2-[4-(Carb­oxy­meth­yl)phen­oxy]acetic acid

Fu, J.-D.; Wen, Y.-H.

doi:10.1107/S1600536810051810

organic compounds

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Volume 67| Part 1| January 2011| Page o167

https://doi.org/10.1107/S1600536810051810

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2-[4-(Carboxymethyl)phenoxy]acetic acid

Jun-Dan Fu ^a and Yi-Hang Wen ^a ^*

^aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: wyh@zjnu.edu.cn

(Received 26 November 2010; accepted 10 December 2010; online 18 December 2010)

The title compound, C₁₀H₁₀O₅, was obtained by the reaction of 4-hydroxyphenylacetic acid with chloroacetic acid. In the crystal, the molecules form a three-dimensional network by way of intermolecular 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_r = 210.18
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 1.07
1315 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810051810/ds2074sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051810/ds2074Isup2.hkl

checkCIF report

Comment top

Various aromatic carboxylic acid ligands are being used in designing versatile metal-organic frameworks (MOFs) having potential applications (Kuppler et al., 2009; Jahan et al., 2010; Armelao et al., 2010; Yashima et al., 2009). In present work, we report the synthesis and single crystal structure of a new aromatic dicarboxylic acid ligand namely 4-carboxymethoxy phenylacetic acid (I) containing two flexible carboxylic acid groups, obtained by the reaction of 4-hydroxyphenylacetic (Gracin et al., 2005) and chloroacetic acid (Sandhu et al., 1991).

The molecular structure of the title compound is presented in Fig.1. The carboxymethoxy group is almost parallel to the benzene ring with a dihedral angle of 11.4 (1)° between the two least-squares planes,while the acetic acid unit is almost perpendicular to the benzene ring, making a dihedral angle of 72.4 (2)°.In addtion, the moleculars were linked by the intermolecular O—H···O hydrogen bonding forming a three-dimensional network (Fig.2).

Related literature top

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 top

The solution of 4-hydroxyphenylacetic acid (1.522 g, 10.0 mmol) in water (10 ml) neutralized with NaOH (0.8 g, 20 mmol) was added to a 1:1 mixture of chloroacetic acid (3.78 g, 40 mmol) and NaOH (1.600 g, 40 mmol) with stirring to adjust the pH value of the mixture to ca 11 and refluxed at 90 ⁰C for 3 h. The pH value was adjusted to 2–3 with concentrated hydrochloric acid. While cooling the mixture to room temperature, a white precipitate was appeared rapidly. The solid was filtrated, washed by water. Single crystals suitable for X-ray diffraction were obtained in the mother liquid after evaporation within a few days.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I), the hydrogen bonds are depicted as green dashed lines.

2-[4-(Carboxymethyl)phenoxy]acetic acid top

Crystal data top

C₁₀H₁₀O₅	F(000) = 440
M_r = 210.18	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0425P)² + 0.2342P] where P = (F_o² + 2F_c²)/3
1315 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₀H₁₀O₅	V = 957.43 (7) Å³
M_r = 210.18	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.4640 (2) Å	µ = 0.12 mm⁻¹
b = 10.7798 (5) Å	T = 296 K
c = 16.2550 (7) Å	0.42 × 0.38 × 0.31 mm

Data collection top

Bruker APEXII area-detector diffractometer	1315 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1162 reflections with I > 2σ(I)
T_min = 0.95, T_max = 0.96	R_int = 0.049
11814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	Δρ_max = 0.14 e Å⁻³
1315 reflections	Δρ_min = −0.19 e Å⁻³
136 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y+1, z+1/2; (ii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀O₅
M_r	210.18
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.4640 (2), 10.7798 (5), 16.2550 (7)
V (Å³)	957.43 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.42 × 0.38 × 0.31

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.95, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	11814, 1315, 1162
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.07
No. of reflections	1315
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, −y+1, z+1/2; (ii) x+1/2, −y+1/2, −z+1.

References

Armelao, L., Quici, S., Barigelletti, F., Accorsi, G., Bottaro, G., Cavazzini, M. & Tondello, E.et al. (2010). Coord. Chem. Rev. 254, 487–505. Web of Science CrossRef CAS Google Scholar
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gracin, S. & Fischer, A. (2005). Acta Cryst. E61, o1919–o1920. Web of Science CSD CrossRef IUCr Journals Google Scholar
Jahan, M., Bao, Q. L., Yang, J. X. & Loh, K. P. (2010). J. Am. Chem. Soc. 132, 14487–14495. Web of Science CrossRef CAS PubMed Google Scholar
Kuppler, R. J., Timmons, D. J., Fang, Q. R., Li, J. R. & Makal, T. A. (2009). Coord. Chem. Rev. 253, 3042–3066. Web of Science CrossRef CAS Google Scholar
Sandhu, G. K., Sharma, N. & Tiekink, E. R. T. (1991). J. Organomet. Chem. 403, 119–131. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Goéttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yashima, E., Maeda, K., Iida, H., Furusho, Y. & Nagai, K. (2009). Chem. Rev. 109, 6102–6211. Web of Science CrossRef PubMed CAS Google Scholar

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CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o167

https://doi.org/10.1107/S1600536810051810

Open

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