(E)-1,5-Dimethyl-4-[3-(4-nitro­benz­yloxy)benzyl­ideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Shou-Xin Liu; Xia Tian; Xiao-Li Zhen; Zhen-Chao Li; Jian-Rong Han

doi:10.1107/S1600536808035046

. 2008 Oct 31;64(Pt 11):o2245. doi: 10.1107/S1600536808035046

(E)-1,5-Dimethyl-4-[3-(4-nitrobenzyloxy)benzylideneamino]-2-phenyl-1H-pyrazol-3(2H)-one

Shou-Xin Liu ^a,^*, Xia Tian ^b, Xiao-Li Zhen ^b, Zhen-Chao Li ^b, Jian-Rong Han ^b,^‡

PMCID: PMC2959699 PMID: 21581099

Abstract

In the title compound, C₂₅H₂₂N₄O₄, the central benzene ring, makes dihedral angles of 74.35 (6), 17.01 (8) and 62.19 (7)°, respectively, with the nitrobenzyl ring, the pyrazolone ring and the terminal phenyl ring. Intermolecular C—H⋯O hydrogen bonds help to consolidate the crystal packing.

Related literature

For the potential applications of Schiff bases, see: Jones et al. (1979 ▶); Larson & Pecoraro (1991 ▶); Santos et al. (2001 ▶). For a related structure, see: Han & Zhen (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₅H₂₂N₄O₄
M _r = 442.47
Triclinic,
a = 8.003 (2) Å
b = 9.798 (3) Å
c = 14.425 (5) Å
α = 90.844 (5)°
β = 92.310 (6)°
γ = 101.202 (6)°
V = 1108.4 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 294 (2) K
0.20 × 0.18 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.956, T _max = 0.991
5780 measured reflections
3898 independent reflections
2302 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.125
S = 1.01
3898 reflections
300 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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/S1600536808035046/hb2829sup1.cif

e-64-o2245-sup1.cif^{(23KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035046/hb2829Isup2.hkl

e-64-o2245-Isup2.hkl^{(191KB, 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
C7—H7B⋯O4ⁱ	0.97	2.50	3.293 (3)	139

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Symmetry code: (i) Inline graphic .

Acknowledgments

The project was supported by the Foundation of the Education Department of Hebei Province (grant No. 606022).

supplementary crystallographic information

Comment

There has been a steady growth of interest in the synthesis, structure, and reactivity of Schiff bases due to their potential applications in areas such as biological modelling, catalysis, and molecular magnets (Jones et al., 1979; Larson & Pecoraro, 1991). One of the aims of investigating the structural chemistry of Schiff bases is to develop protein and enzyme mimics (Santos et al., 2001). Among the large number of the compounds, 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one forms a variety of Schiff bases with aldehydes, and the synthesis and crystal structures of them, such as (E)-(4)-(3-ethoxy-4-hydroxybenzylideneamino)- 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (Han & Zhen, 2005) have been reported. In present study we report the syntheses and molecular structure of the title compound, (I), (Fig. 1).

The bond lengths and angles in (I) are within their normal ranges (Allen et al., 1987). The pyrazolone ring (C15—C17/N2—N4/O4) is close to planar, with an r.m.s. deviation for the fitted atoms of 0.0441 Å. It makes a dihedral angle of 49.38 (8)° with the attached phenyl ring (C20—C25). The central benzene ring (C8—C14/O3) is also planar, with an r.m.s. deviation for the fitted atoms of 0.0079 Å, and it makes dihedral angles of 74.35 (6)°, 17.01 (8)° and 62.19 (7)° with the nitrobenzyl ring (C1—C7), the pyrazolone ring (C15—C17/N2—N4/O4) and the terminal phenyl ring (C20—C25), respectively.

Packing is stabilized by weak, non-classical intermolecular C7—H7B···O4ⁱ (symmetry code (i): 2 - x, 1 - y, -z) hydrogen bonds that form inversion related dimers, (Fig. 2, Table 1).

Experimental

An anhydrous ethanol solution (50 ml) of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one (2.03 g, 10 mmol) was added to an anhydrous ethanol solution (100 ml) of 3-(4-nitrobenzyloxy)benzaldehyde (2.57 g, 10 mmol) and the mixture stirred at 350 K for 5 h under nitrogen, giving a yellow precipitate. The product was isolated, recrystallized from acetonitrile and then dried in a vacuum to give the pure compound in 81% yield. Yellow single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetonitrile solution.