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Crystal and Molecular Structures of the 2:1 Cocrystal of 4-Nitrophenylacetic acid and N,N′-bis(pyridin-3-ylmethyl)oxalamide, and with the Thioxalamide Analogue

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Abstract

The common feature of each of the title 2:1 cocrystals is the formation of the O–H···N(pyridyl) hydrogen bonds leading to three-molecule aggregates. The persistent formation of the O–H···N(pyridyl) hydrogen bonds where other functionalities are present, e.g. amide, indicates the robustness of this supramolecular synthon. In the structure of the 2:1 4-nitrophenylacetic acid N,N′-bis(pyridin-3-ylmethyl)oxalamide cocrystal, (1), the amide-H forms a hydrogen bond with the hydroxyl group so that rows of N,N′-bis(pyridin-3-ylmethyl)oxalamide molecules are linked into a supramolecular tape via 4-nitrophenylacetic acid molecules. In the N,N′-bis(pyridin-3-ylmethyl)thioxalamide derivative, (2), the thioamide-H atom only forms an intramolecular N–H···S contact. Nevertheless, a supramolecular tape is formed but mediated by C–H···O(nitro) interactions. Compound (1) crystallizes in the triclinic space group P¯1 with a = 8.195(2) Å, b = 9.502(3) Å, c = 9.999(3) Å, α = 90.631(3)º, β = 102.796(5)º, γ = 108.075(5)º, and Z = 1 (three molecule aggregate). Compound (2) also crystallizes in the triclinic space group P¯1 with a = 8.0772(12) Å, b = 10.2111(12) Å, c = 10.2563(17) Å, α = 71.319(10)º, β = 77.777(11)º, γ = 67.660(9)º, and Z = 1 (three molecule aggregate).

Graphical Abstract

In each cocrystal the carboxylic acid-OH interacts with the pyridyl-N atom via a hydrogen bond to result in a three-molecule aggregate. In the N,N′-bis(pyridin-3-ylmethyl)oxalamide cocrystal, these are linked into a chain via amine-H···O(carboxylic acid) interactions.

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Acknowledgments

Support from the Ministry of Higher Education, Malaysia, High-Impact Research scheme (UM.C/HIR/MOHE/SC/12) and the University of Malaya (UMRG RG125) is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, TX, 78249-0698, USA

    Hadi D. Arman, Trupta Kaulgud & Tyler Miller

  2. Chemical Abstracts Service, 2540 Olentangy River Rd, Columbus, OH, 43202, USA

    Pavel Poplaukhin

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

    Edward R. T. Tiekink

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  1. Hadi D. Arman
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  2. Trupta Kaulgud
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  3. Tyler Miller
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Correspondence to Edward R. T. Tiekink.

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Arman, H.D., Kaulgud, T., Miller, T. et al. Crystal and Molecular Structures of the 2:1 Cocrystal of 4-Nitrophenylacetic acid and N,N′-bis(pyridin-3-ylmethyl)oxalamide, and with the Thioxalamide Analogue. J Chem Crystallogr 42, 673–679 (2012). https://doi.org/10.1007/s10870-012-0298-5

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  • DOI: https://doi.org/10.1007/s10870-012-0298-5

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