Supramolecular organization of bis(3-halo-4-dimethylaminobenzylidene)hydrazines

Abstract

Bis(3-bromo-4-dimethylaminobenzylidene)hydrazine and bis(3-chloro-4-dimethylaminobenzylidene)hydrazine have been synthesized, and their monoclinic crystal structures solved in space group P2(1)/c. For the bromo derivative at 150 K, a = 10.4505(2), b = 8.0358(2), c = 11.3208(2) angstrom, beta = 102.56(2)degrees, Z = 2, V = 927(9) angstrom(3), Dx = 1.618 g cm(-3), refinement on 2217 reflections, R = 0.023. For the chloro derivative at 150K, a = 10.3416(8), b = 8.0605(5), c = 11.1573(8) angstrom, beta = 102.70(8)degrees, Z = 2, V = 907(3) angstrom(3), Dx = 1.330 g cm(-3), refinement on 2429 reflections, R = 0.038. The molecules are close to planar, the crystal packing shows Br center dot center dot center dot Br or Cl center dot center dot center dot Cl intermolecular halogen bonds, and some C-H center dot center dot center dot Br or Cl contacts. There are no Cl center dot center dot center dot N or Br center dot center dot center dot N interactions. (c) 2012 Elsevier B.V. All rights reserved.