4-{(Z)-(sec-Butyl­amino)(phen­yl)methyl­ene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Xu, H.-Z.; Xu, J.-P.; Yuan, Y.-W.; Zhang, J.; Zhu, Y.-Q.

doi:10.1107/S160053680902950X

Volume 65
Part 9
Page o2116
September 2009

Received 8 July 2009
Accepted 24 July 2009
Online 8 August 2009

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R = 0.047
wR = 0.135
Data-to-parameter ratio = 15.8
Details

4-{(Z)-(sec-Butylamino)(phenyl)methylene}-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Hai-Zhen Xu,^a ^* Jian-Ping Xu,^b Yan-Wei Yuan,^c Jin Zhang ^c and You-Quan Zhu ^c

^aCollege of Chemistry and Life Science, Tianjin Normal University, Weijin Road No. 241, Tianjin, People's Republic of China,^bElementary Education College, Tianjin Normal University, Weijin Road No. 241, Tianjin, 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

In the title compound, C₂₁H₂₃N₃O, the dihedral angles formed by the pyrazolone ring with two phenyl rings are 10.38 (8) and 76.94 (6)°. The sec-butylamino group is disordered over two positions, with refined site-occupancy factors of 0.730 (4) and 0.270 (4). The compound could potentially be ligand stabilized in the solid state in a keto-enamine tautomeric form. The amine functionality is involved in an intramolecular N-HO hydrogen bond, while weak intermolecular C-HO and C-HN hydrogen bonds participate in the formation of the crystal structure.

Related literature

For the antibacterial, biological and analgesic activity of metal complexes of 1-phenyl-3-methyl-4-benzoylpyrazolon-5-one, see: Li et al. (1997); Liu et al. (1980); Zhou et al. (1999).

Experimental

Crystal data

C₂₁H₂₃N₃O
M_r = 333.42
Triclinic, $[P \overline 1]$
a = 9.3631 (19) Å
b = 10.077 (2) Å
c = 10.687 (2) Å
= 107.07 (3)°
= 100.30 (3)°
= 100.14 (3)°
V = 920.0 (4) Å³
Z = 2
Mo K radiation
= 0.08 mm^-1
T = 113 K
0.20 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.985, T_max = 0.988
8309 measured reflections
4296 independent reflections
2944 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.135
S = 1.08
4296 reflections
272 parameters
16 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.21 e Å^-3

Table 1
Selected bond lengths (Å)

O1-C7	1.2529 (17)
C7-C8	1.4382 (19)
C8-C11	1.402 (2)
C11-N3'	1.311 (5)
C11-N3	1.359 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3'-H3'O1	0.904 (10)	1.99 (4)	2.705 (6)	135 (5)
N3-H3O1	0.902 (10)	1.933 (15)	2.699 (2)	141.6 (18)
C16-H16AO1ⁱ	0.95	2.53	3.2743 (19)	135
C13-H13AN2ⁱⁱ	0.95	2.60	3.537 (2)	167
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); 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: 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: BH2238 ).

Acknowledgements

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

References

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 (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhou, Y.-P., Yang, Zh.-Y., Yu, H.-J. & Yang, R.-D. (1999). Chin. J. Appl. Chem. 16, 37-41.

organic compounds