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

Kausar, R.; Badshah, A.; Zia ul Haq, M.; Hasan, A.; Bolte, M.

doi:10.1107/S1600536809004012

Volume 65
Part 3
Page o589
March 2009

Received 28 January 2009
Accepted 3 February 2009
Online 25 February 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.096
Data-to-parameter ratio = 17.0
Details

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 ^* and Michael Bolte ^c

^aAllama Iqbal Open University, Islamabad, Pakistan,^bDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^cInstitut für Anorganische Chemie, J. W. Goethe-Universität, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: h.aurangzeb@yahoo.com

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-HN 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, P 2₁ /c
a = 9.5880 (5) Å
b = 13.7397 (8) Å
c = 14.2771 (7) Å
= 109.340 (4)°
V = 1774.68 (16) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.051

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.096
S = 1.02
4085 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2N2ⁱ	0.91 (2)	1.88 (2)	2.7894 (11)	175.0 (17)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: PK2149 ).

Acknowledgements

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

References

Ahmad, R., Zia-ul-Haq, M., Duddeck, H., Stefaniak, L. & Sitkowski, J. S. (1997). Monatsh. Chem. 128, 633-640.
Beeam, C. F., Hall, H. L., Huff, A. M., Tummons, R. C. & Grady, S. A. O. (1984). J. Heteroat. Chem. 21, 1897-1902.
Bonati, F. (1980). Chim. Ind. (Roma), 62, 323-328.
Elguero, J. (1983). Comprehensive Heterocyclic Chemistry, Vol. 5, Part 4A, pp. 167, 304. Elmford, New York: Pergamon Press.
Freyer, W. & Radeglia, R. (1981). Monatsh. Chem. 112, 105-117.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.
Trofinenko, S. (1972). Chem. Rev. 72, 497-500.

organic compounds