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

Xu, H.-Z.; Yang, Y.-X.; Yan, J.; Zhu, Y.-Q.

doi:10.1107/S160053681001384X

Volume 66
Part 6
Page o1309
June 2010

Received 5 April 2010
Accepted 14 April 2010
Online 12 May 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.047
wR = 0.133
Data-to-parameter ratio = 16.2
Details

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

Hai-Zhen Xu,^a ^* Yan-Xia Yang,^b Jing Yan ^a and You-Quan Zhu ^c ^*

^aCollege of Chemistry, Tianjin Normal University, 393 Binshuixi Road, Xiqing District, Tianjin 300387, People's Republic of China,^bNankai High School, 100 Sima Road, Nankai District, Tianjin 300100, People's Republic of China, and ^cState Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
Correspondence e-mail: hsxyxhz@mail.tjnu.edu.cn, zyq8165@nankai.edu.cn

The title compound, C₂₀H₁₉N₃O, exists in a keto-enamine tautomeric form. The pyrazolone ring makes dihedral angles of 20.52 (10) and 77.73 (5)° with the two phenyl rings and an intramolecular N-HO hydrogen bond occurs. A weak intermolecular C-HO hydrogen bond is observed in the crystal structure. The allyl group is disordered over two positions, with site-occupancy factors of 0.533 (5) and 0.467 (5).

Related literature

For the analgesic activity of metal complexes with 1-phenyl-3-methyl-4-benzoylpyrazolon-5-one, see: Li et al. (1997); Liu et al. (1980); Zhou et al. (1999). For related structures, see: Bao et al. (2004); Sun et al. (2007); Zhu et al. (2005).

Experimental

Crystal data

C₂₀H₁₉N₃O
M_r = 317.38
Triclinic, $[P \overline 1]$
a = 9.295 (1) Å
b = 9.8440 (12) Å
c = 10.0670 (14) Å
= 86.175 (8)°
= 89.280 (9)°
= 74.329 (7)°
V = 884.90 (19) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.22 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn724 CCD camera diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2009) T_min = 0.984, T_max = 0.988
10726 measured reflections
3910 independent reflections
2135 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.133
S = 0.94
3910 reflections
242 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3O1	1.06 (2)	1.75 (2)	2.687 (2)	145 (2)
C17-H17O1ⁱ	0.95	2.41	3.345 (2)	168
Symmetry code: (i) -x, -y+2, -z+2.

Data collection: CrystalClear (Rigaku, 2009); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2009); software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2538 ).

Acknowledgements

The authors gratefully acknowledge the financial support of the National Natural Science Foundation of China (grant No. 20772066).

References

Bao, F., Lü, X.-Q., Qiao, Y.-Q., Wu, Q. & Ng, S. W. (2004). Acta Cryst. E60, o2191-o2192.
Li, J.-Z., Yu, W.-J. & Du, X.-Y. (1997). Chin. J. Appl. Chem. 14, 98-100.
Liu, J.-M., Yang, R.-D. & Ma, T.-R. (1980). Chem. J. Chin. Univ. 1, 23-29.
Rigaku (2009). CrystalClear and CrystalStrcuture. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, Y.-F., Li, J.-K., Wu, R.-T. & Zheng, Z.-B. (2007). Acta Cryst. E63, o2176-o2177.
Zhou, Y.-P., Yang, Zh.-Y., Yu, H.-J. & Yang, R.-D. (1999). Chin. J. Appl. Chem. 16, 37-41.
Zhu, H., Zhang, X., Song, Y., Xu, H. & Dong, M. (2005). Acta Cryst. E61, o2387-o2388.

organic compounds