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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o456.
Published online 2010 January 27. doi:  10.1107/S1600536810002679
PMCID: PMC2979787

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

Abstract

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 [triangle]); Bianchi et al. (1983 [triangle]); Clark et al. (1978 [triangle]); Janssens et al. (1985 [triangle]); Temple et al. (1987 [triangle]).

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Object name is e-66-0o456-scheme1.jpg

Experimental

Crystal data

  • C11H11BrN4O3
  • M r = 327.15
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o456-efi1.jpg
  • 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 [triangle]) T min = 0.356, T max = 0.854
  • 9174 measured reflections
  • 2224 independent reflections
  • 1633 reflections with I > 2σ(I)
  • R int = 0.062
  • Standard reflections: 0

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 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

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002679/bt5180sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002679/bt5180Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

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

Bruker APEXII diffractometer2224 independent reflections
Radiation source: fine-focus sealed tube1633 reflections with I > 2σ(I)
graphiteRint = 0.062
[var phi] and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −26→32
Tmin = 0.356, Tmax = 0.854k = −7→7
9174 measured reflectionsl = −19→19

Refinement

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 = 1.02w = 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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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—N3−176.1 (3)
C3—N1—C1—O2171.9 (4)C8—N4—C7—N3−179.2 (3)
C4—N1—C1—O1−171.3 (3)C8—N4—C7—C112.5 (5)
C3—N1—C1—O1−9.7 (4)C6—N3—C7—N4−177.8 (3)
C2—O1—C1—O2174.3 (4)C6—N3—C7—C110.8 (4)
C2—O1—C1—N1−4.2 (4)C7—N4—C8—C9−0.2 (5)
C1—O1—C2—C315.5 (5)N4—C8—C9—C10−1.6 (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—N1−19.6 (4)Br1—C9—C10—C11−177.2 (3)
C1—N1—C4—C5−107.3 (4)C9—C10—C11—N2−178.5 (4)
C3—N1—C4—C593.6 (4)C9—C10—C11—C70.9 (5)
C6—N2—C5—C475.4 (4)C6—N2—C11—C10−178.0 (4)
C11—N2—C5—C4−97.5 (4)C5—N2—C11—C10−4.3 (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—C10−2.9 (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—N3−2.1 (4)N3—C7—C11—N2−2.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O3i0.86 (1)1.94 (1)2.781 (4)167 (3)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5180).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • 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 [PubMed]
  • Bianchi, M., Butti, A., Rossi, S., Barzaghi, F. & Marcaria, V. (1983). Eur. J. Med. Chem. Chim. Ther 18, 501–506.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • 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. [PubMed]
  • Janssens, F., Torremans, J., Janssen, M., Stokbroekx, R. A., Luyckx, M. & Janssen, P. A. J. (1985). J. Med. Chem 28, 1943–1947. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Temple, C., Rose, J. D., Comber, R. N. & Rener, G. A. (1987). J. Med. Chem 30, 1746–1751 [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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