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Crystal Structure and Hirshfeld Surface Analysis of Bis(3-thienoyl) Disulfide

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Abstract

The spectroscopic characterization (1H, 13C{1H} NMR, UV–Vis) and single-crystal X-ray diffraction (scXRD) analysis accomplished by inspection of the Hirshfeld surface of bis(3-thienoyl) disulfide (1) is described. The title compound 1 crystallizes in the monoclinic space group P21/n. The unit cell parameters are a = 7.9959(3) Å, b = 6.4348(3) Å, c = 22.4924(9) Å, β = 100.108(4)°, V = 1139.32(8) Å3, Z = 4, Rgt(F) = 0.0278, wRref(F2) = 0.0667. The packing of 1 is dominated by S⋯O and S⋯S interactions, giving a 2D layer structure parallel to (101). The X‐ray crystal structure analysis revealed the packing of 1 is dominated by S⋯O and S⋯S interactions, giving a 2D layer structure parallel to (101). The intermolecular interactions in 1 were analyzed using the Hirshfeld surface method including 2D fingerprint plots and enrichment ratios (E), which shows that the most favored intermolecular contacts are the O⋯H and C⋯S indicated by E values above 1.30. The interaction energies between molecular pairs revealed the importance of the weak O⋯H and C⋯S interactions in stabilizing the molecular structure of 1.

Graphic Abstract

Single crystal X-ray structure analysis, DFT calculations and Hirshfeld surface analysis to identify intermolecular interactions within the solid state structure of bis(3-thienoyl) disulfide (1).

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Acknowledgements

We are grateful to the Deutsche Forschungsgemeinschaft (DFG) for a visiting fellowship of Al Khalyfeh, Kahled.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Natural Sciences, Al-Hussein Bin Talal University, Ma’an, 71111, Jordan

    Khaled Al Khalyfeh

  2. Department of Chemistry, The University of Jordan, Amman, 11942, Jordan

    Deeb Taher, Wissam Helal & Hazem Amarne

  3. School of Molecular Sciences, The University of Western Australia, Crawley, Perth, WA, 6009, Australia

    Marcus Korb

  4. Faculty of Natural Sciences, Institute of Chemistry, Inorganic Chemistry, Technische Universität Chemnitz, 09107, Chemnitz, Germany

    Heinrich Lang

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  1. Khaled Al Khalyfeh
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  2. Deeb Taher
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Correspondence to Khaled Al Khalyfeh or Deeb Taher.

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Al Khalyfeh, K., Taher, D., Helal, W. et al. Crystal Structure and Hirshfeld Surface Analysis of Bis(3-thienoyl) Disulfide. J Chem Crystallogr 52, 113–121 (2022). https://doi.org/10.1007/s10870-021-00896-z

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