2-[3-(4-Methoxyphen­yl)-1-phenyl-1H-pyrazol-5-yl]phenol

Rukhsana Kausar; Amir Badshah; Muhammad Zia ul Haq; Aurangzeb Hasan; Michael Bolte

doi:10.1107/S1600536809004012

. 2009 Feb 25;65(Pt 3):o589. doi: 10.1107/S1600536809004012

2-[3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazol-5-yl]phenol

Rukhsana Kausar ^a, Amir Badshah ^b, Muhammad Zia ul Haq ^b, Aurangzeb Hasan ^b,^*, Michael Bolte ^c

PMCID: PMC2968556 PMID: 21582244

Abstract

The title compound, C₂₂H₁₈N₂O₂, was derived from 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione. The central pyrazole ring forms dihedral angles of 16.83 (5), 48.97 (4) and 51.68 (4)°, respectively, with the methoxyphenyl, phenyl and hydroxyphenyl rings. The crystal packing is stabilized by O—H⋯N hydrogen bonding.

Related literature

For general synthesis, see: Ahmad et al. (1997 ▶). For synthetic applications, see: Beeam et al. (1984 ▶); Bonati (1980 ▶); Elguero (1983 ▶); Freyer & Radeglia (1981 ▶); Trofinenko (1972 ▶).

Experimental

Crystal data

C₂₂H₁₈N₂O₂
M _r = 342.38
Monoclinic,
a = 9.5880 (5) Å
b = 13.7397 (8) Å
c = 14.2771 (7) Å
β = 109.340 (4)°
V = 1774.68 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 (2) K
0.33 × 0.31 × 0.26 mm

Data collection

Stoe IPDS-II two-circle diffractometer
Absorption correction: none
24784 measured reflections
4085 independent reflections
3676 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.096
S = 1.02
4085 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004012/pk2149sup1.cif

e-65-0o589-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004012/pk2149Isup2.hkl

e-65-0o589-Isup2.hkl^{(200.2KB, 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⋯N2ⁱ	0.91 (2)	1.88 (2)	2.7894 (11)	175.0 (17)

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Symmetry code: (i) Inline graphic .

Acknowledgments

AB is grateful to the Higher Education Commission of Pakistan for the grant that supported this work.

supplementary crystallographic information

Comment

Pyrazoles are important because of their potential for biological activity. They have antipruritic, anti-inflammatory and antirheumatic effects (Beeam et al., 1984). Both traditional and new scientific methods have been used to prepare new materials for medicine (Elguero et al., 1983) and agriculture (Trofinenko, 1972). Neutral and anionic pyrazoles are excellent ligands and their coordination chemistry has been extensively studied (Bonati, 1980). Pyrazoles are also used as analytical reagents (Freyer & Radeglia, 1981). In the molecular structure of the title compound, C₂₂H₁₈N₂O₂, (Scheme 1, Fig. 1) the central pyrazole ring forms dihedral angles of 16.83 (5)°, 48.97 (4)° and 51.68 (4)° with the methoxyphenyl, phenyl and hydroxyphenyl rings, respectively. The crystal packing is stabilized by an O-H···N hydrogen bond (Table 1).

Experimental

1-(2'-Hydroxyphenyl)-3-(4"-methoxyphenyl) propane-1,3-dione was prepared by a modified Baker Venkataram rearrangement as reported earlier (Ahmad et al. 1997). 2-(3-(4-methxyphenyl)-1-Phenyl-1H-pyrazol-5-yl)phenol was prepared by refluxing 1-(2'-hydroxyphenyl)-3-(4"-methoxyphenyl) propane-1,3-dione (2.7 g, 10 mmol) with phenyl hydrazine (1.08 g,0.99 ml, 10 mmol) in a mixture of 50 ml absolute ethanol and 15 ml glacial acetic acid for seven hours as shown in scheme 2.The oily mixture obtained was purified by a dry silica gel column. The product was recrystallized using absolute ethanol. (Yield: 45%, m.p: 449k)