(E)-1,5-Dimethyl-4-[3-(4-nitro­benz­yloxy)benzyl­ideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Liu, S.-X.; Tian, X.; Zhen, X.-L.; Li, Z.-C.; Han, J.-R.

doi:10.1107/S1600536808035046

Volume 64
Part 11
Page o2245
November 2008

Received 27 October 2008
Accepted 28 October 2008
Online 31 October 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R = 0.046
wR = 0.125
Data-to-parameter ratio = 13.0
Details

(E)-1,5-Dimethyl-4-[3-(4-nitrobenzyloxy)benzylideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Shou-Xin Liu,^a ^* Xia Tian,^b Xiao-Li Zhen,^b Zhen-Chao Li ^b and Jian-Rong Han ^b ⁺

^aCollege of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China, and ^bCollege of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
Correspondence e-mail: liu_shouxin@163.com

In the title compound, C₂₅H₂₂N₄O₄, the central benzene ring, makes dihedral angles of 74.35 (6), 17.01 (8) and 62.19 (7)°, respectively, with the nitrobenzyl ring, the pyrazolone ring and the terminal phenyl ring. Intermolecular C-HO hydrogen bonds help to consolidate the crystal packing.

Related literature

For the potential applications of Schiff bases, see: Jones et al. (1979); Larson & Pecoraro (1991); Santos et al. (2001). For a related structure, see: Han & Zhen (2005). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₂₅H₂₂N₄O₄
M_r = 442.47
Triclinic, $[P \overline 1]$
a = 8.003 (2) Å
b = 9.798 (3) Å
c = 14.425 (5) Å
= 90.844 (5)°
= 92.310 (6)°
= 101.202 (6)°
V = 1108.4 (6) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 294 (2) K
0.20 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.956, T_max = 0.991
5780 measured reflections
3898 independent reflections
2302 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.125
S = 1.01
3898 reflections
300 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7BO4ⁱ	0.97	2.50	3.293 (3)	139
Symmetry code: (i) -x+2, -y+1, -z.

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); 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: HB2829 ).

Acknowledgements

The project was supported by the Foundation of the Education Department of Hebei Province (grant No. 606022).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Han, J.-R. & Zhen, X.-L. (2005). Acta Cryst. E61, o3815-o3816.
Jones, R. D., Summerville, D. A. & Basolo, F. (1979). Chem. Rev. 17, 139-179.
Larson, E. J. & Pecoraro, V. L. (1991). J. Am. Chem. Soc. 113, 3810-3818.
Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds