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Mechanochemical Complexation of Diethyl N,N´-[1,3-(2-methyl)phenyl]dioxalamate and Resorcinol: Conformational Twist and X-Ray Helical Supramolecular Architecture

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Abstract

The cocrystal formed by diethyl N,N´-[1,3-(2-methyl)phenyl]dioxalamate (1) and resorcinol (2), namely 1·2 cryst (C21H24N2O8) was prepared by mechanochemical complexation. IR spectroscopy and powder X-ray diffraction studies allowed to determine the complexation and the conformational switching of the ethyl oxalamate side arms. In the crystal structure of 1·2 cryst , complexation occurs through O–H···O=C hydrogen-bonding interactions with the participation of phenolic O–H as donor and amide carbonyl group as acceptor. The steric hindrance of the CH3 group in the C-2 position of the aromatic ring leads to a meso–helical supramolecular architecture forming a C 22 (16) chain motif. Crystal data: monoclinic, C2/c space group, a = 34.9054(13) Å, b = 8.0434(5) Å, c = 5.1577(8) Å, β = 97.521(3)°.

Graphical Abstract

The cocrystal formed by diethyl N,N´-[1,3-(2-methyl)phenyl]dioxalamate and resorcinol, prepared by mechanochemical complexation.

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Acknowledgments

We acknowledge to CONACYT (Grant 179674), for the financial support for the purchase of the IR spectrophotometer.

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Authors and Affiliations

  1. Instituto de Farmacobiología, Universidad de la Cañada, Carretera Teotitlán-San Antonio Nanahuatipan km 1.7 s/n, 68540, Teotitlán de Flores Magón, Oaxaca, Mexico

    Juan Saulo González-González & Oscar Zúñiga-Lemus

  2. Facultad de Ciencias Químicas, Universidad de Colima, km 9 Carretera Colima-Coquimatlán, 28400, Coquimatlán, Colima, Mexico

    Francisco J. Martínez-Martínez & Jorge Gonzalez

  3. Departamento de Ciencias Básicas, Unidad Profesional Interdisciplinaria de Biotecnología del Instituto Politécnico Nacional, Av. Acueducto s/n Barrio la Laguna Ticomán, 07340, Mexico, DF, Mexico

    Efrén V. García-Báez & Itzia I. Padilla-Martínez

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  1. Juan Saulo González-González
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  2. Oscar Zúñiga-Lemus
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  3. Francisco J. Martínez-Martínez
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  4. Jorge Gonzalez
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  6. Itzia I. Padilla-Martínez
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Correspondence to Juan Saulo González-González.

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González-González, J.S., Zúñiga-Lemus, O., Martínez-Martínez, F.J. et al. Mechanochemical Complexation of Diethyl N,N´-[1,3-(2-methyl)phenyl]dioxalamate and Resorcinol: Conformational Twist and X-Ray Helical Supramolecular Architecture. J Chem Crystallogr 45, 244–250 (2015). https://doi.org/10.1007/s10870-015-0589-8

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  • DOI: https://doi.org/10.1007/s10870-015-0589-8

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