Basavaraju Yeriyur B, Yathirajan Hemmige S, Parkin Sean
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru-570 006, India.
Department of Chemistry, University of Kentucky, Lexington, KY, 40506-0055, USA.
Acta Crystallogr E Crystallogr Commun. 2023 Mar 23;79(Pt 4):380-385. doi: 10.1107/S2056989023002529. eCollection 2023 Mar 1.
Syntheses and X-ray crystal structures of four 4-(4-meth-oxy-phen-yl)piperazin-1-ium (MeOPP) salts, with 2,2,2-tri-fluoro-acetate, CHNO·CFO (), 2,3,4,5,6-penta-fluoro-benzoate, CHNO·CFO ·HO (), 4-iodo-benzoate CHNO·CHIO ·HO (), and 4-methyl-benzoate, CHNO·CHO ·HO () anions are presented. The salts form directly from equimolar qu-anti-ties of -(4-meth-oxy-phen-yl)piperazine and the corresponding organic acid in methanol and crystallize from 1:1 methanol/ethyl acetate. Salt is anhydrous whereas , , and are all monohydrates. In all cases, the MeOPP cation conformation is determined by the torsion about the N-C bond between the piperazinium and 4-meth-oxy-benzene rings. Crystal packing in each structure is largely dictated by N-H⋯O and (in , , and ) O-H⋯O hydrogen bonds, although each also features weak C-H⋯O-type hydrogen bonds. Salt also has π-π-stacking inter-actions between cation and anion arene rings, and exhibits I⋯I close contacts.
本文报道了四种4-(4-甲氧基苯基)哌嗪-1-鎓(MeOPP)盐的合成及其X射线晶体结构,这些盐分别含有2,2,2-三氟乙酸根、C₇H₆NO·CF₃COO⁻(化合物1)、2,3,4,5,6-五氟苯甲酸根、C₇H₆NO·C₇F₅COO⁻·H₂O(化合物2)、4-碘苯甲酸根、C₇H₆NO·C₇H₄IO₂·H₂O(化合物3)和4-甲基苯甲酸根、C₇H₆NO·C₈H₈O₂·H₂O(化合物4)阴离子。这些盐由等摩尔量的4-(4-甲氧基苯基)哌嗪和相应的有机酸在甲醇中直接形成,并从1:1的甲醇/乙酸乙酯中结晶出来。化合物1是无水的,而化合物2、3和4都是一水合物。在所有情况下,MeOPP阳离子的构象由哌嗪鎓环和4-甲氧基苯环之间的N-C键扭转决定。尽管每种结构中还存在弱的C-H⋯O型氢键,但每个结构中的晶体堆积主要由N-H⋯O和(在化合物2、3和4中)O-H⋯O氢键决定。化合物1的阳离子和阴离子芳环之间还存在π-π堆积相互作用,化合物3表现出I⋯I紧密接触。