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1.  Ethyl 2-[4-(morpholin-4-yl)phen­yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-1,3-benzimidazole-5-carboxyl­ate monohydrate 
The asymmetric unit of the title compound, C27H32N4O4·H2O, contains two independent benzimidazole-5-carboxyl­ate mol­ecules and two water mol­ecules. In both main mol­ecules, the pyrrolidine rings are in an envelope conformation with a methyl­ene C atom as the flap. The morpholine rings adopt chair conformations. Both benzimidazole rings are essentially planar, with maximum deviations of 0.008 (1) Å, and form dihedral angles of 37.65 (6) and 45.44 (6)° with the benzene rings. In one mol­ecule, an intra­molecular C—H⋯O hydrogen bond forms an S(7) ring motif. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds connect pairs of main mol­ecules and pairs of water mol­ecules into two independent centrosymmetric four-compoment aggregates. These aggregates are connect by C—H⋯O hydrogen bonds leading to the formation of a three-dimensional network, which is stabilized by C—H⋯π interactions.
doi:10.1107/S1600536812039268
PMCID: PMC3470336  PMID: 23125749
2.  Ethyl 1-phenyl-2-[4-(trifluoro­meth­oxy)phen­yl]-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C23H17F3N2O3, an intra­molecular C—H⋯F hydrogen bond generates an S(6) ring motif. The essentially planar 1H-benzimidazole ring system [maximum deviation = 0.021 (2) Å] forms dihedral angles of 25.00 (10) and 62.53 (11)° with the trifluoro­meth­oxy-substituted benzene and phenyl rings, respectively. The twist of the ethyl acetate group from the least-squares plane of the 1H-benzimidazole ring system is defined by a C(=O)—O—C—C torsion angle of 79.5 (3)°. In the crystal, mol­ecules are linked into a two-dimensional network parallel to the bc plane by weak C—H⋯N and C—H⋯O hydrogen bonds. Weak C—H⋯π inter­actions also observed.
doi:10.1107/S1600536812034903
PMCID: PMC3435731  PMID: 22969602
3.  Ethyl 2-(4-chloro­phen­yl)-1-phenyl-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C22H17ClN2O2, the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, mol­ecules are linked into a zigzag chain along the a axis by inter­molecular C—H⋯O hydrogen bonds. C—H⋯π inter­actions are also present.
doi:10.1107/S1600536812022192
PMCID: PMC3379429  PMID: 22719627
4.  Ethyl 1-phenyl-2-[4-(trifluoro­meth­yl)phen­yl]-1H-benzimidazole-5-carboxyl­ate 
The asymmetric unit of the title compound, C23H17F3N2O2, contains two mol­ecules. In one of the mol­ecules, the phenyl and triflouromethyl-substituted benzene rings form dihedral angles of 52.05 (8) and 33.70 (8)°, respectively, with the benzimidazole ring system, while the dihedral angle between them is 58.24 (10)°. The corresponding values in the other mol­ecule are 58.40 (8), 25.90 (8) and 60.83 (10)°, respectively. In the crystal, mol­ecules are linked into chains along [100] by C—H⋯O and C—H⋯N hydrogen bonds. Aromatic π–π stacking inter­actions [centroid–centroid distance = 3.6700 (12) Å] also occur.
doi:10.1107/S1600536812022210
PMCID: PMC3379430  PMID: 22719628
5.  Ethyl 2-(4-bromo­phen­yl)-1-phenyl-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C22H17BrN2O2, the benzimidazole ring system is essentially planar, with a maximum deviation of 0.017 (1) Å, and forms dihedral angles of 27.79 (6) and 64.43 (6)° with the phenyl and bromo-substituted benzene rings, respectively. In the crystal, mol­ecules are linked into one-dimensional chains along the a axis by weak C—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯π inter­actions are also present.
doi:10.1107/S1600536812019897
PMCID: PMC3379279  PMID: 22719477
6.  Ethyl 1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-2-phenyl-1H-benzimidazole-5-carboxyl­ate 
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.
doi:10.1107/S1600536811054833
PMCID: PMC3274946  PMID: 22346899
7.  Ethyl 2-(4-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
The asymmetric unit of the title compound, C24H27N3O4, contains two mol­ecules, A and B. The benzimidazole rings are essentially planar [maximum deviations = 0.0144 (10) and 0.0311 (8) Å in A and B, respectively]. The dihedral angle between the benzimidazole mean plane and its attached benzene ring is 36.90 (5) ° for mol­ecule A and 51.40 (5) ° for mol­ecule B. In both mol­ecules, the pyrrolidine ring adopts an envelope conformation with a C atom as the flap. In molecule B, the flap C atom is disordered over two positions in a 0.711 (6):0.289 (6) ratio. In the crystal, C—H⋯O inter­actions link the mol­ecules, generating [100] chains. The crystal packing also features weak π–π inter­actions between the imidazole and benzene rings [centroid–centroid distances = 3.8007 (7) and 3.8086 (7) Å] and between the benzene rings [centroid–centroid distance = 3.7001 (7) Å] and C—H⋯π inter­actions involving the benzene rings.
doi:10.1107/S1600536811055966
PMCID: PMC3275001  PMID: 22346946
8.  Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C23H22N4O4, the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methyl­ene C atom at the flap. In the crystal, C—H⋯O and C—H⋯N inter­actions link the mol­ecules into a ribbon along the a axis. The crystal packing is further stabilized by weak π–π stacking inter­actions [centroid–centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C—H⋯π inter­actions.
doi:10.1107/S1600536811054572
PMCID: PMC3254578  PMID: 22259529
9.  Ethyl 2-(4-nitro­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
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].
doi:10.1107/S1600536811052408
PMCID: PMC3254415  PMID: 22259559
10.  Ethyl 2-(4-hy­droxy-3-meth­oxy­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate 
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.
doi:10.1107/S1600536811052391
PMCID: PMC3254439  PMID: 22259586
11.  Ethyl 2-(4-bromophenyl)-1-[3-(1H-imidazol-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate monohydrate 
In the title compound, C22H21BrN4O2·H2O, the two pyrazole rings are essentially planar [maximum deviations 0.002 (1) and 0.002 (1) Å], and form a dihedral angle of 73.46 (9)°. The dihedral angle between the benzene rings is 29.33 (7)°. In the crystal, mol­ecules are connected via C—H⋯O and O—H⋯N hydrogen bonds, forming layers in the ab plane.
doi:10.1107/S160053681104342X
PMCID: PMC3247451  PMID: 22220069
12.  Ethyl 4-[3-(1H-imidazol-1-yl)propyl­amino]-3-nitro­benzoate 
In the title compound, C15H18N4O4, the 1H-imidazole ring forms a dihedral angle of 67.12 (8)° with the benzene ring. An S(6) ring motif is formed via an intra­molecular N—H⋯O hydrogen bond. In the crystal, neighbouring mol­ecules are linked by a pair of inter­molecular N—H⋯N hydrogen bonds, forming an inversion dimer. The dimers are further linked by a pair of C—H⋯O hydrogen bonds, leading to the formation of chain along [021]. A C—H⋯π inter­action involving the centroid of the benzene ring is also observed between the chains.
doi:10.1107/S1600536811036300
PMCID: PMC3201243  PMID: 22058754
13.  Ethyl 1-[2-(morpholin-4-yl)eth­yl]-2-[4-(trifluoro­meth­yl)phen­yl]-1H-benzimid­azole-5-carboxyl­ate 
In the title compound, C23H24F3N3O3, the morpholine ring adopts a chair conformation. The benzimidazole ring is approximately planar, with a maximum deviation of 0.028 (1) Å for one of the unsubstituted C atoms. The benzimidazole ring makes dihedral angles of 35.66 (4) and 75.45 (5)° with the attached phenyl and morpholine rings, respectively. In the crystal structure, adjacent mol­ecules are linked via C—H⋯F and C—H⋯O hydrogen bonds to form a two-dimensional network.
doi:10.1107/S1600536811014619
PMCID: PMC3089142  PMID: 21754513

Results 1-13 (13)