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Volume 68 
Part 1 
Pages o29-o30  
January 2012  

Received 15 August 2011
Accepted 30 November 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.123
Data-to-parameter ratio = 12.3
Details
Open access

Trimethylammonium 2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate

aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India, and bDepartment of Chemistry, Faculty of Engineering and Technology, SRM University, Kattankulathur 603 203, Tamil Nadu, India
Correspondence e-mail: kalaivbalaj@yahoo.co.in

In the title barbiturate salt (trivial name: trimethylammonium 2,4,6-trinitrophenylbarbiturate), C3H10N+·C10H4N5O9-, the asymmetric unit contains two sets of anion-cation moieties. The dihedral angle between the rings in the anions are 44.0 (3) and 45.7 (3)°. Adjacent anions are connected into ribbons along [100] through R22(8) ring motifs formed by N-H...O hydrogen bonds involving the barbiturate rings. Attached to both sides of these ribbons via N-H...O hydrogen bonds are the trimethylammonium cations. C-H...O hydrogen bonds are also observed.

Related literature

For the biological activity of barbiturates, see: Nogrady (1988[Nogrady, T. (1988). Medicinal Chemistry. New York: Oxford University Press Inc.]); Gitto et al. (2006[Gitto, R. S., Caruso, R., Pagano, B., De Luca, L., Citraro, R., Russo, E., De Sarro, G. & Chimirri, A. (2006). J. Med. Chem. 49, 5618-5622.]). For side effects of barbiturates, see: Hardman & Limbird (2001[Hardman, J. G. & Limbird, L. E. (2001). The Pharmacological Basis of Therapeutics, 10th ed., pp. 1143-1170. New York: McGraw-Hill.]); Rana et al. (2007[Rana, A., Siddiqui, N. & Khan, S. A. (2007). Indian J. Pharm. Sci. 69, 10-17.]). For barbiturates related to the title compound, see: Kalaivani et al. (2008[Kalaivani, D., Malarvizhi, R. & Subbalakshmi, R. (2008). Med. Chem. Res. 17, 369-373.]); Kalaivani & Malarvizhi (2009[Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548.]).

[Scheme 1]

Experimental

Crystal data
  • C3H10N+·C10H4N5O9-

  • Mr = 398.30

  • Monoclinic, P 21 /c

  • a = 11.9828 (12) Å

  • b = 30.802 (3) Å

  • c = 9.5516 (11) Å

  • [beta] = 105.895 (6)°

  • V = 3390.6 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 296 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEX II CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.90, Tmax = 0.97

  • 31796 measured reflections

  • 6580 independent reflections

  • 4977 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.123

  • S = 1.02

  • 6580 reflections

  • 536 parameters

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

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...O17i 0.85 (2) 1.94 (2) 2.780 (2) 170 (2)
N5-H5...O16 0.86 (3) 1.93 (3) 2.778 (2) 170 (2)
N9-H9...O8 0.85 (2) 1.95 (2) 2.790 (2) 172 (2)
N10-H10...O7ii 0.83 (2) 1.96 (2) 2.786 (2) 173 (2)
N11-H11A...O9iii 0.94 (3) 1.82 (3) 2.730 (2) 160 (3)
N12-H12A...O18 0.94 (3) 2.02 (3) 2.803 (3) 139 (3)
N12-H12A...O5iv 0.94 (3) 2.16 (3) 2.856 (3) 130 (2)
C2-H2...O4v 0.93 2.58 3.265 (3) 131
C16-H16...O2vi 0.93 2.27 3.146 (3) 156
C24-H24B...O5 0.96 2.51 3.448 (4) 164
C24-H24C...O10iii 0.96 2.57 3.457 (4) 154
C26-H26B...O18iv 0.96 2.50 3.400 (5) 156
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) -x+1, -y, -z+1; (v) -x, -y, -z+2; (vi) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2022 ).


Acknowledgements

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

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gitto, R. S., Caruso, R., Pagano, B., De Luca, L., Citraro, R., Russo, E., De Sarro, G. & Chimirri, A. (2006). J. Med. Chem. 49, 5618-5622.  [ISI] [CrossRef] [PubMed] [ChemPort]
Hardman, J. G. & Limbird, L. E. (2001). The Pharmacological Basis of Therapeutics, 10th ed., pp. 1143-1170. New York: McGraw-Hill.
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., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Nogrady, T. (1988). Medicinal Chemistry. New York: Oxford University Press Inc.
Rana, A., Siddiqui, N. & Khan, S. A. (2007). Indian J. Pharm. Sci. 69, 10-17.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o29-o30   [ doi:10.1107/S1600536811051610 ]

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