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1.  1-[3,5-Bis(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the asymmetric unit of the title compound, C17H14F2N2O, there are three independent mol­ecules (A, B and C) which differ slightly in the relative orientations of the two fluoro­phenyl rings. In mol­ecules A and C one of the fluoro­phenyl rings is disordered over two positions, with occupancy ratios of 0.72 (2):0.28 (2) for mol­ecule A and 0.67 (2):0.33 (2) for mol­ecule C. The dihedral angle between the two fluoro­phenyl rings in the independent mol­ecules lie in the range 70.3 (3)–84.0 (3)°. In the crystal structure, the mol­ecules are linked via inter­molecular C—H⋯O and C—H⋯F hydrogen bonds and π⋯π stacking inter­actions [centroid–centroid distance = 3.7508 (13) Å], forming a three-dimensional network.
doi:10.1107/S1600536810004435
PMCID: PMC2983722  PMID: 21580348
2.  4,6-Bis(4-fluoro­phen­yl)-2-phenyl-1H-indazol-3(2H)-one 
In the title compound, C25H16F2N2O, the pyrazole ring is almost planar (r.m.s. deviation = 0.028 Å) and makes a dihedral angle of 5.86 (11)° with the indazole benzene ring. The dihedral angle between the pyrazole ring and the unsubstituted phenyl ring is 28.19 (11)°. The dihedral angles between the unsubstituted phenyl and the two fluoro­phenyl groups are 57.69 (10) and 18.01 (10)°. In the crystal, mol­ecules are linked by inter­molecular N—H⋯O and C—H⋯F inter­actions, forming infinite chains along the b axis with graph-set motif R 3 2(19). The crystal structure is further consolidated by π–π stacking [centroid–centroid distances = 3.5916 (13) and 3.6890 (13) Å] and C—H⋯π inter­actions.
doi:10.1107/S1600536811016369
PMCID: PMC3120412  PMID: 21754741
3.  5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-N-phenyl-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C26H23FN6S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The thio­urea group is close to being coplanar with the pyrazole N atoms [N—N—C—S torsion angle = 176.78 (15)°], which allows for an intra­molecular N—H⋯N hydrogen bond; the connected triazole ring is nearly coplanar with this ring [N—C—C—N = −172.65 (19)°]. There is a significant twist between the pyrazole ring and attached fluoro­benzene ring [N—C—C—C = −18.8 (3)°] and a greater twist between triazole and attached tolyl ring [dihedral angle = 58.25 (14)°]. In the crystal, supra­molecular chains aligned along [40,10] are consolidated by π–π inter­actions between the triazole and phenyl rings [centroid–centroid distance = 3.7053 (13) Å].
doi:10.1107/S1600536813008155
PMCID: PMC3629654  PMID: 23634141
4.  4-{2-[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]thia­zol-4-yl}benzonitrile 
The asymmetric unit of the title compound, C25H14ClFN4S, contains two independent mol­ecules (A and B). Each mol­ecule consists of five rings, namely chloro­phenyl, fluoro­phenyl, 1H-pyrazole, thia­zole and benzonitrile. In mol­ecule A, the 1H-pyrazole ring makes dihedral angles of 52.54 (8), 35.96 (8) and 15.43 (8)° with respect to the attached chloro­phenyl, fluoro­phenyl and thia­zole rings. The corresponding values in mol­ecule B are 51.65 (8), 37.26 (8) and 8.32 (8)°. In the crystal, mol­ecules are linked into dimers by C—H⋯N hydrogen bonds, generating R 2 2(10) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the ab plane via inter­molecular weak C—H⋯N and C—H⋯F hydrogen bonds. The crystal structure is further stabilized by weak π-π inter­actions [with centroid–centroid distances of 3.4303 (9) and 3.6826 (9) Å] and weak C—H⋯π inter­actions.
doi:10.1107/S1600536810031405
PMCID: PMC3007991  PMID: 21588640
5.  2-(2-Fluoro­phen­yl)-5-iodo-7-methyl-3-methyl­sulfinyl-1-benzo­furan 
In the title compound, C16H12FIO2S, the dihedral angle between the plane of the benzo­furan ring system (r.m.s. deviation = 0.023 Å) and that of the 2-fluoro­phenyl ring is 39.78 (7)°. In the crystal, mol­ecules are linked via pairs of I⋯π contacts [3.812 (2) Å] and a π–π inter­action between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.821 (2) Å] into inversion dimers. These dimers are further linked by π–π inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.668 (2) Å]. The mol­ecules stack along the a-axis direction. In addition, C—H⋯O hydrogen bonds are observed between inversion-related dimers.
doi:10.1107/S1600536814010459
PMCID: PMC4051089  PMID: 24940242
6.  5-Benzoyl-4-(4-fluoro­phen­yl)-3,4-dihydro­pyrimidin-2(1H)-one 
In the title mol­ecule, C17H13FN2O2, the 3,4-dihydro­pyrimidine ring adopts a flattened sofa conformation with the flap atom (which bears the fluoro­phenyl substituent) deviating from the plane defined by the remaining five ring atoms by 0.281 (2) Å. This plane forms dihedral angles of 85.98 (6) and 60.63 (6)° with the 4-fluoro­phenyl and benzoyl-phenyl rings, respectively. The dihedral angle between the 4-fluoro­phenyl group and the benzene ring is 71.78 (6)°. In the crystal, N—H⋯O hydrogen bonds link mol­ecules into inversion dimers that are further connected by another N—H⋯O inter­action into a two-dimensional supra­molecular structure parallel to (101).
doi:10.1107/S1600536812052105
PMCID: PMC3569257  PMID: 23424480
7.  2-[3,5-Bis­(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]-4,6-bis(4-fluoro­phenyl)pyrimidine 
In the title compound, C31H20F4N4, the pyrazole ring adopts an envelope conformation and forms a dihedral angle of 9.91 (6)° with the adjacent pyrimidine ring. The pyrimidine ring forms dihedral angles of 9.23 (6) and 2.16 (5)° with its adjacent fluoro-substituted benzene rings, whereas these angles are 88.22 (6) and 9.66 (6)° for the pyrazole ring and its adjacent benzene rings. In the crystal, mol­ecules are linked by C—H⋯F hydrogen bonds into ribbons along [01-1]. The crystal packing is further stabilized by C—H⋯π and by π–π inter­actions, with centroid–centroid distances of 3.7428 (7) and 3.7630 (6) Å.
doi:10.1107/S1600536812006976
PMCID: PMC3297871  PMID: 22412674
8.  1-{4-Chloro-2-[2-(2-fluoro­phen­yl)-1,3-dithio­lan-2-yl]phen­yl}-2-methyl-1H-imidazole-5-carbaldehyde 
There are two mol­ecules in the asymmetric unit of the title imidazole derivative, C20H16ClFN2OS2. In one mol­ecule, the dithiol­ane ring is disordered over two positions in a 0.849 (9):0.151 (10) ratio. The imidazole ring makes dihedral angles of 79.56 (9) and 18.45 (9)° with the 4-chloro­phenyl and 2-fluoro­phenyl rings, respectively, in one mol­ecule; in the other mol­ecule, the corresponding angles are 82.72 (9) and 17.39 (10)°. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions and these linked mol­ecules are stacked along the b axis by π–π inter­actions with a centroid–centroid distance of 3.4922 (11) Å. In addition, π–π inter­actions between the imidazole and 2-fluoro­phenyl rings are also observed, with centroid–centroid distances of 3.4867 (11) and 3.4326 (10) Å. The crystal is further consolidated by weak C—H⋯π inter­actions. Cl⋯S [3.5185 (8) Å], C⋯O [3.192 (3) Å] and C⋯C [3.326 (2)–3.393 (3) Å] short contacts are also observed.
doi:10.1107/S1600536811002595
PMCID: PMC3051534  PMID: 21523151
9.  3-Ethyl­sulfinyl-2-(4-fluoro­phen­yl)-5-iodo-1-benzofuran 
In the title compound, C16H12FIO2S, the 4-fluoro­phenyl ring is rotated slightly out of the benzofuran plane, as indicated by the dihedral angle of 4.48 (5)°. In the crystal structure, pairs of I⋯O halogen bonds [I⋯O = 3.123 (1) Å] link the mol­ecules into centrosymmetric dimers. These dimers are further linked via aromatic π–π inter­actions between the benzene and 4-fluoro­phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.620 (3) Å].
doi:10.1107/S1600536810012717
PMCID: PMC2979084  PMID: 21579104
10.  2-(4-Fluoro­phen­yl)-5-iodo-7-methyl-3-methyl­sulfinyl-1-benzofuran 
In the title compound, C16H12FIO2S, the O atom and the methyl group of the methyl­sulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-fluoro­phenyl ring is rotated slightly out of the benzofuran plane, as indicated by the dihedral angle of 7.43 (6)°. In the crystal structure, pairs of short I⋯O [3.074 (2) Å] contacts link the mol­ecules into centrosymmetric dimers. These dimers are further linked via aromatic π–π inter­actions between the benzene and the 4-fluoro­phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.617 (3) Å].
doi:10.1107/S1600536810022397
PMCID: PMC3006691  PMID: 21587905
11.  3-Ethyl­sulfinyl-2-(3-fluoro­phen­yl)-5-phenyl-1-benzo­furan 
In the title compound, C22H17FO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzo­furan ring system and the pendant 3-fluoro­phenyl and phenyl rings are 23.92 (5) and 32.44 (5)°, respectively. In the crystal, mol­ecules are linked by two weak C—H⋯O(sulfin­yl) hydrogen bonds and a C—H⋯π inter­action, forming a sheet, which lies in the ab plane. A π–π inter­action between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.976 (2) Å] links the mol­ecules into inversion dimers and connects adjacent sheets, resulting in a three-dimensional network.
doi:10.1107/S1600536813015924
PMCID: PMC3770370  PMID: 24046655
12.  1-[3-(2,4-Dichloro-5-fluoro­phen­yl)-5-(3-methyl-2-thien­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title mol­ecule, C16H13Cl2FN2OS, the dihedral angle between the thio­phene and benzene rings is 80.34 (12)°. The pyrazoline ring is in an envelope conformation, and the plane through the four coplanar atoms makes dihedral angles of 85.13 (9) and 6.89 (10)° with the thio­phene and benzene rings, respectively. The C and O atoms of the acetyl group are nearly coplanar with the attached pyrazoline ring. In the crystal structure, inversion dimers arise from pairs of inter­molecular C—H⋯O hydrogen bonds. A short inter­molecular Cl⋯S contact of 3.4250 (13) Å is also found.
doi:10.1107/S1600536808033837
PMCID: PMC2959565  PMID: 21581020
13.  5-Cyclo­pentyl-2-(4-fluoro­phen­yl)-3-isopropyl­sulfonyl-1-benzofuran 
In the title compound, C22H23FO3S, the cyclo­pentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The 4-fluoro­phenyl ring makes a dihedral angle of 43.67 (3)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯π inter­actions, forming a three--dimensional network. The crystal structure also exhibits slipped π–π inter­actions between the benzene and furan rings of neighbouring mol­ecules [centroid–centroid distance = 3.883 (2) Å and slippage = 1.731 (2) Å].
doi:10.1107/S1600536812045916
PMCID: PMC3588938  PMID: 23476174
14.  1-(4-Chloro­phenyl­sulfon­yl)-5-(4-fluoro­phen­yl)-5-methyl­imidazolidine-2,4-dione 
The title compound, C16H12ClFN2O4S, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. The two mol­ecules are U-shaped with similar geometries and conformations. The mean planes through the benzene rings are inclined to one another by 6.07 (8)° in mol­ecule A and 8.67 (8)° in mol­ecule B. They are separated with a centroid–centroid distance of 3.9096 (10) Å in mol­ecule A and 3.9118 (10) Å in mol­ecule B. Mol­ecules A and B lie adjacent to one another, with a centroid–centroid distance of 3.7592 (10) Å between the fluoro­phenyl ring of mol­ecule A and the chloro­phenyl­sulfonyl ring of mol­ecule B and with a dihedral angle of 5.75 (8)° between the ring planes. In the crystal structure, A and B mol­ecules are linked by N—H⋯O hydrogen bonds, forming centrosymmetric dimers. These dimers stack along the [110] direction and are linked by C—H⋯O and C—H⋯F inter­actions. There are also some short halide⋯halide contacts [Cl⋯F = 3.0499 (14) and 3.1224 (13) Å, and F⋯F = 3.0612 (17) Å].
doi:10.1107/S160053680901037X
PMCID: PMC2968985  PMID: 21582575
15.  5-(3,5-Di­fluoro­phen­yl)-1-(4-fluoro­phen­yl)-3-tri­fluoro­methyl-1H-pyrazole 
In the title compound, C16H8F6N2, the dihedral angle between the pyrazole and di­fluoro­benzene rings is 50.30 (13)°, while those between the pyrazole and fluoro­benzene rings and between the di­fluoro­benzene and fluoro­benzene rings are 38.56 (13) and 53.50 (11)°, respectively. Aromatic π–π stacking inter­actions between adjacent di­fluoro­benzene rings [centroid–centroid separation = 3.6082 (11) Å] link the mol­ecules into dimers parallel to [21-2].
doi:10.1107/S1600536813032650
PMCID: PMC3914069  PMID: 24526970
16.  3-[(4-Fluoro­phen­yl)sulfon­yl]-5-iodo-2-methyl-1-benzofuran 
In the title compound, C15H10FIO3S, the 4-fluoro­phenyl ring makes a dihedral angle of 72.27 (6)° with the mean plane of the benzofuran fragment [mean deviation of 0.014 (2) Å from the plane defined by the nine constituent atoms]. In the crystal, pairs of weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into centrosymmetric dimers, which are further linked via an aromatic π–π inter­actions between the iodo­benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.569 (3) Å].
doi:10.1107/S1600536810034069
PMCID: PMC3007891  PMID: 21588749
17.  1-(4-Fluoro­phen­yl)-3-methyl-4-phenyl­sulfanyl-1H-pyrazol-5(4H)-one 
The title compound, C16H13FN2OS, has undergone enol-to-keto tautomerism during the crystallization process. The 1H-pyrazole-5-one ring [maximum deviation = 0.0198 (11) Å] is inclined at angles of 33.10 (5) and 79.57 (5)° with respect to the fluoro­phenyl [maximum deviation = 0.0090 (12) Å] and phenyl­thiol [maximum deviation = 0.0229 (3) Å] rings attached to it. In the crystal, neighbouring mol­ecules are linked into inversion dimers, generating R 2 2(8) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the bc plane via inter­molecular N—H⋯O, C—H⋯F and C—H⋯O hydrogen bonds. The crystal is further stabilized by weak π–π [centroid–centroid distance = 3.6921 (7) Å] and C—H⋯π inter­actions.
doi:10.1107/S1600536810040596
PMCID: PMC3009262  PMID: 21589006
18.  2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C25H20FN3S, two independent mol­ecules comprise the asymmetric unit, which differ in the relative orientation of the fluoro­benzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two mol­ecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the mol­ecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thia­zole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each mol­ecule has a T-shape. In the crystal, mol­ecules are connected into a three-dimensional architecture by weak C—H⋯π inter­actions.
doi:10.1107/S1600536813004339
PMCID: PMC3588500  PMID: 23476577
19.  6-(4-Fluoro­phen­yl)-3-phenyl-7H-1,2,4-tri­azolo[3,4-b][1,3,4]thia­diazine 
In the title compound, C16H11FN4S, the dihedral angles between the triazole ring and the phenyl and fluoro­benzene rings are 23.22 (17) and 18.06 (17)°, respectively. The six-membered heterocyclic ring adopts a distorted envelope conformation, with the methyl­ene C atom as the flap. In the crystal, the mol­ecules are linked by two C—H⋯N and C—H⋯F inter­actions along [010], forming C(5), C(8) and C(13) chains repectively. C—H⋯π inter­actions involving the phenyl ring and π–π inter­actions [centroid–centroid separation for triazole rings = 3.5660 (18) Å] are also observed.
doi:10.1107/S1600536814003262
PMCID: PMC3998453  PMID: 24765056
20.  5-Bromo-2-(4-fluoro­phen­yl)-3-phenyl­sulfinyl-1-benzofuran 
In the title compound, C20H12BrFO2S, the 4-fluoro­phenyl ring makes a dihedral angle of 2.63 (6)° with the mean plane of the benzofuran fragment. The dihedral angle between the phenyl ring and the mean plane of the benzofuran fragment is 84.60 (6)°. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds, and slipped π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.719 (3) Å, inter­planar distance = 3.000 (3) Å and slippage = 1.520 (3) Å].
doi:10.1107/S1600536811032387
PMCID: PMC3200819  PMID: 22064889
21.  3-(4-Fluoro­phen­yl)-6-meth­oxy-2-(4-pyrid­yl)quinoxaline 
In the title compound, C20H14FN3O, the quinoxaline system makes dihedral angles of 32.38 (7) and 48.04 (7)° with the 4-fluoro­phenyl and pyridine rings, respectively. The 4-fluoro­phenyl ring makes a dihedral angle of 57.77 (9)° with the pyridine ring. In the crystal, the mol­ecules form dimeric C—H⋯N hydrogen-bonded R 2 2(20) ring motifs lying about crystallographic inversion centers. The dimeric units stack via π–π inter­actions between methoxy­phenyl rings and pyridine–fluoro­phenyl rings with centroid–centroid distances of 3.720 (1) and 3.823 (1) Å, respectively. The respective average perpendicular distances are 3.421 and 3.378 Å, with dihedral angles between the rings of 1.31 (9) and 11.64 (9)°.
doi:10.1107/S1600536809022119
PMCID: PMC2969274  PMID: 21582893
22.  2-(4-Fluoro­phen­yl)-5-iodo-3-phenyl­sulfinyl-1-benzofuran 
In the title compound, C20H12FIO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.014 (1) Å] of the benzofuran fragment and the pendant 4-fluoro­phenyl and phenyl rings are 8.0 (1) and 86.06 (6)°, respectively. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds. The crystal structure also exhibits weak π–π inter­actions between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.547 (2) Å, inter­planar distance = 3.397 (2) Å and slippage = 1.021 (2) Å].
doi:10.1107/S1600536812013086
PMCID: PMC3344167  PMID: 22606170
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.  (E)-1-(2,4-Dinitro­phen­yl)-2-[1-(3-fluoro­phen­yl)ethyl­idene]hydrazine 
The mol­ecule of the title hydrazone derivative, C14H11FN4O4, is nearly planar, with a dihedral angle between the benzene rings of 3.71 (7)°. The central ethyl­idenehydrazine N—N=C—C plane makes dihedral angles of 5.32 (10) and 9.02 (10)° with the 2,4-dinitro- and 3-fluoro-substituted benzene rings, respectively. An intra­molecular N—H⋯O bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions into a sheet parallel to (10-1). The mol­ecules are further stacked along the a axis by π–π inter­actions with centroid–centroid distances of 3.6314 (9) and 3.7567 (10) Å. A C⋯F short contact [2.842 (3) Å] is observed. The 3-fluoro­phenyl group is disordered over two orientations with a site-occupancy ratio of 0.636 (3):0.364 (3).
doi:10.1107/S160053681201937X
PMCID: PMC3379246  PMID: 22719444
25.  2-(3-Fluoro­phen­yl)-3-methyl­sulfanyl-5-phenyl-1-benzofuran 
In the title compound, C21H15FOS, the dihedral angles between the mean plane of the benzofuran fragment and the pendant 3-fluoro­phenyl and phenyl rings are 1.76 (5) and 32.29 (5)°, respectively. In the crystal, mol­ecules are linked by a slipped π–π inter­action between the furan and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.665 (2) Å, inter­planar distance = 3.391 (2) Å and slippage = 1.390 (2) Å].
doi:10.1107/S1600536811042541
PMCID: PMC3247405  PMID: 22220023

Results 1-25 (271985)