4-(4-Fluoro-phen-yl)-1-phenyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine.

In the title compound, C(20)H(15)FN(4), the pyrazole ring forms dihedral angles of 43.51 (6), 39.95 (6) and 32.23 (6)° with the directly attached 4-fluoro-phenyl, pyridine and phenyl rings, respectively. The crystal packing is stabilized by inter-molecular N-H⋯N and N-H⋯F hydrogen bonds.

Related literature

For p38α MAP kinase inhibitors having a vicinal 4-fluoro­phen­yl/pyridin-4-yl system connected to a five-membered heterocyclic core, see: Abu Thaher et al. (2009 ▶); Peifer et al. (2006 ▶). For inhibitory activity and preparation of the title compound, see: Abu Thaher et al. (2012 ▶).

Experimental

Crystal data

C20H15FN4

M = 330.36

Monoclinic,

a = 12.2408 (3) Å

b = 10.4427 (2) Å

c = 12.9099 (3) Å

β = 101.951 (1)°

V = 1614.46 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 193 K

0.39 × 0.38 × 0.24 mm

Data collection

Bruker SMART CCD diffractometer

29688 measured reflections

5459 independent reflections

3972 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.139

S = 1.07

5459 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004096/bt5808sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004096/bt5808Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004096/bt5808Isup3.cml

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

C20H15FN4	F(000) = 688
Mr = 330.36	Dx = 1.359 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8198 reflections
a = 12.2408 (3) Å	θ = 2.5–31°
b = 10.4427 (2) Å	µ = 0.09 mm−1
c = 12.9099 (3) Å	T = 193 K
β = 101.951 (1)°	Plate, colourless
V = 1614.46 (6) Å3	0.39 × 0.38 × 0.24 mm
Z = 4

Bruker SMART CCD diffractometer	3972 reflections with I > 2σ(I)
Radiation source: sealed Tube	Rint = 0.092
Graphite monochromator	θmax = 31.7°, θmin = 2.1°
CCD scan	h = −17→18
29688 measured reflections	k = −15→15
5459 independent reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0759P)2] where P = (Fo2 + 2Fc2)/3
5459 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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
N1	0.42742 (8)	0.43838 (8)	0.21818 (7)	0.01963 (19)
N2	0.42901 (8)	0.56672 (8)	0.24356 (7)	0.0203 (2)
C3	0.38505 (9)	0.62463 (9)	0.15232 (8)	0.0186 (2)
C4	0.35487 (9)	0.53683 (9)	0.06717 (8)	0.0188 (2)
C5	0.38251 (9)	0.41737 (9)	0.11336 (8)	0.0196 (2)
C6	0.47171 (9)	0.34914 (9)	0.29983 (8)	0.0200 (2)
C7	0.52687 (9)	0.23961 (10)	0.27749 (9)	0.0253 (2)
H7	0.5349	0.2224	0.2072	0.030*
C8	0.57028 (11)	0.15549 (11)	0.35910 (10)	0.0310 (3)
H8	0.6058	0.0789	0.3440	0.037*
C9	0.56218 (11)	0.18236 (11)	0.46214 (10)	0.0323 (3)
H9	0.5923	0.1245	0.5175	0.039*
C10	0.50995 (10)	0.29421 (12)	0.48467 (9)	0.0290 (3)
H10	0.5067	0.3143	0.5557	0.035*
C11	0.46249 (10)	0.37644 (10)	0.40313 (9)	0.0243 (2)
H11	0.4239	0.4510	0.4179	0.029*
C12	0.37406 (8)	0.76535 (9)	0.15138 (8)	0.0193 (2)
C13	0.34059 (10)	0.82967 (10)	0.23403 (9)	0.0235 (2)
H13	0.3249	0.7833	0.2926	0.028*
C14	0.33030 (10)	0.96196 (10)	0.23020 (10)	0.0276 (3)
H14	0.3088	1.0042	0.2880	0.033*
N15	0.34895 (9)	1.03314 (9)	0.14963 (8)	0.0298 (2)
C16	0.38196 (11)	0.97073 (11)	0.07086 (10)	0.0299 (3)
H16	0.3964	1.0196	0.0131	0.036*
C17	0.39641 (10)	0.83907 (10)	0.06831 (9)	0.0258 (2)
H17	0.4211	0.7999	0.0108	0.031*
C18	0.30291 (9)	0.56329 (9)	−0.04437 (8)	0.0193 (2)
C19	0.21579 (9)	0.65213 (10)	−0.06991 (9)	0.0238 (2)
H19	0.1874	0.6914	−0.0146	0.029*
C20	0.17003 (10)	0.68406 (11)	−0.17433 (9)	0.0273 (3)
H20	0.1119	0.7456	−0.1910	0.033*
C21	0.21154 (10)	0.62388 (11)	−0.25283 (9)	0.0276 (3)
C22	0.29435 (10)	0.53254 (11)	−0.23223 (9)	0.0269 (2)
H22	0.3194	0.4908	−0.2884	0.032*
C23	0.34046 (9)	0.50288 (10)	−0.12725 (9)	0.0229 (2)
H23	0.3982	0.4408	−0.1116	0.027*
F24	0.16930 (7)	0.65754 (7)	−0.35554 (6)	0.0425 (2)
N25	0.37049 (9)	0.29779 (8)	0.06845 (7)	0.0264 (2)
H25A	0.3602	0.2335	0.1059	0.040*
H25B	0.3307	0.3008	0.0053	0.040*

	U11	U22	U33	U12	U13	U23
N1	0.0270 (5)	0.0128 (4)	0.0171 (4)	0.0019 (3)	−0.0001 (3)	−0.0001 (3)
N2	0.0273 (5)	0.0125 (4)	0.0195 (4)	0.0005 (3)	0.0010 (3)	−0.0006 (3)
C3	0.0216 (5)	0.0137 (4)	0.0197 (5)	0.0004 (4)	0.0024 (4)	−0.0001 (3)
C4	0.0219 (5)	0.0147 (4)	0.0184 (5)	0.0008 (4)	0.0010 (4)	0.0006 (3)
C5	0.0238 (5)	0.0150 (4)	0.0186 (5)	0.0005 (4)	0.0014 (4)	−0.0006 (3)
C6	0.0232 (5)	0.0149 (4)	0.0195 (5)	0.0000 (4)	−0.0008 (4)	0.0032 (3)
C7	0.0293 (6)	0.0213 (5)	0.0230 (5)	0.0043 (4)	0.0002 (4)	0.0003 (4)
C8	0.0342 (6)	0.0212 (5)	0.0335 (7)	0.0082 (5)	−0.0024 (5)	0.0023 (4)
C9	0.0372 (7)	0.0264 (6)	0.0282 (6)	0.0021 (5)	−0.0047 (5)	0.0098 (5)
C10	0.0357 (6)	0.0289 (6)	0.0205 (5)	−0.0018 (5)	0.0016 (5)	0.0048 (4)
C11	0.0298 (6)	0.0203 (5)	0.0218 (5)	0.0016 (4)	0.0035 (4)	0.0013 (4)
C12	0.0206 (5)	0.0135 (4)	0.0216 (5)	0.0005 (4)	−0.0008 (4)	0.0000 (3)
C13	0.0293 (6)	0.0169 (4)	0.0234 (5)	0.0018 (4)	0.0038 (4)	0.0008 (4)
C14	0.0329 (6)	0.0178 (5)	0.0314 (6)	0.0025 (4)	0.0054 (5)	−0.0033 (4)
N15	0.0364 (6)	0.0164 (4)	0.0342 (6)	0.0003 (4)	0.0018 (4)	0.0003 (4)
C16	0.0412 (7)	0.0171 (5)	0.0303 (6)	−0.0028 (5)	0.0047 (5)	0.0056 (4)
C17	0.0360 (6)	0.0181 (5)	0.0232 (6)	−0.0016 (4)	0.0063 (5)	0.0003 (4)
C18	0.0214 (5)	0.0152 (4)	0.0196 (5)	−0.0018 (4)	0.0002 (4)	0.0008 (3)
C19	0.0253 (5)	0.0203 (5)	0.0235 (5)	0.0024 (4)	0.0002 (4)	−0.0003 (4)
C20	0.0276 (6)	0.0222 (5)	0.0276 (6)	0.0018 (4)	−0.0044 (5)	0.0035 (4)
C21	0.0331 (6)	0.0269 (5)	0.0187 (5)	−0.0057 (5)	−0.0044 (4)	0.0045 (4)
C22	0.0326 (6)	0.0280 (5)	0.0196 (5)	−0.0029 (5)	0.0042 (4)	−0.0011 (4)
C23	0.0244 (5)	0.0203 (5)	0.0230 (5)	0.0010 (4)	0.0031 (4)	0.0003 (4)
F24	0.0545 (5)	0.0467 (5)	0.0197 (4)	−0.0003 (4)	−0.0078 (3)	0.0087 (3)
N25	0.0409 (6)	0.0144 (4)	0.0202 (5)	−0.0002 (4)	−0.0025 (4)	−0.0008 (3)

N1—C5	1.3687 (13)	C13—C14	1.3871 (14)
N1—N2	1.3789 (11)	C13—H13	0.9500
N1—C6	1.4272 (13)	C14—N15	1.3360 (16)
N2—C3	1.3342 (13)	C14—H14	0.9500
C3—C4	1.4202 (13)	N15—C16	1.3389 (17)
C3—C12	1.4755 (13)	C16—C17	1.3875 (15)
C4—C5	1.3938 (13)	C16—H16	0.9500
C4—C18	1.4748 (13)	C17—H17	0.9500
C5—N25	1.3718 (12)	C18—C23	1.3992 (15)
C6—C7	1.3885 (15)	C18—C19	1.4004 (14)
C6—C11	1.3910 (16)	C19—C20	1.3891 (15)
C7—C8	1.3900 (15)	C19—H19	0.9500
C7—H7	0.9500	C20—C21	1.3760 (17)
C8—C9	1.3830 (19)	C20—H20	0.9500
C8—H8	0.9500	C21—F24	1.3658 (12)
C9—C10	1.3909 (17)	C21—C22	1.3771 (17)
C9—H9	0.9500	C22—C23	1.3909 (15)
C10—C11	1.3891 (15)	C22—H22	0.9500
C10—H10	0.9500	C23—H23	0.9500
C11—H11	0.9500	N25—H25A	0.8520
C12—C13	1.3924 (15)	N25—H25B	0.8591
C12—C17	1.3925 (15)
C5—N1—N2	111.95 (8)	C14—C13—C12	119.48 (11)
C5—N1—C6	129.72 (8)	C14—C13—H13	120.3
N2—N1—C6	118.33 (8)	C12—C13—H13	120.3
C3—N2—N1	104.32 (8)	N15—C14—C13	123.58 (11)
N2—C3—C4	112.55 (9)	N15—C14—H14	118.2
N2—C3—C12	118.56 (9)	C13—C14—H14	118.2
C4—C3—C12	128.89 (9)	C14—N15—C16	116.59 (10)
C5—C4—C3	104.21 (9)	N15—C16—C17	124.09 (11)
C5—C4—C18	127.07 (9)	N15—C16—H16	118.0
C3—C4—C18	128.70 (9)	C17—C16—H16	118.0
N1—C5—N25	123.35 (9)	C16—C17—C12	118.90 (11)
N1—C5—C4	106.96 (8)	C16—C17—H17	120.6
N25—C5—C4	129.69 (10)	C12—C17—H17	120.6
C7—C6—C11	120.49 (10)	C23—C18—C19	118.25 (10)
C7—C6—N1	120.74 (10)	C23—C18—C4	121.24 (9)
C11—C6—N1	118.72 (9)	C19—C18—C4	120.50 (10)
C6—C7—C8	119.29 (11)	C20—C19—C18	121.46 (11)
C6—C7—H7	120.4	C20—C19—H19	119.3
C8—C7—H7	120.4	C18—C19—H19	119.3
C9—C8—C7	120.56 (11)	C21—C20—C19	117.96 (10)
C9—C8—H8	119.7	C21—C20—H20	121.0
C7—C8—H8	119.7	C19—C20—H20	121.0
C8—C9—C10	119.94 (10)	F24—C21—C20	118.31 (11)
C8—C9—H9	120.0	F24—C21—C22	118.77 (11)
C10—C9—H9	120.0	C20—C21—C22	122.92 (10)
C11—C10—C9	119.93 (11)	C21—C22—C23	118.44 (11)
C11—C10—H10	120.0	C21—C22—H22	120.8
C9—C10—H10	120.0	C23—C22—H22	120.8
C10—C11—C6	119.71 (11)	C22—C23—C18	120.90 (10)
C10—C11—H11	120.1	C22—C23—H23	119.6
C6—C11—H11	120.1	C18—C23—H23	119.6
C13—C12—C17	117.35 (9)	C5—N25—H25A	119.6
C13—C12—C3	121.00 (9)	C5—N25—H25B	111.0
C17—C12—C3	121.66 (10)	H25A—N25—H25B	116.5
C5—N1—N2—C3	−0.46 (12)	N1—C6—C11—C10	−176.75 (10)
C6—N1—N2—C3	178.81 (9)	N2—C3—C12—C13	−40.18 (15)
N1—N2—C3—C4	−0.21 (12)	C4—C3—C12—C13	139.92 (12)
N1—N2—C3—C12	179.88 (9)	N2—C3—C12—C17	139.91 (11)
N2—C3—C4—C5	0.76 (13)	C4—C3—C12—C17	−39.99 (17)
C12—C3—C4—C5	−179.34 (11)	C17—C12—C13—C14	0.40 (16)
N2—C3—C4—C18	179.05 (10)	C3—C12—C13—C14	−179.51 (10)
C12—C3—C4—C18	−1.05 (19)	C12—C13—C14—N15	1.25 (18)
N2—N1—C5—N25	−179.34 (10)	C13—C14—N15—C16	−1.73 (18)
C6—N1—C5—N25	1.49 (18)	C14—N15—C16—C17	0.61 (18)
N2—N1—C5—C4	0.95 (13)	N15—C16—C17—C12	0.97 (19)
C6—N1—C5—C4	−178.22 (11)	C13—C12—C17—C16	−1.43 (16)
C3—C4—C5—N1	−0.99 (12)	C3—C12—C17—C16	178.48 (10)
C18—C4—C5—N1	−179.31 (10)	C5—C4—C18—C23	−45.51 (16)
C3—C4—C5—N25	179.33 (12)	C3—C4—C18—C23	136.58 (12)
C18—C4—C5—N25	1.0 (2)	C5—C4—C18—C19	135.85 (12)
C5—N1—C6—C7	33.57 (17)	C3—C4—C18—C19	−42.06 (16)
N2—N1—C6—C7	−145.55 (10)	C23—C18—C19—C20	−2.48 (16)
C5—N1—C6—C11	−148.95 (11)	C4—C18—C19—C20	176.19 (10)
N2—N1—C6—C11	31.93 (15)	C18—C19—C20—C21	1.16 (17)
C11—C6—C7—C8	1.73 (17)	C19—C20—C21—F24	−178.07 (10)
N1—C6—C7—C8	179.17 (10)	C19—C20—C21—C22	1.21 (18)
C6—C7—C8—C9	−2.19 (18)	F24—C21—C22—C23	177.17 (10)
C7—C8—C9—C10	0.18 (19)	C20—C21—C22—C23	−2.11 (18)
C8—C9—C10—C11	2.31 (19)	C21—C22—C23—C18	0.67 (17)
C9—C10—C11—C6	−2.76 (18)	C19—C18—C23—C22	1.54 (16)
C7—C6—C11—C10	0.74 (17)	C4—C18—C23—C22	−177.13 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N25—H25A···N15i	0.85	2.18	2.9866 (13)	158
N25—H25B···F24ii	0.86	2.44	3.0631 (11)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N25—H25A⋯N15i	0.85	2.18	2.9866 (13)	158
N25—H25B⋯F24ii	0.86	2.44	3.0631 (11)	130

Symmetry codes: (i) ; (ii) .