 (4)
C24—Fe2—C28121.4 (3)C25—C26—Fe269.3 (4)
C20—Fe2—C25107.8 (3)C27—C26—H26126.7
C21—Fe2—C25124.4 (3)C25—C26—H26126.7
C24—Fe2—C25123.3 (3)Fe2—C26—H26126.1
C28—Fe2—C2568.0 (3)C28—C27—C26108.4 (6)
C20—Fe2—C2369.3 (3)C28—C27—Fe269.5 (4)
C21—Fe2—C2368.3 (3)C26—C27—Fe269.6 (4)
C24—Fe2—C2340.6 (3)C28—C27—H27125.8
C28—Fe2—C23106.1 (3)C26—C27—H27125.8
C25—Fe2—C23158.5 (3)Fe2—C27—H27126.6
C20—Fe2—C27160.7 (3)C27—C28—C29108.9 (6)
C21—Fe2—C27124.2 (3)C27—C28—Fe270.2 (4)
C24—Fe2—C27157.1 (3)C29—C28—Fe270.1 (4)
C28—Fe2—C2740.3 (3)C27—C28—H28125.5
C25—Fe2—C2768.2 (3)C29—C28—H28125.5
C23—Fe2—C27121.6 (3)Fe2—C28—H28125.7
C20—Fe2—C26123.8 (3)C25—C29—C28107.1 (6)
C21—Fe2—C26108.8 (3)C25—C29—Fe269.4 (4)
C24—Fe2—C26160.2 (3)C28—C29—Fe269.3 (4)
C28—Fe2—C2668.4 (3)C25—C29—H29126.4
C25—Fe2—C2640.9 (3)C28—C29—H29126.4
C23—Fe2—C26158.3 (3)Fe2—C29—H29126.4
C27—Fe2—C2640.8 (3)C10—C111—N1111.8 (5)
C20—Fe2—C29121.8 (3)C10—C111—H11A109.3
C21—Fe2—C29159.5 (3)N1—C111—H11A109.3
C24—Fe2—C29106.6 (3)C10—C111—H11B109.3
C28—Fe2—C2940.6 (3)N1—C111—H11B109.3
C25—Fe2—C2940.6 (3)H11A—C111—H11B107.9
C23—Fe2—C29121.6 (3)N1—C112—H11C109.5
C27—Fe2—C2968.2 (3)N1—C112—H11D109.5
C26—Fe2—C2968.8 (3)H11C—C112—H11D109.5
C20—Fe2—C2269.4 (3)N1—C112—H11E109.5
C21—Fe2—C2240.5 (2)H11C—C112—H11E109.5
C24—Fe2—C2268.5 (3)H11D—C112—H11E109.5
C28—Fe2—C22122.3 (3)N1—C113—H11F109.5
C25—Fe2—C22159.8 (3)N1—C113—H11G109.5
C23—Fe2—C2240.8 (3)H11F—C113—H11G109.5
C27—Fe2—C22107.5 (3)N1—C113—H11H109.5
C26—Fe2—C22123.0 (3)H11F—C113—H11H109.5
C29—Fe2—C22158.1 (3)H11G—C113—H11H109.5
C11—C10—C14107.1 (6)N2—C211—C20111.3 (5)
C11—C10—C111121.9 (6)N2—C211—H21A109.4
C14—C10—C111130.9 (6)C20—C211—H21A109.4
C11—C10—Fe168.2 (4)N2—C211—H21B109.4
C14—C10—Fe170.2 (4)C20—C211—H21B109.4
C111—C10—Fe1129.7 (5)H21A—C211—H21B108.0
C12—C11—C10108.7 (6)N2—C212—H21C109.5
C12—C11—Se2133.6 (5)N2—C212—H21D109.5
C10—C11—Se2117.8 (4)H21C—C212—H21D109.5
C12—C11—Fe170.2 (4)N2—C212—H21E109.5
C10—C11—Fe170.6 (4)H21C—C212—H21E109.5
Se2—C11—Fe1124.4 (3)H21D—C212—H21E109.5
C13—C12—C11107.5 (6)N2—C213—H21F109.5
C13—C12—Fe170.3 (4)N2—C213—H21G109.5
C11—C12—Fe169.0 (4)H21F—C213—H21G109.5
C13—C12—H12126.3N2—C213—H21H109.5
C11—C12—H12126.3H21F—C213—H21H109.5
Fe1—C12—H12126.0H21G—C213—H21H109.5
C14—C10—C11—C120.6 (7)C24—C20—C21—Fe260.2 (4)
C111—C10—C11—C12175.7 (6)C211—C20—C21—Fe2122.5 (6)
Fe1—C10—C11—C1260.2 (4)C20—C21—C22—C230.5 (7)
C14—C10—C11—Se2179.1 (4)Se1—C21—C22—C23179.0 (5)
C111—C10—C11—Se24.6 (8)Fe2—C21—C22—C2358.9 (4)
Fe1—C10—C11—Se2119.5 (4)C20—C21—C22—Fe258.4 (4)
C14—C10—C11—Fe159.6 (4)Se1—C21—C22—Fe2122.1 (5)
C111—C10—C11—Fe1124.1 (6)C21—C22—C23—C240.4 (7)
C10—C11—C12—C130.4 (7)Fe2—C22—C23—C2459.3 (4)
Se2—C11—C12—C13179.2 (5)C21—C22—C23—Fe259.0 (4)
Fe1—C11—C12—C1360.0 (5)C22—C23—C24—C201.2 (7)
C10—C11—C12—Fe160.4 (4)Fe2—C23—C24—C2058.4 (5)
Se2—C11—C12—Fe1119.2 (6)C22—C23—C24—Fe259.6 (4)
C11—C12—C13—C140.1 (8)C21—C20—C24—C231.5 (7)
Fe1—C12—C13—C1459.3 (5)C211—C20—C24—C23178.5 (6)
C11—C12—C13—Fe159.2 (4)Fe2—C20—C24—C2358.6 (5)
C12—C13—C14—C100.3 (8)C21—C20—C24—Fe260.1 (4)
Fe1—C13—C14—C1058.8 (4)C211—C20—C24—Fe2122.8 (7)
C12—C13—C14—Fe158.5 (5)C29—C25—C26—C270.5 (8)
C11—C10—C14—C130.5 (7)Fe2—C25—C26—C2759.8 (5)
C111—C10—C14—C13175.3 (6)C29—C25—C26—Fe259.3 (5)
Fe1—C10—C14—C1358.9 (5)C25—C26—C27—C280.7 (7)
C11—C10—C14—Fe158.3 (4)Fe2—C26—C27—C2858.9 (5)
C111—C10—C14—Fe1125.8 (7)C25—C26—C27—Fe259.6 (5)
C19—C15—C16—C170.5 (8)C26—C27—C28—C290.7 (8)
Fe1—C15—C16—C1758.8 (5)Fe2—C27—C28—C2959.6 (5)
C19—C15—C16—Fe159.4 (5)C26—C27—C28—Fe259.0 (5)
C15—C16—C17—C180.4 (8)C26—C25—C29—C280.1 (8)
Fe1—C16—C17—C1859.8 (5)Fe2—C25—C29—C2859.3 (5)
C15—C16—C17—Fe159.4 (5)C26—C25—C29—Fe259.2 (5)
C16—C17—C18—C190.1 (8)C27—C28—C29—C250.3 (8)
Fe1—C17—C18—C1960.2 (5)Fe2—C28—C29—C2559.4 (5)
C16—C17—C18—Fe160.3 (5)C27—C28—C29—Fe259.7 (5)
C16—C15—C19—C180.5 (8)C11—C10—C111—N169.5 (8)
Fe1—C15—C19—C1858.6 (5)C14—C10—C111—N1105.8 (8)
C16—C15—C19—Fe159.1 (5)Fe1—C10—C111—N1156.5 (5)
C17—C18—C19—C150.2 (8)C112—N1—C111—C10174.3 (6)
Fe1—C18—C19—C1559.2 (5)C113—N1—C111—C1067.0 (7)
C17—C18—C19—Fe159.4 (5)Pd1—N1—C111—C1055.5 (6)
C24—C20—C21—C221.2 (7)C212—N2—C211—C2059.8 (7)
C211—C20—C21—C22178.5 (6)C213—N2—C211—C20177.0 (5)
Fe2—C20—C21—C2259.0 (4)Pd2—N2—C211—C2060.7 (6)
C24—C20—C21—Se1178.4 (4)C24—C20—C211—N2105.3 (7)
C211—C20—C21—Se11.1 (8)C21—C20—C211—N271.2 (8)
Fe2—C20—C21—Se1121.4 (4)Fe2—C20—C211—N2160.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C113—H11F···Cl10.982.703.347 (8)124
C212—H21D···Cl20.982.753.394 (8)124
C213—H21H···Cl20.982.743.384 (8)124
C22—H22···Cl10.952.823.537 (7)133
Selected geometric parameters (Å, º) top
Pd1—N12.182 (5)Pd2—N22.152 (5)
Pd1—Cl12.3585 (17)Pd2—Cl22.3540 (17)
Pd1—Se22.3898 (8)Pd2—Se22.3716 (8)
Pd1—Se12.4051 (9)Pd2—Se12.4166 (8)
N1—Pd1—Cl192.99 (15)N2—Pd2—Cl292.05 (15)
N1—Pd1—Se293.62 (14)N2—Pd2—Se2175.53 (15)
Cl1—Pd1—Se2173.39 (5)Cl2—Pd2—Se291.22 (5)
N1—Pd1—Se1172.87 (15)N2—Pd2—Se196.84 (14)
Cl1—Pd1—Se193.59 (5)Cl2—Pd2—Se1171.10 (5)
Se2—Pd1—Se179.80 (3)Se2—Pd2—Se179.92 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C113—H11F···Cl10.982.703.347 (8)124
C212—H21D···Cl20.982.753.394 (8)124
C213—H21H···Cl20.982.743.384 (8)124
C22—H22···Cl10.952.823.537 (7)133
 

Acknowledgements

Financial support from the Jenni and Antti Wihuri Foundation (EMT) and from the Academy of Finland is gratefully acknowledged.

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Volume 70| Part 10| October 2014| Pages m343-m344
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