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Two 1-(2-Furoyl)-3-phenylthiourea Derivatives: Synthesis, Characterization and Structural Study from X-ray Powder Diffraction Using Simulated Annealing

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Abstract

1-(2-furoyl)-3-p-cyanophenylthiourea (1) and 1-(2-furoyl)-3-o-fluorophenylthiourea (2) were synthesized by converting 2-furoyl chloride into 2-furoyl isothiocyanate and then condensing with the appropriated aniline derivatives. Both products were characterized by elemental analysis, Fourier transform infrared spectroscopy, Raman, 1H, 13C nuclear magnetic resonance and ab initio X-ray powder structure analysis. Compound 1 crystallizes in the monoclinic space group P21/n with unit cell dimensions a = 23.169(2) Å, b = 11.353(2) Å, c = 4.798(3) Å, β = 90.30(2)°, V = 1,259.87(3) Å3, Z = 4, R p = 4.62, and R wp = 7.86. Compound 2 crystallizes also in the monoclinic space group P21/n with unit cell dimensions a = 12.072(1) Å, b = 20.801(2) Å, c = 4.737(2) Å, β = 93.34(2)°, V = 1,189.62(3) Å3, Z = 4, R p = 3.95, and R wp = 7.06. The crystal structures have been determined from laboratory X-ray powder diffraction data using direct space global optimization strategy (simulated annealing) followed by the Rietveld refinement. The thiourea group makes a dihedral angle of 9.4(5)° and 33.5(4)° with the furoyl group in 1 and 2, respectively. In both compounds, the trans–cis geometry of the thiourea unit is stabilized by intramolecular N–H⋯O hydrogen bond between the H atom of the cis thioamide and the carbonyl O atom. In the crystal structure of compound 1, molecules are linked by intermolecular N–H⋯S bonds, forming one-dimensional chains along the c axis. For compound 2, only Van der Waals interactions are observed in the crystal structure, forming one-dimensional chains along the b axis.

Graphical Abstract

Crystal structure analysis from X-ray powder diffraction data and spectroscopic characterization of two 1-(2-furoyl)-3-phenylthiourea derivatives.

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Acknowledgments

JD acknowledge the financial support from Consejo Nacional de Ciencia y Tecnología (CONACyT), México. “Programa de Estancias Posdoctorales y Sabáticas al Extranjero para la Consolidación de Grupos de Investigación”, No de Propuesta: 203824.

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Authors and Affiliations

  1. Instituto de Ciencia y Tecnología de Materiales (IMRE), Universidad de La Habana, Havana, Cuba

    O. Estévez-Hernández & J. Duque

  2. Instituto de Investigaciones en Materiales, UNAM, Ciudad Universitaria, Circuito Exterior, 04510, Mexico, DF, Mexico

    J. Rodríguez-Hernández

  3. Centro de Investigación en Ciencia Aplicada y Tecnología de Avanzada, IPN, Legaria 694, 11500, Mexico, DF, Mexico

    E. Reguera

Authors
  1. O. Estévez-Hernández
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  2. J. Rodríguez-Hernández
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  3. E. Reguera
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  4. J. Duque
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Correspondence to J. Duque.

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Estévez-Hernández, O., Rodríguez-Hernández, J., Reguera, E. et al. Two 1-(2-Furoyl)-3-phenylthiourea Derivatives: Synthesis, Characterization and Structural Study from X-ray Powder Diffraction Using Simulated Annealing. J Chem Crystallogr 45, 51–60 (2015). https://doi.org/10.1007/s10870-014-0563-x

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  • DOI: https://doi.org/10.1007/s10870-014-0563-x

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