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Volume 68 
Part 12 
Page o3440  
December 2012  

Received 27 October 2012
Accepted 19 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.066
wR = 0.227
Data-to-parameter ratio = 14.9
Details
Open access

4-Methyl-2,6-bis(pyrrolidin-1-yl)pyrimidine

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the crystal of the title compound, C13H20N4, the molecule is nearly planar, the dihedral angles between the pyrimidine and the two pyrrolidine rings being 4.71 (2) and 4.50 (2)°. The crystal features inversion-related dimers linked by pairs of C-H...N hydrogen bonds generating R22(16) patterns. The dimeric units are further linked into C(6) chains via an additional C-H...N hydrogen bond.

Related literature

For the synthesis and biological activity of pyrrolidine derivatives, see: Li et al. (2006[Li, X., Li, Y. & Xu, W. (2006). Bioorg. Med. Chem. 14, 1287-1293.]); Lokhande et al. (2003[Lokhande, T. N., Bobade, A. S. & Khadse, B. G. (2003). Indian Drugs, 40, 147-150.]); Imamura et al. (2004[Imamura, S., Ishihara, Y., Hattori, T., Kurasawa, O., Matsushita, Y. & Sugihara, Y. (2004). Chem. Pharm. Bull. 52, 63-73.]); Wyrzykiewicz, et al. (1993[Wyrzykiewicz, E., Bartkowiak, G. & Kedzia, B. (1993). Il Farmaco, 48, 979-988.]) and of pyrimidine derivatives, see: Holla et al. (2006[Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Akberali, P. M. & Shetty, N. S. (2006). Bioorg. Med. Chem. 14, 2040-2047.]); Zhao et al. (2007[Zhao, X.-L., Zhao, Y.-F., Guo, S.-C., Song, H.-S., Wang, D. & Gong, P. (2007). Molecules, 12, 1136-1146.]); Sondhi et al. (2005[Sondhi, S. M., Singh, N., Johar, M. & Kumar, A. (2005). Bioorg. Med. Chem. 13, 6158-6166.]); Khalifa et al. (2005[Khalifa, N. M., Ismail, N. S. & Abdulla, M. M. (2005). Egypt. Pharm. J. 4, 277-288.]). For the graph-set description of hydrogen-bond motifs, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C13H20N4

  • Mr = 232.33

  • Triclinic, [P \overline 1]

  • a = 6.344 (3) Å

  • b = 8.766 (4) Å

  • c = 12.056 (6) Å

  • [alpha] = 79.10 (3)°

  • [beta] = 86.05 (3)°

  • [gamma] = 85.72 (3)°

  • V = 655.6 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 296 K

  • 0.2 × 0.18 × 0.02 mm

Data collection
  • Bruker SMART X2S diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.986, Tmax = 0.999

  • 8712 measured reflections

  • 2302 independent reflections

  • 1600 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.227

  • S = 1.13

  • 2302 reflections

  • 155 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2B...N3i 0.97 (1) 2.82 3.793 (2) 175
C9-H9C...N2ii 0.96 (1) 2.93 3.742 (2) 143
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2009[Bruker (2009). APEX2, 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2214 ).


Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, Tumkur, for his constant encouragement, Professor T. N. Guru Row and Vijithkumar, S. S. C. U., Indian Institute of Science, Bangalore, for their help in collecting single-crystal data. The authors also thank Dr H. C. Devaraje Gowda, Department of Physics Yuvarajas College (constituent), University of Mysore, for his support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Holla, B. S., Mahalinga, M., Karthikeyan, M. S., Akberali, P. M. & Shetty, N. S. (2006). Bioorg. Med. Chem. 14, 2040-2047.  [CrossRef] [PubMed] [ChemPort]
Imamura, S., Ishihara, Y., Hattori, T., Kurasawa, O., Matsushita, Y. & Sugihara, Y. (2004). Chem. Pharm. Bull. 52, 63-73.  [CrossRef] [PubMed] [ChemPort]
Khalifa, N. M., Ismail, N. S. & Abdulla, M. M. (2005). Egypt. Pharm. J. 4, 277-288.
Li, X., Li, Y. & Xu, W. (2006). Bioorg. Med. Chem. 14, 1287-1293.  [CrossRef] [PubMed] [ChemPort]
Lokhande, T. N., Bobade, A. S. & Khadse, B. G. (2003). Indian Drugs, 40, 147-150.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sondhi, S. M., Singh, N., Johar, M. & Kumar, A. (2005). Bioorg. Med. Chem. 13, 6158-6166.  [CrossRef] [PubMed] [ChemPort]
Wyrzykiewicz, E., Bartkowiak, G. & Kedzia, B. (1993). Il Farmaco, 48, 979-988.  [ChemPort] [PubMed]
Zhao, X.-L., Zhao, Y.-F., Guo, S.-C., Song, H.-S., Wang, D. & Gong, P. (2007). Molecules, 12, 1136-1146.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o3440  [ doi:10.1107/S160053681204740X ]

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