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Volume 69 
Part 4 
Page o526  
April 2013  

Received 2 March 2013
Accepted 4 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 130 K
Mean [sigma](C-C) = 0.002 Å
R = 0.048
wR = 0.122
Data-to-parameter ratio = 15.3
Details
Open access

N-(4-Hydroxyphenyl)-4-nitrobenzamide

aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan,bUniversität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany, and cDepartment of Materials and Metallurgical Engineering (DMME), Pakistan Institute of Engineering and Applied Sciences (PIEAS), Islamabad 45650, Pakistan
Correspondence e-mail: humaira_siddiqi@yahoo.com

The molecular structure of the title compound, C13H10N2O4, shows an almost planar conformation as the benzene rings make a dihedral angle of 2.31 (7)°. The nitro group lies in plane with the benzamide ring, with a C-C-N-O torsion angle of 0.6 (2)°. In the crystal, N-H...O and O-H...O hydrogen bonds link molecules into sheets stacked along [10-1].

Related literature

For background to aromatic polyimides, see: Sheng et al. (2009[Sheng, S.-R., Pei, X.-L., Huang, Z.-Z., Liu, X.-L. & Song, C.-S. (2009). Eur. Polym. J. 45, 230-236.]). For the solubilizing role of ether and amide groups in polyimides, see: Litvinov et al. (2010[Litvinov, V. M., Persyn, O., Miri, V. & Lefebvre, J. M. (2010). Macromolecules, 43, 7668-7679.]). For a related structure, see: Raza et al. (2010[Raza, A. R., Nisar, B. & Tahir, M. N. (2010). Acta Cryst. E66, o2435.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10N2O4

  • Mr = 258.23

  • Monoclinic, P 21 /c

  • a = 7.5187 (5) Å

  • b = 12.5695 (9) Å

  • c = 11.7932 (8) Å

  • [beta] = 90.033 (2)°

  • V = 1114.53 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 130 K

  • 0.50 × 0.16 × 0.12 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.944, Tmax = 0.986

  • 10323 measured reflections

  • 2657 independent reflections

  • 2255 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.122

  • S = 1.12

  • 2657 reflections

  • 174 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4...O1i 0.84 1.94 2.7803 (17) 175
N1-H1A...O3ii 0.88 2.33 3.1664 (18) 159
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5203 ).


Acknowledgements

The contribution to this project of the Higher Education Commission of Pakistan by providing financial assistance through the International Research Support Initiative Programme (IRSIP) is acknowledged by the authors.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Litvinov, V. M., Persyn, O., Miri, V. & Lefebvre, J. M. (2010). Macromolecules, 43, 7668-7679.  [ISI] [CrossRef] [ChemPort]
Raza, A. R., Nisar, B. & Tahir, M. N. (2010). Acta Cryst. E66, o2435.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sheng, S.-R., Pei, X.-L., Huang, Z.-Z., Liu, X.-L. & Song, C.-S. (2009). Eur. Polym. J. 45, 230-236.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o526  [ doi:10.1107/S1600536813006132 ]

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