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Crystal Structure of D(−)-amino-(4-hydroxyphenyl)acetate, the Zwitter Ionic Form of Biologically Active D(−)-4-hydroxyphenylglycine

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Abstract

Crystals of D(−)-amino-(4-hydroxyphenyl)acetate were analyzed by single crystal X-ray diffraction. The compound crystallizes in the chiral space group, P21 (No. 4) with one molecule in the asymmetric unit and a = 5.0994(10) Å, b = 9.3169(19) Å, c = 8.6960(17) Å, β = 91.50(3)°. The intermolecular interactions in the crystal have been visualised by plotting the Hirshfeld surface of the molecule.

Graphical Abstract

The extensive hydrogen bonding network in D(−)-amino-(4-hydroxyphenyl)acetate has been described and visualised by plotting its Hirshfeld surface.

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Acknowledgments

Authors acknowledge Dr. Sophie Rees Jones for measuring optical activity. Financial support was received from the South African National Research Foundation (FA2006030100003) and NBB thanks the NRF (SPF2005072700016) and the University of Cape Town for a postdoctoral scholarship.

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Authors and Affiliations

  1. Centre for Supramolecular Chemistry Research, Department of Chemistry, University of Cape Town, Rondebosch 7701, Cape Town, South Africa

    Nikoletta B. Báthori & Susan A. Bourne

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  1. Nikoletta B. Báthori
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  2. Susan A. Bourne
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Correspondence to Nikoletta B. Báthori.

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Báthori, N.B., Bourne, S.A. Crystal Structure of D(−)-amino-(4-hydroxyphenyl)acetate, the Zwitter Ionic Form of Biologically Active D(−)-4-hydroxyphenylglycine. J Chem Crystallogr 39, 539–543 (2009). https://doi.org/10.1007/s10870-009-9566-4

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