1,5-Dimethyl-4-[(5-methyl-2-furyl)­methyl­ene­amino]-2-phenyl-1H-pyrazol-3(2H)-one

Yaning Guo

doi:10.1107/S1600536808015419

. 2008 May 30;64(Pt 6):o1170. doi: 10.1107/S1600536808015419

1,5-Dimethyl-4-[(5-methyl-2-furyl)methyleneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Yaning Guo ^a,^*

PMCID: PMC2961514 PMID: 21202677

Abstract

In the title compound, C₁₇H₁₇N₃O₂, a derivative of 4-aminoantipyrine, the structure displays a trans configuration with respect to the imine C=N double bond. The pyrazoline ring is essentially planar and makes a dihedral angle of 55.80 (1)° with the phenyl ring.

Related literature

For related literature, see: Ali et al. (2002 ▶); Allen et al. (1987 ▶); Carlton et al. (1995 ▶); Coolen et al. (1999 ▶); Cukurovali et al. (2002 ▶); Greisen & Andreasen (1976 ▶); Jiang et al. (2000 ▶); Liang et al. (2002 ▶); Tarafder et al. (2002 ▶).

Experimental

Crystal data

C₁₇H₁₇N₃O₂
M _r = 295.34
Monoclinic,
a = 11.811 (7) Å
b = 9.997 (6) Å
c = 14.116 (9) Å
β = 110.963 (9)°
V = 1556.4 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.40 × 0.40 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T _min = 0.967, T _max = 0.967
5012 measured reflections
2670 independent reflections
1904 reflections with I > 2σ(I)
R _int = 0.097

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.154
S = 1.07
2670 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 I, global. DOI: 10.1107/S1600536808015419/bq2080sup1.cif

e-64-o1170-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015419/bq2080Isup2.hkl

e-64-o1170-Isup2.hkl^{(131.2KB, hkl)}

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

Acknowledgments

The author is grateful for the support of a special research grant (No. 05jk136) of the Education Department of Shaanxi Province.

supplementary crystallographic information

Comment

In recent years, the role of antipyrine and antipyridine derivatives in biological processes have become a topic of study (Carlton et al., 1995; Coolen et al., 1999; Jiang et al., 2000). Antipyrine is an antipyretic drug that is still being used to measure the total hepatic oxidase activity. The properties of antipyrine make it a suitable marker for oxidative stress (Greisen & Andereasen, 1976). Schiff base ligands have demonstrated significant biological activities and new examples are being tested for their antitumor, antimicrobial and antiviral activities (Tarafder et al., 2002; Cukurovali et al., 2002; Ali et al., 2002). These properties stimulated our interest in this field. Crystals of the title compound, (I), were obtained as a new antipyrine Schiff base compound.

The perspective view of the structure and a packing diagram of (I) are illustrated in Fig.1 and 2, respectively. All the bond lengths and angles are in normal ranges (Allen et al., 1987) and comparable to those observed in a similar antipyrine Schiff base (Liang et al., 2002). As seen from Fig. 1, the pyrazoline ring is essentially planar. Atom O2 deviates from the pyrazoline mean plane by -0.117 (5) Å, whereas atoms C10 and C11 by 0.115 (7) and 0.582 (7) Å, on the same side. The dihedral angle between the pyrazoline ring and the C12—C17 phenyl ring is 55.80 (1) °. The furan ring and the pyrazoline ring are approximately coplanar with the dihedral angle between them of 4.79 (2) °. As expected, the molecular structure adopts a trans configuration about the C6═N1 bond.

Experimental

A mixture of 5-methyl-2-furaldehyd (0.1 mmol, 11.0 mg) and 4-aminoantipyrine (0.1 mmol, 20.3 mg) was dissolved in 10 ml methanol, and stirred for about 30 min at room temperature to give a clear yellow solution. After keeping this solution in air for 7 d, yellow block crystals were formed at the bottom of vessel by slowly evaporating the solvent.