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1.  3-Benzyl-7-meth­oxy-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-pyrrolo[3,4-b]quinoline 
In the title compound, C32H32N2O3S, the pyrrolidine ring adopts an envelope conformation with the methine C atom nearest to the phenyl ring as the flap atom. The tetra­hydro­pyridine ring has a half-chair conformation. The two rings are trans-fused. The phenyl ring bound to the tetra­hydro­pyridine is oriented almost perpendicular [dihedral angle = 86.35 (10)°] to the fused benzene ring. The dihedral angle between the benzyl­phenyl ring and the sulfonyl-bound phenyl ring is 69.43 (10)°. A very weak N—H⋯π inter­action is observed in the mol­ecular structure. In the crystal, mol­ecules translated one unit along the b axis are linked into C(10) chains by C—H⋯O hydrogen bonds; adjacent chains are linked via C—H⋯π inter­actions, forming a two-dimensional network parallel to the bc plane.
doi:10.1107/S1600536809044973
PMCID: PMC2971011  PMID: 21578528
2.  1-[(3RS,4RS)-1-Benzyl-4-methyl­piperi­din-3-yl]-1,6-dihydro­imidazo[4,5-d]pyrrolo­[2,3-b]pyridine hemihydrate 
The benzyl residue in the title compound, C21H23N5·0.5H2O, is oriented at a dihedral angle of 83.8 (3)° towards the 1,6-dihydro­imidazo[4,5-d]pyrrolo­[2,3-b]pyridine system. The piperidine ring adopts a chair conformation with the cis substituents displaying a torsion angle of −45.91 (16)°. In the crystal, mol­ecules are accumulated as racemic dimers by two inter­molecular hydrogen bonds between the pyrrolo­pyridine systems. Another hydrogen bond is formed between the imidazole ring and the cocrystallized water mol­ecule, which is located on a twofold rotation axis.
doi:10.1107/S1600536812039980
PMCID: PMC3470401  PMID: 23125814
3.  1-Benzyl-6,8-dimethyl-4-phenyl-2-tosyl-1,2,3,3a,4,6,7,8,9,9b-deca­hydro­pyrrolo[3,4-c]pyrano[6,5-d]pyrimidine-7,9-dione 
The mol­ecule of the title compound, C31H31N3O5S, adopts a folded conformation, with the sulfonyl-bound phenyl ring lying over the pyrimidine ring [dihedral angle = 12.04 (6)° and centroid–centroid separation = 3.6986 (8) Å]. The pyrrolidine ring adopts a twist conformation, the dihydro­pyran ring is in a half-chair conformation and the two rings are cis-fused. The tosyl group is attached to the pyrrolidine ring in an equatorial position while the benzyl group is axially attached. The mol­ecular structure is stabilized by weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions. In the crystal, pairs of mol­ecules related by inversion symmetry are linked by C—H⋯O hydrogen bonds, forming chains propagating along the c axis which are cross-linked into a three-dimensional framework by further C—H⋯O links.
doi:10.1107/S1600536809044341
PMCID: PMC2971200  PMID: 21578488
4.  3-Benzyl-7-bromo-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-pyrrolo[3,4-b]quinoline 
In the title compound, C31H29BrN2O2S, the pyrrolidine ring is in a twist conformation and the tetra­hydro­pyridine ring adopts an envelope conformation with the methine C atom adjacent to the NH group as the flap atom; the two rings are trans-fused. The bromo­benzene ring and the nearest phenyl ring form a dihedral angle of 82.72 (10)°. The benzyl phenyl and the tosyl phenyl rings are oriented at a dihedral angle of 75.57 (11)°. An intra­molecular N—H⋯π inter­action is observed. In the crystal, mol­ecules are linked into chains running along [101] by C—H⋯O hydrogen bonds and the chains are cross-linked via weak C—H⋯π inter­actions.
doi:10.1107/S1600536809045875
PMCID: PMC2971917  PMID: 21578741
5.  3-Benzyl-7-methyl-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-pyrrolo[3,4-b]quinoline 
In the title compound, C32H32N2O2S, the pyrrolidine ring adopts a twist conformation while the tetra­hydro­pyridine ring is in a distorted half-chair conformation. The two rings are trans-fused. The dihedral angle between the sulfonyl and benzyl phenyl rings is 72.54 (14)°. The mol­ecular structure is stabilized by C—H⋯O hydrogen bonds, and N—H⋯π inter­actions involving the benzyl phenyl ring. The screw-related mol­ecules are linked into chains along the b axis by C—H⋯O hydrogen bonds and C—H⋯π inter­actions. Adjacent inversion-related chains inter­act via C—H⋯π inter­actions, forming a two-dimensional network parallel to the bc plane.
doi:10.1107/S1600536809044481
PMCID: PMC2971294  PMID: 21578502
6.  N-[(3RS,4RS)-1-Benzyl-4-methyl­piperidin-3-yl]-5-nitro-1-phenyl­sulfonyl-1H-pyrrolo­[2,3-b]pyridine-4-amine 
The pyrrolo­pyridine system in the title compound, C27H29N5O4S, is oriented at a dihedral angle of 71.20 (5)° towards the phenyl ring of the tosyl residue and at a dihedral angle of 45.43 (4)° towards the benzyl group. The structure shows an intra­molecular N—H⋯O and a weak intra­molecular N—H⋯N hydrogen bond. The piperidine ring adopts a chair conformation, with the cis substituents displaying a torsion angle of −54.59 (18)°.
doi:10.1107/S1600536812039979
PMCID: PMC3470400  PMID: 23125813
7.  7-(4-Chloro­phen­yl)-9-phenyl-7H-pyrrolo[3,2-e]tetra­zolo[1,5-c]pyrimidine 
In the title compound, C18H11ClN6, the pyrrole, pyrimidine and tetra­zole rings form a nearly planar fused trihetrocyclic system with an r.m.s. deviation of 0.0387 (13) Å, to which the 4-chloro­phenyl group and the phenyl group are substituted at the 7 and 9 positions, respectively. The dihedral angles between the pyrrole ring and the 4-chloro­phenyl and phenyl rings are 32.1 (4) and 7.87 (7)°, respectively. In the crystal, weak inter­molecular C—H⋯N and C—H⋯Cl hydrogen bonds link the mol­ecules into a layer parallel to the (001) plane. The layers are further connected by π–π stacking inter­actions [centroid–centroid distances: 3.8413 (8) and 3.5352 (8) Å]. Intra­molecular C—H⋯N hydrogen bonds are also present.
doi:10.1107/S160053681000485X
PMCID: PMC2983688  PMID: 21580361
8.  7-(4-Methoxy­phen­yl)-5-methyl-9-phenyl-7H-pyrrolo[2′,3′:4,5]pyrimido[1,6-d]tetrazole 
The title compound, C20H16N6O, is composed of a tetra­zolo ring and a 4-methoxy­phenyl and a benzene-substituted pyrrole ring at the 7 and 9 positions fused to a pyrimidine ring in a nearly planar fashion [maximum deviation of 0.018 (1) Å for the fused ring system]. A methyl group at the 5 position is also in the plane of the hetero cyclic system. The dihedral angle between the mean planes of the benzene and 4-methoxy­phenyl rings is 40.4 (2)°. The dihedral angles between the mean planes of the pyrimidine and the benzene and 4-methoxy­phenyl rings are 15.6 (5)° and 52.6 (7)°, respectively. A weak intra­molecular C—H⋯N hydrogen bond inter­action, which forms an S(7) graph-set motif, helps to establish the relative conformations of the tetrazolo and benzene rings. In the crystal, weak inter­molecular C—H⋯O, C—H⋯π and π–π stacking inter­actions [centroid–centroid distances = 3.5270 (16), 3.5113 (16), 3.7275 (17) and 3.7866 (17) Å] link the mol­ecules into a two-dimensional array obliquely parallel to (101) and propagating along the b axis.
doi:10.1107/S1600536809053653
PMCID: PMC2980237  PMID: 21580097
9.  3-Benzyl-7-chloro-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-pyrrolo[3,4-b]quinoline 
In the title compound, C31H29ClN2O2S, the pyrrolidine ring adopts an envelope conformation with the methine C atom adjacent to the NH group as the flap atom. The tetra­hydro­pyridine ring has a half-chair conformation. The two rings are trans-fused. The chloro­benzene ring and the adjacent phenyl ring form a dihedral angle of 77.9 (1)°. The benzyl phenyl and the tosyl phenyl rings are oriented at a dihedral angle of 88.0 (1)°. In the crystal, mol­ecules are linked into chains along the a axis by N—H⋯Cl and C—H⋯Cl hydrogen bonds and the adjacent chains are cross-linked via C—H⋯π inter­actions.
doi:10.1107/S1600536809045267
PMCID: PMC2972055  PMID: 21578714
10.  3-Benzyl-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa­hydro-1H-pyrrolo[3,4-b]quinoline 
In the title compound, C31H30N2O2S, the pyrrolidine ring adopts a twist conformation while the tetra­hydro­pyridine ring is in a half-chair conformation. The two rings are trans-fused. The pyridine-bound phenyl ring forms dihedral angles of 17.7 (1) and 48.1 (1)°, respectively, with the tosyl and benzyl phenyl rings. The mol­ecular structure is stabilized by an N—H⋯π inter­action involving the benzyl phenyl ring. In the crystal structure, mol­ecules translated by one unit along the a axis are linked into chains by C—H⋯π inter­actions involving the benzene ring of the tosyl group.
doi:10.1107/S1600536809044547
PMCID: PMC2971326  PMID: 21578501
11.  7-(4-Bromo­phen­yl)-9-phenyl-7H-pyrrolo[3,2-e]tetra­zolo[1,5-c]pyrimidine 
In the title compound, C18H11BrN6, the phenyl ring is almost coplanar [dihedral angle 7.2 (1)°] with the planar (r.m.s. deviation 0.039 Å) tricyclic ring system while the 4-bromo­phenyl ring makes a dihedral angle of 33.98 (6)° with the ring system. Weak inter­molecular C—H⋯N and C—H⋯Br hydrogen-bonding inter­actions and π–π stacking [centroid–centroid distances = 3.7971 (17) and 3.5599 (16) Å] stabilize the crystal packing. A comparison of the structure to a MOPAC PM3 geometry optimization calculation in vacuo supports these observations.
doi:10.1107/S1600536810004368
PMCID: PMC2983701  PMID: 21580341
12.  2-Methyl-3-(5-methyl-2-thien­yl)-5-phenyl­perhydro­pyrrolo[3,4-d]isoxazole-4,6-dione 
In the mol­ecule of the title compound, C17H16N2O3S, the phenyl ring is oriented with respect to the thio­phene and succinimide rings at dihedral angles of 88.08 (3) and 57.81 (3)°, respectively; the dihedral angle between the thio­phene and succinimide rings is 35.69 (3)°. The isoxazole ring adopts an envelope conformation with the N atom at the flap position. In the crystal structure, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into infinite chains along the b axis. Weak C—H⋯π inter­actions may further stabilize the structure.
doi:10.1107/S1600536809009209
PMCID: PMC2968779  PMID: 21582577
13.  4-Chloro-7-methoxy­methyl-2-phenyl-7H-pyrrolo[2,3-b]pyridine 
In the title compound, C15H13ClN2O, the phenyl group makes a dihedral angle of 7.91 (8)° with the pyrrole ring. The crystal structure forms a three-dimensional network stabilized by π–π inter­actions [centroid–centroid distances = 3.807 (1) Å] between the pyridine and phenyl rings and via inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536810008822
PMCID: PMC2983947  PMID: 21580653
14.  Ethyl 2-phenyl-5,6-dihydro­pyrrolo­[2,1-a]isoquinoline-3-carboxyl­ate 
In the title compound, C21H19NO2, the six-membered heterocycle assumes a screw-boat conformation. The phenyl ring is oriented with respect to the pyrrole ring at a dihedral angle of 64.76 (10)°. An intra­molecular C—H⋯O hydrogen bond helps to stabilize the mol­ecular structure. There are weak C—H⋯π inter­actions between inversion-related mol­ecules in the crystal.
doi:10.1107/S1600536812024853
PMCID: PMC3393290  PMID: 22807847
15.  2-(4-Methoxy­phen­yl)-6-trifluoro­methyl-1H-pyrrolo[3,2-c]quinoline monohydrate 
In the title compound, C19H13F3N2O·H2O, the phenyl and pyrroloquinoline ring system are close to coplanar [dihedral angle = 10.94 (4)°]. The meth­oxy group also is almost coplanar with the phenyl ring [5.4 (1)°]. In the crystal structure N—H⋯O(water) and water–quinoline O—H⋯N hydrogen bonds build up a supra­molecular chain-like arrangement along [001]. The remaining H atom of the water mol­ecule does not take part in classical hydrogen bonds. Instead, this O—H bond points toward the center of the phenyl ring of a neighbouring mol­ecule. Weak C—H⋯O and C—H⋯π inter­actions are also present.
doi:10.1107/S1600536810013644
PMCID: PMC2979020  PMID: 21579163
16.  (4-Nitrophenyl)(1,2,3,9-tetrahydro­pyrrolo[2,1-b]quinazolin-3-yl)methanol monohydrate 
In the crystal structure of the title compound, C18H17N3O3·H2O, the mol­ecules are linked by O—H⋯O and O—H⋯N hydrogen bonds, resulting in a chain along the a axis. The crystal structure is stabilized by weak inter­molecular C—H⋯π (ring) hydrogen bonds and aromatic π⋯π stacking inter­actions [centroid–centroid distance = 3.902 (1) Å] between the pyrimidino rings of the quinazoline system. The tricyclic quinazoline fragment is almost planar (rms deviation = 0.0139 Å) with the two methylene C atoms of the pyrrolo ring deviating by 0.148 (2) and −0.081 (3) Å from the plane through the other atoms. The 4-nitrophenyl ring makes a dihedral angle of 12.55 (7)° with the tricyclic ring system.
doi:10.1107/S1600536811021775
PMCID: PMC3151778  PMID: 21837078
17.  (3R,3aS,6aR)-2,5-Dimethyl-3-(5-phenyl-2-thien­yl)perhydro­pyrrolo[3,4-d][1,2]oxazole-4,6-dione 
The crystal structure of the title compound, C17H16N2O3S, exhibits intra­molecular C—H⋯S and inter­molecular C—H⋯S and C—H⋯O hydrogen bonds, C—S⋯N [S⋯N = 3.033 (2) Å and C—S⋯N = 142.76 (9)°] inter­actions, and C—H⋯π inter­actions; these inter­actions generate S(4), S(6) and R 2 2(14) ring motifs. The isoxazole ring adopts an envelope conformation, with the N atom displaced by 0.672 (2) Å from the plane of the other ring atoms. The thio­phene ring is oriented with respect to the succinimide and phenyl rings at dihedral angles of 40.03 (12) and 5.21 (13)°, respectively. The dihedral angle between the succinimide and phenyl rings is 39.38 (12)°.
doi:10.1107/S1600536808020102
PMCID: PMC2962057  PMID: 21203142
18.  4-Phenyl­sulfon­yl-2-(p-tolyl­sulfon­yl)-1H,8H-pyrrolo­[2,3-b]indole 
The title compound, C23H18N2O4S2, contains a pyrrolo group fused onto the plane of an indole ring with phenyl­sulfonyl and p-toluene­sulfonyl groups bonded to the indole and pyrrolo rings. The angles between the mean planes of the pyrrolo-indole ring and the phenyl­sulfonyl and p-toluene­sulfonyl rings are 73.7 (6) and 80.6 (0)°, respectively. The dihedral angle between the mean planes of the two benzene rings is 78.7 (4)°. In the crystal, both classical N—H⋯O and non-classical C—H⋯O inter­molecular hydrogen-bonding inter­actions are observed, as well as weak π–π inter­actions [centroid–centroid distances = 3.6258 (8) and 3.9298 (8) Å], which contribute to the stability of the packing.
doi:10.1107/S1600536810039425
PMCID: PMC3009299  PMID: 21588961
19.  N-[(3RS,4SR)-1-Benzyl-4-methyl­piperi­din-3-yl]-1-(4-methylphenyl­sulfonyl)-5-nitro-1H-pyrrolo­[2,3-b]pyridin-4-amine 
The structure of the title compound, C27H29N5O4S, displays an intra­molecular N—H⋯O hydrogen bond. The pyrrolo­[2,3-b]pyridine core makes a dihedral angle of 85.5 (4)° with the benzyl residue and a dihedral angle of 89.4 (9)° with the tosyl ring. The nitro group is slightly twisted out of the plane of the planar pyrrolo­pyridine system [(—N—)C—C—N—O torsion angle = −4.61 (18)° and (—NH—)C—C—N—O = −6.46 (18)°].
doi:10.1107/S160053681203961X
PMCID: PMC3470359  PMID: 23125772
20.  10-{4-[(2-Hy­droxy­benzyl­idene)amino]­phen­yl}-5,5-di­fluoro-1,3,7,9-tetra­methyl-5H-di­pyrrolo­[1,2-c:2′,1′-f][1,3,2]di­aza­borinin-4-ium-5-uide 
The title compound, C26H24BF2N3O, comprises a boron–dipyrromethene (BODIPY) framework and a phenolic Schiff base substituent group. The BODIPY unit is close to planar [maximum deviation from the least-squares plane = 0.040 (3) Å], and forms a dihedral angle of 80.38 (13)° with the meso-substituent phenyl ring and an angle of 56.57 (13)° with the phenolic ring in the extended substituent chain. An intra­molecular O—H⋯N hydrogen bond is formed between the phenolic hydroxyl group and the Schiff base N-atom. The crystal studied was a non-merohedral twin with a BASF factor of 0.447 (3) for the two components.
doi:10.1107/S1600536813015523
PMCID: PMC3770354  PMID: 24046639
21.  3-(4-Chloro­phen­yl)-4-(4-methoxyphen­yl)-6-(phenyl­selenylmeth­yl)-2,3,3a,3b,4,5,5a,6,1′′,2′′,3′′,4′′-do­deca­hydro­azeto[2′,3′:3,4]pyrrolo[1,2-b]isoxazole-2-spiro-2′′-naphthalene-5,1′′-dione 
In the title compound, C36H31ClN2O4Se, the four-membered β-lactam ring is fused to a pyrrolidine ring. The central five-membered ring of the fused tricyclic system exhibits an envelope conformation with the N atom as the flap, while the other five-membered ring exhibits a twist conformation. The chloro­phenyl ring is almost perpendicular to the pyrrolidine ring, making a dihedral angle of 73.45 (1)°. The crystal structure is stabilized by weak inter­molecular C—H⋯O inter­actions and the packing is further enhanced by C—H ⋯N inter­actions and π–π inter­actions between benzene rings of tetra­lone groups in mol­ecules related by an inversion center, with a centroid–centroid separation of 3.8923 (2) Å.
doi:10.1107/S1600536808006570
PMCID: PMC2960925  PMID: 21202107
22.  2-[(1RS,3RS,3aRS,6aSR)-5-Benzyl-4,6-dioxo-3-phenyl­octa­hydro­pyrrolo­[3,4-c]pyrrol-1-yl]acetamide 
In the title compound, C21H21N3O3, the relative stereochemistry of the four stereogenic C atoms has been determined. The dihedral angle between the phenyl rings is 77.63 (7)°. In the crystal, ribbons spread along the a axis are formed by N—H⋯O hydrogen bonds. C—H⋯π inter­actions also occur.
doi:10.1107/S1600536811045181
PMCID: PMC3238854  PMID: 22199707
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.  1-[2-(Benzyl­amino)-4-pyrid­yl]-2-(4-fluoro­phen­yl)ethane-1,2-dione 
The crystal structure of the title compound, C20H15FN2O2, contains two crystallographically independent mol­ecules, which are related by a pseudo-inversion center and linked into dimers via inter­molecular N—H⋯N hydrogen bonds. The 4-fluoro­phenyl ring of mol­ecule A makes dihedral angles of 17.17 (16) and 62.25 (15)°, respectively, with the phenyl and pyridine rings. The 4-fluoro­phenyl ring of mol­ecule B makes dihedral angles of 8.50 (16) and 64.59 (15)°, respectively, with the phenyl and pyridine rings. The dihedral angle between the pyridine ring and the phenyl ring of mol­ecule A [60.97 (15)°] is bigger than in mol­ecule B [59.49 (15)°]. The dihedral angle between the two pyridine rings is 1.37 (14)° and between the two phenyl rings is 3.64 (16)°.
doi:10.1107/S1600536809019801
PMCID: PMC2969582  PMID: 21583289
25.  (E)-3-[4-(Dimethyl­amino)­benzyl­idene]-2,3-di­hydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one 
The title compound, C20H19N3O, was obtained by condensation of 2,3-dihydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one (alkaloid de­oxy­vasicinone, isolated from Peganum Harmala) with 4-(dimethyl­amino)­benzaldehyde in the presence of sodium methoxide. The 2,3-dihydro-1H,9H-pyrrolo­[2,1-b]quinazolin-9-one part of the mol­ecule is roughly planar (r.m.s. deviation = 0.0178 Å) and is essentially coplanar with the benzil­idene ring (r.m.s. deviation = 0.0080 Å), forming a dihedral angle of 5.0 (1)°. The crystal structure is stabilized by two aromatic π–π stacking inter­actions observed between the benzene rings of neighboring mol­ecules [centroid–centroid distance = 3.7555 (19) Å.
doi:10.1107/S1600536810020878
PMCID: PMC3006833  PMID: 21587830

Results 1-25 (1274686)