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

Naz, S.S.; Islam, N.U.; Tahir, M.N.; Shah, M.R.

doi:10.1107/S1600536813000457

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 (C-C) = 0.006 Å
R = 0.065
wR = 0.168
Data-to-parameter ratio = 13.1
Details

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

Syeda Sohaila Naz,^a Nazar Ul Islam,^a M. Nawaz Tahir ^b ^* and Muhammad Raza Shah ^c

^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-HO and O-HO hydrogen bonds generate S(5) and S(6) rings, respectively. In the crystal, molecules are linked by O-HO 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); Naz et al. (2013).

Experimental

Crystal data

C₁₂H₁₅NO₅
M_r = 253.25
Monoclinic, C 2/c
a = 22.732 (4) Å
b = 8.2338 (16) Å
c = 14.743 (3) Å
= 113.506 (9)°
V = 2530.4 (9) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.981, T_max = 0.985
8480 measured reflections
2218 independent reflections
950 reflections with I > 2(I)
R_int = 0.090

Refinement

R[F² > 2(F²)] = 0.065
wR(F²) = 0.168
S = 0.96
2218 reflections
169 parameters
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O4	0.86	2.19	2.604 (4)	109
O3-H3O2	0.82	1.87	2.595 (4)	146
O4-H4O5ⁱ	0.82	1.820	2.633 (4)	174
Symmetry code: (i) $[x, -y+2, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) 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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Naz, S. S., Islam, N. U., Tahir, M. N. & Shah, M. R. (2013). Acta Cryst. E69, o207.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds