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Volume 68 
Part 12 
Page o3399  
December 2012  

Received 5 November 2012
Accepted 13 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.135
Data-to-parameter ratio = 12.2
Details
Open access

1-[(3,5-Dimethyl-1H-pyrazol-1-yl)carbonyl]-5-methylindolizine-3-carbonitrile

aDepartment of Applied Chemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China, and bKey Laboratory of Applied Photochemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China
Correspondence e-mail: guweijin2010@163.com

In the title molecule, C16H14N4O, the indolizine ring system is essentially planar, with a maximum deviation of 0.013 (3) Å, and forms a dihedral angle of 7.52 (12)° with the pyrazole ring. In the crystal, weak C-H...O hydrogen bonds and [pi]-[pi] stacking interactions, with a centroid-centroid distance of 3.6378 (16) Å, link molecules along [001].

Related literature

For biological applications of indolizines and pyrazoles, see: Tukulula et al. (2010[Tukulula, M., Klein, R. & Kaye, P. T. (2010). Synth. Commun. 40, 2018-2028.]); James et al. (2008[James, D. A., Koya, K., Li, H., Liang, G. Q., Xia, Z. Q., Ying, W. W., Wu, Y. M. & Sun, L. J. (2008). Bioorg. Med. Chem. Lett. 18, 1784-1787.]); Teklu et al. (2005[Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E. & Rise, F. (2005). Bioorg. Med. Chem. 13, 3127-3139.]); McDonald et al. (2006[McDonald, E., Workman, P. & Jones, K. (2006). Curr. Top. Med. Chem. 6, 1091-1107.]); Jagerovic et al. (2002[Jagerovic, N., Cano, C., Elguero, J. & Goya, P. (2002). Bioorg. Med. Chem. 10, 817-827.]). For background and the synthesis of related hetrocycles, see: Gu et al. (2011[Gu, W.-J., Zhuang, J., Jiang, Y.-L. & Wang, B.-X. (2011). Acta Cryst. E67, o123.]); Shen et al. (2006[Shen, Y.-M., Wang, B.-X., Feng, Y.-Y., Shen, Z.-Y., Shen, J., Li, C. & Hu, H.-W. (2006). Chem. J. Chin. Univ. 27, 651-653.], 2008[Shen, Z.-Y., Wang, B.-X., Shen, J. & Hu, H.-W. (2008). Chem. J. Chin. Univ. 29, 916-918.]); Wang, et al. (2000[Wang, B.-X., Hu, J.-X., Zhang, X.-C., Hu, Y.-F. & Hu, H.-W. (2000). J. Heterocycl. Chem. 37, 1533-1537.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14N4O

  • Mr = 278.31

  • Monoclinic, P 21 /c

  • a = 8.5911 (18) Å

  • b = 23.3760 (15) Å

  • c = 7.5816 (12) Å

  • [beta] = 114.775 (3)°

  • V = 1382.4 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 291 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.974, Tmax = 0.983

  • 7822 measured reflections

  • 2361 independent reflections

  • 1728 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.135

  • S = 1.05

  • 2361 reflections

  • 194 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10B...O1i 0.96 2.56 3.435 (4) 151
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5554 ).


Acknowledgements

We thank the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD) for financial support.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Gu, W.-J., Zhuang, J., Jiang, Y.-L. & Wang, B.-X. (2011). Acta Cryst. E67, o123.  [CrossRef] [details]
Jagerovic, N., Cano, C., Elguero, J. & Goya, P. (2002). Bioorg. Med. Chem. 10, 817-827.  [CrossRef] [PubMed] [ChemPort]
James, D. A., Koya, K., Li, H., Liang, G. Q., Xia, Z. Q., Ying, W. W., Wu, Y. M. & Sun, L. J. (2008). Bioorg. Med. Chem. Lett. 18, 1784-1787.  [CrossRef] [PubMed] [ChemPort]
McDonald, E., Workman, P. & Jones, K. (2006). Curr. Top. Med. Chem. 6, 1091-1107.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shen, Y.-M., Wang, B.-X., Feng, Y.-Y., Shen, Z.-Y., Shen, J., Li, C. & Hu, H.-W. (2006). Chem. J. Chin. Univ. 27, 651-653.  [ChemPort]
Shen, Z.-Y., Wang, B.-X., Shen, J. & Hu, H.-W. (2008). Chem. J. Chin. Univ. 29, 916-918.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E. & Rise, F. (2005). Bioorg. Med. Chem. 13, 3127-3139.  [CrossRef] [PubMed] [ChemPort]
Tukulula, M., Klein, R. & Kaye, P. T. (2010). Synth. Commun. 40, 2018-2028.  [ISI] [CrossRef] [ChemPort]
Wang, B.-X., Hu, J.-X., Zhang, X.-C., Hu, Y.-F. & Hu, H.-W. (2000). J. Heterocycl. Chem. 37, 1533-1537.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3399  [ doi:10.1107/S1600536812046727 ]

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