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The title substance, tripotassium naphthalene-1,8-dicarboxylate bicarbonate, 3K+.C12H6O4(2-).HCO3-, crystallized in the centrosymmetric space group Pbca. There is a single hydrogen bond. In it, the O and H atoms are ordered and OD...OA is 2.651 (3) A. There is a single significant intermolecular C-H...O interaction, with C...OA = 3.480 (5) A. Each potassium ion is coordinated by an irregular polyhedron of O atoms. These three polyhedra contain eight, eight and five members; each O atom is a member of at least two polyhedra. Structural comparisons are made with tetrapotassium naphthalene-1,4,5,8-tetracarboxylate hexahydrate.

The title substance, C12H6O3, crystallized in the centrosymmetric space group P2(1)/c with one molecule in the asymmetric unit. Four significant C-H...O interactions have C...O distances ranging from 3.313 (2) to 3.453 (2) A. They link each molecule directly to eight neighbors, generating a three-dimensional network. The anhydride group is compared with those in phthalic anhydride and 1,4,5,8-naphthalenetetracarboxylic 1,8:4,5-dianhydride.

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.

The title compound, C14H12O6, crystallized in the centrosymmetric space group Pbca but does not exhibit hydrogen bonding of the usual cyclic dimer type about a center of symmetry or otherwise. Each molecule is linked to six neighbors by eight hydrogen bonds, which leads, in this structure, to a rich pattern of chains. Of the nine patterns of chains described, six propagate along the a direction, while three propagate along the c direction. The Odonor...Oacceptor distances in these hydrogen bonds are 2.683 (2), 2.706 (2), 3.011 (2) and 3.218 (3) A. In addition, each C-H group in the molecule is involved in one or more significantly attractive C-H...O interactions, while every O atom is involved in two or more. The two carboxylic H atoms are ordered, as are the carboxylic O atoms.

1,4,5,8-Naphthalenetetracarboxylic acid cyclic 1,8-anhydride crystallized from dimethyl sulfoxide (DMSO) as the solvate, C14H6O7.2C2H6OS, in the centrosymmetric space group P1. Two O-H...O hydrogen bonds with O...O distances of 2.592 (3) and 2.598 (3) A are formed, with the two carboxylic acid OH groups as donors and the O atoms of the two inequivalent DMSO molecules as acceptors. The carboxylic H atoms are ordered, as are the carboxylic O atoms. In addition to the conventional hydrogen bonds, there are numerous C-H...O interactions consistent with the large number of potential CH donors and O-atom acceptors. 1,4,5,8-Naphthalenetetracarboxylic 1,8:4,5-dianhydride, C14H4O6, crystallized in the centrosymmetric space group P2(1)/c with half the molecule as the asymmetric unit. Each molecule is involved in four significant C-H...O interactions as a donor and in an additional four as an acceptor. These eight interactions link each molecule to six neighboring molecules, forming a three-dimensional network. Geometric parameters of both substances are in general agreement with analogous parameters for naphthalic anhydride, monosodium 1,4,5,8-naphthalenetetracarboxylic acid cyclic 1,8-anhydride monohydrate and 1,4,5,8-naphthalenetetracarboxylic 1,8:4,5-dianhydride, as reported previously.

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.

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 structure of 2-naphthoic acid, C11H8O2, has been investigated at 153 K in order to determine the degree of disorder of the carboxylic acid group for comparison with that of the room-temperature structure. Analysis of the anisotropic displacement ellipsoids of the carboxyl-O atoms demonstrated that these parameters are wholly consistent with thermal motion of the O atoms. A model with ordered carboxyl-O atoms, but with the acid-H atom refined at two sites with 0.5 occupancy at each, was found to be statistically significantly better than a model with ordered carboxyl-O atoms and an ordered acid-H atom. Thus, as in the room-temperature study, the best structural description is that the O atoms are ordered and the acid-H atom is disordered. Nonetheless, comparisons of the geometric parameters of the carboxyl groups at 296 and 153 K suggest progress toward a fully ordered structure at the lower temperature. Except for the expected slight overall contraction and the slightly altered geometry of the carboxyl group, the structure is virtually the same as at room temperature.

In the title structure, the 1,4,5,8-naphthalenetetra-carboxylate anion possesses 2/m symmetry with the twofold axis coincident with the central C--C bond of the naphthalene rings. The ten atoms comprising the naphthalene core have a mean deviation of 0.033 A from the best least-squares plane describing these atoms, with the carboxyl C atom 0.395 (2) A removed from the plane. The dihedral angle between the carboxylate plane and the least-squares plane of the naphthalene rings is 46.2 (3) degrees. The O--C--O angle of the carboxylate group, 121.13(12) degrees, is smaller than normally expected, presumably due to the bidentate interaction with the Ca ion. The Ca ion is coordinated by eight O atoms: six carboxylate O atoms and two water O atoms. Because the Ca ion resides on a twofold axis there are only four independent Ca--O distances, which are in the range 2.368 (1)-2.681 (1)A. In this structure, the organic anions are separated by Ca ions and water molecules such that there are no short-range organic-organic interactions. One of the water molecules separating the organic anions is not involved in coordination with Ca, and is disordered.

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)

1,8-Naphthalenedimethanol, C12H12O2, M(r) = 188.24, monoclinic, P2(1)/n, a = 8.549(4), b = 4.856(3), c = 22.604(4) A, beta = 94.24(3) degrees, V = 935.8(7) A 3, Z = 4, Dx = 1.34 g cm-3, lambda(Mo K alpha) = 0.71073 A, mu = 0.84 cm-1, F(000) = 400, T = 295 K, R = 0.042 for 1455 unique reflections having I > 3 sigma I. In the title structure the exterior angles at ring atoms C(1), C(8) and C(9) deviate significantly from 120 degrees as a result of the steric interactions of the hydroxymethyl substituents. The ten C atoms comprising the naphthalene core have an average deviation of 0.012 (7) A from the best least-squares plane describing the core. The conformation of the title compound is compared to those of other 1,8-disubstituted naphthalenes. Each hydroxy group is involved in hydrogen bonding as both acceptor and donor, creating infinite chains that propagate in the [010] directions. The neutron-adjusted parameters for the two H...O(acceptor) distances are 1.78 (3) and 1.80 (3) A and for the two O--H...O(acceptor) angles are 165 (2) and 170 (2) degrees. The packing arrangement can be described as a modified herringbone structure with the shortest crystallographic axis coinciding with the b axis of the standard monoclinic setting.

C12H8O4, M(r) = 216.20, monoclinic, C2/c, a = 5.087 (2), b = 19.222 (3), c = 9.552 (2) A, beta = 93.81 (3) degrees, V = 932.0 (5) A3, Z = 4, Dx = 1.54 g cm-3, lambda = 0.71073 A, mu = 1.09 cm-1, F(000) = 488, T = 295 K, R = 0.037 for 687 unique reflections having I > 3 sigma (I). In the structure reported here, a twofold axis lies in the plane of the molecule and bisects the three central ring bonds. The average C--C bond distance in the naphthalene core is 1.401 (27) A and the average interior angle 120.0 (14) degrees. The average deviation of the C atoms comprising the naphthalene rings from the best least-squares plane describing the rings is 0.021 (8) A. The plane of the single unique carboxylic acid group makes a dihedral angle of 33.1 (1) degrees with the least-squares plane of the naphthalene core. The carboxylic acid group, in which the observed O--H distance is 1.00 (3) A, forms a cyclic-dimer hydrogen bond across a center of inversion with the H...O(acceptor) distance 1.68 (3) A, the O...O-(acceptor) distance 2.676 (2) A and the O--H...O-(acceptor) angle 174 (3) degrees. The C--O bond lengths indicate no disorder in the carboxylic acid dimers. The molecules are arranged in stacks with the naphthalene cores parallel to the (102) plane and with the hydrogen bonds of the acid groups linking adjacent stacks. This structure of 2,3-naphthalenedicarboxylic acid is essentially the same as that of o-phthalic acid, but with the b cell edge correspondingly larger to accommodate the additional aromatic ring.

4Li+.C14H4O8(4-).12H2O, M(r) = 544.18, triclinic, P1, a = 9.608 (2), b = 10.034 (2), c = 7.033 (1) A, alpha = 94.29 (1), beta = 96.95 (1), gamma = 64.52 (1) degree, V = 607.4 (2) A3, Z = 1, D chi = 1.49 g cm-3, lambda (Mo K alpha) = 0.71073 A, mu = 1.29 cm-1, T = 295 K, F(000) = 284, R = 0.039 for 2781 unique reflections having I greater than sigma I. The two inequivalent carboxyl groups adopt a non-planar arrangement with respect to the naphthalene core, making dihedral angles of 52.7 (1) and 54.6 (1) degree with it. The Li+ ions are tetrahedrally coordinated by carboxyl and water O atoms. The Li-O distances are in the range 1.906 (3)-2.041 (3) A, averaging 1.97 (4) A; O-Li-O angles are 101.5 (1)-123.9 (1) degree, averaging 109 (6) degrees. Each of the 12 inequivalent water H atoms is involved in hydrogen bonding. Of these bonds, 11 are typical two-centered hydrogen bonds with an average H...O (acceptor) distance of 1.92 (11) A and an average O-H...O (acceptor) angle of 172 (5) degrees. One water H atom is involved in a three-centered hydrogen bond with an average H...O (acceptor) distance of 2.61 (4) A and an average O-H...O (acceptor) angle of 120 (3) degrees. Adjacent organic anions are separated by the Li+ ions and their coordination polyhedra, with the water molecules occupying positions above and below the naphthalene rings and participating in a three-dimensional hydrogen-bonded network.

(1) 1,2-Naphthalenedicarboxylic acid-diethyl ether, C12H8O4.nC4H10O, M(r) = 216.19, tetragonal, I4(1)/a, a = 22.086 (3), c = 9.463 (3) A, V = 4616 (2) A3, Z = 16, F(000) = 1792 (without ether), F(000) = 1873 (with 2.7 molecules of ether per unit cell), Dx = 1.24 g cm-3 (without ether), Dx = 1.31 g cm-3 (with 2.7 molecules of ether per unit cell), lambda(Mo K alpha) = 0.71073 A, T = 296 K, mu = 0.88 cm-1, R = 0.052 for 1130 unique reflections having I greater than 3 sigma I. (2) 1,2-Naphthalenedicarboxylic acid, C12H8O4, M(r) = 216.19, triclinic, P1, a = 9.027 (1), b = 9.234 (1), c = 7.256 (1) A, alpha = 106.08 (1), beta = 90.79 (1), gamma = 111.80 (1) degrees, V = 535.0 (1) A3, Z = 2, F(000) = 224, Dx = 1.34 g cm-3, lambda (Mo K alpha) = 0.71073 A, T = 296 K, mu = 0.95 cm-1, R = 0.043 for 1216 unique reflections having I greater than 3 sigma I. (3) 1,2-Naphthalenedicarboxylic acid-dimethoxyethane, C12H8O4.nC4H10O2, M(r) = 216.19, tetragonal, I4(1)/a, a = 22.067 (2), c = 9.465 (2) A, V = 4609 (1) A3, Z = 16, Dx = 1.25 g cm-3 (without dimethoxyethane), Dx = 1.39 g cm-3 (with 4.4 molecules of dimethoxyethane per unit cell), lambda(Mo K alpha) = 0.71073 A, T = 296 K.(ABSTRACT TRUNCATED AT 250 WORDS)

Sodium hydrogen 1,3-dioxo-1H,3H-naphtho[1,8-cd]pyran-6,7-dicarboxylate hydrate, Na[C14H5O7].H2O, Mr = 326.2, triclinic, P1, a = 9.520 (2), b = 9.549 (3), c = 7.860 (1) A, alpha = 105.88 (2), beta = 110.29 (1), gamma = 100.89 (2) degrees, V = 611.9 (3) A3, Z = 2, Dx = 1.77 g cm-3, lambda(Mo K alpha) = 0.71073 A, mu = 1.67 cm-1, F(000) = 332, T = 295 K, R = 0.042 for 1665 unique reflections having I greater than 3 sigma I. The organic portion of this structure demonstrates near-C2 symmetry with a pseudo-twofold axis coincident with the central C-C naphthalene ring bond. The atoms of the naphthopyran three-ring system deviate by an average of 0.037 (19) A from the best least-squares plane through the three rings. Each of the carboxyl group planes is substantially inclined to the naphthopyran ring plane, the average dihedral angle measuring 62 (1) degree. The Na ion is coordinated by O atoms in a highly distorted octahedral geometry with a mean Na--O distance of 2.49 (12) A. A short hydrogen bond is formed between a carboxylic acid group and a carboxylate anion; the H...O(acceptor) distance is 1.35 (5) A and the O...O(acceptor) distance is 2.475 (3) A. The acid H-atom position is located asymmetrically with respect to the O atoms. The water H atoms are involved in unequal three-centered hydrogen bonds. The molecules are stacked such that the naphthopyran ring portion of the structure is nearly parallel to the ab cell face and the stacks are connected by the hydrogen bonds.(ABSTRACT TRUNCATED AT 250 WORDS)

Na4[C14H4O8].8H2O, Mr = 536.3, monoclinic, P2(1)/n, a = 6.142 (1), b = 8.144 (3), c = 20.527 (4) A, beta = 93.97 (1) degrees, V = 1024.4 (5) A3, Z = 2, Dx = 1.74 g cm-3, lambda(Mo K alpha) = 0.71073 A, mu = 2.14 cm-1, F(000) = 552 T = 295 K, R = 0.039 for 1769 unique reflections having I greater than sigma I. In this structure, the title compound has an inversion center at the midpoint of the central naphthalene ring bond. The average C-C bond length in the naphthalene core is 1.41 (3) A; the average interior angle is 119.9 (1.0) degrees. The exterior angle at the central naphthalene carbon is 122.7 (3) degrees, significantly smaller than in 1.8-substituted naphthalenes. The two inequivalent carboxyl groups adopt a non-planar arrangement with respect to the naphthalene core, making an average dihedral angle of 53.8 (1) degree with it. The two inequivalent sodium ions have quite different environments. Na(1) is coordinated by six O atoms in a highly distorted octahedral arrangement with an average Na-O distance of 2.44 (10) A. Na(2) is coordinated by five O atoms in a highly distorted trigonal bipyramidal arrangement with an average Na-O distance of 2.36 (3) A. Each of the eight inequivalent water H atoms is involved in a single hydrogen bond. The average H...O (acceptor) distance is 2.00 (5) A, the average O...O (acceptor) distance is 2.85 (5) A and the average O-H...O (acceptor) angle is 165 (8) degrees for these hydrogen bonds.(ABSTRACT TRUNCATED AT 250 WORDS)

C12H8O4, Mr = 216.19, orthorhombic, Pbca, a = 15.308 (2), b = 17.926 (2), c = 7.093 (2) A, V = 1946.4 (5) A3, Z = 8, Dx = 1.48 g cm-3, lambda (Mo K alpha) = 0.71073 A, mu = 1.05 cm-1, F(000) = 896, T = 296 K, R = 0.043 for 912 unique reflections having I greater than 3 sigma (I). In this structure, 1,8-naphthalenedicarboxylic acid departs significantly from planarity. While the average deviation of carbons from the best least-squares plane for the naphthalene core is 0.055 (4) A, the carboxyl carbons adopt positions +0.403 (4) and -0.350 (4) A from that plane. The carboxyl groups are twisted in the same direction with respect to that plane and make an average dihedral angle of 42.6 (3) degrees with it. The nearly equal lengths of the C--O distances within the carboxyl groups [mean value 1.267 (5) A] indicate almost complete disorder of the H atoms of these groups. Hydrogen bonding occurs in cyclic dimer fashion between two molecules related by a center of inversion. The carboxyl hydrogens appear to be subject to a symmetric double-minimum potential and to be disordered via tunneling; there is no evidence that the carboxyl oxygens are disordered. The mean carboxyl H--O acceptor distance is 1.90 (7) A.