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

ABSTRACT: 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].

SUBMITTER: Ouzidan Y

PROVIDER: S-EPMC3006925 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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)°.

| S-EPMC3099998 | biostudies-literature

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

Project description: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.

| S-EPMC3151993 | biostudies-literature

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

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].

| S-EPMC2983780 | biostudies-literature

4-Benzyl-6-bromo-2-(4-methoxy-phen-yl)-4H-imidazo[4,5-b]pyridine monohydrate.

Project description:The imidazopyridine fused ring in the title compound, C(20)H(16)BrN(3)O·H(2)O, is coplanar with the aromatic ring at the 2-position [dihedral angle = 5.2?(1)°]. In the five-membered imidazo portion, the C-N bond whose C atom is also connected to the pyridine N atom has predominantly double-bond character [1.334?(2)?Å] whereas the C-N bond whose atom is connected to the pyridine C atom has predominantly single-bond character [1.371?(2)?Å]. The water mol-ecule engages in hydrogen bonding with the latter N atom; it is also connected to a symmetry-related water mol-ecule, generating a linear chain structure.

| S-EPMC2983875 | biostudies-other

Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromo-hex-yl)-2-[4-(di-methyl-amino)-phen-yl]-3H-imidazo[4,5-b]pyridine.

Project description:In the title mol-ecule, C20H24Br2N4, the imidazo-pyridine moiety is not planar as indicated by the dihedral angle of 2.0?(2)° between the constituent rings; the 4-di-methyl-amino-phenyl ring is inclined to the mean plane of the imidazole ring by 27.4?(1)°. In the crystal, two sets of C-H??(ring) inter-actions form stacks of mol-ecules extending parallel to the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H?H (42.2%), H?C/C?H (23.1%) and H?Br/Br?H (22.3%) inter-actions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6-311?G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO-LUMO energy gap is 2.3591?eV.

| S-EPMC7405593 | biostudies-literature

6-Bromo-1,3-bis-[(1,3-dioxolan-2-yl)meth-yl]-1H-imidazo[4,5-b]pyridin-2(3H)-one.

Project description:In the title compound, C14H16BrN3O5, the N atoms adjacent to the carbonyl group in the five-membered ring are substituted by (1,3-dioxolan-2-yl)methyl groups. The fused ring system is essentially planar, with the largest deviation from the mean plane being 0.014?(2)?Å for the C atom bearing the Br atom. The first oxolane ring, attached on the side of the N atom belonging to the pyridine ring, has an envelope conformation with one of the O atoms as the flap, whereas the second oxolane ring displays a twisted boat conformation. The two oxolane rings display envelope and twisted boat conformations. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds, building chains parallel to the a-axis direction.

| S-EPMC3772466 | biostudies-literature

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

Project description:The reaction of propargyl bromide and 6-bromo-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in refluxing dimethyl-formamide yields the title compound, C(12)H(8)BrN(3)O, which features nitro-gen-bound propadienyl and propynyl substituents. The imidazolopyridine fused ring is planar (r.m.s. deviation = 0.012?Å); the propadienyl chain is coplanar with the fused ring as it is conjugated with it, whereas the propynyl chain is not as the nitro-gen-bound C atom is a methyl-ene linkage. The acetyl-enic H atom is hydrogen bonded to the carbonyl O atom of an adjacent mol-ecule, forming a helical chain runnning along the b axis.

| S-EPMC2983773 | biostudies-literature

3-Ethyl-5-(4-meth-oxy-phen-oxy)-2-(pyridin-4-yl)-3H-imidazo[4,5-b]pyridine.

Project description:In the title compound, C(20)H(18)N(4)O(2), the imidazopyridine fused ring system is almost perpendicular to the benzene ring [dihedral angle = 87.6?(5)°]. The pyridine ring makes a dihedral angle of 35.5?(5)° with the mean plane of the imidazopyridine fragment. The crystal structure is stabilized by an aromatic ?-? stacking inter-action between the phenyl rings of neighbouring mol-ecules [centroid-centroid distance = 3.772?(2)?Å, inter-planar distance = 3.546?(2)?Å and slippage = 1.286?(2)?Å].

| S-EPMC3152004 | biostudies-literature

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.

| S-EPMC2979211 | biostudies-literature

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