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Structure, vibrational characterization and DFT calculations of 1-(diaminomethylene)thiouron-1-ium 2,3-pyridinedicarboxylate

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Abstract

The single crystals of the title compound (1) were grown from a water solution. The compound crystallizes in the centrosymmetric space group P21/c of the monoclinic system with eight molecules per unit cell. Multiple recrystallizations of the crystals from heavy water gives deuterated analogue 1d. The asymmetric unit of 1 contains two salt molecules. Both independent cations interact with anions via N−H…O hydrogen bonds with R22(8) and R21(6) graphs forming 1:1 salt molecules. Both salt molecules are linked by additional N−H…O and O−H…O hydrogen bonds with a graph R22(9). The oppositely charged components of the crystals, i.e., 1-(diaminomethylene)thiouron-1-ium cations and 2,3-pyridine-dicarboxylate anions, interact each other forming three-dimensional supramolecular hydrogen bonded network. The interactions between the components as well as between the 1:1 salt molecules were analysed using the Hirshfeld surface. The compound was also characterized by vibrational spectroscopy. The vibrational bands were interpreted based on the optimized structure and force field calculations of normal coordinates based on the density functional theory (DFT) with the base set 6-31G(d,p). Isotopic frequency shift and potential energy distribution (PED) were used to assign the bands. The electronic absorption spectra of 1 in the gas phase, as well as in polar and non-polar solvents, were calculated.

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Acknowledgements

Calculations have been carried out in Wroclaw Centre for Networking and Supercomputing (http://www.wcss.wroc.pl).

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    Jan Janczak

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Supplementary file1 Additional material comprising experimental and simulated XRD diagrams confirming the purity of the compounds, the DFT optimized parameters, hydrogen-bond geometry, the TD DFT results of 1 in the gas-phase and in solvents, DFT calculated IR and Raman spectra of 1 and its deuterated analogue 1d, the definitions of the local modes calculated for the protiated and deuterated samples and the numbering scheme used in the calculation by VEDA program, detailed band assignments along with PED analysis and the full details of the X-ray data collection and final refinement parameters including anisotropic thermal parameters and full list of the bond lengths and angles have been deposited with the Cambridge Crystallographic Data Center in the CIF format as supplementary publications no. CCDC 2280816. Copies of the data can be obtained free of charge on the application to CCDC, 12 Union Road, Cambridge, CB21EZ, UK, (fax: (+44) 1223-336-033; email: deposit@ccdc.cam.ac.uk). (DOCX 4602 KB)

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Janczak, J. Structure, vibrational characterization and DFT calculations of 1-(diaminomethylene)thiouron-1-ium 2,3-pyridinedicarboxylate. Struct Chem (2023). https://doi.org/10.1007/s11224-023-02262-5

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