2,13-Dibenzyl-5,16-diethyl-2,6,13,17-tetra-aza-tricyclo-[16.4.0.0]docosan-2-ium nitrate

Abstract

One of the tertiary amine atoms has been protonated in the title salt, C(36)H(57)N(4) (+)·NO(3) (-). The four N atoms of the macrocycle are almost coplanar (r.m.s. deviation = 0.0053 Å), a result correlated with the formation of intra-molecular N-H⋯N and N-H⋯(N,N) hydrogen bonds. With respect to this plane, the benzyl groups lie to either side; a similar arrangement pertains for the cyclo-hexyl rings (each with a chair conformation). Helical supra-molecular chains are evident in the crystal, whereby alternating cations and anions are linked by C-H⋯O inter-actions. The chains are consolidated into supra-molecular arrays in the ab plane via C-H⋯π contacts involving both benzene rings.

Fig. 1.

Molecular structures of the ions in (I) showing displacement ellipsoids at the 50% probability level.

Fig. 2.

Helical supramolecular chain aligned along the b-axis in (I) mediated by C—H···O interactions shown as orange dashed lines. Intramolecular N—H···N hydrogen bonds are shown as blue dashed lines.

Fig. 3.

A view of the crystal packing of (I) in projection down the a-axis. The C—H···O and C—H···π interactions shown as orange and purple dashed lines, respectively.