Centrosymmetric and Noncentrosymmetric <i>R</i>⁴₄(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (2−4), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 2−7 have the columns linked to form 2-D hydrogen bonded sheets and 8−10 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids

Centrosymmetric and Noncentrosymmetric <i>R</i>⁴₄(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (2−4), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 2−7 have the columns linked to form 2-D hydrogen bonded sheets and 8−10 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids

Centrosymmetric and Noncentrosymmetric <i>R</i>⁴₄(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (2−4), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 2−7 have the columns linked to form 2-D hydrogen bonded sheets and 8−10 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids

Centrosymmetric and Noncentrosymmetric <i>R</i>⁴₄(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (2−4), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 2−7 have the columns linked to form 2-D hydrogen bonded sheets and 8−10 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids

Centrosymmetric and Noncentrosymmetric <i>R</i>⁴₄(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (2−4), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 2−7 have the columns linked to form 2-D hydrogen bonded sheets and 8−10 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids

Centrosymmetric and Noncentrosymmetric <i>R</i>⁴₄(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (2−4), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 2−7 have the columns linked to form 2-D hydrogen bonded sheets and 8−10 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids

Centrosymmetric and Noncentrosymmetric <i>R</i>⁴₄(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (2−4), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 2−7 have the columns linked to form 2-D hydrogen bonded sheets and 8−10 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids

Hydrogen-Bonding Networks in a Bipodal Acyl-thiourea and Its Ni^II 2:2 Metallamacrocyclic Complex

The crystal structures of 3,3,3‘,3‘-tetra(2-hydroxyethyl)-1,1‘-isophthaloylbis(thiourea) (1) and its green metallamacrocyclic complex cis-[Ni(L-S,O)(pyridine)2]2 (2) are reported in the context of their supramolecular behavior dictated by the use of hydrogen-bonding end-groups on the ligand. In 1, each molecule forms a junction between two 4-fold chiral helices formed by the hydrogen bonding of hydroxyl moieties and sulfur atoms. The structure of 2 is laminar, consisting of layers of water-linked metallamacrocyclic cis-[Ni(L-S,O)(pyridine)2]2 units separated by layers of pyridine guest molecules. Thermogravimetric analysis of 2 shows that on heating the guest pyridine and water molecules are released at ca. 60 °C, followed quickly by the further release of coordinated pyridines from cis-[Ni(L-S,O)(pyridine)2]2 to yield cis-[Ni(L-S,O)]2

Centrosymmetric and Noncentrosymmetric <i>R</i>⁴₄(12) Rings As Primary Motifs in Salts of Sulfonate Anions and Chiral Primary Ammonium Cations: Their Occurrence in Hydrates, Nonhydrates, and the Zöllner Illusion

The acid−base reaction of naphthalene-1,5-disulfonic acid and naphthalene-2-sulfonic acid with homochiral (R)-1-phenylethylamine or (S)-1-phenylethylamine or heterochiral (RS)-1-phenethylamine give rise to 9 new organic salts: ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (2), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (3), ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate)•(H2O)2 (4), ((R)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (5), ((S)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (6) ((RS)-1-phenylethylammonium)2•(naphthalene-1,5-disulfonate) (7), ((R)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (8), ((S)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (9) and ((RS)-1-phenylethylammonium)•(naphthalene-2-sulfonate) (10). All nine ammonium sulfonate salts have different 1-D hydrogen bonded columns, some containing water molecules (2−4), which are made up of different sequences of hydrogen bonded rings. The most common hydrogen bonded ring formed by the ammonium and sulfonate ions has graph set notation R44(12). Structures 2−7 have the columns linked to form 2-D hydrogen bonded sheets and 8−10 have simple 1-D chains. The results of this work as well as an analysis of the Cambridge Structural Database indicate that the R44(12) is a dominant motif in crystals composed of ammonium sulfonate salts in the same way that R22(8) is the dominant motif in carboxylic acids

Robust Supramolecular Heterosynthons in Chiral Ammonium Carboxylate Salts

The ammonium carboxylate salts (m-iodobenzoate)·((R)-1-phenylethylammonium) (1), (m-iodobenzoate)·((S)-1-phenylethylammonium) (2), and (m-iodobenzoate)·((±)-1-phenylethylammonium) (3) self-assemble to form two types of one-dimensional hydrogen bonded columns, depending on the homo- or heterochirality of the cation: 1 and 2 form noncentrosymmetric hydrogen bonded columns having a 2-fold screw axis, whereas 3 forms centrosymmetric hydrogen bonded columns having an inversion center