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

Ouzidan, Y.; Jasinski, J.P.; Butcher, R.J.; Golen, J.A.; Essassi, E.M.; El Ammari, L.

doi:10.1107/S1600536811012669

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1095

doi:10.1107/S1600536811012669

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

Younes Ouzidan,^a ^* Jerry P. Jasinski,^b Raymond J. Butcher,^c James A. Golen,^b El Mokhtar Essassi ^d and Lahcen El Ammari ^e

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^dLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Avenue Ibn Battouta, Rabat, Morocco, and ^eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: ouzidan@yahoo.fr

(Received 28 March 2011; accepted 5 April 2011; online 13 April 2011)

In the title molecule, C₁₇H₁₅BrN₄O₂, 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 molecule is stabilized by an intramolecular π⋯π interaction [centroid–centroid distance = 3.855(2) Å] between oxazolidine and phenyl rings. The crystal packing features intermolecular C—H⋯N and C—H⋯O interactions.

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_r = 387.24
Monoclinic, P 2₁ /n
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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.091
S = 1.03
3791 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) -x+1, -y+2, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

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

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

checkCIF report

Comment top

Oxazolidin-2-ones are a very important class of heterocyclic compounds and their derivatives have attracted attention in various areas of drug development for antibacterial activity (Diekema & Jones, 2000; Mukhtar & Wright, 2004). Some oxazolidin-2-ones have been used as chiral auxiliaries in a wide range of asymmetric reactions (Evans et al.,1993; Matsunaga et al., 2005). As a continuation of our research works devoted to the development of substituted imidazo[4,5-b]pyridine derivatives (Ouzidan et al., 2010a,b), we report in this paper the synthesis of a new 2,6-disubstituted imidazo[4,5-b]pyridine possessing the oxazolidin-2-one ring (Scheme 1) by the action of bis(2-chloroethyl)amine hydrochloride on 6-bromo-2-phenyl-3H-imidazo [4,5-b]pyridine in boiling DMF.

The title molecule is shown in Fig. 1. The two cycles forming the imidazo[4,5-b]pyridine are almost planar with a maximum deviation of 0.015 (1) Å for N3 atom and form dihedral angles of 37.8 (2)° and 35.5 (2)° with the phenyl and the oxazolidine rings respectively. The oxazolidinone group is linked to the phenyl group by a weak intramolecular C-H···π interaction. The crystal structure is stabilized by two intermolecular C–H···N and C–H···O interactions as shown in Fig. 2 and Table 2.

Related literature top

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 top

To 6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridine (0.3 g, 1.09 mmol), potassium carbonate (0.33 g, 2.4 mmol) and tetra-n-butylammonium bromide (0.05 g, 0.1 mmol) in DMF (15 ml) was added bis(2-chloroethyl)amine hydrochloride (0.23 g, 1.31 mmol). The mixture was heated for 48 h. After the completion of the reaction (as monitored by TLC), the inorganic salt was filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel by using (ethanol/ethyl acetate: 1/4) as eluent. The product was recrystallized from ethanol to furnish colourless crystals (m.p. 454 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. : Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. : Partial packing view showing the C—H···O and C—H···N interactions (dashed lines).

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

Crystal data top

C₁₇H₁₅BrN₄O₂	F(000) = 784
M_r = 387.24	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0373P)² + 0.4211P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3791 reflections	Δρ_max = 0.50 e Å⁻³
218 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₁₅BrN₄O₂	V = 1594.46 (15) Å³
M_r = 387.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.3553 (6) Å	µ = 2.60 mm⁻¹
b = 11.5915 (5) Å	T = 170 K
c = 12.2542 (8) Å	0.22 × 0.20 × 0.18 mm
β = 98.685 (6)°

Data collection top

Oxford Diffraction XcaliburE Gemini diffractometer	3791 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2839 reflections with I > 2σ(I)
T_min = 0.599, T_max = 0.652	R_int = 0.028
7850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.03	Δρ_max = 0.50 e Å⁻³
3791 reflections	Δρ_min = −0.35 e Å⁻³
218 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1; (ii) x−1/2, −y+3/2, z−1/2; (iii) x−1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrN₄O₂
M_r	387.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	170
a, b, c (Å)	11.3553 (6), 11.5915 (5), 12.2542 (8)
β (°)	98.685 (6)
V (Å³)	1594.46 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.60
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Oxford Diffraction XcaliburE Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.599, 0.652
No. of measured, independent and observed [I > 2σ(I)] reflections	7850, 3791, 2839
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.091, 1.03
No. of reflections	3791
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.35

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+1; (ii) x−1/2, −y+3/2, z−1/2; (iii) x−1/2, −y+3/2, z+1/2.

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Diekema, D. J. & Jones, R. N. (2000). Drugs, 59, 7–16. Web of Science CrossRef PubMed CAS Google Scholar
Evans, D. A., Ny, H. P. & Rieger, D. L. (1993). J. Am. Chem. Soc. 115, 11446–11459. CrossRef CAS Web of Science Google Scholar
Matsunaga, H., Ishizuka, T. & Kunieda, T. (2005). Tetrahedron, 61, 8073–8094. Web of Science CrossRef CAS Google Scholar
Mukhtar, T. A. & Wright, G. D. (2004). Chem. Rev. 105, 529–542. CrossRef Google Scholar
Ouzidan, Y., Kandri Rodi, Y., Obbade, S., Essassi, E. M. & Ng, S. W. (2010a). Acta Cryst. E66, o947. Web of Science CrossRef IUCr Journals Google Scholar
Ouzidan, Y., Obbade, S., Capet, F., Essassi, E. M. & Ng, S. W. (2010b). Acta Cryst. E66, o946. Web of Science CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1095

doi:10.1107/S1600536811012669

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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