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1.  (2E)-1-(4,4′′-Difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-(2,6-difluoro­phen­yl)prop-2-en-1-one 
In the title compound, C28H18F4O2, the central benzene ring makes dihedral angles of 44.27 (6), 56.33 (5) and 77.27 (6)° with the two adjacent fluoro­benzene rings and terminal difluoro-substituted benzene ring, respectively. The dihedral angle between the fluoro­benzene rings is 87.81 (6)°. The meth­oxy and prop-2-en-1-one groups are essentially coplanar with their attached benzene rings, as indicated by their C—O—Car—Car [−0.06 (15)°] and C—C—Car—Car [4.5 (2)°] (ar = aromatic) torsion angles. In the crystal, mol­ecules are linked by C—H⋯F and C—H⋯O hydrogen bonds into sheets lying parallel to the ac plane. The crystal structure also features C—H⋯π inter­actions.
doi:10.1107/S160053681201820X
PMCID: PMC3344658  PMID: 22590420
2.  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
3.  (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
4.  (2E)-3-(4-Cyano­phen­yl)-1-(4,4′′-difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one 
In the title compound, C29H19F2NO2, the central benzene ring forms a dihedral angle of 56.92 (12)° with the cyano­benzene ring and dihedral angles of 40.91 (12) and 44.76 (12)° with the two fluoro­benzene rings. In the crystal, C—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules into sheets lying parallel to the ab plane. The crystal packing also features C—H⋯π inter­actions involving the central benzene ring.
doi:10.1107/S1600536812023124
PMCID: PMC3379440  PMID: 22719638
5.  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
6.  (2E)-1-(2,6-Dichloro-3-fluoro­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one 
There are two independent mol­ecules in the asymmetric unit of the title compound, C16H11Cl2FO2. The F atom equally populates both meta positions of the 6-dichloro-3-fluoro­phenyl ring in each mol­ecule, resulting in 0.5 occupancy for both the F and H atoms in these positions. The dihedral angle between the mean planes of the benzene rings are 77.5 (2) and 89.8 (8)°in the two mol­ecules. In the crystal, weak C—H⋯F and C—H⋯O inter­actions involving the half-occupied H and F atoms are observed. Weak π–π stacking inter­actions [centroid—centroid distance = 3.150 (2) Å] also contribute to the crystal stability.
doi:10.1107/S1600536812011841
PMCID: PMC3344105  PMID: 22606108
7.  (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
8.  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
9.  Ethyl 2-amino-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carboxyl­ate 
In the title compound, C23H20FNO4, the fluoro-substituted benzene ring is approximately perpendicular to the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.264 (1) Å], with a dihedral angle of 83.79 (6)°. The pyran ring adopts a flattened boat conformation. The meth­oxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −2.1 (2)°]. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by N—H⋯O and N—H⋯F hydrogen bonds into a layer parallel to the bc plane. The crystal packing also features C—H⋯π inter­actions.
doi:10.1107/S1600536812021939
PMCID: PMC3379378  PMID: 22719576
10.  4-[Bis(4-fluoro­phen­yl)meth­yl]-1-[(2E)-3-phenyl­prop-2-en-1-yl]piperazin-1-ium 3-carb­oxy­propano­ate 
In the title salt, C26H27F2N2 +·C4H5O4 −, the piperazine N atom bearing the vinylic substituent is protonated. The piperazine ring adopts a chair conformation. In ther crystal, the succinate monoanions are connected via short O—H⋯O hydrogen bonds between the carb­oxy­lic acid and carboxyl­ate groups into undulating chains extending along [001] and the flunarizinium monocations are attached to these chains via N+—H⋯O− hydrogen bonds. C—H⋯O inter­actions connect these chains into a three-dimensional network. The shortest centroid–centroid distance of 3.7256 (10) Å was found between one of the fluorinated benzene rings and the non-fluorinated phenyl ring in the neighbouring mol­ecule related by a glide plane.
doi:10.1107/S1600536813000706
PMCID: PMC3569791  PMID: 23424537
11.  1-[Bis(4-fluoro­phen­yl)meth­yl]-4-[(2Z)-3-phenyl­prop-2-en-1-yl]piperazine-1,4-diium dichloride hemihydrate 
The asymmetric unit of the title monohydrated salt, 2C26H28F2N2 2+·4Cl−.H2O, consists of a 1-[bis­(4-fluoro­phen­yl)meth­yl]-4-[(2Z)-3-phenyl­prop-2-en-1-yl]piperazine-1,4-diium cation with a diprotonated piperizine ring in close proximity to two chloride anions and a single water mol­ecule that lies on a twofold rotation axis. In the cation, the piperazine ring adopts a slightly distorted chair conformation. The dihedral angles between the phenyl ring and the 4-fluoro­phenyl rings are 89.3 (9) and 35.0 (5)°. The two fluoro­phenyl rings are inclined at 65.0 (5)° to one another. In the crystal, N—H⋯Cl hydrogen bonds and weak C—H⋯Cl inter­molecular inter­actions link the mol­ecules into chains along [010]. In addition, weak C—H⋯O inter­actions between the piperizine and prop-2-en-1-yl groups with the water mol­ecule, along with weak C—H⋯Cl inter­actions between the prop-2en-1-yl and methyl groups with the chloride ions, weak C—H⋯F inter­actions between the two fluoro­phenyl groups and weak O—H⋯Cl inter­actions between the water mol­ecule and chloride ions form a three-dimensional supra­molecular network.
doi:10.1107/S1600536814011064
PMCID: PMC4051083  PMID: 24940270
12.  4-(2-Fluoro­phen­yl)-2-meth­oxy-5,6,7,8,9,10-hexa­hydro­cyclo­octa­[b]pyridine-3-carbo­nitrile 
In the title compound, C19H19FN2O, the cyclo­octene ring adopts a twisted boat–chair conformation. The dihedral angle between the plane of the fluorophenyl substituent and that of the pyridine ring is 76.39 (8)°. The F and ortho-H atoms of the fluoro­benzene ring are disordered, with occupancy factors of 0.226 (5) and 0.774 (5). In the crystal, no significant inter­actions are observed between the mol­ecules beyond van der Waals contacts.
doi:10.1107/S1600536814016365
PMCID: PMC4158480  PMID: 25249918
crystal structure; cyclo­octa­[b]pyridine; carbo­nitrile compounds
13.  3-Amino-1-(4-fluoro­phen­yl)-8-meth­oxy-1H-benzo[f]chromene-2-carbonitrile 
The title compound, C21H15FN2O2, features an approximately planar 1H-benzo[f]chromene fused-ring system (r.m.s. deviation for the 14 non-H atoms = 0.052 Å), with the fluoro­benzene ring being almost perpendicular to this [dihedral angle = 85.30 (7) °]. The furan ring has a flattened half-chair conformation, with the methine C atom deviating by 0.132 (2) Å from the plane of the remaining atoms (r.m.s. deviation = 0.0107 Å). In the crystal, inversion dimers are formed via pairs of amine–cyano N—H⋯N hydrogen bonds. The dimers are connected into a three-dimensional architecture by C—H⋯N(cyano), C—H⋯π and π–π [inter­centroid distance = 3.6671 (10) Å] inter­actions.
doi:10.1107/S160053681300545X
PMCID: PMC3629515  PMID: 23634033
14.  (E)-1-(4,4′′-Difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)-3-(4-methyl­phen­yl)prop-2-en-1-one 
In the meta-terphenyl fragment of the title mol­ecule, C29H22F2O2, the two fluoro­phenyl rings are twisted from the central benzene ring by 46.72 (6) and 41.70 (6)°, respectively. In the crystal, weak C—H⋯O and C—H⋯F hydrogen bonds link the mol­ecules into layers parallel to the ab plane. The crystal packing exhibits π–π inter­actions, the shortest distance between the centroids of aromatic rings being 3.6364 (7) Å.
doi:10.1107/S160053681104579X
PMCID: PMC3238850  PMID: 22199703
15.  (E)-1-[2-Hy­droxy-4,6-bis­(meth­oxy­meth­oxy)phen­yl]-3-[3-meth­oxy-4-(meth­oxy­meth­oxy)phen­yl]prop-2-en-1-one 
The title compound, C22H26O9, crystallizes with two independent mol­ecules in the asymmetric unit in which the dihedral angles between the two benzene rings are 21.4 (2) and 5.1 (2)°. An intra­molecular O—H⋯O hydrogen bond occurs in each mol­ecule. Inter­molecular C—H⋯O hydrogen bonds stabilize the crystal structure.
doi:10.1107/S1600536811041213
PMCID: PMC3247344  PMID: 22219962
16.  Methyl (2Z)-2-(2-fluoro-4-meth­oxy­benzyl­idene)-5-(4-meth­oxy­phen­yl)-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thia­zolo[3,2-a]pyrimidine-6-carboxyl­ate 
The asymmetric unit of the title compound, C24H21FN2O5S, consists of two crystallographically independent mol­ecules. In each mol­ecule, the central dihydro­pyrimidine ring is significantly puckered and adopts a conformation which is best described as an inter­mediate between a boat and a screw boat. The least-squares planes of the dihydro­pyrimidine rings are almost coplanar with the fluoro-substituted benzene rings, making dihedral angles of 9.04 (7) and 6.68 (7)°, and almost perpendicular to the meth­oxy-substituted benzene rings with dihedral angles of 89.23 (7) and 88.30 (7)°. In the mol­ecular structure, S(6) ring motifs are formed by C—H⋯O and C—H⋯S hydrogen bonds. In the crystal, mol­ecules are linked into a three-dimensional network by inter­molecular C—H⋯O and C—H⋯F hydrogen bonds. The crystal structure is further stabilized by a C—H⋯π inter­action.
doi:10.1107/S1600536811025141
PMCID: PMC3212305  PMID: 22090962
17.  (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
18.  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
19.  3-(4-Fluoro­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one 
The title compound, C16H13FO2, was prepared from 4-methoxy­hypnone and 4-fluoro­benzophenone by Claisen–Schmidt condensation. All the bond lengths and bond angles are in normal ranges. The dihedral angle formed by the two benzene rings is 33.49 (2)°. The crystal packing is stabilized by inter­molecular C—H⋯O hydrogen-bonding inter­actions.
doi:10.1107/S1600536809018121
PMCID: PMC2969700  PMID: 21583247
20.  A second polymorph of (2E)-1-(4-fluoro­phen­yl)-3-(3,4,5-trimethoxy­phen­yl)prop-2-en-1-one 
The crystal structure of the title compound, C18H17FO4, reported here is a polymorph of the structure first reported by Patil et al. [Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A (2007), 461, 123–130]. It is a chalcone analog and consists of substituted phenyl rings bonded at the opposite ends of a propenone group, the biologically active region. The dihedral angle between the mean planes of the aromatic rings within the 4-fluoro­phenyl and trimethoxy­phenyl groups is 28.7 (1)° compared to 20.8 (6)° in the published structure. The angles between the mean plane of the prop-2-ene-1-one group and the mean plane of aromatic rings within the 4-fluoro­phenyl and trimethoxy­phenyl groups are 30.3 (4) and 7.4 (7)°, respectively, in contast to 10.7 (3) and 12.36° for the polymorph. While the two 3-meth­oxy groups are in the plane of the trimeth­oxy-substituted ring, the 4-meth­oxy group is in a synclinical [−sc = −78.1 (2)°] or anti­clinical [+ac = 104.0 (4)°] position, compared to a +sc [53.0 (4)°] or −ac [−132.4 (7)°] position. While no classical hydrogen bonds are present, weak inter­molecular C—H⋯π-ring inter­actions are observed which contribute to the stability of the crystal packing. The two polymorphs crystallize in the same space group, P21/c, but have different cell parameters for the a, b and c axes and the β angle. A comparison of the mol­ecular geometries of both polymorphs to a geometry optimized density functional theory (DFT) calculation at the B3-LYP/6–311+G(d,p) level for each structure provides additional support to these observations.
doi:10.1107/S1600536809028517
PMCID: PMC2977262  PMID: 21583642
21.  (2E)-3-{4-[(1H-1,3-Benzimidazol-2-yl)meth­oxy]-3-eth­oxy­phen­yl}-1-(4-bromo­phen­yl)prop-2-en-1-one monohydrate 
In the title compound, C25H21BrN2O3·H2O, the benzimidazole fragment and the water mol­ecule of crystallization are each disordered over two sets of sites of equal occupancy. The dihedral angles between the least-squares planes of the benzimidazole and the 3-eth­oxy- and 4-bromo­benzene rings are 86.9 (6) and 85.1 (1)°, respectively in one disorder component. The crystal packing is stabilized by inter­molecular O—H⋯O, O—H⋯N and N—H⋯N hydrogen bonds, which link the mol­ecules into chains along the a axis.
doi:10.1107/S1600536811008154
PMCID: PMC3099940  PMID: 21754118
22.  4-(3-Fluoro-4-meth­oxy­phen­yl)-1-(4-meth­oxy­phen­yl)-5-(3,4,5-trimeth­oxy­phen­yl)-1H-imidazole 
In the title mol­ecule, C26H25FN2O5, the fluoro­meth­oxy-, meth­oxy- and trimeth­oxy-substituted benzene rings form dihedral angles of 12.65 (2), 84.15 (2) and 55.67 (2)°, respectively, with the imidazole ring. The crystal structure is stabilized weak inter­molecular C—H⋯F and C—H⋯O hydrogen bonds.
doi:10.1107/S160053681004465X
PMCID: PMC3011382  PMID: 21589391
23.  The chalcone derivative (E)-1-(4-fluoro­phen­yl)-3-(4-hy­droxy-3-meth­oxy­phen­yl)prop-2-en-1-one monohydrate 
The title compound, C16H13FO3·H2O, has a cis disposition of the carbonyl and olefin bonds about the enone single bond. The arene rings are inclined to one another by 10.05 (6) Å. In the crystal, mol­ecules are linked via O—H⋯O hydrogen bonds involving the water mol­ecules, forming loops which are, in turn, linked via O—H.·O and C—H⋯F hydrogen bonds, forming sheets lying parallel to (103). These networks are linked via π–π inter­actions [centroid–centroid distance = 3.641 (1) Å] involving inversion-related 4-fluoro­phenyl and 4-hy­droxy-3-meth­oxy­phenyl rings.
doi:10.1107/S160053681300696X
PMCID: PMC3629610  PMID: 23634097
24.  (2E)-3-(6-Meth­oxy­naphthalen-2-yl)-1-[4-(methyl­sulfan­yl)phen­yl]prop-2-en-1-one 
The asymmetric unit of the title compound, C21H18O2S, consists of two crystallographically independent mol­ecules (A and B). The mol­ecules exist in a trans conformation with respect to the central C=C bond. The naphthalene ring system makes dihedral angles of 51.62 (12) (mol­ecule A) and 52.69 (12)° (mol­ecule B) with the benzene ring. In mol­ecule A, the prop-2-en-1-one group forms dihedral angles of 22.84 (15) and 29.02 (12)° with the adjacent naphthalene ring system and benzene ring, respectively, whereas the corresponding angles are 30.04 (12) and 23.33 (12)° in mol­ecule B. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds into head-to-tail chains along the a axis. The crystal packing also features C—H⋯π inter­actions. The crystal studied was a pseudo-merohedral twin with twin law (100 0-10 00-1) and a refined component ratio of 0.6103 (16):0.3897 (16).
doi:10.1107/S1600536812028930
PMCID: PMC3394057  PMID: 22798922
25.  (2E)-3-[4-(1H-Benzimidazol-2-ylmeth­oxy)phen­yl]-1-(4-meth­oxy­phen­yl)prop-2-en-1-one 
In the title compound, C24H20N2O3, the mean plane of the benzimidazole unit makes dihedral angles of 79.88 (11) and 85.44 (12)° with the benzene and 4-meth­oxy­benzene rings, respectively. The benzene and 4-meth­oxy­benzene rings maske a dihedral angle of 16.10 (14)°. A pair of inter­molecular N—H⋯O hydrogen bonds connects adjacent mol­ecules into an inversion dimer, generating an R 2 2(26) ring motif. The crystal structure is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536811012645
PMCID: PMC3089334  PMID: 21754409

Results 1-25 (267555)