4-[(Z)-(n-Butyl­amino)(phenyl)methyl­idene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Hai-Wen Wang

doi:10.1107/S1600536812009166

. 2012 Mar 7;68(Pt 4):o969. doi: 10.1107/S1600536812009166

4-[(Z)-(n-Butylamino)(phenyl)methylidene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one

Hai-Wen Wang ^a,^*

PMCID: PMC3343944 PMID: 22590025

Abstract

The title compound, C₂₁H₂₃N₃O, exists in an enamine–keto form with the amino group involved in an intramolecular N—H⋯O hydrogen bond. The dihedral angle between the phenyl rings is 73.59 (6)°. The five-membered ring is nearly planar, the largest deviation being 0.0004 (7) Å, and makes dihedral angles of 4.81 (6) and 69.81 (5)° wth the phenyl rings. In the crystal, pairs of weak C—H⋯O interactions link the molecules into centrosymmetric dimers.

Related literature

For applications of Schiff bases derived from 4-acylpyrazolones, see: Bernardino et al. (2006 ▶); Zhang et al. (2008 ▶). For related structures, see: Zhang et al. (2007 ▶); Chi et al. (2010 ▶); Zhen & Han (2005 ▶); Wang (2010 ▶).

Experimental

Crystal data

C₂₁H₂₃N₃O
M _r = 333.42
Monoclinic,
a = 9.5215 (9) Å
b = 14.7867 (14) Å
c = 12.8055 (12) Å
β = 100.645 (2)°
V = 1771.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.28 × 0.20 × 0.16 mm

Data collection

Bruker SMART 1000 CCD diffractometer
16506 measured reflections
4368 independent reflections
3362 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.103
S = 1.01
4368 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009166/cv5252sup1.cif

e-68-0o969-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009166/cv5252Isup2.hkl

e-68-0o969-Isup2.hkl^{(214.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009166/cv5252Isup3.cml

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—H3A⋯O1	0.921 (16)	1.873 (16)	2.6704 (14)	143.5 (14)
C13—H13⋯O1ⁱ	0.93	2.39	3.3175 (15)	172

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the College of Chemistry and Molecular Engineering, East China University of Science and Technology.

supplementary crystallographic information

Comment

The Schiff bases derived from 4-acylpyrazolones have attracted much attention due to their applications in pharmaceutical and agrochemical fields (e.g. Bernardino et al., 2006; Zhang et al., 2008). In order to expand this field, we now report the synthesis and structure of the title compound, (I) (Fig. 1).

In (I), the Schiff base molecule adopts an E geometry with respect to the C=N bond (Fig. 1). All bond lengths and angles are comparable with those found in the related compounds (Chi et al., 2010; Wang et al., 2010; Zhen et al., 2005; Zhang et al.., 2007). The dihedral angle between the two phenyl rings is 73.59 (6)°. The five-membered ring of the title compound is nearly planar, with the largest deviation being 0.0004 (7)%A for atom N1. The dihedral angles between this mean plane and two benzene rings are 4.81 (6)° and 69.81 (5)%. Weak intermolecular C—H···O interactions (Table 1) link the molecules into centrosymmetric dimers.

Experimental

A mixture of a 10 ml HPMBP (2 mmol, 0.5566 g) anhydrous ethanol solution, and a 0.2 ml n-butylamine (2 mmol, 0.1463 g) solution was refluxed for ca 8 h, with addition of a few drops of glacial acetic acid as a catalyst. The ethanol was removed by evaporation and the resulting green precipitate formed was filtered off, washed with cold anhydrous ethanol and dried in air. Yellow block single crystals suitable for analysis were obtained by slow evaporation of a solution in anhydrous ethanol at room temperature for a few days.