Home Physical Sciences The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
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The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2

  • Deng-Zheng Lin , Zi-Yang Zhan , Jia-jun Liang , Zong-Wen Mo ORCID logo EMAIL logo and Hai-Ping Wang ORCID logo EMAIL logo
Published/Copyright: May 27, 2024

Abstract

C12H20N2PdCl2, monoclinic, P21/c (no. 14), a = 16.2780(2) Å, b = 6.97160(10) Å, c = 13.07070(10) Å, β = 102.780(1)°, V = 1446.56(3) Å3, Z = 4, Rgt (F) = 0.0261, wRref (F 2) = 0.0707, T = 291 K.

CCDC no.: 2339923

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Yellow block
Size: 0.15 × 0.13 × 0.12 mm
Wavelength:

μ:
Cu Kα radiation (1.54184 Å)

13.6 mm−1
Diffractometer, scan mode:

θ max, completeness:
XtaLAB Synergy, ω

78.2°, >99 %
N(hkl)measured, N(hkl)unique, R int: 17250, 3009, 0.043
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2835
N(param)refined: 159
Programs: CrysAlisPRO, 1 SHELX , 2 Olex2 3
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
C1 0.56820 (17) 0.7529 (4) 0.6126 (2) 0.0423 (6)
H1 0.551638 0.647948 0.569039 0.051*
C2 0.5107 (2) 0.8943 (5) 0.6173 (3) 0.0519 (7)
H2 0.455837 0.885166 0.577576 0.062*
C3 0.5351 (2) 1.0493 (5) 0.6814 (3) 0.0535 (8)
H3 0.497194 1.147612 0.684795 0.064*
C4 0.6162 (2) 1.0579 (4) 0.7405 (3) 0.0482 (7)
H4 0.633395 1.161500 0.784883 0.058*
C5 0.67182 (17) 0.9117 (3) 0.7335 (2) 0.0326 (5)
C6 0.76145 (16) 0.9151 (3) 0.7930 (2) 0.0326 (5)
H6A 0.763641 0.966486 0.862503 0.039*
H6B 0.793125 1.000921 0.757732 0.039*
C7 0.91021 (18) 0.8196 (4) 0.7008 (2) 0.0433 (6)
H7A 0.877141 0.745401 0.644620 0.065*
H7B 0.968769 0.808004 0.699630 0.065*
H7C 0.893666 0.951872 0.692237 0.065*
C8 0.89612 (15) 0.7465 (4) 0.8047 (2) 0.0337 (5)
H8 0.921952 0.619020 0.815694 0.040*
C9 0.94166 (19) 0.8733 (5) 0.8948 (3) 0.0516 (7)
H9A 0.918161 1.000154 0.886524 0.077*
H9B 1.000481 0.879178 0.894185 0.077*
H9C 0.934978 0.820361 0.960234 0.077*
C10 0.8407 (3) 0.4440 (5) 0.9319 (3) 0.0577 (9)
H10A 0.828732 0.360444 0.872086 0.087*
H10B 0.824486 0.382551 0.990162 0.087*
H10C 0.899963 0.471583 0.949906 0.087*
C11 0.79163 (17) 0.6299 (4) 0.9060 (2) 0.0369 (5)
H11 0.813695 0.720847 0.962622 0.044*
C12 0.6997 (2) 0.5956 (5) 0.9065 (3) 0.0486 (7)
H12A 0.669927 0.715432 0.897343 0.073*
H12B 0.695513 0.539294 0.972165 0.073*
H12C 0.675466 0.510277 0.850226 0.073*
Cl1 0.84432 (5) 0.34255 (9) 0.67609 (6) 0.04822 (18)
Cl2 0.66262 (5) 0.40557 (11) 0.52671 (6) 0.0539 (2)
N1 0.64802 (13) 0.7615 (3) 0.66918 (16) 0.0330 (4)
N2 0.80279 (12) 0.7216 (3) 0.80350 (15) 0.0267 (4)
Pd1 0.73912 (2) 0.56251 (2) 0.67161 (2) 0.02853 (9)

1 Source of materials

All chemicals were purchased from commercial sources and used as received without further purification. N-isopropyl-N-(pyridin-2- ylmethyl)propan-2-amine was prepared by the alkylation reaction between 2-chloromethylpyridine and bis(isopropyl)amine. 4 A solution of N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine (0.01 mmol) in acetonitrile (5 mL) was added to a stirred solution of PdCl2 (0.01 mmol) in acetonitrile (5 mL) at room temperature for 3 h. After filtration, slow diffusion of diethyl ether into the filtrate over 72 h afforded block yellow crystals.

2 Experimental details

SHELXL 2 refinement package were employed to refine the crystal structure. The Olex2 3 was used to visualize the crystal structure. All hydrogen atoms were placed in idealized positions. Their U iso values were set to 1.2U eq of the parent atoms.

3 Comment

It is well known that palladium (Pd) based coordination compounds have been widely used in organic chemistry and pharmaceutical synthesis due to its capability of promoting a myriad of organic transformations both at laboratory and industrial scales. 5 8 In this respect, the coordinated organic ligands play a critical role attributed to their significant influence on the activity and selectivity of Pd-based catalyst. Compared with the classical 2,2′-dipyridine, the chelating ligand including sp2 hybridized nitrogen atoms and sp3 hybridized nitrogen atoms can give rise to more impact on the electron density distribution of Pd-based complexes.

Each Pd(II) shows a tetrahedral geometry and is ligated by one N atom from one pyridine, one N atom from di-isopropylamine, and two chlorine atoms. The Pd–Cl bond lengths range from 2.2898(7) to 2.3003(7) Å, while the Pd–N bond lengths range from 2.026(2) to 2.1179(18) Å. The Cl–Pd–Cl, and N–Pd–N angles are 88.18(3) and 83.04(8)°, respectively, while those for N–Pd–Cl are 92.96(6) and 178.71(6)°. The C–N–Pd angles range from 105.52(14) to 126.34(19)°. It should be noted that the above bond lengths and angles are consistent with the reported Pd-based complexes. 9 12


Corresponding author: Zong-Wen Mo and Hai-Ping Wang, Jiangmen Key Laboratory of Synthetic Chemistry and Cleaner Production, School of Environmental and Chemical Engineering, Wuyi University, Jiangmen, Guangdong 529020, P.R. China, E-mail: (Z.-W. Mo), (H.-P. Wang)

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: NSFC of China (21703291), the NSF of Guangdong Province (2017A030310258), the Youth Foundation for Team of Wuyi University (2019td07) and Jiangmen Municipal Science and Technology Bureau (Jiangke 2020-135, Jiangke 2021-76).

  3. Competing interests: The authors declare no conflicts of interest regarding this article.

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Received: 2024-03-31
Accepted: 2024-04-30
Published Online: 2024-05-27
Published in Print: 2024-08-27

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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