Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation

The synthesis and crystal structures of three new disubstituted [13]-macrodilactones, namely, trans-4,8-dimethyl-1,10-dioxacyclotridec-5-ene-2,9-dione, C13H20O4, I, cis-4-(4-bromophenyl)-13-methyl-1,10-dioxacyclotridec-5-ene-2,9-dione C18H21BrO4, II, and trans-11-methyl-4-phenyl-1,10-dioxacyclotride...

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Main Authors:	Kelli M. Rutledge, Caleb Griesbach, Brandon Q. Mercado, Mark W. Peczuh
Format:	Article
Language:	English
Published:	International Union of Crystallography 2020-10-01
Series:	Acta Crystallographica Section E: Crystallographic Communications
Subjects:	macrocycle conformation planar chirality crystal structure
Online Access:	http://scripts.iucr.org/cgi-bin/paper?S2056989020012037

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spelling	doaj-5adb92381916462081ae7245fe86502e2020-11-25T03:59:36ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-10-0176101617162310.1107/S2056989020012037mw2168Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformationKelli M. Rutledge0Caleb Griesbach1Brandon Q. Mercado2Mark W. Peczuh3Department of Chemistry, University of Connecticut, 55 N. Eagleville Road, U3060, Storrs, CT 06269, USADepartment of Chemistry, University of Connecticut, 55 N. Eagleville Road, U3060, Storrs, CT 06269, USADepartment of Chemistry, Yale University, PO Box 208107, New Haven, CT 06520, USADepartment of Chemistry, University of Connecticut, 55 N. Eagleville Road, U3060, Storrs, CT 06269, USAThe synthesis and crystal structures of three new disubstituted [13]-macrodilactones, namely, trans-4,8-dimethyl-1,10-dioxacyclotridec-5-ene-2,9-dione, C13H20O4, I, cis-4-(4-bromophenyl)-13-methyl-1,10-dioxacyclotridec-5-ene-2,9-dione C18H21BrO4, II, and trans-11-methyl-4-phenyl-1,10-dioxacyclotridec-5-ene-2,9-dione, C18H22O4, III, are reported and their conformations are put in the context of other [13]-macrodilactone structures reported previously. Together, they show that the number, location, and relative disposition of groups attached at the termini of planar units of the [13]-macrodilactones subtly influence their aspect ratios.http://scripts.iucr.org/cgi-bin/paper?S2056989020012037macrocycleconformationplanar chiralitycrystal structure
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Kelli M. Rutledge Caleb Griesbach Brandon Q. Mercado Mark W. Peczuh
spellingShingle	Kelli M. Rutledge Caleb Griesbach Brandon Q. Mercado Mark W. Peczuh Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation Acta Crystallographica Section E: Crystallographic Communications macrocycle conformation planar chirality crystal structure
author_facet	Kelli M. Rutledge Caleb Griesbach Brandon Q. Mercado Mark W. Peczuh
author_sort	Kelli M. Rutledge
title	Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation
title_short	Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation
title_full	Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation
title_fullStr	Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation
title_full_unstemmed	Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation
title_sort	structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation
publisher	International Union of Crystallography
series	Acta Crystallographica Section E: Crystallographic Communications
issn	2056-9890
publishDate	2020-10-01
description	The synthesis and crystal structures of three new disubstituted [13]-macrodilactones, namely, trans-4,8-dimethyl-1,10-dioxacyclotridec-5-ene-2,9-dione, C13H20O4, I, cis-4-(4-bromophenyl)-13-methyl-1,10-dioxacyclotridec-5-ene-2,9-dione C18H21BrO4, II, and trans-11-methyl-4-phenyl-1,10-dioxacyclotridec-5-ene-2,9-dione, C18H22O4, III, are reported and their conformations are put in the context of other [13]-macrodilactone structures reported previously. Together, they show that the number, location, and relative disposition of groups attached at the termini of planar units of the [13]-macrodilactones subtly influence their aspect ratios.
topic	macrocycle conformation planar chirality crystal structure
url	http://scripts.iucr.org/cgi-bin/paper?S2056989020012037
work_keys_str_mv	AT kellimrutledge structuresofthreedisubstituted13macrodilactonesrevealeffectsofsubstitutiononmacrocycleconformation AT calebgriesbach structuresofthreedisubstituted13macrodilactonesrevealeffectsofsubstitutiononmacrocycleconformation AT brandonqmercado structuresofthreedisubstituted13macrodilactonesrevealeffectsofsubstitutiononmacrocycleconformation AT markwpeczuh structuresofthreedisubstituted13macrodilactonesrevealeffectsofsubstitutiononmacrocycleconformation
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Structures of three disubstituted [13]-macrodilactones reveal effects of substitution on macrocycle conformation

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