Disodium 4,4'-oxydibenzoate.

The crystal structure of the title compound, 2Na(+)·C(14)H(8)O(5) (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 ▶); Potts et al. (2007 ▶).

Experimental

Crystal data

2Na+·C14H8O5 2−

M = 302.18

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶).

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

2Na+·C14H8O52–	F000 = 616
Mr = 302.18	Dx = 1.562 Mg m−3
Monoclinic, Cc	Mo Kα radiation λ = 0.71073 Å
a = 29.1091 (4) Å	Cell parameters from 4314 reflections
b = 5.7801 (1) Å	θ = 4.0–27.5º
c = 7.6429 (1) Å	µ = 0.18 mm−1
β = 92.4420 (1)º	T = 295 (2) K
V = 1284.78 (3) Å3	Block, colorless
Z = 4	0.5 × 0.4 × 0.2 mm

Bruker SMART APEXII diffractometer	1471 independent reflections
Radiation source: fine-focus sealed tube	1464 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.015
T = 295(2) K	θmax = 27.5º
φ and ω scans	θmin = 4.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −37→37
Tmin = 0.888, Tmax = 1.000	k = −7→7
5002 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-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 reflections	Δρmax = 0.79 e Å−3
203 parameters	Δρmin = −0.27 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (4)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Na1	0.50001 (5)	0.1573 (3)	0.50001 (18)	0.0119 (4)	0.775 (4)
Na2	0.44106 (5)	0.3880 (3)	0.84063 (18)	0.0113 (5)	0.781 (6)
Na3	0.47490 (10)	0.7168 (5)	0.7153 (4)	0.0147 (9)	0.444 (6)
O1	0.53701 (10)	0.4833 (5)	0.9932 (4)	0.0273 (6)
O2	0.51425 (9)	0.1864 (5)	0.8264 (4)	0.0243 (6)
O3	0.91491 (10)	0.5648 (5)	0.9768 (4)	0.0279 (6)
O4	0.92132 (9)	0.1917 (5)	1.0487 (4)	0.0249 (6)
O5	0.72485 (10)	0.1735 (6)	0.6575 (4)	0.0338 (7)
C1	0.54493 (12)	0.3222 (6)	0.8891 (5)	0.0199 (7)
C2	0.59376 (12)	0.2835 (6)	0.8364 (4)	0.0199 (7)
C3	0.60419 (13)	0.0883 (6)	0.7386 (5)	0.0234 (7)
H3	0.5812	−0.0182	0.7088	0.028*
C4	0.64896 (13)	0.0513 (7)	0.6849 (5)	0.0250 (7)
H4	0.6559	−0.0793	0.6201	0.030*
C5	0.68284 (12)	0.2121 (7)	0.7296 (5)	0.0230 (7)
C6	0.67343 (13)	0.4048 (7)	0.8307 (5)	0.0251 (8)
H6	0.6966	0.5089	0.8634	0.030*
C7	0.62823 (12)	0.4391 (7)	0.8825 (5)	0.0228 (7)
H7	0.6214	0.5685	0.9488	0.027*
C8	0.76546 (12)	0.2304 (8)	0.7501 (5)	0.0261 (8)
C9	0.78630 (13)	0.0650 (7)	0.8574 (5)	0.0266 (8)
H9	0.7713	−0.0733	0.8792	0.032*
C10	0.82982 (14)	0.1068 (7)	0.9322 (5)	0.0248 (7)
H10	0.8442	−0.0052	1.0026	0.030*
C11	0.85196 (11)	0.3161 (6)	0.9022 (4)	0.0194 (7)
C12	0.82984 (13)	0.4838 (7)	0.7983 (5)	0.0243 (7)
H12	0.8440	0.6256	0.7813	0.029*
C13	0.78638 (13)	0.4407 (7)	0.7192 (5)	0.0264 (7)
H13	0.7719	0.5509	0.6475	0.032*
C14	0.89941 (12)	0.3616 (6)	0.9821 (5)	0.0200 (7)

	U11	U22	U33	U12	U13	U23
Na1	0.0114 (7)	0.0098 (7)	0.0144 (7)	0.0005 (5)	−0.0009 (5)	−0.0005 (5)
Na2	0.0119 (8)	0.0094 (7)	0.0127 (8)	−0.0011 (5)	0.0003 (5)	0.0001 (5)
Na3	0.0169 (14)	0.0144 (15)	0.0127 (14)	0.0013 (10)	0.0008 (10)	−0.0004 (10)
O1	0.0230 (11)	0.0294 (14)	0.0299 (15)	0.0020 (11)	0.0043 (10)	−0.0037 (11)
O2	0.0183 (11)	0.0254 (13)	0.0293 (13)	−0.0020 (9)	0.0007 (10)	0.0005 (10)
O3	0.0262 (13)	0.0292 (15)	0.0282 (14)	−0.0081 (11)	−0.0015 (11)	0.0009 (11)
O4	0.0209 (12)	0.0281 (13)	0.0254 (13)	0.0042 (10)	−0.0017 (10)	0.0008 (10)
O5	0.0171 (12)	0.056 (2)	0.0288 (14)	−0.0011 (12)	0.0005 (10)	−0.0141 (13)
C1	0.0181 (15)	0.0215 (15)	0.0200 (15)	0.0019 (12)	0.0015 (12)	0.0039 (12)
C2	0.0165 (15)	0.0228 (16)	0.0204 (15)	0.0011 (12)	−0.0006 (12)	0.0030 (12)
C3	0.0187 (16)	0.0241 (17)	0.0274 (18)	−0.0015 (13)	0.0007 (13)	−0.0029 (13)
C4	0.0223 (17)	0.0260 (17)	0.0267 (17)	0.0035 (15)	0.0008 (13)	−0.0051 (14)
C5	0.0179 (16)	0.0299 (17)	0.0211 (15)	0.0015 (13)	0.0003 (12)	−0.0001 (13)
C6	0.0174 (16)	0.0290 (19)	0.0287 (17)	−0.0044 (13)	−0.0014 (13)	−0.0039 (15)
C7	0.0226 (17)	0.0217 (16)	0.0243 (17)	−0.0001 (13)	0.0016 (13)	−0.0034 (12)
C8	0.0159 (16)	0.039 (2)	0.0232 (17)	−0.0016 (14)	0.0031 (13)	−0.0074 (15)
C9	0.0227 (17)	0.0278 (18)	0.0294 (18)	−0.0069 (14)	0.0037 (14)	−0.0022 (14)
C10	0.0260 (18)	0.0237 (16)	0.0247 (17)	−0.0007 (14)	0.0024 (13)	0.0025 (14)
C11	0.0162 (15)	0.0232 (16)	0.0187 (15)	0.0003 (11)	0.0008 (11)	−0.0018 (12)
C12	0.0237 (17)	0.0238 (17)	0.0255 (18)	−0.0004 (13)	0.0028 (13)	0.0033 (13)
C13	0.0210 (16)	0.033 (2)	0.0252 (16)	0.0056 (15)	−0.0003 (12)	0.0026 (15)
C14	0.0188 (16)	0.0252 (16)	0.0162 (14)	−0.0013 (12)	0.0023 (12)	−0.0001 (12)

Na1—O1i	2.342 (3)	O5—C8	1.391 (5)
Na1—O2ii	2.434 (3)	C1—C2	1.511 (5)
Na1—O4iii	2.494 (3)	C2—C7	1.382 (5)
Na1—O2	2.517 (3)	C2—C3	1.394 (5)
Na1—O3iii	2.789 (3)	C3—C4	1.399 (5)
Na2—O3iv	2.285 (3)	C3—H3	0.9300
Na2—O4iii	2.326 (3)	C4—C5	1.388 (5)
Na2—O2	2.435 (3)	C4—H4	0.9300
Na2—O4v	2.453 (3)	C5—C6	1.389 (6)
O1—C1	1.252 (5)	C6—C7	1.404 (5)
O1—Na1vi	2.342 (3)	C6—H6	0.9300
O1—Na3vi	2.784 (4)	C7—H7	0.9300
O2—C1	1.268 (4)	C8—C9	1.382 (6)
O2—Na1vii	2.434 (3)	C8—C13	1.384 (6)
O3—C14	1.260 (5)	C9—C10	1.389 (5)
O3—Na2viii	2.285 (3)	C9—H9	0.9300
O3—Na3ix	2.774 (4)	C10—C11	1.394 (5)
O3—Na1x	2.789 (3)	C10—H10	0.9300
O4—C14	1.266 (5)	C11—C12	1.393 (5)
O4—Na2x	2.326 (3)	C11—C14	1.509 (5)
O4—Na2xi	2.453 (3)	C12—C13	1.401 (5)
O4—Na1x	2.494 (3)	C12—H12	0.9300
O5—C5	1.381 (4)	C13—H13	0.9300
O1i—Na1—O2ii	128.52 (12)	O2—C1—C2	117.6 (3)
O1i—Na1—O4iii	96.84 (11)	C7—C2—C3	119.4 (3)
O2ii—Na1—O4iii	123.07 (11)	C7—C2—C1	121.1 (3)
O1i—Na1—O2	84.62 (11)	C3—C2—C1	119.5 (3)
O2ii—Na1—O2	124.75 (10)	C2—C3—C4	120.5 (3)
O4iii—Na1—O2	86.69 (10)	C2—C3—H3	119.7
O1i—Na1—O3iii	144.60 (11)	C4—C3—H3	119.7
O2ii—Na1—O3iii	76.17 (10)	C5—C4—C3	119.1 (3)
O4iii—Na1—O3iii	49.58 (9)	C5—C4—H4	120.4
O2—Na1—O3iii	101.66 (10)	C3—C4—H4	120.4
O3iv—Na2—O4iii	101.63 (12)	O5—C5—C4	115.2 (3)
O3iv—Na2—O2	86.45 (11)	O5—C5—C6	123.4 (3)
O4iii—Na2—O2	92.48 (11)	C4—C5—C6	121.3 (3)
O3iv—Na2—O4v	101.41 (12)	C5—C6—C7	118.6 (3)
O4iii—Na2—O4v	135.10 (11)	C5—C6—H6	120.7
O2—Na2—O4v	126.93 (11)	C7—C6—H6	120.7
O2—Na2—Na3vi	72.45 (9)	C2—C7—C6	121.0 (3)
C1—O1—Na1vi	140.4 (3)	C2—C7—H7	119.5
C1—O1—Na3vi	102.7 (2)	C6—C7—H7	119.5
Na1vi—O1—Na3vi	92.50 (11)	C9—C8—C13	121.6 (3)
C1—O2—Na1vii	115.6 (2)	C9—C8—O5	118.7 (4)
C1—O2—Na2	106.9 (2)	C13—C8—O5	119.4 (4)
Na1vii—O2—Na2	101.34 (11)	C8—C9—C10	119.6 (3)
C1—O2—Na1	120.0 (2)	C8—C9—H9	120.2
Na1vii—O2—Na1	117.45 (12)	C10—C9—H9	120.2
Na2—O2—Na1	88.21 (10)	C9—C10—C11	120.2 (4)
C14—O3—Na2viii	154.6 (3)	C9—C10—H10	119.9
C14—O3—Na3ix	128.3 (2)	C11—C10—H10	119.9
Na2viii—O3—Na3ix	73.42 (10)	C12—C11—C10	119.4 (3)
C14—O3—Na1x	83.5 (2)	C12—C11—C14	120.1 (3)
Na2viii—O3—Na1x	95.35 (10)	C10—C11—C14	120.4 (3)
Na3ix—O3—Na1x	68.61 (9)	C11—C12—C13	120.6 (3)
C14—O4—Na2x	129.7 (2)	C11—C12—H12	119.7
C14—O4—Na2xi	115.0 (2)	C13—C12—H12	119.7
Na2x—O4—Na2xi	115.15 (12)	C8—C13—C12	118.6 (4)
C14—O4—Na1x	96.8 (2)	C8—C13—H13	120.7
Na2x—O4—Na1x	91.23 (10)	C12—C13—H13	120.7
Na2xi—O4—Na1x	84.93 (10)	O3—C14—O4	124.1 (3)
C5—O5—C8	120.4 (3)	O3—C14—C11	118.2 (3)
O1—C1—O2	123.7 (3)	O4—C14—C11	117.7 (3)
O1—C1—C2	118.7 (3)
O3iv—Na2—O2—C1	−128.5 (2)	C3—C4—C5—O5	−174.1 (4)
O4iii—Na2—O2—C1	130.0 (2)	C3—C4—C5—C6	1.9 (6)
O4v—Na2—O2—C1	−26.9 (3)	O5—C5—C6—C7	173.5 (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—C6	0.7 (6)
O4v—Na2—O2—Na1vii	94.58 (14)	C1—C2—C7—C6	−178.9 (3)
O3iv—Na2—O2—Na1	110.60 (11)	C5—C6—C7—C2	0.9 (6)
O4iii—Na2—O2—Na1	9.09 (11)	C5—O5—C8—C9	90.4 (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—C1	114.3 (2)	O5—C8—C9—C10	171.3 (3)
O4iii—Na1—O2—C1	−117.0 (3)	C8—C9—C10—C11	1.3 (6)
O3iii—Na1—O2—C1	−164.5 (3)	C9—C10—C11—C12	0.7 (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—C13	178.0 (3)
O4iii—Na1—O2—Na1vii	93.37 (13)	C9—C8—C13—C12	0.5 (6)
O3iii—Na1—O2—Na1vii	45.83 (14)	O5—C8—C13—C12	−172.7 (3)
C14iii—Na1—O2—Na1vii	71.53 (14)	C11—C12—C13—C8	1.6 (6)
O1i—Na1—O2—Na2	88.72 (11)	Na2viii—O3—C14—O4	113.0 (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—O4	24.2 (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—C11	148.8 (3)
Na3vi—O1—C1—O2	40.8 (4)	Na1x—O3—C14—C11	−155.1 (3)
Na1vi—O1—C1—C2	111.7 (4)	Na2viii—O3—C14—Na1x	88.8 (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—O3	70.0 (5)
Na2—O2—C1—O1	23.4 (4)	Na2xi—O4—C14—O3	−114.9 (4)
Na1—O2—C1—O1	121.4 (3)	Na1x—O4—C14—O3	−27.3 (4)
Na1vii—O2—C1—C2	90.6 (3)	Na2x—O4—C14—C11	−110.7 (3)
Na2—O2—C1—C2	−157.5 (2)	Na2xi—O4—C14—C11	64.4 (3)
Na1—O2—C1—C2	−59.6 (4)	Na1x—O4—C14—C11	152.0 (3)
O1—C1—C2—C7	−8.4 (5)	Na2x—O4—C14—Na1x	97.3 (3)
O2—C1—C2—C7	172.5 (3)	Na2xi—O4—C14—Na1x	−87.57 (17)
O1—C1—C2—C3	172.0 (4)	C12—C11—C14—O3	11.6 (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—C4	178.6 (3)	C10—C11—C14—O4	12.5 (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—Na1x	84.9 (6)
C8—O5—C5—C6	37.9 (6)