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

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 H-1 NMR, C-13 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 P2(1)/c, a = 4.9556(6) angstrom, b = 10.4549(7) angstrom, c = 27.417(2) angstrom, beta = 93.442(6)degrees, Z = 4, and V = 1417.9(2) angstrom(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...pi 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 horizontal ellipsis H (37.8%), H horizontal ellipsis Br/Br horizontal ellipsis H (17.8%), H horizontal ellipsis N/N horizontal ellipsis H (14.9%), H horizontal ellipsis C/C horizontal ellipsis H (11.0%), and H horizontal ellipsis O/O horizontal ellipsis H (10.8%). Hydrogen bonds and van der Waals interactions are the dominant interactions in crystal packing.