Synthesis and crystal structure of 2,2,2-trichloroethyl <i>N</i>-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate

An orthogonally addressable 3,6-disubstituted 1,2,4,5-tetra-zine, namely 2,2,2-tri-chloro-ethyl <i>N</i>-{4-[6-(1-hy-droxy-eth-yl)-1,2,4,5-tetra-zin-3-yl]benz-yl}carbamate (C₁₄H₁₄Cl₃N₅O₃), was synthesized and characterized by single-crystal X-ray diffraction. The tetra-zine comprises a free hydroxyl and a 2,2,2-tri-chloro-eth-oxy-carbonyl protected amino group, which gives rise to hydrogen-bonding inter-actions each making the tetra-zine highly linked in the solid state. The carbamate moieties form inter-molecular hydrogen bonds, stacking the tetra-zine mol-ecules above each other, while lateral hydrogen bonds are formed between a tetra-zine N atom and a hydroxyl group, the latter inter-action being a scarcely explored structural feature of 1,2,4,5-tetra-zines.