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In the title compound, C
4H
7N
4O
2+·SO
42−·H
2O, the asymmetric unit contains two aminopyrimidinium cations, a sulfate anion and a water molecule. These species are connected by N—H
O and O—H
O hydrogen bonds, resulting in a three-dimensional network.
Supporting information
CCDC reference: 255906
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.075
- wR factor = 0.251
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.251
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.102
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.19
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: FEBO (Belleti, 1996); cell refinement: MolEN (Fair, 1990); data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1997); software used to prepare material for publication: PLATON.
Bis(2,4-diamino-6-oxopyrimidinium) sulfate monohydrate
top
Crystal data top
2C4H7N4O+·O4S2−·H2O | F(000) = 768 |
Mr = 368.36 | Dx = 1.690 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 15.014 (3) Å | θ = 1.4–25.6° |
b = 6.568 (2) Å | µ = 0.28 mm−1 |
c = 15.330 (3) Å | T = 293 K |
β = 106.69 (2)° | Plate, colourless |
V = 1448.0 (6) Å3 | 0.37 × 0.29 × 0.22 mm |
Z = 4 | |
Data collection top
Philips PW 1100 diffractometer | Rint = 0.102 |
Radiation source: fine-focus sealed tube | θmax = 25.6°, θmin = 1.4° |
Graphite monochromator | h = −18→17 |
ω scans | k = 0→7 |
2811 measured reflections | l = 0→18 |
2715 independent reflections | 1 standard reflections every 100 reflections |
2210 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.075 | Hydrogen site location: difmap (O-H) and geom (others) |
wR(F2) = 0.251 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.1166P)2 + 5.4696P] where P = (Fo2 + 2Fc2)/3 |
2715 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.87 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR and all
goodnesses of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The observed criterion of F2 > σ(F2)
is used only for calculating -R-factor-obs 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 | Uiso*/Ueq | |
O6 | 0.9433 (3) | 0.2052 (6) | 0.3260 (3) | 0.0540 (14) | |
N1 | 0.8721 (3) | 0.4855 (6) | 0.2518 (3) | 0.0347 (12) | |
N2 | 0.7978 (3) | 0.7686 (7) | 0.1734 (3) | 0.0433 (14) | |
N3 | 0.9207 (3) | 0.8085 (6) | 0.3033 (3) | 0.0325 (11) | |
N4 | 1.0419 (3) | 0.8692 (7) | 0.4318 (3) | 0.0401 (14) | |
C2 | 0.8625 (4) | 0.6878 (7) | 0.2416 (3) | 0.0325 (14) | |
C4 | 0.9906 (3) | 0.7319 (7) | 0.3751 (3) | 0.0313 (14) | |
C5 | 1.0015 (4) | 0.5219 (7) | 0.3837 (3) | 0.0356 (14) | |
C6 | 0.9410 (4) | 0.3953 (8) | 0.3224 (3) | 0.0358 (16) | |
O6' | 0.5772 (3) | −0.2706 (5) | 0.6978 (3) | 0.0515 (15) | |
N1' | 0.5040 (3) | 0.0093 (6) | 0.6221 (3) | 0.0355 (12) | |
N2' | 0.4244 (3) | 0.2868 (7) | 0.5463 (3) | 0.0419 (16) | |
N3' | 0.5545 (3) | 0.3328 (6) | 0.6690 (3) | 0.0326 (11) | |
N4' | 0.6805 (3) | 0.3970 (7) | 0.7935 (3) | 0.0395 (14) | |
C2' | 0.4933 (3) | 0.2101 (7) | 0.6113 (3) | 0.0336 (14) | |
C4' | 0.6259 (3) | 0.2581 (7) | 0.7405 (3) | 0.0314 (14) | |
C5' | 0.6356 (4) | 0.0516 (7) | 0.7531 (3) | 0.0346 (14) | |
C6' | 0.5748 (4) | −0.0816 (7) | 0.6930 (3) | 0.0356 (16) | |
S1 | 0.71820 (8) | 0.22463 (17) | 0.52743 (8) | 0.0302 (4) | |
O1 | 0.6211 (3) | 0.2917 (6) | 0.4887 (3) | 0.0429 (12) | |
O2 | 0.7188 (3) | −0.0021 (5) | 0.5300 (2) | 0.0422 (11) | |
O3 | 0.7582 (3) | 0.3025 (6) | 0.6202 (2) | 0.0444 (11) | |
O4 | 0.7748 (3) | 0.2920 (6) | 0.4684 (2) | 0.0405 (11) | |
O1W | 0.8049 (4) | 0.7181 (8) | 0.4316 (4) | 0.081 (2) | |
H1 | 0.83420 | 0.40800 | 0.21320 | 0.0420* | |
H2A | 0.76060 | 0.69120 | 0.13410 | 0.0520* | |
H2B | 0.79280 | 0.89880 | 0.16800 | 0.0520* | |
H3 | 0.91410 | 0.93830 | 0.29780 | 0.0390* | |
H4A | 1.03040 | 0.99700 | 0.42240 | 0.0480* | |
H4B | 1.08640 | 0.83010 | 0.47780 | 0.0480* | |
H5 | 1.04930 | 0.46700 | 0.43050 | 0.0420* | |
H1' | 0.46600 | −0.06900 | 0.58400 | 0.0420* | |
H2A' | 0.38530 | 0.20710 | 0.51000 | 0.0510* | |
H2B' | 0.41820 | 0.41660 | 0.54010 | 0.0510* | |
H3' | 0.54910 | 0.46240 | 0.66120 | 0.0390* | |
H5' | 0.68270 | −0.00010 | 0.80150 | 0.0410* | |
H41' | 0.72550 | 0.35910 | 0.83930 | 0.0480* | |
H42' | 0.67060 | 0.52450 | 0.78180 | 0.0480* | |
H1W | 0.78650 | 0.57950 | 0.43480 | 0.0420* | |
H2W | 0.78120 | 0.79440 | 0.47400 | 0.0420* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O6 | 0.078 (3) | 0.0182 (19) | 0.058 (2) | 0.0000 (18) | 0.007 (2) | 0.0000 (16) |
N1 | 0.048 (2) | 0.021 (2) | 0.036 (2) | −0.0019 (17) | 0.0135 (18) | −0.0029 (16) |
N2 | 0.053 (3) | 0.027 (2) | 0.042 (2) | −0.0016 (19) | 0.001 (2) | 0.0004 (18) |
N3 | 0.046 (2) | 0.0157 (18) | 0.038 (2) | −0.0013 (16) | 0.0154 (18) | 0.0000 (15) |
N4 | 0.049 (3) | 0.025 (2) | 0.043 (2) | 0.0020 (18) | 0.008 (2) | −0.0046 (18) |
C2 | 0.043 (3) | 0.023 (2) | 0.035 (2) | −0.0006 (19) | 0.017 (2) | 0.0010 (19) |
C4 | 0.037 (3) | 0.026 (2) | 0.035 (2) | −0.0007 (19) | 0.017 (2) | −0.0020 (19) |
C5 | 0.046 (3) | 0.026 (2) | 0.035 (2) | 0.006 (2) | 0.012 (2) | 0.0016 (19) |
C6 | 0.048 (3) | 0.025 (2) | 0.038 (3) | 0.002 (2) | 0.018 (2) | 0.0034 (19) |
O6' | 0.063 (3) | 0.0150 (18) | 0.069 (3) | 0.0001 (16) | 0.007 (2) | −0.0009 (17) |
N1' | 0.040 (2) | 0.024 (2) | 0.043 (2) | −0.0010 (17) | 0.0129 (18) | −0.0049 (17) |
N2' | 0.046 (3) | 0.026 (2) | 0.049 (3) | −0.0007 (19) | 0.006 (2) | 0.0014 (19) |
N3' | 0.044 (2) | 0.0182 (19) | 0.038 (2) | −0.0013 (16) | 0.0158 (18) | 0.0015 (16) |
N4' | 0.051 (3) | 0.027 (2) | 0.037 (2) | −0.0040 (19) | 0.0069 (19) | −0.0011 (17) |
C2' | 0.041 (3) | 0.025 (2) | 0.039 (2) | 0.000 (2) | 0.018 (2) | 0.0000 (19) |
C4' | 0.040 (3) | 0.028 (2) | 0.031 (2) | −0.0008 (19) | 0.018 (2) | 0.0007 (18) |
C5' | 0.046 (3) | 0.021 (2) | 0.038 (2) | 0.001 (2) | 0.014 (2) | 0.0023 (19) |
C6' | 0.045 (3) | 0.019 (2) | 0.046 (3) | 0.000 (2) | 0.018 (2) | 0.005 (2) |
S1 | 0.0375 (7) | 0.0216 (6) | 0.0324 (6) | 0.0001 (4) | 0.0114 (5) | 0.0004 (4) |
O1 | 0.043 (2) | 0.032 (2) | 0.054 (2) | 0.0048 (16) | 0.0143 (17) | 0.0050 (16) |
O2 | 0.056 (2) | 0.0201 (18) | 0.046 (2) | −0.0002 (15) | 0.0074 (17) | 0.0006 (14) |
O3 | 0.061 (2) | 0.036 (2) | 0.0377 (19) | −0.0023 (18) | 0.0166 (18) | −0.0025 (16) |
O4 | 0.046 (2) | 0.040 (2) | 0.0382 (19) | −0.0056 (16) | 0.0166 (16) | 0.0004 (15) |
O1W | 0.108 (4) | 0.055 (3) | 0.107 (4) | −0.002 (3) | 0.073 (4) | 0.001 (3) |
Geometric parameters (Å, º) top
S1—O3 | 1.468 (3) | N4—H4B | 0.8596 |
S1—O1 | 1.475 (5) | N1'—C6' | 1.416 (7) |
S1—O2 | 1.490 (3) | N1'—C2' | 1.333 (6) |
S1—O4 | 1.476 (4) | N2'—C2' | 1.313 (6) |
O6—C6 | 1.250 (7) | N3'—C4' | 1.384 (6) |
O6'—C6' | 1.243 (6) | N3'—C2' | 1.345 (6) |
O1W—H1W | 0.9567 | N4'—C4' | 1.335 (6) |
O1W—H2W | 0.9660 | N1'—H1' | 0.8601 |
N1—C2 | 1.341 (6) | N2'—H2A' | 0.8606 |
N1—C6 | 1.396 (7) | N2'—H2B' | 0.8599 |
N2—C2 | 1.317 (7) | N3'—H3' | 0.8602 |
N3—C4 | 1.379 (6) | N4'—H42' | 0.8604 |
N3—C2 | 1.346 (7) | N4'—H41' | 0.8596 |
N4—C4 | 1.333 (6) | C4—C5 | 1.391 (7) |
N1—H1 | 0.8600 | C5—C6 | 1.382 (7) |
N2—H2A | 0.8603 | C5—H5 | 0.9295 |
N2—H2B | 0.8604 | C4'—C5' | 1.372 (7) |
N3—H3 | 0.8596 | C5'—C6' | 1.402 (7) |
N4—H4A | 0.8607 | C5'—H5' | 0.9298 |
| | | |
O3—S1—O4 | 110.0 (2) | C4'—N4'—H42' | 119.95 |
O1—S1—O4 | 109.9 (2) | C4'—N4'—H41' | 120.03 |
O1—S1—O2 | 107.9 (2) | H41'—N4'—H42' | 120.02 |
O1—S1—O3 | 111.6 (3) | N1—C2—N2 | 121.5 (5) |
O2—S1—O3 | 109.0 (2) | N1—C2—N3 | 118.4 (4) |
O2—S1—O4 | 108.4 (2) | N2—C2—N3 | 120.2 (4) |
H1W—O1W—H2W | 106.95 | N4—C4—C5 | 125.4 (4) |
C2—N1—C6 | 122.8 (4) | N3—C4—C5 | 118.6 (4) |
C2—N3—C4 | 122.5 (4) | N3—C4—N4 | 116.0 (4) |
C2—N1—H1 | 118.59 | C4—C5—C6 | 119.7 (5) |
C6—N1—H1 | 118.60 | O6—C6—C5 | 124.5 (5) |
C2—N2—H2A | 120.02 | N1—C6—C5 | 117.9 (5) |
H2A—N2—H2B | 119.92 | O6—C6—N1 | 117.6 (5) |
C2—N2—H2B | 120.06 | C4—C5—H5 | 120.11 |
C4—N3—H3 | 118.68 | C6—C5—H5 | 120.17 |
C2—N3—H3 | 118.81 | N1'—C2'—N3' | 118.4 (4) |
H4A—N4—H4B | 120.00 | N2'—C2'—N3' | 120.6 (4) |
C4—N4—H4A | 120.00 | N1'—C2'—N2' | 120.9 (4) |
C4—N4—H4B | 120.01 | N4'—C4'—C5' | 124.6 (4) |
C2'—N1'—C6' | 123.3 (4) | N3'—C4'—C5' | 119.3 (4) |
C2'—N3'—C4' | 122.4 (4) | N3'—C4'—N4' | 116.1 (4) |
C6'—N1'—H1' | 118.33 | C4'—C5'—C6' | 120.1 (4) |
C2'—N1'—H1' | 118.32 | N1'—C6'—C5' | 116.4 (4) |
C2'—N2'—H2A' | 119.98 | O6'—C6'—N1' | 118.0 (5) |
H2A'—N2'—H2B' | 119.97 | O6'—C6'—C5' | 125.6 (5) |
C2'—N2'—H2B' | 120.06 | C4'—C5'—H5' | 119.94 |
C4'—N3'—H3' | 118.78 | C6'—C5'—H5' | 119.94 |
C2'—N3'—H3' | 118.83 | | |
| | | |
C6—N1—C2—N2 | 178.8 (5) | C2'—N3'—C4'—N4' | −178.8 (5) |
C6—N1—C2—N3 | −1.4 (8) | C2'—N3'—C4'—C5' | 0.5 (7) |
C2—N1—C6—O6 | 179.4 (5) | C4'—N3'—C2'—N1' | −2.1 (7) |
C2—N1—C6—C5 | −0.2 (8) | C4'—N3'—C2'—N2' | 177.5 (5) |
C4—N3—C2—N1 | 1.4 (8) | N4—C4—C5—C6 | 177.2 (5) |
C2—N3—C4—C5 | 0.3 (7) | N3—C4—C5—C6 | −1.9 (8) |
C4—N3—C2—N2 | −178.9 (5) | C4—C5—C6—N1 | 1.8 (8) |
C2—N3—C4—N4 | −178.9 (5) | C4—C5—C6—O6 | −177.7 (5) |
C2'—N1'—C6'—C5' | −0.4 (8) | N3'—C4'—C5'—C6' | 1.2 (8) |
C6'—N1'—C2'—N3' | 2.1 (7) | N4'—C4'—C5'—C6' | −179.5 (5) |
C2'—N1'—C6'—O6' | 178.5 (5) | C4'—C5'—C6'—O6' | 179.9 (5) |
C6'—N1'—C2'—N2' | −177.5 (5) | C4'—C5'—C6'—N1' | −1.3 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.08 | 2.931 (6) | 172 |
N1′—H1′···O1ii | 0.86 | 2.06 | 2.914 (6) | 170 |
N2′—H2A′···O2ii | 0.86 | 2.02 | 2.836 (6) | 158 |
O1W—H1W···O4 | 0.96 | 1.98 | 2.916 (7) | 166 |
N2′—H2B′···O1iii | 0.86 | 2.02 | 2.865 (6) | 169 |
N2—H2A···O2i | 0.86 | 1.98 | 2.794 (6) | 158 |
N2—H2B···O3iv | 0.86 | 2.11 | 2.945 (6) | 165 |
O1W—H2W···O2v | 0.97 | 1.97 | 2.906 (7) | 164 |
N3—H3···O6v | 0.86 | 1.83 | 2.638 (6) | 156 |
N3′—H3′···O6′v | 0.86 | 1.85 | 2.648 (5) | 153 |
N4—H4A···O6v | 0.86 | 2.16 | 2.883 (6) | 142 |
N4—H4B···O4vi | 0.86 | 2.16 | 2.935 (6) | 149 |
N4′—H41′···O4vii | 0.86 | 2.15 | 2.925 (6) | 150 |
N4′—H42′···O6′v | 0.86 | 2.10 | 2.831 (6) | 143 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) x, −y+3/2, z−1/2; (v) x, y+1, z; (vi) −x+2, −y+1, −z+1; (vii) x, −y+1/2, z+1/2. |
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