2-Amino­pyrimidin-1-ium 4-methyl­benzene­sulfonate

Masoumeh Tabatabaee; Najmeh Noozari

doi:10.1107/S1600536811018198

. 2011 May 20;67(Pt 6):o1457. doi: 10.1107/S1600536811018198

2-Aminopyrimidin-1-ium 4-methylbenzenesulfonate

Masoumeh Tabatabaee ^a,^*, Najmeh Noozari ^a

PMCID: PMC3120468 PMID: 21754830

Abstract

In the crystal structure of the title compound, C₄H₆N₃ ⁺·C₇H₇O₃S⁻, intermolecular N—H⋯O hydrogen bonds link the cations and anions into chains along [100]. Additional stabilization is provided by weak C—H⋯O hydrogen bonds. An intermolecular π–π stacking interaction with a centroid–centroid distance of 3.6957 (7) Å is also observed. The H atoms of the methyl group were refined as disordered over two sets of sites with equal occupancies

Related literature

For related structures, see: Tabatabaee et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₄H₆N₃ ⁺·C₇H₇O₃S⁻
M _r = 267.30
Monoclinic,
a = 6.2567 (3) Å
b = 13.3756 (6) Å
c = 15.2512 (7) Å
β = 101.335 (1)°
V = 1251.43 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.50 × 0.36 × 0.32 mm

Data collection

Bruker SMART APEXII diffractometer
12275 measured reflections
3617 independent reflections
3160 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.088
S = 1.04
3617 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018198/lh5246sup1.cif

e-67-o1457-sup1.cif^{(17.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018198/lh5246Isup2.hkl

e-67-o1457-Isup2.hkl^{(177.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018198/lh5246Isup3.cml

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⋯O1	0.88	1.79	2.674 (1)	176
N3—H3B⋯O1ⁱ	0.88	2.03	2.835 (1)	151
N3—H3C⋯O2	0.88	2.08	2.902 (1)	155
C10—H10A⋯O3ⁱⁱ	0.95	2.46	3.1035 (14)	124
C11—H11A⋯O3ⁱⁱⁱ	0.95	2.56	3.3629 (14)	143

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

Acknowledgments

This research was supported by the Islamic Azad University, Yazd Branch.

supplementary crystallographic information

Comment

The treatment of sulfonylchloride compounds with amines at room temperature leads to the corresponding sulfonamides (Tabatabaee et al., 2010, 2011). The title compound was obtained as a side product from the reaction of 4-methylbenzenesulfonyl chloride and 2-amino-pyrimidine in CH₂Cl₂ under reflux conditions. The compound was formed due to the hydrolysis of 4-methylbenzenesulfonyl chloride to 4-methylbenzenesulfonic acid and an H atom being transferred to an imine nitrogen atom of 2-amino-pyrimidine molecule. The molecular structure of the title compound is shown in Fig. 1. The H atoms of the methyl group are disordered over two sets of sites with equal occupancies. In the crystal, cations and anions are linked into one dimensional chains parallel to [100] (Fig. 2) by intermolecular N—H··· O hydrogen bonds and further stabilization is provided by weak C—H··· O hydrogen bonds. There is an intermolecular π···π stacking interaction involving pyrimidine and benzene rings with a centroid to centroid distance of 3.6957 (7)Å.

Experimental

A solution of 2-amino-pyrimidine (0.095 g, 1 mmol) in CH₂Cl₂ (30 ml) was treated with 4-methylbenzenesulfonyl chloride (0.190 g, 1 mmol) and the pH of reaction mixture was adjusted to 8 with sodium carbonate solution (10%). The reaction mixture was refluxed. the solid crude was filtered. The clear filtrate solution was kept at 277K to give the colorless single crystals of the title compound.