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5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione

The title mol­ecule, C(14)H(14)O(4), lies on a twofold rotation axis that bis­ects the central benzene ring, with only one half-mol­ecule in the asymmetric unit. The pyran­one systems adopt distorted twist- boat conformations, with the two methyl­ene C atoms displaced by 0.537 (1) and 0.163 (2) Å fr...

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Autores principales: Goswami, Shailesh K., Hanton, Lyall R., McAdam, C. John, Moratti, Stephen C., Simpson, Jim
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3394011/
https://www.ncbi.nlm.nih.gov/pubmed/22798876
http://dx.doi.org/10.1107/S1600536812027699
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author Goswami, Shailesh K.
Hanton, Lyall R.
McAdam, C. John
Moratti, Stephen C.
Simpson, Jim
author_facet Goswami, Shailesh K.
Hanton, Lyall R.
McAdam, C. John
Moratti, Stephen C.
Simpson, Jim
author_sort Goswami, Shailesh K.
collection PubMed
description The title mol­ecule, C(14)H(14)O(4), lies on a twofold rotation axis that bis­ects the central benzene ring, with only one half-mol­ecule in the asymmetric unit. The pyran­one systems adopt distorted twist- boat conformations, with the two methyl­ene C atoms displaced by 0.537 (1) and 0.163 (2) Å from the best-fit plane through the remaining five C and O atoms (r.m.s. deviation = 0.073 Å). In the crystal, bifurcated C—H⋯(O,O) hydrogen bonds link pairs of adjacent mol­ecules in an obverse fashion, stacking mol­ecules along c. These contacts are further stabilized by very weak π–π inter­actions between adjacent benzene rings with centroid–centroid distances of 4.1951 (4) Å. Additional C—H⋯O contacts link these stacks, giving a three-dimensional network.
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spelling pubmed-33940112012-07-13 5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione Goswami, Shailesh K. Hanton, Lyall R. McAdam, C. John Moratti, Stephen C. Simpson, Jim Acta Crystallogr Sect E Struct Rep Online Organic Papers The title mol­ecule, C(14)H(14)O(4), lies on a twofold rotation axis that bis­ects the central benzene ring, with only one half-mol­ecule in the asymmetric unit. The pyran­one systems adopt distorted twist- boat conformations, with the two methyl­ene C atoms displaced by 0.537 (1) and 0.163 (2) Å from the best-fit plane through the remaining five C and O atoms (r.m.s. deviation = 0.073 Å). In the crystal, bifurcated C—H⋯(O,O) hydrogen bonds link pairs of adjacent mol­ecules in an obverse fashion, stacking mol­ecules along c. These contacts are further stabilized by very weak π–π inter­actions between adjacent benzene rings with centroid–centroid distances of 4.1951 (4) Å. Additional C—H⋯O contacts link these stacks, giving a three-dimensional network. International Union of Crystallography 2012-06-27 /pmc/articles/PMC3394011/ /pubmed/22798876 http://dx.doi.org/10.1107/S1600536812027699 Text en © Goswami et al. 2012 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
Goswami, Shailesh K.
Hanton, Lyall R.
McAdam, C. John
Moratti, Stephen C.
Simpson, Jim
5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione
title 5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione
title_full 5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione
title_fullStr 5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione
title_full_unstemmed 5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione
title_short 5,6-Dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione
title_sort 5,6-dimethyl-1,2,9,10-tetra­hydro­pyrano[3,2-f]chromene-3,8-dione
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3394011/
https://www.ncbi.nlm.nih.gov/pubmed/22798876
http://dx.doi.org/10.1107/S1600536812027699
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