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Crystal Structure Analysis and Topological Study of Non-covalent Interactions in 2,2-Biimidazole:Salicylic Acid 2:1 Co-crystal

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Abstract

The 1:2 ratio salicylic acid/biimidazole co-crystal is studied in this work. I This compound was obtained from a flux with methanol followed by slow evaporation, rendering colorless plates, that crystallize in the monoclinic system, space group P21/n, with unit cell parameters a = 12.0969 (4) Å, b = 5.0714 (1) Å and c = 15.4825 (4) Å, β = 99.007(2)º, and V = 938.11(4) Å3. The experimental characterization is achieved through X-ray diffraction structure analyzes, infrared spectroscopy (FTIR) and thermal analysis (TGA/DSC). This characterization is complemented by theoretical calculations at the DFT/6–31++G(d,p) level, employing the HCTH407 functional. Geometrical optimizations are performed and a detailed Non-Covalent-Index analysis is carried out. It is found that the crystal structure is maintained by conventional and non-conventional hydrogen bonds, of the type N–H···O, O–H···N and C–H···O hydrogen bonds responsible for the formation of planar supramolecular units forming R2 2(9) rings and slip-stacked packing, which, through DFT/HCTH calculations, are shown to stabilize the structure.

Graphical Abstract

The synthesis and crystal structure of the title compound, C10H9N2O3, is reported. The bimidazole and salicylic acid form a co-crystal in a 1:2 ratio. Its crystal structure is maintained by conventional and non-conventional hydrogen bonds. Two conventional hydrogen bonds, of the type N–H···O and O–H···N, form planar supramolecular unit through R2 2(9) rings, the DFT/HCTH calculations shows us that the R2 2(9) rings formation stabilize the supramolecular structure.

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Acknowledgements

The authors thank the financial support to CDCHTA-ULA (Grant No. C-1921-15-08-AA).

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Authors and Affiliations

  1. Laboratorio de Materiales para Tecnologías Emergentes (LaMTE), Centro de Investigación en Tecnología de Materiales y Ambiente (CITeMA), Instituto Venezolano de Investigaciones Científicas (IVIC), Maracaibo, 4001, Zulia, Venezuela

    Julia Bruno-Colmenarez & Reinaldo Atencio

  2. Departamento de Química, Facultad Experimental de Ciencias, La Universidad del Zulia (LUZ), Maracaibo, Zulia, Venezuela

    Marinel Quintero

  3. Laboratorio de Procesos Dinámicos en Química, Departamento de Química, Facultad de Ciencias, Universidad de Los Andes (ULA), Mérida, Venezuela

    Luis Seijas & Rafael Almeida

  4. Grupo de Química Computacional y Teórica (QCT-USFQ), Dpto. de Ingeniería Química, Universidad San Francisco de Quito (USFQ), 17-1200-841, Quito, Ecuador

    Luis Rincón

Authors
  1. Julia Bruno-Colmenarez
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  2. Reinaldo Atencio
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  3. Marinel Quintero
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  4. Luis Seijas
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  5. Rafael Almeida
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  6. Luis Rincón
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Correspondence to Julia Bruno-Colmenarez.

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Bruno-Colmenarez, J., Atencio, R., Quintero, M. et al. Crystal Structure Analysis and Topological Study of Non-covalent Interactions in 2,2-Biimidazole:Salicylic Acid 2:1 Co-crystal. J Chem Crystallogr 47, 47–58 (2017). https://doi.org/10.1007/s10870-017-0679-x

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  • DOI: https://doi.org/10.1007/s10870-017-0679-x

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