title: Cocrystallization of adamantane-1,3-dicarboxylic acid and 4,4'-bipyridine.
abstract: The cocrystallization of adamantane-1,3-dicarboxylic acid (adc) and 4,4'-bipyridine (4,4'-bpy) yields a unique 1:1 cocrystal, C(12)H(16)O(4).C(10)H(8)N(2), in the C2/c space group, with half of each molecule in the asymmetric unit. The mid-point of the central C-C bond of the 4,4'-bpy molecule rests on a center of inversion, while the adc molecule straddles a twofold rotation axis that passes through two of the adamantyl C atoms. The constituents of this cocrystal are joined by hydrogen bonds, the stronger of which are O-H...N hydrogen bonds [O...N = 2.6801 (17) A] and the weaker of which are C-H...O hydrogen bonds [C...O = 3.367 (2) A]. Alternate adc and 4,4'-bpy molecules engage in these hydrogen bonds to form zigzag chains. In turn, these chains are linked through pi-pi interactions along the c axis to generate two-dimensional layers. These layers are neatly packed into a stable crystalline three-dimensional form via weak C-H...O hydrogen bonds [C...O = 3.2744 (19) A] and van der Waals attractions.
authors.affiliation: Department of Chemistry and Chemical Biology, Rutgers University, Piscataway, NJ 08854, USA.
authors.forename: Yue
authors.initials: Y
authors.lastname: Pan
authors.forename: Kunhao
authors.initials: K
authors.lastname: Li
authors.forename: Wenhua
authors.initials: W
authors.lastname: Bi
authors.forename: Jing
authors.initials: J
authors.lastname: Li
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000737:chemistry; D003460:Crystallization; D003998:Dicarboxylic Acids / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*
chemical_list: C421745:1,3-adamantanedicarboxylic acid; D003998:Dicarboxylic Acids; D011725:Pyridines; D000218:Adamantane; C034306:4,4'-bipyridyl