Date Published: June 01, 2010
Publisher: International Union of Crystallography
Author(s): H. S. Naveenkumar, Amirin Sadikun, Pazilah Ibrahim, Madhukar Hemamalini, Hoong-Kun Fun.
The title compound, C20H17N3O2·CH4O·H2O, was synthesized by the condensation reaction of 2-benzyloxybenzaldehyde with isoniazid (isonicotinic acid hydrazide). The tricyclic compound displays a trans configuration with respect to the C=N double bond. The central benzene ring makes dihedral angles of 8.83 (7) and 70.39 (8)° with the pyridine ring and the terminal benzene ring, respectively. The dihedral angle between the pyridine ring and the terminal benzene ring is 73.11 (8)°. In the crystal structure, molecules are connected by intermolecular N—H⋯O, O—H⋯O, O—H⋯(N,N) and C—H⋯O hydrogen bonds, forming a two-dimensional network perpendicular to the a axis.
For applications of isoniazid derivatives, see: Janin, 2007 ▶; Maccari et al. (2005 ▶); Slayden & Barry (2000 ▶). For the biological activity of Schiff bases, see: Kahwa et al. (1986 ▶). For related structures, see: Naveenkumar et al. (2010a ▶, 2010b ▶, 2010c ▶). For the synthesis of isoniazid derivatives, see: Lourenco et al. (2008 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).