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1.  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
2.  5-Ethyl-2-(4-fluoro­phen­yl)-4-phen­oxy-1H-pyrazol-3(2H)-one 
In the title compound, C17H15FN2O2, the essentially planar pyrazole ring [maximum deviation = 0.026 (1) Å] makes dihedral angles of 72.06 (7) and 33.05 (7)°, with the phenyl and fluoro­benzene rings, respectively. The dihedral angle between the two six-membered rings is 87.88 (7)°. In the crystal, inter­molecular N—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules into layers lying parallel to the bc plane.
doi:10.1107/S1600536811000754
PMCID: PMC3051690  PMID: 21523133
3.  tert-Butyl 4-{[5-(4-chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]carbon­yl}piperazine-1-carboxyl­ate 
In the title pyrazole derivative, C25H26ClFN4O3, both benzene rings are twisted out of the plane through the pyrazole ring, with dihedral angles of 67.62 (10) and 27.63 (10)° for the fluoro- and chloro-substituted rings, respectively. The dihedral angle between the two benzene rings is 64.54 (9)°. The piperazine ring (with a chair conformation) is linked to the pyrazole ring via a carbonyl spacer and is orientated to lie to one side of the pyrazole plane. In addition to an intra­molecular C—H⋯N contact, there are inter­molecular C—H⋯O inter­actions, which generate a supra­molecular chain with an undulating topology along the c axis that is sustained by alternating centrosymmetric ten-membered {⋯HCNCO}2 and {⋯HC3O}2 synthons.
doi:10.1107/S1600536810038560
PMCID: PMC2983130  PMID: 21587650
4.  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
5.  11-[(E)-2-Fluoro­benzyl­idene]-8-(2-fluoro­phen­yl)-14-hy­droxy-6-thia-3,13-diaza­hepta­cyclo­[13.7.1.19,13.02,9.02,14.03,7.019,23]tetra­cosa-1(22),15(23),16,18,20-pentaen-10-one 
In the title compound, C34H26F2N2O2S, an intra­molecular O—H⋯N hydrogen bond forms an S(5) ring motif. The piperidine ring adopts a chair conformation. The thia­zolidine ring and one of the pyrrolidine rings adopt envolope conformations with methyl­ene C atoms at the flap, whereas the other pyrrolidine ring adopts a half-chair conformation. The fluoro-substituted benzene rings form dihedral angles of 32.25 (10) and 38.27 (10)°, respectively, with the mean plane of the dihydro­acenaphthyl­ene ring system [maximum deviation = 0.043 (2) Å]. The dihedral angle between the fluoro-substituted benzene rings is 64.13 (14)°. In the crystal, mol­ecules are linked by weak C—H⋯O, C—H⋯F and C—H⋯S hydrogen bonds into a three-dimensional network.
doi:10.1107/S1600536812025512
PMCID: PMC3393908  PMID: 22798773
6.  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
7.  5-(2-Hy­droxy­phen­yl)-3-methyl-4,5-di­hydro-1H-pyrazole-1-carbaldehyde 
In the title compound, C11H12N2O2, the dihydro­pyrazole and benzene rings are oriented at a dihedral angle of 68.35 (5)°. The dihydro­pyrazole ring is planar, with a mean deviation from the mean plane of 0.0409 Å. The crystal structure is stabilized by O—H⋯O and C—H⋯O hydrogen bonds.
doi:10.1107/S1600536810031600
PMCID: PMC3008072  PMID: 21588694
8.  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
9.  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
10.  2-[3-(4-Chloro­phen­yl)-5-(4-fluoro­phenyl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C24H17ClFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.030 Å). With the exception of the methine-bound benzene ring, which forms a dihedral angle of 85.77 (13)° with the pyrazole ring, the remaining non-C atoms lie in an approximate plane (r.m.s. deviation = 0.084 Å) so that overall the mol­ecule has a T-shape. In the crystal, centrosymmetrically related mol­ecules are connected via π–π inter­actions between pyrazole rings [centroid–centroid distance = 3.5370 (15) Å] and these stack along the a axis with no specific inter­actions between them.
doi:10.1107/S1600536813007496
PMCID: PMC3629623  PMID: 23634110
11.  1-[5-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone 
In the title mol­ecule, C17H14BrFN2O, the benzene rings form dihedral angles of 6.58 (6) and 85.31 (6)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0231 Å). The latter ring is planar with a maximum deviation of 0.032 (1) Å The dihedral angle between the benzene rings is 78.75 (6)°. In the crystal, weak C—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules into corrugated layers parallel to the ab plane.
doi:10.1107/S1600536812033351
PMCID: PMC3415024  PMID: 22905011
12.  5-(4-Fluoro­phen­yl)-3-[5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazol-4-yl]-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C20H19FN6S, the pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angle between the least-squares plane through the pyrazole and triazole rings is 7.59 (9)°, and the triazole and attached benzene ring form a dihedral angle of 74.79 (9)°. The thio­urea group is coplanar with the pyrazole ring [N—N—C—S torsion angle = −179.93 (11)°], which enables the formation of an intra­molecular N—H⋯N hydrogen bond. In the crystal, inversion-related mol­ecules associate via N—H⋯S hydrogen bonds and eight-membered {⋯HNCS}2 synthons feature in the crystal packing. These synthons are connected into supra­molecular chains along the a axis via N—H⋯F hydrogen bonds, and the chains are consolidated into layers in the ab plane via C—H⋯S and C—H⋯F contacts.
doi:10.1107/S1600536812024245
PMCID: PMC3379505  PMID: 22719703
13.  1-(3-Fluoro­phen­yl)-4,4,6-trimethyl-3,4-dihydro­pyrimidine-2(1H)-thione 
In the title compound, C13H15FN2S, the dihydro­pyrimidine ring is essentially planar, with a maximum deviation of 0.086 (3) Å from the mean plane of the rest of the ring for the dimethyl­ated C atom. The benzene ring is almost perpendicular to the dihydro­pyrimidine ring, with a dihedral angle of 83.97 (14)°. The crystal packing is characterized by centrosymmetric dimers resulting from pairs of inter­molecular N—H⋯S hydrogen bonds. There are also C—H⋯π inter­actions.
doi:10.1107/S1600536811023671
PMCID: PMC3152063  PMID: 21837181
14.  3-(4-Chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
In the title compound, C16H13ClFN3S, the pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. The chloro- and fluoro­benzene rings are twisted out of the plane of the pyrazole ring [dihedral angles = 15.12 (11) and 80.55 (10)°, respectively]. The amine group is orientated towards a ring N atom, forming an intra­molecular N—H⋯N hydrogen bond. This H atom also forms a hydrogen bond to the F atom, which along with N—H⋯S hydrogen bonding leads to a supra­molecular chain along the c axis. Connections between chains of the type Cl⋯π lead to a layer in the bc plane.
doi:10.1107/S1600536813004492
PMCID: PMC3588515  PMID: 23476591
15.  (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
16.  1-[5-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]butan-1-one 
In the title compound, C19H18BrFN2O, the benzene rings form dihedral angles of 5.38 (7) and 85.48 (7)° with the mean plane of the 4,5-dihydro-1H-pyrazole ring (r.m.s. deviation = 0.0849 Å), which approximates to an envelope conformation with the –CH2– group as the flap. The dihedral angle between the benzene rings is 82.86 (7)°. In the crystal, C—H⋯F and C—H⋯O hydrogen bonds link the mol­ecules to form inversion dimers and together these generate chains along [011]. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S1600536812034368
PMCID: PMC3435682  PMID: 22969553
17.  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
18.  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
19.  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
20.  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
21.  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
22.  (2E)-3-(2-Fluoro­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-one 
In the title compouund, C15H10F2O, the mol­ecule exists in an E conformation with respect to the C=C bond [1.3382 (16) Å]. The dihedral angle between the fluoro-substituted benzene rings is 6.80 (6)° and the whole mol­ecule is roughly planar (r.m.s. deviation for the non-H atoms = 0.069 Å). In the crystal, mol­ecules are linked by C—H⋯F and C—H⋯O inter­actions into sheets lying parallel to the bc plane.
doi:10.1107/S1600536812034411
PMCID: PMC3435684  PMID: 22969555
23.  Dimethyl [(4-fluoro­phen­yl)(6-methoxy­benzothia­zol-2-ylamino)meth­yl]phospho­nate 
In the mol­ecule of title compound, C17H18FN2O4PS, both the benzene ring with its conjunction C atom and the benzothia­zole ring with its conjunction N atom are close to planar (the maximum deviations are 0.0267 and 0.0427 Å for the benzene and benzothiazole rings, respectively), the dihedral angle between the planes of the benzothia­zole and benzene rings is 119.05 (3)°. The mol­ecular packing is stabilized by inter­molecular N—H⋯O, C—H⋯N and C—H⋯F hydrogen bonding, and by C—H⋯π and π–π stacking inter­actions [centroid–centroid distances = 2.99 (2), 2.96 (3), 2.88 (2) and 3.773 (4) Å].
doi:10.1107/S1600536809015384
PMCID: PMC2969702  PMID: 21583070
24.  3-Amino-1-(4-fluoro­phen­yl)-7-meth­oxy-1H-benzo[f]chromene-2-carbonitrile 
In the title compound, C21H15FN2O2, the furan ring has a flattened half-chair conformation [the methine C atom lies 0.136 (2) Å above the C5 plane which has an r.m.s. deviation of 0.0229 Å]. Overall, the 1H-benzo[f]chromene fused-ring system approximates a plane (r.m.s. deviation of the 14 non-H atoms = 0.049 Å). The fluoro­benzene ring is almost perpendicular to this plane [dihedral angle = 89.58 (8)°]. Zigzag supra­molecular tapes along the b axis are the most notable feature of the crystal packing. This arises through an alternating sequence of 12-membered {⋯HNC3N}2 and eight-membered {⋯HNCO}2 synthons. These are connected into a three-dimensional architecture by π–π [inter­centroid distance for centrosymmetrically related fluoro­benzene rings = 3.5181 (10) Å] and C—H⋯π inter­actions.
doi:10.1107/S1600536813005473
PMCID: PMC3629516  PMID: 23634034
25.  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

Results 1-25 (250998)