7-[4-(4-Fluoro-phen-yl)-2-methyl-sulfanyl-1H-imidazol-5-yl]tetra-zolo[1,5-a]pyridine.

The crystal structure of the title compound, C(15)H(11)FN(6)S, forms a three-dimensional network stabilized by π-π inter-actions between the imidazole core and the tetra-zole ring of the tetra-zolopyridine-unit; the centroid-centroid distance is 3.627 (1) Å. The crystal structure also displays bifurcated N-H⋯(N,N) hydrogen bonding and C-H⋯F inter-actions. The former involve the NH H atom of the imidazole core and the tetra-zolopyridine N atoms, while the latter involve a methyl H atom, of the methyl-sulfanyl group, and the 4-fluoro-phenyl F atom. In the mol-ecule, the imidazole ring makes dihedral angles of 40.45 (9) and 17.09 (8)°, respectively, with the 4-fluoro-phenyl ring and the tetra-zolopyridine ring mean plane.

Related literature

For the biological relevance and the development of p38 MAP kinase inhibitors, see: see: Peifer et al. (2006 ▶). For the preparation of 2-fluoro-4-[4-(4-fluoro­phen­yl)-2-(methyl­thio)-1H-imidazol-5-yl]pyridine, see: Laufer & Liedtke (2006 ▶). For the preparation of tetra­zolopyridines, see: Capelli et al. (2008 ▶).

Experimental

Crystal data

C15H11FN6S

M = 326.36

Monoclinic,

a = 9.8342 (7) Å

b = 18.1908 (6) Å

c = 8.2374 (7) Å

β = 100.292 (3)°

V = 1449.89 (17) Å3

Z = 4

Cu Kα radiation

μ = 2.17 mm−1

T = 193 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971 ▶) T min = 0.866, T max = 0.999

5760 measured reflections

2733 independent reflections

2403 reflections with I > 2σ(I)

R int = 0.056

3 standard reflections every 60 min intensity decay: 3%

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.06

2733 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.30 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/S1600536810002680/su2158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002680/su2158Isup2.hkl

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

C15H11FN6S	F(000) = 672
Mr = 326.36	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.8342 (7) Å	θ = 65–70°
b = 18.1908 (6) Å	µ = 2.17 mm−1
c = 8.2374 (7) Å	T = 193 K
β = 100.292 (3)°	Plate, colourless
V = 1449.89 (17) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2403 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.056
graphite	θmax = 69.9°, θmin = 4.6°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971)	k = −22→22
Tmin = 0.866, Tmax = 0.999	l = −10→0
5760 measured reflections	3 standard reflections every 60 min
2733 independent reflections	intensity decay: 3%

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.051P)2 + 0.5315P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2733 reflections	Δρmax = 0.37 e Å−3
210 parameters	Δρmin = −0.30 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: 0.0014 (2)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
S20	0.84423 (5)	0.32567 (2)	0.15709 (8)	0.0423 (2)
F19	0.09192 (12)	0.08344 (6)	0.37488 (16)	0.0442 (4)
N1	0.29691 (15)	0.61704 (7)	0.31439 (19)	0.0284 (4)
N2	0.18289 (15)	0.63452 (8)	0.3762 (2)	0.0315 (4)
N3	0.12953 (15)	0.57831 (8)	0.4381 (2)	0.0304 (4)
N3A	0.21213 (13)	0.52053 (7)	0.41594 (17)	0.0232 (4)
N8	0.62050 (14)	0.39105 (8)	0.25381 (18)	0.0265 (4)
N10	0.61319 (14)	0.26910 (7)	0.24463 (18)	0.0271 (4)
C4	0.20076 (17)	0.44913 (9)	0.4666 (2)	0.0267 (5)
C5	0.29443 (17)	0.40040 (9)	0.4318 (2)	0.0264 (5)
C6	0.40054 (16)	0.42075 (8)	0.3415 (2)	0.0221 (4)
C7	0.41195 (16)	0.49369 (9)	0.2991 (2)	0.0231 (4)
C7A	0.31553 (16)	0.54434 (9)	0.3388 (2)	0.0230 (4)
C9	0.68541 (17)	0.33087 (9)	0.2239 (2)	0.0275 (5)
C11	0.49088 (16)	0.29071 (9)	0.2895 (2)	0.0239 (5)
C12	0.49810 (16)	0.36671 (9)	0.2974 (2)	0.0233 (5)
C13	0.38534 (16)	0.23580 (9)	0.3073 (2)	0.0241 (5)
C14	0.24524 (17)	0.24835 (9)	0.2461 (2)	0.0286 (5)
C15	0.14573 (18)	0.19732 (10)	0.2673 (2)	0.0313 (5)
C16	0.18916 (19)	0.13307 (9)	0.3491 (2)	0.0301 (5)
C17	0.32598 (19)	0.11634 (9)	0.4043 (2)	0.0297 (5)
C18	0.42396 (18)	0.16837 (9)	0.3835 (2)	0.0266 (5)
C21	0.8749 (2)	0.42202 (11)	0.1351 (3)	0.0420 (7)
H4	0.12940	0.43470	0.52390	0.0320*
H5	0.29010	0.35100	0.46820	0.0320*
H7	0.48390	0.50930	0.24390	0.0280*
H10	0.64590	0.22270	0.23220	0.0320*
H14	0.21790	0.29280	0.18890	0.0340*
H15	0.05050	0.20630	0.22690	0.0380*
H17	0.35240	0.07040	0.45520	0.0360*
H18	0.51900	0.15820	0.42160	0.0320*
H21A	0.80250	0.44270	0.05010	0.0630*
H21B	0.96520	0.42910	0.10280	0.0630*
H21C	0.87380	0.44690	0.24030	0.0630*

	U11	U22	U33	U12	U13	U23
S20	0.0311 (3)	0.0261 (3)	0.0757 (4)	0.0036 (2)	0.0258 (2)	−0.0011 (2)
F19	0.0400 (6)	0.0307 (6)	0.0661 (8)	−0.0095 (5)	0.0210 (6)	0.0042 (5)
N1	0.0261 (7)	0.0188 (7)	0.0413 (8)	0.0027 (5)	0.0087 (6)	0.0029 (6)
N2	0.0264 (7)	0.0217 (7)	0.0478 (9)	0.0046 (6)	0.0104 (6)	0.0033 (6)
N3	0.0264 (7)	0.0230 (7)	0.0436 (9)	0.0066 (6)	0.0112 (6)	0.0017 (6)
N3A	0.0207 (6)	0.0193 (6)	0.0304 (7)	0.0018 (5)	0.0066 (5)	0.0006 (5)
N8	0.0218 (7)	0.0208 (7)	0.0377 (8)	0.0005 (5)	0.0073 (6)	−0.0022 (6)
N10	0.0239 (7)	0.0182 (6)	0.0395 (8)	0.0026 (5)	0.0067 (6)	−0.0020 (6)
C4	0.0273 (8)	0.0208 (8)	0.0342 (9)	−0.0014 (6)	0.0113 (7)	0.0034 (7)
C5	0.0304 (8)	0.0185 (8)	0.0311 (9)	−0.0003 (6)	0.0076 (7)	0.0027 (7)
C6	0.0209 (7)	0.0192 (7)	0.0255 (8)	0.0000 (6)	0.0019 (6)	−0.0016 (6)
C7	0.0202 (7)	0.0204 (7)	0.0293 (8)	−0.0014 (6)	0.0059 (6)	−0.0012 (6)
C7A	0.0211 (7)	0.0191 (7)	0.0286 (8)	−0.0018 (6)	0.0037 (6)	0.0000 (6)
C9	0.0219 (8)	0.0219 (8)	0.0390 (9)	0.0005 (6)	0.0062 (7)	−0.0014 (7)
C11	0.0228 (8)	0.0194 (8)	0.0287 (8)	0.0020 (6)	0.0027 (6)	−0.0015 (6)
C12	0.0221 (8)	0.0198 (8)	0.0275 (8)	0.0007 (6)	0.0031 (6)	−0.0004 (6)
C13	0.0265 (8)	0.0193 (8)	0.0262 (8)	0.0003 (6)	0.0043 (6)	−0.0028 (6)
C14	0.0283 (9)	0.0198 (8)	0.0364 (10)	0.0018 (7)	0.0022 (7)	0.0005 (7)
C15	0.0246 (8)	0.0256 (8)	0.0432 (10)	0.0009 (7)	0.0044 (7)	−0.0034 (8)
C16	0.0320 (9)	0.0227 (8)	0.0382 (9)	−0.0057 (7)	0.0133 (7)	−0.0041 (7)
C17	0.0389 (10)	0.0212 (8)	0.0299 (9)	0.0016 (7)	0.0088 (7)	0.0025 (7)
C18	0.0280 (8)	0.0222 (8)	0.0288 (8)	0.0027 (6)	0.0026 (7)	−0.0005 (6)
C21	0.0417 (11)	0.0295 (10)	0.0608 (13)	−0.0047 (8)	0.0255 (10)	−0.0009 (9)

S20—C9	1.7488 (18)	C11—C12	1.385 (2)
S20—C21	1.793 (2)	C11—C13	1.467 (2)
F19—C16	1.359 (2)	C13—C18	1.399 (2)
N1—N2	1.350 (2)	C13—C14	1.399 (2)
N1—C7A	1.345 (2)	C14—C15	1.382 (2)
N2—N3	1.295 (2)	C15—C16	1.378 (2)
N3—N3A	1.361 (2)	C16—C17	1.375 (3)
N3A—C4	1.375 (2)	C17—C18	1.383 (2)
N3A—C7A	1.362 (2)	C4—H4	0.9500
N8—C9	1.313 (2)	C5—H5	0.9500
N8—C12	1.389 (2)	C7—H7	0.9500
N10—C9	1.356 (2)	C14—H14	0.9500
N10—C11	1.377 (2)	C15—H15	0.9500
N10—H10	0.9200	C17—H17	0.9500
C4—C5	1.346 (2)	C18—H18	0.9500
C5—C6	1.434 (2)	C21—H21A	0.9800
C6—C7	1.382 (2)	C21—H21B	0.9800
C6—C12	1.464 (2)	C21—H21C	0.9800
C7—C7A	1.402 (2)
C9—S20—C21	98.90 (9)	C11—C13—C14	121.46 (15)
N2—N1—C7A	105.98 (13)	C11—C13—C18	120.11 (15)
N1—N2—N3	112.64 (14)	C13—C14—C15	121.26 (15)
N2—N3—N3A	105.28 (14)	C14—C15—C16	117.82 (16)
N3—N3A—C4	127.32 (14)	F19—C16—C17	118.39 (15)
N3—N3A—C7A	109.28 (13)	F19—C16—C15	118.32 (16)
C4—N3A—C7A	123.36 (14)	C15—C16—C17	123.28 (17)
C9—N8—C12	104.82 (14)	C16—C17—C18	118.02 (15)
C9—N10—C11	107.42 (13)	C13—C18—C17	121.08 (16)
C11—N10—H10	129.00	N3A—C4—H4	121.00
C9—N10—H10	123.00	C5—C4—H4	121.00
N3A—C4—C5	117.50 (15)	C4—C5—H5	119.00
C4—C5—C6	121.98 (15)	C6—C5—H5	119.00
C5—C6—C7	118.59 (14)	C6—C7—H7	121.00
C5—C6—C12	121.68 (14)	C7A—C7—H7	121.00
C7—C6—C12	119.71 (14)	C13—C14—H14	119.00
C6—C7—C7A	118.90 (15)	C15—C14—H14	119.00
N3A—C7A—C7	119.48 (14)	C14—C15—H15	121.00
N1—C7A—N3A	106.81 (14)	C16—C15—H15	121.00
N1—C7A—C7	133.70 (15)	C16—C17—H17	121.00
S20—C9—N8	126.57 (13)	C18—C17—H17	121.00
S20—C9—N10	120.80 (12)	C13—C18—H18	119.00
N8—C9—N10	112.59 (15)	C17—C18—H18	119.00
N10—C11—C12	104.93 (14)	S20—C21—H21A	109.00
C12—C11—C13	134.93 (15)	S20—C21—H21B	109.00
N10—C11—C13	120.00 (14)	S20—C21—H21C	109.00
N8—C12—C11	110.22 (14)	H21A—C21—H21B	109.00
C6—C12—C11	130.65 (15)	H21A—C21—H21C	109.00
N8—C12—C6	119.13 (14)	H21B—C21—H21C	109.00
C14—C13—C18	118.41 (15)
C21—S20—C9—N8	−3.16 (18)	C5—C6—C12—C11	18.8 (3)
C21—S20—C9—N10	174.43 (15)	C7—C6—C12—N8	16.8 (2)
N2—N1—C7A—C7	178.07 (18)	C7—C6—C12—C11	−162.78 (17)
N2—N1—C7A—N3A	−0.43 (18)	C5—C6—C12—N8	−161.63 (15)
C7A—N1—N2—N3	0.4 (2)	C12—C6—C7—C7A	178.46 (15)
N1—N2—N3—N3A	−0.1 (2)	C6—C7—C7A—N3A	−0.9 (2)
N2—N3—N3A—C7A	−0.15 (18)	C6—C7—C7A—N1	−179.22 (18)
N2—N3—N3A—C4	177.50 (16)	N10—C11—C12—N8	1.62 (18)
N3—N3A—C7A—N1	0.37 (18)	N10—C11—C12—C6	−178.74 (16)
N3—N3A—C4—C5	−179.88 (15)	C13—C11—C12—N8	−173.91 (17)
C7A—N3A—C4—C5	−2.5 (2)	C13—C11—C12—C6	5.7 (3)
C4—N3A—C7A—C7	3.9 (2)	N10—C11—C13—C14	−136.99 (17)
N3—N3A—C7A—C7	−178.39 (15)	N10—C11—C13—C18	41.5 (2)
C4—N3A—C7A—N1	−177.39 (15)	C12—C11—C13—C14	38.0 (3)
C12—N8—C9—S20	177.95 (13)	C12—C11—C13—C18	−143.46 (19)
C9—N8—C12—C11	−1.15 (18)	C11—C13—C14—C15	−178.13 (15)
C12—N8—C9—N10	0.20 (19)	C18—C13—C14—C15	3.3 (2)
C9—N8—C12—C6	179.17 (15)	C11—C13—C18—C17	178.80 (15)
C9—N10—C11—C12	−1.45 (18)	C14—C13—C18—C17	−2.6 (2)
C9—N10—C11—C13	174.90 (15)	C13—C14—C15—C16	−0.8 (2)
C11—N10—C9—S20	−177.08 (12)	C14—C15—C16—F19	178.12 (15)
C11—N10—C9—N8	0.82 (19)	C14—C15—C16—C17	−2.6 (3)
N3A—C4—C5—C6	−1.7 (2)	F19—C16—C17—C18	−177.45 (15)
C4—C5—C6—C7	4.4 (2)	C15—C16—C17—C18	3.3 (3)
C4—C5—C6—C12	−177.10 (16)	C16—C17—C18—C13	−0.6 (2)
C5—C6—C7—C7A	−3.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N10—H10···N1i	0.92	2.06	2.9703 (19)	174
N10—H10···N2i	0.92	2.60	3.423 (2)	151
C7—H7···N8	0.95	2.53	2.847 (2)	100
C21—H21B···F19ii	0.98	2.44	3.286 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N10—H10⋯N1i	0.92	2.06	2.9703 (19)	174
N10—H10⋯N2i	0.92	2.60	3.423 (2)	151
C21—H21B⋯F19ii	0.98	2.44	3.286 (3)	144

Symmetry codes: (i) ; (ii) .