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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 9| September 2012| Page m1145
doi:10.1107/S1600536812033958

Bis(di-2-pyridyl­amine-κ2N2,N2′)palladium(II) bis­­(thio­cyanate)

Kwang Haa*

aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea
*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 28 July 2012; accepted 30 July 2012; online 4 August 2012)

The PdII atom of the title salt, [Pd(C10H9N3)2](NCS)2, lies on a center of inversion and exists in a square-planar environment defined by the four pyridine N atoms derived from the two chelating di-2-pyridyl­amine (dpa) ligands. The chelate ring displays a boat conformation with a dihedral angle between the pyridine rings of 43.0 (1)°. Adjacent thio­cyanate ions are linked to the cations by N—H⋯N hydrogen bonds.

Related literature

For the crystal structures of the related cationic PdII and PtII complexes, [Pd(dpa)2](X)2 (X = Cl, PF6 or NO3) and [Pt(dpa)2]Br2·H2O, see: Živković et al. (2007[Živković, M. D., Rajković, S., Rychlewska, U., Warżajtis, B. & Djuran, M. (2007). Polyhedron, 26, 1541-1549.]); Antonioli et al. (2008[Antonioli, B., Bray, D. J., Clegg, J. K., Gloe, K., Gloe, K., Jäger, A., Jolliffe, K. A., Kataeva, O., Lindoy, L. F., Steel, P. J., Sumby, C. J. & Wenzel, M. (2008). Polyhedron, 27, 2889-2898.]); Ha (2012a[Ha, K. (2012a). Acta Cryst. E68, m501.],b[Ha, K. (2012b). Acta Cryst. E68, m518.]).

[Scheme 1]

Experimental

Crystal data

  • [Pd(C10H9N3)2](NCS)2

  • Mr = 564.96

  • Monoclinic, P 21 /c

  • a = 7.7353 (9) Å

  • b = 17.478 (2) Å

  • c = 8.3822 (10) Å

  • β = 102.137 (2)°

  • V = 1107.9 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.06 mm−1

  • T = 200 K

  • 0.16 × 0.09 × 0.09 mm
Data collection

  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.876, Tmax = 1.000

  • 6810 measured reflections

  • 2172 independent reflections

  • 1552 reflections with I > 2σ(I)

  • Rint = 0.046
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.088

  • S = 1.07

  • 2172 reflections

  • 151 parameters

  • H-atom parameters constrained

  • Δρmax = 1.10 e Å−3

  • Δρmin = −0.61 e Å−3

Table 1
Selected bond lengths (Å)

Pd1—N3 2.021 (3)
Pd1—N1 2.032 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2N⋯N4i 0.92 1.94 2.846 (5) 170
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812033958/ng5285sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033958/ng5285Isup2.hkl

checkCIF report


Comment top

Crystal structures of the related cationic PdII and PtII complexes, such as [Pd(dpa)2](X)2 (dpa = di-2-pyridylamine, C10H9N3; X = Cl, PF6 or NO3) (Živković et al., 2007; Antonioli et al., 2008; Ha, 2012a) and [Pt(dpa)2]Br2.H2O (Ha, 2012b), have been investigated previously.

The asymmetric unit of the title compound, [Pd(dpa)2](SCN)2, contains one half of a cationic PdII complex and one SCN- anion (Fig. 1). In the complex, the PdII ion is four-coordinated in a distorted square-planar environment by the four pyridine N atoms derived from the two chelating dpa ligands. The PdII ion is located on an inversion centre, and thus the PdN4 unit is exactly planar. The dpa ligands display a boat conformation with a dihedral angle between the least-squares planes of the two pyridine rings of 43.0 (1)°. The nearly planar pyridine rings [maximum deviation = 0.039 (2) Å] are considerably inclined to the PdN4 unit, making dihedral angles of 40.1 (2)° and 42.5 (1)°. The two Pd—N bond lengths are nearly equivalent [Pd—N: 2.021 (3) and 2.032 (3) Å] (Table 1). The SCN- anion is almost linear (Table 1), and two anions are linked to the cationic complex by intermolecular N—H···N hydrogen bonds between the N atom of the anions and the N—H group of the cation (Fig. 2 and Table 2). The complex molecules are stacked into columns along the a axis. In the columns, several intermolecular π-π interactions between the pyridine rings are present, the shortest ring centroid-centroid distance being 3.436 (2) Å.

Related literature top

For the crystal structures of the related cationic PdII and PtII complexes, [Pd(dpa)2](X)2 (X = Cl, PF6 or NO3) and [Pt(dpa)2]Br2.H2O, see: Živković et al. (2007); Antonioli et al. (2008); Ha (2012a,b).

Experimental top

The title complex was obtained as a byproduct from the reaction of Na2PdCl4 (0.1462 g, 0.497 mmol) with KSCN (0.4688 g, 4.824 mmol) and di-2-pyridylamine (0.0877 g, 0.512 mmol) in MeOH (30 ml)/acetone (30 ml). After stirring of the reaction mixture for 24 h at room temperature, the formed precipitate was separated by filtration, washed with H2O and acetone, to give the main product as a pale red powder (0.1562 g). A small amount of the yellow byproduct was obtained from the mixture of filtrate and washing solution. Yellow crystals were obtained by slow evaporation from a CH3CN solution of the byproduct at room temperature.

Refinement top

Carbon-bound H atoms were positioned geometrically and allowed to ride on their respective parent atoms: C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). Nitrogen-bound H atom was located from the difference Fourier map then allowed to ride on its parent atom in the final cycles of refinement with N—H = 0.92 Å and Uiso(H) = 1.5Ueq(N). The highest peak (1.10 e Å-3) and the deepest hole (-0.61 e Å-3) in the difference Fourier map are located 0.85 Å and 1.48 Å, respectively, from the atoms C1 and H1.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A structure detail of the title compound, with displacement ellipsoids drawn at the 50% probability level for non-H atoms. Unlabelled atoms are generated by the application of the inversion centre.
[Figure 2] Fig. 2. A view of the unit-cell contents of the title compound. Intermolecular N—H···N hydrogen-bond interactions are drawn with dashed lines.
Bis(di-2-pyridylamine-κ2N2,N2')palladium(II) bis(thiocyanate) top
Crystal data top
[Pd(C10H9N3)2](NCS)2F(000) = 568
Mr = 564.96Dx = 1.694 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2711 reflections
a = 7.7353 (9) Åθ = 2.3–25.9°
b = 17.478 (2) ŵ = 1.06 mm−1
c = 8.3822 (10) ÅT = 200 K
β = 102.137 (2)°Block, yellow
V = 1107.9 (2) Å30.16 × 0.09 × 0.09 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD
diffractometer		2172 independent reflections
Radiation source: fine-focus sealed tube1552 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ϕ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −9→6
Tmin = 0.876, Tmax = 1.000k = −21→20
6810 measured reflectionsl = −10→10
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0333P)2 + 0.3195P]
where P = (Fo2 + 2Fc2)/3
2172 reflections(Δ/σ)max < 0.001
151 parametersΔρmax = 1.10 e Å−3
0 restraintsΔρmin = −0.61 e Å−3
Crystal data top
[Pd(C10H9N3)2](NCS)2V = 1107.9 (2) Å3
Mr = 564.96Z = 2
Monoclinic, P21/cMo Kα radiation
a = 7.7353 (9) ŵ = 1.06 mm−1
b = 17.478 (2) ÅT = 200 K
c = 8.3822 (10) Å0.16 × 0.09 × 0.09 mm
β = 102.137 (2)°
Data collection top
Bruker SMART 1000 CCD
diffractometer		2172 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1552 reflections with I > 2σ(I)
Tmin = 0.876, Tmax = 1.000Rint = 0.046
6810 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.07Δρmax = 1.10 e Å−3
2172 reflectionsΔρmin = −0.61 e Å−3
151 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
xyzUiso*/Ueq
Pd10.50000.00000.50000.02072 (15)
N10.6536 (4)0.08760 (17)0.6087 (4)0.0216 (7)
N20.4264 (4)0.12533 (17)0.7419 (4)0.0240 (8)
H2N0.38030.16690.78590.036*
N30.4123 (4)−0.00805 (17)0.7101 (4)0.0199 (7)
C10.8191 (5)0.0992 (2)0.5843 (5)0.0274 (9)
H10.86880.06160.52530.033*
C20.9181 (5)0.1620 (2)0.6399 (5)0.0319 (10)
H21.03390.16810.62040.038*
C30.8453 (6)0.2168 (2)0.7258 (5)0.0329 (11)
H30.90970.26190.76330.039*
C40.6808 (5)0.2056 (2)0.7562 (5)0.0283 (10)
H40.63030.24270.81550.034*
C50.5868 (5)0.1392 (2)0.6995 (4)0.0223 (9)
C60.3700 (5)0.0553 (2)0.7841 (4)0.0207 (9)
C70.2737 (5)0.0502 (2)0.9079 (5)0.0283 (10)
H70.23710.09540.95450.034*
C80.2331 (5)−0.0194 (2)0.9605 (5)0.0303 (11)
H80.1663−0.02341.04320.036*
C90.2900 (5)−0.0854 (2)0.8927 (5)0.0293 (10)
H90.2673−0.13460.93150.035*
C100.3784 (5)−0.0773 (2)0.7701 (5)0.0247 (9)
H100.4184−0.12200.72440.030*
S10.15609 (16)0.10410 (7)0.31675 (16)0.0421 (3)
N40.3250 (5)0.2438 (2)0.4024 (5)0.0511 (11)
C110.2561 (6)0.1855 (3)0.3654 (5)0.0326 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0234 (3)0.0179 (2)0.0213 (2)−0.00227 (18)0.00572 (16)−0.00236 (19)
N10.0248 (19)0.0182 (18)0.0214 (18)−0.0019 (13)0.0037 (14)−0.0016 (14)
N20.0285 (19)0.0178 (18)0.0275 (19)0.0043 (14)0.0099 (15)−0.0034 (14)
N30.0189 (17)0.0213 (18)0.0186 (16)−0.0031 (13)0.0023 (13)−0.0019 (14)
C10.019 (2)0.025 (2)0.040 (3)0.0017 (17)0.0094 (18)0.0015 (19)
C20.024 (2)0.040 (3)0.031 (2)−0.0078 (19)0.0037 (19)0.003 (2)
C30.038 (3)0.023 (2)0.034 (3)−0.0071 (19)−0.001 (2)0.0007 (19)
C40.035 (3)0.019 (2)0.029 (2)−0.0023 (17)0.0043 (19)−0.0002 (18)
C50.024 (2)0.021 (2)0.019 (2)0.0034 (16)−0.0014 (16)0.0011 (17)
C60.019 (2)0.024 (2)0.017 (2)0.0009 (16)0.0000 (16)−0.0010 (17)
C70.025 (2)0.034 (3)0.026 (2)0.0012 (18)0.0031 (18)−0.0058 (19)
C80.021 (2)0.049 (3)0.022 (2)−0.0057 (18)0.0057 (17)0.0035 (19)
C90.028 (2)0.030 (2)0.026 (2)−0.0100 (18)−0.0002 (18)0.0047 (19)
C100.025 (2)0.024 (2)0.024 (2)−0.0045 (17)0.0036 (18)0.0033 (18)
S10.0391 (7)0.0371 (7)0.0512 (8)0.0015 (5)0.0122 (6)−0.0057 (6)
N40.053 (3)0.041 (3)0.060 (3)−0.011 (2)0.013 (2)0.018 (2)
C110.029 (3)0.039 (3)0.031 (3)0.008 (2)0.010 (2)0.013 (2)
Geometric parameters (Å, º) top
Pd1—N32.021 (3)C3—C41.363 (5)
Pd1—N3i2.021 (3)C3—H30.9500
Pd1—N12.032 (3)C4—C51.399 (5)
Pd1—N1i2.032 (3)C4—H40.9500
N1—C51.350 (5)C6—C71.402 (5)
N1—C11.354 (5)C7—C81.355 (6)
N2—C61.371 (5)C7—H70.9500
N2—C51.382 (5)C8—C91.396 (6)
N2—H2N0.9200C8—H80.9500
N3—C61.342 (5)C9—C101.356 (5)
N3—C101.358 (5)C9—H90.9500
C1—C21.364 (5)C10—H100.9500
C1—H10.9500S1—C111.630 (5)
C2—C31.387 (6)N4—C111.161 (5)
C2—H20.9500
N3—Pd1—N3i180.0C2—C3—H3120.2
N3—Pd1—N186.18 (12)C3—C4—C5119.6 (4)
N3i—Pd1—N193.82 (12)C3—C4—H4120.2
N3—Pd1—N1i93.82 (12)C5—C4—H4120.2
N3i—Pd1—N1i86.18 (12)N1—C5—N2119.9 (3)
N1—Pd1—N1i180.00 (11)N1—C5—C4120.8 (4)
C5—N1—C1118.1 (3)N2—C5—C4119.2 (3)
C5—N1—Pd1119.9 (3)N3—C6—N2119.7 (3)
C1—N1—Pd1121.8 (3)N3—C6—C7120.6 (4)
C6—N2—C5125.0 (3)N2—C6—C7119.6 (4)
C6—N2—H2N115.5C8—C7—C6119.6 (4)
C5—N2—H2N114.2C8—C7—H7120.2
C6—N3—C10118.6 (3)C6—C7—H7120.2
C6—N3—Pd1120.3 (2)C7—C8—C9119.6 (4)
C10—N3—Pd1120.8 (3)C7—C8—H8120.2
N1—C1—C2123.3 (4)C9—C8—H8120.2
N1—C1—H1118.3C10—C9—C8118.4 (4)
C2—C1—H1118.3C10—C9—H9120.8
C1—C2—C3118.2 (4)C8—C9—H9120.8
C1—C2—H2120.9C9—C10—N3122.7 (4)
C3—C2—H2120.9C9—C10—H10118.6
C4—C3—C2119.7 (4)N3—C10—H10118.6
C4—C3—H3120.2N4—C11—S1178.6 (4)
N3—Pd1—N1—C5−41.3 (3)C6—N2—C5—N138.3 (5)
N3i—Pd1—N1—C5138.7 (3)C6—N2—C5—C4−139.6 (4)
N3—Pd1—N1—C1143.2 (3)C3—C4—C5—N1−3.0 (6)
N3i—Pd1—N1—C1−36.8 (3)C3—C4—C5—N2174.9 (3)
N1—Pd1—N3—C644.1 (3)C10—N3—C6—N2170.2 (3)
N1i—Pd1—N3—C6−135.9 (3)Pd1—N3—C6—N2−16.2 (4)
N1—Pd1—N3—C10−142.4 (3)C10—N3—C6—C7−7.7 (5)
N1i—Pd1—N3—C1037.6 (3)Pd1—N3—C6—C7165.9 (3)
C5—N1—C1—C2−3.3 (6)C5—N2—C6—N3−35.6 (5)
Pd1—N1—C1—C2172.3 (3)C5—N2—C6—C7142.3 (4)
N1—C1—C2—C30.0 (6)N3—C6—C7—C84.4 (5)
C1—C2—C3—C41.9 (6)N2—C6—C7—C8−173.5 (3)
C2—C3—C4—C5−0.4 (6)C6—C7—C8—C91.0 (6)
C1—N1—C5—N2−173.1 (3)C7—C8—C9—C10−2.8 (6)
Pd1—N1—C5—N211.2 (5)C8—C9—C10—N3−0.6 (6)
C1—N1—C5—C44.7 (5)C6—N3—C10—C95.9 (5)
Pd1—N1—C5—C4−170.9 (3)Pd1—N3—C10—C9−167.7 (3)
Symmetry code: (i) −x+1, −y, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···N4ii0.921.942.846 (5)170
Symmetry code: (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Pd(C10H9N3)2](NCS)2
Mr564.96
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)7.7353 (9), 17.478 (2), 8.3822 (10)
β (°) 102.137 (2)
V (Å3)1107.9 (2)
Z2
Radiation typeMo Kα
µ (mm−1)1.06
Crystal size (mm)0.16 × 0.09 × 0.09
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.876, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		6810, 2172, 1552
Rint0.046
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.088, 1.07
No. of reflections2172
No. of parameters151
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)1.10, −0.61

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Selected bond lengths (Å) top
Pd1—N32.021 (3)Pd1—N12.032 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2N···N4i0.921.942.846 (5)169.8
Symmetry code: (i) x, −y+1/2, z+1/2.
 

Acknowledgements

This work was supported by the Priority Research Centers Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (2011–0030747).

References

First citationAntonioli, B., Bray, D. J., Clegg, J. K., Gloe, K., Gloe, K., Jäger, A., Jolliffe, K. A., Kataeva, O., Lindoy, L. F., Steel, P. J., Sumby, C. J. & Wenzel, M. (2008). Polyhedron, 27, 2889–2898.  Web of Science CSD CrossRef CAS Google Scholar
 First citationBruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationHa, K. (2012a). Acta Cryst. E68, m501.  CSD CrossRef IUCr Journals Google Scholar
 First citationHa, K. (2012b). Acta Cryst. E68, m518.  CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationŽivković, M. D., Rajković, S., Rychlewska, U., Warżajtis, B. & Djuran, M. (2007). Polyhedron, 26, 1541–1549.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 9| September 2012| Page m1145
doi:10.1107/S1600536812033958
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