[2-(3,4-Dimethyl­benzo­yl)phen­yl](4-meth­oxy­phen­yl)methanone

The title mol­ecule, C₂₃H₂₀O₃, is disordered with a 180° rotation about an axis normal to the length of the mol­ecule, with the major and minor components in a 0.545 (5):0.455 (5) ratio. In the major component, the central benzene ring forms dihedral angles of 72.34 (3) and 69.46 (3)° with the dimethyl-substituted and meth­oxy-substituted benzene rings, respectively. Moreover, the central benzene ring forms dihedral angles of 50.86 (5) and 58.43 (4)° with the mean planes of the ketone groups. In the minor component, the corresponding dihedral angles between the benzene rings are 71.36 (4) and 67.94 (4)° and the dihedral angles between the benzene ring and the ketone groups are 56.44 (9) and 55.51 (8)°. In the crystal, C—H...O inter­actions generate a C(9) chain along the a-axis direction.

1′-(1,3-Diphenyl-1H-pyrazol-4-yl)-1′′-methyl-2′,3′,5′,6′,7′,7a'-octa­hydro-1′H-dispiro­[1-benzopyran-3,2′-pyrrolizine-3′,3′′-indoline]-2′′,4-dione

In the title compound C₃₈H₃₂N₄O₃, one pyrrolidine ring adopts an envelope conformation with the N atom as the flap while other pyrrolidine ring adopts an twisted conformation. The pyrrolizine ring forms dihedral angles of 79.24 (5) and 77.57 (5)° with the chromene and indole rings, respectively. The carbonyl O atoms deviate from the least-square planes through the chromene and indole rings by 0.0113 (12) and 0.0247 (12) Å, respectively. In the crystal, non-classical C—H...O inter­actions link the mol­ecules, generating an C(9) chain along the b-axis direction.

Methyl (2Z)-2-bromo­methyl-3-(2,4-dichloro­phen­yl)prop-2-enoate

In the title compound C₁₁H₉BrCl₂O₂, which represents the Z isomer, the methyl­acrylate moiety is essentially planar within 0.039 (2) Å and has an extended trans configuration. The benzene ring makes a dihedral angle of 28.3 (1)° with the mean plane of the methyl­acrylate moiety. The crystal packing is characterized by C—H...O hydrogen bonding and halogen–halogen inter­actions [Cl...Cl = 3.486 (3) Å], resulting in the formation of R₂²(11) ring motifs and connecting the mol­ecules into chains propagating along the b axis.

1′-(1,3-Diphenyl-1H-pyrazol-4-yl)-2′,3′,5′,6′,7′,7a'-hexa­hydro-1′H-di­spiro­[ace­naphthyl­ene-1,3′-pyrrolizine-2′,3′′-chromane]-2,4′′(1H)-dione

In the title compound, C₄₁H₃₁N₃O₃, the pyrazole and pyrrolidine rings adopt twisted conformations. The mean plane of the pyrazole ring forms dihedral angles of 9.11 (12) and 39.65 (11)° with the phenyl rings. The O atoms deviate from the mean planes of the chromene and ace­naphthyl­ene ring systems by 0.194 (15) and 0.079 (15) Å, respectively. In the crystal, molecules are linked via pairs of C—H...O inter­actions,forming inversion dimers with an R₂²(12) ring motif.

Methyl (2Z)-2-bromo­meth­yl-3-(3-chloro­phen­yl)prop-2-enoate

There are two independent mol­ecules (A and B) in the asymmetric unit of the title compound C₁₁H₁₀BrClO₂, which represents the Z isomer. The methyl­acrylate moieties are essentially planar, within 0.084 (2) and 0.027 (5) Å in mol­ecules A and B, respectively. The benzene ring makes dihedral angles of 13.17 (7) and 27.89 (9)° with the methyl­acrylate moiety in mol­ecules A and B, respectively. The methyl­bromide moiety is almost orthogonal to the benzene ring, making dihedral angles of 81.46 (16)° in mol­ecule A and 79.61 (16)° in mol­ecule B. The methyl­acrylate moiety exhibits an extended trans conformation in both mol­ecules. In the crystal, pairs of C—H...O hydrogen bonds result in the formation of quasi-centrosymmetric R₂²(14) AB dimers.

4-(4-Bromo­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one

In the title compound, C₁₆H₁₅BrN₂O₄, the six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation with the disordered methyl­ene C atom as the flap. The pyran ring is almost orthogonal to the chloro­phenyl ring, making a dihedral angle of 87.11 (12)°. The amine-group N atom deviates significantly from the pyran ring [0.238 (3) Å]. The mol­ecular structure is stabilized by an intra­molecular N—H...O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds, which generate C(8) chains running parallel to the b axis. The chains are linked by C—H...π inter­actions. The methyl­ene-group C atom of the chromene system that is disordered, along with its attached H atoms and the H atoms on the two adjacent C atoms, has an occupancy ratio of 0.791 (7):0.209 (7).

rac-4-(4-Chloro­phen­yl)-2-methyl­amino-3-nitro-5,6,7,8-tetra­hydro-4H-chromen-5-one

The title compound, C₁₆H₁₅ClN₂O₄, contains a chiral centre and crystallizes as a racemate. The methyl­ene group β-positioned to the carbonyl group is partially (21%) disordered. It flips to the opposite sides of the corresponding six-membered carbocycle by −0.304 (3) and 0.197 (11) Å, producing alternative envelope conformations. The planes of the pyran and chloro­phenyl rings form a dihedral angle of 86.25 (9)°. The mol­ecular structure is characterized by an intra­molecular N—H...O inter­action, which generates an S(6) ring motif. The corresponding amino N atom deviates from the plane of the pyran ring by 0.1634 (19) Å. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds, forming C(8) chains running parallel to the b-axis direction. The crystal structure also features C—H...π inter­actions.

Methyl 4-anilino-2′,5-dioxo-1′,2′-di­hydro-5H-spiro­[furan-2,3′-indole]-3-carboxyl­ate

In the title compound, C₁₉H₁₄N₂O₅, the spiro junction links an oxindole moeity and a furan ring, which subtend a dihedral angle of 83.49 (6)°. The mol­ecular structure features an N—H...O hydrogen bond, which generates an S(6) ring motif. The crystal packing is governed by two N—H...O inter­actions, one of which generates a centrosymmetric R₂²(14) dimer. The other N—H...O inter­action along with a C—H...O hydrogen bond contributes to the formation of a C₂²[R₂²(9)] dimeric chain running along the b-axis direction.

1′-(1,3-Diphenyl-1H-pyrazol-4-yl)-1′′-(prop-2-en-1-yl)-2′,3′,5′,6′,7′,7a'-hexa­hydro-1′H-di­spiro­[1-benzo­pyran-3,2′-pyrrolizine-3′,3′′-indoline]-2′′,4-dione 0.75-hydrate

In the central aza-bi­cyclo­octane unit of the title compound, C₄₀H₃₄N₄O₃·0.75H₂O, the peripheral pyrrolidine ring adopts an envelope conformation with the N atom deviating by 0.209 (2) Å, whereas the other pyrrolidine ring adopts a twisted conformation with the bridging N and C atoms deviating by −0.218 (2) and 0.236 (3) Å, respectively, from the rest of the ring. The pyrazole ring forms dihedral angles of 42.36 (7) and 24.07 (8)° with its C- and N-attached phenyl groups, respectively. The solvent water mol­ecule has a partial occupancy of 0.75. In the crystal, the water mol­ecules link the fused-ring mol­ecules into chains along the b axis via O—H...N and O—H...O hydrogen bonds. The crystal packing is further stabilized by C—H...π inter­actions involving a methyl­ene group of the pyran ring and the C-attached benzene ring on the pyrazole ring.

1-Ethyl-4′-(1H-indol-3-ylcarbon­yl)-1′-methyl-2,2′′-dioxodi­spiro­[indoline-3,2′-pyrrolidine-3′,3′′-indoline]-4′-carbo­nitrile dimethyl sulfoxide monosolvate

In the title compound, C₃₁H₂₅N₅O₃·C₂H₆OS, the three indole/indoline units are all essentially planar with maximum deviations of 0.0172 (3), 0.053 (2) and 0.07 (2) Å. The pyrrolidine ring adopts an envelope conformation with the C atoms bearing the 1-ethyl-2-oxo­indole substituent (in which the five-membered ring adopts a twisted conformation) as the flap. The dimethyl sulfoxide solvent mol­ecule is disordered over two positions, with an occupancy factor ratio of 0.871 (4):0.129 (4). The solvent components are linked to the heterocyclic mol­ecule via C—H...O and C—H...S hydrogen bonds. In the crystal, the solvent components are linked to the heterocyclic molecule via C—H...O and C—H...S inter­actions, forming R₂²(10) ring motifs. The mol­ecules are further connected into a chain along the a-axis direction via N—H...O hydrogen bonds.

(4S*)-2-Methyl­amino-3-nitro-4-(4-nitro­phen­yl)-5,6,7,8-tetra­hydro-4H-chromen-5-one

The title compound, C₁₆H₁₅N₃O₆, is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The six-membered carbocyclic ring adopts an envelope conformation with the central CH₂ C atom as the flap. The amine N atom deviates from the mean plane of the pyran ring by 0.1365 (15) Å. The nitro­phenyl ring is almost orthogonal to the pyran ring and the mean plane of the six-membered carbocyclic ring, the dihedral angle between their mean planes being 88.30 (7) and 87.61 (8)°, respectively. The mol­ecular structure is stabilized by an intra­molecular N—H...O hydrogen bond, which generates an S(6) ring motif. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds, forming infinite bands lying parallel to (-110) and composed of alternate R₂²(24) and R₂⁴(12) graph-set ring motifs. The crystal structure is further stabilized by C—H...π inter­actions, forming a three-dimensional structure.

2-(4-Chloro-2-nitro­phen­yl)-9-phenyl­sulfonyl-9H-carbazole-3-carbaldehyde

In the title compound, C₂₅H₁₅ClN₂O₆S, the carbazole ring system is essentially planar, with a maximum deviation of 0.152 (3) Å for the C atom to which the 4-chloro-2-nitro­phenyl ring is attached. Its mean plane is almost orthogonal to the phenyl­sulfonyl and nitro­phenyl rings, making dihedral angles of 82.64 (14) and 79.89 (13)°, respectively. The N atom of the nitro group deviates by 0.032 (3) Å from the benzene ring to which it is attached. The mol­ecular structure features intra­molecular O—H...O and C—H...O hydrogen bonds, which generate three S(6) ring motifs. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds, which generate C(6) and C(9) chains running in the [100] and [010] directions, respectively, forming a two-dimensional network lying parallel to (001). There are also R₄³(28) supra­molecular graph-set ring motifs enclosed within these networks.

1-{2-[(E)-2-(2-Nitro­phen­yl)ethen­yl]-1-phenyl­sulfonyl-1H-indol-3-yl}ethanone

In the title compound, C₂₄H₁₈N₂O₅S, the S atom has a distorted tetra­hedral configuration, with bond angles varying from 105.11 (7) to 119.98 (8)°. As a result of the electron-withdrawing character of the phenyl­sulfonyl group, the N—Csp² bond lengths [1.414 (2) and 1.413 (2) Å] are slightly longer than the reported value of 1.355 (14) Å for N atoms with a planar configuration. The indole moiety is essentially planar, with a maximum deviation of 0.0177 (14) Å for the N atom. The phenyl ring of the sulfonyl substituent makes a dihedral angle of 85.70 (7)° with the mean plane of the indole moiety. The mol­ecular structure features intra­molecular C—H...O hydrogen bonds, which generate S(6) and S(12) ring motifs. In the crystal, adjacent mol­ecules are linked via C—H...O hydrogen bonds, forming infinite C(7) chains running along the a-axis direction. The crystal packing also features C—H...π inter­actions, which form a three-dimensional structure.

4′-(1H-Imidazol-2-yl)-3′-[(1H-indol-3-yl)carbon­yl]-1′-methyl-2-oxo­spiro­[indoline-3,2′-pyrrolidine]-3′-carbo­nitrile 0.15-hydrate

In the title compound, C₂₅H₂₀N₆O₂·0.15H₂O, the dihedral angles between the least-squares planes of the indole and pyrrolidine rings and between the oxindole and imidazole rings are 77.66 (7) and 45.31 (7)°, respectively. The pyrrolidine ring and the fused five-membered pyrrolidine ring of the oxindole moiety exhibit twisted conformations. The amide N atom is involved in both intra- and inter­molecular hydrogen bonding, having a bifurcated character. The mol­ecular structure is characterized by an intra­molecular N—H...O hydrogen bond, which generates an S(7) ring motif while an inter­molecular N—H...O hydrogen bond links the organic and solvent water mol­ecules. In the crystal, N—H...N hydrogen bonds generate a zigzag chain running parallel to c-axis direction. The H atoms of the solvent water mol­ecule were not located.

Ethyl 1′-methyl-2-oxo-4′-[(3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetra­methyl­tetra­hydro-3aH-bis­[1,3]dioxolo[4,5-b:4′,5′-d]pyran-5-yl]-2H-spiro­[ace­naphthyl­ene-1,2′-pyrrolidine]-3′-carboxyl­ate

In the title mol­ecule, C₃₀H₃₅NO₈, the ace­naphthyl­enone moiety, two atoms of a methyl pyrrolidine ring (N and C atoms) and four atoms of an ethyl acetate moiety (two C and two O atoms) are disordered over two sets of sites in ratio 0.532 (7):0.468 (7). The three C atoms of a di­meth­oxy­ethane ring and dioxolane ring attached with two methyl groups are disordered over two sets of sites in 0.66 (2):0.34 (2) and 0.62 (2):0.38 (2) ratios, respectively. The major and minor components of the ace­naphthyl­ene ring are essentially planar (r.m.s. deviations = 0.0254 and 0.0436 Å, respectively). The major and minor components of the pyrrolidine ring adopt C-envelope conformations with C atoms displaced by 0.492 (11) and 0.595 (7) Å from the remaining ring atoms. One of the dioxolane rings is disordered with its major component in an envelope conformation [C displaced by 0.511 (11) Å] and the minor fraction is more or less planar with an r.m.s. deviation of 0.070 Å. The other dioxolane ring is in an envelope conformation, with a C atom displaced by 0.438 (3) Å from the remainder of the ring atoms. The crystal packing features C—H...O inter­actions, which generate C(9) chains.

3′-[(1H-Indol-3-yl)carbon­yl]-1′-methyl-2-oxo-4′-(thio­phen-2-yl)­spiro­[indoline-3,2′-pyrrolidine]-3′-carbo­nitrile

In the title compound, C₂₆H₂₀N₄O₂S, the central pyrrolidine ring adopts a twist conformation on the C—C bond involving the spiro C atom. Its mean plane makes dihedral angles of 78.83 (14), 65.91 (15) and 44.49 (18)° with the mean planes of the adjacent oxindole ring system, the indole system and the thio­phene ring, respectively. The indole and indoline units are essentially planar, with maximum deviations of 0.019 (3) and 0.090 (3) Å, respectively. In the oxindole fused-ring system, the pyrrole ring adopts an envelope conformation with the spiro C atom as the flap. In the crystal, pairs of N—H...O hydrogen bonds link the mol­ecules, forming inversion dimers with an R²₂(8) ring motif. The dimers are linked by further N—H...O hydrogen bonds, forming a two-dimensional network lying parallel to (100).

2-Amino-6-(piperidin-1-yl)-4-p-tolyl­pyridine-3,5-dicarbo­nitrile

In the title compound, C₁₉H₁₉N₅, the piperidine ring adopts a chair conformation. The pyridine ring is essentially planar, with a maximum deviation of 0.039 (2) Å for a C atom substituted with a carbonitrile group. The mean plane of the central pyridine ring makes the dihedral angles of 37.90 (14) and 56.10 (12)° with the piperidine and benzene rings, respectively. In the crystal, mol­ecules are linked via N—H...N and C—H...N hydrogen bonds, forming chains along [101], and enclosing R₂²(17) ring motifs. The chains are linked by further C—H...N hydrogen bonds, forming two-dimensional networks lying parallel to (10-1), and enclosing inversion dimers with R₂²(20) ring motifs.