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

Gu, W.-J.; Xie, W.-L.; Wang, T.-T.

doi:10.1107/S1600536812046727

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 (C-C) = 0.003 Å
R = 0.048
wR = 0.135
Data-to-parameter ratio = 12.2
Details

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

Wei-Jin Gu,^a,^b ^* Wen-Li Xie ^a and Ting-Ting Wang ^a

^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-HO 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); James et al. (2008); Teklu et al. (2005); McDonald et al. (2006); Jagerovic et al. (2002). For background and the synthesis of related hetrocycles, see: Gu et al. (2011); Shen et al. (2006, 2008); Wang, et al. (2000).

Experimental

Crystal data

C₁₆H₁₄N₄O
M_r = 278.31
Monoclinic, P 2₁ /c
a = 8.5911 (18) Å
b = 23.3760 (15) Å
c = 7.5816 (12) Å
= 114.775 (3)°
V = 1382.4 (4) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.974, T_max = 0.983
7822 measured reflections
2361 independent reflections
1728 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.135
S = 1.05
2361 reflections
194 parameters
1 restraint
H-atom parameters constrained
_max = 0.19 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10BO1ⁱ	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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009); 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.
Jagerovic, N., Cano, C., Elguero, J. & Goya, P. (2002). Bioorg. Med. Chem. 10, 817-827.
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.
McDonald, E., Workman, P. & Jones, K. (2006). Curr. Top. Med. Chem. 6, 1091-1107.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Shen, Z.-Y., Wang, B.-X., Shen, J. & Hu, H.-W. (2008). Chem. J. Chin. Univ. 29, 916-918.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Teklu, S., Gundersen, L. L., Larsen, T., Malterud, K. E. & Rise, F. (2005). Bioorg. Med. Chem. 13, 3127-3139.
Tukulula, M., Klein, R. & Kaye, P. T. (2010). Synth. Commun. 40, 2018-2028.
Wang, B.-X., Hu, J.-X., Zhang, X.-C., Hu, Y.-F. & Hu, H.-W. (2000). J. Heterocycl. Chem. 37, 1533-1537.

organic compounds