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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.

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 (A and B) in the asymmetric unit. In the crystal, the individual molecules are linked by pairs of N—H...O hydrogen bonds forming A–A and B–B inversion dimers, with R22(10) rings. They stack alternately up the a-axis direction and are linked by C—H...π interactions, forming sheets parallel to the ab plane.

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 title compound, C14H13NO, is not planar with the dihedral angle between the planes of the two aryl rings being 6.22 (11)°. The configuration about the imine bond is E. An intramolecular O—H...N hydrogen bond generates an S(6) loop. In the crystal, molecules assemble into columns parallel to the a axis. The methyl group is disordered over two positions rotated from each other by 60°.

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 an S(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 plane m of space group Pnma and 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 another via C—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.

In the title compound, C24H24N2O [systematic name: (E)-3-benzyl-2,6-diphenylpiperidin-4-one oxime], the piperidine ring adopts a slightly distorted chair conformation and the phenyl rings and the benzyl group substituents are attached equatorially. The oxime group makes a dihedral angle of 42.88 (12)° with the piperidine ring. The dihedral angle between the phenyl rings is 71.96 (8)°. The benzyl ring makes dihedral angles of 63.01 (8) and 59.35 (8)° with the two phenyl rings. In the crystal, molecules are linked by O—H...N hydrogen bonds, forming C(7) chains along the c axis. The chains are linked by C—H...π interactions, forming slabs lying parallel to the bc plane.

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 R22(10) and R22(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 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.

In the title compound, C13H10N2O3, the dihedral angle between the planes of the two aryl rings is 7.42 (10)°. An intramolecular O—H...N hydrogen bond generates an S(6) ring. The crystal structure features C—H...O hydrogen bonds.

In the title salt, poly[aqua[μ4-bis(malonato)borato]sodium], {[Na(C6H4BO8)]·H2O}n or Na+·[B(C3H2O4)2]−·H2O, the sodium cation exhibits fivefold coordination by four carbonyl O atoms of the bis(malonato)borate anions and a water O atom. The tetrahedral B atom at the centre of the anion leads to the formation of a polymeric three-dimensional framework, which is consolidated by C—H...O and O—H...O hydrogen bonds. A Hirshfeld surface analysis indicates that the most significant contacts in the crystal packing are H...O/O...H (49.7%), Na...O/O...Na (16.1%), O...O (12.6%), H...H (10.7%) and C...O/O...C (7.3%).

In the title compound, C21H15NO3, the molecule has an E conformation 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 linked via C—H...π interactions, involving the terminal benzene rings, forming corrugated layers parallel to (100).

In the title molecule, C22H18O, the o-tolyl ring is connected through a conjugated double bond. The molecule adopts an E conformation 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 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 an S(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 compound, C26H30O2, the central benzene ring forms dihedral angles of 14.85 (15) and 28.17 (14)° with the terminal benzene rings. The dihedral angle between the terminal benzene rings is 32.14 (13)°. The crystal packing exhibits two strong intermolecular O—H...O hydrogen bonds, forming directed four-membered co-operative rings. A region of disordered electron density, most probably disordered ethyl acetate solvent molecules, occupying voids of ca 519 Å3 for an electron count of 59, was treated using the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148–155]. Their formula mass and unit-cell characteristics were not taken into account during refinement. The structure was refined as an inversion twin [absolute structure parameter = −0.3 (4)].

In the title compound, C23H16N2·0.5C6H6, the benzimidazole unit [maximum deviation = 0.0258 (6) Å] and the naphthalene ring system [maximum deviation = 0.0254 (6) Å] are both essentially planar and make a dihedral angle of 61.955 (17)°. The imidazole ring makes dihedral angle of 61.73 (4)° with the phenyl ring. An intramolecular C—H...N hydrogen bond generates an S(6) ring motif. In the crystal, seven weak C—H...π interactions involving the fused ring system, the benzene solvent molecule, the imidazole phenyl rings are observed, leading to a three-dimensional architecture.

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, 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 an R22(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.

In the title compound, C19H20Cl2N2O, the seven-membered 1,4-diazepane ring adopts a chair conformation while the 4-chlorophenyl substituents adopt equatorial orientations. The chlorophenyl ring at position 7 is disordered over two positions [site occupancies 0.480 (16):0.520 (16)]. The dihedral angle between the two benzene rings is 63.0 (4)°. The methyl groups at position 3 have an axial and an equatorial orientation. The compound exists as a dimer exhibiting intermolecular N—H...O hydrogen bonding with R22(8) graph-set motifs. The crystal structure is further stabilized by C—H...O hydrogen bonds together with two C—Cl...π (ring) interactions. The geometry was optimized by DFT using the B3LYP/6–31 G(d,p) level basis set. In addition, the HOMO and LUMO energies, chemical reactivity parameters and molecular electrostatic potential were calculated at the same level of theory. Hirshfeld surface analysis indicated that the most important contributions to the crystal packing are from H...H (45.6%), Cl...H/H...Cl (23.8%), H...C/C...H (12.6%), H...O/O...H (8.7%) and C...Cl/Cl...C (7.1%) interactions. Analysis of the interaction energies showed that the dispersion energy is greater than the electrostatic energy. A crystal void volume of 237.16 Å3 is observed. A molecular docking study with the human oestrogen receptor 3ERT protein revealed good docking with a score of −8.9 kcal mol−1.

In the title molecule, C19H14N2, the benzimidazole unit is close to being planar [maximum deviation = 0.0102 (6) Å] and forms dihedral angles of 55.80 (2) and 40.67 (3)° with the adjacent phenyl rings; the dihedral angle between the phenyl rings is 62.37 (3)°. In the crystal, one C—H...N hydrogen bond and three weak C—H...π interactions involving the fused benzene ring and the imidazole ring are observed, leading to a three-dimensional architecture.

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.

The phenanthrene tricyclic ring system in the title molecule, C28H19FN2, is slightly skewed with a dihedral angle of 7.50 (6)° between the outer benzene rings. The p-tolyl and fluorobenzene rings are twisted from the attached imidazole ring by 70.40 (7) and 28.33 (7)°, respectively. In the crystal, C—H...F hydrogen bonds link the molecules into zigzag chains in [001], and weak C—H...π interactions further consolidate the crystal packing.

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 molecule, C13H13FN2OS, the heterocyclic ring adopts a slightly distorted flattened boat conformation, and the plane through the four coplanar atoms makes a dihedral angle of 87.45 (14)° with the benzene ring. The thione, acetyl and methyl groups lie on the opposite side of the heterocyclic mean plane to the fluorophenyl group, which has an axial orientation. N—H...O, N—H...S, C—H...F and C—H...O intermolecular hydrogen bonds and a weak C—H...π interaction involving the benzene ring are found in the crystal structure.

In the title molecule, C19H13FN2, the benzimidazole unit is close to planar [maximum deviation = 0.0342 (9) Å] and forms dihedral angles of 58.94 (3) and 51.43 (3)° with the phenyl and fluorobenzene rings, respectively; the dihedral angle between the phenyl and fluorobenzene rings is 60.17 (6)°. In the crystal, three C—H...F hydrogen bonds and two weak C—H...π interactions involving the fused benzene ring lead to a three-dimensional architecture.

In the title molecule, C13H12ClNO, the dihedral angle between the benzene and pyrrole rings is 1.38 (9)°. The cycloheptene ring adopts a distorted twist chair and sofa conformation. Intermolecular N—H...O hydrogen bonds form an R22(10) loop in the crystal packing. Further, weak C—H...O and C—H...π (involving the benzene ring) interactions are found in the crystal structure.

In the title compound, C19H19FN2O2, the imidazole ring is essentially planar [maximum deviation = 0.0030 (8) Å] and makes dihedral angles of 66.45 (7) and 29.98 (7)° with the benzene rings attached to the ring N and C atoms, respectively. The dihedral angle between the two benzene rings is 64.79 (7)°. A C—H...π interaction is found in the crystal structure. The two methoxy groups were found to be disordered over two sets of sites with occupancy factors of 0.803 (4) and 0.197 (4). The F atom is disordered over two sites with occupancy factors of 0.929 (4) and 0.071 (4).

The title compound, C22H20N2, crystallizes with two independent molecules (A and B) in the asymmetric unit. The benzimidazole units are almost planar [maximum deviations = 0.0161 (8) Å for A and 0.0276 (8) Å for B]. The dihedral angles between the benzimidazole unit and the benzene rings of the 4-methylbenzyl and 4-methylphenyl groups are 76.64 (3) and 46.87 (4)°, respectively, in molecule A. The corresponding values in molecule B are 86.31 (2) and 39.14 (4)°. The dihedral angles between the planes of the two benzene rings are 73.73 (3) and 80.69 (4)° in molecules A and B, respectively. Pairs of weak intermolecular C—H...N hydrogen bonds link B molecules, forming centrosymmetric dimers with R22(8) ring motifs. There are no significant corresponding interactions involving the A molecules.

In the title molecule, C23H19ClN2, the heterocyclic ring adopts a screw-boat conformation, with all substituents equatorial. The benzene ring at position 2 makes dihedral angles of 77.88 (12) and 76.31 (12)° with the phenyl rings at positions 5 and 6, respectively. The dihedral angle between the phenyl rings at positions 5 and 6 is 70.05 (10)°. The Cl atom is disordered over two positions with occupancy factors of 0.946 (5) and 0.054 (5). In the crystal, C—H...π interactions are found.

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.

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

In the title compound, C19H19FN2, the imidazole ring is essentially planar [maximum deviation of 0.0015 (9) Å] and makes dihedral angles of 77.61 (9) and 26.93 (10)° with the benzene rings attached to nitrogen and carbon, respectively. The dihedral angle between the two benzene rings is 78.84 (8)°. A C—H...π interaction is found in the crystal structure.

In the title compound, C25H16N4, the fused ring system is essentially planar [maximum deviation = 0.1012 (15) Å]. The imidazole ring makes dihedral angles of 77.41 (8) and 56.26 (8)° with the phenyl rings attached to nitrogen and carbon, respectively. The dihedral angle between the two phenyl rings is 65.50 (8)°. Weak C—H...π interactions are found in the crystal structure.

In the title compound, C17H12ClNO2, the carbazole unit is nearly planar [maximum deviation = 0.052 (1) Å]. The pyrrole ring makes dihedral angles of 1.92 (8) and 4.71 (11)° with the benzene and furan rings, respectively. Intermolecular N—H...O hydrogen bonds form R22(10) rings in the crystal structure.

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.

In the title molecule, C18H15NO2, the carbazole unit is not planar [maximum deviation from mean plane = 0.236 (2) Å]. The pyrrole ring makes dihedral angles of 1.21 (10) and 16.74 (12)° with the benzene and the furan rings, respectively. The cyclohexene ring adopts a half-chair conformation. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds generate R22(10) loops.

In the title compound, C19H20N2·0.5H2O, the imidazole ring is essentially planar [maximum deviation = 0.005 (1) Å]. The imidazole ring makes dihedral angles of 67.46 (10) and 23.10 (11)° with the attached benzene and phenyl rings, respectively. The dihedral angle between the benzene and phenyl rings is 68.22 (10)°. Intermolecular O—H...N and C—H...N hydrogen bonds are found in the crystal structure.

In the title molecule, C15H17NO, the dihedral angle between the benzene and pyrrole rings is 1.45 (13)°. The cycloheptene ring adopts a slightly distorted boat conformation. In the crystal structure, intermolecular C—H...O hydrogen bonds are found.

In the title molecule, C25H26N4O, the piperidine ring adopts a chair conformation, with the plane through the four coplanar atoms making dihedral angles of 84.76 (6), 82.28 (5) and 81.91 (6)° with the pyridinering and the phenyl rings at the 2 and 6 positions, respectively. The pyridine ring makes dihedral angles of 64.13 (8) and 10.75 (8)° with the phenyl rings at the 2 and 6 positions, respectively. The dihedral angle between the two phenyl rings is 53.57 (8)°. The phenyl rings and one of the methyl groups at position 3 have an equatorial orientation. In the crystal, molecules are linked by N—H...O and C—H...O hydrogen bonds.

In the title compound, C18H18N2, the imidazole ring is essentially planar [maximum deviation = 0.004 (1) Å] and makes dihedral angles of 68.91 (8) and 20.43 (9)° with the tolyl and phenyl rings, respectively. The dihedral angle between the latter rings is 73.62 (8)°. The crystal packing is stabilized by intermolecular C—H...N hydrogen bonds.

In the title molecule, C27H19FN2, the imidazole ring is essentially planar [maximum deviation = 0.004 (1) Å] and makes dihedral angles of 62.80 (6), 36.98 (6), 33.16 (6) and 46.24 (6)°, respectively, with the substituent rings in the 1-, 2-, 4- and 5-positions. No classical hydrogen bonds are observed in the crystal structure.

In the title compound, C13H13NO, the dihedral angle between the benzene ring and the fused pyrrole ring is 0.96 (7)°. The cyclohexenone ring adopts an envelope conformation. Intermolecular N—H...O hydrogen bonds form R22(10) ring motifs in the crystal structure. Weak C—H...π interactions involving the benzene ring also occur.

In the title compound, C17H16N2·H2O, the imidazole ring is essentially planar [maximum deviation = 0.0037 (7) Å]. The imidazole ring makes dihedral angles of 80.74 (7) and 41.62 (7)° with the phenyl rings attached to the N and C atoms, respectively. The dihedral angle between the two phenyl rings is 75.83 (8)°. Intermolecular O—H...N and O—H...O hydrogen bonds are found in the crystal structure.