1-(Prop-2-yn­yl)-1H-benzimidazol-2(3H)-one

The benzimidazolone part of the title mol­ecule, C₁₀H₈N₂O, is almost planar [r.m.s. deviation = 0.014 (1) Å] and the NCH₂C[triple bond]CH group forms a dihedral angle of 67.95 (6)° with its best plane. In the crystal, mol­ecules form inversion dimers via pairs of N—H...O hydrogen bonds. C—H...O inter­actions connect the dimers, forming a two-dimensional polymeric network parallel to (100).

1-(4-Methyl­benz­yl)-1H-benzimidazol-2(3H)-one

In the title compound, C₁₅H₁₄N₂O, the fused five- and six-membered ring system is essentially planar, the maximum deviation from the mean plane being 0.009 (1) Å. The benzimidazol-2(3H)-one residue is nearly perpendicular to the benzyl ring, forming a dihedral angle of 77.41 (6)°. In the crystal, inversion dimers are formed by pairs of N—H...O hydrogen bonds; these dimers are linked by weak C—H...O inter­actions into a two-dimensional array in the (102) plane.

1-Allyl-5-nitro-1H-benzimidazol-2(3H)-one

The benzimidazolone residue in the title mol­ecule, C₁₀H₉N₃O₃, is almost planar, with the largest deviation from the mean plane being 0.016 (2) Å for the C atom linked to the nitro group. This plane is nearly perpendicular to the 1-allyl chain as indicated by the C—N—C—C torsion angle of 90.9 (3)°. The fused-ring system makes a dihedral angle of 5.6 (3)° with the nitro group, leading to a synperiplanar conformation. In the crystal, zigzag supra­molecular chains are formed along the a axis by N—H...O hydrogen bonds.

Ethyl 2-oxo-3-(3-phthalimidoprop­yl)-2,3-dihydro-1H-1,3-benzimidazole-1-carboxyl­ate

In the title compound, C₂₁H₁₉N₃O₅, the phthalimide and benzamidazole ring systems are linked by a propyl chain. The benzamidazole unit also carries an eth­oxy­carbonyl substit­uent. The phthalimido and benzimidazole ring systems are essentially planar, the maximum deviations from their mean planes being 0.008 (2) and 0.020 (2) Å, respectively. The two ring systems are almost orthogonal to one another, making a dihedral angle of 82.37 (8)°. In the crystal, C—H...O hydrogen bonds and C—H...π contacts stack the mol­ecules along the b axis.

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

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, mol­ecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers.

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

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, mol­ecules are linked by C—H...O hydrogen bonds, building chains parallel to the a-axis direction.

5-Nitro-1,3-bis­(prop-2-yn­yl)-1H-1,3-benzimidazol-2(3H)-one

The title compound, C₁₃H₉N₃O₃, crystallizes with two identical but differently oriented mol­ecules in the asymmetric unit, the dihedral angle between the fused-ring systems of the two molecules being 64.39 (7)°. The two prop-2-ynyl chains are located on opposite sides of the mol­ecule and are nearly perpendicular to the fused ring plane, as indicated by the C—N—C—C torsion angles in the range 106.0 (3)–113.4 (3)°. In the crystal, the two mol­ecules are linked through C—H...O hydrogen bonds into dimers, which are subsequently linked by further C—H...O inter­actions, building a three-dimensional network.

3-Benzyl-1-{[3-(4-chloro­phen­yl)isoxazol-5-yl]meth­yl}-1H-benzimidazol-2(3H)-one

In the title compound, C₂₄H₁₈ClN₃O₂, the benzimidazole plane is nearly perpendicular to the phenyl ring and to the isoxazole ring, making dihedral angles of 75.95 (7) and 73.04 (8)°, respectively, but the two residues point in opposite directions with respect to the benzimidazole plane. The dihedral angle between the chloro­phenyl and isoxazole rings is 7.95 (8)°. In the crystal, mol­ecules are linked by pairs of C—H...O hydrogen bonds into inversion dimers.

1-Allyl-3-benzyl-1H-benzimidazol-2(3H)-one

In the title compound, C₁₇H₁₆N₂O, the fused benzimidazol-2(3H)-one system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å for the carbonyl C atom. Its mean plane is almost perpendicular to the benzyl plane and to the allyl group, making dihedral angles of 80.6 (1) and 77.4 (3)°, respectively. The benzyl group and the allyl subsituent lie on opposite sides of the fused ring system. In the crystal, mol­ecules are linked by bifurcated C—H...O hydrogen bonds in which the carbonyl O atom acts as accepter to two aromatic C—H groups, forming a two-dimensional network parallel to (001).

1-Octylindoline-2,3-dione

In the title compound, C₁₆H₂₁NO₂, the indoline ring and the two ketone O atoms are approximately coplanar, the largest deviation from the mean plane being 0.063 (2) Å. The mean plane through the fused ring system is nearly perpendicular to the mean plane passing through the 1-octyl chain [dihedral angle = 77.53 (17)°]. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds, forming a three-dimensional network.