Abstract
The title compound exists in a dipolar form both in the solvent-free and in the dihydrate crystal. Unit cell dimensions: 23.303(5), 7.3100(10), 15.030(3) Å, β = 101.78(3)∘; space group C2/c (monoclinic) with Z = 8. The molecule is flat due to extended conjugation in the central N=C(pyr)–N(3)H–N=C–S– fragment and three assisted intramolecular hydrogen bonds, one of them between the pyridine N atom (acceptor) and the N(3)H amine group as a hydrogen bond donor. As a result the molecule adopts an antiperiplanar conformation along the N–N bond and synperiplanar conformation along the neighbouring N–C bonds. Presence of two water molecules results in a very extensive network of intermolecular hydrogen bonds (eight) as compared with the crystal structure of the anhydrous compound.
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Foks, H.; Orlewska, C. Acta Polon. Pharm. Drug Res. 1992, 49, 47–52.
Mamolo, M.G.; Vio, L.; Banfi, E.; Cinco, M. Eur. J. Med. Chem. Chim. Ther. 1986, 21, 467–474.
Orlewska, C.; Foks, H.; Sowiński, P.; Martynowski, D.; Olczak, A.; Główka, M.L. Polish J. Chem. 2001, 75, 1237–1245.
KM-4 Manual, KUMA Diffraction: Wrocław, Poland, 1992.
Sheldrick, G.M. SHELXTL/PC, Version 4.1, An integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data, Siemens Analytical X-Ray Instruments; Inc. Medison: Wisconsin, USA, 1990.
Sheldrick, G.M. SHELXL97, Program for Refinement of Crystal Structures; University of Göttingen: Germany, 1997.
Radics, U.; Liebscher, J.; Ziemer, B.; Rybakov, V. Chem. Ber. 1992, 125, 1389–1395.
Główka, M.L.; Martynowski, D.; Olczak, A.; Kozłowska, K.; Ołubek, Z.; Orlewska, C.; Foks, H. Polish J. Chem. 1999, 73, 845–851.
Spek, A.L. PLATON, A Multipurpose Crystallographic Tool; Utrecht University: The Netherlands, 2003.
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Główka, M.L., Martynowski, D., Olczak, A. et al. Planarity of N′-(amino-2-pyridylmethylene)-hydrazide carbodithioic acid frame and crystal structure of its methyl ester dihydrate. J Chem Crystallogr 35, 477–480 (2005). https://doi.org/10.1007/s10870-005-2360-z
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DOI: https://doi.org/10.1007/s10870-005-2360-z