N,N-Diethyl-2-hy­droxy­ethanaminium 2,6-dioxo-5-(2,4,6-trinitro­phen­yl)-1,2,3,6-tetra­hydro­pyrimidin-4-olate dihydrate

Buvaneswari, M.; Kalaivani, D.

doi:10.1107/S1600536811017363

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1433-o1434

doi:10.1107/S1600536811017363

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N,N-Diethyl-2-hydroxyethanaminium 2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate dihydrate

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 14 March 2011; accepted 8 May 2011; online 20 May 2011)

In the title molecular salt, C₆H₁₆NO⁺·C₁₀H₄N₅O₉⁻·2H₂O, which crystallizes as a dihydrate, O—H⋯O hydrogen bonds link the barbiturate anion, the ethanaminium cation and the water molecules of crystallization. The dihedral angle between the rings in the anion is 43.71 (8)°. In the crystal, an R₂²(8) ring motif hydrogen-bonding pattern is also found involving inversion-related barbiturate rings with N—H⋯O hydrogen bonds. As a result of the various hydrogen bonds an infinite two-dimensional network, propagating in (10 $[\overline{1}]$ ), is formed.

Related literature

For the anti-epileptic properties of barbiturates, see: Tripathi (2009 ); Kalaivani & Malarvizhi (2009 ); Kalaivani et al. (2008 ). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₆H₁₆NO⁺·C₁₀H₄N₅O₉⁻·2H₂O
M_r = 492.41
Monoclinic, P 2₁ /n
a = 8.3792 (2) Å
b = 21.7673 (4) Å
c = 12.0894 (2) Å
β = 96.118 (1)°
V = 2192.46 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 1999 ) T_min = 0.892, T_max = 0.975
23280 measured reflections
4686 independent reflections
3492 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.131
S = 1.08
4686 reflections
338 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10⋯O2Wⁱ	0.82	2.05	2.792 (2)	150
O10—H10⋯O4ⁱⁱ	0.82	2.49	3.0648 (19)	129
N6—H6⋯O1Wⁱⁱⁱ	0.91 (3)	1.95 (3)	2.846 (2)	170 (2)
N1—H1A⋯O10^iv	0.85 (2)	2.05 (3)	2.884 (2)	166 (2)
N2—H2A⋯O2^v	0.83 (2)	2.03 (2)	2.847 (2)	173 (2)
O1W—H2W⋯O2^v	0.91 (1)	1.90 (2)	2.7431 (19)	154 (2)
O2W—H4W⋯O1W^vi	0.93 (1)	1.94 (2)	2.796 (3)	152 (3)
O1W—H1W⋯O3	0.91 (1)	1.91 (1)	2.7783 (17)	160 (2)
O2W—H3W⋯O1	0.93 (1)	1.89 (2)	2.792 (2)	162 (4)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (v) -x+1, -y+1, -z; (vi) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus 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, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017363/su2264sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017363/su2264Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017363/su2264Isup3.cml

checkCIF report

Comment top

Most of the barbituric acid derivatives (barbiturates) are antiepileptic agents (Tripathi, 2009). The barbiturate prepared in our laboratory from 1-chloro-2,4-dinitrobenzene was obtained as maroon blocks when recrystallized from absolute alcohol (Kalaivani & Malarvizhi, 2009) and has antiepileptic activity (Kalaivani et al., 2008). We report here the crystal structure of a related barbiturate obtained from 1-chloro-2,4,6-trinitrobenzene (TNCB) and barbituric acid in the presence of 2(N,N-diethyl) ethanolamine. It shows an extra ordinary stability and very high solubility in dipolar aprotic solvents, such as dimethyl sulfoxide, which may be attributed to its salt-like structure.

The molecular structure of the title compound is illustrated in Fig. 1. The anion and cation are involved in O—H···O hydrogen bonds with the water molecules of crystallization (Table 1).

In the crystal a R₂²(8) ring motif hydrogen bonding pattern (Bernstein et al., 1995) is also found involving inversion-related barbiturate rings with N—H···O hydrogen bonds (Table 1 and Fig. 2). These various hydrogen bonds lead finally to the formation of an infinite two-dimensional network propagating in (10–1).

Related literature top

For the anti-epileptic properties of barbiturates, see: Tripathi (2009); Kalaivani & Malarvizhi (2009); Kalaivani et al. (2008). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995.)

Experimental top

Equimolar solutions of 1-chloro-2,4,6-trinitrobenzene (TNCB) and barbituric acid were prepared in ethanol and mixed. A three fold excess of 2(N,N-diethyl) ethanolamine was then added and the mixture was shaken well for 5–6 h. Maroon red coloured crystals were obtained after 24 hrs. The crystals were filtered and recrystallized from absolute alcohol (yield of pure crystals 70%, m.p. 507 K). 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.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus 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, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound with the numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. The O—H···O and N—H···O hydrogen bonds are shown as dashed lines (see Table 1 for details; C-bound H-atoms have been omitted for clarity).

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

Crystal data top

C₆H₁₆NO⁺·C₁₀H₄N₅O₉⁻·2H₂O	F(000) = 1032
M_r = 492.41	D_x = 1.492 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5467 reflections
a = 8.3792 (2) Å	θ = 2.6–24.8°
b = 21.7673 (4) Å	µ = 0.13 mm⁻¹
c = 12.0894 (2) Å	T = 293 K
β = 96.118 (1)°	Block, red
V = 2192.46 (8) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4686 independent reflections
Radiation source: fine-focus sealed tube	3492 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω and ϕ scans	θ_max = 26.8°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker 1999)	h = −10→10
T_min = 0.892, T_max = 0.975	k = −27→27
23280 measured reflections	l = −15→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0694P)² + 0.4079P] where P = (F_o² + 2F_c²)/3
4686 reflections	(Δ/σ)_max < 0.001
338 parameters	Δρ_max = 0.36 e Å⁻³
6 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₆H₁₆NO⁺·C₁₀H₄N₅O₉⁻·2H₂O	V = 2192.46 (8) Å³
M_r = 492.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.3792 (2) Å	µ = 0.13 mm⁻¹
b = 21.7673 (4) Å	T = 293 K
c = 12.0894 (2) Å	0.30 × 0.25 × 0.20 mm
β = 96.118 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4686 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 1999)	3492 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.975	R_int = 0.037
23280 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	6 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.36 e Å⁻³
4686 reflections	Δρ_min = −0.32 e Å⁻³
338 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.7186 (2)	0.41169 (8)	0.30054 (14)	0.0306 (4)
C2	0.5959 (2)	0.43691 (8)	0.11393 (15)	0.0388 (4)
C3	0.6102 (2)	0.51490 (7)	0.25866 (14)	0.0300 (4)
C4	0.6886 (2)	0.47250 (7)	0.33442 (14)	0.0292 (4)
C5	0.73603 (19)	0.49194 (7)	0.44825 (13)	0.0266 (3)
C6	0.81044 (19)	0.54867 (8)	0.47588 (14)	0.0302 (4)
C7	0.8515 (2)	0.56930 (8)	0.58266 (15)	0.0356 (4)
H7	0.8973	0.6079	0.5960	0.043*
C8	0.8230 (2)	0.53139 (8)	0.66853 (15)	0.0350 (4)
C9	0.7534 (2)	0.47444 (8)	0.65025 (15)	0.0327 (4)
H9	0.7364	0.4487	0.7092	0.039*
C10	0.70989 (19)	0.45705 (7)	0.54204 (14)	0.0286 (4)
C11	0.4444 (3)	0.22119 (12)	0.27523 (19)	0.0554 (6)
H11A	0.5560	0.2339	0.2822	0.067*
H11B	0.4334	0.1863	0.2251	0.067*
C12	0.3427 (4)	0.27264 (14)	0.2257 (2)	0.0765 (8)
H12A	0.2315	0.2631	0.2295	0.115*
H12B	0.3616	0.2782	0.1494	0.115*
H12C	0.3695	0.3098	0.2664	0.115*
C13	0.4327 (3)	0.25114 (9)	0.47133 (18)	0.0488 (5)
H13A	0.3762	0.2878	0.4436	0.059*
H13B	0.5466	0.2604	0.4794	0.059*
C14	0.3828 (3)	0.23605 (10)	0.58351 (17)	0.0475 (5)
H14A	0.4519	0.2039	0.6172	0.057*
H14B	0.3969	0.2721	0.6307	0.057*
C15	0.4762 (3)	0.14050 (9)	0.42105 (19)	0.0504 (5)
H15A	0.4378	0.1276	0.4903	0.060*
H15B	0.4401	0.1103	0.3648	0.060*
C16	0.6552 (3)	0.14057 (14)	0.4358 (2)	0.0731 (8)
H16A	0.6949	0.1503	0.3663	0.110*
H16B	0.6933	0.1007	0.4602	0.110*
H16C	0.6926	0.1707	0.4905	0.110*
N1	0.6672 (2)	0.39757 (7)	0.19009 (13)	0.0372 (4)
N2	0.5695 (2)	0.49417 (7)	0.15108 (13)	0.0399 (4)
N3	0.85714 (19)	0.59043 (7)	0.38903 (14)	0.0390 (4)
N4	0.8702 (2)	0.55069 (9)	0.78267 (15)	0.0504 (4)
N5	0.62095 (18)	0.39864 (6)	0.53118 (12)	0.0323 (3)
N6	0.4013 (2)	0.20141 (7)	0.38774 (14)	0.0391 (4)
O1	0.78610 (16)	0.37089 (6)	0.35927 (10)	0.0405 (3)
O2	0.5564 (2)	0.42190 (6)	0.01670 (11)	0.0583 (4)
O1W	0.42307 (17)	0.66131 (6)	0.15158 (11)	0.0433 (3)
O3	0.57236 (15)	0.56815 (5)	0.28132 (10)	0.0351 (3)
O2W	0.9751 (3)	0.27123 (10)	0.4379 (2)	0.1173 (10)
O4	0.8348 (2)	0.64511 (6)	0.40147 (14)	0.0615 (4)
O5	0.92002 (16)	0.56847 (7)	0.31178 (12)	0.0482 (4)
O6	0.9235 (3)	0.60220 (9)	0.79794 (14)	0.0794 (6)
O7	0.8528 (3)	0.51453 (9)	0.85712 (14)	0.0882 (7)
O8	0.66984 (18)	0.35673 (6)	0.59242 (12)	0.0486 (4)
O9	0.50041 (15)	0.39638 (6)	0.46545 (11)	0.0408 (3)
O10	0.22086 (17)	0.21639 (6)	0.57806 (12)	0.0449 (3)
H10	0.1618	0.2438	0.5511	0.071 (8)*
H6	0.294 (3)	0.1935 (11)	0.377 (2)	0.063 (7)*
H1A	0.686 (3)	0.3612 (11)	0.1685 (19)	0.052 (6)*
H2A	0.526 (3)	0.5191 (10)	0.1057 (18)	0.044 (6)*
H1W	0.467 (3)	0.6368 (9)	0.2074 (13)	0.071 (8)*
H2W	0.424 (4)	0.6446 (11)	0.0830 (10)	0.091 (10)*
H4W	0.978 (5)	0.2365 (12)	0.393 (3)	0.162 (18)*
H3W	0.895 (4)	0.2983 (15)	0.411 (3)	0.160 (17)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0348 (9)	0.0271 (8)	0.0296 (9)	0.0051 (7)	0.0016 (7)	−0.0002 (7)
C2	0.0517 (11)	0.0312 (9)	0.0317 (9)	0.0083 (8)	−0.0043 (8)	−0.0032 (8)
C3	0.0314 (8)	0.0280 (8)	0.0301 (9)	0.0034 (7)	0.0004 (7)	−0.0016 (7)
C4	0.0326 (9)	0.0261 (8)	0.0279 (8)	0.0042 (7)	−0.0011 (7)	−0.0002 (7)
C5	0.0244 (8)	0.0238 (8)	0.0306 (8)	0.0049 (6)	−0.0014 (6)	−0.0006 (6)
C6	0.0292 (8)	0.0260 (8)	0.0347 (9)	0.0010 (6)	−0.0005 (7)	0.0006 (7)
C7	0.0334 (9)	0.0296 (9)	0.0425 (10)	−0.0024 (7)	−0.0016 (7)	−0.0068 (8)
C8	0.0330 (9)	0.0385 (10)	0.0318 (9)	0.0007 (7)	−0.0046 (7)	−0.0087 (8)
C9	0.0334 (9)	0.0329 (9)	0.0306 (9)	0.0022 (7)	−0.0021 (7)	0.0028 (7)
C10	0.0282 (8)	0.0234 (8)	0.0332 (9)	0.0010 (6)	−0.0017 (6)	−0.0008 (7)
C11	0.0560 (13)	0.0660 (15)	0.0457 (12)	−0.0002 (11)	0.0114 (10)	0.0030 (11)
C12	0.0832 (19)	0.085 (2)	0.0612 (16)	0.0084 (15)	0.0074 (14)	0.0235 (14)
C13	0.0556 (13)	0.0366 (10)	0.0552 (13)	−0.0108 (9)	0.0103 (10)	−0.0117 (9)
C14	0.0560 (13)	0.0404 (11)	0.0445 (11)	−0.0031 (9)	−0.0013 (9)	−0.0096 (9)
C15	0.0569 (13)	0.0376 (11)	0.0558 (13)	0.0069 (9)	0.0021 (10)	−0.0051 (9)
C16	0.0578 (15)	0.0869 (19)	0.0718 (17)	0.0213 (14)	−0.0061 (12)	−0.0082 (15)
N1	0.0529 (10)	0.0254 (8)	0.0319 (8)	0.0097 (7)	−0.0019 (7)	−0.0048 (6)
N2	0.0599 (11)	0.0290 (8)	0.0278 (8)	0.0144 (7)	−0.0094 (7)	−0.0010 (6)
N3	0.0379 (8)	0.0326 (8)	0.0460 (9)	−0.0053 (6)	0.0016 (7)	0.0030 (7)
N4	0.0570 (11)	0.0543 (11)	0.0378 (9)	−0.0070 (9)	−0.0040 (8)	−0.0117 (8)
N5	0.0382 (8)	0.0256 (7)	0.0328 (8)	−0.0008 (6)	0.0016 (6)	0.0000 (6)
N6	0.0398 (9)	0.0343 (8)	0.0432 (9)	−0.0031 (7)	0.0049 (7)	−0.0058 (7)
O1	0.0522 (8)	0.0303 (6)	0.0374 (7)	0.0153 (6)	−0.0020 (6)	0.0024 (5)
O2	0.0989 (13)	0.0384 (8)	0.0327 (7)	0.0199 (8)	−0.0160 (7)	−0.0091 (6)
O1W	0.0544 (8)	0.0367 (7)	0.0372 (8)	0.0126 (6)	−0.0024 (6)	0.0005 (6)
O3	0.0445 (7)	0.0252 (6)	0.0340 (6)	0.0100 (5)	−0.0029 (5)	−0.0019 (5)
O2W	0.142 (2)	0.0625 (13)	0.128 (2)	0.0511 (14)	−0.0737 (17)	−0.0340 (13)
O4	0.0903 (13)	0.0250 (7)	0.0697 (11)	−0.0070 (7)	0.0110 (9)	0.0037 (7)
O5	0.0441 (8)	0.0523 (8)	0.0502 (8)	0.0017 (6)	0.0148 (7)	0.0066 (7)
O6	0.1110 (16)	0.0719 (12)	0.0536 (10)	−0.0391 (11)	0.0006 (10)	−0.0260 (9)
O7	0.150 (2)	0.0752 (13)	0.0342 (9)	−0.0199 (13)	−0.0119 (10)	−0.0011 (9)
O8	0.0660 (10)	0.0280 (7)	0.0497 (8)	−0.0008 (6)	−0.0039 (7)	0.0100 (6)
O9	0.0360 (7)	0.0376 (7)	0.0469 (8)	−0.0067 (5)	−0.0036 (6)	−0.0036 (6)
O10	0.0520 (8)	0.0322 (7)	0.0504 (8)	−0.0001 (6)	0.0049 (6)	0.0069 (6)

Geometric parameters (Å, º) top

C1—O1	1.236 (2)	C13—N6	1.485 (2)
C1—N1	1.393 (2)	C13—C14	1.497 (3)
C1—C4	1.416 (2)	C13—H13A	0.9700
C2—O2	1.231 (2)	C13—H13B	0.9700
C2—N1	1.350 (2)	C14—O10	1.418 (3)
C2—N2	1.351 (2)	C14—H14A	0.9700
C3—O3	1.240 (2)	C14—H14B	0.9700
C3—N2	1.385 (2)	C15—C16	1.492 (3)
C3—C4	1.412 (2)	C15—N6	1.503 (3)
C4—C5	1.454 (2)	C15—H15A	0.9700
C5—C10	1.401 (2)	C15—H15B	0.9700
C5—C6	1.407 (2)	C16—H16A	0.9600
C6—C7	1.376 (2)	C16—H16B	0.9600
C6—N3	1.473 (2)	C16—H16C	0.9600
C7—C8	1.367 (3)	N1—H1A	0.85 (2)
C7—H7	0.9300	N2—H2A	0.83 (2)
C8—C9	1.378 (2)	N3—O4	1.217 (2)
C8—N4	1.456 (2)	N3—O5	1.218 (2)
C9—C10	1.373 (2)	N4—O6	1.214 (2)
C9—H9	0.9300	N4—O7	1.216 (2)
C10—N5	1.472 (2)	N5—O9	1.2177 (19)
C11—C12	1.493 (3)	N5—O8	1.2180 (18)
C11—N6	1.507 (3)	N6—H6	0.91 (3)
C11—H11A	0.9700	O1W—H1W	0.908 (9)
C11—H11B	0.9700	O1W—H2W	0.907 (9)
C12—H12A	0.9600	O2W—H4W	0.933 (10)
C12—H12B	0.9600	O2W—H3W	0.929 (10)
C12—H12C	0.9600	O10—H10	0.8200

O1—C1—N1	117.90 (15)	N6—C13—H13B	108.7
O1—C1—C4	126.17 (15)	C14—C13—H13B	108.7
N1—C1—C4	115.93 (14)	H13A—C13—H13B	107.6
O2—C2—N1	122.52 (17)	O10—C14—C13	112.47 (17)
O2—C2—N2	121.69 (17)	O10—C14—H14A	109.1
N1—C2—N2	115.79 (16)	C13—C14—H14A	109.1
O3—C3—N2	117.98 (15)	O10—C14—H14B	109.1
O3—C3—C4	125.44 (15)	C13—C14—H14B	109.1
N2—C3—C4	116.56 (15)	H14A—C14—H14B	107.8
C3—C4—C1	120.54 (15)	C16—C15—N6	114.6 (2)
C3—C4—C5	119.01 (14)	C16—C15—H15A	108.6
C1—C4—C5	120.44 (14)	N6—C15—H15A	108.6
C10—C5—C6	112.77 (14)	C16—C15—H15B	108.6
C10—C5—C4	123.89 (15)	N6—C15—H15B	108.6
C6—C5—C4	123.33 (15)	H15A—C15—H15B	107.6
C7—C6—C5	124.70 (16)	C15—C16—H16A	109.5
C7—C6—N3	114.12 (15)	C15—C16—H16B	109.5
C5—C6—N3	121.13 (15)	H16A—C16—H16B	109.5
C8—C7—C6	117.98 (16)	C15—C16—H16C	109.5
C8—C7—H7	121.0	H16A—C16—H16C	109.5
C6—C7—H7	121.0	H16B—C16—H16C	109.5
C7—C8—C9	121.78 (16)	C2—N1—C1	125.68 (15)
C7—C8—N4	119.59 (16)	C2—N1—H1A	117.5 (15)
C9—C8—N4	118.62 (17)	C1—N1—H1A	116.8 (15)
C10—C9—C8	117.76 (16)	C2—N2—C3	125.47 (16)
C10—C9—H9	121.1	C2—N2—H2A	117.4 (15)
C8—C9—H9	121.1	C3—N2—H2A	117.1 (15)
C9—C10—C5	124.95 (15)	O4—N3—O5	124.29 (17)
C9—C10—N5	113.79 (15)	O4—N3—C6	117.36 (16)
C5—C10—N5	121.14 (14)	O5—N3—C6	118.30 (15)
C12—C11—N6	113.3 (2)	O6—N4—O7	123.81 (18)
C12—C11—H11A	108.9	O6—N4—C8	117.96 (19)
N6—C11—H11A	108.9	O7—N4—C8	118.22 (17)
C12—C11—H11B	108.9	O9—N5—O8	124.63 (15)
N6—C11—H11B	108.9	O9—N5—C10	118.02 (14)
H11A—C11—H11B	107.7	O8—N5—C10	117.27 (14)
C11—C12—H12A	109.5	C13—N6—C15	114.97 (17)
C11—C12—H12B	109.5	C13—N6—C11	111.34 (16)
H12A—C12—H12B	109.5	C15—N6—C11	111.13 (17)
C11—C12—H12C	109.5	C13—N6—H6	109.8 (16)
H12A—C12—H12C	109.5	C15—N6—H6	104.4 (16)
H12B—C12—H12C	109.5	C11—N6—H6	104.5 (16)
N6—C13—C14	114.21 (16)	H1W—O1W—H2W	113.6 (14)
N6—C13—H13A	108.7	H4W—O2W—H3W	111.6 (16)
C14—C13—H13A	108.7	C14—O10—H10	109.5

O3—C3—C4—C1	176.75 (17)	N6—C13—C14—O10	−53.0 (2)
N2—C3—C4—C1	−1.6 (2)	O2—C2—N1—C1	178.4 (2)
O3—C3—C4—C5	−2.4 (3)	N2—C2—N1—C1	−2.0 (3)
N2—C3—C4—C5	179.24 (16)	O1—C1—N1—C2	−178.03 (18)
O1—C1—C4—C3	179.91 (17)	C4—C1—N1—C2	1.6 (3)
N1—C1—C4—C3	0.3 (2)	O2—C2—N2—C3	−179.9 (2)
O1—C1—C4—C5	−1.0 (3)	N1—C2—N2—C3	0.4 (3)
N1—C1—C4—C5	179.45 (15)	O3—C3—N2—C2	−177.22 (18)
C3—C4—C5—C10	134.25 (17)	C4—C3—N2—C2	1.3 (3)
C1—C4—C5—C10	−44.9 (2)	C7—C6—N3—O4	−42.6 (2)
C3—C4—C5—C6	−44.4 (2)	C5—C6—N3—O4	139.73 (18)
C1—C4—C5—C6	136.50 (17)	C7—C6—N3—O5	135.05 (17)
C10—C5—C6—C7	−1.2 (2)	C5—C6—N3—O5	−42.6 (2)
C4—C5—C6—C7	177.56 (16)	C7—C8—N4—O6	5.1 (3)
C10—C5—C6—N3	176.24 (15)	C9—C8—N4—O6	−176.2 (2)
C4—C5—C6—N3	−5.0 (2)	C7—C8—N4—O7	−175.4 (2)
C5—C6—C7—C8	2.2 (3)	C9—C8—N4—O7	3.3 (3)
N3—C6—C7—C8	−175.40 (16)	C9—C10—N5—O9	133.96 (16)
C6—C7—C8—C9	−0.9 (3)	C5—C10—N5—O9	−42.3 (2)
C6—C7—C8—N4	177.78 (16)	C9—C10—N5—O8	−42.9 (2)
C7—C8—C9—C10	−1.3 (3)	C5—C10—N5—O8	140.79 (16)
N4—C8—C9—C10	−179.93 (16)	C14—C13—N6—C15	−56.2 (2)
C8—C9—C10—C5	2.4 (3)	C14—C13—N6—C11	176.34 (19)
C8—C9—C10—N5	−173.72 (15)	C16—C15—N6—C13	−64.0 (3)
C6—C5—C10—C9	−1.2 (2)	C16—C15—N6—C11	63.6 (2)
C4—C5—C10—C9	−179.92 (16)	C12—C11—N6—C13	−64.7 (3)
C6—C5—C10—N5	174.67 (14)	C12—C11—N6—C15	165.7 (2)
C4—C5—C10—N5	−4.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O2Wⁱ	0.82	2.05	2.792 (2)	150
O10—H10···O4ⁱⁱ	0.82	2.49	3.0648 (19)	129
N6—H6···O1Wⁱⁱⁱ	0.91 (3)	1.95 (3)	2.846 (2)	170 (2)
N1—H1A···O10^iv	0.85 (2)	2.05 (3)	2.884 (2)	166 (2)
N2—H2A···O2^v	0.83 (2)	2.03 (2)	2.847 (2)	173 (2)
O1W—H2W···O2^v	0.91 (1)	1.90 (2)	2.7431 (19)	154 (2)
O2W—H4W···O1W^vi	0.93 (1)	1.94 (2)	2.796 (3)	152 (3)
O1W—H1W···O3	0.91 (1)	1.91 (1)	2.7783 (17)	160 (2)
O2W—H3W···O1	0.93 (1)	1.89 (2)	2.792 (2)	162 (4)

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

Experimental details

Crystal data
Chemical formula	C₆H₁₆NO⁺·C₁₀H₄N₅O₉⁻·2H₂O
M_r	492.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.3792 (2), 21.7673 (4), 12.0894 (2)
β (°)	96.118 (1)
V (Å³)	2192.46 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 1999)
T_min, T_max	0.892, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	23280, 4686, 3492
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.131, 1.08
No. of reflections	4686
No. of parameters	338
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.32

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O2Wⁱ	0.82	2.05	2.792 (2)	150
O10—H10···O4ⁱⁱ	0.82	2.49	3.0648 (19)	129
N6—H6···O1Wⁱⁱⁱ	0.91 (3)	1.95 (3)	2.846 (2)	170 (2)
N1—H1A···O10^iv	0.85 (2)	2.05 (3)	2.884 (2)	166 (2)
N2—H2A···O2^v	0.83 (2)	2.03 (2)	2.847 (2)	173 (2)
O1W—H2W···O2^v	0.907 (9)	1.902 (15)	2.7431 (19)	154 (2)
O2W—H4W···O1W^vi	0.933 (10)	1.937 (18)	2.796 (3)	152 (3)
O1W—H1W···O3	0.908 (9)	1.908 (13)	2.7783 (17)	160 (2)
O2W—H3W···O1	0.929 (10)	1.894 (16)	2.792 (2)	162 (4)

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

Acknowledgements

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

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1999). SADABS, Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2, XPREP and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals 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., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 6| June 2011| Pages o1433-o1434

doi:10.1107/S1600536811017363

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

N,N-Di­ethyl-2-hy­dr­oxy­ethanaminium 2,6-dioxo-5-(2,4,6-tri­nitro­phen­yl)-1,2,3,6-tetra­hydro­pyrimidin-4-olate dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N-Diethyl-2-hydroxyethanaminium 2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate dihydrate