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

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o29-o30

doi:10.1107/S1600536811051610

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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

(Received 15 August 2011; accepted 30 November 2011; online 7 December 2011)

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—H⋯O hydrogen bonds involving the barbiturate rings. Attached to both sides of these ribbons via N—H⋯O hydrogen bonds are the trimethylammonium cations. C—H⋯O 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
β = 105.895 (6)°
V = 3390.6 (6) Å³
Z = 8
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(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
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O17ⁱ	0.85 (2)	1.94 (2)	2.780 (2)	170 (2)
N5—H5⋯O16	0.86 (3)	1.93 (3)	2.778 (2)	170 (2)
N9—H9⋯O8	0.85 (2)	1.95 (2)	2.790 (2)	172 (2)
N10—H10⋯O7ⁱⁱ	0.83 (2)	1.96 (2)	2.786 (2)	173 (2)
N11—H11A⋯O9ⁱⁱⁱ	0.94 (3)	1.82 (3)	2.730 (2)	160 (3)
N12—H12A⋯O18	0.94 (3)	2.02 (3)	2.803 (3)	139 (3)
N12—H12A⋯O5^iv	0.94 (3)	2.16 (3)	2.856 (3)	130 (2)
C2—H2⋯O4^v	0.93	2.58	3.265 (3)	131
C16—H16⋯O2^vi	0.93	2.27	3.146 (3)	156
C24—H24B⋯O5	0.96	2.51	3.448 (4)	164
C24—H24C⋯O10ⁱⁱⁱ	0.96	2.57	3.457 (4)	154
C26—H26B⋯O18^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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051610/qk2022sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051610/qk2022Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051610/qk2022Isup3.cml

checkCIF report

Comment top

Barbiturates are biologically active molecules (Nogrady, 1988; Gitto et al., 2006). Many reported barbiturates have noticeable side effects (Hardman & Limbird, 2001; Rana et al., 2007). The growing interest in preparing new barbiturates prompted the present work. A barbiturate previously synthesized in our laboratory from 1-chloro-2,4-dinitrobenzene, barbituric acid and triethylamine has only one anion-cation pair in the asymmetric unit (Kalaivani et al., 2008; Kalaivani & Malarvizhi, 2009). However, the asymmetric unit of the title barbiturate (Scheme), prepared from 1-chloro-2,4,6-trinitrobenzene, barbituric acid and trimethylamine, comprises two sets of anion-cation moieties (Fig. 1). Two sets of R₂²(8) hydrogen bond motifs are noticed between the adjacent anions. The hydrogen bonds N9—H9···O8 and N5—H5···O16 form the first set of R₂²(8) motif and the hydrogen bonds N10—H10···O7 and N4—H4···O17 form the second set of R₂²(8) motif. The aggregations of these motifs form an infinite one dimensional anionic ribbon extending along [100] direction. To either side of the anionic ribbon the trimethylammonium cations are hydrogen bonded through N11—H11A···O9 and N12—H12A···O18 hydrogen bonds in the terminal positions as depicted in Fig. 2. Furthermore a number of weak C—H···O interactions (cf. Table 1) contribute to the three-dimensional coherence of the crystal structure.

Related literature top

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 top

1-Chloro-2,4,6-trinitrobenzene (2.5 g, 0.01 mol) in 20 ml of absolute ethanol was mixed with barbituric acid (1.3 g, 0.01 mol) in 30 ml of absolute ethanol and heated to 40°C. Trimethylamine (3 ml ~0.05 mol) was then added and the mixture was shaken well for 2 hrs. Dark maroon red crystals obtained were filtered. The filtered crystals were powdered well and washed with 50 ml of dry ether and recrystallized from absolute ethanol (yield 80%; m.p. 245 °C). Good quality crystals, suitable for single-crystal X-ray studies were obtained by slow evaporation of the ethanolic solution of title compound at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (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, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP diagram of (I) showing 30% probability displacement ellipsoids and the atomic numbering scheme.
	Fig. 2. View of a hydrogen bonded ribbon of barbiturate anions with the attached trimethylammonium cations.

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

Crystal data top

C₃H₁₀N⁺·C₁₀H₄N₅O₉⁻	F(000) = 1648
M_r = 398.30	D_x = 1.561 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8488 reflections
a = 11.9828 (12) Å	θ = 2.2–29.2°
b = 30.802 (3) Å	µ = 0.13 mm⁻¹
c = 9.5516 (11) Å	T = 296 K
β = 105.895 (6)°	Block, brown
V = 3390.6 (6) Å³	0.30 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker Kappa APEX II CCD diffractometer	6580 independent reflections
Radiation source: fine-focus sealed tube	4977 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scan	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
T_min = 0.90, T_max = 0.97	k = −37→37
31796 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0538P)² + 1.671P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
6580 reflections	Δρ_max = 0.34 e Å⁻³
536 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (4)

Crystal data top

C₃H₁₀N⁺·C₁₀H₄N₅O₉⁻	V = 3390.6 (6) Å³
M_r = 398.30	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9828 (12) Å	µ = 0.13 mm⁻¹
b = 30.802 (3) Å	T = 296 K
c = 9.5516 (11) Å	0.30 × 0.20 × 0.20 mm
β = 105.895 (6)°

Data collection top

Bruker Kappa APEX II CCD diffractometer	6580 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4977 reflections with I > 2σ(I)
T_min = 0.90, T_max = 0.97	R_int = 0.030
31796 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.34 e Å⁻³
6580 reflections	Δρ_min = −0.30 e Å⁻³
536 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.1280 (2)	−0.04978 (7)	0.6975 (3)	0.0520 (6)
C2	0.07387 (19)	−0.02594 (7)	0.7794 (3)	0.0507 (6)
H2	0.0396	−0.0393	0.8444	0.061*
C3	0.07113 (16)	0.01807 (6)	0.7636 (2)	0.0379 (5)
C4	0.11767 (14)	0.04061 (6)	0.6661 (2)	0.0301 (4)
C5	0.16732 (16)	0.01315 (6)	0.5837 (2)	0.0371 (4)
C6	0.17509 (19)	−0.03096 (7)	0.5989 (3)	0.0492 (6)
H6	0.2116	−0.0476	0.5431	0.059*
C7	0.11546 (15)	0.08708 (6)	0.6514 (2)	0.0294 (4)
C8	0.01360 (15)	0.11016 (6)	0.6479 (2)	0.0284 (4)
C9	0.10703 (16)	0.17708 (6)	0.6088 (2)	0.0330 (4)
C10	0.21401 (15)	0.10922 (6)	0.6360 (2)	0.0314 (4)
C11	0.57418 (19)	0.33262 (6)	0.5258 (2)	0.0418 (5)
C12	0.49039 (18)	0.30675 (6)	0.4401 (2)	0.0386 (5)
H12	0.4260	0.3186	0.3735	0.046*
C13	0.50449 (16)	0.26296 (6)	0.4557 (2)	0.0322 (4)
C14	0.59422 (15)	0.24254 (6)	0.5597 (2)	0.0288 (4)
C15	0.67477 (16)	0.27170 (6)	0.6415 (2)	0.0321 (4)
C16	0.66866 (19)	0.31572 (6)	0.6246 (2)	0.0417 (5)
H16	0.7272	0.3336	0.6788	0.050*
C17	0.60067 (15)	0.19623 (6)	0.5822 (2)	0.0303 (4)
C18	0.50129 (15)	0.17370 (6)	0.5898 (2)	0.0314 (4)
C19	0.61320 (16)	0.10691 (6)	0.6373 (2)	0.0372 (5)
C20	0.70684 (16)	0.17435 (6)	0.6027 (2)	0.0326 (4)
C21	−0.0029 (3)	0.19000 (12)	1.0012 (4)	0.0901 (10)
H21A	−0.0174	0.1597	0.9804	0.135*
H21B	−0.0129	0.2057	0.9117	0.135*
H21C	−0.0563	0.2008	1.0515	0.135*
C22	0.1314 (3)	0.17431 (12)	1.2299 (4)	0.0930 (11)
H22A	0.1229	0.1435	1.2147	0.140*
H22B	0.0744	0.1845	1.2757	0.140*
H22C	0.2077	0.1805	1.2913	0.140*
C23	0.1971 (3)	0.18289 (12)	1.0133 (4)	0.0934 (11)
H23A	0.2747	0.1878	1.0727	0.140*
H23B	0.1837	0.1997	0.9255	0.140*
H23C	0.1871	0.1526	0.9892	0.140*
C24	0.4800 (3)	0.00605 (12)	0.8010 (4)	0.0884 (10)
H24A	0.4493	−0.0136	0.8593	0.133*
H24B	0.4214	0.0122	0.7123	0.133*
H24C	0.5033	0.0325	0.8538	0.133*
C25	0.6768 (3)	−0.01717 (14)	0.8925 (4)	0.0988 (12)
H25A	0.6566	−0.0353	0.9635	0.148*
H25B	0.6975	0.0112	0.9329	0.148*
H25C	0.7414	−0.0297	0.8656	0.148*
C26	0.5432 (5)	−0.05449 (12)	0.6919 (5)	0.137 (2)
H26A	0.6101	−0.0716	0.6914	0.205*
H26B	0.4992	−0.0487	0.5935	0.205*
H26C	0.4959	−0.0702	0.7411	0.205*
N1	0.1341 (2)	−0.09686 (8)	0.7141 (3)	0.0774 (8)
N2	0.02277 (18)	0.04092 (7)	0.8676 (2)	0.0520 (5)
N3	0.20994 (17)	0.02933 (6)	0.4651 (2)	0.0493 (5)
N4	0.01520 (13)	0.15431 (5)	0.62608 (18)	0.0327 (4)
N5	0.20410 (14)	0.15362 (5)	0.61741 (19)	0.0352 (4)
N6	0.5592 (2)	0.37934 (6)	0.5148 (2)	0.0626 (6)
N7	0.42027 (15)	0.23778 (6)	0.34613 (19)	0.0409 (4)
N8	0.76942 (14)	0.25697 (5)	0.7650 (2)	0.0396 (4)
N9	0.51370 (14)	0.12959 (5)	0.6177 (2)	0.0383 (4)
N10	0.70604 (14)	0.13030 (5)	0.6297 (2)	0.0380 (4)
N11	0.11542 (19)	0.19574 (6)	1.0921 (2)	0.0538 (5)
N12	0.5802 (2)	−0.01380 (7)	0.7670 (2)	0.0569 (5)
O1	0.0869 (2)	−0.11310 (7)	0.7939 (5)	0.1399 (14)
O2	0.1908 (3)	−0.11639 (7)	0.6489 (2)	0.1265 (13)
O3	0.08047 (18)	0.06930 (6)	0.9405 (2)	0.0659 (5)
O4	−0.06914 (17)	0.02796 (7)	0.8806 (2)	0.0788 (6)
O5	0.29880 (18)	0.01269 (7)	0.4523 (2)	0.0780 (6)
O6	0.15519 (15)	0.05664 (6)	0.38352 (18)	0.0575 (4)
O7	−0.07663 (10)	0.09318 (4)	0.65984 (16)	0.0365 (3)
O8	0.30776 (11)	0.09178 (4)	0.64047 (17)	0.0423 (4)
O9	0.10310 (12)	0.21575 (4)	0.58780 (19)	0.0506 (4)
O10	0.4647 (2)	0.39359 (6)	0.4567 (3)	0.0874 (7)
O11	0.6406 (2)	0.40236 (6)	0.5663 (3)	0.1089 (9)
O12	0.32075 (13)	0.25037 (6)	0.3120 (2)	0.0589 (5)
O13	0.45480 (14)	0.20692 (5)	0.29116 (18)	0.0547 (4)
O14	0.86373 (13)	0.27312 (5)	0.7787 (2)	0.0605 (5)
O15	0.74674 (14)	0.23106 (5)	0.84766 (17)	0.0493 (4)
O16	0.40506 (11)	0.19019 (4)	0.57728 (17)	0.0403 (3)
O17	0.79831 (11)	0.19122 (4)	0.59685 (18)	0.0438 (4)
O18	0.61782 (13)	0.06785 (5)	0.6586 (2)	0.0563 (5)
H4	−0.046 (2)	0.1686 (7)	0.619 (2)	0.037 (6)*
H5	0.263 (2)	0.1680 (8)	0.607 (3)	0.050 (7)*
H9	0.455 (2)	0.1158 (7)	0.627 (2)	0.042 (6)*
H10	0.769 (2)	0.1172 (7)	0.640 (2)	0.046 (6)*
H11A	0.123 (3)	0.2258 (11)	1.111 (3)	0.091 (10)*
H12A	0.605 (3)	0.0039 (10)	0.701 (3)	0.082 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0435 (12)	0.0251 (11)	0.0709 (16)	−0.0001 (9)	−0.0121 (11)	0.0031 (10)
C2	0.0354 (11)	0.0391 (12)	0.0711 (16)	−0.0048 (9)	0.0038 (11)	0.0197 (11)
C3	0.0274 (9)	0.0334 (10)	0.0516 (12)	0.0023 (8)	0.0089 (9)	0.0086 (9)
C4	0.0186 (8)	0.0273 (9)	0.0423 (11)	−0.0002 (7)	0.0046 (7)	0.0010 (8)
C5	0.0285 (10)	0.0337 (10)	0.0459 (12)	0.0032 (8)	0.0049 (8)	−0.0036 (9)
C6	0.0440 (12)	0.0348 (12)	0.0580 (14)	0.0105 (9)	−0.0043 (10)	−0.0105 (10)
C7	0.0226 (9)	0.0255 (9)	0.0406 (11)	−0.0002 (7)	0.0095 (7)	0.0016 (8)
C8	0.0240 (9)	0.0277 (9)	0.0336 (10)	−0.0004 (7)	0.0081 (7)	0.0008 (7)
C9	0.0278 (9)	0.0263 (10)	0.0427 (11)	−0.0017 (7)	0.0059 (8)	−0.0004 (8)
C10	0.0245 (9)	0.0288 (10)	0.0408 (11)	−0.0003 (7)	0.0089 (8)	0.0009 (8)
C11	0.0509 (12)	0.0252 (10)	0.0488 (13)	0.0038 (9)	0.0130 (10)	0.0035 (9)
C12	0.0382 (11)	0.0354 (11)	0.0426 (12)	0.0077 (8)	0.0118 (9)	0.0050 (9)
C13	0.0265 (9)	0.0338 (10)	0.0384 (11)	−0.0005 (8)	0.0123 (8)	−0.0006 (8)
C14	0.0233 (9)	0.0283 (9)	0.0389 (10)	0.0007 (7)	0.0153 (8)	−0.0004 (8)
C15	0.0274 (9)	0.0295 (10)	0.0400 (11)	0.0016 (7)	0.0103 (8)	0.0011 (8)
C16	0.0427 (11)	0.0287 (10)	0.0512 (13)	−0.0056 (9)	0.0086 (10)	−0.0027 (9)
C17	0.0236 (9)	0.0265 (9)	0.0432 (11)	0.0007 (7)	0.0133 (8)	−0.0007 (8)
C18	0.0248 (9)	0.0280 (9)	0.0436 (11)	0.0008 (7)	0.0131 (8)	−0.0007 (8)
C19	0.0317 (10)	0.0266 (10)	0.0558 (13)	−0.0001 (8)	0.0163 (9)	−0.0003 (9)
C20	0.0269 (9)	0.0252 (9)	0.0493 (12)	−0.0001 (7)	0.0166 (8)	−0.0011 (8)
C21	0.077 (2)	0.102 (3)	0.090 (2)	0.0316 (19)	0.0213 (18)	0.024 (2)
C22	0.103 (3)	0.100 (3)	0.068 (2)	−0.043 (2)	0.0111 (18)	0.0178 (18)
C23	0.082 (2)	0.116 (3)	0.091 (2)	−0.029 (2)	0.0376 (19)	−0.039 (2)
C24	0.0619 (18)	0.112 (3)	0.096 (2)	−0.0006 (18)	0.0298 (17)	0.028 (2)
C25	0.0619 (19)	0.140 (3)	0.087 (2)	0.003 (2)	0.0083 (17)	0.040 (2)
C26	0.227 (6)	0.081 (3)	0.130 (4)	−0.076 (3)	0.098 (4)	−0.039 (2)
N1	0.0761 (17)	0.0366 (13)	0.0909 (19)	0.0052 (12)	−0.0255 (14)	0.0109 (13)
N2	0.0495 (12)	0.0541 (12)	0.0587 (13)	0.0159 (10)	0.0256 (10)	0.0248 (10)
N3	0.0479 (11)	0.0517 (11)	0.0497 (11)	0.0081 (9)	0.0159 (9)	−0.0082 (9)
N4	0.0220 (8)	0.0269 (8)	0.0493 (10)	0.0040 (6)	0.0099 (7)	0.0017 (7)
N5	0.0226 (8)	0.0275 (8)	0.0561 (11)	−0.0036 (6)	0.0118 (7)	0.0042 (7)
N6	0.0797 (16)	0.0325 (11)	0.0665 (14)	0.0076 (11)	0.0046 (12)	0.0024 (10)
N7	0.0344 (9)	0.0435 (10)	0.0429 (10)	−0.0040 (8)	0.0071 (8)	0.0002 (8)
N8	0.0327 (9)	0.0342 (9)	0.0491 (11)	0.0004 (7)	0.0064 (8)	−0.0017 (8)
N9	0.0260 (8)	0.0278 (9)	0.0655 (12)	−0.0035 (7)	0.0201 (8)	0.0033 (8)
N10	0.0246 (8)	0.0279 (9)	0.0656 (12)	0.0049 (7)	0.0190 (8)	0.0027 (8)
N11	0.0733 (14)	0.0327 (10)	0.0583 (13)	−0.0046 (9)	0.0231 (11)	−0.0020 (9)
N12	0.0711 (14)	0.0527 (12)	0.0529 (12)	−0.0156 (10)	0.0272 (11)	0.0002 (10)
O1	0.0936 (19)	0.0485 (14)	0.275 (4)	−0.0012 (12)	0.047 (2)	0.064 (2)
O2	0.250 (4)	0.0466 (12)	0.0588 (13)	0.0597 (18)	0.0027 (17)	0.0002 (10)
O3	0.0789 (13)	0.0684 (12)	0.0515 (11)	0.0184 (11)	0.0197 (9)	0.0022 (9)
O4	0.0603 (11)	0.0869 (14)	0.1081 (16)	0.0190 (10)	0.0548 (11)	0.0474 (12)
O5	0.0752 (13)	0.0907 (14)	0.0825 (14)	0.0325 (11)	0.0459 (11)	−0.0048 (11)
O6	0.0557 (10)	0.0671 (11)	0.0479 (10)	0.0038 (9)	0.0113 (8)	0.0038 (8)
O7	0.0227 (6)	0.0326 (7)	0.0565 (9)	0.0023 (5)	0.0148 (6)	0.0072 (6)
O8	0.0217 (7)	0.0344 (8)	0.0731 (10)	0.0015 (5)	0.0169 (6)	0.0040 (7)
O9	0.0389 (8)	0.0248 (7)	0.0857 (12)	−0.0013 (6)	0.0131 (8)	0.0057 (7)
O10	0.1006 (17)	0.0439 (11)	0.0996 (16)	0.0302 (11)	−0.0035 (13)	0.0065 (10)
O11	0.1089 (18)	0.0312 (10)	0.151 (2)	−0.0119 (11)	−0.0244 (16)	0.0059 (12)
O12	0.0320 (8)	0.0625 (11)	0.0721 (11)	0.0003 (7)	−0.0030 (8)	0.0016 (9)
O13	0.0582 (10)	0.0518 (10)	0.0515 (10)	−0.0026 (8)	0.0108 (8)	−0.0162 (8)
O14	0.0315 (8)	0.0539 (10)	0.0856 (13)	−0.0096 (7)	−0.0015 (8)	0.0053 (9)
O15	0.0519 (9)	0.0494 (9)	0.0450 (9)	0.0027 (7)	0.0102 (7)	0.0097 (7)
O16	0.0236 (7)	0.0332 (7)	0.0684 (10)	0.0024 (5)	0.0197 (6)	0.0052 (7)
O17	0.0264 (7)	0.0306 (7)	0.0810 (11)	0.0005 (6)	0.0261 (7)	0.0031 (7)
O18	0.0430 (9)	0.0255 (8)	0.1043 (14)	0.0015 (6)	0.0269 (9)	0.0071 (8)

Geometric parameters (Å, º) top

C1—C6	1.354 (4)	C21—N11	1.456 (4)
C1—C2	1.360 (4)	C21—H21A	0.9600
C1—N1	1.458 (3)	C21—H21B	0.9600
C2—C3	1.363 (3)	C21—H21C	0.9600
C2—H2	0.9300	C22—N11	1.438 (4)
C3—C4	1.395 (3)	C22—H22A	0.9600
C3—N2	1.460 (3)	C22—H22B	0.9600
C4—C5	1.395 (3)	C22—H22C	0.9600
C4—C7	1.438 (3)	C23—N11	1.443 (4)
C5—C6	1.367 (3)	C23—H23A	0.9600
C5—N3	1.452 (3)	C23—H23B	0.9600
C6—H6	0.9300	C23—H23C	0.9600
C7—C8	1.405 (2)	C24—N12	1.461 (4)
C7—C10	1.405 (2)	C24—H24A	0.9600
C8—O7	1.234 (2)	C24—H24B	0.9600
C8—N4	1.377 (2)	C24—H24C	0.9600
C9—O9	1.207 (2)	C25—N12	1.424 (4)
C9—N4	1.352 (2)	C25—H25A	0.9600
C9—N5	1.352 (2)	C25—H25B	0.9600
C10—O8	1.235 (2)	C25—H25C	0.9600
C10—N5	1.380 (2)	C26—N12	1.452 (4)
C11—C16	1.363 (3)	C26—H26A	0.9600
C11—C12	1.365 (3)	C26—H26B	0.9600
C11—N6	1.451 (3)	C26—H26C	0.9600
C12—C13	1.362 (3)	N1—O1	1.178 (4)
C12—H12	0.9300	N1—O2	1.201 (4)
C13—C14	1.398 (3)	N2—O4	1.209 (3)
C13—N7	1.462 (3)	N2—O3	1.210 (3)
C14—C15	1.391 (3)	N3—O6	1.210 (2)
C14—C17	1.441 (2)	N3—O5	1.218 (2)
C15—C16	1.365 (3)	N4—H4	0.85 (2)
C15—N8	1.466 (3)	N5—H5	0.86 (3)
C16—H16	0.9300	N6—O11	1.198 (3)
C17—C18	1.398 (2)	N6—O10	1.199 (3)
C17—C20	1.405 (2)	N7—O12	1.211 (2)
C18—O16	1.235 (2)	N7—O13	1.212 (2)
C18—N9	1.384 (2)	N8—O15	1.205 (2)
C19—O18	1.219 (2)	N8—O14	1.208 (2)
C19—N10	1.344 (2)	N9—H9	0.85 (2)
C19—N9	1.350 (2)	N10—H10	0.83 (2)
C20—O17	1.228 (2)	N11—H11A	0.94 (3)
C20—N10	1.381 (2)	N12—H12A	0.94 (3)

C6—C1—C2	121.6 (2)	N11—C22—H22C	109.5
C6—C1—N1	118.9 (3)	H22A—C22—H22C	109.5
C2—C1—N1	119.5 (3)	H22B—C22—H22C	109.5
C1—C2—C3	118.3 (2)	N11—C23—H23A	109.5
C1—C2—H2	120.8	N11—C23—H23B	109.5
C3—C2—H2	120.8	H23A—C23—H23B	109.5
C2—C3—C4	124.5 (2)	N11—C23—H23C	109.5
C2—C3—N2	114.0 (2)	H23A—C23—H23C	109.5
C4—C3—N2	121.33 (18)	H23B—C23—H23C	109.5
C5—C4—C3	112.67 (17)	N12—C24—H24A	109.5
C5—C4—C7	123.22 (17)	N12—C24—H24B	109.5
C3—C4—C7	124.11 (17)	H24A—C24—H24B	109.5
C6—C5—C4	124.8 (2)	N12—C24—H24C	109.5
C6—C5—N3	113.30 (19)	H24A—C24—H24C	109.5
C4—C5—N3	121.83 (18)	H24B—C24—H24C	109.5
C1—C6—C5	118.0 (2)	N12—C25—H25A	109.5
C1—C6—H6	121.0	N12—C25—H25B	109.5
C5—C6—H6	121.0	H25A—C25—H25B	109.5
C8—C7—C10	120.10 (16)	N12—C25—H25C	109.5
C8—C7—C4	119.90 (15)	H25A—C25—H25C	109.5
C10—C7—C4	119.97 (16)	H25B—C25—H25C	109.5
O7—C8—N4	118.79 (16)	N12—C26—H26A	109.5
O7—C8—C7	124.11 (16)	N12—C26—H26B	109.5
N4—C8—C7	117.08 (15)	H26A—C26—H26B	109.5
O9—C9—N4	122.42 (17)	N12—C26—H26C	109.5
O9—C9—N5	122.07 (17)	H26A—C26—H26C	109.5
N4—C9—N5	115.51 (16)	H26B—C26—H26C	109.5
O8—C10—N5	118.72 (16)	O1—N1—O2	124.3 (3)
O8—C10—C7	124.59 (17)	O1—N1—C1	118.2 (3)
N5—C10—C7	116.68 (16)	O2—N1—C1	117.4 (3)
C16—C11—C12	121.82 (18)	O4—N2—O3	124.9 (2)
C16—C11—N6	119.5 (2)	O4—N2—C3	116.9 (2)
C12—C11—N6	118.7 (2)	O3—N2—C3	117.97 (19)
C13—C12—C11	117.63 (19)	O6—N3—O5	124.2 (2)
C13—C12—H12	121.2	O6—N3—C5	119.76 (17)
C11—C12—H12	121.2	O5—N3—C5	116.0 (2)
C12—C13—C14	124.84 (18)	C9—N4—C8	125.18 (16)
C12—C13—N7	113.99 (18)	C9—N4—H4	116.2 (14)
C14—C13—N7	121.06 (16)	C8—N4—H4	118.5 (14)
C15—C14—C13	112.90 (16)	C9—N5—C10	125.41 (16)
C15—C14—C17	123.66 (17)	C9—N5—H5	115.7 (16)
C13—C14—C17	123.42 (17)	C10—N5—H5	118.8 (16)
C16—C15—C14	124.62 (18)	O11—N6—O10	122.2 (2)
C16—C15—N8	114.02 (17)	O11—N6—C11	119.1 (2)
C14—C15—N8	121.13 (16)	O10—N6—C11	118.6 (2)
C11—C16—C15	117.95 (19)	O12—N7—O13	124.23 (18)
C11—C16—H16	121.0	O12—N7—C13	117.30 (17)
C15—C16—H16	121.0	O13—N7—C13	118.40 (17)
C18—C17—C20	120.41 (16)	O15—N8—O14	124.99 (18)
C18—C17—C14	119.19 (15)	O15—N8—C15	117.93 (16)
C20—C17—C14	120.34 (15)	O14—N8—C15	117.02 (17)
O16—C18—N9	118.05 (16)	C19—N9—C18	125.36 (16)
O16—C18—C17	125.23 (17)	C19—N9—H9	117.0 (15)
N9—C18—C17	116.70 (16)	C18—N9—H9	117.6 (15)
O18—C19—N10	122.54 (18)	C19—N10—C20	125.79 (16)
O18—C19—N9	122.14 (18)	C19—N10—H10	117.8 (16)
N10—C19—N9	115.32 (17)	C20—N10—H10	116.4 (16)
O17—C20—N10	118.43 (16)	C22—N11—C23	114.3 (3)
O17—C20—C17	125.15 (17)	C22—N11—C21	110.7 (2)
N10—C20—C17	116.42 (16)	C23—N11—C21	110.1 (2)
N11—C21—H21A	109.5	C22—N11—H11A	107 (2)
N11—C21—H21B	109.5	C23—N11—H11A	108.9 (19)
H21A—C21—H21B	109.5	C21—N11—H11A	105 (2)
N11—C21—H21C	109.5	C25—N12—C26	114.9 (3)
H21A—C21—H21C	109.5	C25—N12—C24	111.8 (3)
H21B—C21—H21C	109.5	C26—N12—C24	108.2 (3)
N11—C22—H22A	109.5	C25—N12—H12A	105.4 (18)
N11—C22—H22B	109.5	C26—N12—H12A	106.4 (19)
H22A—C22—H22B	109.5	C24—N12—H12A	109.8 (18)

C6—C1—C2—C3	−2.2 (3)	C20—C17—C18—O16	177.9 (2)
N1—C1—C2—C3	178.9 (2)	C14—C17—C18—O16	0.8 (3)
C1—C2—C3—C4	1.7 (3)	C20—C17—C18—N9	−0.2 (3)
C1—C2—C3—N2	−173.5 (2)	C14—C17—C18—N9	−177.35 (18)
C2—C3—C4—C5	0.6 (3)	C18—C17—C20—O17	179.4 (2)
N2—C3—C4—C5	175.41 (18)	C14—C17—C20—O17	−3.5 (3)
C2—C3—C4—C7	−179.3 (2)	C18—C17—C20—N10	0.2 (3)
N2—C3—C4—C7	−4.5 (3)	C14—C17—C20—N10	177.31 (18)
C3—C4—C5—C6	−2.6 (3)	C6—C1—N1—O1	−175.5 (3)
C7—C4—C5—C6	177.25 (19)	C2—C1—N1—O1	3.5 (4)
C3—C4—C5—N3	173.45 (18)	C6—C1—N1—O2	7.0 (4)
C7—C4—C5—N3	−6.7 (3)	C2—C1—N1—O2	−174.0 (3)
C2—C1—C6—C5	0.3 (3)	C2—C3—N2—O4	−49.6 (3)
N1—C1—C6—C5	179.3 (2)	C4—C3—N2—O4	135.1 (2)
C4—C5—C6—C1	2.3 (3)	C2—C3—N2—O3	125.8 (2)
N3—C5—C6—C1	−174.08 (19)	C4—C3—N2—O3	−49.6 (3)
C5—C4—C7—C8	136.11 (19)	C6—C5—N3—O6	135.8 (2)
C3—C4—C7—C8	−44.0 (3)	C4—C5—N3—O6	−40.7 (3)
C5—C4—C7—C10	−42.0 (3)	C6—C5—N3—O5	−41.6 (3)
C3—C4—C7—C10	137.9 (2)	C4—C5—N3—O5	141.9 (2)
C10—C7—C8—O7	179.62 (18)	O9—C9—N4—C8	178.88 (19)
C4—C7—C8—O7	1.5 (3)	N5—C9—N4—C8	−1.4 (3)
C10—C7—C8—N4	1.4 (3)	O7—C8—N4—C9	−178.87 (18)
C4—C7—C8—N4	−176.73 (17)	C7—C8—N4—C9	−0.5 (3)
C8—C7—C10—O8	178.54 (19)	O9—C9—N5—C10	−177.6 (2)
C4—C7—C10—O8	−3.4 (3)	N4—C9—N5—C10	2.7 (3)
C8—C7—C10—N5	−0.3 (3)	O8—C10—N5—C9	179.20 (19)
C4—C7—C10—N5	177.84 (17)	C7—C10—N5—C9	−1.9 (3)
C16—C11—C12—C13	−0.5 (3)	C16—C11—N6—O11	17.1 (4)
N6—C11—C12—C13	−177.93 (19)	C12—C11—N6—O11	−165.3 (3)
C11—C12—C13—C14	4.6 (3)	C16—C11—N6—O10	−161.4 (2)
C11—C12—C13—N7	−171.62 (18)	C12—C11—N6—O10	16.2 (3)
C12—C13—C14—C15	−4.4 (3)	C12—C13—N7—O12	−40.6 (2)
N7—C13—C14—C15	171.59 (16)	C14—C13—N7—O12	143.01 (19)
C12—C13—C14—C17	174.00 (18)	C12—C13—N7—O13	136.46 (19)
N7—C13—C14—C17	−10.0 (3)	C14—C13—N7—O13	−39.9 (3)
C13—C14—C15—C16	0.2 (3)	C16—C15—N8—O15	131.1 (2)
C17—C14—C15—C16	−178.20 (19)	C14—C15—N8—O15	−43.6 (3)
C13—C14—C15—N8	174.30 (16)	C16—C15—N8—O14	−46.3 (3)
C17—C14—C15—N8	−4.1 (3)	C14—C15—N8—O14	139.05 (19)
C12—C11—C16—C15	−3.3 (3)	O18—C19—N9—C18	−178.5 (2)
N6—C11—C16—C15	174.1 (2)	N10—C19—N9—C18	0.7 (3)
C14—C15—C16—C11	3.5 (3)	O16—C18—N9—C19	−178.6 (2)
N8—C15—C16—C11	−170.99 (18)	C17—C18—N9—C19	−0.3 (3)
C15—C14—C17—C18	132.5 (2)	O18—C19—N10—C20	178.5 (2)
C13—C14—C17—C18	−45.7 (3)	N9—C19—N10—C20	−0.7 (3)
C15—C14—C17—C20	−44.6 (3)	O17—C20—N10—C19	−178.9 (2)
C13—C14—C17—C20	137.12 (19)	C17—C20—N10—C19	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O17ⁱ	0.85 (2)	1.94 (2)	2.780 (2)	170 (2)
N5—H5···O16	0.86 (3)	1.93 (3)	2.778 (2)	170 (2)
N9—H9···O8	0.85 (2)	1.95 (2)	2.790 (2)	172 (2)
N10—H10···O7ⁱⁱ	0.83 (2)	1.96 (2)	2.786 (2)	173 (2)
N11—H11A···O9ⁱⁱⁱ	0.94 (3)	1.82 (3)	2.730 (2)	160 (3)
N12—H12A···O18	0.94 (3)	2.02 (3)	2.803 (3)	139 (3)
N12—H12A···O5^iv	0.94 (3)	2.16 (3)	2.856 (3)	130 (2)
C2—H2···O4^v	0.93	2.58	3.265 (3)	131
C16—H16···O2^vi	0.93	2.27	3.146 (3)	156
C24—H24B···O5	0.96	2.51	3.448 (4)	164
C24—H24C···O10ⁱⁱⁱ	0.96	2.57	3.457 (4)	154
C26—H26B···O18^iv	0.96	2.50	3.400 (5)	156

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y, −z+1; (v) −x, −y, −z+2; (vi) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₃H₁₀N⁺·C₁₀H₄N₅O₉⁻
M_r	398.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.9828 (12), 30.802 (3), 9.5516 (11)
β (°)	105.895 (6)
V (Å³)	3390.6 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEX II CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.90, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	31796, 6580, 4977
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.123, 1.02
No. of reflections	6580
No. of parameters	536
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.30

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O17ⁱ	0.85 (2)	1.94 (2)	2.780 (2)	170 (2)
N5—H5···O16	0.86 (3)	1.93 (3)	2.778 (2)	170 (2)
N9—H9···O8	0.85 (2)	1.95 (2)	2.790 (2)	172 (2)
N10—H10···O7ⁱⁱ	0.83 (2)	1.96 (2)	2.786 (2)	173 (2)
N11—H11A···O9ⁱⁱⁱ	0.94 (3)	1.82 (3)	2.730 (2)	160 (3)
N12—H12A···O18	0.94 (3)	2.02 (3)	2.803 (3)	139 (3)
N12—H12A···O5^iv	0.94 (3)	2.16 (3)	2.856 (3)	130 (2)
C2—H2···O4^v	0.93	2.58	3.265 (3)	131.2
C16—H16···O2^vi	0.93	2.27	3.146 (3)	156.3
C24—H24B···O5	0.96	2.51	3.448 (4)	163.9
C24—H24C···O10ⁱⁱⁱ	0.96	2.57	3.457 (4)	153.7
C26—H26B···O18^iv	0.96	2.50	3.400 (5)	155.5

Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, −y, −z+1; (v) −x, −y, −z+2; (vi) −x+1, y+1/2, −z+3/2.

Acknowledgements

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

References

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Volume 68| Part 1| January 2012| Pages o29-o30

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

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Supporting information

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organic compounds

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