pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene

Fernando de C. da Silva; James L. Wardell; Solange M. S. V. Wardell; Vitor F. Ferreira; John N. Low; Christopher Glidewell

doi:10.1107/S0108270107039194

pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene

Fernando de C. da Silva, James L. Wardell, Solange M. S. V. Wardell, Vitor F. Ferreira, John N. Low, Christopher Glidewell

School of Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The title compounds, namely 6- methoxy- 3,3- dimethyl- 3Hbenzo[ f] chromene, C16H16O2, ( III), and racemic 3- bromo2,2,6,6- tetramethyl- 3,4- dihydro- 2H, 6H- 1,5- dioxatriphenylene, C20H21BrO2, ( IV), were both synthesized in one- step regioselective Wittig reactions from substituted 1,2- naphthoquinones. The new ring in both compounds adopts a screw- boat conformation. A single pi-pi stacking interaction links the molecules of ( III) into centrosymmetric dimeric aggregates, and a single C - H center dot center dot center dot pi( arene) hydrogen bond links the molecules of ( IV) into centrosymmetric dimers.

Original language	English
Number of pages	4
Journal	Acta Crystallographica Section C-Crystal Structure Communications
Volume	63
DOIs	https://doi.org/10.1107/S0108270107039194
Publication status	Published - Oct 2007

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da Silva, F. D. C., Wardell, J. L., Wardell, S. M. S. V., Ferreira, V. F., Low, J. N., & Glidewell, C. (2007). pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene. Acta Crystallographica Section C-Crystal Structure Communications, 63. https://doi.org/10.1107/S0108270107039194

da Silva, Fernando de C. ; Wardell, James L. ; Wardell, Solange M. S. V. et al. / pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene. In: Acta Crystallographica Section C-Crystal Structure Communications. 2007 ; Vol. 63.

@article{eac1c8923868483dbcf72241e35cf346,

title = "pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene",

abstract = "The title compounds, namely 6- methoxy- 3,3- dimethyl- 3Hbenzo[ f] chromene, C16H16O2, ( III), and racemic 3- bromo2,2,6,6- tetramethyl- 3,4- dihydro- 2H, 6H- 1,5- dioxatriphenylene, C20H21BrO2, ( IV), were both synthesized in one- step regioselective Wittig reactions from substituted 1,2- naphthoquinones. The new ring in both compounds adopts a screw- boat conformation. A single pi-pi stacking interaction links the molecules of ( III) into centrosymmetric dimeric aggregates, and a single C - H center dot center dot center dot pi( arene) hydrogen bond links the molecules of ( IV) into centrosymmetric dimers.",

author = "{da Silva}, {Fernando de C.} and Wardell, {James L.} and Wardell, {Solange M. S. V.} and Ferreira, {Vitor F.} and Low, {John N.} and Christopher Glidewell",

year = "2007",

month = oct,

doi = "10.1107/S0108270107039194",

language = "English",

volume = "63",

journal = "Acta Crystallographica Section C-Crystal Structure Communications",

issn = "1600-5759",

publisher = "International Union of Crystallography",

}

da Silva, FDC, Wardell, JL, Wardell, SMSV, Ferreira, VF, Low, JN & Glidewell, C 2007, 'pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene', Acta Crystallographica Section C-Crystal Structure Communications, vol. 63. https://doi.org/10.1107/S0108270107039194

pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene. / da Silva, Fernando de C.; Wardell, James L.; Wardell, Solange M. S. V. et al.
In: Acta Crystallographica Section C-Crystal Structure Communications, Vol. 63, 10.2007.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene

AU - da Silva, Fernando de C.

AU - Wardell, James L.

AU - Wardell, Solange M. S. V.

AU - Ferreira, Vitor F.

AU - Low, John N.

AU - Glidewell, Christopher

PY - 2007/10

Y1 - 2007/10

N2 - The title compounds, namely 6- methoxy- 3,3- dimethyl- 3Hbenzo[ f] chromene, C16H16O2, ( III), and racemic 3- bromo2,2,6,6- tetramethyl- 3,4- dihydro- 2H, 6H- 1,5- dioxatriphenylene, C20H21BrO2, ( IV), were both synthesized in one- step regioselective Wittig reactions from substituted 1,2- naphthoquinones. The new ring in both compounds adopts a screw- boat conformation. A single pi-pi stacking interaction links the molecules of ( III) into centrosymmetric dimeric aggregates, and a single C - H center dot center dot center dot pi( arene) hydrogen bond links the molecules of ( IV) into centrosymmetric dimers.

AB - The title compounds, namely 6- methoxy- 3,3- dimethyl- 3Hbenzo[ f] chromene, C16H16O2, ( III), and racemic 3- bromo2,2,6,6- tetramethyl- 3,4- dihydro- 2H, 6H- 1,5- dioxatriphenylene, C20H21BrO2, ( IV), were both synthesized in one- step regioselective Wittig reactions from substituted 1,2- naphthoquinones. The new ring in both compounds adopts a screw- boat conformation. A single pi-pi stacking interaction links the molecules of ( III) into centrosymmetric dimeric aggregates, and a single C - H center dot center dot center dot pi( arene) hydrogen bond links the molecules of ( IV) into centrosymmetric dimers.

U2 - 10.1107/S0108270107039194

DO - 10.1107/S0108270107039194

M3 - Article

SN - 1600-5759

VL - 63

JO - Acta Crystallographica Section C-Crystal Structure Communications

JF - Acta Crystallographica Section C-Crystal Structure Communications

ER -

da Silva FDC, Wardell JL, Wardell SMSV, Ferreira VF, Low JN, Glidewell C. pi-Stacked dimers in 6-methoxy-3,3-dimethyl-3H-benzo[f]chromene, and centrosymmetric dimers containing C-H center dot center dot center dot pi(arene) hydrogen bonds in racemic 3-bromo-2,2,6,6-tetramethyl-3,4-dihydro-2H,6H-1,5-dioxatriphenylene. Acta Crystallographica Section C-Crystal Structure Communications. 2007 Oct;63. doi: 10.1107/S0108270107039194