Research Article: N1,N4,3,6-Tetra­methyl-1,2,4,5-tetra­zine-1,4-dicarboxamide

Date Published: June 01, 2012

Publisher: International Union of Crystallography

Author(s): Na-Bo Sun, Guo-Wu Rao, Qun Shen.

http://doi.org/10.1107/S1600536812022519

Abstract

The asymmetric unit of the title compound, C8H14N6O2, contains two independent mol­ecules. In one mol­ecule, the amide-substituted N atoms of the tetra­zine ring deviate from the plane [maximum deviation = 0.028 (1) Å] through the four other atoms in the ring by 0.350 (2) and 0.344 (2) Å, forming a boat conformation, and the mean planes of the two carboxamide groups form dihedral angles of 10.46 (13) and 20.41 (12)° with the four approximtely planar atoms in the tetra­zine ring. In the other mol­ecule, the amide-substituted N atoms of the tetra­zine ring deviate from the plane [maximum deviation = 0.033 (1) Å] through the four other atoms in the ring by 0.324 (2) and 0.307 (2) Å, forming a boat conformation, and the mean planes of the two carboxamide groups form dihedral angles of 14.66 (11) and 17.08 (10)° with the four approximately planar atoms of the tetra­zine ring. In the crystal, N—H⋯O hydrogen bonds connect mol­ecules to form a two-dimensional network parallel to (1-1-1). Intra­molecular N—H⋯N hydrogen bonds are observed.

Partial Text

For chemical reactions of 1,2,4,5-tetra­zine derivatives, see: Domingo et al. (2009 ▶); Lorincz et al. (2010 ▶) and for their biological activity, see: Devaraj et al. (2009 ▶); Eremeev et al. (1978 ▶, 1980 ▶); Han et al. (2010 ▶); Neunhoeffer (1984 ▶); Sauer (1996 ▶). For the anti­tumor activity of 1,2,4,5-tetra­zine derivatives, see: Hu et al. (2002 ▶, 2004 ▶); Rao & Hu (2005 ▶, 2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the synthesis of the title compound, see: Hu et al. (2004 ▶); Rao et al. (2012 ▶); Sun et al. (2003 ▶).

 

Source:

http://doi.org/10.1107/S1600536812022519

 

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