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Structure of a monoclinic polymorph of N-[4-(acetyloxy)-phenyl]acetamide, a prodrug of acetaminophen

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Abstract

The preparation, single crystal x-ray structure and the computed powder XRD pattern of a monoclinic polymorph of N-[4-(acetyloxy)phenyl]acetamide, a prodrug of acetaminophen, are reported. The polymorph crystallizes in the space group P21/n with Z = 4 and unit cell dimensions a = 7.219(2), b = 8.015(2), c = 16.575(2) Å, β = 92.07(1)°, and V = 958.4(4) Å3. Infinite spiral molecular arrays result from intermolecular head-to-tail hydrogen bonding between the amidic H atom of one molecule and the acetoxy carbonyl oxygen atom of a 21-related molecule.

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Authors and Affiliations

  1. Department of Chemistry, University of Cape Town, Rondebosch, 7701, South Africa

    M. R. Caira

  2. Research Institute for Industrial Pharmacy, Potchefstroom University for CHE, Potchefstroom, 2520, South Africa

    F. N. de Wet & J. J. Gerber

Authors
  1. M. R. Caira
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  2. F. N. de Wet
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  3. J. J. Gerber
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Caira, M.R., de Wet, F.N. & Gerber, J.J. Structure of a monoclinic polymorph of N-[4-(acetyloxy)-phenyl]acetamide, a prodrug of acetaminophen. Journal of Chemical Crystallography 29, 175–178 (1999). https://doi.org/10.1023/A:1009565926282

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