3-Ethyl-5-(4-meth-oxy-phen-oxy)-2-(pyridin-4-yl)-3H-imidazo[4,5-b]pyridine.

In the title compound, C(20)H(18)N(4)O(2), the imidazopyridine fused ring system is almost perpendicular to the benzene ring [dihedral angle = 87.6 (5)°]. The pyridine ring makes a dihedral angle of 35.5 (5)° with the mean plane of the imidazopyridine fragment. The crystal structure is stabilized by an aromatic π-π stacking inter-action between the phenyl rings of neighbouring mol-ecules [centroid-centroid distance = 3.772 (2) Å, inter-planar distance = 3.546 (2) Å and slippage = 1.286 (2) Å].

Related literature

For the biological activity of pyridine derivatives, see: Passannanti et al. (1998 ▶); Jiyeon et al. (2010 ▶); Abdel-Alim et al. (2005 ▶); Girgis et al. (2006 ▶); Slominska et al. (2008 ▶); Spanka et al. (2010 ▶). For a related structure, see: Ouzidan et al. (2010 ▶). For sp 3 hybridization, see: Beddoes et al. (1986 ▶).

Experimental

Crystal data

C20H18N4O2

M = 346.38

Monoclinic,

a = 13.6591 (4) Å

b = 13.7104 (4) Å

c = 9.3177 (2) Å

β = 98.940 (1)°

V = 1723.74 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.985

24827 measured reflections

5887 independent reflections

3938 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.140

S = 1.00

5887 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023543/lx2189sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023543/lx2189Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023543/lx2189Isup3.cml

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

C20H18N4O2	F(000) = 728
Mr = 346.38	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5887 reflections
a = 13.6591 (4) Å	θ = 1.5–32.0°
b = 13.7104 (4) Å	µ = 0.09 mm−1
c = 9.3177 (2) Å	T = 293 K
β = 98.940 (1)°	Block, white crystalline
V = 1723.74 (8) Å3	0.25 × 0.22 × 0.19 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	5887 independent reflections
Radiation source: fine-focus sealed tube	3938 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 32.1°, θmin = 1.5°
ω and φ scans	h = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −20→20
Tmin = 0.981, Tmax = 0.985	l = −13→12
24827 measured reflections

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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F2) = 0.140	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.068P)2 + 0.2334P] where P = (Fo2 + 2Fc2)/3
5887 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.20 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
C1	0.34424 (9)	0.10472 (9)	0.42615 (13)	0.0383 (3)
C2	0.34457 (9)	0.18018 (9)	0.52777 (14)	0.0406 (3)
H2	0.3850	0.2344	0.5240	0.049*
C3	0.28465 (9)	0.17335 (9)	0.63296 (13)	0.0389 (3)
H3	0.2834	0.2222	0.7020	0.047*
C4	0.22585 (8)	0.09028 (8)	0.63192 (12)	0.0335 (2)
C5	0.23419 (8)	0.02078 (8)	0.52553 (12)	0.0330 (2)
C6	0.12671 (8)	−0.02604 (8)	0.66320 (12)	0.0332 (2)
C7	0.16889 (10)	−0.14643 (8)	0.46766 (13)	0.0403 (3)
H7A	0.1356	−0.1952	0.5182	0.048*
H7B	0.2363	−0.1683	0.4670	0.048*
C8	0.11655 (12)	−0.13785 (11)	0.31346 (15)	0.0547 (4)
H8A	0.0490	−0.1186	0.3137	0.082*
H8B	0.1181	−0.1997	0.2655	0.082*
H8C	0.1493	−0.0897	0.2629	0.082*
C9	0.05197 (8)	−0.08407 (8)	0.72257 (12)	0.0341 (2)
C10	0.05089 (10)	−0.08248 (9)	0.87147 (13)	0.0427 (3)
H10	0.0986	−0.0476	0.9329	0.051*
C11	−0.02193 (11)	−0.13343 (10)	0.92665 (15)	0.0500 (3)
H11	−0.0225	−0.1305	1.0262	0.060*
C12	−0.08936 (10)	−0.18810 (10)	0.70402 (15)	0.0459 (3)
H12	−0.1370	−0.2251	0.6457	0.055*
C13	−0.02073 (9)	−0.13820 (9)	0.63755 (13)	0.0386 (3)
H13	−0.0233	−0.1409	0.5373	0.046*
C14	0.40351 (9)	0.04175 (9)	0.22118 (14)	0.0425 (3)
C15	0.33767 (10)	0.04307 (10)	0.09494 (15)	0.0488 (3)
H15	0.2913	0.0930	0.0769	0.059*
C16	0.34062 (10)	−0.03057 (11)	−0.00606 (15)	0.0508 (3)
H16	0.2964	−0.0299	−0.0927	0.061*
C17	0.40900 (10)	−0.10480 (10)	0.02181 (15)	0.0479 (3)
C18	0.47462 (11)	−0.10467 (11)	0.14910 (16)	0.0546 (4)
H18	0.5211	−0.1544	0.1679	0.066*
C19	0.47204 (10)	−0.03162 (11)	0.24862 (16)	0.0512 (3)
H19	0.5167	−0.0318	0.3348	0.061*
C20	0.35584 (16)	−0.18189 (16)	−0.2055 (2)	0.0799 (5)
H20A	0.2878	−0.1767	−0.1920	0.120*
H20B	0.3653	−0.2416	−0.2555	0.120*
H20C	0.3727	−0.1276	−0.2621	0.120*
N1	0.29165 (7)	0.02406 (7)	0.42238 (11)	0.0374 (2)
N2	0.17080 (7)	−0.05379 (7)	0.54614 (10)	0.0340 (2)
N3	0.15774 (7)	0.05932 (7)	0.71772 (10)	0.0357 (2)
N4	−0.09155 (9)	−0.18655 (9)	0.84645 (13)	0.0512 (3)
O1	0.40353 (7)	0.11775 (7)	0.32231 (11)	0.0511 (2)
O2	0.41700 (9)	−0.18162 (9)	−0.06945 (12)	0.0716 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0354 (6)	0.0366 (6)	0.0433 (6)	−0.0005 (4)	0.0079 (5)	0.0034 (5)
C2	0.0382 (6)	0.0315 (6)	0.0517 (7)	−0.0044 (5)	0.0052 (5)	−0.0009 (5)
C3	0.0407 (6)	0.0313 (5)	0.0433 (6)	−0.0008 (5)	0.0022 (5)	−0.0056 (5)
C4	0.0353 (5)	0.0304 (5)	0.0338 (5)	0.0009 (4)	0.0027 (4)	−0.0008 (4)
C5	0.0350 (5)	0.0299 (5)	0.0338 (5)	0.0000 (4)	0.0042 (4)	0.0004 (4)
C6	0.0364 (5)	0.0316 (5)	0.0318 (5)	0.0020 (4)	0.0057 (4)	0.0008 (4)
C7	0.0471 (7)	0.0287 (5)	0.0468 (7)	−0.0017 (5)	0.0128 (5)	−0.0070 (5)
C8	0.0681 (9)	0.0502 (8)	0.0454 (7)	−0.0077 (7)	0.0075 (7)	−0.0135 (6)
C9	0.0375 (6)	0.0297 (5)	0.0360 (5)	0.0038 (4)	0.0084 (4)	0.0031 (4)
C10	0.0508 (7)	0.0416 (6)	0.0365 (6)	−0.0059 (5)	0.0091 (5)	−0.0021 (5)
C11	0.0647 (9)	0.0483 (7)	0.0403 (7)	−0.0071 (6)	0.0187 (6)	0.0014 (6)
C12	0.0408 (7)	0.0469 (7)	0.0496 (7)	−0.0049 (5)	0.0064 (5)	0.0004 (6)
C13	0.0394 (6)	0.0402 (6)	0.0357 (6)	0.0012 (5)	0.0044 (5)	0.0025 (5)
C14	0.0419 (6)	0.0421 (6)	0.0470 (7)	−0.0027 (5)	0.0181 (5)	0.0038 (5)
C15	0.0454 (7)	0.0443 (7)	0.0571 (8)	0.0077 (6)	0.0097 (6)	0.0095 (6)
C16	0.0489 (7)	0.0559 (8)	0.0462 (7)	0.0039 (6)	0.0025 (6)	0.0070 (6)
C17	0.0490 (7)	0.0491 (7)	0.0473 (7)	0.0052 (6)	0.0129 (6)	0.0019 (6)
C18	0.0499 (8)	0.0579 (9)	0.0554 (8)	0.0177 (7)	0.0060 (6)	0.0030 (7)
C19	0.0466 (7)	0.0594 (9)	0.0468 (7)	0.0080 (6)	0.0045 (6)	0.0042 (6)
C20	0.0881 (13)	0.0854 (13)	0.0627 (11)	0.0002 (11)	0.0005 (9)	−0.0198 (10)
N1	0.0399 (5)	0.0342 (5)	0.0396 (5)	−0.0011 (4)	0.0109 (4)	−0.0010 (4)
N2	0.0402 (5)	0.0285 (4)	0.0342 (5)	−0.0025 (4)	0.0085 (4)	−0.0030 (4)
N3	0.0396 (5)	0.0329 (5)	0.0346 (5)	0.0001 (4)	0.0060 (4)	−0.0017 (4)
N4	0.0538 (7)	0.0511 (7)	0.0517 (7)	−0.0089 (5)	0.0174 (5)	0.0016 (5)
O1	0.0557 (6)	0.0447 (5)	0.0585 (6)	−0.0112 (4)	0.0262 (5)	−0.0036 (4)
O2	0.0796 (8)	0.0689 (7)	0.0634 (7)	0.0212 (6)	0.0021 (6)	−0.0142 (6)

C1—N1	1.3161 (15)	C10—H10	0.9300
C1—O1	1.3667 (14)	C11—N4	1.3312 (18)
C1—C2	1.4020 (17)	C11—H11	0.9300
C2—C3	1.3744 (17)	C12—N4	1.3322 (17)
C2—H2	0.9300	C12—C13	1.3823 (17)
C3—C4	1.3928 (16)	C12—H12	0.9300
C3—H3	0.9300	C13—H13	0.9300
C4—N3	1.3842 (14)	C14—C15	1.365 (2)
C4—C5	1.3924 (15)	C14—C19	1.3708 (19)
C5—N1	1.3328 (14)	C14—O1	1.4048 (16)
C5—N2	1.3724 (14)	C15—C16	1.385 (2)
C6—N3	1.3192 (14)	C15—H15	0.9300
C6—N2	1.3788 (13)	C16—C17	1.3784 (19)
C6—C9	1.4686 (15)	C16—H16	0.9300
C7—N2	1.4638 (14)	C17—O2	1.3687 (17)
C7—C8	1.5066 (19)	C17—C18	1.371 (2)
C7—H7A	0.9700	C18—C19	1.369 (2)
C7—H7B	0.9700	C18—H18	0.9300
C8—H8A	0.9600	C19—H19	0.9300
C8—H8B	0.9600	C20—O2	1.406 (2)
C8—H8C	0.9600	C20—H20A	0.9600
C9—C13	1.3857 (17)	C20—H20B	0.9600
C9—C10	1.3899 (16)	C20—H20C	0.9600
C10—C11	1.3786 (18)
N1—C1—O1	118.16 (10)	N4—C12—C13	124.07 (13)
N1—C1—C2	125.63 (11)	N4—C12—H12	118.0
O1—C1—C2	116.21 (10)	C13—C12—H12	118.0
C3—C2—C1	119.44 (11)	C12—C13—C9	118.98 (11)
C3—C2—H2	120.3	C12—C13—H13	120.5
C1—C2—H2	120.3	C9—C13—H13	120.5
C2—C3—C4	117.22 (11)	C15—C14—C19	120.64 (13)
C2—C3—H3	121.4	C15—C14—O1	119.97 (12)
C4—C3—H3	121.4	C19—C14—O1	119.35 (13)
N3—C4—C5	109.76 (10)	C14—C15—C16	119.40 (13)
N3—C4—C3	133.26 (10)	C14—C15—H15	120.3
C5—C4—C3	116.98 (10)	C16—C15—H15	120.3
N1—C5—N2	125.53 (10)	C17—C16—C15	120.04 (13)
N1—C5—C4	127.79 (10)	C17—C16—H16	120.0
N2—C5—C4	106.68 (9)	C15—C16—H16	120.0
N3—C6—N2	113.32 (9)	O2—C17—C18	115.72 (12)
N3—C6—C9	122.41 (10)	O2—C17—C16	124.63 (13)
N2—C6—C9	124.27 (10)	C18—C17—C16	119.66 (13)
N2—C7—C8	112.19 (10)	C19—C18—C17	120.31 (13)
N2—C7—H7A	109.2	C19—C18—H18	119.8
C8—C7—H7A	109.2	C17—C18—H18	119.8
N2—C7—H7B	109.2	C18—C19—C14	119.94 (13)
C8—C7—H7B	109.2	C18—C19—H19	120.0
H7A—C7—H7B	107.9	C14—C19—H19	120.0
C7—C8—H8A	109.5	O2—C20—H20A	109.5
C7—C8—H8B	109.5	O2—C20—H20B	109.5
H8A—C8—H8B	109.5	H20A—C20—H20B	109.5
C7—C8—H8C	109.5	O2—C20—H20C	109.5
H8A—C8—H8C	109.5	H20A—C20—H20C	109.5
H8B—C8—H8C	109.5	H20B—C20—H20C	109.5
C13—C9—C10	117.46 (11)	C1—N1—C5	112.91 (10)
C13—C9—C6	123.59 (10)	C5—N2—C6	105.53 (9)
C10—C9—C6	118.91 (11)	C5—N2—C7	122.62 (9)
C11—C10—C9	118.99 (12)	C6—N2—C7	131.19 (9)
C11—C10—H10	120.5	C6—N3—C4	104.72 (9)
C9—C10—H10	120.5	C11—N4—C12	116.31 (11)
N4—C11—C10	124.17 (12)	C1—O1—C14	116.08 (9)
N4—C11—H11	117.9	C17—O2—C20	117.96 (13)
C10—C11—H11	117.9
N1—C1—C2—C3	−1.3 (2)	O1—C14—C19—C18	−178.17 (12)
O1—C1—C2—C3	178.21 (11)	O1—C1—N1—C5	−177.83 (11)
C1—C2—C3—C4	−0.17 (18)	C2—C1—N1—C5	1.63 (18)
C2—C3—C4—N3	−179.45 (12)	N2—C5—N1—C1	179.15 (11)
C2—C3—C4—C5	0.96 (16)	C4—C5—N1—C1	−0.73 (17)
N3—C4—C5—N1	179.77 (11)	N1—C5—N2—C6	−179.62 (11)
C3—C4—C5—N1	−0.54 (18)	C4—C5—N2—C6	0.28 (12)
N3—C4—C5—N2	−0.12 (13)	N1—C5—N2—C7	8.72 (18)
C3—C4—C5—N2	179.56 (10)	C4—C5—N2—C7	−171.38 (10)
N3—C6—C9—C13	142.45 (12)	N3—C6—N2—C5	−0.36 (13)
N2—C6—C9—C13	−37.09 (17)	C9—C6—N2—C5	179.21 (10)
N3—C6—C9—C10	−35.08 (17)	N3—C6—N2—C7	170.30 (11)
N2—C6—C9—C10	145.39 (12)	C9—C6—N2—C7	−10.13 (19)
C13—C9—C10—C11	−0.54 (19)	C8—C7—N2—C5	−76.72 (15)
C6—C9—C10—C11	177.14 (12)	C8—C7—N2—C6	113.98 (14)
C9—C10—C11—N4	1.3 (2)	N2—C6—N3—C4	0.28 (13)
N4—C12—C13—C9	1.1 (2)	C9—C6—N3—C4	−179.30 (10)
C10—C9—C13—C12	−0.60 (17)	C5—C4—N3—C6	−0.09 (13)
C6—C9—C13—C12	−178.16 (11)	C3—C4—N3—C6	−179.70 (13)
C19—C14—C15—C16	−0.1 (2)	C10—C11—N4—C12	−0.8 (2)
O1—C14—C15—C16	177.83 (11)	C13—C12—N4—C11	−0.4 (2)
C14—C15—C16—C17	0.6 (2)	N1—C1—O1—C14	−0.86 (17)
C15—C16—C17—O2	178.89 (13)	C2—C1—O1—C14	179.63 (11)
C15—C16—C17—C18	−0.7 (2)	C15—C14—O1—C1	90.64 (14)
O2—C17—C18—C19	−179.25 (14)	C19—C14—O1—C1	−91.40 (14)
C16—C17—C18—C19	0.4 (2)	C18—C17—O2—C20	−175.90 (15)
C17—C18—C19—C14	0.1 (2)	C16—C17—O2—C20	4.5 (2)
C15—C14—C19—C18	−0.2 (2)