Literature DB >> 21754812

N,N-Diethyl-2-hy-droxy-ethanaminium 2,6-dioxo-5-(2,4,6-trinitro-phen-yl)-1,2,3,6-tetra-hydro-pyrimidin-4-olate dihydrate.

Manickam Buvaneswari1, Doraisamyraja Kalaivani.   

Abstract

In the title mol-ecular salt, C(6)H(16)NO(+)·C(10)H(4)N(5)O(9) (-)·2H(2)O, which crystallizes as a dihydrate, O-H⋯O hydrogen bonds link the barbiturate anion, the ethanaminium cation and the water mol-ecules of crystallization. The dihedral angle between the rings in the anion is 43.71 (8)°. In the crystal, an R(2) (2)(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[Formula: see text]), is formed.

Entities:  

Year:  2011        PMID: 21754812      PMCID: PMC3120611          DOI: 10.1107/S1600536811017363

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


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 = 492.41 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.131 S = 1.08 4686 reflections 338 parameters 6 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.36 e Å−3 Δρmin = −0.32 e Å−3 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017363/su2264sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811017363/su2264Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811017363/su2264Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C6H16NO+·C10H4N5O9·2H2OF(000) = 1032
Mr = 492.41Dx = 1.492 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5467 reflections
a = 8.3792 (2) Åθ = 2.6–24.8°
b = 21.7673 (4) ŵ = 0.13 mm1
c = 12.0894 (2) ÅT = 293 K
β = 96.118 (1)°Block, red
V = 2192.46 (8) Å30.30 × 0.25 × 0.20 mm
Z = 4
Bruker Kappa APEXII CCD diffractometer4686 independent reflections
Radiation source: fine-focus sealed tube3492 reflections with I > 2σ(I)
graphiteRint = 0.037
ω and φ scansθmax = 26.8°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker 1999)h = −10→10
Tmin = 0.892, Tmax = 0.975k = −27→27
23280 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0694P)2 + 0.4079P] where P = (Fo2 + 2Fc2)/3
4686 reflections(Δ/σ)max < 0.001
338 parametersΔρmax = 0.36 e Å3
6 restraintsΔρmin = −0.32 e Å3
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.
xyzUiso*/Ueq
C10.7186 (2)0.41169 (8)0.30054 (14)0.0306 (4)
C20.5959 (2)0.43691 (8)0.11393 (15)0.0388 (4)
C30.6102 (2)0.51490 (7)0.25866 (14)0.0300 (4)
C40.6886 (2)0.47250 (7)0.33442 (14)0.0292 (4)
C50.73603 (19)0.49194 (7)0.44825 (13)0.0266 (3)
C60.81044 (19)0.54867 (8)0.47588 (14)0.0302 (4)
C70.8515 (2)0.56930 (8)0.58266 (15)0.0356 (4)
H70.89730.60790.59600.043*
C80.8230 (2)0.53139 (8)0.66853 (15)0.0350 (4)
C90.7534 (2)0.47444 (8)0.65025 (15)0.0327 (4)
H90.73640.44870.70920.039*
C100.70989 (19)0.45705 (7)0.54204 (14)0.0286 (4)
C110.4444 (3)0.22119 (12)0.27523 (19)0.0554 (6)
H11A0.55600.23390.28220.067*
H11B0.43340.18630.22510.067*
C120.3427 (4)0.27264 (14)0.2257 (2)0.0765 (8)
H12A0.23150.26310.22950.115*
H12B0.36160.27820.14940.115*
H12C0.36950.30980.26640.115*
C130.4327 (3)0.25114 (9)0.47133 (18)0.0488 (5)
H13A0.37620.28780.44360.059*
H13B0.54660.26040.47940.059*
C140.3828 (3)0.23605 (10)0.58351 (17)0.0475 (5)
H14A0.45190.20390.61720.057*
H14B0.39690.27210.63070.057*
C150.4762 (3)0.14050 (9)0.42105 (19)0.0504 (5)
H15A0.43780.12760.49030.060*
H15B0.44010.11030.36480.060*
C160.6552 (3)0.14057 (14)0.4358 (2)0.0731 (8)
H16A0.69490.15030.36630.110*
H16B0.69330.10070.46020.110*
H16C0.69260.17070.49050.110*
N10.6672 (2)0.39757 (7)0.19009 (13)0.0372 (4)
N20.5695 (2)0.49417 (7)0.15108 (13)0.0399 (4)
N30.85714 (19)0.59043 (7)0.38903 (14)0.0390 (4)
N40.8702 (2)0.55069 (9)0.78267 (15)0.0504 (4)
N50.62095 (18)0.39864 (6)0.53118 (12)0.0323 (3)
N60.4013 (2)0.20141 (7)0.38774 (14)0.0391 (4)
O10.78610 (16)0.37089 (6)0.35927 (10)0.0405 (3)
O20.5564 (2)0.42190 (6)0.01670 (11)0.0583 (4)
O1W0.42307 (17)0.66131 (6)0.15158 (11)0.0433 (3)
O30.57236 (15)0.56815 (5)0.28132 (10)0.0351 (3)
O2W0.9751 (3)0.27123 (10)0.4379 (2)0.1173 (10)
O40.8348 (2)0.64511 (6)0.40147 (14)0.0615 (4)
O50.92002 (16)0.56847 (7)0.31178 (12)0.0482 (4)
O60.9235 (3)0.60220 (9)0.79794 (14)0.0794 (6)
O70.8528 (3)0.51453 (9)0.85712 (14)0.0882 (7)
O80.66984 (18)0.35673 (6)0.59242 (12)0.0486 (4)
O90.50041 (15)0.39638 (6)0.46545 (11)0.0408 (3)
O100.22086 (17)0.21639 (6)0.57806 (12)0.0449 (3)
H100.16180.24380.55110.071 (8)*
H60.294 (3)0.1935 (11)0.377 (2)0.063 (7)*
H1A0.686 (3)0.3612 (11)0.1685 (19)0.052 (6)*
H2A0.526 (3)0.5191 (10)0.1057 (18)0.044 (6)*
H1W0.467 (3)0.6368 (9)0.2074 (13)0.071 (8)*
H2W0.424 (4)0.6446 (11)0.0830 (10)0.091 (10)*
H4W0.978 (5)0.2365 (12)0.393 (3)0.162 (18)*
H3W0.895 (4)0.2983 (15)0.411 (3)0.160 (17)*
U11U22U33U12U13U23
C10.0348 (9)0.0271 (8)0.0296 (9)0.0051 (7)0.0016 (7)−0.0002 (7)
C20.0517 (11)0.0312 (9)0.0317 (9)0.0083 (8)−0.0043 (8)−0.0032 (8)
C30.0314 (8)0.0280 (8)0.0301 (9)0.0034 (7)0.0004 (7)−0.0016 (7)
C40.0326 (9)0.0261 (8)0.0279 (8)0.0042 (7)−0.0011 (7)−0.0002 (7)
C50.0244 (8)0.0238 (8)0.0306 (8)0.0049 (6)−0.0014 (6)−0.0006 (6)
C60.0292 (8)0.0260 (8)0.0347 (9)0.0010 (6)−0.0005 (7)0.0006 (7)
C70.0334 (9)0.0296 (9)0.0425 (10)−0.0024 (7)−0.0016 (7)−0.0068 (8)
C80.0330 (9)0.0385 (10)0.0318 (9)0.0007 (7)−0.0046 (7)−0.0087 (8)
C90.0334 (9)0.0329 (9)0.0306 (9)0.0022 (7)−0.0021 (7)0.0028 (7)
C100.0282 (8)0.0234 (8)0.0332 (9)0.0010 (6)−0.0017 (6)−0.0008 (7)
C110.0560 (13)0.0660 (15)0.0457 (12)−0.0002 (11)0.0114 (10)0.0030 (11)
C120.0832 (19)0.085 (2)0.0612 (16)0.0084 (15)0.0074 (14)0.0235 (14)
C130.0556 (13)0.0366 (10)0.0552 (13)−0.0108 (9)0.0103 (10)−0.0117 (9)
C140.0560 (13)0.0404 (11)0.0445 (11)−0.0031 (9)−0.0013 (9)−0.0096 (9)
C150.0569 (13)0.0376 (11)0.0558 (13)0.0069 (9)0.0021 (10)−0.0051 (9)
C160.0578 (15)0.0869 (19)0.0718 (17)0.0213 (14)−0.0061 (12)−0.0082 (15)
N10.0529 (10)0.0254 (8)0.0319 (8)0.0097 (7)−0.0019 (7)−0.0048 (6)
N20.0599 (11)0.0290 (8)0.0278 (8)0.0144 (7)−0.0094 (7)−0.0010 (6)
N30.0379 (8)0.0326 (8)0.0460 (9)−0.0053 (6)0.0016 (7)0.0030 (7)
N40.0570 (11)0.0543 (11)0.0378 (9)−0.0070 (9)−0.0040 (8)−0.0117 (8)
N50.0382 (8)0.0256 (7)0.0328 (8)−0.0008 (6)0.0016 (6)0.0000 (6)
N60.0398 (9)0.0343 (8)0.0432 (9)−0.0031 (7)0.0049 (7)−0.0058 (7)
O10.0522 (8)0.0303 (6)0.0374 (7)0.0153 (6)−0.0020 (6)0.0024 (5)
O20.0989 (13)0.0384 (8)0.0327 (7)0.0199 (8)−0.0160 (7)−0.0091 (6)
O1W0.0544 (8)0.0367 (7)0.0372 (8)0.0126 (6)−0.0024 (6)0.0005 (6)
O30.0445 (7)0.0252 (6)0.0340 (6)0.0100 (5)−0.0029 (5)−0.0019 (5)
O2W0.142 (2)0.0625 (13)0.128 (2)0.0511 (14)−0.0737 (17)−0.0340 (13)
O40.0903 (13)0.0250 (7)0.0697 (11)−0.0070 (7)0.0110 (9)0.0037 (7)
O50.0441 (8)0.0523 (8)0.0502 (8)0.0017 (6)0.0148 (7)0.0066 (7)
O60.1110 (16)0.0719 (12)0.0536 (10)−0.0391 (11)0.0006 (10)−0.0260 (9)
O70.150 (2)0.0752 (13)0.0342 (9)−0.0199 (13)−0.0119 (10)−0.0011 (9)
O80.0660 (10)0.0280 (7)0.0497 (8)−0.0008 (6)−0.0039 (7)0.0100 (6)
O90.0360 (7)0.0376 (7)0.0469 (8)−0.0067 (5)−0.0036 (6)−0.0036 (6)
O100.0520 (8)0.0322 (7)0.0504 (8)−0.0001 (6)0.0049 (6)0.0069 (6)
C1—O11.236 (2)C13—N61.485 (2)
C1—N11.393 (2)C13—C141.497 (3)
C1—C41.416 (2)C13—H13A0.9700
C2—O21.231 (2)C13—H13B0.9700
C2—N11.350 (2)C14—O101.418 (3)
C2—N21.351 (2)C14—H14A0.9700
C3—O31.240 (2)C14—H14B0.9700
C3—N21.385 (2)C15—C161.492 (3)
C3—C41.412 (2)C15—N61.503 (3)
C4—C51.454 (2)C15—H15A0.9700
C5—C101.401 (2)C15—H15B0.9700
C5—C61.407 (2)C16—H16A0.9600
C6—C71.376 (2)C16—H16B0.9600
C6—N31.473 (2)C16—H16C0.9600
C7—C81.367 (3)N1—H1A0.85 (2)
C7—H70.9300N2—H2A0.83 (2)
C8—C91.378 (2)N3—O41.217 (2)
C8—N41.456 (2)N3—O51.218 (2)
C9—C101.373 (2)N4—O61.214 (2)
C9—H90.9300N4—O71.216 (2)
C10—N51.472 (2)N5—O91.2177 (19)
C11—C121.493 (3)N5—O81.2180 (18)
C11—N61.507 (3)N6—H60.91 (3)
C11—H11A0.9700O1W—H1W0.908 (9)
C11—H11B0.9700O1W—H2W0.907 (9)
C12—H12A0.9600O2W—H4W0.933 (10)
C12—H12B0.9600O2W—H3W0.929 (10)
C12—H12C0.9600O10—H100.8200
O1—C1—N1117.90 (15)N6—C13—H13B108.7
O1—C1—C4126.17 (15)C14—C13—H13B108.7
N1—C1—C4115.93 (14)H13A—C13—H13B107.6
O2—C2—N1122.52 (17)O10—C14—C13112.47 (17)
O2—C2—N2121.69 (17)O10—C14—H14A109.1
N1—C2—N2115.79 (16)C13—C14—H14A109.1
O3—C3—N2117.98 (15)O10—C14—H14B109.1
O3—C3—C4125.44 (15)C13—C14—H14B109.1
N2—C3—C4116.56 (15)H14A—C14—H14B107.8
C3—C4—C1120.54 (15)C16—C15—N6114.6 (2)
C3—C4—C5119.01 (14)C16—C15—H15A108.6
C1—C4—C5120.44 (14)N6—C15—H15A108.6
C10—C5—C6112.77 (14)C16—C15—H15B108.6
C10—C5—C4123.89 (15)N6—C15—H15B108.6
C6—C5—C4123.33 (15)H15A—C15—H15B107.6
C7—C6—C5124.70 (16)C15—C16—H16A109.5
C7—C6—N3114.12 (15)C15—C16—H16B109.5
C5—C6—N3121.13 (15)H16A—C16—H16B109.5
C8—C7—C6117.98 (16)C15—C16—H16C109.5
C8—C7—H7121.0H16A—C16—H16C109.5
C6—C7—H7121.0H16B—C16—H16C109.5
C7—C8—C9121.78 (16)C2—N1—C1125.68 (15)
C7—C8—N4119.59 (16)C2—N1—H1A117.5 (15)
C9—C8—N4118.62 (17)C1—N1—H1A116.8 (15)
C10—C9—C8117.76 (16)C2—N2—C3125.47 (16)
C10—C9—H9121.1C2—N2—H2A117.4 (15)
C8—C9—H9121.1C3—N2—H2A117.1 (15)
C9—C10—C5124.95 (15)O4—N3—O5124.29 (17)
C9—C10—N5113.79 (15)O4—N3—C6117.36 (16)
C5—C10—N5121.14 (14)O5—N3—C6118.30 (15)
C12—C11—N6113.3 (2)O6—N4—O7123.81 (18)
C12—C11—H11A108.9O6—N4—C8117.96 (19)
N6—C11—H11A108.9O7—N4—C8118.22 (17)
C12—C11—H11B108.9O9—N5—O8124.63 (15)
N6—C11—H11B108.9O9—N5—C10118.02 (14)
H11A—C11—H11B107.7O8—N5—C10117.27 (14)
C11—C12—H12A109.5C13—N6—C15114.97 (17)
C11—C12—H12B109.5C13—N6—C11111.34 (16)
H12A—C12—H12B109.5C15—N6—C11111.13 (17)
C11—C12—H12C109.5C13—N6—H6109.8 (16)
H12A—C12—H12C109.5C15—N6—H6104.4 (16)
H12B—C12—H12C109.5C11—N6—H6104.5 (16)
N6—C13—C14114.21 (16)H1W—O1W—H2W113.6 (14)
N6—C13—H13A108.7H4W—O2W—H3W111.6 (16)
C14—C13—H13A108.7C14—O10—H10109.5
O3—C3—C4—C1176.75 (17)N6—C13—C14—O10−53.0 (2)
N2—C3—C4—C1−1.6 (2)O2—C2—N1—C1178.4 (2)
O3—C3—C4—C5−2.4 (3)N2—C2—N1—C1−2.0 (3)
N2—C3—C4—C5179.24 (16)O1—C1—N1—C2−178.03 (18)
O1—C1—C4—C3179.91 (17)C4—C1—N1—C21.6 (3)
N1—C1—C4—C30.3 (2)O2—C2—N2—C3−179.9 (2)
O1—C1—C4—C5−1.0 (3)N1—C2—N2—C30.4 (3)
N1—C1—C4—C5179.45 (15)O3—C3—N2—C2−177.22 (18)
C3—C4—C5—C10134.25 (17)C4—C3—N2—C21.3 (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—O4139.73 (18)
C1—C4—C5—C6136.50 (17)C7—C6—N3—O5135.05 (17)
C10—C5—C6—C7−1.2 (2)C5—C6—N3—O5−42.6 (2)
C4—C5—C6—C7177.56 (16)C7—C8—N4—O65.1 (3)
C10—C5—C6—N3176.24 (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—C82.2 (3)C9—C8—N4—O73.3 (3)
N3—C6—C7—C8−175.40 (16)C9—C10—N5—O9133.96 (16)
C6—C7—C8—C9−0.9 (3)C5—C10—N5—O9−42.3 (2)
C6—C7—C8—N4177.78 (16)C9—C10—N5—O8−42.9 (2)
C7—C8—C9—C10−1.3 (3)C5—C10—N5—O8140.79 (16)
N4—C8—C9—C10−179.93 (16)C14—C13—N6—C15−56.2 (2)
C8—C9—C10—C52.4 (3)C14—C13—N6—C11176.34 (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—C1163.6 (2)
C4—C5—C10—C9−179.92 (16)C12—C11—N6—C13−64.7 (3)
C6—C5—C10—N5174.67 (14)C12—C11—N6—C15165.7 (2)
C4—C5—C10—N5−4.1 (2)
D—H···AD—HH···AD···AD—H···A
O10—H10···O2Wi0.822.052.792 (2)150
O10—H10···O4ii0.822.493.0648 (19)129
N6—H6···O1Wiii0.91 (3)1.95 (3)2.846 (2)170 (2)
N1—H1A···O10iv0.85 (2)2.05 (3)2.884 (2)166 (2)
N2—H2A···O2v0.83 (2)2.03 (2)2.847 (2)173 (2)
O1W—H2W···O2v0.91 (1)1.90 (2)2.7431 (19)154 (2)
O2W—H4W···O1Wvi0.93 (1)1.94 (2)2.796 (3)152 (3)
O1W—H1W···O30.91 (1)1.91 (1)2.7783 (17)160 (2)
O2W—H3W···O10.93 (1)1.89 (2)2.792 (2)162 (4)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O10—H10⋯O2Wi0.822.052.792 (2)150
O10—H10⋯O4ii0.822.493.0648 (19)129
N6—H6⋯O1Wiii0.91 (3)1.95 (3)2.846 (2)170 (2)
N1—H1A⋯O10iv0.85 (2)2.05 (3)2.884 (2)166 (2)
N2—H2A⋯O2v0.83 (2)2.03 (2)2.847 (2)173 (2)
O1W—H2W⋯O2v0.91 (1)1.90 (2)2.7431 (19)154 (2)
O2W—H4W⋯O1Wvi0.93 (1)1.94 (2)2.796 (3)152 (3)
O1W—H1W⋯O30.91 (1)1.91 (1)2.7783 (17)160 (2)
O2W—H3W⋯O10.93 (1)1.89 (2)2.792 (2)162 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

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Authors:  Doraisamyraja Kalaivani; Rangasamy Malarvizhi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-09-26

3.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  3 in total
  7 in total

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Authors:  Govindan Mangaiyarkarasi; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-05-11

2.  N,N-Diethyl-anilinium 2,4-dioxo-5-(2,4,6-trinitro-phen-yl)-1,2,3,4-tetra-hydro-pyrimi-din-6-olate.

Authors:  Manickam Buvaneswari; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-30

3.  N,N-Diethyl-2-hy-droxy-ethanaminium 5-(5-chloro-2,4-dinitro-phen-yl)-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate hemihydrate.

Authors:  Rajamanickam Babykala; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-31

4.  Triethyl-ammonium 1,3-dimethyl-5-(2,4,6-trinitro-phenyl)barbiturate.

Authors:  Kulandaiya Rajamani; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-10

5.  2-Methyl-pyridinium 5-(2,4-dinitro-phen-yl)-1,3-dimethyl-barbiturate.

Authors:  Gunaseelan Sridevi; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-14

6.  N,N-Diethyl-anilinium 5-(2,4-dinitro-phen-yl)-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate.

Authors:  Doraisamyraja Kalaivani; Govindan Mangaiyarkarasi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-05

7.  Crystal structure of tri-methyl-ammonium 5-(2,4-di-nitro-phen-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate.

Authors:  Sridevi Gunaseelan; Kalaivani Doraisamyraja
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-09-13
  7 in total

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