2-[5-(2-Fluoro-phen-yl)-3-isobutyl-1H-pyrazol-1-yl]benzoic acid.

In the title compound, C(20)H(19)FN(2)O(2), the dihedral angle between the aromatic rings is 62.1 (1)°, and those between the pyrazole ring and the fluoro-benzene and benzoic acid rings are 52.1 (1) and 53.1 (1)°, respectively. In the crystal, mol-ecules 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 = 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

Δρmax = 0.23 e Å−3

Δρmin = −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.

Click here for additional data file.

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

Click here for additional data file.

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

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H19FN2O2	Prism
Mr = 338.37	Dx = 1.284 Mg m−3
Monoclinic, P21/c	Melting point: 514 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.7732 (14) Å	Cell parameters from 228 reflections
b = 12.2671 (16) Å	θ = 2.2–25°
c = 15.257 (2) Å	µ = 0.09 mm−1
β = 106.836 (5)°	T = 293 K
V = 1750.7 (4) Å3	Prism, colourless
Z = 4	0.28 × 0.26 × 0.22 mm
F(000) = 712

Bruker SMART X2S CCD diffractometer	3094 independent reflections
Radiation source: fine-focus sealed tube	2517 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 1.20 pixels mm-1	θmax = 25.0°, θmin = 2.2°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −14→13
Tmin = 0.975, Tmax = 0.980	l = −13→18
16424 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0699P)2 + 0.3164P] where P = (Fo2 + 2Fc2)/3
3094 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.21 e Å−3
0 constraints

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.67611 (17)	0.18408 (13)	0.80869 (11)	0.0433 (4)
C2	0.57943 (19)	0.10016 (18)	0.78124 (12)	0.0593 (5)
H2	0.4818	0.1141	0.7611	0.071*
C3	0.6306 (2)	−0.00440 (16)	0.78423 (13)	0.0650 (6)
H3	0.5671	−0.0621	0.7658	0.078*
C4	0.7749 (2)	−0.02427 (14)	0.81427 (13)	0.0610 (5)
H4	0.8088	−0.0953	0.8160	0.073*
C5	0.86956 (18)	0.06077 (13)	0.84190 (12)	0.0477 (4)
H5	0.9671	0.0463	0.8628	0.057*
C6	0.82182 (15)	0.16797 (12)	0.83906 (9)	0.0357 (3)
C7	0.92409 (15)	0.25727 (11)	0.87236 (10)	0.0340 (3)
C8	1.02695 (16)	0.26669 (12)	0.95519 (10)	0.0392 (4)
H8	1.0485	0.2159	1.0024	0.047*
C9	1.09279 (16)	0.36759 (12)	0.95454 (10)	0.0378 (4)
C10	1.21498 (18)	0.41685 (14)	1.02714 (11)	0.0511 (4)
H10A	1.1961	0.4095	1.0859	0.061*
H10B	1.2195	0.4941	1.0147	0.061*
C11	1.36062 (19)	0.36548 (15)	1.03400 (12)	0.0583 (5)
H11	1.4327	0.4099	1.0773	0.070*
C12	1.3732 (2)	0.25065 (17)	1.07315 (17)	0.0761 (6)
H12A	1.3115	0.2026	1.0295	0.114*
H12B	1.3458	0.2508	1.1287	0.114*
H12C	1.4703	0.2261	1.0859	0.114*
C13	1.3945 (3)	0.3702 (3)	0.94334 (17)	0.0942 (8)
H13A	1.3313	0.3224	0.9003	0.141*
H13B	1.4916	0.3478	0.9519	0.141*
H13C	1.3821	0.4435	0.9203	0.141*
C14	0.85515 (14)	0.37883 (11)	0.73233 (9)	0.0314 (3)
C15	0.78672 (16)	0.47868 (12)	0.71577 (10)	0.0393 (4)
H15	0.7900	0.5255	0.7643	0.047*
C16	0.71348 (18)	0.50905 (13)	0.62735 (11)	0.0461 (4)
H16	0.6707	0.5774	0.6164	0.055*
C17	0.70354 (17)	0.43865 (14)	0.55532 (11)	0.0484 (4)
H17	0.6529	0.4588	0.4960	0.058*
C18	0.76933 (17)	0.33819 (13)	0.57190 (10)	0.0426 (4)
H18	0.7602	0.2898	0.5236	0.051*
C19	0.84933 (15)	0.30803 (11)	0.65991 (10)	0.0332 (3)
C20	0.93555 (17)	0.20534 (11)	0.67171 (10)	0.0372 (4)
N1	0.93084 (12)	0.35052 (9)	0.82486 (8)	0.0327 (3)
N2	1.03412 (13)	0.41900 (9)	0.87541 (8)	0.0376 (3)
O1	0.85946 (13)	0.12237 (8)	0.62925 (8)	0.0525 (3)
H1	0.9097	0.0676	0.6370	0.079*
O2	1.06073 (13)	0.20202 (9)	0.71308 (9)	0.0558 (3)
F1	0.62576 (11)	0.28686 (9)	0.80786 (9)	0.0691 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0448 (9)	0.0438 (9)	0.0405 (8)	−0.0036 (7)	0.0111 (7)	0.0071 (7)
C2	0.0467 (9)	0.0770 (14)	0.0486 (10)	−0.0214 (9)	0.0049 (8)	0.0101 (9)
C3	0.0784 (14)	0.0570 (12)	0.0561 (11)	−0.0366 (11)	0.0141 (10)	−0.0011 (9)
C4	0.0837 (14)	0.0359 (10)	0.0670 (12)	−0.0172 (9)	0.0278 (10)	−0.0013 (8)
C5	0.0543 (10)	0.0357 (9)	0.0553 (10)	−0.0059 (7)	0.0194 (8)	0.0044 (7)
C6	0.0424 (8)	0.0345 (8)	0.0312 (7)	−0.0066 (6)	0.0123 (6)	0.0035 (6)
C7	0.0395 (7)	0.0287 (7)	0.0352 (8)	−0.0021 (6)	0.0131 (6)	0.0026 (6)
C8	0.0459 (8)	0.0357 (8)	0.0341 (8)	−0.0034 (7)	0.0084 (6)	0.0070 (6)
C9	0.0454 (8)	0.0327 (8)	0.0326 (7)	−0.0025 (6)	0.0071 (6)	−0.0008 (6)
C10	0.0680 (11)	0.0402 (9)	0.0363 (8)	−0.0133 (8)	0.0013 (8)	−0.0011 (7)
C11	0.0505 (10)	0.0629 (12)	0.0505 (10)	−0.0212 (9)	−0.0026 (8)	0.0073 (9)
C12	0.0611 (12)	0.0631 (13)	0.0900 (16)	−0.0011 (10)	−0.0006 (11)	0.0129 (11)
C13	0.0682 (14)	0.141 (2)	0.0767 (15)	−0.0206 (15)	0.0256 (12)	0.0082 (15)
C14	0.0346 (7)	0.0262 (7)	0.0332 (7)	−0.0011 (6)	0.0095 (6)	0.0012 (6)
C15	0.0470 (8)	0.0290 (8)	0.0410 (8)	0.0044 (6)	0.0114 (7)	−0.0041 (6)
C16	0.0530 (9)	0.0337 (8)	0.0495 (9)	0.0118 (7)	0.0116 (7)	0.0075 (7)
C17	0.0515 (9)	0.0511 (10)	0.0376 (8)	0.0099 (8)	0.0048 (7)	0.0091 (7)
C18	0.0515 (9)	0.0414 (9)	0.0331 (8)	0.0039 (7)	0.0092 (7)	−0.0032 (7)
C19	0.0376 (7)	0.0275 (7)	0.0352 (7)	−0.0005 (6)	0.0117 (6)	−0.0016 (6)
C20	0.0500 (9)	0.0292 (8)	0.0336 (7)	0.0022 (7)	0.0140 (7)	−0.0009 (6)
N1	0.0405 (6)	0.0240 (6)	0.0314 (6)	−0.0026 (5)	0.0070 (5)	−0.0009 (5)
N2	0.0484 (7)	0.0258 (6)	0.0349 (7)	−0.0045 (5)	0.0062 (5)	−0.0029 (5)
O1	0.0647 (7)	0.0282 (6)	0.0586 (7)	0.0048 (5)	0.0083 (6)	−0.0092 (5)
O2	0.0485 (7)	0.0389 (7)	0.0751 (9)	0.0092 (5)	0.0103 (6)	−0.0032 (6)
F1	0.0516 (6)	0.0598 (7)	0.0958 (9)	0.0099 (5)	0.0212 (6)	0.0115 (6)

C1—F1	1.3522 (19)	C11—H11	0.9800
C1—C6	1.378 (2)	C12—H12A	0.9600
C1—C2	1.378 (2)	C12—H12B	0.9600
C2—C3	1.373 (3)	C12—H12C	0.9600
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.373 (3)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.377 (2)	C14—C15	1.3832 (19)
C4—H4	0.9300	C14—C19	1.394 (2)
C5—C6	1.392 (2)	C14—N1	1.4338 (17)
C5—H5	0.9300	C15—C16	1.383 (2)
C6—C7	1.471 (2)	C15—H15	0.9300
C7—N1	1.3659 (18)	C16—C17	1.379 (2)
C7—C8	1.373 (2)	C16—H16	0.9300
C8—C9	1.396 (2)	C17—C18	1.379 (2)
C8—H8	0.9300	C17—H17	0.9300
C9—N2	1.3352 (18)	C18—C19	1.394 (2)
C9—C10	1.501 (2)	C18—H18	0.9300
C10—C11	1.532 (3)	C19—C20	1.497 (2)
C10—H10A	0.9700	C20—O2	1.2039 (19)
C10—H10B	0.9700	C20—O1	1.3151 (18)
C11—C13	1.514 (3)	N1—N2	1.3669 (16)
C11—C12	1.521 (3)	O1—H1	0.8200
F1—C1—C6	118.34 (14)	C11—C12—H12A	109.5
F1—C1—C2	118.56 (15)	C11—C12—H12B	109.5
C6—C1—C2	123.09 (16)	H12A—C12—H12B	109.5
C3—C2—C1	118.49 (17)	C11—C12—H12C	109.5
C3—C2—H2	120.8	H12A—C12—H12C	109.5
C1—C2—H2	120.8	H12B—C12—H12C	109.5
C2—C3—C4	120.41 (16)	C11—C13—H13A	109.5
C2—C3—H3	119.8	C11—C13—H13B	109.5
C4—C3—H3	119.8	H13A—C13—H13B	109.5
C3—C4—C5	120.13 (18)	C11—C13—H13C	109.5
C3—C4—H4	119.9	H13A—C13—H13C	109.5
C5—C4—H4	119.9	H13B—C13—H13C	109.5
C4—C5—C6	121.12 (17)	C15—C14—C19	120.03 (13)
C4—C5—H5	119.4	C15—C14—N1	118.60 (12)
C6—C5—H5	119.4	C19—C14—N1	121.37 (12)
C1—C6—C5	116.77 (14)	C16—C15—C14	120.21 (14)
C1—C6—C7	122.82 (14)	C16—C15—H15	119.9
C5—C6—C7	120.32 (14)	C14—C15—H15	119.9
N1—C7—C8	106.43 (12)	C17—C16—C15	120.39 (14)
N1—C7—C6	124.95 (12)	C17—C16—H16	119.8
C8—C7—C6	128.60 (13)	C15—C16—H16	119.8
C7—C8—C9	106.51 (13)	C16—C17—C18	119.48 (14)
C7—C8—H8	126.7	C16—C17—H17	120.3
C9—C8—H8	126.7	C18—C17—H17	120.3
N2—C9—C8	110.30 (12)	C17—C18—C19	121.03 (14)
N2—C9—C10	121.24 (13)	C17—C18—H18	119.5
C8—C9—C10	128.43 (13)	C19—C18—H18	119.5
C9—C10—C11	114.19 (15)	C14—C19—C18	118.75 (13)
C9—C10—H10A	108.7	C14—C19—C20	122.46 (13)
C11—C10—H10A	108.7	C18—C19—C20	118.58 (13)
C9—C10—H10B	108.7	O2—C20—O1	125.16 (13)
C11—C10—H10B	108.7	O2—C20—C19	122.86 (13)
H10A—C10—H10B	107.6	O1—C20—C19	111.94 (13)
C13—C11—C12	112.3 (2)	C7—N1—N2	110.89 (11)
C13—C11—C10	111.49 (16)	C7—N1—C14	129.41 (11)
C12—C11—C10	112.06 (16)	N2—N1—C14	119.52 (11)
C13—C11—H11	106.8	C9—N2—N1	105.87 (11)
C12—C11—H11	106.8	C20—O1—H1	109.5
C10—C11—H11	106.8
F1—C1—C2—C3	−178.45 (15)	C14—C15—C16—C17	2.4 (2)
C6—C1—C2—C3	0.0 (3)	C15—C16—C17—C18	−1.1 (3)
C1—C2—C3—C4	0.2 (3)	C16—C17—C18—C19	−2.0 (3)
C2—C3—C4—C5	0.2 (3)	C15—C14—C19—C18	−2.4 (2)
C3—C4—C5—C6	−0.8 (3)	N1—C14—C19—C18	177.45 (13)
F1—C1—C6—C5	177.89 (14)	C15—C14—C19—C20	172.29 (13)
C2—C1—C6—C5	−0.5 (2)	N1—C14—C19—C20	−7.9 (2)
F1—C1—C6—C7	1.4 (2)	C17—C18—C19—C14	3.7 (2)
C2—C1—C6—C7	−177.03 (15)	C17—C18—C19—C20	−171.20 (15)
C4—C5—C6—C1	0.9 (2)	C14—C19—C20—O2	−46.5 (2)
C4—C5—C6—C7	177.51 (15)	C18—C19—C20—O2	128.16 (17)
C1—C6—C7—N1	−54.0 (2)	C14—C19—C20—O1	135.65 (15)
C5—C6—C7—N1	129.63 (16)	C18—C19—C20—O1	−49.67 (19)
C1—C6—C7—C8	124.18 (18)	C8—C7—N1—N2	−0.46 (16)
C5—C6—C7—C8	−52.2 (2)	C6—C7—N1—N2	178.04 (13)
N1—C7—C8—C9	0.22 (17)	C8—C7—N1—C14	174.51 (14)
C6—C7—C8—C9	−178.22 (14)	C6—C7—N1—C14	−7.0 (2)
C7—C8—C9—N2	0.10 (18)	C15—C14—N1—C7	130.38 (16)
C7—C8—C9—C10	−178.06 (16)	C19—C14—N1—C7	−49.4 (2)
N2—C9—C10—C11	−104.15 (18)	C15—C14—N1—N2	−55.02 (18)
C8—C9—C10—C11	73.8 (2)	C19—C14—N1—N2	125.15 (14)
C9—C10—C11—C13	56.3 (2)	C8—C9—N2—N1	−0.37 (17)
C9—C10—C11—C12	−70.6 (2)	C10—C9—N2—N1	177.94 (14)
C19—C14—C15—C16	−0.6 (2)	C7—N1—N2—C9	0.52 (16)
N1—C14—C15—C16	179.57 (14)	C14—N1—N2—C9	−175.02 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.82	1.93	2.7118 (16)	159

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

Symmetry code: (i) .