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

Buvaneswari, M.; Kalaivani, D.

doi:10.1107/S1600536811049506

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3452

https://doi.org/10.1107/S1600536811049506

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

Manickam Buvaneswari ^a and Doraisamyraja Kalaivani ^a ^*

^aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
^*Correspondence e-mail: kalaivbalaj@yahoo.co.in

(Received 1 September 2011; accepted 19 November 2011; online 30 November 2011)

In the crystal structure of the title molecular salt, C₁₀H₁₆N⁺·C₁₀H₄N₅O₉⁻, the components are linked through a N—H⋯O hydrogen bonds. R₂²(8) ring motifs are formed between inversion-related barbiturate residues. Two intramoleculer N—H⋯O hydrogen bonds are observed in the anion. The dihedral angle between 2,4,6-trinitrophenyl and barbiturate rings is 53.6 (2)°. The N,N-diethylamine substituent is disordered and was modeled as two geometrically equivalent conformers with occupancies of 0.737 (2) and 0.273 (2).

Related literature

N,N-Dialkylaniline (aromatic amine) usually forms donor–acceptor adducts with electron-deficient nitro aromatics, see: Radha et al. (1987 ); Rizk et al. (1993 ). For similar structures containing the barbiturate anion, see: Buvaneswari & Kalaivani (2011 ); Kalaivani & Buvaneswari (2010 ); Kalaivani & Malarvizhi (2009 ); Kalaivani et al. (2008 ).

Experimental

Crystal data

C₁₀H₁₆N⁺·C₁₀H₄N₅O₉⁻
M_r = 488.42
Monoclinic, P 2₁ /c
a = 17.1903 (7) Å
b = 10.3925 (5) Å
c = 13.3613 (5) Å
β = 110.272 (2)°
V = 2239.14 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.923, T_max = 0.962
3550 measured reflections
3550 independent reflections
2763 reflections with I > 2σ(I)
θ_max = 24.1°

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.03
3550 reflections
337 parameters
9 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.01	2.8451 (18)	162
N2—H2A⋯O3ⁱⁱ	0.86	1.98	2.8230 (16)	167
N6A—H6AA⋯O2	0.91	1.88	2.790 (3)	175
N6B—H6BA⋯O2	0.91	1.71	2.617 (8)	174
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1.

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: SHELXS97 (Sheldrick, 2008 ); 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: https://doi.org/10.1107/S1600536811049506/bv2193sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049506/bv2193Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049506/bv2193Isup3.cml

checkCIF report

Comment top

N,N-Dialkylaniline (aromatic amine) usually forms donor-acceptor adducts with electron-deficient nitro aromatics (Radha et al., 1987, Rizk et al., 1993). In the present investigation, it forms a different type of molecular salt (scheme) with the electron-deficient nitro aromatic compound, 1-chloro-2,4,6-trinitrobenzene (picryl chloride) in the presence of barbituric acid. We have already reported molecular salts of a similar type obtained from chlorine containing nitro aromatic compounds, barbituric acid and aliphatic amines (Kalaivani et al., 2008, Kalaivani & Malarvizhi, 2009, Kalaivani & Buvaneswari, 2010, Buvaneswari & Kalaivani, 2011). As noticed in other barbiturates, ring motifs are observed in the crystal structure of the title molecule. The protonated nitrogen atom of N,N-diethylaniline forms a hydrogen bond with the oxygen atom of the barbiturate anion and this may probably be the driving force for the formation of the title molecular salt.The negative charge on the oxygen atom of olate is delocalized over the nitro groups of the trinitrophenyl moiety and due to this extended conjugation the salt appears bright maroon red in colour.The title molecular salt is obtained with high purity in good yield (90%). Fig.1and 2 represent the ORTEP and packing view of the title molecule.

Related literature top

N,N-Dialkylaniline (aromatic amine) usually forms donor–acceptor adducts with electron-deficient nitro aromatics, see: Radha et al. (1987); Rizk et al. (1993). For similar structures containing the barbiturate anion, see: Buvaneswari & Kalaivani (2011); Kalaivani & Buvaneswari (2010); Kalaivani & Malarvizhi (2009); Kalaivani et al. (2008).

Experimental top

Picryl chloride(1.3.g, 0.005 mol) was dissolved in 15 ml absolute alcohol. Barbituric acid (0.6 g, 0.005 mol)was dissolved in 30 ml of absolute alcohol. These two solutions were mixed and heated to 50°C.To this hot mixture, 4 ml of N,N-diethylaniline (0.03 mol) was added and shaken well for 3hrs. The crystals obtained were filtered, washed with 50 ml of dry ether and recrystallized from absolute alcohol (yield of pure crystals 90%, m.p.> 573 K). Maroon red block-like single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of an ethanolic solution of the title compound at room temperature.

Structure description top

N,N-Dialkylaniline (aromatic amine) usually forms donor–acceptor adducts with electron-deficient nitro aromatics, see: Radha et al. (1987); Rizk et al. (1993). For similar structures containing the barbiturate anion, see: Buvaneswari & Kalaivani (2011); Kalaivani & Buvaneswari (2010); Kalaivani & Malarvizhi (2009); Kalaivani et al. (2008).

Computing details top

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: SHELXS97 (Sheldrick, 2008); 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 view of N,N-diethylanilinium 2,4,6-trinitrophenyl barbiturate showing atom labeling.
	Fig. 2. Packing view of N,N-diethylanilinium 2,4,6-trinitrophenyl barbiturate. Hydrogen bonds are shown by dashed lines.

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

Crystal data top

C₁₀H₁₆N⁺·C₁₀H₄N₅O₉⁻	F(000) = 1016
M_r = 488.42	D_x = 1.449 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5399 reflections
a = 17.1903 (7) Å	θ = 2.4–23.5°
b = 10.3925 (5) Å	µ = 0.12 mm⁻¹
c = 13.3613 (5) Å	T = 293 K
β = 110.272 (2)°	Block, red
V = 2239.14 (16) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3550 independent reflections
Radiation source: fine-focus sealed tube	2763 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ω and φ scan	θ_max = 24.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −19→18
T_min = 0.923, T_max = 0.962	k = 0→11
3550 measured reflections	l = 0→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0501P)² + 0.6573P] where P = (F_o² + 2F_c²)/3
3550 reflections	(Δ/σ)_max < 0.001
337 parameters	Δρ_max = 0.20 e Å⁻³
9 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₀H₁₆N⁺·C₁₀H₄N₅O₉⁻	V = 2239.14 (16) Å³
M_r = 488.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.1903 (7) Å	µ = 0.12 mm⁻¹
b = 10.3925 (5) Å	T = 293 K
c = 13.3613 (5) Å	0.30 × 0.20 × 0.20 mm
β = 110.272 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3550 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2763 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.962	R_int = 0.000
3550 measured reflections	θ_max = 24.1°

Refinement top

R[F² > 2σ(F²)] = 0.038	9 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
3550 reflections	Δρ_min = −0.17 e Å⁻³
337 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	Occ. (<1)
O1	0.55484 (7)	0.34991 (11)	0.49281 (10)	0.0450 (3)
O2	0.29232 (6)	0.41484 (10)	0.48379 (9)	0.0409 (3)
O3	0.40988 (7)	0.00160 (10)	0.53210 (10)	0.0440 (3)
O4	0.21699 (8)	0.20296 (15)	0.31509 (10)	0.0606 (4)
O5	0.11256 (9)	0.30015 (17)	0.33237 (13)	0.0803 (5)
O6	0.00042 (9)	0.10375 (17)	0.58155 (14)	0.0813 (5)
O7	0.07485 (10)	−0.03877 (17)	0.68980 (15)	0.0881 (5)
O8	0.37537 (10)	−0.03623 (15)	0.75870 (11)	0.0737 (4)
O9	0.41237 (9)	0.15682 (15)	0.73996 (11)	0.0692 (4)
N1	0.42299 (7)	0.37873 (12)	0.48839 (10)	0.0361 (3)
H1A	0.4271	0.4600	0.4792	0.043*
N2	0.47941 (8)	0.17627 (12)	0.50602 (11)	0.0359 (3)
H2A	0.5187	0.1261	0.5042	0.043*
N3	0.17306 (9)	0.23115 (15)	0.36562 (12)	0.0484 (4)
N4	0.06518 (11)	0.04642 (19)	0.62447 (15)	0.0641 (5)
N5	0.36317 (10)	0.06897 (16)	0.71637 (11)	0.0505 (4)
C1	0.34912 (9)	0.33433 (15)	0.49459 (12)	0.0321 (4)
C2	0.34512 (9)	0.20346 (15)	0.51552 (12)	0.0317 (4)
C3	0.41044 (9)	0.11993 (15)	0.51931 (12)	0.0332 (4)
C4	0.48971 (9)	0.30453 (15)	0.49560 (13)	0.0336 (4)
C5	0.27378 (9)	0.15512 (14)	0.53912 (13)	0.0327 (4)
C6	0.19142 (9)	0.17548 (16)	0.47270 (13)	0.0376 (4)
C7	0.12349 (10)	0.14351 (18)	0.49944 (15)	0.0472 (5)
H7	0.0701	0.1631	0.4542	0.057*
C8	0.13670 (11)	0.08212 (18)	0.59447 (15)	0.0478 (5)
C9	0.21488 (11)	0.05304 (17)	0.66264 (14)	0.0465 (4)
H9	0.2229	0.0089	0.7260	0.056*
C10	0.28116 (10)	0.09117 (16)	0.63455 (13)	0.0386 (4)
C11	0.17516 (17)	0.6686 (3)	0.6939 (2)	0.0944 (8)
H11	0.2048	0.7429	0.7222	0.113*
C12	0.10144 (18)	0.6418 (3)	0.7087 (2)	0.1087 (10)
H12	0.0811	0.6995	0.7468	0.130*
C13	0.05792 (17)	0.5336 (3)	0.6692 (2)	0.0902 (8)
H13	0.0093	0.5154	0.6822	0.108*
C14	0.08618 (15)	0.4522 (3)	0.6104 (2)	0.0843 (7)
H14	0.0561	0.3786	0.5813	0.101*
C15	0.15923 (13)	0.4777 (2)	0.59356 (18)	0.0665 (6)
H15	0.1779	0.4218	0.5524	0.080*
C16	0.20396 (9)	0.58369 (19)	0.63669 (15)	0.0555 (5)
N6A	0.28140 (9)	0.6169 (2)	0.61581 (18)	0.0508 (7)	0.737 (2)
H6AA	0.2861	0.5546	0.5703	0.061*	0.737 (2)
C17A	0.36242 (16)	0.6089 (3)	0.7110 (2)	0.0598 (8)	0.737 (2)
H17A	0.4083	0.6324	0.6882	0.072*	0.737 (2)
H17B	0.3607	0.6698	0.7652	0.072*	0.737 (2)
C18A	0.3765 (2)	0.4769 (4)	0.7577 (2)	0.0781 (10)	0.737 (2)
H18A	0.4310	0.4720	0.8107	0.117*	0.737 (2)
H18B	0.3718	0.4153	0.7024	0.117*	0.737 (2)
H18C	0.3359	0.4586	0.7901	0.117*	0.737 (2)
C19A	0.2816 (2)	0.7424 (3)	0.5574 (3)	0.0638 (9)	0.737 (2)
H19A	0.2816	0.8141	0.6039	0.077*	0.737 (2)
H19B	0.3320	0.7475	0.5403	0.077*	0.737 (2)
C20A	0.2099 (3)	0.7533 (5)	0.4591 (4)	0.1084 (14)	0.737 (2)
H20A	0.2135	0.8320	0.4233	0.163*	0.737 (2)
H20B	0.1600	0.7534	0.4760	0.163*	0.737 (2)
H20C	0.2091	0.6817	0.4134	0.163*	0.737 (2)
N6B	0.28886 (16)	0.5796 (9)	0.6304 (5)	0.0508 (7)	0.263 (2)
H6BA	0.2935	0.5249	0.5795	0.061*	0.263 (2)
C17B	0.3394 (5)	0.5389 (10)	0.7432 (6)	0.0598 (8)	0.263 (2)
H17C	0.3420	0.6074	0.7936	0.072*	0.263 (2)
H17D	0.3159	0.4628	0.7638	0.072*	0.263 (2)
C18B	0.4219 (5)	0.5117 (11)	0.7381 (7)	0.0781 (10)	0.263 (2)
H18D	0.4552	0.4690	0.8023	0.117*	0.263 (2)
H18E	0.4480	0.5911	0.7307	0.117*	0.263 (2)
H18F	0.4163	0.4575	0.6778	0.117*	0.263 (2)
C19B	0.2941 (7)	0.7145 (10)	0.6051 (8)	0.0638 (9)	0.263 (2)
H19C	0.3516	0.7369	0.6184	0.077*	0.263 (2)
H19D	0.2743	0.7669	0.6514	0.077*	0.263 (2)
C20B	0.2441 (10)	0.7433 (17)	0.4914 (12)	0.1084 (14)	0.263 (2)
H20D	0.2631	0.8222	0.4705	0.163*	0.263 (2)
H20E	0.1867	0.7518	0.4840	0.163*	0.263 (2)
H20F	0.2502	0.6745	0.4468	0.163*	0.263 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0372 (6)	0.0335 (6)	0.0746 (8)	−0.0036 (5)	0.0323 (6)	−0.0024 (6)
O2	0.0355 (6)	0.0302 (6)	0.0627 (7)	0.0057 (5)	0.0241 (5)	−0.0005 (5)
O3	0.0436 (6)	0.0261 (6)	0.0720 (8)	0.0025 (5)	0.0322 (6)	0.0053 (6)
O4	0.0579 (8)	0.0797 (10)	0.0482 (7)	0.0027 (7)	0.0235 (6)	0.0003 (7)
O5	0.0564 (8)	0.0960 (12)	0.0855 (10)	0.0309 (8)	0.0208 (8)	0.0313 (9)
O6	0.0544 (8)	0.0975 (12)	0.1116 (12)	−0.0154 (9)	0.0535 (8)	−0.0263 (10)
O7	0.1076 (11)	0.0718 (11)	0.1226 (12)	−0.0225 (9)	0.0878 (10)	−0.0006 (10)
O8	0.0922 (11)	0.0574 (9)	0.0622 (9)	0.0063 (8)	0.0150 (8)	0.0182 (8)
O9	0.0671 (9)	0.0756 (10)	0.0556 (8)	−0.0225 (8)	0.0096 (7)	0.0040 (7)
N1	0.0354 (7)	0.0232 (7)	0.0567 (8)	0.0000 (6)	0.0248 (6)	0.0023 (6)
N2	0.0313 (7)	0.0268 (7)	0.0563 (8)	0.0036 (6)	0.0236 (6)	0.0000 (6)
N3	0.0389 (8)	0.0511 (10)	0.0536 (9)	−0.0006 (7)	0.0138 (7)	0.0033 (8)
N4	0.0679 (11)	0.0595 (11)	0.0883 (12)	−0.0223 (9)	0.0566 (9)	−0.0235 (10)
N5	0.0605 (10)	0.0497 (10)	0.0437 (8)	−0.0040 (8)	0.0213 (7)	0.0023 (8)
C1	0.0316 (8)	0.0305 (9)	0.0387 (8)	−0.0003 (7)	0.0180 (6)	−0.0021 (7)
C2	0.0300 (8)	0.0283 (8)	0.0409 (8)	0.0002 (7)	0.0175 (6)	−0.0010 (7)
C3	0.0328 (8)	0.0292 (9)	0.0415 (8)	−0.0015 (7)	0.0179 (7)	0.0001 (7)
C4	0.0341 (8)	0.0286 (9)	0.0435 (9)	−0.0013 (7)	0.0201 (7)	−0.0019 (7)
C5	0.0363 (8)	0.0230 (8)	0.0451 (9)	−0.0019 (7)	0.0221 (7)	−0.0055 (7)
C6	0.0358 (9)	0.0333 (9)	0.0485 (9)	−0.0016 (7)	0.0208 (7)	−0.0025 (7)
C7	0.0354 (9)	0.0438 (11)	0.0681 (12)	−0.0048 (8)	0.0250 (8)	−0.0088 (9)
C8	0.0490 (10)	0.0422 (11)	0.0682 (11)	−0.0136 (8)	0.0406 (9)	−0.0126 (9)
C9	0.0634 (11)	0.0361 (10)	0.0535 (10)	−0.0092 (9)	0.0371 (9)	−0.0032 (8)
C10	0.0439 (9)	0.0325 (9)	0.0444 (9)	−0.0031 (8)	0.0218 (7)	−0.0027 (7)
C11	0.1104 (17)	0.0874 (18)	0.1162 (19)	−0.0050 (15)	0.0782 (16)	−0.0365 (15)
C12	0.129 (2)	0.108 (2)	0.132 (2)	0.0100 (19)	0.0998 (18)	−0.0271 (18)
C13	0.0945 (16)	0.0876 (19)	0.120 (2)	0.0151 (16)	0.0767 (15)	0.0126 (16)
C14	0.0768 (15)	0.0693 (16)	0.123 (2)	0.0049 (13)	0.0556 (15)	−0.0040 (15)
C15	0.0652 (13)	0.0612 (14)	0.0858 (14)	0.0126 (11)	0.0423 (11)	−0.0077 (12)
C16	0.0614 (12)	0.0582 (13)	0.0528 (11)	0.0163 (10)	0.0274 (9)	−0.0032 (10)
N6A	0.0481 (9)	0.0417 (18)	0.0603 (11)	0.0222 (9)	0.0158 (8)	−0.0099 (11)
C17A	0.0508 (15)	0.066 (2)	0.0615 (16)	−0.0104 (14)	0.0186 (12)	−0.0075 (14)
C18A	0.083 (3)	0.088 (2)	0.0538 (17)	0.006 (2)	0.0123 (16)	0.0138 (16)
C19A	0.0846 (17)	0.0416 (17)	0.089 (3)	0.0056 (15)	0.0606 (19)	0.0075 (17)
C20A	0.116 (4)	0.103 (3)	0.104 (3)	0.038 (3)	0.035 (3)	0.049 (2)
N6B	0.0481 (9)	0.0417 (18)	0.0603 (11)	0.0222 (9)	0.0158 (8)	−0.0099 (11)
C17B	0.0508 (15)	0.066 (2)	0.0615 (16)	−0.0104 (14)	0.0186 (12)	−0.0075 (14)
C18B	0.083 (3)	0.088 (2)	0.0538 (17)	0.006 (2)	0.0123 (16)	0.0138 (16)
C19B	0.0846 (17)	0.0416 (17)	0.089 (3)	0.0056 (15)	0.0606 (19)	0.0075 (17)
C20B	0.116 (4)	0.103 (3)	0.104 (3)	0.038 (3)	0.035 (3)	0.049 (2)

Geometric parameters (Å, º) top

O1—C4	1.2273 (18)	C14—C15	1.376 (3)
O2—C1	1.2556 (18)	C14—H14	0.9300
O3—C3	1.2420 (19)	C15—C16	1.353 (3)
O4—N3	1.2104 (19)	C15—H15	0.9300
O5—N3	1.2137 (19)	C16—N6B	1.4915 (17)
O6—N4	1.217 (2)	C16—N6A	1.4921 (16)
O7—N4	1.214 (2)	N6A—C19A	1.521 (4)
O8—N5	1.215 (2)	N6A—C17A	1.528 (3)
O9—N5	1.210 (2)	N6A—H6AA	0.9100
N1—C4	1.357 (2)	C17A—C18A	1.491 (4)
N1—C1	1.3804 (19)	C17A—H17A	0.9700
N1—H1A	0.8600	C17A—H17B	0.9700
N2—C4	1.358 (2)	C18A—H18A	0.9600
N2—C3	1.388 (2)	C18A—H18B	0.9600
N2—H2A	0.8600	C18A—H18C	0.9600
N3—C6	1.473 (2)	C19A—C20A	1.462 (5)
N4—C8	1.467 (2)	C19A—H19A	0.9700
N5—C10	1.472 (2)	C19A—H19B	0.9700
C1—C2	1.395 (2)	C20A—H20A	0.9600
C2—C3	1.406 (2)	C20A—H20B	0.9600
C2—C5	1.457 (2)	C20A—H20C	0.9600
C5—C6	1.402 (2)	N6B—C19B	1.452 (11)
C5—C10	1.404 (2)	N6B—C17B	1.516 (10)
C6—C7	1.375 (2)	N6B—H6BA	0.9100
C7—C8	1.368 (3)	C17B—C18B	1.471 (11)
C7—H7	0.9300	C17B—H17C	0.9700
C8—C9	1.371 (3)	C17B—H17D	0.9700
C9—C10	1.376 (2)	C18B—H18D	0.9600
C9—H9	0.9300	C18B—H18E	0.9600
C11—C16	1.367 (3)	C18B—H18F	0.9600
C11—C12	1.377 (4)	C19B—C20B	1.493 (13)
C11—H11	0.9300	C19B—H19C	0.9700
C12—C13	1.352 (4)	C19B—H19D	0.9700
C12—H12	0.9300	C20B—H20D	0.9600
C13—C14	1.354 (4)	C20B—H20E	0.9600
C13—H13	0.9300	C20B—H20F	0.9600

C4—N1—C1	125.32 (13)	C16—C15—C14	120.2 (2)
C4—N1—H1A	117.3	C16—C15—H15	119.9
C1—N1—H1A	117.3	C14—C15—H15	119.9
C4—N2—C3	125.07 (13)	C15—C16—C11	120.07 (19)
C4—N2—H2A	117.5	C15—C16—N6B	112.1 (4)
C3—N2—H2A	117.5	C11—C16—N6B	126.9 (4)
O4—N3—O5	124.05 (17)	C15—C16—N6A	121.40 (18)
O4—N3—C6	118.80 (14)	C11—C16—N6A	118.3 (2)
O5—N3—C6	117.11 (16)	N6B—C16—N6A	16.7 (3)
O7—N4—O6	124.83 (18)	C16—N6A—C19A	117.10 (19)
O7—N4—C8	117.53 (18)	C16—N6A—C17A	116.53 (19)
O6—N4—C8	117.64 (19)	C19A—N6A—C17A	108.1 (2)
O9—N5—O8	124.43 (16)	C16—N6A—H6AA	104.5
O9—N5—C10	118.58 (15)	C19A—N6A—H6AA	104.5
O8—N5—C10	116.93 (16)	C17A—N6A—H6AA	104.5
O2—C1—N1	117.73 (14)	C18A—C17A—N6A	111.6 (2)
O2—C1—C2	125.62 (14)	C18A—C17A—H17A	109.3
N1—C1—C2	116.63 (13)	N6A—C17A—H17A	109.3
C1—C2—C3	120.99 (14)	C18A—C17A—H17B	109.3
C1—C2—C5	118.89 (13)	N6A—C17A—H17B	109.3
C3—C2—C5	120.04 (14)	H17A—C17A—H17B	108.0
O3—C3—N2	118.88 (14)	C20A—C19A—N6A	112.1 (3)
O3—C3—C2	124.89 (14)	C20A—C19A—H19A	109.2
N2—C3—C2	116.22 (14)	N6A—C19A—H19A	109.2
O1—C4—N1	122.47 (15)	C20A—C19A—H19B	109.2
O1—C4—N2	122.20 (14)	N6A—C19A—H19B	109.2
N1—C4—N2	115.33 (13)	H19A—C19A—H19B	107.9
C6—C5—C10	113.57 (14)	C19B—N6B—C16	97.3 (6)
C6—C5—C2	123.50 (14)	C19B—N6B—C17B	116.1 (7)
C10—C5—C2	122.79 (14)	C16—N6B—C17B	100.7 (4)
C7—C6—C5	124.14 (16)	C19B—N6B—H6BA	113.6
C7—C6—N3	115.60 (14)	C16—N6B—H6BA	113.6
C5—C6—N3	120.24 (14)	C17B—N6B—H6BA	113.6
C8—C7—C6	118.10 (16)	C18B—C17B—N6B	103.7 (6)
C8—C7—H7	120.9	C18B—C17B—H17C	111.0
C6—C7—H7	120.9	N6B—C17B—H17C	111.0
C7—C8—C9	121.94 (16)	C18B—C17B—H17D	111.0
C7—C8—N4	119.10 (17)	N6B—C17B—H17D	111.0
C9—C8—N4	118.97 (18)	H17C—C17B—H17D	109.0
C8—C9—C10	117.99 (17)	C17B—C18B—H18D	109.5
C8—C9—H9	121.0	C17B—C18B—H18E	109.5
C10—C9—H9	121.0	H18D—C18B—H18E	109.5
C9—C10—C5	124.14 (16)	C17B—C18B—H18F	109.5
C9—C10—N5	115.01 (15)	H18D—C18B—H18F	109.5
C5—C10—N5	120.69 (15)	H18E—C18B—H18F	109.5
C16—C11—C12	118.6 (3)	N6B—C19B—C20B	111.7 (10)
C16—C11—H11	120.7	N6B—C19B—H19C	109.3
C12—C11—H11	120.7	C20B—C19B—H19C	109.3
C13—C12—C11	121.6 (2)	N6B—C19B—H19D	109.3
C13—C12—H12	119.2	C20B—C19B—H19D	109.3
C11—C12—H12	119.2	H19C—C19B—H19D	107.9
C12—C13—C14	119.0 (2)	C19B—C20B—H20D	109.5
C12—C13—H13	120.5	C19B—C20B—H20E	109.5
C14—C13—H13	120.5	H20D—C20B—H20E	109.5
C13—C14—C15	120.4 (3)	C19B—C20B—H20F	109.5
C13—C14—H14	119.8	H20D—C20B—H20F	109.5
C15—C14—H14	119.8	H20E—C20B—H20F	109.5

C4—N1—C1—O2	−178.27 (14)	C8—C9—C10—N5	173.85 (15)
C4—N1—C1—C2	3.5 (2)	C6—C5—C10—C9	−1.0 (2)
O2—C1—C2—C3	175.83 (15)	C2—C5—C10—C9	174.90 (16)
N1—C1—C2—C3	−6.1 (2)	C6—C5—C10—N5	−176.29 (15)
O2—C1—C2—C5	−7.4 (2)	C2—C5—C10—N5	−0.4 (2)
N1—C1—C2—C5	170.69 (13)	O9—N5—C10—C9	−130.27 (18)
C4—N2—C3—O3	−177.23 (15)	O8—N5—C10—C9	46.9 (2)
C4—N2—C3—C2	3.7 (2)	O9—N5—C10—C5	45.5 (2)
C1—C2—C3—O3	−176.19 (15)	O8—N5—C10—C5	−137.36 (17)
C5—C2—C3—O3	7.0 (2)	C16—C11—C12—C13	0.7 (5)
C1—C2—C3—N2	2.8 (2)	C11—C12—C13—C14	−2.4 (5)
C5—C2—C3—N2	−173.94 (13)	C12—C13—C14—C15	1.6 (4)
C1—N1—C4—O1	−177.69 (15)	C13—C14—C15—C16	0.8 (4)
C1—N1—C4—N2	2.4 (2)	C14—C15—C16—C11	−2.5 (3)
C3—N2—C4—O1	173.89 (15)	C14—C15—C16—N6B	167.2 (3)
C3—N2—C4—N1	−6.2 (2)	C14—C15—C16—N6A	−177.3 (2)
C1—C2—C5—C6	53.8 (2)	C12—C11—C16—C15	1.7 (4)
C3—C2—C5—C6	−129.40 (17)	C12—C11—C16—N6B	−166.3 (4)
C1—C2—C5—C10	−121.69 (17)	C12—C11—C16—N6A	176.6 (2)
C3—C2—C5—C10	55.2 (2)	C15—C16—N6A—C19A	117.0 (3)
C10—C5—C6—C7	3.6 (2)	C11—C16—N6A—C19A	−57.9 (3)
C2—C5—C6—C7	−172.22 (16)	N6B—C16—N6A—C19A	176.7 (13)
C10—C5—C6—N3	−174.67 (14)	C15—C16—N6A—C17A	−112.9 (3)
C2—C5—C6—N3	9.5 (2)	C11—C16—N6A—C17A	72.3 (3)
O4—N3—C6—C7	−142.67 (17)	N6B—C16—N6A—C17A	−53.1 (11)
O5—N3—C6—C7	35.2 (2)	C16—N6A—C17A—C18A	59.0 (3)
O4—N3—C6—C5	35.8 (2)	C19A—N6A—C17A—C18A	−166.7 (3)
O5—N3—C6—C5	−146.41 (17)	C16—N6A—C19A—C20A	−51.4 (4)
C5—C6—C7—C8	−3.4 (3)	C17A—N6A—C19A—C20A	174.7 (3)
N3—C6—C7—C8	174.92 (16)	C15—C16—N6B—C19B	140.7 (5)
C6—C7—C8—C9	0.4 (3)	C11—C16—N6B—C19B	−50.4 (6)
C6—C7—C8—N4	−179.68 (16)	N6A—C16—N6B—C19B	13.4 (10)
O7—N4—C8—C7	158.40 (18)	C15—C16—N6B—C17B	−100.9 (6)
O6—N4—C8—C7	−21.1 (3)	C11—C16—N6B—C17B	68.0 (7)
O7—N4—C8—C9	−21.7 (3)	N6A—C16—N6B—C17B	131.8 (15)
O6—N4—C8—C9	158.82 (18)	C19B—N6B—C17B—C18B	−85.5 (9)
C7—C8—C9—C10	2.0 (3)	C16—N6B—C17B—C18B	170.8 (7)
N4—C8—C9—C10	−177.89 (15)	C16—N6B—C19B—C20B	−75.9 (11)
C8—C9—C10—C5	−1.7 (3)	C17B—N6B—C19B—C20B	178.4 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.01	2.8451 (18)	162
N2—H2A···O3ⁱⁱ	0.86	1.98	2.8230 (16)	167
N6A—H6AA···O2	0.91	1.88	2.790 (3)	175
N6B—H6BA···O2	0.91	1.71	2.617 (8)	174

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₆N⁺·C₁₀H₄N₅O₉⁻
M_r	488.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	17.1903 (7), 10.3925 (5), 13.3613 (5)
β (°)	110.272 (2)
V (Å³)	2239.14 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.923, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	3550, 3550, 2763
R_int	0.000
θ_max (°)	24.1
(sin θ/λ)_max (Å⁻¹)	0.575

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.03
No. of reflections	3550
No. of parameters	337
No. of restraints	9
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), 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
N1—H1A···O1ⁱ	0.86	2.01	2.8451 (18)	162.1
N2—H2A···O3ⁱⁱ	0.86	1.98	2.8230 (16)	166.7
N6A—H6AA···O2	0.91	1.88	2.790 (3)	174.7
N6B—H6BA···O2	0.91	1.71	2.617 (8)	173.8

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1.

Acknowledgements

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

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buvaneswari, M. & Kalaivani, D. (2011). Acta Cryst. E67, o1433–o1434. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 255–260. UK: WSEAS publication. Google Scholar
Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kalaivani, D., Malarvizhi, R. & Subbalakshmi, R. (2008). Med. Chem. Res. 17, 369–373. Web of Science CrossRef CAS Google Scholar
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. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Rizk, M. S., Issa, Y. M., Ahmed, M. A. & Shaaban, S. M. (1993). J. Mater. Sci. 4, 109–112. CAS Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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