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Three New Polymorphs of 2-Amino-4-nitrobenzoic Acid

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Abstract

Three polymorphs, designated monoclinic-1B, monoclinic-1C and triclinic-1, of 2-amino-4-nitrobenzoic acid, 1, have been characterized. These, and the previously reported monoclinic-1A form [J Chem Crystallogr. (2011) 41: 1418] exhibit classical intermolecular interactions, O–H···O(COH) and N–H···O(nitro) as well as π···π stacking interactions. Compound monoclinic-1B crystallizes in the space group P21/c with a = 4.039(4), b = 27.23(2), c = 7.284(7) Å, β = 112.783(15)°; compound monoclinic-1C crystallizes in the space group P21/c with a = 3.71050(10), b = 25.3092(8), c = 24.3555(17) Å, β = 93.459(7)°, and triclinic-1 crystallizes in the space group P−1 with a = 3.7522(3), b = 8.5536(6), c = 24.4118(17) Å, α = 88.738(9), β = 86.625(9), γ = 87.769(9)° .

Graphical Abstract

Three new polymorphs, designated monoclinic-1B, monoclinic-1C and triclinic-1, of 2-amino-4-nitrobenzoic acid, 1, have been characterized. These, and the previously reported monoclinic-1A form exhibit classical intermolecular interactions, O–H⋯O(COH) and N–H⋯O(nitro) as well as π⋯π stacking interactions.

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Acknowledgments

The use of the NCS X-ray crystallographic service at Southampton and the valuable assistance of the staff there is gratefully acknowledged. JLW thanks FAPERJ for support.

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Authors and Affiliations

  1. CHEMSOL, 1 Harcourt Road, Aberdeen, AB15 5NY, Scotland, UK

    Solange M. S. V. Wardell

  2. Instituto de Tecnologia em Fármacos-Far-Manguinhos, Rua Sizenando Nabuco, 100, Manguinhos, 21041-250, Rio De Janeiro, RJ, Brazil

    James L. Wardell

  3. Department of Chemistry, University of Aberdeen, Old Aberdeen, AB24 3UE, Scotland, UK

    James L. Wardell

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  1. Solange M. S. V. Wardell
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  2. James L. Wardell
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Correspondence to James L. Wardell.

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Wardell, S.M.S.V., Wardell, J.L. Three New Polymorphs of 2-Amino-4-nitrobenzoic Acid. J Chem Crystallogr 46, 34–43 (2016). https://doi.org/10.1007/s10870-015-0625-8

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  • DOI: https://doi.org/10.1007/s10870-015-0625-8

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