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Analysis of intermolecular interactions in 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol

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Abstract

In the present study, we have prepared and structurally characterized a derivative of 1,2,4 triazoles, namely 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol (T-1) via single crystal X-ray diffraction. The crystal structure was observed to be stabilized by the presence of various intermolecular interactions in the crystalline solid such as O-H ⋯S, C-H ⋯F, C-H ⋯S, C-H ⋯N, C-H ⋯O, C-H ⋯π, lp⋯π and π⋯π intermolecular interactions. The interaction energy of these interactions was evaluated through PIXEL method with decomposition of the total energy into the coulombic, polarization, dispersion and repulsion contribution. The study of the nature of H-bonds with sulfur reveals that stabilization due to contribution from polarization plays a significant role. It is noteworthy that the presence of the solvent molecules in the crystal structure were observed to provide stabilization to an otherwise destabilized molecular pair (comprising of two molecules of 1,2,4 triazoles in the asymmetric unit).

This study highlights the significant role of intermolecular H-bonds of an organic molecule with the solvent in the formation of the crystalline solid.

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Acknowledgements

PP thanks UGC for SRF fellowship. RS thanks IISER Bhopal for PhD scholarship. DC thanks IISER Bhopal for infrastructure and research facilities (experimental and computational) and DST for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal, 462 066, Madhya Pradesh, India

    PIYUSH PANINI, RAHUL SHUKLA & DEEPAK CHOPRA

  2. Rallis India Ltd, Bangalore, 560 091, Karnataka, India

    T P MOHAN

  3. Department of Chemistry, Mangalore University, Bangalore, 574 199, Karnataka, India

    B VISHALAKSHI

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  1. PIYUSH PANINI
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  2. RAHUL SHUKLA
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  3. T P MOHAN
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  4. B VISHALAKSHI
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Correspondence to DEEPAK CHOPRA.

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Supplementary Information

The information on yield, melting point, DSC trace and the Hirshfeld surface depicting di, de, dnorm, shape index and curvedness and the associated 2D-Fingerprint plots are included in supplementary information. Supplementary information is available at www.ias.ac.in/chemsci.

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PANINI, P., SHUKLA, R., MOHAN, T.P. et al. Analysis of intermolecular interactions in 3-(4-fluoro-3-phenoxyphenyl)-1-((4-methylpiperazin-1-yl)methyl)-1H-1,2,4-triazole-5-thiol. J Chem Sci 126, 1337–1345 (2014). https://doi.org/10.1007/s12039-014-0700-2

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