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1.  (8aRS)-8,8a-Dihydro­furo[3,2-f]indolizine-6,9(4H,7H)-dione 
The title compound, C10H9NO3, is a chiral mol­ecule with one stereogenic carbon atom, but which crystallizes as a racemate in the centrosymmetric space group P21/n. The central six-membered ring of the indolizine moiety adopts a definite envelope conformation, while the conformation of the oxopyrrolidine ring is close to that of a flat-envelope with a maximum deviation of 0.352 (1) Å for the flap atom.
doi:10.1107/S1600536811027383
PMCID: PMC3213484  PMID: 22091063
2.  (6S,7S,8S,8aS)-6-Ethyl-7,8-dihy­droxy-1,5,6,7,8,8a-hexa­hydro­indolizin-3(2H)-one monohydrate 
The absolute configuration of the title compound, C10H17NO3·H2O, was assigned from the synthesis. In the mol­ecular structure, the central six-membered ring of the indolizine moiety adopts a chair conformation, with two atoms displaced by −0.578 (2) and 0.651 (1) Å from the plane of the other four atoms [maximum deviation 0.019 (2) Å] The conformation of the fused oxopyrrolidine ring is close to that of a flat envelope, with the flap atom displaced by 0.294 (1) Å from the plane through the remaining four atoms. In the crystal, one of the hy­droxy groups is hydrogen-bonded to two water mol­ecules, while the other hy­droxy group exhibits an inter­molecular hydrogen bond to the carbonyl O atom, resulting in a chain parallel to the b axis.
doi:10.1107/S1600536810044855
PMCID: PMC3011597  PMID: 21589417
3.  (4R,6S,7S,8S,8aS)-6-Ethyl-7,8-dihy­droxy-4-methyl-1,2,3,5,6,7,8,8a-octa­hydro­indolizin-4-ium iodide 
The title compound, C11H22NO2 +·I−, is a chiral mol­ecule with five stereogenic centres. The absolute configuration was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine system adopts a chair conformation, with two atoms displaced by −0.690 (2) and 0.550 (2) Å from the plane of the other four atoms. The conformation of the pyrrolidine ring is close to that of an envelope, with the flap atom displaced by 0.563 (2) Å from the plane of the remaining four atoms. In the crystal, there are two O—H⋯I hydrogen bonds.
doi:10.1107/S1600536811051099
PMCID: PMC3239140  PMID: 22199988
4.  9-[(2-Meth­oxy­benz­yl)amino]-5-(3,4,5-trimeth­oxy­phen­yl)-5,5a,8a,9-tetra­hydro­furo[3′,4′:6,7]naphtho­[2,3-d][1,3]dioxol-6(8H)-one 
In the title compound, C30H31NO8, the tetra­hydro­furan ring and the six-membered ring fused to it both display envelope conformations, both having the same C atom as the flap. The dihedral angles between the benzene ring of the benzo[d][1,3]dioxole ring system and the other two benzene rings are 53.73 (3) and 83.30 (2)°. An intra­molecular N—H⋯O hydrogen bond is present. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains parallel to the c axis.
doi:10.1107/S160053681202572X
PMCID: PMC3393313  PMID: 22807870
5.  (3aR,8aS,9S,9aR)-9-Hydroxy­perhydro­furo[3,2-f]indolizin-6-one 
In the title compound, C10H15NO3, the central six-membered ring of the indolizine system adopts a chair conformation, while the oxopyrrolidine and hydro­furan rings attached to the indolizine ring system have envelope conformations. In the crystal, the mol­ecules form chains parallel to the b axis via inter­molecular O—H⋯O hydrogen bonds. The absolute configuration was assigned from the synthesis.
doi:10.1107/S1600536809024283
PMCID: PMC2977186  PMID: 21583447
6.  9-[(Furan-2-ylmeth­yl)amino]-5-(3,4,5-trimeth­oxy­phen­yl)-5,5a,8a,9-tetra­hydro­furo[3′,4′:6,7]naphtho­[2,3-d][1,3]dioxol-6(8H)-one 
In title compound, C27H27NO8, the dihydrofuran-2(3H)-one ring and the six-membered ring fused to it both display envelope conformations. The dihedral angle between the benzene ring of the benzo[d][1,3]dioxole group and the other benzene ring is 60.59 (2)°. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. The furan ring is disordered over two sets of sites with occupancies of 0.722 (7) and 0.278 (7)
doi:10.1107/S1600536811027735
PMCID: PMC3213528  PMID: 22091107
7.  9-{[4-(Dimethyl­amino)­benz­yl]amino}-5-(3,4,5-trimeth­oxy­phen­yl)-5,5a,8a,9-tetra­hydro­furo[3′,4′:6,7]naphtho­[2,3-d][1,3]dioxol-6(8H)-one 
In the title compound, C31H34N2O7, the fused tetra­hydro­furan and six-membered rings each display an envelope conformation. The dihedral angles between the benzene ring of the benzo[d][1,3]dioxole and the other two benzene rings are 89.68 (3) and 63.38 (2)°. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules.
doi:10.1107/S1600536811019234
PMCID: PMC3120627  PMID: 21754898
8.  9-{[4-(Dimethyl­amino)­benzyl]amino}-5-(4-hy­droxy-3,5-dimeth­oxy­phenyl)-5,5a,8a,9-tetra­hydro­furo[3′,4′:6,7]naphtho­[2,3-d][1,3]dioxol-6(8H)-one methanol monosolvate 
In the title compound, C30H32N2O7·CH4O, the tetra­hydro­furan ring and the six-membered ring fused to it both display envelope conformations, with the ring C atom opposite the carbonyl group and the adjacent bridgehead C atom as the flaps, respectively. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds link all moieties into ribbons along [010]. Weak inter­molecular C—H⋯O inter­actions consolidate the crystal packing further.
doi:10.1107/S1600536811043054
PMCID: PMC3247436  PMID: 22220054
9.  (11aS)-1,5,11,11a-Tetra­hydro-1-benzo­thieno[3,2-f]indolizin-3(2H)-one 
The absolute configuration of the title compound, C14H13NOS, was assigned from the synthesis and confirmed by the structure determination. There are two independent mol­ecules in the asymmetric unit. The central six-membered ring of the indolizine moiety adopts an envelope conformation, with the greatest deviations from the mean planes being 0.569 (3) and 0.561 (3) Å for the indolizine bridgehead C atoms of the two mol­ecules. The benzothieno ring attached to the indolizine ring system is planar to within 0.015 (3) Å in both mol­ecules. In the crystal, weak C—H⋯O and C—H⋯π inter­actions lead to the formation of a three-dimensional framework structure.
doi:10.1107/S1600536813031693
PMCID: PMC3885070  PMID: 24454246
10.  7′-Methyl-5′-oxo-2′,3′-dihydro­spiro­[1,3-dioxolane-2,1′(5′H)-indolizine]-6′-carbonitrile 
In the title compound, C12H12N2O3, the five-membered ring attached to the aromatic ring adopts an envelope conformation with a C atom in the flap position. The spiro-linked five-membered ring adopts a twisted conformation. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into C(5) chains propagating in [001].
doi:10.1107/S160053681003285X
PMCID: PMC3008056  PMID: 21588755
11.  (5S,11aS)-5-Hydro­per­oxy-1,5,11,11a-tetra­hydro­[1]benzothieno[3,2-f]indol­izin-3(2H)-one 
The absolute configuration of the title compound, C14H13NO3S, was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine moiety adopts an envelope conformation, with the greatest deviation from the mean plane of the ring being 0.661 (2) Å for the bridgehead C atom. The benzothiene ring attached to the indolizine ring system is planar to within 0.008 (2) Å. In the crystal, mol­ecules form chains parallel to the b axis via O—H⋯O hydrogen bonds.
doi:10.1107/S1600536812045394
PMCID: PMC3588932  PMID: 23476168
12.  (11R,11aS)-11-Hydr­oxy-1,5,11,11a-tetra­hydro-1-benzothieno[2,3-f]indolizin-3(2H)-one 
The absolute configuration of the title compound, C14H13NO2S, was assigned from the synthesis and confirmed by the structure determination. The central six-membered ring of the indolizine system adopts an envelope conformation, the greatest deviation from the mean plane of the ring being 0.459 (2) Å for the N atom. The benzothieno system is planar [mean deviation = 0.009 (2) Å]. In the crystal structure, mol­ecules form chains parallel to the b axis via inter­molecular O—H⋯O hydrogen bonds.
doi:10.1107/S1600536808015456
PMCID: PMC2961476  PMID: 21202672
13.  5′′-(2-Fluoro­benzyl­idene)-1′-(2-fluoro­phen­yl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a’-octa­hydro­dispiro­[ace­naphthyl­ene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione 
In the title compound, C37H32F2N2O2, the central six-membered piperidine ring adopts a twisted half-chair conformation, with the N and methyl­ene C atoms deviating by −0.2875 (16) and 0.4965 (15) Å, respectively, from the mean plane defined by the other four atoms. The piperidine connected to the octa­hydro­indolizine ring is in a half-chair conformation. The five-membered pyrrole ring adopts a slightly twisted envelope conformation with the piperidine C atom as the flap atom. The F and H atoms of both fluoro­benzene rings are disordered, with occupancy factors of 0.941 (3):0.059 (3) and 0.863 (3):0.137 (3). The mol­ecular structure features some intra­molecular C—H⋯O inter­actions. In the crystal, a supra­molecular zigzag chain sustained by C—H⋯F inter­actions parallel to the c axis is formed, generating a C(12) graph-set motif.
doi:10.1107/S1600536813019594
PMCID: PMC3793784  PMID: 24109371
14.  (7R,8R,8aS)-8-Hydr­oxy-7-phenyl­per­hydro­indolizin-3-one 
The absolute configuration of the title compound, C14H17NO2, was assigned from the synthesis. There are two mol­ecules in the asymmetric unit. Their geometries are very similar and corresponding bond lengths are almost identical [mean deviation for all non-H atoms = 0.015 (2) Å]. The six-membered ring of the indolizine system adopts a chair conformation. In the crystal structure, mol­ecules form chains parallel to the a axis via inter­molecular O—H⋯O hydrogen bonds, which help to stabilize the crystal structure.
doi:10.1107/S160053680901085X
PMCID: PMC2968891  PMID: 21582602
15.  (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
16.  (6S,7S,8R,8aS)-6-Ethyl­perhydro­indolizine-7,8-diol 
In the title compound, C10H19NO2, the piperidine and pyrrolidine rings of the perhydro­indolizine ring system adopt chair and envelope conformations, respectively. In the crystal structure, inter­molecular O—H⋯N and O—H⋯O hydrogen bonds link the mol­ecules into a chain running along the a axis.
doi:10.1107/S1600536810021240
PMCID: PMC3006912  PMID: 21587892
17.  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
18.  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
19.  5′′-(4-Meth­oxy­benzyl­idene)-1′-(4-meth­oxy­phen­yl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a′-octa­hydro­dispiro­[acenaphthyl­ene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione 
In the title compound, C39H38N2O4, the pyridinone ring adopts a twisted half-chair conformation with the N atom deviating by 0.3304 (1) and with the methyl­ene C atom adjacent to the octa­hydro­indolizine unit deviating by 0.444 (3) Å from the mean plane defined by the other four atoms. In the octa­hydro­indolizine system, the pyrrolidine ring exhibits an envelope conformation, with the fused methyne C atom deviating by 0.6315 (1) Å from the mean plane defined by the other four atoms, and the piperidine ring exhibits a distorted chair conformation, as reflected in the puckering parameters Q = 0.568 (4) Å, θ = 1.5 (4) and ϕ = 161 (16)°. In the crystal pairs of weak C—H⋯O inter­actions form centrosymmetric dimers, which are further connected by C—H⋯π inter­actions. The crystal studied was a non-merohedral twin, with a domain ratio of 0.91:0.09.
doi:10.1107/S1600536813001177
PMCID: PMC3569788  PMID: 23424534
20.  rac-5′′-(4-Fluoro­benzyl­idene)-1′-(4-fluoro­phen­yl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a′-octa­hydro­dispiro­[acenaphthyl­ene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione 
In the title E isomer of the racemic compound, C37H32F2N2O2, the pyridinone ring adopts a twisted half-chair conformation with the N atom deviating by −0.355 (3) Å and with the methyl­ene C atom next to octa­hydro­indolizine moiety deviating by 0.415 (3) Å from the mean plane defined by other four atoms. In the octa­hydro­indolizine system, the pyrrolidine ring exhibits an envelope conformation with the fused methyne C atom deviating by 0.6496 (1) Å from the mean plane defined by four other atoms, and the piperidine ring exhibits a distorted chair conformation as evident from the puckering parameters Q = 0.568 (2) Å, θ = 1.0 (2) and Φ = 256 (11)°. In the crystal, C—H⋯O inter­actions connect the mol­ecules into chains along [101].
doi:10.1107/S1600536812051094
PMCID: PMC3588349  PMID: 23476397
21.  (3,5-Dimethyl-1H-pyrazol-1-yl){3-[(3,5-dimethyl-1H-pyrazol-1-yl)carbon­yl]-5-methyl­indolizin-1-yl}methanone 
There are two independent mol­ecules in the asymmetric unit of the title compound, C21H21N5O2. In each mol­ecule, the indolizine ring system is essentially planar, with r.m.s. deviations of 0.030 and 0.028 Å. The dihedral angles between the indolizine ring system and the pyrazole rings are 54.7 (3) and 8.6 (3)° in one mol­ecule and 54.4 (3) and 6.6 (3)° in the other. In the crystal, weak C—H⋯O and C—H⋯N hydrogen bonds link mol­ecules, forming a two-dimensional network parallel to (100).
doi:10.1107/S1600536813005060
PMCID: PMC3588476  PMID: 23476618
22.  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
23.  {(3aR,5S,6R,6aR)-5-[(R)-1,2-Di­hydroxy­eth­yl]-2,2-di­methyl­tetra­hydro­furo[2,3-d][1,3]dioxol-6-yl}methyl methane­sulfonate 
In the title compound, C11H20O8S, the furan­ose ring has a pseudorotation phase angle equal to 31.3° and assumes a 3 T 4 conformation, with deviations of 0.297 (4) and −0.152 (4) Å for the corresponding C atoms. The dioxolane ring adopts an envelope conformation. One of the O atoms is at the flap and deviates from the least-squares plane formed by the other four ring atoms by 0.405 (2) Å. The dihedral angle between the planar fragments of the rings is 63.53 (8)°. In the crystal, mol­ecules are associated into sheets perpendiculer to the b axis by means of O—H⋯O hydrogen bonds. A few weak C—H⋯O inter­actions are also observed.
doi:10.1107/S1600536814007387
PMCID: PMC4011227  PMID: 24860338
24.  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
25.  (6S,7S,8S,8aS)-6-Ethyl-3-oxo-1,2,3,5,6,7,8,8a-octa­hydro­indolizine-7,8-diyl diacetate 
In the mol­ecular structure of the title compound, C14H21NO5, the six-membered ring of the indolizine moiety adopts a chair conformation. There are two independent mol­ecules in the asymmetric unit. The oxopyrrolidine ring attached to the indolizine ring system is nearly planar, with mean deviations of 0.018 (3) and 0.010 (3) Å for the two mol­ecules. The absolute configuration of the title compound was assigned from the synthesis.
doi:10.1107/S1600536812005144
PMCID: PMC3295453  PMID: 22412564

Results 1-25 (217262)