In this study, N-(3-halophenyl)-2-pyrazinecarboxamide ligands, L3-F, L3-Cl, L3-Br, and L3-I, carrying a different halogen atom on the phenyl meta-position and N-phenyl-2-pyrazinecarboxamide ligand, L-H, have been employed for the synthesis of 12 mercury(II) complexes, [HgCl2(L-H)](n), 1, [HgCl2(L3-Cl)](n), 2, [Hg2Cl4(L3-Br)(2)], 3, [Hg2Cl4(L3-I)(2)], 4, [Hg2Br4(L-H)(2)], 5, [HgBr2(L3-F)], 6, [HgBr2(1(3-Cl))], 7, (HgBr2(L3-Br], 8, [HgBr2(L3-I)], 9, [Hg2I4(L-H)(2)], 10, [HgI2(L3-Br)], 11, and [HgI2(L3-I)](n), 12. Interestingly, structural analysis clearly shows that, by the replacing of coordinated anions from chloride with bromide and iodide in each series containing the same ligand, the coordination geometry and structural motif of the resulting compounds have been dramatically affected. One of the common features in the crystal structures of these complexes is that there is a strong tendency to form halogen bonding synthons between adjacent halophenyl and pyrazine rings. The influence of these halogen bonding interactions on the supramolecular assemblies has been discussed with the help of geometrical analysis and theoretical calculations. The X center dot center dot center dot N halogen bonding distances are 2.5-9.4% shorter than the sum of the van der Waals radii of nitrogen and halogen atoms. Theoretical methods also show the halogen bonding energies within a range of -27.86 to -46.15 kJ.mol(-1). In all complexes synthesized here, the pyrazine ring is coordinated to the mercury(II) ion through the N atom syn to the carbonyl. Therefore, the second common feature of the crystal structures for complexes studied here is the selectivity of the metal ion coordination site. The halogen bond synthon repetitivity across these compounds and selectivity in the mercury(II) ion coordination site further point to application in the coordination crystal engineering research field.