5-(4-Chloro­phen­yl)-1-(2,4-dichloro­phen­yl)-4-methyl-1H-pyrazole-3-carboxylic acid

Wang, W.; Fang, Z.

doi:10.1107/S1600536808038105

Volume 64
Part 12
Page o2413
December 2008

Received 13 November 2008
Accepted 16 November 2008
Online 22 November 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.009 Å
R = 0.072
wR = 0.181
Data-to-parameter ratio = 14.3
Details

5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

Wei Wang ^a and Zheng Fang ^a ^*

^aCollege of Life Sciences and Pharmaceutical Engineering, Nanjing University of Technolgy, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
Correspondence e-mail: fzcpu@163.com

The asymmetric unit of the title compound, C₁₇H₁₁Cl₃N₂O₂, contains two independent molecules; the pyrazole rings are oriented with respect to the chlorophenyl and dichlorophenyl rings at dihedral angles of 43.00 (3) and 65.06 (4)°, respectively, in one molecule, and 51.17 (3) and 69.99 (3)°, respectively, in the other. Pairs of intermolecular O-HO hydrogen bonds link the molecules into dimers. In the crystal structure, there are [pi] - [pi] contacts between the pyrazole rings and dichlorophenyl rings [centroid-centroid distances = 3.859 (3) and 3.835 (3) Å].

Related literature

For bond-length data, see: Allen et al. (1987). For the chemical background, see: Tang et al. (2007).

Experimental

Crystal data

C₁₇H₁₁Cl₃N₂O₂
M_r = 381.63
Monoclinic, P 2/c
a = 13.192 (3) Å
b = 8.8170 (18) Å
c = 30.012 (6) Å
= 102.42 (3)°
V = 3409.1 (13) Å³
Z = 8
Mo K radiation
= 0.55 mm^-1
T = 294 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.853, T_max = 0.947
6479 measured reflections
6190 independent reflections
2893 reflections with I > 2(I)
R_int = 0.038
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.072
wR(F²) = 0.181
S = 0.99
6190 reflections
433 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.28 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO4	0.85	1.74	2.564 (7)	163
O3-H3BO1	0.85	1.89	2.723 (6)	165
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z.

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2574 ).

Acknowledgements

The authors thank the Center for Testing and Analysis, Nanjing University, for the support.

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.
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Tang, L. H., Tao, L, Chen, H. B. & Zhong, B. H. (2007). Chin. J. Pharm. 38, 252-254.

organic compounds