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Volume 69 
Part 12 
Page o1796  
December 2013  

Received 29 October 2013
Accepted 6 November 2013
Online 20 November 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.055
wR = 0.170
Data-to-parameter ratio = 13.6
Details
Open access

Ethyl 8-(2,4-di­chloro­phen­yl)-6-methyl-1,2,4-triazolo[1,5-a]pyridine-7-carboxyl­ate

aSchool of Chemical Engineering, Taishan Medical University, Taian 271016, People's Republic of China
Correspondence e-mail: chemyangli@gmail.com

In the title compound, C16H13Cl2N3O2, the carboxyl­ate group and the benzene ring attached to the central 1,2,4-triazolo[1,5-a]pyridine bicycle are twisted from its mean plane by 55.6 (1) and 72.6 (1)°, respectively. In the crystal, weak C-H...O inter­actions link the mol­ecules into zigzag chains propagating in [100].

Related literature

For applications of [1,2,4]triazolo[1,5-a]pyridine derivatives, see: Luo & Hu (2006[Luo, Y. & Hu, Y. (2006). Arch. Pharm. Chem. Life Sci. 339, 262-266.]); Liu & Hu (2002[Liu, T. & Hu, Y. (2002). Bioorg. Med. Chem. Lett. 12, 2411-2413.]). For details of the synthesis, see: Jones & Sliskovic (1983[Jones, G. & Sliskovic, D. R. (1983). Adv. Heterocycl. Chem. 34, 79-143.]); Wang et al. (2003[Wang, J. W., Jia, J., Hou, D. J., li, H. M. & Yin, J. (2003). Chin. J. Org. Chem. 23, 173-175.]); Ge et al. (2009[Ge, Y. Q., Jia, J., Yang, H., Zhao, G. L., Zhan, F. X. & Wang, J. W. (2009). Heterocycles, 78, 725-736.]); Jia et al. (2010[Jia, J., Ge, Y. Q., Tao, X. T. & Wang, J. W. (2010). Heterocycles, 81, 185-194.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13Cl2N3O2

  • Mr = 350.19

  • Orthorhombic, P b c a

  • a = 14.693 (2) Å

  • b = 13.531 (2) Å

  • c = 16.347 (2) Å

  • V = 3250.0 (8) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.41 mm-1

  • T = 298 K

  • 0.33 × 0.26 × 0.21 mm

Data collection
  • Brucker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.876, Tmax = 0.919

  • 15766 measured reflections

  • 2860 independent reflections

  • 2206 reflections with I > 2[sigma](I)

  • Rint = 0.090

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.170

  • S = 1.07

  • 2860 reflections

  • 210 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O1i 0.93 2.55 3.296 (4) 137
Symmetry code: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SADABS 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5435 ).


References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Ge, Y. Q., Jia, J., Yang, H., Zhao, G. L., Zhan, F. X. & Wang, J. W. (2009). Heterocycles, 78, 725-736.  [ChemPort]
Jia, J., Ge, Y. Q., Tao, X. T. & Wang, J. W. (2010). Heterocycles, 81, 185-194.  [ChemPort]
Jones, G. & Sliskovic, D. R. (1983). Adv. Heterocycl. Chem. 34, 79-143.  [CrossRef] [ChemPort]
Liu, T. & Hu, Y. (2002). Bioorg. Med. Chem. Lett. 12, 2411-2413.  [CrossRef] [PubMed] [ChemPort]
Luo, Y. & Hu, Y. (2006). Arch. Pharm. Chem. Life Sci. 339, 262-266.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Wang, J. W., Jia, J., Hou, D. J., li, H. M. & Yin, J. (2003). Chin. J. Org. Chem. 23, 173-175.  [ChemPort]


Acta Cryst (2013). E69, o1796  [ doi:10.1107/S160053681303033X ]

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