organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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6-Bromo-1-[2-(2-oxo-1,3-oxazolidin-3-yl)eth­yl]-1H-imidazo[4,5-b]pyridin-2(3H)-one

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, 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 20 January 2010; accepted 21 January 2010; online 27 January 2010)

The title compound, C11H11BrN4O3, features an ethane fragment substituted with an almost planar (r.m.s. deviation = 0.019 Å) imidazo[4,5-b]pyridone ring system and an envelope-shaped oxazolidine unit on separate C atoms. The N—CH2—CH2—N torsion angle is 52.5 (4)°. In the crystal, pairs of mol­ecules are linked by N—H⋯O hydrogen bonds into centrosymmetric dimers.

Related literature

For the medicinal properties of imidazo[4,5-b]pyridines, see: Barraclough et al. (1990[Barraclough, P., Black, J. W., Cambridge, D., Collard, D., Firmin, D., Gerskowitch, V. P., Glen, R. C., Giles, H., Hill, A. P., Hull, R. A. D., Iyer, R., King, W. R., Kneen, C. O., Lindon, J. C., Nobbs, M. S., Randall, P., Shah, G. P., Smith, S., Vine, S. J., Whiting, M. V. & Williams, J. M. (1990). J. Med. Chem. 33, 2231-2239]); Bianchi et al. (1983[Bianchi, M., Butti, A., Rossi, S., Barzaghi, F. & Marcaria, V. (1983). Eur. J. Med. Chem. Chim. Ther. 18, 501-506.]); Clark et al. (1978[Clark, R. L., Pessolano, A. A., Shen, T.-Y., Jocobus, D. P., Jones, H., Lotti, V. J. & Flataker, L. M. (1978). J. Med. Chem. 21, 965-978.]); Janssens et al. (1985[Janssens, F., Torremans, J., Janssen, M., Stokbroekx, R. A., Luyckx, M. & Janssen, P. A. J. (1985). J. Med. Chem. 28, 1943-1947.]); Temple et al. (1987[Temple, C., Rose, J. D., Comber, R. N. & Rener, G. A. (1987). J. Med. Chem. 30, 1746-1751]).

[Scheme 1]

Experimental

Crystal data
  • C11H11BrN4O3

  • Mr = 327.15

  • Monoclinic, C 2/c

  • a = 27.0174 (11) Å

  • b = 6.0141 (2) Å

  • c = 16.6121 (6) Å

  • β = 110.343 (2)°

  • V = 2530.87 (16) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.26 mm−1

  • T = 173 K

  • 0.40 × 0.20 × 0.05 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.356, Tmax = 0.854

  • 9174 measured reflections

  • 2224 independent reflections

  • 1633 reflections with I > 2σ(I)

  • Rint = 0.062

  • Standard reflections: 0

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.077

  • S = 1.02

  • 2224 reflections

  • 176 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.36 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3⋯O3i 0.86 (1) 1.94 (1) 2.781 (4) 167 (3)
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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). publCIF. In preparation.]).

Supporting information


Related literature top

For the medicinal properties of imidazo[4,5-b]pyridines, see: Barraclough et al. (1990); Bianchi et al. (1983); Clark et al. (1978); Janssens et al. (1985); Temple et al. (1987).

Experimental top

To 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one (1 mmol), potassium carbonate (4 mmol), and tetra-n-butylammonium bromide (0.1 mmol) in DMF (30 ml) was added bis(2-chloroethyl)amine hydrochloride (2.5 mmol). The mixture was heated for 48 h. After the completion of the reaction (as monitored by TLC), the inorganic material salt was filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel by using (ethylacetate/hexane: 2/1) as eluent to furnish colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.94-0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.86±0.01 Å; its displacement parameter was refined isotropically.

Structure description top

For the medicinal properties of imidazo[4,5-b]pyridines, see: Barraclough et al. (1990); Bianchi et al. (1983); Clark et al. (1978); Janssens et al. (1985); Temple et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C11H11BrN4O3 at the 70% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.
6-Bromo-1-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H- imidazo[4,5-b]pyridin-2(3H)-one top
Crystal data top
C11H11BrN4O3F(000) = 1312
Mr = 327.15Dx = 1.717 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1559 reflections
a = 27.0174 (11) Åθ = 2.6–22.4°
b = 6.0141 (2) ŵ = 3.26 mm1
c = 16.6121 (6) ÅT = 173 K
β = 110.343 (2)°Plate, colorless
V = 2530.87 (16) Å30.40 × 0.20 × 0.05 mm
Z = 8
Data collection top
Bruker APEXII
diffractometer
2224 independent reflections
Radiation source: fine-focus sealed tube1633 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2632
Tmin = 0.356, Tmax = 0.854k = 77
9174 measured reflectionsl = 1919
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0269P)2 + 1.8498P]
where P = (Fo2 + 2Fc2)/3
2224 reflections(Δ/σ)max = 0.001
176 parametersΔρmax = 0.36 e Å3
1 restraintΔρmin = 0.36 e Å3
Crystal data top
C11H11BrN4O3V = 2530.87 (16) Å3
Mr = 327.15Z = 8
Monoclinic, C2/cMo Kα radiation
a = 27.0174 (11) ŵ = 3.26 mm1
b = 6.0141 (2) ÅT = 173 K
c = 16.6121 (6) Å0.40 × 0.20 × 0.05 mm
β = 110.343 (2)°
Data collection top
Bruker APEXII
diffractometer
2224 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1633 reflections with I > 2σ(I)
Tmin = 0.356, Tmax = 0.854Rint = 0.062
9174 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0381 restraint
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.36 e Å3
2224 reflectionsΔρmin = 0.36 e Å3
176 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.030317 (17)1.14052 (7)0.39869 (3)0.03436 (15)
O10.07133 (11)0.4365 (4)0.17338 (18)0.0398 (8)
O20.14847 (12)0.2803 (5)0.25167 (18)0.0447 (8)
O30.26482 (10)0.4281 (4)0.42343 (15)0.0266 (6)
N10.14287 (12)0.6468 (5)0.21101 (17)0.0236 (7)
N20.20224 (12)0.7116 (5)0.38942 (18)0.0197 (7)
N30.19871 (12)0.4599 (5)0.48386 (18)0.0225 (7)
H30.2052 (13)0.339 (3)0.5132 (18)0.022 (10)*
N40.12421 (12)0.6066 (5)0.51587 (18)0.0242 (7)
C10.12398 (18)0.4418 (7)0.2151 (2)0.0307 (10)
C20.05337 (18)0.6589 (7)0.1444 (3)0.0565 (14)
H2A0.03540.72660.18120.068*
H2B0.02860.65680.08430.068*
C30.10292 (17)0.7865 (6)0.1514 (3)0.0366 (11)
H3A0.10790.79750.09530.044*
H3B0.10260.93760.17490.044*
C40.19838 (15)0.6905 (6)0.2399 (2)0.0261 (9)
H4A0.20650.77620.19510.031*
H4B0.21760.54740.24740.031*
C50.21827 (15)0.8193 (6)0.3239 (2)0.0221 (9)
H5A0.25730.82900.34390.027*
H5B0.20400.97250.31430.027*
C60.22613 (15)0.5212 (6)0.4313 (2)0.0220 (9)
C70.15790 (14)0.6070 (6)0.4745 (2)0.0198 (8)
C80.08786 (15)0.7701 (6)0.4925 (2)0.0268 (9)
H80.06240.77770.52010.032*
C90.08554 (15)0.9282 (6)0.4302 (2)0.0227 (9)
C100.12232 (15)0.9304 (6)0.3887 (2)0.0220 (9)
H100.12181.03860.34680.026*
C110.15928 (14)0.7649 (6)0.4130 (2)0.0183 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0348 (3)0.0294 (3)0.0412 (2)0.0106 (2)0.01603 (19)0.0026 (2)
O10.0332 (19)0.0294 (17)0.0488 (19)0.0102 (14)0.0042 (15)0.0006 (14)
O20.055 (2)0.0231 (17)0.0475 (19)0.0033 (15)0.0068 (16)0.0151 (14)
O30.0277 (17)0.0288 (16)0.0264 (14)0.0084 (13)0.0134 (13)0.0087 (11)
N10.029 (2)0.0179 (18)0.0216 (16)0.0027 (16)0.0057 (14)0.0021 (14)
N20.0232 (18)0.0189 (17)0.0178 (15)0.0005 (14)0.0081 (14)0.0051 (13)
N30.030 (2)0.0186 (19)0.0194 (17)0.0056 (15)0.0091 (15)0.0093 (14)
N40.0270 (19)0.0258 (19)0.0222 (16)0.0046 (15)0.0116 (15)0.0050 (14)
C10.042 (3)0.024 (2)0.026 (2)0.005 (2)0.010 (2)0.0023 (18)
C20.043 (3)0.035 (3)0.072 (3)0.003 (3)0.005 (3)0.003 (3)
C30.047 (3)0.021 (2)0.033 (2)0.006 (2)0.003 (2)0.0018 (18)
C40.031 (2)0.029 (2)0.025 (2)0.0018 (18)0.0185 (19)0.0000 (17)
C50.023 (2)0.023 (2)0.0200 (19)0.0004 (17)0.0075 (16)0.0040 (16)
C60.025 (2)0.022 (2)0.0183 (19)0.0003 (18)0.0070 (18)0.0022 (16)
C70.021 (2)0.018 (2)0.0183 (18)0.0015 (17)0.0048 (16)0.0007 (16)
C80.026 (2)0.031 (2)0.027 (2)0.0008 (19)0.0140 (19)0.0025 (18)
C90.024 (2)0.019 (2)0.025 (2)0.0039 (16)0.0088 (18)0.0012 (16)
C100.029 (2)0.018 (2)0.0182 (19)0.0031 (17)0.0066 (17)0.0022 (15)
C110.022 (2)0.019 (2)0.0143 (18)0.0030 (17)0.0064 (17)0.0032 (16)
Geometric parameters (Å, º) top
Br1—C91.894 (4)C2—C31.512 (6)
O1—C11.349 (5)C2—H2A0.9900
O1—C21.447 (5)C2—H2B0.9900
O2—C11.213 (4)C3—H3A0.9900
O3—C61.232 (4)C3—H3B0.9900
N1—C11.345 (5)C4—C51.521 (5)
N1—C41.431 (4)C4—H4A0.9900
N1—C31.452 (5)C4—H4B0.9900
N2—C61.378 (4)C5—H5A0.9900
N2—C111.385 (4)C5—H5B0.9900
N2—C51.457 (4)C7—C111.405 (5)
N3—C61.377 (4)C8—C91.390 (5)
N3—C71.380 (4)C8—H80.9500
N3—H30.859 (10)C9—C101.393 (5)
N4—C71.318 (4)C10—C111.368 (5)
N4—C81.348 (4)C10—H100.9500
C1—O1—C2108.7 (3)C5—C4—H4A108.9
C1—N1—C4121.6 (3)N1—C4—H4B108.9
C1—N1—C3111.1 (3)C5—C4—H4B108.9
C4—N1—C3124.5 (3)H4A—C4—H4B107.7
C6—N2—C11109.9 (3)N2—C5—C4110.9 (3)
C6—N2—C5122.6 (3)N2—C5—H5A109.5
C11—N2—C5127.2 (3)C4—C5—H5A109.5
C6—N3—C7110.0 (3)N2—C5—H5B109.5
C6—N3—H3123 (2)C4—C5—H5B109.5
C7—N3—H3127 (2)H5A—C5—H5B108.0
C7—N4—C8114.5 (3)O3—C6—N3127.5 (3)
O2—C1—N1127.5 (4)O3—C6—N2126.1 (3)
O2—C1—O1122.2 (4)N3—C6—N2106.4 (3)
N1—C1—O1110.3 (3)N4—C7—N3127.6 (3)
O1—C2—C3104.9 (3)N4—C7—C11125.3 (3)
O1—C2—H2A110.8N3—C7—C11107.1 (3)
C3—C2—H2A110.8N4—C8—C9123.6 (3)
O1—C2—H2B110.8N4—C8—H8118.2
C3—C2—H2B110.8C9—C8—H8118.2
H2A—C2—H2B108.8C8—C9—C10121.3 (3)
N1—C3—C2100.8 (3)C8—C9—Br1119.6 (3)
N1—C3—H3A111.6C10—C9—Br1119.1 (3)
C2—C3—H3A111.6C11—C10—C9114.9 (3)
N1—C3—H3B111.6C11—C10—H10122.6
C2—C3—H3B111.6C9—C10—H10122.6
H3A—C3—H3B109.4C10—C11—N2133.1 (3)
N1—C4—C5113.3 (3)C10—C11—C7120.3 (3)
N1—C4—H4A108.9N2—C11—C7106.6 (3)
C4—N1—C1—O210.3 (6)C5—N2—C6—N3176.1 (3)
C3—N1—C1—O2171.9 (4)C8—N4—C7—N3179.2 (3)
C4—N1—C1—O1171.3 (3)C8—N4—C7—C112.5 (5)
C3—N1—C1—O19.7 (4)C6—N3—C7—N4177.8 (3)
C2—O1—C1—O2174.3 (4)C6—N3—C7—C110.8 (4)
C2—O1—C1—N14.2 (4)C7—N4—C8—C90.2 (5)
C1—O1—C2—C315.5 (5)N4—C8—C9—C101.6 (6)
C1—N1—C3—C218.3 (4)N4—C8—C9—Br1176.7 (3)
C4—N1—C3—C2179.3 (3)C8—C9—C10—C111.2 (5)
O1—C2—C3—N119.6 (4)Br1—C9—C10—C11177.2 (3)
C1—N1—C4—C5107.3 (4)C9—C10—C11—N2178.5 (4)
C3—N1—C4—C593.6 (4)C9—C10—C11—C70.9 (5)
C6—N2—C5—C475.4 (4)C6—N2—C11—C10178.0 (4)
C11—N2—C5—C497.5 (4)C5—N2—C11—C104.3 (6)
N1—C4—C5—N252.5 (4)C6—N2—C11—C72.6 (4)
C7—N3—C6—O3179.9 (4)C5—N2—C11—C7176.2 (3)
C7—N3—C6—N20.8 (4)N4—C7—C11—C102.9 (6)
C11—N2—C6—O3178.8 (4)N3—C7—C11—C10178.5 (3)
C5—N2—C6—O34.8 (6)N4—C7—C11—N2176.6 (3)
C11—N2—C6—N32.1 (4)N3—C7—C11—N22.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O3i0.86 (1)1.94 (1)2.781 (4)167 (3)
Symmetry code: (i) x+1/2, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC11H11BrN4O3
Mr327.15
Crystal system, space groupMonoclinic, C2/c
Temperature (K)173
a, b, c (Å)27.0174 (11), 6.0141 (2), 16.6121 (6)
β (°) 110.343 (2)
V3)2530.87 (16)
Z8
Radiation typeMo Kα
µ (mm1)3.26
Crystal size (mm)0.40 × 0.20 × 0.05
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.356, 0.854
No. of measured, independent and
observed [I > 2σ(I)] reflections
9174, 2224, 1633
Rint0.062
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.077, 1.02
No. of reflections2224
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.36, 0.36

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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
N3—H3···O3i0.86 (1)1.94 (1)2.781 (4)167 (3)
Symmetry code: (i) x+1/2, y+1/2, z+1.
 

Acknowledgements

We 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 citationBarraclough, P., Black, J. W., Cambridge, D., Collard, D., Firmin, D., Gerskowitch, V. P., Glen, R. C., Giles, H., Hill, A. P., Hull, R. A. D., Iyer, R., King, W. R., Kneen, C. O., Lindon, J. C., Nobbs, M. S., Randall, P., Shah, G. P., Smith, S., Vine, S. J., Whiting, M. V. & Williams, J. M. (1990). J. Med. Chem. 33, 2231–2239  CrossRef CAS PubMed Web of Science Google Scholar
First citationBianchi, M., Butti, A., Rossi, S., Barzaghi, F. & Marcaria, V. (1983). Eur. J. Med. Chem. Chim. Ther. 18, 501–506.  CAS Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationClark, R. L., Pessolano, A. A., Shen, T.-Y., Jocobus, D. P., Jones, H., Lotti, V. J. & Flataker, L. M. (1978). J. Med. Chem. 21, 965–978.  CrossRef CAS PubMed Web of Science Google Scholar
First citationJanssens, F., Torremans, J., Janssen, M., Stokbroekx, R. A., Luyckx, M. & Janssen, P. A. J. (1985). J. Med. Chem. 28, 1943–1947.  CrossRef CAS PubMed Web of Science 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 citationTemple, C., Rose, J. D., Comber, R. N. & Rener, G. A. (1987). J. Med. Chem. 30, 1746–1751  CrossRef CAS PubMed Web of Science Google Scholar
First citationWestrip, S. P. (2010). publCIF. In preparation.  Google Scholar

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