1,3-Dibenzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

The imidazopyridine fused-ring in the title compound, C(20)H(16)BrN(3)O, is planar (r.m.s. deviation = 0.011 Å). The phenyl rings of the benzyl substitutents twist away from the central five-membered ring in opposite directions; the rings are aligned at 61.3 (1) and 71.2 (1)° with respect to this ring.

Related literature

For the medicinal applications of 1,3-dihydro-imidazo[4,5-b]pyridin-2-ones, see: Barraclough et al. (1990 ▶); Cundy et al. (1997 ▶); Desarro et al. (1994 ▶); Liu et al. (2008 ▶); Mader et al. (2008 ▶); Zaki & Proença (2007 ▶). For the product of the reaction of propargyl bromide with 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in DMF at room and high temperatures, see: Dahmani et al. (2010a ▶,b ▶).

Experimental

Crystal data

C20H16BrN3O

M = 394.27

Monoclinic,

a = 9.1627 (1) Å

b = 25.5071 (3) Å

c = 8.0629 (1) Å

β = 115.571 (1)°

V = 1699.84 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.43 mm−1

T = 293 K

0.42 × 0.18 × 0.13 mm

Data collection

Bruker X8 APEX2 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.428, T max = 0.743

38010 measured reflections

3903 independent reflections

2967 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.138

S = 1.07

3903 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.84 e Å−3

Δρmin = −0.90 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810007713/hg2651sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007713/hg2651Isup2.hkl

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

C20H16BrN3O	F(000) = 800
Mr = 394.27	Dx = 1.541 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9890 reflections
a = 9.1627 (1) Å	θ = 2.5–25.0°
b = 25.5071 (3) Å	µ = 2.43 mm−1
c = 8.0629 (1) Å	T = 293 K
β = 115.571 (1)°	Prism, colorless
V = 1699.84 (3) Å3	0.42 × 0.18 × 0.13 mm
Z = 4

Bruker X8 APEX2 diffractometer	3903 independent reflections
Radiation source: fine-focus sealed tube	2967 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.428, Tmax = 0.743	k = −33→33
38010 measured reflections	l = −9→10

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0688P)2 + 1.1691P] where P = (Fo2 + 2Fc2)/3
3903 reflections	(Δ/σ)max = 0.001
226 parameters	Δρmax = 0.84 e Å−3
0 restraints	Δρmin = −0.90 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.75465 (4)	0.225888 (14)	0.48173 (6)	0.07328 (18)
O1	0.2072 (3)	0.45942 (8)	0.3332 (3)	0.0570 (5)
N1	0.3210 (3)	0.28134 (9)	0.4493 (3)	0.0480 (6)
N2	0.2208 (3)	0.36984 (9)	0.3920 (3)	0.0399 (5)
N3	0.4318 (3)	0.40833 (8)	0.3767 (3)	0.0398 (5)
C1	0.4498 (4)	0.25184 (12)	0.4685 (4)	0.0515 (7)
H1	0.4465	0.2160	0.4879	0.062*
C2	0.5858 (4)	0.27231 (11)	0.4606 (4)	0.0473 (7)
C3	0.6008 (3)	0.32553 (11)	0.4321 (4)	0.0428 (6)
H3	0.6926	0.3396	0.4275	0.051*
C4	0.4695 (3)	0.35553 (10)	0.4115 (3)	0.0366 (5)
C5	0.3351 (3)	0.33129 (10)	0.4207 (3)	0.0366 (5)
C6	0.2777 (3)	0.41774 (10)	0.3635 (4)	0.0401 (6)
C7	0.0593 (3)	0.36191 (13)	0.3822 (4)	0.0482 (7)
H7A	0.0226	0.3269	0.3356	0.058*
H7B	−0.0145	0.3867	0.2952	0.058*
C8	0.0513 (3)	0.36830 (10)	0.5637 (4)	0.0376 (5)
C9	0.0052 (3)	0.41597 (11)	0.6102 (4)	0.0448 (6)
H9	−0.0162	0.4444	0.5310	0.054*
C10	−0.0090 (4)	0.42129 (13)	0.7723 (4)	0.0530 (7)
H10	−0.0399	0.4533	0.8023	0.064*
C11	0.0223 (4)	0.37940 (15)	0.8905 (4)	0.0572 (8)
H11	0.0105	0.3829	0.9989	0.069*
C12	0.0711 (4)	0.33231 (14)	0.8480 (5)	0.0581 (8)
H12	0.0946	0.3042	0.9291	0.070*
C13	0.0854 (3)	0.32658 (12)	0.6849 (4)	0.0490 (7)
H13	0.1180	0.2946	0.6565	0.059*
C14	0.5321 (4)	0.44829 (11)	0.3487 (4)	0.0431 (6)
H14A	0.6349	0.4498	0.4570	0.052*
H14B	0.4797	0.4821	0.3362	0.052*
C15	0.5641 (3)	0.43916 (9)	0.1821 (3)	0.0349 (5)
C16	0.6900 (3)	0.46603 (11)	0.1695 (4)	0.0437 (6)
H16	0.7526	0.4889	0.2630	0.052*
C17	0.7240 (4)	0.45935 (14)	0.0203 (4)	0.0549 (8)
H17	0.8092	0.4777	0.0137	0.066*
C18	0.6319 (4)	0.42548 (13)	−0.1197 (4)	0.0533 (7)
H18	0.6559	0.4204	−0.2194	0.064*
C19	0.5046 (4)	0.39937 (12)	−0.1105 (4)	0.0498 (7)
H19	0.4411	0.3770	−0.2055	0.060*
C20	0.4702 (3)	0.40613 (11)	0.0401 (4)	0.0445 (6)
H20	0.3836	0.3884	0.0453	0.053*

	U11	U22	U33	U12	U13	U23
Br1	0.0600 (2)	0.0554 (2)	0.0961 (3)	0.01808 (15)	0.0259 (2)	0.00089 (17)
O1	0.0630 (13)	0.0486 (12)	0.0681 (14)	0.0147 (10)	0.0364 (11)	0.0062 (10)
N1	0.0528 (14)	0.0437 (13)	0.0526 (14)	−0.0072 (10)	0.0274 (12)	0.0003 (10)
N2	0.0410 (11)	0.0455 (12)	0.0394 (12)	−0.0017 (9)	0.0233 (10)	−0.0020 (9)
N3	0.0454 (12)	0.0371 (11)	0.0455 (12)	−0.0015 (9)	0.0277 (10)	0.0009 (9)
C1	0.0595 (18)	0.0372 (15)	0.0584 (18)	−0.0029 (13)	0.0261 (15)	0.0018 (13)
C2	0.0459 (15)	0.0424 (15)	0.0494 (16)	0.0071 (12)	0.0166 (13)	−0.0007 (12)
C3	0.0398 (13)	0.0436 (14)	0.0478 (15)	0.0001 (11)	0.0214 (12)	−0.0026 (12)
C4	0.0424 (13)	0.0371 (12)	0.0336 (12)	−0.0029 (10)	0.0194 (11)	−0.0028 (10)
C5	0.0392 (13)	0.0400 (13)	0.0336 (12)	−0.0026 (10)	0.0186 (10)	−0.0031 (10)
C6	0.0482 (15)	0.0438 (14)	0.0346 (13)	0.0014 (12)	0.0239 (11)	−0.0020 (11)
C7	0.0359 (13)	0.0663 (19)	0.0426 (15)	−0.0056 (12)	0.0172 (12)	−0.0081 (13)
C8	0.0291 (11)	0.0463 (14)	0.0404 (13)	−0.0053 (10)	0.0177 (10)	−0.0025 (11)
C9	0.0402 (14)	0.0445 (15)	0.0506 (16)	0.0020 (11)	0.0204 (12)	0.0050 (12)
C10	0.0482 (16)	0.0594 (18)	0.0570 (18)	0.0009 (14)	0.0279 (14)	−0.0135 (15)
C11	0.0468 (16)	0.090 (2)	0.0415 (16)	−0.0001 (16)	0.0251 (13)	−0.0038 (16)
C12	0.0531 (18)	0.069 (2)	0.0566 (19)	0.0009 (15)	0.0276 (15)	0.0177 (16)
C13	0.0460 (15)	0.0441 (15)	0.0637 (18)	0.0007 (12)	0.0302 (14)	0.0014 (13)
C14	0.0544 (16)	0.0379 (13)	0.0447 (15)	−0.0103 (12)	0.0287 (13)	−0.0057 (11)
C15	0.0382 (12)	0.0309 (12)	0.0383 (13)	0.0023 (10)	0.0190 (11)	0.0031 (10)
C16	0.0412 (14)	0.0442 (15)	0.0437 (15)	−0.0059 (11)	0.0166 (12)	0.0001 (11)
C17	0.0486 (17)	0.066 (2)	0.0605 (19)	−0.0051 (14)	0.0338 (16)	0.0068 (15)
C18	0.0600 (18)	0.0642 (19)	0.0467 (16)	0.0081 (15)	0.0333 (15)	0.0053 (14)
C19	0.0571 (17)	0.0519 (16)	0.0401 (15)	−0.0015 (13)	0.0206 (13)	−0.0074 (12)
C20	0.0460 (15)	0.0461 (15)	0.0463 (15)	−0.0085 (12)	0.0245 (13)	−0.0048 (12)

Br1—C2	1.897 (3)	C9—H9	0.9300
O1—C6	1.213 (3)	C10—C11	1.377 (5)
N1—C5	1.311 (3)	C10—H10	0.9300
N1—C1	1.351 (4)	C11—C12	1.376 (5)
N2—C5	1.382 (3)	C11—H11	0.9300
N2—C6	1.386 (3)	C12—C13	1.384 (5)
N2—C7	1.462 (3)	C12—H12	0.9300
N3—C4	1.389 (3)	C13—H13	0.9300
N3—C6	1.391 (3)	C14—C15	1.512 (4)
N3—C14	1.453 (3)	C14—H14A	0.9700
C1—C2	1.377 (4)	C14—H14B	0.9700
C1—H1	0.9300	C15—C20	1.382 (4)
C2—C3	1.393 (4)	C15—C16	1.383 (4)
C3—C4	1.374 (4)	C16—C17	1.377 (4)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.408 (4)	C17—C18	1.382 (5)
C7—C8	1.505 (4)	C17—H17	0.9300
C7—H7A	0.9700	C18—C19	1.372 (5)
C7—H7B	0.9700	C18—H18	0.9300
C8—C13	1.386 (4)	C19—C20	1.391 (4)
C8—C9	1.390 (4)	C19—H19	0.9300
C9—C10	1.376 (4)	C20—H20	0.9300
C5—N1—C1	114.4 (2)	C9—C10—C11	120.3 (3)
C5—N2—C6	110.0 (2)	C9—C10—H10	119.9
C5—N2—C7	126.0 (2)	C11—C10—H10	119.9
C6—N2—C7	123.9 (2)	C12—C11—C10	119.9 (3)
C4—N3—C6	109.8 (2)	C12—C11—H11	120.1
C4—N3—C14	126.4 (2)	C10—C11—H11	120.1
C6—N3—C14	123.8 (2)	C11—C12—C13	120.2 (3)
N1—C1—C2	123.1 (3)	C11—C12—H12	119.9
N1—C1—H1	118.4	C13—C12—H12	119.9
C2—C1—H1	118.4	C12—C13—C8	120.2 (3)
C1—C2—C3	122.2 (3)	C12—C13—H13	119.9
C1—C2—Br1	118.6 (2)	C8—C13—H13	119.9
C3—C2—Br1	119.2 (2)	N3—C14—C15	114.1 (2)
C4—C3—C2	114.8 (3)	N3—C14—H14A	108.7
C4—C3—H3	122.6	C15—C14—H14A	108.7
C2—C3—H3	122.6	N3—C14—H14B	108.7
C3—C4—N3	133.9 (2)	C15—C14—H14B	108.7
C3—C4—C5	119.3 (2)	H14A—C14—H14B	107.6
N3—C4—C5	106.9 (2)	C20—C15—C16	118.8 (2)
N1—C5—N2	126.6 (2)	C20—C15—C14	122.7 (2)
N1—C5—C4	126.2 (3)	C16—C15—C14	118.5 (2)
N2—C5—C4	107.2 (2)	C17—C16—C15	120.9 (3)
O1—C6—N2	126.9 (3)	C17—C16—H16	119.6
O1—C6—N3	127.0 (3)	C15—C16—H16	119.6
N2—C6—N3	106.1 (2)	C16—C17—C18	120.1 (3)
N2—C7—C8	113.9 (2)	C16—C17—H17	120.0
N2—C7—H7A	108.8	C18—C17—H17	120.0
C8—C7—H7A	108.8	C19—C18—C17	119.6 (3)
N2—C7—H7B	108.8	C19—C18—H18	120.2
C8—C7—H7B	108.8	C17—C18—H18	120.2
H7A—C7—H7B	107.7	C18—C19—C20	120.3 (3)
C13—C8—C9	118.9 (2)	C18—C19—H19	119.8
C13—C8—C7	120.7 (3)	C20—C19—H19	119.8
C9—C8—C7	120.3 (3)	C15—C20—C19	120.3 (3)
C10—C9—C8	120.4 (3)	C15—C20—H20	119.9
C10—C9—H9	119.8	C19—C20—H20	119.9
C8—C9—H9	119.8
C5—N1—C1—C2	0.6 (4)	C4—N3—C6—N2	0.4 (3)
N1—C1—C2—C3	0.0 (5)	C14—N3—C6—N2	177.7 (2)
N1—C1—C2—Br1	−178.0 (2)	C5—N2—C7—C8	92.2 (3)
C1—C2—C3—C4	−0.4 (4)	C6—N2—C7—C8	−91.5 (3)
Br1—C2—C3—C4	177.6 (2)	N2—C7—C8—C13	−86.0 (3)
C2—C3—C4—N3	−178.0 (3)	N2—C7—C8—C9	95.7 (3)
C2—C3—C4—C5	0.1 (4)	C13—C8—C9—C10	−1.1 (4)
C6—N3—C4—C3	178.2 (3)	C7—C8—C9—C10	177.2 (3)
C14—N3—C4—C3	0.9 (5)	C8—C9—C10—C11	0.0 (4)
C6—N3—C4—C5	−0.1 (3)	C9—C10—C11—C12	1.3 (5)
C14—N3—C4—C5	−177.4 (2)	C10—C11—C12—C13	−1.4 (5)
C1—N1—C5—N2	178.3 (3)	C11—C12—C13—C8	0.3 (5)
C1—N1—C5—C4	−1.0 (4)	C9—C8—C13—C12	1.0 (4)
C6—N2—C5—N1	−178.9 (3)	C7—C8—C13—C12	−177.3 (3)
C7—N2—C5—N1	−2.1 (4)	C4—N3—C14—C15	62.6 (4)
C6—N2—C5—C4	0.5 (3)	C6—N3—C14—C15	−114.3 (3)
C7—N2—C5—C4	177.3 (2)	N3—C14—C15—C20	18.6 (4)
C3—C4—C5—N1	0.6 (4)	N3—C14—C15—C16	−163.1 (2)
N3—C4—C5—N1	179.2 (3)	C20—C15—C16—C17	−1.3 (4)
C3—C4—C5—N2	−178.8 (2)	C14—C15—C16—C17	−179.7 (3)
N3—C4—C5—N2	−0.2 (3)	C15—C16—C17—C18	0.1 (5)
C5—N2—C6—O1	179.4 (3)	C16—C17—C18—C19	1.2 (5)
C7—N2—C6—O1	2.6 (4)	C17—C18—C19—C20	−1.2 (5)
C5—N2—C6—N3	−0.5 (3)	C16—C15—C20—C19	1.4 (4)
C7—N2—C6—N3	−177.4 (2)	C14—C15—C20—C19	179.7 (3)
C4—N3—C6—O1	−179.6 (3)	C18—C19—C20—C15	−0.1 (5)
C14—N3—C6—O1	−2.2 (4)