The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by π-π stacking interactions and I···N halogen bonds

Ninganayaka Mahesha; Hemmige S. Yathirajan; Tetsundo Furuya; Takashiro Akitsu; Christopher Glidewell

doi:10.1107/S205698901801811X

The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by π-π stacking interactions and I···N halogen bonds

Ninganayaka Mahesha, Hemmige S. Yathirajan, Tetsundo Furuya, Takashiro Akitsu, Christopher Glidewell

School of Chemistry

Research output: Contribution to journal › Article › peer-review

4 Citations (Scopus)

1 Downloads (Pure)

Abstract

In 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine, C₁₅H ₁₅IN ₄O, the central piperazine ring adopts an almost perfect chair conformation with the pyrimidine substituent in an equatorial site. The planar amide unit makes a dihedral angle of 80.44 (7)° with the phenyl ring. A combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds links the molecules into a complex three-dimensional network structure, augmented by a π– π stacking interaction and an I⋯N halogen bond, all involving different pairs of inversion-related molecules. Comparisons are made with the structures of a number of related compounds.

Original language	English
Pages (from-to)	129-133
Number of pages	5
Journal	Acta Crystallographica Section E
Volume	75
Issue number	2
Early online date	4 Jan 2019
DOIs	https://doi.org/10.1107/S205698901801811X
Publication status	Published - 1 Feb 2019

Keywords

Pyrimidine
Piperazine
Crystal structure
Molecular conformation
Hydrogen bonding
Supramolecular assembly

Access to Document

10.1107/S205698901801811XLicence: CC BY

Mahesha_2019_ACCCE_Crystalstructure_CC
Copyright © 2019 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.
Final published version, 1.06 MBLicence: CC BY

The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by π-π stacking interactions and I···N halogen bonds (crystallography data)
Mahesha, N. (Creator), Yathirajan, H. S. (Creator), Furuya, T. (Creator), Akitsu, T. (Creator) & Glidewell, C. (Creator), Cambridge Crystallographic Data Centre, 2019
https://dx.doi.org/10.5517/ccdc.csd.cc21b43n
Dataset

Cite this

@article{1647a34a09ef482da6b3ade349c2d7b1,

title = "The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by π-π stacking interactions and I···N halogen bonds",

abstract = "In 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine, C15H 15IN 4O, the central piperazine ring adopts an almost perfect chair conformation with the pyrimidine substituent in an equatorial site. The planar amide unit makes a dihedral angle of 80.44 (7)° with the phenyl ring. A combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds links the molecules into a complex three-dimensional network structure, augmented by a π– π stacking interaction and an I⋯N halogen bond, all involving different pairs of inversion-related molecules. Comparisons are made with the structures of a number of related compounds.",

keywords = "Pyrimidine, Piperazine, Crystal structure, Molecular conformation, Hydrogen bonding, Supramolecular assembly",

author = "Ninganayaka Mahesha and Yathirajan, {Hemmige S.} and Tetsundo Furuya and Takashiro Akitsu and Christopher Glidewell",

note = "HSY is grateful to the UGC, New Delhi for the award of a BSR Faculty Fellowship for three years.",

year = "2019",

month = feb,

day = "1",

doi = "10.1107/S205698901801811X",

language = "English",

volume = "75",

pages = "129--133",

journal = "Acta Crystallographica Section E",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "2",

}

The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by π-π stacking interactions and I···N halogen bonds. / Mahesha, Ninganayaka; Yathirajan, Hemmige S.; Furuya, Tetsundo et al.
In: Acta Crystallographica Section E, Vol. 75, No. 2, 01.02.2019, p. 129-133.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine

T2 - a three-dimensional hydrogen-bonded framework, augmented by π-π stacking interactions and I···N halogen bonds

AU - Mahesha, Ninganayaka

AU - Yathirajan, Hemmige S.

AU - Furuya, Tetsundo

AU - Akitsu, Takashiro

AU - Glidewell, Christopher

N1 - HSY is grateful to the UGC, New Delhi for the award of a BSR Faculty Fellowship for three years.

PY - 2019/2/1

Y1 - 2019/2/1

N2 - In 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine, C15H 15IN 4O, the central piperazine ring adopts an almost perfect chair conformation with the pyrimidine substituent in an equatorial site. The planar amide unit makes a dihedral angle of 80.44 (7)° with the phenyl ring. A combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds links the molecules into a complex three-dimensional network structure, augmented by a π– π stacking interaction and an I⋯N halogen bond, all involving different pairs of inversion-related molecules. Comparisons are made with the structures of a number of related compounds.

AB - In 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine, C15H 15IN 4O, the central piperazine ring adopts an almost perfect chair conformation with the pyrimidine substituent in an equatorial site. The planar amide unit makes a dihedral angle of 80.44 (7)° with the phenyl ring. A combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds links the molecules into a complex three-dimensional network structure, augmented by a π– π stacking interaction and an I⋯N halogen bond, all involving different pairs of inversion-related molecules. Comparisons are made with the structures of a number of related compounds.

KW - Pyrimidine

KW - Piperazine

KW - Crystal structure

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S205698901801811X

DO - 10.1107/S205698901801811X

M3 - Article

SN - 2056-9890

VL - 75

SP - 129

EP - 133

JO - Acta Crystallographica Section E

JF - Acta Crystallographica Section E

IS - 2

ER -

The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by π-π stacking interactions and I···N halogen bonds

Abstract

Keywords

Access to Document

Fingerprint

Datasets

The crystal structure of 1-(2-iodobenzoyl)-4-(pyrimidin-2-yl)piperazine: a three-dimensional hydrogen-bonded framework, augmented by π-π stacking interactions and I···N halogen bonds (crystallography data)

Cite this