Literature DB >> 25484695

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.

Sridevi Gunaseelan1, Kalaivani Doraisamyraja1.   

Abstract

The asymmetric unit of the title mol-ecular salt, C3H10N(+)·C12H9N4O7 (-) [alternative name: tri-methyl-ammonium 5-(2,4-di-nitro-phen-yl)-1,3-dimethyl barbiturate], contains one anion and two half-occupancy cations. The cations are disordered about inversion centres. The tetra-hydro-pyrimidine ring is essentially planar [maximum deviation = 0.007 (2) Å] and forms a dihedral angle of 41.12 (6)° with the plane of the benzene ring. In the crystal, N-H⋯O hydrogen bonds link the cations to the anions.

Entities:  

Keywords:  anionic σ-complexes; barbiturates; biological activity; crystal structure; tetra­hydro­pyrimidin-4-olate salt; tri­methyl­ammonium salt

Year:  2014        PMID： 25484695      PMCID： PMC4257181          DOI： 10.1107/S1600536814019977

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


Related literature

For the biological activity of barbiturates, see: Hueso et al. (2003 ▶); Kalaivani et al. (2008 ▶); Tripathi (2009 ▶); Kalaivani & Buvaneswari (2010 ▶). For various types of anionic σ-complexes, see: Terrier (1982 ▶); Gnanadoss & Kalaivani (1985 ▶); Al-Kaysi et al. (2005 ▶); For barbiturates as carbon-bonded σ-complexes, see: Kalaivani & Malarvizhi (2009 ▶); Buvaneswari & Kalaivani (2011 ▶); Kalaivani et al. (2012 ▶); Babykala & Kalaivani (2012 ▶, 2013 ▶); Sridevi & Kalaivani (2012 ▶); Rajamani & Kalaivani (2012 ▶). For the crystal structure of a related barbiturate, see: Mangaiyarkarasi & Kalaivani (2013 ▶)

Experimental

Crystal data

C3H10N+·C12H9N4O7 − M = 381.35 Triclinic, a = 9.8417 (5) Å b = 9.9474 (6) Å c = 10.4241 (5) Å α = 103.454 (2)° β = 106.479 (2)° γ = 100.856 (2)° V = 915.66 (9) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 293 K 0.35 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 9536, T max = 9865 16319 measured reflections 4271 independent reflections 2922 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.164 S = 0.99 4271 reflections 341 parameters 76 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.20 e Å−3

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: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814019977/lh5722sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019977/lh5722Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814019977/lh5722Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814019977/lh5722fig1.tif The asymmetric unit of title compound showing 30% probability displacement ellipsoids. The cations are half occupancy. CCDC reference: 1022943 Additional supporting information: crystallographic information; 3D view; checkCIF report
C3H10N+·C12H9N4O7−Z = 2
Mr = 381.35F(000) = 400
Triclinic, P1Dx = 1.383 Mg m−3
a = 9.8417 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.9474 (6) ÅCell parameters from 5386 reflections
c = 10.4241 (5) Åθ = 2.1–27.5°
α = 103.454 (2)°µ = 0.11 mm−1
β = 106.479 (2)°T = 293 K
γ = 100.856 (2)°Block, red
V = 915.66 (9) Å30.35 × 0.35 × 0.30 mm
Bruker Kappa APEXII CCD diffractometer2922 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
ω and φ scanθmax = 27.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −12→12
Tmin = 9536, Tmax = 9865k = −12→12
16319 measured reflectionsl = −13→13
4271 independent reflections
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.051w = 1/[σ2(Fo2) + (0.0891P)2 + 0.1912P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.164(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.23 e Å−3
4271 reflectionsΔρmin = −0.20 e Å−3
341 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
76 restraintsExtinction coefficient: 0.020 (4)
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.
xyzUiso*/UeqOcc. (<1)
C10.3976 (2)0.7207 (3)0.07803 (19)0.0655 (6)
C20.2837 (2)0.6256 (2)0.08545 (17)0.0548 (5)
H20.24340.53420.02080.066*
C30.22965 (18)0.66915 (18)0.19261 (16)0.0440 (4)
C40.29063 (16)0.80221 (18)0.29787 (16)0.0424 (4)
C50.40705 (19)0.8947 (2)0.28249 (19)0.0584 (5)
H50.45080.98530.34810.070*
C60.4590 (2)0.8561 (3)0.1734 (2)0.0712 (6)
H60.53470.92080.16440.085*
C70.24320 (16)0.84301 (17)0.41888 (15)0.0415 (4)
C80.21150 (17)0.74090 (18)0.48671 (16)0.0435 (4)
C90.1589 (2)0.9213 (2)0.65492 (18)0.0560 (5)
C100.23385 (19)0.98455 (19)0.46730 (18)0.0507 (4)
C110.1303 (3)0.6789 (3)0.6741 (3)0.0840 (7)
H11A0.14150.58840.62770.126*
H11B0.03010.66740.67040.126*
H11C0.19440.71160.77040.126*
C120.1746 (3)1.1619 (2)0.6375 (2)0.0740 (6)
H12A0.19871.21850.57990.111*
H12B0.24051.20610.73260.111*
H12C0.07521.15590.63420.111*
N10.4546 (2)0.6754 (3)−0.0364 (2)0.0970 (8)
N20.09232 (17)0.56946 (15)0.18014 (14)0.0511 (4)
N30.18912 (16)1.01709 (16)0.58517 (15)0.0531 (4)
N40.16852 (17)0.78490 (17)0.60370 (15)0.0529 (4)
O10.4045 (2)0.5528 (3)−0.1143 (2)0.1098 (7)
O20.5474 (3)0.7651 (4)−0.0482 (3)0.1804 (16)
O30.0792 (2)0.44075 (15)0.13971 (17)0.0812 (5)
O4−0.00550 (14)0.61913 (14)0.20145 (14)0.0609 (4)
O50.22047 (16)0.61540 (14)0.45327 (13)0.0597 (4)
O60.2581 (2)1.08059 (16)0.41394 (18)0.0814 (5)
O70.1253 (2)0.95645 (19)0.75936 (16)0.0872 (5)
N5−0.0051 (4)0.9761 (3)0.9524 (3)0.0548 (8)0.5
H5A0.0157 (18)0.9501 (17)0.8715 (19)0.066*0.5
C130.0093 (9)1.1276 (5)0.9872 (7)0.0839 (16)0.5
H13A−0.062 (5)1.134 (8)0.905 (4)0.126*0.5
H13B0.106 (3)1.180 (6)0.993 (6)0.126*0.5
H13C−0.010 (6)1.166 (6)1.070 (4)0.126*0.5
C14−0.1578 (5)0.8892 (6)0.9182 (5)0.0772 (12)0.5
H14A−0.155 (6)0.791 (3)0.896 (5)0.116*0.5
H14B−0.217 (6)0.909 (5)0.841 (3)0.116*0.5
H14C−0.188 (6)0.913 (5)0.998 (4)0.116*0.5
C150.0966 (8)0.9352 (8)1.0574 (6)0.0886 (17)0.5
H15A0.094 (7)0.834 (2)1.037 (7)0.133*0.5
H15B0.087 (7)0.966 (6)1.148 (4)0.133*0.5
H15C0.193 (4)0.987 (5)1.062 (7)0.133*0.5
N60.4670 (5)0.5181 (5)0.4932 (5)0.0741 (11)0.5
H6A0.381 (2)0.544 (2)0.4697 (18)0.089*0.5
C160.4046 (7)0.3737 (6)0.3630 (6)0.0930 (15)0.5
H16A0.426 (6)0.307 (6)0.413 (6)0.140*0.5
H16B0.441 (6)0.364 (7)0.288 (5)0.140*0.5
H16C0.302 (3)0.367 (7)0.334 (6)0.140*0.5
C170.5736 (8)0.6071 (8)0.4681 (12)0.117 (3)0.5
H17A0.623 (8)0.537 (7)0.436 (7)0.176*0.5
H17B0.647 (7)0.679 (6)0.551 (4)0.176*0.5
H17C0.545 (4)0.651 (6)0.396 (5)0.176*0.5
C180.4811 (9)0.4741 (12)0.6114 (7)0.111 (3)0.5
H18A0.393 (3)0.443 (7)0.631 (5)0.166*0.5
H18B0.558 (5)0.536 (7)0.695 (5)0.166*0.5
H18C0.510 (8)0.389 (5)0.574 (8)0.166*0.5
U11U22U33U12U13U23
C10.0500 (10)0.1118 (17)0.0387 (9)0.0263 (11)0.0228 (8)0.0172 (10)
C20.0573 (10)0.0737 (12)0.0377 (8)0.0300 (9)0.0197 (7)0.0106 (8)
C30.0482 (8)0.0543 (10)0.0350 (8)0.0210 (7)0.0183 (6)0.0129 (7)
C40.0397 (7)0.0541 (9)0.0346 (7)0.0155 (7)0.0139 (6)0.0121 (7)
C50.0464 (9)0.0752 (13)0.0454 (9)0.0029 (8)0.0181 (7)0.0112 (9)
C60.0459 (9)0.1101 (18)0.0544 (11)0.0043 (10)0.0249 (8)0.0231 (12)
C70.0404 (7)0.0468 (9)0.0351 (8)0.0110 (6)0.0152 (6)0.0064 (6)
C80.0445 (8)0.0548 (10)0.0349 (8)0.0194 (7)0.0168 (6)0.0117 (7)
C90.0517 (9)0.0693 (12)0.0403 (9)0.0141 (8)0.0210 (7)−0.0002 (8)
C100.0517 (9)0.0468 (10)0.0464 (9)0.0059 (7)0.0196 (7)0.0038 (7)
C110.119 (2)0.0999 (18)0.0632 (13)0.0394 (15)0.0570 (14)0.0414 (13)
C120.0747 (13)0.0577 (12)0.0777 (14)0.0182 (10)0.0309 (11)−0.0072 (10)
N10.0689 (12)0.170 (2)0.0540 (11)0.0302 (14)0.0373 (10)0.0186 (14)
N20.0666 (9)0.0447 (8)0.0390 (7)0.0118 (7)0.0222 (6)0.0046 (6)
N30.0530 (8)0.0492 (8)0.0498 (8)0.0115 (6)0.0226 (6)−0.0024 (7)
N40.0604 (9)0.0676 (10)0.0393 (7)0.0214 (7)0.0264 (6)0.0172 (7)
O10.1167 (15)0.164 (2)0.0614 (10)0.0629 (14)0.0513 (10)0.0114 (12)
O20.145 (2)0.251 (3)0.1205 (19)−0.023 (2)0.1083 (19)−0.003 (2)
O30.1220 (13)0.0443 (8)0.0793 (10)0.0157 (8)0.0525 (10)0.0058 (7)
O40.0511 (7)0.0642 (8)0.0588 (8)0.0074 (6)0.0239 (6)0.0030 (6)
O50.0829 (9)0.0629 (8)0.0538 (7)0.0374 (7)0.0356 (7)0.0264 (6)
O60.1232 (13)0.0492 (8)0.0846 (11)0.0192 (8)0.0583 (10)0.0191 (7)
O70.1065 (12)0.1035 (12)0.0624 (9)0.0314 (10)0.0580 (9)0.0071 (8)
N50.086 (2)0.0557 (19)0.0494 (17)0.0395 (17)0.0426 (18)0.0251 (15)
C130.126 (5)0.060 (3)0.094 (4)0.042 (3)0.063 (4)0.031 (3)
C140.082 (3)0.080 (3)0.064 (3)0.016 (2)0.030 (2)0.010 (2)
C150.100 (4)0.117 (5)0.077 (3)0.063 (4)0.032 (3)0.050 (4)
N60.081 (3)0.082 (3)0.104 (3)0.048 (2)0.059 (3)0.055 (2)
C160.106 (4)0.081 (4)0.090 (4)0.026 (3)0.039 (3)0.016 (3)
C170.087 (4)0.076 (4)0.195 (9)0.017 (3)0.042 (5)0.065 (5)
C180.106 (5)0.192 (9)0.083 (4)0.090 (6)0.054 (4)0.067 (5)
C1—C21.358 (3)C13—C14i1.577 (10)
C1—C61.377 (3)C13—H13A0.962 (19)
C1—N11.471 (2)C13—H13B0.971 (19)
C2—C31.385 (2)C13—H13C0.944 (18)
C2—H20.9300C14—C13i1.577 (10)
C3—C41.403 (2)C14—C15i1.669 (9)
C3—N21.471 (2)C14—N5i1.819 (6)
C4—C51.400 (2)C14—H14A0.962 (18)
C4—C71.463 (2)C14—H14B0.938 (18)
C5—C61.379 (3)C14—H14C0.956 (18)
C5—H50.9300C15—C13i1.019 (8)
C6—H60.9300C15—N5i1.375 (6)
C7—C81.403 (2)C15—C14i1.669 (9)
C7—C101.411 (2)C15—H15A0.972 (19)
C8—O51.243 (2)C15—H15B0.960 (19)
C8—N41.404 (2)C15—H15C0.973 (19)
C9—O71.219 (2)N6—N6ii0.796 (6)
C9—N31.365 (3)N6—C18ii1.340 (8)
C9—N41.370 (2)N6—C171.367 (8)
C10—O61.231 (2)N6—C181.381 (7)
C10—N31.408 (2)N6—C17ii1.419 (8)
C11—N41.470 (3)N6—C161.603 (7)
C11—H11A0.9600N6—C16ii1.632 (8)
C11—H11B0.9600N6—H6A0.92 (2)
C11—H11C0.9600C16—C18ii1.621 (12)
C12—N31.466 (2)C16—N6ii1.633 (8)
C12—H12A0.9600C16—C17ii1.673 (13)
C12—H12B0.9600C16—H16A0.955 (19)
C12—H12C0.9600C16—H16B0.938 (19)
N1—O21.206 (3)C16—H16C0.953 (19)
N1—O11.215 (3)C17—C18ii0.949 (9)
N2—O41.2122 (19)C17—N6ii1.419 (8)
N2—O31.2205 (19)C17—C16ii1.673 (13)
N5—N5i0.964 (5)C17—H17A0.98 (2)
N5—C13i1.328 (6)C17—H17B0.97 (2)
N5—C15i1.375 (6)C17—H17C0.955 (18)
N5—C131.435 (6)C18—C17ii0.949 (9)
N5—C151.450 (6)C18—N6ii1.340 (8)
N5—C141.482 (6)C18—C16ii1.621 (12)
N5—C14i1.819 (6)C18—H18A0.957 (18)
N5—H5A0.914 (19)C18—H18B0.956 (19)
C13—C15i1.019 (8)C18—H18C0.971 (19)
C13—N5i1.328 (6)
C2—C1—C6121.79 (16)N5—C14—H14C110 (4)
C2—C1—N1117.9 (2)C13i—C14—H14C90 (3)
C6—C1—N1120.3 (2)C15i—C14—H14C89 (3)
C1—C2—C3117.72 (17)N5i—C14—H14C78 (3)
C1—C2—H2121.1H14A—C14—H14C109 (3)
C3—C2—H2121.1H14B—C14—H14C113 (3)
C2—C3—C4123.94 (16)C13i—C15—N5i72.0 (5)
C2—C3—N2114.20 (15)C13i—C15—N562.2 (4)
C4—C3—N2121.62 (13)N5i—C15—N539.8 (2)
C5—C4—C3114.84 (14)C13i—C15—C14i127.8 (6)
C5—C4—C7121.04 (15)N5i—C15—C14i57.3 (3)
C3—C4—C7124.08 (14)N5—C15—C14i70.9 (4)
C6—C5—C4122.27 (18)C13i—C15—H15A69 (4)
C6—C5—H5118.9N5i—C15—H15A141 (4)
C4—C5—H5118.9N5—C15—H15A117 (5)
C5—C6—C1119.30 (18)C14i—C15—H15A159 (3)
C5—C6—H6120.3C13i—C15—H15B93 (4)
C1—C6—H6120.3N5i—C15—H15B73 (4)
C8—C7—C10121.30 (14)N5—C15—H15B112 (4)
C8—C7—C4119.04 (14)C14i—C15—H15B84 (4)
C10—C7—C4119.64 (15)H15A—C15—H15B108 (3)
O5—C8—N4117.22 (15)C13i—C15—H15C158 (4)
O5—C8—C7125.47 (14)N5i—C15—H15C109 (4)
N4—C8—C7117.30 (15)N5—C15—H15C104 (4)
O7—C9—N3121.10 (19)C14i—C15—H15C53 (4)
O7—C9—N4121.4 (2)H15A—C15—H15C107 (3)
N3—C9—N4117.52 (14)H15B—C15—H15C109 (3)
O6—C10—N3117.41 (16)N6ii—N6—C18ii75.8 (6)
O6—C10—C7125.85 (16)N6ii—N6—C1777.1 (7)
N3—C10—C7116.72 (16)C18ii—N6—C1741.0 (4)
N4—C11—H11A109.5N6ii—N6—C1870.2 (7)
N4—C11—H11B109.5C18ii—N6—C18146.0 (3)
H11A—C11—H11B109.5C17—N6—C18127.1 (6)
N4—C11—H11C109.5N6ii—N6—C17ii69.8 (7)
H11A—C11—H11C109.5C18ii—N6—C17ii126.1 (6)
H11B—C11—H11C109.5C17—N6—C17ii146.9 (3)
N3—C12—H12A109.5C18—N6—C17ii39.6 (4)
N3—C12—H12B109.5N6ii—N6—C1677.8 (7)
H12A—C12—H12B109.5C18ii—N6—C1666.1 (5)
N3—C12—H12C109.5C17—N6—C16106.5 (6)
H12A—C12—H12C109.5C18—N6—C16105.7 (6)
H12B—C12—H12C109.5C17ii—N6—C1666.9 (6)
O2—N1—O1124.0 (2)N6ii—N6—C16ii73.7 (8)
O2—N1—C1116.9 (3)C18ii—N6—C16ii106.1 (5)
O1—N1—C1119.1 (2)C17—N6—C16ii67.1 (6)
O4—N2—O3123.40 (16)C18—N6—C16ii64.5 (5)
O4—N2—C3118.26 (14)C17ii—N6—C16ii102.6 (6)
O3—N2—C3118.14 (15)C16—N6—C16ii151.5 (2)
C9—N3—C10123.73 (15)N6ii—N6—H6A170.3 (15)
C9—N3—C12117.55 (16)C18ii—N6—H6A104.8 (11)
C10—N3—C12118.73 (17)C17—N6—H6A109.9 (11)
C9—N4—C8123.40 (15)C18—N6—H6A108.7 (11)
C9—N4—C11118.16 (15)C17ii—N6—H6A103.0 (11)
C8—N4—C11118.44 (17)C16—N6—H6A93.5 (12)
N5i—N5—C13i75.7 (4)C16ii—N6—H6A114.8 (11)
N5i—N5—C15i74.3 (4)N6—C16—C18ii49.1 (3)
C13i—N5—C15i127.0 (4)N6—C16—N6ii28.5 (2)
N5i—N5—C1363.7 (4)C18ii—C16—N6ii50.2 (3)
C13i—N5—C13139.4 (3)N6—C16—C17ii51.3 (3)
C15i—N5—C1342.4 (3)C18ii—C16—C17ii96.6 (4)
N5i—N5—C1565.9 (4)N6ii—C16—C17ii48.8 (3)
C13i—N5—C1542.7 (4)N6—C16—H16A99 (4)
C15i—N5—C15140.2 (2)C18ii—C16—H16A125 (4)
C13—N5—C15113.9 (4)N6ii—C16—H16A80 (4)
N5i—N5—C1493.7 (4)C17ii—C16—H16A53 (4)
C13i—N5—C1468.1 (4)N6—C16—H16B121 (4)
C15i—N5—C1471.4 (4)C18ii—C16—H16B72 (4)
C13—N5—C14112.9 (4)N6ii—C16—H16B110 (4)
C15—N5—C14110.2 (4)C17ii—C16—H16B152 (4)
N5i—N5—C14i54.4 (4)H16A—C16—H16B112 (3)
C13i—N5—C14i100.0 (4)N6—C16—H16C101 (4)
C15i—N5—C14i96.7 (4)C18ii—C16—H16C119 (4)
C13—N5—C14i56.5 (4)N6ii—C16—H16C127 (4)
C15—N5—C14i60.2 (4)C17ii—C16—H16C96 (4)
C14—N5—C14i148.1 (2)H16A—C16—H16C110 (3)
N5i—N5—H5A161.2 (12)H16B—C16—H16C113 (3)
C13i—N5—H5A111.6 (10)C18ii—C17—N668.0 (6)
C15i—N5—H5A110.8 (10)C18ii—C17—N6ii68.0 (6)
C13—N5—H5A107.2 (11)N6—C17—N6ii33.1 (3)
C15—N5—H5A107.0 (11)C18ii—C17—C16ii128.5 (9)
C14—N5—H5A105.1 (11)N6—C17—C16ii64.0 (5)
C14i—N5—H5A106.8 (11)N6ii—C17—C16ii61.8 (5)
C15i—C13—N5i75.1 (5)C18ii—C17—H17A61 (5)
C15i—C13—N565.6 (5)N6—C17—H17A99 (5)
N5i—C13—N540.6 (3)N6ii—C17—H17A70 (5)
C15i—C13—C14i134.6 (6)C16ii—C17—H17A109 (4)
N5i—C13—C14i60.6 (4)C18ii—C17—H17B167 (4)
N5—C13—C14i74.1 (4)N6—C17—H17B115 (5)
C15i—C13—H13A56 (4)N6ii—C17—H17B107 (4)
N5i—C13—H13A129 (4)C16ii—C17—H17B51 (5)
N5—C13—H13A102 (5)H17A—C17—H17B106 (3)
C14i—C13—H13A159 (4)C18ii—C17—H17C78 (4)
C15i—C13—H13B158 (3)N6—C17—H17C119.0 (18)
N5i—C13—H13B117 (4)N6ii—C17—H17C143 (3)
N5—C13—H13B111 (4)C16ii—C17—H17C142 (4)
C14i—C13—H13B57 (4)H17A—C17—H17C108 (3)
H13A—C13—H13B107 (3)H17B—C17—H17C109 (3)
C15i—C13—H13C89 (3)C17ii—C18—N6ii71.0 (7)
N5i—C13—H13C76 (4)C17ii—C18—N672.4 (7)
N5—C13—H13C114 (4)N6ii—C18—N634.0 (3)
C14i—C13—H13C89 (4)C17ii—C18—C16ii134.5 (9)
H13A—C13—H13C112 (3)N6ii—C18—C16ii64.8 (5)
H13B—C13—H13C111 (3)N6—C18—C16ii65.3 (5)
N5—C14—C13i51.3 (3)C17ii—C18—H18A78 (4)
N5—C14—C15i51.3 (3)N6ii—C18—H18A143 (3)
C13i—C14—C15i96.3 (3)N6—C18—H18A117.4 (17)
N5—C14—N5i31.9 (2)C16ii—C18—H18A136 (4)
C13i—C14—N5i49.4 (3)C17ii—C18—H18B161 (5)
C15i—C14—N5i48.9 (3)N6ii—C18—H18B105 (4)
N5—C14—H14A106 (4)N6—C18—H18B116 (5)
C13i—C14—H14A69 (3)C16ii—C18—H18B50 (5)
C15i—C14—H14A156 (3)H18A—C18—H18B110 (3)
N5i—C14—H14A118 (3)C17ii—C18—H18C51 (5)
N5—C14—H14B107 (4)N6ii—C18—H18C67 (5)
C13i—C14—H14B154 (4)N6—C18—H18C94 (5)
C15i—C14—H14B73 (3)C16ii—C18—H18C116 (4)
N5i—C14—H14B122 (4)H18A—C18—H18C108 (3)
H14A—C14—H14B112 (3)H18B—C18—H18C110 (3)
C6—C1—C2—C30.4 (3)C13i—N5—C14—C15i145.1 (4)
N1—C1—C2—C3−179.46 (18)C13—N5—C14—C15i9.2 (4)
C1—C2—C3—C4−3.7 (3)C15—N5—C14—C15i137.8 (3)
C1—C2—C3—N2170.69 (17)C14i—N5—C14—C15i72.1 (4)
C2—C3—C4—C54.0 (3)C13i—N5—C14—N5i73.0 (4)
N2—C3—C4—C5−169.94 (16)C15i—N5—C14—N5i−72.1 (4)
C2—C3—C4—C7−173.67 (16)C13—N5—C14—N5i−62.9 (4)
N2—C3—C4—C712.4 (2)C15—N5—C14—N5i65.6 (4)
C3—C4—C5—C6−1.2 (3)C14i—N5—C14—N5i−0.002 (2)
C7—C4—C5—C6176.58 (18)N5i—N5—C15—C13i95.0 (6)
C4—C5—C6—C1−1.8 (3)C15i—N5—C15—C13i95.0 (6)
C2—C1—C6—C52.3 (3)C13—N5—C15—C13i138.1 (4)
N1—C1—C6—C5−177.9 (2)C14—N5—C15—C13i10.1 (6)
C5—C4—C7—C8−136.83 (18)C14i—N5—C15—C13i156.4 (6)
C3—C4—C7—C840.7 (2)C13i—N5—C15—N5i−95.0 (6)
C5—C4—C7—C1041.5 (2)C15i—N5—C15—N5i0.000 (1)
C3—C4—C7—C10−140.90 (17)C13—N5—C15—N5i43.1 (4)
C10—C7—C8—O5−178.11 (16)C14—N5—C15—N5i−84.9 (5)
C4—C7—C8—O50.2 (2)C14i—N5—C15—N5i61.4 (4)
C10—C7—C8—N40.7 (2)N5i—N5—C15—C14i−61.4 (4)
C4—C7—C8—N4179.05 (14)C13i—N5—C15—C14i−156.4 (6)
C8—C7—C10—O6−179.24 (18)C15i—N5—C15—C14i−61.4 (4)
C4—C7—C10—O62.4 (3)C13—N5—C15—C14i−18.3 (4)
C8—C7—C10—N3−0.9 (2)C14—N5—C15—C14i−146.3 (2)
C4—C7—C10—N3−179.29 (14)N6ii—N6—C16—C18ii−79.7 (6)
C2—C1—N1—O2174.1 (3)C17—N6—C16—C18ii−7.4 (6)
C6—C1—N1—O2−5.7 (4)C18—N6—C16—C18ii−144.9 (3)
C2—C1—N1—O1−4.5 (3)C17ii—N6—C16—C18ii−152.8 (6)
C6—C1—N1—O1175.7 (2)C16ii—N6—C16—C18ii−79.7 (6)
C2—C3—N2—O4−135.67 (17)C18ii—N6—C16—N6ii79.7 (6)
C4—C3—N2—O438.8 (2)C17—N6—C16—N6ii72.4 (7)
C2—C3—N2—O339.5 (2)C18—N6—C16—N6ii−65.1 (6)
C4—C3—N2—O3−146.01 (17)C17ii—N6—C16—N6ii−73.0 (7)
O7—C9—N3—C10177.49 (17)C16ii—N6—C16—N6ii0.004 (2)
N4—C9—N3—C10−2.1 (3)N6ii—N6—C16—C17ii73.0 (7)
O7—C9—N3—C12−2.2 (3)C18ii—N6—C16—C17ii152.8 (6)
N4—C9—N3—C12178.26 (16)C17—N6—C16—C17ii145.4 (4)
O6—C10—N3—C9−179.88 (18)C18—N6—C16—C17ii7.9 (6)
C7—C10—N3—C91.7 (2)C16ii—N6—C16—C17ii73.0 (7)
O6—C10—N3—C12−0.2 (3)N6ii—N6—C17—C18ii83.2 (10)
C7—C10—N3—C12−178.68 (16)C18—N6—C17—C18ii135.7 (5)
O7—C9—N4—C8−177.78 (17)C17ii—N6—C17—C18ii83.2 (10)
N3—C9—N4—C81.8 (3)C16—N6—C17—C18ii10.3 (8)
O7—C9—N4—C112.9 (3)C16ii—N6—C17—C18ii160.8 (9)
N3—C9—N4—C11−177.50 (18)C18ii—N6—C17—N6ii−83.2 (10)
O5—C8—N4—C9177.77 (15)C18—N6—C17—N6ii52.5 (7)
C7—C8—N4—C9−1.1 (2)C17ii—N6—C17—N6ii−0.001 (2)
O5—C8—N4—C11−2.9 (2)C16—N6—C17—N6ii−72.9 (7)
C7—C8—N4—C11178.16 (17)C16ii—N6—C17—N6ii77.6 (8)
N5i—N5—C13—C15i−95.4 (6)N6ii—N6—C17—C16ii−77.6 (8)
C13i—N5—C13—C15i−95.4 (6)C18ii—N6—C17—C16ii−160.8 (9)
C15—N5—C13—C15i−139.6 (4)C18—N6—C17—C16ii−25.1 (7)
C14—N5—C13—C15i−13.0 (6)C17ii—N6—C17—C16ii−77.6 (8)
C14i—N5—C13—C15i−158.6 (6)C16—N6—C17—C16ii−150.5 (3)
C13i—N5—C13—N5i0.000 (1)N6ii—N6—C18—C17ii−81.9 (10)
C15i—N5—C13—N5i95.4 (6)C18ii—N6—C18—C17ii−81.9 (10)
C15—N5—C13—N5i−44.1 (4)C17—N6—C18—C17ii−137.2 (5)
C14—N5—C13—N5i82.5 (5)C16—N6—C18—C17ii−11.5 (8)
C14i—N5—C13—N5i−63.1 (4)C16ii—N6—C18—C17ii−162.9 (8)
N5i—N5—C13—C14i63.1 (4)C18ii—N6—C18—N6ii−0.002 (2)
C13i—N5—C13—C14i63.1 (4)C17—N6—C18—N6ii−55.2 (8)
C15i—N5—C13—C14i158.6 (6)C17ii—N6—C18—N6ii81.9 (10)
C15—N5—C13—C14i19.0 (4)C16—N6—C18—N6ii70.4 (7)
C14—N5—C13—C14i145.6 (3)C16ii—N6—C18—N6ii−80.9 (7)
N5i—N5—C14—C13i−73.0 (4)N6ii—N6—C18—C16ii80.9 (7)
C15i—N5—C14—C13i−145.1 (4)C18ii—N6—C18—C16ii80.9 (7)
C13—N5—C14—C13i−135.9 (3)C17—N6—C18—C16ii25.7 (7)
C15—N5—C14—C13i−7.4 (4)C17ii—N6—C18—C16ii162.9 (8)
C14i—N5—C14—C13i−73.0 (4)C16—N6—C18—C16ii151.4 (3)
N5i—N5—C14—C15i72.1 (4)
D—H···AD—HH···AD···AD—H···A
N5—H5A···O70.91 (2)1.80 (2)2.666 (3)156 (2)
N6—H6A···O50.92 (2)1.83 (2)2.737 (3)171 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N5—H5A⋯O70.91 (2)1.80 (2)2.666 (3)156 (2)
N6—H6A⋯O50.92 (2)1.83 (2)2.737 (3)171 (2)
  11 in total

1.  A short history of SHELX.

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

2.  Synthesis and spectroscopic studies on the new Schiff base derived from the 1:2 condensation of 2,6-diformyl-4-methylphenol with 5-aminouracil (BDF5AU) and its transition metal complexes. Influence on biologically active peptides-regulating aminopeptidases.

Authors:  Francisco Hueso-Ureña; Nuria A Illán-Cabeza; Miguel N Moreno-Carretero; José M Martínez-Martos; María J Ramírez-Expósito
Journal:  J Inorg Biochem       Date:  2003-04-01       Impact factor: 4.155

3.  Triethyl-ammonium 2,4-dinitro-phenyl-barbiturate.

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

4.  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.

Authors:  Manickam Buvaneswari; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-20

5.  Trimethyl-ammonium 2,6-dioxo-5-(2,4,6-trinitro-phen-yl)-1,2,3,6-tetra-hydro-pyrimidin-4-olate.

Authors:  D Kalaivani; M Buvaneswari; S Rajeswari
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-07

6.  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

7.  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

8.  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

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

Authors:  R Babykala; D Kalaivani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-02-20

10.  Trimethyl-ammonium 5-(2,4-dinitro-phenyl)-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate 0.125-hydrate.

Authors:  Govindan Mangaiyarkarasi; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-03-28
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  3 in total

1.  Crystal structure and biological evaluation of 4-methyl-morpholin-4-ium 1,3-dimethyl-2,6-dioxo-5-(2,4,6-tri-nitro-phen-yl)-1,2,3,6-tetra-hydro-pyrimidin-4-olate.

Authors:  Jeganathan Gomathi; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-05-30

2.  Crystal structure of creatininium 5-(2,4-di-nitro-phen-yl)-1,3-di-methyl-barbiturate monohydrate: a potential anti-convulsant agent.

Authors:  Ponnusamy Poornima Devi; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-04-05

3.  Isoquinolinium 5-(2,4-di-nitro-phen-yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate: crystal structure, Hirshfeld surface analysis and pharmacological evaluation.

Authors:  Ponnusamy Poornima Devi; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-03-31
  3 in total

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