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Volume 69 
Part 2 
Page o221  
February 2013  

Received 5 January 2013
Accepted 5 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.006 Å
R = 0.065
wR = 0.168
Data-to-parameter ratio = 13.1
Details
Open access

Methyl 2,4-dihydroxy-5-(2-methylpropanamido)benzoate

aUniversity of Peshawar, Institute of Chemical Sciences, Peshawar, Pakistan,bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C12H15NO5, the dihedral angle between the benzene ring and the C atoms of the terminal isopropyl group is 83.48 (16)°. Intramolecular N-H...O and O-H...O hydrogen bonds generate S(5) and S(6) rings, respectively. In the crystal, molecules are linked by O-H...O hydrogen bonds, generating C(7) chains propagating in [001]. Weak aromatic [pi]-[pi] stacking [centroid-centroid separation = 3.604 (3) Å] is also observed.

Related literature

For related structures, see: Chen et al. (2011[Chen, G., Gao, H., Tang, J., Huang, Y., Chen, Y., Wang, Y., Zhao, H., Lin, H., Xie, Q., Hong, K., Li, J. & Yao, X. (2011). Chem. Pharm. Bull. 59, 447-451.]); Naz et al. (2013[Naz, S. S., Islam, N. U., Tahir, M. N. & Shah, M. R. (2013). Acta Cryst. E69, o207.]).

[Scheme 1]

Experimental

Crystal data
  • C12H15NO5

  • Mr = 253.25

  • Monoclinic, C 2/c

  • a = 22.732 (4) Å

  • b = 8.2338 (16) Å

  • c = 14.743 (3) Å

  • [beta] = 113.506 (9)°

  • V = 2530.4 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 296 K

  • 0.26 × 0.16 × 0.14 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.981, Tmax = 0.985

  • 8480 measured reflections

  • 2218 independent reflections

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

  • Rint = 0.090

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.168

  • S = 0.96

  • 2218 reflections

  • 169 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O4 0.86 2.19 2.604 (4) 109
O3-H3...O2 0.82 1.87 2.595 (4) 146
O4-H4...O5i 0.82 1.820 2.633 (4) 174
Symmetry code: (i) [x, -y+2, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7024 ).


Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha. Pakistan.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, G., Gao, H., Tang, J., Huang, Y., Chen, Y., Wang, Y., Zhao, H., Lin, H., Xie, Q., Hong, K., Li, J. & Yao, X. (2011). Chem. Pharm. Bull. 59, 447-451.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Naz, S. S., Islam, N. U., Tahir, M. N. & Shah, M. R. (2013). Acta Cryst. E69, o207.  [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]


Acta Cryst (2013). E69, o221  [ doi:10.1107/S1600536813000457 ]

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