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A cocrystal of caffeine and dipicolinic acid: synthesis, characterization, X-ray crystallography, and solution studies

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Abstract

A reaction between caffeine (caff) and dipicolinic acid = 2,6-pyridine dicarboxylic acid (pydc.H2) in water results in the formation of a cocrystal compound (pydc.H2.H2O)(caff) 1. The characterization of the resulting crystallohydrate is performed using 1H, 13C NMR and IR spectroscopy and X-ray crystallography. X-ray crystal structure analysis reveals the presence of both starting materials and water in the lattice. It also indicates intensive intermolecular H bonding interactions between carboxylic acid, caffeine, and water as well as π-π stacking between the pydc.H2 and caff rings as constituents of the cocrystal. The hydrogen bonding and non-covalent interactions play roles in the formation of the cocrystal. The crystal system is triclinic with the space group P-1 and two formula units per unit cell. The unit cell parameters are a = 6.906(2) Å, b = 8.451(3) Å, c = 14.68 (4) Å with α = 81.51(3)°, β = 78.47(3)°, and γ = 78.14(3)°. The final R value is 0.0660 for 7943 measured reflections.

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Authors and Affiliations

  1. Department of Chemistry, Islamic Azad University, Tehran North Branch, Tehran, Iran

    A. Moghimi, F. Dashtestani & E. Behboodi

  2. Department of Chemistry, Shahid Beheshti University, G. C., Tehran, Iran

    H. R. Khavasi

  3. Department of Chemistry, Razi University, Kermanshah, Iran

    D. Kordestani

  4. Department of Chemistry, Imam Hossein University, Tehran, Iran

    B. Maddah

Authors
  1. A. Moghimi
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  2. H. R. Khavasi
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  3. F. Dashtestani
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  4. D. Kordestani
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  5. E. Behboodi
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  6. B. Maddah
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Correspondence to A. Moghimi.

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Original Russian Text Copyright © 2013 by A. Moghimi, H. R. Khavasi, F. Dashtestani, D. Kordestani, E. Behboodi, B. Maddah

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 54, No. 5, pp. 950–955, September–October, 2013.

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Moghimi, A., Khavasi, H.R., Dashtestani, F. et al. A cocrystal of caffeine and dipicolinic acid: synthesis, characterization, X-ray crystallography, and solution studies. J Struct Chem 54, 990–995 (2013). https://doi.org/10.1134/S0022476613050247

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  • DOI: https://doi.org/10.1134/S0022476613050247

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