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

Babykala, R.; Kalaivani, D.

doi:10.1107/S1600536813004352

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 (C-C) = 0.004 Å
R = 0.042
wR = 0.117
Data-to-parameter ratio = 12.3
Details

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

R. Babykala ^a and D. Kalaivani ^a ^*

^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-HO 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); Mulliken (1952); Russell & Janzen (1962); Blake et al. (1966). For donor-acceptor interactions see: Mulliken (1952); Radha et al. (1987). For [pi] - [pi] stacking interactions, see: Vembu & Fronczek (2009). For the biological activity of pyrimidine and barbiturate derivatives, see: Jain et al. (2006); Tripathi (2009) and of related barbiturates, see: Kalaivani & Buvaneswari (2010). For the crystal structures of related barbiturates, see: Kalaivani & Malarvizhi (2009); Buvaneswari & Kalaivani (2011); Kalaivani & Mangaiyarkarasi (2013). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₀H₁₆N⁺·C₁₀H₄ClN₄O₇^-
M_r = 477.86
Triclinic, $[P \overline 1]$
a = 9.8040 (2) Å
b = 10.2870 (2) Å
c = 11.8260 (2) Å
= 74.727 (1)°
= 82.761 (1)°
= 71.817 (1)°
V = 1091.87 (4) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.913, T_max = 0.985
18678 measured reflections
3836 independent reflections
3123 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(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
_max = 0.40 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4AO5ⁱ	0.83 (2)	2.06 (2)	2.892 (2)	175 (2)
N3-H3AO7ⁱⁱ	0.83 (2)	1.96 (2)	2.794 (2)	180 (3)
N5-H5AO6ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (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: LH5583 ).

Acknowledgements

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

References

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organic compounds