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Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate

The title compound (systematic name: 3,7-dihy­droxy-9-meth­oxy-1-methyl-6H-benzo[c]chromen-6-one dimethyl sulfoxide monosolvate), C(15)H(12)O(5)·C(2)H(6)OS, was isolated from an unidentified endophytic fungus (belonging to class Ascomycetes) of Taxus sp. In the crystal, both the alternariol 9-O-meth...

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Autores principales: Dasari, Sreekanth, Miller, Kristin I., Kalaitzis, John A., Bhadbhade, Mohan, Neilan, Brett A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685032/
https://www.ncbi.nlm.nih.gov/pubmed/23795051
http://dx.doi.org/10.1107/S1600536813012294
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author Dasari, Sreekanth
Miller, Kristin I.
Kalaitzis, John A.
Bhadbhade, Mohan
Neilan, Brett A.
author_facet Dasari, Sreekanth
Miller, Kristin I.
Kalaitzis, John A.
Bhadbhade, Mohan
Neilan, Brett A.
author_sort Dasari, Sreekanth
collection PubMed
description The title compound (systematic name: 3,7-dihy­droxy-9-meth­oxy-1-methyl-6H-benzo[c]chromen-6-one dimethyl sulfoxide monosolvate), C(15)H(12)O(5)·C(2)H(6)OS, was isolated from an unidentified endophytic fungus (belonging to class Ascomycetes) of Taxus sp. In the crystal, both the alternariol 9-O-methyl ether (AME) and the dimethyl sulfoxide (DMSO) mol­ecules exhibit crystallographic mirror symmetry. One of the hy­droxy groups makes bifurcated hydrogen bonds, viz. an intra­molecular bond with the carbonyl group and an inter­molecular bond with the carbonyl group in an inversion-related AME mol­ecule. In the crystal, the AME mol­ecules are organized into stacks parallel with the b axis by π–π inter­actions between centrosymmetrically related mol­ecules [the distance between the centroid of the central ring and the centroid of the meth­oxy-substituted benzene ring in the next mol­ecule of the stack is 3.6184 (5) Å]. Pairs of DMSO mol­ecules, linked via centrosymmetric C—H⋯O contacts, are inserted into the voids created by the AME mol­ecules, making O—H⋯O and C—H⋯O contacts with the hosts.
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spelling pubmed-36850322013-06-21 Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate Dasari, Sreekanth Miller, Kristin I. Kalaitzis, John A. Bhadbhade, Mohan Neilan, Brett A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound (systematic name: 3,7-dihy­droxy-9-meth­oxy-1-methyl-6H-benzo[c]chromen-6-one dimethyl sulfoxide monosolvate), C(15)H(12)O(5)·C(2)H(6)OS, was isolated from an unidentified endophytic fungus (belonging to class Ascomycetes) of Taxus sp. In the crystal, both the alternariol 9-O-methyl ether (AME) and the dimethyl sulfoxide (DMSO) mol­ecules exhibit crystallographic mirror symmetry. One of the hy­droxy groups makes bifurcated hydrogen bonds, viz. an intra­molecular bond with the carbonyl group and an inter­molecular bond with the carbonyl group in an inversion-related AME mol­ecule. In the crystal, the AME mol­ecules are organized into stacks parallel with the b axis by π–π inter­actions between centrosymmetrically related mol­ecules [the distance between the centroid of the central ring and the centroid of the meth­oxy-substituted benzene ring in the next mol­ecule of the stack is 3.6184 (5) Å]. Pairs of DMSO mol­ecules, linked via centrosymmetric C—H⋯O contacts, are inserted into the voids created by the AME mol­ecules, making O—H⋯O and C—H⋯O contacts with the hosts. International Union of Crystallography 2013-05-11 /pmc/articles/PMC3685032/ /pubmed/23795051 http://dx.doi.org/10.1107/S1600536813012294 Text en © Dasari et al. 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Dasari, Sreekanth
Miller, Kristin I.
Kalaitzis, John A.
Bhadbhade, Mohan
Neilan, Brett A.
Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate
title Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate
title_full Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate
title_fullStr Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate
title_full_unstemmed Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate
title_short Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate
title_sort alternariol 9-o-methyl ether dimethyl sulfoxide monosolvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685032/
https://www.ncbi.nlm.nih.gov/pubmed/23795051
http://dx.doi.org/10.1107/S1600536813012294
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