Conformation and bonding in unsymmetrically 3,6‐disubstituted dihydro‐1,2,4,5‐tetrazine

Abstract

The molecular structure of the title compound, I, has been determined by single‐crystal X‐ray diffraction. The crystals are triclinic, space group PI. The analysis revealed that the dihydro‐s‐tetrazine molecule is in a slightly twisted boat conformation with the nitrogen atoms carrying the two hydrogens, N(2) and N(4), pointing upward. All substituents on the dihydro‐s‐tetrazine ring exist in pseudo‐equatorial configurations. Adjacent hydrogen and bulky groups (CF3 and p‐Cl‐C6H4) have cis‐relationships. The p‐chlorophenyl group is twisted with respect to the dihydro‐s‐tetrazine ring. The unit cell for I contains six molecules. Each dihydro‐s‐tetrazine ring participates in four intermolecular hydrogen bonds (N···H bond distance 2.23 to 2.41 A), two hydrogen bonds to each adjacent tetrazine ring in the same unit cell.