4-(<i>o</i>-Tolyl)piperazin-1-ium chloride

Fun, Hoong‐Kun; Asik, Safra Izuani Jama; Chandrakantha, B.; Isloor, Arun M.; Shetty, Prakash

doi:10.1107/s1600536811044394

Cited by 2 publications

(1 citation statement)

References 7 publications

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“…2). That type of interleaved zigzag packing is known among chloride salts of secondary amines, both for alkyl-and arylamines (Adams et al, 1997;Nancy et al, 2003;Muller et al, 2007) and heterocyclic systems (Gribkov et al, 2006;Wang et al, 2011;Fun et al, 2011).…”

Section: Supramolecular Featuresmentioning

confidence: 94%

The 7-azanorbornane nucleus of epibatidine: 7-azabicyclo[2.2.1]heptan-7-ium chloride

Britvin

Rumyantsev

2017

Acta Cryst E

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7-Azabicyclo[2.2.1]heptane (7-azanorbornane) is a bridged heterocyclic nucleus found in epibatidine, the alkaloid isolated from the skin of the tropical poison frog Epipedobates tricolor. Since epibatidine is known as one of the most potent acetylcholine nicotinic receptor agonists, a plethora of literature has been devoted to this alkaloid. However, there are no structural data on the unsubstituted 7-azanorbornane, the parent bicyclic ring of epibatidine and its derivatives. We herein present the structural characterization of the 7-azabicyclo[2.2.1]heptane parent ring as its hydrochloride salt, namely 7-azabicyclo[2.2.1]heptan-7-ium chloride, C 6 H 12 N + ÁCl À . The compete cation is generated by a crystallographic mirror plane with the N atom lying on the mirror, as does the chloride anion. In the crystal, the cations are linked to the anions by N-HÁ Á ÁCl hydrogen bonds, which generate [001] chains.

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Section: Supramolecular Featuresmentioning

confidence: 94%

The 7-azanorbornane nucleus of epibatidine: 7-azabicyclo[2.2.1]heptan-7-ium chloride

Britvin

Rumyantsev

2017

Acta Cryst E

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An amide cyclophane

et al. 2014

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The title compound, 8,18-dithia-2,6-diaza-13(1,4)-piperidina-1(1,2),4(1,3),7(1,2)-tribenzenaoctadecaphane-10,15-diyne-3,6-dione, C32H30N4O2S2, is composed of a relatively planar bis(2-mercaptophenyl)isophthalamide unit linked to a bridging 1,4-di(but-2-yn-1-yl)piperazine unit, forming a macrocycle. The isophthalamide ring is inclined to the outer mercaptophenyl rings by 8.18 (11) and 5.59 (10)°, while these two rings are inclined to one another by 9.10 (12)°. The piperazine ring adopts a chair conformation. There are two intramolecular N—H⋯S hydrogen bonds generating S(5) ring motifs. In the crystal, molecules are linked via C—H⋯S and C—H⋯O hydrogen bonds, forming slabs lying parallel to (001). An O atom in the isophthalamide group is disordered over two positions with an occupancy ratio of 0.41 (6):0.59 (6).

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4-(o-Tolyl)piperazin-1-ium chloride

Cited by 2 publications

References 7 publications

The 7-azanorbornane nucleus of epibatidine: 7-azabicyclo[2.2.1]heptan-7-ium chloride

The 7-azanorbornane nucleus of epibatidine: 7-azabicyclo[2.2.1]heptan-7-ium chloride

An amide cyclophane

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