Investigations into the construction of the pentasubstituted ring C of Neosurugatoxin – a crystallographic study

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Abstract

The crystal structures of three cyclo­penta­[c]furans with various substituents at the 4-, 5- and 6-positions of the ring system are reported, namely, (±)-(3aR,4S,5S,6aS)-4-methyl-5-phenyl­hexa­hydro-1H-cyclo­penta­[c]furan-4,5-diol, C14H18O3, (I), (±)-(3aR,4S,5S,6aS)-4-benz­yloxy-4-methyl-5-phenyl­hexa­hydro-1H-cyclo­penta­[c]furan-5-ol, C21H24O3, (II), and (±)-(1aR,1bS,4aR,5S,5aR)-5-benz­yloxy-5-methyl-5a-phenyl­hexa­hydro-2H-oxireno[2′,3′:3,4]cyclopenta­[1,2-c]furan, C21H22O3, (III). The dominant inter­action in (I) and (II) is an O—H⋯O hydrogen bond across the bicyclic 5,5-ring system between the non-functionalized hy­droxy group and the tetra­hydro­furan O atom, which appears to influence the envelope conformations of the fused five-membered rings, whereas in (III), the rings have different conformations. A weak intra­molecular C—H⋯O inter­action appears to influence the degree of tilt of the phenyl ring attached to the 5-position and is different in (I) compared to (II) and (III).
Original languageEnglish
Pages (from-to)44-48
Number of pages5
JournalActa Crystallographica Section E: Crystallographic Communications
Volume72
Issue number1
DOIs
Publication statusPublished - 1 Jan 2016

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furans
Conformations
rings
Furans
Hydrogen bonds
Crystal structure
Atoms
tetrahydrofuran
envelopes
furan
neosurugatoxin
interactions
hydrogen bonds
crystal structure
atoms

Keywords

  • fused rings
  • conformation
  • intra­molecular O—H⋯O hydrogen bonds
  • weak interactions
  • crystal structure

Cite this

@article{79cb2535906047be8cb3ef75c090ed90,
title = "Investigations into the construction of the pentasubstituted ring C of Neosurugatoxin – a crystallographic study",
abstract = "The crystal structures of three cyclo­penta­[c]furans with various substituents at the 4-, 5- and 6-positions of the ring system are reported, namely, (±)-(3aR,4S,5S,6aS)-4-methyl-5-phenyl­hexa­hydro-1H-cyclo­penta­[c]furan-4,5-diol, C14H18O3, (I), (±)-(3aR,4S,5S,6aS)-4-benz­yloxy-4-methyl-5-phenyl­hexa­hydro-1H-cyclo­penta­[c]furan-5-ol, C21H24O3, (II), and (±)-(1aR,1bS,4aR,5S,5aR)-5-benz­yloxy-5-methyl-5a-phenyl­hexa­hydro-2H-oxireno[2′,3′:3,4]cyclopenta­[1,2-c]furan, C21H22O3, (III). The dominant inter­action in (I) and (II) is an O—H⋯O hydrogen bond across the bicyclic 5,5-ring system between the non-functionalized hy­droxy group and the tetra­hydro­furan O atom, which appears to influence the envelope conformations of the fused five-membered rings, whereas in (III), the rings have different conformations. A weak intra­molecular C—H⋯O inter­action appears to influence the degree of tilt of the phenyl ring attached to the 5-position and is different in (I) compared to (II) and (III).",
keywords = "fused rings, conformation, intra­molecular O—H⋯O hydrogen bonds, weak interactions, crystal structure",
author = "Jones, {Alan M.} and Storey, {John M. D.} and Harrison, {William T. A.}",
note = "We thank the EPSRC National Crystallography Service (University of Southampton) for the data collections.",
year = "2016",
month = "1",
day = "1",
doi = "10.1107/S2056989015023506",
language = "English",
volume = "72",
pages = "44--48",
journal = "Acta Crystallographica Section E: Crystallographic Communications",
issn = "2056-9890",
publisher = "International Union of Crystallography",
number = "1",

}

TY - JOUR

T1 - Investigations into the construction of the pentasubstituted ring C of Neosurugatoxin – a crystallographic study

AU - Jones, Alan M.

AU - Storey, John M. D.

AU - Harrison, William T. A.

N1 - We thank the EPSRC National Crystallography Service (University of Southampton) for the data collections.

PY - 2016/1/1

Y1 - 2016/1/1

N2 - The crystal structures of three cyclo­penta­[c]furans with various substituents at the 4-, 5- and 6-positions of the ring system are reported, namely, (±)-(3aR,4S,5S,6aS)-4-methyl-5-phenyl­hexa­hydro-1H-cyclo­penta­[c]furan-4,5-diol, C14H18O3, (I), (±)-(3aR,4S,5S,6aS)-4-benz­yloxy-4-methyl-5-phenyl­hexa­hydro-1H-cyclo­penta­[c]furan-5-ol, C21H24O3, (II), and (±)-(1aR,1bS,4aR,5S,5aR)-5-benz­yloxy-5-methyl-5a-phenyl­hexa­hydro-2H-oxireno[2′,3′:3,4]cyclopenta­[1,2-c]furan, C21H22O3, (III). The dominant inter­action in (I) and (II) is an O—H⋯O hydrogen bond across the bicyclic 5,5-ring system between the non-functionalized hy­droxy group and the tetra­hydro­furan O atom, which appears to influence the envelope conformations of the fused five-membered rings, whereas in (III), the rings have different conformations. A weak intra­molecular C—H⋯O inter­action appears to influence the degree of tilt of the phenyl ring attached to the 5-position and is different in (I) compared to (II) and (III).

AB - The crystal structures of three cyclo­penta­[c]furans with various substituents at the 4-, 5- and 6-positions of the ring system are reported, namely, (±)-(3aR,4S,5S,6aS)-4-methyl-5-phenyl­hexa­hydro-1H-cyclo­penta­[c]furan-4,5-diol, C14H18O3, (I), (±)-(3aR,4S,5S,6aS)-4-benz­yloxy-4-methyl-5-phenyl­hexa­hydro-1H-cyclo­penta­[c]furan-5-ol, C21H24O3, (II), and (±)-(1aR,1bS,4aR,5S,5aR)-5-benz­yloxy-5-methyl-5a-phenyl­hexa­hydro-2H-oxireno[2′,3′:3,4]cyclopenta­[1,2-c]furan, C21H22O3, (III). The dominant inter­action in (I) and (II) is an O—H⋯O hydrogen bond across the bicyclic 5,5-ring system between the non-functionalized hy­droxy group and the tetra­hydro­furan O atom, which appears to influence the envelope conformations of the fused five-membered rings, whereas in (III), the rings have different conformations. A weak intra­molecular C—H⋯O inter­action appears to influence the degree of tilt of the phenyl ring attached to the 5-position and is different in (I) compared to (II) and (III).

KW - fused rings

KW - conformation

KW - intra­molecular O—H⋯O hydrogen bonds

KW - weak interactions

KW - crystal structure

U2 - 10.1107/S2056989015023506

DO - 10.1107/S2056989015023506

M3 - Article

VL - 72

SP - 44

EP - 48

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

SN - 2056-9890

IS - 1

ER -