3 (4 Carb­oxy­phen­­oxy)propionic acid

organic papers

o3420

10H10O5 doi:10.1107/S1600536806027577 Acta Cryst.(2006). E62, o3420–o3421 Acta Crystallographica Section E

Structure Reports Online

ISSN 1600-5368

3-(4-Carboxyphenoxy)propionic acid

Shan Gaoaand Seik Weng Ngb*

a_{College of Chemistry and Materials Science,}

Heilongjiang University, Harbin 150080, People’s Republic of China, andb_{Department of} Chemistry, University of Malaya, Kuala Lumpur 50603, Malaysia

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 295 K

Mean(C–C) = 0.002 A˚

Rfactor = 0.046

wRfactor = 0.153

Data-to-parameter ratio = 15.2

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 13 July 2006 Accepted 17 July 2006

#2006 International Union of Crystallography

All rights reserved

The molecules of the title compound, C10H10O5, are linked by

O—H O hydrogen bonds into a linear chain along [201].

Comment

The crystal structures of 2- and 3-carboxyphenoxyacetic acid have been reported previously. The 2-isomer exists as a zigzag chain polymer hydrogen-bonded through a pair of hydrogen bonds (Byriel et al., 1991), whereas the 3-isomer exists as a monohydrate that displays a three-dimensional hydrogen-bonded network (Gu et al., 2004). The structure of the 4-isomer has not been reported to date, as the compound does not furnish single crystals. Interest in the 4-isomer is extended to the title compound, (I), which has an extra methylene linkage.

The title compound is anhydrous (Fig. 1). A pair of hydrogen bonds (Table 1) links adjacent molecules into a linear chain along [201] (Fig. 2).

Experimental

4-Carboxyphenoxyacetic acid was synthesized in a manner analogous to that used for synthesizing 3-carboxyphenoxyacetic acid (Guet al., 2004), but with 4-hydroxybenzoic acid in place of 3-hydroxybenzoic acid and 3-chloropropionic acid in place of chloroacetic acid. Colourless crystals of (I) separated from the aqueous solution after several days.

Crystal data

C10H10O5

Mr= 210.18

Monoclinic,P21=c

a= 7.813 (4) A˚ b= 9.032 (6) A˚ c= 13.631 (9) A˚ = 94.92 (2) V= 958 (1) A˚3

Z= 4

Dx= 1.457 Mg m 3

MoKradiation = 0.12 mm1

T= 295 (2) K Plate, colourless 0.420.170.08 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

!scans

Absorption correction: multi-scan (ABSCOR; Higashi, 1995) Tmin= 0.722,Tmax= 0.937

(expected range = 0.763–0.991)

9176 measured reflections 2188 independent reflections 1359 reflections withI> 2(I) Rint= 0.035

Refinement

Refinement onF2

R[F2> 2(F2)] = 0.046 wR(F2_{) = 0.153}

S= 1.00 2188 reflections 144 parameters

H atoms treated by a mixture of independent and constrained refinement

w= 1/[2

(Fo2) + (0.0912P)2]

whereP= (Fo2+ 2Fc2)/3

(/)max= 0.001

max= 0.23 e A˚

3

min=0.20 e A˚

3

Table 1

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

O1—H1O O4i

0.83 (1) 1.82 (2) 2.618 (2) 162 (5) O5—H5O O2ii

0.84 (1) 1.85 (1) 2.676 (2) 173 (5)

Symmetry codes: (i)xþ1;yþ3 2;z

1

2; (ii)x1;yþ 3 2;zþ

1 2.

Carbon-bound H atoms were positioned geometrically, with C—H = 0.93 or 0.97 A˚ , and were included in the refinement in the riding-model approximation, withUiso(H) = 1.2Ueq(C). The acid H atoms were located in a difference Fourier map and were refined with a distance restraint of O—H = 0.82 (1) A˚ ; their displacement para-meters were freely refined.

Data collection: RAPID-AUTO(Rigaku, 1998); cell refinement:

RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:ORTEPII(Johnson, 1976); software used to prepare material for publication:SHELXL97.

The authors thank the National Natural Science Foundation of China (grant No. 20101003), the Scientific Fund for

Remarkable Teachers of Heilongjiang Province (grant No. 1054 G036) and the University of Malaya for supporting this study.

References

Byriel, K. A., Smith, D. E. & Kennard, C. H. L. (1991).Aust. J. Chem.44, 1459– 1464.

Gu, C.-S., Liu, J.-W., Huo, L.-H., Zhao, H., Zhao, J.-G. & Gao, S. (2004).Acta Cryst.E60, o760–o761.

Higashi, T. (1995).ABSCOR. Rigaku Corporation, Tokyo, Japan.

Johnson, C. K. (1976).ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.

Rigaku (1998).RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc. The Woodlands,

Texas, USA.

Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Go¨ttingen, Germany.

Figure 1

The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as spheres of arbitrary radii.

Figure 2

supporting information

sup-1 Acta Cryst. (2006). E62, o3420–o3421

supporting information

Acta Cryst. (2006). E62, o3420–o3421 [https://doi.org/10.1107/S1600536806027577]

3-(4-Carboxyphenoxy)propionic acid

Shan Gao and Seik Weng Ng

3-(4-Carboxyphenoxy)propionic acid

Crystal data

C10H10O5

Mr = 210.18 Monoclinic, P21/c Hall symbol: -P 2ybc

a = 7.813 (4) Å

b = 9.032 (6) Å

c = 13.631 (9) Å

β = 94.92 (2)°

V = 958 (1) Å3

Z = 4

F(000) = 440

Dx = 1.457 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 5947 reflections

θ = 3.0–27.5°

µ = 0.12 mm−1

T = 295 K Plate, colourless 0.42 × 0.17 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ω scans

Absorption correction: multi-scan (ABSCOR; Higashi, 1995)

Tmin = 0.722, Tmax = 0.937

9176 measured reflections 2188 independent reflections 1359 reflections with I > 2σ(I)

Rint = 0.035

θmax = 27.5°, θmin = 3.0°

h = −10→8

k = −11→11

l = −17→17

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.046}

wR(F2_{) = 0.153}

S = 1.00 2188 reflections 144 parameters 2 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2_(F

o2) + (0.0912P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001

Δρmax = 0.23 e Å−3 Δρmin = −0.20 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2₎

x y z Uiso*/Ueq

O1 0.7570 (2) 0.4302 (2) 0.2068 (1) 0.0650 (5)

O3 0.3768 (2) 0.4912 (2) 0.3441 (1) 0.0454 (4)

O4 −0.0388 (2) 0.9064 (2) 0.6092 (1) 0.0628 (5)

O5 −0.2541 (2) 0.8132 (2) 0.5119 (1) 0.0608 (5)

C1 0.5972 (2) 0.4410 (2) 0.1810 (1) 0.0402 (4)

C2 0.4826 (2) 0.3328 (2) 0.2264 (2) 0.0461 (5)

C3 0.3230 (2) 0.4016 (2) 0.2608 (2) 0.0432 (5)

C4 0.2544 (2) 0.5667 (2) 0.3894 (1) 0.0380 (4)

C5 0.0802 (2) 0.5598 (2) 0.3607 (1) 0.0426 (5)

C6 −0.0322 (2) 0.6431 (2) 0.4101 (1) 0.0434 (5)

C7 0.0258 (2) 0.7344 (2) 0.4873 (1) 0.0392 (4)

C8 0.2008 (2) 0.7377 (2) 0.5162 (1) 0.0441 (5)

C9 0.3143 (2) 0.6542 (2) 0.4687 (1) 0.0441 (5)

C10 −0.0943 (2) 0.8237 (2) 0.5398 (1) 0.0432 (5)

H1O 0.804 (7) 0.494 (4) 0.174 (4) 0.21 (2)*

H5O −0.325 (4) 0.856 (5) 0.544 (3) 0.18 (2)*

H2A 0.5466 0.2857 0.2820 0.055*

H2B 0.4493 0.2564 0.1785 0.055*

H3A 0.2656 0.4617 0.2089 0.052*

H3B 0.2442 0.3255 0.2790 0.052*

H5 0.0396 0.4995 0.3086 0.051*

H6 −0.1493 0.6379 0.3913 0.052*

H8 0.2414 0.7976 0.5686 0.053*

H9 0.4308 0.6560 0.4894 0.053*

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

O1 0.0463 (8) 0.0904 (12) 0.0569 (10) −0.0101 (8) −0.0033 (7) 0.0161 (9)

O2 0.0430 (8) 0.0649 (10) 0.0663 (10) 0.0041 (7) 0.0112 (7) 0.0194 (8)

O3 0.0385 (7) 0.0534 (8) 0.0446 (8) 0.0016 (6) 0.0059 (6) −0.0088 (6)

O4 0.0530 (9) 0.0779 (11) 0.0566 (10) 0.0052 (8) 0.0004 (7) −0.0228 (8)

O5 0.0387 (8) 0.0706 (10) 0.0733 (11) 0.0035 (7) 0.0067 (7) −0.0202 (8)

C1 0.0406 (9) 0.0434 (10) 0.0368 (10) 0.0016 (8) 0.0047 (8) −0.0052 (8)

C2 0.0492 (11) 0.0406 (11) 0.0497 (12) −0.0001 (9) 0.0117 (9) −0.0005 (9)

C3 0.0409 (10) 0.0468 (10) 0.0425 (11) −0.0033 (8) 0.0065 (8) −0.0028 (8)

C4 0.0360 (9) 0.0422 (10) 0.0361 (10) −0.0008 (8) 0.0049 (8) 0.0023 (8)

C5 0.0373 (9) 0.0488 (11) 0.0410 (10) −0.0017 (8) −0.0001 (8) −0.0058 (9)

C6 0.0330 (9) 0.0523 (11) 0.0446 (11) 0.0001 (8) 0.0010 (8) 0.0005 (9)

C7 0.0374 (10) 0.0423 (10) 0.0384 (10) 0.0004 (8) 0.0057 (8) 0.0017 (8)

C8 0.0401 (10) 0.0500 (11) 0.0420 (11) −0.0022 (8) 0.0011 (8) −0.0060 (9)

C9 0.0336 (9) 0.0525 (11) 0.0455 (11) −0.0014 (8) −0.0003 (8) −0.0027 (9)

C10 0.0390 (10) 0.0495 (11) 0.0413 (10) −0.0007 (9) 0.0037 (9) 0.0016 (9)

Geometric parameters (Å, º)

O1—C1 1.271 (2) C7—C10 1.469 (3)

O2—C1 1.241 (2) C8—C9 1.369 (3)

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sup-3 Acta Cryst. (2006). E62, o3420–o3421

O3—C3 1.428 (2) O5—H5O 0.84 (1)

O4—C10 1.253 (2) C2—H2A 0.97

O5—C10 1.277 (2) C2—H2B 0.97

C1—C2 1.494 (3) C3—H3A 0.97

C2—C3 1.504 (3) C3—H3B 0.97

C4—C5 1.385 (2) C5—H5 0.93

C4—C9 1.387 (3) C6—H6 0.93

C5—C6 1.375 (3) C8—H8 0.93

C6—C7 1.382 (3) C9—H9 0.93

C7—C8 1.390 (2)

C4—O3—C3 118.3 (1) C10—O5—H5O 119 (3)

O2—C1—O1 123.1 (2) C1—C2—H2A 108.8

O2—C1—C2 120.3 (2) C3—C2—H2A 108.8

O1—C1—C2 116.4 (2) C1—C2—H2B 108.8

C1—C2—C3 113.7 (2) C3—C2—H2B 108.8

O3—C3—C2 106.7 (2) H2A—C2—H2B 107.7

O3—C4—C5 124.0 (2) O3—C3—H3A 110.4

O3—C4—C9 115.7 (2) C2—C3—H3A 110.4

C5—C4—C9 120.2 (2) O3—C3—H3B 110.4

C6—C5—C4 119.4 (2) C2—C3—H3B 110.4

C5—C6—C7 121.1 (2) H3A—C3—H3B 108.6

C6—C7—C8 118.6 (2) C6—C5—H5 120.3

C6—C7—C10 121.1 (2) C4—C5—H5 120.3

C8—C7—C10 120.3 (2) C5—C6—H6 119.4

C9—C8—C7 121.1 (2) C7—C6—H6 119.4

C8—C9—C4 119.6 (2) C9—C8—H8 119.5

O4—C10—O5 122.4 (2) C7—C8—H8 119.5

O4—C10—C7 120.0 (2) C8—C9—H9 120.2

O5—C10—C7 117.6 (2) C4—C9—H9 120.2

C1—O1—H1O 106 (4)

O2—C1—C2—C3 −48.1 (3) C5—C6—C7—C10 179.8 (2)

O1—C1—C2—C3 135.7 (2) C6—C7—C8—C9 0.9 (3)

C4—O3—C3—C2 179.9 (2) C10—C7—C8—C9 179.4 (2)

C1—C2—C3—O3 −69.8 (2) C7—C8—C9—C4 1.1 (3)

C3—O3—C4—C5 1.3 (3) O3—C4—C9—C8 177.7 (2)

C3—O3—C4—C9 −178.8 (2) C5—C4—C9—C8 −2.3 (3)

O3—C4—C5—C6 −178.6 (2) C6—C7—C10—O4 −179.6 (2)

C9—C4—C5—C6 1.5 (3) C8—C7—C10—O4 1.9 (3)

C4—C5—C6—C7 0.5 (3) C6—C7—C10—O5 0.4 (3)

C5—C6—C7—C8 −1.7 (3) C8—C7—C10—O5 −178.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

O5—H5O···O2ii _{0.84 (1) 1.85 (1) 2.676 (2) 173 (5)}