Download citation
Download citation
link to html
In the title compound, sodium 2-hydr­oxy-3,4-dioxocyclo­but-1-en-1-olate monohydrate, Na+·C4HO4-·H2O, the Na atom is six-coordinated by the O atoms from four hydrogensquarate anions and two water mol­ecules. The three-dimensional packing is stabilized by a system of hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601806X/ob2016sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601806X/ob2016Isup2.hkl
Contains datablock I

CCDC reference: 610859

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.058
  • wR factor = 0.145
  • Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C REFLT03_ALERT_1_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 29.93 From the CIF: _diffrn_reflns_theta_full 29.93 From the CIF: _reflns_number_total 760 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 801 Completeness (_total/calc) 94.88% PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.21 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 29.93 From the CIF: _reflns_number_total 760 Count of symmetry unique reflns 801 Completeness (_total/calc) 94.88% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX (Farrugia, 1999).

sodium 2-hydroxy-3,4-dioxocyclobut-1-en-1-olate hydrate top
Crystal data top
Na+·C4HO4·H2OF(000) = 156
Mr = 154.05Dx = 1.867 Mg m3
Monoclinic, PcMelting point: not measured K
Hall symbol: P -2ycMo Kα radiation, λ = 0.71073 Å
a = 3.6239 (10) ÅCell parameters from 22 reflections
b = 8.1320 (11) Åθ = 20.2–21.3°
c = 9.392 (4) ŵ = 0.24 mm1
β = 97.97 (3)°T = 290 K
V = 274.10 (14) Å3Prism, colorless
Z = 20.26 × 0.25 × 0.24 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.077
Radiation source: fine-focus sealed tubeθmax = 29.9°, θmin = 2.5°
Graphite monochromatorh = 05
non–profiled ω/2θ scansk = 1111
1413 measured reflectionsl = 1313
760 independent reflections3 standard reflections every 120 min
543 reflections with I > 2σ(I) intensity decay: 2%
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.20 w = 1/[σ2(Fo2) + (0.0298P)2 + 0.6752P]
where P = (Fo2 + 2Fc2)/3
760 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.38 e Å3
2 restraintsΔρmin = 0.43 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3223 (18)0.5547 (8)0.2768 (7)0.0166 (13)
C20.0859 (18)0.5585 (9)0.1439 (7)0.0175 (14)
C30.0926 (19)0.7337 (9)0.1359 (8)0.0188 (14)
C40.3383 (19)0.7378 (8)0.2784 (8)0.0188 (14)
Na10.4546 (8)0.1373 (4)0.3563 (4)0.0262 (6)
O0.9008 (14)0.1342 (6)0.1946 (5)0.0280 (12)
H1A0.88030.03570.13580.034*
H1B0.87930.23040.13290.034*
O10.4713 (17)0.4414 (6)0.3569 (6)0.0225 (10)
O20.0862 (13)0.4435 (6)0.0638 (5)0.0204 (11)
H10.25080.46710.00280.024*
O30.0347 (15)0.8401 (6)0.0462 (6)0.0253 (12)
O40.482 (2)0.8418 (6)0.3596 (8)0.0289 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.018 (3)0.017 (3)0.015 (3)0.001 (3)0.000 (2)0.000 (3)
C20.018 (3)0.016 (3)0.017 (3)0.002 (3)0.002 (2)0.004 (3)
C30.021 (3)0.019 (3)0.015 (3)0.004 (3)0.001 (2)0.001 (3)
C40.019 (3)0.015 (3)0.020 (3)0.003 (3)0.004 (3)0.000 (3)
Na10.0257 (13)0.0232 (13)0.0268 (13)0.0005 (16)0.0059 (10)0.0056 (17)
O0.042 (3)0.017 (2)0.024 (3)0.001 (3)0.001 (2)0.002 (2)
O10.029 (2)0.019 (2)0.016 (2)0.000 (3)0.0104 (17)0.000 (3)
O20.025 (2)0.016 (2)0.017 (2)0.004 (2)0.0085 (19)0.003 (2)
O30.035 (3)0.018 (2)0.019 (2)0.007 (2)0.009 (2)0.002 (2)
O40.035 (3)0.018 (2)0.030 (2)0.005 (3)0.010 (2)0.004 (3)
Geometric parameters (Å, º) top
C1—O11.262 (8)Na1—O2.367 (6)
C1—C21.412 (8)Na1—O3ii2.393 (7)
C1—C41.490 (9)Na1—O4iii2.405 (6)
C2—O21.304 (7)Na1—O12.474 (6)
C2—C31.427 (10)Na1—O3iv2.691 (7)
C3—O31.250 (9)O—Na1v2.343 (6)
C3—C41.502 (8)O—H1A0.9700
C4—O41.207 (9)O—H1B0.9700
Na1—Oi2.343 (6)O2—H10.8245
O1—C1—C2134.4 (7)O1—Na1—O3iv87.0 (2)
O1—C1—C4135.2 (7)Oi—Na1—Na1i39.93 (14)
C2—C1—C490.3 (6)O—Na1—Na1i140.54 (15)
O2—C2—C1132.6 (7)O3ii—Na1—Na1i132.06 (16)
O2—C2—C3134.1 (6)O4iii—Na1—Na1i92.2 (2)
C1—C2—C393.2 (7)O1—Na1—Na1i91.38 (17)
O3—C3—C2136.0 (7)O3iv—Na1—Na1i41.32 (14)
O3—C3—C4134.7 (7)Oi—Na1—Na1v140.07 (14)
C2—C3—C489.2 (6)O—Na1—Na1v39.46 (15)
O4—C4—C1136.0 (7)O3ii—Na1—Na1v47.94 (16)
O4—C4—C3136.8 (7)O4iii—Na1—Na1v87.8 (2)
C1—C4—C387.2 (6)O1—Na1—Na1v88.62 (17)
Oi—Na1—O100.6 (2)O3iv—Na1—Na1v138.68 (14)
Oi—Na1—O3ii171.3 (2)Na1i—Na1—Na1v180.00 (18)
O—Na1—O3ii87.3 (2)Na1v—O—Na1100.6 (2)
Oi—Na1—O4iii91.6 (2)Na1v—O—H1A111.6
O—Na1—O4iii88.1 (3)Na1—O—H1A111.6
O3ii—Na1—O4iii92.3 (2)Na1v—O—H1B111.6
Oi—Na1—O191.8 (2)Na1—O—H1B111.6
O—Na1—O189.6 (2)H1A—O—H1B109.4
O3ii—Na1—O184.6 (2)C1—O1—Na1136.0 (4)
O4iii—Na1—O1176.3 (3)C2—O2—H1120.6
Oi—Na1—O3iv81.2 (2)C3—O3—Na1vi136.9 (5)
O—Na1—O3iv176.3 (2)C3—O3—Na1vii106.1 (5)
O3ii—Na1—O3iv90.7 (2)Na1vi—O3—Na1vii90.7 (2)
O4iii—Na1—O3iv95.1 (2)C4—O4—Na1viii132.7 (6)
Symmetry codes: (i) x1, y, z; (ii) x+1, y+1, z+1/2; (iii) x, y1, z; (iv) x, y+1, z+1/2; (v) x+1, y, z; (vi) x1, y+1, z1/2; (vii) x, y+1, z1/2; (viii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1vi0.821.712.522 (7)166
O—H1B···O2v0.971.862.803 (7)163
O—H1A···O3ix0.971.842.794 (7)165
Symmetry codes: (v) x+1, y, z; (vi) x1, y+1, z1/2; (ix) x+1, y1, z.
 

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