4,4′-Oxydibenzoic acid

In the title compound, C₁₄H₁₀O₅, each carboxyl group is coplanar with the attached aromatic ring. The dihedral angle between these planes is 72.56 (5)°. The carboxyl groups are linked by a pair of centrosymmetric O—H...O hydrogen bonds, creating a zigzag chain along the [21] direction.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.123
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSMU01_ALERT_1_C  The ratio of given/expected absorption coefficient lies
               outside the range 0.99 <> 1.01
            Calculated value of mu =     0.117
            Value of mu given      =     0.120
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        300 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Considerable attention is focused on the synthesis of new ligands for the construction of metal organic frameworks (MOF's) since they add structural diversity to these materials. This study originates from our interest in U-shaped ligands of the rigid aromatics containing their coordinating groups at the terminal site. Two such ligands may coordinate two metal centers, closing the circle and thus forming a box-like aperture. Upon crystallization these boxed structures may form a porous material. Materials of this type are increasingly in demand for applications in gas storage since they are selective to the shapes and sizes of the molecules that can pass through the enclosed pore. This selectivity is dependent on their structural framework and the pore size formed therein (Férey et al., 2005). It has been found that multidentate linkers such as carboxylates allow the formation of more rigid frameworks than, for example, commonly used poly-topic N-bound organic linkers. This functionality is due to their ability to incorporate metal ions into M—O—C clusters (Eddaoudi et al., 2001). To this end the dicarboxylic acid had been selected as an organic linker.

One such linker that was selected is 4,4'-oxydibenzoic acid, (I), commercially available from Sigma-Aldrich. However, its crystal structure has not been reported.

In the crystal structure, the respective acid groups are co-planar with their aromatic rings (Fig. 1). The angle subtended at the central oxygen atom, O3, is 117.97 (12)°. This is higher than the average C—O—C angle of 115° owing to the steric interactions between H6 and H13.

The angle between the least squares planes defined by the 6 carbon atoms of each benzene ring is 72.56 (0.05) °.

This structure forms a one-dimensional zigzag chain that is linked via the H-bonds between the acid proton of one molecule and the carbonyl oxygen of another. The infinite chain of intermolecular H-bonded molecules packs along [2 - 3 1].

Related literature

For related literature, see: Eddaoudi et al. (2001); Férey et al. (2005).

S2. Experimental

The compound was purchased from Sigma-Aldrich [CAS 2215–89-6] and recrystallized from ethanol without further purification.

S3. Refinement

Structure solution and refinement was performed using the SHELX-97 suite of programs. Hydrogen atoms were refined in calculated positions, using a riding model (C–H = 0.95 Å; O–H = 0.84 Å).

Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of (I) viewed along [010] showing zigzag chain. H-bonds are displayed as dashed lines.

4,4'-Oxydibenzoic acid

Crystal data

C14H10O5	Z = 2
Mr = 258.22	F(000) = 268
Triclinic, P1	Dx = 1.518 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3654 (9) Å	Cell parameters from 2085 reflections
b = 6.4093 (11) Å	θ = 2.4–27.7°
c = 16.847 (3) Å	µ = 0.12 mm^−1
α = 86.848 (3)°	T = 100 K
β = 83.106 (3)°	Needle, colourless
γ = 79.309 (3)°	0.33 × 0.24 × 0.10 mm
V = 564.86 (16) Å^3

Data collection

Bruker APEX CCD area-detector diffractometer	1901 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 28.3°, θmin = 2.4°
ω scans	h = −7→6
6444 measured reflections	k = −8→8
2582 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.0103P] where P = (Fo^2 + 2Fc^2)/3
2582 reflections	(Δ/σ)max = 0.009
172 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
O1	0.1763 (2)	1.24541 (18)	0.02374 (7)	0.0251 (3)
H1	0.0651	1.3129	−0.0037	0.030*
C1	0.2712 (3)	1.3777 (3)	0.06123 (10)	0.0176 (4)
O2	0.2019 (2)	1.57409 (18)	0.05702 (7)	0.0242 (3)
C2	0.4720 (3)	1.2816 (3)	0.11236 (10)	0.0171 (4)
O3	1.0046 (2)	1.03887 (17)	0.26827 (7)	0.0196 (3)
C3	0.5979 (3)	1.4139 (3)	0.14919 (10)	0.0179 (4)
H3	0.5621	1.5629	0.1385	0.022*
O4	1.1999 (2)	0.12156 (17)	0.43485 (7)	0.0206 (3)
C4	0.7753 (3)	1.3304 (3)	0.20139 (10)	0.0187 (4)
H4	0.8604	1.4211	0.2268	0.022*
O5	0.7865 (2)	0.22879 (18)	0.47782 (7)	0.0219 (3)
H5	0.8076	0.1086	0.5012	0.026*
C5	0.8262 (3)	1.1128 (3)	0.21581 (10)	0.0166 (4)
C6	0.7121 (3)	0.9777 (3)	0.17638 (10)	0.0199 (4)
H6	0.7564	0.8282	0.1845	0.024*
C7	0.5332 (3)	1.0625 (3)	0.12509 (10)	0.0194 (4)
H7	0.4522	0.9711	0.0986	0.023*
C8	0.9921 (3)	0.8447 (3)	0.30857 (10)	0.0167 (4)
C9	1.2095 (3)	0.6890 (3)	0.30130 (10)	0.0186 (4)
H9	1.3571	0.7134	0.2676	0.022*
C10	1.2098 (3)	0.4977 (3)	0.34358 (10)	0.0185 (4)
H10	1.3584	0.3903	0.3391	0.022*
C11	0.9941 (3)	0.4623 (2)	0.39243 (9)	0.0155 (4)
C12	0.7761 (3)	0.6215 (2)	0.39935 (10)	0.0174 (4)
H12	0.6280	0.5976	0.4329	0.021*
C13	0.7753 (3)	0.8134 (3)	0.35746 (10)	0.0184 (4)
H13	0.6280	0.9219	0.3622	0.022*
C14	0.9955 (3)	0.2569 (3)	0.43785 (10)	0.0153 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0253 (7)	0.0267 (7)	0.0242 (7)	0.0004 (6)	−0.0133 (6)	−0.0030 (6)
C1	0.0180 (9)	0.0188 (9)	0.0151 (8)	−0.0022 (7)	−0.0004 (7)	−0.0008 (7)
O2	0.0258 (7)	0.0194 (7)	0.0262 (7)	0.0009 (5)	−0.0077 (6)	0.0036 (5)
C2	0.0160 (9)	0.0213 (9)	0.0131 (8)	−0.0024 (7)	−0.0003 (7)	0.0000 (7)
O3	0.0204 (7)	0.0165 (6)	0.0236 (7)	−0.0055 (5)	−0.0086 (5)	0.0050 (5)
C3	0.0207 (9)	0.0132 (8)	0.0185 (9)	−0.0003 (7)	−0.0013 (7)	0.0003 (7)
O4	0.0185 (7)	0.0183 (7)	0.0236 (7)	0.0011 (5)	−0.0034 (5)	−0.0004 (5)
C4	0.0209 (9)	0.0189 (9)	0.0171 (9)	−0.0057 (7)	−0.0024 (7)	−0.0007 (7)
O5	0.0215 (7)	0.0182 (6)	0.0249 (7)	−0.0045 (5)	0.0007 (5)	0.0047 (5)
C5	0.0138 (8)	0.0203 (9)	0.0149 (8)	−0.0018 (7)	−0.0016 (7)	0.0016 (7)
C6	0.0212 (9)	0.0166 (9)	0.0215 (9)	−0.0018 (7)	−0.0044 (7)	0.0002 (7)
C7	0.0211 (9)	0.0180 (9)	0.0202 (9)	−0.0047 (7)	−0.0042 (7)	−0.0009 (7)
C8	0.0215 (9)	0.0136 (8)	0.0164 (9)	−0.0049 (7)	−0.0058 (7)	−0.0003 (7)
C9	0.0146 (9)	0.0226 (9)	0.0190 (9)	−0.0047 (7)	−0.0015 (7)	0.0002 (7)
C10	0.0165 (9)	0.0165 (9)	0.0216 (9)	−0.0005 (7)	−0.0022 (7)	−0.0015 (7)
C11	0.0182 (9)	0.0157 (9)	0.0137 (8)	−0.0036 (7)	−0.0053 (7)	−0.0008 (7)
C12	0.0147 (8)	0.0204 (9)	0.0174 (9)	−0.0035 (7)	−0.0022 (7)	−0.0023 (7)
C13	0.0175 (9)	0.0167 (9)	0.0203 (9)	0.0006 (7)	−0.0046 (7)	−0.0024 (7)
C14	0.0168 (9)	0.0147 (8)	0.0160 (8)	−0.0038 (7)	−0.0049 (7)	−0.0033 (7)

Geometric parameters (Å, º)

O1—C1	1.2933 (19)	C5—C6	1.386 (2)
O1—H1	0.8400	C6—C7	1.385 (2)
C1—O2	1.2455 (19)	C6—H6	0.9500
C1—C2	1.484 (2)	C7—H7	0.9500
C2—C7	1.392 (2)	C8—C13	1.382 (2)
C2—C3	1.390 (2)	C8—C9	1.385 (2)
O3—C5	1.3820 (19)	C9—C10	1.384 (2)
O3—C8	1.3930 (19)	C9—H9	0.9500
C3—C4	1.388 (2)	C10—C11	1.384 (2)
C3—H3	0.9500	C10—H10	0.9500
O4—C14	1.2633 (19)	C11—C12	1.400 (2)
C4—C5	1.385 (2)	C11—C14	1.485 (2)
C4—H4	0.9500	C12—C13	1.383 (2)
O5—C14	1.274 (2)	C12—H12	0.9500
O5—H5	0.8400	C13—H13	0.9500
C1—O1—H1	109.5	C2—C7—H7	120.0
O2—C1—O1	124.03 (15)	C13—C8—C9	121.36 (16)
O2—C1—C2	120.17 (15)	C13—C8—O3	121.04 (15)
O1—C1—C2	115.80 (15)	C9—C8—O3	117.50 (15)
C7—C2—C3	119.63 (16)	C10—C9—C8	119.44 (16)
C7—C2—C1	121.30 (15)	C10—C9—H9	120.3
C3—C2—C1	119.06 (15)	C8—C9—H9	120.3
C5—O3—C8	117.97 (12)	C9—C10—C11	120.15 (15)
C4—C3—C2	120.62 (16)	C9—C10—H10	119.9
C4—C3—H3	119.7	C11—C10—H10	119.9
C2—C3—H3	119.7	C10—C11—C12	119.74 (15)
C5—C4—C3	118.89 (16)	C10—C11—C14	119.96 (15)
C5—C4—H4	120.6	C12—C11—C14	120.29 (15)
C3—C4—H4	120.6	C13—C12—C11	120.30 (16)
C14—O5—H5	109.5	C13—C12—H12	119.9
O3—C5—C4	116.30 (14)	C11—C12—H12	119.9
O3—C5—C6	122.47 (15)	C8—C13—C12	119.01 (16)
C4—C5—C6	121.16 (16)	C8—C13—H13	120.5
C7—C6—C5	119.48 (16)	C12—C13—H13	120.5
C7—C6—H6	120.3	O4—C14—O5	123.99 (15)
C5—C6—H6	120.3	O4—C14—C11	119.03 (15)
C6—C7—C2	120.07 (16)	O5—C14—C11	116.98 (14)
C6—C7—H7	120.0
O2—C1—C2—C7	172.85 (16)	C5—O3—C8—C13	−59.0 (2)
O1—C1—C2—C7	−6.4 (2)	C5—O3—C8—C9	124.55 (16)
O2—C1—C2—C3	−6.1 (2)	C13—C8—C9—C10	0.2 (3)
O1—C1—C2—C3	174.68 (15)	O3—C8—C9—C10	176.70 (14)
C7—C2—C3—C4	−3.0 (3)	C8—C9—C10—C11	0.3 (2)
C1—C2—C3—C4	175.93 (15)	C9—C10—C11—C12	−0.5 (2)
C2—C3—C4—C5	0.4 (3)	C9—C10—C11—C14	−179.86 (14)
C8—O3—C5—C4	155.32 (15)	C10—C11—C12—C13	0.2 (2)
C8—O3—C5—C6	−27.7 (2)	C14—C11—C12—C13	179.56 (14)
C3—C4—C5—O3	179.98 (14)	C9—C8—C13—C12	−0.5 (2)
C3—C4—C5—C6	3.0 (3)	O3—C8—C13—C12	−176.87 (14)
O3—C5—C6—C7	179.47 (15)	C11—C12—C13—C8	0.3 (2)
C4—C5—C6—C7	−3.7 (3)	C10—C11—C14—O4	4.2 (2)
C5—C6—C7—C2	1.1 (3)	C12—C11—C14—O4	−175.22 (15)
C3—C2—C7—C6	2.3 (3)	C10—C11—C14—O5	−175.75 (14)
C1—C2—C7—C6	−176.65 (15)	C12—C11—C14—O5	4.9 (2)