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1.  17α-Acet­oxy-11β-hy­droxy-6α-methyl­pregn-4-ene-3,20-dione 
The title compound, C24H34O5, a fungal-transformed metabolite of the injecta­ble contraceptive medroxyprogesterone acetate, consists of four fused rings (A, B, C and D; steroid labelling). Ring A exists in a half-chair conformation while trans-fused rings B and C adopt chair conformations. The five-membered ring D adopts an envelope conformation with the C atom bound to the methyl group at the flap. In the crystal, adjacent mol­ecules are linked by O—H⋯O and C—H⋯O hydrogen bonds, forming infinite chains along the a axis.
doi:10.1107/S1600536812017631
PMCID: PMC3393278  PMID: 22807835
2.  2-Hy­droxy-16-[(E)-4-methyl­benzyl­idene]-13-(4-methyl­phen­yl)-12-phenyl-1,11-diaza­penta­cyclo­[12.3.1.02,10.03,8.010,14]octa­deca-3(8),4,6-triene-9,15-dione 
In the title compound, C37H32N2O3, an intra­molecular O—H⋯N hydrogen bond generates a five-membered ring, producing an S(5) motif. The piperidone ring adopts a half-chair conformation. The two fused pyrrolidine rings have similar envelope conformations. The interplanar angles between the benzene rings A/B and C/D are 75.68 (7) and 30.22 (6)°, respectively. In the crystal structure, adjacent mol­ecules are inter­connected into chains propagating along the [010] direction via inter­molecular C—H⋯O hydrogen bonds. Further stabilization is provided by weak C—H⋯π inter­actions.
doi:10.1107/S1600536810028357
PMCID: PMC3007522  PMID: 21588384
3.  4a-Hy­droxy-9-(2-meth­oxy­phen­yl)-4,4a,5,6,7,8,9,9a-octa­hydro-3H-xanthene-1,8(2H)-dione 
In the title compound, C20H22O5, an S(6) ring motif is formed by an intra­molecular C—H⋯O hydrogen bond, which contributes to the stabilization of the mol­ecule. In the xanthene system, the cyclo­hexane ring adopts a chair conformation, the cyclo­hexene ring adopts a half-boat conformation and the tetra­hydro­pyran ring adopts a half-chair conformation. The mean plane of the four essentially planar atoms of the tetra­hydro­pyran ring [r.m.s deviation = 0.092 (1) Å] forms a dihedral angle of 64.13 (6)° with the mean plane of the meth­oxy­phenyl group. In the crystal, inter­molecular O—H⋯O and weak C—H⋯O hydrogen bonds link mol­ecules into chains along the a axis, which are further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536810050191
PMCID: PMC3050262  PMID: 21522746
4.  9α-Hy­droxy-12-{[4-(4-hy­droxy­phen­yl)piperazin-1-yl]meth­yl}-4,8-dimethyl-3,14-dioxatri­cyclo­[9.3.0.02,4]tetra­dec-7-en-13-one 
The title compound, C25H34N2O5, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tri­cyclo­[9.3.0.02,4]tetra­dec-7-en-13-one), which in turn was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule comprises a ten-membered ring fused to a five-membered ring with an additional ep­oxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hy­droxy­phenyl-piperazin-1-ylmethyl substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53 (5):0.47 (5). An intra­molecular O—H⋯N hydrogen-bond stabilizes the mol­ecular conformation. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into zigzag chains running along the a-axis direction.
doi:10.1107/S1600536814007430
PMCID: PMC4011210  PMID: 24860343
5.  6-Hy­droxy-5-[(2-hy­droxy-4,4-dimethyl-6-oxo­cyclo­hex-1-en­yl)(4-nitro­phen­yl)meth­yl]-1,3-di­methyl­pyrimidine-2,4(1H,3H)-dione 
In the title compound, C21H23N3O7, the pyrimidine­dione ring adopts a screw-boat conformation, whereas the cyclo­hexenone ring adopts an envelope conformation, with the C atom bearing the methyl groups as the flap atom. The dihedral angle between the mean planes of the pyrimidine­dione and cyclo­hexenone rings is 58.78 (2)°. The pyrimidine­dione and cyclo­hexenone rings form dihedral angles of 59.94 (3) and 54.73 (2)°, respectively, with the 4-nitro­phenyl ring. Relatively strong intra­molecular O—H⋯O hydrogen bonds are observed. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds, forming a chain along the c-axis direction.
doi:10.1107/S1600536813028584
PMCID: PMC3884343  PMID: 24454119
6.  Pregna-1,4,20-trien-3-one, a cytotoxic marine steroid from the marine soft coral Nephthea sp. 
The title compound, C21H28O, was isolated from the cytotoxic lipid extract of the Fidjian soft coral Nephthea sp. The steroid showed inhibitory activity to human colon adenocarcinoma SW480 cells (IC50 = 2.5 µg ml−1). The mol­ecular structure indicates that the A ring is almost planar (r.m.s. deviation = 0.032 Å), the B and C rings adopt chair conformations and the five-membered D ring is a half-chair. The B/C and C/D ring junctions are trans-fused.
doi:10.1107/S1600536810027352
PMCID: PMC3007447  PMID: 21588349
7.  16-[(E)-Benzyl­idene]-2-hy­droxy-12,13-diphenyl-1,11-diaza­penta­cyclo­[12.3.1.02,10.03,8.010,14]octa­deca-3(8),4,6-triene-9,15-dione 
In the title compound, C35H28N2O3, an intra­molecular O—H⋯N hydrogen bonds generates a five-membered ring, producing an S(5) ring motif. The piperidone ring adopts a half-chair conformation and the two pyrrolidine rings adopt an envelope conformation. The dihedral angles formed between adjacent benzene rings are 74.39 (5) and 37.70 (6)°. In the crystal crystal, inter­molecular C—H⋯O hydrogen bonds link mol­ecules into dimers, which are further inter­connected into two-dimensional networks parallel to the ac plane by inter­molecular C—H⋯O hydrogen bonds. The crystal structure is consolidated by weak C—H⋯π inter­actions.
doi:10.1107/S1600536810028345
PMCID: PMC3007256  PMID: 21588383
8.  2-Hy­droxy-2,3,5,10,11,11a-hexa­hydro-1H-pyrrolo­[2,1-c][1,4]benzodiazepine-5,11-dione 
The seven-membered ring of the title compound, C12H12N2O3, which is fused with the phenyl­ene ring, adopts a boat-shaped conformation (with the methine C atom as the prow and the phenyl­ene C atoms as the stern); the H atom on the methine linkage exists in an axial position. The five-membered ring that is fused with the seven-membered ring adopts an envelope conformation (with the C atom bearing the hy­droxy substituent representing the flap) [the deviation from the plane defined by the other four atoms is 0.200 (7) Å in one mol­ecule and 0.627 (5) Å in the other]. The two independent mol­ecules are disposed about a pseudo center of inversion and are connected by a pair of N—H⋯O hydrogen bonds. Adjacent dimers are linked by a pair of O—H⋯O hydrogen bonds, generating a chain running along the b axis.
doi:10.1107/S1600536811025244
PMCID: PMC3212299  PMID: 22090956
9.  5α-Pregna-1,20-dien-3-one 
The title compound, C21H30O, was isolated from the soft coral Sinularia sp. The mol­ecule contains four alicyclic rings, all trans-fused, among which three six-membered rings are in different distorted chair conformations while a five-membered ring assumes an envelope form.
doi:10.1107/S1600536810000863
PMCID: PMC2979690  PMID: 21579778
10.  1-(2-Hy­droxy­eth­yl)-1′-methyl-4′-(naph­thal­en-1-yl)-1′′,2′′,3′′,4′′-tetra­hydro­dispiro­[indoline-3,2′-pyrrolidine-3′,2′′-naphthalene]-2,1′′-dione 
In the title compound, C33H30N2O3, the pyrrolidine ring adopts an envelope conformation in which the H atom attached the an ortho-C atom deviates from the plane, whereas the cyclo­hexa­none ring in the tetra­hydro­naphthalene fused-ring system adopts a sofa conformation. The oxindoline ring system is almost perpendicular with respect to the mean plane of the pyrrolidine ring, with a dihedral angle of 89.0 (1)°. Five intra­molecular C—H⋯O close contacts are observed. In the crystal, mol­ecules associate via O—H⋯O hydrogen bonds, forming R 2 2(14) dimers. In addition, there are weak C—H⋯π inter­actions.
doi:10.1107/S1600536812006617
PMCID: PMC3297867  PMID: 22412670
11.  9-(4-Chloro­phen­yl)-4a-hy­droxy-4,4a,5,6,9,9a-hexa­hydro-3H-xanthene-1,8(2H,7H)-dione 
In the title compound, C19H19ClO4, the central fused ring and the attached cyclo­hexene ring adopt envelope conformations, while the cyclo­hexane ring adopts a chair conformation. The crystal packing is stabilized by O—H⋯O hydrogen bonds, which link the mol­ecules into a chain along the b axis. Weak C—H⋯O bonds also occur.
doi:10.1107/S1600536811031977
PMCID: PMC3200887  PMID: 22058985
12.  12-{[4-(4-Bromo­phen­yl)piperazin-1-yl]meth­yl}-9α-hy­droxy-4,8-dimethyl-3,14-dioxatri­cyclo­[9.3.0.02,4]tetra­dec-7-en-13-one 
The title compound, C25H33BrN2O4, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tri­cyclo­[9.3.0.02,4]tetra­dec-7-en-13-one), which was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule is built up from two fused five- and ten-membered rings with an additional ep­oxy ring system and a bromo­phenyl­piperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy­droxy group forming the flap. An intra­molecular O—H⋯N hydrogen bond stabilizes the mol­ecular conformation. The crystal packing features C—H⋯O hydrogen bonds, which link the mol­ecules into zigzag chains running along the b-axis direction.
doi:10.1107/S1600536814006473
PMCID: PMC3998562  PMID: 24826186
13.  8-[(2-Hy­droxy­phen­yl)imino]-3,5a,9-trimethyl-3a,4,5,5a,8,9b-hexa­hydro­naphtho­[1,2-b]furan-2(3H)-one 
The title compound, C21H23NO3, is a phenyl­imine derivative of the well known anthelmintic agent α-santonin. The trans-fused cyclo­hexane and γ-lactone rings of the α-santonin ring system adopt chair and envelope conformations, respectively, whereas the hexa­diene ring is approximately planar [maximum deviation = 0.029 (4) Å] and forms a dihedral angle of 62.30 (11)° with the benzene ring. An intra­molecular O—H⋯N hydrogen bond is observed.
doi:10.1107/S1600536812027146
PMCID: PMC3393965  PMID: 22798830
14.  9-(2-Chloro­phen­yl)-4a-hy­droxy-3,4,4a,5,6,7,9,9a-octa­hydro-2H-xanthene-1,8-dione 
In the title compound, C19H19ClO4, the di­hydro­pyran ring and the cyclo­hexane ring adopt a half-chair conformation and a chair conformation, respectively. The cyclo­hexene ring has an envelope conformation with the central CH2 C atom as the flap. This atom is disordered over two positions [site-occupancy ratio = 0.744 (12):0.256 (12)] above and below the mean plane formed by the other five atoms. In the crystal, O—H⋯O hydrogen bonds between hy­droxy and carbonyl groups link mol­ecules into chains propagating along [001].
doi:10.1107/S1600536814005297
PMCID: PMC3998631  PMID: 24826146
15.  10-(2-Hy­droxy­eth­yl)-9-(2-hy­droxy­phen­yl)-3,3,6,6-tetra­methyl-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione 
The dihydro­pyridine ring in the title compound, C25H31NO4, adopts an envelope conformation with the methine C atom representing the flap. The cyclo­hexenone rings also adopt envelope conformations with the C atoms bearing the methyl C atoms representing the flaps. The phenolic hy­droxy group forms an intra­molecular hydrogen bond to one of the two keto O atoms. The hy­droxy group of the N-bonded alkyl chain forms an inter­molecular hydrogen bond to the other keto O atom of an adjacent mol­ecule. The latter hydrogen bond leads to the formation of a helical chain running along the b axis.
doi:10.1107/S1600536811006969
PMCID: PMC3051986  PMID: 21522483
16.  5-Hy­droxy-8,8-dimethyl-10-(2-methyl­but-3-en-2-yl)-2H,6H-7,8-dihydro­pyrano[3,2-g]chromene-2,6-dione 
In the title compound, C19H20O5, the pyran ring is in an envelope conformation, whereas the benzene and dihydro­pyran ring system is planar with an r.m.s. deviation of 0.0190 (1) Å. The hy­droxy group is coplanar with the attached benzene ring [r.m.s. deviation = 0.0106 (1) Å]. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked into chains along the b axis by weak C—H⋯O inter­actions. These chains are stacked along the a axis. C—H⋯π and weak π–π inter­actions [centroid–centroid distance = 3.7698 (7) Å] are also observed.
doi:10.1107/S1600536811001565
PMCID: PMC3051790  PMID: 21523091
17.  10-(4-Chloro­phen­yl)-14a-hy­droxy-12-methyl-8,9,9a,10,12,13,14,14a-octa­hydro-5H-10a,14-methano­indeno­[2′,1′:4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione 
The asymmetric unit of the title compound, C26H25ClN2O3, contains two independent mol­ecules (A and B). The conformation of the two mol­ecules differs essentially in the dihedral angle involving the two benzene rings. They are inclined to one another by 52.47 (10) in A and by 31.75 (11)° in B. In both mol­ecules, the six-membered piperidin-3-one rings have chair conformations. In mol­ecule A, all four five-membered rings have twist conformations. In mol­ecule B, only three of the four five-membered rings have twist conformations. The fourth, of the inden-1-one moiety, has an envelope conformation with the spiro C atom, bonded to the N atom of the pyrrolidine ring, as the flap. A weak intra­molecular O—H⋯N hydrogen bond occurs in each independent mol­ecule while a C—H⋯O inter­action is also observed in mol­ecule A. In the crystal, pairs of O—H⋯O hydrogen bonds link the mol­ecules, forming inversion dimers with graph-set motif R 2 2(12). These dimers are further inter­connected by C—H⋯O and C—H⋯π inter­actions, forming a three-dimensional network.
doi:10.1107/S1600536813034107
PMCID: PMC3914117  PMID: 24527024
18.  2-Hy­droxy-2-(3-oxobutan-2-yl)indan-1,3-dione 
In the indane ring system of the title mol­ecule, C13H12O4, the hy­droxy-bearing C atom is 0.134 (1) Å out of the plane of the remaining essentially planar atoms (r.m.s. deviation = 0.010 Å). In the crystal, mol­ecules are linked into chains along the b axis by inter­molecular O—H⋯O hydrogen bonds. Additional stabilization is provided by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811020253
PMCID: PMC3152143  PMID: 21836987
19.  12-Acetyl-6-hy­droxy-3,3,9,9-tetra­methyl­furo[3,4-b]pyrano[3,2-h]xanthene-7,11(3H,9H)-dione 
The title compound, Artonol B, C24H20O7, isolated from the stem bark of Artocarpus kemando, consists of four six-membered rings and one five-membered ring. The tricyclic xanthone ring system is almost planar [maximum deviation 0.115 (5) Å], whereas the pyran­oid ring is in a distorted boat conformation·The furan ring is almost coplanar with the fused aromatic ring, making a dihedral angle of 3.76 (9)°. The phenol ring serves as a intra­molecular hydrogen-bond donor to the adjacent carbonyl group and also acts as an inter­molecular hydrogen-bond acceptor for the methyl groups of adjacent mol­ecules, forming a three-dimensional network in the crystal.
doi:10.1107/S1600536810048592
PMCID: PMC3011782  PMID: 21589606
20.  1′′-Benzyl-1′-methyl-4′-(naphthalen-1-yl)naphthalene-2-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-1,2′′-dione 
In the title compound, C38H32N2O2, the pyrrolidine ring adopts an envelope conformation, whereas the cyclo­hexa­none ring in the tetra­hydro­naphthalene fused-ring system adopts a half-chair conformation. The benzyl ring is oriented at an angle of 67.1 (1)° with respect to the naphthyl ring system. Four intra­molecular C—H⋯O close contacts and C—H⋯π inter­action are observed. In the crystal, mol­ecules associate via C—H⋯O hydrogen bonds, forming a C(12) chain motif along the ac plane.
doi:10.1107/S1600536811021908
PMCID: PMC3151757  PMID: 21837077
21.  6β-Hy­droxy­eremophil-7(11)-en-8β,12-olide 
The title eremophilenolide, C15H22O3, is a natural compound isolated from Senecio laetus Edgew. The two cis-fused six-membered rings have chair confomations and the five-membered ring has a planar envelope conformation [maximum deviation = 0.010 (1) Å]. The β-hy­droxy group participates in inter­molecular O—H⋯O hydrogen bonding, forming mol­ecular chains along the a axis.
doi:10.1107/S1600536811016308
PMCID: PMC3120521  PMID: 21754755
22.  (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[10.6.0.02,9.03,7.013,17]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.
doi:10.1107/S1600536813005436
PMCID: PMC3629507  PMID: 23634025
23.  14-Hy­droxy-8,14-secogammacera-7-ene-3,21-dione from the bark of Lansium domesticum Corr. 
In the title compound (kokosanolide B), C30H48O3, the hexa­hydro- and octa­hydro­naphthalen-2-one ring systems are connected through an ethyl­ene fragment, with a C—CH2—CH2—C torsion angle of 176.2 (2)°. The cyclo­hexene ring adopts a half-chair conformation, while the other six-membered rings adopt distorted chair conformations. In the crystal, adjacent mol­ecules are linked into a zigzag chain along the b axis by O—H⋯O hydrogen bonds involving the hy­droxy and carbonyl groups.
doi:10.1107/S1600536810021136
PMCID: PMC3006935  PMID: 21587852
24.  3-Ethyl-3-hy­droxy-8-meth­oxy­quinoline-2,4(1H,3H)-dione monohydrate 
In the title hydrate, C12H13NO4·H2O, the piperidine ring that is fused to the benzene ring is in a sofa conformation with the chiral C atom lying 0.4084 (18) Å out of the plane of the nine fused-ring atoms. In the crystal, O—H⋯O and N—H⋯O hydrogen bonds link the organic mol­ecules and water mol­ecules into chains running along the b-axis direction. The chains are further connected into layers parallel to the bc plane by π–π inter­actions between inversion-related benzene rings [centroid–centroid distance = 3.8846 (9) Å].
doi:10.1107/S1600536812043280
PMCID: PMC3515289  PMID: 23284509
25.  2-[2-(3-Chloro­phen­yl)-2-oxoeth­yl]-4-hy­droxy-3-(3-meth­oxy­benzo­yl)-2H-1λ6,2-benzothia­zine-1,1-dione 
In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half chair conformation with the S and N atoms displaced by 0.318 (3) and 0.387 (3) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia­zin unit and meth­oxy­benzoyl group are more or less coplanar, the dihedral angle between the mean planes of these rings being 12.37 (10)° while the chloro­phenyl ring is inclined at 81.87 (4) and 73.30 (5)°, respectively, to these rings. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯N inter­actions and the crystal packing is stabilized by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812009014
PMCID: PMC3343952  PMID: 22590033

Results 1-25 (201238)