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6-Bromo-3-methyl-2-phenyl-3H-imidazo[4,5-b]pyridine.

ABSTRACT: The two fused five- and six-membered rings building the mol-ecule of the title compound, C(13)H(10)BrN(3), are approximately planar, the largest deviation from the mean plane being 0.004 (2) Å. The dihedral angle between the imidazo[4,5-b]pyridine mean plane and that of the phenyl ring is 41.84 (11)°. The structure is held together by slipped π-π stacking between symmetry-related mol-ecules, with an inter-planar distance of 3.583 (1) Å and a centroid-centroid vector of 3.670 (2) Å.

SUBMITTER: Ouzidan Y

PROVIDER: S-EPMC3151993 | biostudies-literature |

REPOSITORIES: biostudies-literature

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4-Benzyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine.

Project description:The imidazopyridine fused ring in the title compound, C(19)H(14)BrN(3), is almost coplanar with the phenyl ring at the 2-position of the five-membered ring [dihedral angle = 2.4?(1). The crystal structure features short Br?Br contacts [3.562?(1)?Å].

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3-Benzyl-6-bromo-2-(2-fur-yl)-3H-imidazo[4,5-b]pyridine.

Project description:In the title mol-ecule, C(17)H(12)BrN(3)O, the imidazopyridine ring system is almost coplanar with the furan ring [dihedral angle = 2.0 (3)°]. The benzyl phenyl ring is oriented at dihedral angles of 85.2 (2) and 85.5 (1)°, respectively, with respect to the furan ring and the imidazopyridine ring system. In the crystal, mol-ecules are linked into chains propagating along the b axis by C-H⋯N hydrogen bonds. Adjacent chains are linked via short Br⋯Br contacts [3.493 (1) Å].

| S-EPMC3006925 | biostudies-literature

3-[(1-Benzyl-1H-1,2,3-triazol-5-yl)meth-yl]-6-bromo-2-phenyl-3H-imidazo[4,5-b]pyridine.

Project description:There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(22)H(17)BrN(6). The dihedral angles between the imidazo[4,5-b]pyridine mean plane and the phenyl rings are 20.4 (2) and 24.0 (2)° in the two mol-ecules. The orientation of triazoles compared to the imidazo[4,5-b]pyridine system is almost the same in both mol-ecules, with dihedral angles of 64.2 (2) and 65.1 (2)°. However, the main difference between the two mol-ecules lies in the arrangement of the phenyl groups compared to imidazo[4,5-b]pyridine in each mol-ecule. Indeed, in the first mol-ecule the dihedral angle between the plane of the phenyl ring and that of the imidazo[4,5-b]pyridine system is 67.7 (2)°, while in the second mol-ecule the plane of the phenyl ring is almost perpendicular to that of the imidazo[4,5-b]pyridine system with a dihedral angle of 86.0 (2)°.

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6-Bromo-3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The title compound, C(7)H(6)BrN(3)O, was obtained from the reaction of 6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one with methyl iodide. All non-H atoms lie in a common plane [r.m.s deviation = 0.017?(1)?Å]. The amino group is a hydrogen-bond donor to the carbonyl group of an inversion-related mol-ecule, the pair of hydrogen bonds giving rise to a hydrogen-bonded dimer.

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4-Allyl-6-bromo-2-phenyl-4H-imidazo[4,5-b]pyridine monohydrate.

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Crystal structures of methyl 3-phenyl-4,5-di-hydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl-ate and methyl 1-methyl-3-phenyl-4,5-di-hydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl-ate.

Project description:The title compounds, C19H18N2O3, (I), and C20H20N2O3, (II), differ only by a methyl substituent on the seven-membered oxazepine ring in (II). In both compounds, these rings have a twist-chair conformation. The phenyl ring makes a dihedral angle of 73.42?(10)° with the benzimidazole ring system mean plane (r.m.s. deviation = 0.015?Å) in (I) and 83.07?(7)° in (II) (r.m.s. deviation = 0.026?Å). The methyl carboxyl-ate groups are planar to within 0.031?(2) in (I) and 0.003?(2)?Å in (II). They are inclined to the phenyl and benzimidazole ring system by 33.78?(16) and 87.56?(14)°, respectively, in (I) and by 53.04?(12) and 60.22?(11)°, respectively, in (II). In the crystal of (I), mol-ecules stack in a herringbone fashion and are linked by C-H?O hydrogen bonds, forming chains along [100]. In the crystal of (II), there are no significant inter-molecular inter-actions present.

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6-Bromo-1,3-dimethyl-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The non-H atoms of the two independent mol-ecules in the asymmetric unit of the title compound, C(8)H(8)BrN(3)O, are planar (r.m.s. deviations = 0.015 and 0.019?Å). In the crystal, the mol-ecules are linked into a zigzag chain along the c axis by C-H?O hydrogen bonds.

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1-Acetyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The two fused five- and six-membered rings in the mol-ecule of the title compound, C(8)H(6)BrN(3)O(2), are approximately coplanar, the largest deviation from the mean plane being 0.011?(3)?Å at the NH atom. The acetyl group is slightly twisted with respect to the imidazo[4,5-b]pyridine system, making a dihedral angle of 2.7?(2)°. In the crystal, adjacent mol-ecules are linked by inter-molecular N-H?N and C-H?O hydrogen bonds, forming infinite chains.

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1,3-Diallyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:In the mol-ecule of the title compound, C(12)H(12)BrN(3)O, the fused-ring system is essentially planar, the largest deviation from the mean plane being 0.0148?(3)?Å. The two allyl groups are nearly perpendicular to the imidazo[4,5-b]pyridine plane [C-C-N-C torsion angles of 81.6?(4) and -77.2?(4)°] and point in the same direction. The planes through the atoms forming each allyl group are nearly perpendicular to the imidazo[4,5-b]pyridin-2-one system, as indicated by the dihedral angles between them of 80.8?(5) and 73.6?(5)°.

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3-Benzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:The fused imidazole and pyridine rings in the title compound, C13H10BrN3O, are linked to a benzyl group. The fused ring system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å. The phenyl ring is not coplanar with the fused ring system, as indicated by the dihedral angle of 67.04 (12)°. In the crystal, mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming inversion dimers.

| S-EPMC3685101 | biostudies-literature

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