Literature DB >> 21579287

Dichlorido{(E)-2,4,6-trimethyl-N-[phen-yl(2-pyridyl)methyl-idene]aniline-κN,N'}palladium(II).

Cheng-Hsien Yang, Ya-Liu Peng, Mei-Hua Wang, Kuo-Chen Shih, Mao-Lin Hsueh.   

Abstract

The title complex, [PdCl(2)(C(21)H(20)N(2))], contains a Pd(II) atom in a slightly distorted square-planar coordination environment defined by two N atoms from one 2,4,6-trimethyl-N-[phen-yl(2-pyrid-yl)methyl-idene]aniline ligand and two Cl atoms, forming a five-membered ring (N-Pd-N-C-C).

Entities:  

Year:  2010        PMID： 21579287      PMCID： PMC2979545          DOI： 10.1107/S1600536810016466

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


Related literature

For the synthesis of pyridyl-imine ligands, see: Meneghetti et al. (1999 ▶). For the design and synthesis of metal-organic frameworks, see: Lai et al. (2005 ▶); Pelagattia et al. (2005 ▶); Zhang et al. (2008 ▶). For related structures, see: Hsueh et al. (2006 ▶); Zhang et al. (2008 ▶). For the application of the title compound in Suzuki–Miyaura reactions, see: Li (2003 ▶); Miyaura & Suzuki (1995 ▶); Na et al. (2004 ▶); Nicolaou et al. (2005 ▶); Rajagopal et al. (2002 ▶); Tomioka et al. (2004 ▶).

Experimental

Crystal data

[PdCl2(C21H20N2)] M = 477.69 Orthorhombic, a = 7.4807 (6) Å b = 15.1483 (13) Å c = 17.7147 (15) Å V = 2007.4 (3) Å3 Z = 4 Mo Kα radiation μ = 1.20 mm−1 T = 298 K 0.35 × 0.33 × 0.22 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.738, T max = 1.000 11233 measured reflections 3956 independent reflections 3871 reflections with I > 2σ(I) R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.019 wR(F 2) = 0.052 S = 1.01 3956 reflections 238 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.52 e Å−3 Absolute structure: Flack (1983 ▶), 1670 Friedel pairs Flack parameter: 0.02 (2) Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016466/pk2244sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016466/pk2244Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[PdCl2(C21H20N2)]F(000) = 960
Mr = 477.69Dx = 1.581 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4812 reflections
a = 7.4807 (6) Åθ = 2.9–2.6°
b = 15.1483 (13) ŵ = 1.20 mm−1
c = 17.7147 (15) ÅT = 298 K
V = 2007.4 (3) Å3Parallelpiped, yellow
Z = 40.35 × 0.33 × 0.22 mm
Bruker SMART 1000 CCD diffractometer3956 independent reflections
Radiation source: fine-focus sealed tube3871 reflections with I > 2σ(I)
graphiteRint = 0.024
φ and ω scansθmax = 26.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→9
Tmin = 0.738, Tmax = 1.000k = −16→18
11233 measured reflectionsl = −21→15
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.052w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.002
3956 reflectionsΔρmax = 0.20 e Å−3
238 parametersΔρmin = −0.52 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1670 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (2)
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Pd10.262038 (18)0.612368 (9)0.476057 (8)0.02890 (6)
Cl10.41648 (8)0.68412 (4)0.56891 (3)0.04639 (14)
Cl20.19993 (9)0.49999 (4)0.55734 (3)0.04722 (15)
N10.3065 (2)0.70552 (11)0.39625 (10)0.0321 (4)
N20.1064 (2)0.56451 (11)0.39132 (10)0.0308 (3)
C10.4227 (3)0.77241 (15)0.39906 (14)0.0424 (5)
H1A0.49740.77760.44080.051*
C20.4354 (4)0.83417 (17)0.34181 (16)0.0527 (6)
H2A0.51910.87940.34460.063*
C30.3231 (4)0.82774 (16)0.28102 (14)0.0498 (6)
H3A0.32740.86960.24260.060*
C40.2022 (3)0.75775 (15)0.27725 (13)0.0418 (5)
H4A0.12580.75180.23620.050*
C50.1982 (3)0.69758 (13)0.33577 (11)0.0314 (4)
C60.0837 (3)0.61804 (13)0.33544 (11)0.0302 (4)
C7−0.0452 (3)0.60379 (14)0.27275 (12)0.0344 (4)
C8−0.2010 (4)0.65290 (18)0.27039 (14)0.0493 (6)
H8A−0.22340.69500.30740.059*
C9−0.3241 (4)0.6395 (2)0.21285 (17)0.0622 (8)
H9A−0.43060.67120.21230.075*
C10−0.2883 (4)0.5791 (2)0.15659 (15)0.0594 (7)
H10A−0.37040.57010.11790.071*
C11−0.1303 (5)0.5321 (2)0.15769 (16)0.0674 (8)
H11A−0.10520.49240.11910.081*
C12−0.0104 (4)0.54350 (19)0.21532 (15)0.0526 (7)
H12A0.09480.51080.21610.063*
C130.0126 (3)0.48204 (13)0.39711 (12)0.0316 (4)
C14−0.1580 (3)0.48020 (14)0.42893 (12)0.0364 (5)
C15−0.2372 (3)0.39752 (15)0.43887 (13)0.0451 (5)
H15A−0.35130.39460.45960.054*
C16−0.1526 (4)0.32013 (15)0.41912 (13)0.0513 (7)
C170.0171 (4)0.32429 (15)0.38896 (14)0.0469 (6)
H17A0.07570.27230.37610.056*
C180.1027 (3)0.40533 (14)0.37726 (13)0.0392 (5)
C19−0.2509 (4)0.56211 (18)0.45550 (16)0.0563 (6)
H19A−0.34510.54640.48970.084*
H19B−0.30040.59280.41290.084*
H19C−0.16670.59970.48080.084*
C20−0.2428 (7)0.23101 (19)0.43118 (19)0.0839 (11)
H20A−0.36720.23990.44210.126*
H20B−0.18710.20110.47270.126*
H20C−0.23100.19590.38630.126*
C210.2913 (4)0.40809 (18)0.34700 (18)0.0607 (7)
H21A0.35150.45920.36640.091*
H21B0.28820.41090.29290.091*
H21C0.35410.35590.36250.091*
U11U22U33U12U13U23
Pd10.02800 (8)0.02850 (8)0.03020 (9)0.00077 (6)−0.00266 (6)−0.00482 (5)
Cl10.0497 (3)0.0470 (3)0.0424 (3)−0.0033 (2)−0.0130 (3)−0.0131 (2)
Cl20.0583 (4)0.0409 (3)0.0424 (3)−0.0035 (2)−0.0076 (3)0.0079 (2)
N10.0311 (9)0.0286 (8)0.0366 (9)−0.0025 (7)0.0017 (7)−0.0065 (7)
N20.0283 (8)0.0309 (8)0.0331 (9)−0.0014 (7)0.0009 (7)−0.0058 (7)
C10.0406 (12)0.0392 (12)0.0472 (13)−0.0095 (10)−0.0008 (11)−0.0067 (10)
C20.0574 (16)0.0424 (13)0.0583 (15)−0.0211 (12)0.0032 (13)−0.0013 (12)
C30.0617 (16)0.0399 (13)0.0478 (13)−0.0088 (12)0.0065 (12)0.0057 (11)
C40.0473 (14)0.0419 (12)0.0360 (11)−0.0059 (10)−0.0007 (10)0.0045 (9)
C50.0307 (10)0.0310 (10)0.0325 (10)−0.0008 (8)0.0022 (8)−0.0056 (8)
C60.0313 (10)0.0280 (9)0.0313 (10)0.0004 (9)0.0013 (8)−0.0044 (8)
C70.0379 (11)0.0348 (10)0.0306 (10)−0.0073 (9)−0.0021 (8)−0.0017 (8)
C80.0466 (15)0.0562 (14)0.0450 (13)0.0096 (12)−0.0083 (11)−0.0094 (11)
C90.0431 (14)0.079 (2)0.0646 (18)0.0041 (13)−0.0127 (13)0.0015 (15)
C100.0598 (18)0.0728 (18)0.0457 (14)−0.0164 (14)−0.0216 (13)−0.0035 (13)
C110.076 (2)0.082 (2)0.0443 (15)−0.0021 (17)−0.0119 (15)−0.0287 (15)
C120.0534 (15)0.0607 (16)0.0439 (14)0.0069 (12)−0.0049 (11)−0.0176 (12)
C130.0360 (11)0.0277 (10)0.0309 (10)−0.0030 (8)−0.0043 (8)−0.0030 (8)
C140.0372 (11)0.0379 (11)0.0342 (11)−0.0042 (9)−0.0007 (9)−0.0016 (9)
C150.0440 (12)0.0521 (13)0.0392 (11)−0.0149 (12)−0.0013 (10)0.0018 (9)
C160.081 (2)0.0354 (12)0.0378 (12)−0.0186 (12)−0.0085 (12)0.0033 (10)
C170.0682 (17)0.0292 (11)0.0433 (13)−0.0007 (11)−0.0094 (12)−0.0043 (10)
C180.0442 (12)0.0351 (11)0.0383 (12)0.0021 (9)−0.0060 (9)−0.0054 (9)
C190.0447 (13)0.0544 (14)0.0696 (15)0.0053 (12)0.0157 (13)−0.0040 (12)
C200.130 (3)0.0479 (15)0.0738 (19)−0.040 (2)0.011 (3)0.0052 (14)
C210.0497 (15)0.0511 (15)0.0814 (19)0.0127 (12)0.0105 (14)−0.0107 (14)
Pd1—N12.0250 (18)C10—H10A0.9300
Pd1—N22.0334 (17)C11—C121.370 (4)
Pd1—Cl22.2776 (6)C11—H11A0.9300
Pd1—Cl12.2851 (5)C12—H12A0.9300
N1—C11.336 (3)C13—C181.389 (3)
N1—C51.348 (3)C13—C141.396 (3)
N2—C61.291 (3)C14—C151.397 (3)
N2—C131.436 (3)C14—C191.498 (3)
C1—C21.383 (4)C15—C161.377 (4)
C1—H1A0.9300C15—H15A0.9300
C2—C31.369 (4)C16—C171.378 (4)
C2—H2A0.9300C16—C201.525 (3)
C3—C41.395 (3)C17—C181.400 (3)
C3—H3A0.9300C17—H17A0.9300
C4—C51.381 (3)C18—C211.509 (4)
C4—H4A0.9300C19—H19A0.9600
C5—C61.479 (3)C19—H19B0.9600
C6—C71.486 (3)C19—H19C0.9600
C7—C81.384 (3)C20—H20A0.9600
C7—C121.392 (3)C20—H20B0.9600
C8—C91.389 (4)C20—H20C0.9600
C8—H8A0.9300C21—H21A0.9600
C9—C101.379 (4)C21—H21B0.9600
C9—H9A0.9300C21—H21C0.9600
C10—C111.380 (5)
N1—Pd1—N280.04 (7)C10—C11—C12120.4 (3)
N1—Pd1—Cl2174.72 (5)C10—C11—H11A119.8
N2—Pd1—Cl294.79 (5)C12—C11—H11A119.8
N1—Pd1—Cl195.05 (5)C11—C12—C7120.3 (3)
N2—Pd1—Cl1172.09 (5)C11—C12—H12A119.8
Cl2—Pd1—Cl190.21 (2)C7—C12—H12A119.8
C1—N1—C5119.2 (2)C18—C13—C14122.0 (2)
C1—N1—Pd1127.55 (16)C18—C13—N2118.19 (19)
C5—N1—Pd1113.20 (13)C14—C13—N2119.53 (18)
C6—N2—C13122.46 (17)C15—C14—C13117.2 (2)
C6—N2—Pd1114.68 (13)C15—C14—C19120.4 (2)
C13—N2—Pd1122.48 (13)C13—C14—C19122.3 (2)
N1—C1—C2122.0 (2)C16—C15—C14122.4 (2)
N1—C1—H1A119.0C16—C15—H15A118.8
C2—C1—H1A119.0C14—C15—H15A118.8
C3—C2—C1119.1 (2)C15—C16—C17118.9 (2)
C3—C2—H2A120.5C15—C16—C20121.0 (3)
C1—C2—H2A120.5C17—C16—C20120.2 (3)
C2—C3—C4119.3 (2)C18—C17—C16121.3 (2)
C2—C3—H3A120.3C18—C17—H17A119.4
C4—C3—H3A120.3C16—C17—H17A119.4
C5—C4—C3118.7 (2)C13—C18—C17118.3 (2)
C5—C4—H4A120.7C13—C18—C21121.4 (2)
C3—C4—H4A120.7C17—C18—C21120.3 (2)
N1—C5—C4121.65 (19)C14—C19—H19A109.5
N1—C5—C6115.08 (18)C14—C19—H19B109.5
C4—C5—C6123.19 (19)H19A—C19—H19B109.5
N2—C6—C5115.63 (17)C14—C19—H19C109.5
N2—C6—C7124.55 (18)H19A—C19—H19C109.5
C5—C6—C7119.82 (17)H19B—C19—H19C109.5
C8—C7—C12119.2 (2)C16—C20—H20A109.5
C8—C7—C6119.40 (19)C16—C20—H20B109.5
C12—C7—C6121.3 (2)H20A—C20—H20B109.5
C7—C8—C9120.1 (2)C16—C20—H20C109.5
C7—C8—H8A119.9H20A—C20—H20C109.5
C9—C8—H8A119.9H20B—C20—H20C109.5
C8—C9—C10119.9 (3)C18—C21—H21A109.5
C8—C9—H9A120.0C18—C21—H21B109.5
C10—C9—H9A120.0H21A—C21—H21B109.5
C11—C10—C9119.9 (2)C18—C21—H21C109.5
C11—C10—H10A120.0H21A—C21—H21C109.5
C9—C10—H10A120.0H21B—C21—H21C109.5
  5 in total

1.  Suzuki reaction takes a "naked hot bath": coupling in high-temperature water without transition metals.

Authors:  Chao-Jun Li
Journal:  Angew Chem Int Ed Engl       Date:  2003-10-20       Impact factor: 15.336

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Ultrasound promoted Suzuki cross-coupling reactions in ionic liquid at ambient conditions.

Authors:  R Rajagopal; Dilip V Jarikote; K V Srinivasan
Journal:  Chem Commun (Camb)       Date:  2002-03-21       Impact factor: 6.222

4.  Ruthenium-catalyzed Heck-type olefination and Suzuki coupling reactions: studies on the nature of catalytic species.

Authors:  Youngim Na; Soyoung Park; Soo Bong Han; Hoon Han; Sangwon Ko; Sukbok Chang
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419

5.  Preparation of oligodiazo compounds by using the suzuki coupling reaction and characterization of their photoproducts.

Authors:  Tetsuji Itoh; Katsuyuki Hirai; Hideo Tomioka
Journal:  J Am Chem Soc       Date:  2004-02-04       Impact factor: 15.419
  5 in total
  1 in total

1.  Crystal structure of {N-[(6-bromo-pyridin-2-yl)(phen-yl)methyl-idene]-2,6-di-methyl-aniline-κ2N,N'}di-chlorido-zinc di-chloro-methane hemisolvate.

Authors:  Bradley M Wile
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2017-06-02
  1 in total

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