Literature DB >> 21200638

Dichlorido[1-(1-naphthyl-meth-yl)-3-(2-pyrid-yl)-1H-pyrazole-κN,N]palladium(II).

Chun-Sen Liu, Guang-Hui Sun, Liang-Qi Guo.   

Abstract

In the title compound, [PdCl(2)(C(19)H(15)N(3))], the Pd(II) centre is four-coordinated by two N-atom donors from one 1-[3-(2-pyrid-yl)pyrazol-1-ylmeth-yl]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 inter-molecular C-H⋯π inter-actions involving the benzene and pyridine rings of different L ligands and π-π stacking inter-actions between the pyrazolyl-pyridine and naphthalene rings of neighbouring L ligands, with a centroid-centroid separation of 3.522 (1) Å.

Entities:  

Year:  2007        PMID： 21200638      PMCID： PMC2914949          DOI： 10.1107/S1600536807062927

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 462.64 Orthorhombic, 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[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.054 S = 1.03 3702 reflections 226 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.37 e Å−3 Absolute structure: Flack (1983 ▶), 1580 Friedel pairs Flack parameter: 0.00 (3) 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 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062927/bi2262sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062927/bi2262Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[PdCl2(C19H15N3)]F000 = 920
Mr = 462.64Dx = 1.705 Mg m−3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 970 reflections
a = 9.330 (6) Åθ = 3.4–26.4º
b = 12.139 (8) ŵ = 1.33 mm−1
c = 15.918 (11) ÅT = 293 (2) K
V = 1803 (2) Å3Block, yellow
Z = 40.20 × 0.16 × 0.12 mm
Bruker SMART CCD diffractometer3702 independent reflections
Radiation source: fine-focus sealed tube3340 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 293(2) Kθmax = 26.5º
ω scansθmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 1998)h = −10→11
Tmin = 0.772, Tmax = 0.848k = −14→15
10453 measured reflectionsl = −19→15
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.024  w = 1/[σ2(Fo2) + (0.0227P)2 + 0.3859P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.054(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.27 e Å−3
3702 reflectionsΔρmin = −0.37 e Å−3
226 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1580 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.00 (3)
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.
xyzUiso*/Ueq
Pd10.83064 (2)0.490954 (17)0.051890 (13)0.03837 (7)
C10.5698 (4)0.9043 (3)0.1086 (3)0.0546 (9)
H1A0.63810.90010.06620.065*
C20.5637 (4)0.9961 (3)0.1585 (3)0.0654 (10)
H2A0.62811.05340.14980.079*
C30.4620 (4)1.0044 (4)0.2221 (2)0.0704 (12)
H3A0.45891.06700.25570.084*
C40.3679 (4)0.9219 (4)0.2351 (2)0.0651 (11)
H4A0.29930.92900.27710.078*
C50.3714 (3)0.8245 (3)0.1859 (2)0.0511 (9)
C60.2756 (4)0.7376 (4)0.1995 (2)0.0639 (11)
H6A0.20780.74330.24210.077*
C70.2800 (4)0.6453 (3)0.1516 (3)0.0613 (10)
H7A0.21680.58780.16220.074*
C80.3806 (4)0.6365 (3)0.0856 (2)0.0505 (8)
H8A0.38240.57300.05300.061*
C90.4752 (3)0.7192 (2)0.0689 (2)0.0408 (7)
C100.4739 (3)0.8161 (3)0.1208 (2)0.0430 (7)
C110.5803 (3)0.7164 (2)−0.0027 (2)0.0444 (8)
H11A0.55760.7758−0.04120.053*
H11B0.67560.73010.01930.053*
C120.5032 (4)0.5886 (3)−0.1173 (2)0.0534 (8)
H12A0.43230.6329−0.14060.064*
C130.5448 (3)0.4872 (3)−0.1465 (2)0.0512 (8)
H13A0.50900.4492−0.19270.061*
C140.6522 (3)0.4540 (2)−0.09185 (19)0.0397 (7)
C150.7469 (3)0.3595 (2)−0.0911 (2)0.0394 (7)
C160.7465 (4)0.2785 (3)−0.1518 (2)0.0479 (8)
H16A0.67990.2806−0.19520.058*
C170.8446 (4)0.1953 (3)−0.1477 (3)0.0612 (10)
H17A0.84590.1404−0.18850.073*
C180.9416 (5)0.1935 (3)−0.0826 (3)0.0675 (13)
H18A1.00960.1377−0.07890.081*
C190.9366 (4)0.2753 (3)−0.0231 (3)0.0619 (11)
H19A1.00220.27400.02090.074*
N10.5823 (3)0.6132 (2)−0.04930 (19)0.0434 (6)
N20.6739 (3)0.53078 (17)−0.03249 (14)0.0378 (5)
N30.8397 (3)0.35759 (19)−0.02653 (16)0.0438 (6)
Cl11.00048 (11)0.42155 (9)0.13879 (7)0.0708 (3)
Cl20.81909 (11)0.64162 (6)0.13707 (5)0.0521 (2)
U11U22U33U12U13U23
Pd10.03920 (11)0.03896 (11)0.03696 (11)0.00037 (11)0.00213 (10)0.00045 (11)
C10.058 (2)0.0449 (19)0.060 (2)0.0110 (17)−0.0040 (18)0.0000 (17)
C20.075 (2)0.0455 (19)0.076 (3)0.013 (2)−0.024 (2)−0.010 (2)
C30.077 (3)0.066 (3)0.068 (2)0.035 (3)−0.030 (2)−0.022 (2)
C40.062 (3)0.083 (3)0.051 (2)0.038 (2)−0.0089 (18)−0.015 (2)
C50.043 (2)0.064 (2)0.045 (2)0.0218 (16)−0.0049 (15)0.0039 (17)
C60.054 (2)0.091 (3)0.047 (2)0.019 (2)0.0085 (18)0.009 (2)
C70.052 (2)0.067 (3)0.065 (3)−0.0033 (18)0.0031 (19)0.016 (2)
C80.0479 (19)0.0458 (18)0.058 (2)0.0036 (15)−0.0020 (16)0.0069 (16)
C90.0423 (17)0.0381 (15)0.0422 (19)0.0102 (13)0.0011 (15)0.0071 (13)
C100.0429 (18)0.0443 (17)0.0417 (18)0.0133 (14)−0.0067 (14)−0.0004 (14)
C110.0485 (19)0.0372 (17)0.048 (2)0.0078 (15)0.0034 (15)0.0021 (16)
C120.056 (2)0.060 (2)0.045 (2)0.0141 (18)−0.0071 (18)0.0007 (16)
C130.0554 (18)0.057 (2)0.0416 (17)0.0038 (19)−0.0077 (14)−0.0047 (18)
C140.0411 (17)0.0422 (15)0.0357 (16)−0.0023 (14)0.0045 (14)0.0002 (12)
C150.0440 (18)0.0360 (16)0.0381 (18)−0.0043 (14)0.0079 (14)0.0011 (13)
C160.058 (2)0.0444 (19)0.041 (2)−0.0048 (15)0.0079 (16)−0.0053 (15)
C170.075 (3)0.0427 (18)0.065 (2)0.005 (2)0.015 (3)−0.0149 (16)
C180.074 (3)0.055 (2)0.073 (3)0.022 (2)−0.002 (2)−0.013 (2)
C190.070 (3)0.054 (2)0.062 (3)0.0214 (19)−0.011 (2)−0.0067 (17)
N10.0465 (15)0.0424 (13)0.0414 (15)0.0105 (11)0.0035 (13)0.0016 (14)
N20.0408 (12)0.0366 (11)0.0361 (13)0.0021 (11)0.0040 (11)0.0018 (9)
N30.0489 (15)0.0385 (12)0.0440 (15)0.0071 (14)0.0022 (14)0.0013 (10)
Cl10.0659 (6)0.0788 (6)0.0677 (6)0.0211 (5)−0.0224 (5)−0.0102 (5)
Cl20.0678 (5)0.0452 (4)0.0435 (4)−0.0047 (4)0.0009 (5)−0.0056 (3)
Pd1—N22.043 (3)C9—C111.504 (5)
Pd1—N32.046 (3)C11—N11.456 (4)
Pd1—Cl12.2658 (14)C11—H11A0.970
Pd1—Cl22.2792 (14)C11—H11B0.970
C1—C21.370 (5)C12—N11.343 (5)
C1—C101.408 (5)C12—C131.372 (5)
C1—H1A0.930C12—H12A0.930
C2—C31.390 (6)C13—C141.387 (4)
C2—H2A0.930C13—H13A0.930
C3—C41.347 (6)C14—N21.342 (4)
C3—H3A0.930C14—C151.448 (4)
C4—C51.418 (5)C15—N31.343 (4)
C4—H4A0.930C15—C161.379 (4)
C5—C61.399 (5)C16—C171.365 (5)
C5—C101.414 (5)C16—H16A0.930
C6—C71.356 (6)C17—C181.377 (6)
C6—H6A0.930C17—H17A0.930
C7—C81.413 (5)C18—C191.373 (5)
C7—H7A0.930C18—H18A0.930
C8—C91.363 (5)C19—N31.348 (4)
C8—H8A0.930C19—H19A0.930
C9—C101.438 (4)N1—N21.343 (3)
N2—Pd1—N379.38 (10)C9—C11—H11A108.7
N2—Pd1—Cl1171.74 (7)N1—C11—H11B108.7
N3—Pd1—Cl192.83 (9)C9—C11—H11B108.7
N2—Pd1—Cl299.63 (7)H11A—C11—H11B107.6
N3—Pd1—Cl2178.86 (7)N1—C12—C13108.5 (3)
Cl1—Pd1—Cl288.18 (5)N1—C12—H12A125.8
C2—C1—C10120.8 (4)C13—C12—H12A125.8
C2—C1—H1A119.6C12—C13—C14104.6 (3)
C10—C1—H1A119.6C12—C13—H13A127.7
C1—C2—C3120.6 (4)C14—C13—H13A127.7
C1—C2—H2A119.7N2—C14—C13110.4 (3)
C3—C2—H2A119.7N2—C14—C15116.8 (3)
C4—C3—C2120.2 (4)C13—C14—C15132.6 (3)
C4—C3—H3A119.9N3—C15—C16121.7 (3)
C2—C3—H3A119.9N3—C15—C14114.4 (3)
C3—C4—C5121.3 (4)C16—C15—C14123.9 (3)
C3—C4—H4A119.3C17—C16—C15119.5 (4)
C5—C4—H4A119.3C17—C16—H16A120.2
C6—C5—C10119.4 (3)C15—C16—H16A120.2
C6—C5—C4121.9 (4)C16—C17—C18119.2 (3)
C10—C5—C4118.6 (4)C16—C17—H17A120.4
C7—C6—C5121.1 (4)C18—C17—H17A120.4
C7—C6—H6A119.5C19—C18—C17119.1 (4)
C5—C6—H6A119.5C19—C18—H18A120.5
C6—C7—C8120.1 (4)C17—C18—H18A120.5
C6—C7—H7A120.0N3—C19—C18122.0 (4)
C8—C7—H7A120.0N3—C19—H19A119.0
C9—C8—C7121.3 (3)C18—C19—H19A119.0
C9—C8—H8A119.4C12—N1—N2110.2 (3)
C7—C8—H8A119.4C12—N1—C11126.5 (3)
C8—C9—C10119.0 (3)N2—N1—C11123.2 (3)
C8—C9—C11123.6 (3)C14—N2—N1106.3 (2)
C10—C9—C11117.3 (3)C14—N2—Pd1113.99 (19)
C1—C10—C5118.5 (3)N1—N2—Pd1139.7 (2)
C1—C10—C9122.5 (3)C15—N3—C19118.4 (3)
C5—C10—C9119.1 (3)C15—N3—Pd1115.2 (2)
N1—C11—C9114.4 (3)C19—N3—Pd1126.1 (2)
N1—C11—H11A108.7
C10—C1—C2—C3−0.3 (5)C14—C15—C16—C17176.9 (3)
C1—C2—C3—C4−0.2 (6)C15—C16—C17—C180.4 (6)
C2—C3—C4—C51.1 (6)C16—C17—C18—C190.3 (6)
C3—C4—C5—C6179.1 (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—C70.4 (5)C13—C12—N1—C11175.1 (3)
C4—C5—C6—C7179.6 (4)C9—C11—N1—C1290.9 (4)
C5—C6—C7—C8−1.2 (6)C9—C11—N1—N2−94.1 (3)
C6—C7—C8—C90.4 (6)C13—C14—N2—N1−0.6 (3)
C7—C8—C9—C101.3 (5)C15—C14—N2—N1175.4 (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—C9178.9 (3)C12—N1—N2—C140.6 (3)
C6—C5—C10—C1−179.6 (3)C11—N1—N2—C14−175.1 (3)
C4—C5—C10—C11.1 (5)C12—N1—N2—Pd1179.6 (2)
C6—C5—C10—C91.3 (5)C11—N1—N2—Pd14.0 (5)
C4—C5—C10—C9−178.0 (3)N3—Pd1—N2—C142.0 (2)
C8—C9—C10—C1178.8 (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—N12.4 (3)
C11—C9—C10—C5176.6 (3)C16—C15—N3—C191.7 (5)
C8—C9—C11—N1−5.1 (5)C14—C15—N3—C19−176.8 (3)
C10—C9—C11—N1176.2 (3)C16—C15—N3—Pd1176.1 (2)
N1—C12—C13—C140.0 (4)C14—C15—N3—Pd1−2.4 (3)
C12—C13—C14—N20.3 (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—N34.2 (4)N2—Pd1—N3—C150.3 (2)
C13—C14—C15—N3179.2 (3)Cl1—Pd1—N3—C15177.6 (2)
N2—C14—C15—C16−174.3 (3)N2—Pd1—N3—C19174.2 (3)
C13—C14—C15—C160.7 (6)Cl1—Pd1—N3—C19−8.5 (3)
N3—C15—C16—C17−1.5 (5)
D—H···AD—HH···AD···AD—H···A
C17—H17A···Cg1i0.932.893.602134
C18—H18A···Cg2ii0.933.053.803139
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C17—H17A⋯Cg1i0.932.893.602134
C18—H18A⋯Cg2ii0.933.053.803139

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of atoms C1–C5/C10 and Cg2 is the centroid of atoms Pd1/N2/C14/C15/N3.

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