2-[4-(Carb-oxy-meth-yl)phen-oxy]acetic acid.

The title compound, C(10)H(10)O(5), was obtained by the reaction of 4-hy-droxy-phenyl-acetic acid with chloro-acetic acid. In the crystal, the mol-ecules form a three-dimensional network by way of inter-molecular O-H⋯O hydrogen bonding.

Related literature

For applications of metal-organic frameworks with carb­oxy­lic acid ligands, see: Kuppler et al. (2009) ▶; Jahan et al. (2010 ▶); Armelao et al. (2010 ▶); Yashima et al. (2009 ▶). The title compound was obtained by the reaction of 4-hy­droxy­phenyl­acetic (Gracin et al., 2005 ▶) and chloro­acetic acid (Sandhu et al., 1991 ▶).

Experimental

Crystal data

C10H10O5

M = 210.18

Orthorhombic,

a = 5.4640 (2) Å

b = 10.7798 (5) Å

c = 16.2550 (7) Å

V = 957.43 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.42 × 0.38 × 0.31 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.95, T max = 0.96

11814 measured reflections

1315 independent reflections

1162 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.099

S = 1.07

1315 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536810051810/ds2074sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810051810/ds2074Isup2.hkl

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

C10H10O5	F(000) = 440
Mr = 210.18	Dx = 1.458 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6173 reflections
a = 5.4640 (2) Å	θ = 2.3–27.7°
b = 10.7798 (5) Å	µ = 0.12 mm−1
c = 16.2550 (7) Å	T = 296 K
V = 957.43 (7) Å3	Block, colourless
Z = 4	0.42 × 0.38 × 0.31 mm

Bruker APEXII area-detector diffractometer	1315 independent reflections
Radiation source: fine-focus sealed tube	1162 reflections with I > 2σ(I)
graphite	Rint = 0.049
phi and ω scans	θmax = 27.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.95, Tmax = 0.96	k = −13→14
11814 measured reflections	l = −20→21

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.2342P] where P = (Fo2 + 2Fc2)/3
1315 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.19 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 > 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.

	x	y	z	Uiso*/Ueq
O1	0.4626 (4)	0.67278 (16)	0.64905 (10)	0.0651 (5)
O2	0.7484 (4)	0.79234 (17)	0.59564 (10)	0.0645 (5)
H2	0.7132	0.8367	0.6349	0.077*
O3	0.4929 (3)	0.51339 (14)	0.52607 (9)	0.0489 (4)
O4	0.8002 (3)	0.06923 (15)	0.22690 (11)	0.0536 (4)
O5	0.6100 (4)	−0.00299 (16)	0.33749 (9)	0.0589 (5)
H5	0.7257	−0.0515	0.3374	0.071*
C1	0.6127 (4)	0.6927 (2)	0.59700 (12)	0.0440 (5)
C2	0.6695 (4)	0.6081 (2)	0.52593 (12)	0.0443 (5)
H2A	0.6632	0.6538	0.4746	0.053*
H2B	0.8320	0.5731	0.5320	0.053*
C3	0.4856 (4)	0.43389 (19)	0.46020 (12)	0.0401 (4)
C4	0.2906 (4)	0.3526 (2)	0.45967 (13)	0.0449 (5)
H4A	0.1741	0.3559	0.5013	0.054*
C5	0.2681 (4)	0.2661 (2)	0.39733 (13)	0.0467 (5)
H5A	0.1357	0.2119	0.3972	0.056*
C6	0.4405 (4)	0.2592 (2)	0.33498 (12)	0.0427 (5)
C7	0.6354 (4)	0.3416 (2)	0.33640 (13)	0.0457 (5)
H7A	0.7520	0.3381	0.2948	0.055*
C8	0.6606 (4)	0.4294 (2)	0.39878 (12)	0.0445 (5)
H8A	0.7925	0.4839	0.3991	0.053*
C9	0.4187 (4)	0.1613 (2)	0.26811 (13)	0.0502 (5)
H9A	0.2651	0.1171	0.2741	0.060*
H9B	0.4198	0.2009	0.2145	0.060*
C10	0.6279 (4)	0.07182 (19)	0.27412 (13)	0.0431 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0757 (12)	0.0593 (11)	0.0602 (9)	−0.0208 (10)	0.0218 (10)	−0.0149 (8)
O2	0.0736 (12)	0.0572 (10)	0.0627 (10)	−0.0251 (10)	0.0144 (10)	−0.0129 (8)
O3	0.0598 (9)	0.0426 (8)	0.0444 (7)	−0.0102 (8)	0.0096 (8)	−0.0050 (6)
O4	0.0479 (8)	0.0490 (9)	0.0639 (9)	0.0009 (8)	0.0033 (8)	0.0069 (8)
O5	0.0625 (10)	0.0639 (10)	0.0503 (8)	0.0177 (10)	0.0026 (8)	0.0099 (8)
C1	0.0475 (11)	0.0409 (10)	0.0437 (10)	−0.0063 (10)	−0.0009 (10)	0.0025 (9)
C2	0.0446 (11)	0.0461 (11)	0.0423 (10)	−0.0056 (10)	0.0009 (10)	0.0003 (9)
C3	0.0448 (10)	0.0376 (9)	0.0378 (9)	0.0010 (9)	0.0000 (9)	0.0026 (8)
C4	0.0447 (11)	0.0452 (11)	0.0448 (10)	−0.0008 (10)	0.0034 (10)	0.0012 (9)
C5	0.0435 (11)	0.0452 (11)	0.0515 (11)	−0.0016 (10)	−0.0029 (10)	0.0017 (9)
C6	0.0436 (11)	0.0428 (10)	0.0416 (9)	0.0092 (10)	−0.0067 (9)	0.0012 (8)
C7	0.0436 (11)	0.0512 (12)	0.0422 (10)	0.0051 (10)	0.0030 (9)	0.0011 (9)
C8	0.0412 (10)	0.0465 (11)	0.0457 (10)	−0.0023 (10)	0.0002 (9)	0.0018 (9)
C9	0.0493 (12)	0.0541 (12)	0.0473 (11)	0.0129 (11)	−0.0122 (10)	−0.0060 (10)
C10	0.0455 (11)	0.0389 (10)	0.0451 (10)	0.0010 (10)	−0.0084 (10)	−0.0040 (9)

O1—C1	1.198 (3)	C4—C5	1.383 (3)
O2—C1	1.305 (3)	C4—H4A	0.9300
O2—H2	0.8200	C5—C6	1.386 (3)
O3—C3	1.372 (2)	C5—H5A	0.9300
O3—C2	1.405 (3)	C6—C7	1.387 (3)
O4—C10	1.215 (3)	C6—C9	1.519 (3)
O5—C10	1.312 (3)	C7—C8	1.394 (3)
O5—H5	0.8200	C7—H7A	0.9300
C1—C2	1.504 (3)	C8—H8A	0.9300
C2—H2A	0.9700	C9—C10	1.499 (3)
C2—H2B	0.9700	C9—H9A	0.9700
C3—C4	1.380 (3)	C9—H9B	0.9700
C3—C8	1.383 (3)
C1—O2—H2	109.5	C6—C5—H5A	119.6
C3—O3—C2	118.19 (16)	C5—C6—C7	118.39 (19)
C10—O5—H5	109.5	C5—C6—C9	120.5 (2)
O1—C1—O2	123.3 (2)	C7—C6—C9	121.11 (19)
O1—C1—C2	125.1 (2)	C6—C7—C8	121.5 (2)
O2—C1—C2	111.64 (18)	C6—C7—H7A	119.2
O3—C2—C1	107.31 (17)	C8—C7—H7A	119.2
O3—C2—H2A	110.3	C3—C8—C7	118.7 (2)
C1—C2—H2A	110.3	C3—C8—H8A	120.6
O3—C2—H2B	110.3	C7—C8—H8A	120.6
C1—C2—H2B	110.3	C10—C9—C6	109.89 (17)
H2A—C2—H2B	108.5	C10—C9—H9A	109.7
O3—C3—C4	115.09 (18)	C6—C9—H9A	109.7
O3—C3—C8	124.41 (19)	C10—C9—H9B	109.7
C4—C3—C8	120.47 (19)	C6—C9—H9B	109.7
C3—C4—C5	120.1 (2)	H9A—C9—H9B	108.2
C3—C4—H4A	119.9	O4—C10—O5	122.6 (2)
C5—C4—H4A	119.9	O4—C10—C9	124.4 (2)
C4—C5—C6	120.8 (2)	O5—C10—C9	112.97 (19)
C4—C5—H5A	119.6
C3—O3—C2—C1	171.19 (18)	C5—C6—C7—C8	0.3 (3)
O1—C1—C2—O3	8.2 (3)	C9—C6—C7—C8	−178.2 (2)
O2—C1—C2—O3	−171.83 (18)	O3—C3—C8—C7	178.09 (19)
C2—O3—C3—C4	−172.77 (18)	C4—C3—C8—C7	0.2 (3)
C2—O3—C3—C8	9.3 (3)	C6—C7—C8—C3	−0.2 (3)
O3—C3—C4—C5	−178.35 (19)	C5—C6—C9—C10	−114.2 (2)
C8—C3—C4—C5	−0.3 (3)	C7—C6—C9—C10	64.2 (3)
C3—C4—C5—C6	0.4 (3)	C6—C9—C10—O4	−106.1 (2)
C4—C5—C6—C7	−0.3 (3)	C6—C9—C10—O5	72.4 (2)
C4—C5—C6—C9	178.15 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4i	0.82	1.81	2.617 (2)	168
O5—H5···O1ii	0.82	1.85	2.666 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4i	0.82	1.81	2.617 (2)	168
O5—H5⋯O1ii	0.82	1.85	2.666 (2)	171

Symmetry codes: (i) ; (ii) .