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Acta Cryst. (2008). E64, m1637    [ doi:10.1107/S1600536808039640 ]

Poly[[[mu]-1,4-anhydroerythritolato-di-[mu]-aqua-sodium(I)] monohydrate]

T. Kerscher, P. Zeller, P. Mayer and P. Klüfers

Abstract top

In the title compound, {[Na(C4H7O3)(H2O)2]·H2O}n, the sodium ion is octahedrally coordinated by two bridging 1,4-anhydroerythritolate ligands, unexpectedly coordinated by the ring oxygen and four water ligands. This bonding pattern leads to one-dimensional antitactical polymeric chains along [010]. One of the exocyclic O atoms of the anhydroerythritolate group is an acceptor in four hydrogen bonds, giving further evidence that it is deprotonated.

Comment top

The title compound was obtained as a byproduct in a reaction involving sodium hydroxide, anhydroerytritole and iron(II) chloride. .

Sodium is octahedrically coordinated by bridging anhydroerythritolate and water ligands. The anhydroerythritolate coordinates the sodium unexpectedly by its ring oxygen atom while the alkoxide group is stabilized by intramolecular hydrogen bonding from the hydroxyl group. The anhydroerythitolate contains a five-membered ring containing O1, C1, C2, C3 and C4 which can be described according to Cremer & Pople (1975) by the puckering parameters q2 = 0.3903 Å and Φ2 = 180.9772. The closest pucker descriptor is an envelope EO1.

The bridging ligands lead to a linear chain-like structure along [010] which resembles an antitactical polymer well known from organic chemistry.

Related literature top

For the neutral 1,4-anhydroerytritole as a coordination ligand on sodium with either the hydoxyl groups coordinating sodium or a mixed coordination by both the ring oxygen and the hydroxyl groups, see: Ballard et al. (1974, 1976). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was obtained as a byproduct by the reaction of 40 mMol anhydroerytritol with 160 mMol sodiumhydoxide in 15 mL water at room temperature.

Upon standing for about 14 days at room temperature, colorless platelets of the title compound crystalized from the solution.

Refinement top

Carbon hydrogen atoms and hydoxide hydrogen atoms were calculated in ideal geometry with U(H)=1.2*U(C) for all C-bound hydrogen atoms and U(H)=1.5*U(O) for the hydroxide hydrogen atom. The water-bound hydrogen atoms were found from the difference map, the O-H distances were fixed to 0.84 Å and the H-H distances within the water molecules were fixed to 1.36 Å.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED Oxford Diffraction (2006); data reduction: CrysAlis RED Oxford Diffraction (2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
[Figure 2] Fig. 2. Part of the antitactical polymer-like chain structure of the title compound along [010]. Symmetry code: (iii) -x + 1/2, y - 1/2, -z + 1/2.
Poly[[µ-1,4-anhydroerythritolato-di-µ-aqua-sodium(I)] monohydrate] top
Crystal data top
[Na(C4H7O3)(H2O)2]·H2OF(000) = 768
Mr = 180.13Dx = 1.474 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2600 reflections
a = 23.155 (6) Åθ = 3.8–26.5°
b = 6.0900 (16) ŵ = 0.18 mm−1
c = 14.543 (5) ÅT = 200 K
β = 127.678 (17)°Platelet, colourless
V = 1623.1 (9) Å30.23 × 0.20 × 0.10 mm
Z = 8
Data collection top
Oxford Diffraction KappaCCD
diffractometer		1088 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
graphiteθmax = 26.5°, θmin = 4.2°
ω scansh = −21→28
6310 measured reflectionsk = −7→6
1699 independent reflectionsl = −17→18
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0484P)2]
where P = (Fo2 + 2Fc2)/3
1699 reflections(Δ/σ)max < 0.001
118 parametersΔρmax = 0.20 e Å−3
9 restraintsΔρmin = −0.24 e Å−3
Crystal data top
[Na(C4H7O3)(H2O)2]·H2OV = 1623.1 (9) Å3
Mr = 180.13Z = 8
Monoclinic, C2/cMo Kα radiation
a = 23.155 (6) ŵ = 0.18 mm−1
b = 6.0900 (16) ÅT = 200 K
c = 14.543 (5) Å0.23 × 0.20 × 0.10 mm
β = 127.678 (17)°
Data collection top
Oxford Diffraction KappaCCD
diffractometer		1088 reflections with I > 2σ(I)
6310 measured reflectionsRint = 0.044
1699 independent reflectionsθmax = 26.5°
Refinement top
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086Δρmax = 0.20 e Å−3
S = 0.95Δρmin = −0.24 e Å−3
1699 reflectionsAbsolute structure: ?
118 parametersFlack parameter: ?
9 restraintsRogers parameter: ?
Special details top

Refinement. Carbon hydrogen atoms and hydroxide hydrogen atoms were calculated in ideal geometry with U(H)=1.2*U(C) for all C-bound hydrogen atoms and U(H)=1.5*U(O) for the hydroxide hydrogen atom. The water-bound hydrogen atoms were found from the difference map, the O-H distances were restrained to 0.84 Å and the H-H distances within the water molecules were restrained to 1.36 Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Na10.24809 (3)0.43051 (10)0.24000 (5)0.0238 (2)
O10.16736 (6)0.16529 (17)0.09168 (9)0.0238 (3)
O20.05729 (6)−0.21567 (19)−0.03931 (10)0.0322 (3)
H20.0846−0.2907−0.04450.048*
O30.14255 (6)−0.19459 (18)−0.08460 (9)0.0295 (3)
O40.24091 (7)0.19528 (18)0.36644 (10)0.0261 (3)
H410.2075 (8)0.196 (3)0.3733 (15)0.039*
H420.2796 (8)0.222 (3)0.4385 (13)0.039*
O60.34457 (6)0.18090 (18)0.30154 (10)0.0285 (3)
H610.3781 (9)0.212 (3)0.3752 (12)0.043*
H620.3710 (10)0.123 (3)0.2850 (14)0.043*
C10.09012 (9)0.1596 (3)0.03391 (15)0.0288 (4)
H110.06860.30800.00670.035*
H120.08010.10410.08680.035*
C20.05911 (9)0.0052 (3)−0.06810 (14)0.0282 (4)
H10.00970.0547−0.13670.034*
C30.11567 (9)0.0160 (3)−0.09473 (14)0.0272 (4)
H30.09220.0765−0.17420.033*
C40.17244 (9)0.1743 (3)−0.00250 (14)0.0284 (4)
H430.22180.13040.02510.034*
H440.16260.3251−0.03430.034*
O50.06903 (7)0.4653 (2)0.23361 (12)0.0439 (4)
H510.0915 (10)0.384 (3)0.2926 (14)0.066*
H520.0326 (9)0.400 (3)0.1783 (15)0.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0278 (4)0.0183 (4)0.0225 (4)−0.0002 (3)0.0140 (3)−0.0003 (3)
O10.0232 (7)0.0270 (6)0.0190 (6)−0.0019 (5)0.0116 (5)−0.0015 (5)
O20.0308 (7)0.0304 (7)0.0336 (7)−0.0053 (5)0.0188 (6)−0.0022 (5)
O30.0292 (7)0.0322 (7)0.0242 (7)0.0002 (5)0.0149 (6)−0.0048 (5)
O40.0268 (7)0.0304 (7)0.0229 (7)−0.0016 (6)0.0160 (6)−0.0025 (5)
O60.0269 (7)0.0299 (7)0.0281 (7)0.0016 (5)0.0165 (6)−0.0036 (5)
C10.0238 (10)0.0310 (10)0.0292 (10)0.0037 (7)0.0149 (8)0.0005 (8)
C20.0202 (9)0.0307 (10)0.0232 (9)0.0007 (8)0.0079 (8)0.0013 (8)
C30.0282 (9)0.0310 (10)0.0180 (9)0.0006 (8)0.0119 (8)0.0017 (7)
C40.0332 (10)0.0290 (10)0.0248 (10)−0.0031 (8)0.0186 (9)0.0014 (7)
O50.0361 (8)0.0447 (9)0.0349 (8)−0.0085 (6)0.0136 (7)0.0117 (6)
Geometric parameters (Å, °) top
Na1—O4i2.3544 (13)O4—H420.883 (14)
Na1—O62.3787 (14)O6—Na1ii2.3893 (14)
Na1—O6i2.3893 (14)O6—H610.877 (14)
Na1—O12.4139 (13)O6—H620.859 (14)
Na1—O42.4155 (14)C1—C21.516 (2)
Na1—O1i2.4517 (14)C1—H110.9900
Na1—Na1i3.0550 (8)C1—H120.9900
Na1—Na1ii3.0550 (8)C2—C31.578 (2)
O1—C11.438 (2)C2—H11.0000
O1—C41.445 (2)C3—C41.517 (2)
O1—Na1ii2.4517 (14)C3—H31.0000
O2—C21.417 (2)C4—H430.9900
O2—H20.8200C4—H440.9900
O3—C31.394 (2)O5—H510.842 (15)
O4—Na1ii2.3544 (13)O5—H520.828 (14)
O4—H410.839 (14)
?···??
O4i—Na1—O6103.35 (5)Na1ii—O4—H41124.1 (12)
O4i—Na1—O6i80.67 (5)Na1—O4—H41125.9 (13)
O6—Na1—O6i174.07 (3)Na1ii—O4—H42117.9 (12)
O4i—Na1—O1101.92 (5)Na1—O4—H42107.6 (12)
O6—Na1—O186.84 (5)H41—O4—H42101.5 (14)
O6i—Na1—O196.65 (5)Na1—O6—Na1ii79.69 (4)
O4i—Na1—O4172.80 (5)Na1—O6—H61104.5 (12)
O6—Na1—O479.65 (5)Na1ii—O6—H61115.6 (13)
O6i—Na1—O495.86 (5)Na1—O6—H62145.5 (12)
O1—Na1—O484.69 (5)Na1ii—O6—H62110.5 (13)
O4i—Na1—O1i85.17 (5)H61—O6—H62100.4 (15)
O6—Na1—O1i90.22 (5)O1—C1—C2105.23 (13)
O6i—Na1—O1i85.75 (5)O1—C1—H11110.7
O1—Na1—O1i172.78 (4)C2—C1—H11110.7
O4—Na1—O1i88.30 (5)O1—C1—H12110.7
O4i—Na1—Na1i51.06 (3)C2—C1—H12110.7
O6—Na1—Na1i129.44 (5)H11—C1—H12108.8
O6i—Na1—Na1i50.00 (3)O2—C2—C1112.42 (14)
O1—Na1—Na1i135.52 (4)O2—C2—C3106.92 (13)
O4—Na1—Na1i122.01 (4)C1—C2—C3104.28 (13)
O1i—Na1—Na1i50.56 (3)O2—C2—H1111.0
O4i—Na1—Na1ii137.46 (4)C1—C2—H1111.0
O6—Na1—Na1ii50.31 (3)C3—C2—H1111.0
O6i—Na1—Na1ii129.01 (4)O3—C3—C4113.69 (14)
O1—Na1—Na1ii51.66 (3)O3—C3—C2108.65 (13)
O4—Na1—Na1ii49.30 (3)C4—C3—C2102.13 (13)
O1i—Na1—Na1ii121.82 (4)O3—C3—H3110.7
Na1i—Na1—Na1ii170.73 (4)C4—C3—H3110.7
C1—O1—C4103.87 (12)C2—C3—H3110.7
C1—O1—Na1123.05 (9)O1—C4—C3106.58 (13)
C4—O1—Na1110.75 (9)O1—C4—H43110.4
C1—O1—Na1ii121.20 (10)C3—C4—H43110.4
C4—O1—Na1ii119.37 (9)O1—C4—H44110.4
Na1—O1—Na1ii77.78 (4)C3—C4—H44110.4
C2—O2—H2109.7H43—C4—H44108.6
Na1ii—O4—Na179.64 (4)H51—O5—H52109.6 (19)
O4i—Na1—O1—C1−98.09 (11)Na1i—Na1—O4—Na1ii−175.97 (5)
O6—Na1—O1—C1158.92 (11)O4i—Na1—O6—Na1ii−141.91 (5)
O6i—Na1—O1—C1−16.27 (12)O1—Na1—O6—Na1ii−40.40 (4)
O4—Na1—O1—C179.03 (12)O4—Na1—O6—Na1ii44.77 (4)
Na1i—Na1—O1—C1−52.67 (13)O1i—Na1—O6—Na1ii133.00 (5)
Na1ii—Na1—O1—C1119.44 (12)Na1i—Na1—O6—Na1ii167.97 (6)
O4i—Na1—O1—C425.43 (10)C4—O1—C1—C241.42 (15)
O6—Na1—O1—C4−77.55 (10)Na1—O1—C1—C2168.00 (9)
O6i—Na1—O1—C4107.26 (10)Na1ii—O1—C1—C2−96.32 (14)
O4—Na1—O1—C4−157.45 (10)O1—C1—C2—O290.07 (16)
Na1i—Na1—O1—C470.85 (11)O1—C1—C2—C3−25.39 (17)
Na1ii—Na1—O1—C4−117.04 (10)O2—C2—C3—O31.87 (17)
O4i—Na1—O1—Na1ii142.47 (5)C1—C2—C3—O3121.13 (14)
O6—Na1—O1—Na1ii39.48 (4)O2—C2—C3—C4−118.55 (14)
O6i—Na1—O1—Na1ii−135.70 (5)C1—C2—C3—C40.71 (16)
O4—Na1—O1—Na1ii−40.41 (4)C1—O1—C4—C3−41.55 (15)
Na1i—Na1—O1—Na1ii−172.11 (6)Na1—O1—C4—C3−175.52 (10)
O6—Na1—O4—Na1ii−45.63 (4)Na1ii—O1—C4—C397.14 (13)
O6i—Na1—O4—Na1ii138.29 (5)O3—C3—C4—O1−92.61 (16)
O1—Na1—O4—Na1ii42.12 (4)C2—C3—C4—O124.23 (16)
O1i—Na1—O4—Na1ii−136.17 (5)
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.821.852.4367 (17)127
O4—H41···O3iii0.84 (1)1.94 (2)2.7706 (17)171 (2)
O4—H42···O3i0.88 (1)1.83 (1)2.7078 (19)175 (2)
O6—H61···O2i0.88 (1)1.94 (1)2.813 (2)173 (2)
O6—H62···O5ii0.86 (1)1.84 (1)2.6903 (18)171 (2)
O5—H51···O3iii0.84 (2)1.83 (2)2.6653 (18)176 (2)
O5—H52···O2iv0.83 (1)2.13 (2)2.958 (2)177 (2)
Symmetry codes: (iii) x, −y, z+1/2; (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iv) −x, −y, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O30.821.852.4367 (17)127
O4—H41···O3i0.84 (1)1.94 (2)2.7706 (17)171 (2)
O4—H42···O3ii0.88 (1)1.83 (1)2.7078 (19)175 (2)
O6—H61···O2ii0.88 (1)1.94 (1)2.813 (2)173 (2)
O6—H62···O5iii0.86 (1)1.84 (1)2.6903 (18)171 (2)
O5—H51···O3i0.84 (2)1.83 (2)2.6653 (18)176 (2)
O5—H52···O2iv0.83 (1)2.13 (2)2.958 (2)177 (2)
Symmetry codes: (i) x, −y, z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x, −y, −z.
Acknowledgements top

TK is indebted to the Hanns-Seidel Stiftung for a PhD grant funded by the German Bundesministerium für Bildung und Forschung.

references
References top

Ballard, R. E., Haines, A. H., Norris, E. K. & Wells, A. G. (1974). Acta Cryst. B30, 1590–1593.

Ballard, R. E., Haines, A. H., Norris, E. H. & Wells, A. G. (1976). Acta Cryst. B32, 1577–1578.

Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.