(4Z)-4-[(4-Chloro­anilino)(phen­yl)methyl­ene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Chi, X.; Xiao, J.; Yin, Y.; Xia, M.

doi:10.1107/S1600536809054816

Volume 66
Part 1
Page o249
January 2010

Received 11 December 2009
Accepted 20 December 2009
Online 24 December 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.055
wR = 0.142
Data-to-parameter ratio = 13.5
Details

(4Z)-4-[(4-Chloroanilino)(phenyl)methylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Xiaodong Chi,^a Jing Xiao,^a Yuhong Yin ^a and Min Xia ^a ^*

^aDepartment of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China
Correspondence e-mail: xiamin@hzcnc.com

The title compound, C₂₃H₁₈ClN₃O, was synthesized by the reaction of 4-chloroaniline and 4-benzoyl-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one. The terminal benzene rings are twisted at dihedral angles of 48.3 (2), 71.4 (2) and 36.1 (2)° with respect to the central eight-atom methylpyrazolone/aminomethylene unit. An intramolecular N-HO hydrogen bond stabilizes the planar conformation [mean deviation = 0.0398 (5) Å] of the central unit, generating an S(6) ring motif. The crystal packing is stabilized by van der Waals forces.

Related literature

For the properties of [beta] -enaminoketones, see: Li et al. (2000); Zhang et al. (2003, 2008); Cingolani et al. (2006); Marchetti et al. (2005). For the preparation of [beta] -enaminoketones, see: Yang et al. (2004). For graph-set notation, see: Bernstein et al. (1995).

Experimental

Crystal data

C₂₃H₁₈ClN₃O
M_r = 387.85
Triclinic, $[P \overline 1]$
a = 7.4305 (15) Å
b = 11.069 (2) Å
c = 13.518 (3) Å
= 109.28 (3)°
= 98.78 (3)°
= 105.08 (3)°
V = 978.0 (5) Å³
Z = 2
Mo K radiation
= 0.21 mm^-1
T = 293 K
0.34 × 0.31 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.921, T_max = 0.985
7818 measured reflections
3506 independent reflections
2198 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.142
S = 1.05
3506 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.61 e Å^-3
_min = -0.56 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1	0.93 (3)	1.87 (3)	2.701 (3)	146 (2)

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2229 ).

Acknowledgements

We are grateful for financial support from the Xinmiao Project in the Science and Technology Department of Zhejiang Province (2008R40G2060018).

References

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organic compounds