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Volume 69 
Part 8 
Page o1334  
August 2013  

Received 30 April 2013
Accepted 21 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 213 K
Mean [sigma](C-C) = 0.004 Å
R = 0.043
wR = 0.099
Data-to-parameter ratio = 8.0
Details
Open access

5-[1-(1,3-Dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl)-2-oxopropyl]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione

aDepartment of Chemistry, The University of Jordan, Amman 11942, Jordan, and bInstitut für Anorganische Chemie der Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany
Correspondence e-mail: k.sweidan@ju.edu.jo

The title compound, C15H18N4O7, is a product of the substitution reaction of 5,5-dibromo-1,3-dimethylbarbituric acid with sodium sulfide in aqueous acetone. In the crystal, molecules display neither intermolecular nor intramolecular hydrogen bonding and the two barbiturate rings adopt the keto form.

Related literature

For general applications of barbituric acid, see: Negwer (2001[Negwer, M. (2001). Organic-Chemical Drugs and their Synonyms, 7th rev. and Engl. ed., Vol. 4, pp. 2873-2957, Berlin: Akademie.]); Bojarski et al. (1985[Bojarski, J. T., Mokrocz, J. L., Barton, H. J. & Paluchowska, M. H. (1985). Adv. Heterocycl. Chem. 38, 229-297.]); Sans & Chosaz (1988[Sans, S. R. G. & Chosaz, M. G. (1988). Pharmazie, 43, 827-829.]). For the structures of related compounds, see: Sweidan et al. (2009[Sweidan, K., Abu-Salem, Q., Al-Sheikh, A. & Abu-Sheikha, G. (2009). Lett. Org. Chem. 6, 669-672.]); Ahadi et al. (2012[Ahadi, S., Abaszadeh, M., Khavasi, H. R. & Bazgir, A. (2012). Tetrahedron, 68, 2906-2916.]). For the synthesis of the starting material, see: Sweidan et al. (2010[Sweidan, K., Abu-Salem, Q., Al-Sheikh, A. & Abu-Sheikha, G. (2010). J. Struct. Chem. 51, 793-797.]).

[Scheme 1]

Experimental

Crystal data
  • C15H18N4O7

  • Mr = 366.33

  • Orthorhombic, P 21 21 21

  • a = 9.253 (2) Å

  • b = 13.179 (3) Å

  • c = 13.360 (3) Å

  • V = 1629.2 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 213 K

  • 0.50 × 0.35 × 0.25 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 1911 measured reflections

  • 1911 independent reflections

  • 1265 reflections with I > 2[sigma](I)

  • 3 standard reflections every 200 reflections intensity decay: 1.0%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.099

  • S = 1.07

  • 1911 reflections

  • 240 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Data collection: CAD-4 Software (Enraf-Nonius, 1998[Enraf-Nonius (1998). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: SET4 and CEKDIM in CAD-4 Software; data reduction: HELENA/PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2109 ).


Acknowledgements

KS gratefully acknowledges financial support from the Deanship of Scientific Research at the University of Jordan.

References

Ahadi, S., Abaszadeh, M., Khavasi, H. R. & Bazgir, A. (2012). Tetrahedron, 68, 2906-2916.  [CrossRef] [ChemPort]
Bojarski, J. T., Mokrocz, J. L., Barton, H. J. & Paluchowska, M. H. (1985). Adv. Heterocycl. Chem. 38, 229-297.  [CrossRef] [ChemPort]
Enraf-Nonius (1998). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Negwer, M. (2001). Organic-Chemical Drugs and their Synonyms, 7th rev. and Engl. ed., Vol. 4, pp. 2873-2957, Berlin: Akademie.
Sans, S. R. G. & Chosaz, M. G. (1988). Pharmazie, 43, 827-829.  [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sweidan, K., Abu-Salem, Q., Al-Sheikh, A. & Abu-Sheikha, G. (2009). Lett. Org. Chem. 6, 669-672.  [CrossRef] [ChemPort]
Sweidan, K., Abu-Salem, Q., Al-Sheikh, A. & Abu-Sheikha, G. (2010). J. Struct. Chem. 51, 793-797.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1334  [ doi:10.1107/S1600536813020138 ]

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