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

In the title mol-ecule, C(17)H(15)BrN(4)O(2), the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.015 (2) Å, and forms dihedral angles of 37.8 (2) and 35.5 (2)° with the phenyl and oxazolidine rings, respectively. The conformation adopted by the mol-ecule is stabilized by an intra-molecular π⋯π inter-action [centroid-centroid distance = 3.855(2) Å] between oxazolidine and phenyl rings. The crystal packing features inter-molecular C-H⋯N and C-H⋯O inter-actions.

Related literature

For background to the medicinal chemistry of oxazolidin-2-ones and their application in asymmetric synthesis, see: Diekema & Jones (2000 ▶); Mukhtar & Wright (2004 ▶); Evans et al. (1993 ▶); Matsunaga et al. (2005 ▶). For similar compounds with an imidazo[4,5-b]pyridine group, see: Ouzidan et al. (2010a ▶,b ▶).

Experimental

Crystal data

C17H15BrN4O2

M = 387.24

Monoclinic,

a = 11.3553 (6) Å

b = 11.5915 (5) Å

c = 12.2542 (8) Å

β = 98.685 (6)°

V = 1594.46 (15) Å3

Z = 4

Mo Kα radiation

μ = 2.60 mm−1

T = 170 K

0.22 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction XcaliburE Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.599, T max = 0.652

7850 measured reflections

3791 independent reflections

2839 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.091

S = 1.03

3791 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012669/gk2362sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012669/gk2362Isup2.hkl

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

C17H15BrN4O2	F(000) = 784
Mr = 387.24	Dx = 1.613 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3008 reflections
a = 11.3553 (6) Å	θ = 3.5–32.3°
b = 11.5915 (5) Å	µ = 2.60 mm−1
c = 12.2542 (8) Å	T = 170 K
β = 98.685 (6)°	Block, colourless
V = 1594.46 (15) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Oxford Diffraction XcaliburE Gemini diffractometer	3791 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2839 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 16.1500 pixels mm-1	θmax = 27.9°, θmin = 3.5°
ω scans	h = −9→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→6
Tmin = 0.599, Tmax = 0.652	l = −15→16
7850 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.4211P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3791 reflections	Δρmax = 0.50 e Å−3
218 parameters	Δρmin = −0.35 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (7)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.83535 (2)	0.94591 (2)	0.34797 (3)	0.05968 (13)
O1	0.28122 (17)	0.80153 (15)	0.18265 (18)	0.0643 (6)
O2	0.09323 (15)	0.76454 (14)	0.20646 (16)	0.0521 (5)
N1	0.61867 (17)	0.66117 (16)	0.33964 (18)	0.0444 (5)
N2	0.42350 (16)	0.82558 (14)	0.48010 (15)	0.0331 (4)
N3	0.43353 (16)	0.64555 (14)	0.41210 (15)	0.0341 (4)
N4	0.22330 (16)	0.62233 (15)	0.23253 (16)	0.0380 (4)
C1	0.53419 (19)	0.70349 (17)	0.39157 (18)	0.0336 (5)
C2	0.7057 (2)	0.7361 (2)	0.3310 (2)	0.0476 (6)
H2A	0.7694	0.7119	0.2943	0.057*
C3	0.7086 (2)	0.84809 (19)	0.3727 (2)	0.0386 (5)
C4	0.61915 (19)	0.89053 (18)	0.42593 (18)	0.0347 (5)
H4A	0.6204	0.9668	0.4544	0.042*
C5	0.52729 (19)	0.81425 (17)	0.43494 (18)	0.0313 (5)
C6	0.37023 (19)	0.72409 (17)	0.46453 (17)	0.0314 (5)
C7	0.3943 (2)	0.53819 (17)	0.3543 (2)	0.0397 (5)
H7A	0.3378	0.4977	0.3952	0.048*
H7B	0.4640	0.4872	0.3526	0.048*
C8	0.3343 (2)	0.56137 (19)	0.2369 (2)	0.0427 (6)
H8A	0.3888	0.6072	0.1981	0.051*
H8B	0.3195	0.4870	0.1975	0.051*
C9	0.2077 (2)	0.7339 (2)	0.2053 (2)	0.0422 (6)
C10	0.0290 (2)	0.6685 (2)	0.2428 (2)	0.0473 (6)
H10A	−0.0444	0.6533	0.1900	0.057*
H10B	0.0066	0.6841	0.3164	0.057*
C11	0.1133 (2)	0.5666 (2)	0.2479 (2)	0.0494 (6)
H11A	0.1207	0.5270	0.3201	0.059*
H11B	0.0873	0.5104	0.1882	0.059*
C12	0.25728 (19)	0.69848 (18)	0.50368 (17)	0.0331 (5)
C13	0.2346 (2)	0.5929 (2)	0.5501 (2)	0.0491 (6)
H13A	0.2927	0.5333	0.5559	0.059*
C14	0.1272 (3)	0.5745 (2)	0.5880 (2)	0.0582 (7)
H14A	0.1116	0.5019	0.6188	0.070*
C15	0.0434 (2)	0.6598 (3)	0.5815 (2)	0.0572 (7)
H15A	−0.0304	0.6462	0.6069	0.069*
C16	0.0661 (2)	0.7651 (2)	0.5383 (2)	0.0511 (6)
H16A	0.0085	0.8249	0.5350	0.061*
C17	0.1725 (2)	0.7849 (2)	0.49934 (19)	0.0407 (5)
H17A	0.1875	0.8581	0.4695	0.049*

	U11	U22	U33	U12	U13	U23
Br1	0.04820 (18)	0.05086 (18)	0.0845 (3)	−0.01581 (12)	0.02468 (15)	−0.00566 (14)
O1	0.0624 (12)	0.0360 (9)	0.0993 (16)	−0.0107 (9)	0.0285 (11)	0.0095 (10)
O2	0.0458 (10)	0.0376 (9)	0.0730 (13)	0.0032 (8)	0.0094 (9)	0.0075 (8)
N1	0.0396 (11)	0.0275 (9)	0.0690 (14)	0.0033 (8)	0.0182 (10)	−0.0068 (9)
N2	0.0361 (10)	0.0268 (9)	0.0377 (10)	−0.0006 (8)	0.0093 (8)	−0.0039 (7)
N3	0.0339 (10)	0.0215 (8)	0.0468 (11)	−0.0001 (7)	0.0063 (8)	−0.0022 (8)
N4	0.0378 (11)	0.0287 (9)	0.0472 (12)	−0.0055 (8)	0.0061 (9)	0.0012 (8)
C1	0.0321 (11)	0.0243 (10)	0.0440 (13)	0.0016 (9)	0.0038 (9)	0.0011 (9)
C2	0.0388 (13)	0.0367 (12)	0.0708 (18)	0.0047 (11)	0.0200 (12)	−0.0055 (12)
C3	0.0328 (12)	0.0334 (11)	0.0498 (14)	−0.0021 (9)	0.0071 (10)	0.0032 (10)
C4	0.0375 (12)	0.0246 (10)	0.0412 (13)	−0.0019 (9)	0.0033 (9)	−0.0021 (9)
C5	0.0345 (11)	0.0241 (10)	0.0349 (12)	0.0018 (8)	0.0039 (9)	0.0000 (8)
C6	0.0333 (11)	0.0263 (10)	0.0342 (12)	0.0024 (9)	0.0034 (9)	0.0015 (9)
C7	0.0419 (13)	0.0184 (10)	0.0593 (16)	0.0013 (9)	0.0094 (11)	−0.0036 (9)
C8	0.0491 (14)	0.0297 (11)	0.0517 (15)	−0.0020 (10)	0.0154 (11)	−0.0099 (10)
C9	0.0505 (15)	0.0314 (12)	0.0450 (14)	−0.0046 (11)	0.0084 (11)	−0.0009 (10)
C10	0.0428 (14)	0.0531 (15)	0.0459 (15)	−0.0086 (12)	0.0063 (11)	0.0027 (12)
C11	0.0421 (14)	0.0404 (14)	0.0644 (18)	−0.0132 (11)	0.0037 (12)	0.0041 (12)
C12	0.0341 (11)	0.0336 (11)	0.0319 (12)	−0.0022 (9)	0.0057 (9)	−0.0017 (9)
C13	0.0509 (15)	0.0385 (13)	0.0595 (17)	0.0001 (11)	0.0140 (12)	0.0078 (12)
C14	0.0626 (18)	0.0510 (16)	0.0657 (19)	−0.0159 (14)	0.0248 (15)	0.0080 (13)
C15	0.0475 (16)	0.0679 (18)	0.0607 (18)	−0.0146 (14)	0.0228 (13)	−0.0063 (14)
C16	0.0446 (14)	0.0599 (16)	0.0514 (16)	0.0073 (13)	0.0152 (12)	−0.0050 (13)
C17	0.0453 (13)	0.0374 (12)	0.0418 (13)	0.0017 (10)	0.0139 (10)	−0.0003 (10)

Br1—C3	1.892 (2)	C7—C8	1.520 (4)
O1—C9	1.208 (3)	C7—H7A	0.9900
O2—C9	1.349 (3)	C7—H7B	0.9900
O2—C10	1.438 (3)	C8—H8A	0.9900
N1—C1	1.323 (3)	C8—H8B	0.9900
N1—C2	1.332 (3)	C10—C11	1.516 (4)
N2—C6	1.323 (3)	C10—H10A	0.9900
N2—C5	1.382 (3)	C10—H10B	0.9900
N3—C6	1.378 (3)	C11—H11A	0.9900
N3—C1	1.381 (3)	C11—H11B	0.9900
N3—C7	1.467 (3)	C12—C17	1.385 (3)
N4—C9	1.340 (3)	C12—C13	1.390 (3)
N4—C8	1.439 (3)	C13—C14	1.385 (4)
N4—C11	1.443 (3)	C13—H13A	0.9500
C1—C5	1.396 (3)	C14—C15	1.366 (4)
C2—C3	1.393 (3)	C14—H14A	0.9500
C2—H2A	0.9500	C15—C16	1.370 (4)
C3—C4	1.378 (3)	C15—H15A	0.9500
C4—C5	1.385 (3)	C16—C17	1.383 (3)
C4—H4A	0.9500	C16—H16A	0.9500
C6—C12	1.466 (3)	C17—H17A	0.9500
C9—O2—C10	109.50 (18)	N4—C8—H8B	109.0
C1—N1—C2	113.39 (19)	C7—C8—H8B	109.0
C6—N2—C5	104.87 (17)	H8A—C8—H8B	107.8
C6—N3—C1	105.55 (16)	O1—C9—N4	127.8 (2)
C6—N3—C7	130.08 (18)	O1—C9—O2	122.1 (2)
C1—N3—C7	121.58 (18)	N4—C9—O2	110.1 (2)
C9—N4—C8	124.4 (2)	O2—C10—C11	105.60 (19)
C9—N4—C11	112.3 (2)	O2—C10—H10A	110.6
C8—N4—C11	123.08 (18)	C11—C10—H10A	110.6
N1—C1—N3	125.98 (19)	O2—C10—H10B	110.6
N1—C1—C5	127.6 (2)	C11—C10—H10B	110.6
N3—C1—C5	106.39 (18)	H10A—C10—H10B	108.8
N1—C2—C3	123.7 (2)	N4—C11—C10	101.52 (18)
N1—C2—H2A	118.1	N4—C11—H11A	111.5
C3—C2—H2A	118.1	C10—C11—H11A	111.5
C4—C3—C2	121.8 (2)	N4—C11—H11B	111.5
C4—C3—Br1	119.65 (16)	C10—C11—H11B	111.5
C2—C3—Br1	118.43 (17)	H11A—C11—H11B	109.3
C3—C4—C5	115.34 (19)	C17—C12—C13	118.8 (2)
C3—C4—H4A	122.3	C17—C12—C6	118.60 (19)
C5—C4—H4A	122.3	C13—C12—C6	122.5 (2)
N2—C5—C4	132.04 (18)	C14—C13—C12	119.9 (2)
N2—C5—C1	109.89 (18)	C14—C13—H13A	120.0
C4—C5—C1	118.07 (19)	C12—C13—H13A	120.0
N2—C6—N3	113.29 (18)	C15—C14—C13	120.7 (2)
N2—C6—C12	122.43 (19)	C15—C14—H14A	119.7
N3—C6—C12	124.24 (18)	C13—C14—H14A	119.7
N3—C7—C8	111.52 (17)	C14—C15—C16	119.8 (2)
N3—C7—H7A	109.3	C14—C15—H15A	120.1
C8—C7—H7A	109.3	C16—C15—H15A	120.1
N3—C7—H7B	109.3	C15—C16—C17	120.4 (2)
C8—C7—H7B	109.3	C15—C16—H16A	119.8
H7A—C7—H7B	108.0	C17—C16—H16A	119.8
N4—C8—C7	112.74 (19)	C16—C17—C12	120.3 (2)
N4—C8—H8A	109.0	C16—C17—H17A	119.8
C7—C8—H8A	109.0	C12—C17—H17A	119.8
C2—N1—C1—N3	179.8 (2)	C1—N3—C7—C8	−76.4 (3)
C2—N1—C1—C5	0.7 (4)	C9—N4—C8—C7	106.1 (3)
C6—N3—C1—N1	−178.2 (2)	C11—N4—C8—C7	−79.5 (3)
C7—N3—C1—N1	−15.3 (3)	N3—C7—C8—N4	−66.7 (2)
C6—N3—C1—C5	1.1 (2)	C8—N4—C9—O1	−1.6 (4)
C7—N3—C1—C5	163.93 (19)	C11—N4—C9—O1	−176.5 (3)
C1—N1—C2—C3	0.3 (4)	C8—N4—C9—O2	178.6 (2)
N1—C2—C3—C4	−0.7 (4)	C11—N4—C9—O2	3.7 (3)
N1—C2—C3—Br1	−177.4 (2)	C10—O2—C9—O1	−176.5 (2)
C2—C3—C4—C5	0.2 (3)	C10—O2—C9—N4	3.3 (3)
Br1—C3—C4—C5	176.72 (16)	C9—O2—C10—C11	−8.5 (3)
C6—N2—C5—C4	179.9 (2)	C9—N4—C11—C10	−8.5 (3)
C6—N2—C5—C1	0.3 (2)	C8—N4—C11—C10	176.5 (2)
C3—C4—C5—N2	−178.8 (2)	O2—C10—C11—N4	9.8 (3)
C3—C4—C5—C1	0.8 (3)	N2—C6—C12—C17	36.7 (3)
N1—C1—C5—N2	178.3 (2)	N3—C6—C12—C17	−145.7 (2)
N3—C1—C5—N2	−0.9 (2)	N2—C6—C12—C13	−139.9 (2)
N1—C1—C5—C4	−1.3 (4)	N3—C6—C12—C13	37.7 (3)
N3—C1—C5—C4	179.46 (19)	C17—C12—C13—C14	1.9 (4)
C5—N2—C6—N3	0.4 (2)	C6—C12—C13—C14	178.5 (2)
C5—N2—C6—C12	178.28 (19)	C12—C13—C14—C15	−0.8 (4)
C1—N3—C6—N2	−1.0 (2)	C13—C14—C15—C16	−0.7 (5)
C7—N3—C6—N2	−161.8 (2)	C14—C15—C16—C17	1.1 (4)
C1—N3—C6—C12	−178.78 (19)	C15—C16—C17—C12	0.0 (4)
C7—N3—C6—C12	20.4 (3)	C13—C12—C17—C16	−1.5 (4)
C6—N3—C7—C8	81.7 (3)	C6—C12—C17—C16	−178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···N2i	0.95	2.61	3.544 (3)	168
C10—H10A···N2ii	0.99	2.55	3.261 (3)	128
C15—H15A···O1iii	0.95	2.53	3.423 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯N2i	0.95	2.61	3.544 (3)	168
C10—H10A⋯N2ii	0.99	2.55	3.261 (3)	128
C15—H15A⋯O1iii	0.95	2.53	3.423 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) .