5-(4-Fluoro-phen-yl)-4-(4-pyrid-yl)-1,3-oxazol-2-amine.

In the crystal structure of the title compound, C(14)H(10)FN(3)O, the plane of the isoxazole ring makes dihedral angles of 35.72 (9) and 30.00 (9)°, respectively, with those of the 4-fluoro-phenyl and pyridine rings. The plane of the 4-fluoro-phenyl ring makes a dihedral angle of 45.85 (8)° with that of the pyridine ring. The crystal structure is stabilized by inter-molecular N-H⋯N hydrogen bonding. The two types of hydrogen bonds result in two chains, extending along the a axis, which are related by centres of symmetry.

Related literature

For the biological activity of pyridinyloxazoles, see: Peifer et al. (2006 ▶). 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 ▶).

Experimental

Crystal data

C14H10FN3O

M = 255.25

Orthorhombic,

a = 10.1017 (4) Å

b = 8.3889 (8) Å

c = 29.127 (2) Å

V = 2468.3 (3) Å3

Z = 8

Cu Kα radiation

μ = 0.84 mm−1

T = 193 K

0.40 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.899, T max = 0.997

2331 measured reflections

2331 independent reflections

1859 reflections with I > 2σ(I)

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.119

S = 1.05

2331 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 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 datablocks I, global. DOI: 10.1107/S1600536810009189/nc2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009189/nc2179Isup2.hkl

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

C14H10FN3O	F(000) = 1056
Mr = 255.25	Dx = 1.374 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 10.1017 (4) Å	θ = 30–46°
b = 8.3889 (8) Å	µ = 0.84 mm−1
c = 29.127 (2) Å	T = 193 K
V = 2468.3 (3) Å3	Plate, yellow
Z = 8	0.40 × 0.30 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1859 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.0000
graphite	θmax = 69.9°, θmin = 3.0°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = 0→10
Tmin = 0.899, Tmax = 0.997	l = −35→0
2331 measured reflections	3 standard reflections every 60 min
2331 independent reflections	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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.5691P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2331 reflections	Δρmax = 0.20 e Å−3
173 parameters	Δρmin = −0.17 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: 0.00056 (12)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
F1	0.14358 (14)	0.10350 (16)	0.19761 (4)	0.0644 (4)
N1	−0.13607 (15)	0.4430 (3)	0.45720 (6)	0.0541 (5)
H1A	−0.1264	0.4860	0.4890	0.081*
H1B	−0.2133	0.4266	0.4415	0.081*
O1	−0.03766 (11)	0.36315 (17)	0.39018 (4)	0.0382 (3)
C2	0.09228 (16)	0.3491 (2)	0.37416 (6)	0.0329 (4)
C3	0.17254 (16)	0.3972 (2)	0.40860 (6)	0.0321 (4)
N4	0.09727 (14)	0.44405 (19)	0.44663 (5)	0.0362 (4)
C5	−0.02508 (16)	0.4204 (2)	0.43365 (6)	0.0378 (4)
C6	0.10541 (15)	0.2869 (2)	0.32790 (6)	0.0325 (4)
C7	0.20470 (17)	0.3409 (2)	0.29845 (6)	0.0371 (4)
H7	0.2644	0.4208	0.3087	0.044*
C8	0.21765 (18)	0.2803 (2)	0.25471 (6)	0.0423 (5)
H8	0.2856	0.3175	0.2348	0.051*
C9	0.1303 (2)	0.1652 (2)	0.24045 (6)	0.0435 (5)
C10	0.0300 (2)	0.1098 (2)	0.26787 (7)	0.0463 (5)
H10	−0.0300	0.0314	0.2569	0.056*
C11	0.01776 (17)	0.1703 (2)	0.31191 (6)	0.0394 (4)
H11	−0.0507	0.1324	0.3314	0.047*
C12	0.31809 (16)	0.4044 (2)	0.41163 (6)	0.0316 (4)
C13	0.37771 (16)	0.5163 (2)	0.43992 (6)	0.0348 (4)
H13	0.3254	0.5891	0.4571	0.042*
C14	0.51470 (17)	0.5205 (2)	0.44293 (6)	0.0395 (4)
H14	0.5539	0.5991	0.4621	0.047*
N15	0.59471 (15)	0.4203 (2)	0.42047 (5)	0.0439 (4)
C16	0.53651 (17)	0.3118 (3)	0.39376 (7)	0.0434 (5)
H16	0.5915	0.2388	0.3777	0.052*
C17	0.40105 (17)	0.2992 (2)	0.38802 (6)	0.0371 (4)
H17	0.3649	0.2201	0.3683	0.045*

	U11	U22	U33	U12	U13	U23
F1	0.0878 (10)	0.0654 (8)	0.0399 (6)	0.0139 (7)	−0.0042 (6)	−0.0098 (6)
N1	0.0211 (7)	0.0942 (14)	0.0470 (9)	0.0003 (8)	0.0007 (7)	−0.0199 (9)
O1	0.0204 (6)	0.0547 (8)	0.0394 (7)	0.0007 (5)	−0.0015 (5)	−0.0051 (6)
C2	0.0199 (8)	0.0389 (9)	0.0400 (9)	0.0008 (7)	0.0013 (7)	0.0024 (7)
C3	0.0233 (8)	0.0345 (8)	0.0383 (9)	−0.0002 (7)	0.0002 (7)	0.0010 (7)
N4	0.0236 (7)	0.0476 (9)	0.0375 (8)	−0.0002 (6)	−0.0009 (6)	−0.0051 (7)
C5	0.0237 (8)	0.0513 (11)	0.0384 (10)	0.0011 (8)	−0.0010 (7)	−0.0059 (8)
C6	0.0229 (7)	0.0369 (9)	0.0378 (9)	0.0032 (7)	−0.0047 (7)	0.0036 (7)
C7	0.0294 (8)	0.0396 (9)	0.0422 (10)	0.0006 (7)	−0.0020 (7)	0.0017 (8)
C8	0.0394 (10)	0.0465 (11)	0.0410 (10)	0.0096 (8)	0.0044 (8)	0.0064 (9)
C9	0.0513 (11)	0.0455 (11)	0.0339 (9)	0.0147 (9)	−0.0062 (8)	−0.0038 (8)
C10	0.0401 (10)	0.0481 (12)	0.0507 (11)	0.0015 (9)	−0.0138 (9)	−0.0063 (9)
C11	0.0258 (8)	0.0480 (11)	0.0444 (10)	−0.0017 (8)	−0.0047 (7)	−0.0005 (9)
C12	0.0222 (8)	0.0362 (9)	0.0364 (9)	0.0005 (7)	−0.0014 (7)	0.0050 (7)
C13	0.0269 (8)	0.0406 (10)	0.0368 (9)	−0.0008 (7)	0.0002 (7)	−0.0003 (8)
C14	0.0279 (8)	0.0510 (11)	0.0396 (10)	−0.0071 (8)	−0.0049 (7)	0.0010 (9)
N15	0.0245 (7)	0.0632 (11)	0.0441 (9)	−0.0009 (7)	−0.0029 (6)	0.0010 (8)
C16	0.0274 (9)	0.0548 (12)	0.0480 (11)	0.0074 (8)	−0.0006 (8)	−0.0032 (9)
C17	0.0281 (9)	0.0391 (10)	0.0442 (10)	0.0020 (7)	−0.0034 (7)	−0.0023 (8)

F1—C9	1.358 (2)	C8—H8	0.9500
N1—C5	1.328 (2)	C9—C10	1.372 (3)
N1—H1A	0.9994	C10—C11	1.385 (3)
N1—H1B	0.9144	C10—H10	0.9500
O1—C5	1.360 (2)	C11—H11	0.9500
O1—C2	1.3981 (19)	C12—C13	1.386 (2)
C2—C3	1.351 (2)	C12—C17	1.398 (2)
C2—C6	1.451 (2)	C13—C14	1.387 (2)
C3—N4	1.400 (2)	C13—H13	0.9500
C3—C12	1.474 (2)	C14—N15	1.337 (3)
N4—C5	1.308 (2)	C14—H14	0.9500
C6—C7	1.395 (2)	N15—C16	1.334 (3)
C6—C11	1.399 (2)	C16—C17	1.383 (2)
C7—C8	1.378 (3)	C16—H16	0.9500
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.372 (3)
C5—N1—H1A	116.6	F1—C9—C8	118.89 (18)
C5—N1—H1B	116.2	C10—C9—C8	122.51 (17)
H1A—N1—H1B	126.9	C9—C10—C11	118.74 (18)
C5—O1—C2	104.64 (13)	C9—C10—H10	120.6
C3—C2—O1	106.88 (15)	C11—C10—H10	120.6
C3—C2—C6	137.89 (15)	C10—C11—C6	120.54 (18)
O1—C2—C6	115.22 (14)	C10—C11—H11	119.7
C2—C3—N4	110.20 (14)	C6—C11—H11	119.7
C2—C3—C12	130.92 (17)	C13—C12—C17	117.35 (15)
N4—C3—C12	118.87 (15)	C13—C12—C3	119.78 (16)
C5—N4—C3	104.01 (14)	C17—C12—C3	122.85 (16)
N4—C5—N1	128.84 (17)	C12—C13—C14	119.23 (17)
N4—C5—O1	114.27 (15)	C12—C13—H13	120.4
N1—C5—O1	116.89 (15)	C14—C13—H13	120.4
C7—C6—C11	118.51 (17)	N15—C14—C13	123.78 (18)
C7—C6—C2	121.31 (15)	N15—C14—H14	118.1
C11—C6—C2	120.18 (16)	C13—C14—H14	118.1
C8—C7—C6	121.12 (17)	C16—N15—C14	116.61 (16)
C8—C7—H7	119.4	N15—C16—C17	123.99 (18)
C6—C7—H7	119.4	N15—C16—H16	118.0
C9—C8—C7	118.57 (18)	C17—C16—H16	118.0
C9—C8—H8	120.7	C16—C17—C12	119.03 (17)
C7—C8—H8	120.7	C16—C17—H17	120.5
F1—C9—C10	118.59 (19)	C12—C17—H17	120.5
C5—O1—C2—C3	0.36 (19)	C7—C8—C9—F1	−179.13 (16)
C5—O1—C2—C6	179.09 (15)	C7—C8—C9—C10	0.8 (3)
O1—C2—C3—N4	−0.7 (2)	F1—C9—C10—C11	178.78 (17)
C6—C2—C3—N4	−179.0 (2)	C8—C9—C10—C11	−1.1 (3)
O1—C2—C3—C12	178.41 (17)	C9—C10—C11—C6	0.6 (3)
C6—C2—C3—C12	0.1 (4)	C7—C6—C11—C10	0.3 (3)
C2—C3—N4—C5	0.7 (2)	C2—C6—C11—C10	−179.70 (16)
C12—C3—N4—C5	−178.50 (16)	C2—C3—C12—C13	151.88 (19)
C3—N4—C5—N1	178.7 (2)	N4—C3—C12—C13	−29.1 (2)
C3—N4—C5—O1	−0.5 (2)	C2—C3—C12—C17	−30.1 (3)
C2—O1—C5—N4	0.1 (2)	N4—C3—C12—C17	148.94 (17)
C2—O1—C5—N1	−179.15 (18)	C17—C12—C13—C14	1.0 (3)
C3—C2—C6—C7	−37.0 (3)	C3—C12—C13—C14	179.18 (17)
O1—C2—C6—C7	144.77 (16)	C12—C13—C14—N15	−1.1 (3)
C3—C2—C6—C11	142.9 (2)	C13—C14—N15—C16	0.3 (3)
O1—C2—C6—C11	−35.3 (2)	C14—N15—C16—C17	0.5 (3)
C11—C6—C7—C8	−0.6 (3)	N15—C16—C17—C12	−0.6 (3)
C2—C6—C7—C8	179.34 (16)	C13—C12—C17—C16	−0.3 (3)
C6—C7—C8—C9	0.1 (3)	C3—C12—C17—C16	−178.35 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4i	1.00	1.99	2.983 (2)	175
N1—H1B···N15ii	0.91	2.03	2.929 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4i	1.00	1.99	2.983 (2)	175
N1—H1B⋯N15ii	0.91	2.03	2.929 (2)	165

Symmetry codes: (i) ; (ii) .