2-Amino-4,6-dimethyl­pyrimidin-1-ium chloride

Hu, H.-L.; Yeh, C.-W.

doi:10.1107/S1600536812046569

Volume 68
Part 12
Page o3372
December 2012

Received 13 October 2012
Accepted 11 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.003 Å
R = 0.039
wR = 0.105
Data-to-parameter ratio = 17.4
Details

2-Amino-4,6-dimethylpyrimidin-1-ium chloride

Hui-Ling Hu ^a and Chun-Wei Yeh ^b,^a ^*

^aDepartment of Hospitality Management, Taoyuan Innovation Institute of Technology, Jhongli 32091, Taiwan, and ^bDepartment of Chemistry, Chung-Yuan Christian University, Jhongli 32023, Taiwan
Correspondence e-mail: cwyeh@cycu.org.tw

In the title compound, C₆H₁₀N₃⁺·Cl^-, the cation is essentially planar with an r.m.s. deviations of the fitted atoms of 0.008 Å. In the crystal, adjacent ions are linked by weak N-HCl hydrogen bonds involving the pyrimidine and amine N atoms, forming a three-dimensional network. C-H [pi] interactions between the methyl and pyrimidine groups and [pi] - [pi] stacking [centroid-centroid distance = 3.474 (1) Å] between parallel pyrimidine ring systems are also observed.

Related literature

For the crystal structures of 2-aminopyrimidinium salts with other anions, see: Cheng et al. (2010); Eshtiagh-Hosseini et al. (2010); Hu & Yeh (2012).

Experimental

Crystal data

C₆H₁₀N₃⁺·Cl^-
M_r = 159.62
Monoclinic, C 2/c
a = 16.372 (4) Å
b = 8.795 (2) Å
c = 12.007 (3) Å
= 108.133 (5)°
V = 1642.9 (8) Å³
Z = 8
Mo K radiation
= 0.40 mm^-1
T = 273 K
0.4 × 0.4 × 0.3 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.869, T_max = 0.982
5044 measured reflections
1620 independent reflections
1008 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.105
S = 0.90
1620 reflections
93 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C4/N2/N3 ring.

D-HA	D-H	HA	DA	D-HA
N1-H1AClⁱ	0.86	2.42	3.260 (2)	167
N1-H1BClⁱⁱ	0.86	2.57	3.262 (2)	138
N2-H2NCl	0.86	2.22	3.042 (2)	161
C5-H5ACg1ⁱⁱⁱ	0.96	3.00	3.446 (3)	110
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x, y, -z+{\script{3\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2128 ).

Acknowledgements

We are grateful to the National Science Council of the Republic of China and the Taoyuan Innovation Institute of Technology for support.

References

Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cheng, X.-L., Gao, S. & Ng, S. W. (2010). Acta Cryst. E66, o127.
Eshtiagh-Hosseini, H., Mahjoobizadeh, M. & Mirzaei, M. (2010). Acta Cryst. E66, o2210.
Hu, H.-L. & Yeh, C.-W. (2012). Acta Cryst. E68, o2925.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds