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Volume 69 
Part 3 
Pages o398-o399  
March 2013  

Received 31 January 2013
Accepted 13 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.042
wR = 0.117
Data-to-parameter ratio = 12.3
Details
Open access

N,N-Diethylanilinium 5-(5-chloro-2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate

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

In the anion of the title salt, C10H16N+·C10H4ClN4O7- [trivial name = N,N-diethylanilinium 5-(3-chloro-4,6,-dinitrophenyl)barbiturate], the dihedral angle between the benzene and pyrimidine rings is 45.49 (6)°. The mean plane of the nitro group, which is ortho-substituted with respect to the pyrimidine ring, is twisted by 41.57 (13)° from the benzene ring, while the mean plane of the nitro group, which is para-substituted, is twisted by 14.41 (12)° from this ring. In the crystal, N-H...O hydrogen bonds link cations and anions into chains along [1-10]. Within the chains, inversion-related anionic barbiturate anions form R22(8) ring motifs.

Related literature

For different types of interactions between electron-deficient nitro aromatics and bases, see: Jackson & Gazzolo (1900[Jackson, C. J. & Gazzolo, F. H. (1900). Am. Chem. J. 23, 376-396.]); Mulliken (1952[Mulliken, R. S. (1952). J. Am. Chem. Soc. 74, 811-824.]); Russell & Janzen (1962[Russell, G. A. & Janzen, E. G. (1962). J. Am. Chem. Soc. 4, 4153-4154.]); Blake et al. (1966[Blake, J. A., Evans, M. J. B. & Russell, K. E. (1966). Can. J. Chem. 44, 119-124.]). For donor-acceptor interactions see: Mulliken (1952[Mulliken, R. S. (1952). J. Am. Chem. Soc. 74, 811-824.]); Radha et al. (1987[Radha, N., Dhoulethbegum, S. & Sahayamary, J. (1987). Indian J. Chem. Sect. A, 26, 1006-1008.]). For [pi]-[pi] stacking interactions, see: Vembu & Fronczek (2009[Vembu, N. & Fronczek, F. R. (2009). Acta Cryst. E65, o111-o112.]). For the biological activity of pyrimidine and barbiturate derivatives, see: Jain et al. (2006[Jain, S., Chitre, T. S., Miniyar, P. B., Kathiravan, M. K., Bendre, V. S., Veer, S., Shahane, S. R. & Shishoo, C. J. (2006). Curr. Sci. 90, 793-803.]); Tripathi (2009[Tripathi, K. D. (2009). In Essentials of Medical Pharmacology, 6th ed. Chennai: Jaypee Brothers.]) and of related barbiturates, see: Kalaivani & Buvaneswari (2010[Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 255-260. UK: WSEAS Publications.]). For the crystal structures of related barbiturates, see: Kalaivani & Malarvizhi (2009[Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548.]); Buvaneswari & Kalaivani (2011[Buvaneswari, M. & Kalaivani, D. (2011). Acta Cryst. E67, o3452.]); Kalaivani & Mangaiyarkarasi (2013[Kalaivani, D. & Mangaiyarkarasi, G. (2013). Acta Cryst. E69, o3-o4.]). 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
  • C10H16N+·C10H4ClN4O7-

  • Mr = 477.86

  • Triclinic, [P \overline 1]

  • a = 9.8040 (2) Å

  • b = 10.2870 (2) Å

  • c = 11.8260 (2) Å

  • [alpha] = 74.727 (1)°

  • [beta] = 82.761 (1)°

  • [gamma] = 71.817 (1)°

  • V = 1091.87 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 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 = 0.913, Tmax = 0.985

  • 18678 measured reflections

  • 3836 independent reflections

  • 3123 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.04

  • 3836 reflections

  • 312 parameters

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

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4A...O5i 0.83 (2) 2.06 (2) 2.892 (2) 175 (2)
N3-H3A...O7ii 0.83 (2) 1.96 (2) 2.794 (2) 180 (3)
N5-H5A...O6iii 0.87 (3) 1.82 (3) 2.677 (2) 168 (3)
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z.

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., 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: LH5583 ).


Acknowledgements

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

References

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]
Blake, J. A., Evans, M. J. B. & Russell, K. E. (1966). Can. J. Chem. 44, 119-124.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Buvaneswari, M. & Kalaivani, D. (2011). Acta Cryst. E67, o3452.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jackson, C. J. & Gazzolo, F. H. (1900). Am. Chem. J. 23, 376-396.  [ChemPort]
Jain, S., Chitre, T. S., Miniyar, P. B., Kathiravan, M. K., Bendre, V. S., Veer, S., Shahane, S. R. & Shishoo, C. J. (2006). Curr. Sci. 90, 793-803.  [ChemPort]
Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 255-260. UK: WSEAS Publications.
Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548.  [CSD] [CrossRef] [details]
Kalaivani, D. & Mangaiyarkarasi, G. (2013). Acta Cryst. E69, o3-o4.  [CSD] [CrossRef] [details]
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]
Mulliken, R. S. (1952). J. Am. Chem. Soc. 74, 811-824.  [CrossRef] [ChemPort] [ISI]
Radha, N., Dhoulethbegum, S. & Sahayamary, J. (1987). Indian J. Chem. Sect. A, 26, 1006-1008.
Russell, G. A. & Janzen, E. G. (1962). J. Am. Chem. Soc. 4, 4153-4154.  [CrossRef] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tripathi, K. D. (2009). In Essentials of Medical Pharmacology, 6th ed. Chennai: Jaypee Brothers.
Vembu, N. & Fronczek, F. R. (2009). Acta Cryst. E65, o111-o112.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o398-o399   [ doi:10.1107/S1600536813004352 ]

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