2,4-Diamino-5-(1-naphthyl)-3,5-diaza-1-azoniaspiro[5.5]undeca-1,3-diene chloride

Acta Crystallogr C. 2002 Dec;58(Pt 12):o730-2. doi: 10.1107/s0108270102019108. Epub 2002 Nov 26.

Abstract

The title salt, C(18)H(22)N(5)(+).Cl(-), is a member of a new series of lipophilic 4,6-diamino spiro-s-triazines which are potent inhibitors of dihydrofolate reductase. The protonated triazine ring deviates from planarity, whereas the cyclohexane ring adopts a chair conformation. A rather unusual hydrogen-bonding scheme exists in the crystal. There is a centrosymmetric arrangement involving two amino groups and two triazine ring N atoms, with graph-set R(2)(2)(8) and an N.N distance of 3.098 (3) A, flanked by two additional R(3)(2)(8) systems, involving two amino groups, a triazine ring N atom and a Cl(-) anion, with N.Cl distances in the range 3.179 (2)-3.278 (2) A. Furthermore, the Cl(-) anion, the protonated triazine ring N atom and an amino group form a hydrogen-bonding system with graph-set R(2)(1)(6).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Crystallography
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Spiro Compounds / chemistry*

Substances

  • 2,4-diamino-5-(1-naphthyl)-3,5-diaza-1-azoniaspiro(5.5)undeca-1,3-diene chloride
  • Naphthalenes
  • Spiro Compounds