Issue 26, 2013
From the journal:

CrystEngComm

Evaluation of viability of halogen⋯O2N interactions: Insight from crystal packing in a series of isomeric halo and nitro substituted triaryl compounds with modular positioning of halogen and NO2 groups†

C. V. Ramana,*a   Yogesh Goriya,a   Kulbhushan A. Durugkar,a   Soumitra Chatterjee,a   Shobhana Krishnaswamyb  and  Rajesh G. Gonnade*b  

* Corresponding authors

a Division of Organic Chemistry, National Chemical Laboratory (CSIR-NCL), Pune, India
E-mail: vr.chepurix@ncl.res.in
Fax: +91 20 2590 2629
Tel: +91 20 2590 2277

b Center for Materials Characterization, National Chemical Laboratory (CSIR-NCL), Pune, India
E-mail: rg.gonnade@ncl.res.in
Fax: +91 20 2590 2642
Tel: +91 20 2590 2225

Abstract

A series of isomeric triaryl compounds with a modular positioning of the halogen and NO2 groups have been synthesized by the azide–alkyne “click reaction” and have been characterized by single crystal X-ray structure analysis. This isomeric series has provided an opportunity for understanding the efficiency of the bifurcated halogen⋯NO2 synthon in the organization of the molecules in the crystalline lattice. The changes in molecular conformation, crystal packing and supramolecular aggregation due to the change in the relative positioning of the complementary groups, halogen atom and the NO2 group on ring A and ring C respectively, have been discussed. All the isomers synthesized are crystalline and establish the triazole as a reliable linker for crystal engineering oriented molecular synthesis. The 2-NO2 derivatives display in general, a helical architecture and 3-NO2 derivatives exhibit a centrosymmetric dimeric assembly via the complementary C–H⋯O interactions leading to either a helical or a 2-dimensional sheet pattern. The molecular organization in 4-NO2 derivatives revealed in general a 2D sheet pattern.

Graphical abstract: Evaluation of viability of halogen⋯O2N interactions: Insight from crystal packing in a series of isomeric halo and nitro substituted triaryl compounds with modular positioning of halogen and NO2 groups

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Article information

DOI
https://doi.org/10.1039/C3CE40192H
Article type
Paper
Submitted
29 Jan 2013
Accepted
26 Apr 2013
First published
30 Apr 2013

CrystEngComm, 2013,15, 5283-5300

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Evaluation of viability of halogen⋯O2N interactions: Insight from crystal packing in a series of isomeric halo and nitro substituted triaryl compounds with modular positioning of halogen and NO2 groups

C. V. Ramana, Y. Goriya, K. A. Durugkar, S. Chatterjee, S. Krishnaswamy and R. G. Gonnade, CrystEngComm, 2013, 15, 5283 DOI: 10.1039/C3CE40192H

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