The crystal structures of salts of N-(4-fluorophenyl)piperazine with four aromatic carboxylic acids and with picric acid
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The structures are reported for five salts formed by reactions between N-(4-fluorophenyl)piperazine and aromatic acids. In 4-(4-fluorophenyl)piperazin-1-ium 2-fluorobenzoate monohydrate, C10H14FN2+·C7H4FO2−·H2O, (I), the components are linked by a combination of N—H⋯O and O—H⋯O hydrogen bonds to form a chain of alternating R46(12) and R66(16) rings. The ionic components of 4-(4-fluorophenyl)piperazin-1-ium 2-bromobenzoate 0.353-hydrate, C10H14FN2+·C7H4BrO2−·0.353H2O, (II), are linked by N—H⋯O hydrogen bonds to form a centrosymmetric four-ion aggregate containing an R44(12) motif, and these aggregates are linked into a molecular ladder by a single C—H⋯π(arene) hydrogen bond. 4-(4-Fluorophenyl)piperazin-1-ium 2-iodobenzoate, C10H14FN2+·C7H4IO2−, (III), crystallizes with Z′ = 2 in space group P: the four independent ions are linked by N—H⋯O hydrogen bonds to form a non-centrosymmetric aggregate again containing an R44(12) motif, and aggregates of this type are linked into a ribbon by a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds. The anion in 4-(4-fluorophenyl)piperazin-1-ium 2,4,6-trinitrophenolate, C10H14FN2+·C6H2N3O7−, (IV), shows clear evidence of extensive electronic delocalization from the phenolate O atom into the adjacent ring. The ions are linked by a combination of two-centre N—H⋯O and three-centre N—H⋯(O)2 hydrogen bonds to form centrosymmetric four-ion aggregates containing three types of ring. The ions in 4-(4-fluorophenyl)piperazin-1-ium 3,5-dinitrobenzoate, C10H14FN2+·C7H3N2O6−, (V), are again linked by N—H⋯O hydrogen bonds to form centrosymmetric R44(12) aggregates, which are themselves linked by a C—H⋯π(arene) hydrogen bond to form sheets, the stacking of which leads to the formation of narrow channels, containing disordered and/or mobile solvent entities. Comparisons are made with some related structures.
Harish Chinthal , C , Yathirajan , H S , Kavitha , C N , Foro , S & Glidewell , C 2020 , ' The crystal structures of salts of N -(4-fluorophenyl)piperazine with four aromatic carboxylic acids and with picric acid ' , Acta Crystallographica Section E Crystallographic Communications , vol. 76 , no. Part 8 , pp. 1179-1186 . https://doi.org/10.1107/S2056989020008749
Acta Crystallographica Section E Crystallographic Communications
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DescriptionHSY thanks the University Grants Commission, New Delhi, for the award of a BSR Faculty Fellowship for three years.
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