6-Bromo-1,3-di-2-propynyl-1H-imidazo[4,5-b]pyridin-2(3H)-one.

The room-temperature reaction of propargyl bromide and 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in dimethyl-formamide yields the title compound, C(12)H(8)BrN(3)O, which features nitro-gen-bound propynyl substituents. The imidazopyridine fused ring is almost planar (r.m.s. deviation = 0.011 Å); the propynyl chains point in opposite directions relative to the fused ring. One acetyl-enic H atom is hydrogen bonded to the carbonyl O atom of an inversion-related mol-ecule, forming a dimer; adjacent dimers are linked by a second acetyl-ene-pyridine C-H⋯N inter-action, forming a layer motif.

Related literature

For the crystal structures of other imidazo[4,5-b]pyridin-2-ones, see: Kourafalos et al. (2002 ▶); Meanwell et al. (1995 ▶).

Experimental

Crystal data

C12H8BrN3O

M = 290.12

Monoclinic,

a = 9.0725 (3) Å

b = 18.6212 (5) Å

c = 7.0684 (2) Å

β = 102.995 (1)°

V = 1163.56 (6) Å3

Z = 4

Mo Kα radiation

μ = 3.52 mm−1

T = 293 K

0.35 × 0.30 × 0.15 mm

Data collection

Bruker X8 APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.372, T max = 0.620

27315 measured reflections

3383 independent reflections

2810 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.085

S = 1.03

3383 reflections

162 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.87 e Å−3

Δρmin = −0.80 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/S1600536810007701/hg2650sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007701/hg2650Isup2.hkl

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

C12H8BrN3O	F(000) = 576
Mr = 290.12	Dx = 1.656 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9924 reflections
a = 9.0725 (3) Å	θ = 2.3–31.8°
b = 18.6212 (5) Å	µ = 3.52 mm−1
c = 7.0684 (2) Å	T = 293 K
β = 102.995 (1)°	Prism, yellow
V = 1163.56 (6) Å3	0.35 × 0.30 × 0.15 mm
Z = 4

Bruker X8 APEXII diffractometer	3383 independent reflections
Radiation source: fine-focus sealed tube	2810 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.372, Tmax = 0.620	k = −26→26
27315 measured reflections	l = −9→9

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0475P)2 + 0.4099P] where P = (Fo2 + 2Fc2)/3
3383 reflections	(Δ/σ)max = 0.001
162 parameters	Δρmax = 0.87 e Å−3
2 restraints	Δρmin = −0.80 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.40313 (3)	0.071904 (9)	0.35455 (3)	0.05174 (9)
O1	0.32318 (15)	0.47483 (7)	0.3528 (2)	0.0435 (3)
N1	0.12161 (15)	0.24467 (8)	0.3731 (2)	0.0354 (3)
N2	0.18505 (15)	0.37028 (8)	0.3651 (2)	0.0326 (3)
N3	0.42693 (14)	0.35966 (7)	0.35770 (18)	0.0289 (3)
C1	0.1822 (2)	0.17839 (9)	0.3720 (2)	0.0368 (4)
H1	0.1213	0.1387	0.3786	0.044*
C2	0.3302 (2)	0.16693 (8)	0.3614 (2)	0.0322 (3)
C3	0.43018 (17)	0.22350 (8)	0.3550 (2)	0.0289 (3)
H3	0.5302	0.2161	0.3481	0.035*
C4	0.21635 (17)	0.29782 (8)	0.3662 (2)	0.0279 (3)
C5	0.36927 (16)	0.29091 (8)	0.3596 (2)	0.0251 (3)
C6	0.0418 (2)	0.40256 (12)	0.3799 (3)	0.0457 (4)
H6A	0.0621	0.4471	0.4522	0.055*
H6B	−0.0093	0.3705	0.4524	0.055*
C7	−0.0586 (2)	0.41743 (12)	0.1911 (3)	0.0484 (5)
C8	−0.1389 (3)	0.43130 (16)	0.0410 (4)	0.0699 (8)
H8	−0.212 (3)	0.442 (2)	−0.073 (3)	0.108 (13)*
C9	0.31325 (18)	0.40998 (9)	0.3577 (2)	0.0307 (3)
C10	0.58352 (18)	0.38016 (10)	0.3664 (3)	0.0380 (4)
H10A	0.5957	0.4311	0.3946	0.046*
H10B	0.6068	0.3718	0.2408	0.046*
C11	0.68988 (18)	0.33965 (10)	0.5150 (3)	0.0397 (4)
C12	0.7772 (2)	0.30575 (14)	0.6294 (4)	0.0559 (6)
H12	0.849 (2)	0.2804 (13)	0.721 (3)	0.070 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.07831 (18)	0.02651 (10)	0.04492 (13)	0.00475 (8)	0.00231 (10)	−0.00343 (6)
O1	0.0484 (7)	0.0281 (6)	0.0488 (7)	0.0041 (5)	−0.0001 (6)	0.0039 (5)
N1	0.0277 (6)	0.0436 (8)	0.0344 (7)	−0.0079 (6)	0.0059 (5)	−0.0006 (6)
N2	0.0261 (6)	0.0344 (7)	0.0357 (7)	0.0063 (5)	0.0039 (5)	0.0004 (5)
N3	0.0234 (6)	0.0261 (6)	0.0353 (6)	−0.0012 (4)	0.0023 (5)	0.0030 (5)
C1	0.0402 (9)	0.0356 (8)	0.0330 (8)	−0.0124 (7)	0.0050 (7)	−0.0002 (6)
C2	0.0437 (9)	0.0262 (7)	0.0246 (7)	−0.0018 (6)	0.0036 (6)	−0.0010 (5)
C3	0.0291 (7)	0.0294 (7)	0.0276 (7)	0.0028 (5)	0.0051 (6)	0.0003 (5)
C4	0.0248 (7)	0.0332 (7)	0.0240 (6)	0.0005 (5)	0.0022 (5)	−0.0001 (5)
C5	0.0237 (6)	0.0269 (7)	0.0236 (6)	−0.0015 (5)	0.0034 (5)	0.0005 (5)
C6	0.0346 (9)	0.0554 (11)	0.0481 (10)	0.0163 (8)	0.0114 (8)	−0.0029 (9)
C7	0.0306 (9)	0.0535 (11)	0.0610 (12)	0.0143 (8)	0.0101 (8)	0.0079 (9)
C8	0.0452 (13)	0.093 (2)	0.0672 (16)	0.0256 (12)	0.0040 (11)	0.0159 (13)
C9	0.0304 (7)	0.0294 (7)	0.0286 (7)	0.0028 (6)	−0.0014 (6)	0.0018 (6)
C10	0.0274 (7)	0.0392 (9)	0.0457 (9)	−0.0064 (6)	0.0047 (7)	0.0103 (7)
C11	0.0236 (7)	0.0455 (9)	0.0482 (10)	−0.0043 (6)	0.0042 (7)	0.0049 (8)
C12	0.0307 (9)	0.0659 (14)	0.0661 (14)	0.0016 (9)	0.0002 (9)	0.0171 (11)

Br1—C2	1.8935 (16)	C3—C5	1.375 (2)
O1—C9	1.212 (2)	C3—H3	0.9300
N1—C4	1.319 (2)	C4—C5	1.405 (2)
N1—C1	1.352 (2)	C6—C7	1.463 (3)
N2—C4	1.378 (2)	C6—H6A	0.9700
N2—C9	1.389 (2)	C6—H6B	0.9700
N2—C6	1.457 (2)	C7—C8	1.173 (3)
N3—C5	1.3842 (19)	C8—H8	0.948 (10)
N3—C9	1.394 (2)	C10—C11	1.466 (2)
N3—C10	1.459 (2)	C10—H10A	0.9700
C1—C2	1.379 (3)	C10—H10B	0.9700
C1—H1	0.9300	C11—C12	1.179 (3)
C2—C3	1.397 (2)	C12—H12	0.939 (10)
C4—N1—C1	114.56 (14)	N3—C5—C4	107.09 (13)
C4—N2—C9	110.37 (13)	N2—C6—C7	113.27 (16)
C4—N2—C6	126.11 (16)	N2—C6—H6A	108.9
C9—N2—C6	123.44 (15)	C7—C6—H6A	108.9
C5—N3—C9	109.91 (13)	N2—C6—H6B	108.9
C5—N3—C10	127.46 (14)	C7—C6—H6B	108.9
C9—N3—C10	122.53 (14)	H6A—C6—H6B	107.7
N1—C1—C2	122.96 (15)	C8—C7—C6	178.2 (3)
N1—C1—H1	118.5	C7—C8—H8	174 (2)
C2—C1—H1	118.5	O1—C9—N2	126.84 (15)
C1—C2—C3	122.16 (15)	O1—C9—N3	127.61 (16)
C1—C2—Br1	119.74 (12)	N2—C9—N3	105.55 (13)
C3—C2—Br1	118.10 (13)	N3—C10—C11	111.93 (14)
C5—C3—C2	114.86 (14)	N3—C10—H10A	109.2
C5—C3—H3	122.6	C11—C10—H10A	109.2
C2—C3—H3	122.6	N3—C10—H10B	109.2
N1—C4—N2	126.85 (15)	C11—C10—H10B	109.2
N1—C4—C5	126.10 (15)	H10A—C10—H10B	107.9
N2—C4—C5	107.05 (13)	C12—C11—C10	177.6 (2)
C3—C5—N3	133.58 (14)	C11—C12—H12	177.7 (17)
C3—C5—C4	119.33 (14)
C4—N1—C1—C2	−1.0 (2)	N1—C4—C5—C3	1.7 (2)
N1—C1—C2—C3	1.4 (3)	N2—C4—C5—C3	−178.61 (13)
N1—C1—C2—Br1	−178.53 (12)	N1—C4—C5—N3	−178.81 (14)
C1—C2—C3—C5	−0.2 (2)	N2—C4—C5—N3	0.92 (16)
Br1—C2—C3—C5	179.73 (10)	C4—N2—C6—C7	−93.3 (2)
C1—N1—C4—N2	179.82 (15)	C9—N2—C6—C7	90.2 (2)
C1—N1—C4—C5	−0.5 (2)	C4—N2—C9—O1	179.15 (16)
C9—N2—C4—N1	179.78 (15)	C6—N2—C9—O1	−3.9 (3)
C6—N2—C4—N1	2.9 (3)	C4—N2—C9—N3	−0.99 (17)
C9—N2—C4—C5	0.05 (17)	C6—N2—C9—N3	175.99 (15)
C6—N2—C4—C5	−176.84 (15)	C5—N3—C9—O1	−178.56 (16)
C2—C3—C5—N3	179.41 (15)	C10—N3—C9—O1	4.8 (3)
C2—C3—C5—C4	−1.2 (2)	C5—N3—C9—N2	1.58 (17)
C9—N3—C5—C3	177.86 (16)	C10—N3—C9—N2	−175.03 (14)
C10—N3—C5—C3	−5.7 (3)	C5—N3—C10—C11	−45.0 (2)
C9—N3—C5—C4	−1.58 (16)	C9—N3—C10—C11	131.00 (17)
C10—N3—C5—C4	174.83 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.95 (1)	2.53 (2)	3.392 (3)	151 (3)
C12—H12···N1ii	0.94 (1)	2.51 (2)	3.346 (2)	149 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.95 (1)	2.53 (2)	3.392 (3)	151 (3)
C12—H12⋯N1ii	0.94 (1)	2.51 (2)	3.346 (2)	149 (2)

Symmetry codes: (i) ; (ii) .