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(±)-(4bS,8aR,10aS)-10a-Ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-octa-hydro-phenanthrene-2,6-dicarbonitrile.

ABSTRACT: The anti-inflammatory and cytoprotective tricyclic title compound, C(21)H(18)N(2)O(2), also known as TBE-31, crystallizes with two nearly superimposable mol-ecules in the asymmetric unit. In both mol-ecules, the three ring systems conform to an envelope-chair-planar arrangement. The central ring, in a cyclohexane chair conformation, contains an axial ethynyl group that bends slightly off from a nearby axial methyl group because of the 1,3-diaxial repulsion between the two groups. In the crystal, weak C-H?N and C-H?O inter-actions form chains along [001].

SUBMITTER: Zheng S

PROVIDER: S-EPMC3515197 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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(±)-(4bS,8aR,10aS)-10a-Ethynyl-4b,8,8-trimethyl-3,7-dioxo-3,4b,7,8,8a,9,10,10a-octa-hydro-phenanthrene-2,6-dicarbonitrile.

Zheng Suqing S Resch Daniel D Honda Tadashi T Jasinski Jerry P JP

Acta crystallographica. Section E, Structure reports online 20121010 Pt 11

The anti-inflammatory and cytoprotective tricyclic title compound, C(21)H(18)N(2)O(2), also known as TBE-31, crystallizes with two nearly superimposable mol-ecules in the asymmetric unit. In both mol-ecules, the three ring systems conform to an envelope-chair-planar arrangement. The central ring, in a cyclohexane chair conformation, contains an axial ethynyl group that bends slightly off from a nearby axial methyl group because of the 1,3-diaxial repulsion between the two groups. In the crystal, ...[more]

PMID: 23284424

Similar Datasets

Crystal structure of (4bS,8aR)-1-isopropyl-4b,8,8-trimethyl-7-oxo-4b,7,8,8a,9,10-hexa-hydro-phenanthren-2-yl acetate.

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(8aR,9R)-9-Hy-droxy-7,8,8a,9-tetra-hydro-furo[3,2-f]indolizin-6(4H)-one.

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Project description:In the title compound, C(22)H(14)BrN(3), the fused-ring system is buckled owing to the ethyl-ene linkage in the central ring; the two flanking aromatic rings are twisted by 25.9?(1) ° with respect to each other. The phenyl ring is twisted by 77.0?(1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, adjacent mol-ecules are linked by two N-H?N hydrogen bonds, generating a zigzag chain along [101].

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Project description:In the title compound, C(20)H(13)N(3)S, the partially saturated ring adopts a twisted half-boat conformation with the methyl-ene C atom closest to the amino-benzene ring lying 0.690 (6) Å out of the plane defined by the five remaining atoms. The dihydro-phenanthrene residue has a folded conformation [dihedral angle between the outer benzene rings = 26.27 (18)°]. The thio-phen-2-yl ring forms a dihedral angle of 63.76 (19)° with the benzene ring to which it is attached. In the crystal, inversion dimers linked by pairs of N-H⋯N hydrogen bonds generate R(2) (2)(12) loops. The dimers are linked into layers in the bc plane by weak C-H⋯π inter-actions. The thio-phen-2-yl ring is disordered over two essentially coplanar but opposite orientations in a 0.918 (4):0.082 (4) ratio.

| S-EPMC3343991 | biostudies-literature

3-Amino-1-(3,4-dimeth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Project description:In the title compound, C(24)H(19)N(3)O(2), the partially saturated ring adopts a distorted half-chair conformation with the methyl-ene-C atom closest to the amino-benzene ring lying 0.664?(3)?Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.1429?Å. The dihedral angle [32.01?(10)°] between the benzene rings on either side of this ring indicates a significant fold in this part of the mol-ecule. The dimeth-oxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03?(9)°]. The mol-ecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimeth-oxy-phen-yl)-5,6-dihydro-benzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873-o2873]. Supra-molecular chains with base vector [201] are formed in the crystal structure via N-H?O hydrogen bonds between the amino H atoms of one mol-ecule inter-acting with the meth-oxy O atoms of a neighbouring mol-ecule. The chains are linked into a three-dimensional architecture by C-H?? inter-actions.

| S-EPMC3344065 | biostudies-literature

3-Amino-1-(2H-1,3-benzodioxol-5-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

Project description:In the title compound, C(23)H(15)N(3)O(2), significant deviations from planarity are evidenced in the values of the dihedral angles formed between the amino-benzene ring and the benzene rings of the 1,3-benzodioxole [65.38 (12)°] and 1,2-dihydro-naphthalene [26.27 (14)°] residues; the dioxole ring has an envelope conformation with the methyl-ene-C being the flap atom. The amino-H atoms form hydrogen bonds to one of the dioxole-O atoms and to one of the cyano-N atoms to generate a two-dimensional array with a zigzag topology that stacks along the ([Formula: see text] 0 2) plane.

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(4aS,10aS)-7-Hydr-oxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phenanthrene: a new diterpenoid compound.

Project description:The new title diterpenoid compound, C(20)H(30)O, is a natural product isolated from Tetra-clinis articulata wood via chloro-form extraction. The asymmetric unit contains four mol-ecules with the same S,S configuration, deduced from the chemical synthesis. Indeed, an overlay analysis, calculated using structure-matching software, shows that the four mol-ecules can be superimposed. The central ring has a half-chair conformation, whereas the saturated ring displays a chair conformation.

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