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

TitleEvaluation of viability of halogen•••O2N interactions: insight form crystal packing in a series of isomeric halo and nitro substituted triaryl compounds with modular positioning of halogen and NO2 groups
Publication TypeJournal Article
Year of Publication2013
AuthorsRamana, CV, Goriya, Y, Durugkar, KA, Chatterjee, S, Krishnaswamy, S, Gonnade, RG
JournalCrystEngComm
Volume15
Issue26
Pagination5283-5300
Date PublishedAPR
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.

DOI10.1039/C3CE40192H
Funding Agency

Council of Scientific & Industrial Research (CSIR) - India

Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.858

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry