4-[5-(4-Fluoro-phen-yl)-1H-imidazol-4-yl]pyridine.

In the title compound, C(14)H(10)FN(3), the imidazole ring makes dihedral angles of 28.2 (1) and 36.60 (9)° with the pyridine ring and the 4-fluoro-phenyl ring, respectively. The pyridine ring forms a dihedral angle of 44.68 (9)° with the 4-fluoro-phenyl ring. Inter-molecular N-H⋯N hydrogen bonds are observed in the crystal structure.

Related literature

For the biological activity of the title compound, see: Liverton et al. (1999 ▶). For applications of functionalized 5(4)-(4-fluoro­phen­yl)-4(5)-(pyridin-4-yl)imidazoles, see: Koch et al. (2008 ▶), Peifer et al. (2006 ▶).

Experimental

Crystal data

C14H10FN3

M = 239.25

Orthorhombic,

a = 9.217 (2) Å

b = 8.1064 (5) Å

c = 30.665 (5) Å

V = 2291.1 (6) Å3

Z = 8

Cu Kα radiation

μ = 0.80 mm−1

T = 193 K

0.54 × 0.20 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2121 measured reflections

2121 independent reflections

1707 reflections with I > 2σ(I)

3 standard reflections frequency: 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.201

S = 1.09

2121 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.54 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/S1600536809005650/im2099sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005650/im2099Isup2.hkl

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

C14H10FN3	Dx = 1.387 Mg m−3
Mr = 239.25	Melting point: 285.5 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 9.217 (2) Å	θ = 31–53°
b = 8.1064 (5) Å	µ = 0.80 mm−1
c = 30.665 (5) Å	T = 193 K
V = 2291.1 (6) Å3	Needle, colourless
Z = 8	0.54 × 0.20 × 0.13 mm
F(000) = 992

Enraf–Nonius CAD-4 diffractometer	Rint = 0.0000
Radiation source: rotating anode	θmax = 69.6°, θmin = 2.9°
graphite	h = 0→11
ω/2θ scans	k = 0→9
2121 measured reflections	l = −36→0
2121 independent reflections	3 standard reflections every 60 min
1707 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1422P)2 + 0.0554P] where P = (Fo2 + 2Fc2)/3
2121 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.54 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
F1	0.0873 (2)	0.0708 (3)	0.21998 (6)	0.0596 (6)
N1	−0.0150 (2)	0.2988 (2)	0.42177 (7)	0.0243 (5)
H1	−0.1070	0.2883	0.4130	0.029*
C2	0.1085 (2)	0.2755 (3)	0.39720 (8)	0.0224 (5)
C3	0.2212 (3)	0.3123 (3)	0.42585 (8)	0.0227 (5)
N4	0.1672 (2)	0.3595 (3)	0.46674 (7)	0.0285 (5)
C5	0.0257 (3)	0.3479 (3)	0.46279 (9)	0.0279 (6)
H5	−0.0408	0.3708	0.4857	0.033*
C6	0.1015 (2)	0.2250 (3)	0.35030 (8)	0.0228 (5)
C7	0.1984 (3)	0.2872 (3)	0.31898 (9)	0.0286 (6)
H7	0.2682	0.3669	0.3277	0.034*
C8	0.1955 (3)	0.2353 (3)	0.27519 (9)	0.0338 (6)
H8	0.2639	0.2764	0.2547	0.041*
C9	0.0907 (3)	0.1233 (3)	0.26276 (9)	0.0365 (7)
C10	−0.0096 (3)	0.0625 (3)	0.29215 (9)	0.0353 (6)
H10	−0.0819	−0.0131	0.2828	0.042*
C11	−0.0043 (3)	0.1128 (3)	0.33599 (8)	0.0274 (6)
H11	−0.0731	0.0705	0.3562	0.033*
C12	0.3785 (3)	0.3036 (3)	0.41935 (8)	0.0216 (5)
C13	0.4700 (3)	0.4057 (3)	0.44398 (8)	0.0246 (5)
H13	0.4299	0.4814	0.4643	0.030*
C14	0.6182 (3)	0.3961 (3)	0.43855 (8)	0.0282 (6)
H14	0.6783	0.4650	0.4559	0.034*
N15	0.6824 (2)	0.2927 (3)	0.40951 (7)	0.0287 (5)
C16	0.5937 (3)	0.1937 (3)	0.38606 (9)	0.0290 (6)
H16	0.6367	0.1193	0.3659	0.035*
C17	0.4456 (3)	0.1942 (3)	0.38966 (8)	0.0264 (6)
H17	0.3885	0.1218	0.3724	0.032*

	U11	U22	U33	U12	U13	U23
F1	0.0846 (15)	0.0588 (13)	0.0354 (10)	−0.0016 (11)	−0.0071 (9)	−0.0100 (9)
N1	0.0210 (10)	0.0106 (9)	0.0414 (12)	−0.0012 (7)	0.0000 (8)	−0.0015 (8)
C2	0.0225 (11)	0.0050 (10)	0.0398 (14)	0.0003 (7)	0.0019 (9)	0.0031 (9)
C3	0.0277 (13)	0.0048 (10)	0.0355 (12)	−0.0005 (8)	0.0005 (9)	0.0007 (8)
N4	0.0293 (11)	0.0182 (10)	0.0379 (12)	−0.0021 (8)	0.0020 (9)	−0.0029 (8)
C5	0.0273 (12)	0.0166 (11)	0.0399 (14)	−0.0008 (9)	0.0058 (10)	−0.0027 (10)
C6	0.0234 (11)	0.0078 (10)	0.0371 (13)	0.0037 (8)	−0.0022 (9)	0.0011 (9)
C7	0.0308 (12)	0.0139 (11)	0.0410 (15)	0.0016 (9)	−0.0012 (10)	0.0027 (10)
C8	0.0379 (14)	0.0257 (13)	0.0377 (15)	0.0053 (10)	0.0035 (11)	0.0069 (11)
C9	0.0499 (17)	0.0278 (14)	0.0319 (14)	0.0083 (11)	−0.0085 (12)	−0.0012 (11)
C10	0.0383 (14)	0.0215 (12)	0.0460 (16)	−0.0033 (11)	−0.0113 (12)	−0.0041 (11)
C11	0.0277 (12)	0.0139 (11)	0.0407 (14)	−0.0017 (9)	−0.0044 (10)	0.0020 (9)
C12	0.0239 (12)	0.0070 (10)	0.0337 (13)	−0.0007 (8)	−0.0014 (9)	0.0044 (8)
C13	0.0282 (12)	0.0151 (11)	0.0306 (12)	−0.0020 (9)	−0.0004 (9)	−0.0006 (9)
C14	0.0294 (13)	0.0194 (12)	0.0357 (13)	−0.0036 (9)	−0.0039 (10)	−0.0016 (10)
N15	0.0231 (10)	0.0223 (11)	0.0408 (12)	0.0008 (8)	−0.0016 (9)	0.0022 (9)
C16	0.0286 (13)	0.0156 (12)	0.0429 (15)	0.0050 (9)	−0.0006 (10)	−0.0024 (10)
C17	0.0273 (12)	0.0091 (10)	0.0427 (15)	−0.0001 (9)	−0.0044 (10)	−0.0017 (9)

F1—C9	1.380 (3)	C8—H8	0.9500
N1—C5	1.372 (3)	C9—C10	1.382 (4)
N1—C2	1.378 (3)	C10—C11	1.406 (4)
N1—H1	0.8936	C10—H10	0.9500
C2—C3	1.393 (3)	C11—H11	0.9500
C2—C6	1.496 (3)	C12—C13	1.402 (3)
C3—N4	1.402 (3)	C12—C17	1.414 (3)
C3—C12	1.465 (3)	C13—C14	1.379 (3)
N4—C5	1.313 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—N15	1.359 (3)
C6—C11	1.403 (3)	C14—H14	0.9500
C6—C7	1.405 (3)	N15—C16	1.353 (3)
C7—C8	1.407 (4)	C16—C17	1.370 (3)
C7—H7	0.9500	C16—H16	0.9500
C8—C9	1.379 (4)	C17—H17	0.9500
C5—N1—C2	108.4 (2)	F1—C9—C10	119.7 (3)
C5—N1—H1	124.3	C9—C10—C11	119.8 (2)
C2—N1—H1	127.3	C9—C10—H10	120.1
N1—C2—C3	104.0 (2)	C11—C10—H10	120.1
N1—C2—C6	121.9 (2)	C6—C11—C10	120.7 (2)
C3—C2—C6	134.2 (2)	C6—C11—H11	119.6
C2—C3—N4	111.0 (2)	C10—C11—H11	119.6
C2—C3—C12	129.9 (2)	C13—C12—C17	117.0 (2)
N4—C3—C12	119.0 (2)	C13—C12—C3	119.6 (2)
C5—N4—C3	104.5 (2)	C17—C12—C3	123.4 (2)
N4—C5—N1	112.1 (2)	C14—C13—C12	119.8 (2)
N4—C5—H5	123.9	C14—C13—H13	120.1
N1—C5—H5	123.9	C12—C13—H13	120.1
C11—C6—C7	117.4 (2)	N15—C14—C13	123.1 (2)
C11—C6—C2	120.5 (2)	N15—C14—H14	118.5
C7—C6—C2	122.1 (2)	C13—C14—H14	118.5
C6—C7—C8	122.2 (2)	C16—N15—C14	116.8 (2)
C6—C7—H7	118.9	N15—C16—C17	123.9 (2)
C8—C7—H7	118.9	N15—C16—H16	118.0
C9—C8—C7	118.3 (3)	C17—C16—H16	118.0
C9—C8—H8	120.9	C16—C17—C12	119.3 (2)
C7—C8—H8	120.9	C16—C17—H17	120.3
C8—C9—F1	118.8 (3)	C12—C17—H17	120.3
C8—C9—C10	121.5 (3)
C5—N1—C2—C3	0.3 (2)	C7—C8—C9—C10	0.0 (4)
C5—N1—C2—C6	−178.6 (2)	C8—C9—C10—C11	−1.1 (4)
N1—C2—C3—N4	−0.9 (2)	F1—C9—C10—C11	178.5 (2)
C6—C2—C3—N4	177.8 (2)	C7—C6—C11—C10	1.6 (3)
N1—C2—C3—C12	177.2 (2)	C2—C6—C11—C10	−178.8 (2)
C6—C2—C3—C12	−4.1 (4)	C9—C10—C11—C6	0.2 (4)
C2—C3—N4—C5	1.2 (2)	C2—C3—C12—C13	153.7 (2)
C12—C3—N4—C5	−177.14 (19)	N4—C3—C12—C13	−28.4 (3)
C3—N4—C5—N1	−1.0 (3)	C2—C3—C12—C17	−27.5 (4)
C2—N1—C5—N4	0.4 (3)	N4—C3—C12—C17	150.5 (2)
N1—C2—C6—C11	−37.4 (3)	C17—C12—C13—C14	0.0 (3)
C3—C2—C6—C11	144.1 (2)	C3—C12—C13—C14	178.9 (2)
N1—C2—C6—C7	142.3 (2)	C12—C13—C14—N15	1.1 (4)
C3—C2—C6—C7	−36.3 (4)	C13—C14—N15—C16	−1.5 (4)
C11—C6—C7—C8	−2.7 (3)	C14—N15—C16—C17	0.9 (4)
C2—C6—C7—C8	177.6 (2)	N15—C16—C17—C12	0.1 (4)
C6—C7—C8—C9	2.0 (4)	C13—C12—C17—C16	−0.5 (3)
C7—C8—C9—F1	−179.6 (2)	C3—C12—C17—C16	−179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N15i	0.89	1.94	2.815 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N15i	0.89	1.94	2.815 (3)	164

Symmetry code: (i) .