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Issue 31, 2003

Supramolecular synthons in phenol–isonicotinamide adducts

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Abstract

Molecular complexes of four phenols (hydroquinone, resorcinol, phloroglucinol and 4-hydroxybenzoic acid) with isonicotinamide are characterized by X-ray diffraction. (Hydroquinone)0.5·(isonicotinamide) 1 and (resorcinol)·(isonicotinamide)22 have tapes of O–H⋯N and amide N–H⋯O dimer synthons. In (phloroglucinol)·(isonicotinamide)2·(H2O)23, six component self-assembly results in stacked dimers with four O–H⋯N and four amide N–H⋯O hydrogen bonds and the third phenol OH aggregates with two water molecules in a supramolecular chair cyclohexane array. Phenolpyridine and amide N–H⋯O dimers are robust synthons in 1–3 for the self-assembly of 0D discrete aggregates and infinite 1D chains. Hydrogen bonding of amide dimers via N–H⋯Ophenol/water is ascribed to cooperative effects. The crystal structure of (4-hydroxybenzoic acid)·(isonicotinamide) 4 establishes the robustness of phenolpyridine hydrogen bonding in the presence of carboxylic acid groups. Molecular components in 4 are arranged as zigzag tapes of O–H⋯N hydrogen bonds and acid⋯amide heterodimers. Supramolecular synthesis with phenolisonicotinamide adducts expands the versatility of isonicotinamide as a co-crystallizing agent in crystal engineering.

Graphical abstract: Supramolecular synthons in phenol–isonicotinamide adducts

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Article information


Submitted
14 Apr 2003
Accepted
08 May 2003
First published
20 May 2003

CrystEngComm, 2003,5, 164-168
Article type
Paper

Supramolecular synthons in phenolisonicotinamide adducts

P. Vishweshwar, A. Nangia and V. M. Lynch, CrystEngComm, 2003, 5, 164
DOI: 10.1039/B304078J

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