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Volume 69 
Part 1 
Pages o3-o4  
January 2013  

Received 25 November 2012
Accepted 27 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.042
wR = 0.122
Data-to-parameter ratio = 12.4
Details
Open access

N,N-Diethylanilinium 5-(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

The asymmetric unit of the title molecular salt, C10H16N+·C10H5N4O7- (trivial name: N,N-diethylanilinium 2,4-dinitrophenylbarbiturate), comprises two anion-cation units. In the anions, the dinitrophenyl ring and the mean plane of the barbiturate ring [planar to within 0.011 (2) and 0.023 (2) Å in the two anions] are inclined to one another by 41.47 (9) and 45.12 (9)°. In the crystal, the anions are linked via strong N-H...O hydrogen bonds, forming chains propagating along [10-1]. Within the chains, adjacent inversion-related anionic barbiturate entities are joined through R22(8) ring motifs. The cations are linked to the chains via N-H...O hydrogen bonds. The chains are linked via a number of C-H...O interactions, forming a three-dimensional structure.

Related literature

For the crystal structures of related barbiturates, see: Kalaivani & Malarvizhi (2009[Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548.]); Buvaneswari & Kalaivani (2011a[Buvaneswari, M. & Kalaivani, D. (2011a). Acta Cryst. E67, o1433-o1434.],b[Buvaneswari, M. & Kalaivani, D. (2011b). Acta Cryst. E67, o3452.]); Kalaivani et al. (2012[Kalaivani, D., Buvaneswari, M. & Rajeswari, S. (2012). Acta Cryst. E68, o29-o30.]); Babykala & Kalaivani (2012[Babykala, R. & Kalaivani, D. (2012). Acta Cryst. E68, o541.]). For the biological activity of barbiturates, see: Hueso et al. (2003[Hueso, F., Illan, N. A., Mareno, M. N., Martinex, J. & Ramirez, M. J. (2003). J. Inorg. Biochem. 94,326-334.]); Kalaivani et al. (2008[Kalaivani, D., Malarvizhi, R. & Subbalakshmi, R. (2008). Med. Chem. Res. 17, 369-373.]); Tripathi (2009[Tripathi, K. D. (2009). In Essentials of Medical Pharmacology, 6th ed. Chennai: Jaypee Brothers.]); Kalaivani & Buvaneswari (2010[Kalaivani, D. & Buvaneswari, M. (2010). In Recent Advances in Clinical Medicine, pp. 225-260. UK: WSEAS Publications.]).

[Scheme 1]

Experimental

Crystal data
  • C10H16N+·C10H5N4O7-

  • Mr = 443.42

  • Triclinic, [P \overline 1]

  • a = 8.7260 (2) Å

  • b = 14.2930 (3) Å

  • c = 18.1080 (5) Å

  • [alpha] = 106.712 (1)°

  • [beta] = 96.490 (1)°

  • [gamma] = 97.667 (1)°

  • V = 2116.27 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.944, Tmax = 0.996

  • 36083 measured reflections

  • 7482 independent reflections

  • 5563 reflections with I > 2[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.122

  • S = 1.02

  • 7482 reflections

  • 601 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.39 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
N3-H3A...O7i 0.89 (2) 2.00 (2) 2.878 (2) 172 (2)
N4-H4A...O14ii 0.87 (2) 1.93 (2) 2.802 (2) 172 (2)
N7-H7A...O13iii 0.88 (2) 2.06 (2) 2.931 (2) 175 (2)
N8-H8A...O6iv 0.89 (2) 1.98 (2) 2.852 (2) 164 (2)
N9-H9A...O12 0.90 (2) 1.83 (2) 2.726 (2) 176 (1)
N10-H10A...O5v 0.92 (2) 1.69 (2) 2.598 (3) 166 (2)
C12-H12...O4vi 0.93 2.52 3.451 (3) 174
C26-H26...O12 0.93 2.59 3.272 (3) 131
C26-H26...O13iii 0.93 2.56 3.281 (3) 135
C29-H29B...O11 0.97 2.57 3.215 (3) 124
C38-H38A...O7i 0.96 2.52 3.484 (3) 177
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) x-1, y, z; (v) -x+1, -y+1, -z+1; (vi) x, y-1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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, 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: SU2535 ).


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]
Babykala, R. & Kalaivani, D. (2012). Acta Cryst. E68, o541.  [CSD] [CrossRef] [details]
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Buvaneswari, M. & Kalaivani, D. (2011a). Acta Cryst. E67, o1433-o1434.  [CSD] [CrossRef] [details]
Buvaneswari, M. & Kalaivani, D. (2011b). Acta Cryst. E67, o3452.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hueso, F., Illan, N. A., Mareno, M. N., Martinex, J. & Ramirez, M. J. (2003). J. Inorg. Biochem. 94,326-334.  [ISI] [PubMed]
Kalaivani, D. & Buvaneswari, M. (2010). In 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., 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]
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.


Acta Cryst (2013). E69, o3-o4   [ doi:10.1107/S160053681204874X ]

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