(E)-N′-[1-(4-Bromophenyl)ethylidene]-2-hydroxybenzohydrazide

Abstract

In the title compound, C15H13BrN2O2, the two aromatic rings form a dihedral angle of 7.9 (1)° and an intra­molecular N—H⋯O hydrogen bond influences the mol­ecular conformation. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains propagated in [001]. The crystal packing exhibits also π–π inter­actions, which pair mol­ecules into centrosymmetric dimers with short inter­molecular distances of 3.671 (4) Å between the centroids of aromatic rings.

The crystal structure of (E)-N′-(1-(3-chloro-4-fluorophenyl) ethylidene)-2-hydroxybenzohydrazide, C15H12ClFN2O2

“…Compared with those of closely related structure, such a structural feature is uncommon [15]. The bond lengths and angles are in the expected ranges which fit with those of related compounds in literature [11][12][13][14][15][16][17]. The C=N double bond lengths in the independent molecule are 1.277(3) Å (C8=N4) and 1.271(4) Å (C23=N2), respectively, exhibiting the double bond character.…”

“…In recent years, Schiff bases as one of the important synthetic intermediates have attracted more and more attention due to the wide applications in the fields of coordination chemistry, biochemistry, pharmacy, nanotechnology, and photochemistry [3][4][5][6][7][8][9][10]. From the structural point of view, o-hydroxy Schiff bases are attractive because of their intramolecular H-bond, and thus have been extensively investigated and reported [11][12][13][14][15][16][17]. In addition, the heteroatoms (such as N, F, Cl, Br, S) can act as hydrogen bonding acceptors for bioactive molecules in order to exhibit higher biological activity [18,19].…”