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Volume 69 
Part 12 
Page o1812  
December 2013  

Received 29 October 2013
Accepted 13 November 2013
Online 23 November 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.152
Data-to-parameter ratio = 13.6
Details
Open access

Ethyl 6-methyl-8-phenyl-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 title compound, C16H15N3O2, the 1,2,4-triazolo[1,5-a]pyridine ring system is almost planar (r.m.s. deviation = 0.0068 Å) and forms a dihedral angle of 61.4 (3)° with the phenyl ring. In the structure, centrosymmetrically related mol­ecules are linked into dimers by pairs of C-H...N hydrogen bonds.

Related literature

For application 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 the synthesis of [1,2,4]triazolo[1,5-a]pyridine derivatives, 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
  • C16H15N3O2

  • Mr = 281.31

  • Monoclinic, P 21 /n

  • a = 13.401 (3) Å

  • b = 7.4825 (19) Å

  • c = 15.068 (4) Å

  • [beta] = 98.986 (4)°

  • V = 1492.4 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.23 × 0.19 × 0.15 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 = 0.981, Tmax = 0.987

  • 7312 measured reflections

  • 2611 independent reflections

  • 1920 reflections with I > 2[sigma](I)

  • Rint = 0.086

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.152

  • S = 1.05

  • 2611 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...N2i 0.93 2.49 3.332 (3) 151
Symmetry code: (i) -x, -y+2, -z+1.

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 (Bruker, 1999[Bruker (1999). SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5092 ).


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, o1812  [ doi:10.1107/S1600536813031152 ]

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