2-[5-(2-Fluoro­phen­yl)-3-isobutyl-1H-pyrazol-1-yl]benzoic acid

Sreenivasa, S.; Manojkumar, K.E.; Suchetan, P.A.; Mohan, N.R.; Kumar, V.; Palakshamurthy, B.S.

doi:10.1107/S1600536812050702

Volume 69
Part 2
Page o176
February 2013

Received 7 December 2012
Accepted 13 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.041
wR = 0.114
Data-to-parameter ratio = 13.6
Details

2-[5-(2-Fluorophenyl)-3-isobutyl-1H-pyrazol-1-yl]benzoic acid

S. Sreenivasa,^a ^* K. E. Manojkumar,^a P. A. Suchetan,^b N. R. Mohan,^a Vijith Kumar ^c and B. S. Palakshamurthy ^d

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,^bDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India,^cSoild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012 India, and ^dDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C₂₀H₁₉FN₂O₂, the dihedral angle between the aromatic rings is 62.1 (1)°, and those between the pyrazole ring and the fluorobenzene and benzoic acid rings are 52.1 (1) and 53.1 (1)°, respectively. In the crystal, molecules are linked into [010] C(7) chains by O-HN hydrogen bonds.

Related literature

For background to pyrazole derivatives and their uses, see: Ramaiah et al. (1999).

Experimental

Crystal data

C₂₀H₁₉FN₂O₂
M_r = 338.37
Monoclinic, P 2₁ /c
a = 9.7732 (14) Å
b = 12.2671 (16) Å
c = 15.257 (2) Å
= 106.836 (5)°
V = 1750.7 (4) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.28 × 0.26 × 0.22 mm

Data collection

Bruker SMART X2S CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.975, T_max = 0.980
16424 measured reflections
3094 independent reflections
2517 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.114
S = 0.98
3094 reflections
228 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N2ⁱ	0.82	1.93	2.7118 (16)	159
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7011 ).

Acknowledgements

The authors thank Dr S. C. Sharma, Vice Chancellor, Tumkur University, for his constant encouragement and Professor T. N. Guru Row, Soild State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions. BSP thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his guidance.

References

Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Ramaiah, K., Grossert, J. S., Hooper, D. L., Dubey, P. K. & Ramanatham, J. (1999). J. Indian Chem. Soc. 76, 140-144.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds