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Volume 69 
Part 2 
Page o152  
February 2013  

Received 11 December 2012
Accepted 19 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 93 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 13.6
Details
Open access

A second monoclinic polymorph of N-(2,4-dinitrophenyl)-2,4-dinitroaniline

aDepartment of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama, 640-8510, Japan
Correspondence e-mail: okuno@center.wakayama-u.ac.jp

The title compound, C12H7N5O8, was previously described in space group P21/n with Z = 4 [Wu et al. (2007[Wu, D.-L., Jia, Z.-L., Shi, J.-P. & Lu, G.-Y. (2007). Acta Cryst. E63, o4194.]). Acta Cryst. E63, o4194]. The current monoclinic P21/c polymorph was obtained from a mixed solution of dichloromethane and hexane. The dihedral angle between the benzene rings is 44.16 (5)°, smaller than in the previously reported polymorph [56.3 (2)°]. As a result of the steric hinderance of the nitro groups, hydrogen bonding is limited intramolecularly. The dihedral angles between the phenyl rings and their attached nitro groups are 18.97 (6) and 17.71 (5)° at the 2-position, and 18.52 (6) and 32.41 (6)° at the 4-position.

Related literature

For the preparation of the title compound, see: Elliot & Smith (2000[Elliot, M. S. & Smith, F. J. (2000). Propell. Explos. Pyrot. 25, 31-36.]). For general background, see Espinoza & Thornton (1994[Espinoza, E. & Thornton, J. (1994). Anal. Chim. Acta, 288, 57-69.]); Farrell et al. (1985[Farrell, P. G., Terrier, F. & Schaal, R. (1985). Tetrahedron Lett. 26, 2435-2438.]); Chattanathan & Kalidas (1971[Chattanathan, N. & Kalidas, C. (1971). Aust. J. Chem. 24, 83-88.]); Southgate & Hall (1971[Southgate, P. D. & Hall, D. S. (1971). Appl. Phys. Lett. 18, 456-459.]); Stewart & O'Donnell (1964[Stewart, R. & O'Donnell, J. P. (1964). Can. J. Chem. 42, 1694-1698.]). For the first monoclinic polymorph, see: Wu et al. (2007[Wu, D.-L., Jia, Z.-L., Shi, J.-P. & Lu, G.-Y. (2007). Acta Cryst. E63, o4194.]).

[Scheme 1]

Experimental

Crystal data
  • C12H7N5O8

  • Mr = 349.22

  • Monoclinic, P 21 /c

  • a = 12.827 (4) Å

  • b = 7.4997 (18) Å

  • c = 15.486 (4) Å

  • [beta] = 113.906 (4)°

  • V = 1362.0 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 93 K

  • 0.10 × 0.10 × 0.06 mm

Data collection
  • Rigaku Saturn724+ diffractometer

  • Absorption correction: numerical (NUMABS; Rigaku, 1999[Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.980, Tmax = 0.991

  • 10755 measured reflections

  • 3119 independent reflections

  • 2767 reflections with F2 > 2[sigma](F2)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.06

  • 3119 reflections

  • 230 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider, et al., 2002[Schneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772-1779.]); 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: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2093 ).


Acknowledgements

This work was supported by Research for Promoting Technological Seeds from the Japan Science and Technology Agency (JST).

References

Chattanathan, N. & Kalidas, C. (1971). Aust. J. Chem. 24, 83-88.  [CrossRef] [ChemPort]
Elliot, M. S. & Smith, F. J. (2000). Propell. Explos. Pyrot. 25, 31-36.  [CrossRef] [ChemPort]
Espinoza, E. & Thornton, J. (1994). Anal. Chim. Acta, 288, 57-69.  [CrossRef] [ChemPort] [ISI]
Farrell, P. G., Terrier, F. & Schaal, R. (1985). Tetrahedron Lett. 26, 2435-2438.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Rigaku (1999). NUMABS. Rigaku Corporation, Tokyo, Japan.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Schneider, T. R. & Sheldrick, G. M. (2002). Acta Cryst. D58, 1772-1779.  [ISI] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Southgate, P. D. & Hall, D. S. (1971). Appl. Phys. Lett. 18, 456-459.  [CrossRef] [ChemPort] [ISI]
Stewart, R. & O'Donnell, J. P. (1964). Can. J. Chem. 42, 1694-1698.  [CrossRef] [ChemPort] [ISI]
Wu, D.-L., Jia, Z.-L., Shi, J.-P. & Lu, G.-Y. (2007). Acta Cryst. E63, o4194.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o152  [ doi:10.1107/S1600536812051288 ]

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