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Volume 68 
Part 1 
Page o213  
January 2012  

Received 20 November 2011
Accepted 12 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.057
wR = 0.158
Data-to-parameter ratio = 12.8
Details
Open access

2-(2-Nitroanilino)benzoic acid

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: zhuhjnjut@hotmail.com

In the title compound, C13H10N2O4, the nitro N atom deviates by 0.031 (2) Å from the plane of the benzene ring to which it is attached. The aromatic rings are oriented at a dihedral angle of 50.6 (1)°. An intramolecular N-H...O hydrogen bond occurs. In the crystal, inversion dimers are formed by pairs of O-H...O interactions.

Related literature

For the use of the title compound as an intermediate in the synthesis pharmacologically important compounds, see: Kelleher et al. (2007[Kelleher, J. M., Mc Auliffe, M. T., Moynihan, H. A. & Mullins, M. D. (2007). Arkivoc, xvi, 209-226.]). For the synthesis, see: Rewcastle et al. (1987[Rewcastle, G. W., Denny, W. A. & Baguley, B. C. (1987). J. Med. Chem. 30, 843-851.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10N2O4

  • Mr = 258.23

  • Monoclinic, P 21 /c

  • a = 7.1840 (14) Å

  • b = 21.546 (4) Å

  • c = 7.9070 (16) Å

  • [beta] = 101.62 (3)°

  • V = 1198.8 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 4704 measured reflections

  • 2209 independent reflections

  • 1437 reflections with I > 2[sigma](I)

  • Rint = 0.046

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.158

  • S = 1.01

  • 2209 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O3 0.86 2.02 2.636 (3) 128
O1-H1C...O2i 0.82 1.82 2.636 (2) 176
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: SET4 (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); data reduction: MolEN (Harms & Wocadlo,1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2343 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1994). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Kelleher, J. M., Mc Auliffe, M. T., Moynihan, H. A. & Mullins, M. D. (2007). Arkivoc, xvi, 209-226.
Rewcastle, G. W., Denny, W. A. & Baguley, B. C. (1987). J. Med. Chem. 30, 843-851.  [CrossRef] [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o213  [ doi:10.1107/S1600536811053529 ]

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