Issue 14, 2015

Using halogen⋯halogen interactions or C/N–H⋯Cl hydrogen bonding to direct crystal packing in tetrachlorophthalic acid with N-heterocyclic compounds

Abstract

In exploring tetrachlorophthalic acid (H2-tcpH) with a series of N-heterocyclic compounds, eight different types of supramolecular complexes have been obtained, namely, [(H-1,10-phen)·(H-tcpH)·(H2-tcpH)·(CH3OH)] (1), [(H-Hatz)·(H-tcpH)] (2), [(H2-L5)·(H-tcpH)2] (3), [(H-Hampym)·(H-tcpH)] (4), [(H2-edm)·(H-tcpH)2] (5), [(H-ahmp)2·(tcpH)·2(H2O)] (6), [(H2-L7)·(tcpH)·2(H2O)] (7), and [(H-Bim)·(H-tcpH)·(H2O)] (8) (in which 1,10-phen = 1,10-phenanthroline, Hatz = 3-amino-1,2,4-triazole, L5 = 1,4-bis[(2-methylimidazole-1-yl)methyl]benzene, Hampym = 2-aminopyrimidine, edm = ethylenediamine, ahmp = 2-amino-4-hydroxy-6-methylpyrimidine, L7 = 1,2-bis[(2-methylimidazole-1-yl)methyl]benzene, Bim = benzimidazole). These eight complexes displayed amusing structural characteristics and a large amount of hydrogen bonding. Of these, crystals 1–5 generated a 3D supramolecular structure through Cl⋯Cl interactions, whilst C–H⋯Cl and N–H⋯Cl hydrogen bonding exists in the 3D construction of complexes 6–8. In addition, all the complexes were fully characterized by single crystal X-ray diffraction analysis, elemental analysis, infrared spectroscopy (IR), and thermogravimetric analysis (TGA).

Graphical abstract: Using halogen⋯halogen interactions or C/N–H⋯Cl hydrogen bonding to direct crystal packing in tetrachlorophthalic acid with N-heterocyclic compounds

Supplementary files

Article information

Article type
Paper
Submitted
28 Nov 2014
Accepted
24 Dec 2014
First published
24 Dec 2014

RSC Adv., 2015,5, 10275-10289

Author version available

Using halogen⋯halogen interactions or C/N–H⋯Cl hydrogen bonding to direct crystal packing in tetrachlorophthalic acid with N-heterocyclic compounds

Y. Hu, Z. Li, Y. Zhao, Y. Yang, F. Liu and L. Wang, RSC Adv., 2015, 5, 10275 DOI: 10.1039/C4RA15392H

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