Literature DB >> 25161543

Bis(2-amino-4-methyl-6-oxo-3,6-di-hydro-pyrimidin-1-ium) sulfate monohydrate.

Sarra Soudani1, Emmanuel Wenger2, Christian Jelsch2, Cherif Ben Nasr3.   

Abstract

In the title hydrated mol-ecular salt, 2C5H8N3O(+)·SO4 (2-)·H2O, the components are linked by N-H⋯Os and Ow-H⋯Os (s = sulphate, w = water) hydrogen bonds, generating a layer by a+b+c and 2a-b translations. The cations are arranged nearly in parallel and show displaced π-π stacking centroid-centroid distance = 4.661 (2) Å between adjacent layers.

Entities:  

Year:  2014        PMID： 25161543      PMCID： PMC4120550          DOI： 10.1107/S1600536814012513

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


Related literature

For the applications of oxoanion compounds, see: Vollano et al. (1984 ▶); Molloy (1988 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For the stability of the quinonic and phenolic form in polar solvents, see: Fragoso et al. (2010 ▶). For C—N single bond lengths, see: Yang et al. (1995 ▶); Grobelny et al. (1995 ▶). For the geometrical characteristics of the sulfate anion, see: Das et al. (2009 ▶); Norquist et al. (2005 ▶).

Experimental

Crystal data

2C5H8N3O+·SO4 2−·H2O M = 366.36 Triclinic, a = 6.797 (5) Å b = 10.339 (6) Å c = 12.110 (7) Å α = 113.480 (5)° β = 91.009 (7)° γ = 98.906 (5)° V = 768.2 (8) Å3 Z = 2 Mo Kα radiation μ = 0.26 mm−1 T = 100 K 0.27 × 0.19 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.92, T max = 0.97 5784 measured reflections 5784 independent reflections 5347 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.081 wR(F 2) = 0.131 S = 1.35 5784 reflections 289 parameters 15 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.64 e Å−3 Δρmin = −0.38 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814012513/bg2531sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012513/bg2531Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814012513/bg2531Isup3.cml CCDC reference: 1005732 Additional supporting information: crystallographic information; 3D view; checkCIF report
2C5H8N3O+·SO42−·H2OV = 768.2 (8) Å3
Mr = 366.36Z = 2
Triclinic, P1F(000) = 384
Hall symbol: -P 1Dx = 1.584 Mg m−3
a = 6.797 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.339 (6) Åθ = 2.2–33.4°
c = 12.110 (7) ŵ = 0.26 mm−1
α = 113.480 (5)°T = 100 K
β = 91.009 (7)°Prism, colourless
γ = 98.906 (5)°0.27 × 0.19 × 0.12 mm
Bruker APEXII CCD diffractometer5784 independent reflections
Radiation source: fine-focus sealed tube5347 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.000
ω scansθmax = 33.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)h = 0→10
Tmin = 0.92, Tmax = 0.97k = −15→15
5784 measured reflectionsl = −18→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.35w = 1/[σ2(Fo2) + (0.044P)2 + 0.4148P] where P = (Fo2 + 2Fc2)/3
5784 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.64 e Å−3
15 restraintsΔρmin = −0.38 e Å−3
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
S10.32594 (6)0.79761 (4)0.06036 (4)0.00888 (9)
O40.10950 (17)0.75634 (13)0.01545 (11)0.0129 (2)
O50.39545 (18)0.67318 (13)0.06868 (11)0.0136 (2)
O60.44256 (18)0.84309 (13)−0.02448 (11)0.0137 (2)
O70.34949 (19)0.91648 (13)0.18190 (11)0.0161 (3)
C1−0.1015 (2)0.07187 (17)0.18509 (14)0.0097 (3)
N1−0.1580 (2)−0.04398 (16)0.08537 (13)0.0125 (3)
N2−0.2110 (2)0.17792 (15)0.22132 (13)0.0113 (3)
C3−0.1599 (2)0.30560 (18)0.32540 (15)0.0121 (3)
O3−0.2627 (2)0.39938 (14)0.34694 (12)0.0188 (3)
C40.0171 (3)0.31382 (18)0.39715 (15)0.0128 (3)
C50.1275 (2)0.20844 (17)0.35890 (15)0.0109 (3)
C60.3178 (3)0.2130 (2)0.42459 (17)0.0171 (3)
N70.0687 (2)0.08908 (15)0.25224 (13)0.0108 (3)
C11−0.0959 (2)0.61151 (17)0.19155 (15)0.0113 (3)
N11−0.2643 (2)0.58800 (17)0.12550 (14)0.0145 (3)
N12−0.0358 (2)0.73732 (16)0.28733 (13)0.0138 (3)
C130.1415 (3)0.76947 (19)0.36118 (16)0.0151 (3)
O130.1845 (2)0.88853 (14)0.44418 (12)0.0226 (3)
C140.2552 (3)0.65558 (19)0.33060 (16)0.0153 (3)
C150.1953 (2)0.53064 (18)0.23358 (15)0.0119 (3)
C160.3067 (3)0.4085 (2)0.18954 (17)0.0149 (3)
N170.0195 (2)0.51065 (15)0.16497 (13)0.0111 (3)
O80.6783 (2)0.91155 (15)0.32711 (12)0.0190 (3)
H1A−0.274 (4)−0.063 (3)0.046 (2)0.020 (6)*
H1B−0.082 (4)−0.104 (3)0.064 (2)0.019 (6)*
H2−0.310 (4)0.173 (3)0.168 (2)0.028 (7)*
H40.060 (4)0.398 (2)0.472 (2)0.019 (6)*
H6A0.344 (3)0.302 (3)0.4979 (18)0.032 (7)*
H6B0.425 (2)0.212 (3)0.379 (2)0.031 (7)*
H6C0.306 (4)0.130 (3)0.444 (2)0.038 (8)*
H70.143 (4)0.028 (3)0.230 (2)0.029 (7)*
H11A−0.303 (4)0.505 (3)0.065 (3)0.029 (7)*
H11B−0.337 (4)0.657 (3)0.143 (2)0.026 (6)*
H12−0.118 (4)0.804 (3)0.305 (2)0.027 (6)*
H140.374 (4)0.672 (3)0.378 (2)0.023 (6)*
H16A0.417 (3)0.424 (3)0.245 (2)0.031 (7)*
H16B0.351 (3)0.397 (2)0.1108 (18)0.024 (6)*
H16C0.220 (4)0.3214 (14)0.178 (2)0.021 (6)*
H17−0.020 (4)0.432 (3)0.109 (3)0.030 (7)*
H8A0.694 (5)0.983 (3)0.396 (3)0.041 (8)*
H8B0.577 (4)0.914 (3)0.290 (3)0.030 (7)*
U11U22U33U12U13U23
S10.00752 (16)0.00803 (17)0.00983 (17)0.00195 (12)−0.00157 (12)0.00220 (13)
O40.0068 (5)0.0115 (5)0.0166 (6)0.0011 (4)−0.0022 (4)0.0021 (4)
O50.0146 (6)0.0110 (5)0.0163 (6)0.0039 (4)−0.0024 (5)0.0062 (5)
O60.0106 (5)0.0167 (6)0.0154 (6)0.0004 (4)−0.0017 (4)0.0090 (5)
O70.0152 (6)0.0146 (6)0.0124 (6)0.0066 (5)−0.0038 (5)−0.0022 (4)
C10.0081 (6)0.0115 (7)0.0100 (7)0.0016 (5)0.0006 (5)0.0048 (6)
N10.0091 (6)0.0125 (6)0.0126 (6)0.0027 (5)−0.0017 (5)0.0015 (5)
N20.0098 (6)0.0124 (6)0.0113 (6)0.0043 (5)−0.0009 (5)0.0034 (5)
C30.0113 (7)0.0123 (7)0.0119 (7)0.0020 (6)0.0001 (6)0.0041 (6)
O30.0181 (6)0.0157 (6)0.0202 (6)0.0088 (5)−0.0010 (5)0.0028 (5)
C40.0133 (7)0.0115 (7)0.0116 (7)0.0019 (6)−0.0020 (6)0.0026 (6)
C50.0099 (7)0.0110 (7)0.0111 (7)0.0000 (5)−0.0015 (5)0.0044 (6)
C60.0141 (8)0.0163 (8)0.0184 (8)0.0029 (6)−0.0066 (6)0.0048 (7)
N70.0088 (6)0.0101 (6)0.0117 (6)0.0030 (5)−0.0013 (5)0.0022 (5)
C110.0107 (7)0.0110 (7)0.0121 (7)0.0009 (6)0.0004 (6)0.0051 (6)
N110.0112 (6)0.0115 (6)0.0186 (7)0.0032 (5)−0.0040 (5)0.0037 (6)
N120.0143 (7)0.0109 (6)0.0132 (6)0.0026 (5)−0.0013 (5)0.0019 (5)
C130.0162 (8)0.0151 (8)0.0122 (7)0.0002 (6)−0.0014 (6)0.0048 (6)
O130.0290 (7)0.0153 (6)0.0152 (6)−0.0003 (5)−0.0051 (5)−0.0007 (5)
C140.0135 (8)0.0181 (8)0.0128 (7)0.0004 (6)−0.0038 (6)0.0056 (6)
C150.0092 (7)0.0156 (7)0.0129 (7)0.0018 (6)−0.0003 (6)0.0081 (6)
C160.0111 (7)0.0178 (8)0.0173 (8)0.0052 (6)0.0008 (6)0.0077 (7)
N170.0093 (6)0.0100 (6)0.0116 (6)0.0015 (5)−0.0019 (5)0.0021 (5)
O80.0199 (7)0.0198 (7)0.0130 (6)0.0092 (5)−0.0041 (5)0.0004 (5)
S1—O51.4759 (14)N7—H70.83 (3)
S1—O71.4805 (14)C11—N111.318 (2)
S1—O61.4843 (14)C11—N171.342 (2)
S1—O41.4949 (16)C11—N121.349 (2)
C1—N11.315 (2)N11—H11A0.87 (3)
C1—N71.349 (2)N11—H11B0.89 (3)
C1—N21.353 (2)N12—C131.402 (2)
N1—H1A0.87 (3)N12—H120.91 (3)
N1—H1B0.83 (3)C13—O131.226 (2)
N2—C31.403 (2)C13—C141.437 (3)
N2—H20.91 (3)C14—C151.351 (2)
C3—O31.229 (2)C14—H140.94 (3)
C3—C41.443 (2)C15—N171.383 (2)
C4—C51.352 (2)C15—C161.492 (3)
C4—H40.97 (2)C16—H16A0.95 (2)
C5—N71.382 (2)C16—H16B0.972 (19)
C5—C61.491 (2)C16—H16C0.953 (19)
C6—H6A0.98 (2)N17—H170.83 (3)
C6—H6B0.92 (2)O8—H8A0.86 (3)
C6—H6C0.97 (2)O8—H8B0.82 (3)
O5—S1—O7109.31 (8)C1—N7—H7120.5 (19)
O5—S1—O6109.99 (8)C5—N7—H7117.9 (19)
O7—S1—O6110.24 (9)N11—C11—N17120.64 (15)
O5—S1—O4108.97 (8)N11—C11—N12120.77 (16)
O7—S1—O4108.81 (7)N17—C11—N12118.59 (15)
O6—S1—O4109.49 (8)C11—N11—H11A119.9 (18)
N1—C1—N7120.88 (15)C11—N11—H11B119.6 (17)
N1—C1—N2120.63 (15)H11A—N11—H11B120 (2)
N7—C1—N2118.48 (15)C11—N12—C13123.73 (15)
C1—N1—H1A122.7 (16)C11—N12—H12117.5 (17)
C1—N1—H1B117.4 (17)C13—N12—H12118.8 (17)
H1A—N1—H1B120 (2)O13—C13—N12118.40 (17)
C1—N2—C3124.22 (14)O13—C13—C14126.54 (17)
C1—N2—H2116.8 (17)N12—C13—C14115.06 (15)
C3—N2—H2118.0 (17)C15—C14—C13120.77 (16)
O3—C3—N2119.39 (15)C15—C14—H14121.2 (15)
O3—C3—C4125.98 (16)C13—C14—H14118.0 (15)
N2—C3—C4114.61 (14)C14—C15—N17119.59 (16)
C5—C4—C3120.56 (15)C14—C15—C16125.40 (16)
C5—C4—H4120.1 (14)N17—C15—C16115.00 (15)
C3—C4—H4119.2 (14)C15—C16—H16A110.6 (13)
C4—C5—N7120.36 (15)C15—C16—H16B109.0 (12)
C4—C5—C6123.67 (15)H16A—C16—H16B111 (2)
N7—C5—C6115.96 (15)C15—C16—H16C110.2 (12)
C5—C6—H6A108.6 (13)H16A—C16—H16C110 (2)
C5—C6—H6B112.1 (14)H16B—C16—H16C106 (2)
H6A—C6—H6B108 (2)C11—N17—C15122.20 (15)
C5—C6—H6C109.4 (14)C11—N17—H17119.0 (19)
H6A—C6—H6C111 (2)C15—N17—H17118.7 (19)
H6B—C6—H6C108 (2)H8A—O8—H8B108 (3)
C1—N7—C5121.60 (14)
D—H···AD—HH···AD···AD—H···A
N1—H1A···O6i0.87 (3)2.02 (3)2.856 (3)161 (3)
N1—H1B···O4ii0.83 (3)2.01 (3)2.847 (4)178 (2)
N2—H2···O6iii0.91 (3)1.88 (2)2.749 (4)161 (2)
N7—H7···O7ii0.83 (3)1.91 (3)2.730 (4)170 (3)
N11—H11A···O5iii0.87 (3)1.91 (3)2.782 (6)178 (3)
N11—H11B···O5iv0.89 (3)2.07 (3)2.767 (3)134 (2)
N12—H12···O8iv0.92 (3)1.87 (3)2.771 (4)170 (3)
N17—H17···O4iii0.82 (3)1.92 (3)2.746 (6)177 (3)
O8—H8A···O13v0.86 (3)1.94 (3)2.750 (5)158 (3)
O8—H8B···O70.83 (3)2.02 (3)2.839 (4)173 (3)
C4—H4···O3vi0.97 (2)2.54 (2)3.485 (3)165 (2)
C6—H6C···O13ii0.972.513.440 (3)162 (2)
C16—H16A···O3vii0.952.583.499 (5)163 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1A⋯O6i 0.87 (3)2.02 (3)2.856 (3)161 (3)
N1—H1B⋯O4ii 0.83 (3)2.01 (3)2.847 (4)178 (2)
N2—H2⋯O6iii 0.91 (3)1.88 (2)2.749 (4)161 (2)
N7—H7⋯O7ii 0.83 (3)1.91 (3)2.730 (4)170 (3)
N11—H11A⋯O5iii 0.87 (3)1.91 (3)2.782 (6)178 (3)
N11—H11B⋯O5iv 0.89 (3)2.07 (3)2.767 (3)134 (2)
N12—H12⋯O8iv 0.92 (3)1.87 (3)2.771 (4)170 (3)
N17—H17⋯O4iii 0.82 (3)1.92 (3)2.746 (6)177 (3)
O8—H8A⋯O13v 0.86 (3)1.94 (3)2.750 (5)158 (3)
O8—H8B⋯O70.83 (3)2.02 (3)2.839 (4)173 (3)
C4—H4⋯O3vi 0.97 (2)2.54 (2)3.485 (3)165 (2)
C6—H6C⋯O13ii 0.972.513.440 (3)162 (2)
C16—H16A⋯O3vii 0.952.583.499 (5)163 (2)

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

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