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ISSN: 2056-9890

3-Benzyl-6-bromo-2-(2-fur­yl)-3H-imidazo[4,5-b]pyridine

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 23 June 2010; accepted 24 June 2010; online 30 June 2010)

In the title mol­ecule, C17H12BrN3O, the imidazopyridine ring system is almost coplanar with the furan ring [dihedral angle = 2.0 (3)°]. The benzyl phenyl ring is oriented at dihedral angles of 85.2 (2) and 85.5 (1)°, respectively, with respect to the furan ring and the imidazopyridine ring system. In the crystal, mol­ecules are linked into chains propagating along the b axis by C—H⋯N hydrogen bonds. Adjacent chains are linked via short Br⋯Br contacts [3.493 (1) Å].

Related literature

For a related structure, see: Ouzidan et al. (2010[Ouzidan, Y., Obbade, S., Capet, F., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o946.]).

[Scheme 1]

Experimental

Crystal data
  • C17H12BrN3O

  • Mr = 354.21

  • Monoclinic, P 21 /c

  • a = 15.8422 (3) Å

  • b = 5.4747 (1) Å

  • c = 18.4243 (3) Å

  • β = 111.509 (1)°

  • V = 1486.68 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.77 mm−1

  • T = 293 K

  • 0.25 × 0.25 × 0.10 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 = 0.544, Tmax = 0.769

  • 19471 measured reflections

  • 2614 independent reflections

  • 2105 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.110

  • S = 0.97

  • 2614 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯N3i 0.93 2.51 3.399 (4) 160
Symmetry code: (i) [-x+1, y+{\script{1\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. Submitted.]).

Supporting information


Comment top

The imidazo[4,5-b]pyridine unit is an important heterocyclic nucleus found in a large number of molecules in medicinal chemistry. Heterocycles derived from such compounds posess useful medicinal properties. Owing to their importance, strategies have been developed for their synthesis. The most popular synthetic approach involves the cyclocondensation of 2,3-pyridinediamine with carboxylic acid derivatives or on condensation with aldehydes. An earlier study reported the crystal structure of 4-benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine (Ouzidan et al., 2010), which was synthesized by using a much more convenient route. The synthesis is extended to the title compound.

In the title molecule (Scheme and Fig. 1), the imidazopyridine ring system is almost coplanar with the furan ring at the 2-position of the five-membered ring [dihedral angle = 2.0 (3) °]. The molecules are linked into chains along the b axis by C—H···N hydrogen bonds (Table 1). The adjacent chains are linked via short Br···Br contacts [3.493 (1) Å].

Related literature top

For a related structure, see: Ouzidan et al. (2010).

Experimental top

6-Bromo-2-furyl-3H-imidazo[4,5-b]pyridine (0.30 g, 1.13 mmol) was dissolved in DMF (15 ml). Potassium carbonate (0.2 g, 1,48 mmol), tetra-n-butylammonium bromide (0.04 g, 0.1 mmol) and benzyl chloride (0.15 ml, 1.36 mmol) were added. Stirring was continued at room temperature for 12 h. The mixture was filtered and the solvent removed under reduced pressure. The residue was chromatographed on a column of silica gel with ethyl acetate-hexane (1/2) as eluent. The compound was recrystallized from chloroform to give orange crystals.

Refinement top

H atoms were placed in calculated positions (C–H = 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

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 molecule of C17H12BrN3O at the 50% probability level. H atoms are shown as spheres of arbitrary radii.
3-Benzyl-6-bromo-2-(2-furyl)-3H-imidazo[4,5-b]pyridine top
Crystal data top
C17H12BrN3OF(000) = 712
Mr = 354.21Dx = 1.583 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5830 reflections
a = 15.8422 (3) Åθ = 2.7–23.3°
b = 5.4747 (1) ŵ = 2.77 mm1
c = 18.4243 (3) ÅT = 293 K
β = 111.509 (1)°Prism, orange
V = 1486.68 (5) Å30.25 × 0.25 × 0.10 mm
Z = 4
Data collection top
Bruker X8 APEXII area-detector
diffractometer
2614 independent reflections
Radiation source: fine-focus sealed tube2105 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1718
Tmin = 0.544, Tmax = 0.769k = 65
19471 measured reflectionsl = 2118
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) = 0.110H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0848P)2 + 0.0891P]
where P = (Fo2 + 2Fc2)/3
2614 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
C17H12BrN3OV = 1486.68 (5) Å3
Mr = 354.21Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.8422 (3) ŵ = 2.77 mm1
b = 5.4747 (1) ÅT = 293 K
c = 18.4243 (3) Å0.25 × 0.25 × 0.10 mm
β = 111.509 (1)°
Data collection top
Bruker X8 APEXII area-detector
diffractometer
2614 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2105 reflections with I > 2σ(I)
Tmin = 0.544, Tmax = 0.769Rint = 0.036
19471 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 0.97Δρmax = 0.33 e Å3
2614 reflectionsΔρmin = 0.44 e Å3
199 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.47189 (2)1.27997 (6)0.426257 (19)0.05859 (18)
O10.21672 (14)0.1051 (4)0.11117 (12)0.0605 (6)
N10.28026 (15)0.7379 (4)0.34628 (14)0.0407 (6)
N20.26035 (13)0.4610 (4)0.23929 (12)0.0362 (5)
N30.37245 (14)0.6006 (4)0.20155 (13)0.0415 (5)
C10.33253 (18)0.9234 (5)0.38466 (16)0.0437 (6)
H10.32140.99160.42650.052*
C20.40263 (16)1.0193 (5)0.36533 (15)0.0399 (6)
C30.42374 (17)0.9297 (5)0.30393 (15)0.0400 (6)
H30.47010.99490.29040.048*
C40.37115 (19)0.7370 (4)0.26428 (18)0.0364 (6)
C50.30126 (16)0.6536 (5)0.28810 (15)0.0347 (6)
C60.18408 (17)0.3215 (5)0.24445 (16)0.0398 (6)
H6A0.18510.33350.29730.048*
H6B0.19230.15090.23440.048*
C70.09249 (16)0.4032 (4)0.18891 (15)0.0373 (6)
C80.0798 (2)0.6091 (6)0.1437 (2)0.0660 (9)
H80.12940.70500.14670.079*
C90.0063 (3)0.6757 (7)0.0935 (3)0.0863 (13)
H90.01390.81380.06230.104*
C100.0799 (2)0.5399 (7)0.0897 (2)0.0752 (10)
H100.13750.58390.05560.090*
C110.0687 (2)0.3409 (8)0.1356 (2)0.0706 (10)
H110.11900.25050.13400.085*
C120.0171 (2)0.2703 (5)0.1851 (2)0.0549 (8)
H120.02390.13190.21600.066*
C130.30648 (16)0.4385 (5)0.18846 (15)0.0369 (6)
C140.2871 (2)0.2623 (4)0.12615 (18)0.0428 (7)
C150.3289 (2)0.2287 (6)0.0754 (2)0.0587 (9)
H150.37870.31470.07370.070*
C160.2825 (2)0.0376 (6)0.02513 (19)0.0651 (9)
H160.29560.02660.01630.078*
C170.2169 (3)0.0318 (6)0.04850 (19)0.0683 (9)
H170.17610.15700.02570.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0540 (3)0.0519 (2)0.0593 (3)0.00676 (12)0.00831 (18)0.01181 (13)
O10.0659 (14)0.0602 (13)0.0594 (14)0.0183 (11)0.0276 (11)0.0162 (10)
N10.0330 (13)0.0534 (13)0.0395 (14)0.0029 (9)0.0176 (11)0.0003 (10)
N20.0268 (11)0.0449 (11)0.0378 (13)0.0025 (9)0.0130 (9)0.0003 (9)
N30.0317 (12)0.0538 (14)0.0424 (13)0.0020 (10)0.0175 (10)0.0037 (10)
C10.0380 (15)0.0519 (15)0.0416 (16)0.0036 (12)0.0150 (12)0.0047 (12)
C20.0330 (14)0.0416 (13)0.0391 (16)0.0017 (11)0.0061 (12)0.0006 (11)
C30.0296 (14)0.0464 (14)0.0440 (16)0.0006 (11)0.0135 (12)0.0030 (11)
C40.0281 (15)0.0436 (14)0.0396 (17)0.0007 (10)0.0147 (13)0.0028 (11)
C50.0253 (13)0.0419 (13)0.0361 (15)0.0025 (10)0.0101 (11)0.0027 (11)
C60.0345 (15)0.0458 (14)0.0414 (16)0.0046 (11)0.0165 (13)0.0047 (11)
C70.0288 (13)0.0408 (13)0.0437 (16)0.0052 (10)0.0152 (12)0.0047 (11)
C80.0388 (17)0.063 (2)0.086 (2)0.0040 (14)0.0108 (17)0.0219 (17)
C90.062 (2)0.069 (2)0.102 (3)0.0088 (19)0.001 (2)0.025 (2)
C100.0368 (19)0.089 (3)0.083 (3)0.0077 (17)0.0013 (17)0.012 (2)
C110.0350 (19)0.093 (3)0.081 (3)0.0156 (17)0.0181 (19)0.015 (2)
C120.0417 (19)0.0643 (19)0.061 (2)0.0119 (13)0.0216 (16)0.0033 (14)
C130.0291 (13)0.0446 (13)0.0366 (15)0.0046 (10)0.0116 (11)0.0011 (11)
C140.0353 (16)0.0481 (15)0.0427 (18)0.0018 (11)0.0117 (13)0.0002 (11)
C150.053 (2)0.074 (2)0.054 (2)0.0036 (14)0.0244 (18)0.0152 (15)
C160.076 (2)0.070 (2)0.049 (2)0.0112 (18)0.0221 (17)0.0105 (15)
C170.091 (3)0.0550 (18)0.054 (2)0.0113 (18)0.0199 (19)0.0155 (15)
Geometric parameters (Å, º) top
Br1—C21.897 (3)C7—C81.372 (4)
O1—C141.355 (3)C7—C121.377 (4)
O1—C171.378 (4)C8—C91.387 (5)
N1—C51.317 (3)C8—H80.93
N1—C11.337 (3)C9—C101.362 (5)
N2—C51.383 (3)C9—H90.93
N2—C131.388 (3)C10—C111.351 (5)
N2—C61.462 (3)C10—H100.93
N3—C131.324 (3)C11—C121.385 (5)
N3—C41.382 (4)C11—H110.93
C1—C21.388 (4)C12—H120.93
C1—H10.93C13—C141.444 (4)
C2—C31.382 (4)C14—C151.341 (5)
C3—C41.376 (4)C15—C161.412 (4)
C3—H30.93C15—H150.93
C4—C51.408 (4)C16—C171.317 (5)
C6—C71.505 (4)C16—H160.93
C6—H6A0.97C17—H170.93
C6—H6B0.97
C14—O1—C17105.2 (2)C7—C8—C9120.7 (3)
C5—N1—C1113.9 (2)C7—C8—H8119.7
C5—N2—C13105.62 (19)C9—C8—H8119.7
C5—N2—C6123.9 (2)C10—C9—C8120.3 (4)
C13—N2—C6130.5 (2)C10—C9—H9119.8
C13—N3—C4105.2 (2)C8—C9—H9119.8
N1—C1—C2123.4 (3)C11—C10—C9119.6 (3)
N1—C1—H1118.3C11—C10—H10120.2
C2—C1—H1118.3C9—C10—H10120.2
C3—C2—C1122.2 (2)C10—C11—C12120.6 (3)
C3—C2—Br1119.38 (19)C10—C11—H11119.7
C1—C2—Br1118.46 (19)C12—C11—H11119.7
C4—C3—C2115.2 (2)C7—C12—C11120.6 (3)
C4—C3—H3122.4C7—C12—H12119.7
C2—C3—H3122.4C11—C12—H12119.7
C3—C4—N3131.8 (2)N3—C13—N2113.1 (2)
C3—C4—C5118.4 (3)N3—C13—C14121.1 (2)
N3—C4—C5109.9 (2)N2—C13—C14125.8 (2)
N1—C5—N2126.8 (2)C15—C14—O1110.5 (3)
N1—C5—C4127.0 (2)C15—C14—C13129.1 (3)
N2—C5—C4106.2 (2)O1—C14—C13120.3 (3)
N2—C6—C7114.5 (2)C14—C15—C16106.7 (3)
N2—C6—H6A108.6C14—C15—H15126.6
C7—C6—H6A108.6C16—C15—H15126.6
N2—C6—H6B108.6C17—C16—C15106.4 (3)
C7—C6—H6B108.6C17—C16—H16126.8
H6A—C6—H6B107.6C15—C16—H16126.8
C8—C7—C12118.1 (3)C16—C17—O1111.2 (3)
C8—C7—C6123.2 (2)C16—C17—H17124.4
C12—C7—C6118.6 (2)O1—C17—H17124.4
C5—N1—C1—C20.0 (4)C6—C7—C8—C9180.0 (3)
N1—C1—C2—C30.2 (4)C7—C8—C9—C101.4 (7)
N1—C1—C2—Br1179.2 (2)C8—C9—C10—C110.7 (7)
C1—C2—C3—C40.8 (4)C9—C10—C11—C121.7 (6)
Br1—C2—C3—C4178.56 (19)C8—C7—C12—C111.3 (5)
C2—C3—C4—N3179.3 (3)C6—C7—C12—C11179.1 (3)
C2—C3—C4—C51.2 (4)C10—C11—C12—C70.7 (6)
C13—N3—C4—C3179.7 (3)C4—N3—C13—N20.5 (3)
C13—N3—C4—C50.7 (3)C4—N3—C13—C14179.9 (2)
C1—N1—C5—N2178.7 (2)C5—N2—C13—N30.0 (3)
C1—N1—C5—C40.4 (4)C6—N2—C13—N3179.7 (2)
C13—N2—C5—N1179.0 (2)C5—N2—C13—C14179.4 (2)
C6—N2—C5—N11.3 (4)C6—N2—C13—C140.3 (4)
C13—N2—C5—C40.4 (3)C17—O1—C14—C150.7 (4)
C6—N2—C5—C4179.9 (2)C17—O1—C14—C13179.1 (3)
C3—C4—C5—N11.1 (4)N3—C13—C14—C151.2 (5)
N3—C4—C5—N1179.3 (2)N2—C13—C14—C15179.5 (3)
C3—C4—C5—N2179.7 (2)N3—C13—C14—O1176.9 (2)
N3—C4—C5—N20.7 (3)N2—C13—C14—O12.4 (4)
C5—N2—C6—C796.8 (3)O1—C14—C15—C160.3 (4)
C13—N2—C6—C782.8 (3)C13—C14—C15—C16178.5 (3)
N2—C6—C7—C87.5 (4)C14—C15—C16—C170.3 (4)
N2—C6—C7—C12174.8 (2)C15—C16—C17—O10.7 (4)
C12—C7—C8—C92.3 (5)C14—O1—C17—C160.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···N3i0.932.513.399 (4)160
Symmetry code: (i) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H12BrN3O
Mr354.21
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)15.8422 (3), 5.4747 (1), 18.4243 (3)
β (°) 111.509 (1)
V3)1486.68 (5)
Z4
Radiation typeMo Kα
µ (mm1)2.77
Crystal size (mm)0.25 × 0.25 × 0.10
Data collection
DiffractometerBruker X8 APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.544, 0.769
No. of measured, independent and
observed [I > 2σ(I)] reflections
19471, 2614, 2105
Rint0.036
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.110, 0.97
No. of reflections2614
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.44

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
C3—H3···N3i0.932.513.399 (4)160
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA..  Google Scholar
First citationOuzidan, Y., Obbade, S., Capet, F., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o946.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43. Submitted.  Google Scholar

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