4-[(Ethoxy­imino)(phen­yl)meth­yl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Jiu-Si Wang; Yan-Ling Jiang; Wen-Kui Dong; Li Xu; Ai-Ping Kong

doi:10.1107/S1600536808026263

. 2008 Aug 20;64(Pt 9):o1794. doi: 10.1107/S1600536808026263

4-[(Ethoxyimino)(phenyl)methyl]-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Jiu-Si Wang ^a, Yan-Ling Jiang ^a, Wen-Kui Dong ^a,^*, Li Xu ^a, Ai-Ping Kong ^a

PMCID: PMC2960692 PMID: 21201773

Abstract

In the molecule of the title compound, C₁₉H₁₉N₃O₂, the central pyrazole ring makes dihedral angles of 9.89 (3) and 66.06 (5)° with the two phenyl rings, and the two phenyl rings form an angle of 74.05 (5)°. An intramolecular C—H⋯O hydrogen bond forms a six-membered ring, producing an S(6) ring motif. In the crystal structure, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link each molecule to two others, forming an infinite one-dimensional supramolecular structure along the c axis.

Related literature

For related literature, see: Beeam et al. (1984 ▶); Bonati (1980 ▶); Dong & Feng (2006 ▶); Dong et al. (2008a ▶,b ▶); Duan et al. (2007 ▶).

Experimental

Crystal data

C₁₉H₁₉N₃O₂
M _r = 321.37
Monoclinic,
a = 13.0046 (15) Å
b = 11.4657 (11) Å
c = 11.6874 (12) Å
β = 99.4530 (10)°
V = 1719.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.50 × 0.18 × 0.16 mm

Data collection

Brucker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.960, T _max = 0.987
8480 measured reflections
3028 independent reflections
1756 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.140
S = 1.02
3028 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026263/zl2137sup1.cif

e-64-o1794-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026263/zl2137Isup2.hkl

e-64-o1794-Isup2.hkl^{(148.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2ⁱ	0.86	1.80	2.653 (2)	171
C15—H15⋯O2ⁱ	0.93	2.42	3.200 (3)	141
C19—H19⋯O2	0.93	2.32	2.900 (3)	120

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604–01) and the ‘Qing Lan’ Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03–01 A), which are gratefully acknowledged.

supplementary crystallographic information

Comment

The pyrazole ring is a prominent structural motif found in numerous pharmaceutically active compounds. Due to the easy preparation and rich biological activity, the pyrazole framework plays an essential role in biologically active compounds and therefore represents an interesting template for combinatorial as well as medicinal chemistry (Beeam et al., 1984; Bonati et al., 1980). As an extension of our work (Dong et al., 2006; Duan et al., 2007; Dong et al., 2008a; Dong et al., 2008b) on the structural characterization of oxime compounds, the title compound, (Fig. 1), is reported here.

The single-crystal structure of the title compound is built up by only the C₁₉H₁₉N₃O₂ molecules, in which all bond lengths are in normal ranges. In the title compound, the central pyrazole ring makes dihedral angles of 9.89 (3) and 66.06 (5)° with the two outer benzene rings, and the two outer benzene rings form an angle of 74.05 (5)°. An intramolecular C—H···O hydrogen bond forms a six-membered ring, producing an S(6) ring motif. In the crystal structure, intermolecular N—H···O and C—H···O hydrogen bonds link each molecule to two others, forming an infinite one-dimensional supramolecular structure along the c axis (Fig. 2).

Experimental

To a solution of 1-phenyl-3-methyl-4-benzoyl-5-pyrazolon (5 mmol) in warm ethanol (5 ml) was added an ethanol (5 ml) solution of ethoxyamine (10 mmol). After stirring the reaction mixture at 338 K for 6 h, the solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound. Yield, 68%. mp. 444–445 K. Anal. Calc. for C₁₉H₁₉N₃O₂: C, 71.01; H, 5.96; N, 13.08. Found: C, 71.32; H, 5.81; N, 13.15.

Colorless prismatic crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from ethanol at room temperature.