3-Methyl-1-phenyl-4-[(Z)-phen­yl(4-acetamido­anilino)methyl­idene]-1H-pyrazol-5(4H)-one

Zhi, L.-H.; Wang, Y.

doi:10.1107/S1600536812026840

Volume 68
Part 7
Page o2132
July 2012

Received 9 June 2012
Accepted 13 June 2012
Online 20 June 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.053
wR = 0.169
Data-to-parameter ratio = 18.5
Details

3-Methyl-1-phenyl-4-[(Z)-phenyl(4-acetamidoanilino)methylidene]-1H-pyrazol-5(4H)-one

Li-Hua Zhi ^a and Yuan Wang ^a ^*

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
Correspondence e-mail: wangyuan08@hpu.edu.cn

In the title compound, C₂₅H₂₂N₄O₂, the dihedral angles between the central pyrazole ring and the phenyl and benzene rings are 37.01 (3), 75.58 (7) and 49.67 (8)°. An intramolecular N-HO hydrogen bond generates an S(6) motif. In the crystal, N-HO hydrogen bonds link molecules into a zigzag chain extended along the b axis.

Related literature

For the synthesis of Schiff bases derived from 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone and the DNA binding properties of their transition metal complexes, see: Wang & Yang (2005). For the structure of (E,E)-3,3'-dimethyl-1,1'-diphenyl-4,4'-{[3-azapentane-1,5-diylbis(azanediyl)]-bis(phenylmethylidyne)}di-1H-pyrazol-5(4H)-one, see: Zhang et al. (2010).

Experimental

Crystal data

C₂₅H₂₂N₄O₂
M_r = 410.47
Monoclinic, P 2₁ /n
a = 7.1800 (4) Å
b = 11.0562 (7) Å
c = 27.3932 (16) Å
= 95.138 (4)°
V = 2165.8 (2) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 296 K
0.19 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.985, T_max = 0.988
19323 measured reflections
5168 independent reflections
3047 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.169
S = 1.02
5168 reflections
280 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H4AO1ⁱ	0.86	2.05	2.874 (2)	161
N3-H3AO1	0.86	1.96	2.696 (2)	143
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: GK2501 ).

Acknowledgements

The authors are grateful for financial support from the Natural Science Foundation of Henan Province (No.12B150011).

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Y. & Yang, Z.-Y. (2005). Transition Met. Chem. 30, 902-906.
Zhang, Z.-P., Wang, Y., Li, X.-X. & Li, Y.-W. (2010). Acta Cryst. E66, o3326.

organic compounds