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

Kalaivani, D.; Mangaiyarkarasi, G.

doi:10.1107/S160053681204874X

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 (C-C) = 0.004 Å
R = 0.042
wR = 0.122
Data-to-parameter ratio = 12.4
Details

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

Doraisamyraja Kalaivani ^a ^* and Govindan Mangaiyarkarasi ^a

^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-HO 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-HO hydrogen bonds. The chains are linked via a number of C-HO interactions, forming a three-dimensional structure.

Related literature

For the crystal structures of related barbiturates, see: Kalaivani & Malarvizhi (2009); Buvaneswari & Kalaivani (2011a,b); Kalaivani et al. (2012); Babykala & Kalaivani (2012). For the biological activity of barbiturates, see: Hueso et al. (2003); Kalaivani et al. (2008); Tripathi (2009); Kalaivani & Buvaneswari (2010).

Experimental

Crystal data

C₁₀H₁₆N⁺·C₁₀H₅N₄O₇^-
M_r = 443.42
Triclinic, $[P \overline 1]$
a = 8.7260 (2) Å
b = 14.2930 (3) Å
c = 18.1080 (5) Å
= 106.712 (1)°
= 96.490 (1)°
= 97.667 (1)°
V = 2116.27 (9) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.944, T_max = 0.996
36083 measured reflections
7482 independent reflections
5563 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(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
_max = 0.39 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO7ⁱ	0.89 (2)	2.00 (2)	2.878 (2)	172 (2)
N4-H4AO14ⁱⁱ	0.87 (2)	1.93 (2)	2.802 (2)	172 (2)
N7-H7AO13ⁱⁱⁱ	0.88 (2)	2.06 (2)	2.931 (2)	175 (2)
N8-H8AO6^iv	0.89 (2)	1.98 (2)	2.852 (2)	164 (2)
N9-H9AO12	0.90 (2)	1.83 (2)	2.726 (2)	176 (1)
N10-H10AO5^v	0.92 (2)	1.69 (2)	2.598 (3)	166 (2)
C12-H12O4^vi	0.93	2.52	3.451 (3)	174
C26-H26O12	0.93	2.59	3.272 (3)	131
C26-H26O13ⁱⁱⁱ	0.93	2.56	3.281 (3)	135
C29-H29BO11	0.97	2.57	3.215 (3)	124
C38-H38AO7ⁱ	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); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); 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

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Babykala, R. & Kalaivani, D. (2012). Acta Cryst. E68, o541.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Buvaneswari, M. & Kalaivani, D. (2011a). Acta Cryst. E67, o1433-o1434.
Buvaneswari, M. & Kalaivani, D. (2011b). Acta Cryst. E67, o3452.
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Kalaivani, D. & Buvaneswari, M. (2010). In Recent Advances in Clinical Medicine, pp. 225-260. UK: WSEAS Publications.
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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.
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organic compounds