Supramolecular Hydrogen-Bond Motifs in Chiral and Racemic Molecular Salts: A Comparison of (S)-2-Methyl Piperizinium Hydrogen Phosphite Monohydrate, C5H14N2·HPO3·H2O and (R,S)-2-Methyl Piperizinium Hydrogen Phosphite 2.23 Hydrate, C5H14N2·HPO3·2.23H2O

doi:10.3390/cryst1040236

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Crystals 2011, 1(4), 236-243; doi:10.3390/cryst1040236

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Supramolecular Hydrogen-Bond Motifs in Chiral and Racemic Molecular Salts: A Comparison of (S)-2-Methyl Piperizinium Hydrogen Phosphite Monohydrate, C₅H₁₄N₂·HPO₃·H₂O and (R,S)-2-Methyl Piperizinium Hydrogen Phosphite 2.23 Hydrate, C₅H₁₄N₂·HPO₃·2.23H₂O

William T. A. Harrison

Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland

Received: 25 August 2011; in revised form: 25 October 2011 / Accepted: 15 November 2011 / Published: 17 November 2011

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Abstract: The crystal structures of C₅H₁₄N₂·HPO₃·H₂O (1) and C₅H₁₄N₂·HPO₃·2.23H₂O (2) are described and compared. Compound 1 contains homochiral (S)-2-methyl piperizinium cations, hydrogen phosphite ions and water molecules. The components are linked by N–H⋯O and O–H⋯O hydrogen bonds into a three-dimensional network. In compound 2, racemic (R,S)-2-methyl piperizinium cations combine with the same anions and water molecules to generate a far more complex, high symmetry “supramolecular” structure, which features distinctive R⁶₆(12) loops and helical C(2) chain hydrogen-bonding motifs involving the water molecules. Crystal data: 1 (C₅H₁₇N₂O₄P), M_r = 200.18, orthorhombic, P2₁2₁2₁ (No. 19), Z = 4, a = 8.564 (5) Å, b = 9.593 (6) Å, c = 11.607 (6) Å, V = 953.6 (9) Å³, R(F) = 0.066, wR(F²) = 0.081. 2 (C₅H_19.47N₂O_5.24P), M_r = 222.49, trigonal, (No. 148), Z = 18, a = 31.075 (2) Å, c = 6.1875 (4) Å, V = 5174.5 (6) Å³, R(F) = 0.044, wR(F²) = 0.107.

Keywords: molecular salt; supramolecular network; O–H⋯O hydrogen bonds

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MDPI and ACS Style

Harrison, W.T.A. Supramolecular Hydrogen-Bond Motifs in Chiral and Racemic Molecular Salts: A Comparison of (S)-2-Methyl Piperizinium Hydrogen Phosphite Monohydrate, C₅H₁₄N₂·HPO₃·H₂O and (R,S)-2-Methyl Piperizinium Hydrogen Phosphite 2.23 Hydrate, C₅H₁₄N₂·HPO₃·2.23H₂O. Crystals 2011, 1, 236-243.

AMA Style

Harrison WTA. Supramolecular Hydrogen-Bond Motifs in Chiral and Racemic Molecular Salts: A Comparison of (S)-2-Methyl Piperizinium Hydrogen Phosphite Monohydrate, C₅H₁₄N₂·HPO₃·H₂O and (R,S)-2-Methyl Piperizinium Hydrogen Phosphite 2.23 Hydrate, C₅H₁₄N₂·HPO₃·2.23H₂O. Crystals. 2011; 1(4):236-243.

Chicago/Turabian Style

Harrison, William T. A. 2011. "Supramolecular Hydrogen-Bond Motifs in Chiral and Racemic Molecular Salts: A Comparison of (S)-2-Methyl Piperizinium Hydrogen Phosphite Monohydrate, C₅H₁₄N₂·HPO₃·H₂O and (R,S)-2-Methyl Piperizinium Hydrogen Phosphite 2.23 Hydrate, C₅H₁₄N₂·HPO₃·2.23H₂O." Crystals 1, no. 4: 236-243.

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