9,10-Diiodo-phenanthrene.
Ontology highlight
ABSTRACT:
SUBMITTER: Yokota R
PROVIDER: S-EPMC3588929 | biostudies-literature |
REPOSITORIES: biostudies-literature
Similar Datasets
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Project description:In this data article, we present the single-crystal XRD data of phenanthrene-9,10-dicarbonitriles. Detailed structure analysis and photophysical properties were discussed in our previous study, "Intermolecular interactions-photophysical properties relationships in phenanthrene-9,10-dicarbonitrile assemblies" (Afanasenko et al., 2020). The data include the intra- and intermolecular bond lengths and angles.
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Project description:The asymmetric unit of the title compound, C(17)H(13)N(3), contains two independent mol-ecules, which are non-planar as they are buckled owing to the ethyl-ene portion. The dihedral angle between the benzene rings is 26.4?(1)° in one mol-ecule and 32.9?(1)° in the other. In the crystal, the mol-ecules are disposed about a false inversion center, and are linked by two N-H?N hydrogen bonds, generating a dimer. The dimers are linked by further N-H?N hydrogen bonds, resulting in a chain that runs along the longest axis of the ortho-rhom-bic unit cell.
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Project description:A trinuclear nickel complex of phenanthrene-9,10-dione dioxime (H2pqd), namely bis-[μ2-9,10-bis-(oxido-imino)-phenanthrene]-bis-[μ2-10-(oxido-imino)phenanthrene-9-one oxime](phenanthrene-9,10-dione dioxime)trinickel(II) toluene disolvate, [Ni3(C14H8N2O2)2(C14H9N2O2)2(C14H10N2O2)]·2C7H8, has been isolated and its crystal structure determined. This complex features three independent Ni(II) atoms that are arranged in a triangular fashion along with five supporting ligands. There are two square-planar Ni(II) atoms and a third pseudo-octa-hedral Ni(II) atom. While the square-planar Ni(II) atoms are stacked, there are no ligand bridges between them. Each square-planar Ni(II) atom, however, bridges with the pseudo-octa--hedral Ni(II) atom through Ni-N-O-Ni and Ni-O-Ni bonds. A fluorido-bor-ation reaction of the proton-bridged species gave the analogous complex bis-(μ2-bis-{[10-(oxido-imino)-9,10-di-hydro-phenanthren-9-yl-idene]amino}di-fluorido-borato)(phenanthrene-9,10-dione dioxime)trinickel(II) dichloromethane trisolvate, [Ni3(C28H16BF2N4O2)4(C14H10N2O2)]·3CH2Cl2, which shows the same binding structure, but features a widened Ni-Ni inter-action between the square-planar Ni(II) atoms. The proton-bridged complex completes the macrocyclic coordination around the square-planar Ni(II) atoms by means of an O-H⋯O hydrogen bond. Both compounds feature O-H⋯N hydrogen bonds between the oxime and the N atoms attached to square-planar nickel atom. The nickel units show no direct inter-action with their nearest neighbors in the extended lattice. Two π-stacking inter-actions between adjacent mol-ecules are found: one with a centroid-centroid distance of 3.886 (2) Å and the other with a centroid-centroid distance of 4.256 (3) Å. In the latter case, although not aromatic, the distance to the centroid of the central phenanthrene ring is shorter, with a distance of 3.528 (3) Å. Toluene mol-ecules occupy the solvent channels that are oriented along the c axis. In the fluorido-boronate structure, the solvent (DCM) was too badly disordered to be modelled, so its contribution was removed using SQUEEZE [Spek (2015 ▸). Acta Cryst. C71, 9-18].
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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.
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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
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.
| S-EPMC3200934 | biostudies-literature
Project description:In the title compound, C(23)H(17)N(3)O, significant deviations from planarity are evidenced. This is quanti-fied in the dihedral angles formed between the central amino-benzene ring and the benzene rings of the meth-oxy-benzene [67.93?(8)°] and 1,2-dihydro-naphthalene [28.27?(8)°] residues. In the crystal the amino-H atoms form hydrogen bonds to the meth-oxy-O atom 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][Formula: see text] 1) plane.
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Project description:Exposure to polycyclic aromatic hydrocarbons (PAHs) in the food chain is the major human health hazard associated with the Deepwater Horizon oil spill. Phenanthrene is a representative PAH present in crude oil, and it undergoes biological transformation, photooxidation, and chemical oxidation to produce its signature oxygenated derivative, phenanthrene-9,10-quinone. We report the downstream metabolic fate of phenanthrene-9,10-quinone in HepG2 cells. The structures of the metabolites were identified by HPLC-UV-fluorescence detection and LC-MS/MS. O-mono-Glucuronosyl-phenanthrene-9,10-catechol was identified, as reported previously. A novel bis-conjugate, O-mono-methyl-O-mono-sulfonated-phenanthrene-9,10-catechol, was discovered for the first time, and evidence for both of its precursor mono conjugates was obtained. The identities of these four metabolites were unequivocally validated by comparison to authentic enzymatically synthesized standards. Evidence was also obtained for a minor metabolic pathway of phenanthrene-9,10-quinone involving bis-hydroxylation followed by O-mono-sulfonation. The identification of 9,10-catechol conjugates supports metabolic detoxification of phenanthrene-9,10-quinone through interception of redox cycling by UGT, COMT, and SULT isozymes and indicates the possible use of phenanthrene-9,10-catechol conjugates as biomarkers of human exposure to oxygenated PAH.
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