Crystal structures of N-tert-butyl-3-(4-fluoro-phenyl)-5-oxo-4-[2-(trifluoromethoxy)phenyl]-2,5-dihydrofuran-2-carboxamide and 4-(2H-1,3-benzo-dioxol-5-yl)-N-cyclohexyl-5-oxo-3-[4-(trifluoro-methyl)phenyl]-2,5-dihydrofuran-2-carboxamide

Sue A Roberts, Guillermo Martinez-Ariza, Christopher Hulme, A. J. Lough

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The title compounds, C<inf>22</inf>H<inf>19</inf>F<inf>4</inf>NO<inf>4</inf>, (I), and C<inf>25</inf>H<inf>22</inf>F<inf>3</inf>NO<inf>5</inf>, (II), each contain a central nearly planar dihydrofuranone ring. The r.m.s. deviation from planarity of these rings is 0.015 Å in (I) and 0.027 Å in (II). The molecules are T-shaped, with the major conformational difference being the O - C - C - O torsion angle [-178.9 (1) in (I) and 37.7 (2)° in (II)]. In the crystal of (I), molecules are linked by N - H⋯O hydrogen bonds, forming chains along [001] while in (II) molecules are linked by N - H⋯O hydrogen bonds, forming chains along [010]. In (II), the trifluoromethyl substituent is disordered over two sets of sites, with refined occupancies of 0.751 (3) and 0.249 (3).

Original languageEnglish (US)
Pages (from-to)199-202
Number of pages4
JournalActa Crystallographica Section E: Structure Reports Online
Volume71
Issue number2
DOIs
StatePublished - Feb 1 2015

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Crystal structure
crystal structure
Molecules
Hydrogen bonds
hydrogen bonds
molecules
rings
Torsional stress
torsion
deviation
Crystals
crystals
2,5-dihydrofuran

Keywords

  • Butenolides
  • Crystal structure
  • N - H⋯O hydrogen bonding
  • Pharmaceuticals

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Materials Science(all)
  • Chemistry(all)

Cite this

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title = "Crystal structures of N-tert-butyl-3-(4-fluoro-phenyl)-5-oxo-4-[2-(trifluoromethoxy)phenyl]-2,5-dihydrofuran-2-carboxamide and 4-(2H-1,3-benzo-dioxol-5-yl)-N-cyclohexyl-5-oxo-3-[4-(trifluoro-methyl)phenyl]-2,5-dihydrofuran-2-carboxamide",
abstract = "The title compounds, C22H19F4NO4, (I), and C25H22F3NO5, (II), each contain a central nearly planar dihydrofuranone ring. The r.m.s. deviation from planarity of these rings is 0.015 {\AA} in (I) and 0.027 {\AA} in (II). The molecules are T-shaped, with the major conformational difference being the O - C - C - O torsion angle [-178.9 (1) in (I) and 37.7 (2)° in (II)]. In the crystal of (I), molecules are linked by N - H⋯O hydrogen bonds, forming chains along [001] while in (II) molecules are linked by N - H⋯O hydrogen bonds, forming chains along [010]. In (II), the trifluoromethyl substituent is disordered over two sets of sites, with refined occupancies of 0.751 (3) and 0.249 (3).",
keywords = "Butenolides, Crystal structure, N - H⋯O hydrogen bonding, Pharmaceuticals",
author = "Roberts, {Sue A} and Guillermo Martinez-Ariza and Christopher Hulme and Lough, {A. J.}",
year = "2015",
month = "2",
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language = "English (US)",
volume = "71",
pages = "199--202",
journal = "Acta Crystallographica Section E: Structure Reports Online",
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TY - JOUR

T1 - Crystal structures of N-tert-butyl-3-(4-fluoro-phenyl)-5-oxo-4-[2-(trifluoromethoxy)phenyl]-2,5-dihydrofuran-2-carboxamide and 4-(2H-1,3-benzo-dioxol-5-yl)-N-cyclohexyl-5-oxo-3-[4-(trifluoro-methyl)phenyl]-2,5-dihydrofuran-2-carboxamide

AU - Roberts, Sue A

AU - Martinez-Ariza, Guillermo

AU - Hulme, Christopher

AU - Lough, A. J.

PY - 2015/2/1

Y1 - 2015/2/1

N2 - The title compounds, C22H19F4NO4, (I), and C25H22F3NO5, (II), each contain a central nearly planar dihydrofuranone ring. The r.m.s. deviation from planarity of these rings is 0.015 Å in (I) and 0.027 Å in (II). The molecules are T-shaped, with the major conformational difference being the O - C - C - O torsion angle [-178.9 (1) in (I) and 37.7 (2)° in (II)]. In the crystal of (I), molecules are linked by N - H⋯O hydrogen bonds, forming chains along [001] while in (II) molecules are linked by N - H⋯O hydrogen bonds, forming chains along [010]. In (II), the trifluoromethyl substituent is disordered over two sets of sites, with refined occupancies of 0.751 (3) and 0.249 (3).

AB - The title compounds, C22H19F4NO4, (I), and C25H22F3NO5, (II), each contain a central nearly planar dihydrofuranone ring. The r.m.s. deviation from planarity of these rings is 0.015 Å in (I) and 0.027 Å in (II). The molecules are T-shaped, with the major conformational difference being the O - C - C - O torsion angle [-178.9 (1) in (I) and 37.7 (2)° in (II)]. In the crystal of (I), molecules are linked by N - H⋯O hydrogen bonds, forming chains along [001] while in (II) molecules are linked by N - H⋯O hydrogen bonds, forming chains along [010]. In (II), the trifluoromethyl substituent is disordered over two sets of sites, with refined occupancies of 0.751 (3) and 0.249 (3).

KW - Butenolides

KW - Crystal structure

KW - N - H⋯O hydrogen bonding

KW - Pharmaceuticals

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