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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810049469/xu5075sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810049469/xu5075Isup2.hkl
Contains datablock I

CCDC reference: 803332

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.040
  • wR factor = 0.137
  • Data-to-parameter ratio = 7.6

checkCIF/PLATON results

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Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.64 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 7 PLAT918_ALERT_3_C Reflection(s) # with I(obs) much smaller I(calc) 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.94 From the CIF: _reflns_number_total 924 Count of symmetry unique reflns 923 Completeness (_total/calc) 100.11% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3 PLAT791_ALERT_4_G Note: The Model has Chirality at C7 (Verify) R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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.

Refinement top

The carboxyl H atom was located in a difference Fourier map and positional parameters were refined, Uiso(H) = 1.5Ueq(O). Other H atoms were positioned geometrically with C—H = 0.93-0.98 Å and O—H = 0.85 Å, and refined in ride mode with Uiso(H) = 1.5Ueq(C,O) for methyl H and hydroxyl H atoms and 1.2Ueq(C) for the other H atoms.

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.

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.

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
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.
2-(4-hydroxyphenoxy)propanoic acid top
Crystal data top
C9H10O4F(000) = 192
Mr = 182.17Dx = 1.349 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 6.205 (1) Åθ = 10–13°
b = 11.853 (2) ŵ = 0.11 mm1
c = 6.716 (1) ÅT = 298 K
β = 114.78 (3)°Block, colorless
V = 448.47 (15) Å30.40 × 0.30 × 0.20 mm
Z = 2
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.018
Radiation source: fine-focus sealed tubeθmax = 25.9°, θmin = 3.3°
Graphite monochromatorh = 76
ω/2θ scansk = 014
924 measured reflectionsl = 08
924 independent reflections3 standard reflections every 200 reflections
829 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.05P)2 + 0.6P]
where P = (Fo2 + 2Fc2)/3
924 reflections(Δ/σ)max < 0.001
121 parametersΔρmax = 0.24 e Å3
3 restraintsΔρmin = 0.28 e Å3
Crystal data top
C9H10O4V = 448.47 (15) Å3
Mr = 182.17Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.205 (1) ŵ = 0.11 mm1
b = 11.853 (2) ÅT = 298 K
c = 6.716 (1) Å0.40 × 0.30 × 0.20 mm
β = 114.78 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.018
924 measured reflections3 standard reflections every 200 reflections
924 independent reflections intensity decay: none
829 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0403 restraints
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.24 e Å3
924 reflectionsΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
O10.4177 (6)0.4704 (4)0.2174 (6)0.0527 (10)
H1B0.29180.43360.19400.079*
O20.8378 (5)0.7346 (3)0.9648 (5)0.0431 (9)
O31.0305 (6)0.9182 (3)0.8307 (6)0.0506 (10)
O41.3803 (5)0.8319 (3)0.9703 (6)0.0487 (9)
C10.7253 (9)0.5920 (5)0.4402 (8)0.0473 (13)
H1A0.78720.58760.33600.057*
C20.5225 (8)0.5344 (4)0.4072 (8)0.0381 (11)
C30.4318 (8)0.5400 (4)0.5642 (9)0.0401 (11)
H3A0.29590.49970.54490.048*
C40.5441 (8)0.6055 (4)0.7487 (8)0.0373 (10)
H4A0.48320.60920.85370.045*
C50.7453 (8)0.6655 (5)0.7789 (7)0.0375 (10)
C60.8398 (9)0.6568 (5)0.6261 (8)0.0505 (14)
H6A0.97970.69430.64830.061*
C71.0878 (7)0.7533 (4)1.0603 (7)0.0380 (11)
H7A1.17010.68241.06260.046*
C81.1531 (10)0.7924 (6)1.2920 (8)0.0538 (14)
H8A1.10810.73591.36980.081*
H8B1.07150.86161.28960.081*
H8C1.32140.80471.36430.081*
C91.1595 (7)0.8419 (4)0.9378 (7)0.0362 (10)
H4B1.448 (5)0.883 (3)0.928 (8)0.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0343 (17)0.065 (3)0.059 (2)0.0158 (18)0.0201 (16)0.030 (2)
O20.0322 (16)0.055 (2)0.0446 (18)0.0092 (16)0.0189 (14)0.0137 (17)
O30.0359 (17)0.050 (2)0.061 (2)0.0072 (17)0.0158 (16)0.0174 (19)
O40.0335 (17)0.048 (2)0.070 (2)0.0068 (17)0.0267 (16)0.0125 (19)
C10.052 (3)0.055 (3)0.048 (3)0.015 (3)0.034 (2)0.008 (3)
C20.030 (2)0.036 (2)0.046 (3)0.001 (2)0.015 (2)0.011 (2)
C30.029 (2)0.035 (2)0.056 (3)0.002 (2)0.018 (2)0.000 (2)
C40.035 (2)0.041 (3)0.040 (2)0.001 (2)0.0199 (19)0.001 (2)
C50.033 (2)0.046 (3)0.035 (2)0.002 (2)0.0162 (18)0.011 (2)
C60.047 (3)0.064 (4)0.051 (3)0.025 (3)0.031 (2)0.011 (3)
C70.031 (2)0.043 (3)0.037 (2)0.006 (2)0.0114 (18)0.001 (2)
C80.055 (3)0.066 (3)0.039 (3)0.014 (3)0.019 (2)0.000 (3)
C90.028 (2)0.043 (3)0.035 (2)0.003 (2)0.0115 (17)0.001 (2)
Geometric parameters (Å, º) top
O1—C21.389 (6)C3—H3A0.9300
O1—H1B0.8500C4—C51.376 (7)
O2—C51.399 (5)C4—H4A0.9300
O2—C71.426 (5)C5—C61.382 (6)
O3—C91.221 (6)C6—H6A0.9300
O4—C91.300 (5)C7—C81.508 (7)
O4—H4B0.85 (4)C7—C91.511 (6)
C1—C21.366 (6)C7—H7A0.9800
C1—C61.382 (7)C8—H8A0.9600
C1—H1A0.9300C8—H8B0.9600
C2—C31.389 (6)C8—H8C0.9600
C3—C41.378 (7)
C2—O1—H1B119.4C1—C6—C5119.7 (4)
C5—O2—C7117.0 (4)C1—C6—H6A120.2
C9—O4—H4B121 (3)C5—C6—H6A120.2
C2—C1—C6120.9 (4)O2—C7—C8106.5 (4)
C2—C1—H1A119.5O2—C7—C9112.1 (4)
C6—C1—H1A119.5C8—C7—C9109.6 (4)
C1—C2—O1117.8 (4)O2—C7—H7A109.6
C1—C2—C3119.5 (4)C8—C7—H7A109.6
O1—C2—C3122.7 (4)C9—C7—H7A109.6
C4—C3—C2119.8 (4)C7—C8—H8A109.5
C4—C3—H3A120.1C7—C8—H8B109.5
C2—C3—H3A120.1H8A—C8—H8B109.5
C5—C4—C3120.6 (4)C7—C8—H8C109.5
C5—C4—H4A119.7H8A—C8—H8C109.5
C3—C4—H4A119.7H8B—C8—H8C109.5
C4—C5—C6119.5 (4)O3—C9—O4123.4 (4)
C4—C5—O2116.2 (4)O3—C9—C7124.4 (4)
C6—C5—O2124.3 (4)O4—C9—C7112.0 (4)
C6—C1—C2—O1179.6 (5)C2—C1—C6—C51.4 (9)
C6—C1—C2—C30.8 (8)C4—C5—C6—C12.9 (9)
C1—C2—C3—C41.5 (7)O2—C5—C6—C1175.5 (5)
O1—C2—C3—C4179.8 (5)C5—O2—C7—C8160.4 (5)
C2—C3—C4—C50.0 (7)C5—O2—C7—C979.9 (6)
C3—C4—C5—C62.2 (8)O2—C7—C9—O326.7 (7)
C3—C4—C5—O2176.3 (4)C8—C7—C9—O391.3 (6)
C7—O2—C5—C4150.4 (4)O2—C7—C9—O4157.2 (4)
C7—O2—C5—C631.1 (7)C8—C7—C9—O484.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O3i0.851.942.733 (6)154
O4—H4B···O1ii0.85 (4)1.84 (4)2.679 (6)166 (4)
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC9H10O4
Mr182.17
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)6.205 (1), 11.853 (2), 6.716 (1)
β (°) 114.78 (3)
V3)448.47 (15)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
924, 924, 829
Rint0.018
(sin θ/λ)max1)0.615
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.137, 1.02
No. of reflections924
No. of parameters121
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1B···O3i0.851.942.733 (6)154
O4—H4B···O1ii0.85 (4)1.84 (4)2.679 (6)166 (4)
Symmetry codes: (i) x+1, y1/2, z+1; (ii) x+2, y+1/2, z+1.
 

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