Abstract

In the title compound, C20H20N4O2·H2O, the planes of the phen-oxy and phthalo-nitrile rings are oriented at a dihedral angle of 60.39 (5)°. The 3-(di--methyl-amino)-propyl chain has an extended conformation and is cis with respect to the phthalo-nitrile ring. In the crystal, O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules to form slabs parallel to (100). There are also C-H⋯O and C-H⋯N hydrogen bonds and C-H⋯π inter-actions present within the slabs. The slabs are linked by a pair of inversion-related C-H⋯N hydrogen bonds, involving phthalo-nitrile rings, forming a three-dimensional structure.

Highlights

  • C20H20N4O2H2O, the planes of the phenoxy and phthalonitrile rings are oriented at a dihedral angle of 60.39 (5)

  • Amido amine derivatives are suggested as exhibiting an outstanding combination of surfactant properties

  • H atoms involved in hydrogen bonding have been included for clarity

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Summary

Chemical context

Amido amine derivatives are suggested as exhibiting an outstanding combination of surfactant properties. Well-known application fields for amino derivatives are their use as synthetic intermediates of anticancer agents, antibiotics and other drugs. They exhibit exceptionally low ocular irritation and oral toxicity, being well tolerated by human tissue (Roy et al, 2010). Polyamines play an important role in cell growth and bind to the phosphate residues of DNA, stabilizing the specific conformation of the latter (Karaoğlan et al, 2011; Göksel et al, 2013; Kim et al., 2012; Çolak et al, 2014). In this context, we synthesized 4-(3,4dicyanophenoxy)-N-[3-(dimethylamino)propyl]benzamide monohydrate and report on its crystal structure

Structural commentary
Supramolecular features
Refinement
Synthesis and crystallization
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