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1.  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
2.  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
3.  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
4.  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
5.  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
6.  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
7.  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
8.  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
9.  Methyl 3-[(1H-benzimidazol-1-yl)meth­yl]-1-methyl-4-(4-methyl­phen­yl)-2′-oxopyrrolidine-2-spiro-3′-1-benzimidazole-3-carboxyl­ate 
In the title compound, C29H28N4O3, the pyrrolidine ring adopts a twist conformation whereas the oxindole and benzimidazole residues are approximately planar with maximum deviations of 0.159 (1) and 0.011 (1) Å, respectively. The oxindole residue is almost perpendicular to the benzimidazole residue, making a dihedral angle of 89.2 (1)°. The methyl-substituted benzene ring is oriented at angles of 47.7 (1) and 71.0 (1)°, respectively, with respect to the oxindole and benzimidazole residues. An intra­molecular C—H⋯O hydrogen bond is observed. In the crystal, mol­ecules associate via N—H⋯N hydrogen bonds, forming R 2 2(9) dimers.
doi:10.1107/S1600536810035312
PMCID: PMC2983424  PMID: 21587504
10.  1-Butyl-3-ethyl-1H-benzimidazol-3-ium tetra­fluoro­borate 
In the title salt, C13H19N2 +·BF4 −, an ionic liquid, the butyl and ethyl substituents bonded to the N atoms of the imidazole ring [r.m.s. deviation = 0.019 (1) Å] adopt equatorial positions. The crystal structure exhibits slipped π–π inter­actions between the imidazole and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.529 (2) Å]. In the tetra­fluoro­borate anion, the B and F atoms are disordered over two sets of sites with site-occupancy factors of 0.813 (7) and 0.187 (7).
doi:10.1107/S1600536812037476
PMCID: PMC3470219  PMID: 23125663
11.  1-(Prop-2-en-1-yl)-3-[(trimethyl­sil­yl)meth­yl]benzimidazolium bromide monohydrate 
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].
doi:10.1107/S1600536810033015
PMCID: PMC3008061  PMID: 21588727
12.  1-[4-(Prop-2-en-1-yl­oxy)benz­yl]-2-[4-(prop-2-en-1-yl­oxy)phen­yl]-1H-benzimidazole 
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].
doi:10.1107/S160053681204559X
PMCID: PMC3588921  PMID: 23476157
13.  Ethyl 1-[3-(1H-imidazol-1-yl)prop­yl]-2-(4-chloro­phen­yl)-1H-benzo[d]imidazole-5-carboxyl­ate dihydrate 
In the title compound, C22H21ClN4O2·2H2O, the almost-planar benzimidazole ring system [maximum deviation 0.014 (1) Å] is inclined at angles of 36.32 (5) and 74.75 (7)° with respect to the phenyl and imidazole rings, respectively. In the crystal structure, the water mol­ecules are linked to the organic mol­ecules to form a three-dimensional network via O—H⋯N and O—H⋯O hydrogen bonds. The packing is further consolidated by a pair of bifurcated C—H⋯O bonds, generating R 1 2(6) loops. C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536811033654
PMCID: PMC3200625  PMID: 22058996
14.  2-Meth­oxy-6-(6-methyl-1H-benzimid­azol-2-yl)phenol 
In the title mol­ecule, C15H14N2O2, the substituted benzene ring forms a dihedral angle of 4.15 (1)° with the benzimidazole ring system. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the solid state, mol­ecules are linked into chains along the [001] via inter­molecular bifurcated N—H⋯(O,O) hydrogen bonds, which generate R 1 2(5) ring motifs. The crystal packing is also consolidated by C—H⋯π inter­actions, and π–π stacking inter­actions between the imidazole and substituted benzene rings [centroid–centroid distance = 3.5746 (13) Å]. The methyl group attached to the benzimidazole ring system is disordered over two positions with occupancies of 0.587 (6) and 0.413 (6), suggesting 180° rotational disorder for the benzimidazole group.
doi:10.1107/S1600536809022478
PMCID: PMC2969490  PMID: 21582885
15.  11-Hy­droxy-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propano­anthracen-12-one 
In the title compound, C20H18O2, the central six-membered ring adopts a boat conformation and the terminal benzene rings make a dihedral angle of 42.66 (4)° with each other. In the crystal structure, the O—H group forms both an intra- and an inter­molecular O—H⋯O hydrogen bond; the former generates an S(5) ring and the latter leads to inversion-generated R 2 2(10) loops. The dimers are further linked into ribbons propagating along the a axis by C—H⋯O inter­actions, and the packing is consolidated by weak C—H⋯π inter­actions.
doi:10.1107/S1600536811033538
PMCID: PMC3200828  PMID: 22059039
16.  1,3-Bis(3-phenyl­prop­yl)benzimidazolium bromide monohydrate 
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.
doi:10.1107/S1600536808030432
PMCID: PMC2959260  PMID: 21201214
17.  Ethyl 1-sec-butyl-2-p-tolyl-1H-benzimidazole-5-carboxyl­ate 
In the title compound, C21H24N2O2, the butyl group is disordered over two orientations with refined site occupancies of 0.883 (3) and 0.117 (3). The dihedral angle between the mean plane of benzimidazole ring system and the benzene ring is 39.32 (4)° and the dihedral angle between the mean plane of carboxyl­ate group and the benzimidazole ring system is 6.87 (5)°. A weak intra­molecular C—H⋯π inter­action may have some influence on the conformation of the mol­ecule. In the crystal structure, mol­ecules are linked into infinite chains along the b axis by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536810015242
PMCID: PMC2979236  PMID: 21579242
18.  (2E)-3-[4-(1H-Benzimidazol-2-ylmeth­oxy)phen­yl]-1-(4-meth­oxy­phen­yl)prop-2-en-1-one 
In the title compound, C24H20N2O3, the mean plane of the benzimidazole unit makes dihedral angles of 79.88 (11) and 85.44 (12)° with the benzene and 4-meth­oxy­benzene rings, respectively. The benzene and 4-meth­oxy­benzene rings maske a dihedral angle of 16.10 (14)°. A pair of inter­molecular N—H⋯O hydrogen bonds connects adjacent mol­ecules into an inversion dimer, generating an R 2 2(26) ring motif. The crystal structure is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536811012645
PMCID: PMC3089334  PMID: 21754409
19.  (S)-2-(2-Pyrrolidinio)-1H-benzimidazol-3-ium dichloride monohydrate 
In the title compound, C11H15N3 2+·2Cl−·H2O, one N atom of the imidazole ring and the N atom of the pyrrolidine ring are protonated. The crystal structure is stabilized by aromatic π–π inter­actions between the benzene rings of neighbouring benzimidazole systems [centroid–centroid duistance = 3.712 (2) Å]. The crystal structure is further stabilized by inter­molecular N—H⋯Cl, O—H⋯Cl and N—H⋯O hydrogen bonds.
doi:10.1107/S1600536809019084
PMCID: PMC2969638  PMID: 21583238
20.  (E)-3-[4-(Dimethyl­amino)­phen­yl]-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one 0.7-hydrate 
In the title compound, C27H24N2O·0.7H2O, the quinoline ring system is approximately planar, with a maximum deviation of 0.011 (1) Å, and forms dihedral angles of 74.70 (4) and 80.14 (4)° with the phenyl and benzene rings, respectively. In the crystal, the mol­ecules are linked to the water mol­ecules via inter­molecular O—H⋯N hydrogen bonds and further stabilized by C—H⋯π inter­actions involving the centroid of the benzene ring of the quinoline group. This benzene ring is observed to form a π–π inter­action with an adjacent pyridine ring [centroid–centroid distance = 3.7120 (6) Å].
doi:10.1107/S1600536811019088
PMCID: PMC3120557  PMID: 21754884
21.  2-(3,4-Di­fluoro­phen­yl)-1H-benzimidazole 
In the title mol­ecule, C13H8F2N2, the dihedral angle between the benzimidazole ring system and the di­fluoro-substituted benzene ring is 30.0 (1)°. In the crystal, mol­ecules are linked by N—H⋯N hydrogen bonds, forming chains along [010]. In addition, weak C—H⋯F hydrogen bonds connect chains into a two-dimensional network parallel to (001). A weak C—H⋯π inter­action is observed between an H atom of the benzimidazole ring sytem and the π system of the di­fluoro-substituted benzene ring.
doi:10.1107/S1600536813028559
PMCID: PMC3884342  PMID: 24454118
22.  1-(4-Bromo­phen­yl)-3-(4-ethoxy­phen­yl)­prop-2-en-1-one 
The title compound, C17H15BrO2, consists of two substituted benzene rings connected by a prop-2-en-1-one group. The mol­ecule is nearly planar and adopts an E configuration. The dihedral angle between the two benzene rings is 8.51 (19)°. The enone plane makes dihedral angles of 11.06 (19) and 7.69 (19)°, respectively, with the bromo­phenyl and ethoxy­phenyl rings. The mol­ecules are linked by C—H⋯O hydrogen bonds to form a zigzag ribbon-like structure along the b direction. The crystal structure is stabilized by weak intra- and inter­molecular C—H⋯O inter­actions.
doi:10.1107/S1600536808021776
PMCID: PMC2962165  PMID: 21203245
23.  2-(Naphthalen-1-yl)-1-phenyl-1H-benzimid­azole benzene hemisolvate 
In the title compound, C23H16N2·0.5C6H6, the benzimidazole unit [maximum deviation = 0.0258 (6) Å] and the naphthalene ring system [maximum deviation = 0.0254 (6) Å] are both essentially planar and make a dihedral angle of 61.955 (17)°. The imidazole ring makes dihedral angle of 61.73 (4)° with the phenyl ring. An intra­molecular C—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, seven weak C—H⋯π inter­actions involving the fused ring system, the benzene solvent mol­ecule, the imidazole phenyl rings are observed, leading to a three-dimensional architecture.
doi:10.1107/S160053681303331X
PMCID: PMC3914093  PMID: 24526997
24.  (Z)-3-(4-Chloro­phen­yl)-2-{[N-(2-formyl­phen­yl)-4-methyl­benzene­sulfonamido]­meth­yl}prop-2-ene­nitrile 
In the title compound, C24H19ClN2O3S, the sulfonyl-bound benzene ring forms dihedral angles of 38.1 (2) and 81.2 (1)°, respectively, with the formyl benzene and benzene rings. The mol­ecular conformation is stabilized by a weak intra­molecular C—H⋯O hydrogen bond, which generates an S(5) ring motif. The crystal packing is stabilized by C—H⋯O hydrogen bonds, which generate C(7) zigzag chains along [010] and R 3 3(19) ring motifs along [010]. The crystal packing is further stabilized by C—Cl⋯π inter­actions [Cl⋯centroid = 3.456 (2) Å and C—Cl⋯centroid = 173.4 (2)°].
doi:10.1107/S160053681105241X
PMCID: PMC3254413  PMID: 22259557
25.  1,3-Bis(3-phenyl­prop­yl)-1H-benzimidazol-3-ium-2-carbodithio­ate 
The title compound, C26H26N2S2, was synthesized from bis­[1,3-bis­(3-phenyl­prop­yl)benzimidazolidine-2-yl­idene] and CS2 in toluene. The mol­ecular structure is composed of a benzimidazole ring system with two phenyl­propyl substituents and a dithio­carboxyl­ate group in the 2-position. The benzimidazole unit is essentially planar, with a maximum atomic deviation of 0.008 (2) Å, and makes dihedral angles of 72.72 (10) and 27.62 (12)°, with the two phenyl rings. The dihedral angle between the two phenyl rings is 55.98 (15)°. The mol­ecular packing is stabilized by a C—H⋯S inter­molecular hydrogen-bonding inter­action and a C—H⋯π inter­action between a benzene H atom and the phenyl ring of a neighbouring mol­ecule.
doi:10.1107/S1600536808042761
PMCID: PMC2968085  PMID: 21581631

Results 1-25 (472188)