(Z)-4-[(2-Amino-4,5-dichloro­anilino)(phenyl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Zou, D.; Lü, X.; Zhao, S.; Liu, X.

doi:10.1107/S160053681204086X

Volume 68
Part 11
Page o3148
November 2012

Received 1 August 2012
Accepted 28 September 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.007 Å
R = 0.060
wR = 0.189
Data-to-parameter ratio = 13.2
Details

(Z)-4-[(2-Amino-4,5-dichloroanilino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Dan Zou,^a Xingqiang Lü,^a Shunsheng Zhao ^b and Xiangrong Liu ^b ^*

^aCollege of Chemical Engineering, Northwest University, Xi'an 710069, Shannxi, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Xian University of Science and Technology, Xi'an 710054, Shannxi, People's Republic of China
Correspondence e-mail: lvxq@nwu.edu.cn

The molecule of the title compound, C₂₃H₁₈Cl₂N₄O, assumes a non-planar conformation in which the pyrazolone ring forms dihedral angles of 32.61 (19), 76.73 (14) and 52.57 (19)° with the three benzene rings. The secondary amino group is involved in an intramolecular N-HO hydrogen bond. In the crystal, molecules are linked by pairs of N-HO hydrogen bonds, forming inversion dimers. An offset stacking interaction is observed between the chloro-substituted benzene rings protruding on both sides of these dimers [centroid-centroid distance = 3.862 (1) Å].

Related literature

For related structures, see: Lu et al. (2011). For bond-length data, see: Allen et al. (1987). For the catalytic properties of asymmetric Schiff bases, see: Caboni et al. (2012). For the synthesis, see: Hennig & Mann (1988).

Experimental

Crystal data

C₂₃H₁₈Cl₂N₄O
M_r = 437.31
Triclinic, $[P \overline 1]$
a = 8.0653 (16) Å
b = 10.931 (2) Å
c = 13.851 (3) Å
= 111.627 (3)°
= 90.775 (3)°
= 110.226 (3)°
V = 1051.1 (4) Å³
Z = 2
Mo K radiation
= 0.33 mm^-1
T = 296 K
0.30 × 0.21 × 0.18 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.857, T_max = 1.000
5308 measured reflections
3688 independent reflections
1992 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.060
wR(F²) = 0.189
S = 1.03
3688 reflections
280 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.51 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO1	0.86	2.01	2.735 (4)	141
N4-H4BO1ⁱ	0.88 (2)	2.18 (2)	3.022 (5)	162 (4)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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 and local programs.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2067 ).

Acknowledgements

The project was supported by the National Natural Science Foundation of China (program Nos. 21103135 and 21073139), the Natural Science Basic Research Plan in Shaanxi Province of China (program No. 2011JQ2011) and the Scientific Research Program Funded by Shaanxi Provincial Education Department (program No.12 J K0622).

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-S19.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Caboni, L., Kinsella, G. K., Blanco, F., Fayne, D., Jagoe, W. N., Carr, M., Williams, D. C., Meegan, M. J. & Lloyd, D. G. (2012). J. Med. Chem. 55, 1635-1644.
Hennig, L. & Mann, G. (1988). Z. Chem. 28, 364-365.
Lu, R., Xia, H., Lü, X. & Zhao, S. (2011). Acta Cryst. E67, o2701.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds