The whole of the title mol­ecule, C13H14ClNO, is disordered over two sets of sites with a refined occupancy ratio of 0.560 (6):0.440 (6). The oxime group having a C=N double bond adopts an E conformation. The dihedral angles between the rings (all atoms) are 89.5 (5) (major componenent) and 88.0 (6)° (minor component).

The title compound, C19H18O3, crystallizes with three mol­ecules (A, B and C) in the asymmetric unit. The carbonyl O atom shows positional disorder over two sites in mol­ecules A and B; the site-occupancy ratios are 0.76 (3):0.24 (3) and 0.86 (3):0.14 (3), respectively. The ethyl­ene fragments in each mol­ecule have an E conformation, while the C—O—C—C torsion angles indicate near planarity. The dihedral angles formed by the aromatic rings are 20.0 (1), 23.7 (1) and 16.1 (1)° for mol­ecules A, B and C, respectively. Intra­molecular C—H⋯O hydrogen bonds occur in each mol­ecule.

In the title compound, C26H22N2O4, the central pyrrolidine ring adopts a twist conformation and the cyclo­pentane ring of the dihydro­acenapthylene group adopts an envelope conformation with the spiro C atom as the flap. The naphthalene ring system of the dihydro­acenaphthyl­ene group forms dihedral angles of 83.4 (9) and 61.3 (7)°, respectively, with the mean planes of the pyrrolidine and indole rings. The crystal packing is stabilized by inter­molecular C—H⋯O hydrogen bonds. The title compound is a diastereomer of a previously reported structure.

In the title compound, C26H22N2O4, the pyrrolidine ring adopts a twisted conformation and the other five-membered rings adopt envelope conformations with the spiro C atoms as the flap atoms. The naphthalene ring system of the dihydro­acenaphthyl­ene group forms dihedral angles of 89.2 (9) and 75.5 (6)° with the pyrrolidine and indole rings, respectively. The pyrrolidine ring makes a dihedral angle of 80.1 (9)° with the indole ring. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming chains along the b-axis direction.

In the title compound, C22H21N3O4, the central pyrrolidine ring adopts a C-envelope conformation with a C atom 0.6593 (13) Å displaced from the mean plane formed by the remaining ring atoms. The indoline ring systems (r.m.s. devisations of 0.0356 and 0.0547 Å) are almost perpendicular to the mean plane of the pyrrolidine ring, making dihedral angles of 89.7 (6) and 82.5 (6)°. The acetate group attached to the pyrrolidine ring assumes an extended conformation. In the crystal,N—H⋯O and C—H⋯O hydrogen bonds connect adjacent molecules, forming an infinite tape extending along [1-1-1]. The crystal packing is further consolidated by strong π–π inter­actions with a centroid–centroid distance of 3.2585 (8) Å. The title compound is a polymorph of previously reported monoclinic structure [Ganesh et al. (2012 ▶). Acta Cryst. E68, o2902–o2903].

In the title compound, C24H16O2, the naphthalene ring system makes dihedral angles of 78.5 (6) and 65.5 (7)° with the terminal and central benzene rings, respectively. The dihedral angle between the benzene rings is 74.5 (8)°. In the crystal, neighbouring molecules are interlinked through two C—H⋯π interactions, which construct a two-dimensional supramolecular framework extending infinitely along (010).

In the title compound, C25H25N3O4, the central pyrrolidine ring and the two pyrrolidine rings adopt twisted conformations, whereas the piperidine ring in the octa­hydro­indolizine fused ring system adopts a chair conformation. The indoline ring systems are almost perpendicular with respect to the mean plane of the octa­hydro­indolizine ring system, making dihedral angles of 84.4 (5) and 79.4 (5)°. The acetate group attached to the octa­hydro­indolizine ring system assumes an extended conformation. In the crystal, N—H⋯O hydrogen bonds result in the formation of a helical C(7) chain running parallel to [101]. The crystal packing features C—H⋯O hydrogen bonds and C—H⋯π inter­actions.

In the title compound, C22H21N3O4, the central pyrrolidine ring adopts an envelope conformation with the N atom in the flap position. The indoline ring systems are almost perpendic­ular to the mean plane of the pyrrolidine ring, making dihedral angles of 86.4 (8) and 83.1 (8)°. The acetate group attached to the pyrrolidine ring assumes an extended conformation. In thecrystal, N—H⋯O hydrogen bonds result in the formation of a C(7) chain running along [100]. The crystal packing also features π–π inter­actions [centroid–centroid distance = 3.2032 (11) Å].

In the title compound, C20H16O4S, the thiophene ring makes dihedral angles of 72.9 (2) and 60.5 (2)°, respectively, with the dimethoxy benzene and phenyl rings. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into a C(9) chain along the b axis. The S and C atoms of the thio­phene ring are disordered over two sets of sites [site occupancies = 0.675 (3) and 0.325 (3)]. A short inter­molecular S⋯O contact [3.084 (2) Å] is observed in the crystal structure, which also features C—H⋯π inter­actions.

In the title compound, C19H19NO4, the dihedral angle between the mean planes through the benzene rings is 82.18 (7)°. The C=N double bond is trans-configured. The mol­ecules are linked into centrosymmetric dimers via pairs of O—H⋯N hydrogen bonds with the motif R 2 2(6). The crystal packing also features C—H⋯O inter­actions. The methyl group attached to one of the aromatic rings is disordered over two almost equally occupied positions [occpancy ratio = 0.51 (4):0.49 (4)].

In the title compound, C20H21NO5, the dihedral angle between the mean planes through the two rings is 47.1 (8)°. The enoate group assumes an extended conformation. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.061 (1) Å for the O atom. In the crystal, mol­ecules are linked into cyclic centrosymmetric dimers with an R 2 2(6) motif via pairs of O—H⋯N hydrogen bonds. Inter­molecular C—H⋯O hydrogen bonds form a C(8) chain along the b axis. The crystal packing is further stabilized by C—H⋯π inter­actions.

In the title compound, C18H16N2O2, the dihedral angle between the mean planes through the two benzene rings is 56.8 (6)°. The enoate group assumes an extended conformation. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.047 (1) Å for the hy­droxy­imino O atom. In the crystal, the mol­ecules are linked into cyclic centrosymmetric dimers with R 2 2(6) motifs via O—H⋯N hydrogen bonds.

In the title compound, C23H19N3O4, the pyran ring adopts a half-chair conformation, while the pyrrolidine (with a C atom as the flap atom) and the five-membered ring in the indoline (with a C atom as the flap atom) ring system adopt slight envelope conformations. The pyrrolidine ring makes dihedral angles of 83.3 (1) and 60.4 (1)° with the mean plane through all non-H atoms of the indoline and chromene ring systems, respectively. In the crystal, mol­ecules are connected by two unique N—H⋯O and O—H⋯O hydrogen-bonding inter­actions, which form centrosymmetric patterns described by graph-set motifs R 2 2(18) and R 2 2(14). These two motifs combine to form a hydrogen-bonded chain which propagates in the a-axis direction. The crystal structure is also stablized by C—H⋯O inter­actions and by aromatic π–π stacking inter­actions between the pyran and benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.755 (1) Å and slippage = 1.371 (2) Å].

In the title compound, C20H21NO4, the two benzene rings are almost perpendicular to each other, making a dihedral angle of 86.1 (7)°. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hy­droxy­ethanimine [C=N—OH] group being 0.011 (1) Å for the O atom. An intra­molecular C—H⋯O hydrogen bond occurs. The mol­ecules are linked into cyclic centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds. Inter­molecular C—H⋯O hydrogen bonds link the mol­ecules, forming a C(8) chain along the a axis. The crystal packing is further stabilized by C—H⋯π inter­actions.

In the title compound, C18H16ClNO4, the dihedral angle between the mean planes through the aromatic rings is 83.8 (8)°. The hy­droxy­ethanimine group is essentially coplanar with the ring to which it is attached [O—N—C—C torsion angle = −177.96 (13)°]. The mol­ecules are linked into centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds. The crystal packing is further stabilized by C—H⋯O inter­actions.

In the title compound, C29H26N2O3S, the central imidazolidine ring adopts an envelope conformation with the N atom bearing the benzyl ring at the flap. The S atom has distorted tetra­hedral geometry. The benzyl and tosyl rings are oriented at a dihedral angle of 52.1 (1)°. The phenyl rings connected to the imidazolidine ring form a dihedral angle of 28.7 (1)°.

In the title compound, C28H27ClN2O3S, the central imidazolidine ring adopts an envelope conformation with the C atom bearing the chloro­phenyl ring at the flap. The geometry around the S atom is distorted tetra­hedral. Three methyl­ene groups of the cyclo­hexene ring are disordered over two sets of sites [site occupancies = 0.562 (10) and 0.438 (10)]. The crystal packing is stabilized by C—H⋯π inter­actions.

In the title compound, C20H18N4O2, the imidazopyridine fused ring system is almost perpendicular to the benzene ring [dihedral angle = 87.6 (5)°]. The pyridine ring makes a dihedral angle of 35.5 (5)° with the mean plane of the imidazopyridine fragment. The crystal structure is stabilized by an aromatic π–π stacking inter­action between the phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.772 (2) Å, inter­planar distance = 3.546 (2) Å and slippage = 1.286 (2) Å].

In the title compound, C23H19NO4S2, the indole ring system makes dihedral angles of 89.6 (1) and 84.5 (8)° with the phenyl­sulfonyl and phenyl­sulfanyl rings, respectively. In the crystal, the mol­ecules are linked into C(10) chains running along the c axis by an inter­molecular C—H⋯O hydrogen bond. In addition, the crystal packing is stabilized by C—H⋯π inter­actions.

In the title compound, C22H17NO3S, the N atom of the indole ring system deviates by 0.031 (3) Å from a least-squares plane fitted through all nine non-H ring atoms. The geometry around the S atom can be described as distorted tetra­hedral. As a result of the electron-withdrawing character of the phenyl­sulfonyl groups, the N—Csp 2 bond lengths are longer than the typical mean value for N atoms with a planar configuration.

The title compound, C17H12S, which crystallises with two molecules in the asymmetric unit, features four fused rings forming an essentially planar mol­ecule, with maximum deviations from the mean plane of 0.078 (2) and 0.080 (2) Å for C atoms of the thio­phene and phenanthrene groups in both the mol­ecules. The crystal packing features weak C—H⋯π inter­actions.

In the title compound, C28H23ClN2O3S, the central imidazolidine ring adopts a twisted conformation and the S atom has distorted tetra­hedral geometry. The crystal packing is stabilized by C—H⋯O, C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.8302 (10) Å].

The asymmetric unit of the title compound, C21H15NO3S, contains two crystallographically independent mol­ecules. As a result of the electron-withdrawing character of the phenyl­sulfonyl groups, the N—Csp 2 bond lengths are slightly longer than the anti­cipated value of approximately 1.35 Å for N atoms with planar configurations. Both unique S atoms have a distorted tetra­hedral configuration. In each mol­ecule, the indole ring system is essentially planar (r.m.s. deviations for all non-H atoms of 0.020 and 0.023 Å). In one mol­ecule, the indole ring system makes dihedral angles of 65.7 (8) and 73.4 (8)°, respectively, with the benzene and phenyl rings [62.2 (7) and 72.1 (7)°, respectively, in the other mol­ecule].

In the title compound, C32H25NO2S2, the mean plane through the five-membered pyrrolidine ring, which exhibits an envelope conformation, makes dihedral angles of 82.3 (1) and 83.9 (9)° with the benzene ring and the acenaphthyl­ene ring system, respectively. The dihedral angle between the thiophene rings is 19.0(3)°. The crystal structure shows C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.869 (2) Å].

In the title compound, C31H22ClNO2S2, the five-membered pyrrolidine ring, which exhibits an envelope conformation, makes a dihedral angle of 87.4 (2)° with the acenaphthyl­ene ring system. The crystal structure is stabilized by π–π inter­actions [centroid–centroid distance = 3.869 (2) Å]. A C atom and the S atom of the thiophene ring are disordered over two positions with refined occupancies of 0.629 (7) and 0.372 (7).