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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1119.
Published online 2008 August 6. doi:  10.1107/S1600536808024331
PMCID: PMC2960567

Disodium 4,4′-oxydibenzoate

Abstract

The crystal structure of the title compound, 2Na+·C14H8O5 2−, consists of alternating layers of sodium cations and 4,4′-oxydibenzoate anions; the layers are perpendicular to the a axis, with the distance between the layers of cations (or anions) being half this axial length. The Na atoms are disordered over three sites [occupancies 0.775 (4), 0.781 (6) 0.444 (6)].

Related literature

For the crystal structure of 4,4′-oxybis(benzoic acid), see: Dey & Desiraju (2005 [triangle]); Potts et al. (2007 [triangle]).

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Object name is e-64-m1119-scheme1.jpg

Experimental

Crystal data

  • 2Na+·C14H8O5 2−
  • M r = 302.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1119-efi1.jpg
  • a = 29.1091 (4) Å
  • b = 5.7801 (1) Å
  • c = 7.6429 (1) Å
  • β = 92.4420 (1)°
  • V = 1284.78 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 295 (2) K
  • 0.5 × 0.4 × 0.2 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.888, T max = 1.000 (expected range = 0.857–0.966)
  • 5002 measured reflections
  • 1471 independent reflections
  • 1464 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.135
  • S = 1.27
  • 1471 reflections
  • 203 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.79 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024331/bt2752sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024331/bt2752Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Beijing Normal University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The crystal structure of disodium 4,4'-oxydibenzoate (Scheme I, Fig. 1) consists of alternating bands of sodium cations and 4,4'-oxydibenzoate anions. The two symmetry-independent sodium atoms over three positions. The lowest occupancy sodium atom is only weakly linked to two oxygen atoms, and probably "rattles" about in the crystal structure.

Experimental

Betaine (0.047 g, 0.4 mmol), 4,4'-oxybis(benzoic acid) (0.103 g, 0.4 mmol) and guanidine hydrochloride (0.076 g, 0.8 mmol) were mixed in a molar ratio 1:1:2. The mixture was dissolved in mixture of ethanol (4 ml), 1 M sodium hydroxide (0.5 ml) and water (0.5 ml). Colorless crystals were obtained after about 10 days.

Refinement

The Na1, Na2 and Na3 atoms were refined such that the total occupancy is two.

Carbon bound H-atoms were placed in calculated positions (C—H 0.93 Å) and were included in the refinement in the riding model approximation, with Uiso(H) 1.2Ueq(C).

Friedel pairs were merged as there are no anomalous scatterers.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the asymmetric unit of the title compound; displac ement ellipsoids are set at the 70% probability level. Hydrogeatoms are drawn as spheres of arbitrary radius. The two sodium atoms are disordered over three positions. ...

Crystal data

2Na+·C14H8O52–F000 = 616
Mr = 302.18Dx = 1.562 Mg m3
Monoclinic, CcMo Kα radiation λ = 0.71073 Å
a = 29.1091 (4) ÅCell parameters from 4314 reflections
b = 5.7801 (1) Åθ = 4.0–27.5º
c = 7.6429 (1) ŵ = 0.18 mm1
β = 92.4420 (1)ºT = 295 (2) K
V = 1284.78 (3) Å3Block, colorless
Z = 40.5 × 0.4 × 0.2 mm

Data collection

Bruker SMART APEXII diffractometer1471 independent reflections
Radiation source: fine-focus sealed tube1464 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.015
T = 295(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 4.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −37→37
Tmin = 0.888, Tmax = 1.000k = −7→7
5002 measured reflectionsl = −9→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.135  w = 1/[σ2(Fo2) + (0.0883P)2 + 0.9438P] where P = (Fo2 + 2Fc2)/3
S = 1.27(Δ/σ)max = 0.001
1471 reflectionsΔρmax = 0.79 e Å3
203 parametersΔρmin = −0.27 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (4)

Special details

Experimental. A somewhat large crystal was used in the measurements, but this does not seem to have an adverse efffect on the quality of the diffraction data.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Na10.50001 (5)0.1573 (3)0.50001 (18)0.0119 (4)0.775 (4)
Na20.44106 (5)0.3880 (3)0.84063 (18)0.0113 (5)0.781 (6)
Na30.47490 (10)0.7168 (5)0.7153 (4)0.0147 (9)0.444 (6)
O10.53701 (10)0.4833 (5)0.9932 (4)0.0273 (6)
O20.51425 (9)0.1864 (5)0.8264 (4)0.0243 (6)
O30.91491 (10)0.5648 (5)0.9768 (4)0.0279 (6)
O40.92132 (9)0.1917 (5)1.0487 (4)0.0249 (6)
O50.72485 (10)0.1735 (6)0.6575 (4)0.0338 (7)
C10.54493 (12)0.3222 (6)0.8891 (5)0.0199 (7)
C20.59376 (12)0.2835 (6)0.8364 (4)0.0199 (7)
C30.60419 (13)0.0883 (6)0.7386 (5)0.0234 (7)
H30.5812−0.01820.70880.028*
C40.64896 (13)0.0513 (7)0.6849 (5)0.0250 (7)
H40.6559−0.07930.62010.030*
C50.68284 (12)0.2121 (7)0.7296 (5)0.0230 (7)
C60.67343 (13)0.4048 (7)0.8307 (5)0.0251 (8)
H60.69660.50890.86340.030*
C70.62823 (12)0.4391 (7)0.8825 (5)0.0228 (7)
H70.62140.56850.94880.027*
C80.76546 (12)0.2304 (8)0.7501 (5)0.0261 (8)
C90.78630 (13)0.0650 (7)0.8574 (5)0.0266 (8)
H90.7713−0.07330.87920.032*
C100.82982 (14)0.1068 (7)0.9322 (5)0.0248 (7)
H100.8442−0.00521.00260.030*
C110.85196 (11)0.3161 (6)0.9022 (4)0.0194 (7)
C120.82984 (13)0.4838 (7)0.7983 (5)0.0243 (7)
H120.84400.62560.78130.029*
C130.78638 (13)0.4407 (7)0.7192 (5)0.0264 (7)
H130.77190.55090.64750.032*
C140.89941 (12)0.3616 (6)0.9821 (5)0.0200 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Na10.0114 (7)0.0098 (7)0.0144 (7)0.0005 (5)−0.0009 (5)−0.0005 (5)
Na20.0119 (8)0.0094 (7)0.0127 (8)−0.0011 (5)0.0003 (5)0.0001 (5)
Na30.0169 (14)0.0144 (15)0.0127 (14)0.0013 (10)0.0008 (10)−0.0004 (10)
O10.0230 (11)0.0294 (14)0.0299 (15)0.0020 (11)0.0043 (10)−0.0037 (11)
O20.0183 (11)0.0254 (13)0.0293 (13)−0.0020 (9)0.0007 (10)0.0005 (10)
O30.0262 (13)0.0292 (15)0.0282 (14)−0.0081 (11)−0.0015 (11)0.0009 (11)
O40.0209 (12)0.0281 (13)0.0254 (13)0.0042 (10)−0.0017 (10)0.0008 (10)
O50.0171 (12)0.056 (2)0.0288 (14)−0.0011 (12)0.0005 (10)−0.0141 (13)
C10.0181 (15)0.0215 (15)0.0200 (15)0.0019 (12)0.0015 (12)0.0039 (12)
C20.0165 (15)0.0228 (16)0.0204 (15)0.0011 (12)−0.0006 (12)0.0030 (12)
C30.0187 (16)0.0241 (17)0.0274 (18)−0.0015 (13)0.0007 (13)−0.0029 (13)
C40.0223 (17)0.0260 (17)0.0267 (17)0.0035 (15)0.0008 (13)−0.0051 (14)
C50.0179 (16)0.0299 (17)0.0211 (15)0.0015 (13)0.0003 (12)−0.0001 (13)
C60.0174 (16)0.0290 (19)0.0287 (17)−0.0044 (13)−0.0014 (13)−0.0039 (15)
C70.0226 (17)0.0217 (16)0.0243 (17)−0.0001 (13)0.0016 (13)−0.0034 (12)
C80.0159 (16)0.039 (2)0.0232 (17)−0.0016 (14)0.0031 (13)−0.0074 (15)
C90.0227 (17)0.0278 (18)0.0294 (18)−0.0069 (14)0.0037 (14)−0.0022 (14)
C100.0260 (18)0.0237 (16)0.0247 (17)−0.0007 (14)0.0024 (13)0.0025 (14)
C110.0162 (15)0.0232 (16)0.0187 (15)0.0003 (11)0.0008 (11)−0.0018 (12)
C120.0237 (17)0.0238 (17)0.0255 (18)−0.0004 (13)0.0028 (13)0.0033 (13)
C130.0210 (16)0.033 (2)0.0252 (16)0.0056 (15)−0.0003 (12)0.0026 (15)
C140.0188 (16)0.0252 (16)0.0162 (14)−0.0013 (12)0.0023 (12)−0.0001 (12)

Geometric parameters (Å, °)

Na1—O1i2.342 (3)O5—C81.391 (5)
Na1—O2ii2.434 (3)C1—C21.511 (5)
Na1—O4iii2.494 (3)C2—C71.382 (5)
Na1—O22.517 (3)C2—C31.394 (5)
Na1—O3iii2.789 (3)C3—C41.399 (5)
Na2—O3iv2.285 (3)C3—H30.9300
Na2—O4iii2.326 (3)C4—C51.388 (5)
Na2—O22.435 (3)C4—H40.9300
Na2—O4v2.453 (3)C5—C61.389 (6)
O1—C11.252 (5)C6—C71.404 (5)
O1—Na1vi2.342 (3)C6—H60.9300
O1—Na3vi2.784 (4)C7—H70.9300
O2—C11.268 (4)C8—C91.382 (6)
O2—Na1vii2.434 (3)C8—C131.384 (6)
O3—C141.260 (5)C9—C101.389 (5)
O3—Na2viii2.285 (3)C9—H90.9300
O3—Na3ix2.774 (4)C10—C111.394 (5)
O3—Na1x2.789 (3)C10—H100.9300
O4—C141.266 (5)C11—C121.393 (5)
O4—Na2x2.326 (3)C11—C141.509 (5)
O4—Na2xi2.453 (3)C12—C131.401 (5)
O4—Na1x2.494 (3)C12—H120.9300
O5—C51.381 (4)C13—H130.9300
O1i—Na1—O2ii128.52 (12)O2—C1—C2117.6 (3)
O1i—Na1—O4iii96.84 (11)C7—C2—C3119.4 (3)
O2ii—Na1—O4iii123.07 (11)C7—C2—C1121.1 (3)
O1i—Na1—O284.62 (11)C3—C2—C1119.5 (3)
O2ii—Na1—O2124.75 (10)C2—C3—C4120.5 (3)
O4iii—Na1—O286.69 (10)C2—C3—H3119.7
O1i—Na1—O3iii144.60 (11)C4—C3—H3119.7
O2ii—Na1—O3iii76.17 (10)C5—C4—C3119.1 (3)
O4iii—Na1—O3iii49.58 (9)C5—C4—H4120.4
O2—Na1—O3iii101.66 (10)C3—C4—H4120.4
O3iv—Na2—O4iii101.63 (12)O5—C5—C4115.2 (3)
O3iv—Na2—O286.45 (11)O5—C5—C6123.4 (3)
O4iii—Na2—O292.48 (11)C4—C5—C6121.3 (3)
O3iv—Na2—O4v101.41 (12)C5—C6—C7118.6 (3)
O4iii—Na2—O4v135.10 (11)C5—C6—H6120.7
O2—Na2—O4v126.93 (11)C7—C6—H6120.7
O2—Na2—Na3vi72.45 (9)C2—C7—C6121.0 (3)
C1—O1—Na1vi140.4 (3)C2—C7—H7119.5
C1—O1—Na3vi102.7 (2)C6—C7—H7119.5
Na1vi—O1—Na3vi92.50 (11)C9—C8—C13121.6 (3)
C1—O2—Na1vii115.6 (2)C9—C8—O5118.7 (4)
C1—O2—Na2106.9 (2)C13—C8—O5119.4 (4)
Na1vii—O2—Na2101.34 (11)C8—C9—C10119.6 (3)
C1—O2—Na1120.0 (2)C8—C9—H9120.2
Na1vii—O2—Na1117.45 (12)C10—C9—H9120.2
Na2—O2—Na188.21 (10)C9—C10—C11120.2 (4)
C14—O3—Na2viii154.6 (3)C9—C10—H10119.9
C14—O3—Na3ix128.3 (2)C11—C10—H10119.9
Na2viii—O3—Na3ix73.42 (10)C12—C11—C10119.4 (3)
C14—O3—Na1x83.5 (2)C12—C11—C14120.1 (3)
Na2viii—O3—Na1x95.35 (10)C10—C11—C14120.4 (3)
Na3ix—O3—Na1x68.61 (9)C11—C12—C13120.6 (3)
C14—O4—Na2x129.7 (2)C11—C12—H12119.7
C14—O4—Na2xi115.0 (2)C13—C12—H12119.7
Na2x—O4—Na2xi115.15 (12)C8—C13—C12118.6 (4)
C14—O4—Na1x96.8 (2)C8—C13—H13120.7
Na2x—O4—Na1x91.23 (10)C12—C13—H13120.7
Na2xi—O4—Na1x84.93 (10)O3—C14—O4124.1 (3)
C5—O5—C8120.4 (3)O3—C14—C11118.2 (3)
O1—C1—O2123.7 (3)O4—C14—C11117.7 (3)
O1—C1—C2118.7 (3)
O3iv—Na2—O2—C1−128.5 (2)C3—C4—C5—O5−174.1 (4)
O4iii—Na2—O2—C1130.0 (2)C3—C4—C5—C61.9 (6)
O4v—Na2—O2—C1−26.9 (3)O5—C5—C6—C7173.5 (3)
O3iv—Na2—O2—Na1vii−7.05 (12)C4—C5—C6—C7−2.2 (6)
O4iii—Na2—O2—Na1vii−108.56 (12)C3—C2—C7—C60.7 (6)
O4v—Na2—O2—Na1vii94.58 (14)C1—C2—C7—C6−178.9 (3)
O3iv—Na2—O2—Na1110.60 (11)C5—C6—C7—C20.9 (6)
O4iii—Na2—O2—Na19.09 (11)C5—O5—C8—C990.4 (5)
O4v—Na2—O2—Na1−147.78 (12)C5—O5—C8—C13−96.2 (5)
O1i—Na1—O2—C1−19.8 (3)C13—C8—C9—C10−1.9 (6)
O2ii—Na1—O2—C1114.3 (2)O5—C8—C9—C10171.3 (3)
O4iii—Na1—O2—C1−117.0 (3)C8—C9—C10—C111.3 (6)
O3iii—Na1—O2—C1−164.5 (3)C9—C10—C11—C120.7 (5)
C14iii—Na1—O2—C1−138.8 (3)C9—C10—C11—C14−179.5 (3)
O1i—Na1—O2—Na1vii−169.42 (13)C10—C11—C12—C13−2.2 (5)
O2ii—Na1—O2—Na1vii−35.3 (2)C14—C11—C12—C13178.0 (3)
O4iii—Na1—O2—Na1vii93.37 (13)C9—C8—C13—C120.5 (6)
O3iii—Na1—O2—Na1vii45.83 (14)O5—C8—C13—C12−172.7 (3)
C14iii—Na1—O2—Na1vii71.53 (14)C11—C12—C13—C81.6 (6)
O1i—Na1—O2—Na288.72 (11)Na2viii—O3—C14—O4113.0 (6)
O2ii—Na1—O2—Na2−137.17 (13)Na3ix—O3—C14—O4−31.9 (5)
O4iii—Na1—O2—Na2−8.48 (10)Na1x—O3—C14—O424.2 (3)
O3iii—Na1—O2—Na2−56.02 (11)Na2viii—O3—C14—C11−66.2 (7)
Na1vi—O1—C1—O2−69.3 (5)Na3ix—O3—C14—C11148.8 (3)
Na3vi—O1—C1—O240.8 (4)Na1x—O3—C14—C11−155.1 (3)
Na1vi—O1—C1—C2111.7 (4)Na2viii—O3—C14—Na1x88.8 (6)
Na3vi—O1—C1—C2−138.3 (3)Na3ix—O3—C14—Na1x−56.1 (2)
Na1vii—O2—C1—O1−88.5 (4)Na2x—O4—C14—O370.0 (5)
Na2—O2—C1—O123.4 (4)Na2xi—O4—C14—O3−114.9 (4)
Na1—O2—C1—O1121.4 (3)Na1x—O4—C14—O3−27.3 (4)
Na1vii—O2—C1—C290.6 (3)Na2x—O4—C14—C11−110.7 (3)
Na2—O2—C1—C2−157.5 (2)Na2xi—O4—C14—C1164.4 (3)
Na1—O2—C1—C2−59.6 (4)Na1x—O4—C14—C11152.0 (3)
O1—C1—C2—C7−8.4 (5)Na2x—O4—C14—Na1x97.3 (3)
O2—C1—C2—C7172.5 (3)Na2xi—O4—C14—Na1x−87.57 (17)
O1—C1—C2—C3172.0 (4)C12—C11—C14—O311.6 (5)
O2—C1—C2—C3−7.1 (5)C10—C11—C14—O3−168.2 (3)
C7—C2—C3—C4−1.0 (5)C12—C11—C14—O4−167.7 (3)
C1—C2—C3—C4178.6 (3)C10—C11—C14—O412.5 (5)
C2—C3—C4—C5−0.3 (6)C12—C11—C14—Na1x−95.3 (6)
C8—O5—C5—C4−146.1 (4)C10—C11—C14—Na1x84.9 (6)
C8—O5—C5—C637.9 (6)

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y, z−1/2; (iii) x−1/2, −y+1/2, z−1/2; (iv) x−1/2, y−1/2, z; (v) x−1/2, y+1/2, z; (vi) x, −y+1, z+1/2; (vii) x, −y, z+1/2; (viii) x+1/2, y+1/2, z; (ix) x+1/2, −y+3/2, z+1/2; (x) x+1/2, −y+1/2, z+1/2; (xi) x+1/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2752).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dey, A. & Desiraju, G. R. (2005). Chem. Commun. pp. 2486–2488. [PubMed]
  • Potts, S., Bredenkamp, M. W. & Gertenbach, J.-A. (2007). Acta Cryst. E63, o2887.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography