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Volume 69 
Part 3 
Page o443  
March 2013  

Received 15 January 2013
Accepted 19 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.098
Data-to-parameter ratio = 13.5
Details
Open access

2-(4-Acetamidophenoxy)-2-methylpropanoic acid

aFacultad de Farmacia, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001 Col., Chamilapa, CP 62100, Cuernavaca Mor., Mexico,bCentro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001 Col., Chamilpa, CP 62100, Cuernavaca Mor., Mexico, and cCentro de Investigaciones Químicas, Universidad A. del Estado de Hidalgo, Carr. Pachuca-Tulancingo Km. 4.5, Mineral de la reforma, CP 42184, Hidalgo, Mexico
Correspondence e-mail: tlahuext@ciq.uaem.mx

In the title compound, C12H15NO4, the dihedral angle between the acetamide group and the ring is 29.6 (2)(su?)°. In the crystal molecules are linked through N-H...O and O-H...O hydrogen bonds, thereby forming corrugated sheets propagating in the ac plane. These sheets are composed of R44(28) graph-set motifs.

Related literature

For related literature on analogous structures with analgesic and antidyslipidemic activities, see: Kis et al. (2005[Kis, B., Snipes, J. A. & Busija, D. W. (2005). J. Pharmacol. Exp. Ther. 315, 1-7.]); Navarrete-Vázquez et al. (2008[Navarrete-Vázquez, G., Torres-Gómez, H., Hidalgo-Figueroa, S. & Tlahuext, H. (2008). Acta Cryst. E64, o2261.], 2011[Navarrete-Vázquez, G., Torres-Gomez, H., Guerrero-Alvarez, J. & Tlahuext, H. (2011). J. Chem. Crystallogr. 41, 732-736.]); Thorp & Waring (1962[Thorp, J. M. & Waring, W. S. (1962). Nature, 194, 948-949.]); Miller & Spence (1998[Miller, D. B. & Spence, J. D. (1998). Clin. Pharmacokinet. 34, 155-162.]); Forcheron et al. (2002[Forcheron, F., Cachefo, A., Thevenon, S., Pinteur, C. & Beylot, M. (2002). Diabetes, 51, 3486-3491.]). For information on hydrogen bonding, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Jeffrey (1997[Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding, ch. 5. New York: Oxford University Press Inc.]); Desiraju (1996[Desiraju, G. R. (1996). Acc. Chem. Res. 29, 441-449.]).

[Scheme 1]

Experimental

Crystal data
  • C12H15NO4

  • Mr = 237.25

  • Monoclinic, P 21 /c

  • a = 8.3184 (4) Å

  • b = 13.1554 (6) Å

  • c = 12.0452 (5) Å

  • [beta] = 109.959 (5)°

  • V = 1238.96 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.19 × 0.14 × 0.13 mm

Data collection
  • Agilent Xcalibur Atlas Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.982, Tmax = 0.988

  • 34747 measured reflections

  • 2179 independent reflections

  • 1738 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.04

  • 2179 reflections

  • 161 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.87 (2) 2.21 (2) 3.081 (2) 174 (2)
O2-H2...O4ii 0.82 1.76 2.572 (2) 172
C2-H2A...O1iii 0.93 2.63 3.536 166
C5-H5...O3iv 0.93 2.69 3.333 127
Symmetry codes: (i) x+1, y, z; (ii) [x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+2, -z+2; (iv) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and DIAMOND (Crystal Impact, 2006[Crystal Impact (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2131 ).


Acknowledgements

This work was supported by the Consejo Nacional de Ciencia y Tecnología (CONACyT) under grant No. 100608.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Crystal Impact (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Desiraju, G. R. (1996). Acc. Chem. Res. 29, 441-449.  [CrossRef] [ChemPort] [ISI]
Forcheron, F., Cachefo, A., Thevenon, S., Pinteur, C. & Beylot, M. (2002). Diabetes, 51, 3486-3491.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding, ch. 5. New York: Oxford University Press Inc.
Kis, B., Snipes, J. A. & Busija, D. W. (2005). J. Pharmacol. Exp. Ther. 315, 1-7.  [CrossRef] [PubMed] [ChemPort]
Miller, D. B. & Spence, J. D. (1998). Clin. Pharmacokinet. 34, 155-162.  [ISI] [CrossRef] [ChemPort] [PubMed]
Navarrete-Vázquez, G., Torres-Gomez, H., Guerrero-Alvarez, J. & Tlahuext, H. (2011). J. Chem. Crystallogr. 41, 732-736.
Navarrete-Vázquez, G., Torres-Gómez, H., Hidalgo-Figueroa, S. & Tlahuext, H. (2008). Acta Cryst. E64, o2261.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thorp, J. M. & Waring, W. S. (1962). Nature, 194, 948-949.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o443  [ doi:10.1107/S1600536813004856 ]

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