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Crystal structure of ortho-rhom-bic {bis-[(pyridin-2-yl)meth-yl](3,5,5,5-tetra-chloro-pent-yl)amine-κ(3) N,N',N''}chlorido-copper(II) perchlorate.

Bussey KA, Cavalier AR, Connell JR, Mraz ME, Oshin KD, Pintauer T, Gray DL, Parkin S - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The perchlorate counter-ion is disordered over three sets of sites with refined occupancies 0.0634 (17), 0.221 (16) and 0.145 (7).In addition, the hetero-scorpionate arm of the bis-[(pyridin-2-yl)meth-yl](3,5,5,5-tetra-chloro-pent-yl)amine ligand is disordered over two sets of sites with refined occupancies 0.839 (2) and 0.161 (2).In the crystal, weak Cu⋯Cl inter-actions between symmetry-related mol-ecules create a dimerization with a chloride occupying the apical position of the square-pyramidal geometry typical of many copper(II) chloride hetero-scorpionate complexes.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry & Physics, Saint Mary's College, Notre Dame, IN 46556, USA.

ABSTRACT
In the title compound, [CuCl(C17H19Cl4N3)]ClO4, the Cu(II) ion adopts a distorted square-planar geometry defined by one chloride ligand and the three nitro-gen atoms from the bis-[(pyridin-2-yl)meth-yl](3,5,5,5-tetra-chloro-pent-yl)amine ligand. The perchlorate counter-ion is disordered over three sets of sites with refined occupancies 0.0634 (17), 0.221 (16) and 0.145 (7). In addition, the hetero-scorpionate arm of the bis-[(pyridin-2-yl)meth-yl](3,5,5,5-tetra-chloro-pent-yl)amine ligand is disordered over two sets of sites with refined occupancies 0.839 (2) and 0.161 (2). In the crystal, weak Cu⋯Cl inter-actions between symmetry-related mol-ecules create a dimerization with a chloride occupying the apical position of the square-pyramidal geometry typical of many copper(II) chloride hetero-scorpionate complexes.

No MeSH data available.


The synthetic scheme.
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fig4: The synthetic scheme.

Mentions: The synthetic procedure is outlined in Fig. 4 ▸. Synthesis of 1-butene-bis(pyridin-2-ylmeth­yl)amine, (B): bis­(pyridin-2-ylmeth­yl) amine (BPMA) precursor (A) was synthesized and purified following literature procedures (Carvalho et al., 2006 ▸). BPMA (8.064 g, 40.5 mmol) was dissolved in 15 mL of aceto­nitrile followed by the addition of tri­ethyl­amine (4.098 g, 40.5 mmol) and 4-bromo­butene (5.468 g 40.5 mmol). The reaction was sealed and allowed to mix for 4 days to ensure complete deprotonation and coupling occurred. Generation of the tri­ethyl­amine hydrogen bromide salt Et3NH+·Br− was observed as white crystals in the brown-colored solution. The mixture was filtered and the desired product extracted from the filtrate using a hexa­ne/water mixture. The hexane layer was separated and solvent removed to yield the ligand as a yellow-colored oil (8.516 g, 83%). The ligand was stored in a septum sealed round-bottom flask under argon gas in a refrigerator. 1H NMR (CDCl3, 400 MHz): δ2.31 (dd, J = 8.0 and 21.6 Hz, 2H), δ2.64 (t, J = 7.2 Hz, 2H), δ3.83 (s, 4H), δ4.97 (d, J = 10.4 Hz, 1H), δ5.01 (d, J = 18.8 Hz, 1H), δ5.75 (m, J = 10.4 Hz, 1H), δ7.13 (t, J = 6.4 Hz, 2H), δ 7.53 (d, J = 8.0 Hz, 2H), δ 7.64 (t, J = 7.6 Hz, 2H), δ8.51 (d, J = 4.4 Hz, 2H). 13C NMR (CDCl3, 400 MHz): δ 159.75, 149.01, 136.38, 135.38, 122.80, 121.88, 117.93, 77.13, 59.90, 57.32. FT–IR (liquid): v (cm−1) = 3066 (w), 2922 (w), 2816 (w), 2158 (s), 1639 (s), 1588 (s), 1361 (s), 994 (w), 756 (s). FT–IR (solid): v (cm−1) = 3394 (w), 3067 (w), 3008 (s), 2923 (w), 2817 (s), 2359 (s), 1619 (s), 1589 (s), 1432 (s).


Crystal structure of ortho-rhom-bic {bis-[(pyridin-2-yl)meth-yl](3,5,5,5-tetra-chloro-pent-yl)amine-κ(3) N,N',N''}chlorido-copper(II) perchlorate.

Bussey KA, Cavalier AR, Connell JR, Mraz ME, Oshin KD, Pintauer T, Gray DL, Parkin S - Acta Crystallogr E Crystallogr Commun (2015)

The synthetic scheme.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518935&req=5

fig4: The synthetic scheme.
Mentions: The synthetic procedure is outlined in Fig. 4 ▸. Synthesis of 1-butene-bis(pyridin-2-ylmeth­yl)amine, (B): bis­(pyridin-2-ylmeth­yl) amine (BPMA) precursor (A) was synthesized and purified following literature procedures (Carvalho et al., 2006 ▸). BPMA (8.064 g, 40.5 mmol) was dissolved in 15 mL of aceto­nitrile followed by the addition of tri­ethyl­amine (4.098 g, 40.5 mmol) and 4-bromo­butene (5.468 g 40.5 mmol). The reaction was sealed and allowed to mix for 4 days to ensure complete deprotonation and coupling occurred. Generation of the tri­ethyl­amine hydrogen bromide salt Et3NH+·Br− was observed as white crystals in the brown-colored solution. The mixture was filtered and the desired product extracted from the filtrate using a hexa­ne/water mixture. The hexane layer was separated and solvent removed to yield the ligand as a yellow-colored oil (8.516 g, 83%). The ligand was stored in a septum sealed round-bottom flask under argon gas in a refrigerator. 1H NMR (CDCl3, 400 MHz): δ2.31 (dd, J = 8.0 and 21.6 Hz, 2H), δ2.64 (t, J = 7.2 Hz, 2H), δ3.83 (s, 4H), δ4.97 (d, J = 10.4 Hz, 1H), δ5.01 (d, J = 18.8 Hz, 1H), δ5.75 (m, J = 10.4 Hz, 1H), δ7.13 (t, J = 6.4 Hz, 2H), δ 7.53 (d, J = 8.0 Hz, 2H), δ 7.64 (t, J = 7.6 Hz, 2H), δ8.51 (d, J = 4.4 Hz, 2H). 13C NMR (CDCl3, 400 MHz): δ 159.75, 149.01, 136.38, 135.38, 122.80, 121.88, 117.93, 77.13, 59.90, 57.32. FT–IR (liquid): v (cm−1) = 3066 (w), 2922 (w), 2816 (w), 2158 (s), 1639 (s), 1588 (s), 1361 (s), 994 (w), 756 (s). FT–IR (solid): v (cm−1) = 3394 (w), 3067 (w), 3008 (s), 2923 (w), 2817 (s), 2359 (s), 1619 (s), 1589 (s), 1432 (s).

Bottom Line: The perchlorate counter-ion is disordered over three sets of sites with refined occupancies 0.0634 (17), 0.221 (16) and 0.145 (7).In addition, the hetero-scorpionate arm of the bis-[(pyridin-2-yl)meth-yl](3,5,5,5-tetra-chloro-pent-yl)amine ligand is disordered over two sets of sites with refined occupancies 0.839 (2) and 0.161 (2).In the crystal, weak Cu⋯Cl inter-actions between symmetry-related mol-ecules create a dimerization with a chloride occupying the apical position of the square-pyramidal geometry typical of many copper(II) chloride hetero-scorpionate complexes.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry & Physics, Saint Mary's College, Notre Dame, IN 46556, USA.

ABSTRACT
In the title compound, [CuCl(C17H19Cl4N3)]ClO4, the Cu(II) ion adopts a distorted square-planar geometry defined by one chloride ligand and the three nitro-gen atoms from the bis-[(pyridin-2-yl)meth-yl](3,5,5,5-tetra-chloro-pent-yl)amine ligand. The perchlorate counter-ion is disordered over three sets of sites with refined occupancies 0.0634 (17), 0.221 (16) and 0.145 (7). In addition, the hetero-scorpionate arm of the bis-[(pyridin-2-yl)meth-yl](3,5,5,5-tetra-chloro-pent-yl)amine ligand is disordered over two sets of sites with refined occupancies 0.839 (2) and 0.161 (2). In the crystal, weak Cu⋯Cl inter-actions between symmetry-related mol-ecules create a dimerization with a chloride occupying the apical position of the square-pyramidal geometry typical of many copper(II) chloride hetero-scorpionate complexes.

No MeSH data available.