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

Tokutome, Y.; Okuno, T.

doi:10.1107/S1600536812051288

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 (C-C) = 0.002 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 13.6
Details

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

Yui Tokutome ^a and Tsunehisa Okuno ^a ^*

^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). 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). For general background, see Espinoza & Thornton (1994); Farrell et al. (1985); Chattanathan & Kalidas (1971); Southgate & Hall (1971); Stewart & O'Donnell (1964). For the first monoclinic polymorph, see: Wu et al. (2007).

Experimental

Crystal data

C₁₂H₇N₅O₈
M_r = 349.22
Monoclinic, P 2₁ /c
a = 12.827 (4) Å
b = 7.4997 (18) Å
c = 15.486 (4) Å
= 113.906 (4)°
V = 1362.0 (6) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.980, T_max = 0.991
10755 measured reflections
3119 independent reflections
2767 reflections with F² > 2(F²)
R_int = 0.025

Refinement

R[F² > 2(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
_max = 0.30 e Å^-3
_min = -0.24 e Å^-3

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXD (Schneider, et al., 2002); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

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.
Elliot, M. S. & Smith, F. J. (2000). Propell. Explos. Pyrot. 25, 31-36.
Espinoza, E. & Thornton, J. (1994). Anal. Chim. Acta, 288, 57-69.
Farrell, P. G., Terrier, F. & Schaal, R. (1985). Tetrahedron Lett. 26, 2435-2438.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Southgate, P. D. & Hall, D. S. (1971). Appl. Phys. Lett. 18, 456-459.
Stewart, R. & O'Donnell, J. P. (1964). Can. J. Chem. 42, 1694-1698.
Wu, D.-L., Jia, Z.-L., Shi, J.-P. & Lu, G.-Y. (2007). Acta Cryst. E63, o4194.

organic compounds