Abstract
The title compound, C10H13Cl2NO2·C6H4Cl2O, was formed from the incomplete Mannich condensation reaction of 3-amino-propan-1-ol, formaldehyde and 2,4-di-chloro-phenol in methanol. This resulted in the formation of a co-crystal of the zwitterionic Mannich base, 2,4-di-chloro-6-{[(3-hy-droxy-prop-yl)azaniumyl]-meth-yl}phenolate and the unreacted 2,4-di-chloro-phenol. The compound crystallizes in the monoclinic crystal system (in space group Cc) and the asymmetric unit contains a mol-ecule each of the 2,4-di-chloro-phenol and 2,4-di-chloro-6-{[(3-hy-droxy-prop-yl)azaniumyl]-meth-yl}phenolate. Examination of the crystal structure shows that the two components are clearly linked together by hydrogen bonds. The packing patterns are most inter-esting along the b and the c axes, where the co-crystal in the unit cell packs in a manner that shows alternating aromatic di-chloro-phenol fragments and polar hydrogen-bonded channels. The 2,4-di-chloro-phenol rings stack on top of one another, and these are held together by π-π inter-actions. The crystal studied was refined as an inversion twin.
Highlights
The Mannich condensation is an important reaction in synthetic organic chemistry
The title compound crystallizes in the monoclinic crystal system, in the space group Cc
The organic Mannich base exists as a zwitterion with the negative charge of phenolate being stabilized by the positively charged ammonium moiety
Summary
The Mannich condensation is an important reaction in synthetic organic chemistry. The formation of the C—N bond in the resulting Mannich base is often an important step in the biosynthesis of several natural products, such as alkaloids and flavanoids (Sarhan et al, 2006). Amino-phenolic ligands have versatile applications in inorganic as well as analytical chemistry. The flexible C—N bond in these ligands offers a tractable three-dimensional structure when coordinated to different metal centres (Riisioet al., 2012). This provides numerous applications, in enzyme mimicking and catalysis, as well as extraction of trace metals (Maurya et al, 2015; Riisioet al., 2013; Lee et al, 2010). The zwitterion co-crystallized with the unreacted phenol, resulting in the serendipitous isolation of the title compound
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