Structure Reports Online

Volume 68, Part 6 (June 2012)

organic compounds

lh5475 scheme

Acta Cryst. (2012). E68, o1841-o1842 [ doi:10.1107/S1600536812022519 ]

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

N.-B. Sun, G.-W. Rao and Q. Shen

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-HO hydrogen bonds connect molecules to form a two-dimensional network parallel to (1-1-1). Intramolecular N-HN hydrogen bonds are observed.