supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

bt2752 scheme

Acta Cryst. (2008). E64, m1119    [ doi:10.1107/S1600536808024331 ]

Disodium 4,4'-oxydibenzoate

Y. Yang, Q. Li and S. W. Ng

Abstract top

The crystal structure of the title compound, 2Na+·C14H8O52-, 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)].

Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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. Dashed lines denote the distances between them.
Disodium 4,4'-oxydibenzoate top
Crystal data top
2Na+·C14H8O52–F000 = 616
Mr = 302.18Dx = 1.562 Mg m−3
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 mm−1
β = 92.4420 (1)ºT = 295 (2) K
V = 1284.78 (3) Å3Block, colorless
Z = 40.5 × 0.4 × 0.2 mm
Data collection top
Bruker SMART APEXII
diffractometer		1471 independent reflections
Radiation source: fine-focus sealed tube1464 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.015
T = 295(2) Kθmax = 27.5º
φ 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 top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-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 Å−3
203 parametersΔρmin = −0.27 e Å−3
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)
Crystal data top
2Na+·C14H8O52–V = 1284.78 (3) Å3
Mr = 302.18Z = 4
Monoclinic, CcMo Kα
a = 29.1091 (4) ŵ = 0.18 mm−1
b = 5.7801 (1) ÅT = 295 (2) K
c = 7.6429 (1) Å0.5 × 0.4 × 0.2 mm
β = 92.4420 (1)º
Data collection top
Bruker SMART APEXII
diffractometer		1471 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1464 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 1.000Rint = 0.015
5002 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.135Δρmax = 0.79 e Å−3
S = 1.27Δρmin = −0.27 e Å−3
1471 reflectionsAbsolute structure: ?
203 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Special details top

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) top
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) top
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, °) top
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.
Acknowledgements top

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

references
References top

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.

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.

Westrip, S. P. (2008). publCIF. In preparation.