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Volume 69 
Part 12 
Page o1747  
December 2013  

Received 14 September 2013
Accepted 24 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 15.4
Details
Open access

1-Nitro-4-(4-nitro­phen­oxy)benzene: a second monoclinic polymorph

aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and bChemistry Department, Loughborough University, Loughborough, LE11 3TU, England
Correspondence e-mail: zareenakhter@yahoo.com

In the title compound, C12H8N2O5, the aromatic rings are inclined to one another by 56.14 (7)°. The nitro groups are inclined by to the benzene rings to which they are attached by 3.86 (17) and 9.65 (15)°. In the crystal, mol­ecules are linked by C-H...O hydrogen bonds, forming a three-dimensional structure. The title compound is a new monoclinic polymorph, crystallizing in space group P21/c. The first polymorph crystallized in space group C2/c and the mol­ecule possesses twofold rotation symmetry. Two low-temperature structures of this polymorph (150 K and 100 K, respectively) have been reported [Meciarova et al. (2004). Private Communication (refcode IXOGAD). CCDC, Cambridge, England, and Dey & Desiraju (2005). Chem. Commun. pp. 2486-2488].

Related literature

For the crystal structure of the monoclinic C2/c polymorph of the title compound, see: Meciarova et al. (2004[Meciarova, M., Toma, S., Podlesna, J., Kiripolsky, M. & Cisarova, I. (2004). Private Communication (refcode IXOGAD). CCDC, Cambridge, England.]); Dey & Desiraju (2005[Dey, A. & Desiraju, G. R. (2005). Chem. Commun. pp. 2486-2488.]).

[Scheme 1]

Experimental

Crystal data
  • C12H8N2O5

  • Mr = 260.20

  • Monoclinic, P 21 /c

  • a = 8.1114 (5) Å

  • b = 11.8942 (7) Å

  • c = 12.3970 (7) Å

  • [beta] = 106.402 (1)°

  • V = 1147.37 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 150 K

  • 0.36 × 0.35 × 0.25 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2012[Sheldrick, G. M. (2012). SADABS. University of Göttingen, Germany.]) Tmin = 0.794, Tmax = 0.862

  • 10808 measured reflections

  • 2641 independent reflections

  • 2149 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.104

  • S = 1.06

  • 2641 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C13-H13...O21i 0.95 2.56 3.4413 (18) 153
C23-H23...O11ii 0.95 2.31 3.1933 (18) 154
C26-H26...O12iii 0.95 2.42 3.227 (2) 143
Symmetry codes: (i) x, y-1, z; (ii) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) -x, -y, -z.

Data collection: APEX2 (Bruker 1998[Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker 1998[Bruker (1998). APEX2 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: SHELXL2012 (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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2235 ).


Acknowledgements

The authors are grateful to the Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and the Chemistry Department, Loughborough University, Loughborough, UK, for providing laboratory and analytical facilities.

References

Bruker (1998). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dey, A. & Desiraju, G. R. (2005). Chem. Commun. pp. 2486-2488.  [CSD] [CrossRef]
Meciarova, M., Toma, S., Podlesna, J., Kiripolsky, M. & Cisarova, I. (2004). Private Communication (refcode IXOGAD). CCDC, Cambridge, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2012). SADABS. University of Göttingen, Germany.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1747  [ doi:10.1107/S1600536813029346 ]

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