Synthesis and Crystal Structures of Nickel(II) and Copper(II) Complexes of Meso‐3,6,6,9‐Tetramethyl‐4,8‐Diazaundecane‐2,10‐Dione Dioxime

Hoong‐Kun ‐K Fun, Tsong‐Jen ‐J Lee, Tahir Tahirov, Tian‐Huey ‐H Lu, Hung Luh, Chung‐Sun ‐S Chung

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Abstract

The nickel(II) and copper(II) complexes of meso‐3,6,6,9‐tetramethyl‐4,8‐diazaundecane‐2,10‐dione dioxime (meso‐HM‐PAO) have an intramolecular hydrogen bond between cis oxime groups. [Cu(meso‐HM‐PAO‐H)(H2O)](NCS) crystallizes in space group P21/n with a = 7.692(1), b = 12.028(2), c=20.235(3) Å, β=93.03(1)°, Z = 4 and Dc=1.46 g/cm3. The final R value for this complex was 0.034 for 2223 observed reflections with I ≥ 2.5σ (I). The Cu(II) coordination is a distorted square pyramid. The Cu(II) ion is five‐coorinated with the diazadioxime N atoms equatorial and water O atom axial. The Cu(II) is 0.12 Å from the equatorial plane towards the hydrate. The equatorial Cu‐N distances span a narrow range, 1.953(3)‐1.999(3) Å. The axial Cu‐O distance is 2.314(3) Å. The thiocyanate group is almost linear. The intramolecular O ⃛O hydrogen bond length is 2.479(4) Å. [Ni(meso‐HM‐PAO‐H)](ClO4) crystallizes in space group P21/c with a = 14.774(3), b = 12.752(3), c = 20.035(4) Å, β = 92.94(3)°, Z = 8 and Dc = 1.51 g/cm3. The final R value for the complex was 0.053 for 4794 observed reflections with F ≥ 4σ (F). The coordination about Ni(II) is a slightly distorted square plane. The Ni(II) ion is 0.0673(7) Å from the best plane of the four donor nitrogen atoms away from the perchlorate ion. The Ni‐N distances span a narrow range 1.863(4)‐1.927(4) Å. There are two molecules per asymmetrical unit resulting in eight molecules being packed in an unit cell; they are bound together by van der Waals interactions. The O‐H ⃛O bonds of these complexes give characteristic infrared absorptions as well as chemical shift of the 1H NMR signal (Ni complex).

Original languageEnglish (US)
Pages (from-to)429-435
Number of pages7
JournalJournal of the Chinese Chemical Society
Volume40
Issue number5
DOIs
StatePublished - Oct 1993

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Nickel
Copper
Crystal structure
Atoms
Hydrogen bonds
Ions
Molecules
Oximes
Infrared absorption
Chemical shift
Bond length
Hydrates
Nitrogen
Nuclear magnetic resonance
Water
perchlorate

Keywords

  • Copper(II) complex
  • Hydrogen bonding
  • Nickel(II) complex
  • X‐ray structure
  • meso‐HM‐PAO

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis and Crystal Structures of Nickel(II) and Copper(II) Complexes of Meso‐3,6,6,9‐Tetramethyl‐4,8‐Diazaundecane‐2,10‐Dione Dioxime. / Fun, Hoong‐Kun ‐K; Lee, Tsong‐Jen ‐J; Tahirov, Tahir; Lu, Tian‐Huey ‐H; Luh, Hung; Chung, Chung‐Sun ‐S.

In: Journal of the Chinese Chemical Society, Vol. 40, No. 5, 10.1993, p. 429-435.

Research output: Contribution to journalArticle

Fun, Hoong‐Kun ‐K ; Lee, Tsong‐Jen ‐J ; Tahirov, Tahir ; Lu, Tian‐Huey ‐H ; Luh, Hung ; Chung, Chung‐Sun ‐S. / Synthesis and Crystal Structures of Nickel(II) and Copper(II) Complexes of Meso‐3,6,6,9‐Tetramethyl‐4,8‐Diazaundecane‐2,10‐Dione Dioxime. In: Journal of the Chinese Chemical Society. 1993 ; Vol. 40, No. 5. pp. 429-435.
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title = "Synthesis and Crystal Structures of Nickel(II) and Copper(II) Complexes of Meso‐3,6,6,9‐Tetramethyl‐4,8‐Diazaundecane‐2,10‐Dione Dioxime",
abstract = "The nickel(II) and copper(II) complexes of meso‐3,6,6,9‐tetramethyl‐4,8‐diazaundecane‐2,10‐dione dioxime (meso‐HM‐PAO) have an intramolecular hydrogen bond between cis oxime groups. [Cu(meso‐HM‐PAO‐H)(H2O)](NCS) crystallizes in space group P21/n with a = 7.692(1), b = 12.028(2), c=20.235(3) {\AA}, β=93.03(1)°, Z = 4 and Dc=1.46 g/cm3. The final R value for this complex was 0.034 for 2223 observed reflections with I ≥ 2.5σ (I). The Cu(II) coordination is a distorted square pyramid. The Cu(II) ion is five‐coorinated with the diazadioxime N atoms equatorial and water O atom axial. The Cu(II) is 0.12 {\AA} from the equatorial plane towards the hydrate. The equatorial Cu‐N distances span a narrow range, 1.953(3)‐1.999(3) {\AA}. The axial Cu‐O distance is 2.314(3) {\AA}. The thiocyanate group is almost linear. The intramolecular O ⃛O hydrogen bond length is 2.479(4) {\AA}. [Ni(meso‐HM‐PAO‐H)](ClO4) crystallizes in space group P21/c with a = 14.774(3), b = 12.752(3), c = 20.035(4) {\AA}, β = 92.94(3)°, Z = 8 and Dc = 1.51 g/cm3. The final R value for the complex was 0.053 for 4794 observed reflections with F ≥ 4σ (F). The coordination about Ni(II) is a slightly distorted square plane. The Ni(II) ion is 0.0673(7) {\AA} from the best plane of the four donor nitrogen atoms away from the perchlorate ion. The Ni‐N distances span a narrow range 1.863(4)‐1.927(4) {\AA}. There are two molecules per asymmetrical unit resulting in eight molecules being packed in an unit cell; they are bound together by van der Waals interactions. The O‐H ⃛O bonds of these complexes give characteristic infrared absorptions as well as chemical shift of the 1H NMR signal (Ni complex).",
keywords = "Copper(II) complex, Hydrogen bonding, Nickel(II) complex, X‐ray structure, meso‐HM‐PAO",
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TY - JOUR

T1 - Synthesis and Crystal Structures of Nickel(II) and Copper(II) Complexes of Meso‐3,6,6,9‐Tetramethyl‐4,8‐Diazaundecane‐2,10‐Dione Dioxime

AU - Fun, Hoong‐Kun ‐K

AU - Lee, Tsong‐Jen ‐J

AU - Tahirov, Tahir

AU - Lu, Tian‐Huey ‐H

AU - Luh, Hung

AU - Chung, Chung‐Sun ‐S

PY - 1993/10

Y1 - 1993/10

N2 - The nickel(II) and copper(II) complexes of meso‐3,6,6,9‐tetramethyl‐4,8‐diazaundecane‐2,10‐dione dioxime (meso‐HM‐PAO) have an intramolecular hydrogen bond between cis oxime groups. [Cu(meso‐HM‐PAO‐H)(H2O)](NCS) crystallizes in space group P21/n with a = 7.692(1), b = 12.028(2), c=20.235(3) Å, β=93.03(1)°, Z = 4 and Dc=1.46 g/cm3. The final R value for this complex was 0.034 for 2223 observed reflections with I ≥ 2.5σ (I). The Cu(II) coordination is a distorted square pyramid. The Cu(II) ion is five‐coorinated with the diazadioxime N atoms equatorial and water O atom axial. The Cu(II) is 0.12 Å from the equatorial plane towards the hydrate. The equatorial Cu‐N distances span a narrow range, 1.953(3)‐1.999(3) Å. The axial Cu‐O distance is 2.314(3) Å. The thiocyanate group is almost linear. The intramolecular O ⃛O hydrogen bond length is 2.479(4) Å. [Ni(meso‐HM‐PAO‐H)](ClO4) crystallizes in space group P21/c with a = 14.774(3), b = 12.752(3), c = 20.035(4) Å, β = 92.94(3)°, Z = 8 and Dc = 1.51 g/cm3. The final R value for the complex was 0.053 for 4794 observed reflections with F ≥ 4σ (F). The coordination about Ni(II) is a slightly distorted square plane. The Ni(II) ion is 0.0673(7) Å from the best plane of the four donor nitrogen atoms away from the perchlorate ion. The Ni‐N distances span a narrow range 1.863(4)‐1.927(4) Å. There are two molecules per asymmetrical unit resulting in eight molecules being packed in an unit cell; they are bound together by van der Waals interactions. The O‐H ⃛O bonds of these complexes give characteristic infrared absorptions as well as chemical shift of the 1H NMR signal (Ni complex).

AB - The nickel(II) and copper(II) complexes of meso‐3,6,6,9‐tetramethyl‐4,8‐diazaundecane‐2,10‐dione dioxime (meso‐HM‐PAO) have an intramolecular hydrogen bond between cis oxime groups. [Cu(meso‐HM‐PAO‐H)(H2O)](NCS) crystallizes in space group P21/n with a = 7.692(1), b = 12.028(2), c=20.235(3) Å, β=93.03(1)°, Z = 4 and Dc=1.46 g/cm3. The final R value for this complex was 0.034 for 2223 observed reflections with I ≥ 2.5σ (I). The Cu(II) coordination is a distorted square pyramid. The Cu(II) ion is five‐coorinated with the diazadioxime N atoms equatorial and water O atom axial. The Cu(II) is 0.12 Å from the equatorial plane towards the hydrate. The equatorial Cu‐N distances span a narrow range, 1.953(3)‐1.999(3) Å. The axial Cu‐O distance is 2.314(3) Å. The thiocyanate group is almost linear. The intramolecular O ⃛O hydrogen bond length is 2.479(4) Å. [Ni(meso‐HM‐PAO‐H)](ClO4) crystallizes in space group P21/c with a = 14.774(3), b = 12.752(3), c = 20.035(4) Å, β = 92.94(3)°, Z = 8 and Dc = 1.51 g/cm3. The final R value for the complex was 0.053 for 4794 observed reflections with F ≥ 4σ (F). The coordination about Ni(II) is a slightly distorted square plane. The Ni(II) ion is 0.0673(7) Å from the best plane of the four donor nitrogen atoms away from the perchlorate ion. The Ni‐N distances span a narrow range 1.863(4)‐1.927(4) Å. There are two molecules per asymmetrical unit resulting in eight molecules being packed in an unit cell; they are bound together by van der Waals interactions. The O‐H ⃛O bonds of these complexes give characteristic infrared absorptions as well as chemical shift of the 1H NMR signal (Ni complex).

KW - Copper(II) complex

KW - Hydrogen bonding

KW - Nickel(II) complex

KW - X‐ray structure

KW - meso‐HM‐PAO

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DO - 10.1002/jccs.199300068

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