Crystal structures of the recreational drug <i>N</i>-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts
H. Kiran Kumar, H.S. Yathirajan, C. Harish Chinthal, Sabine Foro, Christopher Glidewell
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, C 11 H 16 N 2 O, (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. , C 11 H 17 N 2 O + ·C 7 H 3 N 2 O 6 − , (II), C 11 H 17 N 2 O + ·C 6 H 2 N 3 O 7 − , (III), and C 11 H 17 N 2 O + ·C 7 H 6 NO 2 − ·H 2 O, (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.