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Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly

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Six 1-aroyl-4-(4-methoxyphenyl)piperazines : similar molecular structures but different patterns of supramolecular assembly. / Kiran Kumar, Haruvegowda; Yathirajan, Hemmige S.; Sagar, Belakavadi K.; Foro, Sabine; Glidewell, Christopher.

In: Acta Crystallographica Section E, Vol. 75, No. 8, 08.2019, p. 1253-1260.

Research output: Contribution to journalArticlepeer-review

Harvard

Kiran Kumar, H, Yathirajan, HS, Sagar, BK, Foro, S & Glidewell, C 2019, 'Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly', Acta Crystallographica Section E, vol. 75, no. 8, pp. 1253-1260. https://doi.org/10.1107/S2056989019010491

APA

Kiran Kumar, H., Yathirajan, H. S., Sagar, B. K., Foro, S., & Glidewell, C. (2019). Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly. Acta Crystallographica Section E, 75(8), 1253-1260. https://doi.org/10.1107/S2056989019010491

Vancouver

Kiran Kumar H, Yathirajan HS, Sagar BK, Foro S, Glidewell C. Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly. Acta Crystallographica Section E. 2019 Aug;75(8):1253-1260. https://doi.org/10.1107/S2056989019010491

Author

Kiran Kumar, Haruvegowda ; Yathirajan, Hemmige S. ; Sagar, Belakavadi K. ; Foro, Sabine ; Glidewell, Christopher. / Six 1-aroyl-4-(4-methoxyphenyl)piperazines : similar molecular structures but different patterns of supramolecular assembly. In: Acta Crystallographica Section E. 2019 ; Vol. 75, No. 8. pp. 1253-1260.

Bibtex - Download

@article{1b256ebfeb574d2288a294dcfc31dc8f,
title = "Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly",
abstract = "Six new 1-aroyl-4-(4-meth­oxy­phen­yl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-meth­oxy­phen­yl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-meth­oxy­phen­yl)piperazine, C18H20N2O2, (I). The mol­ecules of 1-(2-fluoro­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19FN2O2, (II), are linked by two C—H⋯O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π–π stacking inter­action. 1-(2-Chloro­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19ClN2O2, (III), 1-(2-bromo­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19BrN2O2, (IV), and 1-(2-iodo­benzo­yl)-4-(4-meth­oxyphen­yl)piperazine, C18H19IN2O2, (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)–(V), a combination of two C—H⋯π(arene) hydrogen bonds links the mol­ecules into sheets. A single O—H⋯O hydrogen bond links the mol­ecules of 1-(2-hy­droxy­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H20N2O3, (VI), into simple chains. Comparisons are made with the structures of some related compounds.",
keywords = "Piperazines, Crystal structure, Isomorphism problem, Disorder, Hydrogen bonding, Supramolecular assembly",
author = "{Kiran Kumar}, Haruvegowda and Yathirajan, {Hemmige S.} and Sagar, {Belakavadi K.} 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 = "2019",
month = aug,
doi = "10.1107/S2056989019010491",
language = "English",
volume = "75",
pages = "1253--1260",
journal = "Acta Crystallographica Section E Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "8",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - Six 1-aroyl-4-(4-methoxyphenyl)piperazines

T2 - similar molecular structures but different patterns of supramolecular assembly

AU - Kiran Kumar, Haruvegowda

AU - Yathirajan, Hemmige S.

AU - Sagar, Belakavadi K.

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 - 2019/8

Y1 - 2019/8

N2 - Six new 1-aroyl-4-(4-meth­oxy­phen­yl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-meth­oxy­phen­yl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-meth­oxy­phen­yl)piperazine, C18H20N2O2, (I). The mol­ecules of 1-(2-fluoro­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19FN2O2, (II), are linked by two C—H⋯O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π–π stacking inter­action. 1-(2-Chloro­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19ClN2O2, (III), 1-(2-bromo­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19BrN2O2, (IV), and 1-(2-iodo­benzo­yl)-4-(4-meth­oxyphen­yl)piperazine, C18H19IN2O2, (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)–(V), a combination of two C—H⋯π(arene) hydrogen bonds links the mol­ecules into sheets. A single O—H⋯O hydrogen bond links the mol­ecules of 1-(2-hy­droxy­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H20N2O3, (VI), into simple chains. Comparisons are made with the structures of some related compounds.

AB - Six new 1-aroyl-4-(4-meth­oxy­phen­yl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-meth­oxy­phen­yl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-meth­oxy­phen­yl)piperazine, C18H20N2O2, (I). The mol­ecules of 1-(2-fluoro­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19FN2O2, (II), are linked by two C—H⋯O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π–π stacking inter­action. 1-(2-Chloro­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19ClN2O2, (III), 1-(2-bromo­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H19BrN2O2, (IV), and 1-(2-iodo­benzo­yl)-4-(4-meth­oxyphen­yl)piperazine, C18H19IN2O2, (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)–(V), a combination of two C—H⋯π(arene) hydrogen bonds links the mol­ecules into sheets. A single O—H⋯O hydrogen bond links the mol­ecules of 1-(2-hy­droxy­benzo­yl)-4-(4-meth­oxy­phen­yl)piperazine, C18H20N2O3, (VI), into simple chains. Comparisons are made with the structures of some related compounds.

KW - Piperazines

KW - Crystal structure

KW - Isomorphism problem

KW - Disorder

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S2056989019010491

DO - 10.1107/S2056989019010491

M3 - Article

VL - 75

SP - 1253

EP - 1260

JO - Acta Crystallographica Section E Crystallographic Communications

JF - Acta Crystallographica Section E Crystallographic Communications

SN - 2056-9890

IS - 8

ER -

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