Abstract
2H-Imidazole derivative 5 has been synthesized and characterized by the X-ray diffraction (XRD) method. The compound crystallizes in the monoclinic space group Cc with cell parameters a = 19.398(1), b = 8.890(1), c = 10.247(1), β = 110.76(1), Z = 4. The molecules are inter-linked through C–H⋅sO and C–H⋅sπ interactions forming infinite chains.
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Sánchez-Migallón, A.; de la Hoz, A.; López, C.; Claramunt, R. M.; Infantes, L.; Motherwell, S.; Shankland, K.; Nowell, H.; Alkorta, I.; Elguero, J. Helv. Chim. Acta 2003, 86, 1026.
Clark, B. A. J.; Evans, T. J.; Simmonds, R. G. J. Chem. Soc. Perkin Trans. I 1975, 1803.
Kirilyuk, I. A.; Grigor’ev, I. A.; Volodarsky, L. B. Izv. Akad. Nauk SSSR Ser. Khim. 1991, 2113 [Bull. Acad. Sci. USSR Div. Chem. Sci. 1991, 40, 1871 (Engl. Transl.)]. Kirilyuk, I. A.; Grigor’ev, I. A.; Volodarsky, L. B. Izv. Akad. Nauk SSSR. Ser. Khim. 1991, 2122 [Bull. Acad. Sci. USSR Div. Chem. Sci. 1991, 40, 1880 (Engl. Transl.)]. Dikalov, S. I.; Kirilyuk, I. A.; Grigor’ev, I. A.; Volodarsky, L. B. Izv. Akad. Nauk SSSR Ser. Khim. 1992, 1064. Kirilyuk, I. A.; Grigor’ev, I. A.; Petrenko, O. P.; Volodarsky, L. B. Izv. Akad. Nauk SSSR Ser. Khim. 1993, 2096 [Russ. Chem. Bull. 1993, 42, 2009 (Engl. Transl.)]. Reznikov, V. A.; Volodarsky, L. B. Tetrahedron 1993, 49, 10669. Dikalov, S. I.; Kirilyuk, I. A.; Grigor’ev, I. A. Biochem. Biophys. Res. Commun. 1996, 218, 616. Haseloff, R. F.; Kirilyuk, I. A.; Dikalov, S. I.; Khramtsov, V. V.; Utepbergenov, D. I.; Blasig, I. E.; Grigor’ev, I. A. Free Radic. Res. 1997, 26, 159. Bakunova, S. M.; Grigor’ev, I. A.; Kirilyuk, I. A.; Volodarskii, L. B. Izv. Akad. Nauk Ser. Khim. 1999, 2160 [Russ. Chem. Bull. 1999, 48, 2136 (Engl. Transl.)]. Grigor’ev, I. A.; Bakunova, S. M.; Kirilyuk, I. A. Izv. Akad. Nauk Ser. Khim. 2000, 2066 [Russ. Chem. Bull. 2000, 49, 2031 (Engl. Transl.)]. Bakunova, S. M.; Kirilyuk, I. A.; Grigor’ev, I. A. Izv. Akad. Nauk Ser. Khim. 2001, 845 [Russ. Chem. Bull. 2001, 50, 882 (Engl. Transl.)]. Irtegova, I. G.; Starichenko, V. F.; Kirilyuk, I. A.; Grigor’ev, I. A. Izv. Akad. Nauk Ser. Khim. 2002, 1910.
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Kudin, K. N.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomellli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannerberg, J. J.; Zarkzevski, V. G.; Dapprisch, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskortz, P.; Komaroni, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 2003.
Becke, A. D. J. Chem. Phys. 1993, 98, 5648. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
Hariharan, P. A.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
ORTEP3 for Windows – Farrujia, L. J. J. Appl. Cryst. 1997, 30, 565.
Cremer, D.; Pople, J. A. J. Am. Chem. Soc. 1975, 97, 1354.
DENZO – Otwinowski, Z.; Minor, W. In Methods in Enzymology: Macromolecular Crystallography; Carter, C. W., Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, p. 307.
SIR97 – Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Cryst. 1999, 32, 115.
SHELXL97 – Program for Crystal Structure Refinement. Sheldrick, G. M., Institüt für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400 Göttingen, Germany, 1998.
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Hoz, A.d.l., Sánchez-Migallón, A., Mateo, M.d.C. et al. The Unusual Transformation of an Aromatic 1H-Imidazole into a Non-Aromatic 2H-Imidazole. Struct Chem 16, 485–490 (2005). https://doi.org/10.1007/s11224-005-4467-4
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DOI: https://doi.org/10.1007/s11224-005-4467-4