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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-(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
5.  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
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.  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
10.  2-Methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol–2-methyl-6-(5-methyl-1H-benzimidazol-2-yl)phenol (3/1) 
The title compound, 0.75C15H14N2O·0.25C15H14N2O, is a co-crystal of 2-methyl-6-(6-methyl-1H-benzimidazol-2-yl)phenol as the major component and 2-methyl-6-(5-methyl-1H-benz­imidazol-2-yl)phenol as the minor component. The refined site-occupancy ratio is 0.746 (4)/0.254 (4). The conformations of both components are identical except for that of the methyl substituent on the benzene ring of the benzimidazole unit which is positionally disordered over two positions. The mol­ecule is essentially planar, the dihedral angle between the benzimidazole plane and the benzene ring being 3.49 (4)°. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal packing, mol­ecules are linked through N—H⋯O hydrogen bonds into chains along [201]. These chains are stacked approximately along the a-axis direction. The crystal packing is further stabilized by weak N—H⋯O and O⋯H⋯N hydrogen bonds, together with weak inter­molecular C—H⋯π inter­actions. A π–π inter­action with a centroid–centroid distance of 3.6241 (6) Å is also observed between the substituted phenyl ring and that of the benzimidazole system.
doi:10.1107/S1600536809049770
PMCID: PMC2972110  PMID: 21578934
11.  2-[1-(2-Hydroxy-3-methoxybenzyl)-1H-benzimidazol-2-yl]-6-methoxyphenol monohydrate 
The asymmetric unit of the title compound, C22H20N2O4·H2O, comprises a substituted benzimidazole molecule and a water mol­ecule of crystallization. The dihedral angles between the benzimidazole ring system and the two outer benzene rings are 16.54 (4) and 86.13 (4)°. The dihedral angle between the two hydr­oxy-substituted benzene rings is 82.20 (5)°. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds, involving the hydr­oxy groups and water mol­ecules, form R 4 4(8) ring motifs, and link symmetry-related mol­ecules into extended chains along the c axis. The crystal structure is further stabilized by weak inter­molecular C—H⋯O hydrogen bonds, weak C—H⋯π and π–π stacking [centroid–centroid = 3.6495 (6)–3.7130 (6) Å] inter­actions. Intra­molecular O—H⋯O and O—H⋯N inter­actions are also present.
doi:10.1107/S1600536809010769
PMCID: PMC2968983  PMID: 21582616
12.  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
13.  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
14.  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
15.  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
16.  (2-{[2-(1H-Benzimidazol-2-yl-κN 3)phen­yl]imino­methyl-κN}-5-methyl­phenolato-κO)chloridozinc(II) 
In the title mononuclear complex, [Zn(C21H16N3O)Cl], the ZnII ion is coordinated in a distorted tetra­hedral geometry by two benzimidazole N atoms and one phenolate O atom from the tridentate Schiff base ligand and a chloride ligand. The benzimidazole ring system forms dihedral angles of 26.68 (9) and 56.16 (9)° with the adjacent benzene ring and the methyl­phenolate group benzene ring, respectively. In the crystal, mol­ecules are linked by N—H⋯Cl hydrogen bonds into chains along [100]. Furthermore, weak C—H⋯O and C—H⋯π inter­actions, in addition to π–π inter­actions with centroid–centroid distances in the range 3.5826 (13)–3.9681 (13) Å, are also observed.
doi:10.1107/S1600536811030170
PMCID: PMC3200787  PMID: 22065469
17.  1-{2-(4-Chloro­benz­yloxy)-2-[4-(mor­pho­lin-4-yl)phen­yl]eth­yl}-1H-benzimidazole propan-2-ol monosolvate 
In the title compound, C26H26ClN3O2·C3H7OH, the benzimid­azole ring system is essentially planar [maximum deviation = −0.018 (2) Å] and its mean plane is oriented with respect to the two benzene rings at dihedral angles of 4.51 (6) and 56.16 (6)°, and the dihedral angle between the two benzene rings is 59.11 (7)°. The morpholine ring displays a chair conformation. The propan-2-ol solvent mol­ecule links with the benzimidazole ring via an O—H⋯N hydrogen bond. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into inversion dimers with an R 2 2(28) motif. π–π stacking occurs between the parallel chloro­benzene rings [centroid–centroid distance = 3.792 (1) Å]. Weak C—H⋯π inter­actions and short Cl⋯Cl [3.2037 (10) Å] contacts are also observed.
doi:10.1107/S1600536813022599
PMCID: PMC3884486  PMID: 24427066
18.  Methyl 7,8-diacet­oxy-11-oxo-5-(2-oxo­pyrrolidin-1-yl)-7,9-epoxy­cyclo­penta­[4,5]pyrido[1,2-a]quinoline-10-carboxyl­ate sesquihydrate 
The title compound, C26H28N2O9·1.5H2O, the product of an acid-catalysed Wagner–Meerwein skeletal rearrangement, crystallizes as a sesquihydrate with the O atom of one of the two independent water mol­ecules occupying a special position on a twofold axis. The organic mol­ecule comprises a fused penta­cyclic system containing two five-membered rings (cyclo­pentane and tetra­hydro­furan) and three six-membered rings (piperidinone, tetra­hydro­pyridine and benzene). The five-membered rings have the usual envelope conformations, and the central six-membered piperidinone and tetra­hydro­pyridine rings adopt boat and sofa conformations, respectively. In the crystal, there are three independent O—H⋯O hydrogen bonds, which link the organic mol­ecules and water mol­ecules into complex two-tier layers parallel to (001). The layers are further linked into a three-dimensional framework by attractive inter­molecular carbon­yl–carbonyl inter­actions.
doi:10.1107/S160053680905363X
PMCID: PMC2980137  PMID: 21580091
19.  (E)-1-(1-Hy­droxy­naphthalen-2-yl)-3-(2,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one 
In the title mol­ecule, C22H20O5, the C=C bond of the central enone group adopts an E conformation. The dihedral angle formed by the benzene ring and the naphthalene ring system is 12.6 (4)°. The hy­droxy group attached to the naphthalene ring is involved in an intra­molecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯O hydrogen bonds link the mol­ecules into chains along [010]. In addition, π–π stacking inter­actions are present, with centroid–centroid distances of 3.6648 (15) and 3.8661 (15) Å between the benzene and two naphthalene rings.
doi:10.1107/S1600536813006843
PMCID: PMC3629594  PMID: 23634081
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.  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
22.  (E)-3-(1,3-Benzodioxol-5-yl)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfon­amido]methyl}prop-2-enenitrile 
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.
doi:10.1107/S1600536812042663
PMCID: PMC3515259  PMID: 23284479
23.  (1Z)-1-[(2E)-3-(4-Bromo­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-yl­idene]-2-(2,4-dinitro­phen­yl)hydrazine 
In the title mol­ecule, C21H14BrFN4O4, the mean planes of the two nitro groups form dihedral angles of 3.1 (2) and 7.1 (5)° with the benzene ring to which they are attached. The dinitro-substituted ring forms dihedral angles of 8.6 (2) and 71.9 (2)° with the bromo- and fluoro-substituted benzene rings, respectively. The dihedral angle between the bromo- and fluoro-substituted benzene rings is 80.6 (2)°. There is an intra­molecular N—H⋯O hydrogen bond. In the crystal, pairs of weak C—H⋯O hydrogen bonds form inversion dimers. In addition, π–π stacking inter­actions between the bromo- and dinitro-substituted rings [centroid–centroid separation = 3.768 (2) Å] are observed.
doi:10.1107/S1600536812027328
PMCID: PMC3393993  PMID: 22798858
24.  2-(4-Chloro­phen­yl)-4,5-diphenyl-1-(prop-2-en-1-yl)-1H-imidazole 
The title compound, C24H19ClN2, crystallizes with two independent mol­ecules in the asymmetric unit. The prop-2-enyl substituents on the imidazole rings adopt similar conformations in the two mol­ecules. The 4-and 5-substituted phenyl rings and the benzene ring make dihedral angles of 67.06 (8), 5.61 (8) and 41.09 (8)°, respectively, with the imadazole ring in one mol­ecule and 71.53 (8), 28.85 (8) and 41.87 (8)°, respectively, in the other. The crystal structure features C—H⋯π inter­actions and weak π–π stacking inter­actions [centroid–centroid distances = 3.6937 (10) and 4.0232 (10) Å] between the chloro­phenyl rings, which form a three-dimensional supramolecular structure.
doi:10.1107/S1600536813012592
PMCID: PMC3685034  PMID: 23795053
25.  6-[3-(p-Tolyl­sulfonyl­amino)­prop­yl]diquino­thia­zine1  
In the title mol­ecule {systematic name: N-[3-(diquino[3,2-b;2′,3′-e][1,4]thia­zin-6-yl)prop­yl]-4-methyl­benzene­sulfon­amide}, C28H24N4O2S2, the penta­cyclic system is relatively planar [maximum deviation from the mean plane = 0.242 (1) Å]. The dihedral angle between two quinoline ring systems is 8.23 (2)° and that between the two halves of the 1,4-thia­zine ring is 5.68 (3)°. The conformation adopted by the 3-(p-tolyl­sulfonyl­amino)­propyl substituent allows for the formation of an intra­molecular N—H⋯N hydrogen bond and places the benzene ring of this substituent above one of the quinoline fragments of the penta­cyclic system. In the crystal, mol­ecules are arranged via π–π stacking inter­actions into (0-11) layers [centroid–centroid distances = 3.981 (1)–4.320 (1) Å for the rings in the penta­cyclic system and 3.645 (1) Å for the tolyl benzene rings]. In addition, mol­ecules are involved in weak C—H⋯O, which connect the layers, and C—H⋯S hydrogen bonds. The title compound shows promising anti­cancer activity against renal cancer cell line UO-31.
doi:10.1107/S1600536813013950
PMCID: PMC3685109  PMID: 23795128

Results 1-25 (568446)