1,3-Bis[(4-nitro­benzyl­idene)amino­oxy]propane

Dong, W.-K.; Sun, Y.-X.; Tong, J.-F.; Zhao, H.-H.; Wang, L.

doi:10.1107/S1600536809031316

Volume 65
Part 9
Pages o2141-o2142
September 2009

Received 13 July 2009
Accepted 8 August 2009
Online 12 August 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.039
wR = 0.094
Data-to-parameter ratio = 7.1
Details

1,3-Bis[(4-nitrobenzylidene)aminooxy]propane

Wen-Kui Dong,^a ^* Yin-Xia Sun,^a Jun-Feng Tong,^a Hai-Hong Zhao ^a and Li Wang ^a

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
Correspondence e-mail: dongwk@mail.lzjtu.cn

The complete molecule of title compound, C₁₇H₁₆N₄O₆, is generated by a crystallographic twofold axis. Within the molecule, the two benzene units are approximately perpendicular, making a dihedral angle of 85.91 (4)°. In the crystal, molecules are linked into a three-dimensional network by C-HO hydrogen bonds and short OO and NO interactions, with distances of 2.998 (2) and 2.968 (3) Å, respectively.

Related literature

For general background to Schiff base complexes and their applications, see: Niederhoffer et al. (1984); Zhang et al. (1990); Tisato et al. (1994); Lacroix (2001); Sundari et al. (1997); Koehler et al. (1964); Cordes & Jencks (1962); Akine et al. (2006). For related structures, see: Fun et al. (2008a,b); Kia et al. (2009); Shi et al. (2007); Ren et al. (2008); Ding et al. (2009); Dong et al. (2008a). For a related Schiff base bisoxime compound synthesized using a similar route, see: Dong et al. (2008b).

Experimental

Crystal data

C₁₇H₁₆N₄O₆
M_r = 372.34
Monoclinic, C 2
a = 29.005 (3) Å
b = 4.7878 (5) Å
c = 6.3579 (7) Å
= 99.144 (1)°
V = 871.71 (16) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 298 K
0.45 × 0.17 × 0.06 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.952, T_max = 0.993
2321 measured reflections
872 independent reflections
675 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.094
S = 0.96
872 reflections
123 parameters
1 restraint
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O3ⁱ	0.93	2.40	3.206 (4)	145
C9-H9O3ⁱ	0.93	2.63	3.395 (4)	139
C9-H9O2ⁱⁱ	0.93	2.71	3.374 (4)	129
Symmetry codes: (i) x, y-1, z+1; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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: FL2256 ).

Acknowledgements

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0904-11) and the `Jing Lan' Talent Engineering Funds of Lanzhou Jiaotong University, which are gratefully acknowledged.

References

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organic compounds