[1-(4-Chloro­phen­yl)-5-hy­droxy-3-phenyl-1H-pyrazol-4-yl](thio­phen-2-yl)methanone

Deng, G.-M.; Zhang, H.-M.; Ou-Yang, L.-Q.; Tong, Q.-Z.; Li, S.

doi:10.1107/S1600536812019253

Volume 68
Part 6
Page o1639
June 2012

Received 27 April 2012
Accepted 29 April 2012
Online 5 May 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.031
wR = 0.088
Data-to-parameter ratio = 14.3
Details

[1-(4-Chlorophenyl)-5-hydroxy-3-phenyl-1H-pyrazol-4-yl](thiophen-2-yl)methanone

Gui-Ming Deng,^a,^b He-Ming Zhang,^a ^* Lin-Qi Ou-Yang,^b Qiao-Zhen Tong ^b and Shan Li ^b

^aMOE Key Laboratory of Laser Life Science & Institute of Laser Life Science, College of Biophotonics, South China Normal University, Guangzhou 510631, People's Republic of China, and ^bThe First Affiliated Hospital of Hunan University of Chinese Medicine, Changsha 410007, People's Republic of China
Correspondence e-mail: zhang_heming88@yahoo.com.cn

In the title compound, C₂₀H₁₃ClN₂O₂S, the chlorophenyl, phenyl and thienoyl rings are oriented at dihedral angles 17.84 (7), 53.13 (8) and 34.03 (8)°, respectively, to the central pyrazole ring. An intramolecular O-HO hydrogen bond occurs. In the crystal, pairs of bifurcated O-HO hydrogen bonds link molecules into inversion dimers with R₂²(12) graph-set motifs.

Related literature

For general background to pyrazolone and its complexes, see: Li et al. (2000); Kimata et al. (2007). For related structures, see: Li et al. (2007); Cingolani et al. (2004); Holzer et al. (1999). For the synthesis of the title compound, see: Jensen (1959). For bond-length data, see: Allen et al. (1987); Foces-Foces et al. (1997). For graph-set motifs, see: Etter et al. (1990).

Experimental

Crystal data

C₂₀H₁₃ClN₂O₂S
M_r = 380.84
Monoclinic, P 2₁ /c
a = 6.0686 (2) Å
b = 18.6887 (5) Å
c = 14.9734 (4) Å
= 91.559 (1)°
V = 1697.57 (9) Å³
Z = 4
Mo K radiation
= 0.37 mm^-1
T = 296 K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
20900 measured reflections
3351 independent reflections
3072 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.031
wR(F²) = 0.088
S = 1.06
3351 reflections
235 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2	0.82	2.08	2.7233 (15)	135
O1-H1O2ⁱ	0.82	2.12	2.7964 (15)	140
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; 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 data and figures for this paper are available from the IUCr electronic archives (Reference: XU5526 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (30940094) and the Science Foundation for Excellent Youth Scholars of Educational Commission of Hunan Province, China (10B077).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cingolani, A., Marchetti, F., Pettinari, C., Pettinari, R., Skelton, B. W. & White, A. H. (2004). Inorg. Chem. Commun. 7, 235-237.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Foces-Foces, C., Fontenas, C., Elguero, J. & Sobrados, I. (1997). An. Quim. Int. Ed. 93, 219-224.
Holzer, W., Mereiter, K. & Plagens, B. (1999). Heterocycles, 50, 799-818.
Jensen, B. S. (1959). Acta Chem. Scand. 13, 1668-1670.
Kimata, A., Nakagawa, H., Ohyama, R., Fukuuchi, T., Ohta, S., Suzuki, T. & Miyata, N. (2007). J. Med. Chem. 50, 5053-5056.
Li, J. Z., Li, G. & Yu, W. J. (2000). J. Rare Earths, 18, 233-236.
Li, J.-Z., Zhang, H.-Q., Li, H.-X., Che, P.-Z. & Wang, T.-C. (2007). Acta Cryst. E63, o1289-o1290.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds