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

The title compound, C(11)H(11)BrN(4)O(3), 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-CH(2)-CH(2)-N torsion angle is 52.5 (4)°. In the crystal, pairs of mol-ecules 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 ▶); Bianchi et al. (1983 ▶); Clark et al. (1978 ▶); Janssens et al. (1985 ▶); Temple et al. (1987 ▶).

Experimental

Crystal data

C11H11BrN4O3

M = 327.15

Monoclinic,

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 ▶) 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 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536810002679/bt5180sup1.cif

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

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

C11H11BrN4O3	F(000) = 1312
Mr = 327.15	Dx = 1.717 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1559 reflections
a = 27.0174 (11) Å	θ = 2.6–22.4°
b = 6.0141 (2) Å	µ = 3.26 mm−1
c = 16.6121 (6) Å	T = 173 K
β = 110.343 (2)°	Plate, colorless
V = 2530.87 (16) Å3	0.40 × 0.20 × 0.05 mm
Z = 8

Bruker APEXII diffractometer	2224 independent reflections
Radiation source: fine-focus sealed tube	1633 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→32
Tmin = 0.356, Tmax = 0.854	k = −7→7
9174 measured reflections	l = −19→19

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H 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 parameters	Δρmax = 0.36 e Å−3
1 restraint	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.030317 (17)	1.14052 (7)	0.39869 (3)	0.03436 (15)
O1	0.07133 (11)	0.4365 (4)	0.17338 (18)	0.0398 (8)
O2	0.14847 (12)	0.2803 (5)	0.25167 (18)	0.0447 (8)
O3	0.26482 (10)	0.4281 (4)	0.42343 (15)	0.0266 (6)
N1	0.14287 (12)	0.6468 (5)	0.21101 (17)	0.0236 (7)
N2	0.20224 (12)	0.7116 (5)	0.38942 (18)	0.0197 (7)
N3	0.19871 (12)	0.4599 (5)	0.48386 (18)	0.0225 (7)
H3	0.2052 (13)	0.339 (3)	0.5132 (18)	0.022 (10)*
N4	0.12421 (12)	0.6066 (5)	0.51587 (18)	0.0242 (7)
C1	0.12398 (18)	0.4418 (7)	0.2151 (2)	0.0307 (10)
C2	0.05337 (18)	0.6589 (7)	0.1444 (3)	0.0565 (14)
H2A	0.0354	0.7266	0.1812	0.068*
H2B	0.0286	0.6568	0.0843	0.068*
C3	0.10292 (17)	0.7865 (6)	0.1514 (3)	0.0366 (11)
H3A	0.1079	0.7975	0.0953	0.044*
H3B	0.1026	0.9376	0.1749	0.044*
C4	0.19838 (15)	0.6905 (6)	0.2399 (2)	0.0261 (9)
H4A	0.2065	0.7762	0.1951	0.031*
H4B	0.2176	0.5474	0.2474	0.031*
C5	0.21827 (15)	0.8193 (6)	0.3239 (2)	0.0221 (9)
H5A	0.2573	0.8290	0.3439	0.027*
H5B	0.2040	0.9725	0.3143	0.027*
C6	0.22613 (15)	0.5212 (6)	0.4313 (2)	0.0220 (9)
C7	0.15790 (14)	0.6070 (6)	0.4745 (2)	0.0198 (8)
C8	0.08786 (15)	0.7701 (6)	0.4925 (2)	0.0268 (9)
H8	0.0624	0.7777	0.5201	0.032*
C9	0.08554 (15)	0.9282 (6)	0.4302 (2)	0.0227 (9)
C10	0.12232 (15)	0.9304 (6)	0.3887 (2)	0.0220 (9)
H10	0.1218	1.0386	0.3468	0.026*
C11	0.15928 (14)	0.7649 (6)	0.4130 (2)	0.0183 (8)

	U11	U22	U33	U12	U13	U23
Br1	0.0348 (3)	0.0294 (3)	0.0412 (2)	0.0106 (2)	0.01603 (19)	0.0026 (2)
O1	0.0332 (19)	0.0294 (17)	0.0488 (19)	−0.0102 (14)	0.0042 (15)	−0.0006 (14)
O2	0.055 (2)	0.0231 (17)	0.0475 (19)	0.0033 (15)	0.0068 (16)	0.0151 (14)
O3	0.0277 (17)	0.0288 (16)	0.0264 (14)	0.0084 (13)	0.0134 (13)	0.0087 (11)
N1	0.029 (2)	0.0179 (18)	0.0216 (16)	−0.0027 (16)	0.0057 (14)	0.0021 (14)
N2	0.0232 (18)	0.0189 (17)	0.0178 (15)	−0.0005 (14)	0.0081 (14)	0.0051 (13)
N3	0.030 (2)	0.0186 (19)	0.0194 (17)	0.0056 (15)	0.0091 (15)	0.0093 (14)
N4	0.0270 (19)	0.0258 (19)	0.0222 (16)	0.0046 (15)	0.0116 (15)	0.0050 (14)
C1	0.042 (3)	0.024 (2)	0.026 (2)	−0.005 (2)	0.010 (2)	−0.0023 (18)
C2	0.043 (3)	0.035 (3)	0.072 (3)	0.003 (3)	−0.005 (3)	0.003 (3)
C3	0.047 (3)	0.021 (2)	0.033 (2)	0.006 (2)	0.003 (2)	0.0018 (18)
C4	0.031 (2)	0.029 (2)	0.025 (2)	−0.0018 (18)	0.0185 (19)	0.0000 (17)
C5	0.023 (2)	0.023 (2)	0.0200 (19)	−0.0004 (17)	0.0075 (16)	0.0040 (16)
C6	0.025 (2)	0.022 (2)	0.0183 (19)	−0.0003 (18)	0.0070 (18)	0.0022 (16)
C7	0.021 (2)	0.018 (2)	0.0183 (18)	0.0015 (17)	0.0048 (16)	0.0007 (16)
C8	0.026 (2)	0.031 (2)	0.027 (2)	−0.0008 (19)	0.0140 (19)	−0.0025 (18)
C9	0.024 (2)	0.019 (2)	0.025 (2)	0.0039 (16)	0.0088 (18)	−0.0012 (16)
C10	0.029 (2)	0.018 (2)	0.0182 (19)	0.0031 (17)	0.0066 (17)	0.0022 (15)
C11	0.022 (2)	0.019 (2)	0.0143 (18)	−0.0030 (17)	0.0064 (17)	−0.0032 (16)

Br1—C9	1.894 (4)	C2—C3	1.512 (6)
O1—C1	1.349 (5)	C2—H2A	0.9900
O1—C2	1.447 (5)	C2—H2B	0.9900
O2—C1	1.213 (4)	C3—H3A	0.9900
O3—C6	1.232 (4)	C3—H3B	0.9900
N1—C1	1.345 (5)	C4—C5	1.521 (5)
N1—C4	1.431 (4)	C4—H4A	0.9900
N1—C3	1.452 (5)	C4—H4B	0.9900
N2—C6	1.378 (4)	C5—H5A	0.9900
N2—C11	1.385 (4)	C5—H5B	0.9900
N2—C5	1.457 (4)	C7—C11	1.405 (5)
N3—C6	1.377 (4)	C8—C9	1.390 (5)
N3—C7	1.380 (4)	C8—H8	0.9500
N3—H3	0.859 (10)	C9—C10	1.393 (5)
N4—C7	1.318 (4)	C10—C11	1.368 (5)
N4—C8	1.348 (4)	C10—H10	0.9500
C1—O1—C2	108.7 (3)	C5—C4—H4A	108.9
C1—N1—C4	121.6 (3)	N1—C4—H4B	108.9
C1—N1—C3	111.1 (3)	C5—C4—H4B	108.9
C4—N1—C3	124.5 (3)	H4A—C4—H4B	107.7
C6—N2—C11	109.9 (3)	N2—C5—C4	110.9 (3)
C6—N2—C5	122.6 (3)	N2—C5—H5A	109.5
C11—N2—C5	127.2 (3)	C4—C5—H5A	109.5
C6—N3—C7	110.0 (3)	N2—C5—H5B	109.5
C6—N3—H3	123 (2)	C4—C5—H5B	109.5
C7—N3—H3	127 (2)	H5A—C5—H5B	108.0
C7—N4—C8	114.5 (3)	O3—C6—N3	127.5 (3)
O2—C1—N1	127.5 (4)	O3—C6—N2	126.1 (3)
O2—C1—O1	122.2 (4)	N3—C6—N2	106.4 (3)
N1—C1—O1	110.3 (3)	N4—C7—N3	127.6 (3)
O1—C2—C3	104.9 (3)	N4—C7—C11	125.3 (3)
O1—C2—H2A	110.8	N3—C7—C11	107.1 (3)
C3—C2—H2A	110.8	N4—C8—C9	123.6 (3)
O1—C2—H2B	110.8	N4—C8—H8	118.2
C3—C2—H2B	110.8	C9—C8—H8	118.2
H2A—C2—H2B	108.8	C8—C9—C10	121.3 (3)
N1—C3—C2	100.8 (3)	C8—C9—Br1	119.6 (3)
N1—C3—H3A	111.6	C10—C9—Br1	119.1 (3)
C2—C3—H3A	111.6	C11—C10—C9	114.9 (3)
N1—C3—H3B	111.6	C11—C10—H10	122.6
C2—C3—H3B	111.6	C9—C10—H10	122.6
H3A—C3—H3B	109.4	C10—C11—N2	133.1 (3)
N1—C4—C5	113.3 (3)	C10—C11—C7	120.3 (3)
N1—C4—H4A	108.9	N2—C11—C7	106.6 (3)
C4—N1—C1—O2	10.3 (6)	C5—N2—C6—N3	−176.1 (3)
C3—N1—C1—O2	171.9 (4)	C8—N4—C7—N3	−179.2 (3)
C4—N1—C1—O1	−171.3 (3)	C8—N4—C7—C11	2.5 (5)
C3—N1—C1—O1	−9.7 (4)	C6—N3—C7—N4	−177.8 (3)
C2—O1—C1—O2	174.3 (4)	C6—N3—C7—C11	0.8 (4)
C2—O1—C1—N1	−4.2 (4)	C7—N4—C8—C9	−0.2 (5)
C1—O1—C2—C3	15.5 (5)	N4—C8—C9—C10	−1.6 (6)
C1—N1—C3—C2	18.3 (4)	N4—C8—C9—Br1	176.7 (3)
C4—N1—C3—C2	179.3 (3)	C8—C9—C10—C11	1.2 (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—C5	93.6 (4)	C9—C10—C11—C7	0.9 (5)
C6—N2—C5—C4	75.4 (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—N2	52.5 (4)	C6—N2—C11—C7	2.6 (4)
C7—N3—C6—O3	179.9 (4)	C5—N2—C11—C7	176.2 (3)
C7—N3—C6—N2	0.8 (4)	N4—C7—C11—C10	−2.9 (6)
C11—N2—C6—O3	178.8 (4)	N3—C7—C11—C10	178.5 (3)
C5—N2—C6—O3	4.8 (6)	N4—C7—C11—N2	176.6 (3)
C11—N2—C6—N3	−2.1 (4)	N3—C7—C11—N2	−2.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3i	0.86 (1)	1.94 (1)	2.781 (4)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3i	0.86 (1)	1.94 (1)	2.781 (4)	167 (3)

Symmetry code: (i) .