Abstract
5-(3,4-Dichlorophenyl)-3-{[4-(2-pyridyl)piperazine-1-yl)]methyl}-1,3,4-oxadiazole-2(3H)-one C18H17Cl2N5O2 (3) is synthesized and characterized by IR, 1H NMR, 13C NMR, elemental analyses, single-crystal X-ray diffraction, and the molecular structure is also optimized at the B3LYP/6-31G(d,p) level using density functional theory (DFT). All data obtained from the spectral studies support the structural properties of 3. The molecules are linked principally by C-H…O hydrogen bonds involving carbonyl atoms and carboxylate O atoms, forming R 22 (16) and R 24 (20) rings that link to give a one-dimensional network of molecules. An extensive two-dimensional network of C-H…O hydrogen bonds and π…π interactions are responsible for crystal stabilization.
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Y. Sawada, T. Yanai, H. Nakagawa, et al., Pest Manag. Sci., 59, No. 9, 49 (2003).
A. M. R. Bernardino, A. O. Gomes, K. S. A. Charret, et al., Eur. J. Med. Chem., 41, No. 1, 80 (2006).
H. K. Misra, Arch. Pharm., 316, 487 (2006).
F. Macaev, G. Rusu, S. Pogrebnoi, et al., Bioorg. Med. Chem., 13, No. 16, 4842 (2005).
L. Jin, J. Chen, B. Song, et al., Bioorg Med. Chem. Lett., 16, No. 19, 5036 (2006).
T. M. C. Tan, Y. Chen, K. H. Kong, et al., Antiviral Res., 71, No. 1, 7 (2006).
J. Patole, U. Sandbhor, S. Padhyde, et al., Bioorg. Med. Chem. Lett., 13, No. 1, 51 (2003).
A. Almasirad, S. A. Tabatabai, M. Faizi, et al., Bioorg. Med. Chem. Lett., 14, No. 24, 6057 (2004).
Z. H. Chohan, H. Pervez, K. M. Khan, et al., Enzyme Inhib. Med. Chem., 20, No. 1, 81 (2005).
M. D. Mullican, M. W. Wilson, D. T. Connor, et al., J. Med. Chem., 36, No. 8, 1090 (1993).
M. Amir and S. Kumar, Acta Pharm., 57, 31 (2007).
P. V. Frank, K. S. Girish, and B. Kalluraya, J. Chem. Sci., 119, 41 (2007).
P. Mishra, H. Rajak, and A. Mehta, J. Gen. Appl., Microbiol., 51, 133 (2005).
M. Koksal, S. S. Bilge, A. Bozkurt, et al., Arzneimittel-Forschung (Drug Research), 58, No. 10, 510 (2008).
Stoe & Cie, X-AREA (Version 1.18.) and X-RED32 (Version 1.04.). Stoe & Cie, Germany, Darmstadt (2002).
G. M. Sheldrick, Acta Crystallogr., A64, 112 (2008).
L. J. Farrugia, J. Appl. Crystallogr., 32, 837 (1999).
L. J. Farrugia, J. Appl. Crystallogr., 30, 565 (1997).
A. D. Becke, J. Chem. Phys., 98, 5648 (1993).
C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B, 37, 785 (1988).
H. B. Schlegel, J. Comput. Chem., 3, 214 (1982).
C. Peng, P. Y. Ayala, H. B. Schlegel, et al., J. Comput. Chem., 17, 49 (1996).
M. J. Frisch, G. W. Trucks, H. B. Schlegel, et al. GAUSSIAN-03, Revision E.01, Gaussian, Inc., Pittsburgh, PA (2003).
A. Frisch, R. II Dennington, T. Keith, et al. GAUSSVİEW, Reference, Vol 4.0, Gaussian Inc, Pittsburgh, PA (2007).
A. Thiruvalluvar, M. Subramanyam, B. Lingappa, et al., Acta Crystallogr., E63, o3425 (2007).
J. P. Jasinski, R. J. Butcher, A. N. Mayekar, et al., J. Chem. Crystallogr., 39, 761 (2009).
D. Cremer and J. A. Pople, J. Am. Chem. Soc., 97, 1354 (1975).
J. Bernstein, R. E. Davis, L. Shimoni, et al., Angew. Chem. Int. Ed. Eng., 34, 1555 (1995).
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Original Russian Text Copyright © 2012 by Z. S. Şahin, İ. Özkan, M. Köksal, Ş. Işık
The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 53, No. 5, pp. 957–961, September–October, 2012.
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Şahin, Z.S., Özkan, İ., Köksal, M. et al. 5-(3,4-dichlorophenyl)-3-{[4-(2-pyridyl)piperazine-1-yl]methyl}-1,3,4-oxadiazole-2(3H)-one: Synthesis, characterization, X-ray and DFT structures. J Struct Chem 53, 938–942 (2012). https://doi.org/10.1134/S0022476612050162
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DOI: https://doi.org/10.1134/S0022476612050162