2-Amino-4,6-dimethyl­pyrimidinium chloro­acetate

Cui-Hua Lin; Nai-Sheng Liu; Fang-Fang Jian

doi:10.1107/S1600536809044444

. 2009 Oct 31;65(Pt 11):o2913. doi: 10.1107/S1600536809044444

2-Amino-4,6-dimethylpyrimidinium chloroacetate

Cui-Hua Lin ^a, Nai-Sheng Liu ^b, Fang-Fang Jian ^c,^*

PMCID: PMC2971421 PMID: 21578492

Abstract

There are two cations and two anions in the asymmetric unit of the title compound, C₆H₁₀N₃ ⁺·C₂H₂ClO₂ ⁻. In the crystal, the components are linked by intermolecular N—H⋯O and N—H⋯N hydrogen bonds to form a two-dimensional network. Additional stabilization is provided by weak intermolecular C—H⋯O interactions.

Related literature

For background to pyrimidine derivatives, see: Xue et al. (1993 ▶); Hemamalini et al. (2005 ▶).

Experimental

Crystal data

C₆H₁₀N₃ ⁺·C₂H₂ClO₂ ⁻
M _r = 217.66
Triclinic,
a = 4.4560 (9) Å
b = 12.302 (3) Å
c = 19.441 (4) Å
α = 92.90 (3)°
β = 96.53 (3)°
γ = 91.15 (3)°
V = 1057.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 293 K
0.20 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
10303 measured reflections
4761 independent reflections
3452 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.195
S = 1.08
4761 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809044444/hb5174sup1.cif

e-65-o2913-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044444/hb5174Isup2.hkl

e-65-o2913-Isup2.hkl^{(233.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N3ⁱ	0.86	2.14	2.999 (3)	177
N1—H1B⋯O3ⁱⁱ	0.86	1.98	2.830 (3)	173
N2—H2A⋯O4ⁱⁱ	0.86	1.74	2.593 (3)	175
N4—H4A⋯N6ⁱⁱⁱ	0.86	2.19	3.046 (3)	175
N4—H4B⋯O1^iv	0.86	2.00	2.851 (3)	173
N5—H5A⋯O2^iv	0.86	1.75	2.606 (3)	174
C1—H1C⋯O4ⁱⁱ	0.96	2.56	3.355 (4)	140
C7—H7A⋯O2^iv	0.96	2.57	3.355 (4)	139

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

supplementary crystallographic information

Comment

As useful precursors to potentially bioactive pyrimidine derivatives, methylpyrimidine has attracted considerable attention for many years (Xue et al., 1993). In recent years, new complexes of pyrimidine have been synthesized (Hemamalini et al., 2005). The title compound(I), was synthesized and we report herein its crystal structure (Fig. 1).

There are two 2-amino-4,6-dimethylpyrimidine cations and two chloracetate anions in the asymmetric unit. In the crystal structure, cations and anions are linked by intermolecular N—H···O and N—H···N hydrogen bonds to form a two-dimensional network. Additional stabilization is provided by weak intermolecular C—H···O interactions.

Experimental

A mixture of guanidine hydrochloride (0.1 mol), acetyl acetone (0.2 mol), sodium carbonate (0.03 mol) and 2-chloroacetic acid (0.1 mol) was stirred with water (30 ml) for 3 h to afford the title compound (yield 67%). Colourless blocks of (I) were obtained by recrystallization of the title compound from water at room temperature.