Synthesis and crystal structure of 2-(benzo[ <i>d</i> ]thiazol-2-yl)- <i>N</i> ′-[( <i>E</i> )-1-(4-bromophenyl)ethylidene]acetohydrazide

Abstract

The title compound (<i>E</i>)-2-(benzo[<i>d</i>]thia-zol-2-yl)-<i>N</i>'-(1-(4-bromo-phen-yl)ethyl-idene)acetohydrazide, C₁₇H₁₄BrN₃OS, crystallizes in space group <i>P</i>2₁/<i>c</i> with <i>Z</i> = 4. The configuration across the formal N=C double bond at the hydrazide moiety is <i>E</i>; the atom sequence C-C-C(= O)-N-N=C-(bromo-phen-yl) is very approximately planar (r.m.s. deviation 0.17 Å, when all carbon atoms of the bromo-phenyl group are included), being synperiplanar around the C(=O)-N bond and anti-periplanar (choosing the appropriate final atom C_Ar) elsewhere. The inter-planar angle to the benzo-thia-zole unit (r.m.s. deviation 0.01 Å) is 69.75 (2)°. The main packing feature is a classical inversion-symmetric dimer with hydrogen bonds of the type N-H⋯O=C. This combines with a rather long N_thia-zole⋯Br halogen bond to form a thick layer structure parallel to the <i>bc</i> plane.