N-(2,4-Dinitro­phen­yl)-1,3-dimeth­oxy­isoindolin-2-amine

Du, N.-N.; Xu, H.-J.; Sheng, L.-Q.

doi:10.1107/S1600536811026316

Volume 67
Part 8
Page o1970
August 2011

Received 15 May 2011
Accepted 2 July 2011
Online 9 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.067
wR = 0.225
Data-to-parameter ratio = 13.4
Details

N-(2,4-Dinitrophenyl)-1,3-dimethoxyisoindolin-2-amine

Na-Na Du,^a Hua-Jie Xu ^a and Liang-Quan Sheng ^a ^*

^aDepartment of Chemistry, Fuyang Normal College, Fuyang, Anhui 236041, People's Republic of China
Correspondence e-mail: shenglq@fync.edu.cn

In the title compound, C₁₆H₁₆N₄O₆, the planes of the isoindole and dinitrobenzene groups make a dihedral angle between of 84.15 (8)°. The N atom of the isoindole group is displaced by 0.2937 (3) Å from the plane through the remaining atoms. An intramolecular N-HO interaction occurs. In the crystal, inversion dimers linked by pairs of N-HO hydrogen bonds occur.

Related literature

For general background to isoindoles and their derivatives, see: Mancilla et al. (2007); Toru et al. (1986). For the synthetic method and related structures, see: Maliha et al. (2008, 2009).

Experimental

Crystal data

C₁₆H₁₆N₄O₆
M_r = 360.33
Triclinic, $[P \overline 1]$
a = 7.727 (4) Å
b = 10.244 (5) Å
c = 11.326 (6) Å
= 86.076 (9)°
= 77.705 (8)°
= 70.794 (8)°
V = 827.2 (7) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 296 K
0.16 × 0.14 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.982, T_max = 0.989
4365 measured reflections
3181 independent reflections
2045 reflections with I > 2(I)
R_int = 0.062

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.225
S = 1.02
3181 reflections
237 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2AO1	0.86	1.96	2.593 (3)	130
N2-H2AO1ⁱ	0.86	2.27	3.032 (3)	148
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2248 ).

Acknowledgements

This work was supported by the Key Project of Science and Technology of Anhui, (grant No. 08010302218), the Natural Science Foundation of Anhui Provincial University (grant No. KJ2009A127) and the National Natural Science Foundation of China (grant No. 20971024).

References

Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Maliha, B., Hussain, I., Tahir, M. N., Tariq, M. I. & Siddiqui, H. L. (2008). Acta Cryst. E64, o626.
Maliha, B., Tariq, M. I., Tahir, M. N., Hussain, I. & Ali, M. (2009). Acta Cryst. E65, o41.
Mancilla, T., Correa-Basurto, J. C., Carbajal, K. S. A., Escalante, E. T. J. S. & Ferrara, J. T. (2007). J. Mex. Chem. Soc. E51, 96-102.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Toru, H., Eiki, N., Ryo, Y. & Shunichi, H. (1986). US Patent No. 4 595 409.

organic compounds