PMCC PMCC

Search tips
Search criteria

Advanced
Results 1-25 (352099)

Clipboard (0)
None

Related Articles

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-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
3.  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
4.  (2E)-3-(4-Methyl­phen­yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one monohydrate 
The title hydrate, C26H21NO·H2O, exhibits significant twists of the benzene ring [dihedral angle = 87.24 (6)°] and chalcone residue [C—C—C—C torsion angle = −94.46 (17)°] out of the plane through the quinoline ring system. The conformation about the C=C bond [1.341 (2) Å] is E. The solvent water mol­ecule forms hydrogen bonds to carbonyl O and quinoline N atoms derived from two mol­ecules and through the application of a centre of inversion, a 16-membered {⋯HOH⋯OC3N}2 synthon is formed to stabilize the resulting tetra­meric (two organic mol­ecules plus two water mol­ecules) aggregate. These are connected into a two-dimensional array via two C—H⋯O contacts, also involving the water mol­ecule. The layers stack along the c axis, being linked by C—H⋯π inter­actions.
doi:10.1107/S1600536810038791
PMCID: PMC3009190  PMID: 21588924
5.  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
6.  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
7.  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
8.  2-{[3-Methyl-4-(2,2,2-trifluoro­eth­oxy)pyridin-2-yl]methyl­sulfan­yl}-1H-benzimidazole monohydrate 
The asymmetric unit of the title compound, C16H14F3N3OS·H2O, contains two independent mol­ecules (A and B) and two water mol­ecules, one of which is disordered over two positions in a 0.790 (8):0.210 (8) ratio. The mol­ecular conformations are close, the benzimidazole mean plane and pyridine ring forming dihedral angles of 1.8 (3) and 0.1 (2)° in mol­ecules A and B, respectively. The water mol­ecules are involved in formation of two independent hydrogen-bonded chains via N—H⋯O and O—H⋯N hydrogen bonds. Chains propagating along the a axis are formed by mol­ecule A and one independent water mol­ecule, while chains propagating along the b axis are formed by mol­ecule B and the other independent water mol­ecule. The crystal packing exhibits π–π inter­actions, as indicated by short distances of 3.607 (3) and 3.701 (3) Å between the centroids of the imidazole and pyridine rings of neighbouring mol­ecules.
doi:10.1107/S1600536810053730
PMCID: PMC3051707  PMID: 21522962
9.  (2S,4R)-4-Ammonio-5-oxopyrrolidine-2-carboxylate 
In the crystal structure of the title compound, C5H8N2O3, the mol­ecules exist in the zwitterionic form. The pyrrolidine ring adopts an envelope conformation with the unsubstituted endocyclic C atom situated at the flap. The other four endocyclic atoms are coplanar with the exocyclic carbonyl O atom, with an r.m.s. deviation from the mean plane of 0.06 Å. The carboxyl­ate substituent is located axially, while the ammonium group occupies an equatorial position. In the crystal structure, the mol­ecules are linked through N—H⋯O hydrogen bonds, forming a three-dimensional network.
doi:10.1107/S1600536810004277
PMCID: PMC2984054  PMID: 21580659
10.  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
11.  2-(3-Morpholino­prop­yl)-2,3-dihydro-1H-pyrrolo­[3,4-b]quinolin-1-one monohydrate 
In the title compound, C18H21N3O2·H2O, the fused-ring system is approximately planar [maximum atomic deviation = 0.028 (3) Å]; the morpholine ring displays a chair conformation. The crystal packing is stabilized by classical inter­molecular O—H⋯O and O—H⋯N hydrogen bonds and weak C—H⋯O hydrogen bonds between the organic mol­ecules and the water mol­ecules.
doi:10.1107/S1600536810046349
PMCID: PMC3011724  PMID: 21589475
12.  Moxifloxacinium chloride monohydrate 
The title compound {systematic name: 7-[(1S,6S)-8-aza-2-azonia­bicyclo­[4.3.0]non-8-yl]-1-cyclo­propyl-6-fluoro-8-meth­oxy-4-oxo-1,4-dihydro­quinoline-3-carb­oxy­lic acid chloride monohydrate}, C21H25FN3O4 +·Cl−·H2O, crystallizes with two moxi­floxa­cinium cations, two chloride ions and two uncoordinated water mol­ecules in the unit cell. The crystal structure has a pseudo-inversion center except for the chloride ions. In both moxi­floxa­cinium cations, the quinoline rings are approximately planar, the maximum atomic deviations being 0.107 (3) and 0.118 (3) Å. The piperidine rings adopt a chair conformation while the pyrrolidine rings display a half-chair conformation. In the crystal, the carboxyl groups, the protonated piperidyl groups, the uncoordinated water mol­ecule and chloride anions participate in O—H⋯O, O—H⋯Cl and N—H⋯Cl hydrogen bonding; weak inter­molecular C—H⋯O and C—H⋯Cl hydrogen bonding is also present in the crystal structure.
doi:10.1107/S160053681103707X
PMCID: PMC3201314  PMID: 22058817
13.  (3RS)-S-[1-(3-Chloro­phen­yl)-2-oxopyr­rolidin-3-yl]-N,N′-dimethyl­thio­uronium bromide 
The title mol­ecule, C13H17ClN3OS+·Br−, consists of benzene and pyrrolidine rings and an S–C(NHCH3)2 group. The central C—N bond lengths in the S–C(NHCH3)2 fragment indicate partial double-bond character. Mol­ecules are inter­connected into chains by N—H⋯Br hydrogen bonds and the chains are linked into pairs by weak C—H⋯Br hydrogen bonds.
doi:10.1107/S1600536809002153
PMCID: PMC2968153  PMID: 21582004
14.  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
15.  3,3,3′,3′-Tetra­methyl-6,6′-bis­[(pyridin-4-yl)meth­oxy]-1,1′-spiro­biindane ­monohydrate 
The asymmetric unit in the title compound, C33H34N2O2·H2O, consists of a V-shaped mol­ecule and a water mol­ecule to which it is hydrogen bonded. The angle between the mean planes of the two spiro-connected indane groups is 77.06 (5)°. The two five-membered rings of the indane groups have envelope conformations with the methyl­ene atoms adjacent to the spiro C atom forming the flaps. They have deviations from the mean plane of the other four atoms in the rings of 0.374 (4) and 0.362 (4) Å. In the crystal, molecules are linked to form inversion dimers via O—H⋯N hydrogen bonds involving the pyridine N atoms and the solvent water mol­ecule. The dimers are linked into a chain along the b axis by π–π stacking inter­actions between a pyridine ring and its centrosymmetrically related ring in an adjacent dimer. The centroid–centroid distance between the planes is 3.7756 (17) Å, the perpendicular distance is 3.4478 (11) Å and the offset is 1.539 Å.
doi:10.1107/S1600536812021289
PMCID: PMC3379348  PMID: 22719546
16.  Poly[[μ-aqua-triaqua­[μ6-1,3,4,6-tetra­kis­(carboxyl­atometh­yl)-7,8-diphenyl­glycoluril]dizinc] monohydrate] 
In the crystal structure of the title coordination polymer, {[Zn2(C24H18N4O10)(H2O)4]·H2O}n, the mol­ecular building block (MBB), viz [Zn2(CO2)4(H2O)4], comprises two ZnII cations, each bridged by three carboxyl­ate groups from different ligand mol­ecules. These two ZnII cations exhibit different coordination environments: a distorted trigonal–pyramidal coordination, as an inter­mediate, is formed by the two coordinated water mol­ecules and three carboxyl­ate groups, and a distorted octa­hedral geometry defined by three water mol­ecules and three carboxyl­ate groups, in which two carboxyl­ate groups from the same side of the clip glycoluril ring and one water mol­ecule are bidentate bridging, whereas others are monodentate units. Every ligand mol­ecule connects four MBBs, thus forming a three-dimensional structure. Extensive intra- and inter­molecular O—H⋯O hydrogen bonding is observed.
doi:10.1107/S1600536811049191
PMCID: PMC3238721  PMID: 22199598
17.  1′-(1,3-Diphenyl-1H-pyrazol-4-yl)-1′′-(prop-2-en-1-yl)-2′,3′,5′,6′,7′,7a’-hexa­hydro-1′H-di­spiro­[1-benzo­pyran-3,2′-pyrrolizine-3′,3′′-indoline]-2′′,4-dione 0.75-hydrate 
In the central aza-bi­cyclo­octane unit of the title compound, C40H34N4O3·0.75H2O, the peripheral pyrrolidine ring adopts an envelope conformation with the N atom deviating by 0.209 (2) Å, whereas the other pyrrolidine ring adopts a twisted conformation with the bridging N and C atoms deviating by −0.218 (2) and 0.236 (3) Å, respectively, from the rest of the ring. The pyrazole ring forms dihedral angles of 42.36 (7) and 24.07 (8)° with its C- and N-attached phenyl groups, respectively. The solvent water mol­ecule has a partial occupancy of 0.75. In the crystal, the water mol­ecules link the fused-ring mol­ecules into chains along the b axis via O—H⋯N and O—H⋯O hydrogen bonds. The crystal packing is further stabilized by C—H⋯π inter­actions involving a methyl­ene group of the pyran ring and the C-attached benzene ring on the pyrazole ring.
doi:10.1107/S160053681301773X
PMCID: PMC3793707  PMID: 24109294
18.  (E)-N-(4-{[1-(Prop-2-en-1-yl)-1H-1,2,3-triazol-4-yl]meth­oxy}benzyl­idene)morpholin-4-amine 
The asymmetric unit of the title compound, C17H21N5O2, contains two crystallographically independent mol­ecules, which are linked by a C—H⋯N hydrogen bond. The morpholine rings of both mol­ecules adopt distorted chair conformations. The dihedral angles between the triazole and benzene rings are 12.8 (3)° in the first independent molecule in which the –N=C– group between the morpholine and benzene rings is disordered [site-occupancy ratio = 0.576 (7):0.424 (7)] and 88.1 (2)° in the second independent mol­ecule. In the crystal, mol­ecules are linked by C—H⋯N hydrogen bonds along the [100] direction. In addition, one weak C—H⋯π inter­action and two weak π–π stacking inter­actions [centroid–centroid distances = 3.840 (3) and 3.823 (2) Å] between the triazole rings of adjacent mol­ecules are observed. The atoms of the terminal propenyl groups in both mol­ecules are disordered over two sets of sites [site-occupancy ratios = 0.691 (10):0.309 (10) and 0.705 (15):0.295 (15)].
doi:10.1107/S1600536814002827
PMCID: PMC3998471  PMID: 24764998
19.  (2E)-3-{4-[(1H-1,3-Benzimidazol-2-yl)meth­oxy]-3-eth­oxy­phen­yl}-1-(4-bromo­phen­yl)prop-2-en-1-one monohydrate 
In the title compound, C25H21BrN2O3·H2O, the benzimidazole fragment and the water mol­ecule of crystallization are each disordered over two sets of sites of equal occupancy. The dihedral angles between the least-squares planes of the benzimidazole and the 3-eth­oxy- and 4-bromo­benzene rings are 86.9 (6) and 85.1 (1)°, respectively in one disorder component. The crystal packing is stabilized by inter­molecular O—H⋯O, O—H⋯N and N—H⋯N hydrogen bonds, which link the mol­ecules into chains along the a axis.
doi:10.1107/S1600536811008154
PMCID: PMC3099940  PMID: 21754118
20.  Crystal structure of (1S,2R,4S)-1-[(morpholin-4-yl)meth­yl]-4-(prop-1-en-2-yl)cyclo­hexane-1,2-diol 
Besides intra­molecular O—H⋯N hydrogen bonds, the crystal structure displays inter­molecular O—H⋯O and C—H⋯O hydrogen bonds linking the mol­ecules into undulating layers parallel to the (01) plane.
The asymmetric unit of the title compound, C14H25NO3, contains two independent mol­ecules with similar geometry. The morpholine and cyclo­hexane rings of both mol­ecules adopt a chair conformation. Intra­molecular O—H⋯N hydrogen bonds are observed. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds into chains parallel to the [101] direction. The chains are further connected through C—H⋯O hydrogen bonds forming undulating layers parallel to the (-101) plane. The absolute configuration was assigned by reference to an unchanging chiral centre in the synthetic procedure.
doi:10.1107/S2056989014027169
PMCID: PMC4331882
crystal structure; hydrogen bonds; amino-1,2-diol; chiral ligand for catalytic enanti­oselective transformations
21.  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
22.  3-Carboxy­methyl-1,3-benzimidazolium-1-acetate monohydrate 
The title compound, C11H10N2O4·H2O, has a zwitterionic structure, in which the benzimidazole ring system is planar, with a maximum deviation of 0.007 (3) Å. The carbox­yl/carboxyl­ate groups adopt a trans configuration. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds involving the hydr­oxy/oxide O atoms link the mol­ecules into a one-dimensional chain. These chains are further linked by O—H⋯O hydrogen bonds involving the water mol­ecules into a two-dimensional network. π–π contacts between the benzimidazole rings [centroid–centroid distance = 3.5716 (4) Å] lead to the formation of a three-dimensional supra­molecular structure.
doi:10.1107/S1600536809027391
PMCID: PMC2977158  PMID: 21583676
23.  1-Benzyl-2-(1H-indol-3-yl)-5-oxo­pyrrolidine-2-carbonitrile 
In the title compound, C20H17N3O, a potential anti-human immunodeficiency virus type 1 (HIV-1) non-nucleoside reverse-transcriptase inhibitor, the pyrrolidine ring has an envelope conformation. In the crystal structure, adjacent mol­ecules are connected into infinite chains via an N—H⋯O hydrogen bond.
doi:10.1107/S1600536807067670
PMCID: PMC2960201  PMID: 21201400
24.  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
25.  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

Results 1-25 (352099)