Reaction of 2-amino-5-iodopyridine (5IAP) with copper(II) bromide or chloride in alcoholic solution led to four coordination complexes: [(5-IAP)₂CuCl₂](H₂O) (1), (5-IAP)₂CuBr₂ (2), [(5-IAP)₂CuBr₂]₂ (3) and [(5-IAP)₃CuCl₂](H₂O)_n (4). The compounds were characterized by single crystal X-ray diffraction and variable temperature magnetic susceptibility measurements. 1 crystallizes as monomeric units with the 5IAP ligands in the syn-conformation and one lattice water molecule. 2 also exhibits syn-conformation 5IAP ligands, but forms a common bromide bibridged dimer structure. 3 is a conformational polymorph of 2 with anti-oriented 5IAP ligands. Long Cu⋯Br contacts link the molecules into chains. 4 crystallizes with 1.67 lattice water molecules, disordered over three positions. All four compounds exhibit strong halogen bonding. Variable field and temperature magnetic data were obtained on 1-3. 1 is paramagnetic, with no indication of magnetic exchange down to 1.8 K. 2 is well modeled as an antiferromagnetic dimer (J/k_B = -22 K) with significant antiferromagnetic interactions between the dimers. 3 is well modeled as a uniform antiferromagnetic chain (J/k_B = -6 K) with weak interchain interactions.