Crystal structures of monohydrate and methanol solvate compounds of {1-[(3,5-bis{[(4,6-dimethylpyridin-2-yl)amino]methyl}-2,4,6-triethylbenzyl)amino]cyclopentyl}methanol.

Monika Mazik,Wilhelm Seichter,Manuel Stapf

doi:10.1107/s2056989020012554

Monika Mazik, Wilhelm Seichter + Show 1 more

Open Access

https://doi.org/10.1107/s2056989020012554

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Abstract

In the title monohydrate compound, 1a, and the methanol solvate compound, 1b, the tri-ethyl-benzene derivative, C35H51N5O, has three functionalized side arms and three ethyl groups, the former being located on one side of the central benzene ring, while the latter are directed to the opposite side. Both the crystals are constructed of structurally similar dimers of 1:1 host-guest complexes held together by N-H⋯O and O-H⋯N hydrogen bonds, and in 1a additionally by O-H⋯O hydrogen bonds. The structure of 1b contains additional highly disordered solvent mol-ecules. Thus, the SQUEEZE routine [Spek (2015 ▸). Acta Cryst. C71, 9-18] in PLATON was used to generate a modified data set, in which the contribution of the disordered mol-ecules to the structure amplitudes is eliminated. These solvent mol-ecules are not considered in the reported chemical formula.

Highlights

In the title monohydrate compound, 1a, and the methanol solvate compound, 1b, the triethylbenzene derivative, C35H51N5O, has three functionalized side arms and three ethyl groups, the former being located on one side of the central benzene ring, while the latter are directed to the opposite side
Both the crystals are constructed of structurally similar dimers of 1:1 host–guest complexes held together by N—HÁ Á ÁO and O—HÁ Á ÁN hydrogen bonds, and in 1a by O—HÁ Á ÁO hydrogen bonds
The three functionalized side arms point to one face of the central benzene ring and participate in the formation of hydrogen bonds with the guest solvent molecule, while the ethyl groups are directed to the opposite side

Summary

Chemical context

Representatives of the class of 1,3,5-trisubstituted 2,4,6-trialkylbenzenes have been shown to have the ability to act as artificial carbohydrate receptors. Depending on the nature of their building blocks, these compounds display different, interesting binding efficiencies and selectivities towards carbohydrates (Mazik, 2009, 2012; Stapf et al, 2020). Our systematic studies have shown the enormous potential of this acyclic receptor architecture for versatile structural modifications, which enable the identification of interesting structure–activity relationships. We have observed that the combination of two 2-aminopyridine units with another recognition group provides receptors having a binding preference for -glucoside vs -galactoside (Mazik & Kuschel, 2008; Mazik & Geffert, 2011; Stapf et al, 2020). The crystal structures of the monohydrate, 1a, and the methanol solvate, 1b, are described here

Structural commentary

Supramolecular features

Database survey

Synthesis and crystallization

Refinement

Findings

C31 C32 C33 C34 C35 O1W