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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 66| Part 1| January 2010| Page m38
doi:10.1107/S1600536809052313

Di­chlorido(1,10-phenanthroline-κ2N,N′)palladium(II)

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 1 December 2009; accepted 5 December 2009; online 12 December 2009)

In the title complex, [PdCl2(C12H8N2)], the Pd2+ ion is four-coordinated in a slightly distorted square-planar environment by two N atoms of the chelating 1,10-phenanthroline ligand and two chloride ions. The nearly planar mol­ecules, with a maximum deviation of 0.120 (3) Å from the least-squares plane, are stacked in columns along the c axis with a Pd⋯Pd distance of 4.8340 (9) Å. In the column, π–π inter­actions between adjacent six-membered rings are present, the shortest centroid–centroid distance being 3.680 (4) Å. A weak C—H⋯Cl inter­action is observed between the columns.

Related literature

For the syntheses of [PdX2(phen)] (phen = 1,10-phenanthroline; X = Cl, Br, I or SCN), see: Cheng et al. (1977[Cheng, C. P., Plankey, B., Rund, J. V. & Brown, T. L. (1977). J. Am. Chem. Soc. 99, 8413-8417.]). For the crystal structure of yellow [PtCl2(phen)] which is isotypic to the title complex, see: Grzesiak & Matzger (2007[Grzesiak, A. L. & Matzger, A. J. (2007). Inorg. Chem. 46, 453-457.]). For the crystal structures of related Pd–bipy complexes, [PdX2(bipy)] (bipy = 2,2′-bipyridine; X = Cl, Br or I), see: Maekawa et al. (1991[Maekawa, M., Munakata, M., Kitagawa, S. & Nakamura, M. (1991). Anal. Sci. 7, 521-522.]); Smeets et al. (1997[Smeets, W. J. J., Spek, A. L., Hoare, J. L., Canty, A. J., Hovestad, N. & van Koten, G. (1997). Acta Cryst. C53, 1045-1047.]); Ha (2009[Ha, K. (2009). Acta Cryst. E65, m1588.]).

[Scheme 1]

Experimental

Crystal data

  • [PdCl2(C12H8N2)]

  • Mr = 357.50

  • Monoclinic, P 21 /c

  • a = 9.6170 (8) Å

  • b = 17.1402 (14) Å

  • c = 7.2529 (6) Å

  • β = 109.314 (2)°

  • V = 1128.26 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.09 mm−1

  • T = 200 K

  • 0.36 × 0.06 × 0.04 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 = 0.769, Tmax = 0.920

  • 8118 measured reflections

  • 2767 independent reflections

  • 1852 reflections with I > 2σ(I)

  • Rint = 0.060
Refinement

  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.169

  • S = 1.10

  • 2767 reflections

  • 154 parameters

  • H-atom parameters constrained

  • Δρmax = 2.90 e Å−3

  • Δρmin = −1.29 e Å−3

Table 1
Selected geometric parameters (Å, °)

Pd1—N2 2.035 (6)
Pd1—N1 2.036 (6)
Pd1—Cl2 2.283 (2)
Pd1—Cl1 2.2914 (19)
N2—Pd1—N1 81.5 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯Cl1i 0.95 2.80 3.733 (11) 169
Symmetry code: (i) [-x+1, 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/S1600536809052313/is2500sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052313/is2500Isup2.hkl

checkCIF report


Comment top

The title complex, [PdCl2(phen)] (where phen is 1,10-phenanthroline, C12H8N2), is isomorphous with the yellow form of [PtCl2(phen)], whereas the orange form of [PtCl2(phen)] crystallized in the orthorhombic space group Pca21 (Grzesiak & Matzger, 2007).

In the title complex, the Pd2+ ion is four-coordinated in a slightly distorted square-planar environment by two N atoms of the chelating 1,10-phenanthroline ligand and two chloride ions (Fig. 1). The main contribution to the distortion is the tight N1—Pd1—N2 chelate angle [81.5 (2)°], which results in non-linear trans arrangement [<N1—Pd1—Cl1 = 174.64 (17)° and <N2—Pd1—Cl2 = 175.11 (17)°]. The Pd1—N and Pd1—Cl bond lengths are almost equal, respectively [Pd1—N: 2.036 (6) and 2.035 (6) Å; Pd1—Cl 2.2914 (19) and 2.283 (2) Å]. The complex displays numerous intermolecular π-π interactions between adjacent six-membered rings, with a shortest centroid-centroid distance of 3.680 (4) Å and the dihedral angle between the ring planes is 5.6 (4)°. The nearly planar [PdCl2(phen)] molecules with a largest deviation of 0.120 (3) Å from the least-squares plane stack in columns along the c axis with a Pd···Pd distance of 4.8340 (9) Å (Fig. 2).

Related literature top

For the syntheses of [PdX2(phen)] (phen = 1,10-phenanthroline; X = Cl, Br, I or SCN), see: Cheng et al. (1977). For the crystal structure of yellow [PtCl2(phen)] which is isotypic to the title complex, see: Grzesiak & Matzger (2007). For the crystal structures of related Pd–bipy complexes, [PdX2(bipy)] (bipy = 2,2'-bipyridine; X = Cl, Br or I), see: Maekawa et al. (1991); Smeets et al. (1997); Ha (2009).

Experimental top

To a solution of Na2PdCl4 (0.5095 g, 1.732 mmol) in H2O (40 ml) was added 1,10-phenanthroline (0.3122 g, 1.732 mmol) and refluxed for 3 h. The precipitate obtained was separated by filtration, washed with water and acetone, and dried at 70 °C, to give a pale yellow powder (0.5259 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a dimethyl sulfoxide solution at 80 °C.

Refinement top

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)]. The highest peak and the deepest hole in the difference Fourier map are located 1.14 and 0.85 Å, respectively, from atom Pd1.

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. The structure of the title complex, with displacement ellipsoids drawn at the 50% probability level for non-H atoms.
[Figure 2] Fig. 2. Crystal packing diagram of the title complex.
Dichlorido(1,10-phenanthroline-κ2N,N')palladium(II) top
Crystal data top
[PdCl2(C12H8N2)]F(000) = 696
Mr = 357.50Dx = 2.105 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2653 reflections
a = 9.6170 (8) Åθ = 2.4–28.2°
b = 17.1402 (14) ŵ = 2.09 mm−1
c = 7.2529 (6) ÅT = 200 K
β = 109.314 (2)°Needle, yellow
V = 1128.26 (16) Å30.36 × 0.06 × 0.04 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD
diffractometer		2767 independent reflections
Radiation source: fine-focus sealed tube1852 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ϕ and ω scansθmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −12→12
Tmin = 0.769, Tmax = 0.920k = −22→19
8118 measured reflectionsl = −9→9
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.084P)2]
where P = (Fo2 + 2Fc2)/3
2767 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 2.90 e Å−3
0 restraintsΔρmin = −1.29 e Å−3
Crystal data top
[PdCl2(C12H8N2)]V = 1128.26 (16) Å3
Mr = 357.50Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.6170 (8) ŵ = 2.09 mm−1
b = 17.1402 (14) ÅT = 200 K
c = 7.2529 (6) Å0.36 × 0.06 × 0.04 mm
β = 109.314 (2)°
Data collection top
Bruker SMART 1000 CCD
diffractometer		2767 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		1852 reflections with I > 2σ(I)
Tmin = 0.769, Tmax = 0.920Rint = 0.060
8118 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 1.10Δρmax = 2.90 e Å−3
2767 reflectionsΔρmin = −1.29 e Å−3
154 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
Pd10.70739 (6)0.34324 (3)0.39119 (8)0.0214 (2)
Cl10.7453 (2)0.47533 (11)0.4189 (3)0.0313 (5)
Cl20.4658 (2)0.36052 (12)0.2078 (3)0.0366 (5)
N10.6941 (6)0.2247 (3)0.3805 (9)0.0235 (13)
N20.9182 (6)0.3184 (3)0.5594 (9)0.0211 (13)
C10.5819 (9)0.1794 (5)0.2838 (12)0.0319 (18)
H10.49310.20300.20360.038*
C20.5898 (10)0.0983 (5)0.2958 (13)0.039 (2)
H20.50730.06760.22440.046*
C30.7163 (9)0.0629 (4)0.4102 (12)0.033 (2)
H30.72140.00760.42020.040*
C40.8382 (9)0.1085 (4)0.5127 (11)0.0286 (17)
C50.9777 (10)0.0785 (4)0.6369 (12)0.0330 (19)
H50.99040.02380.65610.040*
C61.0895 (9)0.1263 (5)0.7254 (12)0.0318 (18)
H61.18050.10450.80440.038*
C71.0771 (8)0.2089 (4)0.7057 (11)0.0263 (16)
C81.1907 (8)0.2626 (5)0.7913 (12)0.0301 (17)
H81.28500.24450.87020.036*
C91.1660 (8)0.3405 (4)0.7613 (12)0.0287 (17)
H91.24230.37680.82100.034*
C101.0283 (8)0.3669 (4)0.6426 (11)0.0269 (16)
H101.01310.42130.62070.032*
C110.9420 (8)0.2407 (4)0.5896 (10)0.0234 (15)
C120.8212 (8)0.1902 (4)0.4927 (11)0.0224 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.0171 (3)0.0198 (3)0.0258 (3)−0.0001 (2)0.0050 (2)0.0001 (2)
Cl10.0285 (10)0.0198 (9)0.0422 (12)0.0034 (7)0.0070 (9)0.0016 (7)
Cl20.0178 (9)0.0379 (11)0.0457 (13)0.0017 (8)−0.0007 (8)0.0059 (9)
N10.022 (3)0.016 (3)0.031 (3)−0.003 (2)0.006 (3)−0.004 (2)
N20.018 (3)0.014 (3)0.030 (3)0.000 (2)0.006 (3)0.000 (2)
C10.026 (4)0.037 (4)0.031 (4)−0.005 (3)0.007 (4)−0.005 (3)
C20.040 (5)0.029 (5)0.048 (5)−0.017 (4)0.016 (4)−0.015 (4)
C30.043 (5)0.011 (4)0.053 (6)−0.005 (3)0.025 (5)−0.004 (3)
C40.038 (5)0.022 (4)0.030 (4)−0.005 (3)0.018 (4)0.000 (3)
C50.054 (6)0.021 (4)0.029 (4)0.005 (4)0.021 (4)0.006 (3)
C60.039 (5)0.026 (4)0.035 (5)0.013 (4)0.019 (4)0.008 (3)
C70.023 (4)0.026 (4)0.034 (4)0.011 (3)0.015 (3)0.007 (3)
C80.016 (4)0.039 (5)0.033 (5)0.003 (3)0.006 (3)0.005 (3)
C90.020 (4)0.032 (4)0.029 (4)−0.001 (3)0.001 (3)−0.003 (3)
C100.029 (4)0.021 (4)0.031 (4)−0.003 (3)0.009 (3)−0.004 (3)
C110.022 (4)0.026 (4)0.023 (4)0.000 (3)0.009 (3)−0.003 (3)
C120.032 (4)0.013 (3)0.027 (4)−0.003 (3)0.016 (3)−0.005 (3)
Geometric parameters (Å, º) top
Pd1—N22.035 (6)C4—C121.412 (10)
Pd1—N12.036 (6)C4—C51.441 (12)
Pd1—Cl22.283 (2)C5—C61.335 (11)
Pd1—Cl12.2914 (19)C5—H50.9500
N1—C11.327 (9)C6—C71.423 (11)
N1—C121.359 (9)C6—H60.9500
N2—C101.324 (9)C7—C111.404 (10)
N2—C111.357 (9)C7—C81.407 (10)
C1—C21.392 (12)C8—C91.360 (10)
C1—H10.9500C8—H80.9500
C2—C31.368 (12)C9—C101.394 (11)
C2—H20.9500C9—H90.9500
C3—C41.401 (11)C10—H100.9500
C3—H30.9500C11—C121.433 (10)
N2—Pd1—N181.5 (2)C6—C5—C4121.1 (7)
N2—Pd1—Cl2175.11 (17)C6—C5—H5119.5
N1—Pd1—Cl293.93 (17)C4—C5—H5119.5
N2—Pd1—Cl193.20 (17)C5—C6—C7122.3 (7)
N1—Pd1—Cl1174.64 (17)C5—C6—H6118.8
Cl2—Pd1—Cl191.42 (7)C7—C6—H6118.8
C1—N1—C12118.4 (7)C11—C7—C8116.1 (7)
C1—N1—Pd1129.4 (5)C11—C7—C6118.5 (7)
C12—N1—Pd1112.2 (4)C8—C7—C6125.4 (7)
C10—N2—C11118.4 (6)C9—C8—C7120.2 (7)
C10—N2—Pd1129.1 (5)C9—C8—H8119.9
C11—N2—Pd1112.6 (5)C7—C8—H8119.9
N1—C1—C2122.2 (8)C8—C9—C10119.8 (7)
N1—C1—H1118.9C8—C9—H9120.1
C2—C1—H1118.9C10—C9—H9120.1
C3—C2—C1120.0 (7)N2—C10—C9122.1 (7)
C3—C2—H2120.0N2—C10—H10119.0
C1—C2—H2120.0C9—C10—H10119.0
C2—C3—C4119.6 (7)N2—C11—C7123.5 (7)
C2—C3—H3120.2N2—C11—C12116.6 (6)
C4—C3—H3120.2C7—C11—C12119.9 (7)
C3—C4—C12116.8 (7)N1—C12—C4122.9 (6)
C3—C4—C5125.1 (7)N1—C12—C11117.0 (6)
C12—C4—C5118.1 (7)C4—C12—C11120.1 (7)
N2—Pd1—N1—C1−177.2 (7)Pd1—N2—C10—C9177.3 (5)
Cl2—Pd1—N1—C14.4 (7)C8—C9—C10—N21.3 (12)
N2—Pd1—N1—C123.4 (5)C10—N2—C11—C70.5 (11)
Cl2—Pd1—N1—C12−174.9 (5)Pd1—N2—C11—C7−178.0 (6)
N1—Pd1—N2—C10178.1 (7)C10—N2—C11—C12−178.3 (6)
Cl1—Pd1—N2—C10−1.4 (6)Pd1—N2—C11—C123.1 (8)
N1—Pd1—N2—C11−3.6 (5)C8—C7—C11—N2−0.4 (11)
Cl1—Pd1—N2—C11176.9 (5)C6—C7—C11—N2−179.5 (7)
C12—N1—C1—C20.8 (11)C8—C7—C11—C12178.4 (7)
Pd1—N1—C1—C2−178.5 (6)C6—C7—C11—C12−0.7 (10)
N1—C1—C2—C30.1 (13)C1—N1—C12—C4−0.9 (10)
C1—C2—C3—C4−1.0 (12)Pd1—N1—C12—C4178.6 (5)
C2—C3—C4—C120.9 (11)C1—N1—C12—C11177.8 (6)
C2—C3—C4—C5−179.6 (8)Pd1—N1—C12—C11−2.8 (8)
C3—C4—C5—C6178.3 (7)C3—C4—C12—N10.0 (11)
C12—C4—C5—C6−2.2 (11)C5—C4—C12—N1−179.5 (7)
C4—C5—C6—C71.1 (12)C3—C4—C12—C11−178.6 (7)
C5—C6—C7—C110.3 (11)C5—C4—C12—C111.8 (10)
C5—C6—C7—C8−178.7 (8)N2—C11—C12—N1−0.2 (10)
C11—C7—C8—C90.7 (11)C7—C11—C12—N1−179.2 (6)
C6—C7—C8—C9179.7 (7)N2—C11—C12—C4178.5 (6)
C7—C8—C9—C10−1.1 (12)C7—C11—C12—C4−0.5 (10)
C11—N2—C10—C9−1.0 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1i0.952.803.733 (11)169
Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[PdCl2(C12H8N2)]
Mr357.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)9.6170 (8), 17.1402 (14), 7.2529 (6)
β (°) 109.314 (2)
V (Å3)1128.26 (16)
Z4
Radiation typeMo Kα
µ (mm−1)2.09
Crystal size (mm)0.36 × 0.06 × 0.04
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.769, 0.920
No. of measured, independent and
observed [I > 2σ(I)] reflections		8118, 2767, 1852
Rint0.060
(sin θ/λ)max (Å−1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.169, 1.10
No. of reflections2767
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)2.90, −1.29

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

Selected geometric parameters (Å, º) top
Pd1—N22.035 (6)Pd1—Cl22.283 (2)
Pd1—N12.036 (6)Pd1—Cl12.2914 (19)
N2—Pd1—N181.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cl1i0.952.803.733 (11)169
Symmetry code: (i) −x+1, 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 (2009–0094056).

References

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ISSN: 2056-9890
Volume 66| Part 1| January 2010| Page m38
doi:10.1107/S1600536809052313
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