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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès, Morocco, bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 24 June 2010; accepted 26 June 2010; online 3 July 2010)

The non-H atoms of the two independent mol­ecules in the asymmetric unit of the title compound, C8H8BrN3O, are planar (r.m.s. deviations = 0.015 and 0.019 Å). In the crystal, the mol­ecules are linked into a zigzag chain along the c axis by C—H⋯O hydrogen bonds.

Related literature

For the synthesis of the un-brominated compound, see: Yutilov et al. (1998[Yutilov, Yu. M., Malyutina, V. F., Lopatinskaya, Kh. Ya. & Svertilova, I. A. (1998). Russ. J. Org. Chem. 34, 1363-1364.], 2005[Yutilov, Yu. M., Lopatinskaya, Kh. Ya., Smolyar, N. N. & Gres'ko, S. V. (2005). Russ. J. Org. Chem. 41, 575-579.]).

[Scheme 1]

Experimental

Crystal data
  • C8H8BrN3O

  • Mr = 242.08

  • Monoclinic, P 21 /c

  • a = 21.7981 (4) Å

  • b = 3.9929 (1) Å

  • c = 20.6636 (3) Å

  • β = 95.398 (1)°

  • V = 1790.53 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 4.55 mm−1

  • T = 293 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker X8 APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.396, Tmax = 0.548

  • 21586 measured reflections

  • 5229 independent reflections

  • 3539 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.086

  • S = 1.01

  • 5229 reflections

  • 239 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8C⋯O2i 0.96 2.33 3.279 (3) 167
C11—H11⋯O1 0.93 2.49 3.321 (3) 148
Symmetry code: (i) [x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA..]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA..]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The imidazo[4,5-b]pyridine unit is an important heterocyclic nucleus found in a large number of medicinal compounds. The synthesis of 1,3-dimethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one involves several steps (Yutilov et al., 1998, 2005). The 6-bromo derivative (Scheme I) is conveniently synthesized by the direct reaction of 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one with methyl iodide.

The aysmmetric unit (Fig. 1) has two independent molecules. Both are planar.

Related literature top

For the synthesis of the un-brominated compound, see: Yutilov et al. (1998, 2005).

Experimental top

To a mixture of 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (0.15 g, 1 mmol), potassium carbonate (0.38 g, 4 mmol) and tetra-n-butylammonium bromide (0.02 g, 0.1 mmol) in DMF (10 ml) was added methyl iodide (0.1 ml, 2.5 mmol). Stirring was continued at room temperature for 12 h. After the completion of reaction (as monitored by TLC), the mixture was filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel with ethyl acetate-hexane (1:3) as eluent. The compound was recrystallized from ethyl acetate-hexane (1:3) to afford colourless crystals.

Refinement top

H atoms were placed in calculated positions (C-H = 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Structure description top

The imidazo[4,5-b]pyridine unit is an important heterocyclic nucleus found in a large number of medicinal compounds. The synthesis of 1,3-dimethyl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one involves several steps (Yutilov et al., 1998, 2005). The 6-bromo derivative (Scheme I) is conveniently synthesized by the direct reaction of 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one with methyl iodide.

The aysmmetric unit (Fig. 1) has two independent molecules. Both are planar.

For the synthesis of the un-brominated compound, see: Yutilov et al. (1998, 2005).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of the two independent molecules of C8H8BrN3O at the 50% probability level. H atoms are shown as spheres of arbitrary radii.
6-Bromo-1,3-dimethyl-1H-imidazo[4,5-b]pyridin-2(3H)-one top
Crystal data top
C8H8BrN3OF(000) = 960
Mr = 242.08Dx = 1.796 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6375 reflections
a = 21.7981 (4) Åθ = 2.6–25.2°
b = 3.9929 (1) ŵ = 4.55 mm1
c = 20.6636 (3) ÅT = 293 K
β = 95.398 (1)°Prism, colourless
V = 1790.53 (6) Å30.25 × 0.20 × 0.15 mm
Z = 8
Data collection top
Bruker X8 APEXII area-detector
diffractometer
5229 independent reflections
Radiation source: fine-focus sealed tube3539 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3028
Tmin = 0.396, Tmax = 0.548k = 55
21586 measured reflectionsl = 2928
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0438P)2 + 0.1144P]
where P = (Fo2 + 2Fc2)/3
5229 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C8H8BrN3OV = 1790.53 (6) Å3
Mr = 242.08Z = 8
Monoclinic, P21/cMo Kα radiation
a = 21.7981 (4) ŵ = 4.55 mm1
b = 3.9929 (1) ÅT = 293 K
c = 20.6636 (3) Å0.25 × 0.20 × 0.15 mm
β = 95.398 (1)°
Data collection top
Bruker X8 APEXII area-detector
diffractometer
5229 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3539 reflections with I > 2σ(I)
Tmin = 0.396, Tmax = 0.548Rint = 0.036
21586 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 1.01Δρmax = 0.28 e Å3
5229 reflectionsΔρmin = 0.29 e Å3
239 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.407800 (11)0.91753 (7)0.468246 (11)0.05023 (9)
N10.44555 (8)0.5071 (5)0.65032 (9)0.0416 (4)
N20.37942 (8)0.4903 (5)0.73723 (8)0.0400 (4)
N30.29799 (8)0.7480 (5)0.68786 (8)0.0387 (4)
N40.05385 (8)0.5642 (5)0.92033 (9)0.0400 (4)
N50.12070 (8)0.8692 (5)0.99889 (8)0.0391 (4)
N60.19961 (8)0.9449 (5)0.94033 (8)0.0373 (4)
O10.29345 (8)0.5668 (5)0.79455 (8)0.0568 (5)
O20.20597 (8)1.1650 (5)1.04514 (8)0.0576 (5)
C10.44708 (10)0.6147 (6)0.58839 (11)0.0421 (5)
H10.48260.57670.56780.050*
C20.39881 (10)0.7769 (6)0.55465 (10)0.0374 (5)
C30.34349 (10)0.8436 (5)0.58128 (10)0.0356 (5)
H30.31050.95280.55850.043*
C40.34205 (9)0.7335 (5)0.64419 (10)0.0339 (4)
C50.39361 (9)0.5704 (5)0.67562 (10)0.0345 (5)
C60.42023 (12)0.3314 (7)0.78847 (13)0.0546 (7)
H6A0.39600.22310.81880.082*
H6B0.44600.49830.81070.082*
H6C0.44550.16840.76960.082*
C70.32072 (10)0.5976 (6)0.74587 (11)0.0411 (5)
C80.23694 (10)0.8923 (7)0.67783 (13)0.0503 (6)
H8A0.22891.02140.71530.075*
H8B0.20700.71640.67130.075*
H8C0.23441.03480.64020.075*
C90.05044 (10)0.4500 (6)0.85870 (11)0.0415 (5)
H90.01490.33850.84230.050*
C100.09723 (10)0.4905 (5)0.81873 (10)0.0356 (5)
C110.15197 (9)0.6529 (5)0.83943 (10)0.0350 (5)
H110.18390.67950.81300.042*
C120.15516 (9)0.7711 (5)0.90210 (9)0.0311 (4)
C130.10513 (9)0.7226 (5)0.93943 (10)0.0337 (4)
C140.08264 (13)0.8834 (8)1.05313 (13)0.0621 (8)
H14A0.10830.86041.09330.093*
H14B0.05300.70481.04920.093*
H14C0.06151.09451.05260.093*
C150.17830 (10)1.0112 (6)0.99985 (11)0.0408 (5)
C160.25863 (10)1.0616 (6)0.92138 (12)0.0474 (6)
H16A0.28421.13180.95930.071*
H16B0.25201.24680.89190.071*
H16C0.27860.88290.90040.071*
Br20.086179 (12)0.32023 (7)0.732957 (11)0.05183 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.05040 (16)0.06094 (17)0.04140 (14)0.00344 (12)0.01514 (11)0.00544 (11)
N10.0294 (9)0.0492 (12)0.0453 (11)0.0036 (8)0.0008 (8)0.0047 (8)
N20.0366 (10)0.0488 (12)0.0335 (10)0.0022 (8)0.0025 (8)0.0032 (8)
N30.0332 (10)0.0493 (11)0.0343 (9)0.0062 (8)0.0063 (7)0.0052 (8)
N40.0318 (10)0.0484 (11)0.0403 (10)0.0036 (8)0.0061 (8)0.0035 (8)
N50.0396 (10)0.0478 (11)0.0306 (9)0.0006 (8)0.0071 (8)0.0029 (8)
N60.0332 (9)0.0425 (10)0.0357 (9)0.0038 (8)0.0012 (7)0.0002 (8)
O10.0547 (10)0.0782 (13)0.0395 (9)0.0077 (9)0.0152 (8)0.0125 (8)
O20.0627 (12)0.0644 (12)0.0439 (10)0.0092 (9)0.0042 (9)0.0157 (8)
C10.0303 (11)0.0507 (14)0.0463 (13)0.0013 (10)0.0096 (10)0.0058 (10)
C20.0362 (12)0.0429 (12)0.0337 (11)0.0065 (10)0.0069 (9)0.0025 (9)
C30.0322 (11)0.0394 (12)0.0350 (11)0.0000 (9)0.0015 (9)0.0010 (8)
C40.0289 (11)0.0356 (11)0.0373 (11)0.0003 (9)0.0045 (8)0.0016 (9)
C50.0332 (11)0.0370 (11)0.0322 (11)0.0027 (9)0.0028 (8)0.0038 (8)
C60.0565 (16)0.0608 (17)0.0441 (13)0.0095 (13)0.0084 (11)0.0098 (12)
C70.0400 (12)0.0477 (13)0.0357 (12)0.0000 (10)0.0041 (9)0.0006 (9)
C80.0385 (13)0.0615 (16)0.0520 (14)0.0104 (11)0.0101 (11)0.0106 (12)
C90.0333 (12)0.0433 (13)0.0463 (13)0.0043 (10)0.0046 (10)0.0021 (10)
C100.0405 (12)0.0358 (12)0.0295 (10)0.0029 (9)0.0013 (9)0.0024 (8)
C110.0338 (11)0.0393 (12)0.0321 (11)0.0031 (9)0.0048 (8)0.0051 (8)
C120.0293 (10)0.0320 (11)0.0318 (10)0.0012 (8)0.0013 (8)0.0039 (8)
C130.0321 (11)0.0362 (11)0.0327 (10)0.0040 (9)0.0028 (8)0.0046 (8)
C140.0624 (17)0.082 (2)0.0457 (14)0.0051 (15)0.0220 (13)0.0141 (13)
C150.0435 (13)0.0423 (13)0.0357 (11)0.0036 (10)0.0010 (10)0.0011 (9)
C160.0336 (12)0.0531 (14)0.0557 (15)0.0068 (11)0.0049 (10)0.0010 (11)
Br20.06391 (18)0.05326 (16)0.03660 (13)0.00056 (12)0.00434 (11)0.00705 (10)
Geometric parameters (Å, º) top
Br1—C21.899 (2)C3—C41.375 (3)
N1—C51.316 (3)C3—H30.93
N1—C11.353 (3)C4—C51.404 (3)
N2—C51.376 (3)C6—H6A0.96
N2—C71.377 (3)C6—H6B0.96
N2—C61.462 (3)C6—H6C0.96
N3—C41.380 (3)C8—H8A0.96
N3—C71.390 (3)C8—H8B0.96
N3—C81.447 (3)C8—H8C0.96
N4—C131.313 (3)C9—C101.381 (3)
N4—C91.348 (3)C9—H90.93
N5—C131.374 (3)C10—C111.390 (3)
N5—C151.376 (3)C10—Br21.893 (2)
N5—C141.457 (3)C11—C121.374 (3)
N6—C121.379 (3)C11—H110.93
N6—C151.381 (3)C12—C131.407 (3)
N6—C161.456 (3)C14—H14A0.96
O1—C71.222 (3)C14—H14B0.96
O2—C151.229 (3)C14—H14C0.96
C1—C21.369 (3)C16—H16A0.96
C1—H10.93C16—H16B0.96
C2—C31.397 (3)C16—H16C0.96
C5—N1—C1114.43 (18)N2—C7—N3106.43 (18)
C5—N2—C7109.90 (17)N3—C8—H8A109.5
C5—N2—C6126.63 (19)N3—C8—H8B109.5
C7—N2—C6123.40 (19)H8A—C8—H8B109.5
C4—N3—C7109.41 (18)N3—C8—H8C109.5
C4—N3—C8127.62 (19)H8A—C8—H8C109.5
C7—N3—C8122.96 (19)H8B—C8—H8C109.5
C13—N4—C9114.63 (18)N4—C9—C10123.2 (2)
C13—N5—C15109.67 (18)N4—C9—H9118.4
C13—N5—C14126.4 (2)C10—C9—H9118.4
C15—N5—C14123.9 (2)C9—C10—C11122.1 (2)
C12—N6—C15109.26 (17)C9—C10—Br2118.81 (16)
C12—N6—C16126.73 (18)C11—C10—Br2119.06 (16)
C15—N6—C16123.92 (19)C12—C11—C10114.59 (19)
N1—C1—C2123.1 (2)C12—C11—H11122.7
N1—C1—H1118.5C10—C11—H11122.7
C2—C1—H1118.5N6—C12—C11133.1 (2)
C1—C2—C3122.7 (2)N6—C12—C13107.11 (17)
C1—C2—Br1118.44 (16)C11—C12—C13119.8 (2)
C3—C2—Br1118.88 (16)N4—C13—N5127.28 (19)
C4—C3—C2114.1 (2)N4—C13—C12125.70 (19)
C4—C3—H3122.9N5—C13—C12107.02 (18)
C2—C3—H3122.9N5—C14—H14A109.5
C3—C4—N3133.2 (2)N5—C14—H14B109.5
C3—C4—C5119.79 (19)H14A—C14—H14B109.5
N3—C4—C5107.04 (18)N5—C14—H14C109.5
N1—C5—N2126.9 (2)H14A—C14—H14C109.5
N1—C5—C4125.9 (2)H14B—C14—H14C109.5
N2—C5—C4107.22 (18)O2—C15—N6126.3 (2)
N2—C6—H6A109.5O2—C15—N5126.8 (2)
N2—C6—H6B109.5N6—C15—N5106.92 (18)
H6A—C6—H6B109.5N6—C16—H16A109.5
N2—C6—H6C109.5N6—C16—H16B109.5
H6A—C6—H6C109.5H16A—C16—H16B109.5
H6B—C6—H6C109.5N6—C16—H16C109.5
O1—C7—N2127.3 (2)H16A—C16—H16C109.5
O1—C7—N3126.3 (2)H16B—C16—H16C109.5
C5—N1—C1—C20.2 (3)C13—N4—C9—C100.9 (3)
N1—C1—C2—C30.4 (4)N4—C9—C10—C110.2 (3)
N1—C1—C2—Br1179.39 (17)N4—C9—C10—Br2179.59 (17)
C1—C2—C3—C40.3 (3)C9—C10—C11—C120.6 (3)
Br1—C2—C3—C4179.52 (15)Br2—C10—C11—C12179.19 (15)
C2—C3—C4—N3179.6 (2)C15—N6—C12—C11178.1 (2)
C2—C3—C4—C50.0 (3)C16—N6—C12—C111.5 (4)
C7—N3—C4—C3179.7 (2)C15—N6—C12—C131.1 (2)
C8—N3—C4—C30.5 (4)C16—N6—C12—C13177.7 (2)
C7—N3—C4—C50.1 (2)C10—C11—C12—N6179.2 (2)
C8—N3—C4—C5179.9 (2)C10—C11—C12—C130.1 (3)
C1—N1—C5—N2179.9 (2)C9—N4—C13—N5178.9 (2)
C1—N1—C5—C40.1 (3)C9—N4—C13—C121.7 (3)
C7—N2—C5—N1180.0 (2)C15—N5—C13—N4179.7 (2)
C6—N2—C5—N13.0 (4)C14—N5—C13—N41.1 (4)
C7—N2—C5—C40.1 (2)C15—N5—C13—C120.8 (2)
C6—N2—C5—C4177.1 (2)C14—N5—C13—C12179.4 (2)
C3—C4—C5—N10.3 (3)N6—C12—C13—N4179.3 (2)
N3—C4—C5—N1180.0 (2)C11—C12—C13—N41.4 (3)
C3—C4—C5—N2179.80 (19)N6—C12—C13—N50.2 (2)
N3—C4—C5—N20.1 (2)C11—C12—C13—N5179.13 (19)
C5—N2—C7—O1179.8 (2)C12—N6—C15—O2179.2 (2)
C6—N2—C7—O13.1 (4)C16—N6—C15—O22.4 (4)
C5—N2—C7—N30.1 (3)C12—N6—C15—N51.5 (2)
C6—N2—C7—N3177.2 (2)C16—N6—C15—N5178.30 (19)
C4—N3—C7—O1179.7 (2)C13—N5—C15—O2179.3 (2)
C8—N3—C7—O10.1 (4)C14—N5—C15—O20.6 (4)
C4—N3—C7—N20.0 (3)C13—N5—C15—N61.4 (2)
C8—N3—C7—N2179.8 (2)C14—N5—C15—N6179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8C···O2i0.962.333.279 (3)167
C11—H11···O10.932.493.321 (3)148
Symmetry code: (i) x, y+5/2, z1/2.

Experimental details

Crystal data
Chemical formulaC8H8BrN3O
Mr242.08
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)21.7981 (4), 3.9929 (1), 20.6636 (3)
β (°) 95.398 (1)
V3)1790.53 (6)
Z8
Radiation typeMo Kα
µ (mm1)4.55
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker X8 APEXII area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.396, 0.548
No. of measured, independent and
observed [I > 2σ(I)] reflections
21586, 5229, 3539
Rint0.036
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.086, 1.01
No. of reflections5229
No. of parameters239
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.29

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8C···O2i0.962.333.279 (3)167
C11—H11···O10.932.493.321 (3)148
Symmetry code: (i) x, y+5/2, z1/2.
 

Acknowledgements

The authors thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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