Abstract
The title compound, C6H15N4O2+.C4HO4−, crystallizes in the triclinic space group P1 with two independent formula units in the unit cell. The arginine molecules are protonated zwitterions with the amino and guanidyl moieties each accepting a proton from the acid group and the squaric acid. The torsion angles along the central N—C—(CH2)3—N chains are −166.8 (2), 165.7 (2), 168.9 (2), 178.2 (2)° in molecule (I) and −170.0 (1), 148.9 (2), 164.1 (2), 163.7 (2)° in molecule (II), respectively. The C—C bond lengths within the squarate anions are consistent with a delocalized double bond around the hydroxyl-bearing C atom, 1.426 (3) and 1.433 (3) Å versus 1.496 (3) and 1.491 (3) Å for the adjacent and opposite bonds respectively. The crystal structure consists of alternate layers of squarate and argininium moieties stacked along the c axis. The adjacent layers are connected to each other through specific ion-pair interactions (salt bridges) between the guanidyl group of arginine and the squarate moieties.
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