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Volume 69 
Part 2 
Page o207  
February 2013  

Received 3 January 2013
Accepted 3 January 2013
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.052
wR = 0.134
Data-to-parameter ratio = 13.1
Details
Open access

Methyl 2,4-dihydroxy-5-(4-nitrobenzamido)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, C15H12N2O7, the dihedral angle between the aromatic rings is 4.58 (13)° and the nitro group is rotated from its attached ring by 18.07 (17)°. 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 [001] C(7) chains. The chains are linked by C-H...O interactions, forming a three-dimensional network, which incorporates R22(7) and R22(10) loops.

Related literature

For a related structure, see: Gorelik et al. (2010[Gorelik, T., Matveeva, G., Kolb, U., Schleuss, T., Kilbinger, A. F. M., van de Streek, J., Bohle, A. & Brunklaus, G. (2010). CrystEngComm, 12, 1824-1832.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O7

  • Mr = 332.27

  • Monoclinic, C 2/c

  • a = 30.412 (6) Å

  • b = 6.9325 (15) Å

  • c = 14.936 (3) Å

  • [beta] = 111.737 (8)°

  • V = 2925.0 (11) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.28 × 0.18 × 0.16 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.970, Tmax = 0.980

  • 10681 measured reflections

  • 2885 independent reflections

  • 1519 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.134

  • S = 0.98

  • 2885 reflections

  • 220 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.24 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 2.16 2.595 (3) 111
O3-H3A...O2 0.82 1.91 2.619 (3) 144
O4-H4...O5i 0.82 1.86 2.670 (2) 170
C8-H8A...O3ii 0.96 2.51 3.274 (4) 137
C12-H12...O7iii 0.93 2.38 3.297 (4) 171
C15-H15...O4ii 0.93 2.46 3.370 (3) 165
Symmetry codes: (i) [x, -y, z+{\script{1\over 2}}]; (ii) [x, -y, z-{\script{1\over 2}}]; (iii) [-x+1, y, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. 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: HB7022 ).


Acknowledgements

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

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gorelik, T., Matveeva, G., Kolb, U., Schleuss, T., Kilbinger, A. F. M., van de Streek, J., Bohle, A. & Brunklaus, G. (2010). CrystEngComm, 12, 1824-1832.  [ISI] [CSD] [CrossRef] [ChemPort]
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, o207  [ doi:10.1107/S160053681300024X ]

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