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

S Sreenivasa; K E Manojkumar; P A Suchetan; N R Mohan; Vijith Kumar; B S Palakshamurthy

doi:10.1107/S1600536812050702

. 2013 Jan 4;69(Pt 2):o176. doi: 10.1107/S1600536812050702

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, B S Palakshamurthy ^d

PMCID: PMC3569238 PMID: 23424461

Abstract

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—H⋯N 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,
a = 9.7732 (14) Å
b = 12.2671 (16) Å
c = 15.257 (2) Å
β = 106.836 (5)°
V = 1750.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.114
S = 0.98
3094 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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 Material

Click here for additional data file.^{(25.5KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050702/hb7011sup1.cif

e-69-0o176-sup1.cif^{(25.5KB, cif)}

Click here for additional data file.^{(151.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050702/hb7011Isup2.hkl

e-69-0o176-Isup2.hkl^{(151.8KB, hkl)}

Click here for additional data file.^{(6.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812050702/hb7011Isup3.cml

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
O1—H1⋯N2ⁱ	0.82	1.93	2.7118 (16)	159

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Symmetry code: (i) Inline graphic .

Acknowledgments

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.

supplementary crystallographic information

Comment

The pyrazole nucleus is an important structure in numerous natural and synthetic compounds and in medicinal chemistry (e.g. Ramaiah et al., 1999). As part of our studies in this area, the title compound was synthesized and its crystal structure determined.

In the title compound, C₂₀H₁₉FN₂O₂, the dihedral angle between the aromatic rings is 62.1 (1)°, and those between the pyrazole ring and the aromatic ring containing fluorine atom and the pyrazole ring and the aromatic ring containing carboxylic group are 52.1 (1)° and 53.1 (1)°, respectively. In the crystal structure, the molecules are linked into C(7) chains through O—H···N H-bonds.

Experimental

1-(2-Fluorophenyl)-5-methyl-hexane-1,3-dione (0.01 mmol) and 2-hydrazinobenzoic acid (0.01 mmol) were taken in 15 ml ethanol and the mixture was heated for 12 h. The reaction was monitored by TLC. The solvent was removed by vacuum. The crude mass obtained was purified by column chromatography.

Colourless prisms were obtained by slow evaporation of the solution of the compound in a mixture of dichloromethane and methanol (9:1).