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1.  5-Hy­droxy-8,8-dimethyl-10-(2-methyl­but-3-en-2-yl)-2H,6H-7,8-dihydro­pyrano[3,2-g]chromene-2,6-dione 
In the title compound, C19H20O5, the pyran ring is in an envelope conformation, whereas the benzene and dihydro­pyran ring system is planar with an r.m.s. deviation of 0.0190 (1) Å. The hy­droxy group is coplanar with the attached benzene ring [r.m.s. deviation = 0.0106 (1) Å]. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked into chains along the b axis by weak C—H⋯O inter­actions. These chains are stacked along the a axis. C—H⋯π and weak π–π inter­actions [centroid–centroid distance = 3.7698 (7) Å] are also observed.
PMCID: PMC3051790  PMID: 21523091
2.  10-Methyl-2-oxo-4-phenyl-2,11-di­hydro­pyrano[2,3-a]carbazole-3-carbo­nitrile 
In the title mol­ecule, C23H14N2O2, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1018 (8) Å]. The pyrrole ring makes dihedral angles of 4.44 (5), 3.84 (5), 2.18 (5) and 56.44 (5)° with the pyran, fused benzene rings and phenyl ring, respectively. In the crystal, pairs of N—H⋯O hydrogen bonds generate R 2 2(14) loops and a C—H⋯N inter­action is also found. Mol­ecules are further linked by a number of π–π interactions [centroid–centroid distances vary from 3.5702 (5) to 3.7068 (6) Å], forming a three-dimensional network.
PMCID: PMC3684919  PMID: 23795021
3.  6-Amino-1-benzyl-4-(4-chloro­phen­yl)-3-(4-pyrid­yl)-1,4-dihydro­pyrano[2,3-c]pyrazole-5-carbonitrile 
The crystal structure of the title compound, C25H18ClN5O, was determined in the course of our studies on the synthesis of 1,4-dihydro­pyrano[2,3-c]pyrazole as an inhibitor of the p38 mitogen-activated protein kinase (MAPK). The compound was prepared via a base-catalysed synthesis from 1-benzyl-3-(4-pyrid­yl)-1H-pyrazol-5(4H)-one with p-chloro­aldehyde and malononitrile. The crystal data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The phenyl ring is disordered over two positions, with site occupancy factors of 0.55 and 0.45. The dihedral angles between the 1,4-dihydropyrano[2,3-c]pyrazole unit and the chloro­phenyl and pyridine rings are 83.7 (1) and 16.0 (1)°, respectively. The chloro­phenyl and pyridine rings make a dihedral angle of 86.8 (2)°.
PMCID: PMC2960986  PMID: 21202092
4.  4,8-Dimethyl­pyrano[2,3-a]carbazol-2(11H)-one 
The mol­ecule of the title compound, C17H13NO2, is nearly planar, the r.m.s. deviation for all non-H atoms excluding the two methyl C atoms being 0.089 Å. Inter­molecular N—H⋯O and C—H⋯O hydrogen bonds are found in the crystal structure. C—H⋯π inter­actions are also found. The H atoms of the methyl group attached to the benzene ring are disordered equally over two positions.
PMCID: PMC2968986  PMID: 21582550
5.  3-(2,4-Dichloro­phen­yl)-5-(4-fluoro­phen­yl)-2-phenyl-7-(trifluoro­meth­yl)pyrazolo­[1,5-a]pyrimidine 
In the title compound, C25H13Cl2F4N3, there are four planar systems, viz. three benzene rings and a pyrazolo­[1,5-a]pyrim­idine system [r.m.s. deviation = 0.002 Å]. The dihedral angle between the dichloro­phenyl ring and the unsubstituted phenyl ring is 69.95 (5)°, while that between the fluoro­phenyl ring and the unsubstituted phenyl ring is 7.97 (10)°. The crystal packing is dominated by van der Waals inter­actions. A Cl⋯Cl inter­action of 3.475 (3) Å also occurs.
PMCID: PMC3379478  PMID: 22719676
6.  2,2,9-Trimethyl-2,3-dihydro­pyrano[2,3-a]carbazol-4-(11H)-one 
The title compound, C18H17NO2, was prepared from 1-hydr­oxy-7-methyl­carbazole and 3,3-dimethyl­acrylic acid with trifluoro­acetic acid as the cyclization catalyst. The mol­ecules contain an essentially planar 6-methyl­indole unit. The second aromatic ring is significantly bent away from the plane of this unit, with maximum deviations of 0.171 (1) and 0.185 (1) Å for two of the C atoms. In the crystal structure, there are neither N—H⋯O hydrogen bonds nor π–π stacking between the aromatic sections of neighboring mol­ecules. There is only one weak C—H⋯O hydrogen bond and a number of weak C—H⋯π inter­actions.
PMCID: PMC2959763  PMID: 21581016
7.  (E)-1-(2,5-Dichloro­thio­phen-3-yl)ethan­one [8-(trifluoro­meth­yl)quinolin-4-yl]hydrazone 
In the title compound, C16H10Cl2F3N3S, the dihedral angle between the quinoline and thio­phene ring systems is 4.94 (10)°. The NH group of the hydrazone moiety does not form a hydrogen bond, due to a steric crowding. In the crystal, the thio­phene ring takes part in weak π–π stacking inter­actions with the pyridine ring [centroid-to-centroid separation = 3.7553 (19) Å and inter­planar angle = 5.48 (12)°] and the benzene ring [3.7927 (19) Å and 4.58 (12)°]. Together, these lead to [100] stacks of mol­ecules in an alternating head-to-tail arrangement, with two π–π stacking contacts between each adjacent pair.
PMCID: PMC3297859  PMID: 22412662
8.  2-Chloro-N-{3-cyano-1-[2,6-dichloro-4-(trifluoro­meth­yl)phen­yl]-1H-pyrazol-5-yl}acetamide 
The title compound, C13H6Cl3F3N4O, was synthesized by the reaction of 5-amino-1-[2,6-dichloro-4-(trifluoro­meth­yl)phen­yl]-1H-pyrazole-3-carbonitrile and 2-chloro­acetyl chloride. The five-membered pyrazole ring makes a dihedral angle of 71.5 (3)° with the benzene ring. The –CF3 group is disordered by rotation, and the F atoms are split over two sets of sites with occupancies of 0.59 (2) and 0.41 (2). The crystal structure features weak C—H⋯O and N—H⋯N inter­actions involving the carbonyl and cyano groups as acceptors.
PMCID: PMC3254452  PMID: 22259391
9.  2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoro­meth­yl)phen­yl]-1,4,5,6,7,8-hexa­hydro­quinoline-3-carbonitrile 
In the title mol­ecule, C19H18F3N3O, the dihydro­pyridine and cyclo­hexene rings both adopt sofa conformations. The five essentially planar atoms of the dihydro­pyridine ring [maximum deviation = 0.039 (2) Å] form a dihedral angle of 88.19 (8)° with the benzene ring. The F atoms of the trifluoro­methyl group were refined as disordered over two sets of sites in a 0.840 (3):0.160 (3) ratio. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link mol­ecules into a two-dimensional network parallel to (100).
PMCID: PMC3588344  PMID: 23476367
10.  1-Phenyl-2-[4-(trifluoro­meth­yl)phen­yl]-1H-benzimidazole 
In the title mol­ecule, C20H13F3N2, the benzimidazole unit is close to being planar [maximum deviation = 0.012 (1) Å] and forms dihedral angles of 31.43 (7) and 61.45 (9)° with the 4-(trifluoromethyl)phenyl and 1-phenyl rings, respectively; the dihedral angle between these rings is 60.94 (10)°. In the crystal, C—H⋯F hydrogen bonds link the mol­ecules into chains along the c-axis direction. The CF3 group is rotationally disordered with an occupancy ratio of 0.557 (8):0.443 (8) for the F atoms.
PMCID: PMC3569777  PMID: 23424523
11.  8-Meth­oxy-3,3,5-trimethyl-3,11-dihydro­pyrano[3,2-a]carbazole 
In the title compound, C19H19NO2, commonly called koenimbine, the pyran ring adopts a sofa conformation. The carbazole ring system is planar [r.m.s. deviation = 0.063 (1) Å]. A C(10) zigzag chain running along the b axis is formed through inter­molecular C—H⋯O hydrogen bonds. The chains are linked via weak C—H⋯π and N—H⋯π inter­actions.
PMCID: PMC3006796  PMID: 21587821
12.  3-(2,4-Dichloro­phen­yl)-5-(4-fluoro­phen­yl)-2-methyl-7-(trifluoro­meth­yl)pyrazolo­[1,5-a]pyrimidine 
In the title compound, C20H11Cl2F4N3, the central pyrazolo­[1,5-a]pyrimidine unit is almost planar [the mean deviation from the best least-square plane through the nine atoms is 0.006 (2) Å]. The fluoro­benzene ring is rotated out of this plane by 10.3 (3)°, whereas the dichloro­benzene ring is rotated by 46.2 (3)°. The crystal packing is dominated by Cl⋯Cl inter­actions of 3.475 (3) Å and van der Waals inter­actions.
PMCID: PMC3344620  PMID: 22590382
13.  5-Hy­droxy-3-phenyl-5-trifluoro­meth­yl-4,5-dihydro-1H-pyrazole 
The five-membered dihydro­pyrazole ring in the title compound, C10H9F3N2O, is approximately planar (r.m.s. deviation 0.111 Å for all non-H atoms) and its phenyl substituent is aligned at an angle of 14.7 (2)°. Adjacent mol­ecules are linked by N—H⋯O and O—H⋯N hydrogen bonds, generating ribbons running along the b axis of the monoclinic unit cell.
PMCID: PMC3200976  PMID: 22065118
14.  (6bS*,14R*,14aR*)-Methyl 14-(4-methyl­phen­yl)-7-oxo-6b,6c,7,12b,14,14a-hexa­hydro-1H-pyrano[3,2-c:5,4-c′]dichromene-14a-carboxyl­ate 
In the title compound, C28H22O6, the chromeno ring system is almost planar, with a dihedral angle between the mean planes of the pyran and benzene rings of 1.87 (8)°. The pyran ring bearing the methyl­phenyl substituent has a half-chair conformation while the other pyran ring has an envelope conformation with the tetra­substituted C atom as the flap. The benzene ring of the chromeno ring system is inclined to the benzene ring fused to the latter pyran ring by 74.66 (9)°. These aromatic rings are inclined to the 4-methyl­phenyl ring by 52.67 (9) and 66.63 (10)°, respectively. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane.
PMCID: PMC3569797  PMID: 23424543
15.  1-[4-Chloro-3-(trifluoro­meth­yl)phen­yl]-4-phenyl-1H-1,2,3-triazole 
In the title compound, C15H9ClF3N3, the phenyl and chloro-trifluoro­methyl benzene rings are twisted with respect to the planar triazole group, making dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the crystal, the mol­ecules pack in a head-to-tail arrangement along the a axis with closest inter-centroid distances between the triazole rings of 3.7372 (12) Å.
PMCID: PMC3515254  PMID: 23284474
16.  1-[2,6-Dichloro-4-(trifluoro­meth­yl)phen­yl]-5-iodo-4-trifluoro­methyl­sulfinyl-1H-pyrazole-3-carbonitrile 
In the title compound, C12H2Cl2F6IN3OS, the dihedral angle between the planes of the benzene and pyrazole rings is 77.8 (2)°. In the crystal, a short I⋯N contact of 2.897 (5) Å occurs.
PMCID: PMC2977169  PMID: 21583482
17.  3-Meth­oxy-2-[2-({[6-(trifluoro­meth­yl)pyridin-2-yl]­oxy}meth­yl)phen­yl]prop-2-enoic acid 
The title mol­ecule, C17H14F3NO4, consists of two nearly planar fragments, viz. the 2-benzyl­oxypyridine (r.m.s. deviation 0.016 Å) and (E)-3-meth­oxy­prop2-enoic (r.m.s. deviation 0.004 Å) units, which form a dihedral angle of 84.19 (7)°. In the crystal, pairs of O—H⋯O hydrogen bonds link mol­ecules into dimers that are further connected by C—H⋯O and C—H⋯F inter­actions into (001) layers. In addition, π–π stacking inter­actions are observed within a layer between the pyridine and benzene rings [centroid–centroid distance = 3.768 (2) Å]. The F atoms of the trifluoro­methyl group are disordered over two sets of sites in a 0.53 (4):0.47 (4) ratio.
PMCID: PMC3515258  PMID: 23284478
18.  Ethyl 1-(2,4-dichloro­benz­yl)-4-oxo-7-trifluoro­meth­yl-1,4-dihydro­quinoline-3-carboxyl­ate 
In the title compound, C20H14Cl2F3NO3, the trifluromethyl group is disordered over two sets of sites in a 0.784 (10):0.216 (10) ratio. The quinoline ring system is essentially planar with a maximum deviation of 0.058 (2) Å for the N atom and forms dihedral angles of 89.23 (11) and 8.13 (17)°, respectively with the mean planes of the benzene ring and the carboxyl­ate group. In the crystal, pairs of weak C—H⋯O and C—H⋯F hydrogen bonds link mol­ecules into centrosymmetric dimers. The crystal structure is further stabilized by weak π–π [centroid–centroid distance = 3.624 (2) Å] inter­actions.
PMCID: PMC3275192  PMID: 22347048
19.  (E)-1-Methyl-5-(3-methyl-4-chloro­phen­oxy)-3-trifluoro­meth­yl-1H-pyrazole-4-carbaldehyde O-acetyl­oxime 
In the title mol­ecule, C15H13ClF3N3O3, the pyrazole and benzene rings form a dihedral angle of 77.6 (3)°. In the crystal, mol­ecules related by translation along the a axis are linked into chains via C—H⋯O hydrogen bonds. The crystal packing is stabilized further by weak π–π [centroid–centroid distance = 3.734 (6) Å] and dipole–dipole inter­actions [C⋯O = 3.174 (2) Å].
PMCID: PMC3052068  PMID: 21522468
20.  (2E)-1-[2,3-Dichloro-6-methyl-5-(trifluoro­meth­yl)phen­yl]-2-(1-phenyl­ethyl­idene)hydrazine 
The title compound, C16H13Cl2F3N2, exists in an E conformation with respect to the C=N bond [1.2952 (11) Å] and the C—N—N=C torsion angle is 175.65 (8)°. The dihedral angle between the benzene rings is 42.09 (4)°. An intra­molecular C—H⋯F hydrogen bond generates an S(6) ring. In the crystal, the mol­ecules are linked into [101] chains by C—H⋯F hydrogen bonds.
PMCID: PMC3515280  PMID: 23284500
21.  1′-Methyl-4′-[4-(trifluoro­meth­yl)phen­yl]dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C31H22F3NO2, the pyrrolidine and cyclo­pentane rings within the dihydro­indene ring system are in envelope conformations, with the N atom and the spiro-C atom at the flap, respectively. An intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The mean plane through the pyrrolidine ring [r.m.s. deviation = 0.179 (2) Å] makes dihedral angles of 86.30 (13), 88.99 (10) and 79.69 (11)° with the benzene ring, the dihydro­acenaphthyl­ene ring and the mean plane of the indane system, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. C—H⋯π inter­actions further stabilize the crystal structure.
PMCID: PMC3344443  PMID: 22590205
22.  6-Amino-3-methyl-4-(3-nitro­phen­yl)-1-phenyl-1H,4H-pyrano[2,3-c]pyrazole-5-carbonitrile 
The title compound, C20H15N5O3, was synthesized by the one-pot reaction of a four-component reaction protocol in aqueous medium. The pyrano[2,3-c]pyrazole system is essentially planar, with a maximum deviation of 0.026 (2) Å. The 3-nitro­phenyl and phenyl rings make dihedral angles of 81.11 (5) and 13.36 (1)°, respectively, with the mean plane of the pyrano[2,3-c]pyrazole ring. The crystal structure is stabilized by N—H⋯N hydrogen bonds, which form infinite chain propagating along the c axis and by N—H⋯O hydrogen bonds, which form infinite chains propagating along the a axis. There are also N—O⋯N—C dipole–dipole inter­actions along the a axis with an O⋯N distance of 3.061 (3) Å, which is shorter than that of the N—H⋯O hydrogen bond [3.196 (3) Å].
PMCID: PMC3120331  PMID: 21754828
23.  N,N′-{[Bis(trifluoro­meth­yl)methyl­ene]di-p-phenyl­ene}diphthalimide 
The molecule of the title compound, C31H16F6N2O4, consists of two phthalimide units linked by a [bis­(trifluoro­meth­yl)methyl­ene]di-p-phenyl­ene bridge, with the two halves of the mol­ecule related to each other by a twofold rotation axis. The dihedral angle between the planes of the two central benzene rings is 70.5 (3)°. The terminal isoindole groups are approximately planar, with a maximum r.m.s. deviation of 0.006 Å from the mean plane, and they form dihedral angles of 46.03 (3)° to the attached benzene rings. Inter­molecular C—H⋯O hydrogen bonds link neighboring mol­ecules into chains along the c axis.
PMCID: PMC2960178  PMID: 21201418
24.  1-(Pyridin-2-yl)-2-[2-(trifluoro­meth­yl)benz­yl]-3-[2-(trifluoro­meth­yl)phen­yl]propan-1-one 
The title compound, C23H17F6NO, crystallizes with two mol­ecules in the asymmetric unit. The mol­ecules assume an approximate propellar shape, with the three aromatic rings being bent with respect to the plane formed by the C atoms that are connected to the methine C atom [dihedral angles: pyridyl 67.49 (3)°, phenyl 56.82 (4)° and phenyl 77.21 (6)° in one mol­ecule, and corresponding angles of 71.60 (6), 53.68 (4) and 77.53 (6)° in the second mol­ecule].
PMCID: PMC3297303  PMID: 22412493
25.  4-Methyl-9-[(4-methyl­phen­yl)sulfon­yl]thio­pyrano[3,4-b]indole-3(9H)-thione 
The title compound, C19H15NO2S3, is the first example of a dithia analogue of pyrano[3,4-b]indolone. The almost planar thio­pyrano­indole­thione ring system (r.m.s. deviation for all non-H atoms = 0.030 Å) makes a dihedral angle of 80.70 (8)° with the p-tolyl ring. In the crystal, mol­ecules are connected via C—H⋯O hydrogen bonds into two chains along the b axis. These chains are connected via π–π inter­actions between symmetry-related thio­pyrano­indole­thione ring systems [centroid–centroid distance = 3.588 (1) Å].
PMCID: PMC2983115  PMID: 21587636

Results 1-25 (75336)