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1.  2-(4-Fluoro­phen­yl)-1-(4-meth­oxy­phen­yl)-1H-phenanthro[9,10-d]imidazole 
In the title compound, C28H19FN2O, the phenanthrene fused with an imidazole ring, constituting an essentially planar tetra­cyclic system [maximum deviation = 0.032 (2) Å], makes dihedral angles of 60.83 (4) and 80.55 (4)° with the fluoro­benzene and meth­oxy­benzene rings, respectively. The dihedral angle between the the meth­oxy­benzene and fluoro­benzene rings is 69.45 (6)°. In the crystal, C—H⋯O hydrogen bonds connect the mol­ecules into infinite strands along the b axis. The crystal structure is further consolidated by C—H⋯π inter­actions.
doi:10.1107/S1600536813003504
PMCID: PMC3588432  PMID: 23476557
2.  (E)-1-{4-[Bis(4-fluoro­phen­yl)meth­yl]piperazin-1-yl}-3-(4-eth­oxy­phen­yl)prop-2-en-1-one 
In the title mol­ecule, C28H28F2N2O2, the ethene bond exhibits an E conformation and the piperazine ring adopts a chair conformation. The amide-N atom of the piperazine ring is almost planar (bond-angle sum = 358.8°) whereas the other N atom is clearly pyramidal (bond-angle sum = 330.5°). The dihedral angle between the fluoro­benzene rings is 76.36 (17)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(22) loops.
doi:10.1107/S160053681104801X
PMCID: PMC3238988  PMID: 22199837
3.  Ethyl 2-[5-(4-chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]-4-methyl­thia­zole-5-carboxyl­ate 
In the title compound, C22H17ClFN3O2S, the pyrazole ring is approximately planar with a maximum deviation of 0.001 (4) Å and makes dihedral angles of 4.95 (19), 35.78 (18) and 54.73 (18)° with the thia­zole, fluoro­benzene and chloro­benzene rings, respectively. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains along the a axis.
doi:10.1107/S1600536810042066
PMCID: PMC3009042  PMID: 21589099
4.  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
5.  {2-[(1,3-Benzo­thia­zol-2-yl)meth­oxy]-5-fluoro­phen­yl}(4-chloro­phen­yl)methanone 
The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent mol­ecules with similar conformations. In the mol­ecules, the thia­zole ring is essentially planar [maximum atomic deviations = 0.014 (4) and 0.023 (5) Å] and is oriented with respect to the fluoro­phenyl ring and chloro­phenyl rings at 9.96 (18) and 70.39 (18)° in one mol­ecule and at 7.50 (18) and 68.43 (18)° in the other; the dihedral angles between the fluoro­phenyl and chloro­phenyl rings are 64.9 (2) and 64.6 (2)°, respectively. Inter­molecular C—H⋯O and C—H⋯F hydrogen bonds stabilize the three-dimensional supra­molecular architecture. Weak C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.877 (3) Å] lead to a criss-cross mol­ecular packing along the c axis.
doi:10.1107/S1600536813014621
PMCID: PMC3772451  PMID: 24046594
6.  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
7.  3,5-Bis(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde 
In the title mol­ecule, C16H12F2N2O, the pyrazole ring adopts a slight envelope conformation with the methyl­ene C atom deviating by 0.114 (3) Å from the mean plane of the other four atoms [maximum deviation = 0.021 (3) Å]. The dihedral angles between the four essentially planar atoms of the pyrazole ring and the fluoro-substituted benzene rings are 2.6 (2) and 82.2 (2)°. The dihedral angle between the two benzene rings is 83.7 (2)°. The crystal packing is stabilized by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S160053681101587X
PMCID: PMC3120319  PMID: 21754699
8.  5-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)-1-phenyl-4,5-dihydro-1H-pyrazole 
In the title compound, C21H16BrFN2, the fluoro-substituted benzene ring is disordered over two orientations about the C—F bond and the C—C bond between the benzene and pyrazole groups with a site-occupancy ratio of 0.516 (8):0.484 (8). The central pyrazole ring [maximum deviation = 0.035 (3) Å] makes dihedral angles of 22.4 (2), 11.0 (2), 77.19 (16) and 7.44 (17)° with the two disorder components of the benzene ring, the bromo-substituted benzene ring and the phenyl ring, respectively. In the crystal, mol­ecules are linked into a layer parallel to the bc plane through C—H⋯π inter­actions.
doi:10.1107/S160053681203454X
PMCID: PMC3435702  PMID: 22969573
9.  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
10.  4-{[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl}-N-(4-cyano­phen­yl)piperazine-1-carboxamide 
In the title compound, C28H22ClFN6O2, the piperazine ring adopts a chair conformation and the least-squares plane through the four coplanar atoms forms dihedral angles of 69.37 (13) and 56.56 (12)°, respectively, with the pyrazole and cyano­phenyl rings. The dihedral angles formed between the pyrazole and the attached fluoro- and chloro­phenyl rings are 34.16 (10) and 73.27 (12)°, respectively. In the crystal, inter­molecular N—H⋯O, C—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into sheets parallel to the ac plane.
doi:10.1107/S1600536810036159
PMCID: PMC2983346  PMID: 21587549
11.  (E)-3-(2-Eth­oxy­phen­yl)-1-{4-[(2-fluoro­phen­yl)(4-fluoro­phen­yl)meth­yl]piperazin-1-yl}prop-2-en-1-one 
In the title compound, C28H28F2N2O2, the piperazine ring has a chair conformation with the pendant N—C bonds in equatorial orientations. The C=C double bond has an E conformation and the dihedral angle between the fluoro­benzene rings is 70.8 (3)°. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯F hydrogen bonds.
doi:10.1107/S1600536812024130
PMCID: PMC3379522  PMID: 22719720
12.  Two tautomers in the same crystal: 3-(4-fluoro­phen­yl)-1H-pyrazole and 5-(4-fluoro­phen­yl)-1H-pyrazole 
The title co-crystal, 3-(4-fluoro­phen­yl)-1H-pyrazole–5-(4-fluoro­phen­yl)-1H-pyrazole (1/1), C9H7FN2, crystallizes with four independent mol­ecules (A, B, C and D) in the asymmetric unit exhibiting two tautomeric forms (A and D; B and C) due to N—H proton exchange between the two N atoms of the pyrazole ring. The dihedral angles between the mean planes of the pyrazole and benzene rings are 15.6 (1), 19.8 (9), 14.0 (1) and 10.7 (7)° in mol­ecules A, B, C and D, respectively. In the crystal, N—H⋯N hydrogen bonds link the four mol­ecules in the asymmetric unit into a ring with an R 4 4(12) motif. Furthermore, weak C—H⋯F inter­actions link the mol­ecules into a three-dimensional network.
doi:10.1107/S160053681401695X
PMCID: PMC4186127  PMID: 25309273
crystal structure; pyrazole derivative; tautomeric forms; hydrogen bonds
13.  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
14.  2-(4-Fluoro­phen­yl)-1-phenyl-1H-benzimidazole 
In the title mol­ecule, C19H13FN2, the benzimidazole unit is close to planar [maximum deviation = 0.0342 (9) Å] and forms dihedral angles of 58.94 (3) and 51.43 (3)° with the phenyl and fluoro­benzene rings, respectively; the dihedral angle between the phenyl and fluoro­benzene rings is 60.17 (6)°. In the crystal, three C—H⋯F hydrogen bonds and two weak C—H⋯π inter­actions involving the fused benzene ring lead to a three-dimensional architecture.
doi:10.1107/S1600536812035155
PMCID: PMC3435725  PMID: 22969596
15.  (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
16.  5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
The central pyrazole ring in the title compound, C17H16FN3S, adopts an envelope conformation with the methine C atom bearing the 4-fluoro­phenyl substituent as the flap atom. Whereas the tolyl ring is slightly twisted out of the least-squares plane through the pyrazole ring [dihedral angle = 13.51 (11)°], the fluoro­benzene ring is almost perpendicular [dihedral angle = 80.21 (11)°]. The thio­amide group is almost coplanar with the N—N bond of the ring [N—N—C—N torsion angle = 1.2 (3)°] and the amine group forms an intra­molecular hydrogen bond with a ring N atom. In the crystal, supra­molecular double layers in the bc plane are formed via N—H⋯S, N—H⋯F and C—H⋯F inter­actions.
doi:10.1107/S1600536813004194
PMCID: PMC3588501  PMID: 23476571
17.  (2E)-1-(4,4′′-Difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-(2-fluoro­phen­yl)prop-2-en-1-one 
In the title compound, C28H19F3O2, the central benzene ring forms dihedral angles of 48.69 (6), 60.93 (6) and 42.06 (6)° with the fluoro­benzene rings. In the crystal, inter­molecular C—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules, forming an undulating two-dimensional network parallel to the bc plane. C—H⋯π inter­actions further consolidate the crystal packing.
doi:10.1107/S1600536812024981
PMCID: PMC3393293  PMID: 22807850
18.  2-(4-Fluoro­phen­yl)-3-isopropyl­sulfinyl-5,6-methyl­enedi­oxy-1-benzofuran 
In the title compound, C18H15FO4S, the fluoro­benzene ring makes a dihedral angle of 4.3 (1)° with the mean plane of the benzofuran fragment. In the crystal, mol­ecules are linked by weak inter­molecular C—H⋯O hydrogen bonds. The O atom of the sulfinyl group is disordered over two orientations, with site-occupancy factors of 0.940 (3) and 0.060 (3).
doi:10.1107/S1600536811051178
PMCID: PMC3239126  PMID: 22199974
19.  2-(4-Fluoro­phen­yl)-4,5-dimethyl-1-(4-methyl­phen­yl)-1H-imidazole 
In the title mol­ecule, C18H17FN2, the imidazole ring is essentially planar [maximum deviation of 0.005 (1) Å and makes dihedral angles of 72.33 (8) and 18.71 (8)° with the methyl­phenyl and fluoro­phenyl rings, respectively. The dihedral angle between the two benzene rings is 75.05 (7)°. The crystal packing is stabilized by inter­molecular C—H⋯N hydrogen bonds.
doi:10.1107/S1600536810022841
PMCID: PMC3006898  PMID: 21587923
20.  N-(2-Fluoro­phen­yl)cinnamamide 
The title compound, C15H12FNO, was prepared by the reaction of cinnamoyl chloride with 4-fluoro­aniline and crystallizes with two mol­ecules A and B in the asymmetric unit. The two unique mol­ecules are closely similar and overlay with an r.m.s. deviation of 0.0819 Å. The fluoro­benzene and phenyl rings are inclined to one another at 73.89 (7) and 79.46 (7)°, respectively, in mol­ecules A and B. The amide C—N—C(O)—C portions of the mol­ecules are planar (r.m.s. deviations = 0.035 and 0.028 Å) and are inclined at 45.51 (9) and 47.71 (9), respectively, to the fluoro­benzene rings in mol­ecules A and B. The 2-fluoro­acetamide units and the benzene rings each adopt E configurations with respect to the C=C bonds. In the crystal structure, inter­molecular N—H⋯O hydrogen bonds augmented by weak C—H⋯π inter­actions link mol­ecules into rows in a head-to-tail fashion along a. Additional weak C—H⋯O contacts further stabilize the packing, forming a three-dimensional network stacked down a.
doi:10.1107/S1600536810003867
PMCID: PMC2983731  PMID: 21580305
21.  2-Amino-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carbonitrile 
In the title mol­ecule, C21H15FN2O2, the dihedral angle between the fluoro-substituted benzene ring and the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.109 (2) Å] is 83.35 (7)°. The pyran ring adopts a slight sofa conformation with the tertiary C(H) atom forming the flap. The meth­oxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −4.3 (3)°]. In the crystal, mol­ecules are linked by inter­molecular N—H⋯N hydrogen bonds into infinite wave-like chains along the b axis. The crystal packing is further stabilized by π–π inter­actions [centroid–centroid distance = 3.7713 (9) Å].
doi:10.1107/S1600536812023021
PMCID: PMC3379488  PMID: 22719686
22.  (1RS,6SR)-Ethyl 4-(4-chloro­phen­yl)-6-(4-fluoro­phen­yl)-2-oxocyclo­hex-3-ene-1-carboxyl­ate toluene hemisolvate 
In the crystal structure of the title compound, C21H18ClFO3·0.5C7H8, the toluene solvent mol­ecules occupy special positions on centres of symmetry, and consequently are disordered across this site. The cyclo­hexene ring has a slightly distorted sofa conformation; the two benzene rings are inclined by 72.90 (7)° and their planes make dihedral angles of 30.09 (10) (chloro­phen­yl) and 88.13 (6)° (fluoro­phen­yl) with the approximately planar part of the cyclo­hexenone ring [maximum deviation from plane through five atoms is 0.030 (2) Å, the sixth atom is 0.672 (3)Å out of this plane]. Weak inter­molecular C—H⋯O and C—H⋯X (X = F, Cl) inter­actions join mol­ecules into a three-dimensional structure. Also, a relatively short and directional C—Cl⋯F—C contact is observed [Cl⋯F = 3.119 (2) Å, C—Cl⋯F = 157.5 (2)° and C—F⋯Cl 108.3 (2)°]. The solvent mol­ecules fill the voids in the crystal structure and are kept there by relatively short and directional C—H⋯π inter­actions.
doi:10.1107/S1600536811000158
PMCID: PMC3051615  PMID: 21523018
23.  1-{[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl]}piperidin-4-one 
In the title compound, C21H17ClFN3O2, the 1H-pyrazole ring makes dihedral angles of 36.73 (7), 18.73 (7) and 60.88 (8)°, respectively, with the mean planes of the chloro­phenyl, 4-oxo­piperidine and fluoro­phenyl rings. The mol­ecular structure is stabilized by an intra­molecular C—H⋯N hydrogen bond, which forms an S(6) ring motif. In the crystal, inter­molecular C—H⋯O hydrogen bonds link mol­ecules into chains along [101]. In addition, inter­molecular C—H⋯F hydrogen bonds with an R 2 1(7) ring motif connect neighbouring chains into layers parallel to the ac plane.
doi:10.1107/S1600536810047215
PMCID: PMC3011612  PMID: 21589523
24.  4-{[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl}-N-ethyl­piperazine-1-carboxamide 
The asymmetric unit of the title compound, C23H23ClFN5O2, contains two crystallographically independent mol­ecules. In one mol­ecule, the pyrazole ring makes dihedral angles of 43.93 (7) and 35.82 (7)°, respectively, with the fluoro- and chloro-substituted benzene rings, while the corresponding angles in the other mol­ecule are 52.26 (8) and 36.85 (7)°. The piperazine rings adopt chair conformations. In the crystal, adjacent mol­ecules are connected via inter­molecular N—H⋯O, C—H⋯F, C—H⋯N and C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. The crystal structure is further stabilized by a weak π–π inter­action with a centroid–centroid distance of 3.6610 (8) Å and by C—H⋯π inter­actions.
doi:10.1107/S1600536811023178
PMCID: PMC3151813  PMID: 21837133
25.  1-Acetyl-3-(4-chloro­phen­yl)-5-(4-fluoro­phen­yl)-2-pyrazoline 
In the title mol­ecule, C17H14ClFN2O, the mean plane of the pyrazoline ring makes dihedral angles of 18.19 (1) and 83.51 (4)° with the 4-chloro­benzene and 4-fluoro­benzene rings, respectively. The two benzene rings make a dihedral angle of 76.11 (2)°. Weak inter­molecular C—H⋯O hydrogen bonds help stabilize the crystal structure.
doi:10.1107/S1600536808018333
PMCID: PMC2962024  PMID: 21203111

Results 1-25 (96787)