3-({4-[(2-Methyl­benzyl­idene)amino]-5-sulfanyl­idene-1H-1,2,4-triazol-3-yl}meth­yl)-1,3-benzoxazol-2(3H)-one

Aydın, A.; Hekimoğlu, N.; Akkurt, M.; Önkol, T.; Çiçekli, Ş.U.; Büyükgüngör, O.

doi:10.1107/S1600536812051458

Volume 69
Part 2
Pages o169-o170
February 2013

Received 14 December 2012
Accepted 20 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.110
Data-to-parameter ratio = 16.7
Details

3-({4-[(2-Methylbenzylidene)amino]-5-sulfanylidene-1H-1,2,4-triazol-3-yl}methyl)-1,3-benzoxazol-2(3H)-one

Abdullah Aydin,^a ^* Nuray Hekimoglu,^b Mehmet Akkurt,^c Tijen Önkol,^d Sölen Urlu Çiçekli ^d and Orhan Büyükgüngör ^e

^aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey,^bDepartment of Physics, Institute of Science and Technology, Kastamonu University, 37100 Kastamonu, Turkey,^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,^dDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Gazi University, 06330 Ankara, Turkey, and ^eDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: aaydin@kastamonu.edu.tr

In the title compound, C₁₈H₁₅N₅O₂S, a weak intramolecular C-HS hydrogen bond results in a small dihedral angle of 3.71 (9)° between the methylphenyl and triazole rings, which, in turn, form dihedral angles of 80.09 (8) and 77.32 (8)°, respectively, with the benzoxazolone mean plane. In the crystal, N-HO hydrogen bonds link molecules into chains along [001], and weak C-HN hydrogen bonds and [pi] - [pi] interactions between the five- and six-membered rings [centroid-centroid distances = 3.5074 (11) and 3.616 (1) Å] consolidate the crystal packing.

Related literature

For details of the synthesis, see: Urlu-Cicekli et al. (2012). For related structures, see: Aydin et al. (2005, 2012). For a MOPAC AM1 theoretical full-geometry optimization, see: Dewar et al. (1985); Stewart (1993).

Experimental

Crystal data

C₁₈H₁₅N₅O₂S
M_r = 365.42
Monoclinic, P 2₁ /c
a = 18.0823 (13) Å
b = 6.4623 (4) Å
c = 15.1892 (11) Å
= 100.821 (6)°
V = 1743.4 (2) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 296 K
0.62 × 0.48 × 0.22 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.881, T_max = 0.955
10084 measured reflections
3958 independent reflections
3034 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.110
S = 1.03
3958 reflections
237 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO2ⁱ	0.86	2.03	2.856 (2)	162
C4-H4N4ⁱⁱ	0.93	2.52	3.387 (3)	155
C11-H11S1	0.93	2.48	3.2159 (18)	136
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5375 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant No. F.279 of the University Research Fund).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Aydin, A., Önkol, T., Akkurt, M. & Büyükgüngör, O. (2005). Anal. Sci. 21, x119-x120.
Aydin, A., Soyer, Z., Akkurt, M. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1544-o1545.
Dewar, M. J. S., Zoebish, E. G., Healy, E. F. & Stewart, J. J. P. (1985). J. Am. Chem. Soc. 107, 3902-3909.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stewart, J. J. P. (1993). MOPAC7.0. QCPE Program No. 455. Quantum Chemistry Program Exchange, Department of Chemistry, Indiana University, Bloomington, IN, USA.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.
Urlu-Cicekli, S., Onkol, T., Ozgen, S. & Sahin, M. F. (2012). Rev. Roum. Chim. 57, 187-195.

organic compounds