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.
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 . 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.
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
The title compound, C25H33FN2O4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The asymmetric unit contains two independent molecules. In each molecule, the ten-membered ring displays an approximative chair–chair conformation. Each of the piperazine rings adopts a perfect chair conformation, while both lactone rings show an envelope conformation, one with the C atom bearing the piperazin-1-ylmethyl group as the flap, the other with the junction C atom not attached to the ring O atom as the flap. The dihedral angles between the least-squares planes through the ten- and five-membered rings in the two molecules are similar [19.1 (3) and 16.2 (3)°]. An intramolecular O—H⋯N hydrogen bond stabilizes the molecular conformation. The crystal packing is stabilized by C—H⋯O hydrogen bonds.
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.
In the title molecule, C26H28F2N2O, the piperazine ring adopts a chair conformation, with the N-bonded substituents in equatorial orientations. The dihedral angle between the fluorobenzene rings is 69.10 (15).
In the title molecule, C23H18F2N2O3S, the pyrimidine ring is in a half-chair conformation and the 3-fluorophenyl group is in the axial position. The thiazole ring (r.m.s. deviation = 0.0252 Å) forms dihedral angles of 84.8 (7) and 9.6 (7)° with the 3-fluoro-substituted and 4-fluoro-substituted benzene rings, respectively. In the crystal, weak C—H⋯F and C—H⋯O hydrogen bonds connect molecules, forming zigzag chains along the b axis. In addition π–π stacking interactions with a centroid–centroid distance of 3.7633 (9) Å connect these chains into ladders via inversion-related 4-fluorophenyl groups.
crystal structure; pyrimidine; thiazole; hydrogen bonds; π–π stacking interactions
In the title molecule, C29H28F2N2O, the piperazine ring adopts a chair conformation with the pendant N—C bonds in equatorial orientations. The conformation of the N—C—C—O linkage is gauche [torsion angle = −64.6 (4)°] and the dihedral angle between the fluorobenzene rings is 64.02 (15)°.
The conformation of the title molecule, C25H23FN4O, is mainly determined by an intramolecular N—H⋯N hydrogen bond closing a six-membered ring and the dihedral angles between the pyrimidine ring and the three benzene rings which are 12.8 (2), 12.0 (2) and 86.1 (2)°. An intramolecular N—H⋯F interaction also occurs. The crystal stucture is stabilized by weak C—H⋯O and C—H⋯π interactions. An intermolecular N—H⋯N interaction is also observed.
In the title salt, C26H27F2N2
−, 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  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.
The asymmetric unit of the title compound, C29H24FNO5·0.5CH3OH, contains two independent molecules and a one methanol solvent molecule. The methanol molecule is O—H⋯O hydrogen bonded to one of the independent molecules. The pyrrolidine rings in both molecules adopt half-chair conformations, while the cyclopentane rings within the indane groups are in flattened envelope conformations, with the spiro C atoms forming the flaps. The benzene rings of the indane ring systems form a dihedral angle of 35.06 (7)° in one independent molecule and 31.16 (8)° in the other. The fluoro-substituted benzene ring forms dihedral angles of 65.35 (6) and 85.87 (7)° with the indane group benzene rings in one molecule, and 72.78 (8) and 77.27 (8)° in the other. In each molecule, a weak intramolecular C—H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, weak C—H⋯O, C—H⋯N and C—H⋯F hydrogen bonds link the molecules into a three-dimensional network.
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.
In the molecule of the title compound, C31H36N2O5, the piperazine ring displays a chair conformation. The dihedral angle between the benzene rings of the bis(4-methoxyphenyl)methyl group is 83.42 (15)°. In the crystal, centrosymmetrically related molecules are linked through pairs of C—H⋯O hydrogen bonds into dimers, generating an R
2(10) ring motif. The dimers are further connected into chains parallel to [2-10] by C—H⋯O hydrogen bonds involving the methoxy groups.
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.
The title 1,3,4-oxadiazole-2-thione derivative, C18H20N4OS2, crystallized with two independent molecules (A and B) in the asymmetric unit. The 2-thienyl rings in both molecules are rotationally disordered over two orientations by approximately 180° about the single C—C bond that connects it to the oxadiazole thione ring; the ratios of site occupancies for the major and minor components were fixed in the structure refinement at 0.8:0.2 and 0.9:0.1 in molecules A and B, respectively. The 1,3,4-oxadiazole-2-thione ring forms dihedral angles of 7.71 (16), 10.0 (11) and 77.50 (12)° (molecule A), and 6.5 (3), 6.0 (9) and 55.30 (12)° (molecule B) with the major and minor parts of the disordered thiophene ring and the mean plane of the adjacent piperazine ring, respectively, resulting in approximately V-shaped conformations for the molecules. The piperazine ring in both molecules adopts a chair conformation. The terminal benzene ring is inclined towards the mean plane of the piperazine ring with N—C—C—C torsion angles of −58.2 (3) and −66.2 (3)° in molecules A and B, respectively. In the crystal, no intermolecular hydrogen bonds are observed. The crystal packing features short S⋯S contacts [3.4792 (9) Å] and π–π interactions [3.661 (3), 3.664 (11) and 3.5727 (10) Å], producing a three-dimensional network.
crystal structure; 1,3,4-oxadiazole; piperazin-1-yl; disorder; π–π interactions; S⋯S contacts
In the title compound, C14H14F4N2O3S, the central dihydropyrimidine ring adopts a sofa conformation with the C atom bearing the 2-fluorobenzene ring displaced by 0.596 (3) Å from the other five atoms. The 2-fluorobenzene ring is positioned axially and bisects the pyrimidine ring with a dihedral angle of 70.92 (8)°. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(6) ring. The crystal structure features C—H⋯F, N—H⋯S and N—H⋯O hydrogen bonds, which link the molecules into a three-dimensional network.
crystal structure; dihydropyrimidine derivative; organofluorine compounds; hydrogen bonding
The structures of two butenolide derivatives are reported. The conformations are differ largely in the orientation of the amide carbonyl atom.
The title compounds, C22H19F4NO4, (I), and C25H22F3NO5, (II), each contain a central nearly planar dihydrofuranone ring. The r.m.s. deviation from planarity of these rings is 0.015 Å in (I) and 0.027 Å in (II). The molecules are T-shaped, with the major conformational difference being the O—C—C—O torsion angle [−178.9 (1) in (I) and 37.7 (2)° in (II)]. In the crystal of (I), molecules are linked by N—H⋯O hydrogen bonds, forming chains along  while in (II) molecules are linked by N—H⋯O hydrogen bonds, forming chains along . In (II), the trifluoromethyl substituent is disordered over two sets of sites, with refined occupancies of 0.751 (3) and 0.249 (3).
crystal structure; pharmaceuticals; butenolides; N—H⋯O hydrogen bonding
In the title compound, C27H27BrFNO4, which is an inhibitor of acetyl-CoA carboxylase, the cyclohexane ring displays a chair comformation with the spiro-C and methoxy-bearing C atoms deviating by 0.681 (7) and −0.655 (1) Å, resppectively, from the mean plane formed by the other four C atoms of the spiro-C6 ring. The mean planes of the cyclohexane and 2-bromo-4-fluorophenyl rings are nearly perpendicular to that of the pyrrolidine ring, making dihedral angles 89.75 (6) and 87.60 (9)°, respectively. In the crystal, molecules are linked via pairs of N—H⋯O hydrogen bonds, forming inversion dimers.
The title compound, C26H36N2O5, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), wich was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from fused five- and ten-membered rings with the methoxyphenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring a flattened envelope conformation; the C(H)—C—C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.343 (3) Å. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 18.12 (14)°. An intramolecular O—H⋯N hydrogen bond occurs. The crystal structure features weak C—H⋯O interactions.
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 .
The title compound, C31H24F4N2O, exists in a chair–boat conformation with an equatorial orientation of the 2-fluorophenyl groups on both sides of the secondary amino group of the chair form. The benzene rings in the ‘chair’ part are inclined to each other at 19.4 (1)°, while the equivalent angle between the benzene rings in the ‘boat’ part is 75.6 (1)°. One F atom was treated as disordered over two positions in a 0.838 (4):0.162 (4) ratio. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains along  and these chains are held together via weak N—H⋯F and C—H⋯F interactions.
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.
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.
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].
In the title compound, C28H29FN2O3, the conformation about the ethene bond is E. The piperazine ring adopts a chair conformation. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds.