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Volume 68 
Part 12 
Page o3490  
December 2012  

Received 22 November 2012
Accepted 25 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.143
Data-to-parameter ratio = 12.7
Details
Open access

4-Nitrophenyl 4-hydroxy-3-methylbenzoate

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India,bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India,cRaman Research Institute, C. V. Raman Avenue, Sadashivanagar, Bangalore 560 080, Karnataka, India, and dSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

The asymmetric unit of the title compound, C14H11NO5, contains two independent molecules in which the dihedral angles between the benzene rings are 89.27 (16) and 77.14 (12)°. In the crystal, molecules are linked by O-H...O hydrogen bonds, generating C(8) chains propagating in [010] for one molecule and [001] C(8) chains for the other. The chains are connected by C-H...O hydrogen bonds and [pi]-[pi] interactions [shortest centroid-centroid distance = 3.5908 (12)°], generating a three-dimensional network.

Related literature

For general background to aromatic nitro groups, see: Ghosh et al. (2012[Ghosh, P. P., Pal, G., Paul, S. & Das, A. R. (2012). Green Chem. 14, 2691-2698.]); Sugiyama et al. (2002[Sugiyama, T., Meng, J., Wen, Z., Li, J. & Matsuura, T. (2002). Mol. Cryst. Liq. Cryst. 389, 17-23.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11NO5

  • Mr = 273.24

  • Monoclinic, C 2/c

  • a = 42.313 (6) Å

  • b = 8.0047 (11) Å

  • c = 16.1078 (18) Å

  • [beta] = 105.819 (4)°

  • V = 5249.2 (12) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.24 × 0.20 × 0.16 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: [psi] scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.983

  • 28460 measured reflections

  • 4602 independent reflections

  • 3349 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.143

  • S = 1.02

  • 4602 reflections

  • 361 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1A-H1A...O2Ai 0.82 1.94 2.753 (2) 172
O1B-H1B...O2Bii 0.82 1.94 2.727 (3) 160
C7B-H7B1...O4Aiii 0.96 2.50 3.418 (3) 159
C12A-H12A...O2Ai 0.93 2.54 3.245 (2) 132
C19B-H19B...O5Aiv 0.93 2.58 3.476 (4) 163
Symmetry codes: (i) x, y-1, z; (ii) [x, -y+1, z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iv) [x, -y+2, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART 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.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6999 ).


Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, and G. B. Sadananda, Department of Studies and Research in Physics, U.C.S. Tumkur University, Tumkur for their help and suggestions.

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ghosh, P. P., Pal, G., Paul, S. & Das, A. R. (2012). Green Chem. 14, 2691-2698.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sugiyama, T., Meng, J., Wen, Z., Li, J. & Matsuura, T. (2002). Mol. Cryst. Liq. Cryst. 389, 17-23.  [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3490  [ doi:10.1107/S1600536812048271 ]

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