Crystal Structure of 3-Benzyl-4-(3-methyl-3-phenylcyclobut-1-yl)-1,3-thiazole-2(3H)-thione

B. Sen; E. Barim; C. Kirilmis; M. Aygün

doi:10.14233/ajchem.2016.19440

Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Issue Published : December 5, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Crystal Structure of 3-Benzyl-4-(3-methyl-3-phenylcyclobut-1-yl)-1,3-thiazole-2(3H)-thione

https://doi.org/10.14233/ajchem.2016.19440

B. Sen

Department of Physics, Faculty of Science, Dokuz Eylül University, 35160 Buca, Izmir, Turkey

E. Barim

Department of Chemistry, Faculty of Art and Science, Adiyaman University, 02040 Adiyaman, Turkey

C. Kirilmis

Department of Chemistry, Faculty of Art and Science, Adiyaman University, 02040 Adiyaman, Turkey

M. Aygün

Department of Physics, Faculty of Science, Dokuz Eylül University, 35160 Buca, Izmir, Turkey

Corresponding Author(s) : M. Aygün

muhittin.aygun@deu.edu.tr

Asian Journal of Chemistry, Vol. 28 No. 3 (2016): Vol 28 Issue 3
Article Published : December 5, 2015

Abstract

The title compound 3-benzyl-4-(3-methyl-3-phenylcyclobut-1-yl)-1,3-thiazole-2(3H)-thione having m.f. C₂₁H₂₁NS₂, crystallizes in the orthorhombic space group Pna2₁, Z = 4 with a = 10.1027(5) Å, b = 17.3913(8) Å, c = 10.8832(6) Å, V = 1912.17(17) Å³ and D_calc = 1.221 g/cm³. In the title molecule, the cyclobutane ring is puckered, with a dihedral angle of 23.78(18)° between the two planes. The thiazole ring makes dihedral angles of 84.23(11), 55.58(16) and 88.08(10)°, respectively, with the benzene, cyclobutane and phenyl rings. Weak intramolecular C–H···S and C–H···N hydrogen-bonding interactions are present in the molecule. Each of these interactions forms a five-membered ring. The supramolecular aggregation is completed by two types of C–H···p interactions involving the H atoms from C5 and C20 atoms.

Keywords

Crystal structure Cyclobutane 1,3-Thiazole-2(3H)-thione

Sen, B., Barim, E., Kirilmis, C., & Aygün, M. (2015). Crystal Structure of 3-Benzyl-4-(3-methyl-3-phenylcyclobut-1-yl)-1,3-thiazole-2(3H)-thione. Asian Journal of Chemistry, 28(3), 631–633. https://doi.org/10.14233/ajchem.2016.19440

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References

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E. Roger, C.J. Pierre, V. Pualette, G. Gerard, J.P. Chepat and G. Robert, Eur. J. Med. Chem., 12, 501 (1977).

P. Koparir, M. Karaarslan, C. Orek and M. Koparir, Phosphorus Sulfur Silicon Rel. Elem., 186, 2368 (2011); doi:10.1080/10426507.2011.604660.

S. Eid, T. Roisnel and D. Lorcy, J. Organomet. Chem., 693, 2755 (2008); doi:10.1016/j.jorganchem.2008.05.021.

M. Ahmedzade and C. Kirilmis, S. Afr. J. Chem., 56, 21 (2003).

CrysAlisPro Software system, Version 1.171.35.11, Agilent Technologies UK Ltd (2011).

O.V. Dolomanov, L.J. Bourhis, R.J. Gildea, J.A.K. Howard and H. Puschmann, J. Appl. Cryst., 42, 339 (2009); doi:10.1107/S0021889808042726.

G.M. Sheldrick, Acta Crystallogr., A64, 112 (2008); doi:10.1107/S0108767307043930.

A.L. Spek, J. Appl. Cryst., 36, 7 (2003); doi:10.1107/S0021889802022112.

L.J. Farrugia, J. Appl. Cryst., 30, 565 (1997); doi:10.1107/S0021889897003117.

D.C. Swenson, M. Yamamoto and D.J. Burton, Acta Crystallogr., C53, 1445 (1997); doi:10.1107/S0108270197003764.

F.H. Allen, Acta Crystallogr. B, 40, 64 (1984); doi:10.1107/S0108768184001750.

F. Şen, M. Dinçer, A. Çukurovali and I. Yilmaz, Acta Crystallogr., E68, o1052 (2012); doi:10.1107/S1600536812010203.

M. Koca, C. Kirilmiş and C. Arici, Acta Crystallogr., E66, o523 (2010); doi:10.1107/S1600536810003910.

C. Arici, C. Kirilmiş, M. Koca and F.W. Heinemann, Acta Crystallogr., E62, o2783 (2006).

F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc. Perkin Trans. II, S1 (1987); doi:10.1039/p298700000s1.

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J. Hartung, N. Schneiders and U. Bergsträsser, Acta Crystallogr., E61, o421 (2005); doi:10.1107/S1600536805001431.

J. Hartung, N. Schneiders and U. Bergsträsser, Acta Crystallogr., E62, o4713 (2006); doi:10.1107/S1600536806038360.

J. Hartung, S. Altermann, I. Svoboda and H. Fuess, Acta Cryst., E61, o1738 (2005); doi:10.1107/S1600536805013061.

F. Şen, M. Dinçer and A. Cukurovali, J. Mol. Struct., 1076, 1 (2014); doi:10.1016/j.molstruc.2014.07.041.

J. Hartung, K. Daniel, T. Gottwald, I. Svoboda and H. Fuess, Acta Cryst., E61, o1741 (2005).

J. Bernstein, R.E. Davis, L. Shimoni and N.-L. Chang, Angew. Chem. Int. Ed. Engl., 34, 1555 (1995); doi:10.1002/anie.199515551.

Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Crystal Structure of 3-Benzyl-4-(3-methyl-3-phenylcyclobut-1-yl)-1,3-thiazole-2(3H)-thione

Corresponding Author(s) : M. Aygün

Abstract

Keywords

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