9-OXOBICYCLO[3.3.1]NONANE-1-CARBOXYLIC ACID - STRUCTURE AND HYDROGEN-BONDING PATTERN

(1) C10H14O3, M(r) - 182.220, orthorhombic, Iham, a = 12.795 (2), b = 13.178 (2), c = 11.092 (2) angstrom, V(246 K) = 1870.2 (5), V(295 K) - 1891.8 (4) angstrom3, Z - 8, D(m)(295 K) = 1.26 (1), D(x)(295 K) - 1.280 g cm-3, lambda(Cu K-alpha) - 1.5418 angstrom, mu = 7.80 cm-1, F(000) = 784, T - 246 (1) K, R = 0.047 for 418 observed reflections. Compound (I) adopts a conformation having two flattened chair cyclohexanone rings, with the plane of the carboxyl group orthogonal to that of the ketone. Pairs of molecules form centrosymmetric dimers by mutual hydrogen bonding of carboxyl groups, leaving the ketone carbonyls uninvolved. The two conformationally enantiomeric arrangements of the carboxyl group are disordered in the crystal.