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

In the crystal structure of the title compound, C(20)H(14)FN(5)O(2), the pyrazole ring forms dihedral angles of 59.3 (2), 25.6 (2) and 46.0 (2)° with the directly attached 4-fluoro-phenyl, pyridine and nitro-phenyl rings, respectively. The crystal packing is characterized by inter-molecular N-H⋯N and N-H⋯O 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

C20H14FN5O2

M = 375.36

Triclinic,

a = 8.5088 (14) Å

b = 9.8797 (11) Å

c = 10.4264 (14) Å

α = 79.906 (10)°

β = 78.764 (10)°

γ = 86.245 (9)°

V = 845.9 (2) Å3

Z = 2

Cu Kα radiation

μ = 0.89 mm−1

T = 193 K

0.35 × 0.35 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3416 measured reflections

3185 independent reflections

2835 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.247

S = 1.18

3185 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.73 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); 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/S1600536812004102/bt5809sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004102/bt5809Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004102/bt5809Isup3.cml

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

C20H14FN5O2	Z = 2
Mr = 375.36	F(000) = 388
Triclinic, P1	Dx = 1.474 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.5088 (14) Å	Cell parameters from 25 reflections
b = 9.8797 (11) Å	θ = 65–69°
c = 10.4264 (14) Å	µ = 0.89 mm−1
α = 79.906 (10)°	T = 193 K
β = 78.764 (10)°	Block, brown
γ = 86.245 (9)°	0.35 × 0.35 × 0.20 mm
V = 845.9 (2) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.020
Radiation source: rotating anode	θmax = 69.8°, θmin = 4.4°
Graphite monochromator	h = −10→0
ω/2θ scans	k = −12→12
3416 measured reflections	l = −12→12
3185 independent reflections	3 standard reflections every 60 min
2835 reflections with I > 2σ(I)	intensity decay: 2%

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070	H-atom parameters constrained
wR(F2) = 0.247	w = 1/[σ2(Fo2) + (0.1328P)2 + 1.0029P] where P = (Fo2 + 2Fc2)/3
S = 1.18	(Δ/σ)max < 0.001
3185 reflections	Δρmax = 0.49 e Å−3
254 parameters	Δρmin = −0.73 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.056 (6)

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	0.2765 (3)	0.5908 (2)	0.7116 (2)	0.0313 (6)
C2	0.2170 (4)	0.4635 (3)	0.7619 (3)	0.0296 (7)
C3	0.2085 (4)	0.4005 (3)	0.6544 (3)	0.0303 (7)
C4	0.2649 (4)	0.5007 (3)	0.5421 (3)	0.0309 (7)
N5	0.3086 (3)	0.6147 (3)	0.5750 (2)	0.0325 (6)
N6	0.1761 (3)	0.4154 (3)	0.8957 (2)	0.0339 (6)
H6A	0.1666	0.3231	0.9181	0.051*
H6B	0.2382	0.4442	0.9420	0.051*
C7	0.3021 (4)	0.6985 (3)	0.7779 (3)	0.0306 (7)
C8	0.4406 (4)	0.7722 (3)	0.7327 (3)	0.0385 (8)
H8	0.5222	0.7431	0.6661	0.046*
C9	0.4599 (4)	0.8882 (3)	0.7848 (3)	0.0407 (8)
H9	0.5546	0.9394	0.7556	0.049*
C10	0.3373 (4)	0.9277 (3)	0.8805 (3)	0.0365 (8)
C11	0.2029 (4)	0.8520 (3)	0.9310 (3)	0.0369 (7)
H11	0.1230	0.8802	0.9992	0.044*
C12	0.1854 (4)	0.7340 (3)	0.8809 (3)	0.0338 (7)
H12	0.0952	0.6783	0.9163	0.041*
N13	0.3484 (4)	1.0589 (3)	0.9244 (3)	0.0436 (7)
O14	0.2312 (4)	1.1002 (2)	0.9998 (3)	0.0565 (8)
O15	0.4705 (4)	1.1239 (3)	0.8826 (3)	0.0571 (8)
C16	0.1488 (4)	0.2617 (3)	0.6615 (3)	0.0322 (7)
C17	0.2460 (5)	0.1614 (3)	0.6016 (3)	0.0402 (8)
H17	0.3543	0.1802	0.5616	0.048*
C18	0.1847 (6)	0.0344 (4)	0.6006 (4)	0.0535 (11)
H18	0.2493	−0.0331	0.5583	0.064*
C19	0.0299 (6)	0.0088 (4)	0.6616 (4)	0.0530 (11)
C20	−0.0680 (5)	0.1035 (4)	0.7234 (4)	0.0537 (10)
H20	−0.1751	0.0827	0.7655	0.064*
C21	−0.0064 (4)	0.2304 (3)	0.7228 (3)	0.0410 (8)
H21	−0.0724	0.2970	0.7654	0.049*
F22	−0.0294 (4)	−0.1151 (2)	0.6613 (3)	0.0839 (11)
C23	0.2733 (4)	0.4946 (3)	0.4002 (3)	0.0311 (7)
C24	0.3791 (4)	0.5746 (3)	0.3017 (3)	0.0325 (7)
H24	0.4492	0.6336	0.3246	0.039*
C25	0.3810 (4)	0.5674 (3)	0.1697 (3)	0.0351 (7)
H25	0.4530	0.6237	0.1038	0.042*
N26	0.2871 (4)	0.4856 (3)	0.1299 (2)	0.0377 (7)
C27	0.1860 (4)	0.4099 (3)	0.2248 (3)	0.0380 (8)
H27	0.1185	0.3511	0.1985	0.046*
C28	0.1722 (4)	0.4108 (3)	0.3597 (3)	0.0358 (7)
H28	0.0960	0.3559	0.4228	0.043*

	U11	U22	U33	U12	U13	U23
N1	0.0511 (15)	0.0246 (12)	0.0214 (12)	−0.0101 (10)	−0.0109 (10)	−0.0043 (9)
C2	0.0429 (15)	0.0256 (14)	0.0222 (13)	−0.0076 (11)	−0.0086 (11)	−0.0039 (11)
C3	0.0468 (16)	0.0247 (14)	0.0228 (13)	−0.0090 (12)	−0.0129 (12)	−0.0028 (11)
C4	0.0462 (16)	0.0268 (14)	0.0226 (14)	−0.0093 (12)	−0.0126 (12)	−0.0026 (11)
N5	0.0520 (15)	0.0280 (12)	0.0194 (11)	−0.0121 (10)	−0.0087 (10)	−0.0029 (9)
N6	0.0572 (16)	0.0265 (12)	0.0207 (12)	−0.0128 (11)	−0.0116 (11)	−0.0023 (9)
C7	0.0497 (17)	0.0234 (14)	0.0220 (13)	−0.0074 (12)	−0.0134 (12)	−0.0027 (10)
C8	0.0541 (19)	0.0316 (16)	0.0323 (16)	−0.0127 (14)	−0.0101 (14)	−0.0053 (12)
C9	0.0567 (19)	0.0307 (16)	0.0373 (17)	−0.0164 (14)	−0.0114 (14)	−0.0044 (13)
C10	0.063 (2)	0.0234 (15)	0.0271 (14)	−0.0100 (13)	−0.0179 (14)	−0.0027 (11)
C11	0.060 (2)	0.0285 (15)	0.0250 (14)	−0.0076 (13)	−0.0133 (13)	−0.0042 (11)
C12	0.0519 (18)	0.0271 (15)	0.0243 (14)	−0.0106 (13)	−0.0097 (12)	−0.0033 (11)
N13	0.076 (2)	0.0256 (13)	0.0334 (14)	−0.0117 (13)	−0.0178 (14)	−0.0038 (11)
O14	0.094 (2)	0.0309 (13)	0.0451 (14)	−0.0082 (13)	−0.0039 (14)	−0.0144 (11)
O15	0.084 (2)	0.0341 (13)	0.0586 (17)	−0.0257 (13)	−0.0204 (14)	−0.0071 (12)
C16	0.0545 (18)	0.0257 (14)	0.0198 (13)	−0.0108 (12)	−0.0149 (12)	−0.0005 (10)
C17	0.066 (2)	0.0311 (16)	0.0273 (15)	0.0001 (14)	−0.0170 (14)	−0.0058 (12)
C18	0.104 (3)	0.0278 (16)	0.0387 (18)	0.0041 (18)	−0.036 (2)	−0.0099 (14)
C19	0.099 (3)	0.0296 (17)	0.0393 (18)	−0.0258 (18)	−0.037 (2)	0.0055 (14)
C20	0.078 (3)	0.048 (2)	0.0398 (18)	−0.0335 (19)	−0.0242 (18)	0.0077 (16)
C21	0.058 (2)	0.0366 (17)	0.0298 (15)	−0.0182 (15)	−0.0110 (14)	−0.0009 (13)
F22	0.162 (3)	0.0346 (12)	0.0725 (17)	−0.0424 (15)	−0.0671 (19)	0.0075 (11)
C23	0.0493 (17)	0.0246 (14)	0.0227 (14)	−0.0061 (12)	−0.0139 (12)	−0.0027 (11)
C24	0.0458 (16)	0.0280 (14)	0.0264 (14)	−0.0110 (12)	−0.0101 (12)	−0.0041 (11)
C25	0.0506 (18)	0.0321 (15)	0.0231 (14)	−0.0133 (13)	−0.0074 (12)	−0.0006 (11)
N26	0.0587 (17)	0.0333 (14)	0.0249 (12)	−0.0115 (12)	−0.0161 (11)	−0.0024 (10)
C27	0.0579 (19)	0.0326 (16)	0.0286 (15)	−0.0163 (14)	−0.0184 (14)	−0.0023 (12)
C28	0.0558 (18)	0.0292 (15)	0.0252 (14)	−0.0151 (13)	−0.0155 (13)	0.0018 (11)

N1—C2	1.365 (4)	N13—O14	1.238 (4)
N1—N5	1.378 (3)	C16—C21	1.379 (5)
N1—C7	1.416 (3)	C16—C17	1.401 (5)
C2—N6	1.376 (4)	C17—C18	1.393 (5)
C2—C3	1.390 (4)	C17—H17	0.9500
C3—C4	1.420 (4)	C18—C19	1.366 (6)
C3—C16	1.478 (4)	C18—H18	0.9500
C4—N5	1.329 (4)	C19—F22	1.355 (4)
C4—C23	1.479 (4)	C19—C20	1.372 (7)
N6—H6A	0.9055	C20—C21	1.389 (5)
N6—H6B	0.8721	C20—H20	0.9500
C7—C8	1.384 (4)	C21—H21	0.9500
C7—C12	1.390 (4)	C23—C24	1.392 (4)
C8—C9	1.383 (4)	C23—C28	1.400 (4)
C8—H8	0.9500	C24—C25	1.387 (4)
C9—C10	1.383 (5)	C24—H24	0.9500
C9—H9	0.9500	C25—N26	1.340 (4)
C10—C11	1.372 (5)	C25—H25	0.9500
C10—N13	1.463 (4)	N26—C27	1.331 (4)
C11—C12	1.386 (4)	C27—C28	1.390 (4)
C11—H11	0.9500	C27—H27	0.9500
C12—H12	0.9500	C28—H28	0.9500
N13—O15	1.223 (4)
C2—N1—N5	112.1 (2)	O14—N13—C10	118.0 (3)
C2—N1—C7	129.9 (2)	C21—C16—C17	118.8 (3)
N5—N1—C7	117.9 (2)	C21—C16—C3	120.4 (3)
N1—C2—N6	123.1 (2)	C17—C16—C3	120.8 (3)
N1—C2—C3	106.9 (2)	C18—C17—C16	120.3 (4)
N6—C2—C3	130.0 (3)	C18—C17—H17	119.8
C2—C3—C4	104.2 (2)	C16—C17—H17	119.8
C2—C3—C16	125.9 (3)	C19—C18—C17	118.7 (4)
C4—C3—C16	129.9 (2)	C19—C18—H18	120.7
N5—C4—C3	112.7 (2)	C17—C18—H18	120.7
N5—C4—C23	118.7 (2)	F22—C19—C18	118.7 (4)
C3—C4—C23	128.6 (3)	F22—C19—C20	118.7 (4)
C4—N5—N1	104.1 (2)	C18—C19—C20	122.6 (3)
C2—N6—H6A	115.2	C19—C20—C21	118.3 (4)
C2—N6—H6B	113.1	C19—C20—H20	120.9
H6A—N6—H6B	110.1	C21—C20—H20	120.9
C8—C7—C12	121.2 (3)	C16—C21—C20	121.3 (4)
C8—C7—N1	118.5 (3)	C16—C21—H21	119.4
C12—C7—N1	120.2 (3)	C20—C21—H21	119.4
C9—C8—C7	119.8 (3)	C24—C23—C28	117.5 (3)
C9—C8—H8	120.1	C24—C23—C4	121.3 (3)
C7—C8—H8	120.1	C28—C23—C4	121.2 (3)
C10—C9—C8	118.2 (3)	C25—C24—C23	119.3 (3)
C10—C9—H9	120.9	C25—C24—H24	120.3
C8—C9—H9	120.9	C23—C24—H24	120.3
C11—C10—C9	122.6 (3)	N26—C25—C24	123.7 (3)
C11—C10—N13	118.9 (3)	N26—C25—H25	118.1
C9—C10—N13	118.4 (3)	C24—C25—H25	118.1
C10—C11—C12	119.1 (3)	C27—N26—C25	116.5 (3)
C10—C11—H11	120.5	N26—C27—C28	124.6 (3)
C12—C11—H11	120.5	N26—C27—H27	117.7
C11—C12—C7	118.9 (3)	C28—C27—H27	117.7
C11—C12—H12	120.6	C27—C28—C23	118.4 (3)
C7—C12—H12	120.6	C27—C28—H28	120.8
O15—N13—O14	123.3 (3)	C23—C28—H28	120.8
O15—N13—C10	118.7 (3)
N5—N1—C2—N6	179.8 (3)	C11—C10—N13—O15	177.7 (3)
C7—N1—C2—N6	−3.0 (5)	C9—C10—N13—O15	−5.4 (4)
N5—N1—C2—C3	−0.3 (3)	C11—C10—N13—O14	−4.2 (4)
C7—N1—C2—C3	176.9 (3)	C9—C10—N13—O14	172.8 (3)
N1—C2—C3—C4	−0.6 (3)	C2—C3—C16—C21	59.9 (4)
N6—C2—C3—C4	179.2 (3)	C4—C3—C16—C21	−118.1 (4)
N1—C2—C3—C16	−179.1 (3)	C2—C3—C16—C17	−122.7 (3)
N6—C2—C3—C16	0.8 (5)	C4—C3—C16—C17	59.2 (5)
C2—C3—C4—N5	1.4 (4)	C21—C16—C17—C18	2.1 (4)
C16—C3—C4—N5	179.8 (3)	C3—C16—C17—C18	−175.3 (3)
C2—C3—C4—C23	−175.8 (3)	C16—C17—C18—C19	−1.5 (5)
C16—C3—C4—C23	2.5 (6)	C17—C18—C19—F22	−179.6 (3)
C3—C4—N5—N1	−1.6 (3)	C17—C18—C19—C20	0.3 (5)
C23—C4—N5—N1	176.0 (3)	F22—C19—C20—C21	−179.8 (3)
C2—N1—N5—C4	1.1 (3)	C18—C19—C20—C21	0.3 (5)
C7—N1—N5—C4	−176.4 (3)	C17—C16—C21—C20	−1.5 (5)
C2—N1—C7—C8	139.2 (3)	C3—C16—C21—C20	176.0 (3)
N5—N1—C7—C8	−43.8 (4)	C19—C20—C21—C16	0.3 (5)
C2—N1—C7—C12	−44.6 (5)	N5—C4—C23—C24	25.7 (5)
N5—N1—C7—C12	132.4 (3)	C3—C4—C23—C24	−157.2 (3)
C12—C7—C8—C9	−4.0 (5)	N5—C4—C23—C28	−152.6 (3)
N1—C7—C8—C9	172.2 (3)	C3—C4—C23—C28	24.5 (5)
C7—C8—C9—C10	−0.7 (5)	C28—C23—C24—C25	−0.5 (5)
C8—C9—C10—C11	4.0 (5)	C4—C23—C24—C25	−178.9 (3)
C8—C9—C10—N13	−172.8 (3)	C23—C24—C25—N26	−0.8 (5)
C9—C10—C11—C12	−2.6 (5)	C24—C25—N26—C27	1.1 (5)
N13—C10—C11—C12	174.2 (3)	C25—N26—C27—C28	0.1 (5)
C10—C11—C12—C7	−2.2 (4)	N26—C27—C28—C23	−1.4 (5)
C8—C7—C12—C11	5.4 (5)	C24—C23—C28—C27	1.5 (5)
N1—C7—C12—C11	−170.7 (3)	C4—C23—C28—C27	179.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O14i	0.91	2.29	3.149 (4)	158
N6—H6B···N26ii	0.87	2.19	2.985 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6A⋯O14i	0.91	2.29	3.149 (4)	158
N6—H6B⋯N26ii	0.87	2.19	2.985 (3)	151

Symmetry codes: (i) ; (ii) .