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1.  (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
2.  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
3.  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
4.  4-{1-[4-(4-Bromo­phen­yl)-1,3-thia­zol-2-yl]-5-(4-fluoro­phen­yl)-4,5-dihydro-1H-pyrazol-3-yl}-5-methyl-1-(4-methyl­phen­yl)-1H-1,2,3-triazole 
In the title compound, C28H22BrFN6S, the central pyrazole ring has an envelope conformation, with the methine C atom being the flap atom. The dihedral angles between the least-squares plane through this ring and the adjacent thia­zole [18.81 (15)°] and triazole [1.83 (16)°] rings indicate a twist in the mol­ecule. A further twist is evident by the dihedral angle of 64.48 (16)° between the triazole ring and the attached benzene ring. In the crystal, C—H⋯N, C—H⋯F, C—H⋯π and π–π inter­actions [occurring between the thia­zole and triazole rings, centroid–centroid distance = 3.571 (2) Å] link mol­ecules into a three-dimensional architecture. The sample studied was a non-merohedral twin; the minor twin component refined to 47.16 (7)%.
doi:10.1107/S1600536812024257
PMCID: PMC3379506  PMID: 22719704
5.  2-[3-(4-Bromo­phenyl)-5-(4-fluoro­phenyl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C24H17BrFN3S, the pyrazole ring is almost planar (r.m.s. deviation = 0.043 Å), with all but the perpendicular fluoro­benzene ring substituents [dihedral angle = 77.9 (3)°] being very approximately coplanar [dihedral angle with the 2-thienyl ring = 19.4 (3)° and with the bromo­benzene ring = 20.3 (3)°; dihedral angle between the 2-thienyl and attached phenyl ring = 11.0 (4)°], so that the mol­ecule has a T-shape. In the crystal, supra­molecular chains along the b-axis direction are sustained by C—H⋯S and C—Br⋯π inter­actions.
doi:10.1107/S1600536813010039
PMCID: PMC3648267  PMID: 23723887
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.  Ethyl 2-amino-6-(4-bromo­phen­yl)-4-(4-fluoro­phen­yl)cyclo­hexa-1,3-diene-1-carboxyl­ate 
In the title compound, C21H19BrFNO2, two independent mol­ecules crystallize in the asymmetric unit. The cyclo­hexa-1,3-diene ring is in a slightly distorted screw-boat conformation. The dihedral angles between the mean planes of the 4-bromo­phenyl and 4-fluoro­phenyl rings are 81.0 (3) and 76.4 (2)° in the two independent mol­ecules. In the crystal, N—H⋯O hydrogen bonds link the molecules into [100] chains.
doi:10.1107/S1600536813023325
PMCID: PMC3884405  PMID: 24427095
8.  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
9.  Isotypic crystal structures of 1-benzyl-4-(4-bromo­phen­yl)-2-imino-1,2,5,6,7,8,9,10-octa­hydro­cyclo­octa­[b]pyridine-3-carbo­nitrile and 1-benzyl-4-(4-fluoro­phen­yl)-2-imino-1,2,5,6,7,8,9,10-octa­hydro­cyclo­octa­[b]pyridine-3-carbo­nitrile 
Two isotypic title compounds comprise a 2-imino­pyridine ring fused with a cyclo­octane ring. In one compound, the cyclo­octane ring adopts a twisted chair–chair conformation, while in the second, this ring adopts a twisted boat–chair conformation.
The mol­ecules of the two isotypic title compounds, C25H24BrN3, (I), and C25H24FN3, (II), comprise a 2-imino­pyridine ring fused with a cyclo­octane ring. In (I), the cyclo­octane ring adopts a twisted chair–chair conformation, while in (II), this ring adopts a twisted boat–chair conformation. The dihedral angles between the planes of the pyridine ring and the bromo­benzene and phenyl rings are 80.14 (12) and 71.72 (13)°, respectively, in (I). The equivalent angles in (II) are 75.25 (8) and 68.34 (9)°, respectively. In both crystals, inversion dimers linked by pairs of C—H⋯N inter­actions generate R 2 2(14) loops, which are further connected by weak C—H⋯π inter­actions, generating (110) sheets.
doi:10.1107/S1600536814022016
PMCID: PMC4257254  PMID: 25484741
crystal structure; cyclo­octa­pyridine; hydrogen bonding
10.  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
11.  (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
12.  3-(4-Bromo­phen­yl)-5-[4-(dimethyl­amino)­phen­yl]-4,5-dihydro-1H-pyrazole-1-carbothio­amide 
The mol­ecule of the title pyrazole derivative, C18H19BrN4S, is twisted. The central pyrazole ring, which adopts a flattened envelope conformation, is almost coplanar with the 4-bromo­phenyl ring, whereas it is inclined to the 4-(dimethyl­amino)­phenyl ring making dihedral angles of 1.68 (6) and 85.12 (6)°, respectively. The dihedral angle between the two benzene rings is 86.56 (6)°. The dimethyl­amino group is slightly twisted from the attached benzene ring [C—C—N—C torsion angles = 8.4 (2) and 8.9 (2)°]. In the crystal, mol­ecules are linked by inter­molecular N—H⋯S hydrogen bonds into chains along [20]. The crystal is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536811006106
PMCID: PMC3052174  PMID: 21522446
13.  (E)-1-(2-Bromo­phen­yl)-3-(2,5-dimeth­oxy­phen­yl)prop-2-en-1-one 
The title compound, C17H15BrO3, is a chalcone with the 2-bromo­phenyl and 2,5-dimeth­oxy­phenyl rings bonded at opposite ends of a propene group. The dihedral angle between the mean planes of the ortho-bromo and ortho,meta-dimeth­oxy-substituted benzene rings is 77.3 (1)°. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 2-bromo­phenyl and 2,5-dimeth­oxy­phenyl rings are 58.6 (1) and 30.7 (4)°, respectively. Weak C—H⋯O, C—H⋯Br and π–π stacking inter­molecular inter­actions [centroid–centroid distance = 3.650 (2) Å] are present in the structure.
doi:10.1107/S1600536810025638
PMCID: PMC3007330  PMID: 21588276
14.  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
15.  (2E)-1-(2-Bromo­phen­yl)-3-(4-bromo­phen­yl)prop-2-en-1-one 
The title compound, C15H10Br2O, is a chalcone with 2-bromo­phenyl and 4-bromo­phenyl rings bonded to opposite sides of a propenone group. The dihedral angle between mean planes of the benzene rings is 71.3 (1)°. The angle between the mean plane of the prop-2-ene-1-one group and the mean planes of the 2-bromo­phenyl and 4-bromo­phenyl rings are 64.2 (9) and 71.3 (1)°, respectively. A weak inter­molecular C—H⋯O inter­action and two weak C—Br⋯π inter­actions are observed, which contribute to the stability of the crystal packing.
doi:10.1107/S1600536810022956
PMCID: PMC3006939  PMID: 21587921
16.  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
17.  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
18.  4′-(4-Bromo­phen­yl)-1′-methyl­dispiro­[acenaphthyl­ene-1,2′-pyrrolidine-3′,2′′-indane]-2,1′′(1H)-dione 
In the title compound, C30H22BrNO2, the cyclo­pentane ring of the dihydro­acenaphthyl­ene group and the pyrrolidine ring are both in envelope conformations with the spiro C atom and N atom, respectively, as the flap atom. The cyclo­pentane ring of the indane group adopts a half-chair conformation. A weak intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The naphthalene ring system of the dihydro­acenaphthyl­ene group forms dihedral angles of 41.76 (6) and 42.17 (6)° with the benzene ring of the bromo­phenyl group and the benzene ring of the indane group, respectively. The dihedral angle between the two benzene rings is 83.92 (7)°. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. Weak C—H⋯π inter­actions are also observed.
doi:10.1107/S1600536812014213
PMCID: PMC3344476  PMID: 22590238
19.  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
20.  4-(4-Bromo­phen­yl)-3-methyl-1-phenyl-6,7-dihydro-1H-pyrazolo­[3,4-b]thieno[2,3-e]pyridine 5,5-dioxide 
In the title compound, C21H16BrN3O2S, the pyrazole and pyridine rings are nearly coplanar, the dihedral angle between their planes being 3.17 (14)°. The 2,3-dihydro­thio­phene ring adopts an envelope conformation. The 4-bromo­phen­yl/pyridine ring and phen­yl/pyrazole rings form dihedral angles of 60.06 (9) and 33.49 (11)°, respectively. There is an intra­molecular C—H⋯N hydrogen bond. The crystal packing is stabilized by inter­molecular C—H⋯O hydrogen bonding and C—H⋯π inter­actions.
doi:10.1107/S1600536811045697
PMCID: PMC3238837  PMID: 22199690
21.  Ethyl 6-(4-chloro­phen­yl)-4-(4-fluoro­phen­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate 
The asymmetric unit of the title compound, C21H18ClFO3, contains two independent mol­ecules. In one mol­ecule (A), the 4-chloro­phenyl, oxo­cyclo­hex-3-ene, carboxyl­ate, and ethyl groups were refined as disordered over two sets of sites with a 0.684 (5):0.316 (5) ratio. The cyclo­hexene ring in the disordered mol­ecule is in a slightly distorted envelope conformation for the major component (with the C atom bound to the carboxylate group being the flap atom) and in a screw-boat conformation for the minor component. In the ordered mol­ecule (B), the cyclo­hexene ring is in a half-chair conformation. The dihedral angles between the mean planes of the fluoro- and chloro-substituted benzene rings are 89.9 (7) (only the major component is considered for A) and 76.4 (7)° (B). In the crystal, inversion dimers are observed along with weak C—H⋯O hydrogen bonds, which form chains along [100].
doi:10.1107/S1600536813031851
PMCID: PMC3885083  PMID: 24454259
22.  Ethyl 6-(4-bromo­phen­yl)-4-(4-fluoro­phen­yl)-2-oxocyclo­hex-3-ene-1-carboxyl­ate 
There are two independent mol­ecules in the asymmetric unit of the title compound, C21H18BrFO3, in which the dihedral angles between the fluoro­phenyl and bromo­phenyl groups are 77.0 (1) and 85.8 (1)°. In one of the mol­ecules, two methine C—H groups of the cyclo­hexene ring are disordered over two sets of sites in a 0.53 (2):0.47 (2) ratio. In both mol­ecules, the atoms of the ethyl group were refined as disordered over two sets of sites with occupancies of 0.67 (2):0.33 (2) and 0.63 (4):0.37 (4). The cyclo­hexene rings have slightly distorted sofa conformations in both mol­ecules. In the crystal, C—H⋯O inter­actions link mol­ecules into chains along the b axis.
doi:10.1107/S1600536812038202
PMCID: PMC3470264  PMID: 23125708
23.  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
24.  1-(4-Bromo­phen­yl)-3-(4-ethoxy­phen­yl)­prop-2-en-1-one 
The title compound, C17H15BrO2, consists of two substituted benzene rings connected by a prop-2-en-1-one group. The mol­ecule is nearly planar and adopts an E configuration. The dihedral angle between the two benzene rings is 8.51 (19)°. The enone plane makes dihedral angles of 11.06 (19) and 7.69 (19)°, respectively, with the bromo­phenyl and ethoxy­phenyl rings. The mol­ecules are linked by C—H⋯O hydrogen bonds to form a zigzag ribbon-like structure along the b direction. The crystal structure is stabilized by weak intra- and inter­molecular C—H⋯O inter­actions.
doi:10.1107/S1600536808021776
PMCID: PMC2962165  PMID: 21203245
25.  (2E)-1-(2-Bromo­phen­yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one 
In the chalcone title compound, C18H17BrO4, the dihedral angle between the mean planes of the 2-bromo- and 3,4,5-trimethoxy-substituted benzene rings is 89.3 (1)°. The angles between the mean plane of the prop-2-en-1-one group and the 2-bromo­phenyl and 3,4,5-trimeth­oxy­phenyl ring planes are 59.7 (1) and 40.5 (8)°, respectively. While no classical hydrogen bonds are present, three weak inter­molecular C—H⋯O inter­actions and weak C—H⋯Br and C—H⋯Cg π-ring stacking inter­actions [C—H⋯Cg distance = 3.377 (2) Å] are observed, which contribute to the stability of crystal packing.
doi:10.1107/S160053681002235X
PMCID: PMC3006788  PMID: 21587901

Results 1-25 (191807)