Abstract
The crystal structures of seven hexamethylenetetramine (HMTA) complexes, or co-crystals, with carboxylic acid donor molecules are reported to explain the link between the molecular structure of HMTA and the crystal structure of the co-crystals, i.e. the dimension and shape of their hydrogen-bonded assembly. A comprehensive and detailed literature survey of HMTA complexes (38), be they neutral co-crystals or salts, with molecules containing carboxylic acid and phenol functional groups reveals that in general two N acceptors are used for strong O—H...N interactions. Owing to the relative arrangement of two of the four N atoms, the most common type of assembly features one-dimensional zigzag chains. Weak interactions of the C—H...N type are formed by N atoms not involved in strong interactions. These chains also form the basis of two-dimensional assemblies. These one- and two-dimensional assemblies feature either two or three functional groups. If only one functional group is on the donor molecule, then wing or V-shaped zero-dimensional assemblies are formed, which can be considered to be the building blocks for one- and two-dimensional assemblies. In general, the HMTA molecules form two-dimensional layers which are stabilized by weak hydrogen bonds. Co-crystals with cyclohexylcarboxylic acid (I), 4-fluorobenzoic acid (II), 4-methylbenzoic acid (III) and cinnamic acid (IV) all feature the V-shaped zero-dimensional assemblies. Co-crystals with cis-1,4-cyclohexyldicarboxylic acid (VI) and trans-1,4-cyclohexylcarboxylic acid (VII) feature the zigzag chains and can be structurally derived from co-crystal (I). Co-crystal (V), with 4-nitrobenzoic acid, has solvent water included and features hydrogen bonding to all four N atoms of the HMTA molecule.
Publisher
International Union of Crystallography (IUCr)
Subject
General Biochemistry, Genetics and Molecular Biology,General Medicine
Cited by
19 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献
1. Supramolecular structure of bis(1-methyl-1,3,5,7-tetraazatricyclo[3.3.1.13,7]decan-1-ium)2,5-dicarboxybenzene-1,4-dicarboxylate: Synthesis, spectral, structural and third-order nonlinear optical properties;Journal of Molecular Structure;2024-01
2. Synthesis, structural characterization, and Hirshfeld surface analysis of novel NLO active 1-methyl-1,3,5,7-tetraazaadamantan-1-ium 3-carboxy-5-nitrobenzoate hydrate;Journal of Molecular Structure;2022-12
3. Hydrated magnesium (II) with H-bonded hexamethylenetetramine and co-ligands: synthesis, structural characterization, thermal decomposition, and hirshfeld surface analysis;Chemical Papers;2022-06-29
4. Short X···N Halogen Bonds With Hexamethylenetetraamine as the Acceptor;Frontiers in Chemistry;2021-04-29
5. Bulk polarity of 3,5,7-trinitro-1-azaadamantane mediated by asymmetric NO2(lone pair)...NO2(π-hole) supramolecular bonding;Acta Crystallographica Section C Structural Chemistry;2020-05-22