Three closely related 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzoyl)piperazines: similar molecular structures but different intermolecular interactions

Abstract

Three 1-[(1,3-benzodioxol-5-yl)methyl]-4-(halobenzo­yl)piperazines adopt very similar mol­ecular conformations but, while the mol­ecules of the 3-fluoro­benzoyl are linked by hydrogen bonds into a three-dimensional structure, there are no hydrogen bonds in either of the 2,6-di­fluoro­benzoyl and 2,4-di­chloro­benzoyl analogues.

Six 1-halobenzoyl-4-(2-methoxyphenyl)piperazines having Z′ values of one, two or four; disorder, pseudosymmetry, twinning and supramolecular assembly in one, two or three dimensions

“…By contrast with the assembly in (VIII)-(X), there are no significant hydrogen bonds in the structure of the unsubstituted analogue 1-benzoyl-4-(4-methoxyphenyl)piperazine (XI) (Kiran Kumar, Yathirajan, Sagar et al, 2019), just as there are none in the structure of 1-(3,5-dinitrobenzoyl)-4-(2-methoxyphenyl)piperazine (XII) (Harish Chinthal et al, 2020b). Finally, we note that structures have been reported recently for 1-(2iodobenzoyl)-4-(pyrimidin-2-yl)piperazine and for three 1-(1,3-benzodioxol-5-yl)methyl-4-(halobenzoyl)piperazines (Mahesha, Sagar et al, 2019).…”

Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly

“…The molecules of 1-acetyl-4-(4-hydroxyphenyl)piperazine (Kavitha et al, 2013) are linked by O-HÁ Á ÁO hydrogen bonds to form simple C(12) chains, while those of 1-(2-iodobenzoyl)-4-(pyrimidin-2yl)piperazine are linked by a combination of C-HÁ Á ÁO and C-HÁ Á Á(arene) hydrogen bonds to form a three-dimensional framework structure which is further strengthened by both aromaticstacking interactions and IÁ Á ÁN halogen bonds. Finally, we note the structures of three closely related 1-(1,3-benzodioxolol-5-yl)methyl-4-(halobenzoyl) piperazines (Mahesha, Sagar et al, 2019), where the 3-fluorobenzoyl derivative forms a threedimensional framework structure built from C-HÁ Á ÁO and C-HÁ Á Á(arene) hydrogen bonds, whereas the structures of the 2,6-difluorobenzoyl and 2,4-dichlorobenzoyl analogues contain no hydrogen bonds of any sort. Examples of attractive iodoÁ Á Ácarbonyl interactions, as found here in (V), have also been reported in a number of systems (Glidewell et al, 2005;Garden et al, 2006;Sirimulla et al, 2013).…”