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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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Crystal structures of the recreational drug it N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts. / Kiran Kumar, Haruvegowda; Yathirajan, Hemmige S.; Harish Chinthal, Chayanna; Foro, Sabine; Glidewell, Christopher.

In: Acta Crystallographica Section E, Vol. 76, No. 4, 04.2020, p. 488-495.

Research output: Contribution to journalArticlepeer-review

Harvard

Kiran Kumar, H, Yathirajan, HS, 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

APA

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, 76(4), 488-495. https://doi.org/10.1107/S2056989020002844

Vancouver

Kiran Kumar H, Yathirajan HS, Harish Chinthal C, Foro S, Glidewell C. Crystal structures of the recreational drug it N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts. Acta Crystallographica Section E. 2020 Apr;76(4):488-495. https://doi.org/10.1107/S2056989020002844

Author

Kiran Kumar, Haruvegowda ; Yathirajan, Hemmige S. ; Harish Chinthal, Chayanna ; Foro, Sabine ; Glidewell, Christopher. / Crystal structures of the recreational drug it N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts. In: Acta Crystallographica Section E. 2020 ; Vol. 76, No. 4. pp. 488-495.

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@article{c44b586044c240e0ab3fedc8fd0c1529,
title = "Crystal structures of the recreational drug it N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts",
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.",
keywords = "Piperazines, Crystal structure, Molecular dimensions, Molecular conformation, Hydrogen bonding, Supramolecular assembly",
author = "{Kiran Kumar}, Haruvegowda and Yathirajan, {Hemmige S.} and {Harish Chinthal}, Chayanna and Sabine Foro and Christopher Glidewell",
note = "HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.",
year = "2020",
month = apr,
doi = "10.1107/S2056989020002844",
language = "English",
volume = "76",
pages = "488--495",
journal = "Acta Crystallographica Section E Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "4",

}

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TY - JOUR

T1 - Crystal structures of the recreational drug it N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts

AU - Kiran Kumar, Haruvegowda

AU - Yathirajan, Hemmige S.

AU - Harish Chinthal, Chayanna

AU - Foro, Sabine

AU - Glidewell, Christopher

N1 - HSY thanks the University Grants Commission, New Delhi for the award of a BSR Faculty Fellowship for three years.

PY - 2020/4

Y1 - 2020/4

N2 - 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.

AB - 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.

KW - Piperazines

KW - Crystal structure

KW - Molecular dimensions

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S2056989020002844

DO - 10.1107/S2056989020002844

M3 - Article

VL - 76

SP - 488

EP - 495

JO - Acta Crystallographica Section E Crystallographic Communications

JF - Acta Crystallographica Section E Crystallographic Communications

SN - 2056-9890

IS - 4

ER -

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