4,4'-[p-Phenyl-enebis(-oxy)]dibutanoic acid.

The complete mol-ecule of the title compound, C(14)H(18)O(6), has a center of inversion at the centroid of the benzene ring and the asymmetric unit contains one half-mol-ecule. The conformation of the side chain is anti [C-C-C-C = -171.40 (17)°]. In the crystal, pairs of head-to-head carb-oxy-lic acid O-H⋯O hydrogen bonds link the mol-ecules into infinite zigzag chains propagating along [130]. Weak C-H⋯π inter-actions between adjacent chains expand the structure into a layered network in the ac plane.

Related literature

For general background to phen­oxy­acetic acid derivatives, see: Yada (1959 ▶); Zheng et al. (2007 ▶); Deng et al. (2010 ▶); Xiong et al. (2010 ▶); Fu et al. (2011 ▶). For related structures of multidentate O-donor ligands such as benzene-1,4-di­oxy­diacetic acid and benzene-1,4-di­oxy­dibutanoic acid, see: Dai et al. (2009 ▶); Zhu et al. (2008 ▶); Li et al. (2010 ▶); Yang et al. (2010 ▶); Zhao (2011 ▶). For the synthesis of the title compound, see: Zhang et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H18O6

M = 282.28

Triclinic,

a = 4.8389 (11) Å

b = 6.6300 (15) Å

c = 11.406 (3) Å

α = 83.067 (5)°

β = 81.249 (5)°

γ = 71.095 (4)°

V = 341.16 (13) Å3

Z = 1

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.21 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.978, T max = 0.981

1861 measured reflections

1170 independent reflections

1025 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.162

S = 1.02

1170 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036828/hb6398sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036828/hb6398Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036828/hb6398Isup3.cml

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

C14H18O6	Z = 1
Mr = 282.28	F(000) = 150
Triclinic, P1	Dx = 1.374 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8389 (11) Å	Cell parameters from 1172 reflections
b = 6.6300 (15) Å	θ = 3.3–29.3°
c = 11.406 (3) Å	µ = 0.11 mm−1
α = 83.067 (5)°	T = 296 K
β = 81.249 (5)°	Block, colorless
γ = 71.095 (4)°	0.21 × 0.19 × 0.18 mm
V = 341.16 (13) Å3

Bruker SMART CCD diffractometer	1170 independent reflections
Radiation source: fine-focus sealed tube	1025 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.978, Tmax = 0.981	k = −6→7
1861 measured reflections	l = −13→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0972P)2 + 0.1511P] where P = (Fo2 + 2Fc2)/3
1170 reflections	(Δ/σ)max < 0.001
92 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
O1	0.9691 (4)	−0.2476 (3)	0.45159 (18)	0.0672 (6)
O2	0.7156 (4)	−0.4427 (3)	0.40552 (18)	0.0663 (6)
H2	0.8171	−0.5317	0.4509	0.099*
O3	0.4183 (3)	0.2151 (2)	0.13043 (12)	0.0412 (5)
C1	0.7769 (4)	−0.2666 (3)	0.39978 (17)	0.0364 (5)
C2	0.5900 (4)	−0.0856 (3)	0.32641 (18)	0.0410 (6)
H2A	0.4016	−0.0255	0.3730	0.049*
H2B	0.5536	−0.1415	0.2575	0.049*
C3	0.7239 (5)	0.0911 (3)	0.28431 (19)	0.0415 (6)
H3A	0.7874	0.1333	0.3516	0.050*
H3B	0.8965	0.0371	0.2276	0.050*
C4	0.5123 (5)	0.2853 (3)	0.22662 (18)	0.0409 (5)
H4A	0.3448	0.3480	0.2837	0.049*
H4B	0.6090	0.3920	0.1973	0.049*
C5	0.2114 (4)	0.3636 (3)	0.06782 (16)	0.0328 (5)
C6	0.1047 (4)	0.5809 (3)	0.08497 (18)	0.0375 (5)
H6	0.1744	0.6355	0.1417	0.045*
C7	0.1059 (4)	0.2846 (3)	−0.01715 (17)	0.0373 (5)
H7	0.1775	0.1394	−0.0288	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0781 (12)	0.0427 (10)	0.0919 (14)	−0.0226 (9)	−0.0584 (11)	0.0239 (9)
O2	0.0855 (14)	0.0421 (10)	0.0817 (13)	−0.0260 (9)	−0.0510 (11)	0.0240 (8)
O3	0.0462 (9)	0.0296 (8)	0.0429 (8)	−0.0002 (6)	−0.0218 (6)	0.0041 (6)
C1	0.0388 (10)	0.0319 (11)	0.0358 (10)	−0.0068 (8)	−0.0098 (8)	0.0033 (8)
C2	0.0387 (11)	0.0388 (12)	0.0417 (11)	−0.0058 (9)	−0.0149 (9)	0.0063 (9)
C3	0.0424 (11)	0.0360 (11)	0.0446 (12)	−0.0072 (9)	−0.0207 (9)	0.0086 (9)
C4	0.0460 (11)	0.0323 (11)	0.0431 (11)	−0.0073 (9)	−0.0192 (9)	0.0056 (8)
C5	0.0313 (9)	0.0295 (10)	0.0334 (10)	−0.0044 (8)	−0.0095 (7)	0.0065 (7)
C6	0.0420 (11)	0.0323 (11)	0.0377 (10)	−0.0075 (8)	−0.0140 (8)	−0.0002 (8)
C7	0.0428 (11)	0.0252 (9)	0.0394 (11)	−0.0032 (8)	−0.0109 (8)	0.0016 (7)

O1—C1	1.221 (3)	C3—H3A	0.9700
O2—C1	1.287 (3)	C3—H3B	0.9700
O2—H2	0.8200	C4—H4A	0.9700
O3—C5	1.375 (2)	C4—H4B	0.9700
O3—C4	1.428 (2)	C5—C7	1.386 (3)
C1—C2	1.498 (3)	C5—C6	1.391 (3)
C2—C3	1.512 (3)	C6—C7i	1.385 (3)
C2—H2A	0.9700	C6—H6	0.9300
C2—H2B	0.9700	C7—C6i	1.385 (3)
C3—C4	1.512 (3)	C7—H7	0.9300
C1—O2—H2	109.5	H3A—C3—H3B	107.8
C5—O3—C4	117.68 (15)	O3—C4—C3	107.15 (16)
O1—C1—O2	122.66 (18)	O3—C4—H4A	110.3
O1—C1—C2	122.65 (18)	C3—C4—H4A	110.3
O2—C1—C2	114.68 (18)	O3—C4—H4B	110.3
C1—C2—C3	114.15 (16)	C3—C4—H4B	110.3
C1—C2—H2A	108.7	H4A—C4—H4B	108.5
C3—C2—H2A	108.7	O3—C5—C7	115.72 (16)
C1—C2—H2B	108.7	O3—C5—C6	124.72 (18)
C3—C2—H2B	108.7	C7—C5—C6	119.56 (18)
H2A—C2—H2B	107.6	C7i—C6—C5	119.61 (19)
C4—C3—C2	112.76 (16)	C7i—C6—H6	120.2
C4—C3—H3A	109.0	C5—C6—H6	120.2
C2—C3—H3A	109.0	C6i—C7—C5	120.83 (18)
C4—C3—H3B	109.0	C6i—C7—H7	119.6
C2—C3—H3B	109.0	C5—C7—H7	119.6
O1—C1—C2—C3	21.4 (3)	C4—O3—C5—C6	5.5 (3)
O2—C1—C2—C3	−159.7 (2)	O3—C5—C6—C7i	−179.46 (17)
C1—C2—C3—C4	−171.40 (17)	C7—C5—C6—C7i	0.1 (3)
C5—O3—C4—C3	176.81 (16)	O3—C5—C7—C6i	179.49 (16)
C2—C3—C4—O3	−57.1 (2)	C6—C5—C7—C6i	−0.1 (3)
C4—O3—C5—C7	−174.06 (17)

Cg1 is the centroid of the C5–C7/C5'–C7' ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ii	0.82	1.85	2.668 (3)	174
C4—H4B···Cg1iii	0.97	2.89	3.703 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C7/C5′–C7′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.85	2.668 (3)	174
C4—H4B⋯Cg1ii	0.97	2.89	3.703 (3)	142

Symmetry codes: (i) ; (ii) .