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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 [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.110
Data-to-parameter ratio = 16.7
Details
Open access

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

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-H...S 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-H...O hydrogen bonds link molecules into chains along [001], and weak C-H...N 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[Urlu-Cicekli, S., Onkol, T., Ozgen, S. & Sahin, M. F. (2012). Rev. Roum. Chim. 57, 187-195.]). For related structures, see: Aydin et al. (2005[Aydin, A., Önkol, T., Akkurt, M. & Büyükgüngör, O. (2005). Anal. Sci. 21, x119-x120.], 2012[Aydin, A., Soyer, Z., Akkurt, M. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1544-o1545.]). For a MOPAC AM1 theoretical full-geometry optimization, see: Dewar et al. (1985[Dewar, M. J. S., Zoebish, E. G., Healy, E. F. & Stewart, J. J. P. (1985). J. Am. Chem. Soc. 107, 3902-3909.]); Stewart (1993[Stewart, J. J. P. (1993). MOPAC7.0. QCPE Program No. 455. Quantum Chemistry Program Exchange, Department of Chemistry, Indiana University, Bloomington, IN, USA.]).

[Scheme 1]

Experimental

Crystal data
  • C18H15N5O2S

  • Mr = 365.42

  • Monoclinic, P 21 /c

  • a = 18.0823 (13) Å

  • b = 6.4623 (4) Å

  • c = 15.1892 (11) Å

  • [beta] = 100.821 (6)°

  • V = 1743.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.881, Tmax = 0.955

  • 10084 measured reflections

  • 3958 independent reflections

  • 3034 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.110

  • S = 1.03

  • 3958 reflections

  • 237 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O2i 0.86 2.03 2.856 (2) 162
C4-H4...N4ii 0.93 2.52 3.387 (3) 155
C11-H11...S1 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [ChemPort] [details]
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.  [CSD] [CrossRef] [details]
Dewar, M. J. S., Zoebish, E. G., Healy, E. F. & Stewart, J. J. P. (1985). J. Am. Chem. Soc. 107, 3902-3909.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
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.  [ChemPort]


Acta Cryst (2013). E69, o169-o170   [ doi:10.1107/S1600536812051458 ]

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