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

Kalaivani, D.; Buvaneswari, M.; Rajeswari, S.

doi:10.1107/S1600536811051610

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 (C-C) = 0.003 Å
R = 0.046
wR = 0.123
Data-to-parameter ratio = 12.3
Details

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

D. Kalaivani,^a ^* M. Buvaneswari ^a and S. Rajeswari ^b

^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-HO hydrogen bonds involving the barbiturate rings. Attached to both sides of these ribbons via N-HO hydrogen bonds are the trimethylammonium cations. C-HO hydrogen bonds are also observed.

Related literature

For the biological activity of barbiturates, see: Nogrady (1988); Gitto et al. (2006). For side effects of barbiturates, see: Hardman & Limbird (2001); Rana et al. (2007). For barbiturates related to the title compound, see: Kalaivani et al. (2008); Kalaivani & Malarvizhi (2009).

Experimental

Crystal data

C₃H₁₀N⁺·C₁₀H₄N₅O₉^-
M_r = 398.30
Monoclinic, P 2₁ /c
a = 11.9828 (12) Å
b = 30.802 (3) Å
c = 9.5516 (11) Å
= 105.895 (6)°
V = 3390.6 (6) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.90, T_max = 0.97
31796 measured reflections
6580 independent reflections
4977 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(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
_max = 0.34 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4O17ⁱ	0.85 (2)	1.94 (2)	2.780 (2)	170 (2)
N5-H5O16	0.86 (3)	1.93 (3)	2.778 (2)	170 (2)
N9-H9O8	0.85 (2)	1.95 (2)	2.790 (2)	172 (2)
N10-H10O7ⁱⁱ	0.83 (2)	1.96 (2)	2.786 (2)	173 (2)
N11-H11AO9ⁱⁱⁱ	0.94 (3)	1.82 (3)	2.730 (2)	160 (3)
N12-H12AO18	0.94 (3)	2.02 (3)	2.803 (3)	139 (3)
N12-H12AO5^iv	0.94 (3)	2.16 (3)	2.856 (3)	130 (2)
C2-H2O4^v	0.93	2.58	3.265 (3)	131
C16-H16O2^vi	0.93	2.27	3.146 (3)	156
C24-H24BO5	0.96	2.51	3.448 (4)	164
C24-H24CO10ⁱⁱⁱ	0.96	2.57	3.457 (4)	154
C26-H26BO18^iv	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); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; 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, 1997) 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: QK2022 ).

Acknowledgements

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

References

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organic compounds