2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline exhibit entirely different patterns of supramolecular aggregation

C  Glidewell; J N  Low; J M S  Skakle; S M S V  Wardell; J L  Wardell

doi:10.1107/S010827010201140X

2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline exhibit entirely different patterns of supramolecular aggregation

C Glidewell, J N Low, J M S Skakle, S M S V Wardell, J L Wardell

School of Chemistry

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

Abstract

In 2-iodo-N-(3-nitrobenzyl)aniline, C13H11IN2O2, the molecules are linked into a three-dimensional structure by a combination of C-H...O hydrogen bonds, iodo-nitro interactions and aromatic pi-pi-stacking interactions, but N-H...O and C-H...pi(arene) hydrogen bonds are absent. In the isomeric 3-iodo-N-(3-nitrobenzyl)aniline, a two-dimensional array is generated by a combination of N-H...O, C-H...O and C-H...(arene) hydrogen bonds, but iodo-nitro interactions and aromatic pi-pi-stacking interactions are both absent.

Original language	English
Number of pages	4
Journal	Acta Crystallographica Section C-Crystal Structure Communications
Volume	58
DOIs	https://doi.org/10.1107/S010827010201140X
Publication status	Published - Aug 2002

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title = "2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline exhibit entirely different patterns of supramolecular aggregation",

abstract = "In 2-iodo-N-(3-nitrobenzyl)aniline, C13H11IN2O2, the molecules are linked into a three-dimensional structure by a combination of C-H...O hydrogen bonds, iodo-nitro interactions and aromatic pi-pi-stacking interactions, but N-H...O and C-H...pi(arene) hydrogen bonds are absent. In the isomeric 3-iodo-N-(3-nitrobenzyl)aniline, a two-dimensional array is generated by a combination of N-H...O, C-H...O and C-H...(arene) hydrogen bonds, but iodo-nitro interactions and aromatic pi-pi-stacking interactions are both absent.",

author = "C Glidewell and Low, {J N} and Skakle, {J M S} and Wardell, {S M S V} and Wardell, {J L}",

year = "2002",

month = aug,

doi = "10.1107/S010827010201140X",

language = "English",

volume = "58",

journal = "Acta Crystallographica Section C-Crystal Structure Communications",

issn = "1600-5759",

publisher = "International Union of Crystallography",

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TY - JOUR

T1 - 2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline exhibit entirely different patterns of supramolecular aggregation

AU - Glidewell, C

AU - Low, J N

AU - Skakle, J M S

AU - Wardell, S M S V

AU - Wardell, J L

PY - 2002/8

Y1 - 2002/8

N2 - In 2-iodo-N-(3-nitrobenzyl)aniline, C13H11IN2O2, the molecules are linked into a three-dimensional structure by a combination of C-H...O hydrogen bonds, iodo-nitro interactions and aromatic pi-pi-stacking interactions, but N-H...O and C-H...pi(arene) hydrogen bonds are absent. In the isomeric 3-iodo-N-(3-nitrobenzyl)aniline, a two-dimensional array is generated by a combination of N-H...O, C-H...O and C-H...(arene) hydrogen bonds, but iodo-nitro interactions and aromatic pi-pi-stacking interactions are both absent.

AB - In 2-iodo-N-(3-nitrobenzyl)aniline, C13H11IN2O2, the molecules are linked into a three-dimensional structure by a combination of C-H...O hydrogen bonds, iodo-nitro interactions and aromatic pi-pi-stacking interactions, but N-H...O and C-H...pi(arene) hydrogen bonds are absent. In the isomeric 3-iodo-N-(3-nitrobenzyl)aniline, a two-dimensional array is generated by a combination of N-H...O, C-H...O and C-H...(arene) hydrogen bonds, but iodo-nitro interactions and aromatic pi-pi-stacking interactions are both absent.

U2 - 10.1107/S010827010201140X

DO - 10.1107/S010827010201140X

M3 - Article

SN - 1600-5759

VL - 58

JO - Acta Crystallographica Section C-Crystal Structure Communications

JF - Acta Crystallographica Section C-Crystal Structure Communications

ER -

2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline exhibit entirely different patterns of supramolecular aggregation

Abstract

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