Download citation
Download citation
link to html
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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055590/bt2232sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055590/bt2232Isup2.hkl
Contains datablock I

CCDC reference: 636164

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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+·C5H2N3O5·2H2OF(000) = 248
Mr = 243.12Dx = 1.755 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 1757 reflections
a = 3.6392 (5) Åθ = 2.3–28.0°
b = 14.446 (2) ŵ = 0.20 mm1
c = 8.859 (1) ÅT = 295 K
β = 98.876 (1)°Block, yellow–orange
V = 460.2 (1) Å30.40 × 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 tubeRint = 0.015
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
φ and ω scansh = 44
3973 measured reflectionsk = 1818
1101 independent reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-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 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.35 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Na10.3957 (3)0.75000.6585 (1)0.0425 (3)
O10.1324 (6)0.75000.3829 (2)0.0431 (5)
O20.0800 (7)0.5664 (1)0.3390 (2)0.0782 (7)
O30.3062 (7)0.5099 (1)0.1551 (2)0.0823 (7)
O1w0.8680 (4)0.6438 (1)0.6178 (2)0.0460 (4)
N10.2105 (5)0.5768 (1)0.2224 (2)0.0403 (4)
N20.3558 (6)0.75000.0647 (2)0.0393 (5)
C10.1967 (6)0.75000.2496 (2)0.0293 (5)
C20.2422 (5)0.6683 (1)0.1594 (2)0.0315 (4)
C30.3182 (5)0.6717 (1)0.0120 (2)0.0364 (4)
H10.83250.62180.52770.055*
H20.89060.60000.68250.055*
H30.34520.61590.03750.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0475 (6)0.0482 (6)0.0348 (6)0.0000.0158 (4)0.000
O10.069 (1)0.035 (1)0.029 (1)0.0000.021 (1)0.000
O20.151 (2)0.036 (1)0.063 (1)0.004 (1)0.063 (1)0.006 (1)
O30.147 (2)0.034 (1)0.081 (1)0.015 (1)0.063 (1)0.000 (1)
O1w0.063 (1)0.033 (1)0.044 (1)0.001 (1)0.015 (1)0.002 (1)
N10.055 (1)0.030 (1)0.039 (1)0.000 (1)0.014 (1)0.001 (1)
N20.049 (1)0.043 (1)0.028 (1)0.0000.014 (1)0.000
C10.032 (1)0.031 (1)0.026 (1)0.0000.008 (1)0.000
C20.036 (1)0.029 (1)0.030 (1)0.001 (1)0.010 (1)0.001 (1)
C30.043 (1)0.037 (1)0.031 (1)0.001 (1)0.011 (1)0.005 (1)
Geometric parameters (Å, º) top
Na1—O12.482 (2)N1—C21.446 (2)
Na1—O1w2.373 (2)N2—C3iii1.337 (2)
Na1—O1wi2.441 (2)N2—C31.337 (2)
Na1—O1wii2.441 (2)C1—C2iii1.449 (2)
Na1—O1wiii2.373 (2)C1—C21.449 (2)
Na1—N2iv2.479 (2)C2—C31.377 (2)
O1—C11.238 (3)O1w—H10.85
O2—N11.211 (2)O1w—H20.85
O3—N11.214 (2)C3—H30.93
O1—Na1—O1w91.66 (6)O2—N1—C2120.5 (2)
O1—Na1—O1wi71.27 (6)C3iii—N2—C3115.6 (2)
O1—Na1—O1wii71.27 (6)C3iii—N2—Na1vi121.9 (1)
O1—Na1—O1wiii91.66 (6)C3—N2—Na1vi121.9 (1)
O1—Na1—N2iv154.26 (8)O1—C1—C2iii125.4 (1)
O1w—Na1—O1wi98.23 (5)O1—C1—C2125.4 (1)
O1w—Na1—O1wii162.89 (8)C2iii—C1—C2109.1 (2)
O1w—Na1—O1wiii80.55 (7)C3—C2—N1116.0 (1)
O1w—Na1—N2iv107.75 (6)C3—C2—C1123.4 (2)
O1wi—Na1—O1wii77.87 (7)N1—C2—C1120.6 (1)
O1wi—Na1—O1wiii162.89 (8)N2—C3—C2124.3 (2)
O1wi—Na1—N2iv88.94 (6)Na1—O1w—H1112.1
O1wii—Na1—O1wiii98.23 (5)Na1v—O1w—H1112.1
O1wii—Na1—N2iv88.94 (6)Na1—O1w—H2112.1
O1wiii—Na1—N2iv107.75 (6)Na1v—O1w—H2112.1
Na1—O1w—Na1v98.23 (5)H1—O1w—H2109.8
C1—O1—Na1146.8 (2)N2—C3—H3117.9
O3—N1—O2120.0 (2)C2—C3—H3117.9
O3—N1—C2119.5 (2)
O1wiii—Na1—O1—C140.30 (4)O2—N1—C2—C3166.7 (2)
O1w—Na1—O1—C140.30 (4)O3—N1—C2—C1168.5 (2)
O1wi—Na1—O1—C1138.43 (4)O2—N1—C2—C113.6 (3)
O1wii—Na1—O1—C1138.43 (4)O1—C1—C2—C3179.1 (2)
N2iv—Na1—O1—C1180.0C2iii—C1—C2—C30.3 (3)
O1wiii—Na1—O1w—Na1v17.27 (8)O1—C1—C2—N10.6 (3)
O1wi—Na1—O1w—Na1v180.0C2iii—C1—C2—N1180.0 (1)
N2iv—Na1—O1w—Na1v88.47 (6)C3iii—N2—C3—C20.7 (4)
O1—Na1—O1w—Na1v108.68 (6)Na1vi—N2—C3—C2170.4 (2)
Na1—O1—C1—C2iii89.7 (2)N1—C2—C3—N2179.8 (2)
Na1—O1—C1—C289.7 (2)C1—C2—C3—N20.5 (3)
O3—N1—C2—C311.3 (3)
Symmetry codes: (i) x1, y, z; (ii) x1, y+3/2, z; (iii) x, y+3/2, z; (iv) x, y, z+1; (v) x+1, y, z; (vi) x, y, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H2···O2vii0.852.413.063 (2)134
O1w—H2···O3vii0.852.333.127 (2)157
O1w—H1···O2v0.852.172.922 (2)147
Symmetry codes: (v) x+1, y, z; (vii) x+1, y+1, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds