Dichlorido[1-(1-naphthyl­meth­yl)-3-(2-pyrid­yl)-1H-pyrazole-κ2N2,N3]palladium(II)

Liu, C.-S.; Sun, G.-H.; Guo, L.-Q.

doi:10.1107/S1600536807062927

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m69

https://doi.org/10.1107/S1600536807062927

Open

access

Dichlorido[1-(1-naphthylmethyl)-3-(2-pyridyl)-1H-pyrazole-κ²N²,N³]palladium(II)

Chun-Sen Liu,^a,^b ^* Guang-Hui Sun ^a and Liang-Qi Guo ^a

^aZhengzhou University of Light Industry, Henan Provincial Key Laboratory of Surface & Interface Science, Henan, Zhengzhou 450002, People's Republic of China, and ^bDepartment of Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: chunsenliu@mail.nankai.edu.cn

(Received 1 November 2007; accepted 24 November 2007; online 6 December 2007)

In the title compound, [PdCl₂(C₁₉H₁₅N₃)], the Pd^II centre is four-coordinated by two N-atom donors from one 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene (L) ligand and by two Cl atoms in a distorted square-planar coordination geometry. In the crystal structure, adjacent Pd^II mononuclear units form intermolecular C—H⋯π interactions involving the benzene and pyridine rings of different L ligands and π–π stacking interactions between the pyrazolyl-pyridine and naphthalene rings of neighbouring L ligands, with a centroid–centroid separation of 3.522 (1) Å.

Related literature

For related literature, see: Bell et al. (2003 ); Janiak (2000 ); Liu, Li et al. (2007 ); Liu, Zhang et al. (2007 ); Paul et al. (2004 ); Singh et al. (2003 ); Sony & Ponnuswamy (2006 ); Steel (2005 ); Ward et al. (2001 ); Zhang et al. (2005 ); Zou et al. (2004 ).

Experimental

Crystal data

[PdCl₂(C₁₉H₁₅N₃)]
M_r = 462.64
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.330 (6) Å
b = 12.139 (8) Å
c = 15.918 (11) Å
V = 1803 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.33 mm⁻¹
T = 293 (2) K
0.20 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.772, T_max = 0.848
10453 measured reflections
3702 independent reflections
3340 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.054
S = 1.03
3702 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.37 e Å⁻³
Absolute structure: Flack (1983 ), 1580 Friedel pairs
Flack parameter: 0.00 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯Cg1ⁱ	0.93	2.89	3.602	134
C18—H18A⋯Cg2ⁱⁱ	0.93	3.05	3.803	139
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ . Cg1 is the centroid of atoms C1–C5/C10 and Cg2 is the centroid of atoms Pd1/N2/C14/C15/N3.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807062927/bi2262sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062927/bi2262Isup2.hkl

checkCIF report

Comment top

In recent years, attention has been focused on the synthetic approach and the structural control of metal-organic coordination architectures with ligands based on pyrazolyl-pyridine chelating units (Steel, 2005; Ward et al., 2001). In this field, Ward and co-workers have reported novel functional complexes through the use of 3-(2-pyridyl)pyrazole and/or 3-(2-pyridyl)pyrazole-based ligands (Bell et al., 2003; Paul et al., 2004; Singh et al., 2003; Ward et al., 2001; Zou et al., 2004). Recently, we have reported the preparation of a non-planar ligand, 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene (denoted L) (Liu & Li et al., 2007; Liu & Zhang et al., 2007; Zhang et al., 2005). We report here the crystal structure of a palladium complex of this ligand, [(L)PdCl₂].

In the title compound, the Pd^II centre is four-coordinated by two N-atom donors from one L ligand and two Cl atoms. The coordination geometry around the Pd^II center can be described as a slightly distorted square-plane (Fig. 1). In the crystal structure, the Pd^II mononuclear units form intermolecular π···π stacking interactions between pyrazolyl-pyridine and naphthalene rings of neighbouring L ligands with a centroid–centroid separation of 3.522 (1) Å (Janiak, 2000) and C—H···π interactions involving C1/C2/C3/C4/C5/C10 (centroid Cg1) benzene rings of the L ligands as well as five-membered chelate rings Pd1/N2/C14/C15/N3 (centroid Cg2) (Sony and Ponnuswamy, 2006) (Fig. 2).

Related literature top

For related literature, see: Bell et al. (2003); Janiak (2000); Liu, Li et al. (2007); Liu, Zhang et al. (2007); Paul et al. (2004); Singh et al. (2003); Sony & Ponnuswamy (2006); Steel (2005); Ward et al. (2001); Zhang et al. (2005); Zou et al. (2004). Cg1 is the centroid of atoms C1–C5/C10 and Cg2 is the centroid of atoms Pd1/N2/C14/C15/N3.

Experimental top

The ligand 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene (L) was synthesized according to the method reported in the literature (Liu & Li et al., 2007; Liu & Zhang et al., 2007; Zhang et al., 2005). A solution of PdCl₂ (0.1 mmol) in methanol (15 ml) and acetonitrile (5 ml) was added to L (0.1 mmol). A yellow solid formed was filtered off and the resulting solution was kept at room temperature. Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent after several days. Yield: ca 30%. Elemental analysis calculated: C 49.32, H 3.27, N 9.08%; found: C 49.47, H 3.16, N 9.20%.

Structure description top

For related literature, see: Bell et al. (2003); Janiak (2000); Liu, Li et al. (2007); Liu, Zhang et al. (2007); Paul et al. (2004); Singh et al. (2003); Sony & Ponnuswamy (2006); Steel (2005); Ward et al. (2001); Zhang et al. (2005); Zou et al. (2004). Cg1 is the centroid of atoms C1–C5/C10 and Cg2 is the centroid of atoms Pd1/N2/C14/C15/N3.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 199 and PLATON (Spek, 2003).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-H atoms.
	Fig. 2. Part of the crystal packing showing a two-dimensional network structure in the title compound formed by the co-effects of intermolecular C—H···π (dashed solid lines) and π···π stacking (dashed open lines) interactions. For the sake of clarity, only H atoms involved in the interactions are shown.

Dichlorido[1-(1-naphthylmethyl)-3-(2-pyridyl)-1H-pyrazole- κ²N²,N³]palladium(II) top

Crystal data top

[PdCl₂(C₁₉H₁₅N₃)]	F(000) = 920
M_r = 462.64	D_x = 1.705 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 970 reflections
a = 9.330 (6) Å	θ = 3.4–26.4°
b = 12.139 (8) Å	µ = 1.33 mm⁻¹
c = 15.918 (11) Å	T = 293 K
V = 1803 (2) Å³	Block, yellow
Z = 4	0.20 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD diffractometer	3702 independent reflections
Radiation source: fine-focus sealed tube	3340 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 26.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→11
T_min = 0.772, T_max = 0.848	k = −14→15
10453 measured reflections	l = −19→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.0227P)² + 0.3859P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3702 reflections	Δρ_max = 0.27 e Å⁻³
226 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1580 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (3)

Crystal data top

[PdCl₂(C₁₉H₁₅N₃)]	V = 1803 (2) Å³
M_r = 462.64	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.330 (6) Å	µ = 1.33 mm⁻¹
b = 12.139 (8) Å	T = 293 K
c = 15.918 (11) Å	0.20 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD diffractometer	3702 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3340 reflections with I > 2σ(I)
T_min = 0.772, T_max = 0.848	R_int = 0.028
10453 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.054	Δρ_max = 0.27 e Å⁻³
S = 1.03	Δρ_min = −0.37 e Å⁻³
3702 reflections	Absolute structure: Flack (1983), 1580 Friedel pairs
226 parameters	Absolute structure parameter: 0.00 (3)
0 restraints

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	0.83064 (2)	0.490954 (17)	0.051890 (13)	0.03837 (7)
C1	0.5698 (4)	0.9043 (3)	0.1086 (3)	0.0546 (9)
H1A	0.6381	0.9001	0.0662	0.065*
C2	0.5637 (4)	0.9961 (3)	0.1585 (3)	0.0654 (10)
H2A	0.6281	1.0534	0.1498	0.079*
C3	0.4620 (4)	1.0044 (4)	0.2221 (2)	0.0704 (12)
H3A	0.4589	1.0670	0.2557	0.084*
C4	0.3679 (4)	0.9219 (4)	0.2351 (2)	0.0651 (11)
H4A	0.2993	0.9290	0.2771	0.078*
C5	0.3714 (3)	0.8245 (3)	0.1859 (2)	0.0511 (9)
C6	0.2756 (4)	0.7376 (4)	0.1995 (2)	0.0639 (11)
H6A	0.2078	0.7433	0.2421	0.077*
C7	0.2800 (4)	0.6453 (3)	0.1516 (3)	0.0613 (10)
H7A	0.2168	0.5878	0.1622	0.074*
C8	0.3806 (4)	0.6365 (3)	0.0856 (2)	0.0505 (8)
H8A	0.3824	0.5730	0.0530	0.061*
C9	0.4752 (3)	0.7192 (2)	0.0689 (2)	0.0408 (7)
C10	0.4739 (3)	0.8161 (3)	0.1208 (2)	0.0430 (7)
C11	0.5803 (3)	0.7164 (2)	−0.0027 (2)	0.0444 (8)
H11A	0.5576	0.7758	−0.0412	0.053*
H11B	0.6756	0.7301	0.0193	0.053*
C12	0.5032 (4)	0.5886 (3)	−0.1173 (2)	0.0534 (8)
H12A	0.4323	0.6329	−0.1406	0.064*
C13	0.5448 (3)	0.4872 (3)	−0.1465 (2)	0.0512 (8)
H13A	0.5090	0.4492	−0.1927	0.061*
C14	0.6522 (3)	0.4540 (2)	−0.09185 (19)	0.0397 (7)
C15	0.7469 (3)	0.3595 (2)	−0.0911 (2)	0.0394 (7)
C16	0.7465 (4)	0.2785 (3)	−0.1518 (2)	0.0479 (8)
H16A	0.6799	0.2806	−0.1952	0.058*
C17	0.8446 (4)	0.1953 (3)	−0.1477 (3)	0.0612 (10)
H17A	0.8459	0.1404	−0.1885	0.073*
C18	0.9416 (5)	0.1935 (3)	−0.0826 (3)	0.0675 (13)
H18A	1.0096	0.1377	−0.0789	0.081*
C19	0.9366 (4)	0.2753 (3)	−0.0231 (3)	0.0619 (11)
H19A	1.0022	0.2740	0.0209	0.074*
N1	0.5823 (3)	0.6132 (2)	−0.04930 (19)	0.0434 (6)
N2	0.6739 (3)	0.53078 (17)	−0.03249 (14)	0.0378 (5)
N3	0.8397 (3)	0.35759 (19)	−0.02653 (16)	0.0438 (6)
Cl1	1.00048 (11)	0.42155 (9)	0.13879 (7)	0.0708 (3)
Cl2	0.81909 (11)	0.64162 (6)	0.13707 (5)	0.0521 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.03920 (11)	0.03896 (11)	0.03696 (11)	0.00037 (11)	0.00213 (10)	0.00045 (11)
C1	0.058 (2)	0.0449 (19)	0.060 (2)	0.0110 (17)	−0.0040 (18)	0.0000 (17)
C2	0.075 (2)	0.0455 (19)	0.076 (3)	0.013 (2)	−0.024 (2)	−0.010 (2)
C3	0.077 (3)	0.066 (3)	0.068 (2)	0.035 (3)	−0.030 (2)	−0.022 (2)
C4	0.062 (3)	0.083 (3)	0.051 (2)	0.038 (2)	−0.0089 (18)	−0.015 (2)
C5	0.043 (2)	0.064 (2)	0.045 (2)	0.0218 (16)	−0.0049 (15)	0.0039 (17)
C6	0.054 (2)	0.091 (3)	0.047 (2)	0.019 (2)	0.0085 (18)	0.009 (2)
C7	0.052 (2)	0.067 (3)	0.065 (3)	−0.0033 (18)	0.0031 (19)	0.016 (2)
C8	0.0479 (19)	0.0458 (18)	0.058 (2)	0.0036 (15)	−0.0020 (16)	0.0069 (16)
C9	0.0423 (17)	0.0381 (15)	0.0422 (19)	0.0102 (13)	0.0011 (15)	0.0071 (13)
C10	0.0429 (18)	0.0443 (17)	0.0417 (18)	0.0133 (14)	−0.0067 (14)	−0.0004 (14)
C11	0.0485 (19)	0.0372 (17)	0.048 (2)	0.0078 (15)	0.0034 (15)	0.0021 (16)
C12	0.056 (2)	0.060 (2)	0.045 (2)	0.0141 (18)	−0.0071 (18)	0.0007 (16)
C13	0.0554 (18)	0.057 (2)	0.0416 (17)	0.0038 (19)	−0.0077 (14)	−0.0047 (18)
C14	0.0411 (17)	0.0422 (15)	0.0357 (16)	−0.0023 (14)	0.0045 (14)	0.0002 (12)
C15	0.0440 (18)	0.0360 (16)	0.0381 (18)	−0.0043 (14)	0.0079 (14)	0.0011 (13)
C16	0.058 (2)	0.0444 (19)	0.041 (2)	−0.0048 (15)	0.0079 (16)	−0.0053 (15)
C17	0.075 (3)	0.0427 (18)	0.065 (2)	0.005 (2)	0.015 (3)	−0.0149 (16)
C18	0.074 (3)	0.055 (2)	0.073 (3)	0.022 (2)	−0.002 (2)	−0.013 (2)
C19	0.070 (3)	0.054 (2)	0.062 (3)	0.0214 (19)	−0.011 (2)	−0.0067 (17)
N1	0.0465 (15)	0.0424 (13)	0.0414 (15)	0.0105 (11)	0.0035 (13)	0.0016 (14)
N2	0.0408 (12)	0.0366 (11)	0.0361 (13)	0.0021 (11)	0.0040 (11)	0.0018 (9)
N3	0.0489 (15)	0.0385 (12)	0.0440 (15)	0.0071 (14)	0.0022 (14)	0.0013 (10)
Cl1	0.0659 (6)	0.0788 (6)	0.0677 (6)	0.0211 (5)	−0.0224 (5)	−0.0102 (5)
Cl2	0.0678 (5)	0.0452 (4)	0.0435 (4)	−0.0047 (4)	0.0009 (5)	−0.0056 (3)

Geometric parameters (Å, º) top

Pd1—N2	2.043 (3)	C9—C11	1.504 (5)
Pd1—N3	2.046 (3)	C11—N1	1.456 (4)
Pd1—Cl1	2.2658 (14)	C11—H11A	0.970
Pd1—Cl2	2.2792 (14)	C11—H11B	0.970
C1—C2	1.370 (5)	C12—N1	1.343 (5)
C1—C10	1.408 (5)	C12—C13	1.372 (5)
C1—H1A	0.930	C12—H12A	0.930
C2—C3	1.390 (6)	C13—C14	1.387 (4)
C2—H2A	0.930	C13—H13A	0.930
C3—C4	1.347 (6)	C14—N2	1.342 (4)
C3—H3A	0.930	C14—C15	1.448 (4)
C4—C5	1.418 (5)	C15—N3	1.343 (4)
C4—H4A	0.930	C15—C16	1.379 (4)
C5—C6	1.399 (5)	C16—C17	1.365 (5)
C5—C10	1.414 (5)	C16—H16A	0.930
C6—C7	1.356 (6)	C17—C18	1.377 (6)
C6—H6A	0.930	C17—H17A	0.930
C7—C8	1.413 (5)	C18—C19	1.373 (5)
C7—H7A	0.930	C18—H18A	0.930
C8—C9	1.363 (5)	C19—N3	1.348 (4)
C8—H8A	0.930	C19—H19A	0.930
C9—C10	1.438 (4)	N1—N2	1.343 (3)

N2—Pd1—N3	79.38 (10)	C9—C11—H11A	108.7
N2—Pd1—Cl1	171.74 (7)	N1—C11—H11B	108.7
N3—Pd1—Cl1	92.83 (9)	C9—C11—H11B	108.7
N2—Pd1—Cl2	99.63 (7)	H11A—C11—H11B	107.6
N3—Pd1—Cl2	178.86 (7)	N1—C12—C13	108.5 (3)
Cl1—Pd1—Cl2	88.18 (5)	N1—C12—H12A	125.8
C2—C1—C10	120.8 (4)	C13—C12—H12A	125.8
C2—C1—H1A	119.6	C12—C13—C14	104.6 (3)
C10—C1—H1A	119.6	C12—C13—H13A	127.7
C1—C2—C3	120.6 (4)	C14—C13—H13A	127.7
C1—C2—H2A	119.7	N2—C14—C13	110.4 (3)
C3—C2—H2A	119.7	N2—C14—C15	116.8 (3)
C4—C3—C2	120.2 (4)	C13—C14—C15	132.6 (3)
C4—C3—H3A	119.9	N3—C15—C16	121.7 (3)
C2—C3—H3A	119.9	N3—C15—C14	114.4 (3)
C3—C4—C5	121.3 (4)	C16—C15—C14	123.9 (3)
C3—C4—H4A	119.3	C17—C16—C15	119.5 (4)
C5—C4—H4A	119.3	C17—C16—H16A	120.2
C6—C5—C10	119.4 (3)	C15—C16—H16A	120.2
C6—C5—C4	121.9 (4)	C16—C17—C18	119.2 (3)
C10—C5—C4	118.6 (4)	C16—C17—H17A	120.4
C7—C6—C5	121.1 (4)	C18—C17—H17A	120.4
C7—C6—H6A	119.5	C19—C18—C17	119.1 (4)
C5—C6—H6A	119.5	C19—C18—H18A	120.5
C6—C7—C8	120.1 (4)	C17—C18—H18A	120.5
C6—C7—H7A	120.0	N3—C19—C18	122.0 (4)
C8—C7—H7A	120.0	N3—C19—H19A	119.0
C9—C8—C7	121.3 (3)	C18—C19—H19A	119.0
C9—C8—H8A	119.4	C12—N1—N2	110.2 (3)
C7—C8—H8A	119.4	C12—N1—C11	126.5 (3)
C8—C9—C10	119.0 (3)	N2—N1—C11	123.2 (3)
C8—C9—C11	123.6 (3)	C14—N2—N1	106.3 (2)
C10—C9—C11	117.3 (3)	C14—N2—Pd1	113.99 (19)
C1—C10—C5	118.5 (3)	N1—N2—Pd1	139.7 (2)
C1—C10—C9	122.5 (3)	C15—N3—C19	118.4 (3)
C5—C10—C9	119.1 (3)	C15—N3—Pd1	115.2 (2)
N1—C11—C9	114.4 (3)	C19—N3—Pd1	126.1 (2)
N1—C11—H11A	108.7

C10—C1—C2—C3	−0.3 (5)	C14—C15—C16—C17	176.9 (3)
C1—C2—C3—C4	−0.2 (6)	C15—C16—C17—C18	0.4 (6)
C2—C3—C4—C5	1.1 (6)	C16—C17—C18—C19	0.3 (6)
C3—C4—C5—C6	179.1 (3)	C17—C18—C19—N3	−0.1 (7)
C3—C4—C5—C10	−1.6 (5)	C13—C12—N1—N2	−0.4 (4)
C10—C5—C6—C7	0.4 (5)	C13—C12—N1—C11	175.1 (3)
C4—C5—C6—C7	179.6 (4)	C9—C11—N1—C12	90.9 (4)
C5—C6—C7—C8	−1.2 (6)	C9—C11—N1—N2	−94.1 (3)
C6—C7—C8—C9	0.4 (6)	C13—C14—N2—N1	−0.6 (3)
C7—C8—C9—C10	1.3 (5)	C15—C14—N2—N1	175.4 (2)
C7—C8—C9—C11	−177.3 (3)	C13—C14—N2—Pd1	−179.9 (2)
C2—C1—C10—C5	−0.2 (5)	C15—C14—N2—Pd1	−3.9 (3)
C2—C1—C10—C9	178.9 (3)	C12—N1—N2—C14	0.6 (3)
C6—C5—C10—C1	−179.6 (3)	C11—N1—N2—C14	−175.1 (3)
C4—C5—C10—C1	1.1 (5)	C12—N1—N2—Pd1	179.6 (2)
C6—C5—C10—C9	1.3 (5)	C11—N1—N2—Pd1	4.0 (5)
C4—C5—C10—C9	−178.0 (3)	N3—Pd1—N2—C14	2.0 (2)
C8—C9—C10—C1	178.8 (3)	Cl2—Pd1—N2—C14	−178.62 (19)
C11—C9—C10—C1	−2.5 (5)	N3—Pd1—N2—N1	−177.0 (3)
C8—C9—C10—C5	−2.1 (5)	Cl2—Pd1—N2—N1	2.4 (3)
C11—C9—C10—C5	176.6 (3)	C16—C15—N3—C19	1.7 (5)
C8—C9—C11—N1	−5.1 (5)	C14—C15—N3—C19	−176.8 (3)
C10—C9—C11—N1	176.2 (3)	C16—C15—N3—Pd1	176.1 (2)
N1—C12—C13—C14	0.0 (4)	C14—C15—N3—Pd1	−2.4 (3)
C12—C13—C14—N2	0.3 (4)	C18—C19—N3—C15	−0.9 (6)
C12—C13—C14—C15	−174.8 (3)	C18—C19—N3—Pd1	−174.7 (3)
N2—C14—C15—N3	4.2 (4)	N2—Pd1—N3—C15	0.3 (2)
C13—C14—C15—N3	179.2 (3)	Cl1—Pd1—N3—C15	177.6 (2)
N2—C14—C15—C16	−174.3 (3)	N2—Pd1—N3—C19	174.2 (3)
C13—C14—C15—C16	0.7 (6)	Cl1—Pd1—N3—C19	−8.5 (3)
N3—C15—C16—C17	−1.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···Cg1ⁱ	0.93	2.89	3.602	134
C18—H18A···Cg2ⁱⁱ	0.93	3.05	3.803	139

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	[PdCl₂(C₁₉H₁₅N₃)]
M_r	462.64
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.330 (6), 12.139 (8), 15.918 (11)
V (Å³)	1803 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.33
Crystal size (mm)	0.20 × 0.16 × 0.12

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.772, 0.848
No. of measured, independent and observed [I > 2σ(I)] reflections	10453, 3702, 3340
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.054, 1.03
No. of reflections	3702
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.37
Absolute structure	Flack (1983), 1580 Friedel pairs
Absolute structure parameter	0.00 (3)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT (Bruker, 1998, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL (Bruker, 199 and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···Cg1ⁱ	0.93	2.89	3.602	134.4
C18—H18A···Cg2ⁱⁱ	0.93	3.05	3.803	139.4

Symmetry codes: (i) −x+3/2, −y+1, z−1/2; (ii) x+1/2, −y+1/2, −z.

Acknowledgements

This work was supported by the Startup Fund for PhDs in Natural Scientific Research of Zhengzhou University of Light Industry (No. 2008 to C-SL). The authors also thank Nankai University and Henan Provincial Key Laboratory of Surface & Interface Science for supporting this research.

References

Bell, Z. R., Harding, L. P. & Ward, M. D. (2003). Chem. Commun. pp. 2432–2433. Web of Science CSD CrossRef Google Scholar
Bruker (1998). SMART (Version 5.051), SAINT (Version 5.01), SADABS (Version 2.03) and SHELXTL (Version 6.1). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Janiak, C. (2000). J. Chem. Soc. Dalton Trans. pp. 3885–3896. Web of Science CrossRef Google Scholar
Liu, C.-S., Li, J.-R., Zou, R.-Q., Zhou, J.-N., Shi, X.-S., Wang, J.-J. & Bu, X.-H. (2007). J. Mol. Struct. 843, 66–77. Web of Science CSD CrossRef CAS Google Scholar
Liu, C.-S., Zhang, H., Chen, R., Shi, X.-S., Bu, X.-H. & Yang, M. (2007). Chem. Pharm. Bull. 55, 996–1001. Web of Science CSD CrossRef PubMed CAS Google Scholar
Paul, R. L., Argent, S. P., Jeffery, J. C., Harding, L. P., Lynamd, J. M. & Ward, M. D. (2004). J. Chem. Soc. Dalton Trans. pp. 3453–3458. CSD CrossRef Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Singh, S., Mishra, V., Mukherjee, J., Seethalekshmi, N. & Mukherjee, R. (2003). J. Chem. Soc. Dalton Trans. pp. 3392–3397. CSD CrossRef Google Scholar
Sony, S. M. M. & Ponnuswamy, M. N. (2006). Cryst. Growth Des. 6, 736–742. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steel, P. J. (2005). Acc. Chem. Res. 38, 243–250. Web of Science CrossRef PubMed CAS Google Scholar
Ward, M. D., McCleverty, J. A. & Jeffery, J. C. (2001). Coord. Chem. Rev. 222, 251–272. Web of Science CrossRef CAS Google Scholar
Zhang, H., Liu, C.-S., Bu, X.-H. & Yang, M. (2005). J. Inorg. Biochem. 99, 1119–1125. Web of Science CSD CrossRef PubMed CAS Google Scholar
Zou, R.-Q., Bu, X.-H. & Zhang, R.-H. (2004). Inorg. Chem. 43, 5382–5386. Web of Science CSD CrossRef PubMed CAS 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.