[Journal logo]

Volume 69 
Part 3 
Page o450  
March 2013  

Received 28 January 2013
Accepted 21 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.005 Å
R = 0.050
wR = 0.129
Data-to-parameter ratio = 15.4
Details
Open access

(3,5-Dimethyl-1H-pyrazol-1-yl){3-[(3,5-dimethyl-1H-pyrazol-1-yl)carbonyl]-5-methylindolizin-1-yl}methanone

aDepartment of Applied Chemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China,bKey Laboratory of Applied Photochemistry, Nanjing Normal University, Nanjing 210097, People's Republic of China, and cJiangsu Key Laboratory of Biofunctional Materials, Jiangsu Research Center of Biomedical Functional Materials Engineering, Nanjing Normal University, Nanjing 210097, People's Republic of China
Correspondence e-mail: wangnjnuchem@163.com

There are two independent molecules in the asymmetric unit of the title compound, C21H21N5O2. In each molecule, the indolizine ring system is essentially planar, with r.m.s. deviations of 0.030 and 0.028 Å. The dihedral angles between the indolizine ring system and the pyrazole rings are 54.7 (3) and 8.6 (3)° in one molecule and 54.4 (3) and 6.6 (3)° in the other. In the crystal, weak C-H...O and C-H...N hydrogen bonds link molecules, forming a two-dimensional network parallel to (100).

Related literature

For the 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 to 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. Chin. 27, 651-653.], 2008[Shen, Z.-Y., Wang, B.-X., Shen, J. & Hu, H.-W. (2008). Chem. J. Chin. Univ. Chin. 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
  • C21H21N5O2

  • Mr = 375.43

  • Orthorhombic, P c a 21

  • a = 19.7286 (11) Å

  • b = 11.5659 (14) Å

  • c = 17.8088 (18) Å

  • V = 4063.6 (7) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 291 K

  • 0.26 × 0.22 × 0.20 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.984

  • 30693 measured reflections

  • 7955 independent reflections

  • 6221 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.129

  • S = 1.07

  • 7955 reflections

  • 516 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...O2i 0.93 2.37 3.282 (4) 167
C21-H21B...O1ii 0.96 2.59 3.404 (4) 142
C30-H30C...N3iii 0.96 2.52 3.472 (4) 169
C33-H33...O4iv 0.93 2.55 3.393 (4) 152
Symmetry codes: (i) x, y-1, z; (ii) [-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]; (iii) [x-{\script{1\over 2}}, -y+1, z]; (iv) x, y+1, z.

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; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5581 ).


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. Chin. 27, 651-653.  [ChemPort]
Shen, Z.-Y., Wang, B.-X., Shen, J. & Hu, H.-W. (2008). Chem. J. Chin. Univ. Chin. 29, 916-918.  [ChemPort]
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 (2013). E69, o450  [ doi:10.1107/S1600536813005060 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.