Abstract
The molecular structure of the title compound C22H18N4O2S was characterized by single crystal X-ray diffraction method. The compound crystallizes in the orthorhombic space group Pbca with a = 10.1970 (4) Å, b = 26.8880 (5) Å, c = 15.2119 (13) Å, Z = 8, V = 4170.8 (4) Å3. In the title compound, benzyl rings and thiophene ring are bridged by 1,2,4-triazole ring system. The thiophene ring is disordered over two positions, which are approximately parallel and oppositely orientated. The major component refined to a siteoccupancy factor of 0.731 (3). An intramolecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, a C-H⋯O hydrogen bond links the molecules into a C(6) chain along the c axis. A weak C-H⋯π interaction also occurs.
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M. Pitucha, P. Borowski, Z. Karczmarzyk, et al., J. Mol. Struct. 919, 170 (2009).
M. S. Karthikeyan, D. J. Prasad, B. Poojary, et al., Bioorg. Med. Chem. 14, 7482 (2006).
J. L. Kelley, C. S. Koble, R. G. Davis, et al., J. Med. Chem. 38, 4131 (1995).
B. S. Holla, M. Mahalinga, M. S. Karthikeyan, et al., Eur. J. Med. Chem. 40, 1173 (2005).
U. S. Gökçen, N. G. Kelekçi, Ö. Göktaç, et al., Bioorg. Med. Chem. 15, 5738 (2007).
B. S. Holla, B. Veerandra, M. K. Shivanada, et al., Eur. J. Med. Chem. 38, 759 (2003).
S. Joshi, N. Khosla, P. Tiwari, Bioorg. Med. Chem. 12, 571 (2004).
E. Menegola, M. L. Broccia, F. Di Renzo, et al., Reprod. Toxicol. 15, 421 (2001).
H. Khanmohammadi, M. H. Abnosi, A. Hosseinzadeh, et al., Spectrochim. Acta A 71, 1474 (2008).
D. Barton and W.D. Ollis, Comprehensive Organic Chemistry (Pergamon, Oxford, 1979).
R. W. Layer, Chem. Rev. 63, 489 (1963).
C. K. Ingold, Structure and Mechanism in Organic Chemistry (Cornell Univ., Ithaca, 1969).
A. E. Taggi, A. M. Hafez, H. Wack, et al., J. Am. Chem. Soc. 124, 6626 (2002).
P. S. Dixit and K. Srinivasan, Inorg. Chem. 27, 4507 (1988).
D. P. Kessissoglou, W.M. Butler, and V.L. Pecoraro, Inorg. Chem. 26, 495 (1987).
X. B. Lu, Y. L. Zhang, K. Jin, et al., Tetrahedron 60, 7835 (2004).
C. A. Sureshan and P. K. Bhattacharya, J. Mol. Catal. A 136, 285 (1998).
J. C. Moutet and A. Ourari, Electrochim. Acta 42, 2525 (1997).
R. Ramnauth, S. Al-Juaid, M. Motevalli, et al., Inorg. Chem. 43, 4072 (2004).
H. Miyasaka, N. Matsumoto, H. Okawa, et al., J. Am. Chem. Soc. 118, 981 (1996).
H. Tanak, A.A. Ağar, and O. Büyükgüngür, J. Mol. Struct. 1048, 41 (2013).
Y. Ünver, E. Düğdü, K. Sancak, et al., Turk. J. Chem. 33, 135 (2009).
Stoe & Cie X-AREA (Version 1.18) X-RED32 (Version 1.04) (Stoe&Cie, Darmstadt, 2002).
G. M. Sheldrick, Acta Crystallogr. A 64, 112 (2008).
L. J. Farrugia, J. Appl. Crystallogr. 45, 849 (2012).
I. Yılmaz, N. B. Arslan, C. Kazak, et al., Acta Crystallogr. E 62, o3067 (2006).
H. Tanak, M. Yavuz, Z. Lagap, et al., Acta Crystallogr. E 66, o301 (2010).
R. Ustabaç, Y. Ünver, N. Suleymanoğlu, et al., Acta Crystallogr. E 65, o1006 (2009).
Y. Köysal and H. Tanak, Spectrochim. Acta A 93, 106 (2012).
H. Tanak, Y. Köysal, Y. Ünver, et al., Mol. Phys. 108, 127 (2010).
H. Tanak, Y. Köysal, Y. Ünver, et al., Acta Crystallogr. E 65, o3039 (2009).
H. Tanak, A.A. Ağar, and O. Büyükgüngür, Spectrochim. Acta A 118, 672 (2014).
J. Bernstein, R. E. Davies, L. Shimoni, et al., Angew. Chem. Int. Ed. Engl. 34, 1555 (1995).
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Tanak, H., Işik, Ş. Crystal structure of 4-[(Benzylidene-amino)]-2-(2-oxo-2-phenylethyl)-5-thiophen-2-ylmethyl-2,4-dihydro-[1,2,4]triazol-3-one. Crystallogr. Rep. 59, 969–973 (2014). https://doi.org/10.1134/S1063774514070189
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DOI: https://doi.org/10.1134/S1063774514070189