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The title compound, C9H10O3, also known as (m-methoxy­phenyl)­acetic acid, has been found to crystallize in the monoclinic space group P21/c at room temperature. It is the starting material for the synthesis of a large number of 1,2,3,4-tetra­hydro­iso­quinoline compounds [Nagarajan et al. (1985). Indian J. Chem. Sect. B, 24, 83–97]. The compound forms dimers in the crystalline state, with O—H...O hydrogen bonds between the carboxyl groups, across a crystallographic centre of symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012102/cf6192sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802012102/cf6192Isup2.hkl
Contains datablock I

CCDC reference: 193761

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.117
  • Data-to-parameter ratio = 11.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

(3-methoxyphenyl) acetic acid top
Crystal data top
C9H10O3F(000) = 352
Mr = 166.17Dx = 1.317 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3478 reflections
a = 16.266 (3) Åθ = 2.4–21.3°
b = 5.1024 (11) ŵ = 0.10 mm1
c = 10.095 (2) ÅT = 293 K
β = 90.73 (1)°Prism, colourless
V = 837.8 (3) Å30.40 × 0.35 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
1310 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 26.4°, θmin = 1.3°
φ and ω scansh = 2020
6276 measured reflectionsk = 66
1714 independent reflectionsl = 1212
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) = 0.117H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.077P)2 + 0.0041P]
where P = (Fo2 + 2Fc2)/3
1714 reflections(Δ/σ)max = 0.003
149 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.16 e Å3
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
O20.00838 (6)0.7832 (2)0.60937 (12)0.0731 (4)
H20.01850.71490.54930.110*
O30.41770 (7)0.5419 (2)0.63480 (11)0.0737 (4)
O10.08963 (6)0.4467 (2)0.57274 (11)0.0714 (4)
C10.07511 (8)0.6489 (3)0.63060 (13)0.0495 (3)
C40.27706 (8)0.6621 (3)0.68455 (12)0.0487 (3)
H40.27640.79240.62010.058*
C50.34717 (8)0.5141 (3)0.70481 (13)0.0511 (4)
C30.20771 (8)0.6175 (3)0.75966 (12)0.0493 (3)
C60.34836 (9)0.3195 (3)0.80052 (15)0.0612 (4)
H60.39500.21700.81340.073*
C80.21015 (10)0.4272 (3)0.85640 (14)0.0615 (4)
H80.16440.39820.90860.074*
C20.13036 (9)0.7699 (3)0.73258 (15)0.0588 (4)
H2A0.10040.78720.81450.071*
H2B0.14510.94470.70350.071*
C70.28013 (11)0.2797 (3)0.87604 (15)0.0676 (5)
H70.28110.15130.94140.081*
C90.42115 (11)0.7507 (3)0.5427 (2)0.0815 (5)
H9A0.37790.73100.47800.122*
H9B0.47330.74850.49930.122*
H9C0.41460.91430.58840.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0590 (7)0.0726 (7)0.0871 (8)0.0166 (5)0.0215 (5)0.0202 (6)
O30.0543 (7)0.0820 (8)0.0850 (8)0.0105 (5)0.0109 (5)0.0118 (6)
O10.0562 (6)0.0795 (8)0.0780 (7)0.0159 (5)0.0183 (5)0.0306 (6)
C10.0419 (7)0.0573 (8)0.0493 (7)0.0005 (6)0.0024 (5)0.0014 (6)
C40.0533 (8)0.0482 (7)0.0444 (6)0.0007 (6)0.0058 (5)0.0013 (5)
C50.0499 (8)0.0530 (8)0.0501 (7)0.0013 (6)0.0057 (6)0.0037 (6)
C30.0475 (7)0.0537 (7)0.0465 (7)0.0063 (6)0.0071 (5)0.0094 (6)
C60.0640 (10)0.0567 (8)0.0623 (8)0.0035 (7)0.0177 (7)0.0029 (7)
C80.0626 (9)0.0702 (10)0.0517 (8)0.0193 (8)0.0005 (7)0.0006 (7)
C20.0506 (8)0.0656 (9)0.0602 (8)0.0027 (6)0.0023 (6)0.0155 (7)
C70.0833 (12)0.0611 (9)0.0580 (8)0.0110 (8)0.0152 (8)0.0138 (7)
C90.0743 (11)0.0746 (11)0.0963 (13)0.0069 (9)0.0283 (10)0.0097 (10)
Geometric parameters (Å, º) top
O2—C11.2991 (16)C3—C21.5011 (19)
O2—H20.820C6—C71.370 (2)
O3—C51.3626 (17)C6—H60.930
O3—C91.415 (2)C8—C71.377 (2)
O1—C11.2104 (16)C8—H80.930
C1—C21.4917 (19)C2—H2A0.970
C4—C51.3809 (19)C2—H2B0.970
C4—C31.3860 (19)C7—H70.930
C4—H40.930C9—H9A0.960
C5—C61.385 (2)C9—H9B0.960
C3—C81.377 (2)C9—H9C0.960
C1—O2—H2109.5C7—C8—H8119.9
C5—O3—C9117.39 (12)C3—C8—H8119.9
O1—C1—O2122.53 (12)C1—C2—C3114.05 (11)
O1—C1—C2124.49 (12)C1—C2—H2A108.7
O2—C1—C2112.98 (12)C3—C2—H2A108.7
C5—C4—C3120.38 (12)C1—C2—H2B108.7
C5—C4—H4119.8C3—C2—H2B108.7
C3—C4—H4119.8H2A—C2—H2B107.6
O3—C5—C4124.42 (12)C6—C7—C8120.86 (14)
O3—C5—C6115.61 (13)C6—C7—H7119.6
C4—C5—C6119.96 (13)C8—C7—H7119.6
C8—C3—C4119.16 (13)O3—C9—H9A109.5
C8—C3—C2120.72 (13)O3—C9—H9B109.5
C4—C3—C2120.10 (12)H9A—C9—H9B109.5
C7—C6—C5119.37 (14)O3—C9—H9C109.5
C7—C6—H6120.3H9A—C9—H9C109.5
C5—C6—H6120.3H9B—C9—H9C109.5
C7—C8—C3120.25 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.872.687 (2)173
Symmetry code: (i) x, y+1, z+1.
 

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