Abstract
The title compound, C20H17N3O2, was synthesized by the cyclization of a chalcone derivative with malononitrile, and was characterized by 1H NMR and FT-IR spectroscopy techniques. The crystal structure was determined by single crystal X-ray structure determination. In the crystal packing, the molecules are linked by N–H···N hydrogen bonds forming a two dimensional network parallel to the (1 0–2) plane. The crystal structure is further stabilized by weak C–H···π interactions. The compound exhibits greenish-blue fluorescence in acetonitrile with an emission wavelength at 476 nm when was excited at 365 nm.
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F. E. Goda, A. A. M. Abdel-Aziz, and O. A. Attef, Bioorg. Med. Chem. 12, 1845 (2004).
A. Kamal, M. N. A. Khan, K. S. Reddy, and K. Rohini, Bioorg. Med. Chem. 15, 1004 (2007).
A. H. Shamroukh, M. El-Shahat, J. Drabowicz, M.M. Ali, A. E. Rashad, and H. S. Ali, Eur. J. Med. Chem. 69, 521 (2013).
E. R. Kotb, M. A. El-Hashash, M. A. Salama, H. S. Kalf, and N. A. M. A. Wahed, Acta Chim. Slov. 56, 908 (2009).
H. A. El-Sayed, A. H. Moustafa, A. E. F. Z. Haikal, R. Abu-El-Halawa, and E. S. H. E. Ashry, Eur. J. Med. Chem. 46, 2948 (2011).
L. N. Tumey, N. Bhagirath, A. Brennan, N. Brooijmans, J. Lee, X. Yang, and D. H. Boschelli, Bioorg. Med. Chem. 17, 7933 (2009).
N. S. El-Sayed, A. N. Shirazi, M. G. El-Meligy, A. K. El-Ziaty, D. Rowley, J. Sun, Z. A. Nagib, and K. Parang, Tet. Lett. 55, 1154 (2014).
V. Raghukumar, D. Thirumalai, V. T. Ramakrishnan, V. Karunakara, and P. Ramamurthy, Tetrahedron 59, 3761 (2003).
R. R. Koner, S. Sinha, S. Kumar, C. K. Nandi, and S. Ghosh, Tet. Lett. 53, 2302 (2012).
T. Suwunwong, S. Chantrapromma, and H.-K. Fun, Acta Crystallogr. E 68, o2812 (2012).
W.-J. Zhou, S.-J. Ji, and Z.-L. Shen, J. Organomet. Chem. 691, 1356 (2006).
N. A., Al-Jaber, A. S. A. Bougasim, and M. S. Karah, J. Saudi Chem. Soc. 16, 45 (2012).
J. P. Jasinski, R. J. Butcher, B. Narayana, S. Samshuddin, and H. S. Yathirajan, Acta Crystallogr. E 66, o269 (2010).
Bruker (2009). APEX2, SAINT and SADABS (Bruker AXS, Madison, Wisconsin, USA, 2009).
G. M. Sheldrick, Acta Crystallogr. A 64, 112 (2008).
A. L. Spek, Acta Crystallogr. D 65, 148 (2009).
C. F. Macrae, P. R. Edginton, P. McCabe, E. Pidcook, G. P. Shields, R. Taylor, M. Towler, and J. van de Streek, J. Appl. Crystallogr. 39, 453 (2006).
F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc. Perkin Trans. 2. S1–19 (1987).
T. Suwunwong, S. Chantrapromma, C.-K. Quah, and H.-K. Fun, Acta Crystallogr. E 69, o1816 (2013).
A. H. Basta, A. S. Girgis, and H. El-Saied, Dyes Pigments 54, 1 (2002).
A. H. Basta, A. S. Girgis, H. El-Saied, and M. A. Mohamed, Mater. Lett. 65, 1713 (2011).
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Suwunwong, T., Chantrapromma, S. & Fun, HK. Greenish-blue fluorescence of 6-(4-aminophenyl)-4-(4-methoxyphenyl)-2-methoxynicotinonitrile: Synthesis, spectroscopy, crystal structure, and fluorescence property. Crystallogr. Rep. 60, 1065–1071 (2015). https://doi.org/10.1134/S1063774515070287
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DOI: https://doi.org/10.1134/S1063774515070287