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In the title compound, C24H25N3O5, the benzimidazole and benzodioxole ring systems are each approximately planar [maximum deviations = 0.043 (1) and 0.036 (1) Å, respectively]. Their mean planes form a dihedral angle of 42.85 (4)°. The pyrrolidine ring has an envelope conformation with one of the methyl­ene C atoms forming the flap. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The crystal packing is further stabillized by weak π–π inter­actions between the benzene rings within the benzimidazole ring system [centroid–centroid distance = 3.7955 (7) Å]. A weak C—H⋯π inter­action involving the benzodioxole ring is also present.

In the title compound, C23H25N3O3, the benzimidazole ring system is essentially planar [maximum deviation = 0.0240 (18) Å]. The mean plane through this ring system forms a dihedral angle of 42.23 (7)° with the benzene ring. The pyrrolidine ring is in an envelope conformation with the flap atom disordered over two sites with occupancies of 0.813 (11) and 0.187 (11). In the crystal, weak C—H⋯O hydrogen bonds form R 2 2(10) ring motifs, which are connected by further C—H⋯O inter­actions, forming ribbons along the b axis. The crystal structure is further stabilized by weak π–π inter­actions involving the imidazole and benzene rings of the benzimidazole ring system [centroid–centroid distances = 3.6788 (11) and 3.6316 (10) Å] and weak C—H⋯π inter­actions.

In the title compound, C25H20N2O5S, the benzodioxole ring system is essentially planar [maximum deviation = 0.021 (2) Å] and forms dihedral angles of 85.2 (1) and 74.2 (1)°, respectively, with the formyl benzene and sulfonyl-bound benzene rings. In the crystal, C—H⋯O hydrogen bonds generate C(8) chains along [100] and R33(19) ring motifs. In addition, a weak π–π inter­action [centroid–centroid distance = 3.937 (3) Å] is also observed.

In the title compound, C14H9O2S, the benzothia­zole unit is oriented at a dihedral angle of 7.1 (1)° with respect to the benzodioxole unit. The dioxole ring adopts flattened envelope conformation with the methyl­ene C atom at the flap. The crystal packing is stabilized by π–π inter­actions [centroid–centroid distances = 3.705 (1) and 3.752 (1) Å], C—H⋯π inter­actions and a short S⋯S contact of 3.485 (1) Å.

In the title compound, C24H27N3O5·H2O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intra­molecular C—H⋯π inter­action is observed. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π–π stacking [centroid–centroid distance = 3.6632 (9) Å] and C—H⋯O inter­actions.

In the title compound, C14H21N2Si+·Br−·H2O, the benzimidazole ring system is almost planar [maximum deviation = 0.021 (2) Å]. In the crystal, O—H⋯Br and C—H⋯O hydrogen bonds link the ions via the O atoms of the water mol­ecules. In addition, there are π–π stacking inter­actions between the centroids of the benzene and imidazole rings of the benzimidazole ring system [centroid–centroid distances = 3.521 (3) and 3.575 (2) Å].

In the title compound, C9H8O3, the dihedral angle between the mean planes of the benzene and dioxole rings is 1.4 (8)°, with the dioxole group in a slightly distorted envelope configuration with the flap C atom displaced by 0.0645 Å from the plane through the other four atoms. In the crystal, weak inter­molecular C—H⋯O hydrogen-bond inter­actions link the mol­ecules into chains propagating in [011]. The crystal packing exhibits weak π–π inter­actions as evidenced by the relatively short distances [3.801 (9) Å] between the centroids of adjacent benzene rings.

In the title structure, C25H24FN3O5, a strong intra­molecular O—H⋯O hydrogen bond is present between the carb­oxy group at the 3-position and the carbonyl group at the 4-position. In the crystal, mol­ecules are held together by weak C—H⋯O, C—H⋯F and π–π [centroid–centroid distance 3.6080 (8) Å] inter­actions. The 1,4-dihydro­quinoline ring and cyclo­propyl group are not in the same plane, making an inter­planar angle of 57.52 (8)°.

In the title compound, C19H12O4, the dioxole ring adopts a flattened envelope conformation with the methyl­ene C at the flap [deviation = 0.104 (2) Å]. The benzene ring of the benzodioxole ring system makes a dihedral angle of 76.45 (5)° with the planar [maximum deviation = 0.016 (1) Å] 3H-benzo[f]isobenzofuran-1-one ring system. In the crystal structure, the mol­ecules are linked into C(5) chains running along the b axis by inter­molecular C—H⋯O hydrogen bonds. In addition, C—H⋯π inter­actions are observed.

In the title compound, C23H24N4O5, the essentially planar benzimidazole ring system [maximum deviation = 0.008 (2) Å] forms a dihedral angle of 39.22 (7)° with the attached nitro­benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with a C atom as the flap. In the crystal, mol­ecules are connected by C—H⋯O inter­actions, forming sheets propagating in (011). The crystal packing also features weak π–π stacking inter­actions [centroid–centroid = 3.6746 (12) Å].

In the title mol­ecule, C14H9BrO3S, the the prop-2-en-1-one (enone) fragment is close to planar [C—C—C—O = 2.5 (7)°] and it subtends dihedral angles of 12.5 (3) and 5.3 (4)° with respect to the thio­phene and benzene rings, respectively. The dihedral angle between the aromatic ring systems is 12.60 (18)°. Two C—H⋯O inter­actions help to consolidate the non-centrosymmetic crystal packing, which features undulating (100) sheets incorporating C(11) and C(12) chain motifs.

In the title compound, C16H15NO3, the five-membered 1,3-dioxole ring is in an envelope conformation with the methyl­ene C atom as the flap atom [lying 0.202 (3) Å out of the plane formed by the other four atoms]. The benzene ring makes a dihedral angle of 84.65 (4)° with the best least-squares plane through the 1,3-benzodioxole fused-ring system, which substitutes the 2-methoxyphenol moiety in capsaicin. In the crystal, mol­ecules are connected into a zigzag supra­molecular chain along the c-axis direction by N—H⋯O hydrogen bonds. These chains are connected into a layer in the ac plane by C—H⋯π inter­actions.

There are two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C29H30N2O5, each having an E conformation about the C=C double bond. The dihedral angles between the meth­oxy­benzene rings in the two mol­ecules are 71.39 (17) and 68.64 (17)°. In the crystal, mol­ecules are linked by C—H⋯O inter­actions.

The title compound, C18H23N2Si+·Cl−·H2O, was synthesized from 1-[(trimethyl­sil­yl)meth­yl]benzimidazole and benzyl chloride in dimethyl­formamide. The benzimidazole ring system is approximately planar, with a maximum deviation of 0.022 (2) Å, and makes an angle of 74.80 (12)° with the phenyl ring. The crystal packing is stabilized by O—H⋯Cl, C—H⋯Cl, C—H⋯O and C—H⋯π inter­actions between symmetry-related mol­ecules together with π–π stacking inter­actions between the imidazolium and benzene rings [centroid–centroid distance = 3.5690 (15) Å] and between the benzene rings [centroid–centroid distance = 3.7223 (14) Å].

In the title compound, C14H13ClO5, the five-membered ring is in an envelope conformation with the methyl­ene C-atom being the flap. The conformation about the C=C double bond [1.341 (2) Å] is E. The chloro­propan-2-one residue is approximately orthogonal to the remaining mol­ecule [dihedral angle = 88.03 (6)°]. In the crystal, the mol­ecules associate via C—H⋯O inter­actions, involving both carbonyl-O atoms, giving rise to an undulating two-dimensional array in the ac plane.

In the title compound, C25H27N2 +·Br−·H2O, the benzimidazole unit is essentially planar, with a maximum deviation of 0.020 (6) Å. The benzimidazole unit makes dihedral angles of 83.6 (3) and 81.0 (3)° with the two terminal phenyl rings. The dihedral angle between the phenyl rings is 58.5 (4)°. In the crystal structure, there are C—H⋯O hydrogen bonds, a C—H⋯π inter­action between a phenyl H atom and the phenyl ring of a neighbouring mol­ecule, and a π–π inter­action [3.512 (3) Å] between the centroids of the five-membered ring and the benzene ring of the benzimidazole unit of an adjacent mol­ecule.

The 1,3-benzodioxole ring systems in the title compound, C22H22O8, are almost planar. The perhydro­furofuranyl system linking them adopts a distorted double-envelope conformation. Supra­molecular aggregation is effected by C—H⋯O, C—H⋯π and π–π [centroid–centroid distance of 3.755 Å, inter­planar distance of 3.633 Å and dihedral angle of 14.6°] inter­actions.

In the title compound, C26H24N2O2, the benzimidazole ring system is almost planar [maximum displacement = 0.025 (1) Å] and makes dihedral angles of 80.48 (5) and 41.57 (5)° with the benzene rings, which are inclined to one another by 65.33 (6)°. In the crystal, mol­ecules are linked via C—H⋯π and weak π–π inter­actions [centroid–centroid distance = 3.8070 (7) Å and inter­planar distance = 3.6160 (5) Å].

In the mol­ecule of title compound, C12H14O3, the benzodioxole ring system is essentially planar. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into chains along the c axis, and π–π contacts between dioxole rings and between dioxole and benzene rings of the benzodioxole ring systems [centroid–centroid distances 3.702 (3) and 3.903 (3) Å] may further stabilize the structure. Two C—H⋯π inter­actions are also found.

In the title compound, C17H12O3, each of the five-membered rings in the inden-1-one and 1,3-benzodioxole residues is almost planar (r.m.s. deviations = 0.041 and 0.033 Å, respectively). A small twist about the single bond linking the two residues is evident [the C—C—C—C torsion angle = 8.7 (4)°]. Supra­molecular zigzag layers propagating in the ac plane are formed in the crystal via C—H⋯O inter­actions. The layers are linked via π–π inter­actions between the five- and six-membered rings of 1,3-benzodioxole residues [centroid–centroid distance = 3.4977 (14) Å].

In the title compound, [Zn(C8H5N2O2)2(H2O)], the ZnII ion is coordinated in each case by a carboxyl­ate O atom and an imidazole N atom from two different benzimidazole-2-carboxyl­ate (BIC) ligands and one water O atom in a trigonal-bipyramidal geometry. In the complex mol­ecule, the two benzimidazole planes are twisted, making a dihedral angle of 55.93 (11)°. The three-dimensional framework is organized by inter­molecular N—H⋯O hydrogen bonding and O—H⋯O inter­actions and π–π inter­actions between adjacent benzimidazole rings [centroid–centroid distance = 3.586 (3) Å].

The mol­ecule of the title compound, C16H11BrO3, is essentially planar with a maximum deviation of 0.178 (4) Å and the configuration of the keto group with respect to the olefinic double bond is typically s-cis. In the crystal structure, inter­molecular Br⋯O inter­actions [3.187 (3)Å] give rise to chains parallel to the b axis. Adjacent chains are further linked along the a axis by C—H⋯π inter­actions. The crystal studied was a racemic twin with a 0.595 (13):0.405 (13) ratio.

In the title compound, C13H12N4O6, the mean plane through the nitro­benzene forms a dihedral angle of 37.38 (15)° with the plane through the imidazole ring. The crystal packing is stabilized by weak inter­molecular C—H⋯O and C—H⋯N inter­actions together with π–π stacking inter­actions between nitro­benzene rings [centroid–centroid distance = 3.788 (3) Å] and between imidazole rings [centroid–centroid distance = 3.590 (2) Å].

In the title compound, C13H12N2O3, the dihedral angle between the aromatic rings is 7.94 (12)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(6) loops. Weak π–π [centroid–centroid separations = 3.7480 (13) and 3.9047 (13) Å] and C—H⋯π inter­actions help to consolidate the packing.

The title compound, C11H9F3O5, crystallizes with three mol­ecules in the asymmetric unit. One –CF3 group is disordered by rotation, with the F atoms split over two sets of sites with occupancies which converged to 0.888 (6) and 0.112 (6). Weak π–π inter­actions are observed between adjacent benzene rings [the shortest centroid–centroid distance is 3.8858 (4) Å], resulting in the formation of a supra­molecular chain along [100].