Source of material 1,2-Bis-(4-pyridyl)ethylene (bpe, 0.5 mmol), 2-bromo-1,4-benzenedicarboxylic acid (0.5 mmol), and KOH (0.5 mmol) were added to water (12 ml) in a Teflon-lined stainless steel reactor. The mixture was heated at 426 K for three days, and then slowly cooled down to room temperature. Colorless crystals of the title compound were obtained.
Experimental detailsThe Br atoms are disordered over two sites, viz. Br1 (bonded to atom C3) and Br2 (bonded to atom C6). The site occupancy factors of Br1 and Br2 atoms were refined and converged to 0.271(2) and 0.729, respectively.
DiscussionDesigning the solid state with molecules that encode well defined noncovalent interactions has recently become a rapidly growing area of research due to their fascinating molecular and/or supramolecular structural diversity and potential applications for catalysis [1-4] and material sciences [5][6]. Recent progress in this area has generated examples where the design of network structures produced crystals with 1D, 2D, and 3D networks composed either of hydrogen bonding, metal-ligand coordination, or a combination of these with other interactions [7][8][9]. One of the best strategies to design high-dimensional supramolecular systems is to utilize the hydrogen bonding of the bridging ligand in addition to their coordination capability. The aromatic dicarboxylates are used extensively in the synthesis of coordination polymers [10] and the generation of hydrogen-bonding arrays of organic cocrystals [11]. The 2-bromo-1,4-benzene-dicarboxylic acid, possesses several interesting characteristics: (a) it has two carboxyl groups which may be completely or partially deprotonated, inducing rich coordination modes and allowing interesting structures with higher dimensions; (b) it can act not only as hydrogenbond acceptor but also as hydrogen-bond donor, depending upon the numbers of deprotonated carboxyl groups. To propagate noncovalent interactions along one direction only, each unit must have two-point interactions with two adjacent neighbors. The acid and bpe both epitomize this model and exhibit a two-point contact per unit that results in 1-D hydrogen bonding networks. The crystal structure of the title compound comprises a bpe molecule and a 2-bromo-1,4-benzenedicarboxylic acid molecule per asymmetric unit. The H atoms attached to O2 and O3 participate in intramolecular O−H···N hydrogen bonds. Hence there are two H atoms on O2 and O3 available for the formation of hard intermolecular hydrogen bonds. Within the asymmetric unit, carboxylate atom O2 and O3 act as hydrogen-bond donors to N1 and N2, via H2D and H3D, respectively. These O−H···N hydrogen bonds generate, a 1-D chain in which acid and bpe molecules alternate, the acid acting as a double donor of hydrogen bonds and the bpe as a double acceptor. The bromine atoms Br1 and Br2 make strong Br···O interactions with the O3 and O2 atoms [12], respectively, and as a consequence, the 1-D chains are further connected to a 2-D supramolecular architecture. Despite the presence of phen...