2-(4-Hy­droxy­phen­oxy)propanoic acid

Gu, Z.; Jia, H.-S.; Cheng, W.

doi:10.1107/S1600536810049469

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3366

https://doi.org/10.1107/S1600536810049469

Open

access

2-(4-Hydroxyphenoxy)propanoic acid

Zhun Gu,^a ^* Hong-Sheng Jia ^a and Wei Cheng ^a

^aDepartment of Biological and Chemical Engineering, Chien-shiung Institute of Technology, Taicang 215411, Suzhou, People's Republic of China
^*Correspondence e-mail: Larry_18@163.com

(Received 29 October 2010; accepted 26 November 2010; online 30 November 2010)

In the title compound, C₉H₁₀O₄, the carboxyl group is oriented at a dihedral angle of 84.6 (3)° with respect to the benzene ring. In the crystal, molecules are linked via O—H⋯O hydrogen bonds.

Related literature

For the synthesis and applications of the title compound, see: Qin et al. (2004 ).

Experimental

Crystal data

C₉H₁₀O₄
M_r = 182.17
Monoclinic, P 2₁
a = 6.205 (1) Å
b = 11.853 (2) Å
c = 6.716 (1) Å
β = 114.78 (3)°
V = 448.47 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
924 measured reflections
924 independent reflections
829 reflections with I > 2σ(I)
R_int = 0.018
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.137
S = 1.02
924 reflections
121 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O3ⁱ	0.85	1.94	2.733 (6)	154
O4—H4B⋯O1ⁱⁱ	0.85 (4)	1.84 (4)	2.679 (6)	166 (4)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810049469/xu5075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810049469/xu5075Isup2.hkl

checkCIF report

Comment top

The title compound, (I), is an important intermediate of the highly active herbicide R-clodinafop-propargyl (Qin et al., 2004). We herein report its crystal structure.

The unit of the title compound, (I), (Fig. 1), contains one molecule and the bond lengths and angles (Table 1) are generally within normal ranges.

As can be seen from the packing diagram (Fig. 2), the intermolecular C—H···O hydrogen bonds (Table 2) link the molecules into three dimensional network, in which they may be effective in the stabilization of the crystal structure. Dipol-dipol and van der Waals interactions are also effective in the molecular packing.

Related literature top

For the synthesis and applications of the title compound, see: Qin et al. (2004).

Experimental top

The title compound was prepared by the literature method (Qin et al., 2004). The crystals were obtained by dissolving the title compound (0.3 g) in ethanol (50 ml) and evaporating the solvent slowly at room temperature for 15 d.

Structure description top

The title compound, (I), is an important intermediate of the highly active herbicide R-clodinafop-propargyl (Qin et al., 2004). We herein report its crystal structure.

The unit of the title compound, (I), (Fig. 1), contains one molecule and the bond lengths and angles (Table 1) are generally within normal ranges.

For the synthesis and applications of the title compound, see: Qin et al. (2004).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

2-(4-hydroxyphenoxy)propanoic acid top

Crystal data top

C₉H₁₀O₄	F(000) = 192
M_r = 182.17	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 6.205 (1) Å	θ = 10–13°
b = 11.853 (2) Å	µ = 0.11 mm⁻¹
c = 6.716 (1) Å	T = 298 K
β = 114.78 (3)°	Block, colorless
V = 448.47 (15) Å³	0.40 × 0.30 × 0.20 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.018
Radiation source: fine-focus sealed tube	θ_max = 25.9°, θ_min = 3.3°
Graphite monochromator	h = −7→6
ω/2θ scans	k = 0→14
924 measured reflections	l = 0→8
924 independent reflections	3 standard reflections every 200 reflections
829 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.05P)² + 0.6P] where P = (F_o² + 2F_c²)/3
924 reflections	(Δ/σ)_max < 0.001
121 parameters	Δρ_max = 0.24 e Å⁻³
3 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₉H₁₀O₄	V = 448.47 (15) Å³
M_r = 182.17	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.205 (1) Å	µ = 0.11 mm⁻¹
b = 11.853 (2) Å	T = 298 K
c = 6.716 (1) Å	0.40 × 0.30 × 0.20 mm
β = 114.78 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.018
924 measured reflections	3 standard reflections every 200 reflections
924 independent reflections	intensity decay: none
829 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.040	3 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.24 e Å⁻³
924 reflections	Δρ_min = −0.28 e Å⁻³
121 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	0.4177 (6)	0.4704 (4)	0.2174 (6)	0.0527 (10)
H1B	0.2918	0.4336	0.1940	0.079*
O2	0.8378 (5)	0.7346 (3)	0.9648 (5)	0.0431 (9)
O3	1.0305 (6)	0.9182 (3)	0.8307 (6)	0.0506 (10)
O4	1.3803 (5)	0.8319 (3)	0.9703 (6)	0.0487 (9)
C1	0.7253 (9)	0.5920 (5)	0.4402 (8)	0.0473 (13)
H1A	0.7872	0.5876	0.3360	0.057*
C2	0.5225 (8)	0.5344 (4)	0.4072 (8)	0.0381 (11)
C3	0.4318 (8)	0.5400 (4)	0.5642 (9)	0.0401 (11)
H3A	0.2959	0.4997	0.5449	0.048*
C4	0.5441 (8)	0.6055 (4)	0.7487 (8)	0.0373 (10)
H4A	0.4832	0.6092	0.8537	0.045*
C5	0.7453 (8)	0.6655 (5)	0.7789 (7)	0.0375 (10)
C6	0.8398 (9)	0.6568 (5)	0.6261 (8)	0.0505 (14)
H6A	0.9797	0.6943	0.6483	0.061*
C7	1.0878 (7)	0.7533 (4)	1.0603 (7)	0.0380 (11)
H7A	1.1701	0.6824	1.0626	0.046*
C8	1.1531 (10)	0.7924 (6)	1.2920 (8)	0.0538 (14)
H8A	1.1081	0.7359	1.3698	0.081*
H8B	1.0715	0.8616	1.2896	0.081*
H8C	1.3214	0.8047	1.3643	0.081*
C9	1.1595 (7)	0.8419 (4)	0.9378 (7)	0.0362 (10)
H4B	1.448 (5)	0.883 (3)	0.928 (8)	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0343 (17)	0.065 (3)	0.059 (2)	−0.0158 (18)	0.0201 (16)	−0.030 (2)
O2	0.0322 (16)	0.055 (2)	0.0446 (18)	−0.0092 (16)	0.0189 (14)	−0.0137 (17)
O3	0.0359 (17)	0.050 (2)	0.061 (2)	0.0072 (17)	0.0158 (16)	0.0174 (19)
O4	0.0335 (17)	0.048 (2)	0.070 (2)	0.0068 (17)	0.0267 (16)	0.0125 (19)
C1	0.052 (3)	0.055 (3)	0.048 (3)	−0.015 (3)	0.034 (2)	−0.008 (3)
C2	0.030 (2)	0.036 (2)	0.046 (3)	0.001 (2)	0.015 (2)	−0.011 (2)
C3	0.029 (2)	0.035 (2)	0.056 (3)	−0.002 (2)	0.018 (2)	0.000 (2)
C4	0.035 (2)	0.041 (3)	0.040 (2)	0.001 (2)	0.0199 (19)	−0.001 (2)
C5	0.033 (2)	0.046 (3)	0.035 (2)	−0.002 (2)	0.0162 (18)	−0.011 (2)
C6	0.047 (3)	0.064 (4)	0.051 (3)	−0.025 (3)	0.031 (2)	−0.011 (3)
C7	0.031 (2)	0.043 (3)	0.037 (2)	−0.006 (2)	0.0114 (18)	0.001 (2)
C8	0.055 (3)	0.066 (3)	0.039 (3)	−0.014 (3)	0.019 (2)	0.000 (3)
C9	0.028 (2)	0.043 (3)	0.035 (2)	0.003 (2)	0.0115 (17)	0.001 (2)

Geometric parameters (Å, º) top

O1—C2	1.389 (6)	C3—H3A	0.9300
O1—H1B	0.8500	C4—C5	1.376 (7)
O2—C5	1.399 (5)	C4—H4A	0.9300
O2—C7	1.426 (5)	C5—C6	1.382 (6)
O3—C9	1.221 (6)	C6—H6A	0.9300
O4—C9	1.300 (5)	C7—C8	1.508 (7)
O4—H4B	0.85 (4)	C7—C9	1.511 (6)
C1—C2	1.366 (6)	C7—H7A	0.9800
C1—C6	1.382 (7)	C8—H8A	0.9600
C1—H1A	0.9300	C8—H8B	0.9600
C2—C3	1.389 (6)	C8—H8C	0.9600
C3—C4	1.378 (7)

C2—O1—H1B	119.4	C1—C6—C5	119.7 (4)
C5—O2—C7	117.0 (4)	C1—C6—H6A	120.2
C9—O4—H4B	121 (3)	C5—C6—H6A	120.2
C2—C1—C6	120.9 (4)	O2—C7—C8	106.5 (4)
C2—C1—H1A	119.5	O2—C7—C9	112.1 (4)
C6—C1—H1A	119.5	C8—C7—C9	109.6 (4)
C1—C2—O1	117.8 (4)	O2—C7—H7A	109.6
C1—C2—C3	119.5 (4)	C8—C7—H7A	109.6
O1—C2—C3	122.7 (4)	C9—C7—H7A	109.6
C4—C3—C2	119.8 (4)	C7—C8—H8A	109.5
C4—C3—H3A	120.1	C7—C8—H8B	109.5
C2—C3—H3A	120.1	H8A—C8—H8B	109.5
C5—C4—C3	120.6 (4)	C7—C8—H8C	109.5
C5—C4—H4A	119.7	H8A—C8—H8C	109.5
C3—C4—H4A	119.7	H8B—C8—H8C	109.5
C4—C5—C6	119.5 (4)	O3—C9—O4	123.4 (4)
C4—C5—O2	116.2 (4)	O3—C9—C7	124.4 (4)
C6—C5—O2	124.3 (4)	O4—C9—C7	112.0 (4)

C6—C1—C2—O1	−179.6 (5)	C2—C1—C6—C5	−1.4 (9)
C6—C1—C2—C3	−0.8 (8)	C4—C5—C6—C1	2.9 (9)
C1—C2—C3—C4	1.5 (7)	O2—C5—C6—C1	−175.5 (5)
O1—C2—C3—C4	−179.8 (5)	C5—O2—C7—C8	−160.4 (5)
C2—C3—C4—C5	0.0 (7)	C5—O2—C7—C9	79.9 (6)
C3—C4—C5—C6	−2.2 (8)	O2—C7—C9—O3	26.7 (7)
C3—C4—C5—O2	176.3 (4)	C8—C7—C9—O3	−91.3 (6)
C7—O2—C5—C4	150.4 (4)	O2—C7—C9—O4	−157.2 (4)
C7—O2—C5—C6	−31.1 (7)	C8—C7—C9—O4	84.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3ⁱ	0.85	1.94	2.733 (6)	154
O4—H4B···O1ⁱⁱ	0.85 (4)	1.84 (4)	2.679 (6)	166 (4)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₀O₄
M_r	182.17
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	6.205 (1), 11.853 (2), 6.716 (1)
β (°)	114.78 (3)
V (Å³)	448.47 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	924, 924, 829
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.137, 1.02
No. of reflections	924
No. of parameters	121
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O3ⁱ	0.85	1.94	2.733 (6)	154
O4—H4B···O1ⁱⁱ	0.85 (4)	1.84 (4)	2.679 (6)	166 (4)

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+2, y+1/2, −z+1.

Acknowledgements

The authors thank Dr S. Liu of the Center of Testing and Analysis, Nanjing University, for the data collection.

References

Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Qin, Y.-H., Mo, W.-M., Sun, N. & Wang, W. (2004). Chin. J. Pestic. 43, 555–556. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar