(E)-4-(5-Hydr­oxy-2-methyl­benzyl­idene­amino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Yun-Fa Zheng; Ming-Hua Yang

doi:10.1107/S1600536808029930

. 2008 Sep 27;64(Pt 10):o2017. doi: 10.1107/S1600536808029930

(E)-4-(5-Hydroxy-2-methylbenzylideneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Yun-Fa Zheng ^a, Ming-Hua Yang ^a,^*

PMCID: PMC2959250 PMID: 21201212

Abstract

The title compound, C₁₉H₁₉N₃O₂, is a Schiff base compound derived from 4-aminoantipyrine and 5-hydroxy-2-methylbenzaldehyde. The molecule adopts a trans configuration about the central C=N bond. There is an intramolecular O—H⋯N hydrogen bond. Futhermore, weak C—H⋯O hydrogen bonds lead to the formation of a chain developing parallel to the b axis.

Related literature

For related literature, see: Alemi & Shaabani (2000 ▶); Kim & Shin (1999 ▶); Yan et al. (2006 ▶); Zheng et al. (2006 ▶); You et al. (2006 ▶).

Experimental

Crystal data

C₁₉H₁₉N₃O₂
M _r = 321.37
Monoclinic,
a = 12.030 (2) Å
b = 7.1400 (14) Å
c = 20.210 (4) Å
β = 104.01 (3)°
V = 1684.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.28 × 0.27 × 0.23 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.965, T _max = 0.971
12992 measured reflections
3038 independent reflections
2101 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.117
S = 1.11
3038 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); 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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029930/dn2375sup1.cif

e-64-o2017-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029930/dn2375Isup2.hkl

e-64-o2017-Isup2.hkl^{(146.1KB, 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
O2—H2⋯N1	0.82	1.90	2.6275 (19)	148
C10—H10C⋯O1ⁱ	0.96	2.46	3.386 (2)	163

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful to the Natural Science Foundation of Zhejiang Province (No. Y407081) for financial support.

supplementary crystallographic information

Comment

The design, synthesis, characterization, and properties of Schiff bases and Schiff base complexes. (Yan et al., 2006; Zheng et al., 2006; You et al., 2006) are still of great interest. Schiff bases that have solvent dependent UV/vis spectra (solvatochromicity) can be suitable NLO active materials (Alemi & Shaabani, 2000). They are also useful in asymmetric oxidation of methyl phenyl sulfide (Kim & Shin, 1999).

The molecule adopts trans configuration about the central C=N bond (Fig. 1). There is an intramolecular O-H···N hydrogen bond. Futhermore, weak C-H···O hydrogen bonds lead to the formation of a chain developping parallel to the b axis (Table 1, Fig. 2).

Experimental

Under nitrogen, a mixture of 5-hydroxy-2-methylbenzaldehyde (1.36 g,10 mmol) and 4-amino-1,2-dihydro-1,5-dimethyl -1-phenylpyrazol-3-one (2.03 g, 10 mmol) in absolute ethanol (120 ml) was refluxed for about 3 h to yield a yellow precipitate. The product was collected by vacuum filtration and washed with ethanol. The crude solid was redissolved in CH₂Cl₂ (100 ml) and washed with water (2*10 ml)and brine(10 ml). After dried over Na₂SO₄, the solvent was removed under vacuum, and yellow solid was isolated in yield 92% (3.5 g). Colourless single crystals of the compound suitable for X-ray analysis were grown from CH₂Cl₂ and absolute ethanol(5:1) by slow evaporation of the solvent at room temperature over a period of about a week.