Redetermination of (2,2′-bipyridine-κ2N,N′)dichlorido­palladium(II) dichloro­methane solvate

Kim, N.-H.; Hwang, I.-C.; Ha, K.

doi:10.1107/S1600536809016262

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages m615-m616

doi:10.1107/S1600536809016262

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Redetermination of (2,2′-bipyridine-κ²N,N′)dichloridopalladium(II) dichloromethane solvate

Nam-Ho Kim,^a In-Chul Hwang ^b and Kwang Ha ^a ^*

^aSchool of Applied Chemical Engineering, The Research Institute of Catalysis, Chonnam National University, Gwangju 500-757, Republic of Korea, and ^bInstitute of Basic Sciences, Pohang University of Science and Technology, Pohang 790-784, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

(Received 23 April 2009; accepted 30 April 2009; online 7 May 2009)

In the title compound, [PdCl₂(C₁₀H₈N₂)]·CH₂Cl₂, the Pd²⁺ ion is four-coordinated in a slightly distorted square-planar environment by two N atoms of the 2,2′-bipyridine (bipy) ligand and two chloride ions. The compound displays intramolecular C—H⋯Cl hydrogen bonds and pairs of complex molecules are connected by intermolecular C—H⋯Cl hydrogen bonds. Intermolecular π–π interactions are present between the pyridine rings of the ligand, the shortest centroid–centroid distance being 4.096 (3) Å. As a result of the electronic nature of the chelate ring, it is possible to create π–π interactions to its symmetry-related counterpart [3.720 (2) Å] and also with a pyridine ring [3.570 (3) Å] of the bipy unit. The present structure is a redetermination of a previous structure [Vicente et al. (1997 ). Private communication (refcode PYCXMN02). CCDC, Cambridge, England]. In the new structure refinement all H atoms were located in a difference Fourier synthesis. Their coordinates were refined freely, together with isotropic displacement parameters.

Related literature

For crystal structures of [PdX₂(bipy)] (X = Cl or Br), see: Maekawa et al. (1991 ); Vicente et al. (1997); Smeets et al. (1997 ). For related Pt(II, IV)–bipyridine complexes, see: Osborn & Rogers (1974 ); Hambley (1986 ); Sartori et al. (2005 ); Momeni et al. (2007 ); Kim et al. (2009 ).

Experimental

Crystal data

[PdCl₂(C₁₀H₈N₂)]·CH₂Cl₂
M_r = 418.41
Triclinic, $[P \overline 1]$
a = 8.7913 (10) Å
b = 9.1115 (11) Å
c = 10.1846 (12) Å
α = 72.481 (2)°
β = 66.983 (2)°
γ = 81.429 (2)°
V = 715.58 (15) Å³
Z = 2
Mo Kα radiation
μ = 2.03 mm⁻¹
T = 293 K
0.20 × 0.08 × 0.08 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.623, T_max = 0.850
4221 measured reflections
2862 independent reflections
2298 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.097
S = 1.05
2862 reflections
203 parameters
All H-atom parameters refined
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Selected bond lengths (Å)

Pd1—N2	2.025 (4)
Pd1—N1	2.029 (4)
Pd1—Cl2	2.2853 (14)
Pd1—Cl1	2.2964 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl2	0.93 (5)	2.59 (5)	3.230 (6)	126 (4)
C2—H2⋯Cl2ⁱ	0.93 (5)	2.79 (5)	3.595 (7)	145 (4)
C10—H10⋯Cl1	0.86 (5)	2.68 (5)	3.248 (6)	125 (4)
C11—H11B⋯Cl1	0.99 (6)	2.63 (6)	3.578 (8)	161 (5)
Symmetry code: (i) -x, -y+1, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016262/kp2220sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016262/kp2220Isup2.hkl

checkCIF report

Comment top

The asymmetric unit of the title compound, [PdCl₂(C₁₀H₈N₂)].CH₂Cl₂, contains a neutral Pd^II complex and a solvent molecule (Fig. 1). The compound crystallized in the triclinic space group P1, whereas the previously reported complex [PdCl₂(C₁₀H₈N₂)] crystallized in the orthorhombic space group C222₁ (Maekawa et al., 1991). The X-ray structure analysis of the title compound was previously carried out (Vicente et al., 1997) and the structure is stored in CCDC code: RAGVUQ. The stored and our crystal structures are in agreement, however, the new structure determination provides data on hydrogen bonding based on H atoms positions located from a difference Fourier synthesis and refined isotropically.

In the complex, the Pd²⁺ ion is four-coordinated in a distorted square-planar environment by two N atoms of the 2,2'-bipyridine (bipy) ligand and two Cl ions. The main contribution to the distortion is the tight N1—Pd1—N2 chelate angle (81.04 (16)°), which results in non-linear trans arrangement (<N1—Pd1—Cl1 = 175.78 (12)° and <N2—Pd1—Cl2 = 174.97 (12)°). The Pd1—N and Pd1—Cl bond lengths are almost equal (Pd1—N: 2.029 (4) and 2.025 (4) Å; Pd1—Cl 2.2964 (14) and 2.2853 (14) Å), respectively (Table 1), and close to those reported for [PdCl₂(C₁₀H₈N₂)] (Maekawa et al., 1991). The best least-squares plane of the atoms of the planar complex, except Cl2, reveals mean deviation of 0.026 (5) Å; deviation of Cl2 from this plane is 0.184 (2) Å. The compound displays the inter- and intramolecular C—H···Cl hydrogen bonds (Table 2) and molecules are connected by intermolecular hydrogen bonds and stacked in layres along the c axis (Fig. 2). Intermolecular π-π interactions (defined by separation distance between the ring centroids (the symmetry operation for second plane 1-x,1-y,-z) involve the planes: Pd1,N1→ N2 and ity symmetry related counterpart, 3.720 (2) Å, planes are parallel and shifted for 1.506 Å; Pd1,N1→ N2 and N1→ C5, 3.570 (3) Å, the dihedral angle between planes is 1.54 °, no shift; N1→ C5 and N2→ C10, 4.096 (3) Å the dihedral angle between planes is 2.72 °, no shift.

Related literature top

For crystal structures of [PdX₂(bipy)] (X = Cl or Br), see: Maekawa et al. (1991); Vicente et al. (1997); Smeets et al. (1997). For related Pt(II, IV)–bipyridine complexes, see: Osborn & Rogers (1974); Hambley (1986); Sartori et al. (2005); Momeni et al. (2007); Kim et al. (2009).

Experimental top

To a solution of Na₂PdCl₄ (0.300 g, 1.020 mmol) in EtOH (30 ml) was added 2,2'-bipyridine (0.159 g, 1.018 mmol) and stirred for 5 h at room temperature. The precipitate obtained was separated by filtration and washed with EtOH and water and dried under vacuum, to give a yellow powder (0.302 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from a CH₂Cl₂ solution.

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

	Fig. 1. The structure of the title compound, with displacement ellipsoids drawn at the 40% probability level for non-H atoms.
	Fig. 2. Crystal packing of I. Hydrogen-bond interactions are drawn with dashed lines.

(2,2'-Bipyridine-κ²N,N')dichloridopalladium(II) dichloromethane solvate top

Crystal data top

[PdCl₂(C₁₀H₈N₂)]·CH₂Cl₂	Z = 2
M_r = 418.41	F(000) = 408
Triclinic, P1	D_x = 1.942 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7913 (10) Å	Cell parameters from 983 reflections
b = 9.1115 (11) Å	θ = 2.3–21.7°
c = 10.1846 (12) Å	µ = 2.03 mm⁻¹
α = 72.481 (2)°	T = 293 K
β = 66.983 (2)°	Stick, yellow
γ = 81.429 (2)°	0.20 × 0.08 × 0.08 mm
V = 715.58 (15) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	2298 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.623, T_max = 0.850	k = −7→11
4221 measured reflections	l = −12→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	All H-atom parameters refined
S = 1.05	w = 1/[σ²(F_o²) + (0.0352P)² + 0.5604P] where P = (F_o² + 2F_c²)/3
2862 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

[PdCl₂(C₁₀H₈N₂)]·CH₂Cl₂	γ = 81.429 (2)°
M_r = 418.41	V = 715.58 (15) Å³
Triclinic, P1	Z = 2
a = 8.7913 (10) Å	Mo Kα radiation
b = 9.1115 (11) Å	µ = 2.03 mm⁻¹
c = 10.1846 (12) Å	T = 293 K
α = 72.481 (2)°	0.20 × 0.08 × 0.08 mm
β = 66.983 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	2862 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2298 reflections with I > 2σ(I)
T_min = 0.623, T_max = 0.850	R_int = 0.023
4221 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.097	All H-atom parameters refined
S = 1.05	Δρ_max = 0.56 e Å⁻³
2862 reflections	Δρ_min = −0.69 e Å⁻³
203 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
Pd1	0.32112 (5)	0.28572 (4)	0.21130 (4)	0.04479 (15)
Cl1	0.36850 (18)	0.02764 (15)	0.30403 (16)	0.0612 (4)
Cl2	0.1458 (2)	0.22805 (17)	0.11857 (19)	0.0720 (5)
N1	0.2916 (5)	0.5169 (5)	0.1348 (4)	0.0454 (10)
N2	0.4786 (5)	0.3551 (5)	0.2803 (4)	0.0446 (10)
C1	0.1884 (7)	0.5895 (7)	0.0665 (6)	0.0545 (14)
H1	0.126 (6)	0.526 (6)	0.052 (5)	0.058 (16)*
C2	0.1803 (8)	0.7475 (7)	0.0175 (7)	0.0610 (15)
H2	0.101 (7)	0.800 (6)	−0.020 (6)	0.063 (17)*
C3	0.2768 (8)	0.8325 (7)	0.0413 (7)	0.0620 (16)
H3	0.273 (6)	0.930 (6)	0.018 (5)	0.043 (14)*
C4	0.3831 (7)	0.7585 (6)	0.1120 (6)	0.0515 (13)
H4	0.451 (6)	0.809 (6)	0.128 (5)	0.046 (14)*
C5	0.3887 (6)	0.6010 (6)	0.1590 (5)	0.0417 (11)
C6	0.4959 (6)	0.5099 (6)	0.2384 (5)	0.0466 (12)
C7	0.6069 (8)	0.5739 (7)	0.2675 (7)	0.0644 (16)
H7	0.623 (7)	0.683 (7)	0.236 (6)	0.081 (19)*
C8	0.7003 (9)	0.4784 (8)	0.3427 (8)	0.077 (2)
H8	0.775 (8)	0.512 (8)	0.355 (7)	0.09 (2)*
C9	0.6833 (8)	0.3223 (8)	0.3858 (8)	0.0717 (18)
H9	0.734 (6)	0.255 (6)	0.442 (5)	0.049 (15)*
C10	0.5692 (7)	0.2645 (7)	0.3546 (7)	0.0579 (15)
H10	0.562 (6)	0.166 (6)	0.376 (5)	0.043 (14)*
C11	0.0507 (9)	0.1175 (7)	0.6220 (8)	0.0614 (16)
H11A	−0.043 (7)	0.071 (6)	0.685 (6)	0.062 (17)*
H11B	0.115 (7)	0.087 (7)	0.529 (7)	0.09 (2)*
Cl3	−0.0049 (2)	0.31218 (19)	0.55636 (18)	0.0740 (5)
Cl4	0.1895 (2)	0.1016 (2)	0.7099 (2)	0.0887 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.0465 (2)	0.0387 (2)	0.0512 (3)	−0.00670 (17)	−0.01825 (18)	−0.01196 (18)
Cl1	0.0744 (9)	0.0386 (7)	0.0735 (9)	−0.0059 (7)	−0.0309 (8)	−0.0121 (7)
Cl2	0.0836 (11)	0.0561 (9)	0.0965 (12)	−0.0203 (8)	−0.0543 (9)	−0.0117 (8)
N1	0.045 (2)	0.044 (2)	0.048 (2)	−0.005 (2)	−0.017 (2)	−0.0118 (19)
N2	0.049 (2)	0.039 (2)	0.050 (2)	−0.0036 (19)	−0.021 (2)	−0.0121 (19)
C1	0.052 (3)	0.054 (3)	0.062 (3)	−0.002 (3)	−0.028 (3)	−0.012 (3)
C2	0.063 (4)	0.050 (4)	0.068 (4)	0.008 (3)	−0.029 (3)	−0.009 (3)
C3	0.072 (4)	0.039 (3)	0.074 (4)	−0.002 (3)	−0.025 (3)	−0.016 (3)
C4	0.057 (3)	0.039 (3)	0.063 (3)	−0.005 (3)	−0.025 (3)	−0.016 (3)
C5	0.041 (3)	0.039 (3)	0.044 (3)	−0.004 (2)	−0.010 (2)	−0.016 (2)
C6	0.046 (3)	0.044 (3)	0.045 (3)	−0.004 (2)	−0.012 (2)	−0.011 (2)
C7	0.080 (4)	0.052 (4)	0.078 (4)	−0.015 (3)	−0.045 (4)	−0.013 (3)
C8	0.084 (5)	0.070 (5)	0.097 (5)	−0.016 (4)	−0.058 (4)	−0.009 (4)
C9	0.074 (4)	0.063 (4)	0.092 (5)	−0.004 (3)	−0.054 (4)	−0.009 (4)
C10	0.065 (4)	0.045 (3)	0.067 (4)	−0.002 (3)	−0.032 (3)	−0.008 (3)
C11	0.065 (4)	0.052 (4)	0.072 (4)	−0.009 (3)	−0.026 (3)	−0.019 (3)
Cl3	0.0761 (10)	0.0652 (10)	0.0759 (10)	0.0022 (8)	−0.0354 (9)	−0.0044 (8)
Cl4	0.0906 (12)	0.0701 (11)	0.1211 (15)	0.0040 (9)	−0.0663 (12)	−0.0139 (10)

Geometric parameters (Å, º) top

Pd1—N2	2.025 (4)	C4—H4	0.90 (5)
Pd1—N1	2.029 (4)	C5—C6	1.480 (7)
Pd1—Cl2	2.2853 (14)	C6—C7	1.371 (7)
Pd1—Cl1	2.2964 (14)	C7—C8	1.377 (9)
N1—C1	1.335 (6)	C7—H7	0.96 (6)
N1—C5	1.360 (6)	C8—C9	1.369 (9)
N2—C10	1.338 (7)	C8—H8	0.83 (6)
N2—C6	1.359 (6)	C9—C10	1.375 (8)
C1—C2	1.375 (8)	C9—H9	0.90 (5)
C1—H1	0.93 (5)	C10—H10	0.86 (5)
C2—C3	1.360 (8)	C11—Cl4	1.743 (6)
C2—H2	0.93 (5)	C11—Cl3	1.765 (6)
C3—C4	1.376 (8)	C11—H11A	0.90 (5)
C3—H3	0.85 (5)	C11—H11B	0.99 (6)
C4—C5	1.369 (7)

N2—Pd1—N1	81.04 (16)	N1—C5—C4	120.6 (5)
N2—Pd1—Cl2	174.97 (12)	N1—C5—C6	115.2 (4)
N1—Pd1—Cl2	94.27 (12)	C4—C5—C6	124.2 (5)
N2—Pd1—Cl1	94.74 (12)	N2—C6—C7	121.4 (5)
N1—Pd1—Cl1	175.78 (12)	N2—C6—C5	115.0 (4)
Cl2—Pd1—Cl1	89.94 (5)	C7—C6—C5	123.6 (5)
C1—N1—C5	119.3 (5)	C6—C7—C8	118.8 (6)
C1—N1—Pd1	126.5 (4)	C6—C7—H7	122 (4)
C5—N1—Pd1	114.2 (3)	C8—C7—H7	119 (4)
C10—N2—C6	118.9 (4)	C9—C8—C7	120.2 (6)
C10—N2—Pd1	126.6 (4)	C9—C8—H8	118 (5)
C6—N2—Pd1	114.4 (3)	C7—C8—H8	121 (5)
N1—C1—C2	121.4 (6)	C8—C9—C10	118.5 (6)
N1—C1—H1	116 (3)	C8—C9—H9	124 (3)
C2—C1—H1	123 (3)	C10—C9—H9	117 (3)
C3—C2—C1	119.7 (6)	N2—C10—C9	122.2 (6)
C3—C2—H2	118 (4)	N2—C10—H10	118 (3)
C1—C2—H2	122 (4)	C9—C10—H10	119 (3)
C2—C3—C4	119.2 (6)	Cl4—C11—Cl3	111.0 (3)
C2—C3—H3	124 (3)	Cl4—C11—H11A	111 (4)
C4—C3—H3	117 (3)	Cl3—C11—H11A	106 (4)
C5—C4—C3	119.8 (5)	Cl4—C11—H11B	106 (3)
C5—C4—H4	118 (3)	Cl3—C11—H11B	103 (4)
C3—C4—H4	123 (3)	H11A—C11—H11B	120 (5)

N2—Pd1—N1—C1	−177.3 (4)	C3—C4—C5—N1	0.8 (8)
Cl2—Pd1—N1—C1	4.6 (4)	C3—C4—C5—C6	−178.8 (5)
N2—Pd1—N1—C5	2.4 (3)	C10—N2—C6—C7	1.7 (8)
Cl2—Pd1—N1—C5	−175.7 (3)	Pd1—N2—C6—C7	−175.3 (4)
N1—Pd1—N2—C10	179.8 (5)	C10—N2—C6—C5	−179.1 (4)
Cl1—Pd1—N2—C10	−0.3 (5)	Pd1—N2—C6—C5	4.0 (5)
N1—Pd1—N2—C6	−3.5 (3)	N1—C5—C6—N2	−2.0 (6)
Cl1—Pd1—N2—C6	176.4 (3)	C4—C5—C6—N2	177.6 (5)
C5—N1—C1—C2	1.2 (8)	N1—C5—C6—C7	177.3 (5)
Pd1—N1—C1—C2	−179.2 (4)	C4—C5—C6—C7	−3.1 (8)
N1—C1—C2—C3	−1.3 (9)	N2—C6—C7—C8	−1.0 (9)
C1—C2—C3—C4	1.1 (9)	C5—C6—C7—C8	179.8 (6)
C2—C3—C4—C5	−0.8 (9)	C6—C7—C8—C9	0.7 (11)
C1—N1—C5—C4	−0.9 (7)	C7—C8—C9—C10	−1.2 (11)
Pd1—N1—C5—C4	179.4 (4)	C6—N2—C10—C9	−2.2 (9)
C1—N1—C5—C6	178.7 (4)	Pd1—N2—C10—C9	174.4 (5)
Pd1—N1—C5—C6	−1.0 (5)	C8—C9—C10—N2	1.9 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2	0.93 (5)	2.59 (5)	3.230 (6)	126 (4)
C2—H2···Cl2ⁱ	0.93 (5)	2.79 (5)	3.595 (7)	145 (4)
C10—H10···Cl1	0.86 (5)	2.68 (5)	3.248 (6)	125 (4)
C11—H11B···Cl1	0.99 (6)	2.63 (6)	3.578 (8)	161 (5)

Symmetry code: (i) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[PdCl₂(C₁₀H₈N₂)]·CH₂Cl₂
M_r	418.41
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.7913 (10), 9.1115 (11), 10.1846 (12)
α, β, γ (°)	72.481 (2), 66.983 (2), 81.429 (2)
V (Å³)	715.58 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.03
Crystal size (mm)	0.20 × 0.08 × 0.08

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.623, 0.850
No. of measured, independent and observed [I > 2σ(I)] reflections	4221, 2862, 2298
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.097, 1.05
No. of reflections	2862
No. of parameters	203
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.69

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—N2	2.025 (4)	Pd1—Cl2	2.2853 (14)
Pd1—N1	2.029 (4)	Pd1—Cl1	2.2964 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl2	0.93 (5)	2.59 (5)	3.230 (6)	126 (4)
C2—H2···Cl2ⁱ	0.93 (5)	2.79 (5)	3.595 (7)	145 (4)
C10—H10···Cl1	0.86 (5)	2.68 (5)	3.248 (6)	125 (4)
C11—H11B···Cl1	0.99 (6)	2.63 (6)	3.578 (8)	161 (5)

Symmetry code: (i) −x, −y+1, −z.

Acknowledgements

This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2007–412-J02001).

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