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Hydrogen bonding patterns in bis(pyrimethamine hydrogen sulfate) monohydrate

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The crystal structure of the compound bis [2,4-diamino-5-(p-chlorophenyl)-6-ethyl pyrimidinium hydrogen sulfate] monohydrate was studied by X-ray diffraction methods. The compound crystallises in orthorhombic system, space group P212121, a=18.531(2) Å, b=16.190(2) Å, c=10.777(2) Å, V=3233.3(8), Z=4. The asymmetric unit shows the presence of two crystallographically independent pyrimethamine molecules, two hydrogen sulfate anions, and a water molecule. The hydrogen sulfate anions form a cyclic hydrogen bonded motif R2 2(8) with the 2-amino pyrimidine of the respective protonated pyrimethamine cations, through N–H···O hydrogen bonds. Thus the sulfate anions mimic the role of carboxylate anions observed in many aminopyrimidine-carboxylate interactions. This motif self assembles through DDAA array of quadruple hydrogen bonds, N–H···Cl, O–H···O and C–H···O hydrogen bonds.

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Authors and Affiliations

  1. School of Chemistry, Bharathidasan University, Tiruchirappalli, 620024, India

    Periasamy Devi & P. Thomas Muthiah

  2. IMEM-CNR, Parco Area delle Scienze-37a, I-43010, Fontanini Parma, Italy

    Gabriele Bocelli & Andrea Cantoni

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  1. Periasamy Devi
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  2. P. Thomas Muthiah
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  3. Gabriele Bocelli
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  4. Andrea Cantoni
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Correspondence to P. Thomas Muthiah.

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Supplementary material

CCDC-293607 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 IEZ, UK; fax: C44 (0) 1223-336033; e-mail: deposit@ccdc.cam.ac.uk].

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Devi, P., Muthiah, P.T., Bocelli, G. et al. Hydrogen bonding patterns in bis(pyrimethamine hydrogen sulfate) monohydrate. J Chem Crystallogr 36, 857–861 (2006). https://doi.org/10.1007/s10870-006-9145-x

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