Crystal structures of hydrazones, 2-(1,3-benzothiazolyl)-NH—N=CH—Ar, prepared from arenealdehydes and 2-hydrazinyl-1,3-benzothiazole

Abstract

Structures of hydrazones, [1: 2-(1,3-benzothiazolyl)-NH—N=CH—C6H3—XY], prepared from arenecarbäaldehydes and 2-hydrazinyl-1,3-benzothiazole, are reported. Compounds include unsolvated species, (1: X = 4-Cl, 4-Br, 4-NMe2; Y = H), [1: X,Y = 2,4-Me2, 2,4-(OMe)2], and solvated ones, [(1: X = 4-OH; Y = H) · H2O], [(1: X = 3-OMe; Y = 4-OH) · H2O], and [(1: X = 2-OH; Y = 5-NO2) · DMSO]. The solvated compound, [(1: X = 2-OH; Y = 5-NO2) · DMSO], exists in the imino form in contrast to the (E)-2-(1,3-benzothiazolyl)-NH—N=CH—Ar form exhibited by the other compounds. Common intermolecular interactions in the non-solvated compounds, (1: X = 4-Cl, 4-Br, 4-NMe2; Y = H) and [1: X,Y = 2,4-Me2, 2,4-(OMe)2], are strong dimer forming N—H · · · N hyädrogen bonds and weaker π · · · π interactions. The latter involve the benzothazole rings, except in [1: X,Y = 2,4-(OMe)2], where the π · · · π interactions involve thiazole and C6H3(OMe)2 rings. The dimer forming N—H · · · N intermolecular hydrogen bonds and π · · · π stacking interactions persist in the hydrate, [(1: X = 3-OMe; Y = 4-OH) · H2O], but not in the other solvates, [(1: X = 4-OH; Y = H) · H2O] and [(1: X = 2-OH; Y = 5-NO2) · DMSO]. For [(1: X = 4-OH; Y = H) · H2O], the important direct links between [(1: X = 4-OH; Y = H) are chain forming O—H · · · N hydrogen bonds, supplemented by π · · · π interactions. For all solvated compounds, the solvate molecules are involved in indirect links between the hydrazone molecules. In the case of [(1: X = 2-OH; Y = 5-NO2) · DMSO], present in the imino form, a network of rings is generated from the hydrogen bonding interactions of the DMSO solvate with the N—H and N—O(nitro) moieties of (1: X = 2-OH; Y = 5-NO2).

Crystal structures of 1-hydroxylimidazole and imidazole 1-oxide derivatives

“…The supramolecular arrays of compounds 6 in the solid state are made up from different combinations of classical hydrogen bonds, N-H···O, O-H···N and O-H···O, and weaker interactions, such as C-H···X (X = O, N or π), π···π and N-O···π interactions [24][25][26][27][28][29][30], see Tables 4 and 5 for details. As expected, the intermolecular interactions in (6: X = H), being a N-oxide, are different from those in the 1-hydroxy derivatives, (6: X = 4-Br, 4-F and 2-O 2 N).…”

Contrasting the supramolecular structures in the isomeric pair 5-bromo-3-nitrosalicylaldehyde phenylhydrazone and 3-bromo-5-nitrosalicylaldehyde phenylhydrazone

“…In the course of our continuing investigation of supramolecular arrangements in hydrazones, we have studied the supramolecular structures of hydrazones derived from 2-hydroxyacetophenone (Baddeley et al, 2009), bis(pyridin-2-yl) ketone (França et al, 2010), 2-aminoacetophenone (Howie et al, 2012) and iodo-and nitrobenzaldehydes with nitrophenylhydrazines (Glidewell et al, 2003(Glidewell et al, , 2004Wardell et al, 2005;Ferguson et al, 2005), as well as compounds obtained from 5-phenyl-2-hydrazinyl-1,3,4-thiadiazole (Carvalho et al, 2009), (1,3-benzothiazol-2-yl)hydrazine (Nogueira et al, 2011;Lindgren et al, 2012) and 7-chloro-4-hydrazinylquinoline (Howie et al, 2010; de Souza et al, 2012: Ferreira et al, 2012) with arenecarbaldehydes. We have now extended this study to the isomeric hydrazones obtained from the reaction of phenylhydrazine with 3-bromo-5-nitrosalicylaldehyde and 5-bromo-3-nitrosalicylaldehyde, and report here on their molecular and supramolecular structures.…”

2-{(E)-1-[2-(4-Nitrophenyl)hydrazin-1-ylidene]ethyl}benzene-1,3-diol

“…Previous systematic investigations have included the study of substituted phenylhydrazines with substituted benzaldehydes (Glidewell et al, 2004;Ferguson et al, 2005) and 2-hydroxyacetophenone (Baddeley, de Souza França et al, 2009). Hydrazones derived from substituted benzaldehydes and (pyrazinecarbonyl)hydrazine Howie, da Silva Lima et al, 2010), 2-hydrazinyl-benzothiazole (Nogueira et al, 2011), 7-chloroquinoline-4-hydrazide and 2hydrazinylacyl-N-isonicotine (Wardell et al, 2007) have also been investigated along with L-serinyl derivatives, (S)-2-hydroxy-1-[N-(benzylidene)-hydrazinylcarbonyl]ethylcarbamate esters (Howie et al, 2011).…”