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Crystal and Molecular Structures of 2-Amino-4-Nitrobenzoic Acid and Its Cocrystals with 2,2′-Bipyridine (2/1) and Bis(pyridin-2-yl)ketone (1/1)

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Abstract

The eight-membered {···HOC=O}2 synthon featured in the crystal structure of 2-amino-4-nitrobenzoic acid (1) is replaced by carboxylic acid···N-pyridine hydrogen bonds in its cocrystals with 2,2′-bipyridine (2/1; 2) and bis(pyridin-2-yl)ketone (1/1; 3) indicating the robust nature of the latter synthon. Disruption of the three-dimensional architecture based on O–H···O and N–H···O(nitro) hydrogen bonds in (1) is evident in the cocrystals which form supramolecular tubes (2) and chains (3) based on O–H···N and N–H···O hydrogen bonding. Compound (1) crystallizes in the monoclinic space group P21/n with a = 3.6291(1) Å, b = 7.7339(3) Å, c = 26.561(1) Å, β = 91.385(2)°, and Z = 4. Compound (2) crystallizes in the monoclinic space group C2/c with a = 27.562(3) Å, b = 6.8300(6) Å, c = 12.923(1) Å, β = 110.593(5)°, and Z = 4. Compound (3) crystallizes in the monoclinic space group P21/c with a = 3.795(3) Å, b = 12.024(8) Å, c = 35.65(2) Å, β = 92.131(6)°, and Z = 4 (determined from synchrotron data).

Graphical Abstract

The carboxylic acid dimer synthon formed in the acid no longer exists in its cocrystals owing to carboxylic acid-OH···N-pyridine interactions. Based on hydrogen bonding a supramolecular tube is formed in the 2/1 cocrystal with 2,2′-bipyridine.

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Acknowledgments

JLW acknowledges support from CAPES and FAPEMIG (Brazil). The University of Malaya is thanked for support this research (UMRG RG125/10AFR). The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, Prof. W. Clegg and the synchrotron component, based at Daresbury, and the valuable assistance of the staff at those centers are gratefully acknowledged.

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Authors and Affiliations

  1. Centro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, Rio de Janeiro, RJ, 21040-900, Brazil

    James L. Wardell

  2. Department of Chemistry, University of Malaya, Kuala Lumpur, 50603, Malaysia

    Edward R. T. Tiekink

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  1. James L. Wardell
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  2. Edward R. T. Tiekink
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Correspondence to James L. Wardell or Edward R. T. Tiekink.

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Wardell, J.L., Tiekink, E.R.T. Crystal and Molecular Structures of 2-Amino-4-Nitrobenzoic Acid and Its Cocrystals with 2,2′-Bipyridine (2/1) and Bis(pyridin-2-yl)ketone (1/1). J Chem Crystallogr 41, 1418–1424 (2011). https://doi.org/10.1007/s10870-011-0114-7

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