Aminoalkanol derivatives have attracted much interest in the field of medicinal chemistry as part of the search for new anticonvulsant drugs. In order to study the influence of the methyl substituent and N-oxide formation on the geometry of molecules and intermolecular interactions in their crystals, three new examples have been prepared and their crystal structures determined by X-ray diffraction. 1-[(2,6-Dimethylphenoxy)ethyl]piperidin-4-ol, C15H23NO2, 1, and 1-[(2,3-dimethylphenoxy)ethyl]piperidin-4-ol, C15H23NO2, 2, crystallize in the orthorhombic system (space groups P212121 and Pbca, respectively), with one molecule in the asymmetric unit, whereas the N-oxide 1-[(2,3-dimethylphenoxy)ethyl]piperidin-4-ol N-oxide monohydrate, C15H23NO3·H2O, 3, crystallizes in the monoclinic space group P21/c, with one N-oxide molecule and one water molecule in the asymmetric unit. The geometries of the investigated compounds differ significantly with respect to the conformation of the O-C-C linker, the location of the hydroxy group in the piperidine ring and the nature of the intermolecular interactions, which were investigated by Hirshfeld surface and corresponding fingerprint analyses. The crystal packing of 1 and 2 is dominated by a network of O-H...N hydrogen bonds, while in 3, it is dominated by O-H...O hydrogen bonds and results in the formation of chains.

中文翻译：

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甲基取代基的位置和N-氧化物的形成对1-（苯氧乙基）哌啶-4-醇衍生物的几何结构和分子间相互作用的影响。

作为寻找新的抗惊厥药的一部分，氨基链烷醇衍生物在药物化学领域引起了极大的兴趣。为了研究甲基取代基和N-氧化物的形成对其分子的几何形状及其分子间相互作用的影响，制备了三个新的实例，并通过X射线衍射确定了它们的晶体结构。1-[（（2,6-二甲基苯氧基）乙基]哌啶-4-醇，C15H23NO2，1，和1-[（2,3-二甲基苯氧基）乙基]哌啶-4-醇，C15H23NO2，2，在正交晶系中结晶（分别为P212121和Pbca空间群），在不对称单元中具有一个分子，而N-氧化物1-[（（2,3-二甲基苯氧基）乙基]哌啶-4-醇N-氧化物一水合物C15H23NO3·H2O，3在单斜空间群P21 / c中结晶，在不对称单元中带有一个N氧化物分子和一个水分子。通过Hirshfeld表面和相应的指纹分析研究，所研究化合物的几何形状在OCC接头的构象，哌啶环中羟基的位置以及分子间相互作用的性质方面存在显着差异。1和2的晶体堆积以OH ... N氢键网络为主，而3中的结晶堆积以OH ... O氢键为主，并导致形成链。通过Hirshfeld表面和相应的指纹分析对其进行了研究。1和2的晶体堆积以OH ... N氢键网络为主，而3中的结晶堆积以OH ... O氢键为主，并导致形成链。通过Hirshfeld表面和相应的指纹分析对其进行了研究。1和2的晶体堆积以OH ... N氢键网络为主，而3中的结晶堆积以OH ... O氢键为主，并导致形成链。