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

Sreenivasa, S.; ManojKumar, K.E.; Shet Prakash, M.; Suchetan, P.A.; Palakshamurthy, B.S.

doi:10.1107/S160053681204740X

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 (C-C) = 0.004 Å
R = 0.066
wR = 0.227
Data-to-parameter ratio = 14.9
Details

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

S. Sreenivasa,^a ^* K. E. ManojKumar,^a M. Shet Prakash,^b P. A. Suchetan ^b and B. S. Palakshamurthy ^c

^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-HN hydrogen bonds generating R₂²(16) patterns. The dimeric units are further linked into C(6) chains via an additional C-HN hydrogen bond.

Related literature

For the synthesis and biological activity of pyrrolidine derivatives, see: Li et al. (2006); Lokhande et al. (2003); Imamura et al. (2004); Wyrzykiewicz, et al. (1993) and of pyrimidine derivatives, see: Holla et al. (2006); Zhao et al. (2007); Sondhi et al. (2005); Khalifa et al. (2005). For the graph-set description of hydrogen-bond motifs, see: Etter (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₃H₂₀N₄
M_r = 232.33
Triclinic, $[P \overline 1]$
a = 6.344 (3) Å
b = 8.766 (4) Å
c = 12.056 (6) Å
= 79.10 (3)°
= 86.05 (3)°
= 85.72 (3)°
V = 655.6 (6) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.986, T_max = 0.999
8712 measured reflections
2302 independent reflections
1600 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.227
S = 1.13
2302 reflections
155 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2BN3ⁱ	0.97 (1)	2.82	3.793 (2)	175
C9-H9CN2ⁱⁱ	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); cell refinement: APEX2 and SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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

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organic compounds