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The six-membered ring of the 3,5-dinitropyridin-4-olate anion in the title dihydrated sodium derivative, Na+·C5H2N3O5-·2H2O, exists in the pyridone form with C=C and C=O double bonds, and the negative charge formally residing on the N atom. The anions link the Na+ ions, each of which is coordinated by four water molecules, into a linear chain that runs along the c axis of the unit cell. The chains are bridged by the water molecules into a sheet structure. The anion and the Na+ ion lie on a mirror plane.
Supporting information
CCDC reference: 636164
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.132
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.35
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2006).
Sodium 3,5-dinitropyridin-4-olate dihydrate
top
Crystal data top
Na+·C5H2N3O5−·2H2O | F(000) = 248 |
Mr = 243.12 | Dx = 1.755 Mg m−3 |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yb | Cell parameters from 1757 reflections |
a = 3.6392 (5) Å | θ = 2.3–28.0° |
b = 14.446 (2) Å | µ = 0.20 mm−1 |
c = 8.859 (1) Å | T = 295 K |
β = 98.876 (1)° | Block, yellow–orange |
V = 460.2 (1) Å3 | 0.40 × 0.27 × 0.17 mm |
Z = 2 | |
Data collection top
Bruker APEX2 area-detector diffractometer | 957 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 27.5°, θmin = 2.3° |
φ and ω scans | h = −4→4 |
3973 measured reflections | k = −18→18 |
1101 independent reflections | l = −11→11 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0692P)2 + 0.1823P] where P = (Fo2 + 2Fc2)/3 |
1101 reflections | (Δ/σ)max = 0.001 |
79 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Na1 | 0.3957 (3) | 0.7500 | 0.6585 (1) | 0.0425 (3) | |
O1 | 0.1324 (6) | 0.7500 | 0.3829 (2) | 0.0431 (5) | |
O2 | 0.0800 (7) | 0.5664 (1) | 0.3390 (2) | 0.0782 (7) | |
O3 | 0.3062 (7) | 0.5099 (1) | 0.1551 (2) | 0.0823 (7) | |
O1w | 0.8680 (4) | 0.6438 (1) | 0.6178 (2) | 0.0460 (4) | |
N1 | 0.2105 (5) | 0.5768 (1) | 0.2224 (2) | 0.0403 (4) | |
N2 | 0.3558 (6) | 0.7500 | −0.0647 (2) | 0.0393 (5) | |
C1 | 0.1967 (6) | 0.7500 | 0.2496 (2) | 0.0293 (5) | |
C2 | 0.2422 (5) | 0.6683 (1) | 0.1594 (2) | 0.0315 (4) | |
C3 | 0.3182 (5) | 0.6717 (1) | 0.0120 (2) | 0.0364 (4) | |
H1 | 0.8325 | 0.6218 | 0.5277 | 0.055* | |
H2 | 0.8906 | 0.6000 | 0.6825 | 0.055* | |
H3 | 0.3452 | 0.6159 | −0.0375 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Na1 | 0.0475 (6) | 0.0482 (6) | 0.0348 (6) | 0.000 | 0.0158 (4) | 0.000 |
O1 | 0.069 (1) | 0.035 (1) | 0.029 (1) | 0.000 | 0.021 (1) | 0.000 |
O2 | 0.151 (2) | 0.036 (1) | 0.063 (1) | −0.004 (1) | 0.063 (1) | 0.006 (1) |
O3 | 0.147 (2) | 0.034 (1) | 0.081 (1) | 0.015 (1) | 0.063 (1) | 0.000 (1) |
O1w | 0.063 (1) | 0.033 (1) | 0.044 (1) | −0.001 (1) | 0.015 (1) | 0.002 (1) |
N1 | 0.055 (1) | 0.030 (1) | 0.039 (1) | 0.000 (1) | 0.014 (1) | −0.001 (1) |
N2 | 0.049 (1) | 0.043 (1) | 0.028 (1) | 0.000 | 0.014 (1) | 0.000 |
C1 | 0.032 (1) | 0.031 (1) | 0.026 (1) | 0.000 | 0.008 (1) | 0.000 |
C2 | 0.036 (1) | 0.029 (1) | 0.030 (1) | 0.001 (1) | 0.010 (1) | 0.001 (1) |
C3 | 0.043 (1) | 0.037 (1) | 0.031 (1) | 0.001 (1) | 0.011 (1) | −0.005 (1) |
Geometric parameters (Å, º) top
Na1—O1 | 2.482 (2) | N1—C2 | 1.446 (2) |
Na1—O1w | 2.373 (2) | N2—C3iii | 1.337 (2) |
Na1—O1wi | 2.441 (2) | N2—C3 | 1.337 (2) |
Na1—O1wii | 2.441 (2) | C1—C2iii | 1.449 (2) |
Na1—O1wiii | 2.373 (2) | C1—C2 | 1.449 (2) |
Na1—N2iv | 2.479 (2) | C2—C3 | 1.377 (2) |
O1—C1 | 1.238 (3) | O1w—H1 | 0.85 |
O2—N1 | 1.211 (2) | O1w—H2 | 0.85 |
O3—N1 | 1.214 (2) | C3—H3 | 0.93 |
| | | |
O1—Na1—O1w | 91.66 (6) | O2—N1—C2 | 120.5 (2) |
O1—Na1—O1wi | 71.27 (6) | C3iii—N2—C3 | 115.6 (2) |
O1—Na1—O1wii | 71.27 (6) | C3iii—N2—Na1vi | 121.9 (1) |
O1—Na1—O1wiii | 91.66 (6) | C3—N2—Na1vi | 121.9 (1) |
O1—Na1—N2iv | 154.26 (8) | O1—C1—C2iii | 125.4 (1) |
O1w—Na1—O1wi | 98.23 (5) | O1—C1—C2 | 125.4 (1) |
O1w—Na1—O1wii | 162.89 (8) | C2iii—C1—C2 | 109.1 (2) |
O1w—Na1—O1wiii | 80.55 (7) | C3—C2—N1 | 116.0 (1) |
O1w—Na1—N2iv | 107.75 (6) | C3—C2—C1 | 123.4 (2) |
O1wi—Na1—O1wii | 77.87 (7) | N1—C2—C1 | 120.6 (1) |
O1wi—Na1—O1wiii | 162.89 (8) | N2—C3—C2 | 124.3 (2) |
O1wi—Na1—N2iv | 88.94 (6) | Na1—O1w—H1 | 112.1 |
O1wii—Na1—O1wiii | 98.23 (5) | Na1v—O1w—H1 | 112.1 |
O1wii—Na1—N2iv | 88.94 (6) | Na1—O1w—H2 | 112.1 |
O1wiii—Na1—N2iv | 107.75 (6) | Na1v—O1w—H2 | 112.1 |
Na1—O1w—Na1v | 98.23 (5) | H1—O1w—H2 | 109.8 |
C1—O1—Na1 | 146.8 (2) | N2—C3—H3 | 117.9 |
O3—N1—O2 | 120.0 (2) | C2—C3—H3 | 117.9 |
O3—N1—C2 | 119.5 (2) | | |
| | | |
O1wiii—Na1—O1—C1 | 40.30 (4) | O2—N1—C2—C3 | −166.7 (2) |
O1w—Na1—O1—C1 | −40.30 (4) | O3—N1—C2—C1 | −168.5 (2) |
O1wi—Na1—O1—C1 | −138.43 (4) | O2—N1—C2—C1 | 13.6 (3) |
O1wii—Na1—O1—C1 | 138.43 (4) | O1—C1—C2—C3 | −179.1 (2) |
N2iv—Na1—O1—C1 | 180.0 | C2iii—C1—C2—C3 | 0.3 (3) |
O1wiii—Na1—O1w—Na1v | 17.27 (8) | O1—C1—C2—N1 | 0.6 (3) |
O1wi—Na1—O1w—Na1v | 180.0 | C2iii—C1—C2—N1 | 180.0 (1) |
N2iv—Na1—O1w—Na1v | −88.47 (6) | C3iii—N2—C3—C2 | 0.7 (4) |
O1—Na1—O1w—Na1v | 108.68 (6) | Na1vi—N2—C3—C2 | −170.4 (2) |
Na1—O1—C1—C2iii | −89.7 (2) | N1—C2—C3—N2 | 179.8 (2) |
Na1—O1—C1—C2 | 89.7 (2) | C1—C2—C3—N2 | −0.5 (3) |
O3—N1—C2—C3 | 11.3 (3) | | |
Symmetry codes: (i) x−1, y, z; (ii) x−1, −y+3/2, z; (iii) x, −y+3/2, z; (iv) x, y, z+1; (v) x+1, y, z; (vi) x, y, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H2···O2vii | 0.85 | 2.41 | 3.063 (2) | 134 |
O1w—H2···O3vii | 0.85 | 2.33 | 3.127 (2) | 157 |
O1w—H1···O2v | 0.85 | 2.17 | 2.922 (2) | 147 |
Symmetry codes: (v) x+1, y, z; (vii) −x+1, −y+1, −z+1. |
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