Download citation
Download citation
link to html
2-Methoxy-2-phenyl­acetic acid, C9H10O3, forms helical columns of single enantiomers linked by hydrogen bonding between the acidic proton of one mol­ecule and the methoxy O atom of a neighbouring mol­ecule, to give an overall racemic structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028228/fl6069sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028228/fl60691sup2.hkl
Contains datablock 1

CCDC reference: 232161

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.055
  • wR factor = 0.174
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON2002 (Spek, 2002); software used to prepare material for publication: SHELXL97.

2-Methoxy-2-phenylacetic acid top
Crystal data top
C9H10O3Dx = 1.335 Mg m3
Mr = 166.17Melting point = 342–344 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.093 (3) ÅCell parameters from 877 reflections
b = 7.123 (2) Åθ = 3.3–20.9°
c = 12.270 (3) ŵ = 0.10 mm1
β = 110.40 (1)°T = 299 K
V = 826.8 (4) Å3Prism, colourless
Z = 40.60 × 0.48 × 0.16 mm
F(000) = 352
Data collection top
Oxford Diffraction Xcalibur CCD
diffractometer
994 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 26.4°, θmin = 4.3°
Detector resolution: Sapphire CCD detector pixels mm-1h = 1212
Rotation method data acquisition using ω scansk = 88
4076 measured reflectionsl = 158
1665 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.174 w = 1/[σ2(Fo2) + (0.1149P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max = 0.045
1665 reflectionsΔρmax = 0.25 e Å3
128 parametersΔρmin = 0.23 e Å3
0 restraintsExtinction correction: SHELXL97 and Larson (1970), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.051 (11)
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
C10.7339 (3)0.2807 (3)0.8075 (2)0.0435 (6)
C20.7180 (3)0.1526 (3)0.90045 (18)0.0406 (6)
H20.63140.07840.86760.049*
C30.7100 (3)0.2644 (3)1.00170 (18)0.0383 (6)
C40.5909 (3)0.2602 (4)1.0316 (2)0.0482 (7)
H40.516 (3)0.180 (4)0.991 (2)0.058*
C50.5848 (4)0.3663 (4)1.1237 (2)0.0590 (8)
H50.500 (3)0.362 (4)1.140 (3)0.071*
C60.6954 (4)0.4765 (4)1.1850 (2)0.0598 (9)
H60.685 (3)0.555 (4)1.248 (3)0.072*
C70.8143 (4)0.4805 (4)1.1567 (2)0.0577 (8)
H70.892 (3)0.559 (4)1.197 (2)0.069*
C80.8218 (3)0.3738 (4)1.0657 (2)0.0501 (7)
H80.899 (3)0.380 (4)1.045 (2)0.060*
C90.8223 (3)0.1216 (3)1.0022 (2)0.0543 (8)
H9A0.74140.19560.95950.065*
H9B0.81080.07451.07170.065*
H9C0.90570.19811.02270.065*
O10.6155 (2)0.3658 (3)0.75018 (15)0.0576 (6)
H1O0.637 (3)0.442 (4)0.700 (3)0.069*
O20.8413 (2)0.3008 (3)0.78952 (17)0.0765 (8)
O30.83571 (17)0.0315 (2)0.93238 (13)0.0443 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0482 (16)0.0471 (14)0.0372 (12)0.0001 (12)0.0175 (11)0.0026 (11)
C20.0431 (15)0.0417 (13)0.0398 (12)0.0017 (11)0.0179 (11)0.0004 (10)
C30.0497 (15)0.0345 (12)0.0347 (11)0.0029 (11)0.0197 (11)0.0051 (10)
C40.0564 (18)0.0458 (14)0.0487 (14)0.0032 (13)0.0263 (13)0.0071 (12)
C50.073 (2)0.0583 (17)0.0619 (16)0.0150 (16)0.0442 (16)0.0109 (15)
C60.096 (3)0.0469 (16)0.0440 (14)0.0132 (16)0.0333 (16)0.0007 (12)
C70.078 (2)0.0479 (16)0.0437 (14)0.0015 (14)0.0169 (14)0.0055 (12)
C80.0551 (18)0.0533 (15)0.0460 (13)0.0023 (13)0.0228 (12)0.0020 (12)
C90.070 (2)0.0479 (15)0.0507 (14)0.0064 (13)0.0275 (13)0.0123 (12)
O10.0569 (13)0.0685 (13)0.0525 (10)0.0106 (10)0.0255 (9)0.0218 (9)
O20.0549 (14)0.1081 (18)0.0738 (13)0.0062 (12)0.0317 (11)0.0421 (12)
O30.0531 (12)0.0416 (9)0.0426 (9)0.0036 (8)0.0222 (8)0.0011 (7)
Geometric parameters (Å, º) top
C1—O21.187 (3)C5—H50.94 (3)
C1—O11.306 (3)C6—C71.361 (4)
C1—C21.512 (3)C6—H60.99 (3)
C2—O31.408 (3)C7—C81.373 (4)
C2—C31.502 (3)C7—H70.95 (3)
C2—H20.9800C8—H80.90 (3)
C3—C81.371 (4)C9—O31.422 (3)
C3—C41.374 (3)C9—H9A0.9600
C4—C51.379 (4)C9—H9B0.9600
C4—H40.94 (3)C9—H9C0.9600
C5—C61.357 (4)O1—H1O0.90 (3)
O2—C1—O1124.6 (2)C5—C6—C7119.9 (3)
O2—C1—C2123.8 (2)C5—C6—H6117.9 (17)
O1—C1—C2111.6 (2)C7—C6—H6122.1 (17)
O3—C2—C3112.23 (18)C6—C7—C8119.9 (3)
O3—C2—C1106.16 (18)C6—C7—H7121.7 (17)
C3—C2—C1110.75 (19)C8—C7—H7118.4 (17)
O3—C2—H2109.2C3—C8—C7120.8 (3)
C3—C2—H2109.2C3—C8—H8119.2 (18)
C1—C2—H2109.2C7—C8—H8119.9 (18)
C8—C3—C4118.8 (2)O3—C9—H9A109.5
C8—C3—C2120.3 (2)O3—C9—H9B109.5
C4—C3—C2120.9 (2)H9A—C9—H9B109.5
C3—C4—C5120.0 (3)O3—C9—H9C109.5
C3—C4—H4119.4 (16)H9A—C9—H9C109.5
C5—C4—H4120.5 (16)H9B—C9—H9C109.5
C6—C5—C4120.5 (3)C1—O1—H1O104.9 (18)
C6—C5—H5122.2 (18)C2—O3—C9112.89 (17)
C4—C5—H5117.3 (19)
O2—C1—C2—O316.5 (3)C2—C3—C4—C5179.0 (2)
O1—C1—C2—O3163.59 (19)C3—C4—C5—C60.5 (4)
O2—C1—C2—C3105.6 (3)C4—C5—C6—C71.0 (4)
O1—C1—C2—C374.3 (3)C5—C6—C7—C80.4 (4)
O3—C2—C3—C855.9 (3)C4—C3—C8—C71.3 (4)
C1—C2—C3—C862.5 (3)C2—C3—C8—C7178.3 (2)
O3—C2—C3—C4124.5 (2)C6—C7—C8—C30.8 (4)
C1—C2—C3—C4117.1 (2)C3—C2—O3—C970.6 (2)
C8—C3—C4—C50.7 (4)C1—C2—O3—C9168.23 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O3i0.90 (3)1.85 (3)2.725 (2)162 (3)
O1—H1O···O2i0.90 (3)2.57 (3)3.190 (3)127 (2)
Symmetry code: (i) x+3/2, y+1/2, z+3/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds