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Volume 69 
Part 4 
Pages o592-o593  
April 2013  

Received 6 March 2013
Accepted 21 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
H completeness 99%
Disorder in solvent or counterion
R = 0.045
wR = 0.130
Data-to-parameter ratio = 10.7
Details
Open access

Trimethylammonium 5-(2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate 0.125-hydrate

aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
Correspondence e-mail: kalaivbalaj@yahoo.co.in

The asymmetric unit of the title salt C3H10N+·C10H5N4O7-·0.125H2O [trivial name: trimethylammonium 5-(2,4-dinitrophenyl)barbiturate 0.125-hydrate], contains two independent cations, two independent anions and a 0.25-occupancy solvent water molecule. In one of the cations, the C atoms are disordered over two sets of sites with refined occupancies of 0.538 (8) and 0.462 (8). In the anions, the dihedral angles between the pyrimidine and benzene rings are 42.77 (6) and 46.55 (7)°. In the crystal, N-H...O hydrogen bonds connect anions and cations into chains along [010]. Within these chains, R22(8) ring motifs are formed by inversion-related barbiturate anions. The H atoms of the partial occupancy water molecule were not located nor included in the refinement.

Related literature

For the different types of anionic sigma complexes, see: Terrier (1982[Terrier, F. (1982). Chem. Rev. 82, 77-152.]); Al-Kaysi et al. (2005[Al-Kaysi, R. O., Mueller, A. M., Ahn, T. S., Lee, S. & Bardeen, C. J. (2005). Langmuir, 21, 7990-7994.]). For the utility of spiro Meisenheimer complexes, see: Gallardo et al. (2007[Gallardo, I. & Guirado, G. (2007). Electrochem. Commun. 9, 173-179.]); Al-Kaysi et al. 2008[Al-Kaysi, R. O., Gallardo, I. & Guirado, G. (2008). Molecules, 13, 1282-1302.]). For the biological activity of carbanionic sigma complexes related to the title compound, see: Kalaivani et al. (2008[Kalaivani, D., Malarvizhi, R. & Subbalakshmi, R. (2008). Med. Chem. Res. 17, 369-373.]); Kalaivani & Buvaneswari (2010[Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 225-260. UK: WSEAS Publications.]). For the crystal structures of related barbiturates, see: Kalaivani & Malarvizhi (2009[Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548.]); Kalaivani et al. (2012[Kalaivani, D., Buvaneswari, M. & Rajeswari, S. (2012). Acta Cryst. E68, o29-o30.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C3H10N+·C10H5N4O7-·0.125H2O

  • Mr = 355.29

  • Monoclinic, P 21 /c

  • a = 15.0410 (5) Å

  • b = 10.5460 (3) Å

  • c = 20.4170 (8) Å

  • [beta] = 94.953 (1)°

  • V = 3226.50 (19) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.987

  • 26803 measured reflections

  • 5517 independent reflections

  • 3780 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.130

  • S = 1.02

  • 5517 reflections

  • 516 parameters

  • 36 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O9i 0.80 (2) 2.09 (2) 2.888 (2) 175 (2)
N2-H2A...O8ii 0.89 (3) 2.02 (3) 2.905 (2) 173 (2)
N5-H5A...O3i 0.84 (2) 2.10 (2) 2.931 (2) 169 (2)
N6-H6A...O1ii 0.85 (2) 2.04 (3) 2.889 (2) 177 (2)
N9-H9A...O10 1.04 (3) 1.62 (4) 2.650 (2) 167 (3)
N10-H10...O2 1.02 (4) 1.63 (4) 2.644 (3) 173 (3)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006)[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]; software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5595 ).


Acknowledgements

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

References

Al-Kaysi, R. O., Gallardo, I. & Guirado, G. (2008). Molecules, 13, 1282-1302.  [PubMed] [ChemPort]
Al-Kaysi, R. O., Mueller, A. M., Ahn, T. S., Lee, S. & Bardeen, C. J. (2005). Langmuir, 21, 7990-7994.  [PubMed] [ChemPort]
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gallardo, I. & Guirado, G. (2007). Electrochem. Commun. 9, 173-179.  [CrossRef] [ChemPort]
Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 225-260. UK: WSEAS Publications.
Kalaivani, D., Buvaneswari, M. & Rajeswari, S. (2012). Acta Cryst. E68, o29-o30.  [CSD] [CrossRef] [ChemPort] [details]
Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548.  [CSD] [CrossRef] [details]
Kalaivani, D., Malarvizhi, R. & Subbalakshmi, R. (2008). Med. Chem. Res. 17, 369-373.  [ISI] [CrossRef] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Terrier, F. (1982). Chem. Rev. 82, 77-152.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o592-o593   [ doi:10.1107/S1600536813007915 ]

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