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Volume 69 
Part 12 
Page o1768  
December 2013  

Received 17 October 2013
Accepted 6 November 2013
Online 13 November 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.156
Data-to-parameter ratio = 19.9
Details
Open access

Ethyl 2-[1-(3-methyl­but­yl)-4-phenyl-1H-1,2,3-triazol-5-yl]-2-oxo­acetate

aDepartment of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan, and bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C17H21N3O3, the non-planar (r.m.s. deviation = 0.212 Å) ethyl (oxo)acetate group is oriented towards the phenyl substituent. The triazole and benzene rings are twisted with respect to each other, making a dihedral angle of 41.69 (6)°. In the crystal, mol­ecules are arranged into centrosymmetric R22(10) dimers via pairs of C-H...O inter­actions involving the ethyl (oxo)acetate groups. In addition, the triazole rings show [pi]-[pi] stacking inter­actions, with their centroids at a distance of 3.745 (2) Å.

Related literature

For the biological activity of 1,4,5-trisubstituted 1,2,3-triazoles, see: Siddiqi & Ahsan (2010[Siddiqi, N. & Ahsan, W. (2010). Eur. J. Med. Chem. 45, 1536-1543.]); Siddiqi et al. (2011[Siddiqi, N., Ahsan, W., Alam, M. S., Ali, R., Jain, S., Azad, B. & Akhtar, J. (2011). Int. J. Pharm. Sci. Rev. Res. 8, 161-169.]). For the synthesis, see: Wang et al. (2013[Wang, B., Ahmed, M. N., Zhang, J., Chen, W., Wang, X. & Hu, Y. (2013). Tetrahedron Lett. 54, 6097-6100.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C17H21N3O3

  • Mr = 315.37

  • Triclinic, [P \overline 1]

  • a = 8.1710 (8) Å

  • b = 10.0684 (9) Å

  • c = 10.6066 (10) Å

  • [alpha] = 98.331 (3)°

  • [beta] = 94.220 (3)°

  • [gamma] = 95.367 (3)°

  • V = 856.23 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 296 K

  • 0.32 × 0.25 × 0.21 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.982

  • 11605 measured reflections

  • 4189 independent reflections

  • 3196 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.156

  • S = 1.06

  • 4189 reflections

  • 211 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11B...O2i 0.97 2.59 3.338 (2) 134
Symmetry code: (i) -x+3, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: GK2593 ).


Acknowledgements

MNA is very thankful to the Higher Education Commission, Pakistan, for financial support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siddiqi, N. & Ahsan, W. (2010). Eur. J. Med. Chem. 45, 1536-1543.  [Web of Science] [CSD] [CrossRef] [PubMed]
Siddiqi, N., Ahsan, W., Alam, M. S., Ali, R., Jain, S., Azad, B. & Akhtar, J. (2011). Int. J. Pharm. Sci. Rev. Res. 8, 161-169.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wang, B., Ahmed, M. N., Zhang, J., Chen, W., Wang, X. & Hu, Y. (2013). Tetrahedron Lett. 54, 6097-6100.  [Web of Science] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1768  [ doi:10.1107/S1600536813030420 ]

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