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

• Published in: Crystallography reports Vol. 66; no. 6; pp. 977 - 984
• Main Authors: Göktürk, T., Hökelek, T., Güp, R.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 01.11.2021; Springer Nature B.V
• Subjects: Benzoates; Chemical analysis; Chemical synthesis; Crystal structure; Crystallography and Scattering Methods; Hydrogen bonds; Infrared analysis; Infrared spectroscopy; Molecular structure; NMR; Nuclear magnetic resonance; Physics; Physics and Astronomy; Single crystals; Structure of Organic Compounds; Surface analysis (chemical)
• ISSN: 1063-7745; 1562-689X
• DOI: 10.1134/S1063774521060109

The title compound, C 13 H 14 BrN 3 O 2 , was synthesized by click chemistry (CuAAC) using 4-bromobut-1-yne and ethyl 4-azidobenzoate. Its molecular structure was determined by 1 H NMR, 13 C 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 P 2 1 / 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) Å 3 . In the crystal structure, intermolecular hydrogen bonds C–H Trz ⋅⋅⋅N Trz and C–H Brethy ⋅⋅⋅Br Brethy (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.