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(3S,11Z)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10-hexa-hydro-1H-2-benz-oxacyclo-tetra-decine-1,7(8H)-dione (cis-zearalenone): a redetermination.

ABSTRACT: The title compound, also known as cis-zearalenone (cis-ZEN), C(18)H(22)O(5), has already been reported elsewhere [Griffin et al. (1981 ?). ACA Ser.29, 35], but no atomic coordinates are publicly available. The mol-ecule is of inter-est with respect to its toxicity. In the crystal, intra-molecular O-H?O hydrogen bonds stabilize the mol-ecular conformation, while inter-molecular O-H?O hydrogen bonds link the mol-ecules to form infinite chains along the [110] and [1-10] directions. The absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

SUBMITTER: Koppen R

PROVIDER: S-EPMC3297891 | biostudies-other | 2012 Mar

REPOSITORIES: biostudies-other

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(3S,11Z)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10-hexa-hydro-1H-2-benz-oxacyclo-tetra-decine-1,7(8H)-dione (cis-zearalenone): a redetermination.

Köppen Robert R Riedel Juliane J Emmerling Franziska F Koch Matthias M

Acta crystallographica. Section E, Structure reports online 20120224 Pt 3

The title compound, also known as cis-zearalenone (cis-ZEN), C(18)H(22)O(5), has already been reported elsewhere [Griffin et al. (1981 ▶). ACA Ser.29, 35], but no atomic coordinates are publicly available. The mol-ecule is of inter-est with respect to its toxicity. In the crystal, intra-molecular O-H⋯O hydrogen bonds stabilize the mol-ecular conformation, while inter-molecular O-H⋯O hydrogen bonds link the mol-ecules to form infinite chains along the [110] and [1-10] directions. The absolute con ...[more]

PMID: 22412694

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(3S)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10,11,12-octa-hydro-1H-2-benzoxacyclo-tetra-decine-1,7(8H)-dione (zearalanone) monohydrate.

Project description:The absolute configuration of the title compound, C(18)H(24)O(5)·H(2)O, was not been determined by anomalous-dispersion effects, but has been assigned by reference to an unchanging chiral centre in the synthetic procedure. Intra-molecular O-H?O hydrogen bonds stabilize the mol-ecular conformation. In the crystal, O-H?O hydrogen bonds link the main mol-ecules and the water mol-ecules, forming an infinite three-dimensional network.

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cis-3,3-Dimethyl-3,3a,4,5,6,6a-hexa-hydro-1H-cyclo-penta-[c]furan-1,6-dione.

Project description:The bicyclic mol-ecule of the title compound, C(9)H(12)O(3), contains two five-membered rings with different functional groups, viz. a ketone and an ester. Both rings assume an envelope conformation. The mean planes of these functional groups form a dihedral angle of 60.7?(1)°. The crystal structure exhibits weak inter-molecular C-H?O inter-actions, which link the mol-ecules into zigzag chains extended in the [010] direction. The unit cell contains a racemic mixture of enanti-omers.

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6,7,8,9-Tetra-hydro-4b,9b-dihy-droxy-indano[1,2-b]indoline-9,10-dione monohydrate.

Project description:In the title compound, C(15)H(13)NO(4)·H(2)O, the organic mol-ecule adopts a V-shaped conformation in which the dihedral angle between the five-membered rings is 68.33?(5)°. The cyclo-hexenone ring adopts an envelope conformation, with one of the methyl-ene C atoms displaced by 0.607?(4)?Å from the plane through the other atoms. In the crystal, inter-molecular N-H?(O,O) and O-H?O hydrogen bonds link the components into (001) sheeets and C-H?O inter-actions and aromatic ?-? stacking [centroid-centroid separation = 3.6176?(19)?Å] help to consolidate the packing.

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3a,8a-Dihy-droxy-1,3,3a,8a-tetra-hydro-indeno-[1,2-d]imidazole-2,8-dione.

Project description:In the title mol-ecule, C(10)H(8)N(2)O(4), the imidazolidine ring adopts a twisted conformation. In the crystal, the mol-ecules are linked via a pair of bifurcated inter-molecular O-H?O hydrogen bonds, forming an inversion dimer. The dimers are further linked via N-H?O hydrogen bonds into a tape along the b axis.

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Redetermination of di-?-hydrido-hexa-hydridotetra-kis(tetra-hydro-furan)dialuminium(III)magnesium(II).

Project description:The structure of the title compound, [Mg(AlH(4))(2)(C(4)H(8)O)(4)], has been redetermined at 150?K. The Mg(II) ion is hexa-coordinated to four tetra-hydro-furan (THF) ligands, and two AlH(4) (-) anions through bridging H atoms. The Al-H distances are more precise compared to those previously determined [Nöth et al. (1995 ?). Chem. Ber. 128, 999-1006; Fichtner & Fuhr (2002 ?). J. Alloys Compd, 345, 386-396]. The mol-ecule has twofold rotation symmetry.

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(E)-9-(4-Chloro-styr-yl)-3,4,5,6,7,9-hexa-hydro-2H-xanthene-1,8-dione.

Project description:In the title compound, C(21)H(19)ClO(3), the two cyclo-hexenone rings adopt half-chair conformations, whereas the pyran ring adopts a boat conformation. The 4-chloro-phenyl ring is almost perpendicular to the plane through the four C atoms of the pyran ring [dihedral angle = 87.97?(6)°]. In the crystal, weak C-H?O hydrogen bonds link the mol-ecules into a chain parallel to the a-axis.

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2-Hy-droxy-2,3,5,10,11,11a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11-dione.

Project description:The seven-membered ring of the title compound, C(12)H(12)N(2)O(3), which is fused with the phenyl-ene ring, adopts a boat-shaped conformation (with the methine C atom as the prow and the phenyl-ene 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 hy-droxy substituent representing the flap) [the deviation from the plane defined by the other four atoms is 0.200?(7)?Å in one mol-ecule and 0.627?(5)?Å in the other]. The two independent mol-ecules 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.

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(11aS)-7-Bromo-2,3,5,10,11,11a-hexa-hydro-1H-pyrrolo-[2,1-c][1,4]benzodiazepine-3,11-dione.

Project description:The title compound, C(12)H(11)BrN(2)O(2), was prepared by an intra-cyclization reaction of (S)-1-(5-bromo-2-nitro-benz-yl)-5-oxopyrrolidine-2-carb-oxy-lic acid methyl ester in the presence of EtOH/Fe. The five-membered pyrrolidinone ring adopts an approximate envelope conformation, while the seven-membered diazepanone ring displays a twisted boat conformation. Inter-molecular classical N-H?O hydrogen bonds and weak C-H?O inter-actions help to stabilize the crystal structure.

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1-Benzyl-3-(2-furylmeth-yl)-1,2,3,4,5,6-hexa-hydro-spiro-[benzo[h]quinazoline-5,1'-cyclo-hexa-ne]-2,4-dione.

Project description:The title compound, C(29)H(28)N(2)O(3), displays anti-depressant and anti-cancer activities. The furan ring is disordered over two orientations [site occupancies 0.690?(12)/0.310?(12)] related by a rotation of 180°. The ring conformations are chair for the cyclo-hexane ring, boat for the cyclo-hexa-diene ring and twist for the pyrimidine ring. The crystal packing is determined solely by van der Waals inter-actions.

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(6S,7S,8S,8aS)-6-Ethyl-7,8-dihy-droxy-1,5,6,7,8,8a-hexa-hydro-indolizin-3(2H)-one monohydrate.

Project description:The absolute configuration of the title compound, C(10)H(17)NO(3)·H(2)O, was assigned from the synthesis. In the mol-ecular structure, the central six-membered ring of the indolizine moiety adopts a chair conformation, with two atoms displaced by -0.578?(2) and 0.651?(1)?Å from the plane of the other four atoms [maximum deviation 0.019?(2)?Å] The conformation of the fused oxopyrrolidine ring is close to that of a flat envelope, with the flap atom displaced by 0.294?(1)?Å from the plane through the remaining four atoms. In the crystal, one of the hy-droxy groups is hydrogen-bonded to two water mol-ecules, while the other hy-droxy group exhibits an inter-molecular hydrogen bond to the carbonyl O atom, resulting in a chain parallel to the b axis.

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