Crystal structures of the recreational drug it N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts
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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.
Kiran 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 . https://doi.org/10.1107/S2056989020002844
Acta Crystallographica Section E
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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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