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Crystal structures of the recreational drug it N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts

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Author(s)

Haruvegowda Kiran Kumar, Hemmige S. Yathirajan, Chayanna Harish Chinthal, Sabine Foro, Christopher Glidewell

School/Research organisations

Abstract

Crystal structures are reported for N-(4-meth­oxy­phen­yl)piperazine (MeOPP), (I), and for its 3,5-di­nitro­benzoate, 2,4,6-tri­nitro­phenolate (picrate) and 4-amino­benzoate salts, (II)–(IV), the last of which crystallizes as a monohydrate. In MeOPP, C11H16N2O, (I), the 4-meth­oxy­phenyl group is nearly planar and it occupies an equatorial site on the piperazine ring: the mol­ecules are linked into simple C(10) chains by N—H⋯O hydrogen bonds. In each of the salts, i.e., C11H17N2O+·C7H3N2O6, (II), C11H17N2O+·C6H2N3O7, (III), and C11H17N2O+·C7H6NO2·H2O, (IV), the effectively planar 4-meth­oxy­phenyl substituent again occupies an equatorial site on the piperazine ring. In (II), two of the nitro groups are disordered over two sets of atomic sites and the bond distances in the anion indicate considerable delocalization of the negative charge over the C atoms of the ring. The ions in (II) are linked by two N—H⋯O hydrogen bonds to form a cyclic, centrosymmetric four-ion aggregate; those in (III) are linked by a combination of N—H⋯O and C—H⋯π(arene) hydrogen bonds to form sheets; and the components of (IV) are linked by N—H⋯O, O—H⋯O and C—H⋯π(arene) hydrogen bonds to form a three-dimensional framework structure. Comparisons are made with the structures of some related compounds.
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Details

Original languageEnglish
Pages (from-to)488-495
Number of pages8
JournalActa Crystallographica Section E
Volume76
Issue number4
Early online date5 Mar 2020
DOIs
Publication statusPublished - Apr 2020

    Research areas

  • Piperazines, Crystal structure, Molecular dimensions, Molecular conformation, Hydrogen bonding, Supramolecular assembly

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