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dc.contributor.authorKiran Kumar, Haruvegowda
dc.contributor.authorYathirajan, Hemmige S.
dc.contributor.authorHarish Chinthal, Chayanna
dc.contributor.authorForo, Sabine
dc.contributor.authorGlidewell, Christopher
dc.identifier.citationKiran Kumar , H , Yathirajan , H S , Harish Chinthal , C , Foro , S & Glidewell , C 2020 , ' Crystal structures of the recreational drug it N -(4-methoxyphenyl)piperazine (MeOPP) and three of its salts ' , Acta Crystallographica Section E , vol. 76 , no. 4 , pp. 488-495 .
dc.identifier.otherPURE: 267395758
dc.identifier.otherPURE UUID: c44b5860-44c2-40e0-ab3f-edc8fd0c1529
dc.identifier.otherBibtex: KiranKumar:zl2772
dc.identifier.otherScopus: 85083118038
dc.identifier.otherWOS: 000524115100006
dc.descriptionHSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.en
dc.description.abstractCrystal 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.
dc.relation.ispartofActa Crystallographica Section Een
dc.rightsCopyright © 2020 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.en
dc.subjectCrystal structureen
dc.subjectMolecular dimensionsen
dc.subjectMolecular conformationen
dc.subjectHydrogen bondingen
dc.subjectSupramolecular assemblyen
dc.subjectQD Chemistryen
dc.titleCrystal structures of the recreational drug it N-(4-methoxyphenyl)piperazine (MeOPP) and three of its saltsen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.description.statusPeer revieweden

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