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Volume 65 
Part 8 
Pages o1860-o1861  
August 2009  

Received 4 July 2009
Accepted 6 July 2009
Online 15 July 2009


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Key indicators
Single-crystal X-ray study
T = 140 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.068
wR = 0.212
Data-to-parameter ratio = 17.6
Details

Pyridinium 5-[(1,3-diethyl-6-hydroxy-4-oxo-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)(2-methoxyphenyl)methyl]-1,3-diethyl-4,6-dioxo-2-thioxopyrimidin-5-ide

Abdullah Mohamed Asiri,a Salman A. Khana and Seik Weng Ngb*

aChemistry Department, Faculty of Science, King Abdul Aziz University, Jeddah, Saudi Arabia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

1,3-Diethyl-2-thiobarbituric acid reacts with 2-anisaldehyde to form the Michael addition product 2-anisylbis(1,3-diethyl-2-thiobarbitur-5-yl)methanate, which crystallizes as the title pyridinium salt, C5H6N+·C24H29N4O5S2-, when it reacts with the pyridine used to catalyse the reaction. There are two independent ion pairs in the crystal structure. The anion features a methine C atom connected to three six-membered rings; one of the rings carries a hydroxy group, which engages in hydrogen bonding with the carbonyl group belonging to another ring. The monoclinic unit cell emulates an orthorhombic unit cell, and is a twin with a minor twin component of 35%.

Related literature

For the reaction of 1,3-diethyl-2-thiobarbituric acid with aromatic aldehydes to form the Knoevenagel and Michael products, see: Adamson et al. (1999[Adamson, J., Coe, B. J., Grassam, H. L., Jeffery, J. C., Coles, S. J. & Hursthouse, M. B. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 2483-2488.]).

[Scheme 1]

Experimental

Crystal data

  • C5H6N+·C24H29N4O5S2-

  • Mr = 597.74

  • Monoclinic, P 21 /n

  • a = 17.3713 (3) Å

  • b = 19.8285 (3) Å

  • c = 17.3969 (2) Å

  • [beta] = 90.316 (1)°

  • V = 5992.22 (15) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 140 K

  • 0.35 × 0.25 × 0.15 mm
Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.926, Tmax = 0.967

  • 40346 measured reflections

  • 13375 independent reflections

  • 11615 reflections with I > 2[sigma](I)

  • Rint = 0.047
Refinement

  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.212

  • S = 1.02

  • 13375 reflections

  • 762 parameters

  • 20 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.96 e Å-3

  • [Delta][rho]min = -0.65 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O1 0.84 1.63 2.435 (4) 159
O6-H6...O8 0.84 1.67 2.444 (4) 152
N11-H11...O2 0.88 1.93 2.721 (4) 148
N12-H12...O9 0.88 1.89 2.745 (6) 162

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2549 ).

Acknowledgements

We thank King Abdul Aziz University and the University of Malaya for supporting this study.

References

Adamson, J., Coe, B. J., Grassam, H. L., Jeffery, J. C., Coles, S. J. & Hursthouse, M. B. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 2483-2488.  [CrossRef]
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2009). publCIF. In preparation.

Acta Cryst (2009). E65, o1860-o1861   [ doi:10.1107/S160053680902618X ]

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