Ethyl 27-oxo-15-oxa-2,20-diaza­hexa­cyclo­[18.6.1.0^1,8.0^2,6.0^9,14.0^21,26]hepta­cosa-9,11,13,21,23,25-hexa­ene-7-carboxyl­ate

In the title compound, C₂₇H₃₀N₂O₄, the pyrrolidine ring adopts a twisted conformation. The indoline ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 81.7 (8)°. In the crystal, mol­ecules are linked into centrosymmetric dimers with graph-set motif R₂²(16) via pairs of C—H...O hydrogen bonds. The terminal ethyl group of the ester group is disordered over two sets of sites, with a site-occupancy ratio of 0.587 (11):0.413 (11).

Ethyl 8,13-dioxa-21-aza­penta­cyclo­[18.5.1.0^2,7.0^14,19.0^21,25]hexa­cosa-2(7),3,5,14,16,18-hexa­ene-26-carboxyl­ate

In the title compound, C₂₆H₃₁NO₄, the five-membered rings of the central pyrrolizine system adopt N-envelope conformations. The ethyl acetate group adopts an extended conformation. The dihedral angle between the benzene rings is 36.6 (1)°. In the crystal, C—H...O hydrogen bonds form a zigzag chain running along the b-axis directions. The crystal structure is futher consolidated by C—H...π inter­actions.

(E)-1-Ferrocenyl-3-[2-(2-hy­droxy­eth­oxy)phen­yl]prop-2-en-1-one

In the title compound, [Fe(C₅H₅)(C₁₆H₁₅O₃)], the cyclo­penta­dienyl rings are in an eclipsed conformation and the benzene ring makes dihedral angles of 10.84 (9) and 12.35 (9)°, respectively, with the substituted and unsubstituted cyclo­penta­dienyl rings. In the crystal, mol­ecules form inversion dimers through pairs of O—H...O hydrogen bonds. Weak C—H...O hydrogen bonds are observed between the dimers.

1-(4-{2-[(E)-3-(4-Chloro­phen­yl)-3-oxo­prop-1-en-1-yl]phen­oxy}but­yl)-1H-indole-3-carbaldehyde

In the title compound, C₂₈H₂₄ClNO₃, the dihedral angles between the central benzene ring and the indole ring system and the chlorobenzene ring are 70.81 (5) and 78.62 (5)°, respectively. The mol­ecular structure is stabilized by a weak intra­molecular C—H...O inter­action. In the crystal, pairs of C—H...O hydrogen bonds link the mol­ecules into inversion dimers with an R₂²(14) motif.

2-Ferrocenyl-3-nitro-2H-chromene

In the title compound, [Fe(C₅H₅)(C₁₄H₁₀NO₃)], the cyclo­penta­dienyl rings are in an eclipsed conformation and the pyran ring adopts a half-chair conformation. The mean plane of the pyran ring makes dihedral angles of 79.33 (1) and 80.73 (1)°, respectively, with the substituted and unsubstituted cyclo­penta­dienyl rings. In the crystal, pairs of C—H...O hydrogen bonds link the mol­ecules into inversion dimers with R₂²(16) motifs.

Methyl 11-hy­droxy-9-[1-(4-meth­oxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-18-oxo-10-oxa-2-aza­penta­cyclo­[9.7.0.0^1,8.0^2,6.0^12,17]octa­deca-12(17),13,15-triene-8-carboxyl­ate

In the title compound, C₃₄H₃₂N₂O₇, the furan ring adopts a twist conformation and both the pyrrolidine rings adopt envelope conformations with O and C as flap atoms. The β-lactam ring makes a dihedral angles of 80.20 (10)° with the furan ring, of 75.55 (10)° with the pyrrolidine ring, of 12.26 (10)° with the meth­oxy­phenyl ring and of 73.77 (13)° with the phenyl ring. The O atom attached to the β-lactam ring deviates by 0.0385 (13) Å from the ring plane. The mol­ecular conformation is stabilized by intra­molecular O—H...N and C—H...O hydrogen bonds. The packing of the crystal is stabilized by inter­molecular C—H...O hydrogen bonds, which form a chain running along the b axis.

(3E)-11,16-Dioxatricyclo­[15.4.0.0^5,10]henicosa-1(21),3,5,7,9,17,19-heptaen-2-one

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.

(1′S,12′R,13′S,17′S)-15′,15′-Dimethyl-1,2-dihydro-11′,14′,16′,18′-tetra­oxa-7′-aza­spiro­[indole-3,8′-penta­cyclo­[10.6.0.0^2,9.0^3,7.0^13,17]octa­deca­ne]-2,10′-dione

In the title compound, C₂₂H₂₄N₂O₆, the indole ring has a twist conformation and the tetra­hydro-2H-pyran-2-one ring a half-chair conformation. One of the pyrrolidine rings adopts an envelope conformation on the N atom, while the other has a twist conformation; the `butterfly' angle between their mean planes is 62.98 (11)°. The dioxolane ring adopts a twist conformation and the tetra­hydro­furan ring has an envelope conformation on the C atom in the fused tetra­hydro-2H-pyran-2-one ring adjacent to the O atom of the tetra­hydro­furan ring. The `butterfly' angle between the mean planes of these two five-membered rings is 69.14 (10)°. In the crystal, mol­ecules are linked by N—H...O hydrogen bonds, forming chains along the a axis.

6-Ferrocenoyl-7-phenyl­spiro­[hexa­hydro­pyrrolo­[1,2-c][1,3]thia­zole-5,11′-indeno­[1,2-b]quinoxaline]

In the title compound, [Fe(C₅H₅)(C₃₂H₂₄N₃OS)], both the thia­zolidine ring and the pyrrolidine ring adopt an envelope conformation, with the S atom and the phenyl-bearing C atom, respectively, as the flaps. The thia­zolidine ring mean plane makes a dihedral angle of 59.08 (11)° with the pyrrolidine ring mean plane, which in turn makes a dihedral angle of 83.40 (10)° with the cyclo­pentane ring, indicating that the latter two rings are almost orthogonal to one another. In the crystal, a pair of C—H...O hydrogen bonds link the mol­ecules forming inversion dimers. The dimers are linked via π–π inter­actions [centroid–centroid distance = 3.7764 (10) Å] involving the quinoxaline moieties forming chains propagating along [1-10].

6-Ferrocenoyl-7-(4-fluoro­phen­yl)spiro­[hexa­hydro­pyrrolo­[1,2-c][1,3]thia­zole-5,11′-indeno­[1,2-b]quinoxaline]

In the title compound, [Fe(C₅H₅)(C₃₂H₂₃FN₃OS)], both the thia­zolidine ring and the pyrrolidine ring adopt a twist conformation on the N—C(H) bridging bond. Their mean planes are inclined to one another by 10.05 (10)°, and they make dihedral angles of 82.09 (10) and 89.67 (11)°, respectively, with the cyclo­pentane ring. The F atom deviates by −0.0238 (2) Å from the benzene ring to which it is attached. In the crystal, mol­ecules are linked by a pair of C—H...O hydrogen bonds, forming inversion dimers.

2-(4-Bromo­benzo­yl)-1-ferrocenyl­spiro­[11H-pyrrolidizine-3,11′-indeno­[1,2-b]quinoxaline]

In the title compound, [Fe(C₅H₅)(C₃₃H₂₅BrN₃O)], the fused four-ring system, 11H-indeno­[1,2-b]quinoxaline is essentially planar, with a maximum deviation of 0.087 (3) Å from the least-squares plane of the attached benzene ring. The pyrrolidine rings adopt envelope conformation and make a dihedral angle of 51.76 (19)° with each other. The cyclopentadiene rings of the ferrocenyl moiety have an eclipsed conformation. The Br atom deviates by 0.0190 (9) Å from the attached benzene ring. The mol­ecular structure features an intra­molecular C—H...N inter­action, which generates an S(8) ring motif. The crystal packing features C—H...O inter­actions, which generate R₂²(18) centrosymmetric dimers, as well as C—H...π inter­actions.

2-[(Ferrocen-1-yl)(hy­droxy)meth­yl]prop-2-ene­nitrile

In the title ferrocene derivative, [Fe(C₅H₅)(C₉H₈NO)], the dihedral angle between the ene­nitrile group and the substituted cyclo­penta­dienyl ring is 71.2 (1)°. The cyclopentadienyl rings of the ferrocene moiety are arranged in an eclipsed conformation. The hy­droxy group, and the corresponding methine H atom, are disordered over two sets of sites with site-occupancy factors of 0.744 (4) and 0.256 (4). An intra­molecular C—H...O close contact is observed. In the crystal, O—H...N hydrogen bonds form a C(6) chain along [100].

(1S,3′S,3a′R,6′S)-6′-(2-Chloro­phen­yl)-3′-[(2R,3S)-1-(4-meth­oxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetra­hydro-2H,2′H-spiro­[ace­naphthyl­ene-1,1′-pyrrolo­[1,2-c][1,3]thia­zole]-2′,2′-dicarbo­nitrile

The mol­ecular conformation of the title compound, C₄₁H₂₉ClN₄O₃S, is stabilized by intra­molecular C—H...O and C—H...Cl hydrogen bonds. The thia­zole ring adopts an envelope conformation with the N atom as the flap, while the pyrrolidine ring has a twisted conformation on the N—C bond involving the spiro C atom. The β la­ctam ring makes dihedral angles of 39.74 (15) and 16.21 (16)° with the mean planes of the thia­zole and pyrrolidine rings, respectively. The thia­zole ring mean plane makes dihedral angles of 23.79 (13) and 70.88 (13) ° with the pyrrolidine and cyclo­pentane rings, respectively, while the pyrrolidine ring makes a dihedral angle of 85.63 (13)° with the cyclo­pentane ring. The O atom attached to the β la­ctam ring deviates from its mean plane by 0.040 (2) Å, while the O atom attached to the cyclo­pentane ring deviates from its mean plane by 0.132 (2) Å. In the crystal, mol­ecules are linked by C—H...O hydrogen bonds, forming chains along [010], and C—H...π and π-π inter­actions [centroid-centroid distance = 3.6928 (17) Å].

Methyl 9-(4-meth­oxy­phen­yl)-19-methyl-3,12-di­aza­penta­cyclo­[10.7.0.0^2,10.0^3,8.0^13,18]nona­deca-1(19),13(18),14,16-tetra­ene-10-carboxyl­ate

The title ester, C₂₇H₃₀N₂O₃, crystallizes with two independent mol­ecules in the asymmetric unit whose geometrical features are similar. In each mol­ecule, the pyrrolidine ring adopts an envelope conformation, with the fused C atom shared with the piperidine ring as the flap, and the piperidine ring adopts a chair conformation. In the crystal, C—H...π inter­actions link the inversion-related molecules and form a dimeric arrangement in the unit cell.

8,13,26-Trioxa-23-thia-21-aza­penta­cyclo­[18.6.0.0^2,7.0^14,19.0^21,25]hexa­cosa-2(7),3,5,14,16,18-hexa­ene

In the title compound, C₂₁H₂₃NO₃S, both the thia­zole and oxazolidine rings adopt twist conformations. The mean plane of the thia­zole ring makes a dihedral angle of 61.02 (7)° with the oxazolidine ring mean plane, and dihedral angles of 22.72 (6) and 75.07 (6)° with the benzene rings. The benzene rings are almost perpendicular to one another, making a dihedral angle of 89.14 (6)°. There are bifurcated intra­molecular C—H...O hydrogen bonds in the mol­ecular structure. In the crystal, mol­ecules are linked via C—H...π inter­actions, forming chains propagating along [100].

8,11,24-Trioxa-21-thia-19-aza­penta­cyclo­[16.6.0.0^2,7.0^12,17.0^19,23]tetra­cosa-2(7),3,5,12,14,16-hexa­ene

In the title compound, C₁₉H₁₉NO₃S, the thia­zole and oxazolidine rings each adopt an envelope conformation, with the S and O atoms as the respective flap atoms. The thia­zole and oxazolidine rings (all atoms) make a dihedral angle of 66.39 (11)° while the phenyl rings subtend a dihedral angle of 22.71 (10)°.

6a-Nitro-6-phenyl-6,6a,6b,7,8,9,10,12a-octa­hydro­spiro­[chromeno[3,4-a]indol­izine-12,3′-indolin]-2′-one

In the title compound, C₂₈H₂₅N₃O₄, the central pyrrolidine ring adopts adopts an envelope conformation with the N atom as the flap and the piperidine ring adopts a chair conformation. The pendant pyrrolidine ring is almost planar (r.m.s. deviation = 0.008 Å). An intra­molecular C—H...O inter­action closes an S(6) ring. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds generate R₂²(8) loops.

2-Methyl-4-(naphthalen-2-yl)-3a-nitro-3,3a,4,9b-tetra­hydro-2H-spiro­[chromeno[3,4-c]pyrrole-1,3′-indolin]-2′-one

In the title compound, C₂₉H₂₃N₃O₄, the 2-methylpyrrolidine ring adopts a twist conformation on the N—C bond involving the spiro C atom, while the hydropyran ring adopts an envelope conformation with the methine C atom bonded to the O atom as the flap. The mean plane of the indoline-2-one ring system is almost perpendicular to the mean plane of the pyrrolidine ring, making a dihedral angle of 89.73 (8)°. The latter ring makes dihedral angles of 47.80 (8) with the naphthalene ring system and 32.38 (8)° with the hydropyran ring mean plane. There is an intra­molecular C-H...O hydrogen bond involving the indoline-2-one O atom. In the crystal, adjacent mol­ecules are linked via N—H...O hydrogen bonds, forming chains propagating along [100]. The chains are linked via weak C—H...O hydrogen bonds, forming two-dimensional networks, lying parallel to (101), and consolidated by C—H...π inter­actions.

6-(4-Meth­oxy­phen­yl)-6a-nitro-6,6a,6b,7,8,9,10,12a-octa­hydro­spiro­[chromeno[3,4-a]indolizine-12,3′-indolin]-2′-one

In the title compound, C₂₉H₂₇N₃O₅, the hydropyran ring adopts an envelope conformation with the methine C atom bearing the para-meth­oxy­benzene ring as the flap. The central pyrrolidine ring has a twist conformation on the N—C bond involving the spiro C atom. The piperidine ring adopts a chair conformation. An intra­molecular C—H...O contact closes an S(7) ring. In the crystal, inversion dimers linked by C—H...O inter­actions generate R₂²(18) loops and N—H...O hydrogen bonds connect the dimers into [100] chains.

Allyl 2-(2,2-dimethyl-3a,6a-di­hydro­furo[3,2-d][1,3]dioxol-5-yl)-4-oxo-4H-chromene-3-carboxyl­ate

In the title compound, C₂₀H₁₈O₇, the dioxolane ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap, and its mean plane makes a dihedral angle of 73.25 (2)° with the pyran ring mean plane. The furan ring makes dihedral angles of 67.43 (12) and 6.20 (11)° with the mean plane of the dioxolane and pyran rings, respectively. The O atom attached to the pyran ring deviates by 0.0219 (2) Å from its mean plane. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds, forming chains along [010] and enclosing R₂²(9) loops. They stack along the a axis with π–π inter­actions involving the 4H-chromene units [centroid–centroid distances of 3.6389 (13) and 3.6555 (13) Å]. The terminal CH₂=CH- atoms of the allyl acetate group are disordered over two sets of sites with a refined occupancy ratio of 0.717 (6):0.283 (6).

Methyl 2-(2,2-dimethyl-3a,6a-di­hydro­furo[3,2-d][1,3]dioxol-5-yl)-4-oxo-4H-chromene-3-carboxyl­ate

In the title mol­ecule, C₁₈H₁₆O₇, the dioxolane ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap. The furan ring is almost coplanar with the pyran ring, with a dihedral angle of 1.04 (10)° between the planes, and it makes a dihedral angle of 67.97 (11)° with the mean plane of the dioxolane ring. The latter makes a dihedral angle of 67.15 (10)° with the pyran ring. The O atom attached to the pyran ring deviates by −0.009 (1) Å. The crystal packing features C—H...O hydrogen bonds, forming a three-dimensional structure. The meth­oxy­carbonyl atoms are disordered over two positions, with a refined occupancy ratio of 0.508 (18):0.492 (18).

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.

(1S,1'S,2'R,4a'S,9a'S,9b'R)-1'-Acet­yloxy-2,4'-dioxo-2',4',4a',7',8',9',9a',9b'-octa­hydro-1'H,2H-spiro­[ace­naphthyl­ene-1,5'-pyrano[4,3-a]pyrrolizin]-2'-ylmethyl acetate

In the title compound C₂₆H₂₅NO₇, the mean plane through the lactone-substituted ring of the pyrrolizidine moiety forms dihedral angles of 78.46 (6) and 58.28 (8)° with the ace­naphthyl­ene moiety and the sugar based-lactone ring, respectively. The sum of the angles at the the N atom of the pyrrolizidine ring (335.0°) is in accordance with sp³ hybridization. Some atoms of the acetate group are disordered and were refined using a split model [occupancy ratio 0.673 (10):0.327 (10)].

2,15-Dioxa-7,18,19,20,23-penta­aza­hepta­cyclo­[21.6.1.1^17,20.0^1,8.0^3,7.0^9,14.0^24,29]hentriaconta-9,11,13,17(31),18,24,26,28-octaen-30-one

In the title compound, C₂₄H₂₃N₅O₃, the oxindole ring system is nearly planar, with a dihedral angle between the two fused rings of 3.3 (1)°. In the fused pyrrolo–oxazole ring system, the oxazole and pyrrolidine rings adopt envelope conformations with the spiro C atom and one of the methyl­ene C atoms, respectively, as the flap atoms. In the crystal, mol­ecules are linked into a helical chain along the b axis via C—H...O inter­actions generating R₂¹(7) and R₂²(8) ring motifs.

(4′-Acet­yloxy-1,3,1′-trioxo-1,3,4,4a,4b,5,6,7,9,9a-deca­hydro­spiro­[indene-2,9′-pyrano[4,3-a]pyrrolizin]-3′-yl)methyl acetate

In the title compound, C₂₃H₂₃NO₈, the dihedral angle between the five- and six-membered rings of the indene-dione moiety is 3.09 (13)°. The mean plane of the five-membered ring (which has a flat envelope conformation with the spiro C atom as the flap) is inclined to the mean plane of the central five-membered ring of the pyrrolizine unit by 76.48 (12)°. This central ring has a twist conformation on the N—C(spiro) bond. The outer ring of the pyrrolizine unit has an envelope conformation with the N atom as the flap. The mean planes of these two fused rings are inclined to one another by 65.28 (15)°. The pyran ring has a screw-boat conformation and its mean plane makes a dihedral angle of 29.50 (11)° with the mean plane of the central five-membered ring of the pyrrolizine unit. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds, forming two-dimensional networks lying parallel to the ab plane.