2-Methyl­pyridinium 5-(2,4-dinitro­phen­yl)-1,3-dimethyl­barbiturate

Gunaseelan Sridevi; Doraisamyraja Kalaivani

doi:10.1107/S1600536812009440

. 2012 Mar 14;68(Pt 4):o1044. doi: 10.1107/S1600536812009440

2-Methylpyridinium 5-(2,4-dinitrophenyl)-1,3-dimethylbarbiturate

Gunaseelan Sridevi ^a, Doraisamyraja Kalaivani ^a,^*

PMCID: PMC3344005 PMID: 22589914

Abstract

In the title molecular salt [systematic name: 2-methylpyridinium 5-(2,4-dinitrophenyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate], C₆H₈N⁺·C₁₂H₉N₄O₇ ⁻, the cation and anion are linked a through strong N—H⋯O hydrogen bond. In the crystal, C—H⋯O interactions link the ions, generating a chain along [010].

Related literature

For the biological properties of molecules containing pyridine and pyrimidine units, see: Terekhova & Scriba (2007 ▶); Comins et al. (2008 ▶); Hueso et al. (2003 ▶); Jain et al. (2006 ▶). For the structures of barbiturates similar to the title compound, see: Kalaivani & Malarvizhi (2009 ▶); Kalaivani & Buvaneswari (2010 ▶); Buvaneswari & Kalaivani (2011 ▶).

Experimental

Crystal data

C₆H₈N⁺·C₁₂H₉N₄O₇ ⁻
M _r = 415.37
Monoclinic,
a = 12.8242 (8) Å
b = 7.0696 (5) Å
c = 21.5409 (14) Å
β = 101.029 (2)°
V = 1916.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T _min = 0.917, T _max = 0.983
3527 measured reflections
3527 independent reflections
2790 reflections with I > 2σ(I)

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.099
S = 1.04
3527 reflections
275 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009440/bv2197sup1.cif

e-68-o1044-sup1.cif^{(21.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009440/bv2197Isup2.hkl

e-68-o1044-Isup2.hkl^{(173.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009440/bv2197Isup3.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
N5—H5A⋯O3	0.86	1.82	2.6645 (16)	168
C13—H13B⋯O5ⁱ	0.96	2.42	3.340 (2)	161
C13—H13C⋯O1ⁱⁱ	0.96	2.42	3.160 (2)	134
C15—H15⋯O2ⁱⁱⁱ	0.93	2.29	3.021 (2)	135
C16—H16⋯O6^iv	0.93	2.58	3.323 (2)	138
C17—H17⋯O1^v	0.93	2.52	3.303 (2)	143

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

Acknowledgments

The authors are thankful to the SAIF, IIT Madras, for the data collection.

supplementary crystallographic information

Comment

Many molecules containing the pyridine moiety exhibit notable biological activity (Terekhova & Scriba, 2007; Comins et al., 2008). Molecules with pyrimidine ring residues are also biologically active (Hueso et al., 2003; Jain et al., 2006). The title molecular salt comprises of both pyrimidine (barbiturate moiety) and pyridine (2-methyl pyridinium) moieties and hence expected to have significant biological activity. Good crystallinity of the title compound prompted us to undertake single-crystal X-ray studies. The bond lengths and bond angles of the barbiturate residue of the molecular salt reported in the present article are compatible with those of related barbiturates synthesized in our laboratory earlier (Kalaivani & Malarvizhi, 2009; Kalaivani & Buvaneswari, 2010; Buvaneswari & Kalaivani, 2011). The structure of the molecular salt of the present work is shown in scheme 1. The ORTEP view showing 30% probability displacement ellipsoids is indicated in Fig.1. In the title molecule, the one dimensional zigzag chains which run along [010] direction are linked through C13—H13···O1, C17—H17···O1, C16—H16···O6, C13—H13···O3 and C15—H15···O2 weak interactions thus generating a three dimensional network and hence constituting the molecular packing of the crystal (Fig. 2). The 2,4-dinitrophenyl ring and 1,3-dimethylbarbiturate ring of the title molecule are not perfectly planar and the dihedral angle observed between them is 44.54 (2)degree.

Experimental

1-Chloro-2,4-dinitrobenzene(2.02 g,0.01 mol) was dissolved in 20 ml of ethanol. 1,3-Dimethylbarbituric acid (1.56 g,0.01 mol) was also dissolved in 15 ml of ethanol. These two solutions were mixed and to this mixture a five fold excess of 2-methylpyridine (4.65 g, 0.05 mol) was added and the resulting blood red coloured solution was shaken well for about three hours and kept as such at 25 /%C. Dark shiny maroon red coloured crystals were deposited from the solution after seventy two hours. The crystals were filtered and washed with 30 ml of ether. The crystals were powdered well and washed with 40 ml of ether to remove the unreacted reactants and finally with 10 ml of ethanol. The pure powder was recrystallized from hot ethanol (Yield: 75%; m.p.; 451 K). The crystals for X-ray analysis were obtained by slow evaporation of ethanol at room temperature.