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Each of the two acid H atoms in the centrosymmetric [C6H2(CO2H)2(CO2)2]2- dianion of disodium di­hydrogen 1,2,4,5-benzene­tetra­carboxyl­ate dihydrate, 2Na+·C10H4O82-·2H2O, holds together a pair of adjacent carboxyl groups so that all four groups are coplanar with the aromatic ring. The Na+ cation has a distorted octahedral coordination made up of two cis-coordinated water mol­ecules and the O atoms of four carboxyl groups belonging to four different dianions; the water mol­ecule acts as a bridge between two Na+ ions related by an inversion center.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017816/ya6137sup1.cif
Contains datablocks I, ya6137

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017816/ya6137Isup2.hkl
Contains datablock I

CCDC reference: 200719

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.107
  • Data-to-parameter ratio = 11.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.10 From the CIF: _reflns_number_total 1311 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1429 Completeness (_total/calc) 91.74% Alert C: < 95% complete PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C1 - C2 = 1.53 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Disodium dihydrogen 1,2,4,5-benzenetetracarboxylate dihydrate top
Crystal data top
2Na+·C10H4O82·2H2OZ = 1
Mr = 334.14F(000) = 170
Triclinic, P1Dx = 1.888 Mg m3
a = 5.490 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 6.799 (2) ÅCell parameters from 722 reflections
c = 8.716 (2) Åθ = 2.4–28.1°
α = 79.742 (4)°µ = 0.23 mm1
β = 75.852 (3)°T = 298 K
γ = 69.517 (3)°Plate, colorless
V = 294.0 (1) Å30.31 × 0.15 × 0.11 mm
Data collection top
Bruker AXS SMART
diffractometer
962 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 28.1°, θmin = 2.4°
ω scansh = 67
1893 measured reflectionsk = 88
1311 independent reflectionsl = 611
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041All H-atom parameters refined
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0621P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.001
1311 reflectionsΔρmax = 0.24 e Å3
117 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.28 (3)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Na10.6607 (2)0.5560 (1)0.6215 (1)0.0301 (3)
O10.7707 (3)0.8477 (2)0.6957 (2)0.0299 (4)
O20.6462 (3)0.6567 (3)0.9097 (2)0.0337 (4)
O30.6600 (3)0.5898 (3)1.1867 (2)0.0337 (4)
O40.8852 (3)0.6371 (2)1.3456 (2)0.0294 (4)
O1w0.7035 (3)0.2410 (3)0.4935 (2)0.0326 (4)
C10.7563 (4)0.7935 (3)0.8403 (2)0.0237 (5)
C20.8759 (4)0.8928 (3)0.9346 (2)0.0212 (5)
C30.9026 (4)0.8397 (3)1.0946 (2)0.0208 (5)
C40.8134 (4)0.6783 (3)1.2180 (2)0.0227 (5)
C50.9742 (4)1.0492 (3)0.8468 (3)0.0234 (5)
H1o0.639 (6)0.612 (5)1.056 (4)0.07 (1)*
H1w10.850 (7)0.209 (5)0.438 (4)0.06 (1)*
H1w20.697 (5)0.121 (5)0.553 (4)0.05 (1)*
H50.956 (4)1.087 (4)0.740 (3)0.02 (1)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0320 (5)0.0339 (5)0.0292 (5)0.0151 (4)0.0102 (4)0.0002 (4)
O10.043 (1)0.036 (1)0.019 (1)0.021 (1)0.010 (1)0.000 (1)
O20.048 (1)0.043 (1)0.024 (1)0.032 (1)0.010 (1)0.002 (1)
O30.048 (1)0.044 (1)0.023 (1)0.034 (1)0.009 (1)0.004 (1)
O40.037 (1)0.034 (1)0.022 (1)0.019 (1)0.010 (1)0.007 (1)
O1w0.031 (1)0.033 (1)0.031 (1)0.011 (1)0.005 (1)0.004 (1)
C10.026 (1)0.026 (1)0.022 (1)0.011 (1)0.006 (1)0.004 (1)
C20.022 (1)0.024 (1)0.020 (1)0.009 (1)0.005 (1)0.003 (1)
C30.022 (1)0.023 (1)0.018 (1)0.009 (1)0.003 (1)0.002 (1)
C40.025 (1)0.024 (1)0.019 (1)0.010 (1)0.003 (1)0.001 (1)
C50.029 (1)0.025 (1)0.018 (1)0.010 (1)0.008 (1)0.000 (1)
Geometric parameters (Å, º) top
Na1—O12.491 (2)C1—C21.527 (3)
Na1—O22.695 (2)C2—C51.385 (3)
Na1—O3i2.463 (2)C2—C31.407 (3)
Na1—O4ii2.482 (2)C3—C5v1.397 (3)
Na1—O4iii2.439 (2)C3—C41.516 (3)
Na1—O1w2.501 (2)C5—C3v1.397 (3)
Na1—O1wiv2.337 (2)O2—H1o1.25 (3)
O1—C11.240 (3)O3—H1o1.15 (3)
O2—C11.269 (3)O1w—H1w10.81 (3)
O3—C41.293 (2)O1w—H1w20.89 (3)
O4—C41.223 (2)C5—H50.94 (2)
O1—Na1—O249.6 (1)Na1iii—O4—Na1vi97.4 (1)
O1—Na1—O3i118.6 (1)Na1iv—O1w—Na189.0 (1)
O1—Na1—O4ii87.2 (1)O1—C1—O2121.0 (2)
O1—Na1—O4iii81.2 (1)O1—C1—C2118.9 (2)
O1—Na1—O1w160.8 (1)O2—C1—C2120.1 (2)
O1—Na1—O1wiv98.6 (1)C5—C2—C3118.0 (2)
O2—Na1—O3i73.2 (1)C5—C2—C1114.2 (2)
O2—Na1—O4ii135.0 (1)C3—C2—C1127.8 (2)
O2—Na1—O4iii79.2 (1)C5v—C3—C2117.1 (2)
O2—Na1—O1w139.2 (1)C5v—C3—C4113.3 (2)
O2—Na1—O1wiv114.8 (1)C2—C3—C4129.6 (2)
O3i—Na1—O4ii151.6 (1)O4—C4—O3121.6 (2)
O3i—Na1—O4iii111.6 (1)O4—C4—C3119.3 (2)
O3i—Na1—O1w78.6 (1)O3—C4—C3119.1 (2)
O3i—Na1—O1wiv84.8 (1)C2—C5—C3v124.9 (2)
O4ii—Na1—O4iii82.6 (1)C1—O2—H1o117 (1)
O4ii—Na1—O1w78.4 (1)Na1—O2—H1o152 (1)
O4ii—Na1—O1wiv79.1 (1)C4—O3—H1o116 (2)
O4iii—Na1—O1w84.5 (1)Na1i—O3—H1o116 (2)
O4iii—Na1—O1wiv161.6 (1)Na1iv—O1w—H1w1119 (2)
O1w—Na1—O1wiv91.0 (1)Na1—O1w—H1w1106 (2)
C1—O1—Na199.0 (1)Na1iv—O1w—H1w2118 (2)
C1—O2—Na188.5 (1)Na1—O1w—H1w2120 (2)
C4—O3—Na1i127.2 (1)H1w1—O1w—H1w2104 (3)
C4—O4—Na1iii124.2 (1)C2—C5—H5119 (1)
C4—O4—Na1vi132.6 (1)C3v—C5—H5116 (1)
O1wiv—Na1—O1—C1123.2 (1)Na1—O2—C1—C2166.0 (2)
O4iii—Na1—O1—C175.5 (1)O1—C1—C2—C54.5 (3)
O3i—Na1—O1—C134.4 (2)O2—C1—C2—C5176.0 (2)
O4ii—Na1—O1—C1158.4 (1)O1—C1—C2—C3173.6 (2)
O1w—Na1—O1—C1117.5 (2)O2—C1—C2—C36.0 (3)
O2—Na1—O1—C17.8 (1)C5—C2—C3—C5v0.4 (3)
O1wiv—Na1—O2—C187.4 (1)C1—C2—C3—C5v178.4 (2)
O4iii—Na1—O2—C180.1 (1)C5—C2—C3—C4179.5 (2)
O3i—Na1—O2—C1163.3 (1)C1—C2—C3—C42.5 (4)
O4ii—Na1—O2—C112.2 (2)Na1iii—O4—C4—O3110.9 (2)
O1—Na1—O2—C17.5 (1)Na1vi—O4—C4—O336.0 (3)
O1w—Na1—O2—C1148.3 (1)Na1iii—O4—C4—C370.1 (2)
O1wiv—Na1—O1w—Na1iv0.0Na1vi—O4—C4—C3143.0 (2)
O4iii—Na1—O1w—Na1iv162.1 (1)Na1i—O3—C4—O426.0 (3)
O3i—Na1—O1w—Na1iv84.5 (1)Na1i—O3—C4—C3153.0 (1)
O4ii—Na1—O1w—Na1iv78.6 (1)C5v—C3—C4—O410.1 (3)
O1—Na1—O1w—Na1iv120.4 (2)C2—C3—C4—O4170.8 (2)
O2—Na1—O1w—Na1iv131.4 (1)C5v—C3—C4—O3168.9 (2)
Na1—O1—C1—O214.8 (2)C2—C3—C4—O310.2 (3)
Na1—O1—C1—C2164.7 (2)C3—C2—C5—C3v0.4 (4)
Na1—O2—C1—O113.5 (2)C1—C2—C5—C3v178.7 (2)
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y, z1; (iii) x+2, y+1, z+2; (iv) x+1, y+1, z+1; (v) x+2, y+2, z+2; (vi) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O1vii0.81 (3)2.06 (3)2.868 (2)174 (3)
O1w—H1w2···O1viii0.89 (3)2.02 (3)2.888 (2)166 (3)
O3—H1o···O21.15 (3)1.25 (3)2.390 (2)169 (3)
Symmetry codes: (vii) x+2, y+1, z+1; (viii) x, y1, z.
 

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