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1.  Ethyl 2-[5-(4-fluoro­phen­yl)pyridin-3-yl]-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C28H27FN4O3·H2O, the benzimidazole ring system is essentially planar with a maximum deviation of 0.028 (1) Å. It makes dihedral angles of 47.59 (5) and 60.31 (5)°, respectively, with the pyridine and benzene rings, which make a dihedral angle of 22.58 (6)° with each other. The pyrrolidine ring shows an envelope conformation with one of the methyl­ene C atoms as the flap. In the crystal, the components are connected into a tape along the b-axis direction through O—H⋯O and O—H⋯N hydrogen bonds and a π–π inter­action between the pyridine and benzene rings [centroid–centroid distance of 3.685 (8) Å]. The tapes are further linked into layers parallel to the ab plane by C—H⋯O and C—H⋯F inter­actions.
doi:10.1107/S1600536813014177
PMCID: PMC3772454  PMID: 24046597
2.  Ethyl 2-[4-(di­methyl­amino)­phen­yl]-1-phenyl-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C24H23N3O2, the benzimidazole ring system makes dihedral angles of 7.28 (5) and 67.17 (5)°, respectively, with the planes of the benzene and phenyl rings, which in turn make a dihedral angle of 69.77 (6)°. In the crystal, mol­ecules are connected by C—H⋯N and C—H⋯O inter­actions, forming a layer parallel to the bc plane. A π–π inter­action, with a centroid–centroid distance of 3.656 (1) Å, is observed in the layer.
doi:10.1107/S1600536813012440
PMCID: PMC3685043  PMID: 23795062
3.  4′-(4-Fluoro­phen­yl)-1′-methyl­dispiro­[indane-2,2′-pyrrolidine-3′,2′′-indane]-1,3,1′′-trione methanol hemisolvate 
The asymmetric unit of the title compound, C29H24FNO5·0.5CH3OH, contains two independent mol­ecules and a one methanol solvent mol­ecule. The methanol mol­ecule is O—H⋯O hydrogen bonded to one of the independent mol­ecules. The pyrrolidine rings in both mol­ecules adopt half-chair conformations, while the cyclo­pentane rings within the indane groups are in flattened envelope conformations, with the spiro C atoms forming the flaps. The benzene rings of the indane ring systems form a dihedral angle of 35.06 (7)° in one independent mol­ecule and 31.16 (8)° in the other. The fluoro-substituted benzene ring forms dihedral angles of 65.35 (6) and 85.87 (7)° with the indane group benzene rings in one mol­ecule, and 72.78 (8) and 77.27 (8)° in the other. In each mol­ecule, a weak intra­molecular C—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, weak C—H⋯O, C—H⋯N and C—H⋯F hydrogen bonds link the mol­ecules into a three-dimensional network.
doi:10.1107/S1600536813009987
PMCID: PMC3648276  PMID: 23723896
4.  3-{5-Eth­oxy­carbonyl-1-[3-(2-oxopyrrol­idin-1-yl)prop­yl]-1H-benzimidazol-2-yl}benzoic acid 
In the title compound, C24H25N3O5, the eth­oxy group is disordered over two orientations in a 0.853 (14):0.147 (14) ratio. The benzimadazole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 35.47 (7)° with the attached benzene ring. The pyrrolidine ring adopts an envelope conformation with a methyl­ene C atom as the flap. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R 2 2(16) loops. C—H⋯O inter­actions link the dimers into a three-dimensional network.
doi:10.1107/S1600536813001116
PMCID: PMC3569823  PMID: 23424569
5.  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
6.  4′-(3-Bromo­phen­yl)-1′-methyl­dispiro­[indan-2,2′-pyrrolidine-3′,2′′-indan]-1,3,1′′-trione 
In the title compound, C27H20BrNO3, two intra­molecular C—H⋯O hydrogen bonds both form S(6) rings. The pyrrolidine ring adopts a twisted conformation about the C—C bond bearing the indane ring systems. The other two five-membered rings within the indane systems are in shallow envelope conformations, with the spiro C atoms as the flap atoms. The mean plane of the pyrrolidine ring [maximum deviation = 0.275 (1) Å] makes dihedral angles of 65.25 (7), 78.33 (6) and 75.25 (6)° with the bromo-substituted benzene ring and the mean planes of the mono- and dioxo-substituted indane rings, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into a three-dimensional network. In addition, C—H⋯π inter­actions are observed.
doi:10.1107/S1600536812037993
PMCID: PMC3470256  PMID: 23125700
7.  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
8.  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
9.  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
10.  Ethyl 4-anilino-3-nitro­benzoate 
In the title compound, C15H14N2O4, the dihedral angle between the benzene and phenyl rings is 73.20 (6)°. An intra­molecular N—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds into a layer parallel to the bc plane.
doi:10.1107/S1600536812019903
PMCID: PMC3379280  PMID: 22719478
11.  4′-(4-Bromo­phen­yl)-1′-methyl­dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C30H22BrNO2, the cyclo­pentane ring of the dihydro­acenaphthyl­ene group and the pyrrolidine ring are both in envelope conformations with the spiro C atom and N atom, respectively, as the flap atom. The cyclo­pentane ring of the indane group adopts a half-chair conformation. A weak intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The naphthalene ring system of the dihydro­acenaphthyl­ene group forms dihedral angles of 41.76 (6) and 42.17 (6)° with the benzene ring of the bromo­phenyl group and the benzene ring of the indane group, respectively. The dihedral angle between the two benzene rings is 83.92 (7)°. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. Weak C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536812014213
PMCID: PMC3344476  PMID: 22590238
12.  1′-Methyl-4′-[4-(trifluoro­meth­yl)phen­yl]dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C31H22F3NO2, the pyrrolidine and cyclo­pentane rings within the dihydro­indene ring system are in envelope conformations, with the N atom and the spiro-C atom at the flap, respectively. An intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The mean plane through the pyrrolidine ring [r.m.s. deviation = 0.179 (2) Å] makes dihedral angles of 86.30 (13), 88.99 (10) and 79.69 (11)° with the benzene ring, the dihydro­acenaphthyl­ene ring and the mean plane of the indane system, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. C—H⋯π inter­actions further stabilize the crystal structure.
doi:10.1107/S1600536812013645
PMCID: PMC3344443  PMID: 22590205
13.  7′-Phenyl-1′,3′,5′,6′,7′,7a’-hexa­hydro­dipiro[acenaphthyl­ene-1,5′-pyrrolo­[1,2-c]thia­zole-6′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C31H23NO2S, the pyrrolidine ring adopts an envelope conformation (with the spiro C atom as the flap), while the thia­zolidine ring and the two cyclo­pentane rings adopt twisted conformations. The mean plane through the hexa­hydro­pyrrolo­[1,2-c]thia­zole ring [r.m.s deviation = 0.400 (1) Å] forms dihedral angles of 76.83 (4), 80.70 (5) and 79.00 (4)° with the benzene ring and the mean planes of the dihydro­acenaphthyl­ene and the dihydro­indene rings, respectively. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. One of the ketone O atoms accepts three such bonds. Weak C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536812013293
PMCID: PMC3344191  PMID: 22606194
14.  7′-(2,5-Dimeth­oxy­phen­yl)-1′,3′,5′,6′,7′,7a’-hexa­hydro­dispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione 
In the title compound, C30H25NO5S, all the five-membered rings are in envelope conformations with the spiro and methylene C atoms as the flap atoms. Intra­molecular C—H⋯O inter­actions stabilize the mol­ecular structure and form S(6) and S(7) ring motifs. The mean plane through the hexa­hydro­pyrrolo­[1,2-c]thia­zole ring [r.m.s deviation of 0.0393 (1) Å] makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring and the mean planes of the mono and di-oxo substituted indan rings, respectively. Mol­ecules are linked by inter­molecular C—H⋯O inter­actions into a three-dimensional network. In addition, C—H⋯π and π–π inter­actions [centroid-to-centroid distance = 3.4084 (8) Å] further stabilize the crystal structure.
doi:10.1107/S1600536812003169
PMCID: PMC3297291  PMID: 22412481
15.  (E)-2-[4-(Trifluoro­meth­yl)benzyl­idene]-2,3-dihydro-1H-inden-1-one 
In the title mol­ecule, C17H11F3O, the indan ring system and the trifluoro­methyl-substituted benzene ring are approximately individually planar and form a dihedral angle of 1.81 (5)° with each other. In the crystal, mol­ecules are linked by pairs of weak bifurcated (C—H)2⋯O hydrogen bonds to form centrosymmetric dimers, generating R 2 1(6) and R 2 2(10) ring motifs. These dimers are connected by further weak C—H⋯O hydrogen bonds into one-dimensional chains along the b axis. Weak C—H⋯π inter­actions are also present.
doi:10.1107/S1600536812003157
PMCID: PMC3275283  PMID: 22347139
16.  Ethyl 2-(1,3-benzodioxol-5-yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benz­imidazole-5-carboxyl­ate 
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.
doi:10.1107/S1600536812001420
PMCID: PMC3275223  PMID: 22347079
17.  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
18.  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
19.  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
20.  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
21.  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
22.  7′-(4-Bromo­phen­yl)-5′,6′,7′,7a’-tetra­hydro­dispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione 
In the title compound, C28H20BrNO3S, the thia­zolidine, pyrrolidine and two five-membered carbocyclic rings are in envelope conformations. The bromo-bound phenyl ring forms dihedral angles of 61.97 (18) and 88.30 (17)° with the other two benzene rings. The two benzene rings form a dihedral angle of 30.3 (2)°. The mol­ecular structure features an intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked into inversion dimers by pairs of C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811046514
PMCID: PMC3238931  PMID: 22199780
23.  7′-[4-(Trifluoro­meth­yl)phen­yl]-5′,6′,7′,7a’-tetra­hydrodispiro­[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione 
In the title compound, C29H20F3NO3S, the thia­zolidine ringadopts a half-chair conformation. The pyrrolidine and two five-membered carbocyclic rings are in envelope conformations with the spiro C atoms at the flaps. The trifluoro­methyl-substituted benzene ring forms dihedral angles of 62.37 (14) and 87.40 (14)° with the benzene rings of the dihydro-1H-indene units. The two benzene rings form a dihedral angle of 36.94 (15)°. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol­ecules are linked into inversion dimers by pairs of inter­molecular C—H⋯O hydrogen bonds, generating R 2 2(10) ring motifs.
doi:10.1107/S1600536811047118
PMCID: PMC3238947  PMID: 22199796
24.  7′-Phenyl-5′,6′,7′,7a′-tetra­hydro­dipiro[indan-2,5′-pyrrolo­[1,2-c][1,3]thia­zole-6′,2′′-indan]-1,3,1′′-trione 
The asymmetric unit of the title compound, C28H21NO3S, contains two mol­ecules with similar geometries. The thia­zolidine rings adopt half-chair conformations while the pyrrolidine and the diketo-substituted five-membered carbocyclic rings are in envelope conformations with the spiro C atoms at the flaps. In one mol­ecule, the phenyl ring forms dihedral angles of 57.76 (12) and 71.79 (12)° with the fused benzene rings and the fused benzene rings form a dihedral angle of 57.75 (13)°. The corresponding dihedral angles in the other mol­ecule are 60.04 (12), 72.93 (12) and 54.51 (13)°. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol­ecules are linked via C—H⋯O and C—H⋯N hydrogen bonds into layers lying parallel to the ab plane.
doi:10.1107/S1600536811046174
PMCID: PMC3238881  PMID: 22199734
25.  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

Results 1-25 (51)