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

Abstract

A 3,6-disubstituted 1,2,4,5-tetra­zine was synthesized and characterized by single-crystal X-ray diffraction, revealing a complex hydrogen-bonded network with inter­actions between tetra­zine N atoms and hydroxyl groups, thereby complementing the only scarcely explored features of tetra­zines in the solid state.

An orthogonally addressable 3,6-disubstituted 1,2,4,5-tetra­zine, namely 2,2,2-tri­chloro­ethyl N-{4-[6-(1-hy­droxy­eth­yl)-1,2,4,5-tetra­zin-3-yl]benz­yl}carbamate (C₁₄H₁₄Cl₃N₅O₃), was synthesized and characterized by single-crystal X-ray diffraction. The tetra­zine comprises a free hydroxyl and a 2,2,2-tri­chloro­eth­oxy­carbonyl protected amino group, which gives rise to hydrogen-bonding inter­actions each making the tetra­zine highly linked in the solid state. The carbamate moieties form inter­molecular hydrogen bonds, stacking the tetra­zine mol­ecules above each other, while lateral hydrogen bonds are formed between a tetra­zine N atom and a hydroxyl group, the latter inter­action being a scarcely explored structural feature of 1,2,4,5-tetra­zines.