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Two crystallographically independent mol­ecules are present in the asymmetric unit. O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds form rings and chains and π–π stacks further connect mol­ecules in the crystal., Two crystallographically independent mol­ecules are present in the asymmetric unit of the title compound, C14H11NO2, with virtually identical geometries. The carbazole units are planar. The hy­droxy group at position 1, carbaldehyde group at position 2, and methyl group at position 8 (with the exception of two H atoms) are coplanar with the attached benzene rings. The dihedral angle between the two benzene rings is 2.20 (9)° in mol­ecule A and 2.01 (9)° in mol­ecule B. The pyrrole ring makes dihedral angles of 0.82 (10) and 1.40 (10)° [0.84 (10) and 1.18 (10)° in mol­ecule B] with the (–CH3)-substituted and (–OH and –CHO) substituted benzene rings, respectively. The mol­ecular structure is stabilized by the intra­molecular O—H⋯O hydrogen bonds, while the crystal structure features N—H⋯O and C—H⋯O hydrogen bonds. A range of π–π contacts further stabilizes the crystal structure.

In the title compound, C12H14BrN3O2, the pyrazole and benzene rings are nearly co-planar with a dihedral angle between the rings of 2.36 (5)°. In the crystal, inversion dimers linked by pairwise N—H...N hydrogen bonds generate R 2 2(8) loops. The dimers are linked into a three-dimensional network by weak aromatic π–π stacking interactions [centroid–centroid separation = 3.7394 (6) Å] and C—H...O and C—H...Br hydrogen bonds.

The title compound, C20H22ClNO3, [common name: 3-chloro-3-methyl-r(2),c(6)-bis(p-methoxyphenyl)piperidin-4-one] crystallizes in the P21/c space group with unit cell parameters a = 13.4020(11) A, b = 7.7888(5) A and c = 18.1721(14) A, β = 108.250(9)°, Z = 4. The central piperidin-4-one ring (N1/C1–C5), adopts a slightly distorted chair conformation and an equatorial orientation of all its substituents except for chlorine which is axially located. The dihedral angle between the mean planes of the two phenyl rings is 47.9(4)° and between the piperidin-4- one ring and pendant phenyl rings is 68.8(2)° (C6–C11) and 73.1(6)° (C13–C18), respectively. Crystal packing is stabilized by weak C–H⋯O intermolecular interactions forming chains along the b-axis. Additional weak Cg–π interactions between nearby phenyl rings are also observed. A comparison of these bond lengths and angles within the crystal with Density Functional Theory (DFT) geometry optimized calculations at the B3LYP/6-31+G (d) level has been determined. Hirshfeld surface analysis for determining the molecular shape and visually analyzing the intermolecular interactions in the crystal structure employing 3D molecular surface contours and 2D fingerprint plots gave enrichment ratios for H⋯H, O⋯H, Cl⋯H and C⋯H contacts compared to C–C, Cl⋯Cl and C⋯Cl contacts indicating a higher propensity for O–H interactions to form in this crystal. Electronic transitions have also been predicted by DFT Molecular Orbital calculations and compared to experimental absorption spectra. Molecular orbital diagrams provide visual representations of the top level molecular orbital surfaces in the compound.

A new crystal, (4-Methoxyphenyl) methanaminium bromide (4MPMAB) was successfully developed by suitably functionalising the counter anion for nonlinear optical applications. Structural analysis was carried out and explores the monoclinic crystal system of P21/c space group. The methoxy group of the cation is co-planar with the phenylene moiety with an r.m.s deviation of 0.0294 A from the mean plane (C1 C8/O1). The donor mesomeric effect of methoxy group is revealed. The strong bonding nature and intermolecular N H---Br interaction between the ammonium cation and the halide anion are evidenced. In addition to that, C H---Br and C H---π interactions are also observed. As the protonation takes place by the hydrogen of hydrobromic acid (HBr), the contribution of HBr is highlighted in the formation of the 4MPMAB crystal. Powder X-ray diffraction (PXRD) study authenticates the good crystalline nature of the sample. Fourier transform infrared (FT-IR), 1H and 13C Nuclear magnetic resonance (NMR) spectral study ascertained the functional groups, the formation of the molecule and the N H---Br interaction of the grown crystal. The crystal is stable up to 219 °C. 4MPMAB has soft nature. The crystals have 65% optical transmission from 330 nm to 1100 nm with estimated optical band gap value of 3.5 eV. Z-scan study exhibits the higher third-order nonlinearity of 4MPMAB crystal. The influence of charge transfer on third-order nonlinear optical properties were revealed. Further, the optical limiting performance of 4MPMAB crystal has also been investigated.

The syntheses and crystal structures of 3-(2-chloroethyl)-r-2,c-6-diphenylpiperidin-4-one, C19H20ClNO, (I), and 3-(2-chloroethyl)-r-2,c-6-bis(4-fluorophenyl)piperidin-4-one, C19H18ClF2NO, (II), are described. The piperidone ring adopts a chair conformation in (I), whereas a slightly distorted chair conformation is formed in (II). The dihedral angle between the mean plane of the phenyl rings is 59.1 (1)° in (I) and 76.1 (1)° in (II). The crystal packing features weak intermolecular N—H...O hydrogen bonds in each structure.

Herein, new 2-oxo-1,2-dihydroquinoline-4-carboxylate derivatives (2a-5d) have been synthesized based on a developed systematic approach, only by esterification reactions of 2-oxo-1,2-dihydroquinoline-4-carboxylic acid with various kinds of alcohols, followed by an alkylation reactions using a different alkylating agents. All the generated compounds are characterized by NMR spectroscopy (1H and 13C). The structures of compounds (2b, 3c, 4a, and 4d) were confirmed using monocrystalline X-ray crystallography. The docking study of the developed derivatives and targets of protein database inhibitors (PDB: 1M17 -EGFR kinase) showed useful information on possible interactions. The experimental results and the expected spectral data using the DFT method at the B3LYP/6-31G(d,p) level of theory were compared. Bi- and three-dimensions Hirshfeld surface examinations have been realized to reveal the non-bond interactions in solid-phase crystal packing and to identify the neighboring inter-molecular contacts for the three molecules 3c, 4a, and 4d. Monte Carlo simulations in the aqueous phase were used to expect the affinity of these derivatives toward mitigation of iron and copper corrosion in acidic and neutral solutions. A proper protection property is anticipated for compounds 3c and 4d.

The syntheses and crystal structures of 3-chloro-3-methyl-r-2,c-6-di­phenyl­piperidin-4-one and two of its derivatives are described. In each structure, the piperidine ring adopts a chair conformation. In the crystals, mol­ecules are linked into C(6) chains by weak N—H⋯O hydrogen bonds and C—H⋯π inter­actions are also observed., The syntheses and crystal structure of 3-chloro-3-methyl-r-2,c-6-di­phenyl­piperidin-4-one, C18H18ClNO, (I), 3-chloro-3-methyl-r-2,c-6-di-p-tolyl­piperidin-4-one, C20H22ClNO, (II), and 3-chloro-3-methyl-r-2,c-6-bis­(4-chloro­phen­yl)piperidin-4-one, C18H16Cl3NO, (III), are described. In each structure, the piperidine ring adopts a chair conformation and dihedral angles between the mean planes of the phenyl rings are 58.4 (2), 73.5 (5) and 78.6 (2)° in (I), (II) and (III), respectively. In the crystals, mol­ecules are linked into C(6) chains by weak N—H⋯O hydrogen bonds and C—H⋯π inter­actions are also observed.

The title compound, C17H13NO2, crystallizes with two conformationally very similar independent molecules (AandB) in the asymmetric unit. In the crystal, the individual molecules are linked by pairs of N—H...O hydrogen bonds formingA–AandB–Binversion dimers, withR22(10) rings. They stack alternately up thea-axis direction and are linked by C—H...π interactions, forming sheets parallel to theabplane.

The title compound, C13H10INO, is not planar as the dihedral angle between the planes of the two aryl rings is 44.5 (9)°. The configuration about the central C=N bond is E, and there is an intramolecular O—H...N hydrogen bond which generates an S(6) ring. The molecular packing is stabilized by weak C—H...π interactions. The structure was refined as a two-component inversion twin.

The asymmetric unit of the title organic–inorganic hybrid salt, poly[[μ4-bis(2-methyllactato)borato]sodium], [Na(C8H12BO6)] n , comprises a sodium cation and a bis(2-methyllactato)borate anion. The sodium cation exhibits a [4 + 1] coordination by borate and carbonyl O atoms of the bis(2-methyllactato)borate anion, leading to a three-dimensional polymeric structure.

The asymmetric unit of the title organic–inorganic hybrid salt poly[aquabis[μ3-bis(2-methyllactato)borato]dipotassium], [K(C8H12BO6)(H2O)0.5] n , consists of one bis(2-methyllactato)borate anion, one potassium cation and one water molecule that shows half occupancy due to disorder around a twofold rotation axis. The potassium cation is pseudo-octahedrally coordinated by five O atoms of four symmetry-related bis(2-methyllactato)borate ligands and by the half-occupied water molecule. O—H...O hydrogen bonds between the water molecule and one of the borate O atoms of the bis(2-methyllactato)borate ligand are present in the crystal structure.

The asymmetric unit of the inorganic–organic hybrid salt, poly[aqua[μ4-bis(2-methyllactato)borato]rubidium], [Rb(C8H12BO6)(H2O)] n , comprises a rubidium cation, a bis(2-methyllactato)borate anion, and a water molecule of crystallization. The rubidium cation is pseudo-octahedrally coordinated by five O atoms from four bis(2-methyllactato)borate ligands and by a water molecule. The presence of four coordinating O atoms within the anion lead to the formation of a polymeric three-dimensional framework structure that is consolidated by additional O—H...O hydrogen-bonding interactions.

The asymmetric unit of the organic–inorganic hybrid salt, (C8H12NO)2[CdBr4], consists of two 4-methoxybenzylammonium cations and one [CdBr4]2− anion. The cations and anions are connected by a complex series of N—H...Br and C—H...Br hydrogen bonds. No π–π stacking interactions occur between the benzene rings but two C—H...π interactions are observed.

The asymmetric unit of the centrosymmetric organic–inorganic hybrid salt, {(C8H12N)2[CdBr4]} n , comprises of one 4-methylbenzylammonium cation and one half of a disordered [CdBr4]2− anion that is completed by application of mirror symmetry. The resulting CdBr6 octahedra share edges to form 2 ∞[CdBr4/2Br2/2]2− layers parallel to the ac plane. Cations and anions are connected by N—H...Br and C—H...Br hydrogen bonds. No π–π stacking interactions are observed between the benzene rings, but C—H...π interactions towards them are found.

The structure of the non-centrosymmetric organic–inorganic hybrid material, (C8H12N)2[ZnBr4], consists of two 4-methylbenzylammonium cations and one [ZnBr4]2− anion connected by N—H...Br and C—H...Br hydrogen bonds. The ZnII cation has a slightly distorted tetrahedral coordination environment. No π–π stacking interactions between the phenylene rings but C—H...π interactions towards them are observed. The structure was refined as a two-component inversion twin.

In the title hydrated salt, C8H12N+·Br−·0.5H2O, which is isostructural with its chloride congener, the water O atom lies on a crystallographic twofold axis. In the crystal, the components are linkedviaC—H...Br, O—H...Br, N—H...Br and N—H...O hydrogen bonds to generate (100) sheets. The sheets are linked by two weak C—H...π interactions, generating a three-dimensional network.

In the title hydrated salt, C4H10NO3 +·C7H7O3S−·H2O, an intramolecular C—H...O hydrogen bond in the cation generates an S(6) loop. In the crystal, carboxyl-O—H...O(sulfonate), hydroxyl-O—H...O(sulfonate), water-O—H...O(sulfonate, hydroxyl) and ammonium-N—H...O(water, carbonyl) hydrogen bonds link the components of the asymmetric unit into supramolecular layers parallel to (001).

The title compound, C13H10FNO, is essentially planar (r.m.s. deviation = 0.022 Å) and the dihedral angle between the planes of the two aryl rings is 0.69 (15)°. An intramolecular O—H...N hydrogen bond generates anS(6) ring. The crystal structure features C—H...O hydrogen bonds.

In the title salt, C8H12NO+·NO3−, the 4-methoxybenzylammonium cation lies in the mirror planemof space groupPnmaand is thus planar by symmetry. The nitrate anion is also planar by symmetry, with an N...;O group in the mirror plane and one O atom in a general position. The dihedral angle between the benzene ring and the planar nitrate anion is constrained to be exactly 90°, because of the relative special positions for both ions. In the crystal, the cations are connected to the anions by C—H...O, C—H...N, N—H...N and N—H...O hydrogen bonds. Further, the crystal structure also features two C—H...π interactions involving the benzene ring of the cation, forming a three-dimensional network.

In the title hydrated salt, C8H12N+·Cl−·0.5H2O, the water O atom lies on a crystallographic twofold axis. In the crystal, the cation, anion and water molecule are linked to one anotherviaC—H...Cl, O—H...Cl, N—H...O and N—H...Cl hydrogen bonds. The crystal structure is further stabilized by two weak C—H...π interactions involving the benzene ring to form a three-dimensional network.

The title compound, C18H16ClF2NO, contains one independent molecule in the asymmetric unit, with the piperidin-4-one ring adopting a slightly distorted chair conformation and an equatorial orientation of all the substituents except chlorine. A single weak intermolecular C—H...O interaction influences the crystal packing, forming infinite one-dimensional zigzag chains along the a axis. The structure was refined as a two-component inversion twin.

The asymmetric unit of the title compound, C24H23NO, contains two crystallographically independent molecules (AandB). In both molecules, the piperidine rings adopt a chair conformation and the phenyl rings and the benzyl group substituents are attached equatorially. The dihedral angle between the phenyl rings is 60.80 (10)° in moleculeAand 68.43 (9)° in moleculeB. The phenyl ring of the benzyl group makes dihedral angles of 76.95 (9) and 42.25 (10)° with the phenyl rings in moleculeA, and dihedral angles of 81.38 (11) and 30.19 (11)° in moleculeB. In the crystal, the two molecules are linked by N—H...O hydrogen bonds, forming –A–B–A–B– chains along [100]. In addition, five C—H...π interactions are also present, linking the chains to form a three-dimensional structure.

The FT-IR and the high resolution (1)H and (13)C NMR spectra have been recorded for N'-(2-methyl-3-phenylallylidene)nicotinohydrazide (1) and N'-(2-methyl-3-phenylallylidene)isonicotinohydrazide (2) and analyzed. (1)H-(1)H COSY spectra were also recorded for the hydrazides. The spectral studies reveal that both the hydrazides exist in the keto form. Theoretical calculations were performed for some possible conformations of the hydrazide and the minimum energy conformers are predicted to be the one in which the azomethine protons are syn to N-NH bond. From the optimized structures, HOMO-LUMO energy gap and geometrical parameters were derived and these parameters were compared with the XRD measurements of hydrazide 1. The vibrational frequencies in the ground state have been calculated using DFT and HF methods and compared with the observed frequencies. Non-linear optical (NLO) behaviour of the hydrazides was investigated by the determination of the electric dipole moment mu, the polarizability alpha and the hyperpolarizability beta using B(3)LYP method.

In the title compound, C21H15NO3, the molecule has anEconformation about the C=C bond, and the C—C=C—C torsion angle is −178.24 (18)°. In the molecule, the planes of the terminal rings are twisted by an angle of 42.19 (10)°, while the biphenyl part is not planar, with a dihedral angle between the rings of 39.2 (1)°. The dihedral angle between the nitrophenyl ring and the inner benzene ring is 5.56 (9)°. The 3-nitro group is approximately coplanar with the benzene ring to which it is attached [O—N—C—C = 0.1 (3)°]. In the crystal, molecules are linkedviaC—H...π interactions, involving the terminal benzene rings, forming corrugated layers parallel to (100).

The title compound crystallized with two independent mol­ecules in the asymmetric unit. In the crystal, they are linked to one another, forming chains enclosing (10) and (12) ring motifs., The title compound, C22H17NO4, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. Each mol­ecule exists as an E isomer with C—C=C—C torsion angles of −175.69 (17) and −178.41 (17)° in A and B, respectively. In mol­ecule A, the planes of the terminal benzene rings are twisted by an angle of 26.67 (10)°, while the biphenyl unit is non-planar, the dihedral angle between the rings being 30.81 (10)°. The dihedral angle between the nitro­phenyl ring and the inner phenyl ring is 6.50 (9)°. The corresponding values in mol­ecule B are 60.61 (9), 31.07 (8) and 31.05 (9)°. In the crystal, mol­ecules are arranged in a head-to-head manner, with the 3-nitro­phenyl groups nearly parallel to one another. The A and B mol­ecules are linked to one another via C—H⋯O hydrogen bonds, forming chains lying parallel to (-320) and enclosing R 2 2(10) and R 2 2(12) ring motifs. The meth­oxy group in both mol­ecules is positionally disordered with a refined occupancy ratio of 0.979 (4):0.021 (4) for mol­ecule A and 0.55 (4):0.45 (4) for mol­ecule B.

The title molecule, C13H10N2O, is essentially planar, the maximum deviation from the plane of the non-H atoms being 0.016 (2) Å. The imidazole ring makes a dihedral angle of 0.37 (13)° with the attached benzene ring. An intramolecular O—H...N hydrogen bond generates anS(6) ring motif. In the crystal, molecules are linked through N—H...O hydrogen bonds, forming chains propagating in [001]. The crystal packing also features four π–π stacking interactions involving the imidazole ring, fused benzene ring and attached benzene ring system [centroid–centroid distances = 3.6106 (17), 3.6108 (17), 3.6666 (17) and 3.6668 (17) Å].

In the title molecule, C26H28N2O3, the piperidine ring adopts a chair conformation. The two methoxyphenyl groups attached to the piperidine ring at positions 2 and 6 have equatorial orientations, and make a dihedral angle of 80.72 (15)°. The benzyl group at position 3 has an equatorial orientation. The oxime group at position 4 has a bisectional orientation. The ring of the benzyl group makes dihedral angles of 64.71 (16) and 84.79 (17)° with the two benzene rings. Molecules are linked by intermolecular N—H...O, O—H...N and C—H...O hydrogen bonds, and C—H...π interactions. There is also a C—H...O intramolecular interaction.

In the title mol-ecule, C(14)H(16)O, the cyclo-hexene ring adopts an envelope conformation, with all substituents equatorial. Mol-ecules are linked by C-H⋯O hydrogen bonds. A C-H⋯π inter-action involving the benzene ring is also found in the crystal structure. The H atoms of both methyl groups are disordered equally over two positions.

In the title molecule, C15H17NO, the cyclohexane ring adopts a chair conformation. The cyano and methyl groups at position 1 have axial and equatorial orientations, respectively. The benzene ring has an equatorial orientation. A C—H...π interaction involving the benzene ring is found in the crystal structure.

The carbazole unit of the title molecule, C13H13NO2, is not planar. The dihedral angle between the benzene ring and the pyrrole ring is 1.69 (6)°. The cyclohexene ring adopts an envelope conformation. Intermolecular C—H...O and N—H...O hydrogen bonds are present in the crystal structure. A C—H...π interaction, involving the benzene ring, is also found in the crystal structure.

The asymmetric unit of the title compound, C21H15ClN2, contains two crystallographically independent molocules. In one of the mol­ecules, the chloro­phenyl ring is disordered over two orientations; these are approximately related by a rotation through 180° about its bond with the imidazole ring. The independent mol­ecules are linked into a chain along the a axis by N—H⋯N inter­molecular hydrogen bonds.

In the title mol­ecule, C17H19NO4, the piperidine ring adopts a twist-boat conformation. The acetyl group at position 1 has a bis­ectional orientation. The planar furyl rings at positions 2 and 6 have axial and bis­ectional orientations, respectively. The methyl groups at positions 3 and 5 have bis­ectional and equatorial orientations, respectively. In the crystal structure, the mol­ecules are stabilized by inter- and intra­molecular C—H⋯O hydrogen bonds.

In the title compound, C22H17NO3, the molecule has anEconformation about the C=C bond, and the C—C=C—C torsion angle is −177.7 (3)°. The planes of the terminal benzene rings are twisted by 41.62 (16)°, while the biphenyl unit is non-planar, the dihedral angle between the planes of the rings being 38.02 (15)°. The dihedral angle between the nitrophenyl ring and the inner benzene ring is 5.29 (16)°. In the crystal, molecules are linked by two weak C—H...π interactions, forming rectangular tubes propagating along theb-axis direction.

In the title molecule, C24H20Cl2O2, the central methylbenzene ring forms dihedral angles of 42.47 (10) and 34.34 (10)° with the terminal 4-chlorophenyl fragments. The dihedral angle between the chlorobenzene rings is 34.45 (11)°. A weak intramolecular C—H...O interaction generates an S(6) ring motif. The crystal packing exhibits weak C—H...O hydrogen bonds and C—H...π interactions.

In the title molecule, C23H14N2O2, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1018 (8) Å]. The pyrrole ring makes dihedral angles of 4.44 (5), 3.84 (5), 2.18 (5) and 56.44 (5)° with the pyran, fused benzene rings and phenyl ring, respectively. In the crystal, pairs of N—H...O hydrogen bonds generate R22(14) loops and a C—H...N interaction is also found. Molecules are further linked by a number of π–π interactions [centroid–centroid distances vary from 3.5702 (5) to 3.7068 (6) Å], forming a three-dimensional network.

In the title mol­ecule, C20H15N3, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1082 (15) A]. The pyrrole ring makes dihedral angles of 3.17 (8)/4.10 (9), 7.20 (9) and 44.62 (9)° with the fused benzene, pyrazole and phenyl rings, respectively. In the crystal, mol­ecules are linked via N—H⋯N hydrogen bonds, forming an infinite chain along [010]. Mol­ecules are further linked by nine π–π [centroid–centroid distances vary from 3.6864 (11) to 3.9802 (11) A] and one C—H⋯π inter­action, forming a three-dimensional network.

In the title molecule, C18H15NO2, the atoms in the carbazole unit deviate from planarity [maximum deviation from mean plane = 0.1317 (12) Å]. The pyrrole ring makes dihedral angles of 1.01 (8) and 18.56 (10)° with the benzene and furan rings, respectively. The cyclohexene ring adopts a half-chair conformation. In the crystal, pairs of N—H...O hydrogen bonds form anR22(10) ring. Molecules are further linked by C—H...O and C—H...π interactions, forming a three-dimensional network.

In the title molecule, C19H14N2O, the benzimidazole unit is close to being planar [maximum deviation = 0.0253 (11) Å] and forms dihedral angles of 68.98 (6) and 20.38 (7)° with the adjacent phenyl and benzene rings; the dihedral angle between the latter two planes is 64.30 (7)°. An intramolecular O—H...N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by C—H...N and C—H...O hydrogen bonds, and consolidated into a three-dimensional architecture by π–π stacking interactions, with a centroid–centroid distance of 3.8428 (12) Å.

The title molecule, C 29 H 39 N 3 O 4 , consists of a pyrrolidine and a phenanthrene ring. The mean plane through the pyrrolidine ring atoms is almost perpendicular to that through the phenanthrene ring atoms. The pyrrodiline ring adopts a half-chair conformation, while the fused rings of the phenanthrene system are almost coplanar. In the crystal, molecules are stabilized by van der Waals interactions.

In the title molecule, C24H20N2, the pyrazine ring is significantly distorted from planarity, presumably due to steric crowding, and its conformation is well described as a flattened twist-boat. The benzene ring adjacent to the ethyl group forms dihedral angles of 53.79 (13) and 85.47 (12)° with the other benzene rings; the dihedral angle between adjacent benzene rings is 57.90 (12)°. The ethyl group is disordered over two positions; the site-occupancy factor of the major component is 0.546 (4). No hydrogen bonds are found in the crystal structure.

In the title molecule, C16H20N2OS, the heterocyclic ring adopts a slightly distorted flattened boat conformation, and the plane through the four coplanar atoms makes a dihedral angle of 86.98 (6)° with the benzene ring. The thione, acetyl and methyl groups lie on the opposite side of the heterocyclic mean plane to the isopropylphenyl group which has an axial orientation. A weak intramolecular C—H...O hydrogen bond is observed. In the crystal, molecules are linked via N—H...O, N—H...S and C—H...S hydrogen bonds.

In the title compound, C25H15FN4·H2O, the fused ring system is essentially planar [maximum deviation of 0.0822 (14) Å]. The imidazole ring makes dihedral angles of 76.83 (7) and 32.22 (7)° with the phenyl group attached to nitrogen and the fluorobenzene group to carbon, respectively. The dihedral angle between the two phenyl rings is 72.13 (7)°. Intermolecular O—H...N, O—H...F, C—H...F, C—H...O and C—H...N hydrogen bonds are found in the crystal structure.

In the title molecule, C13H13NS, the dihedral angle between the benzene ring and the fused pyrrole ring is 0.71 (8)° and the cyclohexene ring is in an envelope form. The (CH2)3 atoms of the cyclohexene ring are disordered over two positions; the site-occupancy factor for the major component refined to 0.862 (4). In the crystal, intermolecular N—H...S hydrogen bonds lead to the formation of centrosymmetric aggregates via an R22(10) ring.

In the title molecule, C14H15NO, the dihedral angle between the benzene and pyrrole rings is 1.99 (12)°. The cycloheptene ring adopts a slightly distorted boat conformation.

The title compound, C21H17N3O2, crystallizes with two molecules in the asymmetric unit. The carbazole groups show relatively small deviations from planarity [maximum displacements from the mean carbazole plane are 0.077 (7) and 0.101 (7) Å]. The dihedral angles between the 3-nitrobenzylideneamine and carbazole groups are 37.9 (1) and 37.0 (1)° in the two molecules.

In the title molecule, C22H18O, theo-tolyl ring is connected through a conjugated double bond. The molecule adopts anEconformation and the C—C=C—C torsion angle is 178.77 (13)°. The overall conformation may be described by the values of dihedral angles between the different planes. The terminal rings are twisted by an angle of 54.75 (8)°, while the biphenyl part is not planar, the dihedral angle between the planes of the rings being 40.65 (8)°. The dihedral angle between the benzene rings is 14.10 (7)°. There are three weak C—H...π interactions found in the crystal structure. No classic hydrogen bonds are observed.

The title compound, C15H13NO2, crystallizes with four independent molecules (A, B, C and D) in the asymmetric unit. The carbazole units are almost planar [maximum deviations = 0.015 (3) for A, 0.024 (3) for B, 0.026 (3) for C and 0.046 (3) Å for D]. In all four molecules, there is an O—H...O hydrogen bond involving the hydroxy substituent and the carbonyl O atom of the adjacent acetyl group, which forms a six-membered ring. In the crystal, the four independent molecules are linked via N—H...O and C—H...O interactions.