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The title acid, C19H16O2, crystallized in space group P1. In this structure, a hydrogen bond of the 'cyclic dimer' type is formed about a center of symmetry. The O(donor)...O(acceptor) distance is 2.647 (1) A. The carboxylic H and O atoms are ordered. The dihedral angle between the best-fit naphthalene plane and the carboxylic acid group plane is 11.1 (2) degrees.

Phenanthrene-4-carboxylic acid, C15H10O2, crystallized in the centrosymmetric space group P2(1)/n, while 1,2-dihydrophenanthrene-4-carboxylic acid, C15H12O2, crystallized in the centrosymmetric space group Pbca. In each structure, there is a single type of hydrogen bond: it is of the cyclic dimer type about a center of symmetry. The Odonor...Oacceptor distances are 2.634 (2) and 2.651 (2) A, and the O-H...O angles are 176 (3) and 173 (2) degrees, respectively, for the two structures. In each structure, the carboxy H and O atoms are ordered. The phenanthrene core of the fully aromatic acid is roughly planar; the dihedral angle between the best-fit core plane and the carboxy group plane is 63.7 (1) degree. As expected, the hydrogenated ring of the second acid is much less nearly planar; the remaining naphthalenoid core is, however, roughly planar and the dihedral angle between this best-fit plane and the carboxy group plane is 60.4 (1) degree.

The title compound, (+/-)-cis-2-phenylcyclopropanecarboxylic acid, C10H10O2, crystallized in the centrosymmetric space group P2(1)/n. The hydrogen bonding is of the cyclic dimer type about a center of symmetry; the Odonor...Oacceptor distance is 2.645 (2) A. The carboxylic H atom is ordered, as are the O atoms. The cyclopropane ring is asymmetric; the values found for the asymmetry parameters are delta(COOH) = -0.045 (4) A and delta(phenyl) = -0.027 (4) A.

The title compound, C13H12O4, crystallized in the centrosymmetric space group P2(1)/c and exhibits cyclic dimer hydrogen bonding about a center of symmetry. The carboxylic H atom is modeled as disordered over two half-occupancy sites. Overall, the hydrogen bonding is little affected by the methoxyl groups and is very similar to that in 2-naphthoic acid.

The title compound, C10H10O2, crystallized in space group P2(1) with two molecules in the asymmetric unit. In this structure, hydrogen bonding of the cyclic dimer type [with O ... O 2.623(2)-2.637(2)A] links the two molecules of the asymmetric unit. The two carboxylic H atoms are ordered, as are the O atoms. Each of the two non-equivalent molecules exhibits an asymmetric cyclopropane ring; the values found for the asymmetry parameters are delta(COOH) = -0.034(4) and -0.025(4)A, and delta(phenyl) = -0.028(4) and -0.023(4)A.

The title compound, C15H10O2, crystallized in the centrosymmetric space group C2/c. Hydrogen bonding is of the cyclic dimer type about a center of symmetry. The carboxyl H and O atoms are ordered. The phenanthrene core is almost planar and the dihedral angle between the core plane and the carboxyl group plane is only 1.8(1) degrees. The bay H atoms, H4 and H5, lie close to the core plane and 2.02 (2) A from each other; the refinement places them on opposite sides of the core plane, but this result has little statistical significance.

The title compound, C15H10O2, was found to crystallize in the centrosymmetric space group P2(1)/n. The hydrogen bonding is of the cyclic dimer type about a center of symmetry. The carboxyl O atoms are ordered as is the carboxyl H atom. The anthracene core, while less nearly planar, shows good agreement with the anthracene cores of anthracene-9-carboxylic acid and anthracene-1,6-dicarboxylic acid. The carboxyl group plane makes a dihedral angle of 12.4 (2) degrees with the best-fit anthracene core plane.

In 5,8-dimethoxy-1-naphthoic acid, C13H12O4, hydrogen bonding is of the cyclic dimer type. The acid H atom is modelled as being distributed equally over two sites. In addition to the conventional hydrogen bonds, there are three significantly attractive C-H...O interactions. The dihedral angle between the naphthalene core plane and the carboxyl plane is 80.0 (1) degrees. In methyl 5,8-dimethoxy-1-naphthoate, C14H14O4, there are no conventional hydrogen bonds but there are three significantly attractive C-H...O interactions. With the exception of the C-O distances in the carboxyl groups, the molecular geometries of the acid and the ester are quite similar.

The structures of 1-naphthoic acid and 2-naphthoic acid have been investigated in order to determine the degree of disorder of the carboxylic acid groups. 1-Naphthoic acid was found to be completely ordered with C--O bond lengths of 1.214 (3) and 1.312 (3) A, and C--C--O bond angles of 124.8 (2) and 114.2 (2) degrees. 2-Naphthoic acid was found to possess a significant degree of disorder with C--O bond lengths of 1.256 (3) and 1.274 (3) A, and C--C--O bond angles of 117.7 (2) and 119.1 (2) degrees. In 2-naphthoic acid, the acid H atom was refined at two sites with 0.5 occupancy at each. Analysis of the anisotropic displacement ellipsoids of the acid O atoms for each structure demonstrated that these parameters are consistent with thermal motion of the O atoms. These results indicated that the proton, but not the O atoms, is disordered in the carboxylic acid group of 2-naphthoic acid. In each structure, the acid molecules form cyclic dimers about inversion centers, with an O...O(acceptor) distance of 2.653 (3) in 1-naphthoic acid and 2.618 (3) A in 2-naphthoic acid. The cyclic dimers form layers in each of these structures wherein lateral closest intermolecular approaches to the acid O atoms are from ring H atoms. The intermolecular O...H close approaches, together with the intramolecular close approaches, are very uniform in distance and angle of approach for the two O atoms in the 2-naphthoic acid structure.(ABSTRACT TRUNCATED AT 250 WORDS)