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Synthesis, Crystal Structure and Hirshfeld Surface Analysis of Ethyl 4-(4-(2-Bromoethyl)-1H-1,2,3-triazol-1-yl)benzoate

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Abstract

The title compound, C13H14BrN3O2, was synthesized by click chemistry (CuAAC) using 4-bromobut-1-yne and ethyl 4-azidobenzoate. Its molecular structure was determined by 1H NMR, 13C NMR, IR spectra, elemental analysis, and the crystal structure was determined by single crystal X-ray diffraction analysis. It belongs to monoclinic system: space group P21/c, a = 4.9556(6) Å, b = 10.4549(7) Å, c = 27.417(2) Å, β = 93.442(6)°, Z = 4, and V = 1417.9(2) Å3. In the crystal structure, intermolecular hydrogen bonds C–HTrz⋅⋅⋅NTrz and C–HBrethy⋅⋅⋅BrBrethy (Trz = triazole and Brethy = bromoethyl) link the molecules into infinite chains along the a-axis; in this direction, they can be effective in stabilizing the structure. Weak C–H⋅⋅⋅π interaction is also observed. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are made by the interactions H…H (37.8%), H…Br/Br…H (17.8%), H…N/N…H (14.9%), H…C/C…H (11.0%), and H…O/O…H (10.8%). Hydrogen bonds and van der Waals interactions are the dominant interactions in crystal packing.

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Authors and Affiliations

  1. Muğla Sıtkı Koçman University, Department of Chemistry, 48000, Muğla, Turkey

    T. Göktürk & R. Güp

  2. Hacettepe University, Department of Physics, 06800, Ankara, Turkey

    T. Hökelek

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  1. T. Göktürk
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  2. T. Hökelek
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Correspondence to T. Göktürk.

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Göktürk, T., Hökelek, T. & Güp, R. Synthesis, Crystal Structure and Hirshfeld Surface Analysis of Ethyl 4-(4-(2-Bromoethyl)-1H-1,2,3-triazol-1-yl)benzoate. Crystallogr. Rep. 66, 977–984 (2021). https://doi.org/10.1134/S1063774521060109

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