Hugh W. Thompson

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The title compound, (1R,2R,3S,5S,8S)-3-hydr-oxy-8-methyl-8-azoniabicyclo-[3.2.1]octane-2-carboxylic acid chloride, C(9)H(16)NO(3) (+)·Cl(-), is both a metabolite and a precursor of the tropane alkaloid l-cocaine. The carboxyl group is not involved in dimerization, but instead donates a hydrogen bond to the chloride counter-ion, which participates in two(More)
The title racemate, C(7)H(10)O(3), aggregates in the solid as acid-to-ketone hydrogen-bonding catemers [O⋯O = 2.7050 (13) Å and O-H⋯O = 166.1 (17)°] having glide-related components. Four such heterochiral chains, paired centrosymmetrically about (, , ) in the cell, proceed through the cell in the 010 direction, with alignment with respect to the c axis of(More)
The title ketocarboxylic acid, C(5)H(6)O(3), is the smallest carboxy-cyclanone to have its crystal structure determined. It adopts a chiral conformation, by rotation of its carboxyl O atoms away from the plane of skeletal symmetry that passes through the carboxyl carbon and both atoms of the ketone carbonyl. The four-membered ring is non-planar, with a(More)
The title compound, C(15)H(16)O(3), aggregates as hydrogen-bonded catemers progressing from each carboxyl to the ketone of a screw-related neighbor [O⋯O = 2.6675 (14) Å and O-H⋯O = 170°]. Two parallel centrosymmetrically related single-strand hydrogen-bonding helices proceed through the cell in the b-axis direction. The packing includes three(More)
The title racemate, C(11)H(14)O(3), aggregates in the crystal structure as acid-to-ketone O-H⋯O hydrogen-bonding catemers whose components are glide-related. The relative stereochemistry at the carboxyl group arises spontaneously during the synthesis. Two inter-molecular C-H⋯O=C close contacts were found, both involving the acid group.
In the crystal structure of the title compound, C(9)H(8)O(3), essentially planar mol-ecules [the carboxyl group makes a dihedral angle of 4.53 (7)° with the plane of the ring, while the acid group forms a dihedral angle of 3.45 (8)° to the ring] aggregate by centrosymmetric hydrogen-bond pairing of ordered carboxyl groups. This yields dimers which have two(More)
The monohydrate of the title phenolic diacid (C8H6O5.H2O, 2-hydroxybenzene-1,3-dioic acid or 3-carboxysalicylic acid) adopts a planar conformation, with the phenol hydrogen internally hydrogen-bonded to the carbonyl of one highly ordered carboxyl, which, in turn, donates a hydrogen bond to the oxygen of water. The second carboxyl is disordered and(More)
The asymmetric unit of the title compound, C(8)H(12)O(3), consists of a single conformational enanti-omer, which aggregates in the catemeric acid-to-ketone hydrogen-bonding mode [O⋯O = 2.682 (4) Å and O-H⋯O = 172 (6)°]. Four hydrogen-bonding chains of translationally related mol-ecules pass through the cell orthogonal to the 4(3) screw axis along c,(More)
The title keto acid, C(16)H(18)O(3), displays significant twisting of all three ethyl-ene bridges in its bicyclo-[2.2.2]octane structure owing to steric inter-actions; the bridgehead-to-bridgehead torsion angles are 13.14 (12), 13.14 (13) and 9.37 (13)°. The compound crystallizes as centrosymmetric carboxyl dimers [O⋯O = 2.6513 (12) Å and O-H⋯O = 178°],(More)
The title compound, C(16)H(14)O(3), adopts a conformation in which each functional group is almost coplanar with its adjacent ring, while the two aromatic rings are twisted with respect to one another with a dihedral angle of 78.51 (3)°. The compound dimerizes by standard centrosymmetric hydrogen-bonded carboxyl pairing [O⋯O = 2.6218 (11) Å and O-H⋯O = 176(More)